N-Alkyl glucamine-based universal pigment dispersions

Abstract

The invention relates to aqueous binder-free pigment dispersions containing (A) at least one organic and/or inorganic pigment, (B) one or more dispersing agents and/or surfactants, (C) at least one base of formula (I), where R.sup.1 is H, C.sub.1-C.sub.4-alkyl, CH.sub.2CH.sub.2OH or CH.sub.2CH(CH.sub.3)OH, (D) optionally, one or more polyalkylene glycols, (E) optionally, other additives commonly used for making aqueous pigment dispersions, and (F) water. ##STR00001##

Claims

1. An aqueous, water-thinnable or solvent borne varnish comprising at least one aqueous, binder-free pigment dispersion, wherein the at least one aqueous, binder-free pigment dispersion comprises (A) at least one organic and/or inorganic pigment, (B) one or more dispersants and/or surfactants, (C) at least one compound of the formula (I) ##STR00004## in which R.sup.1 is H, C.sub.1-C.sub.4-alkyl, CH.sub.2CH.sub.2OH or CH.sub.2CH(CH.sub.3)OH, and (F) water.

2. The aqueous, water-thinnable or solvent borne varnish as claimed in claim 1, in which R.sup.1 is methyl or CH.sub.2CH.sub.2OH.

3. The aqueous, water-thinnable or solvent borne varnish as claimed in claim 1, in which R.sup.1 is methyl.

4. The aqueous, water-thinnable or solvent borne varnish as claimed in claim 1, wherein the inorganic pigment is a metal oxide pigment.

5. The aqueous, water-thinnable or solvent borne varnish as claimed in claim 1, comprising 5% to 80% by weight of component (A) based on the total weight of the pigment dispersion.

6. The aqueous, water-thinnable or solvent borne varnish as claimed in claim 1, comprising 0.1% to 30% by weight of component (B) based on the total weight of the pigment dispersion.

7. The aqueous, water-thinnable or solvent borne varnish as claimed in claim 1, comprising 0.1% to 10% by weight of component (C) based on the total weight of the pigment dispersion.

8. The aqueous, water-thinnable or solvent borne varnish as claimed in claim 1, comprising one or more polyalkylene glycols as component (D) in an amount of 0.1% to 10% by weight, based on the total weight of the pigment dispersion.

9. The aqueous, water-thinnable or solvent borne varnish as claimed in claim 1, comprising further additives customary for production of aqueous pigment dispersions as components (E) in an amount of 0% to 30% by weight, based on the total weight of the pigment dispersion.

10. An aqueous, water-thinnable or solvent borne paint comprising at least one aqueous, binder-free pigment dispersion, wherein the at least one aqueous, binder-free pigment dispersion comprises (A) at least one organic and/or inorganic pigment, (B) one or more dispersants and/or surfactants, (C) at least one compound of the formula (I) ##STR00005## in which R.sup.1 is H, C.sub.1-C.sub.4-alkyl, CH.sub.2CH.sub.2OH or CH.sub.2CH(CH.sub.3)OH, and (F) water.

11. The aqueous, water-thinnable or solvent borne paint as claimed in claim 10, in which R.sup.1 is methyl or CH.sub.2CH.sub.2OH.

12. The aqueous, water-thinnable or solvent borne paint as claimed in claim 10, in which R.sup.1 is methyl.

13. The aqueous, water-thinnable or solvent borne paint as claimed in claim 10, wherein the inorganic pigment is a metal oxide pigment.

14. The aqueous, water-thinnable or solvent borne paint as claimed in claim 10, comprising 5% to 80% by weight of component (A) based on the total weight of the pigment dispersion.

15. The aqueous, water-thinnable or solvent borne paint as claimed in claim 10, comprising 0.1% to 30% by weight of component (B) based on the total weight of the pigment dispersion.

16. The aqueous, water-thinnable or solvent borne paint as claimed in claim 10, comprising 0.1% to 10% by weight of component (C) based on the total weight of the pigment dispersion.

17. The aqueous, water-thinnable or solvent borne paint as claimed in claim 10, comprising one or more polyalkylene glycols as component (D) in an amount of 0.1% to 10% by weight, based on the total weight of the pigment dispersion.

18. The aqueous, water-thinnable or solvent borne paint as claimed in claim 10, comprising further additives customary for production of aqueous pigment dispersions as components (E) in an amount of 0% to 30% by weight, based on the total weight of the pigment dispersion.

