Ink compositions comprising modified colored pigments and methods for preparing the same

• US 6,641,653 B2
• Filed: 07/19/2001
• Issued: 11/04/2003
• Est. Priority Date: 07/19/2001
• Status: Active Grant

• Current Assignee: Cabot Corporation
• Original Assignee: Cabot Corporation
• Inventors: Yu, Yuan
• Primary Examiner(s): Bell, Mark L.
• Assistant Examiner(s): FAISON GEE, VERONICA FAYE
• Application Number:
  US09/909,328
• Publication Number:
  US 20030024433A1
• Time in Patent Office: 838 Days
• Field of Search: 106/31.6, 106/499, 106/31.43, 106/31.86, 106/31.87
• US Class Current: 106/31.6
• CPC Class Codes: C09B 68/20 characterised by the process features
• CPC Class Codes: C09B 68/423 Cationic groups
• CPC Class Codes: C09B 68/444 Polyether
• CPC Class Codes: C09D 11/322 Pigment inks

Abstract

The present invention describes an ink composition comprising a liquid vehicle and a modified colored pigment. The modified colored pigment comprises the product of a colored pigment having at least one leaving group and a treating agent. The modified colored pigments are also disclosed, as are processes for producing them.

Claims

1. An ink composition comprising a liquid vehicle and a modified colored pigment, wherein the modified colored pigment comprises the product of:

a) a colored pigment having at least one leaving group, wherein the leaving group is selected from the group consisting of;

halogens, substituted or unsubstituted alkyl or aryl sulfonates, substituted or unsubstituted acylates, substituted or unsubstituted benzoates, and mixtures thereof; and

b) a treating agent having the formula B-R-Q, wherein B is a nucleophilic group, R is an alkylene or arylene group, and Q is an ionic or ionizable group.

2. The ink composition of claim 1, wherein the liquid vehicle is an aqueous vehicle.

3. The ink composition of claim 1, wherein the modified colored pigment is a surface modified colored pigment.

4. The ink composition of claim 1, wherein the leaving group is a halogen.

5. The ink composition of claim 4, wherein the halogen is chlorine, bromine, or mixtures thereof.

6. The ink composition of claim 1, wherein the colored pigment is Pigment Green 7, Pigment Green 36, or Pigment Yellow 138.

7. The ink composition of claim 1, wherein the nucleophilic group is OH, SH, or NR′

₂ and wherein each R′

is independently hydrogen, a C₁-C₁₂ alkyl group, or an aryl group.

8. The ink composition of claim 1, wherein Q is a carboxylic acid group or salt thereof, a sulfonic acid group or salt thereof, a phosphonic acid group or salt thereof, an amino group or salt thereof, or a quaternary ammonium group.

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

10. An ink composition comprising a liquid vehicle and a modified colored pigment, wherein the modified colored pigment comprises the product of:

a) a colored pigment having at least one leaving group, wherein the leaving group is selected from the group consisting of;

halogens, substituted or unsubstituted alkyl or aryl sulfonates, substituted or unsubstituted acylates, substituted or unsubstituted benzoates, and mixtures thereof; and

b) a treating agent having the formula B-R-AO, wherein B is a nucleophilic group, R is a bond, an alkylene group, or an arylene group, and AO is an alkylene oxide group.

11. The ink composition of claim 10, wherein the liquid vehicle is an aqueous vehicle.

12. The ink composition of claim 10, wherein the modified colored pigment is a surface modified colored pigment.

13. The ink composition of claim 10, wherein the leaving group is a halogen.

14. The ink composition of claim 13, wherein the halogen is chlorine, bromine, or mixtures thereof.

15. The ink composition of claim 10, wherein the colored pigment is Pigment Green 7, Pigment Green 36, or Pigment Yellow 138.

16. The ink composition of claim 10, wherein the nucleophilic group is OH, SH, or NR′

₂ and wherein each R′

is independently hydrogen, a C₁-C₁₂ alkyl group, or an aryl group.

17. The ink composition of claim 10, wherein the alkylene oxide group is a polymer comprising ethylene oxide, propylene oxide, or mixtures thereof.

18. The ink composition of claim 10, wherein the ink composition is an inkjet ink composition.

19. An ink composition comprising a liquid vehicle and a modified colored pigment, wherein the modified colored pigment comprises the product of:

a) a colored pigment having at least one leaving group; and

b) a sulfite treating agent.

20. The ink composition of claim 19, wherein the liquid vehicle is an aqueous vehicle.

21. The ink composition of claim 19, wherein the modified colored pigment is a surface modified colored pigment.

22. The ink composition of claim 19, wherein the leaving group is selected from the group consisting of:

halogens, substituted or unsubstituted alkyl or aryl sulfonates, substituted or unsubstituted acylates, substituted or unsubstituted benzoates, and mixtures thereof.

