Polymeric colorants having pigment and dye components and corresponding ink compositions

• US 20060089421A1
• Filed: 02/14/2005
• Published: 04/27/2006
• Est. Priority Date: 10/25/2004
• Status: Abandoned Application

• Current Assignee: Hewlett-Packard Development Company, L.P. (HP Inc.)
• Original Assignee: Hewlett-Packard Development Company, L.P. (HP Inc.)
• Inventors: Vasudevan, Sundar
• Application Number:
  US11/058,006
• Publication Number:
  US 20060089421A1
• Time in Patent Office: Days
• US Class Current: 523/160
• CPC Class Codes: C09B 68/20 characterised by the process features
• CPC Class Codes: C09B 68/44 Non-ionic groups, e.g. halogen, OH or SH
• CPC Class Codes: C09B 69/10 Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds addition products of alkylene oxide to dyes, C09B69/00; dyeing with polymeric dyes D06P1/0056
• CPC Class Codes: C09D 11/30 Inkjet printing inks
• CPC Class Codes: C09D 11/322 Pigment inks

Abstract

Colorants having pigment and dye components having improved chroma and good water and lightfastness are disclosed and described. A polymeric colorant can include a pigment having a polymer covalently attached thereto and a dye covalently attached to the polymer. A dispersant can be covalently attached to at least one of the pigment, the polymer, and the dye. By including both a pigment and a dye component in the polymeric colorant, improved chroma, waterfastness, and lightfastness can be realized. The dye and pigment components can be substantially the same color, or can have different colors, depending on the desired appearance. The polymeric colorants of the present invention are well suited to inclusion in ink-jet compositions, although many other applications are considered suitable for the instant polymeric colorants.

Claims

1. A polymeric colorant, comprising:

a) a pigment having a polymer covalently attached thereto;

b) a first dye covalently attached to the polymer; and

c) a dispersant covalently attached to at least one of the pigment, the polymer, and the first dye.

2. The colorant of claim 1, wherein the polymer is a member selected from the group consisting of maleic anhydride copolymers, acrylic copolymers, methacrylic copolymers, amine or alcohol-containing copolymers, and combinations thereof.

3. The colorant of claim 2, wherein the polymer is a maleic anhydride copolymer.

4. The colorant of claim 3, wherein the polymer is selected from the group consisting of styrene-maleic anhydride copolymer, methyl vinyl ether-maleic anhydride copolymer, vinyl pyrrolidone-maleic anhydride copolymer, styrene acrylic acid copolymer, styrene methacrylic acid copolymer, 4-vinylaniline-acrylic acid copolymer, 4-vinylaniline-methacrylic acid copolymer, and combinations thereof.

5. The colorant of claim 1, wherein the polymer is attached to the pigment through a linking group.

6. The colorant of claim 5, wherein the linking group is a member selected from the group consisting of 2-(4-aminophenyl) sulfonylethane sulfonate, 4-aminobenzylamine, 4-aminophenylalanine, and combinations thereof.

7. The colorant of claim 1, wherein the first dye is selected from the group consisting of C.I. Acid Red 440, C.I. Reactive Red 3, C.I. Reactive Red 13, C.I. Reactive Red 23, C.I. Reactive Red 24, C.I. Reactive Red 33, C.I. Reactive Red 43, C.I. Reactive Red 45, C.I. Reactive Red 120, C.I. Reactive Red 180, C.I. Reactive Red 194, C.I. Reactive Red 220, C.I. Reactive Violet 4, C.I. Reactive Blue 19, C.I. Reactive Blue 5, C.I. Reactive Blue 49, C.I. Reactive Yellow 2, C.I. Reactive Yellow 3, C.I. Reactive Black 39, and combinations thereof.

8. The colorant of claim 1, further comprising a second dye covalently attached to the polymer.

9. The colorant of claim 8, wherein the second dye is a different color than the first dye.

10. The colorant of claim 1, wherein the pigment is a different color than the first dye.

11. The colorant of claim 10, wherein the pigment has a black color and the first dye has a cyan or magenta color such that the polymeric colorant has an effective color which is a neutral gray.

12. The colorant of claim 1, wherein the pigment is a member selected from the group consisting of black pigments, cyan pigments, magenta pigments, and yellow pigments.

13. The colorant of claim 12, wherein the pigment is carbon black.

14. The colorant of claim 1, wherein the dispersant is attached to the pigment.

15. The colorant of claim 1, wherein the dispersant is attached to the polymer.

16. The colorant of claim 1, wherein the dispersant is a member selected from the group consisting of polyalkyl glycols, polyalkyl imines, trehalose, acrylates, methacrylates, and combinations thereof.

17. The colorant of claim 1, wherein the polymeric colorant has a ratio of dye molecules per weight of pigment particle from about 10 μ

mole per gram to about 100 mmole per gram.

