Ionic bonding group-containing comb polymers

Abstract

The invention relates to a copolymer that can be used as wetting agent and dispersant and contains i) 40-73 mole percent of a base structural unit (A) and ii) 27-60 mole percent of a substituted dicarboxylic acid derivative structural unit (B), the structural unit (B) containing species having a bisamide structure and species having quaternized amino groups.

Claims

1. A copolymer containing i) 40-73 mole percent of a base structural unit (A) and ii) 27-60 mole percent of a substituted dicarboxylic acid derivative structural unit (B), wherein the base structural unit (A) is generated by reacting a monomer (a) containing an olefinic double bond as well as no species falling under the dicarboxylic acid derivative structural unit (B), wherein the substituted dicarboxylic acid derivative structural unit (B) is present according to one or more of the general formulas of the group consisting of (I-1), (I-2), (I-3), (I-4), (I-5), (I-6), (II-1), (II-2), (II-3), (III-1), (III-2), (III-3), (IV-1) and (IV-2) ##STR00008## ##STR00009## with Z1, Z2, Z3 and Z4 in each case identical or different and in each case independently of one another represented by hydrogen, a linear C.sub.1-C.sub.4 alkyl residue and/or polymer main chain linking sites, with the condition that, for each general formula, there are exactly two polymer main chain linking sites, X.sup.1 and X.sup.2 in each case identical or different and in each case independently of one another represented by NH and/or O, R.sup.1 and R.sup.2 in each case identical or different and in each case independently of one another represented by a branched or unbranched, saturated or unsaturated, organic residue containing at least four carbon atoms as well as at least three oxygen atoms, and which comprises no amine functions and no ammonium functions, E.sup.1 and E.sup.2 in each case identical or different and in each case independently of one another represented by an N,N-disubstituted amine residue of general formula (V-E) ##STR00010## with R.sup.11, R.sup.12 in each case identical or different and in each case independently of one another represented by a substituted or unsubstituted, branched or unbranched, C.sub.1-C.sub.24 alkyl group, by a substituted or unsubstituted C.sub.4-C.sub.10 cycloalkyl group, by a substituted or unsubstituted C.sub.6-C.sub.18 aryl group and/or a substituted or unsubstituted, branched or unbranched C.sub.7-C.sub.18 arylalkyl group, where R.sup.11 and R.sup.12 together with the N atom binding R.sup.11 and R.sup.12 can form an aromatic or aliphatic, substituted or unsubstituted, cyclic C.sub.3-C.sub.10 group, Y identical or different and represented by a substituted or unsubstituted, branched or unbranched, C.sub.1-C.sub.24 alkylene group and/or a substituted or unsubstituted C.sub.6-C.sub.18 arylene group Q.sup.1 and Q.sup.2 in each case identical or different and in each case independently of one another represented by a quaternary ammonium residue of general formula (V-Q) ##STR00011## with R.sup.11, R.sup.12 of the same equivalence as in the general formula (V-E), Y of the same equivalence as in the general formula (V-E), R.sup.13 identical or different and represented by hydrogen, by a substituted or unsubstituted, branched or unbranched, C.sub.1-C.sub.24 alkyl group, by a substituted or unsubstituted C.sub.4-C.sub.10 cycloalkyl group, by a substituted or unsubstituted C.sub.6-C.sub.18 aryl group and/or a substituted or unsubstituted, branched or unbranched, C.sub.7-C.sub.18 arylalkyl group, M.sup. identical or different and represented by an anion, wherein the molar fraction of the structural units that are part of the group consisting of (I-1), (I-2), (I-3), (I-4), (I-5) and (I-6) is 10-80%, relative to the totality of the structural units to be attributed to the dicarboxylic acid derivative structural unit (B), the molar fraction of the structural units that are part of the group consisting of (I-2), (I-3), (I-4), (I-5), (I-6), (II-2), (II-3), (III-2) and (III-3) is 10-90%, relative to the totality of the structural units to be attributed to the dicarboxylic acid derivative structural unit (B), and, regarding the dicarboxylic acid derivative structural unit (B), the molar fraction of the substituents that are part of the group consisting of Q.sup.1 and Q.sup.2 is 20-95%, relative to the totality of the substituents that are part of the group consisting of E.sup.1, E.sup.2, Q.sup.1 and Q.sup.2.

2. The copolymer according to claim 1 containing, i) 48-70 mole percent of the base structural unit (A) and ii) 30-52 mole percent of the substituted dicarboxylic acid derivative structural unit (B).

3. The copolymer according to claim 1, characterized in that the monomer (a) that produces the base structural unit (A) and contains an olefinic double bond is selected from one or more of the monomers of the group consisting of alkyl(meth)acrylates of straight-chain, branched or cycloaliphatic monoalcohols having 1 to 22 carbon atoms or of aromatic or straight-chain or branched mixed aromatic-aliphatic monoalcohols having 1 to 22 carbon atoms, alkenyl(meth)acrylates of straight-chain, branched or cycloaliphatic monoalcohols having 1 to 22 carbon atoms or of aromatic or straight-chain or branched mixed aromatic-aliphatic monoalcohols having 1 to 22 carbon atoms, mono(meth)acrylates of oligomeric or polymeric ethers, (meth)acrylates of halogenated alcohols; oxirane-containing (meth)acrylates, styrene, substituted styrenes, -olefins, vinyl ethers, allyl ethers; methacrylonitrile, acrylonitrile; cycloaliphatic heterocyclic compounds comprising vinyl groups and having at least one N-atom as ring member, vinyl esters of monocarboxylic acids having 1 to 20 carbon atoms, N-alkyl- and N,N-dialkyl-substituted acrylamides with straight-chain, branched or cycloaliphatic alkyl groups having 1-22 carbon atoms, ethylenically unsaturated monomers with at least one carboxylic acid, phosphonic acid, phosphoric acid or sulfonic acid group and unsaturated fatty acids.

4. The copolymer according to claim 1, characterized in that at least 60 mole percent of the structural units that are part of the base structural unit (A) are produced by reaction with styrene.

5. The copolymer according to claim 1, characterized in that M.sup. is present as carboxylate, as phosphate, as phosphate monoester, as phosphate diester, as alkyl sulfonate, as sulfate and/or as halide.

6. The copolymer according to claim 1, containing 12-500 structural units which are selected from the base structural unit (A) and the dicarboxylic acid derivative structural unit (B).

