EP1359008A1 - Mélange photosensible et matériau pour l'enregistrement utilisant ce mélange - Google Patents
Mélange photosensible et matériau pour l'enregistrement utilisant ce mélange Download PDFInfo
- Publication number
- EP1359008A1 EP1359008A1 EP02100424A EP02100424A EP1359008A1 EP 1359008 A1 EP1359008 A1 EP 1359008A1 EP 02100424 A EP02100424 A EP 02100424A EP 02100424 A EP02100424 A EP 02100424A EP 1359008 A1 EP1359008 A1 EP 1359008A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- meth
- acrylate
- mixture
- mixture according
- weight
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 239000000203 mixture Substances 0.000 title claims abstract description 49
- 239000000463 material Substances 0.000 title claims abstract description 27
- 230000005855 radiation Effects 0.000 title claims description 24
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 30
- 239000000178 monomer Substances 0.000 claims abstract description 22
- 238000007639 printing Methods 0.000 claims abstract description 16
- 239000011230 binding agent Substances 0.000 claims abstract description 13
- 238000004519 manufacturing process Methods 0.000 claims abstract description 12
- GDIYMWAMJKRXRE-UHFFFAOYSA-N (2z)-2-[(2e)-2-[2-chloro-3-[(z)-2-(1,3,3-trimethylindol-1-ium-2-yl)ethenyl]cyclohex-2-en-1-ylidene]ethylidene]-1,3,3-trimethylindole Chemical compound CC1(C)C2=CC=CC=C2N(C)C1=CC=C1C(Cl)=C(C=CC=2C(C3=CC=CC=C3[N+]=2C)(C)C)CCC1 GDIYMWAMJKRXRE-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000000034 method Methods 0.000 claims abstract description 8
- 239000012670 alkaline solution Substances 0.000 claims abstract description 4
- 239000000975 dye Substances 0.000 claims description 36
- -1 triazine compound Chemical class 0.000 claims description 32
- 229920001577 copolymer Polymers 0.000 claims description 24
- 150000003254 radicals Chemical class 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
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- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 8
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 5
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 5
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 claims description 4
- 229910000838 Al alloy Inorganic materials 0.000 claims description 4
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 4
- 229910052782 aluminium Inorganic materials 0.000 claims description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
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- 239000001267 polyvinylpyrrolidone Substances 0.000 claims description 4
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 4
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 3
- 239000004952 Polyamide Substances 0.000 claims description 3
- 239000004793 Polystyrene Substances 0.000 claims description 3
- 229940081735 acetylcellulose Drugs 0.000 claims description 3
- 239000004202 carbamide Substances 0.000 claims description 3
- 229920002301 cellulose acetate Polymers 0.000 claims description 3
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- 229920002647 polyamide Polymers 0.000 claims description 3
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- 239000004814 polyurethane Substances 0.000 claims description 3
- 229920002635 polyurethane Polymers 0.000 claims description 3
- 229920001897 terpolymer Polymers 0.000 claims description 3
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
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- 239000004709 Chlorinated polyethylene Substances 0.000 claims description 2
- 229910020366 ClO 4 Inorganic materials 0.000 claims description 2
- 239000001856 Ethyl cellulose Substances 0.000 claims description 2
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 claims description 2
- 229920002845 Poly(methacrylic acid) Polymers 0.000 claims description 2
- 229920000388 Polyphosphate Polymers 0.000 claims description 2
- 239000004743 Polypropylene Substances 0.000 claims description 2
- SMEGJBVQLJJKKX-HOTMZDKISA-N [(2R,3S,4S,5R,6R)-5-acetyloxy-3,4,6-trihydroxyoxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O)OC(=O)C)O)O SMEGJBVQLJJKKX-HOTMZDKISA-N 0.000 claims description 2
- 229920013820 alkyl cellulose Polymers 0.000 claims description 2
- 125000005907 alkyl ester group Chemical group 0.000 claims description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 claims description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 claims description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 claims description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 2
- 229920001249 ethyl cellulose Polymers 0.000 claims description 2
- 235000019325 ethyl cellulose Nutrition 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 229920000609 methyl cellulose Polymers 0.000 claims description 2
- 239000001923 methylcellulose Substances 0.000 claims description 2
- 235000010981 methylcellulose Nutrition 0.000 claims description 2
- 229920003023 plastic Polymers 0.000 claims description 2
- 239000004033 plastic Substances 0.000 claims description 2
- 229920001490 poly(butyl methacrylate) polymer Polymers 0.000 claims description 2
- 229920001483 poly(ethyl methacrylate) polymer Polymers 0.000 claims description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 claims description 2
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 claims description 2
- 229920001633 poly(α-methyl styrene) Polymers 0.000 claims description 2
