Modified colorants and inkjet ink compositions comprising modified colorants

Patent metadata

Field	Value
Publication number	US-9725598-B2
Application number	US-59017006-A
Country	US
Kind code	B2
Filing date	Oct 31, 2006
Priority date	Oct 31, 2005
Publication date	Aug 8, 2017
Grant date	Aug 8, 2017

Abstract

The present invention relates to a modified colorant comprising a colorant having at least one polymer attached or adsorbed thereto. The polymer comprises at least one functional group, and various embodiments of the functional group are disclosed. For each of these embodiments, preferably the functional group has a defined calcium index value. Also disclosed are various uses for these modified colorants, including inkjet ink compositions. Thus, the present invention further relates to an inkjet ink composition comprising a) a liquid vehicle, b) at least one colorant, and c) at least one polymer comprising at least one functional group as described herein.

First claim

What is claimed is:

1. A modified colorant comprising a pigment having attached at least one polymeric group, wherein the polymeric group comprises a polymer having at least one functional group having a calcium index value greater than a calcium binding index value of phenylphosphonic acid,
wherein the at least one functional group comprises at least two phosphonic acid groups, partial esters thereof, or salts thereof, and wherein the at least one functional group is selected from: at least one geminal bisphosphonic acid group; at least one group having the formula —N—[(CH 2 ) m (PO 3 H 2 )] 2 , wherein m, which can be the same or different, is 1 to 3; and at least one group having the formula —CR═C(PO 3 H 2 ) 2 , wherein R is H, a C 1 -C 6 alkyl group, or an aryl group.

2. The modified colorant of claim 1 , wherein the functional group comprises at least one group having 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 H, a C 1 -C 18 alkyl group, a C 1 -C 18 acyl group, an aralkyl group, an alkaryl group, or an aryl group.

3. The modified colorant of claim 2 , wherein the functional group comprises at least one group having the formula —(CH 2 ) n —CQ(PO 3 H 2 ) 2 or salts thereof, wherein n is 1 to 9.

4. The modified colorant of claim 3 , wherein n is 1 to 3.

5. The modified colorant of claim , wherein the functional group comprises a group having the formula —Sp-(CH 2 ) n , —CQ(PO 3 H 2 ) 2 or salt thereof, wherein Sp is a spacer group and wherein n is 0 to 9.

6. The modified colorant of claim 5 , wherein Sp is —CO 2 —, —O 2 C—, —O—, —NR″—, —NR″CO—, —CONR″—, —SO 2 CH 2 CH 2 NR″—, —SO 2 CH 2 CH 2 —O—, or —SO 2 CH 2 CH 2 S—, wherein R″ is H or a C 1 -C 6 alkyl group.

7. The modified colorant of claim 1 , wherein the functional group comprises at least one group having the formula —(CH 2 ) n —N—[(CH 2 ) m (PO 3 H 2 )] 2 or salts thereof, wherein n is 1 to 9.

8. The modified colorant of claim 1 , wherein the functional group comprises a group having the formula —Sp-(CH 2 ) n —N—[(CH 2 ) m (PO 3 H 2 )] 2 or salts thereof, wherein Sp is a spacer group and wherein n is 0 to 9.

9. The modified colorant of claim 8 , wherein Sp is —CO 2 —, —O 2 C—, —O—, —NR″—, —NR″Co—, —CONR″—, —SO 2 CH 2 CH 2 NR″, —SO 2 CH 2 CH 2 O—, or —SO 2 CH 2 CH 2 S—, wherein R″ is H or a C 1 -C 6 alkyl group.

10. The modified colorant of claim 1 , wherein the polymer is prepared by reacting at least one reagent comprising the functional group and a polymer having at least one reactive group.

11. The modified colorant of claim 10 , wherein the reagent is an amine reagent and wherein the reactive group comprises a carboxylic acid group, a carboxylic ester group, or an anhydride.

12. The modified colorant of claim 1 , wherein the polymer is prepared by reacting at least one reagent comprising the functional group, a polymer having at least one reactive group, and at least one linking reagent.

13. The modified colorant of claim 12 , wherein the reagent is an amine reagent, the reactive group is an amino group, and the linking reagent is a dicarboxylic acid reagent or anhydride thereof.

