Imageable composition containing an infrared absorber with counter anion derived from a non-volatile acid

• US 7,056,639 B2
• Filed: 08/20/2004
• Issued: 06/06/2006
• Est. Priority Date: 08/21/2001
• Status: Expired due to Fees

• Current Assignee: Eastman Kodak Company
• Original Assignee: Eastman Kodak Company
• Inventors: Haley, Neil F., Huang, Jianbing, Hayakawa, Eiji, Miyamoto, Yasushi, Kalamen, John, Collins, Jeffrey J., Jordan, Thomas R.
• Primary Examiner(s): CHU, JOHN S Y
• Application Number:
  US10/922,377
• Publication Number:
  US 20050079439A1
• Time in Patent Office: 655 Days
• Field of Search: 430/163, 430/175, 430/176, 430/270.1, 430/302, 430/157
• US Class Current: 430/157
• CPC Class Codes: B41C 1/1008 by removal or destruction of lithographic material on the lithographic support, e.g. by laser or spark ablation; by the use of materials rendered soluble or insoluble by heat exposure, e.g. by heat produced from a light to heat transforming system; by on-the-press exposure or on-the-press development, e.g. by the fountain of photolithographic materials
• CPC Class Codes: B41C 2210/04 Negative working, i.e. the non-exposed (non-imaged) areas are removed
• CPC Class Codes: B41C 2210/06 Developable by an alkaline solution
• CPC Class Codes: B41C 2210/10 Developable by an acidic solution
• CPC Class Codes: B41C 2210/22 characterised by organic non-macromolecular additives, e.g. dyes, UV-absorbers, plasticisers
• CPC Class Codes: B41C 2210/24 characterised by a macromolecular compound or binder obtained by reactions involving carbon-to-carbon unsaturated bonds, e.g. acrylics, vinyl polymers
• CPC Class Codes: B41C 2210/26 characterised by a macromolecular compound or binder obtained by reactions not involving carbon-to-carbon unsaturated bonds
• CPC Class Codes: B41C 2210/262 Phenolic condensation polymers, e.g. novolacs, resols
• CPC Class Codes: B41C 2210/264 Polyesters; Polycarbonates
• CPC Class Codes: B41M 5/368 involving the creation of a soluble/insoluble or hydrophilic/hydrophobic permeability pattern; Peel development B41M5/366 takes precedence
• CPC Class Codes: G03F 7/0045 with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
• CPC Class Codes: G03F 7/016 Diazonium salts or compounds G03F7/075 takes precedence
• CPC Class Codes: G03F 7/021 Macromolecular diazonium compounds; Macromolecular additives, e.g. binders G03F7/0166 takes precedence
• CPC Class Codes: G03F 7/0382 the macromolecular compound being present in a chemically amplified negative photoresist composition

Abstract

The present invention provides an imageable composition including an acid curable composition, an acid generator, an infrared absorber having a counter anion derived from a non-volatile acid, and a strong acid such as a sulfonic acid. The imageable composition may include components such as a crosslinkable binder or a colorant. In one embodiment, the imageable composition further includes a colorant having a counter anion derived from a non-volatile acid. The present invention further provides an imageable element, which includes a substrate and an imageable coating on a surface of the substrate. Also provided is method of producing an imaged element according to the invention.

Claims

1. An imageable composition comprising:

an acid curable composition;

an acid generator;

an infrared absorber having a counter anion derived from a non-volatile acid; and

a sulfonic acid having a pKa of not more than about 8.

2. The composition of claim 1, wherein the acid curable composition comprises:

a crosslinkable binder; and

a crosslinking agent.

3. The composition of claim 2, wherein the binder comprises a polymer having at least two reactive groups each independently selected from the group consisting of:

hydroxy, carboxylic acid, amine, carbamate, amide, sulfonamide and imide.

4. The composition of claim 2, wherein the binder comprises a polymer having at least two reactive hydroxy groups.

5. The composition of claim 2, wherein the binder comprises a polymer selected from the group consisting of:

a polyol, a polyether polyol, a novolak resin, a resole resin, a hydroxyfunctional acrylic resin, a hydroxyfunctional polyester resin, and combinations thereof.

6. The composition of claim 2, wherein the binder comprises a novolak resin.

7. The composition of claim 2, comprising a crosslinking agent selected from the group consisting of:

a resole resin, an amino resin, an amido resin, an epoxy compound having at least two epoxide groups, and combinations thereof.

8. The composition of claim 2, wherein the crosslinking agent comprises a resole resin.

9. The composition of claim 2, wherein the crosslinking agent comprises an amino resin having at least two alkoxymethyl groups.