- 229920001281 polyalkylene Polymers 0.000 claims description 2
- 229920000129 polyhexylmethacrylate Polymers 0.000 claims description 2
- 239000001205 polyphosphate Substances 0.000 claims description 2
- 235000011176 polyphosphates Nutrition 0.000 claims description 2
- 229920001155 polypropylene Polymers 0.000 claims description 2
- 229920002689 polyvinyl acetate Polymers 0.000 claims description 2
- 239000011118 polyvinyl acetate Substances 0.000 claims description 2
- 235000019422 polyvinyl alcohol Nutrition 0.000 claims description 2
- 239000004800 polyvinyl chloride Substances 0.000 claims description 2
- 239000005033 polyvinylidene chloride Substances 0.000 claims description 2
- 235000000346 sugar Nutrition 0.000 claims description 2
- 125000001302 tertiary amino group Chemical group 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 239000003791 organic solvent mixture Substances 0.000 claims 2
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- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 239000000470 constituent Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 abstract description 5
- 239000006096 absorbing agent Substances 0.000 abstract description 3
- 239000000758 substrate Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 22
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 16
- 125000004432 carbon atom Chemical group C* 0.000 description 13
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 12
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- 125000001183 hydrocarbyl group Chemical group 0.000 description 8
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 8
- ATOUXIOKEJWULN-UHFFFAOYSA-N 1,6-diisocyanato-2,2,4-trimethylhexane Chemical compound O=C=NCCC(C)CC(C)(C)CN=C=O ATOUXIOKEJWULN-UHFFFAOYSA-N 0.000 description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 7
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 6
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- 230000035945 sensitivity Effects 0.000 description 6
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 5
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- 125000001931 aliphatic group Chemical group 0.000 description 5
- 125000005442 diisocyanate group Chemical group 0.000 description 5
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- 125000004433 nitrogen atom Chemical group N* 0.000 description 5
- 239000000049 pigment Substances 0.000 description 5
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- IMHBYKMAHXWHRP-UHFFFAOYSA-N anilazine Chemical compound ClC1=CC=CC=C1NC1=NC(Cl)=NC(Cl)=N1 IMHBYKMAHXWHRP-UHFFFAOYSA-N 0.000 description 3
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- 238000003384 imaging method Methods 0.000 description 3
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- 238000002360 preparation method Methods 0.000 description 3
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- 125000003545 alkoxy group Chemical group 0.000 description 2
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- 238000004132 cross linking Methods 0.000 description 2
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- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 description 1
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- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- XUIYVEVRWRRDIR-UHFFFAOYSA-N 2,2,3-tris(hydroxymethyl)-3-methylbutane-1,4-diol Chemical compound OCC(C)(CO)C(CO)(CO)CO XUIYVEVRWRRDIR-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 description 1
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 1
- FDSUVTROAWLVJA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(CO)(CO)COCC(CO)(CO)CO FDSUVTROAWLVJA-UHFFFAOYSA-N 0.000 description 1
- GTELLNMUWNJXMQ-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical class OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.CCC(CO)(CO)CO GTELLNMUWNJXMQ-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- XLLXMBCBJGATSP-UHFFFAOYSA-N 2-phenylethenol Chemical compound OC=CC1=CC=CC=C1 XLLXMBCBJGATSP-UHFFFAOYSA-N 0.000 description 1
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 1
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 description 1
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 description 1
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 1
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical group OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
- UCEYUKWCFYVBKV-UHFFFAOYSA-N C1(CC(C=C2SC3=CC=CC=C3C=C12)=O)=O Chemical compound C1(CC(C=C2SC3=CC=CC=C3C=C12)=O)=O UCEYUKWCFYVBKV-UHFFFAOYSA-N 0.000 description 1
- 125000005915 C6-C14 aryl group Chemical group 0.000 description 1
- SHBTUGJAKBRBBJ-UHFFFAOYSA-N CCN(C(CC(N1CC)=O)=O)C1=S Chemical compound CCN(C(CC(N1CC)=O)=O)C1=S SHBTUGJAKBRBBJ-UHFFFAOYSA-N 0.000 description 1
- RVEPFSQQHDIKRE-UHFFFAOYSA-N CN(C(CC(N1C)=O)O)C1=S Chemical compound CN(C(CC(N1C)=O)O)C1=S RVEPFSQQHDIKRE-UHFFFAOYSA-N 0.000 description 1
- IUVACELPFXBLHY-UHFFFAOYSA-N CSc1nnc(SC)[s]1 Chemical compound CSc1nnc(SC)[s]1 IUVACELPFXBLHY-UHFFFAOYSA-N 0.000 description 1
- RPXUSEGLHQMSIM-UHFFFAOYSA-N CSc1nnn[n]1-c1ccccc1 Chemical compound CSc1nnn[n]1-c1ccccc1 RPXUSEGLHQMSIM-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical group [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- NPKSPKHJBVJUKB-UHFFFAOYSA-N N-phenylglycine Chemical group OC(=O)CNC1=CC=CC=C1 NPKSPKHJBVJUKB-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical group C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- 206010034960 Photophobia Diseases 0.000 description 1
- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000005399 allylmethacrylate group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 150000008365 aromatic ketones Chemical class 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 239000011668 ascorbic acid Chemical group 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229920005601 base polymer Polymers 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- QUZSUMLPWDHKCJ-UHFFFAOYSA-N bisphenol A dimethacrylate Chemical compound C1=CC(OC(=O)C(=C)C)=CC=C1C(C)(C)C1=CC=C(OC(=O)C(C)=C)C=C1 QUZSUMLPWDHKCJ-UHFFFAOYSA-N 0.000 description 1
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical group NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000012986 chain transfer agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical group 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000000386 donor Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000002587 enol group Chemical group 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 238000007646 gravure printing Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 239000000852 hydrogen donor Substances 0.000 description 1
- 125000005191 hydroxyalkylamino group Chemical group 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- TYQCGQRIZGCHNB-JLAZNSOCSA-N l-ascorbic acid Chemical group OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 description 1
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 1
- 208000013469 light sensitivity Diseases 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- JESXATFQYMPTNL-UHFFFAOYSA-N mono-hydroxyphenyl-ethylene Natural products OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 230000006855 networking Effects 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 150000003071 polychlorinated biphenyls Chemical class 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000004149 thio group Chemical group *S* 0.000 description 1
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 1
- DMVQYIHNCKYDDL-UHFFFAOYSA-N thioxanthen-1-one Chemical compound C1=CC=C2C=C3C(=O)C=CC=C3SC2=C1 DMVQYIHNCKYDDL-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- DWWMSEANWMWMCB-UHFFFAOYSA-N tribromomethylsulfonylbenzene Chemical compound BrC(Br)(Br)S(=O)(=O)C1=CC=CC=C1 DWWMSEANWMWMCB-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 150000007934 α,β-unsaturated carboxylic acids Chemical class 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41C—PROCESSES FOR THE MANUFACTURE OR REPRODUCTION OF PRINTING SURFACES
- B41C1/00—Forme preparation
- B41C1/10—Forme preparation for lithographic printing; Master sheets for transferring a lithographic image to the forme
- B41C1/1008—Forme preparation for lithographic printing; Master sheets for transferring a lithographic image to the forme 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41C—PROCESSES FOR THE MANUFACTURE OR REPRODUCTION OF PRINTING SURFACES
- B41C2210/00—Preparation or type or constituents of the imaging layers, in relation to lithographic printing forme preparation
- B41C2210/04—Negative working, i.e. the non-exposed (non-imaged) areas are removed
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41C—PROCESSES FOR THE MANUFACTURE OR REPRODUCTION OF PRINTING SURFACES
- B41C2210/00—Preparation or type or constituents of the imaging layers, in relation to lithographic printing forme preparation
- B41C2210/06—Developable by an alkaline solution
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41C—PROCESSES FOR THE MANUFACTURE OR REPRODUCTION OF PRINTING SURFACES
- B41C2210/00—Preparation or type or constituents of the imaging layers, in relation to lithographic printing forme preparation
- B41C2210/12—Developable by an organic solution
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41C—PROCESSES FOR THE MANUFACTURE OR REPRODUCTION OF PRINTING SURFACES
- B41C2210/00—Preparation or type or constituents of the imaging layers, in relation to lithographic printing forme preparation
- B41C2210/22—Preparation or type or constituents of the imaging layers, in relation to lithographic printing forme preparation characterised by organic non-macromolecular additives, e.g. dyes, UV-absorbers, plasticisers
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41C—PROCESSES FOR THE MANUFACTURE OR REPRODUCTION OF PRINTING SURFACES
- B41C2210/00—Preparation or type or constituents of the imaging layers, in relation to lithographic printing forme preparation
- B41C2210/24—Preparation or type or constituents of the imaging layers, in relation to lithographic printing forme preparation characterised by a macromolecular compound or binder obtained by reactions involving carbon-to-carbon unsaturated bonds, e.g. acrylics, vinyl polymers
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41C—PROCESSES FOR THE MANUFACTURE OR REPRODUCTION OF PRINTING SURFACES
- B41C2210/00—Preparation or type or constituents of the imaging layers, in relation to lithographic printing forme preparation
- B41C2210/26—Preparation or type or constituents of the imaging layers, in relation to lithographic printing forme preparation characterised by a macromolecular compound or binder obtained by reactions not involving carbon-to-carbon unsaturated bonds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41C—PROCESSES FOR THE MANUFACTURE OR REPRODUCTION OF PRINTING SURFACES