14. The modified colorant of claim 1 , wherein the polymer is prepared by the polymerization of at least one monomer comprising the functional group.

15. The modified colorant of claim 14 , wherein the monomer is an acrylamide monomer, a methacrylamide monomer, an acrylate monomer, a methacrylate monomer, a styrene monomer, a vinyl ester monomer, or a vinyl ether monomer.

16. The modified colorant of claim 14 , wherein the monomer is an acrylamide or methacrylamide comprising at least one bisphosphonate group or aryl polyacid group.

17. The modified colorant of claim 14 , wherein the polymer is prepared by polymerization of at least one additional monomer comprising at least one ionic group, at least one ionizable group, or a mixture thereof that does not have a calcium index value greater than that of phenylphosphonic acid.

18. The modified colorant of claim 17 , where the additional monomer is an alkyl acrylamide or alkyl methacrylamide.

19. The modified colorant of claim 1 , wherein the polymer has an acid number less than or equal to 200.

20. The modified colorant of claim 1 , wherein the polymer has a Tg less than 100.

21. The modified colorant of claim 1 , wherein the polymeric group is present in an amount of from 0.1 to 50% by weight of the pigment.

22. The modified colorant of claim 1 , wherein the pigment is an organic colored pigment comprising a blue pigment, a black pigment, a brown pigment, a cyan pigment, a green pigment, a white pigment, a violet pigment, a magenta pigment, a red pigment, a yellow pigment, an orange pigment, or mixtures thereof.

23. The modified colorant of claim 1 , wherein the pigment is carbon black.

24. The modified colorant of claim 1 , wherein the functional group has a calcium index value greater than or equal to a calcium index value of 1,2,3-benzene tricarboxylic acid.

25. A modified colorant comprising a pigment having attached at least one polymeric group, wherein the polymeric group comprises a polymer having at least one functional group comprising at least two phosphonic acid groups, partial esters thereof, or salts thereof,
wherein the at least one functional group is selected from: at least one geminal bisphosphonic acid group; at least one group having the formula —N—[(CH 2 ) m (PO 3 H 2 )] 2 , wherein m, which can be the same or different, is 1 to 3; and at least one group having the formula —CR═C(PO 3 H 2 ) 2 , wherein R is H, a C 1 -C 6 alkyl group, or an aryl group.

26. An inkjet ink composition comprising a) a liquid vehicle and b) at least one modified colorant comprising a pigment having attached at least one polymeric group, wherein the polymeric group comprises a polymer having at least one functional group comprising at least two phosphonic acid groups, partial esters thereof, or salts thereof,
wherein the at least one functional group is selected from: at least one geminal bisphosphonic acid group; at least one group having the formula —N—[(CH 2 ) m (PO 3 H 2 )] 2 , wherein m, which can be the same or different, is 1 to 3; and at least one group having the formula —CR═C(PO 3 H 2 ) 2 , wherein R is H, a C 1 -C 6 alkyl group, or an aryl group.

27. An inkjet ink composition comprising a) a liquid vehicle and b) at least one modified colorant comprising a pigment having attached at least one polymeric group, wherein the polymeric group comprises a polymer having at least one functional group having a calcium index value greater than a calcium binding index value of phenylphosphonic acid,
wherein the at least one functional group is selected from: at least one geminal bisphosphonic acid group; at least one group having the formula —N—[(CH 2 ) m (PO 3 H 2 )] 2 , wherein m, which can be the same or different, is 1 to 3; and at least one group having the formula —CR═C(PO 3 H 2 ) 2 , wherein R is H, a C 1 -C 6 alkyl group, or an aryl group.

Assignees

• Burns Elizabeth G
• Belmont James A
• Nick Robert J
• Gu Feng
• Cabot Corp

Inventors

• Burns Elizabeth G
• Belmont James A
• Nick Robert J
• Gu Feng

Classifications

• C09D7/41

  Organic pigments; Organic dyes · CPC title

• C09B68/4253

  Sulfonic acid groups · CPC title

• C08K9/04

  Ingredients treated with organic substances {(treated with macromolecular compounds C08K9/08)} · CPC title

• C09B67/0001

  Post-treatment of organic pigments or dyes · CPC title

• C08K3/08

  Metals · CPC title