Colored image-forming composition containing phthalocyanine compound, inks, inkjet inks, inkjet recording method and method for improving toleracne to decoloration due to ozone gas

• US 7,270,703 B2
• Filed: 06/21/2002
• Issued: 09/18/2007
• Est. Priority Date: 06/22/2001
• Status: Expired due to Term

• Current Assignee: Fujifilm Corporation (Fujifilm Holdings Corporation)
• Original Assignee: Fujifilm Corporation (Fujifilm Holdings Corporation)
• Inventors: Tateishi, Keiichi, Noro, Masaki, Yabuki, Yoshiharu, Omatsu, Tadashi
• Primary Examiner(s): KLEMANSKI, HELENE G
• Application Number:
  US10/362,140
• Publication Number:
  US 20040099181A1
• Time in Patent Office: 1,915 Days
• Field of Search: 106/31.49, 106/31.47, 106/31.78, 106/31.77, 540/131, 347/100
• US Class Current: 106/31.49
• CPC Class Codes: B41M 5/385 characterised by the transferable dyes or pigments infrared absorbing dyes B41M5/465
• CPC Class Codes: B41M 5/5218 characterised by inorganic additives, e.g. pigments, clays
• CPC Class Codes: C09B 47/0675 having oxygen or sulfur linked directly to the skeleton
• CPC Class Codes: C09B 47/0676 having nitrogen atom(s) linked directly to the skeleton
• CPC Class Codes: C09B 47/073 Preparation from isoindolenines , e.g. pyrrolenines
• CPC Class Codes: C09D 11/037 characterised by the pigment
• CPC Class Codes: C09D 11/32 characterised by colouring agents
• CPC Class Codes: C09D 11/328 characterised by dyes
• CPC Class Codes: C09D 11/40 Ink-sets specially adapted for multi-colour inkjet printing
• CPC Class Codes: D06P 5/30 Ink jet printing
• CPC Class Codes: G03G 9/0918 Phthalocyanine dyes

Abstract

To provide a novel phthalocyanine compound, and an inkjet ink and inkjet recording method capable of an image having an excellent hue, fastness to light and ozone gas resistance. To provide various coloring compositions such as an ink sheet for heat-sensitive recording material, color toner for electrophotography, and color filter, and to provide improving method of oxidation resistance of an image. [Means for Resolution] A phthalocyanine compound substituted with —SO₂NH—Z (Z represents a heterocyclic group) in at least one combination of 2 and 3, 6 and 7, 10 and 11, and 14 and 15-positions, wherein at least one of the 1 to 16-positions has two or more carbon atoms and the total number of the carbon atom thereof is 8 or more, inkjet ink using the compound, ink sheet, color toner and a color filter composition, which use the compound.

Claims

1. An ink comprising a phthalocyanine compound represented by the following general formula (I):

2. The ink according to claim 1, wherein the compound represented by the general formula (I) is a compound represented by the following general formula (V):

3. The ink according to claim 1, wherein the compound represented by the general formula (I) is a compound represented by the following general formula (IX):

4. The ink according to claim 1, wherein the compound represented by the general formula (I) is contained in an amount of 0.2 parts by weight or more and 10 parts by weight or less in 100 parts by weight of the ink.

5. The ink according to claim 2, wherein the compound represented by the general formula (V) is contained in an amount of 0.2 parts by weight or more and 10 parts by weight or less in 100 parts by weight of the ink.

6. The ink according to claim 3, wherein the compound represented by the general formula (IX) is contained in an amount of 0.2 parts by weight or more and 10 parts by weight or less in 100 parts by weight of the ink.

7. The ink according to claim 1, which is an ink for inkjet recording.

8. The ink according to claim 2, which is an ink for inkjet recording.

9. The ink according to claim 3, which is an ink for inkjet recording.

10. An inkjet recording method, which comprises forming images on an image-receiving material having an ink-receiving layer containing white inorganic pigment particles on a support with the ink for inkjet recording according to claim 7.

11. An inkjet recording method, which comprises forming images on an image-receiving material having an ink-receiving layer containing white inorganic pigment particles on a support with the ink for inkjet recording according to claim 8.

12. An inkjet recording method, which comprises forming images on an image-receiving material having an ink-receiving layer containing white inorganic pigment particles on a support with the ink for inkjet recording according to claim 9.

13. A method of improving ozone gas resistance by forming images using the ink for inkjet recording according to claim 9, thereby improving an ozone gas resistance of a colored image material.

14. An ink, comprising a phthalocyanine compound represented by the following general formula (II):

15. The ink according to claim 14, wherein the compound represented by the general formula (II) is a compound represented by the following general formulae (VI):

17. The ink according to claim 14, wherein the compound represented by the general formula (II) is contained in an amount of 0.2 parts by weight or more and 10 parts by weight or less in 100 parts by weight of the ink.

18. The ink according to claim 15, wherein the compound represented by the general formula (VI) is contained in an amount of 0.2 parts by weight or more and 10 parts by weight or less in 100 parts by weight of the ink.

20. The ink according to claim 14, which is an ink for inkjet recording.

21. The ink according to claim 15, which is an ink for inkjet recording.

23. An inkjet recording method, which comprises forming images on an image-receiving material having an ink-receiving layer containing white inorganic pigment particles on a support with the ink for inkjet recording according to claim 20.

24. An inkjet recording method, which comprises forming images on an image-receiving material having an ink-receiving layer containing white inorganic pigment particles on a support with the ink for inkjet recording according to claim 21.