- B41C2210/00—Preparation or type or constituents of the imaging layers, in relation to lithographic printing forme preparation
- B41C2210/26—Preparation or type or constituents of the imaging layers, in relation to lithographic printing forme preparation characterised by a macromolecular compound or binder obtained by reactions not involving carbon-to-carbon unsaturated bonds
- B41C2210/264—Polyesters; Polycarbonates
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41C—PROCESSES FOR THE MANUFACTURE OR REPRODUCTION OF PRINTING SURFACES
- B41C2210/00—Preparation or type or constituents of the imaging layers, in relation to lithographic printing forme preparation
- B41C2210/26—Preparation or type or constituents of the imaging layers, in relation to lithographic printing forme preparation characterised by a macromolecular compound or binder obtained by reactions not involving carbon-to-carbon unsaturated bonds
- B41C2210/266—Polyurethanes; Polyureas
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
- B41M5/40—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used characterised by the base backcoat, intermediate, or covering layers, e.g. for thermal transfer dye-donor or dye-receiver sheets; Heat, radiation filtering or absorbing means or layers; combined with other image registration layers or compositions; Special originals for reproduction by thermography
- B41M5/46—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used characterised by the base backcoat, intermediate, or covering layers, e.g. for thermal transfer dye-donor or dye-receiver sheets; Heat, radiation filtering or absorbing means or layers; combined with other image registration layers or compositions; Special originals for reproduction by thermography characterised by the light-to-heat converting means; characterised by the heat or radiation filtering or absorbing means or layers
- B41M5/465—Infrared radiation-absorbing materials, e.g. dyes, metals, silicates, C black
Definitions
- the invention relates to a radiation sensitive (photopolymerizable) mixture with a polymeric binder, a radically photopolymerizable component, one Infrared absorber and a triazine. It continues to affect one Recording material with a support and a radiation-sensitive Layer.
- a mixture of the type mentioned is already in EP-A 0 369 645. It includes a radically polymerizable one Monomer and a photoinitiator system soluble therein, the trihalomethyl-substituted 1,3,5-triazine, a sensitizer for the triazine and an electron donor compound with a Oxidation potential greater than zero and less than that of 1,4-dimethoxy-benzene contains.
- sensitizers are coumarin, Xanthene, acridine, thiazole, thiazine, oxazine, azine, aminoketone, Methine and polymethine dyes, porphyrins, aminotriarylmethanes, Merocyanines, squarylium and pyridinium dyes called. they are particularly sensitive to radiation in the range from 350 to 700 nm. For radiation in the near IR range (700 to 1200 nm) is the Sensitivity, on the other hand, is only slight.
- EP-A 0 315 988 also describes a photopolymerizable one Mixture disclosed that for radiation in the range of 600 to 700 nm is sensitive. It includes a polymerizable, ethylenic unsaturated compound, a radical generator and a substituted one 2-phenyl-2H-naphtho [6,5,4-a, m, n] thioxanthene-1,3-dione or a substituted 3-alkoxy-2-phenyl-naphtho [6,5,4-a, m, n] thioxanthen-1-one as a sensitizer.
- EP-A 0 441 542 relates to radiation crosslinking composition with a polymer to which mono-, dioder trihalomethyl-substituted [1,3,5] triazine residues via a Bridge group are covalently bound.
- the base polymer can be made from a variety of polymers can be selected. It can for example a polyamide, a polyester, a polyurethane Polysiloxane, a phenolic resin, a polystyrene, a polyacrylate, a Polyacrylic acid, a polyacrylamide, a polyacrylonitrile Polyethylene, a polybutadiene, polyvinylpyrrolidone, polycaprolactone, Gelatin, starch or a polysaccharide.
- EP-A 0 563 925 describes a photopolymerizable mixture discloses a radically polymerizable monomer substituted 2-phenyl-4-halomethyl (or 4,6-bishalogenmethyl) - [1,3,5] triazine as well as a connection that as Sensitizer for the triazine acts. The mixture will used for the production of negative working printing plates.
- a directly imageable recording material for production of planographic printing plates is described in EP-A 1 106 381. It comprises an electrochemically roughened carrier from a special aluminum alloy and a light-sensitive layer, which is an IR absorber and a water-insoluble but alkali-soluble contains polymeric binder.
- a photosensitive layer comprises the a monomer with one or more polymerizable, substituted acrylate group / s or derivatives thereof and one Contains photopolymerization initiator.
- Preferred initiators are aromatic ketones, aromatic onium salts, organic peroxides, Hexaarylbiimidazoles, borates, metallocenes and compounds with Carbon-halogen bonds.
- the latter also include optionally further substituted [1,3,5] triazines with trihalomethyl groups.
- the light-sensitive layer can also Sensitizer dyes included.
- On the photosensitive Layer can also be a polyvinyl alcohol layer.
- the task is solved with a radiation sensitive Mixture that absorbs in the range of 700 to 1,200 nm Contains heptamethine cyanine dye and acrylate and / or Methacrylate monomers with at least one photooxidizable group.