7. A method of preparing the copolymer according to claim 1, characterized in that first a copolymer precursor is produced by polymerization, wherein, by subsequent grafting, the structural units (I-1), (I-2), (I-3), (I-4), (I-5), (I-6), (II-1), (II-2), (II-3), (III-1), (III-2), and/or (III-3) of the dicarboxylic acid derivative structural unit (B) are formed.

8. The method according to claim 7, characterized in that the subsequent grafting is carried out by the use of procedures that get rid of reaction water, optionally by heating to a temperature from 120 to 200 C., until the molar fraction of the structural units which are part of the group consisting of (I-1), (I-2), (I-3), (I-4), (I-5) as well as (I-6), relative to the totality of the structural units that are to be attributed to the dicarboxylic acid derivative structural unit (B) is at least 5%.

9. Dispersion, which contains a dispersant medium as well as a dispersed particulate solid substance, which is optionally present in the form of an inorganic filler, and/or in the form of an inorganic or organic pigment and/or in the form of carbon nanotubes and/or in the form of graphenes, wherein, relative to the weight of the dispersion, 0.1 to 10 wt % of a copolymer according to claim 1 is used as wetting and dispersing agents.

10. The dispersion according to claim 9, which is present as ink or coating agent, optionally as lacquer.

11. Particle preparation containing 30.0 to 99.9 wt % particulate solid as well as 0.1-70.0 wt % of a copolymer according to claim 1.

12. A method comprising stirring or admixing the copolymer according to claim 1, as wetting and/or dispersing agent in a carrier medium, in a solid substance compressed cake containing organic solvent, plasticizer and/or water, or in a solvent-free manner.

13. The dispersion according to claim 9, wherein, relative to the weight of the dispersion, 0.3 to 4.5 wt % of the copolymer is used as wetting and dispersing agents.

14. The copolymer according to claim 1 containing, i) 50-67 mole percent of the base structural unit (A) and ii) 33-50 mole percent of the substituted dicarboxylic acid derivative structural unit (B).

15. The copolymer according to claim 1, characterized in that the molar fraction of the structural units that are part of the group consisting of (I-1), (I-2), (I-3), (I-4), (I-5) and (I-6) is 27-75%, relative to the totality of the structural units to be attributed to the dicarboxylic acid derivative structural unit (B), the molar fraction of the structural units that are part of the group consisting of (I-2), (I-3), (I-4), (I-5), (I-6), (II-2), (II-3), (III-2) and (III-3) is 20-80%, relative to the totality of the structural units to be attributed to the dicarboxylic acid derivative structural unit (B), and, regarding the dicarboxylic acid derivative structural unit (B), the molar fraction of the substituents that are part of the group consisting of Q.sup.1 and Q.sup.2 is 25-90%, relative to the totality of the substituents that are part of the group consisting of E.sup.1, E.sup.2, Q.sup.1 and Q.sup.2.

16. The copolymer according to claim 1, containing 20-200 structural units which are selected from the base structural unit (A) and the dicarboxylic acid derivative structural unit (B).

17. A copolymer containing i) 40-73 mole percent of a base structural unit (A) and ii) 27-60 mole percent of a substituted dicarboxylic acid derivative structural unit (B), wherein the base structural unit (A) is generated by reacting a monomer (a) containing an olefinic double bond as well as no species falling under the dicarboxylic acid derivative structural unit (B), wherein the substituted dicarboxylic acid derivative structural unit (B) is present according to one or more of the general formulas of the group consisting of (I-1), (I-2), (I-3), (I-4), (I-5), (I-6), (II-1), (II-2), (II-3), (III-1), (III-2), (III-3), (IV-1) and (IV-2) ##STR00012## ##STR00013## with Z1, Z2, Z3 and Z4 in each case identical or different and in each case independently of one another represented by hydrogen, a linear C.sub.1-C.sub.4 alkyl residue and/or polymer main chain linking sites, with the condition that, for each general formula, there are exactly two polymer main chain linking sites, X.sup.1 and X.sup.2 in each case identical or different and in each case independently of one another represented by NH and/or O, R.sup.1 and R.sup.2 in each case identical or different and in each case independently of one another represented by a branched or unbranched, saturated or unsaturated, organic residue containing at least four carbon atoms as well as at least three oxygen atoms, and which comprises no amine functions and no ammonium functions, E.sup.1 and E.sup.2 in each case identical or different and in each case independently of one another represented by an N,N-disubstituted amine residue of general formula (V-E) ##STR00014## with R.sup.11, R.sup.12 together with the N atom binding R.sup.11 and R.sup.12 forming an aromatic or aliphatic, substituted or unsubstituted, heterocyclic compound, which comprises in total two N atoms, Y identical or different and represented by a substituted or unsubstituted, branched or unbranched, C.sub.1-C.sub.24 alkylene group and/or a substituted or unsubstituted C.sub.6-C.sub.18 arylene group Q.sup.1 and Q.sup.2 in each case identical or different and in each case independently of one another represented by a quaternary ammonium residue of general formula (V-Q) ##STR00015## with R.sup.11, R.sup.12 of the same equivalence as in the general formula (V-E), Y of the same equivalence as in the general formula (V-E), R.sup.13 identical or different and represented by hydrogen, by a substituted or unsubstituted, branched or unbranched, C.sub.1-C.sub.24 alkyl group, by a substituted or unsubstituted C.sub.4-C.sub.10 cycloalkyl group, by a substituted or unsubstituted C.sub.6-C.sub.18 aryl group and/or a substituted or unsubstituted, branched or unbranched, C.sub.7-C.sub.18 arylalkyl group, M.sup. identical or different and represented by an anion, wherein the molar fraction of the structural units that are part of the group consisting of (I-1), (I-2), (I-3), (I-4), (I-5) and (I-6) is 5-100%, relative to the totality of the structural units to be attributed to the dicarboxylic acid derivative structural unit (B), the molar fraction of the structural units that are part of the group consisting of (I-2), (I-3), (I-4), (I-5), (I-6), (II-2), (II-3), (III-2) and (III-3) is 5-100%, relative to the totality of the structural units to be attributed to the dicarboxylic acid derivative structural unit (B), and, regarding the dicarboxylic acid derivative structural unit (B), the molar fraction of the substituents that are part of the group consisting of Q.sup.1 and Q.sup.2 is 10-100%, relative to the totality of the substituents that are part of the group consisting of E.sup.1, E.sup.2, Q.sup.1 and Q.sup.2.

Description

(1) The invention is explained in further detail below using embodiment examples.

