ADDITIVES FOR COLOR DRIFT REDUCTION IN COPPER-BASED ANTIMICROBIAL POLYMERIC FORMULATIONS

Abstract

Biocidal compositions including a carrier, a copper-containing material, and a copper-coordinating additive are provided. Methods of minimizing the color drift of a carrier are also provided. Methods of accelerating a color endpoint of a carrier are also provided.

Claims

1. A biocidal composition, comprising: a carrier; a copper-containing material in the carrier, wherein the copper-containing materials comprises from 10 to 100 weight % of an amount of extractable copper; and a copper-coordinating additive in the carrier, in a molar ratio of the amount of extractable copper to an amount of the copper-coordinating additive of from 1:0.1 to 1:25, wherein a concentration of the copper-containing material and the copper-coordinating additive in the carrier is from 0.01% weight/weight of the carrier to 5% weight/weight of the carrier.

2. The composition of claim 1, wherein the copper-containing material comprises from 25 to 50 weight % of the amount of extractable copper.

3. The composition of claim 1, wherein the copper-coordinating additive is a compound of formula (I), (II), (III), (IV), (V), (XI), or (XII): ##STR00057## wherein each of R.sup.1 and R.sup.2 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; provided that both of R.sup.1 and R.sup.2 are not simultaneously hydrogen; each R.sup.3 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, substituted or unsubstituted 2-pyridyl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; the substituted 2-pyridyl is substituted with up to four substituents, each substituent independently selected from the group consisting of (C.sub.1-C.sub.30)alkyl, (C.sub.1-C.sub.30)alkoxy, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkenoxy, (C.sub.2-C.sub.30)alkynyl, (C.sub.2-C.sub.30)alkynoxy, aryl, aryloxy, heteroaryl, heteroaryloxy, heterocyclyl, heterocyclyloxy, aryl(C.sub.1-C.sub.4)alkyl, aryl(C.sub.1-C.sub.4)alkoxy, heteroaryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkoxy, heterocyclyl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkoxy; each R.sup.4 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; R.sup.5 is selected from the group consisting of substituted or unsubstituted (C.sub.1-C.sub.30)alkyl, substituted or unsubstituted (C.sub.2-C.sub.30)alkenyl, substituted or unsubstituted (C.sub.2-C.sub.30)alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl(C.sub.1-C.sub.4)alkyl, substituted or unsubstituted heteroaryl(C.sub.1-C.sub.4)alkyl, and substituted or unsubstituted heterocyclyl(C.sub.1-C.sub.4)alkyl; the substituted (C.sub.1-C.sub.30)alkyl, substituted (C.sub.2-C.sub.30)alkenyl, substituted (C.sub.2-C.sub.30)alkynyl, substituted aryl, substituted heteroaryl, substituted heterocyclyl, substituted aryl(C.sub.1-C.sub.4)alkyl, substituted heteroaryl(C.sub.1-C.sub.4)alkyl, and substituted heterocyclyl(C.sub.1-C.sub.4)alkyl are substituted with one or more substituents each of which is independently selected from the group consisting of OH, NH.sub.2, SH, CN, C(O)NH.sub.2, and CO.sub.2H; from S to S, R.sup.6 is selected from the group consisting of substituted or unsubstituted (C.sub.2-C.sub.30)alkylene, substituted or unsubstituted (C.sub.2-C.sub.30)alkenylene, substituted or unsubstituted (C.sub.2-C.sub.30)alkynylene, substituted or unsubstituted aryl(C.sub.1-C.sub.4)alkylene, substituted or unsubstituted (C.sub.1-C.sub.4)alkylarylene, substituted or unsubstituted (C.sub.1-C.sub.4)alkylaryl(C.sub.1-C.sub.4)alkylene, substituted or unsubstituted heteroaryl(C.sub.1-C.sub.4)alkylene, substituted or unsubstituted (C.sub.1-C.sub.4)alkylheteroarylene, substituted or unsubstituted (C.sub.1-C.sub.4)alkylheteroaryl(C.sub.1-C.sub.4)alkylene, substituted or unsubstituted heterocyclyl(C.sub.1-C.sub.4)alkylene, substituted or unsubstituted (C.sub.1-C.sub.4)alkylheterocyclylene, and substituted or unsubstituted (C.sub.1-C.sub.4)alkylheterocyclyl(C.sub.1-C.sub.4)alkylene; the substituted (C.sub.2-C.sub.30)alkylene, substituted (C.sub.2-C.sub.30)alkenylene, substituted (C.sub.2-C.sub.30)alkynylene, substituted aryl(C.sub.1-C.sub.4)alkylene, substituted (C.sub.1-C.sub.4)alkylarylene, substituted (C.sub.1-C.sub.4)alkylaryl(C.sub.1-C.sub.4)alkylene, substituted heteroaryl(C.sub.1-C.sub.4)alkylene, substituted (C.sub.1-C.sub.4)alkylheteroarylene, substituted (C.sub.1-C.sub.4)alkylheteroaryl(C.sub.1-C.sub.4)alkylene, substituted heterocyclyl(C.sub.1-C.sub.4)alkylene, substituted (C.sub.1-C.sub.4)alkylheterocyclylene, and substituted (C.sub.1-C.sub.4)alkylheterocyclyl(C.sub.1-C.sub.4)alkylene are substituted with one or more substituents each independently selected from the group consisting of (C.sub.1-C.sub.30)alkyl, (C.sub.1-C.sub.30)alkoxy, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkenyloxy, (C.sub.2-C.sub.30)alkynyl, (C.sub.2-C.sub.30)alkynyloxy, aryl, aryloxy, heteroaryl, heteroaryloxy, heterocyclyl, heterocyclyloxy, aryl(C.sub.1-C.sub.4)alkyl, aryl(C.sub.1-C.sub.4)alkoxy, heteroaryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkoxy, heterocyclyl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkoxy; provided that the two thiol groups in formula (IV) are not bonded to the same carbon; each R.sup.7 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.1-C.sub.30)alkoxy, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkenyloxy, (C.sub.2-C.sub.30)alkynyl, (C.sub.2-C.sub.30)alkynyloxy, aryl, aryloxy, heteroaryl, heteroaryloxy, heterocyclyl, heterocyclyloxy, aryl(C.sub.1-C.sub.4)alkyl, aryl(C.sub.1-C.sub.4)alkoxy, heteroaryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkoxy, heterocyclyl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkoxy; R.sup.8 is selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, heterocyclyl(C.sub.1-C.sub.4)alkyl, and (C(R.sup.7).sub.2).sub.zOH; each of x, y, and z is independently 2 or 3; each R.sup.19 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; provided that all R.sup.19 are not simultaneously hydrogen; each R.sup.20 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; and provided that all R.sup.20 are not simultaneously hydrogen.

4. The composition of claim 1, wherein the copper-coordinating additive is a compound of formula (I), (III), (VI), (VII), (IX), (X), (XI), or (II): ##STR00058## wherein each of R.sup.1 and R.sup.2 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; provided that both of R.sup.1 and R.sup.2 are not simultaneously hydrogen; R.sup.5 is selected from the group consisting of substituted or unsubstituted (C.sub.1-C.sub.30)alkyl, substituted or unsubstituted (C.sub.2-C.sub.30)alkenyl, substituted or unsubstituted (C.sub.2-C.sub.30)alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl(C.sub.1-C.sub.4)alkyl, substituted or unsubstituted heteroaryl(C.sub.1-C.sub.4)alkyl, and substituted or unsubstituted heterocyclyl(C.sub.1-C.sub.4)alkyl; the substituted (C.sub.1-C.sub.30)alkyl, substituted (C.sub.2-C.sub.30)alkenyl, substituted (C.sub.2-C.sub.30)alkynyl, substituted aryl, substituted heteroaryl, substituted heterocyclyl, substituted aryl(C.sub.1-C.sub.4)alkyl, substituted heteroaryl(C.sub.1-C.sub.4)alkyl, and substituted heterocyclyl(C.sub.1-C.sub.4)alkyl in formula (III) are substituted with one or more substituents each of which is independently selected from the group consisting of OH, NH.sub.2, SH, CN, C(O)NH.sub.2, and CO.sub.2H; X.sup. is selected from the group consisting of fluoride, chloride, bromide, iodide, hexafluorophosphate, sulfate, an alkylsulfonate, and an arylsulfonate; R.sup.9 is selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; each of R.sup.10 and R.sup.11 is independently selected from the group consisting of substituted or unsubstituted (C.sub.1-C.sub.30)alkyl, substituted or unsubstituted (C.sub.2-C.sub.30)alkenyl, substituted or unsubstituted (C.sub.2-C.sub.30)alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl(C.sub.1-C.sub.4)alkyl, substituted or unsubstituted heteroaryl(C.sub.1-C.sub.4)alkyl, and substituted or unsubstituted heterocyclyl(C.sub.1-C.sub.4)alkyl; the substituted (C.sub.1-C.sub.30)alkyl, substituted (C.sub.2-C.sub.30)alkenyl, substituted (C.sub.2-C.sub.30)alkynyl, substituted aryl, substituted heteroaryl, substituted heterocyclyl, substituted aryl(C.sub.1-C.sub.4)alkyl, substituted heteroaryl(C.sub.1-C.sub.4)alkyl, and substituted heterocyclyl(C.sub.1-C.sub.4)alkyl in formula (VII) are substituted with one or more substituents each of which is independently selected from the group consisting of OH, NH.sub.2, SH, CN, C(O)NH.sub.2, C(O)NHR.sup.11, C(O)NR.sup.12, CO.sub.2H, and CO.sub.2R.sup.11; each R.sup.14 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.1-C.sub.30)alkoxy, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkenyloxy, (C.sub.2-C.sub.30)alkynyl, (C.sub.2-C.sub.30)alkynyloxy, aryl, aryloxy, heteroaryl, heteroaryloxy, heterocyclyl, heterocyclyloxy, aryl(C.sub.1-C.sub.4)alkyl, aryl(C.sub.1-C.sub.4)alkoxy, heteroaryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkoxy, heterocyclyl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkoxy; R.sup.15 is selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, heterocyclyl(C.sub.1-C.sub.4)alkyl, and (C(R.sup.14).sub.2).sub.pNH.sub.2; each of m, n, and p is independently 2 or 3; Y is O or S; each R.sup.16 is independently OR.sup.17 or N(R.sup.18).sub.2; R.sup.17 is selected from the group consisting of (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; and each R.sup.18 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; each R.sup.19 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; provided that all R.sup.19 are not simultaneously hydrogen; each R.sup.20 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; and provided that all R.sup.20 are not simultaneously hydrogen.

5. The composition of claim 1, wherein the copper-coordinating additive is a compound of formula (VIII): ##STR00059## wherein R.sup.12 is selected from the group consisting of substituted or unsubstituted (C.sub.1-C.sub.30)alkyl, substituted or unsubstituted (C.sub.2-C.sub.30)alkenyl, substituted or unsubstituted (C.sub.2-C.sub.30)alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl(C.sub.1-C.sub.4)alkyl, substituted or unsubstituted heteroaryl(C.sub.1-C.sub.4)alkyl, and substituted or unsubstituted heterocyclyl(C.sub.1-C.sub.4)alkyl; each R.sup.13 is independently selected from the group consisting of hydrogen, substituted or unsubstituted (C.sub.1-C.sub.30)alkyl, substituted or unsubstituted (C.sub.2-C.sub.30)alkenyl, substituted or unsubstituted (C.sub.2-C.sub.30)alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl(C.sub.1-C.sub.4)alkyl, substituted or unsubstituted heteroaryl(C.sub.1-C.sub.4)alkyl, and substituted or unsubstituted heterocyclyl(C.sub.1-C.sub.4)alkyl; and the substituted (C.sub.1-C.sub.30)alkyl, substituted (C.sub.2-C.sub.30)alkenyl, substituted (C.sub.2-C.sub.30)alkynyl, substituted aryl, substituted heteroaryl, substituted heterocyclyl, substituted aryl(C.sub.1-C.sub.4)alkyl, substituted heteroaryl(C.sub.1-C.sub.4)alkyl, and substituted heterocyclyl(C.sub.1-C.sub.4)alkyl are substituted with one or more substituents each of which is independently selected from the group consisting of OH, NH.sub.2, SH, CN, C(O)NH.sub.2, C(O)NHR.sup.13, C(O)NR.sup.13.sub.2, CO.sub.2H, and CO.sub.2R.sup.13; and wherein the composition further comprises a pretreatment solution.

6. The composition of claim 1, wherein the copper-coordinating additive is a compound selected from the group consisting of 2-ethylhexyl phosphate, bis(2-ethylhexyl)phosphate, methyl phosphate, dimethyl phosphate, trimethyl phosphate, phenyl phosphate, diphenyl phosphate, 2,2-bipyridine, terpyridine, citric acid, diethanolamine, triethanolamine, hydroxyamine hydrochloride, ethoxyamine hydrochloride, triethyl citrate, thiourea, urea, 14-crown-4, 15-crown-5, 18-crown-6, dibenzo-18-crown-6, aza-15-crown-5, aza-18-crown-6, and salen.

7. The composition of claim 1, wherein the composition demonstrates a greater than 3 logarithmic reduction in a concentration of a bacteria selected from the group consisting of Staphylococcus aureus, Enterobacter aerogenes, Pseudomonas aeruginosa, Methicillin Resistant Staphylococcus aureus, E. coli, and mixtures thereof.

8. The composition of claim 1, wherein the copper-coordinating additive is a thiol, zinc, or ascorbic acid, or a compound of formula (IV), (VI), (XI), (XII), (XIX), (XX), or (XXI): ##STR00060## wherein X.sup. is selected from the group consisting of fluoride, chloride, bromide, iodide, hexafluorophosphate, sulfate, an alkylsulfonate, and an arylsulfonate; R.sup.9 is selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; wherein each R.sup.19 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; wherein each R.sup.20 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; wherein each R.sup.21 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; wherein R.sup.22 is selected from the group consisting of (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; wherein each R.sup.23 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; wherein R.sup.24 is selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; wherein R.sup.5 is selected from the group consisting of (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; and wherein, from S to S, R.sup.6 is selected from the group consisting of substituted or unsubstituted (C.sub.2-C.sub.30)alkylene, substituted or unsubstituted (C.sub.2-C.sub.30)alkenylene, substituted or unsubstituted (C.sub.2-C.sub.30)alkynylene, substituted or unsubstituted aryl(C.sub.1-C.sub.4)alkylene, substituted or unsubstituted (C.sub.1-C.sub.4)alkylarylene, substituted or unsubstituted (C.sub.1-C.sub.4)alkylaryl(C.sub.1-C.sub.4)alkylene, substituted or unsubstituted heteroaryl(C.sub.1-C.sub.4)alkylene, substituted or unsubstituted (C.sub.1-C.sub.4)alkylheteroarylene, substituted or unsubstituted (C.sub.1-C.sub.4)alkylheteroaryl(C.sub.1-C.sub.4)alkylene, substituted or unsubstituted heterocyclyl(C.sub.1-C.sub.4)alkylene, substituted or unsubstituted (C.sub.1-C.sub.4)alkylheterocyclylene, and substituted or unsubstituted (C.sub.1-C.sub.4)alkylheterocyclyl(C.sub.1-C.sub.4)alkylene; the substituted (C.sub.2-C.sub.30)alkylene, substituted (C.sub.2-C.sub.30)alkenylene, substituted (C.sub.2-C.sub.30)alkynylene, substituted aryl(C.sub.1-C.sub.4)alkylene, substituted (C.sub.1-C.sub.4)alkylarylene, substituted (C.sub.1-C.sub.4)alkylaryl(C.sub.1-C.sub.4)alkene, substituted heteroaryl(C.sub.1-C.sub.4)alkylene, substituted (C.sub.1-C.sub.4)alkylheteroarylene, substituted (C.sub.1-C.sub.4)alkylheteroaryl(C.sub.1-C.sub.4)alkylene, substituted heterocyclyl(C.sub.1-C.sub.4)alkylene, substituted (C.sub.1-C.sub.4)alkylheterocyclylene, and substituted (C.sub.1-C.sub.4)alkylheterocyclyl(C.sub.1-C.sub.4)alkylene are substituted with one or more substituents each independently selected from the group consisting of (C.sub.1-C.sub.30)alkyl, (C.sub.1-C.sub.30)alkoxy, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkenyloxy, (C.sub.2-C.sub.30)alkynyl, (C.sub.2-C.sub.30)alkynyloxy, aryl, aryloxy, heteroaryl, heteroaryloxy, heterocyclyl, heterocyclyloxy, aryl(C.sub.1-C.sub.4)alkyl, aryl(C.sub.1-C.sub.4)alkoxy, heteroaryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkoxy, heterocyclyl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkoxy; optionally wherein the alpha-carbon of at least one R.sup.19 is a secondary or tertiary carbon; optionally wherein the alpha-carbon of at least one R.sup.21 is a secondary or tertiary carbon; optionally wherein the alpha-carbon of R.sup.22 is a secondary or tertiary carbon; optionally wherein the alpha-carbon of at least one R.sup.23 is a secondary or tertiary carbon; and optionally wherein the alpha-carbon of R.sup.24 is a secondary or tertiary carbon; provided that all R.sup.19 are not simultaneously hydrogen; provided that all R.sup.20 are not simultaneously hydrogen; provided that at least one R.sup.20 includes one or more heteroatoms selected from N, O, and S replacing the beta-carbon or gamma-carbon, and/or one or more heteroatoms selected from N, O, and S substituted for hydrogens on the alpha-carbon, beta-carbon, or gamma-carbon; or an alpha-carbon of at least one R.sup.20 is a secondary carbon or a tertiary carbon; provided that both R.sup.21 are not simultaneously hydrogen; provided that both R.sup.23 are not simultaneously hydrogen; and provided that R.sup.6 has a structure such that the two thiol groups are not bonded to the same carbon.

9. The composition of claim 1, wherein the copper-coordinating additive is a soft base, benzotriazole, an amino acid, a surfactant, a compound comprising an imidazole or a reduced imidazole group, a nitrile compound, or a compound of formula (I), (VI), (VII), (XI), (XII), (XIX), (XX), (XXI), (XXII), (XXIII), (XXIV), (XXV), or (XXVI): ##STR00061## wherein X.sup. is selected from the group consisting of fluoride, chloride, bromide, iodide, hexafluorophosphate, sulfate, an alkylsulfonate, and an arylsulfonate; wherein a is an integer from 1 to 4; wherein b is an integer from 1 to 4, wherein c is an integer from 0 to 3; wherein each of R.sup.1 and R.sup.2 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.3M)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; wherein R.sup.9 is selected from the group consisting of (C.sub.1-C.sub.3M)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; wherein each of R.sup.10 and R.sup.11 is independently selected from the group consisting of (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; wherein each R.sup.19 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; wherein each R.sup.20 is independently selected form the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; wherein each R.sup.21 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; wherein R.sup.22 is selected from the group consisting of (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; wherein each R.sup.23 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl; wherein R.sup.24 is selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; wherein R.sup.25 is selected from the group consisting of (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; wherein each of R.sup.26, R.sup.27, R.sup.28, and R.sup.29 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; wherein each of R.sup.30, R.sup.31, R.sup.32, and R.sup.33 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; wherein each of R.sup.34, R.sup.35, and R.sup.36 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; wherein each of R.sup.37, R.sup.38, and R.sup.39 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; wherein the nitrile compound is selected from the group consisting of a (C.sub.1-C.sub.30)alkylnitrile, a (C.sub.2-C.sub.30)alkenylnitrile, a (C.sub.2-C.sub.30)alkynylnitrile, an arylnitrile, a heteroarylnitrile, a heterocyclylnitrile, an aryl(C.sub.1-C.sub.4)alkylnitrile, a heteroaryl(C.sub.1-C.sub.4)alkylnitrile, and a heterocyclyl(C.sub.1-C.sub.4)alkylnitrile; and wherein a substituted compound of formula (XXIV) includes one or more carbons substituted with one or more substituents selected from the group consisting of (C.sub.1-C.sub.30)alkyl, (C.sub.1-C.sub.30)alkoxy, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkenyloxy, (C.sub.2-C.sub.30)alkynyl, (C.sub.2-C.sub.30)alkynyloxy, aryl, aryloxy, heteroaryl, heteroaryloxy, heterocyclyl, heterocyclyloxy, aryl(C.sub.1-C.sub.4)alkyl, aryl(C.sub.1-C.sub.4)alkoxy, heteroaryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkoxy, heterocyclyl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkoxy; optionally wherein the alpha-carbon of at least one of R.sup.26, R.sup.27, R.sup.28, and R.sup.29 is a secondary or tertiary carbon; optionally wherein the alpha-carbon of at least one of R.sup.30, R.sup.31, R.sup.32, and R.sup.33 is a secondary or tertiary carbon; optionally wherein the alpha-carbon of at least one of R.sup.34, R.sup.35, and R.sup.36 is a secondary or tertiary carbon; optionally wherein the alpha-carbon of at least one of R.sup.37, R.sup.38, and R.sup.39 is a secondary or tertiary carbon; and optionally wherein the alpha-carbon of the nitrile compound is a secondary or tertiary carbon; provided that both of R.sup.1 and R.sup.2 are not simultaneously hydrogen and that the alpha-carbon of at least one of R.sup.1 and R.sup.2 is a secondary or tertiary carbon; provided that the alpha-carbon of R.sup.9 is a secondary or tertiary carbon; provided that the alpha carbon of at least one of R.sup.10 and R.sup.11 is a secondary or tertiary carbon; provided that all R.sup.19 are not simultaneously hydrogen and that the alpha-carbon of at least one R.sup.19 is a secondary or tertiary carbon; provided that all R.sup.20 are not simultaneously hydrogen, and that an alpha-carbon of at least one R.sup.20 is a secondary carbon or a tertiary carbon; provided that both R.sup.21 are not simultaneously hydrogen; provided that the alpha-carbon of at least one R.sup.1 and/or R.sup.22 is a secondary or tertiary carbon; provided that the alpha-carbon of at least one R.sup.23 and/or R.sup.23 is a secondary or tertiary carbon; provided that the alpha-carbon of R.sup.2 is a secondary or tertiary carbon; provided that R.sup.34, R.sup.35, and R.sup.36 are not simultaneously hydrogen; and provided that R.sup.37, R.sup.38, and R.sup.39 are not simultaneously hydrogen.

10. A method of minimizing a color change in a biocidal material, comprising: combining a copper-containing material comprising from 10 to 100 weight % of an amount of extractable copper with an amount of copper-coordinating additive, in a molar ratio of the amount of extractable copper to the amount of copper-coordinating additive of from 1:0.1 to 1:25 to form a copper-containing mixture; and combining the copper-containing mixture with a carrier to form the biocidal material, wherein a concentration of the copper-containing material and the copper-coordinating additive of the copper-containing mixture in the carrier is from 0.01% weight/weight of the carrier to 5% weight/weight of the carrier; and wherein the color change in the biocidal material is minimized relative to a change in color of a mixture of the carrier and the copper-containing material in the absence of the copper-coordinating additive.

11. The method of claim 10, wherein the copper-containing material comprises from 25 to 50 weight % of the amount of extractable copper.

12. The method of claim 10, wherein the copper-coordinating additive is a compound of formula (I), (II), (III), (IV), (V), (XI), or (XII): ##STR00062## wherein each of R.sup.1 and R.sup.2 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; provided that both of R.sup.1 and R.sup.2 are not simultaneously hydrogen; each R.sup.3 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, substituted or unsubstituted 2-pyridyl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; the substituted 2-pyridyl is substituted with up to four substituents, each substituent independently selected from the group consisting of (C.sub.1-C.sub.30)alkyl, (C.sub.1-C.sub.30)alkoxy, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkenoxy, (C.sub.2-C.sub.30)alkynyl, (C.sub.2-C.sub.30)alkynoxy, aryl, aryloxy, heteroaryl, heteroaryloxy, heterocyclyl, heterocyclyloxy, aryl(C.sub.1-C.sub.4)alkyl, aryl(C.sub.1-C.sub.4)alkoxy, heteroaryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkoxy, heterocyclyl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkoxy; each R.sup.4 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; R.sup.5 is selected from the group consisting of substituted or unsubstituted (C.sub.1-C.sub.30)alkyl, substituted or unsubstituted (C.sub.2-C.sub.30)alkenyl, substituted or unsubstituted (C.sub.2-C.sub.30)alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl(C.sub.1-C.sub.4)alkyl, substituted or unsubstituted heteroaryl(C.sub.1-C.sub.4)alkyl, and substituted or unsubstituted heterocyclyl(C.sub.1-C.sub.4)alkyl; the substituted (C.sub.1-C.sub.30)alkyl, substituted (C.sub.2-C.sub.30)alkenyl, substituted (C.sub.2-C.sub.30)alkynyl, substituted aryl, substituted heteroaryl, substituted heterocyclyl, substituted aryl(C.sub.1-C.sub.4)alkyl, substituted heteroaryl(C.sub.1-C.sub.4)alkyl, and substituted heterocyclyl(C.sub.1-C.sub.4)alkyl are substituted with one or more substituents each of which is independently selected from the group consisting of OH, NH.sub.2, SH, CN, C(O)NH.sub.2, and CO.sub.2H; from S to S, R.sup.6 is selected from the group consisting of substituted or unsubstituted (C.sub.2-C.sub.30)alkylene, substituted or unsubstituted (C.sub.2-C.sub.30)alkenylene, substituted or unsubstituted (C.sub.2-C.sub.30)alkynylene, substituted or unsubstituted aryl(C.sub.1-C.sub.4)alkylene, substituted or unsubstituted (C.sub.1-C.sub.4)alkylarylene, substituted or unsubstituted (C.sub.1-C.sub.4)alkylaryl(C.sub.1-C.sub.4)alkylene, substituted or unsubstituted heteroaryl(C.sub.1-C.sub.4)alkylene, substituted or unsubstituted (C.sub.1-C.sub.4)alkylheteroarylene, substituted or unsubstituted (C.sub.1-C.sub.4)alkylheteroaryl(C.sub.1-C.sub.4)alkylene, substituted or unsubstituted heterocyclyl(C.sub.1-C.sub.4)alkylene, substituted or unsubstituted (C.sub.1-C.sub.4)alkylheterocyclylene, and substituted or unsubstituted (C.sub.1-C.sub.4)alkylheterocyclyl(C.sub.1-C.sub.4)alkylene; the substituted (C.sub.2-C.sub.30)alkylene, substituted (C.sub.2-C.sub.30)alkenylene, substituted (C.sub.2-C.sub.30)alkynylene, substituted aryl(C.sub.1-C.sub.4)alkylene, substituted (C.sub.1-C.sub.4)alkylarylene, substituted (C.sub.1-C.sub.4)alkylaryl(C.sub.1-C.sub.4)alkylene, substituted heteroaryl(C.sub.1-C.sub.4)alkylene, substituted (C.sub.1-C.sub.4)alkylheteroarylene, substituted (C.sub.1-C.sub.4)alkylheteroaryl(C.sub.1-C.sub.4)alkylene, substituted heterocyclyl(C.sub.1-C.sub.4)alkylene, substituted (C.sub.1-C.sub.4)alkylheterocyclylene, and substituted (C.sub.1-C.sub.4)alkylheterocyclyl(C.sub.1-C.sub.4)alkylene are substituted with one or more substituents each independently selected from the group consisting of (C.sub.1-C.sub.30)alkyl, (C.sub.1-C.sub.30)alkoxy, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkenyloxy, (C.sub.2-C.sub.30)alkynyl, (C.sub.2-C.sub.30)alkynyloxy, aryl, aryloxy, heteroaryl, heteroaryloxy, heterocyclyl, heterocyclyloxy, aryl(C.sub.1-C.sub.4)alkyl, aryl(C.sub.1-C.sub.4)alkoxy, heteroaryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkoxy, heterocyclyl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkoxy; provided that the two thiol groups in formula (IV) are not bonded to the same carbon; each R.sup.7 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.1-C.sub.30)alkoxy, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkenyloxy, (C.sub.2-C.sub.30)alkynyl, (C.sub.2C.sub.30)alkynyloxy, aryl, aryloxy, heteroaryl, heteroaryloxy, heterocyclyl, heterocyclyloxy, aryl(C.sub.1-C.sub.4)alkyl, aryl(C.sub.1-C.sub.4)alkoxy, heteroaryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkoxy, heterocyclyl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkoxy; R.sup.8 is selected from the group consisting of hydrogen, (C.sub.1-C.sub.3M)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, heterocyclyl(C.sub.1-C.sub.4)alkyl, and (C(R.sup.7).sub.2).sub.zOH; each of x, y, and z is independently 2 or 3; each R.sup.19 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; provided that all R.sup.19 are not simultaneously hydrogen; each R.sup.20 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; and provided that all R.sup.20 are not simultaneously hydrogen.

13. The method of claim 10, wherein the copper-coordinating additive is a thiol, zinc, or ascorbic acid, or a compound of formula (IV), (VI), (XI), (XII), (XIX), (XX), or (XXI): ##STR00063## wherein X.sup. is selected from the group consisting of fluoride, chloride, bromide, iodide, hexafluorophosphate, sulfate, an alkylsulfonate, and an arylsulfonate; R.sup.9 is selected from the group consisting of hydrogen, (C.sub.1-C.sub.3M)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; wherein each R.sup.19 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.3M)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; wherein each R.sup.20 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; wherein each R.sup.21 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.3M)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; wherein R.sup.22 is selected from the group consisting of (C.sub.1-C.sub.3M)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; wherein each R.sup.23 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.3M)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; wherein R.sup.24 is selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; wherein R.sup.25 is selected from the group consisting of (C.sub.1-C.sub.3M)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; and wherein, from S to S, R.sup.6 is selected from the group consisting of substituted or unsubstituted (C.sub.2-C.sub.30)alkylene, substituted or unsubstituted (C.sub.2-C.sub.30)alkenylene, substituted or unsubstituted (C.sub.2-C.sub.30)alkynylene, substituted or unsubstituted aryl(C.sub.1-C.sub.4)alkylene, substituted or unsubstituted (C.sub.1-C.sub.4)alkylarylene, substituted or unsubstituted (C.sub.1-C.sub.4)alkylaryl(C.sub.1-C.sub.4)alkylene, substituted or unsubstituted heteroaryl(C.sub.1-C.sub.4)alkylene, substituted or unsubstituted (C.sub.1-C.sub.4)alkylheteroarylene, substituted or unsubstituted (C.sub.1-C.sub.4)alkylheteroaryl(C.sub.1-C.sub.4)alkylene, substituted or unsubstituted heterocyclyl(C.sub.1-C.sub.4)alkylene, substituted or unsubstituted (C.sub.1-C.sub.4)alkylheterocyclylene, and substituted or unsubstituted (C.sub.1-C.sub.4)alkylheterocyclyl(C.sub.1-C.sub.4)alkylene; the substituted (C.sub.2-C.sub.30)alkylene, substituted (C.sub.2-C.sub.30)alkenylene, substituted (C.sub.2-C.sub.30)alkynylene, substituted aryl(C.sub.1-C.sub.4)alkylene, substituted (C.sub.1-C.sub.4)alkylarylene, substituted (C.sub.1-C.sub.4)alkylaryl(C.sub.1-C.sub.4)alkene, substituted heteroaryl(C.sub.1-C.sub.4)alkylene, substituted (C.sub.1-C.sub.4)alkylheteroarylene, substituted (C.sub.1-C.sub.4)alkylheteroaryl(C.sub.1-C.sub.4)alkylene, substituted heterocyclyl(C.sub.1-C.sub.4)alkylene, substituted (C.sub.1-C.sub.4)alkylheterocyclylene, and substituted (C.sub.1-C.sub.4)alkylheterocyclyl(C.sub.1-C.sub.4)alkylene are substituted with one or more substituents each independently selected from the group consisting of (C.sub.1-C.sub.30)alkyl, (C.sub.1-C.sub.30)alkoxy, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkenyloxy, (C.sub.2-C.sub.30)alkynyl, (C.sub.2-C.sub.30)alkynyloxy, aryl, aryloxy, heteroaryl, heteroaryloxy, heterocyclyl, heterocyclyloxy, aryl(C.sub.1-C.sub.4)alkyl, aryl(C.sub.1-C.sub.4)alkoxy, heteroaryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkoxy, heterocyclyl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkoxy; optionally wherein the alpha-carbon of at least one R.sup.19 is a secondary or tertiary carbon; optionally wherein the alpha-carbon of at least one R.sup.21 is a secondary or tertiary carbon; optionally wherein the alpha-carbon of R.sup.22 is a secondary or tertiary carbon; optionally wherein the alpha-carbon of at least one R.sup.23 is a secondary or tertiary carbon; and optionally wherein the alpha-carbon of R.sup.24 is a secondary or tertiary carbon; provided that all R.sup.19 are not simultaneously hydrogen; provided that all R.sup.20 are not simultaneously hydrogen; provided that at least one R.sup.20 includes one or more heteroatoms selected from N, O, and S replacing the beta-carbon or gamma-carbon, and/or one or more heteroatoms selected from N, O, and S substituted for hydrogens on the alpha-carbon, beta-carbon, or gamma-carbon; or an alpha-carbon of at least one R.sup.20 is a secondary carbon or a tertiary carbon; provided that both R.sup.21 are not simultaneously hydrogen; provided that both R.sup.23 are not simultaneously hydrogen; and provided that R.sup.6 has a structure such that the two thiol groups are not bonded to the same carbon.