- the present invention accordingly relates to radiation sensitive mixture which is a radical polymerizable acrylate or methacrylate monomer and / or oligomer with at least two acrylate and / or meth-acrylate groups and at least one photooxidizable group, a photoinitiator, an IR absorbing dye and an organic polymer Contains binders, and is characterized in that the IR-absorbing Dye is a heptamethine cyanine dye.
- Heptamethine cyanine dyes are preferred in which 3 Methine carbon atoms part of a 5- to 7-membered isocyclic or heterocyclic ring.
- the label "Heptamethine cyanine dyes” includes amphoteric as well as ionic Connections.
- the aromatic end groups in the dyes are preferred indole or indolium groups to which, if appropriate other rings, in particular carbocyclic rings, fused could be.
- the binder can be selected from a whole range of organic polymers. Mixtures of different binders can also be used. For example, chlorinated polyalkylenes (in particular chlorinated polyethylene and chlorinated polypropylene), poly (meth) acrylic acid alkyl esters or alkenyl esters (in particular polymethyl (meth) acrylate, polyethyl (meth) acrylate, polybutyl (meth) acrylate, polyisobutyl (meth) acrylate, Polyhexyl (meth) acrylate, poly [(2-ethylhexyl) - (meth) acrylate] and poly [allyl (meth) acrylate]), copolymers of (meth) acrylic acid alkyl esters or alkenyl esters with other copolymerizable monomers (in particular with (meth ) acrylonitrile, vinyl chloride, vinylidene chloride, styrene and / or butadiene), polyviny
- binders are the Contain carboxy groups, particularly suitable. That is in particular Copolymers with units from ⁇ , ⁇ -unsaturated carboxylic acids or Dicarboxylic acids (preferably acrylic acid, methacrylic acid, crotonic acid, Vinyl acetic acid, maleic acid or itaconic acid).
- copolymers with units of (meth) acrylic acid and Units from alkyl (meth) acrylates, allyl methacrylates and / or (Meth) acrylonitrile as well as copolymers with units Crotonic acid and units from alkyl (meth) acrylates and / or (Meth) acrylonitrile, finally also vinyl acetic acid / Alkyl (meth) acrylate copolymers.
- copolymers with units Maleic anhydride and styrene, substituted styrenes, unsaturated ethers or esters or unsaturated aliphatic Hydrocarbons, as well as those obtainable from such copolymers Esterification.
- products that come from the Implementation of hydroxyl-containing polymers with intramolecular ones Dicarboxylic anhydrides arise.
- copolymers here are polymers with units of at least 2 different Monomers are understood, including terpolymers and higher Copolymers. Polymers in which groups with acidic hydrogen atoms occur, some or all of which have activated isocyanates is implemented.
- Polymers with aliphatic or aromatic sulfonyl isocyanates or phosphinic acid isocyanates are well suited finally also polymers with aliphatic or aromatic Hydroxy groups, for example copolymers with units Hydroxyalkyl (meth) acrylates, from allyl alcohol, from hydroxystyrene or from vinyl alcohol, and epoxy resins, if one wear a sufficient number of free OH groups.
- (meth) acrylic acid is related to the present invention for "acrylic acid and / or methacrylic acid”. The same applies to (meth) acrylonitrile, - (meth) acrylate, - (meth) acrylamide etc.
- the organic polymers used as binders generally an average molecular weight Mw of 600 to 200,000, preferably 1,000 to 100,000. Also preferred are polymers that an acid number between 10 and 250, preferably from 20 to 200, or a hydroxyl number from 50 to 750, preferably from 100 to 500, exhibit.
- the proportion of binder (s) is generally 10 to 90% by weight. %, preferably 20 to 80 wt .-%, each based on the total weight of the non-volatile components of the radiation-sensitive Mixture.
- a group is said to be related with the present invention a group of the formula> N-CO-N ⁇ are understood, in which the valences on the nitrogen atoms with Hydrogen atoms or hydrocarbon residues are saturated (there should be no more than one valence on each of the two Nitrogen atoms must be saturated with a hydrogen atom). It is however, it is also possible that a valence on a nitrogen atom Binding to a carbamoyl group (i.e. a -CO-NH group) produces so that a biuret structure is created.
- Aryl radicals R are generally mononuclear or dinuclear, but preferably mononuclear. They can be substituted by (C 1 -C 5 ) alkyl or (C 1 -C 5 ) alkoxy groups. If R 1 and R 2 are alkyl or alkoxy groups, then they preferably contain 1 to 5 carbon atoms. R 3 is preferably a hydrogen atom or a methyl group.
- X 1 is preferably a straight-chain or branched aliphatic and / or cycloaliphatic radical with preferably 4 to 10 carbon atoms. In a preferred embodiment, X 2 comprises 2 to 15 carbon atoms.
- X 2 is a saturated, straight-chain or branched aliphatic and / or cycloaliphatic radical with this number of carbon atoms. Up to 5 methylene groups in these residues can be replaced by oxygen atoms.