(2) Starting Substances:

(3) Synthetic resin SMA 2000 SMA copolymer with a styrene content of 66 mole percent, pyridine acid number=335; manufacturer Cray Valley Jeffamine M 2070 Polyether monoamine with terminal primary amino group, molar ratio of ethylene oxide to propylene oxide repeated units approximately 31/10, amine number=27; manufacturer Hunstman Jeffamine M 2005 Polyether monoamine with terminal primary amino group, molar ratio of ethylene oxide to propylene oxide repeated units approximately 6/29, amine number=25; manufacturer Huntsman MPEG 750 Polyethylene glycol monomethyl ether, molecular weight approximately 750, OH number=75; manufacturer BASF Polyester PE Caprolactone polyester from WO 2009/103381, intermediate product A1, OH number=51 Polysiloxane S -Butyldimethylsiloxy--(3-(2-hydroxyethoxyl)propyl))-polydimethylsiloxane, M.sub.n=4670 g/mol, OH number=12; from Sigma-Aldrich Grilonit RV 1814 Alkyl glycidyl ether, manufacturer EMS Chemie Uniox Mus 15 -Methyl--(2-propenyloxyl)poly(oxy-1,2-ethanediyl), manufacturer NOF
Measurement Methods
Gel Permeation Chromatography (GPC)

(4) The gel permeation chromatography was carried out at 40 C. with a high-pressure fluid chromatography pump (Bischoff HPLC 2200) and a refractive index detector (Waters 419). As eluent, tetrahydrofuran was used at an elution rate of 1 mL/min. The calibration was carried out with polystyrene standard. The number-average molecular weight Mn, the weight-average molecular weight Mw, and the polymolecularity index PMI=Mw/Mn were calculated using the program NTeqGPC.

(5) Solid Matter

(6) Approximately 2 g of sample are weighed in a previously weighed aluminum dish and dried for 30 minutes at 150 C. in the drying cabinet, cooled in the exsiccator, and then weighed again. The residue corresponds to the solid matter content.

(7) Hydroxy Number

(8) Alcoholic hydroxyl groups are converted by acetylation with an excess of acetic acid anhydride. Subsequently, the excess acetic acid anhydride is cleaved off by water addition to form acetic acid and back titrated with ethanolic KOH. The OH number gives the quantity of KOH in mg equivalent to the quantity of acetic acid bound in the acetylation of 1 g substance.

(9) Amine Number

(10) The amine number (AmN) refers to the quantity of KOH in mg that corresponds to the amine content of 1 g of substance. The mean number is determined according to DIN 16945 by a neutralization reaction with 0.1N perchloric acid in acetic acid as titration agent:
RNH.sub.2+HClO.sub.4.fwdarw.RNH.sub.3.sup.++ClO.sub.4.sup.

(11) The additions of inert solvents, such as cyclohexane, dioxane, chlorobenzene, acetone, methyl ethyl ketone, can improve the titration of very weak bases.

(12) Acid Number

(13) The acid number (AN) refers to the quantity of KOH in mg that is required for the neutralization of 1 g of substance under the established conditions. The acid number is determined according to DIN EN ISO 2114 by a neutralization reaction with 0.1N KOH in ethanol as titration agent:

(14) ##STR00006##
Total Acid Number

(15) The total acid number (TAN) refers to the quantity of KOH in mg that is required for the neutralization of 1 g substance under the established conditions. Here, both the acid groups and also the acid anhydride groups are included.

(16) The total acid number is determined according to DIN EN ISO 2114 by a neutralization reaction with 0.1N KOH in ethanol as titration agent.

(17) ##STR00007##
Different Main Chains
Polymer 1: 0 Mole Percent Succinic Acid Diamide Structure (0 Mole Percent Structural Unit I), 90% Quat (i.e., 90 Mole Percent of the Tertiary Amino Groups Quaternized) (Comparison Example Relative to Polymer 3-6)

(18) 47.5 g synthetic resin SMA 2000 (TAN=335/141.5 mmol anhydride groups) are dissolved in 50 g methoxypropyl acetate and slowly mixed with 47.2 mmol Jeffamin M 2070 (AmN=27.0) at 110 C. After 30 min, 94.3 mmol N,N-dimethylaminopropylamine (AmN=1105) are metered in and reacted for 2 h at 130 C. Thereafter, the temperature is increased to 170 C. and the reaction is continued for an additional 4 h, wherein after 2 h a vacuum is applied in addition. In the process, the methoxypropyl acetate and reaction water are removed by distillation.

(19) The reaction product is dissolved to 50% in butyl glycol. AmN.sub.(theo.)=17 AmN.sub.(measured)=17 AN.sub.(measured)=4

(20) 100 g of the polymer solution are reacted at 120 C. with 3.5 g benzyl chloride for 4 h and adjusted with butyl glycol to a solid matter (solid matter content) of 50%.

(21) Polymer 2: 100 Mole Percent Succinic Acid Diamide Structure (Structural Unit I), Amine; 0% Quat (i.e., 0 Mole Percent of the Tertiary Amino Groups Quaternized) (Comparison Example Relative to Polymer 3-6)

(22) 47.5 g synthetic resin SMA 2000 (TAN=335/141.5 mmol anhydride groups) are dissolved in 50 g methoxypropyl acetate and mixed slowly with 47.2 mmol Jeffamin M 2070 (AmN=27.0) at 110 C. After 30 min, 235.9 mmol N,N-dimethylaminopropylamine (AmN=1105) are metered in and reacted for 2 h at 130 C. Thereafter, the temperature is increased to 170 C. and the reaction is continued for an additional 4 h, wherein after 2 h a vacuum is applied in addition. In the process, the methyl propyl acetate and the reaction water are removed by distillation.

(23) The reaction product is dissolved to 50% in butyl glycol. AmN.sub.(theo.)=40 AmN.sub.(measured)=40 AN.sub.(measured)=1
Polymer 3: 100 Mole Percent Succinic Acid Diamide Structure (Structural Unit I), 90% Quat;

(24) 100 g of the polymer solution Polymer 2 are reacted at 120 C. with 8 g benzyl chloride for 4 h and adjusted to a solid matter content of 50% with butyl glycol.

(25) Polymer 4: 100 Mole Percent Succinic Acid Diamide Structure, 45% Quat;

(26) 100 g of the polymer solution Polymer 2 are reacted at 120 C. with 4 g benzyl chloride for 4 h and adjusted to a solid matter content of 50% with butyl glycol.