14. The method of claim 10, wherein the copper-coordinating additive is a soft base, benzotriazole, an amino acid, a surfactant, a compound comprising an imidazole or a reduced imidazole group, a nitrile compound, or a compound of formula (I), (VI), (VII), (XI), (XII), (XIX), (XX), (XXI), (XXII), (XXIII), (XXIV), (XXV), or (XXVI): ##STR00064## wherein X.sup. is selected from the group consisting of fluoride, chloride, bromide, iodide, hexafluorophosphate, sulfate, an alkylsulfonate, and an arylsulfonate; wherein a is an integer from 1 to 4; wherein b is an integer from 1 to 4, wherein c is an integer from 0 to 3; wherein each of R.sup.1 and R.sup.2 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; wherein R.sup.9 is selected from the group consisting of (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; wherein each of R.sup.10 and R.sup.11 is independently selected from the group consisting of (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; wherein each R.sup.19 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; wherein each R.sup.20 is independently selected form the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; wherein each R.sup.21 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; wherein R.sup.22 is selected from the group consisting of (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; wherein each R.sup.23 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl; wherein R.sup.24 is selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; wherein R.sup.25 is selected from the group consisting of (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; wherein each of R.sup.26, R.sup.27, R.sup.28, and R.sup.29 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; wherein each of R.sup.30, R.sup.31, R.sup.32, and R.sup.33 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; wherein each of R.sup.34, R.sup.35, and R.sup.36 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; wherein each of R.sup.37, R.sup.38, and R.sup.39 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; wherein the nitrile compound is selected from the group consisting of a (C.sub.1-C.sub.30)alkylnitrile, a (C.sub.2-C.sub.30)alkenylnitrile, a (C.sub.2-C.sub.30)alkynylnitrile, an arylnitrile, a heteroarylnitrile, a heterocyclylnitrile, an aryl(C.sub.1-C.sub.4)alkylnitrile, a heteroaryl(C.sub.1-C.sub.4)alkylnitrile, and a heterocyclyl(C.sub.1-C.sub.4)alkylnitrile; and wherein a substituted compound of formula (XXIV) includes one or more carbons substituted with one or more substituents selected from the group consisting of (C.sub.1-C.sub.30)alkyl, (C.sub.1-C.sub.30)alkoxy, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkenyloxy, (C.sub.2-C.sub.30)alkynyl, (C.sub.2-C.sub.30)alkynyloxy, aryl, aryloxy, heteroaryl, heteroaryloxy, heterocyclyl, heterocyclyloxy, aryl(C.sub.1-C.sub.4)alkyl, aryl(C.sub.1-C.sub.4)alkoxy, heteroaryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkoxy, heterocyclyl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkoxy; optionally wherein the alpha-carbon of at least one of R.sup.26, R.sup.27, R.sup.28, and R.sup.29 is a secondary or tertiary carbon; optionally wherein the alpha-carbon of at least one of R.sup.30, R.sup.31, R.sup.32, and R.sup.33 is a secondary or tertiary carbon; optionally wherein the alpha-carbon of at least one of R.sup.34, R.sup.35, and R.sup.36 is a secondary or tertiary carbon; optionally wherein the alpha-carbon of at least one of R.sup.37, R.sup.38, and R.sup.39 is a secondary or tertiary carbon; and optionally wherein the alpha-carbon of the nitrile compound is a secondary or tertiary carbon; provided that both of R.sup.1 and R.sup.2 are not simultaneously hydrogen and that the alpha-carbon of at least one of R.sup.1 and R.sup.2 is a secondary or tertiary carbon; provided that the alpha-carbon of R.sup.9 is a secondary or tertiary carbon; provided that the alpha carbon of at least one of R.sup.10 and R.sup.11 is a secondary or tertiary carbon; provided that all R.sup.19 are not simultaneously hydrogen and that the alpha-carbon of at least one R.sup.19 is a secondary or tertiary carbon; provided that all R.sup.20 are not simultaneously hydrogen, and that an alpha-carbon of at least one R.sup.20 is a secondary carbon or a tertiary carbon; provided that both R.sup.21 are not simultaneously hydrogen; provided that the alpha-carbon of at least one R.sup.21 and/or R.sup.22 is a secondary or tertiary carbon; provided that the alpha-carbon of at least one R.sup.23 and/or R.sup.23 is a secondary or tertiary carbon; provided that the alpha-carbon of R.sup.25 is a secondary or tertiary carbon; provided that R.sup.34, R.sup.35, and R.sup.36 are not simultaneously hydrogen; and provided that R.sup.37, R.sup.38, and R.sup.39 are not simultaneously hydrogen.

15. The method of claim 10, wherein the copper-coordinating additive is a compound selected from the group consisting of 2-ethylhexyl phosphate, bis(2-ethylhexyl)phosphate, methyl phosphate, dimethyl phosphate, trimethyl phosphate, phenyl phosphate, diphenyl phosphate, 2,2-bipyridine, terpyridine, citric acid, diethanolamine, triethanolamine, 14-crown-4, 15-crown-5, 18-crown-6, dibenzo-18-crown-6, aza-15-crown-5, aza-18-crown-6, and salen.

16. The method of claim 10, wherein the biocidal material demonstrates a greater than 3 logarithmic reduction in a concentration of a bacteria selected from the group consisting of Staphylococcus aureus, Enterobacter aerogenes, Pseudomonas aeruginosa, Methicillin Resistant Staphylococcus aureus, E. coli, and mixtures thereof.

17. The method of claim 10, wherein a CIE E* value of the biocidal material is less than about 10, as measured according to formula (XIII): $\begin{matrix} E_{C}^{*} = \sqrt{({(L^{*} - L_{c ontrol}^{*})}^{2} + {(a^{*} - a_{control}^{*})}^{2} + {(b^{*} - b_{c ontrol}^{*})}^{2})} & (XIII) \end{matrix}$ wherein L*, a*, and b* are the CIE L*, a*, and b* values of the biocidal material and the L*.sub.control, a*.sub.control, and b*.sub.control are the CIE L*, a*, and b* values of the carrier.

18. A method of accelerating to a color endpoint in a biocidal material, comprising: combining a copper-containing material comprising from 10 to 100 weight % of an amount of extractable copper with an amount of copper-coordinating additive, in a molar ratio of the amount of extractable copper to the amount of copper-coordinating additive of from 1:0.1 to 1:25 to form a copper-coordinating mixture; and combining the copper-containing mixture with a carrier to form the biocidal material; wherein a concentration of the copper-containing material and the copper-coordinating additive of the copper-containing mixture in the carrier is from 0.01% weight/weight of the carrier to 5% weight/weight of the cater; wherein a CIE E* value of the biocidal material is less than about 10, as measured according to formula (XII): $\begin{matrix} E_{C}^{*} = \sqrt{({(L^{*} - L_{c ontrol}^{*})}^{2} + {(a^{*} - a_{control}^{*})}^{2} + {(b^{*} - b_{c ontrol}^{*})}^{2})} & (XIII) \end{matrix}$ wherein L*, a*, and b* are the CIE L*, a*, and b* values of the color endpoint and the L*.sub.control, a*.sub.control, and b*.sub.control are the initial CIE L*, a*, and b* values of the biocidal material; wherein the color endpoint in the biocidal material is accelerated relative to a change in color to a color endpoint of a mixture of the carrier and the copper-containing material in the absence of the copper-coordinating additive, wherein the copper-containing material comprises from 25 to 50 weight % of the amount of extractable copper; and wherein the biocidal material demonstrates a greater than 3 logarithmic reduction in a concentration of a bacterial selected from the group consisting of Staphvlococcus aureus, Enterobacter aerogenes, Pseudomonas aeruginosa, Methicillin Resistant Staphylococcus aureus, E. coli, and mixtures thereof.

19. (canceled)

20. The method of claim 18, wherein the copper-coordinating additive is a compound of formula (I), (III), (VI), (VII), (IX), (X), (XI), or (XII): ##STR00065## wherein each of R.sup.1 and R.sup.2 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; provided that both of R.sup.1 and R.sup.2 are not simultaneously hydrogen; R.sup.5 is selected from the group consisting of substituted or unsubstituted (C.sub.1-C.sub.30)alkyl, substituted or unsubstituted (C.sub.2-C.sub.30)alkenyl, substituted or unsubstituted (C.sub.2-C.sub.30)alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl(C.sub.1-C.sub.4)alkyl, substituted or unsubstituted heteroaryl(C.sub.1-C.sub.4)alkyl, and substituted or unsubstituted heterocyclyl(C.sub.1-C.sub.4)alkyl; the substituted (C.sub.1-C.sub.30)alkyl, substituted (C.sub.2-C.sub.30)alkenyl, substituted (C.sub.2-C.sub.30)alkynyl, substituted aryl, substituted heteroaryl, substituted heterocyclyl, substituted aryl(C.sub.1-C.sub.4)alkyl, substituted heteroaryl(C.sub.1-C.sub.4)alkyl, and substituted heterocyclyl(C.sub.1-C.sub.4)alkyl in formula (III) are substituted with one or more substituents each of which is independently selected from the group consisting of OH, NH.sub.2, SH, CN, C(O)NH.sub.2, and CO.sub.2H; X.sup. is selected from the group consisting of fluoride, chloride, bromide, iodide, hexafluorophosphate, sulfate, an alkylsulfonate, and an arylsulfonate; R.sup.9 is selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; each of R.sup.10 and R.sup.11 is independently selected from the group consisting of substituted or unsubstituted (C.sub.1-C.sub.30)alkyl, substituted or unsubstituted (C.sub.2-C.sub.30)alkenyl, substituted or unsubstituted (C.sub.2-C.sub.30)alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl(C.sub.1-C.sub.4)alkyl, substituted or unsubstituted heteroaryl(C.sub.1-C.sub.4)alkyl, and substituted or unsubstituted heterocyclyl(C.sub.1-C.sub.4)alkyl; the substituted (C.sub.1-C.sub.30)alkyl, substituted (C.sub.2-C.sub.30)alkenyl, substituted (C.sub.2-C.sub.30)alkynyl, substituted aryl, substituted heteroaryl, substituted heterocyclyl, substituted aryl(C.sub.1-C.sub.4)alkyl, substituted heteroaryl(C.sub.1-C.sub.4)alkyl, and substituted heterocyclyl(C.sub.1-C.sub.4)alkyl in formula (VII) are substituted with one or more substituents each of which is independently selected from the group consisting of OH, NH.sub.2, SH, CN, C(O)NH.sub.2, C(O)NHR.sup.11, C(O)NR.sup.12, CO.sub.2H, and CO.sub.2R.sup.11; each R.sup.14 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.1-C.sub.30)alkoxy, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkenyloxy, (C.sub.2-C.sub.30)alkynyl, (C.sub.2-C.sub.30)alkynyloxy, aryl, aryloxy, heteroaryl, heteroaryloxy, heterocyclyl, heterocyclyloxy, aryl(C.sub.1-C.sub.4)alkyl, aryl(C.sub.1-C.sub.4)alkoxy, heteroaryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkoxy, heterocyclyl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkoxy; R.sup.15 is selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, heterocyclyl(C.sub.1-C.sub.4)alkyl, and (C(R.sup.14).sub.2).sub.pNH.sub.2; each of m, n, and p is independently 2 or 3; Y is O or S; each R.sup.16 is independently OR.sup.17 or N(R.sup.18).sub.2; R.sup.17 is selected from the group consisting of (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; each R.sup.18 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; each R.sup.19 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; provided that all R.sup.19 are not simultaneously hydrogen; each R.sup.20 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; provided that all R.sup.20 are not simultaneously hydrogen; wherein R.sup.12 is selected from the group consisting of substituted or unsubstituted (C.sub.1-C.sub.30 alkyl, substituted or unsubstituted (C.sub.2-C.sub.30)alkenyl, substituted or unsubstituted (C.sub.2-C.sub.30)alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl(C.sub.1C.sub.4)alkyl, substituted or unsubstituted heteroaryl(C.sub.1-C.sub.4)alkyl, and substituted or unsubstituted heterocyclyl(C.sub.1-C.sub.4)alkyl; each R.sup.13 is independently selected from the group consisting of hydrogen, substituted or unsubstituted (C.sub.1-C.sub.30)alkyl, substituted or unsubstituted (C.sub.2-C.sub.30)alkenyl, substituted or unsubstituted (C.sub.2-C.sub.30)alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl(C.sub.1-C.sub.4)alkyl, substituted or unsubstituted heteroaryl(C.sub.1-C.sub.4)alkyl, and substituted or unsubstituted heterocyclyl(C.sub.1-C.sub.4)alkyl; and the substituted (C.sub.1-C.sub.30)alkyl, substituted (C.sub.2-C.sub.30)alkenyl, substituted (C.sub.2-C.sub.30)alkynyl, substituted aryl, substituted heteroaryl, substituted heterocyclyl, substituted aryl(C.sub.1-C.sub.4)alkyl, substituted heteroaryl(C.sub.1-C.sub.4)alkyl, and substituted heterocyclyl(C.sub.1-C.sub.4)alkyl are substituted with one or more substituents each of which is independently selected from the group consisting of OH, NH.sub.2, SR CN, C(O)NH.sub.2, C(O)NHR.sup.13, C(O)NR.sup.13.sub.2, CO.sub.2H, and CO.sub.2R.sup.13.

21. The method of claim 18, wherein the copper-coordinating additive is a compound selected from the group consisting of 2-ethylhexyl phosphate, bis(2-ethylhexyl)phosphate, methyl phosphate, dimethyl phosphate, trimethyl phosphate, phenyl phosphate, diphenyl phosphate, citric acid, ethoxyamine hydrochloride, triethyl citrate, thiourea, urea, 14-crown-4, 15-crown-5, 18-crown-6, dibenzo-18-crown-6, aza-15-crown-5, aza-18-crown-6, and salen.

22.-24. (canceled)

Description

DRAWINGS

[0011] In order that the present disclosure may be well understood, there will now be described various forms thereof, given by way of example, reference being made to the accompanying drawings. The components in the figures are not necessarily to scale. Moreover, in the figures, like-referenced numerals designate corresponding parts throughout the different views.

[0012] FIG. 1 illustrates a plot of total color drift for a control paint sample commercially available from Behr (Control B) and various copper-coordinating additives added to the control paint sample at various molar ratios of extractable copper, in a copper-containing material including from 10 to 70 weight % of an amount of extractable copper, to copper-coordinating additive, at a concentration of 50 grams of the mixture of the copper-coordinating additive and the copper-containing material per gallon of the control paint sample, prepared according to the principles of the present disclosure;

[0013] FIG. 2 illustrates a plot of the antimicrobial efficacy of the control paint samples including the copper-coordinating additives and the copper-containing material at the molar ratios and concentrations in control paint samples indicated in FIG. 1;

[0014] FIG. 3 illustrates a plot of total color drift for a control paint sample and various copper-coordinating additives added to the control paint sample at various molar ratios of extractable copper, in the copper-containing material including from 10 to 70 weight % of an amount of extractable copper, to copper-coordinating additive, at a concentration of 50 grams of the mixture of the copper-coordinating additive and the copper-containing material per gallon of control paint sample, prepared according to the principles of the present disclosure;

[0015] FIG. 4 illustrates a plot of the antimicrobial efficacy of the control paint sample including the copper-coordinating additives and the copper-containing material at the molar ratios and concentrations in control paint samples indicated in FIG. 1;

[0016] FIG. 5 illustrates a plot of total color drift for a control paint sample commercially available from Nippon (Control N) and various copper-coordinating additives added to the control paint sample at various molar ratios of extractable copper, in the copper-containing material including from 10 to 70 weight % of an amount of extractable copper, to the copper-coordinating additive, at a concentration of 50 grams of the mixture of the copper-coordinating additive and the copper-containing material per gallon of the control paint sample, prepared according to the principles of the present disclosure;

[0017] FIG. 6 illustrates a plot of the antimicrobial efficacy of the control paint samples including the copper-coordinating additives and the copper-containing material at the molar ratios and concentrations in control paint samples indicated in FIG. 5;

[0018] FIG. 7 illustrates a plot of total color drift for a control paint sample and various copper-coordinating additives added to the control paint sample at various molar ratios of extractable copper, in the copper-containing material including from 10 to 70 weight % of an amount of extractable copper, to the copper-coordinating additive, at a concentration of 50 grams of the mixture of the copper-coordinating additive and the copper-containing material per gallon of control paint sample, prepared according to the principles of the present disclosure;

[0019] FIG. 8 illustrates a plot of the antimicrobial efficacy of the control paint samples including the copper-coordinating additives and the copper-containing material at various molar ratios of extractable copper, in the copper-containing material including from 10 to 70 weight % of an amount of extractable copper, to the copper-coordinating additive, and a concentration of 15 grams of the mixture of the copper-coordinating additive and the copper-containing material per gallon of control paint sample prepared according to the principles of the present disclosure;

[0020] FIG. 9 illustrates a plot of a retesting of the antimicrobial efficacy of the control paint samples including the copper-coordinating additives and the copper-containing material at the molar ratios and concentrations in paint indicated in FIG. 8;

[0021] FIG. 10 illustrates a plot of total color drift for various copper-coordinating additives added to the control paint sample at a 1:3 molar ratio of extractable copper, in the copper-containing material including from 10 to 70 weight % of an amount of extractable copper, to the copper-coordinating additive, at a concentration of 50 grams of the mixture of the copper-coordinating additive and the copper-containing material per gallon of control paint sample, prepared according to the principles of the present disclosure;

[0022] FIG. 11 illustrates a plot of the antimicrobial efficacy of the control paint samples including the copper-coordinating additives indicated in FIG. 10 and the copper-containing material at a 1:3 molar ratio of extractable copper, in the copper-containing material including from 10 to 70 weight % of an amount of extractable copper, to the copper-coordinating additives, and a concentration of 15 grams of the mixture of the copper-coordinating additive and the copper-containing material per gallon of control paint sample prepared according to the principles of the present disclosure;

[0023] FIG. 12 illustrates a plot of the antimicrobial efficacy of the control paint samples including the copper-coordinating additives indicated in FIG. 10 and the copper-containing material at a 1:3 molar ratio of extractable copper, in the copper-containing material including from 10 to 70 weight % of an amount of extractable copper, to the copper-coordinating additives, and a concentration of 50 grams of the mixture of the copper-coordinating additive and the copper-containing material per gallon of control paint sample, prepared according to the principles of the present disclosure;

[0024] FIG. 13 illustrates a plot of total color drift for various copper-coordinating additives added to the control paint samples at a 1:3 molar ratio of extractable copper, in the copper-containing material including from 10 to 70 weight % of an amount of extractable copper, to the copper-coordinating additives, at a concentration of 50 grams of the mixture of the copper-coordinating additive and the copper-containing material per gallon of control paint sample, prepared according to the principles of the present disclosure;

[0025] FIG. 14 illustrates a plot of the antimicrobial efficacy of the control paint samples in the absence of hydrogen peroxide including the copper-coordinating additives indicated in FIG. 13 and the copper-containing material at a 1:3 molar ratio of extractable copper, in the copper-containing material including from 10 to 70 weight % of an amount of extractable copper, to the copper-coordinating additives, and a concentration of 50 grams of the of the mixture of the copper-coordinating additive and the copper-containing material per gallon of control paint sample, prepared according to the principles of the present disclosure;

[0026] FIG. 15 illustrates the drift in blue color resulting from an increase in the ratio of number of ligand compounds complexed to a copper atom in control paint samples, from a 0:1 ligand compound to copper atom ratio to a 4:1 ligand compound to copper atom ratio;

[0027] FIG. 16 illustrates the differences in color of colorless polymers and tinted polymers mixed with 3.6 weight % of a copper-containing material including from 10 to 70 weight % of an amount of extractable copper;

[0028] FIG. 17 illustrates the differences in color of poly(methyl methacrylate) (PMMA) in chloroform with various amounts of a copper-containing material including from 10 to 70 weight % of an amount of extractable copper and 2-ethylhexyl phosphate (2EHP);

[0029] FIG. 18 illustrates the differences in color of PMMA in toluene with a copper-containing material including from 10 to 70 weight % of an amount of extractable copper in the presence and absence of 2EHP; and

[0030] FIG. 19 illustrates the differences in color of PMMA in N-methylpyrrolidone (NMP) with a copper-containing material including from 10 to 70 weight % of an amount of extractable copper in the presence and absence of 2EHP.

[0031] The drawings described herein are for illustration purposes only and are not intended to limit the scope of the present disclosure in any way.

DETAILED DESCRIPTION

[0032] The following description is merely exemplary in nature and is not intended to limit the present disclosure, application, or uses.

[0033] In describing elements of the present disclosure, the terms 1.sup.st, 2.sup.nd, first, second, A, B, (a), (b), and the like may be used herein. These terms are only used to distinguish one element from another element, but do not limit the corresponding elements irrespective of the nature or order of the corresponding elements.

[0034] Numerical values, including endpoints of ranges, may be expressed herein as approximations preceded by the term about, approximately, or the like. In such cases, other examples include the particular numerical values. Regardless of whether a numerical value is expressed as an approximation, two examples are included in this disclosure: one expressed as an approximation, and another not expressed as an approximation. It will be further understood that an endpoint of each range is significant both in relation to another endpoint, and independently of another endpoint.

[0035] As used herein, the term antimicrobial means a material, or a surface of a material, that will kill or inhibit the growth of microbes including, but not limited to, bacteria, viruses, mildew, mold, algae, and/or fungi. The term antimicrobial, as used herein, does not mean the material or the surface of the material will kill or inhibit the growth of all species of microbes within such families, but that the material or the surface of the material will kill or inhibit the growth of one or more species of microbes from such families.

[0036] As used herein, the term biocidal means a material with an active substance that is intended to destroy, deter, render harmless, prevent the action of, or otherwise exert a controlling effect on undesired organisms such as bacteria, viruses, mildew, mold, algae, and/or fungi.

[0037] As used herein, the term logarithmic reduction means the negative value of log (C.sub.a/C.sub.0), where C.sub.a refers to the colony form unit (CFU) number of the antimicrobial surface and C.sub.0 refers to the CFU of the control surface that is not an antimicrobial surface. As an example, a 3 logarithmic reduction equals about 99.9% of the microbes killed and a logarithmic reduction of 5 equals about 99.999% of microbes killed. The logarithmic reduction value may be measured according to the ASTM D2574-16 (2016) Standard Test Method for Resistance of Emulsion Paints in the Container to Attack by Microorganisms.

[0038] The uses of the terms a and an and the and similar references in the context of describing the present disclosure (especially in the context of the following claims) are to be construed to cover both the singular and the plural, unless otherwise indicated herein or clearly contradicted by context. Recitation of ranges of values herein are merely indicated to serve as a shorthand method of referring individually to each separate value falling within the range, unless otherwise indicated herein, and each separate value is incorporated into the specification as if it were individually recited herein. All methods described herein may be performed in any suitable order unless otherwise indicated herein or otherwise clearly contradicted by context.

[0039] As used herein, the terms comprise(s), include(s), having, has, can, contain(s), and variants thereof, are intended to be open-ended transitional phrases, terms, or words that do not preclude the possibility of additional acts, structures, elements, or components. The present description also contemplates other examples comprising, consisting of, and consisting essentially of, the examples or elements presented herein, whether explicitly set forth or not.

[0040] As used herein, the term about, when used in the context of a numerical value or range set forth means a variation of 15%, or less, of the numerical value. For example, a value differing by 15%, 14%, +10%, or 5%, among others, would satisfy the definition of about, unless more narrowly defined in particular instances.

[0041] The term alkyl, by itself or as part of another substituent, means, unless otherwise stated, a straight, branched, or cyclic chain hydrocarbon (cycloalkyl) having the number of carbon atoms designated (i.e., C.sub.1-C.sub.30 means one to thirty carbons). Examples include methyl, ethyl, propyl, isopropyl, cyclopropyl, butyl, isobutyl, sec-butyl, tert-butyl, cyclobutyl, methylcyclopropyl, cyclopropylmethyl, pentyl, neopentyl, hexyl, and cyclohexyl. Most preferred are (C.sub.1-C.sub.18)alkyl. In certain examples of the present disclosure, a (C.sub.1-C.sub.30)alkyl group, whether straight, branched, or cyclic, may not be a C.sub.1alkyl group, and/or may not be a C.sub.2alkyl group, and/or may not be a C.sub.3alkyl group, and/or may not be a C.sub.4alkyl group, and/or may not be a C.sub.5alkyl group, and/or may not be a C.sub.6alkyl group, and/or may not be a C.sub.7alkyl group, and/or may not be a C.sub.8alkyl group, and/or may not be a C.sub.9alkyl group, and/or may not be a C.sub.10alkyl group, and/or may not be a C.sub.11alkyl group, and/or may not be a C.sub.12alkyl group, and/or may not be a C.sub.13alkyl group, and/or may not be a C.sub.14alkyl group, and/or may not be a C.sub.15alkyl group, and/or may not be a C.sub.16alkyl group, and/or may not be a C.sub.17alkyl group, and/or may not be a C.sub.18alkyl group, and/or may not be a C.sub.19alkyl group, and/or may not be a C.sub.20alkyl group, and/or may not be a C.sub.21alkyl group, and/or may not be a C.sub.22alkyl group, and/or may not be a C.sub.23alkyl group, and/or may not be a C.sub.24alkyl group, and/or may not be a C.sub.25alkyl group, and/or may not be a C.sub.26alkyl group, and/or may not be a C.sub.27alkyl group, and/or may not be a C.sub.28alkyl group, and/or may not be a C.sub.29alkyl group, and/or may not be a C.sub.30alkyl group.

[0042] The term alkylene, by itself or as part of another substituent, means, unless otherwise stated, a straight, branched, or cyclic chain bivalent saturated aliphatic radical having the number of carbon atoms designated (i.e., C.sub.1-C.sub.30 means one to thirty carbon atoms) such as methylene (C.sub.1alkylene, or CH.sub.2) or that may be derived from an alkene by opening of a double bond or from an alkane by removal of two hydrogen atoms from different carbon atoms. Examples include methylene, methylmethylene, ethylene, propylene, ethylmethylene, dimethylmethylene, methylethylene, butylene, cyclopropylmethylene, dimethylethylene, and propylmethylene. In certain examples of the present disclosure, a (C.sub.1-C.sub.30)alkylene group, whether straight, branched, or cyclic, may not be a C.sub.1alkylene group, and/or may not be a -C.sub.2alkylene group, and/or may not be a C.sub.3alkylene group, and/or may not be a C.sub.4alkylene group, and/or may not be a C.sub.5alkylene group, and/or may not be a C.sub.6alkylene group, and/or may not be a C.sub.7alkylene group, and/or may not be a C.sub.8alkylene group, and/or may not be a C.sub.9alkylene group, and/or may not be a C.sub.10alkylene group, and/or may not be a C.sub.11alkylene group, and/or may not be a C.sub.12alkylene group, and/or may not be a C.sub.13alkylene group, and/or may not be a C.sub.14alkylene group, and/or may not be a C.sub.15alkylene group, and/or may not be a C.sub.16alkylene group, and/or may not be a C.sub.17alkylene group, and/or may not be a C.sub.18alkylene group, and/or may not be a C.sub.19alkylene group, and/or may not be a C.sub.20alkylene group, and/or may not be a C.sub.21alkylene group, and/or may not be a C.sub.22alkylene group, and/or may not be a C.sub.23alkylene group, and/or may not be a C.sub.24alkylene group, and/or may not be a C.sub.25alkylene group, and/or may not be a C.sub.26alkylene group, and/or may not be a C.sub.27alkylene group, and/or may not be a C.sub.28alkylene group, and/or may not be a C.sub.29alkylene group, and/or may not be a C.sub.30alkylene group.

[0043] The term alkenyl, by itself or as part of another substituent, means, unless otherwise stated, a stable mono-unsaturated or di-unsaturated straight chain, branched chain, or cyclic hydrocarbon group, with a carbon-carbon double bond (CHCH), and having the stated number of carbon atoms (i.e., C.sub.2-C.sub.30 means two to thirty carbons). Examples include vinyl, propenyl, allyl, crotyl, isopentenyl, butadienyl, 1,3-pentadienyl, 1,4-pentadienyl, cyclopentenyl, cyclopentadienyl, and the higher homologs and isomers. Functional groups representing an alkene are exemplified by CHCHCH.sub.2 and CH.sub.2CHCH.sub.2. In certain examples of the present disclosure, a (C.sub.2-C.sub.30)alkenyl group, whether straight, branched, or cyclic, may not be a C.sub.2alkenyl group, and/or may not be a C.sub.3alkenyl group, and/or may not be a C.sub.4alkenyl group, and/or may not be a C.sub.5alkenyl group, and/or may not be a C.sub.6alkenyl group, and/or may not be a C.sub.7alkenyl group, and/or may not be a C.sub.6alkenyl group, and/or may not be a C.sub.9alkenyl group, and/or may not be a C.sub.10alkenyl group, and/or may not be a C.sub.11alkenyl group, and/or may not be a C.sub.12alkenyl group, and/or may not be a C.sub.13alkenyl group, and/or may not be a C.sub.14alkenyl group, and/or may not be a C.sub.15alkenyl group, and/or may not be a C.sub.15alkenyl group, and/or may not be a C.sub.17alkenyl group, and/or may not be a C.sub.18alkenyl group, and/or may not be a C.sub.19alkenyl group, and/or may not be a C.sub.20alkenyl group, and/or may not be a C.sub.21alkenyl group, and/or may not be a C.sub.22alkenyl group, and/or may not be a C.sub.23alkenyl group, and/or may not be a C.sub.24alkenyl group, and/or may not be a C.sub.25alkenyl group, and/or may not be a C.sub.26alkenyl group, and/or may not be a C.sub.27alkenyl group, and/or may not be a C.sub.28alkenyl group, and/or may not be a C.sub.29alkenyl group, and/or may not be a C.sub.30alkenyl group.

[0044] The term alkenylene, by itself or as part of another substituent, means, unless otherwise stated, a straight, branched, or cyclic chain bivalent unsaturated aliphatic radical containing a double bond having the number of carbon atoms designated (i.e., C.sub.2-C.sub.30 means two to thirty carbons) and that may be derived from an alkyne by opening of a triple bond or from an alkene by removal of two hydrogen atoms from different carbon atoms. In certain examples of the present disclosure, a (C.sub.2-C.sub.30)alkenylene group, whether straight, branched, or cyclic, may not be a C.sub.2alkenylene group, and/or may not be a C.sub.3alkenylene group, and/or may not be a C.sub.4alkenylene group, and/or may not be a C.sub.5alkenylene group, and/or may not be a C.sub.6alkenylene group, and/or may not be a C.sub.7alkenylene group, and/or may not be a C.sub.8alkenylene group, and/or may not be a C.sub.9alkenylene group, and/or may not be a C.sub.10alkenylene group, and/or may not be a C.sub.11alkenylene group, and/or may not be a C.sub.12alkenylene group, and/or may not be a C.sub.13alkenylene group, and/or may not be a C.sub.14alkenylene group, and/or may not be a C.sub.15alkenylene group, and/or may not be a C.sub.16alkenylene group, and/or may not be a C.sub.17alkenylene group, and/or may not be a C.sub.18alkenylene group, and/or may not be a C.sub.19alkenylene group, and/or may not be a C.sub.20alkenylene group, and/or may not be a C.sub.21alkenylene group, and/or may not be a C.sub.22alkenylene group, and/or may not be a C.sub.23alkenylene group, and/or may not be a C.sub.24alkenylene group, and/or may not be a C.sub.25alkenylene group, and/or may not be a C.sub.26alkenylene group, and/or may not be a C.sub.27alkenylene group, and/or may not be a C.sub.28alkenylene group, and/or may not be a C.sub.29alkenylene group, and/or may not be a C.sub.30alkenylene group.