- X 2 consists of pure hydrocarbon chains, the rest generally comprises 2 to 12, preferably 2 to 6, carbon atoms.
- X 2 can also be a cycloaliphatic group with 5 to 10 carbon atoms, in particular a cyclohexanediyl group.
- the saturated heterocyclic ring formed by D 1 , D 2 and the two nitrogen atoms generally comprises 5 to 10 ring members, in particular 6 ring members.
- the heterocyclic ring is accordingly preferably a piperazine and the radical derived therefrom is a piperazine-1,4-diyl radical.
- the radical E is an alkanediyl group which usually comprises about 2 to 6 carbon atoms.
- the divalent 5- to 7-membered, saturated, isocyclic group E is preferably a cyclohexanediyl, in particular a cyclohexane-1,4-diyl group.
- the divalent, isocyclic, aromatic group E is preferably an ortho-, meta- or para-phenylene group.
- the divalent 5- or 6-membered aromatic heterocyclic group E preferably contains nitrogen and / or sulfur atoms in the heterocyclic ring.
- c is preferably 1, ie each of the radicals in the square bracket generally contains only one polymerizable group, in particular only one (meth) acryloyloxy group.
- hydroxyalkylamines used as starting materials are diethanolamine, triethanolamine, tris- (2-hydroxypropyl) amine, Tris (2-hydroxy-butyl) amine and alkyl bis-hydroxyalkyl amines.
- esters containing are preferably hydroxyethyl (meth) acrylate, Hydroxypropyl (meth) acrylate and hydroxyisopropyl (meth) acrylate used.
- the compounds of formula II are analogous to those of Formula I prepared, being instead of reaction products Hydroxy-alkyl acrylates or alkacrylates and diisocyanates corresponding acrylic acid or alkacrylic acid glycide ester used become. Such compounds and processes for their preparation are otherwise disclosed in EP-A 0 316 706.
- X 1 , R 3 , a and b have the meaning given above in formula IV;
- X 2 represents a divalent hydrocarbon group in which up to 5 methylene groups can be replaced by oxygen atoms.
- the running number a is preferably 0 or 1;
- i is preferably a number from 2 to 10.
- polymerizable compounds with photooxidizable groups are also reaction products of mono- or diisocyanates polyhydric alcohols in which all or part of the Hydroxy groups are esterified with (meth) acrylic acid. Products such as those resulting from the implementation of Hydroxyalkyl (meth) acrylates with diisocyanates are formed.
- Such Monomers are known and for example in DE-A 28 22 190 or DE-A 20 64 079 described.
- the mixture according to the invention can moreover photopolymerizable acrylate and / or alkacrylate compounds with 2 or more, preferably 3 to 6, acrylate and / or alkacrylate, in particular contain methacrylate groups.
- These multifunctional Connections act as crosslinkers.
- Preferred crosslinkers are (Meth) acrylates of saturated aliphatic or alicyclic, trihydric or polyhydric alcohols, such as alkanediols (specifically Ethylene glycol and propylene glycol), bis-phenol-A, trimethylolethane, Trimethylolpropane, pentamethylolpropane, pentaerythritol or Dipentaerythritol.
- ethoxylated and propoxylated trimethylolpropane tri (meth) acrylate ditrimethylolpropane tetra (meth) acrylate, Tris (2-hydroxyethyl) -isocyanurattri (meth) acrylate or glycerol tri (meth) acrylate.
- the Proportion of cross-linking acrylic and / or Alkacrylate compounds are generally up to 20% by weight, preferred 5 to 15 wt .-%, each based on the total weight of the non-volatile components of the radiation-sensitive mixture.
- the proportion of all photopolymerizable monomers or oligomers is generally 10 to 85% by weight, preferably 20 to 75% by weight, each based on the total weight of the non-volatile Components of the radiation sensitive mixture.
- the heptamethine cyanine dye preferably corresponds to one of the general formulas V or VI.
- R 3 methyl, ethyl, propyl or butyl
- R 4 H, Cl
- X - (CH 2 ) 3 - or - (CH 2 ) 2 -
- Y Br - , Cl - , I - , pTosO - , ClO 4 - , BF 4 - or PF 6 -
- the proportion of the heptamethine cyanine dye is general 0.01 to 10.0% by weight, preferably 0.5 to 8.0% by weight, in each case based on the total weight of the non-volatile components of the photopolymerizable mixture.
- Triazine compounds are well suited with at least one photolytically cleavable Trihalomethyl group, especially a trichloro or Tribromomethyl.
- the trihalomethyl groups can directly, via a conjugated double bond or via a chain of conjugated double bonds to an aromatic carbocyclic or heterocyclic ring.
- Compounds are preferred with a triazine base on the 2 Trihalomethyl groups are bound. Such connections are for example in DE 2 718 259, EP-A 0 137 452 and in EP-A 0 563,925. Basically absorb the used Triazine is not the radiation used for imaging.
