Imageable composition containing colorant having a counter anion derived from a non-volatile acid

• US 6,921,620 B2
• Filed: 08/21/2001
• Issued: 07/26/2005
• Est. Priority Date: 08/21/2001
• Status: Expired due to Fees

• Current Assignee: Eastman Kodak Company
• Original Assignee: Kodak Polychrome Graphics Company Limited (Eastman Kodak Company)
• Inventors: Hayakawa, Eiji, Miyamoto, Yasushi, Huang, Jianbing, Collins, Jeffrey, Jordan, Thomas
• Primary Examiner(s): CHU, JOHN S Y
• Application Number:
  US09/933,884
• Publication Number:
  US 20030113655A1
• Time in Patent Office: 1,435 Days
• Field of Search: 430/157, 430/176, 430/270.1, 430/302, 430/330
• 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 1/1016 characterised by structural details, e.g. protective layers, backcoat layers or several imaging layers
• 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 2210/14 Multiple imaging layers
• 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: 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, which includes an acid curable composition, an acid generator, a colorant having a counter anion derived from a non-volatile acid, and further optionally, an infrared absorber or photothermal converter material. The present invention further provides an imageable element, which includes a substrate and an imageable composition according to the present invention coated on a surface of the substrate. Also provided is method of producing an imaged element according to the present invention.

Claims

1. An imageable composition comprising:

an acid curable composition;

an acid generator; and

a colorant, wherein the colorant includes a counter anion derived from a non-volatile acid;

and further comprising an infrared absorber, a photothermal converter material, or both.

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 crosslinker 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 iodoniumn 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:

wherein n is from 1 to 11, and combinations thereof.

20. The composition of claim 1, wherein the composition comprises a photothermal converter material.

21. The composition of claim 1, wherein the composition comprises an infrared absorber.

22. The composition of claim 21, wherein the infrared absorber is selected from the group consisting of:

a pigment, a dye, and combinations thereof.

23. The composition of claim 21, wherein the infrared absorber includes a dye selected from the group consisting of:

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

24. The composition of claim 21, wherein the infrared absorber includes an infrared-absorbing dye including a counter anion derived from a non-volatile acid.

25. The composition of claim 24, wherein the infrared-absorbing dye includes a counter anion derived from a non-volatile sulfonic acid.

26. The composition of claim 24, wherein the infrared-absorbing dye is represented by the structure:

27. The composition of claim 24, wherein the infrared-absorbing dye is represented by the structure:

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

29. The composition of claim 1, wherein the colorant includes a compound represented by the structure:

30. 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; and

a colorant, wherein the colorant includes a counter anion derived from a non-volatile acid, and wherein the colorant enhances the visual contrast between image areas and non-image areas after imaging of the imageable element;

and further comprising an infrared absorber, a photothermal converter material, or both.

31. The imageable element of claim 30, wherein the substrate is an aluminum sheet.

32. The imageable element of claim 30, wherein the acid curable composition comprises:

a crosslinkable binder; and

a crosslinking agent.

33. The imageable element of claim 32, wherein the binder comprises a polymer having at least two reactive hydroxy groups.

34. The imageable element of claim 32, 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.

35. The imageable element of claim 32, wherein the binder comprises a novolak resin.

36. The imageable element of claim 32, 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.

37. The imageable element of claim 32, wherein the crosslinking agent comprises a resole resin.

38. The imageable element of claim 30, wherein the acid generator is an ultraviolet, visible or infrared radiation or heat activated compound.

39. The imageable element of claim 30, wherein the acid generator comprises an onium salt.

40. The imageable element of claim 39, 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.

41. The imageable element of claim 30, wherein the acid generator includes a monomeric or oligomeric aromatic diazonium salt.

42. The imageable element of claim 30, wherein the imageable coating comprises a pholothermal converter material.

43. The imageable element of claim 30, wherein the imageable coating comprises an infrared absorber.

44. The imageable element of claim 43, wherein the infrared absorber is selected from the group consisting of:

a pigment, a dye, and combinations thereof.

45. The imageable element of claim 43, wherein the infrared absorber includes a dye selected from the group consisting of:

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

46. The imageable element of claim 43, wherein the infrared absorber includes an infrared-absorbing dye including a counter anion derived from a non-volatile acid.

47. The imageable element of claim 46, wherein the infrared-absorbing dye includes a counter anion derived from a non-volatile sulfonic acid.

48. The imageable element of claim 30, wherein the colorant includes a counter anion derived from a non-volatile sulfonic acid.

49. The imageable element of claim 30, wherein the colorant includes a compound represented by the structure:

50. 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, and

a colorant, wherein the colorant includes a counter anion derived from a non-volatile acid, and wherein the colorant enhances the visual contrast between image areas and non-image areas after imaging of the imageable element;

and further comprises an infrared absorber, a photothermal converter material, or both; and

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

51. 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, and a colorant, wherein the colorant includes a counter anion derived from a non-volatile acid, and further comprising an infrared absorber or a photothermal converter material;

imagewise exposing the imageable element to heat 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;

wherein the colorant enhances the visual contrast between image areas and non-image areas of the imaged element.

52. The method of claim 51, wherein the step of imagewise exposing is carried out using an infrared laser.