18. The colorant of claim 1, further comprising a stabilizing additive.

19. The colorant of claim 1, wherein the polymeric colorant has the general structure:

where x, y, and z are non-zero positive integers such that the polymeric colorant has a molecular weight less than about 20,000;

R1 is the first dye, the dispersant, or a linking group attached to the pigment with the proviso that z is at least three and at least one of each of the first dye, the dispersant, and the linking group is present; and

R2 is a hydrophobic group.

20. The colorant of claim 19, wherein the polymeric colorant has the general structure:

where a, b, and c are non-zero positive integers such that the polymeric colorant has a molecular weight less than about 20,000.

21. An ink-jet ink composition, comprising a liquid vehicle having a polymeric colorant dispersed therein, said polymeric colorant including:

a) a pigment having a polymer covalently attached thereto;

b) a dye covalently attached to the polymer; and

c) a dispersant covalently attached to at least one of the pigment, the polymer, and the dye.

22. The composition of claim 21, wherein the polymer is a maleic anhydride copolymer.

23. The composition of claim 21, wherein the polymer is attached to the pigment through a linking group.

24. The composition of claim 21, wherein the dye has a reactive group selected from the group consisting of hydroxy, amino, carboxylic acid, sulfonic acid, thiol, halotriazine, maleimide sulfone, vinyl sulfone, and combinations thereof.

25. The composition of claim 21, wherein the dispersant is attached to the pigment.

26. The composition of claim 21, wherein the dispersant is attached to the polymer.

27. An ink-jet ink composition, comprising:

a) a liquid vehicle;

b) a polymer attached dye including a dye covalently attached to a polymer, said dye having a first color; and

c) a pigment having a second color which has a substantially different hue from the first color.

28. The composition of claim 27, wherein the pigment is polymer-dispersed.

29. The composition of claim 27, wherein the pigment is covalently attached to the polymer to form a polymeric colorant.

30. The composition of claim 27, further comprising at least two different dyes covalently attached to the polymer.

31. The composition of claim 27, wherein the first color is cyan, magenta, or yellow and the second color is black.

32. The composition of claim 31, wherein the first color is cyan or magenta such that the ink-jet ink composition has an effective color of neutral gray.

33. The composition of claim 27, wherein the polymer is selected from the group consisting of maleic anhydride copolymers, acrylic copolymers, methacrylic copolymers, amine or alcohol-containing copolymers, and combinations thereof.

34. The composition of claim 27, wherein the dye has a reactive group selected from the group consisting of hydroxy, amino, carboxylic acid, sulfonic acid, thiol, halotriazine, maleimide sulfone, vinyl sulfone, and combinations thereof.

35. A method of forming a polymeric colorant, comprising the steps of:

a) attaching a dye to a polymer to form a polymer-dye colorant;

b) attaching the polymer to a pigment; and

c) attaching a dispersant to at least one of the polymer-dye colorant and the pigment.

36. The method of claim 35, wherein said dye has a reactive group selected from the group consisting of hydroxyl, amino, carboxylic acid, sulfonic acid, thiol, halotriazine, maleimide sulfone, vinyl sulfone, and combinations thereof.

37. The method of claim 36, wherein said polymer includes an anhydride group configured for reaction with the reactive group.

38. The method of claim 35, wherein the polymer is a maleic anhydride copolymer.

39. The method of claim 35, wherein the polymer is attached to the pigment through a linking group.

40. The method of claim 35, wherein the dye is selected from the group consisting of C.I. Acid Red 440, C.I. Reactive Red 3, C.I. Reactive Red 13, C.I. Reactive Red 23, C.I. Reactive Red 24, C.I. Reactive Red 33, C.I. Reactive Red 43, C.I. Reactive Red 45, C.I. Reactive Red 120, C.I. Reactive Red 180, C.I. Reactive Red 194, C.I. Reactive Red 220, C.I. Reactive Violet 4, C.I. Reactive Blue 19, C.I. Reactive Blue 5, C.I. Reactive Blue 49, C.I. Reactive Yellow 2, C.I. Reactive Yellow 3, C.I. Reactive Black 39, and combinations thereof.

41. The method of claim 35, wherein the pigment is a member selected from the group consisting of black pigments, cyan pigments, magenta pigments, and yellow pigments.

42. The method of claim 35, wherein the dispersant is attached to the polymer or the pigment prior to attaching the dye to the polymer.

43. The method of claim 35, wherein the dye is attached to the polymer prior to attaching the polymer to the pigment.

44. The method of claim 35, wherein the dispersant is a member selected from the group consisting of polyalkyl glycols, polyalkyl imines, trehalose, acrylates, methacrylates, and combinations thereof.

45. The method of claim 35, wherein the polymeric colorant has the general structure:

where x, y, and z are non-zero positive integers such that the polymeric colorant has a molecular weight less than about 20,000;

R1 is the dye, the dispersant, or a linking group attached to the pigment with the proviso that z is greater than three and at least one of each of the dye, the dispersant, and the linking group is present; and

R2 is a hydrophobic group.