[0045] The term alkynyl, by itself or as part of another substituent, means, unless otherwise stated, a stable carbon-carbon triple bond-containing radical (CC), branched chain, or cyclic hydrocarbon group having the stated number of carbon atoms (i.e., C.sub.2-C.sub.30 means two to thirty carbons). Examples include ethynyl and propargyl. In certain examples of the present disclosure, a (C.sub.2-C.sub.30)alkynyl group, whether straight, branched, or cyclic, may not be a C.sub.2alkynyl group, and/or may not be a C.sub.3alkynyl group, and/or may not be a C.sub.4alkynyl group, and/or may not be a C.sub.5alkynyl group, and/or may not be a C.sub.6alkynyl group, and/or may not be a C.sub.7alkynyl group, and/or may not be a C.sub.8alkynyl group, and/or may not be a C.sub.9alkynyl group, and/or may not be a C.sub.10alkynyl group, and/or may not be a C.sub.11alkynyl group, and/or may not be a C.sub.12alkynyl group, and/or may not be a C.sub.13alkynyl group, and/or may not be a C.sub.14alkynyl group, and/or may not be a C.sub.15alkynyl group, and/or may not be a C.sub.16alkynyl group, and/or may not be a C.sub.17alkynyl group, and/or may not be a C.sub.18alkynyl group, and/or may not be a C.sub.19alkynyl group, and/or may not be a C.sub.20alkynyl group, and/or may not be a C.sub.21alkynyl group, and/or may not be a C.sub.22alkynyl group, and/or may not be a C.sub.23alkynyl group, and/or may not be a C.sub.24alkynyl group, and/or may not be a C.sub.25alkynyl group, and/or may not be a C.sub.26alkynyl group, and/or may not be a C.sub.27alkynyl group, and/or may not be a C.sub.28alkynyl group, and/or may not be a C.sub.29alkynyl group, and/or may not be a C.sub.30alkynyl group.

[0046] The term alkynylene, by itself or as part of another substituent, means, unless otherwise stated, a straight, branched, or cyclic chain bivalent unsaturated aliphatic radical containing a triple bond having the number of carbon atoms designated (i.e., C.sub.2-C.sub.30 means two to thirty carbon atoms) and that may be derived from an alkyne by removal of two hydrogen atoms from different carbon atoms. In certain examples of the present disclosure, a (C.sub.2-C.sub.30)alkynylene group, whether straight, branched, or cyclic, may not be a C.sub.2alkynylene group, and/or may not be a C.sub.3alkynylene group, and/or may not be a C.sub.4alkynylene group, and/or may not be a C.sub.5alkynylene group, and/or may not be a C.sub.6alkynylene group, and/or may not be a C.sub.7alkynylene group, and/or may not be a C.sub.8alkynylene group, and/or may not be a C.sub.9alkynylene group, and/or may not be a C.sub.10alkynylene group, and/or may not be a C.sub.11alkynylene group, and/or may not be a C.sub.12alkynylene group, and/or may not be a C.sub.13alkynylene group, and/or may not be a C.sub.14alkynylene group, and/or may not be a C.sub.15alkynylene group, and/or may not be a C.sub.16alkynylene group, and/or may not be a C.sub.17alkynylene group, and/or may not be a C.sub.18alkynylene group, and/or may not be a C.sub.19alkynylene group, and/or may not be a C.sub.20alkynylene group, and/or may not be a C.sub.21alkynylene group, and/or may not be a C.sub.22alkynylene group, and/or may not be a C.sub.23alkynylene group, and/or may not be a C.sub.24alkynylene group, and/or may not be a C.sub.25alkynylene group, and/or may not be a C.sub.26alkynylene group, and/or may not be a C.sub.27alkynylene group, and/or may not be a C.sub.28alkynylene group, and/or may not be a C.sub.29alkynylene group, and/or may not be a C.sub.30alkynylene group.

[0047] The term alkoxy, by itself or as part of another substituent, means, unless otherwise stated, an alkyl group having the designated number of carbon atoms, as defined above, connected to the rest of the molecule via an oxygen atom, such as, for example, methoxy, ethoxy, 1-propoxy, 2-propoxy (isopropoxy), and the higher homologs and isomers. In certain examples of the present disclosure, a (C.sub.1-C.sub.30)alkoxy group, whether straight, branched, or cyclic, may not be a C.sub.1alkoxy group, and/or may not be a C.sub.2alkoxy group, and/or may not be a C.sub.3alkoxy group, and/or may not be a C.sub.4alkoxy group, and/or may not be a C.sub.5alkoxy group, and/or may not be a C.sub.6alkoxy group, and/or may not be a C.sub.7alkoxy group, and/or may not be a C.sub.8alkoxy group, and/or may not be a C.sub.9alkoxy group, and/or may not be a C.sub.10alkoxy group, and/or may not be a C.sub.11alkoxy group, and/or may not be a C.sub.12alkoxy group, and/or may not be a C.sub.13alkoxy group, and/or may not be a C.sub.14alkoxy group, and/or may not be a C.sub.15alkoxy group, and/or may not be a C.sub.16alkoxy group, and/or may not be a C.sub.17alkoxy group, and/or may not be a C.sub.18alkoxy group, and/or may not be a C.sub.19alkoxy group, and/or may not be a C.sub.20alkoxy group, and/or may not be a C.sub.21alkoxy group, and/or may not be a C.sub.22alkoxy group, and/or may not be a C.sub.23alkoxy group, and/or may not be a C.sub.24alkoxy group, and/or may not be a C.sub.25alkoxy group, and/or may not be a C.sub.26alkoxy group, and/or may not be a C.sub.27alkoxy group, and/or may not be a C.sub.28alkoxy group, and/or may not be a C.sub.29alkoxy group, and/or may not be a C.sub.30alkoxy group.

[0048] The term alkenyloxy, by itself or as part of another substituent, means, unless otherwise stated, an alkenyl group having the designated number of carbon atoms, as defined above, connected to the rest of the molecule via an oxygen atom.

[0049] The term alkynyloxy, by itself or as part of another substituent, means, unless otherwise stated, an alkynyl group having the designated number of carbon atoms, as defined above, connected to the rest of the molecule via an oxygen atom.

[0050] The term aromatic generally refers to a carbocycle or heterocycle having one or more polyunsaturated rings having aromatic character (i.e., having (4n+2) delocalized (pi) electrons where n is an integer).

[0051] The term aryl, by itself or in combination with another substituent, means, unless otherwise stated, a carbocyclic aromatic system containing one or more rings (typically one, two, or three rings) wherein such rings may be attached together in a pendant manner, such as a biphenyl, or may be fused, such as naphthalene. Examples may include phenyl, anthracyl, and naphthyl. Preferred are phenyl and naphthyl, most preferred is phenyl.

[0052] The term aryloxy, by itself or in combination with another substituent, means, unless otherwise stated, an aryl group connected to the rest of the molecule via an oxygen atom.

[0053] The term arylene, by itself or in combination with another substituent, means, unless otherwise stated, a bivalent radical produced by removal of two hydrogen atoms from two different carbon atoms of an aryl group.

[0054] The terms heterocycle or heterocyclyl or heterocyclic, by themselves or as part of other substituents, mean, unless otherwise stated, an unsubstituted or substituted, stable, mono- or multi-cyclic heterocyclic ring system that consists of carbon atoms and at least one heteroatom independently selected from the group consisting of N, O, and S, and wherein the nitrogen and sulfur heteroatoms may be optionally oxidized, and the nitrogen atom may be optionally quaternized. The heterocyclic system may be attached, unless otherwise stated, at any heteroatom or carbon atom that affords a stable structure.

[0055] The term heterocyclyloxy, by itself or in combination with another substituent, means, unless otherwise stated, a heterocyclyl group connected to the rest of the molecule via an oxygen atom.

[0056] The term heterocyclylene, by itself or in combination with another substituent, means, unless otherwise stated, a bivalent radical produced by removal of two hydrogen atoms from two different carbon atoms of a heterocyclyl group.

[0057] The terms heteroaryl or heteroaromatic, by themselves or as part of other substituents, mean, unless otherwise stated, a heterocyclic having aromatic character. A polycyclic heteroaryl may include fused rings. Examples include indole, 1H-indazole, 1H-pyrrolo[2,3-b]pyridine, and the like. A polycyclic heteroaryl may include one or more rings that are partially saturated. Examples include indoline, tetrahydroquinoline, and 2,3-dihydrobenzofuryl.

[0058] Non-limiting examples of heteroaryl groups include: pyridyl; pyrazinyl; pyrimidinyl, particularly 2- and 4-pyrimidinyl; pyridazinyl; thienyl; furyl; pyrrolyl, particularly 2-pyrrolyl; imidazolyl; thiazolyl; oxazolyl; pyrazolyl, particularly 3- and 5-pyrazolyl; isothiazolyl; 1,2,3-triazolyl; 1,2,4-triazolyl; 1,3,4-triazolyl; tetrazolyl; 1,2,3-thiadiazolyl; 1,2,3-oxadiazolyl; 1,3,4-thiadiazolyl; and 1,3,4-oxadiazolyl.

[0059] Polycyclic heterocycles include both aromatic and non-aromatic polycyclic heterocycles. Non-limiting examples of polycyclic heterocyclic include: indolyl, particularly 3-, 4-, 5-, 6-, and 7-indolyl; indolinyl; indazolyl, particularly 1H-indazol-5-yl; quinolyl; tetrahydroquinolyl; isoquinolyl, particularly 1- and 5-isoquinolyl; 1,2,3,4-tetrahydroisoquinolyl; cinnolyl; quinoxalinyl, particularly 2- and 5-quinoxalinyl; quinazolinyl; phthalazinyl; naphthyridinyl, particularly 1,5- and 1,8-naphthyridinyl; 1,4-benzodioxanyl; coumaryl; dihydrocoumaryl; benzofuryl, particularly 3-, 4-, 5-, 6-, and 7-benzofuryl; 2,3-dihydrobenzofuryl; 1,2-benzisoxazoyl; benzothienyl, particularly 3-, 4-, 5-, 6-, and 7-benzothienyl; benzoxazolyl; benzothiazolyl, particularly 2- and 5-benzothiazolyl; purinyl; benzimidazolyl, particularly 2-benzimidazolyl; benztriazolyl; thioxanthinyl; carbazolyl; carbolinyl; acridinyl; pyrrolizidinyl; pyrrolo[2,3-b]pyridinyl, particularly 1H-pyrrolo[2,3-b]pyridine-5-yl; and quinolizidinyl. Particularly preferred are 4-indolyl, 5-indolyl, 6-indolyl, 1H-indazol-5-yl, and 1H-pyrrolo[2,3-b]pyridin-5-yl.

[0060] The term heteroaryloxy, by itself or in combination with another substituent, means, unless otherwise stated, a heteroaryl group connected to the rest of the molecule via an oxygen atom.

[0061] The term heteroarylene, by itself or in combination with another substituent, means, unless otherwise stated, a bivalent radical produced by removal of two hydrogen atoms from two different carbon atoms of a heteroaryl group.

[0062] The term aryl(C.sub.1-C.sub.4)alkyl means a functional group wherein a one to four carbon alkylene chain is attached to an aryl group, e.g., CH.sub.2CH.sub.2-phenyl. Examples may include benzyl. The term heteroaryl(C.sub.1-C.sub.4)alkyl means a functional group wherein a one to four carbon alkylene chain is attached to a heteroaryl group, e.g., CH.sub.2CH.sub.2-pyridyl. The term heterocyclyl(C.sub.1-C.sub.4)alkyl means a functional group wherein a one to four carbon alkylene chain is attached to a heterocyclyl group, e.g., CH.sub.2CH.sub.2-aziridine. The terms aryl(C.sub.1-C.sub.4)alkylene or (C.sub.1-C.sub.4)alkylarylene mean a bivalent radical produced by removal of two hydrogen atoms from two different carbon atoms of an aryl(C.sub.1-C.sub.4)alkyl group, preferably wherein one of the two different carbon atoms is in the (C.sub.1-C.sub.4)alkyl group and the other of the two different carbon atoms is in the aryl group. The term (C.sub.1-C.sub.4)alkylaryl(C.sub.1-C.sub.4)alkylene means a bivalent radical produced by removal of two hydrogen atoms from two different carbon atoms of a (C.sub.1-C.sub.4)alkylaryl(C.sub.1-C.sub.4)alkyl group, wherein one of the two different carbon atoms is in one of the (C.sub.1-C.sub.4)alkyl groups and the other of the two different carbon atoms is in the other of the (C.sub.1-C.sub.4)alkyl groups, e.g., CH.sub.2-phenyl-CH.sub.2. The terms heteroaryl(C.sub.1-C.sub.4)alkylene or (C.sub.1-C.sub.4)alkylheteroarylene mean a bivalent radical produced by removal of two hydrogen atoms from two different carbon atoms of a heteroaryl(C.sub.1-C.sub.4)alkyl group, preferably wherein one of the two different carbon atoms is in the (C.sub.1-C.sub.4)alkyl group and the other of the two different carbon atoms is in the heteroaryl group. The term (C.sub.1-C.sub.4)alkylheteroaryl(C.sub.1-C.sub.4)alkylene means a bivalent radical produced by removal of two hydrogen atoms form two different carbon atoms of a (C.sub.1-C.sub.4)alkylheteroaryl(C.sub.1-C.sub.4)alkyl group, wherein one of the two different carbon atoms is in one of the (C.sub.1-C.sub.4)alkyl groups and the other of the two different carbon atoms is in the other of the (C.sub.1-C.sub.4)alkyl groups, e.g., CH.sub.2-pyridinyl-CH.sub.2. The terms heterocyclyl(C.sub.1-C.sub.4)alkylene or (C.sub.1-C.sub.4)alkylheterocyclylene mean a bivalent radical produced by removal of two hydrogen atoms from two different carbon atoms of a heterocyclyl(C.sub.1-C.sub.4)alkyl group, preferably wherein one of the two different carbon atoms is in the (C.sub.1-C.sub.4)alkyl group and the other of the two different carbon atoms is in the heterocyclyl group. The term (C.sub.1-C.sub.4)alkylheterocyclyl(C.sub.1-C.sub.4)alkylene means a bivalent radical produced by removal of two hydrogen atoms from two different carbon atoms of a (C.sub.1-C.sub.4)alkylheterocyclyl(C.sub.1-C.sub.4)alkyl group, wherein one of the two different carbon atoms is in one of the (C.sub.1-C.sub.4)alkyl groups and the other of the two different carbon atoms is in the other of the (C.sub.1-C.sub.4)alkyl groups, e.g., CH.sub.2-aziridinyl-CH.sub.2.

[0063] The term crown ether refers to a cyclic compound that consists of a ring containing several ether groups. The most common crown ethers are cyclic oligomers of ethylene oxide, the repeating unit being ethyleneoxy, i.e., CH.sub.2CH.sub.2O. Important members of this series of crown ethers are the tetramer (n=4), the pentamer (n=5), and the hexamer (n=6). A crown ether is named as, for example, 15-crown-5. The first number in a crown ether's name refers to the number of atoms in the entire cycle, and the second number refers to the number of those atoms that are evenly spaced oxygen atoms. Examples of crown ethers may include 12-crown-4, 15-crown-5, 18-crown-6, and dibenzo-18-crown-6, which have the following structural formulae:

##STR00004##

[0064] The term aza-crown ether refers to a nitrogen analog of a crown ether. The parent aza-crown ethers have the repeating unit CH.sub.2CH.sub.2NH. Examples of aza-crown ethers may include aza-15-crown-5 and aza-18-crown-6, which have the following structural formulae:

##STR00005##

[0065] The term salen ligand refers to a class of tetradentate C.sub.2-symmetric compounds which are structurally related to the classical salen ligand, primarily bis-Schiff bases, and synthesized from salicylaldehyde (i.e., sal) and ethylenediamine (i.e., en). Examples of a salen ligand may include salen, which has the structural formula:

##STR00006##

[0066] As used herein, the term durable refers to the tendency of the atomic bonds of the durable phase of a copper-containing material to remain intact during and after interaction with a leachate. As used herein, the term degradable refers to the tendency of the atomic bonds of the degradable phase to break during and after interaction with one or more leachates.

[0067] As used herein, unless otherwise specified, the term carrier may refer to polymers, monomers, binders, solvents, or a combination thereof, as described herein. In a specific example, the carrier is a paint that is used for application to surfaces (which may include interior or exterior surfaces). The paint may be a dispersion of finely divided solids in a liquid medium (e.g., water, organic solvent, and/or inorganic solvent) that may be applied to a surface to form a film that adheres to the surface. Examples of solids used in paints may include pigments, fillers, extenders, driers, rheology modifiers, etc. In some examples, the paint may be a latex paint. Examples of solvent may include water and organic solvents.

[0068] As used herein, the term secondary carbon refers to a carbon atom of a compound or substituent group thereof that is covalently bonded to two other carbon atoms.

[0069] As used herein, the term tertiary carbon refers to a carbon atom of a compound or substituent group thereof that is covalently bonded to three other carbon atoms.

[0070] As used herein, the term alpha () carbon refers to a carbon atom in a compound that is covalently bonded to a functional group or to an atom other than a hydrogen or carbon atom.

[0071] As used herein, the term beta () carbon refers to a carbon atom in a carbon that is covalently bonded to an alpha carbon.

[0072] As used herein, the term gamma () carbon refers to a carbon atom that is covalently bonded to a beta carbon but that is not an alpha carbon.

[0073] In an example, the present disclosure provides a biocidal composition, including a carrier, a copper-containing material, and a copper-coordinating additive. For example, the copper-containing material may include copper-containing glass, copper oxide, copper metal, copper salt (e.g., copper halide, copper acetate, or copper sulfate), or a combination thereof. In certain examples, the copper-containing material includes a plurality of copper-containing glass particles. In certain examples, a copper-coordinating additive is combined with a copper-containing material in a molar ratio of extractable copper in copper-containing material to copper-containing material of from 1:0.1 to 1:15. In other examples, the copper-coordinating additive is combined with the copper-containing material at a molar ratio of additive to copper-containing material and added to a carrier at a concentration of from 1 to 75 grams of copper-coordinating additive and the copper-containing material per gallon of carrier. In still other examples, the copper-containing material may be pre-treated with a pretreatment solution.

[0074] According to examples of the present disclosure, the biocidal composition may include a carrier, a copper-containing material that may have been pre-treated with a pretreatment solution, and a copper-coordinating additive. The biocidal composition may ultimately be a paint, a coating, an elastomeric coating, a caulk, a sealant, a floor polish, a fabric treatment, a stain, a clear coat, or a primer. The copper-containing material, which may be pretreated with a pretreatment solution, may be combined with a copper-coordinating additive and a carrier while stabilizing the color of the carrier when the copper-containing material is combined with the copper-coordinating additive and the carrier. Examples of the present disclosure may reduce changes in color of the carrier at the time of combining the copper-containing material with the copper-coordinating additive and the carrier and/or also reduce changes in the color of the carrier between a period of time after combining the copper-containing material with the copper-coordinating additive and the carrier and the final color of the carrier.

[0075] The effectiveness of a composition of the present disclosure as a biocidal composition may be measured as a function of the composition's logarithmic reduction. The composition's logarithmic reduction value may be relevant to its ability to kill a wide variety of biological organisms to which the composition is exposed, but may also allow the copper-containing material to act as a preservative for the composition during storage (e.g., in a container such as, but not limited to a tank, a can, a bucket, a drum, a bottle, or a tube). According to examples of the present disclosure, a logarithmic reduction of the biocidal composition may be at least about 2, at least about 3, at least about 4, at least about 5, at least about 6, at least about 7, at least about 8, at least about 9, at least about 10, in a range from about 1 to about 10, about 3 to about 7, about 4 to about 6, or less than, equal to, or greater than about 1, 2, 3, 4, 5, 6, 7, 8, 9, or about 10. The biocidal properties of the composition may make it effective for substantially killing a wide variety of biological organisms including bacteria, viruses, and fungi. Where the coating is configured to have biocidal properties with respect to bacteria, suitable examples of bacteria include Staphylococcus aureus, Enterobacter aerogenes, Pseudomonas aeruginosa, Methicillin Resistant Staphylococcus aureus, E. coli, and mixtures thereof. In some examples, the copper-containing material exhibits at least a 4 logarithmic reduction, a 5 logarithmic reduction, or even a 6 logarithmic reduction in the concentration of at least one of Staphylococcus aureus, Enterobacter aerogenes, Pseudomonas aeruginosa bacteria, Methicillin Resistant Staphylococcus aureus, and E. coli under the EPA test, or a 4 logarithmic reduction or greater (e.g., 5 logarithmic reduction or greater) under JIS Z 2801 (2000) testing conditions or under the Modified JIS Z 2801 Test for Bacteria. In one or more examples described herein, the copper-containing particles exhibit a 2 logarithmic reduction or greater, a 3 logarithmic reduction or greater, a 4 logarithmic reduction or greater, or a 5 logarithmic reduction or greater in Murine Novovirus under a Modified JIS Z 2801 for Viruses test. The procedure for the Modified JIS Z 2801 (2000) Test for Viruses is provided in International Patent Application Pub. No. 2021/055300 A1, COLOR STABILIZATION OF BIOCIDAL COATINGS, which is incorporated by reference herein in its entirety.

[0076] In some examples, the material may exhibit the logarithmic reductions described herein under one or more of the U.S. Environmental Protection Agency Test Method of Efficacy of Copper Alloy as a Sanitizer (2009) (also referred to herein as the EPA Test), the Modified Japanese Industrial Standard (JIS) Z 2801 Test for Bacteria and/or the Modified JIS Z2801 Test for Viruses, for a period of one month or greater or for a period of three months or greater. The one-month period or three-month period may commence at or after the application of the material to a surface as a layer. In such examples, the layer exhibits the logarithmic reductions described herein.

[0077] However, as described herein, it is possible to combine the copper-containing material with a copper-coordinating additive to limit the shift of the color of the biocidal composition from the color of a standard coating material (e.g., the material in the absence of the copper-containing material and the copper-coordinating additive). For example, it is possible to achieve a CIE L*a*b* E* between the observed color and a standard of less than about 30, less than about 25, less than about 25, less than about 20, less than about 15, less than about 12, less than about 10, less than about 9, less than about 8, less than about 7, less than about 6, less than about 5, less than about 4, less than about 3, less than about 2, less than about 1, in a range of from about 1 to about 30, about 2 to about 25, about 5 to about 15, about 3 to about 8, about 4 to about 7, about 5 to about 6, less than, equal to, or greater than about 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, or about 30.

[0078] As understood, the CIE L*a*b* color space is a color scale for determining a color. The three coordinates (or dimensions/components) of CIE L*a*b* represent the lightness of the color (L*=0 indicates black and L*=100 indicates white), its position between red (sometimes referenced as magenta) and green (negative a* values indicate green while positive a* values indicate red) and its position between yellow and blue (negative b* values indicate blue and positive b* values indicate yellow). The L* component closely matches human perception of lightness. Related to the CIE L*a*b* color space, is the CIE L*C*h color space that is a cylindrical representation of the three perceptual color correlates: lightness, chroma, and hue. The axial component of CIE L*C*h is the same lightless attribute L* as CIE L*a*b*, the radial component is the chroma, and the angular component is hue. Using these color spaces, the difference, (e.g., a E*) in color between a standard and observed color may be measured. In this manner, the extent to which the desired color of a coating is altered by the components therein may be measured.

[0079] The copper-containing glass particles may be a biocidal inorganic glass powder including copper particles. Although the individual particles of the copper-containing glass particles may be effective as a biocidal agent, a potential drawback may be that the copper offers numerous opportunities for ligands that are components of the carrier to bind thereto. Without wishing to be limited by theory, the copper-coordinating additives of the examples of the present disclosure may effectively compete with components of the carrier that may otherwise act as ligands to bind to copper so as to advantageously minimize color drift or accelerate reaching color endpoint.

[0080] The copper-containing glass particles may independently include a Cu metal, Cu.sup.1+, Cu.sup.2+, or a combination of Cu.sup.1+ of Cu.sup.2+. The combined total of the Cu species may be about 10 weight % or more of the copper-containing material. However, as will be discussed in more detail below, the amount of Cu.sup.2+ may be minimized or reduced such that the copper-containing glass particles may be substantially free of Cu.sup.2+. The copper may be non-complexed or may have a ligand bonded thereto to form a complex. The Cu.sup.1+ ions may be present on or in the surface and/or the bulk of the copper-containing glass particles. The copper-containing glass particles may include copper-containing glass, copper (I) oxide, copper (I) halides, copper (I) carbonate, or a combination thereof. In some examples, the copper-containing glass particles may include only one of copper-containing glass, copper (I) oxide, copper (I) halides, or copper (I) carbonate. In some examples, the Cu.sup.1+ ions may be present in a glass network and/or a glass matrix of the copper-containing glass particles. Where the Cu.sup.1+ ions are present in the glass network, the Cu.sup.1+ ions are atomically bonded to the atoms in the glass network. Where the Cu.sup.1+ ions are present in the glass matrix, the Cu.sup.1+ ions may be present in the form of Cu.sup.1+ crystals that are dispersed in the glass matrix. In some examples, the Cu.sup.1+ crystals include cuprite (Cu.sub.2O). In some examples, where Cu.sup.1+ crystals are present, the material may be referred to as a glass ceramic, which is intended to refer to a specific type of glass with crystals that may or may not be subjected to a traditional ceramming process by which one or more crystalline phases are introduced and/or generated in the glass. Where the Cu.sup.1+ ions are present in a non-crystalline form, the material may be referred to as a copper-containing glass. In some examples, both Cu.sup.1+ crystals and Cu.sup.1+ ions not associated with a crystal are present in the copper-containing glasses described herein.

[0081] The copper-containing glasses may include a copper-containing oxide in an amount, in mole percent, in the range from about 10 to about 50, from about 10 to about 49, from about 10 to about 48, from about 10 to about 47, from about 10 to about 46, from about 10 to about 45, from about 10 to about 44, from about 10 to about 43, from about 10 to about 42, from about 10 to about 41, from about 10 to about 40, from about 10 to about 39, from about 10 to about 38, from about 10 to about 37, from about 10 to about 36, from about 10 to about 35, from about 10 to about 34, from about 10 to about 33, from about 10 to about 32, from about 10 to about 31, from about 10 to about 30, from about 10 to about 29, from about 10 to about 28, from about 10 to about 27, from about 10 to about 26, from about 10 to about 25, from about 10 to about 24, from about 10 to about 23, from about 10 to about 22, from about 10 to about 21, from about 10 to about 20, from about 11 to about 50, from about 12 to about 50, from about 13 to about 50, from about 14 to about 50, from about 15 to about 50, from about 16 to about 50, from about 17 to about 50, from about 18 to about 50, from about 19 to about 50, from about 20 to about 50, from about 10 to about 30, from about 11 to about 29, from about 12 to about 28, from about 13 to about 27, from about 14 to about 26, from about 15 to about 25, from about 16 to about 24, from about 17 to about 23, from about 18 to about 22, from about 19 to about 21, and all ranges and sub-ranges therebetween. According to examples of the present disclosure, the copper-containing oxide may be present in the copper-containing glasses in an amount of about 20 mole percent, about 25 mole percent, about 30 mole percent, or about 35 mole percent. The copper-containing oxide may include CuO, Cu.sub.2O, and/or combinations thereof. The copper-containing glass particles may include cuprous oxide in an amount from 29.0 to 36.0 weight percent of the copper-containing glass particles. The copper-containing oxides in the copper-containing glasses form the Cu.sup.1+ ions present in the resulting glass. Copper may be present in a glass composition and/or the glasses including a glass composition in various forms, including Cu.sup.0, Cu.sup.1+, and Cu.sup.2+. Copper in the Cu.sup.0 or Cu.sup.1+ forms provide antimicrobial activity. However, forming and maintaining these states of antimicrobial copper are difficult, and often, in known glass compositions, Cu.sup.2+ may be formed instead of the desired Cu.sup.0 or Cu.sup.1+ ions.

[0082] The copper-containing glass portion of the individual particles of the copper-containing glass particles may be formed from a glass composition that may include, but is not limited to, in mole percent, SiO.sub.2 in the range from about 30 to about 70, Al.sub.2O.sub.3 in the range form about 0 to about 20, a copper-containing oxide in the range from about 10 to about 50, CaO in the range from about 0 to about 15, MgO in the range from about 0 to about 15, P.sub.2O.sub.5 in the range from about 0 to about 25, B.sub.2O.sub.3 in the range from about 0 to about 25, K.sub.2O in the range from about 0 to about 20, ZnO in the range from about 0 to about 5, Na.sub.2O in the range from about 0 to about 20, and/or Fe.sub.2O.sub.3 in the range from about 0 to about 5, nanoparticles thereof, and/or a mixture thereof. In such examples, the amount of the copper-containing oxide is greater than the amount of Al.sub.2O.sub.3. In some examples, the glass composition may include a content of R.sub.2O, where R may include K, Na, Li, Rb, Cs, and combinations thereof.

[0083] In some examples, the copper-containing glasses disclosed herein may be chemically strengthened via an ion exchange process in which the presence of a small amount of alkali oxide (such as Li.sub.2O and Na.sub.2O) is required to facilitate ion exchange with larger alkali ions (e.g., K.sup.1+), for example exchanging smaller alkali ions from a copper-containing glass with larger alkali ions from a molten salt bath containing such larger alkali ions. Three types of ion exchange may generally be carried out. One such ion exchange includes a Na.sup.1+-for-Li.sup.1+ exchange, which results in a deep depth of layer but low compressive stress. Another such ion exchange includes a K.sup.1+-for-Li.sup.1+ exchange, which results in a small depth of layer but a relatively large compressive stress. A third such ion exchange includes a K.sup.1+-for-Na.sup.1+ exchange, which results in intermediate depth of layer and compressive stress. A sufficiently high concentration of the small alkali oxide in glass compositions may be necessary to produce a large compressive stress in the copper-containing glass including such glass compositions, because compressive stress is proportional to the number of alkali ions that are exchanged out of the copper-containing glass.

[0084] In one or more examples, the glass composition may include one or more divalent cation oxides, such as alkaline earth oxides and/or ZnO. Such divalent cation oxides may be included to improve the melting behavior of the glass compositions. With respect to ion exchange performance, the presence of divalent cations may act to decrease alkali mobility and thus, when larger divalent cation oxides are utilized, there may be a negative effect on ion exchange performance. Further, smaller divalent cation oxides generally help the compressive stress developed in an ion-exchanged glass more than the larger divalent cation oxides. Hence, divalent cation oxides such as MgO and ZnO may offer advantages with respect to improved stress relaxation, while minimizing the adverse effects on alkali diffusivity.

[0085] In one or more examples, the glass composition may include one or more colorants. Examples of such colorants may include NiO, TiO.sub.2, Fe.sub.2O.sub.3, Cr.sub.2O.sub.3, Co.sub.3O.sub.4, and other known colorants. In some examples, the one or more colorants may be present in an amount in the range up to about 10 mol %. In some examples, the one or more colorants may be present in an amount in the range from about 0.01 mol % to about 10 mol %, from about 1 mol % to about 10 mol %, from about 2 to about 10 mol %, from about 5 mol % to about 10 mol %, from about 0.01 mol % to about 8 mol %, or from about 0.01 mol % to about 5 mol %.

[0086] The copper-containing glasses formed from the glass compositions may include a plurality of Cu.sup.1+ ions. In some examples, such Cu.sup.1+ ions form part of the glass network and may be characterized as a glass modifier. Without being bound by theory, where Cu.sup.1+ ions are part of the glass network, it is believed that during typical glass formation processes, the cooling step of the molten glass occurs too rapidly to allow crystallization of the copper-containing oxide (e.g., Cu and/or Cu.sub.2O). Thus, the Cu.sup.1+ remains in an amorphous state and becomes part of the glass network. In some cases, the total amount of Cu.sup.1+ ions, whether the Cu.sup.1+ ions are in a crystalline phase or in the glass matrix, may be even higher, such as up to 40 mol %, up to 50 mol %, or up to 60 mol %.

[0087] In one or more examples, the copper-containing glasses formed from the glass compositions disclosed herein include Cu.sup.1+ ions that are dispersed in the glass matrix as Cu.sup.1+ crystals. In one or more examples, the Cu.sup.1+ may be present in the form of cuprite. The cuprite present in the copper-containing glass may form a phase that is distinct form the glass matrix or glass phase. In other examples, the cuprite may form part of or may be associated with one or more glass phases (e.g., the durable phase described herein).

[0088] In some examples, the total amount of extractable copper by weight % in the copper-containing glass particles may be in the range from about 10 to about 100, from about 15 to about 100, from about 20 to about 100, from about 25 to about 100, from about 30 to about 100, from about 10 to about 95, from about 10 to about 90, from about 10 to about 85, from about 10 to about 80, from about 10 to about 75, from about 10 to about 70, from about 15 to about 70, from about 20 to about 70, from about 25 to about 70, from about 10 to about 65, from about 10 to about 60, from about 10 to about 55, from about 10 to about 50, from about 10 to about 45, from about 10 to about 40, from about 10 to about 35, from about 20 to about 50, from about 20 to about 45, from about 20 to about 40, from about 20 to about 35, from about 25 to about 35, from about 21 to about 40, from about 22 to about 40, from about 23 to about 40, from about 24 to about 40, from about 25 to about 40, from about 20 to about 39, from about 20 to about 38, from about 20 to about 37, from about 20 to about 36, from about 20 to about 35, from about 26 to about 34, from about 27 to about 33, from about 28 to about 32, from about 29 to about 31, and all ranges and sub-ranges therebetween; less than, equal to, or greater than about 5 weight %, 10, 15, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, or about 80 weight %. In one or more examples, the ratio of Cu.sup.1+ ions to the total amount of extractable copper in the copper-containing glass particles is about 0.5 or greater, 0.55 or greater, 0.6 or greater, 0.65 or greater, 0.7 or greater, 0.75 or greater, 0.8 or greater, 0.85 or greater, 0.9 or greater, or even 1 or greater, and all ranges and sub-ranges therebetween.