(27) Polymer 5: 100 Mole Percent Succinic Acid Diamide Structure, 23% Quat;

(28) 100 g of the polymer solution Polymer 2 are reacted at 120 C. with 2 g benzyl chloride for 4 h and adjusted to a solid matter content of 50% with butyl glycol.

(29) Polymer 6: 100 Mole Percent Succinic Acid Diamide Structure, 11% Quat;

(30) 100 g of the polymer solution Polymer 2 are reacted at 120 C. with 1 g benzyl chloride for 4 h and adjusted to a solid matter content of 50% with butyl glycol.

(31) Polymer 7: 0 Mole Percent Succinic Acid Diamide Structure, 35% Quat;

(32) (Comparison Example Relative to Polymer 8-11)

(33) 47.5 g synthetic resin SMA 2000 (TAN=335/141.5 mmol anhydride groups) are dissolved in 50 g methoxypropyl acetate and mixed slowly with 70.8 mmol Jeffamin M 2070 (AmN=27.0) at 110 C. After 30 min, 70.8 mmol N,N-dimethylaminopropylamine (AmN=1105) are metered in and reacted at 130 C. for 2 h. Subsequently, the temperature is increased to 170 C., and the reaction is continued for an additional 4 h, wherein after 2 h, a vacuum is applied in addition. In the process, the methoxypropyl acetate and reaction water are removed by distillation. AmN.sub.(theo.)=20 AmN.sub.(measured)=20 AN.sub.(measured)=7

(34) 80 g of the polymer are reacted at 120 C. with 25.1 mmol benzoic acid and 25.1 mmol Grilonit RV1814 (EG=283 g/mol) for 4 h.

(35) Polymer 8: 5 Mole Percent Succinic Acid Diamide Structure, 35% Quat;

(36) 47.5 g synthetic resin SMA 2000 (TAN=335/141.5 mmol anhydride groups) are dissolved in 50 g methoxypropyl acetate and mixed slowly with 70.8 mmol Jeffamin M 2070 (AmN=27.0) at 110 C. After 30 min, 77.8 mmol N,N-dimethylaminopropylamine (AmN=1105) are metered in and reacted at 130 C. for 2 h. Subsequently, the temperature is increased to 170 C. and the reaction is continued for an additional 4 h, wherein after 2 h a vacuum is applied in addition. In the process, the methoxypropyl acetate and reaction water are removed by distillation. AmN.sub.(theo.)=22 AmN.sub.(measured)=22 AN.sub.(measured)=7

(37) 80 g of the polymer are reacted at 120 C. with 27.7 mmol benzoic acid and 27.7 mmol Grilonit RV1814 (EG=283 g/mol) for 4 h.

(38) Polymer 9: 10 Mole Percent Succinic Acid Diamide Structure, 35% Quat;

(39) 47.5 g synthetic resin SMA 2000 (TAN=335/141.5 mmol anhydride groups) are dissolved in 50 g methoxypropyl acetate and mixed slowly with 70.8 mmol Jeffamin M 2070 (AmN=27.0) at 110 C. After 30 min, 84.9 mmol N,N-dimethylaminopropylamine (AmN=1105) are metered in and reacted at 130 C. for 2 h. Subsequently, the temperature is increased to 170 C. and the reaction is continued for an additional 4 h, wherein after 2 h a vacuum is applied in addition. In the process, the methoxypropyl acetate and reaction water are removed by distillation. AmN.sub.(theo.)=24 AmN.sub.(measured)=24 AN.sub.(measured)=19.7

(40) 80 g of the polymer are reacted at 120 C. with 30.1 mmol benzoic acid and 30.1 mmol Grilonit RV1814 (EG=283 g/mol) for 4 h.

(41) Polymer 10: 15 Mole Percent Succinic Acid Diamide Structure, 35% Quat;

(42) 47.5 g synthetic resin SMA 2000 (TAN=335/141.5 mmol anhydride groups) are dissolved in 50 g methoxypropyl acetate and mixed slowly with 70.8 mmol Jeffamin M 2070 (AmN=27.0) at 110 C. After 30 min, 92.0 mmol N,N-dimethylaminopropylamine (AmN=1105) are metered in and reacted at 130 C. for 2 h. Subsequently, the temperature is increased to 170 C. and the reaction is continued for an additional 4 h, wherein after 2 h a vacuum is applied in addition. In the process, the methoxypropyl acetate and reaction water are removed by distillation. AmN.sub.(theo.)=26 AmN.sub.(measured)=26 AN.sub.(measured)=6

(43) 80 g of the polymer are reacted at 120 C. with 32.6 mmol benzoic acid and 32.6 mmol Grilonit RV1814 (EG=283 g/mol) for 4 h.

(44) Polymer 11: 100 Mole Percent Succinic Acid Diamide Structure, 76% Quat;

(45) 47.5 g synthetic resin SMA 2000 (TAN=335/141.5 mmol anhydride groups) are dissolved in 50 g methoxypropyl acetate and mixed slowly with 70.8 mmol Jeffamin M 2070 (AmN=27.0) at 110 C. After 30 min, 92.0 mmol N,N-dimethylaminopropylamine (AmN=1105) are metered in and reacted at 130 C. for 2 h. Subsequently, the temperature is increased to 170 C. and the reaction is continued for an additional 4 h, wherein after 2 h a vacuum is applied in addition. In the process, the methoxypropyl acetate and reaction water are removed by distillation. AmN.sub.(theo.)=55 AmN.sub.(measured)=57 AN.sub.(measured)=1

(46) 80 g of the polymer are reacted at 120 C. with 70.6 mmol benzoic acid and 70.6 mmol Grilonit RV1814 (EG=283 g/mol) for 4 h.

(47) Polymer 12: 100 Mole Percent Succinic Acid Diamide Structure, 43% Quat;

(48) 47.5 g synthetic resin SMA 2000 (TAN=335/141.5 mmol anhydride groups) are dissolved in 50 g methoxypropyl acetate and mixed slowly with 46.7 mmol Jeffamin M 2070 (AmN=27.0) at 110 C. After 30 min, 236 mmol N,N-dimethylaminopropylamine (AmN=1105) are metered in and reacted at 130 C. for 2 h. Subsequently, the temperature is increased to 170 C. and the reaction is continued for an additional 4 h, wherein after 2 h a vacuum is applied in addition. In the process, the methoxypropyl acetate and reaction water are removed by distillation. AmN.sub.(theo.)=79 AmN.sub.(measured)=79 AN.sub.(measured)=1

(49) 80 g of the polymer are reacted at 120 C. with 101.4 mmol benzoic acid and 101.4 mmol Grilonit RV1814 (EG=283 g/mol) for 4 h.

