Imageable composition containing an infrared absorber with counter anion derived from a non-volatile acid
View Patent ↗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.
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:
wherein n is from 1 to 11, and combinations thereof.
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—SO 3 H, 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:
wherein each of R 1 , R 2 , R 3 , R 4 and R 5 is independently selected from the group consisting of: hydrogen, alkyl of 1 to 12 carbon atoms, haloalkyl of 1 to 22 carbon atoms having at least one halogen, aryl of 6 to 12 carbon atoms, halogen, hydroxy, alkoxy, cyano, nitro, alkoxycarbonyl and acyl.
29. The composition of claim 28 , wherein the acyl is represented by the formula:
wherein R 6 is selected from the group consisting of: hydrogen, alkyl of 1 to 12 carbon atoms, haloalkyl of 1 to 12 carbon atoms having at least one halogen, alkoxy, cyano, nitro, alkoxycarbonyl and acetyl.
30. The composition of claim 1 , wherein the sulfonic acid is represented by the formula:
wherein each of R 1 , R 4 and R 6 is independently selected from the group consisting of: hydrogen, alkyl of 1 to 12 carbon atoms, haloalkyl of 1 to 12 carbon atoms having at least one halogen, aryl of 6 to 12 carbon atoms, halogen, hydroxy, alkoxy, cyano, nitro, alkoxycarbonyl and acyl and wherein R 7 is selected from the group consisting of: hydrogen, alkyl of 1 to 12 carbon atoms, haloalkyl of 1 to 12 carbon atoms having at least one halogen, aryl of 6 to 12 carbon atoms, alkoxycarbonyl and acyl.
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—SO 3 H, 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:
wherein each of R 1 , R 2 , R 3 , R 4 and R 5 is independently selected from the group consisting of: hydrogen, alkyl of 1 to 12 carbon atoms, haloalkyl of 1 to 22 carbon atoms having at least one halogen, aryl of 6 to 12 carbon atoms, halogen, hydroxy, alkoxy, cyano, nitro, alkoxycarbonyl and acyl.
56. The imageable element of claim 55 , wherein the acyl is represented by the formula:
wherein R 6 is selected from the group consisting of: hydrogen, alkyl of 1 to 12 carbon atoms, haloalkyl of 1 to 12 carbon atoms having at least one halogen, alkoxy, cyano, nitro, alkoxycarbonyl and acetyl.
57. The imageable element of claim 35 , wherein the sulfonic acid is represented by the formula:
wherein each of R 1 , R 4 and R 6 is independently selected from the group consisting of: hydrogen, alkyl of 1 to 12 carbon atoms, haloalkyl of 1 to 12 carbon atoms having at least one halogen, aryl of 6 to 12 carbon atoms, halogen, hydroxy, alkoxy, cyano, nitro, alkoxycarbonyl and acyl and wherein R 7 is selected from the group consisting of: hydrogen, alkyl of 1 to 12 carbon atoms, haloalkyl of 1 to 12 carbon atoms having at least one halogen, aryl of 6 to 12 carbon atoms, alkoxycarbonyl and acyl.
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.