[0089] According to some examples of the present disclosure, the copper-containing material and/or materials described herein leach the copper ions when exposed or in contact with a leachate. In one or more examples, the copper-containing material leach only copper ions when exposed to leachates, which may be a pretreatment solution according to the present disclosure, including water. The copper-containing material may include at least a first phase and a second phase. In one or more examples, the copper-containing material may include two or more phases wherein the phases differ based on the ability of the atomic bonds in the given phase to withstand interaction with a leachate. Specifically, the copper-containing material of one or more examples may include a first phase that may be described as a degradable phase and a second phase that may be described as a durable phase. In one or more examples, the durable phase includes SiO.sub.2 and the degradable phase includes at least one of B.sub.2O.sub.3, P.sub.2O.sub.5, and R.sub.2O (where R may include any one or more of K, Na, Li, Rb, and Cs). Without wishing to be bound by theory, it is believed that the components of the degradable phase (e.g., B.sub.2O.sub.3, P.sub.2O.sub.5, and/or R.sub.2O) more readily interact with a leachate or a pretreatment solution and the bonds between these components to one another rand to other components in the copper-containing glass more readily break during and after the interaction with the leachate. Leachates may include water, acids or other similar materials. In one or more examples, the degradable phase withstands degradation for 1 week or longer, 1 month or longer, 3 months or longer, or even 6 months or longer. In some examples, longevity may be characterized as maintaining antimicrobial efficacy over a specific period of time. In one or more examples, either one or both of the durable phase and degradable phase may include cuprite. The cuprite in such examples may be dispersed in the respective phase or in both phases.

[0090] As discussed above, the copper-containing glass particles, which may have been pre-treated with a pretreatment solution, may be combined with a copper-coordinating additive. In an example, a copper-coordinating additive may be a compound of formula (I):

##STR00007## [0091] wherein each of R.sup.1 and R.sup.2 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; [0092] provided that both of R.sup.1 and R.sup.2 are not simultaneously hydrogen.

[0093] Certain examples of compounds of formula (I) may include particular combinations of R.sup.1 and R.sup.2 such that the compounds of formula (I) complex with copper, but not as desirably or preferably as other particular combinations of R.sup.1 and R.sup.2 due to the combined effects of chemical phenomena understood by those skilled in the art, including, but not limited to, hydrophobicity, solubility, electronic effects, and/or steric effects resulting from the chemical structure of a particular compound of formula (I). In certain examples of compounds of formula (I), each of R.sup.1 and R.sup.2, independently, may not be (C.sub.1-C.sub.30)alkyl, and/or may not be (C.sub.2-C.sub.30)alkenyl, and/or may not be (C.sub.2-C.sub.30)alkynyl, and/or may not be aryl, and/or may not be heteroaryl, and/or may not be heterocyclyl, and/or may not be aryl(C.sub.1-C.sub.4)alkyl, and/or may not be heteroaryl(C.sub.1-C.sub.4)alkyl, and/or may not be heterocyclyl(C.sub.1-C.sub.4)alkyl.

[0094] Examples of compounds of formula (I) may include 2-ethylhexyl phosphate, bis(2-ethylhexyl)phosphate, methyl phosphate, dimethyl phosphate, phenyl phosphate, and diphenyl phosphate.

[0095] Without being bound by any particular theory, compounds of formula (I) minimize color drift by reducing overall copper complex color and/or by favoring Cu.sup.1+ tetrahedral geometry over Cu.sup.2+ octahedral geometry and/or by providing sterics and hydrophobicity to limit access of water to the copper ion and thereby inhibit oxidation. Further, compounds of formula (I) accelerate reaching color endpoint by enhancing the solubility of Cu.sup.1+.

[0096] In another example, a copper-coordinating additive may be a compound of formula (II):

##STR00008## [0097] wherein each R.sup.3 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, substituted or unsubstituted 2-pyridyl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; [0098] the substituted 2-pyridyl is substituted with up to four substituents, each substituent independently selected from the group consisting of (C.sub.1-C.sub.30)alkyl, (C.sub.1-C.sub.30)alkoxy, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkenoxy, (C.sub.2-C.sub.30)alkynyl, (C.sub.2-C.sub.30)alkynoxy, aryl, aryloxy, heteroaryl, heteroaryloxy, heterocyclyl, heterocyclyloxy, aryl(C.sub.1-C.sub.4)alkyl, aryl(C.sub.1-C.sub.4)alkoxy, heteroaryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkoxy, heterocyclyl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkoxy; and [0099] each R.sup.4 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl.

[0100] Certain examples of compounds of formula (II) may include particular combinations of R.sup.3 and R.sup.4 such that the compounds of formula (II) complex with copper, but not as desirably or preferably as other particular combinations of R.sup.3 and R.sup.4 due to the combined effects of chemical phenomena understood by those skilled in the art, including, but not limited to, hydrophobicity, solubility, electronic effects, and/or steric effects resulting from the chemical structure of a particular compound of formula (II). In certain examples of compounds of formula (II), each R.sup.3, independently, may not be hydrogen, and/or may not be (C.sub.1-C.sub.30)alkyl, and/or may not be (C.sub.2-C.sub.30)alkenyl, and/or may not be (C.sub.2-C.sub.30)alkynyl, and/or may not be aryl, and/or may not be heteroaryl, and/or may not be unsubstituted 2-pyridyl, and/or may not be heterocyclyl, and/or may not be aryl(C.sub.1-C.sub.4)alkyl, and/or may not be heteroaryl(C.sub.1-C.sub.4)alkyl, and/or may not be heterocyclyl(C.sub.1-C.sub.4)alkyl. In certain examples of compounds of formula (II), each of up to four substituents of a substituted 2-pyridyl, independently, may not be (C.sub.1-C.sub.30)alkyl, and/or may not be (C.sub.1-C.sub.30)alkoxy, and/or may not be (C.sub.2-C.sub.30)alkenyl, and/or may not be (C.sub.2-C.sub.30)alkenoxy, and/or may not be (C.sub.2-C.sub.30)alkynyl, and/or may not be (C.sub.2-C.sub.30)alkynoxy, and/or may not be aryl, and/or may not be aryloxy, and/or may not be heteroaryl, and/or may not be heteroaryloxy, and/or may not be heterocyclyl, and/or may not be heterocyclyloxy, and/or may not be aryl(C.sub.1-C.sub.4)alkyl, and/or may not be aryl(C.sub.1-C.sub.4)alkoxy, and/or may not be heteroaryl(C.sub.1-C.sub.4)alkyl, and/or may not be heteroaryl(C.sub.1-C.sub.4)alkoxy, and/or may not be heterocyclyl(C.sub.1-C.sub.4)alkyl, and/or may not be heterocyclyl(C.sub.1-C.sub.4)alkoxy. In certain examples of compounds of formula (II), each R.sup.4, independently, may not be hydrogen, and/or may not be (C.sub.1-C.sub.30)alkyl, and/or may not be (C.sub.2-C.sub.30)alkenyl, and/or may not be (C.sub.2-C.sub.30)alkynyl, and/or may not be aryl, and/or may not be heteroaryl, and/or may not be heterocyclyl, and/or may not be aryl(C.sub.1-C.sub.4)alkyl, and/or may not be heteroaryl(C.sub.1-C.sub.4)alkyl, and/or may not be heterocyclyl(C.sub.1-C.sub.4)alkyl.

[0101] Examples of compounds of formula (II) may include 2,2-bipyridine and terpyridine. 2,2-Bipyridine has the structural formula:

##STR00009##

Terpyridine has the structural formula:

##STR00010##

[0102] Without being bound by any particular theory, compounds of formula (II) minimize color drift by reducing overall copper complex color and/or by favoring Cu.sup.1+ tetrahedral geometry over Cu.sup.2+ octahedral geometry and/or by providing sterics and hydrophobicity to limit access of water to the copper ion and thereby inhibit oxidation.

[0103] In yet another example, a copper-coordinating additive may be a compound of formula (III):

##STR00011## [0104] wherein R.sup.5 is selected from the group consisting of substituted or unsubstituted (C.sub.1-C.sub.30)alkyl, substituted or unsubstituted (C.sub.2-C.sub.30)alkenyl, substituted or unsubstituted (C.sub.2-C.sub.30)alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl(C.sub.1-C.sub.4)alkyl, substituted or unsubstituted heteroaryl(C.sub.1-C.sub.4)alkyl, and substituted or unsubstituted heterocyclyl(C.sub.1-C.sub.4)alkyl; and [0105] the substituted (C.sub.1-C.sub.30)alkyl, substituted (C.sub.2-C.sub.30)alkenyl, substituted (C.sub.2-C.sub.30)alkynyl, substituted aryl, substituted heteroaryl, substituted heterocyclyl, substituted aryl(C.sub.1-C.sub.4)alkyl, substituted heteroaryl(C.sub.1-C.sub.4)alkyl, and substituted heterocyclyl(C.sub.1-C.sub.4)alkyl are substituted with one or more substituents each of which is independently selected from the group consisting of OH, NH.sub.2, SH, CN, C(O)NH.sub.2, and CO.sub.2H.

[0106] Certain examples of compounds of formula (III) may complex with copper, but not as desirably or preferably as other examples of compounds of formula (III) due to the combined effects of chemical phenomena understood by those skilled in the art, including, but not limited to, hydrophobicity, solubility, electronic effects, and/or steric effects resulting from the chemical structure of a particular compound of formula (III). In certain examples of compounds of formula (III), R may not be unsubstituted (C.sub.1-C.sub.30)alkyl, and/or may not be unsubstituted (C.sub.2-C.sub.30)alkenyl, and/or may not be unsubstituted (C.sub.2-C.sub.30)alkynyl, and/or may not be unsubstituted aryl, and/or may not be unsubstituted heteroaryl, and/or may not be unsubstituted heterocyclyl, and/or may not be unsubstituted aryl(C.sub.1-C.sub.4)alkyl, and/or may not be unsubstituted heteroaryl(C.sub.1-C.sub.4)alkyl, and/or may not be unsubstituted heterocyclyl(C.sub.1-C.sub.4)alkyl. In certain examples of compounds of formula (III), R.sup.5 may not be substituted (C.sub.1-C.sub.30)alkyl, and/or may not be substituted (C.sub.2-C.sub.30)alkenyl, and/or may not be substituted (C.sub.2-C.sub.30)alkynyl, and/or may not be substituted aryl, and/or may not be substituted heteroaryl, and/or may not be substituted heterocyclyl, and/or may not be substituted aryl(C.sub.1-C.sub.4)alkyl, and/or may not be substituted heteroaryl(C.sub.1-C.sub.4)alkyl, and/or may not be substituted heterocyclyl(C.sub.1-C.sub.4)alkyl. In certain examples of compounds of formula (III), the one or more substituents, each, independently, may not be OH, and/or may not be NH.sub.2, and/or may not be SH, and/or may not be CN, and/or may not be C(O)NH.sub.2, and/or may not be CO.sub.2H.

[0107] Examples of compounds of formula (III) may include citric acid, which has the structural formula:

##STR00012##

[0108] Without being bound by any particular theory, compounds of formula (III) minimize color drift by reducing overall copper complex color and/or by favoring Cu.sup.1+ tetrahedral geometry over Cu.sup.2+ octahedral geometry and/or by providing sterics and hydrophobicity to limit access of water to the copper ion and thereby inhibit oxidation. Further, compounds of formula (III) accelerate reaching color endpoint by enhancing the solubility of Cu.sup.1+.

[0109] In yet another example, a copper-coordinating additive may be a compound of formula (IV):

##STR00013## [0110] wherein, from S to S, R.sup.6 is selected from the group consisting of substituted or unsubstituted (C.sub.2-C.sub.30)alkylene, substituted or unsubstituted (C.sub.2-C.sub.30)alkenylene, substituted or unsubstituted (C.sub.2-C.sub.30)alkynylene, substituted or unsubstituted aryl(C.sub.1-C.sub.4)alkylene, substituted or unsubstituted (C.sub.1-C.sub.4)alkylarylene, substituted or unsubstituted (C.sub.1-C.sub.4)alkylaryl(C.sub.1-C.sub.4)alkylene, substituted or unsubstituted heteroaryl(C.sub.1-C.sub.4)alkylene, substituted or unsubstituted (C.sub.1-C.sub.4)alkylheteroarylene, substituted or unsubstituted (C.sub.1-C.sub.4)alkylheteroaryl(C.sub.1-C.sub.4)alkylene, substituted or unsubstituted heterocyclyl(C.sub.1-C.sub.4)alkylene, substituted or unsubstituted (C.sub.1-C.sub.4)alkylheterocyclylene, and substituted or unsubstituted (C.sub.1-C.sub.4)alkylheterocyclyl(C.sub.1-C.sub.4)alkylene; [0111] the substituted (C.sub.2-C.sub.30)alkylene, substituted (C.sub.2-C.sub.30)alkenylene, substituted (C.sub.2-C.sub.30)alkynylene, substituted aryl(C.sub.1-C.sub.4)alkylene, substituted (C.sub.1-C.sub.4)alkylarylene, substituted (C.sub.1-C.sub.4)alkylaryl(C.sub.1-C.sub.4)alkylene, substituted heteroaryl(C.sub.1-C.sub.4)alkylene, substituted (C.sub.1-C.sub.4)alkylheteroarylene, substituted (C.sub.1-C.sub.4)alkylheteroaryl(C.sub.1-C.sub.4)alkylene, substituted heterocyclyl(C.sub.1-C.sub.4)alkylene, substituted (C.sub.1-C.sub.4)alkylheterocyclylene, and substituted (C.sub.1-C.sub.4)alkylheterocyclyl(C.sub.1-C.sub.4)alkylene are substituted with one or more substituents each independently selected from the group consisting of (C.sub.1-C.sub.30)alkyl, (C.sub.1-C.sub.30)alkoxy, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkenyloxy, (C.sub.2-C.sub.30)alkynyl, (C.sub.2-C.sub.30)alkynyloxy, aryl, aryloxy, heteroaryl, heteroaryloxy, heterocyclyl, heterocyclyloxy, aryl(C.sub.1-C.sub.4)alkyl, aryl(C.sub.1-C.sub.4)alkoxy, heteroaryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkoxy, heterocyclyl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkoxy; [0112] provided that the two thiol groups are not bonded to the same carbon.

[0113] Certain examples of compounds of formula (IV) may complex with copper, but not as desirably or preferably as other examples of compounds of formula (IV) due to the combined effects of chemical phenomena understood by those skilled in the art, including, but not limited to, hydrophobicity, solubility, electronic effects, and/or steric effects resulting from the chemical structure of a particular compound of formula (IV). In certain examples of compounds of formula (IV), R.sup.6 may not be (C.sub.2-C.sub.30)alkylene, and/or may not be (C.sub.2-C.sub.30)alkenylene, and/or may not be (C.sub.2-C.sub.30)alkynylene, and/or may not be aryl(C.sub.1-C.sub.4)alkylene, and/or may not be (C.sub.1-C.sub.4)alkylarylene, and/or may not be (C.sub.1-C.sub.4)alkylaryl(C.sub.1-C.sub.4)alkylene, and/or may not be heteroaryl(C.sub.1-C.sub.4)alkylene, and/or may not be (C.sub.1-C.sub.4)alkylheteroarylene, and/or may not be (C.sub.1-C.sub.4)alkylheteroaryl(C.sub.1-C.sub.4)alkylene, and/or may not be heterocyclyl(C.sub.1-C.sub.4)alkylene, and/or may not be (C.sub.1-C.sub.4)alkylheterocyclylene, and/or may not be (C.sub.1-C.sub.4)alkylheterocyclyl(C.sub.1-C.sub.4)alkylene. In certain examples of compounds of formula (IV), the one or more substituents, each, independently, may not be (C.sub.1-C.sub.30)alkyl, and/or may not be (C.sub.1-C.sub.30)alkoxy, and/or may not be (C.sub.2-C.sub.30)alkenyl, and/or may not be (C.sub.2-C.sub.30)alkenyloxy, and/or may not be (C.sub.2-C.sub.30)alkynyl, and/or may not be (C.sub.2-C.sub.30)alkynyloxy, and/or may not be aryl, and/or may not be aryloxy, and/or may not be heteroaryl, and/or may not be heteroaryloxy, and/or may not be heterocyclyl, and/or may not be heterocyclyloxy, and/or may not be aryl(C.sub.1-C.sub.4)alkyl, and/or may not be aryl(C.sub.1-C.sub.4)alkoxy, and/or may not be heteroaryl(C.sub.1-C.sub.4)alkyl, and/or may not be heteroaryl(C.sub.1-C.sub.4)alkoxy, and/or may not be heterocyclyl(C.sub.1-C.sub.4)alkyl, and/or may not be heterocyclyl(C.sub.1-C.sub.4)alkoxy.

[0114] Without being bound by any particular theory, compounds of formula (IV) minimize color drift by reducing overall copper complex color and/or by favoring Cu.sup.1+ tetrahedral geometry over Cu.sup.2+ octahedral geometry and/or by providing sterics and hydrophobicity to limit access of water to the copper ion and thereby inhibit oxidation.

[0115] In yet another example, a copper-coordinating additive may be a compound of formula (V):

##STR00014## [0116] wherein each R.sup.7 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.1-C.sub.30)alkoxy, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkenyloxy, (C.sub.2-C.sub.30)alkynyl, (C.sub.2-C.sub.30)alkynyloxy, aryl, aryloxy, heteroaryl, heteroaryloxy, heterocyclyl, heterocyclyloxy, aryl(C.sub.1-C.sub.4)alkyl, aryl(C.sub.1-C.sub.4)alkoxy, heteroaryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkoxy, heterocyclyl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkoxy; [0117] R.sup.8 is selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, heterocyclyl(C.sub.1-C.sub.4)alkyl, and (C(R.sup.7).sub.2).sub.zOH; and [0118] each of x, y, and z is independently 2 or 3.

[0119] Certain examples of compounds of formula (V) may complex with copper, but not as desirably or preferably as other examples of compounds of formula (V) due to the combined effects of chemical phenomena understood by those skilled in the art, including, but not limited to, hydrophobicity, solubility, electronic effects, and/or steric effects resulting from the chemical structure of a particular compound of formula (V). In certain examples of compounds of formula (V), each R.sup.7, independently, may not be hydrogen, and/or may not be (C.sub.1-C.sub.30)alkyl, and/or may not be (C.sub.1-C.sub.30)alkoxy, and/or may not be (C.sub.2-C.sub.30)alkenyl, and/or may not be (C.sub.2-C.sub.30)alkenyloxy, and/or may not be (C.sub.2-C.sub.30)alkynyl, and/or may not be (C.sub.2-C.sub.30)alkynyloxy, and/or may not be aryl, and/or may not be aryloxy, and/or may not be heteroaryl, and/or may not be heteroaryloxy, and/or may not be heterocyclyl, and/or may not be heterocyclyloxy, and/or may not be aryl(C.sub.1-C.sub.4)alkyl, and/or may not be aryl(C.sub.1-C.sub.4)alkoxy, and/or may not be heteroaryl(C.sub.1-C.sub.4)alkyl, and/or may not be heteroaryl(C.sub.1-C.sub.4)alkoxy, and/or may not be heterocyclyl(C.sub.1-C.sub.4)alkyl, and/or may not be heterocyclyl(C.sub.1-C.sub.4)alkoxy. In certain examples of compounds of formula (V), R.sup.8 may not be hydrogen, and/or may not be (C.sub.1-C.sub.30)alkyl, and/or may not be (C.sub.2-C.sub.30)alkenyl, and/or may not be (C.sub.2-C.sub.30)alkynyl, and/or may not be aryl, and/or may not be heteroaryl, and/or may not be heterocyclyl, and/or may not be aryl(C.sub.1-C.sub.4)alkyl, and/or may not be heteroaryl(C.sub.1-C.sub.4)alkyl, and/or may not be heterocyclyl(C.sub.1-C.sub.4)alkyl, and/or may not be (C(R.sup.7).sub.2).sub.zOH. In certain examples of compounds of formula (V), each of x, y, and z, independently, may not be 2 or may not be 3.

[0120] Examples of compounds of formula (V) may include diethanolamine and triethanolamine. Diethanolamine has the structural formula:

##STR00015##

Triethanolamine has the structural formula:

##STR00016##

[0121] Without being bound by any particular theory, compounds of formula (V) minimize color drift by reducing overall copper complex color and/or by favoring Cu.sup.1+ tetrahedral geometry over Cu.sup.2+ octahedral geometry and/or by providing sterics and hydrophobicity to limit access of water to the copper ion and thereby inhibit oxidation.

[0122] In yet another example, a copper-coordinating additive may be a compound of formula (VI):

##STR00017## [0123] wherein X.sup. is selected from the group consisting of fluoride, chloride, bromide, iodide, hexafluorophosphate, sulfate, an alkylsulfonate, and an arylsulfonate; and [0124] R.sup.9 is selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl.

[0125] Certain examples of compounds of formula (VI) may complex with copper, but not as desirably or preferably as other examples of compounds of formula (VI) due to the combined effects of chemical phenomena understood by those skilled in the art, including, but not limited to, hydrophobicity, solubility, electronic effects, and/or steric effects resulting from the chemical structure of a particular compound of formula (VI). In certain examples of compounds of formula (VI), X.sup. may not be fluoride, and/or may not be chloride, and/or may not be bromide, and/or may not be iodide, and/or may not be hexafluorophosphate, and/or may not be sulfate, and/or may not be an alkylsulfonate, and/or may not be an arylsulfonate. In certain examples of compounds of formula (VI), R.sup.9 may not be hydrogen, and/or may not be (C.sub.1-C.sub.30)alkyl, and/or may not be (C.sub.2-C.sub.30)alkenyl, and/or may not be (C.sub.2-C.sub.30)alkynyl, and/or may not be aryl, and/or may not be heteroaryl, and/or may not be heterocyclyl, and/or may not be aryl(C.sub.1-C.sub.4)alkyl, and/or may not be heteroaryl(C.sub.1-C.sub.4)alkyl, and/or may not be heterocyclyl(C.sub.1-C.sub.4)alkyl.

[0126] Without being bound by any particular theory, compounds of formula (VI) accelerate reaching color endpoint by enhancing the solubility of Cu.sup.1+.

[0127] In yet another example, a copper-coordinating additive may be a compound of formula (VII):

##STR00018## [0128] wherein each of R.sup.10 and R.sup.11 is independently selected from the group consisting of substituted or unsubstituted (C.sub.1-C.sub.30)alkyl, substituted or unsubstituted (C.sub.2-C.sub.30)alkenyl, substituted or unsubstituted (C.sub.2-C.sub.30)alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl(C.sub.1-C.sub.4)alkyl, substituted or unsubstituted heteroaryl(C.sub.1-C.sub.4)alkyl, and substituted or unsubstituted heterocyclyl(C.sub.1-C.sub.4)alkyl; and [0129] the substituted (C.sub.1-C.sub.30)alkyl, substituted (C.sub.2-C.sub.30)alkenyl, substituted (C.sub.2-C.sub.30)alkynyl, substituted aryl, substituted heteroaryl, substituted heterocyclyl, substituted aryl(C.sub.1-C.sub.4)alkyl, substituted heteroaryl(C.sub.1-C.sub.4)alkyl, and substituted heterocyclyl(C.sub.1-C.sub.4)alkyl are substituted with one or more substituents each of which is independently selected from the group consisting of OH, NH.sub.2, SH, CN, C(O)NH.sub.2, C(O)NHR.sup.11, C(O)NR.sup.11.sub.2, CO.sub.2H, and CO.sub.2R.sup.11.

[0130] Certain examples of compounds of formula (VII) may complex with copper, but not as desirably or preferably as other examples of compounds of formula (VII) due to the combined effects of chemical phenomena understood by those skilled in the art, including, but not limited to, hydrophobicity, solubility, electronic effects, and/or steric effects resulting from the chemical structure of a particular compound of formula (VII). In certain examples of compounds of formula (VII), each R.sup.10 and R.sup.11 independently may not be unsubstituted (C.sub.1-C.sub.30)alkyl, and/or may not be unsubstituted (C.sub.2-C.sub.30)alkenyl, and/or may not be unsubstituted (C.sub.2-C.sub.30)alkynyl, and/or may not be unsubstituted aryl, and/or may not be unsubstituted heteroaryl, and/or may not be unsubstituted heterocyclyl, and/or may not be unsubstituted aryl(C.sub.1-C.sub.4)alkyl, and/or may not be unsubstituted heteroaryl(C.sub.1-C.sub.4)alkyl, and/or may not be unsubstituted heterocyclyl(C.sub.1-C.sub.4)alkyl. In certain examples of compounds of formula (VII), each R.sup.10 and R.sup.11 independently may not be substituted (C.sub.1-C.sub.30)alkyl, and/or may not be substituted (C.sub.2-C.sub.30)alkenyl, and/or may not be substituted (C.sub.2-C.sub.30)alkynyl, and/or may not be substituted aryl, and/or may not be substituted heteroaryl, and/or may not be substituted heterocyclyl, and/or may not be substituted aryl(C.sub.1-C.sub.4)alkyl, and/or may not be substituted heteroaryl(C.sub.1-C.sub.4)alkyl, and/or may not be substituted heterocyclyl(C.sub.1-C.sub.4)alkyl. In certain examples of compounds of formula (VII), the one or more substituents, each, independently, may not be OH, and/or may not be NH.sub.2, and/or may not be SH, and/or may not be CN, and/or may not be C(O)NH.sub.2, and/or may not be C(O)NHR.sup.11, and/or may not be C(O)NR.sup.12, and/or may not be CO.sub.2H, and/or may not be CO.sub.2R.sup.11.

[0131] Examples of compounds of formula (VII) may include triethyl citrate, which has the structural formula:

##STR00019##

[0132] Without being bound by any particular theory, compounds of formula (VII) accelerate reaching color endpoint by enhancing the solubility of Cu.sup.1+.

[0133] In yet another example, a copper-coordinating additive may be a compound of formula (VIII):

##STR00020## [0134] wherein R.sup.12 is selected from the group consisting of substituted or unsubstituted (C.sub.1-C.sub.30)alkyl, substituted or unsubstituted (C.sub.2-C.sub.30)alkenyl, substituted or unsubstituted (C.sub.2-C.sub.30)alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl(C.sub.1-C.sub.4)alkyl, substituted or unsubstituted heteroaryl(C.sub.1-C.sub.4)alkyl, and substituted or unsubstituted heterocyclyl(C.sub.1-C.sub.4)alkyl; [0135] each R.sup.13 is independently selected from the group consisting of hydrogen, substituted or unsubstituted (C.sub.1-C.sub.30)alkyl, substituted or unsubstituted (C.sub.2-C.sub.30)alkenyl, substituted or unsubstituted (C.sub.2-C.sub.30)alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl(C.sub.1-C.sub.4)alkyl, substituted or unsubstituted heteroaryl(C.sub.1-C.sub.4)alkyl, and substituted or unsubstituted heterocyclyl(C.sub.1-C.sub.4)alkyl; and [0136] the substituted (C.sub.1-C.sub.30)alkyl, substituted (C.sub.2-C.sub.30)alkenyl, substituted (C.sub.2-C.sub.30)alkynyl, substituted aryl, substituted heteroaryl, substituted heterocyclyl, substituted aryl(C.sub.1-C.sub.4)alkyl, substituted heteroaryl(C.sub.1-C.sub.4)alkyl, and substituted heterocyclyl(C.sub.1-C.sub.4)alkyl are substituted with one or more substituents each of which is independently selected from the group consisting of OH, NH.sub.2, SH, CN, C(O)NH.sub.2, C(O)NHR.sup.13, C(O)NR.sup.13.sub.2, CO.sub.2H, and CO.sub.2R.sup.13.

[0137] Certain examples of compounds of formula (VIII) may include particular combinations of R.sup.12 and R.sup.13 such that the compounds of formula (VIII) complex with copper, but not as desirably or preferably as other particular combinations of R.sup.12 and R.sup.13 due to the combined effects of chemical phenomena understood by those skilled in the art, including, but not limited to, hydrophobicity, solubility, electronic effects, and/or steric effects resulting from the chemical structures of a particular compound of formula (VIII). In certain examples of compounds of formula (VIII), R.sup.12 may not be substituted (C.sub.1-C.sub.30)alkyl, and/or may not be unsubstituted (C.sub.1-C.sub.30)alkyl, and/or may not be substituted (C.sub.2-C.sub.30)alkenyl, and/or may not be unsubstituted (C.sub.2-C.sub.30)alkenyl, and/or may not be substituted (C.sub.2-C.sub.30)alkynyl, and/or may not be unsubstituted (C.sub.2-C.sub.30)alkynyl, and/or may not be substituted aryl, and/or may not be unsubstituted aryl, and/or may not be substituted heteroaryl, and/or may not be unsubstituted heteroaryl, and/or may not be substituted heterocyclyl, and/or may not be unsubstituted heterocyclyl, and/or may not be substituted aryl(C.sub.1-C.sub.4)alkyl, and/or may not be unsubstituted aryl(C.sub.1-C.sub.4)alkyl, and/or may not be substituted heteroaryl(C.sub.1-C.sub.4)alkyl, and/or may not be unsubstituted heteroaryl(C.sub.1-C.sub.4)alkyl, and/or may not be substituted heterocyclyl(C.sub.1-C.sub.4)alkyl, and/or may not be unsubstituted heterocyclyl(C.sub.1-C.sub.4)alkyl. In certain examples of compounds of formula (VIII), each R.sup.13 independently may not be hydrogen, and/or may not be substituted (C.sub.1-C.sub.30)alkyl, and/or may not be unsubstituted (C.sub.1-C.sub.30)alkyl, and/or may not be substituted (C.sub.2-C.sub.30)alkenyl, and/or may not be unsubstituted (C.sub.2-C.sub.30)alkenyl, and/or may not be substituted (C.sub.2-C.sub.30)alkynyl, and/or may not be unsubstituted (C.sub.2-C.sub.30)alkynyl, and/or may not be substituted aryl, and/or may not be unsubstituted aryl, and/or may not be substituted heteroaryl, and/or may not be unsubstituted heteroaryl, and/or may not be substituted heterocyclyl, and/or may not be unsubstituted heterocyclyl, and/or may not be substituted aryl(C.sub.1-C.sub.4)alkyl, and/or may not be unsubstituted aryl(C.sub.1-C.sub.4)alkyl, and/or may not be substituted heteroaryl(C.sub.1-C.sub.4)alkyl, and/or may not be unsubstituted heteroaryl(C.sub.1-C.sub.4)alkyl, and/or may not be substituted heterocyclyl(C.sub.1-C.sub.4)alkyl, and/or may not be unsubstituted heterocyclyl(C.sub.1-C.sub.4)alkyl. In certain examples of compounds of formula (VIII), the one or more substituents, each, independently, may not be OH, and/or may not be NH.sub.2, and/or may not be SH, and/or may not be CN, and/or may not be C(O)NH.sub.2, and/or may not be C(O)NHR.sup.13, and/or may not be C(O)NR.sup.132, and/or may not be CO.sub.2H, and/or may not be CO.sub.2R.sup.13.

[0138] Without being bound by any particular theory, compounds of formula (VIII) accelerate color endpoint by extracting Cu.sup.1+ from a copper-containing material as a pretreatment with a pretreatment solution.

[0139] In yet another example, a copper-coordinating additive may be a compound of formula (IX):

##STR00021## [0140] wherein each R.sup.14 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.1-C.sub.30)alkoxy, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkenyloxy, (C.sub.2-C.sub.30)alkynyl, (C.sub.2-C.sub.30)alkynyloxy, aryl, aryloxy, heteroaryl, heteroaryloxy, heterocyclyl, heterocyclyloxy, aryl(C.sub.1-C.sub.4)alkyl, aryl(C.sub.1-C.sub.4)alkoxy, heteroaryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkoxy, heterocyclyl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkoxy; [0141] R.sup.15 is selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, heterocyclyl(C.sub.1-C.sub.4)alkyl, and (C(R.sup.14).sub.2).sub.pNH.sub.2; and [0142] each of m, n, and p is independently 2 or 3.