(50) Polymer 13: Block Copolymer with pMMA-b-pSMA, 100 Mole Percent Structural Unit I, 40% Quat;

(51) Step a:

(52) In a round-bottom flask with reflux cooler, temperature sensor and CPG stirrer, under a nitrogen atmosphere, 59.1 g 2,4-diphenyl-4-methyl-1-pentene and 132.3 g 1-methoxy-2-propyl acetate are placed as starting materials and heated under stirring at 130 C. Subsequently, within 90 min, 250.3 g methyl methacrylate with 3.3 g 2,2-azodi(2-methylbutyronitrile) are metered in. The reaction mixture is stirred for an additional 3 h (product: M.sub.n=630, M.sub.w=2900).

(53) Step b:

(54) In a round-bottom flask with reflux cooler, temperature sensor and CPG stirrer, under a nitrogen atmosphere, 100.00 g of the product of step a) are placed as starting material and heated under stirring at 130 C. Subsequently, within 60 min, in parallel 1.) 27.6 g MSA with 1.5 g 2,2-azodi(2-methylbutyronitrile) in 55.5 g 1-methoxy-2-propyl acetate as well as 2.) 29.4 g styrene are metered in. The reaction mixture is stirred for an additional 5 h. (solid substance: 60% product: M.sub.n=1900, M.sub.w=5400).

(55) Step c):

(56) 50 g step b (64 mmol anhydride groups) are mixed slowly with 40 mmol Jeffamin M 2070 (AmN=27.0) at 110 C. After 30 min, 88 mmol N,N-dimethylaminopropylamine (AmN=1105) are metered in and reacted at 130 C. for 2 h. Subsequently, the temperature is increased to 170 C. and the reaction is continued for an additional 4 h, wherein after 2 h a vacuum is applied in addition. In the process, the methoxypropyl acetate and reaction water are removed by distillation.

(57) The reaction product is dissolved to 50% in butyl glycol. AmN.sub.(theo.)=20 AmN.sub.(measured)=21 AN.sub.(measured)=2

(58) 100 g of the polymer solution are reacted at 120 C. with 2 g benzyl chloride for 4 h and the solid matter content is adjusted to 50% with butyl glycol.

(59) Polymer 14: Copolymer of MSA and Dodecene, 50 Mole Percent Structural Unit I; 57% Quat

(60) Step a:

(61) Into a round-bottom flask with reflux cooler, temperature sensor and CPG stirrer, under nitrogen atmosphere, 84.2 g 1-dodecene and 25.5 g xylene are filled and heated at 140 C. under stirring. Subsequently, in portions, 7 times every, 30 minutes, 7.00 g MSA as well as in each case 1 g di-tert-butyl peroxide are added in parallel. The reaction mixture is stirred for an additional 3 h at 140 C. Since the resulting product solidifies, 82. 00 g xylene are subsequently added. One gets a clear, yellow, medium-viscosity fluid (57% solution; M.sub.n=2500, M.sub.w=7100).

(62) Step b:

(63) 100 g step b (200 mmol anhydride groups) are added slowly with 200 mmol Jeffamin M 2070 (AmN=27.0) at 110 C. After 30 min, 100 mmol N,N-dimethylaminopropylamine (AmN=1105) are metered in and reacted at 130 C. for 2 h. Subsequently, the temperature is increased to 170 C. and the reaction is continued for an additional 4 h, wherein after 2 h a vacuum is applied in addition. In the process, the xylene and reaction water are removed by distillation.

(64) The reaction product is dissolved to 50% in butyl glycol. AmN.sub.(theo.)=6 AmN.sub.(measured)=8 AN.sub.(measured)=3

(65) 100 g of the polymer solution are reacted at 120 C. with 1 g benzyl chloride for 4 h and adjusted to a solid matter content of 50% with butyl glycol.

(66) Polymer 15: Copolymer of MSA and Allyl Polyether, Molar 1.8:1; 35 Mole Percent Structural Unit I; 20% Quat

(67) Step a:

(68) In a round-bottom flask with reflux cooler, temperature sensor and CPG stirrer, under nitrogen atmosphere, 130 g Uniox Mus 15 and 60.00 1-methoxy-2-propyl acetate are placed as starting substances and heated under stirring at 130 C. Subsequently, 20.7 g maleic acid anhydride with 1.84 g 2,2-azodi(2-methylbutyronitrile) in 94 g 1-methoxypropyl acetate are metered in within 90 minutes. The reaction mixture is stirred in addition for a total of 2 h at 130 C., during which time a reinitiation is carried out 3 times each time with 0.50 g 2,2-azodi(2-methylbutyronitrile). One gets a clear, yellow, low-viscosity fluid (50% solution; M.sub.n=4200, M.sub.w11,300).

(69) Step b:

(70) 100 g step a (67 mmol anhydride groups) are mixed slowly with 90 mmol N,N-dimethylaminopropylamine at 130 C. and reacted for 2 h. Thereafter, the temperature is increased to 170 C. and the reaction is continued for an additional 4 h, wherein after 2 h a vacuum is applied in addition. In the process, the methoxypropyl acetate and reaction water are removed by distillation.

(71) The reaction product is dissolved to 50% in butyl glycol. AmN.sub.(theo.)=43 AmN.sub.(measured)=45 AN.sub.(measured)=2

(72) 100 g of the polymer solution are reacted at 120 C. with 2 g benzyl chloride for 4 h and the solid matter content is adjusted to 50% with butyl glycol.

(73) Different Amines/Quaternary Ammonium Salts

(74) Polymer 16: Dimethylaminoethanol, 100 Mole Percent Structural Unit I, 22% Quat;

(75) 47.5 g synthetic resin SMA 2000 (TAN=335/141.5 mmol anhydride groups) are dissolved in 50 g methoxypropyl acetate and mixed slowly with 47.2 mmol Jeffamin M 2070 (AmN=27.0) at 110 C. After 30 min, 235.9 mmol N,N-dimethylaminoethanol are metered in and reacted at 130 C. for 2 h. Thereafter, the temperature is increased to 170 C. and the reaction is continued for an additional 4 h, wherein after 2 h a vacuum is applied in addition. In the process, the methoxypropyl acetate and reaction water are removed by distillation.