10. The composition of claim 2, comprising an isocyanate crosslinking agent having at least two isocyanate groups.

11. The composition of claim 1, wherein the acid generator is an ultraviolet, visible or infrared radiation or heat activated compound.

12. The composition of claim 1, comprising an acid generator selected from the group consisting of:

an onium salt, a covalently bound sulfonate group-containing compound, hydrocarbylsulfonamido-N-hydrocarbyl sulfonate, and combinations thereof.

13. The composition of claim 1, wherein the acid generator comprises an onium salt.

14. The composition of claim 13, wherein the onium salt has a non-nucleophilic counter anion selected from the group consisting of:

tetrafluoroborate, hexafluorophosphate, hexafluoroarsenate, hexafluoroantimonate, triflate, tetrakis(pentafluorophenyl)borate, pentafluoroethyl sulfonate, p-methylbenzene sulfonate, ethyl sulfonate, trifluoromethyl acetate and pentafluoroethyl acetate.

15. The composition of claim 13, wherein the onium salt is selected from the group consisting of:

an iodonium salt, a sulfonium salt, a hydrocarbyloxysulfonium salt, a hydrocarbyloxyammonium salt, an aryl diazonium salt, and combinations thereof.

16. The composition of claim 13, wherein the onium salt is a salt of an N-hydrocarbyloxy-substituted nitrogen-containing heterocyclic compound.

17. The composition of claim 1, wherein the acid generator includes a monomeric or oligomeric aromatic diazonium salt.

18. The composition of claim 17, wherein the diazonium salt is selected from the group consisting of 2-methoxy-4-phenylaminobenzene diazonium hexafluorophosphate, 2-methoxy-4-phenylaminobenzenediazonium p-toluenesulfonate, and combinations thereof.

19. The composition of claim 17, wherein the diazonium salt is an oligomeric diazonium salt represented by one of the structures:

20. The composition of claim 1, wherein the infrared absorber includes an infrared-absorbing dye selected from the group consisting of:

cyanine dyes, squarylium dyes, pyrylium salts and nickel thiolate complexes.

21. The composition of claim 20, wherein the infrared-absorbing dye includes a counter anion derived from a non-volatile sulfonic acid.

22. The composition of claim 20 wherein the infrared-absorbing dye is represented by the structure:

23. The composition of claim 20, wherein the infrared-absorbing dye is represented by the structure:

24. The composition of claim 1, wherein the sulfonic acid is represented by the formula R—

SO₃H, wherein R is a substituted or unsubstituted hydrocarbyl of 1 to 22 carbon atoms, or a substituted or unsubstituted aryl of 6 to 22 carbon atoms.

25. The composition of claim 24, wherein R is selected from the group consisting of:

linear, branched or cyclic alkyl of 1 to 22 carbon atom, linear, branched or cyclic haloalkyl of 1 to 22 carbon atom having at least one halogen and a mixture thereof.

26. The composition of claim 1, wherein the sulfonic acid is an acid having a pKa of not more than about 5.

27. The composition of claim 1, wherein the sulfonic acid is an acid having a pKa of not more than about 4.

28. The composition of claim 1, wherein the sulfonic acid is an aryl sulfonic acid represented by the formula:

29. The composition of claim 28, wherein the acyl is represented by the formula:

30. The composition of claim 1, wherein the sulfonic acid is represented by the formula:

31. The composition of claim 1, wherein the sulfonic acid is 3-benzoyl-4-hydroxy-6-methoxybenzenesulfonic acid.

32. The composition of claim 1, wherein the composition further includes a colorant having a counter anion derived from a non-volatile acid.

33. The composition of claim 32, wherein the colorant includes a counter anion derived from a non-volatile sulfonic acid.

34. The composition of claim 32, wherein the colorant includes a compound represented by the structure:

35. An imageable element comprising:

a substrate; and

an imageable coating on a surface of the substrate, the coating comprising;

an acid curable composition, an acid generator, an infrared absorber having a counter anion derived from a non-volatile acid, and a sulfonic acid having a pKa of not more than about 8.

36. The imageable element of claim 35, wherein the substrate is an aluminum sheet.

37. The imageable element of claim 35, wherein the acid curable composition comprises:

a crosslinkable binder; and

a crosslinking agent.

38. The imageable element of claim 37, wherein the binder comprises a polymer having at least two reactive hydroxy groups.