19. An aqueous, water-thinnable or solvent borne ink comprising at least one aqueous, binder-free pigment dispersion, wherein the at least one aqueous, binder-free pigment dispersion comprises (A) at least one organic and/or inorganic pigment, (B) one or more dispersants and/or surfactants, (C) at least one compound of the formula (I) ##STR00006## in which R.sup.1 is H, C.sub.1-C.sub.4-alkyl, CH.sub.2CH.sub.2OH or CH.sub.2CH(CH.sub.3)OH, and (F) water.

20. The aqueous, water-thinnable or solvent borne ink as claimed in claim 19, in which R.sup.1 is methyl or CH.sub.2CH.sub.2OH.

21. The aqueous, water-thinnable or solvent borne ink as claimed in claim 19, in which R.sup.1 is methyl.

22. The aqueous, water-thinnable or solvent borne ink as claimed in claim 19, wherein the inorganic pigment is a metal oxide pigment.

23. The aqueous, water-thinnable or solvent borne ink as claimed in claim 19, comprising 5% to 80% by weight of component (A) based on the total weight of the pigment dispersion.

24. The aqueous, water-thinnable or solvent borne ink as claimed in claim 19, comprising 0.1% to 30% by weight of component (B) based on the total weight of the pigment dispersion.

25. The aqueous, water-thinnable or solvent borne ink as claimed in claim 19, comprising 0.1% to 10% by weight of component (C) based on the total weight of the pigment dispersion.

26. The aqueous, water-thinnable or solvent borne ink as claimed in claim 19, comprising one or more polyalkylene glycols as component (D) in an amount of 0.1% to 10% by weight, based on the total weight of the pigment dispersion.

27. The aqueous, water-thinnable or solvent borne ink as claimed in claim 19, comprising further additives customary for production of aqueous pigment dispersions as components (E) in an amount of 0% to 30% by weight, based on the total weight of the pigment dispersion.

Description

EXAMPLES

(1) The VOC content of a pigment dispersion is the sum total of the individual components in a dispersion that have a boiling point below 250 C. at 101.3 kPa. In order to formulate a VOC-free pigment dispersion, therefore, only those ingredients having a boiling point greater than 250 C. should be selected. In the case of use of amines that are customary on the market (examples 1 and 2, table 1), depending on their use concentration, these contribute 100% to the VOC content of the dispersion. Polyhydroxyamines of the formula (I) have a low VOC level owing to their high melting point and boiling point.

(2) TABLE-US-00001 TABLE 1 Boiling points of neutralizing agents Boiling point Example Neutralizing agent [ C.] 1 (C) 2-Amino-2-methylpropan-1-ol 165 2 (C) 2-(sec-Butylamino)ethanol 186 3 Compound of the formula (I) with R = H >>250 (m.p. 130 C.) 4 Compound of the formula (I) with R = CH.sub.3 >>250 (m.p. 90 C.)
Production of a Pigment Dispersion

(3) The pigment, in the form of powder, granules or a presscake, together with the dispersants and the other additives, is converted to a paste in deionized water and then homogenized and predispersed with a dissolver (for example from VMA-Getzmann GmbH, AE3-M1 type) or another suitable apparatus, preferably with the aid of a dispersing disk. For dispersion, the liquid components, the dispersant concentrate comprising components (B) and (C), and further components (D) and (F) are initially charged in a grinding vessel and mixed. Subsequently, the pulverulent components (A) and optionally (E) are added and predispersed with the dissolver. The subsequent fine dispersion is effected with the aid of a bead mill (for example AE3-M1 from VMA-Getzmann) or else another suitable dispersing unit, the grinding being effected with mixed zirconia beads of size d=1.3-1.7 mm with cooling. Subsequently, the grinding bodies are removed and the pigment preparation is isolated.