- Trihalomethyltriazines can also be used, the Self absorption is below 300 nm. Such materials are particularly preferred, because the photoreactivity compared to the usual interior lighting is reduced.
- usable Trihalomethyltriazines are, for example, those which (saturated) aliphatic substituents or unsaturated substituents with only slightly extended es electron systems capable of mesomerization contain. Connections to other frameworks, for example Phenyl-trihalomethyl-sulfones (especially phenyl-tribromomethylsulfone) and phenyl-trihalogen-methyl-ketones, which are in the shorter-wave Absorb UV range can in principle also be used.
- the proportion of photoinitiator (s) is generally 0.1 to 20% by weight. preferably 1.0 to 10% by weight, in each case based on the total weight of the non-volatile components of the photopolymerizable Mixture.
- any pre-dispersed phthalocyanine pigments present primarily serve to color the mixture and the layers created with it. Their proportion is generally about 1 to 20 wt .-%, preferably about 2 to 14 wt .-%.
- Particularly suitable predispersed phthalocyanine pigments are described in DE-A 199 15 717 and DE-A 199 33 139. Are preferred especially metal-free phthalocyanine pigments.
- additives that inhibit thermally induced polymerization, hydrogen donors, Dyes, colored and colorless pigments, color formers, Filter dyes, indicator dyes, plasticizers and / or Chain transfer agent.
- additives that inhibit thermally induced polymerization, hydrogen donors, Dyes, colored and colorless pigments, color formers, Filter dyes, indicator dyes, plasticizers and / or Chain transfer agent.
- Appropriately chosen additives are those which do not absorb the radiation acting on the image.
- the radiation-sensitive mixture is appropriately in one organic solvents dissolved or dispersed and the solution or Dispersion applied to the carrier as a thin film.
- the Can be applied by pouring, spraying, dipping, applying with the help of rollers or similar, known to those skilled in the art Procedure. After drying, this is a Obtain recording material from which, for example Printing forms for high pressure, planographic printing, gravure printing or screen printing have it made. It can also be a material that is made up of Relief copies (e.g. for the production of texts in Braille), single copies, tanned images, pigment images or similar Have products structured according to the image.
- the Mixture according to the invention is also suitable for the production of Etching reserves, for example in the manufacture of PCBs or name tags can be used, as well as for molding etching. However, it is preferably used for Production of photoresist layers and printing plates.
- the present invention accordingly also relates to Recording material for the production of printing plates with a Carrier and a layer of the invention photopolymerizable mixture.
- a carrier material for printing plates are suitable foils, tapes or plates made of metal (in particular Made of aluminum or an aluminum alloy, steel, zinc or Copper) or plastic (especially polyester - especially Polyethylene terephthalate or cellulose acetate), for screen printing supports also pearl gauze.
- the surface of the Carrier of a mechanical, chemical and / or electrochemical To undergo pretreatment to ensure adhesion between the wearer and radiation-sensitive layer to adjust optimally or to achieve that the surface of the support acting imagewise Radiation less reflected (anti-halation).
- the preferred Carrier for offset printing plates is made of aluminum or an Al alloy and is electrochemically roughened on its surface, then anodized, if necessary also with a hydrophilizing agents (for example Polyvinylphosphonic acid) has been treated.
- the IR laser sources between 700 and 1200 nm familiar to the person skilled in the art are used for imagewise irradiation. Laser diodes which emit in the NIR range are preferred.
- the recording material according to the invention has a particularly high imaging performance and is therefore particularly suitable for digital imaging with NIR laser beams. In the subsequent development process, a distinction is then made precisely between non-image areas and image areas, so that the dot gain is surprisingly significantly reduced. Even small negative fonts are therefore clearly reproduced. At the same time, the material has a very high sensitivity in the NIR wavelength range.
- the cover layer can be self-supporting and removed before the subsequent development step. It then consists, for example, of a laminated polyester film. Cover layers made of a material which is soluble or dispersible in the developer liquid (at least in the non-hardened areas) can also be used.
- Suitable materials for a top layer which is completely soluble in aqueous alkaline developers are, for example, polyvinyl alcohol, polyvinyl pyrrolidone, polyphosphates, sugar, etc.
- the thickness of the top layer is generally 0.1 to 10 ⁇ m, preferably 1 to 5 ⁇ m.
- the further processing of the imagewise irradiated Recording materials are made according to the generally accepted and Methods known to those skilled in the art. This can be done imagewise before developing irradiated material can still be reheated for better To achieve networking in the irradiated areas.
- organic solvents or mixtures of organic Solvents are used, but preferred are aqueous alkaline Solutions with a pH of 8 to 14, especially from 9 to 13, up to about 20 wt.%, Preferably up to about 15 wt. %, of water-miscible organic solvents.
- the Developers can also use wetting agents, dyes, salts and / or contain other additives.