(76) The reaction product is dissolved to 50% in butyl glycol. AmN.sub.(theo.)=41 AmN.sub.(measured)=41 OHN.sub.(measured)=3 AN.sub.(measured)=3

(77) 100 g of the polymer solution are reacted at 120 C. with 2 g benzyl chloride for 4 h and the solid matter content is adjusted to 50% with butyl glycol.

(78) Polymer 17: N-(3-Aminopropyl)Imidazole, 100 Mole Percent Structural Unit I, 56% Quat;

(79) 47.5 g synthetic resin SMA 2000 (TAN=335/141.5 mmol anhydride groups) are dissolved in 50 g methoxypropyl acetate and mixed slowly with 47.2 mmol Jeffamin M 2070 (AmN=27.0) at 110 C. After 30 min, 235.9 mmol N-(3-aminopropyl)imidazole are metered in and reacted at 130 C. for 2 h. Thereafter, the temperature is increased to 170 C. and the reaction is continued for an additional 4 h, wherein after 2 h a vacuum is applied in addition. In the process, the methoxypropyl acetate and reaction water are removed by distillation.

(80) The reaction product is dissolved to 50% in butyl glycol. AmN.sub.(theo.)=38 AmN.sub.(measured)=39 AN.sub.(measured)=1

(81) 100 g of the polymer solution are reacted at 120 C. with 5 g benzyl chloride for 4 h and the solid matter content is adjusted to 50% with butyl glycol.

(82) Polymer 18: 4-Aminomethylpyridine, 100 Mole Percent Structural Unit I, 11% Quat;

(83) 47.5 g synthetic resin SMA 2000 (TAN=335/141.5 mmol anhydride groups) are dissolved in 50 g methoxypropyl acetate and mixed slowly with 47.2 mmol Jeffamin M 2070 (AmN=27.0) at 110 C. After 30 min, 235.9 mmol 4-aminomethylpyridine are metered in and reacted at 130 C. for 2 h. Thereafter, the temperature is increased to 170 C. and the reaction is continued for an additional 4 h, wherein after 2 h a vacuum is applied in addition. In the process, the methoxypropyl acetate and reaction water are removed by distillation.

(84) The reaction product is dissolved to 50% in butyl glycol. AmN.sub.(theo.)=40 AmN.sub.(measured)=41 AN.sub.(measured)=2

(85) 100 g of the polymer solution are reacted at 120 C. with 1 g benzyl chloride for 4 h and the solid matter content is adjusted to 50% with butyl glycol.

(86) Polymer 19: Quaternization with o-Cresyl Glycidyl Ether, 100 Mole Percent Structural Unit I, 60% Quat;

(87) 47.5 g synthetic resin SMA 2000 (TAN=335/141.5 mmol anhydride groups) are dissolved in 50 g methoxypropyl acetate and mixed slowly with 47.2 mmol Jeffamin M 2070 (AmN=27.0) at 110 C. After 30 min, 235.9 mmol N,N-dimethylaminopropylamine (AmN=1105) are metered in and reacted at 130 C. for 2 h. Thereafter, the temperature is increased to 170 C. and the reaction is continued for an additional 4 h, wherein after 2 h a vacuum is applied in addition. In the process, the methoxypropyl acetate and reaction water are removed by distillation.

(88) The reaction product is dissolved to 50% in butyl glycol. AmN.sub.(theo.)=40 AmN.sub.(measured)=40 AN.sub.(measured)=1

(89) 100 g of the polymer solution are reacted at 120 C. with 7.1 g o-cresyl glycidyl ether and 5.4 g benzoic acid for 4 h and the solid matter content is adjusted to 50% with butyl glycol.

(90) Polymer 20: Quaternization with Styrene Oxide, 100 Mole Percent Structural Unit I, 61% Quat;

(91) 47.5 g synthetic resin SMA 2000 (TAN=335/141.5 mmol anhydride groups) are dissolved in 50 g methoxypropyl acetate and mixed slowly with 47.2 mmol Jeffamin M 2070 (AmN=27.0) at 110 C. After 30 min, 235.9 mmol N,N-dimethylaminopropylamine (AmN=1105) are metered in and reacted at 130 C. for 2 h. Thereafter, the temperature is increased to 170 C. and the reaction is continued for an additional 4 h, wherein after 2 h a vacuum is applied in addition. In the process, the methoxypropyl acetate and reaction water are removed by distillation.

(92) The reaction product is dissolved to 50% in butyl glycol. AmN.sub.(theo.)=40 AmN.sub.(measured)=40 AN.sub.(measured)=1

(93) 100 g of the polymer solution are reacted at 120 C. with 5 g styrene oxide and 5.3 g benzoic acid for 4 h and the solid matter content is adjusted to 50% with butyl glycol.

(94) Different Side Chains

(95) Polymer 21: Jeffamin M 2005, 100 Mole Percent Structural Unit I, 83% Quat;

(96) 47.5 g synthetic resin SMA 2000 (TAN=335/141.5 mmol anhydride groups) are dissolved in 50 g methoxypropyl acetate and mixed slowly with 47.2 mmol Jeffamin M 2005 (AmN=25) at 110 C. After 30 min, 235.9 mmol N,N-dimethylaminopropylamine (AmN=1105) are metered in and reacted at 130 C. for 2 h. Thereafter, the temperature is increased to 170 C. and the reaction is continued for an additional 4 h, wherein, after 2 h, a vacuum is applied in addition. In the process, the methoxypropyl acetate and reaction water are removed by distillation.

(97) The reaction product is dissolved to 50% in butyl glycol. AmN.sub.(theo.)=37 AmN.sub.(measured)=37 AN.sub.(measured)=1

(98) 100 g of the polymer solution are reacted at 120 C. with 7 g benzyl chloride for 4 h, and the solid matter content is adjusted to 50% with butyl glycol.

(99) Polymer 22: Jeffamin M 2070/MPEG 750, 100 Mole Percent Structural Unit I, 49% Quat;

(100) 47.5 g synthetic resin SMA 2000 (TAN=335/141.5 mmol anhydride groups) are dissolved in 50 g methoxypropyl acetate and mixed slowly with 27.2 mmol Jeffamin M 2070 (AmN=27.0) and 20 mmol MPEG 750 at 110 C. After 30 min, 235.9 mmol N,N-dimethylaminopropylamine (AmN=1105) are metered in and reacted at 130 C. for 2 h. Thereafter, the temperature is increased to 170 C. and the reaction is continued for an additional 4 h, wherein, after 2 h, a vacuum is applied in addition. In the process, the methoxypropyl acetate and reaction water are removed by distillation.