Example 5 (Comparative Example)

(4) TABLE-US-00002 65.5 parts C.I. Pigment Red 101 (Bayferrox Red 130, from Lanxess, component (A)), 10.0 parts mixture of an anionic and nonionic dispersant (Dispersogen AN 200, from Clariant, component (B)), 1.1 parts sodium hydroxide solution (10% aqueous solution, component (C)), 6.0 parts glycerol ethoxylate having a molecular weight of 300 g/mol (Polyglykol G 300, from Clariant, component (D)), 0.3 part defoamer (Byk-018, from Byk, component (E)), 0.2 part preservative (Acticide MBS, from Thor, component (E)), 16.9 parts water (component (F))

Example 6 (Comparative Example)

(5) TABLE-US-00003 65.5 parts C.I. Pigment Red 101 (Bayferrox Red 130, from Lanxess, component (A)), 10.0 parts mixture of an anionic and nonionic dispersant (Dispersogen AN 200, from Clariant, component (B)), 0.3 part 2-amino-2-methylpropan-1-ol (95% aqueous solution, AMP-95, from Angus, component (C)), 6.0 parts glycerol ethoxylate having a molecular weight of 300 g/mol (Polyglykol G 300, from Clariant, component (D)), 0.3 part defoamer (Byk-018, from Byk, component (E)), 0.2 part preservative (Acticide MBS, from Thor, component (E)), 17.7 parts water (component (F))

Example 7 (Comparative Example)

(6) TABLE-US-00004 65.5 parts C.I. Pigment Red 101 (Bayferrox Red 130, from Lanxess, component (A)), 10.0 parts mixture of an anionic and nonionic dispersant (Dispersogen AN 200, from Clariant, component (B)), 0.4 part 2-(sec-butylamino)ethanol ((Alpamine N41, from Arkema), component (C)), 6.0 parts glycerol ethoxylate having a molecular weight of 300 g/mol (Polyglykol G 300, from Clariant, component (D)), 0.3 part defoamer (Byk-018, from Byk, component (E)), 0.2 part preservative (Acticide MBS, from Thor, component (E)), 17.6 parts water (component (F))

Example 8

(7) TABLE-US-00005 65.5 parts C.I. Pigment Red 101 (Bayferrox Red 130, from Lanxess, component (A)), 10.0 parts mixture of an anionic and nonionic dispersant (Dispersogen AN 200, from Clariant, component (B)), 1.5 parts compound of the formula (I) with R = H (30% aqueous solution, component (C)), 6.0 parts glycerol ethoxylate having a molecular weight of 300 g/mol (Polyglykol G 300, from Clariant, component (D)), 0.3 part defoamer (Byk-018, from Byk, component (E)), 0.2 part preservative (Acticide MBS, from Thor, component (E)), 16.5 parts water (component (F))

Example 9

(8) TABLE-US-00006 65.5 parts C.I. Pigment Red 101 (Bayferrox Red 130, from Lanxess, component (A)), 10.0 parts mixture of an anionic and nonionic dispersant (Dispersogen AN 200, from Clariant, component (B)), 1.3 parts compound of the formula (I) with R = CH.sub.3 (50% aqueous solution, component (C)), 6.0 parts glycerol ethoxylate having a molecular weight of 300 g/mol (Polyglykol G 300, from Clariant, component (D)), 0.3 part defoamer (Byk-018, from Byk, component (E)), 0.2 part preservative (Acticide MBS, from Thor, component (E)), 16.7 parts water (component (F))

Example 10 (Comparative Example)

(9) TABLE-US-00007 65.5 parts C.I. Pigment Yellow 184 (Sicopal Gelb L 1100, from BASF, component (A)), 10.0 parts mixture of an anionic and nonionic dispersant (Dispersogen AN 200, from Clariant, component (B)), 1.0 parts sodium hydroxide solution (10% aqueous solution, component (C)), 6.0 parts glycerol ethoxylate having a molecular weight of 300 g/mol (Polyglykol G 300, from Clariant, component (D)), 0.3 part defoamer (Byk-018, from Byk, component (E)), 0.2 part preservative (Acticide MBS, from Thor, component (E)), 17.0 parts water (component (F))

Example 11 (Comparative Example)

(10) TABLE-US-00008 65.5 parts C.I. Pigment Yellow 184 (Sicopal Gelb L 1100, from BASF, component (A)), 10.0 parts mixture of an anionic and nonionic dispersant (Dispersogen AN 200, from Clariant, component (B)), 0.2 part 2-amino-2-methylpropan-1-ol (95% aqueous solution, AMP-95, from Angus, component (C)), 6.0 parts glycerol ethoxylate having a molecular weight of 300 g/mol (Polyglykol G 300, from Clariant, component (D)), 0.3 part defoamer (Byk-018, from Byk, component (E)), 0.2 part preservative (Acticide MBS, from Thor, component (E)), 17.8 parts water (component (F))

Example 12 (Comparative Example)

