Modified colorants and inkjet ink compositions comprising modified colorants

Patent metadata

Field	Value
Publication number	US-9732227-B2
Application number	US-201414483712-A
Country	US
Kind code	B2
Filing date	Sep 11, 2014
Priority date	Oct 31, 2005
Publication date	Aug 15, 2017
Grant date	Aug 15, 2017

Abstract

The present invention relates to a modified colorant comprising a colorant having attached at least one organic group. Various embodiments of the organic group are disclosed. For each of these embodiments, preferably the organic group has a defined calcium index value. Also disclosed are various uses for these modified colorants, including inkjet ink compositions.

First claim

What is claimed is:

1. A modified colorant comprising a colorant having attached at least one organic group, wherein the organic group has a calcium index value greater than a calcium index value of 1,2,3-benzene tricarboxylic acid, wherein the colorant is a pigment and wherein the organic group comprises at least one group selected from:
(i) at least one hydroxamic acid group or salt thereof selected from at least one hydroxy pyridonyl group and at least one hydroxy quinolonyl group;
(ii) at least one heterocyclic group having at least one OH group or salt thereof;
(iii) at least one phosphonic acid group or a salt thereof and at least one second ionic, ionizable, or basic group vicinal or geminal to the phosphonic acid group or salt thereof;
(iv) a heteroaryl group having at least one carboxylic acid group or salt thereof;
(v) an aryl group having at least one nitroso group and at least one OH group or a salt thereof; and
(vi) an azoarene group having at least two OH groups, at least two NH 2 groups, or at least one OH group and at least one NH 2 group and has the formula Ar 1 —N═N—Ar 2 , wherein Ar 1 and Ar 2 , which can be the same or different, are an arylene group or an aryl group and at least one of Ar 1 or Ar 2 is an arylene group.

2. The modified colorant of claim 1 , wherein the organic group is selected from (i) and comprises a 1-hydroxy-2-pyridonyl group.

3. The modified colorant of claim 1 , wherein the organic group is selected from (i) and comprises a 1-hydroxy-2-quinolonyl group.

4. The modified colorant of claim 1 , wherein the organic group is selected from (ii) and comprises at least one hydroxy pyridinyl group or at least one hydroxy quinolinyl group.

5. The modified colorant of claim 4 , wherein the organic group comprises a 2-hydroxy-pyridinyl group.

6. The modified colorant of claim 4 , wherein the organic group comprises an 8-hydroxy-quinolinyl group or a 2-hydroxy-quinolinyl group.

7. The modified colorant of claim 1 , wherein the organic group is selected from (ii) and wherein the heterocyclic group has at least two OH groups.

8. The modified colorant of claim 7 , wherein the organic group is a 2,3-dihydroxy-pyridinyl group or a 3,4-dihydroxy-pyridinyl group.

9. The modified colorant of claim 1 , wherein the organic group is selected from (iii) and the second ionic, ionizable, or basic group is a carboxylic acid group, a sulfonic acid group, an hydroxyl group, or a salt thereof.

10. The modified colorant of claim 1 , wherein the organic group is selected from (iii) and comprises at least one group having the formula -CQ(PO 3 H 2 )(CO 2 H) 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.

11. The modified colorant of claim 1 , wherein the organic group is selected from (iii) and comprises at least one group having the formula —CR(PO 3 H 2 )(OH) or salts thereof, wherein R is H or a C 1 -C 6 alkyl group.

12. The modified colorant of claim 1 , wherein the organic group is selected from (iii) and comprises a group having the formula —X—(PO 3 H 2 )(OH) or salts thereof, wherein X is an arylene or heteroarylene group and wherein the PO 3 H 2 and OH group, or salts thereof, are ortho to each other.

13. The modified colorant of claim 1 , wherein the organic group is selected from (iv) and wherein the heteroaryl group has at least two carboxylic acid groups or salts thereof.

14. The modified colorant of claim 13 , wherein the organic group is a 2,6-pyridinyl-dicarboxylic acid group or salts thereof.

15. The modified colorant of claim 1 , wherein the organic group is selected from (v) and is a nitrosophenolic group or salt thereof.

16. The modified colorant of claim 1 , wherein the organic group is selected from (vi) and is a group having the structure —(HO)C 6 H 3 —N═N—C 6 H 3 Z(OH), wherein Z is a chloro or nitro group.

17. The modified colorant of claim 1 , wherein the pigment further has attached at least one second organic group different from the organic group.

18. The modified colorant of claim 17 , wherein the second organic group comprises at least one ionic group, at least one ionizable group, or a mixture thereof.

19. The modified colorant of claim 17 , wherein the second organic group has a calcium index value greater than a calcium index value of phenylphosphonic acid.

20. The modified colorant of claim 17 , wherein the second organic group is a polymeric group.

21. The modified colorant of claim 20 , wherein the polymeric group comprises a polymer having an acid number less than or equal to 200.

22. The modified colorant of claim 20 , wherein the polymeric group comprises a polymer having a Tg less than 100.

23. The modified colorant of claim 20 , wherein the polymeric group is present in an amount of from 0.1 to 50% by weight of the colorant.

24. The modified colorant of claim 1 , wherein the pigment is Pigment Blue 15, Pigment Red 122, Pigment Violet 19, Pigment Yellow 74, Pigment Yellow 155, Pigment Yellow 128, Pigment Yellow 218, Pigment Yellow 220, or Pigment Yellow 221.

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

26. A modified colorant comprising a pigment having attached at least one organic group, wherein the organic group comprises
i) at least one hydroxamic acid group or salt thereof selected from at least one hydroxy pyridonyl group and at least one hydroxy quinolonyl group,
ii) at least one phosphonic acid group or salt thereof and at least one second ionic, ionizable, or basic group, or
iii) an aryl group having at least one nitroso group and at least one OH group or a salt thereof.

27. A modified colorant comprising a pigment having attached at least one organic group, wherein the organic group comprises
i) at least one heterocyclic group having at least one OH group or salt thereof,
ii) at least one heteroaryl group having at least one carboxylic acid group or salts thereof, or
iii) an azoarene group has at least one OH group, at least one NH 2 group, or one OH group and one NH 2 group and has the formula Ar 1 —N═N—Ar 2 , wherein Ar 1 and Ar 2 , which can be the same or different, are an arylene group or an aryl group and at least one of Ar 1 or Ar 2 is an arylene group.

28. A modified colorant comprising a pigment having attached at least one organic group and at least one second organic group, wherein the organic group has a calcium index value greater than a calcium index value of phenylphosphonic acid and wherein the second organic group is a polymeric group.

29. An inkjet ink composition comprising a) a liquid vehicle and b) the modified colorant of claim 1 .

30. The inkjet ink composition of claim 29 , wherein the vehicle is an aqueous vehicle.

31. An inkjet ink composition comprising a) a liquid vehicle and b) the modified pigment of claim 28 .

Assignees

• Cabot Corp

Inventors

• Gu Feng
• Belmont James A
• Burns Elizabeth G
• Palumbo Paul S
• Corden Barry B
• Yu Yuan
• Halim Ervina

Classifications

• C09B67/0001

  Post-treatment of organic pigments or dyes · CPC title

• C09B68/4253

  Sulfonic acid groups · CPC title

• C09B67/0008

  with organic coatings · CPC title

• C09D11/322

  Pigment inks · CPC title

• C08K3/013

  Fillers, pigments or reinforcing additives · CPC title