(101) The reaction product is dissolved to 50% in butyl glycol. AmN.sub.(theo.)=46 AmN.sub.(measured)=46 OHN.sub.(measured)=1 AN.sub.(measured)=1

(102) 100 g of the polymer solution are reacted at 120 C. with 5 g benzyl chloride for 4 h, and the solid matter content is adjusted to 50% with butyl glycol.

(103) Polymer 23: MPEG 750, 100 Mole Percent Structural Unit I, 58% Quat;

(104) 47.5 g synthetic resin SMA 2000 (TAN=335/141.5 mmol anhydride groups) are dissolved in 50 g methoxypropyl acetate, 0.5 g potassium carbonate is added, and the reaction mixture is reacted for 3 h with 47.2 mmol MPEG 750 at 130 C. The OH number after the reaction is 2 mg KOH/g. Subsequently, 235.9 mmol N,N-dimethylaminopropylamine (AmN=1105) are metered in and reacted at 130 C. for 2 h. Thereafter, the temperature is increased to 170 C. and the reaction is continued for an additional 4 h, wherein, after 2 h, a vacuum is applied in addition. In the process, the methoxypropyl acetate and reaction water are removed by distillation.

(105) The reaction product is dissolved to 50% in butyl glycol. AmN.sub.(theo.)=62 AmN.sub.(measured)=61 OHN.sub.(measured)=1 AN.sub.(measured)=2

(106) 100 g of the polymer solution are reacted at 120 C. with 8 g benzyl chloride for 4 h, and the solid matter content is adjusted to 50% with butyl glycol.

(107) Polymer 24: Jeffamin M 2070/Polyester, 100 Mole Percent Structural Unit I, 50% Quat;

(108) 47.5 g synthetic resin SMA 2000 (TAN=335/141.5 mmol anhydride groups) are dissolved in 50 g methoxypropyl acetate and mixed slowly with 27.2 mmol Jeffamin M 2070 (AmN=27.0) and 20 mmol polyester PE at 110 C. After 30 min 235.9 mmol N,N-dimethylaminopropylamine (AmN=1105) are metered in and reacted at 130 C. for 2 h. Thereafter, the temperature is increased to 170 C. and the reaction is continued for an additional 4 h, wherein, after 2 h, a vacuum is applied in addition. In the process, the methoxypropyl acetate and reaction water are removed by distillation.

(109) The reaction product is dissolved to 50% in butyl glycol. AmN.sub.(theo.)=44 AmN.sub.(measured)=45 OHN.sub.(measured)=2 AN.sub.(measured)=2

(110) 100 g of the polymer solution are reacted at 120 C. with 5 g benzyl chloride for 4 h, and the solid matter content is adjusted to 50% with butyl glycol.

(111) Polymer 25: Jeffamin M 2005/Polysiloxane, 100 Mole Percent Structural Unit I, 63% Quat;

(112) 47.5 g synthetic resin SMA 2000 (TAN=335/141.5 mmol anhydride groups) are dissolved in 50 g methoxypropyl acetate and mixed slowly with 42.2 mmol Jeffamin M 2005 and 5 mmol polysiloxane S at 110 C. After 30 min 235.9 mmol N,N-dimethylaminopropylamine (AmN=1105) are metered in and reacted at 130 C. for 2 h. Thereafter, the temperature is increased to 170 C. and the reaction is continued for an additional 4 h, wherein, after 2 h, a vacuum is applied in addition. In the process, the methoxypropyl acetate and reaction water are removed by distillation.

(113) The reaction product is dissolved to 50% in butyl glycol. AmN.sub.(theo.)=35 AmN.sub.(measured)=36 OHN.sub.(measured)=1 AN.sub.(measured)=2

(114) 100 g of the polymer solution are reacted at 120 C. with 5 g benzyl chloride for 4 h, and the solid matter content is adjusted to 50% with butyl glycol.

(115) Polymer 26: No Side Chain, 100 Mole Percent Structural Unit I, 5% Quat;

(116) 47.5 g synthetic resin SMA 2000 (TAN=335/141.5 mmol anhydride groups) are dissolved in 50 g methoxypropyl acetate and 100 g butyl diglycol acetate and heated at 50 C. Subsequently, 283 mmol N,N-dimethylaminopropylamine (AmN=1105) are slowly metered in and the reaction mixture is reacted at 130 C. for 2 h. Thereafter, the temperature is increased to 170 C. and the reaction is continued for an additional 4 h, wherein, after 2 h, a vacuum is applied in addition. In the process, the methoxypropyl acetate and reaction water are removed by distillation.

(117) The polymer solution is adjusted to a solid matter content of 50% with butyl diglycol acetate. AmN.sub.(theo.)=132 AmN.sub.(measured)=131 AN.sub.(measured)=1

(118) 100 g of the polymer solution are reacted at 120 C. with 1 g benzyl chloride and salted with 75 g Disperbyk 111 and the solid matter content is adjusted to 50% with 75 g butyl diglycol acetate.

(119) c) Application Technology Testing

(120) Use of the Polymers According to the Invention as Wetting and Dispersing Agents for the Preparation of Pigment Concentrates and their Use in Lacquer Systems

(121) Starting substances FPD binder Benzyl methacrylate-methacrylic acid copolymer, 35% in methoxypropyl acetate, acid number 53, from Byk-Chemie Vinnol E 15/45 Copolymer of vinyl chloride and vinyl acetate from Wacker Chemie Ebecryl 81 Amine-modified polyester acrylate from Cytec Ebecryl 450 Fatty acid-modified polyester hexaacrylate from Cytec Irgacure 2022 Photoinitiator from BASF Irgacure 2100 Photoinitiator from BASF BYK 085 Silicon-containing polymer defoamer from BYK-Chemie BYK 377 Silicon-containing surface additive from BYK-Chemie BYK UV 3510 Silicon-containing surface additive from BYK-Chemie Spezial Schwarz [Special Soot pigment from Evonik Black] 250 Chromophtal Red A3B Amino anthraquinone pigment from BASF Novoperm yellow PM3R Isoindolin pigment from Clariant Irgalith Rubine L4BH Azo pigment from BASF Sun fast Blue 249-5412 Phthalocyanine pigment from Sun Chemicals PMA Methoxypropyl acetate
Preparation of a Color Resist Pigment Concentrate

(122) TABLE-US-00001 FPD binder 7.14 PMA 30.86 W + DA [Wetting and 4.50 Dispersing Agent] Chromophtal Red A3B 7.5 50.00

(123) Dispersion with Lau Paint Shaker DAS H [/A]200-K: ratio of ground material to zirconium beads (0.4-0.6 mm diameter): 1:2 (parts by weight), 300 min, cooling step 3, normal speed.