(11) TABLE-US-00009 65.5 parts C.I. Pigment Yellow 184 (Sicopal Gelb L 1100, from BASF, component (A)), 10.0 parts mixture of an anionic and nonionic dispersant (Dispersogen AN 200, from Clariant, component (B)), 0.2 part 2-(sec-butylamino)ethanol ((Alpamine N41, from Arkema), component (C)), 6.0 parts glycerol ethoxylate having a molecular weight of 300 g/mol (Polyglykol G 300, from Clariant, component (D)), 0.3 part defoamer (Byk-018, from Byk, component (E)), 0.2 part preservative (Acticide MBS, from Thor, component (E)), 17.8 parts water (component (F))

Example 13

(12) TABLE-US-00010 65.5 parts C.I. Pigment Yellow 184 (Sicopal Gelb L 1100, from BASF, component (A)), 10.0 parts mixture of an anionic and nonionic dispersant (Dispersogen AN 200, from Clariant, component (B)), 1.4 parts compound of the formula (I) with R = H (30% aqueous solution, component (C)), 6.0 parts glycerol ethoxylate having a molecular weight of 300 g/mol (Polyglykol G 300, from Clariant, component (D)), 0.3 part defoamer (Byk-018, from Byk, component (E)), 0.2 part preservative (Acticide MBS, from Thor, component (E)), 16.6 parts water (component (F))

Example 14

(13) TABLE-US-00011 65.5 parts C.I. Pigment Yellow 184 (Sicopal Gelb L 1100, from BASF, component (A)), 10.0 parts mixture of an anionic and nonionic dispersant (Dispersogen AN 200, from Clariant, component (B)), 1.4 parts compound of the formula (I) with R = CH.sub.3 (50% aqueous solution, component (C)), 6.0 parts glycerol ethoxylate having a molecular weight of 300 g/mol (Polyglykol G 300, from Clariant, component (D)), 0.3 part defoamer (Byk-018, from Byk, component (E)), 0.2 part preservative (Acticide MBS, from Thor, component (E)), 16.6 parts water (component (F))

(14) To characterize the dispersions, they were first aged at 60 C. for 7 days; all the pastes were stable over this period. In addition, the viscosity of the pigment dispersions was determined in a Haake VT 550 rheometer at a shear rate of 1/60 s and a temperature of 23 C. The results are listed in table 3 and have a pigment-typical viscosity.

(15) To determine the compatibility of the pigment dispersions based on various base coatings, 2% by weight of the dispersion was stirred into the paints and varnishes A-D (table 2) and drawn down onto a contrast card in a 200 m coat, and the color intensity was determined. The color intensity results are listed in table 3, and have the highest color intensities for the inventive polyhydroxyamines of the formula (I) both for red (examples 8 and 9) and for yellow (examples 13 and 14). The pastes comprising 2-(sec-butylamino)ethanol (comparative examples 7 and 12) are incompatible with solventborne coatings and lead to flocculation in use and hence are not amenable to colorimetry.

(16) TABLE-US-00012 TABLE 2 Coatings used for testing compatibility Paint/ varnish Description A Aqueous clearcoat based on an acrylate and polyurethane dispersion. Solids content: 40% B Aqueous clearcoat based on a polyurethane dispersion. Solids content: 35% C Solventborne alkyd resin clearcoat based on oils and aliphatic solvent. Solids content: 39% D Solventborne alkyd resin clearcoat based on aliphatic solvent. Solids content: 37%

(17) Parts or percentage figures are parts by weight or percent by weight, unless stated otherwise.

(18) TABLE-US-00013 TABLE 3 Results for examples 5 to 14 Outward Viscosity Color intensity/coating [%] Example appearance pH [mPas] A B C D 5 (C) liquid and 8.1 455 96 97 93 81 homogeneous 6 (C) liquid and 8.1 513 96 98 88 81 homogeneous 7 (C) thixotropic 8.1 521 98 95 flocculated flocculated and foamy 8 liquid and 8.1 638 100 99 97 92 homogeneous 9 liquid and 8.1 558 100 100 100 100 homogeneous 10 (C) liquid and 8.5 243 96 99 96 98 homogeneous 11 (C) liquid and 8.5 176 92 97 96 97 homogeneous 12 (C) slight 8.5 135 69 65 flocculated flocculated sediment 13 liquid and 8.5 311 94 95 102 103 homogeneous 14 liquid and 8.5 256 100 100 100 100 homogeneous

(19) For white pigments, the determination of the color intensity is unsuitable in the case of clearcoats. What is more suitable here is the determination of the concealing capacity as evidence of the fine distribution of the pigment in the paint film; complete incompatibility leads to encapsulation of the pigment and the paint film appears clear (zero or barely any concealing capacity). For this purpose, the pigment dispersions which follow (examples 11 to 15) were produced with white pigment and then the concealing capacity was determined. For this purpose, the colorless base paints were admixed with 10% by weight of the titanium dispersions, and a 400 m paint film was drawn down on a black/white contrast card. After drying, the contrast between the white and black region was determined.