[0143] Certain examples of compounds of formula (IX) may complex with copper, but not as desirably or preferably as other examples of compounds of formula (IX) due to the combined effects of chemical phenomena understood by those skilled in the art, including, but not limited to, hydrophobicity, solubility, electronic effects, and/or steric effects resulting from the chemical structure of a particular compound of formula (IX). In certain examples of compounds of formula (IX), each R.sup.14, independently, may not be hydrogen, and/or may not be (C.sub.1-C.sub.30)alkyl, and/or may not be (C.sub.1-C.sub.30)alkoxy, and/or may not be (C.sub.2-C.sub.30)alkenyl, and/or may not be (C.sub.2-C.sub.30)alkenyloxy, and/or may not be (C.sub.2-C.sub.30)alkynyl, and/or may not be (C.sub.2-C.sub.30)alkynyloxy, and/or may not be aryl, and/or may not be aryloxy, and/or may not be heteroaryl, and/or may not be heteroaryloxy, and/or may not be heterocyclyl, and/or may not be heterocyclyloxy, and/or may not be aryl(C.sub.1-C.sub.4)alkyl, and/or may not be aryl(C.sub.1-C.sub.4)alkoxy, and/or may not be heteroaryl(C.sub.1-C.sub.4)alkyl, and/or may not be heteroaryl(C.sub.1-C.sub.4)alkoxy, and/or may not be heterocyclyl(C.sub.1-C.sub.4)alkyl, and/or may not be heterocyclyl(C.sub.1-C.sub.4)alkoxy. In certain examples of compounds of formula (IX), R.sup.15 may not be hydrogen, and/or may not be (C.sub.1-C.sub.30)alkyl, and/or may not be (C.sub.2-C.sub.30)alkenyl, and/or may not be (C.sub.2-C.sub.30)alkynyl, and/or may not be aryl, and/or may not be heteroaryl, and/or may not be heterocyclyl, and/or may not be aryl(C.sub.1-C.sub.4)alkyl, and/or may not be heteroaryl(C.sub.1-C.sub.4)alkyl, and/or may not be heterocyclyl(C.sub.1-C.sub.4)alkyl, and/or may not be (C(R.sup.15).sub.2).sub.pNH.sub.2. In certain examples of compounds of formula (IX), each of m, n, and p, independently, may not be 2 or may not be 3.

[0144] Without being bound by any particular theory, compounds of formula (IX) accelerate reaching color endpoint by enhancing the solubility of Cu.sup.1+.

[0145] In yet another example, a copper-coordinating additive may be a compound of formula (X):

##STR00022## [0146] wherein Y is O or S; [0147] each R.sup.16 is independently OR.sup.17 or N(R.sup.18).sub.2; [0148] R.sup.17 is selected from the group consisting of (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; and [0149] each R.sup.18 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl.

[0150] Certain examples of compounds of formula (X) may complex with copper, but not as desirably or preferably as other examples of compounds of formula (X) due to the combined effects of chemical phenomena understood by those skilled in the art, including, but not limited to, hydrophobicity, solubility, electronic effects, and/or steric effects resulting from the chemical structure of a particular compound of formula (X). In certain examples of compounds of formula (X), Y may not be O or may not be S. In certain examples of compounds of formula (X), each R.sup.16 independently may not be OR.sup.17 or may not be N(R.sup.18).sub.2. In certain examples of compounds of formula (X), R.sup.17 may not be (C.sub.1-C.sub.30)alkyl, and/or may not be (C.sub.2-C.sub.30)alkenyl, and/or may not be (C.sub.2-C.sub.30)alkynyl, and/or may not be aryl, and/or may not be heteroaryl, and/or may not be heterocyclyl, and/or may not be aryl(C.sub.1-C.sub.4)alkyl, and/or may not be heteroaryl(C.sub.1-C.sub.4)alkyl, and/or may not be heterocyclyl(C.sub.1-C.sub.4)alkyl. In certain examples of compounds of formula (X), each R.sup.18, independently, may not be hydrogen, and/or may not be (C.sub.1-C.sub.30)alkyl, and/or may not be (C.sub.2-C.sub.30)alkenyl, and/or may not be (C.sub.2-C.sub.30)alkynyl, and/or may not be aryl, and/or may not be heteroaryl, and/or may not be heterocyclyl, and/or may not be aryl(C.sub.1-C.sub.4)alkyl, and/or may not be heteroaryl(C.sub.1-C.sub.4)alkyl, and/or may not be heterocyclyl(C.sub.1-C.sub.4)alkyl.

[0151] Without being bound by any particular theory, compounds of formula (X) accelerate reaching color endpoint by enhancing the solubility of Cu.sup.1+.

[0152] In yet another example, a copper-coordinating additive may be a compound of formula (XI):

##STR00023## [0153] wherein each R.sup.19 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; and [0154] provided that all R.sup.19 are not simultaneously hydrogen.

[0155] Without being bound by any particular theory, compounds of formula (XI) minimize color drift by reducing overall copper complex color and/or by favoring Cu.sup.1+ tetrahedral geometry over Cu.sup.2+ octahedral geometry and/or by providing sterics and hydrophobicity to limit access of water to the copper ion and thereby inhibit oxidation. Without being bound by any particular theory, compounds of formula (XI) accelerate reaching color endpoint by enhancing the solubility of Cu.sup.1+.

[0156] In yet another example, a copper-coordinating additive may be a compound of formula (XII):

##STR00024## [0157] wherein each R.sup.20 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; and [0158] provided that all R.sup.20 are not simultaneously hydrogen.

[0159] Without being bound by any particular theory, compounds of formula (XII) minimize color drift by reducing overall copper complex color and/or by favoring Cu.sup.1+ tetrahedral geometry over Cu.sup.2+ octahedral geometry and/or by providing sterics and hydrophobicity to limit access of water to the copper ion and thereby inhibit oxidation. Without being bound by any particular theory, compounds of formula (XII) accelerate reaching color endpoint by enhancing the solubility of Cu.sup.1+.

[0160] In yet another example, a copper-coordinating additive may be selected from the group consisting of a crown ether, an aza-crown ether, a salen ligand, and substituted derivatives thereof.

[0161] In some examples, the copper-containing material and copper-coordinating additive are present, combined, in an amount in the range of from about 0.01% weight/weight of the carrier to about 20% weight/weight of the carrier, including, but not limited to, from about 0.01% weight/weight of the carrier to about 19% weight/weight of the carrier, from about 0.01% weight/weight of the carrier to about 18% weight/weight of the carrier, from about 0.01% weight/weight of the carrier to about 17% weight/weight of the carrier, from about 0.01% weight/weight of the carrier to about 16% weight/weight of the carrier, from about 0.01% weight/weight of the carrier to about 15% weight/weight of the carrier, from about 0.01% weight/weight of the carrier to about 14% weight/weight of the carrier, from about 0.01% weight/weight of the carrier to about 13% weight/weight of the carrier, from about 0.01% weight/weight of the carrier to about 12% weight/weight of the carrier, from about 0.01% weight/weight of the carrier to about 11% weight/weight of the carrier, from about 0.01% weight/weight of the carrier to about 10% weight/weight of the carrier, from about 0.01% weight/weight of the carrier to about 9% weight/weight of the carrier, from about 0.01% weight/weight of the carrier to about 8% weight/weight of the carrier, from about 0.01% weight/weight of the carrier to about 7% weight/weight of the carrier, from about 0.01% weight/weight of the carrier to about 6% weight/weight of the carrier, from about 0.01% weight/weight of the carrier to about 5% weight/weight of the carrier, from about 0.01% weight/weight of the carrier to about 4.9% weight/of the carrier, from about 0.01% weight/weight of the carrier to about 4.8% weight/weight of the carrier, from about 0.01% weight/weight of the carrier to about 4.7% weight/weight of the carrier, from about 0.01% weight/weight of the carrier to about 4.6% weight/weight of the carrier, from about 0.01% weight/weight of the carrier to about 4.5% weight/weight of the carrier, from about 0.01% weight/weight of the carrier to about 4.4% weight/weight of the carrier, from about 0.01% weight/weight of the carrier to about 4.3% weight/weight of the carrier, from about 0.01% weight/weight of the carrier to about 4.2% weight/weight of the carrier, from about 0.01% weight/weight of the carrier to about 4.1% weight/weight of the carrier, from about 0.01% weight/weight of the carrier to about 4.0% weight/weight of the carrier, from about 0.01% weight/weight of the carrier to about 3.9% weight/weight of the carrier, from about 0.01% weight/weight of the carrier to about 3.8% weight/weight of the carrier, from about 0.01% weight/weight of the carrier to about 3.7% weight/weight of the carrier, from about 0.01% weight/weight of the carrier to about 3.6% weight/weight of the carrier, from about 0.01% weight/weight of the carrier to about 3.5% weight/weight of the carrier, from about 0.01% weight/weight of the carrier to about 3.4% weight/weight of the carrier, from about 0.01% weight/weight of the carrier to about 3.3% weight/weight of the carrier, from about 0.01% weight/weight of the carrier to about 3.2% weight/weight of the carrier, from about 0.01% weight/weight of the carrier to about 3.1% weight/weight of the carrier, from about 0.01% weight/weight of the carrier to about 3.0% weight/weight of the carrier, from about 0.01% weight/weight of the carrier to about 2.9% weight/weight of the carrier, from about 0.01% weight/weight of the carrier to about 2.8% weight/weight of the carrier, from about 0.01% weight/weight of the carrier to about 2.7% weight/weight of the carrier, from about 0.01% weight/weight of the carrier to about 2.6% weight/weight of the carrier, from about 0.01% weight/weight of the carrier to about 2.5% weight/weight of the carrier, from about 0.01% weight/weight of the carrier to about 2.4% weight/weight of the carrier, from about 0.01% weight/weight of the carrier to about 2.3% weight/weight of the carrier, from about 0.01% weight/weight of the carrier to about 2.2% weight/weight of the carrier, from about 0.01% weight/weight of the carrier to about 2.1% weight/weight of the carrier, from about 0.01% weight/weight of the carrier to about 2.0% weight/weight of the carrier, from about 0.01% weight/weight of the carrier to about 1.9% weight/weight of the carrier, from about 0.01% weight/weight of the carrier to about 1.8% weight/weight of the carrier, from about 0.01% weight/weight of the carrier to about 1.7% weight/weight of the carrier, from about 0.01% weight/weight of the carrier to about 1.6% weight/weight of the carrier, from about 0.01% weight/weight of the carrier to about 1.5% weight/weight of the carrier, from about 0.01% weight/weight of the carrier to about 1.4% weight/weight of the carrier, from about 0.01% weight/weight of the carrier to about 1.3% weight/weight of the carrier, from about 0.01% weight/weight of the carrier to about 1.2% weight/weight of the carrier, from about 0.01% weight/weight of the carrier to about 1.1% weight/weight of the carrier, from about 0.01% weight/weight of the carrier to about 1.0% weight/weight of the carrier, from about 0.01% weight/weight of the carrier to about 0.9% weight/weight of the carrier, from about 0.01% weight/weight of the carrier to about 0.8% weight/weight of the carrier, from about 0.01% weight/weight of the carrier to about 0.7% weight/weight of the carrier, from about 0.01% weight/weight of the carrier to about 0.6% weight/weight of the carrier, from about 0.01% weight/weight of the carrier to about 0.5% weight/weight of the carrier, from about 0.01% weight/weight of the carrier to about 0.4% weight/weight of the carrier, from about 0.01% weight/weight of the carrier to about 0.3% weight/weight of the carrier, from about 0.01% weight/weight of the carrier to about 0.2% weight/weight of the carrier, from about 0.01% weight/weight of the carrier to about 0.1% weight/weight of the carrier, from about 0.02% weight/weight of the carrier to about 5.0% weight/weight of the carrier, from about 0.03% weight/weight of the carrier to about 5.0% weight/weight of the carrier, from about 0.04% weight/weight of the carrier to about 5.0% weight/weight of the carrier, from about 0.05% weight/weight of the carrier to about 5.0% weight/weight of the carrier, from about 0.06% weight/weight of the carrier to about 5.0% weight/weight of the carrier, from about 0.07% weight/weight of the carrier to about 5.0% weight/weight of the carrier, from about 0.08% weight/weight of the carrier to about 5.0% weight/weight of the carrier, from about 0.09% weight/weight of the carrier to about 5.0% weight/weight of the carrier, from about 0.1% weight/weight of the carrier to about 5.0% weight/weight of the carrier, from about 0.2% weight/weight of the carrier to about 5.0% weight/weight of the carrier, from about 0.3% weight/weight of the carrier to about 5.0% weight/weight of the carrier, from about 0.4% weight/weight of the carrier to about 5.0% weight/weight of the carrier, from about 0.5% weight/weight of the carrier to about 5.0% weight/weight of the carrier, from about 0.6% weight/weight of the carrier to about 5.0% weight/weight of the carrier, from about 0.7% weight/weight of the carrier to about 5.0% weight/weight of the carrier, from about 0.8% weight/weight of the carrier to about 5.0% weight/weight of the carrier, from about 0.9% weight/weight of the carrier to about 5.0% weight/weight of the carrier, from about 1.0% weight/weight of the carrier to about 5.0% weight/weight of the carrier, from about 6% weight/weight of the carrier to about 20% weight/weight of the carrier, from about 7% weight/weight of the carrier to about 20% weight/weight of the carrier, from about 8% weight/weight of the carrier to about 20% weight/weight of the carrier, from about 9% weight/weight of the carrier to about 20% weight/weight of the carrier, from about 10% weight/weight of the carrier to about 20% weight/weight of the carrier, from about 11% weight/weight of the carrier to about 20% weight/weight of the carrier, from about 12% weight/weight of the carrier to about 20% weight/weight of the carrier, from about 13% weight/weight of the carrier to about 20% weight/weight of the carrier, from about 14% weight/weight of the carrier to about 20% weight/weight of the carrier, from about 15% weight/weight of the carrier to about 20% weight/weight of the carrier, from about 16% weight/weight of the carrier to about 20% weight/weight of the carrier, from about 17% weight/weight of the carrier to about 20% weight/weight of the carrier, from about 18% weight/weight of the carrier to about 20% weight/weight of the carrier, or from about 19% weight/weight of the carrier to about 20% weight/weight of the carrier.

[0162] In one or more examples, the copper-containing material and copper-coordinating additive are present, combined, in an amount of about 150 grams per gallon of carrier or less, about 125 g/gallon of carrier or less, about 75 g/gallon of carrier or less, or about 50 g/gallon of carrier or less.

[0163] In some examples, the copper-containing material and copper-coordinating additive are present, combined, in an amount in the range of from about 1 g/gallon of carrier to about 150 g/gallon of carrier, from about 1 g/gallon of carrier to about 125 g/gallon of carrier, from about 1 g/gallon of carrier to about 100 g/gallon of carrier, from about 1 g/gallon of carrier to about 75 g/gallon of carrier, from about 1 g/gallon of carrier to about 50 g/gallon of carrier, from about 1 g/gallon of carrier to about 40 g/gallon of carrier, from about 1 g/gallon of carrier to about 30 g/gallon of carrier, from about 1 g/gallon of carrier to about 20 g/gallon of carrier, from about 1 g/gallon of carrier to about 10 g/gallon of carrier, from about 2 g/gallon of carrier to about 150 g/gallon of carrier, from about 2 g/gallon of carrier to about 125 g/gallon of carrier, from about 2 g/gallon of carrier to about 100 g/gallon of carrier, from about 2 g/gallon of carrier to about 75 g/gallon of carrier, from about 2 g/gallon of carrier to about 50 g/gallon of carrier, from about 3 g/gallon of carrier to about 150 g/gallon of carrier, from about 3 g/gallon of carrier to about 125 g/gallon of carrier, from about 3 g/gallon of carrier to about 100 g/gallon of carrier, from about 3 g/gallon of carrier to about 75 g/gallon of carrier, from about 3 g/gallon of carrier to about 50 g/gallon of carrier, from about 4 g/gallon of carrier to about 150 g/gallon of carrier, from about 4 g/gallon of carrier to about 125 g/gallon of carrier, from about 4 g/gallon of carrier to about 100 g/gallon of carrier, from about 4 g/gallon of carrier to about 75 g/gallon of carrier, from about 4 g/gallon of carrier to about 50 g/gallon of carrier, from about 4 g/gallon of carrier to about 40 g/gallon of carrier, from about 4 g/gallon of carrier to about 30 g/gallon of carrier, from about 4 g/gallon of carrier to about 20 g/gallon of carrier, from about 4 g/gallon of carrier to about 10 g/gallon of carrier, from about 5 g/gallon of carrier to about 150 g/gallon of carrier, from about 5 g/gallon of carrier to about 125 g/gallon of carrier, from about 5 g/gallon of carrier to about 100 g/gallon of carrier, from about 5 g/gallon of carrier to about 75 g/gallon of carrier, from about 5 g/gallon of carrier to about 50 g/gallon of carrier, from about 10 g/gallon of carrier to about 150 g/gallon of carrier, from about 10 g/gallon of carrier to about 125 g/gallon of carrier, from about 10 g/gallon of carrier to about 100 g/gallon of carrier, from about 10 g/gallon of carrier to about 75 g/gallon of carrier, from about 10 g/gallon of carrier to about 50 g/gallon of carrier, from about 15 g/gallon of carrier to about 150 g/gallon of carrier, from about 15 g/gallon of carrier to about 125 g/gallon of carrier, from about 15 g/gallon of carrier to about 100 g/gallon of carrier, from about 15 g/gallon of carrier to about 75 g/gallon of carrier, from about 15 g/gallon of carrier to about 50 g/gallon of carrier, from about 20 g/gallon of carrier to about 150 g/gallon of carrier, from about 20 g/gallon of carrier to about 125 g/gallon of carrier, from about 20 g/gallon of carrier to about 100 g/gallon of carrier, from about 20 g/gallon of carrier to about 75 g/gallon of carrier, from about 20 g/gallon of carrier to about 50 g/gallon of carrier, from about 30 g/gallon of carrier to about 150 g/gallon of carrier, from about 30 g/gallon of carrier to about 125 g/gallon of carrier, from about 30 g/gallon of carrier to about 100 g/gallon of carrier, from about 30 g/gallon of carrier to about 75 g/gallon of carrier, from about 30 g/gallon of carrier to about 50 g/gallon of carrier, from about 50 g/gallon of carrier to about 150 g/gallon of carrier, from about 50 g/gallon of carrier to about 125 g/gallon of carrier, from about 50 g/gallon of carrier to about 100 g/gallon of carrier, from about 50 g/gallon of carrier to about 75 g/gallon of carrier, from about 6 g/gallon of carrier to about 75 g/gallon of carrier, from about 6 g/gallon of carrier to about 50 g/gallon of carrier, from about 7 g/gallon of carrier about 75 g/gallon of carrier, from about 7 g/gallon of carrier to about 50 g/gallon of carrier, from about 8 g/gallon of carrier to about 75 g/gallon of carrier, from about 8 g/gallon of carrier to about 50 g/gallon of carrier, from about 9 g/gallon of carrier to about 75 g/gallon of carrier, from about 9 g/gallon of carrier to about 50 g/gallon of carrier, from about 10 g/gallon of carrier to about 60 g/gallon of carrier, from about 10 g/gallon of carrier to about 40 g/gallon of carrier, from about 10 g/gallon of carrier to about 20 g/gallon of carrier, from about 20 g/gallon of carrier to about 40 g/gallon of carrier, from about 20 g/gallon of carrier to about 30 g/gallon of carrier, from about 35 g/gallon of carrier to about 50 g/gallon of carrier, or from about 40 g/gallon of carrier to about 50 g/gallon of carrier.

[0164] In some examples, the molar ratio of the extractable copper in the copper-containing material to the copper-coordinating additive may be from 1:1 to 1:50, from 1:1 to 1:49, from 1:1 to 1:48, from 1:1 to 1:47, from 1:1 to 1:46, from 1:1 to 1:45, from 1:1 to 1:44, from 1:1 to 1:43, from 1:1 to 1:42, from 1:1 to 1:41, from 1:1 to 1:40, from 1:1 to 1:39, from 1:1 to 1:38, from 1:1 to 1:37, from 1:1 to 1:36, from 1:1 to 1:35, from 1:1 to 1:34, from 1:1 to 1:33, from 1:1 to 1:32, from 1:1 to 1:31, from 1:1 to 1:30, from 1:1 to 1:29, from 1:1 to 1:28, from 1:1 to 1:27, from 1:1 to 1:26, from 1:1 to 1:25, from 1:1 to 1:24, from 1:1 to 1:23, from 1:1 to 1:22, from 1:1 to 1:21, from 1:1 to 1:20, from 1:1 to 1:19, from 1:1 to 1:18, from 1:1 to 1:17, from 1:1 to 1:16, from 1:1 to 1:15, from 1:1 to 1:14.9, from 1:1 to 1:14.8, from 1:1 to 1:14.7, from 1:1 to 1:14.6, from 1:1 to 1:14.5, from 1:1 to 1:14.4, from 1:1 to 1:14.3, from 1:1 to 1:14.2, from 1:1 to 1:14.1, from 1:1 to 1:14.0, from 1:1 to 1:13.9, from 1:1 to 1:13.8, from 1:1 to 1:13.7, from 1:1 to 1:13.6, from 1:1 to 1:13.5, from 1:1 to 1:13.4, from 1:1 to 1:13.3, from 1:1 to 1:13.2, from 1:1 to 1:13.1, from 1:1 to 1:13.0, from 1:1 to 1:12.9, from 1:1 to 1:12.8, from 1:1 to 1:12.7, from 1:1 to 1:12.6, from 1:1 to 1:12.5, from 1:1 to 1:12.4, from 1:1 to 1:12.3, from 1:1 to 1:12.2, from 1:1 to 1:12.1, from 1:1 to 1:12.0, from 1:1 to 1:11.9, from 1:1 to 1:11.8, from 1:1 to 1:11.7, from 1:1 to 1:11.6, from 1:1 to 1:11.5, from 1:1 to 1:11.4, from 1:1 to 1:11.3, from 1:1 to 1:11.2, from 1:1 to 1:11.1, from 1:1 to 1:11.0, from 1:1 to 1:10.9, from 1:1 to 1:10.8, from 1:1 to 1:10.7, from 1:1 to 1:10.6, from 1:1 to 1:10.5, from 1:1 to 1:10.4, from 1:1 to 1:10.3, from 1:1 to 1:10.2, from 1:1 to 1:10.1, from 1:1 to 1.10.0, from 1:1 to 1:9.9, from 1:1 to 1:9.8, from 1:1 to 1:9.7, from 1:1 to 1:9.6, from 1:1 to 1:9.5, from 1:1 to 1:9.4, from 1:1 to 1:9.3, from 1:1 to 1:9.2, from 1:1 to 1:9.1, from 1.1 to 1:9.0, from 1:1 to 1:8.9, from 1:1 to 1:8.8, from 1:1 to 1:8.7, from 1:1 to 1:8.6, from 1:1 to 1:8.5, from 1:1 to 1:8.4, from 1:1 to 1:8.3, from 1:1 to 1:8.2, from 1:1 to 1:8.1, from 1:1 to 1:8.0, from 1:1 to 1:7.9, from 1:1 to 1:7.8, from 1:1 to 1:7.7, from 1:1 to 1:7.6, from 1:1 to 1:7.5, from 1:1 to 1:7.4, from 1:1 to 1:7.3, from 1:1 to 1:7.2, from 1:1 to 1:7.1, from 1:1 to 1:7.0, from 1:1 to 1:6.9, from 1:1 to 1:6.8, from 1:1 to 1:6.7, from 1:1 to 1:6.6, from 1:1 to 1:6.5, from 1:1 to 1:6.4, from 1:1 to 1:6.3, from 1:1 to 1:6.2, from 1:1 to 1:6.1, from 1:1 to 1:6.0, from 1:1 to 1:5.9, from 1:1 to 1:5.8, from 1:1 to 1:5.7, from 1:1 to 1:5.6, from 1:1 to 1:5.5, from 1:1 to 1:5.4, from 1:1 to 1:5.3, from 1:1 to 1:5.2, from 1:1 to 1:5.1, from 1:1 to 1:5.0, from 1:1 to 1:4.9, from 1:1 to 1:4.8, from 1:1 to 1:4.7, from 1:1 to 1:4.6, from 1:1 to 1:4.5, from 1:1 to 1:4.4, from 1:1 to 1:4.3, from 1:1 to 1:4.2, from 1:1 to 1:4.1, from 1:1 to 1:4.0, from 1:1 to 1:3.9, from 1:1 to 1:3.8, from 1:1 to 1:3.7, from 1:1 to 1:3.6, from 1:1 to 1:3.5, from 1:1 to 1:3.4, from 1:1 to 1:3.3, from 1:1 to 1:3.2, from 1:1 to 1:3.1, from 1:1 to 1:3.0, from 1:1 to 1:2.9, from 1:1 to 1:2.8, from 1:1 to 1:2.7, from 1:1 to 1:2.6, from 1:1 to 1:2.5, from 1:1 to 1:2.4, from 1:1 to 1:2.3, from 1:1 to 1:2.2, from 1:1 to 1:2.1, from 1:1 to 1:2.0, from 1:1 to 1:1.9, from 1:1 to 1:1.8, from 1:1 to 1:1.7, from 1:1 to 1:1.6, from 1:1 to 1:1.5, from 1:1 to 1:1.4, from 1:1 to 1:1.3, from 1:1 to 1:1.2, from 1:1 to 1:1.1, from 1:1 to 1:0.9, from 1:1 to 1:0.8, from 1:1 to 1:0.7, from 1:1 to 1:0.6, from 1:1 to 1:0.5, from 1:1 to 1:0.4, from 1:1 to 1:0.3, from 1:1 to 1:0.2, from 1:1 to 1:0.1, from 50:1 to 1:1, from 49:1 to 1:1, from 48:1 to 1:1, from 47:1 to 1:1, from 46:1 to 1:1, from 45:1 to 1:1, from 44:1 to 1:1, from 43:1 to 1:1, from 42:1 to 1:1, from 41:1 to 1:1, from 40:1 to 1:1, from 39:1 to 1:1, from 38:1 to 1:1, from 37:1 to 1:1, from 36:1 to 1:1, from 35:1 to 1:1, from 34:1 to 1:1, from 33:1 to 1:1, from 32:1 to 1:1, from 31:1 to 1:1, from 30:1 to 1:1, from 29:1 to 1:1, from 28:1 to 1:1, from 27:1 to 1:1, from 26:1 to 1:1, from 25:1 to 1:1, from 24:1 to 1:1, from 23:1 to 1:1, from 22:1 to 1:1, from 21:1 to 1:1, from 20:1 to 1:1, from 19:1 to 1:1, from 18:1 to 1:1, from 17:1 to 1:1, from 16:1 to 1:1, from 15:1 to 1:1, from 14.9:1 to 1:1, from 14.8:1 to 1:1, from 14.7:1 to 1:1, from 14.6:1 to 1:1, from 14.5:1 to 1:1, from 14.4:1 to 1:1, from 14.3:1 to 1:1, from 14.2:1 to 1:1, from 14.1:1 to 1:1, from 14.0:1 to 1:1, from 13.9:1 to 1:1, from 13.8:1 to 1:1, from 13.7:1 to 1:1, from 13.6:1 to 1:1, from 13.5:1 to 1:1, from 13.4:1 to 1:1, from 13.3:1 to 1:1, from 13.2:1 to 1:1, from 13.1:1 to 1:1, from 13.0:1 to 1:1, from 12.9:1 to 1:1, from 12.8:1 to 1:1, from 12.7:1 to 1:1, from 12.6:1 to 1:1, from 12.5:1 to 1:1, from 12.4:1 to 1:1, from 12.3:1 to 1:1, from 12.2:1 to 1:1, from 12.1:1 to 1:1, from 12.0:1 to 1:1, from 11.9:1 to 1:1, from 11.8:1 to 1:1, from 11.7:1 to 1:1, from 11.6:1 to 1:1, from 11.5:1 to 1:1, from 11.4:1 to 1:1, from 11.3:1 to 1:1, from 11.2:1 to 1:1, from 11.1:1 to 1:1, from 11.0:1 to 1:1, from 10.9:1 to 1:1, from 10.8:1 to 1:1, from 10.7:1 to 1:1, from 10.6:1 to 1:1, from 10.5:1 to 1:1, from 10.4:1 to 1:1, from 10.3:1 to 1:1, from 10.2:1 to 1:1, from 10.1:1 to 1:1, from 10.0:1 to 1:1, from 9.9:1 to 1:1, from 9.8:1 to 1:1, from 9.7:1 to 1:1, from 9.6:1 to 1:1, from 9.5:1 to 1:1, from 9.4:1 to 1:1, from 9.3:1 to 1:1, from 9.2:1 to 1:1, from 9.1:1 to 1:1, from 9.0:1 to 1:1, from 8.9:1 to 1:1, from 8.8:1 to 1:1, from 8.7:1 to 1:1, from 8.6:1 to 1:1, from 8.5:1 to 1:1, from 8.4:1 to 1:1, from 8.3:1 to 1:1, from 8.2:1 to 1:1, from 8.1:1 to 1:1, from 8.0:1 to 1:1, from 7.9:1 to 1:1, from 7.8:1 to 1:1, from 7.7:1 to 1:1, from 7.6:1 to 1:1, from 7.5:1 to 1:1, from 7.4:1 to 1:1, from 7.3:1 to 1:1, from 7.2:1 to 1:1, from 7.1 to 1:1, from 7.0 to 1:1, from 6.9:1 to 1:1, from 6.8:1 to 1:1, from 6.7:1 to 1:1, from 6.6:1 to 1:1, from 6.5:1 to 1:1, from 6.4:1 to 1:1, from 6.3:1 to 1:1, from 6.2:1 to 1:1, from 6.1:1 to 1:1, from 6.0:1 to 1:1, from 5.9:1 to 1:1, from 5.8:1 to 1:1, from 5.7:1 to 1:1, from 5.6:1 to 1:1, from 5.5:1 to 1:1, from 5.4:1 to 1:1, from 5.3:1 to 1:1, from 5.2:1 to 1:1, from 5.1:1 to 1:1, from 5.0:1 to 1:1, from 4.9:1 to 1:1, from 4.8:1 to 1:1, from 4.7:1 to 1:1, from 4.6:1 to 1:1, from 4.5:1 to 1:1, from 4.4:1 to 1:1, from 4.3:1 to 1:1, from 4.2:1 to 1:1, from 4.1:1 to 1:1, from 4.0:1 to 1:1, from 3.9:1 to 1:1, from 3.8:1 to 1:1, from 3.7:1 to 1:1, from 3.6:1 to 1:1, from 3.5:1 to 1:1, from 3.4:1 to 1:1, from 3.3:1 to 1:1, from 3.2:1 to 1:1, from 3.1:1 to 1:1, from 3.0:1 to 1:1, from 2.9:1 to 1:1, from 2.8:1 to 1:1, to 2.7:1 to 1:1, from 2.6:1 to 1:1, from 2.5:1 to 1:1, from 2.4:1 to 1:1, from 2.3:1 to 1:1, from 2.2:1 to 1:1, from 2.1:1 to 1:1, from 2.0:1 to 1:1, from 1.9:1 to 1:1, from 1.8:1 to 1:1, from 1.7:1 to 1:1, from 1.6:1 to 1:1, from 1.5:1 to 1:1, from 1.4:1 to 1:1, from 1.3:1 to 1:1, from 1.2:1 to 1:1, from 1.1:1 to 1:1, from 0.9:1 to 1:1, from 0.8:1 to 1:1, from 0.7:1 to 1:1, from 0.6:1 to 1:1, from 0.5:1 to 1:1, from 0.4:1 to 1:1, from 0.3:1 to 1:1, from 0.2:1 to 1:1, or from 0.1:1 to 1:1.

[0165] Upon combination of the copper-containing material and the copper-coordinating additive with a carrier, as described herein, the composition or resulting material may be formed into a desired article or be applied to a surface. Where the composition includes paint, the paint may be applied to a surface as a layer. Examples of such articles that may be formed using the composition described herein include housings for electronic devices (e.g., mobile phones, smart phones, tablets, video players, information terminal devices, laptop computers, etc.), architectural structures (e.g., countertops, walls, trim, ceilings, floors, exterior facades, and trim), appliances (e.g., cooktops, refrigerator and dishwasher doors, etc.), information displays (e.g., whiteboards), and automotive components (e.g., dashboard panels, windshields, window components, etc.).

[0166] The compositions described herein may include pigments to impart color. Accordingly, the coatings or layers made from such compositions may exhibit a wide variety of colors, depending on the carrier color, mixture of carriers, and amount of particle loading. Moreover, the compositions and/or coatings described herein showed no adverse effect to paint adhesion as measured by ASTM D4541. In some instances, the adhesion of the composition or coating to an underlying substrate was greater than the cohesive strength of the substrate. In other words, in testing, the adhesion between the coating and the substrate was so strong that the underlying substrate failed before the coating was separated from the surface of the substrate.