(124) The viscosity measurements were carried out with the Stresstech apparatus of Reologica Instruments AB. In the process, the cylinder measurement system CC 25 was used. The equilibration time before the start of the measurement was 5 s. 12 measurement points were recorded at a shearing rate of 100 1/s with a total measurement duration of 48 s at a measurement temperature of 25 C. The indicated viscosity value is the mean value of the last 10 measurement points.

(125) The transparency was evaluated visually: 1-5, 1=very good, 5=very poor

(126) Result

(127) TABLE-US-00002 Viscosity Transparency Viscosity Transparency W + DA immediate immediate 14 d/40 C. 14 d/40 C. Polymer 1 16.9 mPas 2 17.5 mPas 2 Polymer 2 25.5 mPas 4 59.1 mPas 4 Polymer 3 13.6 mPas 1 13.8 mPas 1 Polymer 4 14.3 mPas 1 14.8 mPas 1 Polymer 5 15.4 mPas 1 16.3 mPas 1 Polymer 6 19.8 mPas 2 28.6 mPas 2

(128) The results show that with the polymer 3 according to the invention, a lower-viscosity and more storage-stable pigment dispersion compared to Polymer 1 is obtained. Moreover, a transparent lacquer film is obtained. In the variation of the quaternization degree, the quaternized wetting and dispersing agents (Polymer 3-6) showed better results than the unquaternized comparison product Polymer 2.

(129) Preparation of Pigmented Inkjet Inks

(130) TABLE-US-00003 Special Novoperm Black 250 yellow PM3R Butyl glycol acetate 34.25 36.25 Cyclohexanone 3.00 3.00 Vinnol E 15/45 0.75 0.75 W + DA 6.0 5.0 Pigment 6.0 5.0 50.00 50.00

(131) Dispersion with Lau Paint Shaker DAS H [/A]200-K: ratio of ground material to zirconium beads (0.4-0.6 mm diameter): 1:2 (parts by weight), 960 min, cooling step 3, normal speed.

(132) The viscosity measurements were carried out with the Stresstech apparatus of Reologica Instruments AB. In the process, the cylinder measurement system CC 25 was used. The equilibration time before the start of the measurement was 5 s. 12 measurement points were recorded at a shearing rate of 100 1/s with a total measurement duration of 48 s at a measurement temperature of 25 C. The indicated viscosity value is the mean value of the last 10 measurement points.

(133) The transparency was evaluated visually: 1-5, 1=very good, 5=very poor

(134) Result

(135) Spezial Schwarz 250

(136) TABLE-US-00004 Viscosity Transparency Viscosity Transparency W + DA immediate immediate 14 d/40 C. 14 d/40 C. Polymer 1 8.5 mPas 5 11.1 mPas 5 Polymer 3 8.5 mPas 2 10.3 mPas 2
Novoperm Yellow PM3R

(137) TABLE-US-00005 Viscosity Transparency Viscosity Transparency W + DA immediate immediate 14 d/40 C. 14 d/40 C. Polymer 1 10.1 mPas 2 19.8 mPas 2 Polymer 3 7.9 mPas 1-2 7.9 mPas 1-2

(138) The results show that, with the polymer 3 according to the invention, a lower-viscosity and more storage-stable pigment dispersion is obtained in comparison to Polymer 1. Moreover, a transparent lacquer film is obtained.

(139) Preparation of Pigmented UV Printing Inks

(140) Pigment Concentrate:

(141) TABLE-US-00006 Irgalith Sun fast Blue Spezial L4BH 249-5412 Schwarz 250 Ebecryl 81 66.6 66.6 45.78 Ebecrytl 450 10.3 10.3 18.7 W + DA 3.0 3.0 4.25 Byk-085 0.1 0.1 1 Pigment 20.0 20.0 30.0

(142) Dispersion with Dispermat CV: Ratio of ground material to glass beads (1 mm diameter): 1:1 (parts by weight), 30 min, 40 C., 10,000 rpm.

(143) Printing Ink:

(144) TABLE-US-00007 Ebecryl 81 89.80 89.80 79.9 Byk-377 0.20 0.20 Byk UV 3510 0.1 Irgacure 2022 10.0 10.0 Irgacure 2100 20.0
Lacquer Preparation:

(145) TABLE-US-00008 Pigment concentrate 6.0 6.0 5.0 Lacquer 4.0 4.0 5.0

(146) After complete drying, the gloss was measured using a Micro Tri Gloss gloss measurement apparatus (Manufacturer: BYK Gardner, Geretsried) under angles of 20.

(147) The viscosity and color strengths were evaluated visually: 1-5, 1=very good, 5=very poor

(148) Results:

(149) Sun Fast Blue 249-5412

(150) TABLE-US-00009 Viscosity Color Gloss Viscosity Color PC strength immediate PC strength W + DA immediate immediate 20 5 d/40 C. 5 d/40 C. Polymer 7 1 1 54 4 2 Polymer 8 1 1 59 3 1-2 Polymer 9 1 1 60 2 1 Polymer 10 1 1 61 2 1 Polymer 11 1 1 65 2 1 Polymer 12 1 1 62 2 1
Irgalith L4BH

(151) TABLE-US-00010 Viscosity Color Gloss Viscosity Color PC strength immediate PC strength W + DA immediate immediate 20 5 d/40 C. 5 d/40 C. Polymer 7 3/2 2 60 5 3 Polymer 8 2 2 61 3 2 Polymer 9 2 2 62 3 2 Polymer 10 2 2 63 3 2 Polymer 11 2 2 64 3 2 Polymer 12 2 2 63 3 2
Spezial Schwarz 250

(152) TABLE-US-00011 Viscosity Color Gloss Viscosity Color PC strength immediate PC strength W + DA immediate immediate 20 5 d/40 C. 5 d/40 C. Polymer 7 2 2 7 3 3 Polymer 8 1 1 7 2 2 Polymer 9 1 1 8 2 1 Polymer 10 1 1 9 2 1 Polymer 11 1 1 8 2 1 Polymer 12 1 1 8 2 1

(153) The results show that, with copolymers 8-12 according to the invention, which contain bisamide structures, pigmented lacquers with improved properties in terms of viscosity, storage stability, gloss and color strength are obtained in comparison to Polymer 7 which contains no bisamide structures.