Example 15 (Comparative Example)

(20) TABLE-US-00014 65.5 parts C.I. Pigment White 6 (Kronos 2160, from Kronos, component (A)), 10.0 parts mixture of an anionic and nonionic dispersant (Dispersogen AN 200, from Clariant, component (B)), 0.3 part 2-amino-2-methylpropan-1-ol (95% aqueous solution, AMP-95, from Angus, component (C)), 6.0 parts glycerol ethoxylate having a molecular weight of 300 g/mol (Polyglykol G 300, from Clariant, component (D)), 0.3 part defoamer (Byk-018, from Byk, component (E)), 0.2 part preservative (Acticide MBS, from Thor, component (E)), 17.7 parts water (component (F))

Example 16 (Comparative Example)

(21) TABLE-US-00015 65.5 parts C.I. Pigment White 6 (Kronos 2160, from Kronos, component (A)), 10.0 parts mixture of an anionic and nonionic dispersant (Dispersogen AN 200, from Clariant, component (B)), 0.8 part 2-(sec-butylamino)ethanol ((Alpamine N41, from Arkema), component (C)), 6.0 parts glycerol ethoxylate having a molecular weight of 300 g/mol (Polyglykol G 300, from Clariant, component (D)), 0.3 part defoamer (Byk-018, from Byk, component (E)), 0.2 part preservative (Acticide MBS, from Thor, component (E)), 17.2 parts water (component (F))

Example 17

(22) TABLE-US-00016 65.5 parts C.I. Pigment White 6 (Kronos 2160, from Kronos, component (A)), 10.0 parts mixture of an anionic and nonionic dispersant (Dispersogen AN 200, from Clariant, component (B)), 1.5 parts compound of the formula (I) with R = H (30% aqueous solution, component (C)), 6.0 parts glycerol ethoxylate having a molecular weight of 300 g/mol (Polyglykol G 300, from Clariant, component (D)), 0.3 part defoamer (Byk-018, from Byk, component (E)), 0.2 part preservative (Acticide MBS, from Thor, component (E)), 16.5 parts water (component (F))

Example 18

(23) TABLE-US-00017 65.5 parts C.I. Pigment White 6 (Kronos 2160, from Kronos, component (A)), 10.0 parts mixture of an anionic and nonionic dispersant (Dispersogen AN 200, from Clariant, component (B)), 1.3 parts compound of the formula (I) with R = CH.sub.3 (50% aqueous solution, component (C)), 6.0 parts glycerol ethoxylate having a molecular weight of 300 g/mol (Polyglykol G 300, from Clariant, component (D)), 0.3 part defoamer (Byk-018, from Byk, component (E)), 0.2 part preservative (Acticide MBS, from Thor, component (E)), 16.7 parts water (component (F))

(24) The results of the concealing power determination are listed in table 4. Pigment dispersions comprising polyhydroxyamines of the formula (I) are universally suitable for generation of concealing power in aqueous and solventborne coatings alike.

(25) Polyhydroxyamines of the formula (I) are suitable as neutralizing agents for aqueous pigment dispersions without contributing to the VOC content. The pastes are suitable for coloring both aqueous and solventborne paints, varnishes and coatings, in that the polyhydroxyamines of the formula (I) assure high color acceptance and act as mediators between solventborne and aqueous systems.

(26) TABLE-US-00018 TABLE 4 Results for examples 15 to 18 Outward Viscosity Concealing power/coating [%] Example appearance pH [mPas] A B C D 15 (C) pasty and 9.0 1949 97 98 97 98 homogeneous 16 (C) thixotropic and 9.0 1621 96 97 flocculated flocculated homogeneous 17 pasty and 9.0 3348 98 98 98 98 homogeneous 18 pasty and 9.0 4911 99 99 99 99 homogeneous