23. The ink composition of claim 19, wherein the leaving group is a halogen.

24. The ink composition of claim 23, wherein the halogen is chlorine, bromine, or mixtures thereof.

25. The ink composition of claim 19, wherein the colored pigment is Pigment Green 7, Pigment Green 36, or Pigment Yellow 138.

26. The ink composition of claim 19, wherein the sulfite treating agent comprises a sulfite anion and at least one counterion.

27. The ink composition of claim 26, wherein the counterion is Na⁺, K⁺, Li⁺, Cs⁺, or NH₄⁺.

28. The ink composition of claim 19, wherein the sulfite treating agent is sodium sulfite.

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

30. A modified colored pigment comprising the product of:

a) a colored pigment having at least one leaving group, wherein the leaving group is selected from the group consisting of;

halogens, substituted or unsubstituted alkyl or aryl sulfonates, substituted or unsubstituted acylates, substituted or unsubstituted benzoates, and mixtures thereof; and

b) a treating agent having the formula B-R-Q, wherein B is a nucleophilic group, R is an alkylene or arylene group, and Q is an ionic or ionizable group.

31. The modified colored pigment of claim 30, wherein the modified colored pigment is a surface modified colored pigment.

32. The modified colored pigment of claim 30, wherein the leaving group is a halogen.

33. The modified colored pigment of claim 32, wherein the halogen is chlorine, bromine, or mixtures thereof.

34. The modified colored pigment of claim 30, wherein the colored pigment is Pigment Green 7, Pigment Green 36, or Pigment Yellow 138.

35. The modified colored pigment of claim 30, wherein the nucleophilic group is OH, SH, or NR′

₂ and wherein each R′

is independently hydrogen, a C₁-C₁₂ alkyl group, or an aryl group.

36. The modified colored pigment of claim 30, wherein Q is a carboxylic acid group or salt thereof, a sulfonic acid group or salt thereof, a phosphonic acid group or salt thereof, an amino group or salt thereof, or a quaternary ammonium group.

37. A modified colored pigment comprising the product of:

a) a colored pigment having at least one leaving group, wherein the leaving group is selected from the group consisting of;

halogens, substituted or unsubstituted alkyl or aryl sulfonates, substituted or unsubstituted acylates, substituted or unsubstituted benzoates, and mixtures thereof; and

b) a treating agent having the formula B-R-AO, wherein B is a nucleophilic group, R is a bond, an alkylene group, or an arylene group, and AO is an alkylene oxide group.

38. The modified colored pigment of claim 37, wherein the modified colored pigment is a surface modified colored pigment.

39. The modified colored pigment of claim 37, wherein the leaving group is a halogen.

40. The modified colored pigment of claim 39, wherein the halogen is chlorine, bromine, or mixtures thereof.

41. The modified colored pigment of claim 37, wherein the colored pigment is Pigment Green 7, Pigment Green 36, or Pigment Yellow 138.

42. The modified colored pigment of claim 37, wherein the nucleophilic group is OH, SH, or NR′

₂ and wherein each R′

is independently hydrogen, a C₁-C₁₂ alkyl group, or an aryl group.

43. The modified colored pigment of claim 37, wherein the alkylene oxide group is a polymer comprising ethylene oxide, propylene oxide, or mixtures thereof.

44. A modified colored pigment comprising the product of:

a) a colored pigment having at least one leaving group; and

b) a sulfite treating agent.

45. The modified colored pigment of claim 44 wherein the modified colored pigment is a surface modified colored pigment.

46. The modified colored pigment of claim 44, wherein the leaving group is selected from the group consisting of:

halogens, substituted or unsubstituted alkyl or aryl sulfonates, substituted or unsubstituted acylates, substituted or unsubstituted benzoates, and mixtures thereof.

47. The modified colored pigment of claim 44, wherein the leaving group is a halogen.

48. The modified colored pigment of claim 47, wherein the halogen is chlorine, bromine, or mixtures thereof.

49. The modified colored pigment of claim 44, wherein the colored pigment is Pigment Green 7, Pigment Green 36, or Pigment Yellow 138.

50. The modified colored pigment of claim 44, wherein the sulfite treating agent comprises a sulfite anion and at least one counterion.