[0167] One or more examples of the compositions may include the copper-containing material, which may be pre-treated with a pretreatment solution, a copper-coordinating additive, and a carrier with a loading level of the copper-containing material such that the material exhibits resistance or preservation against the presence or growth of foulants. Foulants include fungi, bacteria, viruses, mold, mildew, algae, and combinations thereof. In some instances, the presence of foulants in materials, such as paints, varnishes, and the like may cause color changes to the composition, may degrade the integrity of the composition, and may negatively affect various properties of the composition. By including a minimum loading of copper-containing material (e.g., about 5 weight % or less, about 4 weight % or less, about 3 weight % or less, about 2 weight percent or less, or about 1 weight % or less) and copper-coordinating additive to the carrier, the foulants may be eliminated or reduced. In some instances, the compositions need not include certain components, when fouling is eliminated or reduced. Thus, the formulations used in one or more examples of the compositions described herein may have more flexibility and variations than previously possible, when used in known compositions that do not include the copper-containing material.

[0168] According to examples of the present disclosure, the biocidal composition may include a carrier, a copper-coordinating additive, and a copper-containing material that has been pre-treated with a pretreatment solution prior to combining the copper-containing material with the copper-coordinating additive and the carrier. A copper-containing material that has been pretreated with a pretreatment solution may be referred to as treated copper-containing material. The treated copper-containing material may be present in the pretreatment solution (e.g., dissolved and/or suspended therein), which may then be combined with the copper-coordinating additive and the carrier, optionally without an intermediate step to separate the treated copper-containing material from the pretreatment solution.

[0169] In some examples, the pretreatment solution may contain an ammonia-based material, examples of which may include ammonia and ammonium buffers. For example, the pretreatment solution may include ammonium chloride and/or ammonium phosphate. The ammonium buffers may be made using any suitable material or combination of materials to provide an ammonium buffer having the desired pH, examples of which include ammonium phosphate monobasic, ammonium phosphate dibasic, monoammonium phosphate (NH.sub.4H.sub.2PO.sub.4), ammonium carbonate, and ammonium hydroxide.

[0170] In some examples, the pretreatment solution may contain an ammonia-based and/or amine-based solution having a pH of from 8 to about 12, from about 8 to about 11, from about 8 to about 10, from about 8 to about 9, from about 9 to about 12, from about 9 to about 11, from about 9 to about 10, from about 10 to about 12.

[0171] In some examples, the pretreatment solution may contain a group (I) hydroxide and/or a group (II) hydroxide. In some examples, the pretreatment solution may contain a hard base, examples of which include potassium hydroxide and sodium hydroxide. The group (I) hydroxide, group (II) hydroxides, and/or hard base may be used alone or in combination with other materials to provide a pretreatment solution adapted to react with copper when used to treat the copper-containing material. In some examples, the group (I) hydroxides, group (II) hydroxides, and/or hard base are used to form a pre-treatment solution having a pH of at least 9.

[0172] In some examples, the pretreatment solution may be an alkaline buffer containing one or more components that provide a desired pH and/or a desired chemical group (e.g., an amine-based or ammonium-based group). Examples of suitable alkaline buffers include phosphate buffers, borate buffers, ammonium buffers, carbonate buffers, and combinations thereof. For example, the alkaline buffer may include ammonium phosphate monobasic, potassium phosphate monobasic, ammonium phosphate dibasic, monoammonium phosphate (NH.sub.4H.sub.2PO.sub.4), ammonium carbonate, ammonium hydroxide, boric acid, sodium borate, potassium chloride, sodium hydroxide, dihydrogen potassium phosphate, sodium phosphate dibasic, sodium phosphate monobasic, sodium phosphate tribasic, potassium phosphate tribasic, phosphoric acid, potassium phosphate dibasic, potassium phosphate monobasic, sodium carbonate, ammonium carbonate, potassium bicarbonate, sodium bicarbonate, and ammonium bicarbonate. In one example, the alkaline buffer may contain dihydrogen potassium phosphate and sodium phosphate dibasic. In another example, the alkaline buffer may contain potassium phosphate monobasic and sodium hydroxide. In yet another example, the alkaline buffer may contain boric acid, potassium chloride, and sodium hydroxide. In yet another example, the alkaline buffer may contain ammonium chloride, ammonium phosphate monobasic, and potassium phosphate monobasic. In some examples, the alkaline buffer has a pH of at least 9. For example, the alkaline buffer may have a pH of at least 9, at least 9.5, at least 10, at least 10.5, or at least 11. In some examples, the alkaline buffer may have a pH of from about 9 to about 12, from about 9.5 to about 12, from about 10 to about 12, from about 10.5 to about 12, from about 11 to about 12, from about 9 to about 11.5, from about 9.5 to about 11.5, from about 10 to about 11.5, from about 10.5 to about 11.5, from about 11 to about 11.5, from about 9 to about 11, from about 9.5 to about 11, from about 10 to about 11, from about 10.5 to about 11, from about 9 to about 10.5, from about 9.5 to about 10.5, from about 10 to about 10.5, from about 9 to about 10, or from about 9.5 to about 10.

[0173] The pretreatment solution may have a pH of between about 7 and about 12. For example, the pretreatment solution may have a pH of between about 8 and about 12, or between about 8.5 and about 10.5. In some examples, the pretreatment solution may have a pH of from about 7 to about 12, from about 7 to about 11.5, from about 7 to about 11, from about 7 to about 10.5, from about 7 to about 10, from about 7 to about 9.5, from about 7 to about 9, from about 7 to about 8, from about 7.5 to about 12, from about 7.5 to about 11.5, from about 7.5 to about 11, from about 7.5 to about 10.5, from about 7.5 to about 10, from about 7.5 to about 9.5, from about 7.5 to about 9, from about 7.5 to about 8, from about 8 to about 12, from about 8 to about 11.5, from about 8 to about 11, from about 8 to about 10.5, from about 8 to about 10, from about 8 to about 9.5, from about 8 to about 9, from about 8.5 to about 12, from about 8.5 to about 11.5, from about 8.5 to about 11, from about 8.5 to about 10.5, from about 8.5 to about 10, from about 8.5 to about 9.5, from about 8.5 to about 9, from about 9 to about 12, from about 9 to about 11.5, from about 9 to about 11, from about 9 to about 10.5, from about 9 to about 10, from about 9 to about 9.5, from about 9.5 to about 12, from about 9.5 to about 11.5, from about 9.5 to about 11, from about 9.5 to about 10.5, from about 9.5 to about 10, from about 10 to about 12, from about 10 to about 11.5, or from about 10 to about 11.

[0174] In some examples, an amount and/or a pH of the pretreatment solution may be selected such that a pH of the combined mixture of the carrier and the copper-coordinating additive and the treated copper-containing material (e.g., the copper-containing material that has been already been treated with the pretreatment solution) is within a predetermined range of an initial pH of the carrier (e.g., the pH of the carrier prior to combining with the treated copper-containing material). For example, in some examples, an amount and/or a pH of the pretreatment solution used to treat the copper-containing material may be selected such that the pH of the mixture of the carrier and the copper-coordinating additive and the treated copper-containing material is within 1 units of the initial pH of the carrier. In some examples, an amount and/or a pH of the pretreatment solution used to treat the copper-containing material may be selected such that the pH of the mixture of the carrier and the copper-coordinating additive and the treated copper-containing material is within 0.5, or even 0.3 units of the initial pH of the carrier. Without wishing to be limited by any theory, it is believed that in some applications, the addition of a solution or a suspension of treated copper-containing material that significantly affects the total volume and/or pH of the carrier may result in an undesirable change in one or more characteristics of the carrier. For example, when the carrier is a paint, large changes in volume and/or pH following the addition of the treated copper-containing material may undesirably affect other components of the paint or properties of the paint, such as the color or dispersion of one or more materials in the paint (e.g., pigment dispersion).

[0175] The copper-containing material may be treated in the pretreatment solution for any amount of time, for example, between about 5 minutes and about 24 hours, or between about 1 hour and about 12 hours, and all ranges and sub-ranges therebetween. In some examples, the copper-containing material may be pretreated in the pretreatment solution for greater than 5 minutes, greater than 10 minutes, greater than 1 hour, greater than 2 hours, greater than 5 hours, greater than 10 hours, greater than 15 hours, greater than 20 hours, greater than 24 hours, or greater than 48 hours. For example, the copper-containing material may be pretreated in the pretreatment solution for from about 5 minutes to about 72 hours, from about 5 minutes to about 48 hours, from about 5 minutes to about 36 hours, from about 5 minutes to about 24 hours, from about 5 minutes to about 20 hours, from about 5 minutes to about 10 hours, from about 5 minutes to about 5 hours, from about 5 minutes to about 2 hours, from about 10 minutes to about 72 hours, from about 10 minutes to about 48 hours, from about 10 minutes to about 36 hours, from about 10 minutes to about 24 hours, from about 10 minutes to about 20 hours, from about 10 minutes to about 10 hours, from about 10 minutes to about 5 hours, from about 10 minutes to about 2 hours, from about 60 minutes to about 72 hours, from about 60 minutes to about 48 hours, from about 60 minutes to about 36 hours, from about 60 minutes to about 24 hours, from about 60 minutes to about 20 hours, from about 60 minutes to about 10 hours, from about 60 minutes to about 5 hours, from about 60 minutes to about 2 hours, from about 2 hours to about 72 hours, from about 2 hours to about 48 hours, from about 2 hours to about 36 hours, from about 2 hours to about 24 hours, from about 2 hours to about 20 hours, from about 2 hours to about 10 hours, from about 2 hours to about 5 hours, from about 5 hours to about 72 hours, from about 5 hours to about 48 hours, from about 5 hours to about 36 hours, from about 5 hours to about 24 hours, from about 5 hours to about 20 hours, from about 5 hours to about 10 hours, from about 10 hours to about 72 hours, from about 10 hours to about 48 hours, from about 10 hours to about 36 hours, from about 10 hours to about 24 hours, from about 10 hours to about 20 hours, from about 20 hours to about 72 hours, from about 20 hours to about 48 hours, from about 20 hours to about 36 hours, from about 20 hours to about 24 hours, from about 24 hours to about 72 hours, or from about 24 hours to about 48 hours. In some examples, the copper-containing material may be treated in the pretreatment solution for a predetermined period of time and then immediately combined with the carrier and the copper-coordinating additive. In other examples, the copper-containing material may be treated in the pretreatment solution for a minimum period of time and immediately combined with the carrier and copper-coordinating additive and/or stored for a period of time before combining with the carrier and copper-coordinating additive. In some examples, the mixture of the treated copper-containing material and the pretreatment solution may be combined directly with the carrier and the copper-coordinating additive without an intermediate step to separate the treated copper-containing material from the pretreatment solution. In some examples, following the pretreatment period, the mixture of the treated copper-containing material and the pretreatment solution may be combined with one or more additional materials (e.g., a solvent or additional buffer) prior to combining the mixture with the carrier and the copper-coordinating additive.

[0176] Without wishing to be bound by any particular theory, it is believed that as portions of the copper-containing material dissolve during or after being combined with a carrier and the copper-coordinating additive, more of the compositional components of the copper-containing material are released and become available to interact with the components of the carrier and the copper-coordinating additive. Some of these dissolved components, such as copper ions, may cause changes in a color of the carrier at the time of combining the treated copper-containing material and the copper-coordinating additive and the carrier and/or for a predetermined period of time after combining the treated copper-containing material, the copper-coordinating additive, and the carrier.

[0177] Without wishing to be limited by any theory, it is believed that treated copper-containing material that have been pre-treated with a pretreatment solution as described herein may provide complexing or precipitating agents that, when combined with a carrier and a copper-coordinating additive, may reduce or eliminate the formation of copper-based complexes that would otherwise cause changes to the color of the carrier or may produce a color that does not change substantially. As one example, when a copper-containing material is pretreated with monoammonium phosphate, a copper-based complex of Cu(H.sub.2PO.sub.4).sub.2 and/or Cu(H.sub.2PO.sub.4).sup.2 may be formed, which stabilizes the copper ions released from the copper-containing material and may prevent formation of other copper-based complexes that would otherwise cause changes to the color of the carrier. It is also believed that a copper-containing material, when combined with a carrier and a copper-coordinating additive, may reduce or eliminate the formation of copper-based complexes that would otherwise cause changes to the color of the carrier or may produce a color that does not change substantially.

[0178] In some examples, the formation of a colored solution and/or a precipitate when the copper-containing material or the treated copper-containing material is combined with the copper-coordinating additive may be indicative of an ability of the copper-containing material and the copper-coordinating additive to stabilize the color of the carrier compared to the copper-containing material absent the copper-coordinating additive. Stabilizing the color of the carrier may include decreasing a shift in color of the carrier after mixing and/or decreasing a drift in a color of the carrier over time after mixing and/or increasing a rate of color change such that the color of the mixture stabilizes more quickly (which may involve a large initial change in color). For example, in paint applications, when copper is added to the paint, the copper may affect the color of the paint when initially mixed and/or may affect the color of the paint over time as it is stored and/or after use. In some examples, the copper-containing material combined with the copper-coordinating additive results in a decrease in the color change of the mixture, an initial color change and/or over time, compared to a copper-containing material absent the copper-coordinating additive. In some examples, pretreating the copper-containing material with a pretreatment solution before combining with the copper-coordinating additive and a paint may accelerate the color change of the paint. Accelerating the color change of the paint during the manufacturing process sf the paint may allow the manufacturer to account for the color change induced by the treated copper-containing material and the copper-coordinating additive and thus facilitate providing a final product having a desired color and improved color stability over time. Thus, in some examples, an acceleration in the color change of the carrier when combined with the treated copper-containing material and the copper-coordinating additive may be utilized by manufacturers to account for the color change and adjust accordingly during the manufacturing process. In addition, in some examples, the majority of the color change occurs during the manufacturing process and thus the final paint product may have improved color stability during storage and/or after use. In other examples, the treated copper-containing material and the copper-coordinating additive may result in a decrease in the color change of the carrier and/or an increase in the stability of the color of the carrier over time as compared to the copper-containing material absent the copper-coordinating additive.

[0179] In an example, a method of minimizing a color change in a biocidal material is provided, including: combining a copper-containing material including from 10 to 70 weight % of an amount of extractable copper with an amount of copper-coordinating additive, in a molar ratio of the amount of extractable copper to the amount of copper-coordinating additive of from 1:0.1 to 1:25 to form a copper-containing mixture; and combining the copper-containing mixture with a carrier to form the biocidal material; wherein a concentration of the copper-containing material and the copper-coordinating additive of the copper-containing mixture in the carrier is from 0.01% weight/weight of the carrier to 5% weight/weight of the carrier; and wherein the color change in the biocidal material is minimized relative to a change in color of a mixture of the carrier and the copper-containing material in the absence of the copper-coordinating additive. In another example, a method of minimizing a color change in a carrier of an initial color is provided, wherein the copper-containing material comprises from 25 to 50 weight % of the amount of extractable copper. In yet another example, a method of minimizing a color change in a biocidal material is provided, wherein the copper-coordinating additive is a compound of formula (I), (II), (III), (IV), (V), (XI), or (XII), or a crown ether, an aza-crown ether, or salen. In yet another example, a method of minimizing a color change in a biocidal material is provided, wherein the copper-coordinating additive is a compound selected from the group consisting of 2-ethylhexyl phosphate, bis(2-ethylhexyl)phosphate, methyl phosphate, dimethyl phosphate, phenyl phosphate, diphenyl phosphate, 2,2-bipyridine, terpyridine, citric acid, diethanolamine, triethanolamine, 14-crown-4, 15-crown-5, 18-crown-6, dibenzo-18-crown-6, aza-15-crown-5, aza-18-crown-6, and salen. In yet another example, a method of minimizing a color change in a biocidal material is provided, wherein the composition demonstrates a greater than 3 logarithmic reduction in a concentration of a bacterial selected from the group consisting of Staphylococcus aureus, Enterobacter aerogenes, Pseudomonas aeruginosa, Methicillin Resistant Staphylococcus aureus, E. coli, and mixtures thereof. In yet another example, a method of minimizing a color change in a biocidal material is provided, wherein a CIE E* value of the biocidal material is less than about 10, as measured according to formula (XIII):

[00002] $\begin{matrix} E_{C}^{*} = \sqrt{({(L^{*} - L_{c ontrol}^{*})}^{2} + {(a^{*} - a_{control}^{*})}^{2} + {(b^{*} - b_{c ontrol}^{*})}^{2})} & (XIII) \end{matrix}$

wherein L*, a*, and b* are the CIE L*, a*, and b* values of the biocidal material and the L*.sub.control, a*.sub.control, and b*control are the CIE L*, a*, and b* values of the carrier.

[0180] In an example, a method of accelerating a color endpoint in a biocidal material is provided, including: combining a copper-containing material including from 10 to 70 weight % of an amount of extractable copper with an amount of copper-coordinating additive, in a molar ratio of the amount of extractable copper to the amount of copper-coordinating additive of from 1:0.1 to 1:25 to form a copper-coordinating mixture; and combining the copper-containing mixture with a carrier to form the biocidal material; wherein a concentration of the copper-containing material and the copper-coordinating additive of the copper-containing mixture in the carrier is from 0.01% weight/weight of the carrier to 5% weight/weight of the carrier; and wherein a CIE E* value of the biocidal material is less than about 10, as measured according to formula (XIII):

[00003] $\begin{matrix} E_{C}^{*} = \sqrt{({(L^{*} - L_{c ontrol}^{*})}^{2} + {(a^{*} - a_{control}^{*})}^{2} + {(b^{*} - b_{c ontrol}^{*})}^{2})} & (XIII) \end{matrix}$

wherein L*, a*, and b* are the CIE L*, a*, and b* values of the color endpoint and the L*.sub.control, a*.sub.control, and b*.sub.control are the initial CIE L*, a*, and b* values of the biocidal material; and wherein the color endpoint in the biocidal material is accelerated relative to a change in color to a color endpoint of a mixture of the carrier and the copper-containing material in the absence of the copper-coordinating additive. In another example, a method of accelerating a color endpoint in a biocidal material is provided, wherein the copper-containing material comprises from 25 to 50 weight % of the amount of extractable copper. In yet another example, a method of accelerating a color endpoint in a biocidal material is provided, wherein the copper-coordinating additive is a compound of formula (I), (III), (VI), (VII), (IX), (X), (XI), or (XII), or a crown ether, an aza-crown ether, or salen. In yet another example, a method of accelerating a color endpoint in a biocidal material is provided, wherein the copper-coordinating additive is a compound selected from the group consisting of 2-ethylhexyl phosphate, bis(2-ethylhexyl)phosphate, methyl phosphate, dimethyl phosphate, phenyl phosphate, diphenyl phosphate, citric acid, ethoxyamine hydrochloride, triethyl citrate, thiourea, urea, 14-crown-4, 15-crown-5, 18-crown-6, dibenzo-18-crown-6, aza-15-crown-5, aza-18-crown-6, and salen. In yet another example a method of accelerating a color endpoint in a biocidal material is provided, wherein the composition demonstrates a greater than 3 logarithmic reduction in a concentration of a bacterial selected from the group consisting of Staphylococcus aureus, Enterobacter aerogenes, Pseudomonas aeruginosa, Methicillin Resistant Staphylococcus aureus, E. coli, and mixtures thereof. In yet another example, a method of accelerating a color endpoint in a biocidal material is provided, wherein the method further includes: treating the copper-containing material with a pretreatment solution prior to the combining with the amount of copper-coordinating additive. In yet another example, a method of accelerating a color endpoint in a biocidal material is provided, wherein the copper-coordinating additive is a compound of formula (VIII).

[0181] The compositions and methods described above may be better understood in connection with the following Examples. In addition, the following non-limiting examples are an illustration. The illustrated methods are applicable to other examples of biocidal compositions of the present disclosure. The procedures described as general methods describe what is believed will be typically effective to prepare the compositions indicated. However, the person skilled in the art will appreciate that it may be necessary to vary the procedures for any given example of the present disclosure, e.g., vary the order or steps and/or the chemical reagents used.

Examples

[0182] As used herein, unless otherwise specified, the term color shift, is used to refer to the change of the color of the carrier upon addition of the copper-containing material and/or the chemical additive and compares the color of the mixed carrier and the copper-containing material and/or the chemical additive to the color of the carrier in the absence of the copper-containing material and/or the chemical additive (control). The term color drift is used to refer to the change of the color of the carrier at a predetermined time after addition of the copper-containing material and/or the chemical additive and compares the color of the carrier mixed with the copper-containing material and/or the chemical additive after a predetermined time period to the color of the carrier upon initially being mixed with the copper-containing material and/or the chemical additive (time=0). Color shift and color drift may be reported using E*. Color shift and color drift may be reported in terms of E.sub.c* and E.sub.0* according to formulae (XIII) and (XIV), respectively.

[00004] $\begin{matrix} E_{C}^{*} = \sqrt{({(L^{*} - L_{c ontrol}^{*})}^{2} + {(a^{*} - a_{control}^{*})}^{2} + {(b^{*} - b_{c ontrol}^{*})}^{2})} & (XIII) \end{matrix}$ $and$ $\begin{matrix} E_{0}^{*} = \sqrt{({(L^{*} - L_{0}^{*})}^{2} + {(a^{*} - a_{0}^{*})}^{2} + {(b^{*} - b_{0}^{*})}^{2})} & (XIV) \end{matrix}$

wherein L*, a*, and b* are the CIE L*, a*, and b* values of the mixed carrier material, L*.sub.control, a*.sub.control, and b*.sub.control are the CIE L*, a*, and b* values of the carrier in the absence of the copper-containing material and/or the chemical additive, and L*o, a*o, and b*o are the CIE L*, a*, and b* values of the mixed carrier material at the time of mixing (time=0).

[0183] In some examples, color drift may be reported in terms of an LCh.sup.0 factor. For example, a percent change of the coordinates L*, C*, and h.sup.0 per day may be calculated as the difference between the coordinates measured at the time of adding the copper-containing material and/or the chemical additive to the carrier products and the same coordinates measured at some predetermined time period (e.g., time (t)=72 hours) after adding the copper-containing material and/or the chemical additive to the carrier products to arrive at values for the percent change of the components per day dL*, dC*, and dh.sup.0. Formulae (XV)(XVII) may be used to determine dL*, dC*, and dh.sup.0, respectively:

[00005] $\begin{matrix} {dL}^{*} = ((L_{t}^{*} - L_{0}^{*}) .Math. 24 / (t .Math. L_{0}^{*})) & (XV) \end{matrix}$ $\begin{matrix} {dC}^{*} = ((C_{t}^{*} - C_{0}^{*}) .Math. 24) / (t .Math. C_{0}^{*})) & (XVI) \end{matrix}$ $\begin{matrix} {dh}^{0} = ((h_{t}^{0} - h_{0}^{0}) .Math. 24) / (t .Math. h_{0}^{0})) & (XVII) \end{matrix}$

wherein L.sub.t*, C.sub.t*, and h.sup.0.sub.t are the CIE L*, C*, and h.sup.0.sub.0 values of the mixed carrier material at a predetermined time period after mixing and L.sub.0*, C.sub.0*, and h.sup.0.sub.0 are the CIE L*, C*, and h.sup.0 values of the mixed carrier material at the time of mixing (time=0).

[0184] Color drift may be reported in terms of an LCh.sup.0 factor according to formula (XVIII):

[00006] $\begin{matrix} L C h^{0} = \sqrt{({({dL}^{*})}^{2} + {({dC}^{*})}^{2} + {(d h^{0})}^{2})} & (XVIII) \end{matrix}$ [0185] wherein dL*, dC*, and dh.sup.0 are determined according to formulae (XV)-(XVII) above.

[0186] Representative preparation of biocidal composition samples. In the following examples, a copper-containing material is understood to include extractable copper in an amount from 10 weight % to 70 weight %.

[0187] A copper-containing material (0.504 grams) were mixed with hydroxylamine hydrochloride (0.155 grams, 2.231 mmol) in 2 mL water thoroughly, and allowed to mix for 1 hour until copper was extracted from the copper-containing material and a hydroxylamine-copper complex formed. The mixture was sonicated for 20 to 30 seconds. 50 grams of Control B paint was added to the mixture and agitated with an overhead mixer at 980 rpm for 2 minutes. A drawdown sample was used with a 7 mil (0.007) wet film applicator, which represents the before peroxide comparison example. 2 milliliters of hydrogen peroxide (3%) was added to the paint mixture and stirred until well-mixed. After two hours, a drawdown sample with a 7 mil (0.007) wet film applicator, which represents the after peroxide comparison example.

[0188] The above procedure was performed using the copper-containing material in 1:0.3 and 1:0.6 molar ratios of extractable copper, in the copper-containing material, to phosphate dibasic, in 1:0.5 and 1:1 molar ratios of extractable copper, in the copper-containing material, to 2-ethylhexylphosphate (2EHP), in 1:0.5 and 1:1 molar ratios of extractable copper, in the copper-containing material, to hydroxylamine hydrochloride, and in 1:0.5 and 1:1 molar ratios of extractable copper, in the copper-containing material, to urea. As shown in FIG. 1, total drift in color may be estimated by the gap between paint color before and paint color after peroxide testing. The control (paint dosed with the copper-containing material) results in an a* drift of 2.25 and an endpoint of 2.25. Copper-coordinating additives that reduced color drift included phosphate dibasic (1.75, with endpoint 1.5) and 2EHP (0.25 to 1 of drift, and endpoint of 0.5 to 1). Hydroxylamine hydrochloride and urea did not change the endpoint a*, but reduced drift to 0 for hydroxylamine hydrochloride and 1 for urea. As shown in FIG. 2, copper-coordinating additives do not impact antimicrobial efficacy with the exception of 1:0.6 molar ratio of extractable copper, in the copper-containing material, to phosphate dibasic. All other samples demonstrate antimicrobial efficacy similar to the antimicrobial efficacy of the control sample (the copper-containing material-dosed paint, 50 g/gallon, no copper-coordinating additives).

[0189] Color measurements were performed with a paint film (cured for three days) using an X-Rite VS450 Non-Contact Color Measurement Instrument Spectrophotometer. Three spots of each paint film were measured, and the average reported.

[0190] Similar experiments were performed in which each of phosphate dibasic, 2EHP, hydroxylamine hydrochloride, and urea were added to water and neutralized to a pH of 7. Subsequently, a copper-containing material was added to each neutral solution to prepare samples for color testing with 1:1 and 1:2 molar ratios of extractable copper, in the copper-containing material, to phosphate dibasic, 1:1.5 and 1:3 molar ratios of extractable copper, in the copper-containing material, to 2EHP, 1:1.5 and 1:3 molar ratios of extractable copper, in the copper-containing material, to hydroxylamine hydrochloride, and 1:1.5 and 1:3 molar ratios of extractable copper, in the copper-containing material, to urea. By changing the preparation method slightly, it was found that drift in color was reduced significantly both for 2EHP and for hydroxylamine hydrochloride, as shown in FIG. 3. Further, despite the modified preparation method, antimicrobial efficacy of the test compositions was not impacted, as shown in FIG. 4.

[0191] Experiments were performed using control paint samples, in which each of 2EHP, hydroxylamine hydrochloride, thiourea, and urea were separately added to volumes of water and neutralized to a pH of 7. Subsequently, a copper-containing material was added to each neutral solution to prepare samples for color testing with 1:1 and 1:3 molar ratios of extractable copper, in the copper-containing material, to 2EHP, 1:1 and 1:3 molar ratios of extractable copper, in the copper-containing material, to hydroxylamine hydrochloride, 1:1 and 1:3 molar ratios of extractable copper, in the copper-containing material, to thiourea, and 1:1 and 1:3 molar ratios of extractable copper, in the copper-containing material, to urea. The mixtures were then each combined as above with 50 grams of control paint sample. As shown in FIG. 5, hydroxylamine hydrochloride minimized color drift by accelerating to endpoint quickly, whereas thiourea reduced total color drift, but changed the endpoint color to a higher a* value. 2-Ethylhexylphosphate did not minimize drift as demonstrated in control paint samples, however there was some reduction in drift for 1:3 molar ratio relative to 1:1 molar ratio. As shown in FIG. 6, all copper-coordinating additive loadings demonstrated antimicrobial efficacies of greater than 5 logarithmic reduction.

[0192] Each of RS 410, RE 410, RS 610, and RE 610 were separately added to volumes of water and neutralized to a pH of 7. Subsequently, a copper-containing material was added to each neutral solution to prepare samples for color testing with 1:1 and 1:3 molar ratios of extractable copper, in the copper-containing material, to each of RS 410, RE 410, RS 610, and RE 610. RS 410 and RS 610 are copper-coordinating additives of formula (I) that are available from Solvay, which are polyethylene glycol tridecyl ether phosphate. RE 410 and RE 610 are copper-coordinating additives of formula (I) that are available from Solvay, which are Poly(oxy-1,2-ethane-di-yl), -(nonylphenyl)--hydroxy-, branched, phosphates. RE 410 and RS 410 contain less moles of ethylene oxide than RE 610 and RS 610, and therefore RE 410 and RS 410 have lower molecular weights. The mixtures were then each combined as above with 50 grams of control paint samples. As shown in FIG. 7 the RS 410, RE 410, RS 610, and RE 610 esters did not minimize color drift. Separately, the copper-containing material and copper-coordinating additive mixtures were combined with 15 grams of paint. As shown in FIGS. 8 and 9, the antimicrobial efficacy test was repeated on the RS 410, RE 410, RS 610, and RE 610 phosphate esters, and the RS 410 and RE 410 series at 1:10 ratio outperformed the control paint samples in terms of antimicrobial efficacy and demonstrated full antimicrobial kill.

[0193] Each of methyl phosphate, trimethyl phosphate, ethoxyamine hydrochloride, phenyl phosphate, and diphenyl phosphate were separately added to volumes of water and neutralized to a pH of 7. Subsequently, a copper-containing material was added to each neutral solution to prepare samples for color testing with 1:3 molar ratios of extractable copper, in the copper-containing material, to each of methyl phosphate, trimethyl phosphate, ethoxyamine hydrochloride, phenyl phosphate, and diphenyl phosphate. The mixtures were then each combined as above with 50 grams of control paint samples. As shown in FIG. 10, each of methyl phosphate, trimethyl phosphate, diphenyl phosphate, and ethoxyamine hydrochloride accelerated color shift to endpoint, minimizing color drift. As shown in FIG. 11, the control paint samples including the copper-containing material and copper-coordinating additives demonstrated lower antimicrobial efficacy of 1.5-2 logarithmic reduction at concentrations of 15 g of 1:3 molar ratio of extractable copper to copper-coordinating additive per gallon of control paint sample. By contrast, as shown in FIG. 12, methylphospahte and ethoxyamine hydrochloride demonstrated minimal impact on antimicrobial efficacy at concentrations of 50 g of 1:3 molar ratio of extractable copper to copper-coordinating additive per gallon of control paint samples.

[0194] Color testing samples with 1:3 molar ratios of extractable copper, in the copper-containing material, to each of methyl phosphate, trimethyl phosphate, ethoxyamine hydrochloride, phenyl phosphate, and diphenyl phosphate were prepared, and each mixture was added to 50 grams of control paint samples. As shown in FIG. 13, all copper-coordinating additives except for phenyl phosphate accelerated color shift to endpoint. Further, as shown in FIG. 14, all copper-coordinating additives exhibited antimicrobial efficacies of greater than 5 logarithmic reduction.

[0195] FIG. 15 illustrates the drift in blue color resulting from an increase in the ratio of the number of ligand compounds complexed to a copper atom in control paint samples relative to copper, from a 0:1 ligand compound to copper atom ratio on the far left, to a 1:1 ligand compound to copper atom ratio on the center left, to a 2:1 ligand compound to copper atom ratio on the center right, to a 4:1 ligand compound to copper atom ratio on the far right.

[0196] FIG. 16 illustrates the differences in color of colorless polymers poly(methyl methacrylate) (PMMA, 15.84 weight %; 3.6 weight % copper-containing material; no color shift) and Nylon 6 (15 weight %; 3.6 weight % copper-containing material; green tint) and tinted polymers polyether imide (15 weight %, yellow polymer; 3.6 weight % copper-containing material; green tint) and Torlon (polyamideimide, 15 weight %, brown polymer; 3.6 weight % copper-containing material; green tint).

[0197] FIG. 17 illustrates the change in color of PMMA in chloroform in non-latex control paint samples, with decreasing weight % amounts of 2EHP, of 25.1 weight %, 14.8 weight %, 4.6 weight %, and 1.9 weight %, and as compared to a control of PMMA in chloroform dosed with a copper-containing material. The color shift demonstrated the impact of the amount of phosphate copper-coordinating additive on overall color in non-latex control paint samples.

[0198] FIG. 18 illustrates the change in color of PMMA in chloroform in non-latex paint, with 25.5 weight % 2EHP as compared to a control of heat-treated PMMA in toluene dosed with a copper-containing material. The color shift demonstrated the impact of phosphate copper-coordinating additive on overall color in non-latex control paint samples.