39. The imageable element of claim 37, wherein the binder comprises a polymer selected from the group consisting of:

a polyol, a polyether polyol, a novolak resin, a resole resin, a hydroxyfunctional acrylic resin, a hydroxyfunctional polyester resin, and combinations thereof.

40. The imageable element of claim 37, wherein the binder comprises a novolak resin.

41. The imageable element of claim 37, comprising a crosslinking agent selected from the group consisting of:

a resole resin, an amino resin, an amido resin, an epoxy compound having at least two epoxide groups, and combinations thereof.

42. The imageable element of claim 37, wherein the crosslinking agent comprises a resole resin.

43. The imageable element of claim 35, wherein the acid generator is an ultraviolet, visible or infrared radiation or heat activated compound.

44. The imageable element of claim 35, wherein the acid generator comprises an onium salt.

45. The imageable element of claim 44, wherein the onium salt is selected from the group consisting of:

an iodonium salt, a sulfonium salt, a hydrocarbyloxysulfonium salt, a hydrocarbyloxyammonium salt, an aryl diazonium salt, and combinations thereof.

46. The imageable element of claim 35, wherein the acid generator includes a monomeric or oligomeric aromatic diazonium salt.

47. The imageable element of claim 35, wherein the infrared absorber includes an infrared-absorbing dye selected from the group consisting of:

cyanine dyes, squarylium dyes, pyrylium salts and nickel thiolate complexes.

48. The imageable element of claim 35, wherein the imageable coating further includes a colorant having a counter anion derived from a non-volatile acid.

49. The imageable element of claim 48, wherein the colorant includes a counter anion derived from a non-volatile sulfonic acid.

50. The imageable element of claim 48, wherein the colorant includes a compound represented by the structure:

51. The imageable element of claim 35, wherein the sulfonic acid is represented by the formula R—

SO₃H, wherein R is a substituted or unsubstituted hydrocarbyl of 1 to 22 carbon atoms, or a substituted or unsubstituted aryl of 6 to 22 carbon atoms.

52. The imageable element of claim 51, wherein R is selected from the group consisting of:

linear, branched or cyclic alkyl of 1 to 22 carbon atom, linear, branched or cyclic haloalkyl of 1 to 22 carbon atom having at least one halogen and a mixture thereof.

53. The imageable element of claim 35, wherein the sulfonic acid is an acid having a pKa of not more than about 5.

54. The imageable element of claim 35, wherein the sulfonic acid is an acid having a pKa of not more than about 4.

55. The imageable element of claim 35, wherein the sulfonic acid is an aryl sulfonic acid represented by the formula:

56. The imageable element of claim 55, wherein the acyl is represented by the formula:

57. The imageable element of claim 35, wherein the sulfonic acid is represented by the formula:

58. The imageable element of claim 35, wherein the sulfonic acid is 3-benzoyl-4-hydroxy-6-methoxybenzenesulfonic acid.

59. A method of making an imageable element including a substrate and an imageable coating on the substrate, the method comprising the steps of:

contacting a substrate with an imageable composition dissolved or dispersed in a suitable solvent, wherein the imageable composition comprises an acid curable composition, an acid generator, an infrared absorber having a counter anion derived from a non-volatile acid, and a sulfonic acid having a pKa of not more than about 8; and

drying to remove solvent, leaving an imageable coating on the substrate.

60. The method of claim 59, wherein the imageable composition further includes a colorant having a counter anion derived from a non-volatile acid.

61. The method of claim 60, wherein the colorant includes a counter anion derived from a non-volatile sulfonic acid.

62. The method of claim 60, wherein the colorant includes a compound represented by the structure:

63. A method of producing an imaged element comprising the steps of:

providing a thermally imageable element comprising a substrate and a thermally imageable coating on a surface of the substrate, the coating comprising an acid curable composition, an acid generator an infrared absorber having a counter anion derived from a non-volatile acid, and a sulfonic acid having a pKa of not more than about 8;

imagewise exposing the imageable element to radiation to produce an exposed element having exposed and unexposed regions of the coating;

baking the exposed element at a temperature and period of time sufficient to produce a cured element; and

contacting the cured element with a developer to remove the unexposed regions of the coating and thereby produce the imaged element.

64. The method of claim 63, wherein the imageable composition further includes a colorant having a counter anion derived from a non-volatile acid.

65. The method of claim 64, wherein the colorant includes a counter anion derived from a non-volatile sulfonic acid.

66. The method of claim 64, wherein the colorant includes a compound represented by the structure:

67. The method of claim 63, wherein the step of imagewise exposing is carried out using an infrared laser.