51. The modified colored pigment of claim 50, wherein the counterion is Na⁺, K⁺, Li⁺, Cs⁺, or NH₄⁺.

52. The modified colored pigment of claim 44, wherein the sulfite treating agent is sodium sulfite.

53. A process for preparing a modified colored pigment comprising the steps of:

a) combining, in any order, a colored pigment having at least one leaving group, a treating agent having at least one nucleophilic group, a solvent A, and a solvent B, wherein solvent A is a non-solvent for the colored pigment and wherein solvent B is a solvent for the colored pigment; and

b) heating for a time and to a temperature sufficient to produce a modified colored pigment.

54. The process of claim 53, wherein the combination of colored pigment, treating agent, solvent A, and solvent B is further combined with a base.

55. The process of claim 54, wherein the base is selected from the group consisting of:

alkaline earth metal hydroxides, alkali metal hydroxides, alkali metal carbonates, and alkali metal bicarbonates.

56. The process of claim 54, wherein the base is LiOH, KOH, NaOH, K₂CO₃, KHCO₃, NA₂CO₃, or NaHCO₃.

57. The process of claim 53, wherein the treating agent is combined with solvent A in step a).

58. The process of claim 57, wherein the combination of treating agent and solvent A is further combined with a base.

59. The process of claim 58, wherein the base is selected from the group consisting of:

alkaline earth metal hydroxides, alkali metal hydroxides, alkali metal carbonates, and alkali metal bicarbonates.

60. The process of claim 58, wherein the base is LiOH, KOH, NaOH, K₂CO₃, KHCO₃, Na₂CO₃, or NaHCO₃.

61. The process of claim 58, wherein the combination of treating agent, solvent A, and base is preheated for a time and to a temperature sufficient to dissolve the treating agent.

62. The process of claim 53, wherein the colored pigment is combined with solvent B in step a).

63. The process of claim 62, wherein the combination of colored pigment and solvent B is preheated for a time and to a temperature sufficient to dissolve the colored pigment.

64. The process of claim 53, wherein the ratio of solvent A to solvent B is 1:

4 to 4;

1.

65. The process of claim 53, wherein the ratio of solvent A to solvent B is 1:

1.

66. The process of claim 53, wherein solvent A is selected from the group consisting of:

water, alcohols, ethers, and ketones.

67. The process of claim 53, wherein solvent A is water, methanol, ethanol, iso-propanol, or glycol.

68. The process of claim 53, wherein solvent B is dimethylformamide.

69. The process of claim 53, wherein solvent A is water and solvent B is dimethylformamide.

70. The process of claim 53, wherein the leaving group is selected from the group consisting of:

halogens, substituted or unsubstituted alkyl or aryl sulfonates, substituted or unsubstituted acylates, substituted or unsubstituted benzoates, and mixtures thereof.

71. The process of claim 53, wherein the leaving group is a halogen.

72. The process of claim 71, wherein the halogen is chlorine, bromine, or mixtures thereof.

73. The process of claim 53, wherein the treating agent has the formula B-R-Q, wherein B is a nucleophilic group, R is an alkylene or arylene group, and Q is an ionic or ionizable group.

74. The process of claim 73, wherein the nucleophilic group is OH, SH, or NR′

₂ and wherein each R′

is independently hydrogen, a C₁-C₁₂ alkyl group, or an aryl group.

75. The process of claim 73, wherein Q is a carboxylic acid group or salt thereof, a sulfonic acid group or salt thereof, a phosphonic acid group or salt thereof, an amino group or salt thereof, or a quaternary ammonium group.

76. The process of claim 53, wherein the treating agent has the formula B-R-AO, wherein B is a nucleophilic group, R is a bond, an alkylene group, or an arylene group, and AO is an alkylene oxide group.

77. The process of claim 76, wherein the nucleophilic group is OH, SH, or NR′

₂ and wherein each R′

is independently hydrogen, a C₁-C₁₂ alkyl group, or an aryl group.

78. The process of claim 76, wherein the alkylene oxide group is a polymer comprising ethylene oxide, propylene oxide, or mixtures thereof.

79. The process of claim 53, wherein the treating agent is a sulfite treating agent.

80. The modified colored pigment of claim 79, wherein the sulfite treating agent comprises a sulfite anion and at least one counterion.

81. The modified colored pigment of claim 80, wherein the counterion is Na⁺, K⁺, Li⁺, Cs⁺, or NH₄⁺.

82. The modified colored pigment of claim 80, wherein the sulfite treating agent is sodium sulfite.

83. The process of claim 53, wherein the colored pigment is Pigment Green 7, Pigment Green 36, or Pigment Yellow 138.

84. A process for preparing a modified colored pigment comprising the steps of:

a) combining, in any order, a colored pigment having at least one leaving group, a sulfite treating agent, and a solvent A, wherein solvent A is a non-solvent for the colored pigment, and

b) heating for a time and to a temperature sufficient to produce a modified colored pigment.