[0199] FIG. 19 illustrates the change in color of PMMA in NMP in non-latex control paint samples, with 25.8 weight % 2EHP as compared to a control of PMMA in NMP dosed with a copper-containing material. The color shift demonstrated the impact of phosphate copper-coordinating additive on overall color in non-latex control paint samples.

[0200] The above data demonstrate that minimizing color drift and accelerating color change to endpoint were effective strategies in control paint samples. Thiourea as copper-coordinating additive increased the a* beyond the original paint composition, and hydroxylamine hydrochloride and other examples of additives accelerated color endpoints and reduced color shifts by starting with more negative a* values. In certain control paint samples, copper-coordinating additives generally did not negatively impact antimicrobial efficacies. For other control paint samples, additives impacted antimicrobial efficacy at 50 g per gallon loading, but not at 15 g per gallon loading.

[0201] Without being bound by theory, it is believed that species including Cu.sup.1+ may have greater antimicrobial efficacy. Further, it is believed that Cu.sup.2+ is a more energetically favorable oxidation state than Cu.sup.1+, but Cu.sup.2+ may produce color and may have lower antimicrobial efficacy. Thus, it is believed that while species including Cu.sup.2+ may be generally more stable, species including Cu.sup.1+ are favored for function and color in the examples of compositions and methods of the present disclosure.

[0202] Consequently, without being bound by theory, it is believed that additives that are reducing agents may be effective in reversing color production due to Cu.sup.2+ complexes that have already formed, by reducing the Cu.sup.2+ in the complexes to Cu.sup.1+. Alternatively, it is believed that antioxidants may be effective in scavenging oxidants, so as to minimize further color change.

[0203] In an example, an additive that is a reducing agent and/or an antioxidant may be a compound of formula (XII):

##STR00025##

wherein each R.sup.20 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; provided that all R.sup.20 are not simultaneously hydrogen; and provided that at least one R.sup.20 includes one or more heteroatoms selected from N, O, and S replacing the beta-carbon or gamma-carbon, and/or one or more heteroatoms selected from N, O, and S substituted for hydrogens on the alpha-carbon, beta-carbon, or gamma-carbon; or an alpha-carbon of at least one R.sup.20 is a secondary carbon or a tertiary carbon.

[0204] In another example, an additive that is a reducing agent and/or an antioxidant may be a compound of formula (XIX):

##STR00026##

wherein each R.sup.21 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; provided that both R.sup.21 are not simultaneously hydrogen; and optionally wherein the alpha-carbon of at least one R.sup.21 is a secondary or tertiary carbon; and R.sup.22 is selected from the group consisting of (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl, optionally wherein the alpha-carbon of R.sup.22 is a secondary or tertiary carbon.

[0205] In yet another example, an additive that is a reducing agent and/or an antioxidant may be a compound of formula (XX):

##STR00027##

wherein each R.sup.23 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl, optionally wherein the alpha-carbon of at least one R.sup.23 is a secondary or tertiary carbon; provided that both R.sup.23 are not simultaneously hydrogen; and R.sup.24 is selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl, optionally wherein the alpha-carbon of R.sup.24 is a secondary or tertiary carbon.

[0206] In yet another example, an additive that is a reducing agent and/or an antioxidant may be a compound of formula (XI):

##STR00028##

wherein each R.sup.19 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; and provided that all R.sup.19 are not simultaneously hydrogen; and optionally wherein the alpha-carbon of at least one R.sup.19 is a secondary or tertiary carbon.

[0207] In yet another example, an additive that is a reducing agent and/or an antioxidant may be a compound formula (VI):

##STR00029##

wherein X.sup. is selected from the group consisting of fluoride, chloride, bromide, iodide, hexafluorophosphate, sulfate, an alkylsulfonate, and an arylsulfonate; and R.sup.9 is selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl.

[0208] In yet another example, an additive that is a reducing agent and/or an antioxidant may be ascorbic acid or a compound of formula (XXI):

##STR00030##

wherein R.sup.25 is selected from the group consisting of (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl.

[0209] In yet another example, an additive that is a reducing agent and/or an antioxidant may be zinc of any oxidation state.

[0210] In yet another example, an additive that is a reducing agent and/or an antioxidant may be a thiol selected from the group consisting of (C.sub.1-C.sub.30)alkylthiol, (C.sub.2-C.sub.30)alkenylthiol, (C.sub.2-C.sub.30)alkynylthiol, arylthiol, heteroarylthiol, heterocyclylthiol, aryl(C.sub.1-C.sub.4)alkylthiol, heteroaryl(C.sub.1-C.sub.4)alkylthiol, and heterocyclyl(C.sub.1-C.sub.4)alkylthiol.

[0211] In yet another example, an additive that is a reducing agent and/or an antioxidant may be a compound of formula (IV):

##STR00031##

wherein, from S to S, R.sup.6 is selected from the group consisting of substituted or unsubstituted (C.sub.2-C.sub.30)alkylene, substituted or unsubstituted (C.sub.2-C.sub.30)alkenylene, substituted or unsubstituted (C.sub.2-C.sub.30)alkynylene, substituted or unsubstituted aryl(C.sub.1-C.sub.4)alkylene, substituted or unsubstituted (C.sub.1-C.sub.4)alkylarylene, substituted or unsubstituted (C.sub.1-C.sub.4)alkylaryl(C.sub.1C.sub.4)alkylene, substituted or unsubstituted heteroaryl(C.sub.1-C.sub.4)alkylene, substituted or unsubstituted (C.sub.1-C.sub.4)alkylheteroarylene, substituted or unsubstituted (C.sub.1-C.sub.4)alkylheteroaryl(C.sub.1-C.sub.4)alkylene, substituted or unsubstituted heterocyclyl(C.sub.1-C.sub.4)alkylene, substituted or unsubstituted (C.sub.1-C.sub.4)alkylheterocyclylene, and substituted or unsubstituted (C.sub.1-C.sub.4)alkylheterocyclyl(C.sub.1-C.sub.4)alkylene; the substituted (C.sub.2-C.sub.30)alkylene, substituted (C.sub.2-C.sub.30)alkenylene, substituted (C.sub.2-C.sub.30)alkynylene, substituted aryl(C.sub.1-C.sub.4)alkylene, substituted (C.sub.1-C.sub.4)alkylarylene, substituted (C.sub.1-C.sub.4)alkylaryl(C.sub.1-C.sub.4)alkene, substituted heteroaryl(C.sub.1-C.sub.4)alkylene, substituted (C.sub.1-C.sub.4)alkylheteroarylene, substituted (C.sub.1-C.sub.4)alkylheteroaryl(C.sub.1-C.sub.4)alkylene, substituted heterocyclyl(C.sub.1-C.sub.4)alkylene, substituted (C.sub.1-C.sub.4)alkylheterocyclylene, and substituted (C.sub.1-C.sub.4)alkylheterocyclyl(C.sub.1-C.sub.4)alkylene are substituted with one or more substituents each independently selected from the group consisting of (C.sub.1-C.sub.30)alkyl, (C.sub.1-C.sub.30)alkoxy, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkenyloxy, (C.sub.2-C.sub.30)alkynyl, (C.sub.2-C.sub.30)alkynyloxy, aryl, aryloxy, heteroaryl, heteroaryloxy, heterocyclyl, heterocyclyloxy, aryl(C.sub.1-C.sub.4)alkyl, aryl(C.sub.1-C.sub.4)alkoxy, heteroaryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkoxy, heterocyclyl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkoxy; provided that the two thiol groups are not bonded to the same carbon.

[0212] Without being bound by theory, it is believed that an additive that is sterically hindered may inhibit oxidation of Cu.sup.1+ by limiting accessibility to the Cu.sup.1+ site in Cu(I) complexes, but to do so such an additive has to be competitive with other ligands with respect to the strength of binding to the Cu.sup.1+ site and such an additive has to favor Cu.sup.1+ when complexed so that maintaining the Cu.sup.1+ becomes energetically favorable to oxidation.

[0213] Without being bound by theory, it is believed that an additive that is a reducing agent and/or an antioxidant also may be an oxidation inhibitor so as to not only reverse the oxidation of Cu.sup.1+ to Cu.sup.2+ but also to maintain the reduced state as long as possible.

[0214] In an example, an additive that is an oxidation inhibitor may be a compound of formula (XII):

##STR00032##

wherein each R.sup.20 is independently selected form the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; provided that all R.sup.20 are not simultaneously hydrogen, and that an alpha-carbon of at least one R.sup.20 is a secondary carbon or a tertiary carbon.

[0215] In another example, an additive that is an oxidation inhibitor may be a compound of formula (XIX):

##STR00033##

wherein each R.sup.21 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; R.sup.22 is selected from the group consisting of (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; provided that both R.sup.21 are not simultaneously hydrogen, and provided that the alpha-carbon of at least one R.sup.21 and/or R.sup.22 is a secondary or tertiary carbon.

[0216] In yet another example, an additive that is an oxidation inhibitor may be a compound of formula (XX):

##STR00034##

wherein each R.sup.23 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl; and R.sup.24 is selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; provided that the alpha-carbon of at least one R.sup.23 and/or R.sup.23 is a secondary or tertiary carbon.

[0217] In yet another example, an additive that is an oxidation inhibitor may be a compound of formula (XI):

##STR00035##

wherein each R.sup.19 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; and provided that all R.sup.19 are not simultaneously hydrogen and that the alpha-carbon of at least one R.sup.19 is a secondary or tertiary carbon.

[0218] In yet another example, an additive that is an oxidation inhibitor may be a compound of formula (VI):

##STR00036##

wherein X.sup. is selected from the group consisting of fluoride, chloride, bromide, iodide, hexafluorophosphate, sulfate, an alkylsulfonate, and an arylsulfonate; and R.sup.9 is selected from the group consisting of (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; provided that the alpha-carbon of R.sup.9 is a secondary or tertiary carbon.

[0219] In yet another example, an additive that is an oxidation inhibitor may be a compound of formula (XXI):

##STR00037##

wherein R.sup.25 is selected from the group consisting of (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; provided that the alpha-carbon of R.sup.25 is a secondary or tertiary carbon.

[0220] In yet another example, an additive that is an oxidation inhibitor may be a compound of formula (I):

##STR00038##

wherein each of R.sup.1 and R.sup.2 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; provided that both of R.sup.1 and R.sup.2 are not simultaneously hydrogen and that the alpha-carbon of at least one of R.sup.1 and R.sup.2 is a secondary or tertiary carbon.

[0221] In yet another example, an additive that is an oxidation inhibitor may be a compound of formula (XXII):

##STR00039##

wherein each of R.sup.26, R.sup.27, R.sup.28, and R.sup.29 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; optionally wherein the alpha-carbon of at least one of R.sup.26, R.sup.27, R.sup.28, and R.sup.29 is a secondary or tertiary carbon.

[0222] In yet another example, an additive that is an oxidation inhibitor may be a compound of formula (XXIII):

##STR00040##

wherein each of R.sup.30, R.sup.3, R.sup.32, and R.sup.33 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; optionally wherein the alpha-carbon of at least one of R.sup.30, R.sup.3, R.sup.32, and R.sup.33 is a secondary or tertiary carbon.

[0223] In yet another example, an additive that is an oxidation inhibitor may be a nitrile compound selected from the group consisting of a (C.sub.1-C.sub.30)alkylnitrile, a (C.sub.2-C.sub.30)alkenylnitrile, a (C.sub.2-C.sub.30)alkynylnitrile, an arylnitrile, a heteroarylnitrile, a heterocyclylnitrile, an aryl(C.sub.1-C.sub.4)alkylnitrile, a heteroaryl(C.sub.1-C.sub.4)alkylnitrile, and a heterocyclyl(C.sub.1-C.sub.4)alkylnitrile; optionally wherein the alpha-carbon is a secondary or tertiary carbon.

[0224] In yet another example, an additive that is an oxidation inhibitor may be a substituted or unsubstituted compound of formula (XXIV):

##STR00041##

wherein a may be an integer from 1 to 4; b may be an integer from 1 to 4, and c may be an integer from 0 to 3; and wherein a substituted compound of formula (XXIV) includes one or more carbons substituted with one or more substituents selected from the group consisting of (C.sub.1-C.sub.30)alkyl, (C.sub.1-C.sub.30)alkoxy, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkenyloxy, (C.sub.2-C.sub.30)alkynyl, (C.sub.2-C.sub.30)alkynyloxy, aryl, aryloxy, heteroaryl, heteroaryloxy, heterocyclyl, heterocyclyloxy, aryl(C.sub.1-C.sub.4)alkyl, aryl(C.sub.1-C.sub.4)alkoxy, heteroaryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkoxy, heterocyclyl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkoxy.

[0225] In yet another example, an additive that is an oxidation inhibitor may be a compound of formula (VII):

##STR00042##

wherein each of R.sup.10 and R.sup.11 is independently selected from the group consisting of (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; provided that the alpha carbon of at least one of R.sup.10 and R.sup.11 is a secondary or tertiary carbon.

[0226] In yet another example, an additive that is an oxidation inhibitor may be a compound selected from benzotriazole, an amino acid, and a surfactant. Examples of surfactants may include sodium stearate, 4-(5-dodecyl)benzenesulfonate, docusate, alkyl ether phosphates, and benzalkonium chloride.

[0227] In yet another example, an additive that is an oxidation inhibitor may be a compound including an imidazole group or a reduced imidazole group. Examples may include benzimidazole, imidazole, or 2-imidazoline.

##STR00043##

[0228] In yet another example, an additive that is an oxidation inhibitor may be a soft base. Soft bases may include species that are characterized by large radii, intermediate electronegativities, and high polarizabilities. Examples of soft bases may include H.sup., CO, PR.sub.3, C.sub.6H.sub.6, and SCN.sup..

[0229] In yet another example, an additive that is an oxidation inhibitor may be a compound of formula (XXV):

##STR00044##

wherein each of R.sup.34, R.sup.35, and R.sup.36 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; provided that R.sup.34, R.sup.35, and R.sup.36 are not simultaneously hydrogen; and optionally wherein the alpha-carbon of at least one of R.sup.34, R.sup.35, and R.sup.36 is a secondary or tertiary carbon.

[0230] In yet another example, an additive that is an oxidation inhibitor may be a compound of formula (XXVI):

##STR00045##

wherein each of R.sup.37, R.sup.38, and R.sup.39 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; provided that R.sup.37, R.sup.38, and R.sup.39 are not simultaneously hydrogen; and optionally wherein the alpha-carbon of at least one of R.sup.37, R.sup.38, and R.sup.39 is a secondary or tertiary carbon.

[0231] Copper-coordinating additives may need to be introduced into a carrier to mitigate the color change based on the type of the carrier. Color drift kinetics and overall total drift (magnitude and hue) may be different depending on the carrier formulation and the starting color. It is believed that components in a carrier may change dissolution and oxidation behavior of copper, or be very competitive ligand for coordinating to copper. If a component in a carrier inhibits dissolution and/or oxidation, color drift may still happen, but it is expected that the kinetics will be much slower, as appears to be the case in some control paint sample. If a carrier includes components that are either more strongly binding ligands to copper than the current additive options or that are more intensely colored, more strongly binding or multivalent additives may be required. It is expected that screening carriers based on the dissolution kinetics, oxidation behavior of copper, and color endpoint and gauging ligand strength by use of different types of additives will be helpful to calibrate copper-coordinating additive to carrier type.

[0232] Although the present disclosure has been described with reference to examples and the accompanying figures and charts, the present disclosure is not limited thereto, but may be variously modified and altered by those skilled in the art to which the present disclosure pertains without departing from the spirit and scope of the present disclosure.

[0233] The subject-matter of the disclosure may also relate, among others, to the following aspects:

[0234] A first aspect relates to a composition, comprising: a carrier; a copper-containing material in the carrier, wherein the copper-containing materials comprises from 10 to 100 weight % of an amount of extractable copper; and a copper-coordinating additive in the carrier, in a molar ratio of the amount of extractable copper to an amount of the copper-coordinating additive of from 1:0.1 to 1:25, wherein a concentration of the copper-containing material and the copper-coordinating additive in the carrier is from 0.01% weight/weight of the carrier to 5% weight/weight of the carrier.

[0235] A second aspect relates to the composition of aspect 1, wherein the copper-containing material comprises from 25 to 50 weight % of the amount of extractable copper.

[0236] A third aspect relates to the composition of any preceding aspect, the copper-coordinating additive is a compound of formula (I), (II), (III), (IV), (V), (XI), or (XII):

##STR00046## [0237] wherein each of R.sup.1 and R.sup.2 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; [0238] provided that both of R.sup.1 and R.sup.2 are not simultaneously hydrogen; [0239] each R.sup.3 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, substituted or unsubstituted 2-pyridyl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; [0240] the substituted 2-pyridyl is substituted with up to four substituents, each substituent independently selected from the group consisting of (C.sub.1-C.sub.30)alkyl, (C.sub.1-C.sub.30)alkoxy, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkenoxy, (C.sub.2-C.sub.30)alkynyl, (C.sub.2-C.sub.30)alkynoxy, aryl, aryloxy, heteroaryl, heteroaryloxy, heterocyclyl, heterocyclyloxy, aryl(C.sub.1-C.sub.4)alkyl, aryl(C.sub.1-C.sub.4)alkoxy, heteroaryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkoxy, heterocyclyl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkoxy; [0241] each R.sup.4 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; [0242] R.sup.5 is selected from the group consisting of substituted or unsubstituted (C.sub.1-C.sub.30)alkyl, substituted or unsubstituted (C.sub.2-C.sub.30)alkenyl, substituted or unsubstituted (C.sub.2-C.sub.30)alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl(C.sub.1-C.sub.4)alkyl, substituted or unsubstituted heteroaryl(C.sub.1-C.sub.4)alkyl, and substituted or unsubstituted heterocyclyl(C.sub.1-C.sub.4)alkyl; [0243] the substituted (C.sub.1-C.sub.30)alkyl, substituted (C.sub.2-C.sub.30)alkenyl, substituted (C.sub.2-C.sub.30)alkynyl, substituted aryl, substituted heteroaryl, substituted heterocyclyl, substituted aryl(C.sub.1-C.sub.4)alkyl, substituted heteroaryl(C.sub.1-C.sub.4)alkyl, and substituted heterocyclyl(C.sub.1-C.sub.4)alkyl are substituted with one or more substituents each of which is independently selected from the group consisting of OH, NH.sub.2, SH, CN, C(O)NH.sub.2, and CO.sub.2H; [0244] from S to S, R.sup.6 is selected from the group consisting of substituted or unsubstituted (C.sub.2-C.sub.30)alkylene, substituted or unsubstituted (C.sub.2-C.sub.30)alkenylene, substituted or unsubstituted (C.sub.2-C.sub.30)alkynylene, substituted or unsubstituted aryl(C.sub.1-C.sub.4)alkylene, substituted or unsubstituted (C.sub.1-C.sub.4)alkylarylene, substituted or unsubstituted (C.sub.1-C.sub.4)alkylaryl(C.sub.1-C.sub.4)alkylene, substituted or unsubstituted heteroaryl(C.sub.1-C.sub.4)alkylene, substituted or unsubstituted (C.sub.1-C.sub.4)alkylheteroarylene, substituted or unsubstituted (C.sub.1-C.sub.4)alkylheteroaryl(C.sub.1-C.sub.4)alkylene, substituted or unsubstituted heterocyclyl(C.sub.1-C.sub.4)alkylene, substituted or unsubstituted (C.sub.1-C.sub.4)alkylheterocyclylene, and substituted or unsubstituted (C.sub.1-C.sub.4)alkylheterocyclyl(C.sub.1-C.sub.4)alkylene; [0245] the substituted (C.sub.2-C.sub.30)alkylene, substituted (C.sub.2-C.sub.30)alkenylene, substituted (C.sub.2-C.sub.30)alkynylene, substituted aryl(C.sub.1-C.sub.4)alkylene, substituted (C.sub.1-C.sub.4)alkylarylene, substituted (C.sub.1-C.sub.4)alkylaryl(C.sub.1-C.sub.4)alkylene, substituted heteroaryl(C.sub.1-C.sub.4)alkylene, substituted (C.sub.1-C.sub.4)alkylheteroarylene, substituted (C.sub.1-C.sub.4)alkylheteroaryl(C.sub.1-C.sub.4)alkylene, substituted heterocyclyl(C.sub.1-C.sub.4)alkylene, substituted (C.sub.1-C.sub.4)alkylheterocyclylene, and substituted (C.sub.1-C.sub.4)alkylheterocyclyl(C.sub.1-C.sub.4)alkylene are substituted with one or more substituents each independently selected from the group consisting of (C.sub.1-C.sub.30)alkyl, (C.sub.1-C.sub.30)alkoxy, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkenyloxy, (C.sub.2-C.sub.30)alkynyl, (C.sub.2-C.sub.30)alkynyloxy, aryl, aryloxy, heteroaryl, heteroaryloxy, heterocyclyl, heterocyclyloxy, aryl(C.sub.1-C.sub.4)alkyl, aryl(C.sub.1-C.sub.4)alkoxy, heteroaryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkoxy, heterocyclyl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkoxy; [0246] provided that the two thiol groups in formula (IV) are not bonded to the same carbon; [0247] each R.sup.7 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.1-C.sub.30)alkoxy, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkenyloxy, (C.sub.2-C.sub.30)alkynyl, (C.sub.2-C.sub.30)alkynyloxy, aryl, aryloxy, heteroaryl, heteroaryloxy, heterocyclyl, heterocyclyloxy, aryl(C.sub.1-C.sub.4)alkyl, aryl(C.sub.1-C.sub.4)alkoxy, heteroaryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkoxy, heterocyclyl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkoxy; [0248] R.sup.8 is selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, heterocyclyl(C.sub.1-C.sub.4)alkyl, and (C(R.sup.7).sub.2).sub.zOH; [0249] each of x, y, and z is independently 2 or 3; [0250] each R.sup.19 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; [0251] provided that all R.sup.19 are not simultaneously hydrogen; [0252] each R.sup.20 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; and [0253] provided that all R.sup.20 are not simultaneously hydrogen.

[0254] A fourth aspect relates to the composition of any one of aspects 1 to 2, wherein the copper-coordinating additive is a compound of formula (I), (III), (VI), (VII), (IX), (X), (XI), or (II):

##STR00047## [0255] wherein each of R.sup.1 and R.sup.2 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; [0256] provided that both of R.sup.1 and R.sup.2 are not simultaneously hydrogen; [0257] R is selected from the group consisting of substituted or unsubstituted (C.sub.1-C.sub.30)alkyl, substituted or unsubstituted (C.sub.2-C.sub.30)alkenyl, substituted or unsubstituted (C.sub.2-C.sub.30)alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl(C.sub.1-C.sub.4)alkyl, substituted or unsubstituted heteroaryl(C.sub.1-C.sub.4)alkyl, and substituted or unsubstituted heterocyclyl(C.sub.1-C.sub.4)alkyl; [0258] the substituted (C.sub.1-C.sub.30)alkyl, substituted (C.sub.2-C.sub.30)alkenyl, substituted (C.sub.2-C.sub.30)alkynyl, substituted aryl, substituted heteroaryl, substituted heterocyclyl, substituted aryl(C.sub.1-C.sub.4)alkyl, substituted heteroaryl(C.sub.1-C.sub.4)alkyl, and substituted heterocyclyl(C.sub.1-C.sub.4)alkyl in formula (III) are substituted with one or more substituents each of which is independently selected from the group consisting of OH, NH.sub.2, SH, CN, C(O)NH.sub.2, and CO.sub.2H; [0259] X.sup. is selected from the group consisting of fluoride, chloride, bromide, iodide, hexafluorophosphate, sulfate, an alkylsulfonate, and an arylsulfonate; [0260] R.sup.9 is selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; [0261] each of R.sup.10 and R.sup.11 is independently selected from the group consisting of substituted or unsubstituted (C.sub.1-C.sub.30)alkyl, substituted or unsubstituted (C.sub.2-C.sub.30)alkenyl, substituted or unsubstituted (C.sub.2-C.sub.30)alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl(C.sub.1-C.sub.4)alkyl, substituted or unsubstituted heteroaryl(C.sub.1-C.sub.4)alkyl, and substituted or unsubstituted heterocyclyl(C.sub.1-C.sub.4)alkyl; [0262] the substituted (C.sub.1-C.sub.30)alkyl, substituted (C.sub.2-C.sub.30)alkenyl, substituted (C.sub.2-C.sub.30)alkynyl, substituted aryl, substituted heteroaryl, substituted heterocyclyl, substituted aryl(C.sub.1-C.sub.4)alkyl, substituted heteroaryl(C.sub.1-C.sub.4)alkyl, and substituted heterocyclyl(C.sub.1-C.sub.4)alkyl in formula (VII) are substituted with one or more substituents each of which is independently selected from the group consisting of OH, NH.sub.2, SH, CN, C(O)NH.sub.2, C(O)NHR.sup.11, C(O)NR.sup.11.sub.2, CO.sub.2H, and CO.sub.2R.sup.11; [0263] each R.sup.14 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.1-C.sub.30)alkoxy, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkenyloxy, (C.sub.2-C.sub.30)alkynyl, (C.sub.2-C.sub.30)alkynyloxy, aryl, aryloxy, heteroaryl, heteroaryloxy, heterocyclyl, heterocyclyloxy, aryl(C.sub.1-C.sub.4)alkyl, aryl(C.sub.1-C.sub.4)alkoxy, heteroaryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkoxy, heterocyclyl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkoxy; [0264] R.sup.11 is selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, heterocyclyl(C.sub.1-C.sub.4)alkyl, and (C(R.sup.14).sub.2).sub.pNH.sub.2; [0265] each of m, n, and p is independently 2 or 3; [0266] Y is O or S; [0267] each R.sup.16 is independently OR.sup.17 or N(R.sup.18).sub.2; [0268] R.sup.17 is selected from the group consisting of (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; and [0269] each R.sup.18 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; [0270] each R.sup.19 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; [0271] provided that all R.sup.19 are not simultaneously hydrogen; [0272] each R.sup.20 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; and [0273] provided that all R.sup.20 are not simultaneously hydrogen.

[0274] A fifth aspect relates to the composition of any one of aspects 1 to 2, wherein the copper-coordinating additive is a compound of formula (VIII):

##STR00048## [0275] wherein R.sup.12 is selected from the group consisting of substituted or unsubstituted (C.sub.1-C.sub.30)alkyl, substituted or unsubstituted (C.sub.2-C.sub.30)alkenyl, substituted or unsubstituted (C.sub.2-C.sub.30)alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl(C.sub.1-C.sub.4)alkyl, substituted or unsubstituted heteroaryl(C.sub.1-C.sub.4)alkyl, and substituted or unsubstituted heterocyclyl(C.sub.1-C.sub.4)alkyl; [0276] each R.sup.13 is independently selected from the group consisting of hydrogen, substituted or unsubstituted (C.sub.1-C.sub.30)alkyl, substituted or unsubstituted (C.sub.2-C.sub.30)alkenyl, substituted or unsubstituted (C.sub.2-C.sub.30)alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl(C.sub.1-C.sub.4)alkyl, substituted or unsubstituted heteroaryl(C.sub.1-C.sub.4)alkyl, and substituted or unsubstituted heterocyclyl(C.sub.1-C.sub.4)alkyl; and [0277] the substituted (C.sub.1-C.sub.30)alkyl, substituted (C.sub.2-C.sub.30)alkenyl, substituted (C.sub.2-C.sub.30)alkynyl, substituted aryl, substituted heteroaryl, substituted heterocyclyl, substituted aryl(C.sub.1-C.sub.4)alkyl, substituted heteroaryl(C.sub.1-C.sub.4)alkyl, and substituted heterocyclyl(C.sub.1-C.sub.4)alkyl are substituted with one or more substituents each of which is independently selected from the group consisting of OH, NH.sub.2, SH, CN, C(O)NH.sub.2, C(O)NHR.sup.13, C(O)NR.sup.13.sub.2, CO.sub.2H, and CO.sub.2R.sup.13; and [0278] wherein the composition further comprises a pretreatment solution.

[0279] A sixth aspect relates to the composition of any preceding aspect, wherein the copper-coordinating additive is a compound selected from the group consisting of 2-ethylhexyl phosphate, bis(2-ethylhexyl)phosphate, methyl phosphate, dimethyl phosphate, trimethyl phosphate, phenyl phosphate, diphenyl phosphate, 2,2-bipyridine, terpyridine, citric acid, diethanolamine, triethanolamine, hydroxyamine hydrochloride, ethoxyamine hydrochloride, triethyl citrate, thiourea, urea, 14-crown-4, 15-crown-5, 18-crown-6, dibenzo-18-crown-6, aza-15-crown-5, aza-18-crown-6, and salen.

[0280] A seventh aspect relates to the composition of any preceding aspect, wherein the composition demonstrates a greater than 3 logarithmic reduction in a concentration of a bacteria selected from the group consisting of Staphylococcus aureus, Enterobacter aerogenes, Pseudomonas aeruginosa, Methicillin Resistant Staphylococcus aureus, E. coli, and mixtures thereof.

[0281] An eighth aspect relates to the composition of aspect 1, wherein the copper-coordinating additive is a thiol, zinc, or ascorbic acid, or a compound of formula (IV), (VI), (XI), (XII), (XIX), (XX), or (XXI):

##STR00049## [0282] wherein X.sup. is selected from the group consisting of fluoride, chloride, bromide, iodide, hexafluorophosphate, sulfate, an alkylsulfonate, and an arylsulfonate; [0283] wherein, from S to S, R.sup.6 is selected from the group consisting of substituted or unsubstituted (C.sub.2-C.sub.30)alkylene, substituted or unsubstituted (C.sub.2-C.sub.30)alkenylene, substituted or unsubstituted (C.sub.2-C.sub.30)alkynylene, substituted or unsubstituted aryl(C.sub.1-C.sub.4)alkylene, substituted or unsubstituted (C.sub.1-C.sub.4)alkylarylene, substituted or unsubstituted (C.sub.1-C.sub.4)alkylaryl(C.sub.1-C.sub.4)alkylene, substituted or unsubstituted heteroaryl(C.sub.1-C.sub.4)alkylene, substituted or unsubstituted (C.sub.1-C.sub.4)alkylheteroarylene, substituted or unsubstituted (C.sub.1-C.sub.4)alkylheteroaryl(C.sub.1-C.sub.4)alkylene, substituted or unsubstituted heterocyclyl(C.sub.1-C.sub.4)alkylene, substituted or unsubstituted (C.sub.1-C.sub.4)alkylheterocyclylene, and substituted or unsubstituted (C.sub.1-C.sub.4)alkylheterocyclyl(C.sub.1-C.sub.4)alkylene; the substituted (C.sub.2-C.sub.30)alkylene, substituted (C.sub.2-C.sub.30)alkenylene, substituted (C.sub.2-C.sub.30)alkynylene, substituted aryl(C.sub.1-C.sub.4)alkylene, substituted (C.sub.1-C.sub.4)alkylarylene, substituted (C.sub.1-C.sub.4)alkylaryl(C.sub.1-C.sub.4)alkene, substituted heteroaryl(C.sub.1-C.sub.4)alkylene, substituted (C.sub.1-C.sub.4)alkylheteroarylene, substituted (C.sub.1-C.sub.4)alkylheteroaryl(C.sub.1-C.sub.4)alkylene, substituted heterocyclyl(C.sub.1-C.sub.4)alkylene, substituted (C.sub.1-C.sub.4)alkylheterocyclylene, and substituted (C.sub.1-C.sub.4)alkylheterocyclyl(C.sub.1-C.sub.4)alkylene are substituted with one or more substituents each independently selected from the group consisting of (C.sub.1-C.sub.30)alkyl, (C.sub.1-C.sub.30)alkoxy, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkenyloxy, (C.sub.2-C.sub.30)alkynyl, (C.sub.2-C.sub.30)alkynyloxy, aryl, aryloxy, heteroaryl, heteroaryloxy, heterocyclyl, heterocyclyloxy, aryl(C.sub.1-C.sub.4)alkyl, aryl(C.sub.1-C.sub.4)alkoxy, heteroaryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkoxy, heterocyclyl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkoxy; [0284] wherein R.sup.9 is selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; [0285] wherein each R.sup.19 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; [0286] wherein each R.sup.20 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; [0287] wherein each R.sup.21 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; [0288] wherein R.sup.22 is selected from the group consisting of (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; [0289] wherein each R.sup.23 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; [0290] wherein R.sup.24 is selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; and [0291] wherein R.sup.25 is selected from the group consisting of (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; [0292] optionally wherein the alpha-carbon of at least one R.sup.19 is a secondary or tertiary carbon; [0293] optionally wherein the alpha-carbon of at least one R.sup.21 is a secondary or tertiary carbon; optionally wherein the alpha-carbon of R.sup.22 is a secondary or tertiary carbon; [0294] optionally wherein the alpha-carbon of at least one R.sup.23 is a secondary or tertiary carbon; and [0295] optionally wherein the alpha-carbon of R.sup.24 is a secondary or tertiary carbon; [0296] provided that all R.sup.19 are not simultaneously hydrogen; [0297] provided that all R.sup.20 are not simultaneously hydrogen; [0298] provided that at least one R.sup.20 includes one or more heteroatoms selected from N, O, and S replacing the beta-carbon or gamma-carbon, and/or one or more heteroatoms selected from N, O, and S substituted for hydrogens on the alpha-carbon, beta-carbon, or gamma-carbon; or an alpha-carbon of at least one R.sup.20 is a secondary carbon or a tertiary carbon; [0299] provided that both R.sup.21 are not simultaneously hydrogen; [0300] provided that both R.sup.3 are not simultaneously hydrogen; and [0301] provided that R.sup.6 has a structure such that the two thiol groups are not bonded to the same carbon.

