Polymers for inkjet ink compositions

Patent metadata

Field	Value
Publication number	US-10138388-B2
Application number	US-201715798973-A
Country	US
Kind code	B2
Filing date	Oct 31, 2017
Priority date	Oct 31, 2016
Publication date	Nov 27, 2018
Grant date	Nov 27, 2018

Abstract

Disclosed herein are polymers, which can be incorporated in pigment dispersions and inkjet ink compositions, comprising first monomers selected from ethylenically unsaturated hydrophobic monomers, and second monomers selected from maleic anhydride, maleic acid, and salts, esters, imides, and amides thereof. The polymers can have a portion of the second monomers functionalized with at least one organic group having a calcium index value greater than or equal to a calcium index value of phenylphosphonic acid. Additionally and/or alternatively, the at least one polymer can be crosslinked via the second monomers. Dispersions and inkjet ink compositions comprising such polymers can also further comprise at least one pigment and a liquid vehicle. Also disclosed are methods of making such polymers.

First claim

The invention claimed is:

1. A composition comprising:
at least one pigment;
a liquid vehicle; and
at least one polymer comprising first monomers selected from ethylenically unsaturated hydrophobic monomers, and second monomers selected from maleic anhydride, maleic acid, and salts, esters, imides, and amides thereof,
wherein a portion of the second monomers are functionalized with at least one organic group having a calcium index value greater than or equal to a calcium index value of phenylphosphonic acid, and
wherein the at least one polymer is crosslinked via at least one linkage selected from amide, imide, ether, thioether, and ester linkages.

2. The composition of claim 1 , wherein the at least one organic group comprises at least two phosphonic acid groups, esters thereof, or salts thereof.

3. The composition of claim 1 , wherein the ethylenically unsaturated hydrophobic monomers comprise the formula CH 2 ═CR 1 R 2 , wherein R 1 and R 2 are independently selected from H, C 1 -C 12 alkyl, C 5 -C 20 aryl, and C 6 -C 20 alkaryl, and wherein the carbon atoms of R 1 and R 2 can be optionally substituted with at least one heteroatom selected from O, N, and S.

4. The composition of claim 1 , wherein at least a second portion of the second monomers are functionalized with at least one second organic group comprising the formula -A-N(R 3 )(R 4 ), wherein R 3 and R 4 are independently selected from H, C 1 -C 10 alkyl, C 4 -C 18 aryl, C 4 -C 18 heteroaryl, and C 3 -C 20 heterocycloalkyl, and A is selected from C 1 -C 10 alkylene, C 3 -C 20 cycloalkylene, C 3 -C 20 heterocycloalkylene, arylene, heteroarylene, and C 2 -C 20 ether.

5. The composition of claim 1 , wherein the at least one organic group comprises at least one geminal bisphosphonic acid group, esters thereof, or salts thereof.

6. The composition of claim 1 , wherein the at least one organic group comprises at least one group comprising the formula —CQ(PO 3 H 2 ) 2 or salts thereof, wherein Q is H, R, OR, SR, or NR 2 wherein R, which can be the same or different, is selected from H, C 1 -C 18 alkyl, C 1 -C 18 acyl, aralkyl, alkaryl, and aryl.

7. The composition of claim 1 , wherein the at least one organic group comprises at least one group comprising the formula —(CH 2 ) n —CQ(PO 3 H 2 ) 2 or salts thereof, wherein n is an integer ranging from 1 to 9.

8. The composition of claim 1 , wherein the at least one organic group comprises at least one group selected from carboxylic acids, sulfonic acids, phosphonic acids, hydroxyls, amines, and esters, amides, and salts, and esters thereof.

9. The composition of claim 1 , wherein the portion of the second monomers functionalized with the at least one organic group is at least 3 mol % of the total amount of the second monomers.

10. The composition of claim 1 , wherein the ethylenically unsaturated hydrophobic monomers comprise the formula CH 2 ═CR 1 R 2 , wherein R 1 and R 2 are independently selected from H, C 1 -C 12 alkyl, C 5 -C 20 aryl, C 6 -C 20 aralkyl, and C 6 -C 20 alkaryl.