58. The ink according to claim 14, wherein the substituent of the alkyl group having 2 or more carbon atoms or the aryl group having 2 or more carbon atoms is selected from the group consisting of a halogen atom, an alkyl group, a cyano group, an alkoxy group, an amide group, an ureido group, a sulfonamide group, a carbamoyl group, a sulfamoyl group and an alkoxycarbonyl group.

59. The ink according to claim 15, wherein the substituent of the alkyl group having 2 or more carbon atoms or the aryl group having 2 or more carbon atoms is selected from the group consisting of a halogen atom, an alkyl group, a cyano group, an alkoxy group, an amide group, an ureido group, a sulfonamide group, a carbamoyl group, a sulfamoyl group and an alkoxycarbonyl group.

16. An ink, comprising a phthalocyanine compound represented by the following general formula (X):

19. The ink according to claim 16, wherein the compound represented by the general formula (X) is contained in an amount of 0.2 parts by weight or more and 10 parts by weight or less in 100 parts by weight of the ink.

22. The ink according to claim 16, which is an ink for inkjet recording.

25. An inkjet recording method, which comprises forming images on an image-receiving material having an ink-receiving layer containing white inorganic pigment particles on a support with the ink for inkjet recording according to claim 22.

26. A method of improving ozone gas resistance by forming images using the ink for inkjet recording according to claim 22, thereby improving an ozone gas resistance of a colored image material.

27. An ink comprising a phthalocyanine compound represented by the following general formula (III):

28. The ink according to claim 27, wherein the compound represented by the general formula (III) is a compound represented by the following general formula (VII):

29. The ink according to claim 27, wherein the compound represented by the general formula (III) is a compound represented by the following general formulae (XI):

30. The ink according to claim 27, wherein the compound represented by the general formula (III) is contained in an amount of 0.2 parts by weight or more and 10 parts by weight or less in 100 parts by weight of the ink.

31. The ink according to claim 28, wherein the compound represented by the general formula (VII) is contained in an amount of 0.2 parts by weight or more and 10 parts by weight or less in 100 parts by weight of the ink.

32. The ink according to claim 29, wherein the compound represented by the general formula (XI) is contained in an amount of 0.2 parts by weight or more and 10 parts by weight or less in 100 parts by weight of the ink.

33. The ink according to claim 27, which is an ink for inkjet recording.

34. The ink according to claim 28, which is an ink for inkjet recording.

35. The ink according to claim 29, which is an ink for inkjet recording.

36. An inkjet recording method, which comprises forming images on an image-receiving material having an ink-receiving layer containing white inorganic pigment particles on a support with the ink for inkjet recording according to claim 33.

37. An inkjet recording method, which comprises forming images on an image-receiving material having an ink-receiving layer containing white inorganic pigment particles on a support with the ink for inkjet recording according to claim 34.

38. An inkjet recording method, which comprises forming images on an image-receiving material having an ink-receiving layer containing white inorganic pigment particles on a support with the ink for inkjet recording according to claim 35.

39. A method of improving ozone gas resistance by forming images using the ink for inkjet recording according to claim 35, thereby improving an ozone gas resistance of a colored image material.

40. An ink comprising a phthalocyanine compound represented by the following general formula (IV):

41. The ink according to claim 40, wherein the compound represented by the general formula (IV) is a compound represented by the following general formula (VII):

42. The ink according to claim 40, wherein the compound represented by the general formula (IV) is a compound represented by the following general formula (XII):

43. The ink according to claim 40, wherein the compound represented by the general formula (IV) is contained in an amount of 0.2 parts by weight or more and 10 parts by weight or less in 100 parts by weight of the ink.

44. The ink according to claim 41, wherein the compound represented by the general formula (VIII) is contained in an amount of 0.2 parts by weight or more and 10 parts by weight or less in 100 parts by weight of the ink.

45. The ink according to claim 42, wherein the compound represented by the general formula (XII) is contained in an amount of 0.2 parts by weight or more and 10 parts by weight or less in 100 parts by weight of the ink.

46. The ink according to claim 40, which is an ink for inkjet recording.

47. The ink according to claim 41, which is an ink for inkjet recording.

48. The ink according to claim 42, which is an ink for inkjet recording.

49. An inkjet recording method, which comprises forming images on an image-receiving material having an ink-receiving layer containing white inorganic pigment particles on a support with the ink for inkjet recording according to claim 46.

50. An inkjet recording method, which comprises forming images on an image-receiving material having an ink-receiving layer containing white inorganic pigment particles on a support with the ink for inkjet recording according to claim 47.

51. An inkjet recording method, which comprises forming images on an image-receiving material having an ink-receiving layer containing white inorganic pigment particles on a support with the ink for inkjet recording according to claim 48.

52. A method of improving ozone gas resistance by forming images using the ink for inkjet recording according to claim 48, thereby improving an ozone gas resistance of a colored image material.

53. A phthalocyanine compound, which is represented by the general formulae (IX):

54. The phthalocyanine compound according to claim 53, wherein in the general formula (IX), Z₁, Z₂, Z₃, and Z₄ are each represented by -A₁-L₁-A₂-Q, wherein A₁ and A₂ each represents a substituted or unsubstituted alkylene group;

L₁ represents a divalent connecting group; and

Q represents an alkoxy group.

55. The phthalocyanine compound according to claim 54, wherein in the general formula (IX), L₁ is SO₂NH—

, —

COO—

, —

CONH—

, —

NHSO₂—

, —

NHCO—

, —

SO₂—

, or —

O—

.

56. A phthalocyanine compound, which is represented by the general formulae (X):

57. A phthalocyanine compound, which is represented by the general formulae (XI):