- the printing plate thus obtained was imaged with a CREO Trendsetter 3244T (2400 dpi), heated to 100 ° C. for 1 min and then with an aqueous alkaline developer (Agfa EN 231C) at 28 ° C. at a throughput speed of 1 m / min. (Agfa VSP85) developed.
- the sensitivity indicated corresponded to the laser energy in the image plane that was required to make a 50% field formed from 1x1 and 8x8 pixels appear equally bright. The value determined in this way was 18 mJ / cm 2 .
- compositions, layer weights and specific plate sensitivity used are listed in Table 1: component Examples 2 V1 V2 V3 V4 Gt Gt Gt Gt Gt A 6,900 6,904 6,904 6,904 6,904 B 3,770 - - - - C - 3,270 - - - D - - 3,270 - - e - - - 3,270 - F - - - - 3,270 G 0.163 0.163 0.163 0.163 0.163 H 6,870 6.869 6.869 6.869 6.869 6.869 6.869 6.869 6.869 I 0.408 0.408 0.408 0.408 0.408 0.408 J 0,007 0,007 0,007 0,007 K 0,680 0.679 0.679 0.679 0.679 L 20.48 20.98 20.98 20.98 20.98 M 40.72 40.72 40.72 40.72 40.72 40.72 40.72 Layer weight [g / m 2 ] 1.60 1.
- composition used The composition used, the layer weights and the specific plate sensitivities are listed in Table 2: component Examples 4 5 6 7 8 Gt Gt Gt Gt Gt A 6,430 6,430 6,430 8,090 8.110 B 0,095 - - - - C - 0,095 - - - D - - 0,101 - - e - - - 0.130 - F - - - - 0,120 G 3,310 3,310 3,310 4,170 4,170 H 6,390 6,290 6,160 7,760 7,760 I 0,238 0,238 0,238 0,238 0,300 0,300 J 0,018 0,018 0,018 0,020 0,020 K 0,600 0,600 0,600 0,760 0,760 L 17.67 17.67 17,98 51.04 51.02 M 35.35 35.35 35.48 77.74 77.74 Layer weight [g / m 2 ] 1.50 1.50 1.66 1.10 1.10 Energy value [mJ / cm 2 ] 28 38 61 43 57
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- Optics & Photonics (AREA)
- Thermal Sciences (AREA)
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- Materials For Photolithography (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
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DE50204080T DE50204080D1 (de) | 2002-04-29 | 2002-04-29 | Strahlungsempfindliches Gemisch, damit hergestelltes Aufzeichnungsmaterial, und Verfahren zur Herstellung einer Druckplatte |
EP20020100424 EP1359008B1 (fr) | 2002-04-29 | 2002-04-29 | Mélange photosensible, matériau pour l'enregistrement utilisant ce mélange, et procédé pour la fabrication d'une plaque d'impression |
US10/425,158 US7314699B2 (en) | 2002-04-29 | 2003-04-29 | Radiation-sensitive mixture and recording material produced therewith |
JP2003125528A JP2003344997A (ja) | 2002-04-29 | 2003-04-30 | 放射線感受性混合物およびそれを用いて製造される記録材料 |
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EP20020100424 EP1359008B1 (fr) | 2002-04-29 | 2002-04-29 | Mélange photosensible, matériau pour l'enregistrement utilisant ce mélange, et procédé pour la fabrication d'une plaque d'impression |
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EP1359008A1 true EP1359008A1 (fr) | 2003-11-05 |
EP1359008B1 EP1359008B1 (fr) | 2005-08-31 |
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EP (1) | EP1359008B1 (fr) |
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WO2023011820A1 (fr) | 2021-08-05 | 2023-02-09 | Agfa Offset Bv | Précurseur de plaque d'impression lithographique |
EP4223534A1 (fr) | 2022-02-07 | 2023-08-09 | Agfa Offset Bv | Précurseur de plaque d'impression lithographique |
WO2023148114A1 (fr) | 2022-02-07 | 2023-08-10 | Eco3 | Précurseur de plaque d'impression lithographique |
EP4239411A1 (fr) | 2022-03-04 | 2023-09-06 | Eco3 Bv | Appareil et procédé de traitement d'un précurseur de plaque d'impression lithographique |
WO2023165919A1 (fr) | 2022-03-04 | 2023-09-07 | Eco3 Bv | Procédé et appareil de traitement de précurseur de plaque d'impression lithographique |
EP4382306A1 (fr) | 2022-12-08 | 2024-06-12 | Eco3 Bv | Procédé de préparation de presse d'impression lithographique |
WO2024120763A1 (fr) | 2022-12-08 | 2024-06-13 | Eco3 Bv | Procédé de préparation de presse d'impression lithographique |
Also Published As
Publication number | Publication date |
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DE50204080D1 (de) | 2005-10-06 |
EP1359008B1 (fr) | 2005-08-31 |
JP2003344997A (ja) | 2003-12-03 |
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