11. The composition of claim 1 , wherein the ethylenically unsaturated hydrophobic monomers are selected from styrene, α-methyl styrene, ethylene, propylene, 1-butylene, isobutylene, butadiene, and methyl vinyl ether.

12. The composition of claim 1 , wherein the ethylenically unsaturated hydrophobic monomers are selected from styrene.

13. The composition of claim 1 , wherein the second monomers comprise maleic anhydride.

14. The composition of claim 1 , wherein the second monomers comprise maleic acid, and salts, esters, imides, and amides thereof.

15. The composition of claim 1 , wherein the second monomers comprise a mixture of maleic anhydride and maleic acid, and salts, esters, imides, and amides thereof.

16. The composition of claim 1 , wherein the second monomers are present in the at least one polymer in an amount ranging from 10 to 60 mol % relative to the at least one polymer.

17. The composition of claim 1 , wherein the first monomers are present in the at least one polymer in an amount ranging from 40 to 90 mol % relative to the at least one polymer.

18. The composition of claim 1 , wherein the liquid vehicle is aqueous.

19. The composition of claim 1 , wherein the composition is an inkjet ink composition.

20. The composition of claim 1 , wherein the ethylenically unsaturated hydrophobic monomers are selected from ethylenically unsaturated esters.

21. The composition of claim 20 , wherein the ethylenically unsaturated esters are selected from vinyl acetate, allyl acetate, methyl methacrylate, ethyl acrylate, n-butyl acrylate, n-butyl methacrylate, n-octyl acrylate, benzyl acrylate, acrylonitrile, and, acrylamide.

22. The composition of claim 1 , wherein the at least one polymer is crosslinked through carboxylate-containing groups of the second monomers.

23. The composition of claim 22 , wherein the at least one polymer has an acid number of less than 325.

24. The composition of claim 22 , wherein the at least one polymer has an acid number ranging from 50 to 325.

25. The composition of claim 22 , wherein the composition has a pH ranging from 8 to 11.

26. The composition of claim 1 , wherein the at least one polymer is crosslinked via at least one linkage selected from ester linkages.

27. The composition of claim 26 , wherein the ester linkage is derived from a reaction between epoxy-containing compounds and carboxylate-containing groups of the second monomers.

28. The composition of claim 27 , wherein the epoxy-containing compounds are selected from di- and tri-glycidyl ether compounds.

29. The composition of claim 27 , wherein the epoxy-containing compounds are selected from trimethylolpropane triglycidyl ether.

30. A composition comprising:
at least one pigment;
a liquid vehicle; and
at least one polymer comprising first monomers selected from ethylenically unsaturated hydrophobic monomers, and second monomers selected from maleic anhydride, maleic acid, and salts, esters, imides, and amides thereof,
wherein a portion of the second monomers are functionalized with at least one organic group having a calcium index value greater than or equal to a calcium index value of phenylphosphonic acid, and
wherein at least a second portion of the second monomers are functionalized with at least one second organic group comprising the formula -A-N(R 3 )(R 4 ), wherein R 3 and R 4 are independently selected from H, C 1 -C 10 alkyl, C-Cis aryl, C 4 -C 18 heteroaryl, and C 3 -C 20 heterocycloalkyl, and A is selected from C 1 -C 10 alkylene, C 3 -C 20 cycloalkylene, C 3 -C 20 heterocycloalkylene, arylene, heteroarylene, and C 2 -C 20 ether.

Assignees

• Cabot Corp

Inventors

• Xu Jinqi
• Palumbo Paul S
• Lebed Andrea
• Clarke Heather E
• Shaknovich Alexander I
• Liu Tianqi

Classifications

• C09D11/326 Primary

  characterised by the pigment dispersant · CPC title

• C08F222/08

  with vinyl aromatic monomers · CPC title

• C09D11/107 Primary

  from unsaturated acids or derivatives thereof · CPC title

• C09D11/106 Primary

  containing macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds · CPC title

• C09D135/00

  Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least another carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Coating compositions based on derivatives of such polymers · CPC title