[0302] A ninth aspect relates to the composition of aspect 1, wherein the copper-coordinating additive is a soft base, benzotriazole, an amino acid, a surfactant, a compound comprising an imidazole or a reduced imidazole group, a nitrile compound, or a compound of formula (I), (VI), (VII), (XI), (XII), (XIX), (XX), (XXI), (XXII), (XXIII), (XXIV), (XXV), or (XXVI):

##STR00050## ##STR00051## [0303] wherein X.sup. is selected from the group consisting of fluoride, chloride, bromide, iodide, hexafluorophosphate, sulfate, an alkylsulfonate, and an arylsulfonate; [0304] wherein a is an integer from 1 to 4; [0305] wherein b is an integer from 1 to 4, [0306] wherein c is an integer from 0 to 3; [0307] wherein each of R.sup.1 and R.sup.2 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; [0308] wherein R.sup.9 is selected from the group consisting of (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; [0309] wherein each of R.sup.10 and R.sup.11 is independently selected from the group consisting of (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; [0310] wherein each R.sup.19 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; [0311] wherein each R.sup.20 is independently selected form the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; [0312] wherein each R.sup.21 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; [0313] wherein R.sup.22 is selected from the group consisting of (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; [0314] wherein each R.sup.23 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl; [0315] wherein R.sup.24 is selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; wherein R.sup.25 is selected from the group consisting of (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; [0316] wherein each of R.sup.26, R.sup.27, R.sup.28, and R.sup.29 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; [0317] wherein each of R.sup.30, R.sup.31, R.sup.32, and R.sup.33 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; [0318] wherein each of R.sup.34, R, and R.sup.36 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; [0319] wherein each of R.sup.37, R.sup.38, and R.sup.39 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; wherein the nitrile compound is selected from the group consisting of a (C.sub.1-C.sub.30)alkylnitrile, a (C.sub.2-C.sub.30)alkenylnitrile, a (C.sub.2-C.sub.30)alkynylnitrile, an arylnitrile, a heteroarylnitrile, a heterocyclylnitrile, an aryl(C.sub.1-C.sub.4)alkylnitrile, a heteroaryl(C.sub.1-C.sub.4)alkylnitrile, and a heterocyclyl(C.sub.1-C.sub.4)alkylnitrile; and [0320] wherein a substituted compound of formula (XXIV) includes one or more carbons substituted with one or more substituents selected from the group consisting of (C.sub.1-C.sub.30)alkyl, (C.sub.1-C.sub.30)alkoxy, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkenyloxy, (C.sub.2-C.sub.30)alkynyl, (C.sub.2-C.sub.30)alkynyloxy, aryl, aryloxy, heteroaryl, heteroaryloxy, heterocyclyl, heterocyclyloxy, aryl(C.sub.1-C.sub.4)alkyl, aryl(C.sub.1-C.sub.4)alkoxy, heteroaryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkoxy, heterocyclyl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkoxy; [0321] optionally wherein the alpha-carbon of at least one of R.sup.26, R.sup.27, R.sup.28, and R.sup.29 is a secondary or tertiary carbon; [0322] optionally wherein the alpha-carbon of at least one of R.sup.30, R.sup.31, R.sup.32, and R.sup.33 is a secondary or tertiary carbon; [0323] optionally wherein the alpha-carbon of at least one of R.sup.34, R.sup.35, and R.sup.36 is a secondary or tertiary carbon; [0324] optionally wherein the alpha-carbon of at least one of R.sup.37, R.sup.38, and R.sup.39 is a secondary or tertiary carbon; and [0325] optionally wherein the alpha-carbon of the nitrile compound is a secondary or tertiary carbon; [0326] provided that both of R.sup.1 and R.sup.2 are not simultaneously hydrogen and that the alpha-carbon of at least one of R.sup.1 and R.sup.2 is a secondary or tertiary carbon; [0327] provided that the alpha-carbon of R.sup.9 is a secondary or tertiary carbon; [0328] provided that the alpha carbon of at least one of R.sup.10 and R.sup.11 is a secondary or tertiary carbon; [0329] provided that all R.sup.19 are not simultaneously hydrogen and that the alpha-carbon of at least one R.sup.19 is a secondary or tertiary carbon; [0330] provided that all R.sup.20 are not simultaneously hydrogen, and that an alpha-carbon of at least one R.sup.20 is a secondary carbon or a tertiary carbon; [0331] provided that both R.sup.21 are not simultaneously hydrogen; [0332] provided that the alpha-carbon of at least one R.sup.21 and/or R.sup.22 is a secondary or tertiary carbon; [0333] provided that the alpha-carbon of at least one R.sup.23 and/or R.sup.23 is a secondary or tertiary carbon; [0334] provided that the alpha-carbon of R.sup.W is a secondary or tertiary carbon; [0335] provided that R.sup.34, R.sup.3, and R.sup.36 are not simultaneously hydrogen; and [0336] provided that R.sup.37, R.sup.38, and R.sup.39 are not simultaneously hydrogen.

[0337] A tenth aspect relates to a method of minimizing a color change in a biocidal material, comprising: combining a copper-containing material comprising from 10 to 100 weight % of an amount of extractable copper with an amount of copper-coordinating additive, in a molar ratio of the amount of extractable copper to the amount of copper-coordinating additive of from 1:0.1 to 1:25 to form a copper-containing mixture; and combining the copper-containing mixture with a carrier to form the biocidal material, wherein a concentration of the copper-containing material and the copper-coordinating additive of the copper-containing mixture in the carrier is from 0.01% weight/weight of the carrier to 5% weight/weight of the carrier; and wherein the color change in the biocidal material is minimized relative to a change in color of a mixture of the carrier and the copper-containing material in the absence of the copper-coordinating additive.

[0338] An eleventh aspect relates to the method of aspect 10, wherein the copper-containing material comprises from 25 to 50 weight % of the amount of extractable copper.

[0339] A twelfth aspect relates to the method of aspects 10 or 11, wherein the copper-coordinating additive is a compound of formula (I), (II), (III), (IV), (V), (XI), or (XII):

##STR00052## [0340] wherein each of R.sup.1 and R.sup.2 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; [0341] provided that both of R.sup.1 and R.sup.2 are not simultaneously hydrogen; [0342] each R.sup.3 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, substituted or unsubstituted 2-pyridyl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; [0343] the substituted 2-pyridyl is substituted with up to four substituents, each substituent independently selected from the group consisting of (C.sub.1-C.sub.30)alkyl, (C.sub.1-C.sub.30)alkoxy, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkenoxy, (C.sub.2-C.sub.30)alkynyl, (C.sub.2-C.sub.30)alkynoxy, aryl, aryloxy, heteroaryl, heteroaryloxy, heterocyclyl, heterocyclyloxy, aryl(C.sub.1-C.sub.4)alkyl, aryl(C.sub.1-C.sub.4)alkoxy, heteroaryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkoxy, heterocyclyl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkoxy; [0344] each R.sup.4 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; [0345] R.sup.5 is selected from the group consisting of substituted or unsubstituted (C.sub.1-C.sub.30)alkyl, substituted or unsubstituted (C.sub.2-C.sub.30)alkenyl, substituted or unsubstituted (C.sub.2-C.sub.30)alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl(C.sub.1-C.sub.4)alkyl, substituted or unsubstituted heteroaryl(C.sub.1-C.sub.4)alkyl, and substituted or unsubstituted heterocyclyl(C.sub.1-C.sub.4)alkyl; [0346] the substituted (C.sub.1-C.sub.30)alkyl, substituted (C.sub.2-C.sub.30)alkenyl, substituted (C.sub.2-C.sub.30)alkynyl, substituted aryl, substituted heteroaryl, substituted heterocyclyl, substituted aryl(C.sub.1-C.sub.4)alkyl, substituted heteroaryl(C.sub.1-C.sub.4)alkyl, and substituted heterocyclyl(C.sub.1-C.sub.4)alkyl are substituted with one or more substituents each of which is independently selected from the group consisting of OH, NH.sub.2, SH, CN, C(O)NH.sub.2, and CO.sub.2H; [0347] from S to S, R.sup.6 is selected from the group consisting of substituted or unsubstituted (C.sub.2-C.sub.30)alkylene, substituted or unsubstituted (C.sub.2-C.sub.30)alkenylene, substituted or unsubstituted (C.sub.2-C.sub.30)alkynylene, substituted or unsubstituted aryl(C.sub.1-C.sub.4)alkylene, substituted or unsubstituted (C.sub.1-C.sub.4)alkylarylene, substituted or unsubstituted (C.sub.1-C.sub.4)alkylaryl(C.sub.1-C.sub.4)alkylene, substituted or unsubstituted heteroaryl(C.sub.1-C.sub.4)alkylene, substituted or unsubstituted (C.sub.1-C.sub.4)alkylheteroarylene, substituted or unsubstituted (C.sub.1-C.sub.4)alkylheteroaryl(C.sub.1-C.sub.4)alkylene, substituted or unsubstituted heterocyclyl(C.sub.1-C.sub.4)alkylene, substituted or unsubstituted (C.sub.1-C.sub.4)alkylheterocyclylene, and substituted or unsubstituted (C.sub.1-C.sub.4)alkylheterocyclyl(C.sub.1-C.sub.4)alkylene; [0348] the substituted (C.sub.2-C.sub.30)alkylene, substituted (C.sub.2-C.sub.30)alkenylene, substituted (C.sub.2-C.sub.30)alkynylene, substituted aryl(C.sub.1-C.sub.4)alkylene, substituted (C.sub.1-C.sub.4)alkylarylene, substituted (C.sub.1-C.sub.4)alkylaryl(C.sub.1-C.sub.4)alkylene, substituted heteroaryl(C.sub.1-C.sub.4)alkylene, substituted (C.sub.1-C.sub.4)alkylheteroarylene, substituted (C.sub.1-C.sub.4)alkylheteroaryl(C.sub.1-C.sub.4)alkylene, substituted heterocyclyl(C.sub.1-C.sub.4)alkylene, substituted (C.sub.1-C.sub.4)alkylheterocyclylene, and substituted (C.sub.1-C.sub.4)alkylheterocyclyl(C.sub.1-C.sub.4)alkylene are substituted with one or more substituents each independently selected from the group consisting of (C.sub.1-C.sub.30)alkyl, (C.sub.1-C.sub.30)alkoxy, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkenyloxy, (C.sub.2-C.sub.30)alkynyl, (C.sub.2-C.sub.30)alkynyloxy, aryl, aryloxy, heteroaryl, heteroaryloxy, heterocyclyl, heterocyclyloxy, aryl(C.sub.1-C.sub.4)alkyl, aryl(C.sub.1-C.sub.4)alkoxy, heteroaryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkoxy, heterocyclyl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkoxy; [0349] provided that the two thiol groups in formula (IV) are not bonded to the same carbon; [0350] each R.sup.7 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.1-C.sub.30)alkoxy, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkenyloxy, (C.sub.2-C.sub.30)alkynyl, (C.sub.2-C.sub.30)alkynyloxy, aryl, aryloxy, heteroaryl, heteroaryloxy, heterocyclyl, heterocyclyloxy, aryl(C.sub.1-C.sub.4)alkyl, aryl(C.sub.1-C.sub.4)alkoxy, heteroaryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkoxy, heterocyclyl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkoxy; [0351] R.sup.8 is selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, heterocyclyl(C.sub.1-C.sub.4)alkyl, and (C(R.sup.7).sub.2).sub.zOH; [0352] each of x, y, and z is independently 2 or 3; [0353] each R.sup.19 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; [0354] provided that all R.sup.19 are not simultaneously hydrogen; [0355] each R.sup.20 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; and [0356] provided that all R.sup.20 are not simultaneously hydrogen.

[0357] A thirteenth aspect relates to the method of aspect 1, wherein the copper-coordinating additive is a thiol, zinc, or ascorbic acid, or a compound of formula (IV), (VI), (XI), (XII), (XIX), (XX), or (XXI):

##STR00053## [0358] wherein X.sup. is selected from the group consisting of fluoride, chloride, bromide, iodide, hexafluorophosphate, sulfate, an alkylsulfonate, and an arylsulfonate; [0359] wherein, from S to S, R.sup.6 is selected from the group consisting of substituted or unsubstituted (C.sub.2-C.sub.30)alkylene, substituted or unsubstituted (C.sub.2-C.sub.30)alkenylene, substituted or unsubstituted (C.sub.2-C.sub.30)alkynylene, substituted or unsubstituted aryl(C.sub.1-C.sub.4)alkylene, substituted or unsubstituted (C.sub.1-C.sub.4)alkylarylene, substituted or unsubstituted (C.sub.1-C.sub.4)alkylaryl(C.sub.1-C.sub.4)alkylene, substituted or unsubstituted heteroaryl(C.sub.1-C.sub.4)alkylene, substituted or unsubstituted (C.sub.1-C.sub.4)alkylheteroarylene, substituted or unsubstituted (C.sub.1-C.sub.4)alkylheteroaryl(C.sub.1-C.sub.4)alkylene, substituted or unsubstituted heterocyclyl(C.sub.1-C.sub.4)alkylene, substituted or unsubstituted (C.sub.1-C.sub.4)alkylheterocyclylene, and substituted or unsubstituted (C.sub.1-C.sub.4)alkylheterocyclyl(C.sub.1-C.sub.4)alkylene; the substituted (C.sub.2-C.sub.30)alkylene, substituted (C.sub.2-C.sub.30)alkenylene, substituted (C.sub.2-C.sub.30)alkynylene, substituted aryl(C.sub.1-C.sub.4)alkylene, substituted (C.sub.1-C.sub.4)alkylarylene, substituted (C.sub.1-C.sub.4)alkylaryl(C.sub.1-C.sub.4)alkene, substituted heteroaryl(C.sub.1-C.sub.4)alkylene, substituted (C.sub.1-C.sub.4)alkylheteroarylene, substituted (C.sub.1-C.sub.4)alkylheteroaryl(C.sub.1-C.sub.4)alkylene, substituted heterocyclyl(C.sub.1-C.sub.4)alkylene, substituted (C.sub.1-C.sub.4)alkylheterocyclylene, and substituted (C.sub.1-C.sub.4)alkylheterocyclyl(C.sub.1-C.sub.4)alkylene are substituted with one or more substituents each independently selected from the group consisting of (C.sub.1-C.sub.30)alkyl, (C.sub.1-C.sub.30)alkoxy, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkenyloxy, (C.sub.2-C.sub.30)alkynyl, (C.sub.2-C.sub.30)alkynyloxy, aryl, aryloxy, heteroaryl, heteroaryloxy, heterocyclyl, heterocyclyloxy, aryl(C.sub.1-C.sub.4)alkyl, aryl(C.sub.1-C.sub.4)alkoxy, heteroaryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkoxy, heterocyclyl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkoxy; [0360] wherein R.sup.9 is selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; [0361] wherein each R.sup.19 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; [0362] wherein each R.sup.20 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; [0363] wherein each R.sup.21 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; [0364] wherein R.sup.22 is selected from the group consisting of (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; [0365] wherein each R.sup.23 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; [0366] wherein R.sup.24 is selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; and [0367] wherein R.sup.25 is selected from the group consisting of (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; [0368] optionally wherein the alpha-carbon of at least one R.sup.19 is a secondary or tertiary carbon; [0369] optionally wherein the alpha-carbon of at least one R.sup.21 is a secondary or tertiary carbon; optionally wherein the alpha-carbon of R.sup.22 is a secondary or tertiary carbon; [0370] optionally wherein the alpha-carbon of at least one R.sup.23 is a secondary or tertiary carbon; and [0371] optionally wherein the alpha-carbon of R.sup.24 is a secondary or tertiary carbon; [0372] provided that all R.sup.19 are not simultaneously hydrogen; [0373] provided that all R.sup.20 are not simultaneously hydrogen; [0374] provided that at least one R.sup.20 includes one or more heteroatoms selected from N, O, and S replacing the beta-carbon or gamma-carbon, and/or one or more heteroatoms selected from N, O, and S substituted for hydrogens on the alpha-carbon, beta-carbon, or gamma-carbon; or an alpha-carbon of at least one R.sup.20 is a secondary carbon or a tertiary carbon; [0375] provided that both R.sup.21 are not simultaneously hydrogen; [0376] provided that both R.sup.23 are not simultaneously hydrogen; and [0377] provided that R.sup.6 has a structure such that the two thiol groups are not bonded to the same carbon.

[0378] A fourteenth aspect relates to the method of aspect 10, wherein the copper-coordinating additive is a soft base, benzotriazole, an amino acid, a surfactant, a compound comprising an imidazole or a reduced imidazole group, a nitrile compound, or a compound of formula (I), (VI), (VII), (XI), (XII), (XIX), (XX), (XXI), (XXII), (XXIII), (XXIV), (XXV), or (XXVI):

##STR00054## [0379] wherein X.sup. is selected from the group consisting of fluoride, chloride, bromide, iodide, hexafluorophosphate, sulfate, an alkylsulfonate, and an arylsulfonate; [0380] wherein a is an integer from 1 to 4; [0381] wherein b is an integer from 1 to 4, [0382] wherein c is an integer from 0 to 3; [0383] wherein each of R.sup.1 and R.sup.2 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; [0384] wherein R.sup.9 is selected from the group consisting of (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; [0385] wherein each of R.sup.10 and R.sup.11 is independently selected from the group consisting of (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; [0386] wherein each R.sup.19 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; [0387] wherein each R.sup.20 is independently selected form the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; [0388] wherein each R.sup.21 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; [0389] wherein R.sup.22 is selected from the group consisting of (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; [0390] wherein each R.sup.23 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl; [0391] wherein R.sup.24 is selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; [0392] wherein R.sup.25 is selected from the group consisting of (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; [0393] wherein each of R.sup.26, R.sup.27, R.sup.28, and R.sup.29 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; [0394] wherein each of R.sup.30, R.sup.31, R.sup.32, and R.sup.33 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; [0395] wherein each of R.sup.34, R, and R.sup.36 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; [0396] wherein each of R.sup.37, R.sup.38, and R.sup.39 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; [0397] wherein the nitrile compound is selected from the group consisting of a (C.sub.1-C.sub.30)alkylnitrile, a (C.sub.2-C.sub.30)alkenylnitrile, a (C.sub.2-C.sub.30)alkynylnitrile, an arylnitrile, a heteroarylnitrile, a heterocyclylnitrile, an aryl(C.sub.1-C.sub.4)alkylnitrile, a heteroaryl(C.sub.1-C.sub.4)alkylnitrile, and a heterocyclyl(C.sub.1-C.sub.4)alkylnitrile; and [0398] wherein a substituted compound of formula (XXIV) includes one or more carbons substituted with one or more substituents selected from the group consisting of (C.sub.1-C.sub.30)alkyl, (C.sub.1-C.sub.30)alkoxy, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkenyloxy, (C.sub.2-C.sub.30)alkynyl, (C.sub.2-C.sub.30)alkynyloxy, aryl, aryloxy, heteroaryl, heteroaryloxy, heterocyclyl, heterocyclyloxy, aryl(C.sub.1-C.sub.4)alkyl, aryl(C.sub.1-C.sub.4)alkoxy, heteroaryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkoxy, heterocyclyl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkoxy; [0399] optionally wherein the alpha-carbon of at least one of R.sup.26, R.sup.27, R.sup.28, and R.sup.29 is a secondary or tertiary carbon; [0400] optionally wherein the alpha-carbon of at least one of R.sup.30, R.sup.31, R.sup.32, and R.sup.33 is a secondary or tertiary carbon; [0401] optionally wherein the alpha-carbon of at least one of R.sup.34, R.sup.3, and R.sup.36 is a secondary or tertiary carbon; [0402] optionally wherein the alpha-carbon of at least one of R.sup.37, R.sup.38, and R.sup.39 is a secondary or tertiary carbon; and [0403] optionally wherein the alpha-carbon of the nitrile compound is a secondary or tertiary carbon; [0404] provided that both of R.sup.1 and R.sup.2 are not simultaneously hydrogen and that the alpha-carbon of at least one of R.sup.1 and R.sup.2 is a secondary or tertiary carbon; [0405] provided that the alpha-carbon of R.sup.9 is a secondary or tertiary carbon; [0406] provided that the alpha carbon of at least one of R.sup.10 and R.sup.11 is a secondary or tertiary carbon; [0407] provided that all R.sup.19 are not simultaneously hydrogen and that the alpha-carbon of at least one R.sup.19 is a secondary or tertiary carbon; [0408] provided that all R.sup.20 are not simultaneously hydrogen, and that an alpha-carbon of at least one R.sup.20 is a secondary carbon or a tertiary carbon; [0409] provided that both R.sup.21 are not simultaneously hydrogen; [0410] provided that the alpha-carbon of at least one R.sup.21 and/or R.sup.22 is a secondary or tertiary carbon; [0411] provided that the alpha-carbon of at least one R.sup.23 and/or R.sup.23 is a secondary or tertiary carbon; [0412] provided that the alpha-carbon of R.sup.W is a secondary or tertiary carbon; [0413] provided that R.sup.34, R.sup.35, and R.sup.36 are not simultaneously hydrogen; and [0414] provided that R.sup.37, R.sup.38, and R.sup.39 are not simultaneously hydrogen.

[0415] A fifteenth aspect relates to the method of any one of aspects 10 to 12, wherein the copper-coordinating additive is a compound selected from the group consisting of 2-ethylhexyl phosphate, bis(2-ethylhexyl)phosphate, methyl phosphate, dimethyl phosphate, trimethyl phosphate, phenyl phosphate, diphenyl phosphate, 2,2-bipyridine, terpyridine, citric acid, diethanolamine, triethanolamine, 14-crown-4, 15-crown-5, 18-crown-6, dibenzo-18-crown-6, aza-15-crown-5, aza-18-crown-6, and salen.

[0416] A sixteenth aspect relates to the method of aspects 10 to 15, wherein the biocidal material demonstrates a greater than 3 logarithmic reduction in a concentration of a bacteria selected from the group consisting of Staphylococcus aureus, Enterobacter aerogenes, Pseudomonas aeruginosa, Methicillin Resistant Staphylococcus aureus, E. coli, and mixtures thereof.

[0417] A seventeenth aspect relates to the method of aspects 10 to 16, wherein a CIE E* value of the biocidal material is less than about 10, as measured according to formula (XIII):

[00007] $\begin{matrix} E_{C}^{*} = \sqrt{({(L^{*} - L_{c ontrol}^{*})}^{2} + {(a^{*} - a_{control}^{*})}^{2} + {(b^{*} - b_{c ontrol}^{*})}^{2})} & (XIII) \end{matrix}$

wherein L*, a*, and b* are the CIE L*, a*, and b* values of the biocidal material and the L*.sub.control, a*.sub.control, and b*.sub.control are the CIE L*, a*, and b* values of the carrier.

[0418] An eighteenth aspect relates to a method of accelerating to a color endpoint in a biocidal material, comprising combining a copper-containing material comprising from 10 to 100 weight % of an amount of extractable copper with an amount of copper-coordinating additive, in a molar ratio of the amount of extractable copper to the amount of copper-coordinating additive of from 1:0.1 to 1:25 to form a copper-coordinating mixture; and combining the copper-containing mixture with a carrier to form the biocidal material; wherein a concentration of the copper-containing material and the copper-coordinating additive of the copper-containing mixture in the carrier is from 0.01% weight/weight of the carrier to 5% weight/weight of the carrier; wherein a CIE E* value of the biocidal material is less than about 10, as measured according to formula (XII):

[00008] $\begin{matrix} E_{C}^{*} = \sqrt{({(L^{*} - L_{c ontrol}^{*})}^{2} + {(a^{*} - a_{control}^{*})}^{2} + {(b^{*} - b_{c ontrol}^{*})}^{2})} & (XIII) \end{matrix}$

[0419] A nineteenth aspect relates to the method of aspect 18, wherein the copper-containing material comprises from 25 to 50 weight % of the amount of extractable copper.

[0420] A twentieth aspect relates to the method of aspects 18 or 19, wherein the copper-coordinating additive is a compound of formula (I), (III), (VI), (VII), (IX), (X), (XI), or (XII):

##STR00055## [0421] wherein each of R.sup.1 and R.sup.2 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; [0422] provided that both of R.sup.1 and R.sup.2 are not simultaneously hydrogen; [0423] R.sup.5 is selected from the group consisting of substituted or unsubstituted (C.sub.1-C.sub.30)alkyl, substituted or unsubstituted (C.sub.2-C.sub.30)alkenyl, substituted or unsubstituted (C.sub.2-C.sub.30)alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl(C.sub.1-C.sub.4)alkyl, substituted or unsubstituted heteroaryl(C.sub.1-C.sub.4)alkyl, and substituted or unsubstituted heterocyclyl(C.sub.1-C.sub.4)alkyl; [0424] the substituted (C.sub.1-C.sub.30)alkyl, substituted (C.sub.2-C.sub.30)alkenyl, substituted (C.sub.2-C.sub.30)alkynyl, substituted aryl, substituted heteroaryl, substituted heterocyclyl, substituted aryl(C.sub.1-C.sub.4)alkyl, substituted heteroaryl(C.sub.1-C.sub.4)alkyl, and substituted heterocyclyl(C.sub.1-C.sub.4)alkyl in formula (III) are substituted with one or more substituents each of which is independently selected from the group consisting of OH, NH.sub.2, SH, CN, C(O)NH.sub.2, and CO.sub.2H; [0425] X.sup. is selected from the group consisting of fluoride, chloride, bromide, iodide, hexafluorophosphate, sulfate, an alkylsulfonate, and an arylsulfonate; [0426] R.sup.9 is selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; [0427] each of R.sup.10 and R.sup.11 is independently selected from the group consisting of substituted or unsubstituted (C.sub.1-C.sub.30)alkyl, substituted or unsubstituted (C.sub.2-C.sub.30)alkenyl, substituted or unsubstituted (C.sub.2-C.sub.30)alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl(C.sub.1-C.sub.4)alkyl, substituted or unsubstituted heteroaryl(C.sub.1-C.sub.4)alkyl, and substituted or unsubstituted heterocyclyl(C.sub.1-C.sub.4)alkyl; [0428] the substituted (C.sub.1-C.sub.30)alkyl, substituted (C.sub.2-C.sub.30)alkenyl, substituted (C.sub.2-C.sub.30)alkynyl, substituted aryl, substituted heteroaryl, substituted heterocyclyl, substituted aryl(C.sub.1-C.sub.4)alkyl, substituted heteroaryl(C.sub.1-C.sub.4)alkyl, and substituted heterocyclyl(C.sub.1-C.sub.4)alkyl in formula (VII) are substituted with one or more substituents each of which is independently selected from the group consisting of OH, NH.sub.2, SH, CN, C(O)NH.sub.2, C(O)NHR.sup.11, C(O)NR.sup.112, CO.sub.2H, and CO.sub.2R.sup.11; [0429] each R.sup.14 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.1-C.sub.30)alkoxy, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkenyloxy, (C.sub.2-C.sub.30)alkynyl, (C.sub.2-C.sub.30)alkynyloxy, aryl, aryloxy, heteroaryl, heteroaryloxy, heterocyclyl, heterocyclyloxy, aryl(C.sub.1-C.sub.4)alkyl, aryl(C.sub.1-C.sub.4)alkoxy, heteroaryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkoxy, heterocyclyl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkoxy; [0430] R.sup.15 is selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, heterocyclyl(C.sub.1-C.sub.4)alkyl, and (C(R.sup.14).sub.2).sub.pNH.sub.2; [0431] each of m, n, and p is independently 2 or 3; [0432] Y is O or S; [0433] each R.sup.16 is independently OR.sup.17 or N(R.sup.18).sub.2; [0434] R.sup.17 is selected from the group consisting of (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; [0435] each R.sup.18 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; [0436] each R.sup.19 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; [0437] provided that all R.sup.19 are not simultaneously hydrogen; [0438] each R.sup.20 is independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.30)alkyl, (C.sub.2-C.sub.30)alkenyl, (C.sub.2-C.sub.30)alkynyl, aryl, heteroaryl, heterocyclyl, aryl(C.sub.1-C.sub.4)alkyl, heteroaryl(C.sub.1-C.sub.4)alkyl, and heterocyclyl(C.sub.1-C.sub.4)alkyl; and [0439] provided that all R.sup.20 are not simultaneously hydrogen.

[0440] A twenty-first aspect relates to the method of aspects 18 to 20, wherein the copper-coordinating additive is a compound selected from the group consisting of 2-ethylhexyl phosphate, bis(2-ethylhexyl)phosphate, methyl phosphate, dimethyl phosphate, trimethyl phosphate, phenyl phosphate, diphenyl phosphate, citric acid, ethoxyamine hydrochloride, triethyl citrate, thiourea, urea, 14-crown-4, 15-crown-5, 18-crown-6, dibenzo-18-crown-6, aza-15-crown-5, aza-18-crown-6, and salen.

[0441] A twenty-second aspect relates to the method of aspects 18 to 21, wherein the biocidal material demonstrates a greater than 3 logarithmic reduction in a concentration of a bacterial selected from the group consisting of Staphylococcus aureus, Enterobacter aerogenes, Pseudomonas aeruginosa, Methicillin Resistant Staphylococcus aureus, E. coli, and mixtures thereof.

[0442] A twenty-third aspect relates to the method of aspects 18 to 22, wherein the method further comprises: treating the copper-containing material with a pretreatment solution prior to the combining with the amount of copper-coordinating additive.

[0443] A twenty-fourth aspect relates to the method of aspects 18 to 23, wherein the copper-coordinating additive is a compound of formula (VIII):

##STR00056## [0444] wherein R.sup.12 is selected from the group consisting of substituted or unsubstituted (C.sub.1-C.sub.30)alkyl, substituted or unsubstituted (C.sub.2-C.sub.30)alkenyl, substituted or unsubstituted (C.sub.2-C.sub.30)alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl(C.sub.1-C.sub.4)alkyl, substituted or unsubstituted heteroaryl(C.sub.1-C.sub.4)alkyl, and substituted or unsubstituted heterocyclyl(C.sub.1-C.sub.4)alkyl; [0445] each R.sup.13 is independently selected from the group consisting of hydrogen, substituted or unsubstituted (C.sub.1-C.sub.30)alkyl, substituted or unsubstituted (C.sub.2-C.sub.30)alkenyl, substituted or unsubstituted (C.sub.2-C.sub.30)alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl(C.sub.1-C.sub.4)alkyl, substituted or unsubstituted heteroaryl(C.sub.1-C.sub.4)alkyl, and substituted or unsubstituted heterocyclyl(C.sub.1-C.sub.4)alkyl; and [0446] the substituted (C.sub.1-C.sub.30)alkyl, substituted (C.sub.2-C.sub.30)alkenyl, substituted (C.sub.2-C.sub.30)alkynyl, substituted aryl, substituted heteroaryl, substituted heterocyclyl, substituted aryl(C.sub.1-C.sub.4)alkyl, substituted heteroaryl(C.sub.1-C.sub.4)alkyl, and substituted heterocyclyl(C.sub.1-C.sub.4)alkyl are substituted with one or more substituents each of which is independently selected from the group consisting of OH, NH.sub.2, SH, CN, C(O)NH.sub.2, C(O)NHR.sup.13, C(O)NR.sup.132, CO.sub.2H, and CO.sub.2R.sup.13.

[0447] In addition to the features mentioned in each of the independent aspects enumerated above, some examples may show, alone or in combination, the optional features mentioned in the dependent aspects and/or as disclosed in the description above and shown in the figures.

ADDITIVES FOR COLOR DRIFT REDUCTION IN COPPER-BASED ANTIMICROBIAL POLYMERIC FORMULATIONS

Inventors

Cpc classification

Classification Explorer

A01N59/20

HUMAN NECESSITIES

Classification Explorer

A01N25/22

HUMAN NECESSITIES

Classification Explorer

A01P15/00

HUMAN NECESSITIES

International classification

Classification Explorer

A01N59/20

HUMAN NECESSITIES

Classification Explorer

A01N25/22

HUMAN NECESSITIES

Classification Explorer

A01P15/00

HUMAN NECESSITIES

Abstract

Claims

Description