EP1359008B1 - Mélange photosensible, matériau pour l'enregistrement utilisant ce mélange, et procédé pour la fabrication d'une plaque d'impression - Google Patents
Mélange photosensible, matériau pour l'enregistrement utilisant ce mélange, et procédé pour la fabrication d'une plaque d'impression Download PDFInfo
- Publication number
- EP1359008B1 EP1359008B1 EP20020100424 EP02100424A EP1359008B1 EP 1359008 B1 EP1359008 B1 EP 1359008B1 EP 20020100424 EP20020100424 EP 20020100424 EP 02100424 A EP02100424 A EP 02100424A EP 1359008 B1 EP1359008 B1 EP 1359008B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- meth
- acrylate
- mixture
- weight
- group
- 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.)
- Expired - Lifetime
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- 230000005855 radiation Effects 0.000 title claims description 26
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- -1 triazine compound Chemical class 0.000 claims description 34
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 31
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- 239000000178 monomer Substances 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 239000011230 binding agent Substances 0.000 claims description 15
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
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- 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
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- 235000019325 ethyl cellulose Nutrition 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
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- 229920003023 plastic Polymers 0.000 claims description 2
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- 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
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- 235000000346 sugar Nutrition 0.000 claims description 2
- 125000001302 tertiary amino group Chemical group 0.000 claims description 2
- 125000004149 thio group Chemical group *S* 0.000 claims description 2
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- 239000003791 organic solvent mixture Substances 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
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- 239000004411 aluminium Substances 0.000 claims 1
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
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- 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
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- 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
- NWWZLDXOHWTTKD-UHFFFAOYSA-N CN(C(CC(N1C)=O)=O)C1=S Chemical compound CN(C(CC(N1C)=O)=O)C1=S NWWZLDXOHWTTKD-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
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical group [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 101150065749 Churc1 gene Proteins 0.000 description 1
- LSDAMUMZVDDITM-UHFFFAOYSA-N ClC(C1=NN=NC(=C1)C(Cl)(Cl)Cl)(Cl)Cl Chemical compound ClC(C1=NN=NC(=C1)C(Cl)(Cl)Cl)(Cl)Cl LSDAMUMZVDDITM-UHFFFAOYSA-N 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
- 229920002292 Nylon 6 Polymers 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical group C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 102100038239 Protein Churchill Human genes 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
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000005907 alkyl ester 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
- 238000004040 coloring 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
- 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
- 239000010408 film 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
- 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
- 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
- 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
- 229920001633 poly(α-methyl styrene) Polymers 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
- 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
- 229920001155 polypropylene Polymers 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
- 235000019422 polyvinyl alcohol Nutrition 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
- 150000008163 sugars Chemical class 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 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
- 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
- 229920002554 vinyl polymer Polymers 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 group 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, a Infrared absorber and a triazine. It continues to apply 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 comprises a free-radically polymerizable Monomer and a soluble therein photoinitiator system, the trihalomethyl-substituted 1,3,5-triazine, a sensitizer for the triazine and an electron-donor compound with a Oxidation potential of 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, Called merocyanines, squarylium and pyridinium dyes. you are sensitive especially to radiation in the range of 350 to 700 nm. For radiation in the near IR range (700 to 1200 nm) is the Sensitivity, however, only low.
- EP-A 0 315 988 is a photopolymerizable Mixture disclosed for radiation in the range of 600 to 700 nm is sensitive. It comprises 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.
- the subject of EP-A-0 441 524 is one upon irradiation crosslinking composition with a polymer to which mono-, di- or trihalomethyl-substituted [1,3,5] triazine residues via a Bridge group are covalently bonded.
- the base polymer may be made a variety of polymers are selected.
- a polyamide a polyester, a polyurethane, a Polysiloxane, a phenolic resin, a polystyrene, a polyacrylate, a Polyacrylic acid, a polyacrylamide, a polyacrylonitrile, a Polyethylene, a polybutadiene, polyvinylpyrrolidone, polycaprolactone, Gelatin, starch or a polysaccharide.
- EP-A 0 563 925 is a photopolymerizable mixture discloses a radically polymerizable monomer substituted 2-phenyl-4-halomethyl (or 4,6-bis-halomethyl) - [1,3,5] triazine and a compound known as Sensitizer for the triazine. The mixture is used for the production of negative-working printing plates.
- a directly imageable recording material for the production of planographic printing plates is described in EP-A 1,106,381. It comprises an electrochemically roughened carrier of a special aluminum alloy and a photosensitive layer, an IR absorber and a water-insoluble, but alkali-soluble contains polymeric binder.
- a photosensitive layer comprises a monomer with one or more polymerisable, substituted acrylate group (s) or derivatives thereof and a Photopolymerization initiator contains.
- a Photopolymerization initiator contains.
- Preferred initiators are aromatic ketones, aromatic onium salts, organic peroxides, Hexaarylbiimidazole, borates, metallocenes and compounds with Carbon-halogen bonds. The latter also count optionally further substituted [1,3,5] triazines with Trihalogenmethyl Reliefn.
- the photosensitive layer may be next to it Sensitizer dyes included.
- On the photosensitive Layer may additionally be a polyvinyl alcohol layer.
- a major disadvantage of this recording material is in that the monomers are synthetically difficult to access and thus are correspondingly expensive. Furthermore, the reactivity and so that the photosensitivity of the layer is reduced.
- EP-A-1 176 007 and EP-A-1 162 078 describe a radiation-sensitive A mixture comprising a free-radically polymerizable (meth) acrylate monomer having at least two (Meth) acrylate groups and at least one photooxidizable group, a Radical initiator, an IR-absorbing heptamethine cyanine dye, and an organic contains polymeric binder.
- the radical initiator absorbs near infrared radiation.
- Heptamethine cyanine dye contains and acrylate and / or Methacrylate monomers having at least one photooxidizable group.
- the subject of the present invention is accordingly a radiation-sensitive mixture containing 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 binder, and characterized in that the IR-absorbing Dye is a heptamethine cyanine dye, that the mixture is sensitive to the near infrared region, and the photoinitiator does not absorb this radiation.
- heptamethine cyanine dyes in which 3 Methine carbon atoms part of a 5- to 7-membered isocyclic or heterocyclic ring.
- the name "Heptamethine cyanine dyes” includes amphoteric as well as ionic Connections.
- the aromatic end groups in the dyes are preferably indole or indolium groups, to which, if appropriate still more rings, especially carbocyclic rings, fused could be.
- the binder can be made from a whole range of organic Be selected polymers. Also mixtures of different binders can be used. Suitable examples are chlorinated Polyalkylenes (especially chlorinated polyethylene and chlorinated Polypropylene), poly (meth) acrylic acid alkyl ester or alkenyl ester (in particular polymethyl (meth) acrylate, polyethyl (meth) acrylate, Polybutyl (meth) acrylate, polyisobutyl (meth) acrylate, Polyhexyl (meth) acrylate, poly [(2-ethyl-hexyl) - (meth) acrylate] and Poly [allyl (meth) acrylate]), copolymers of (meth) acrylic acid alkyl esters or alkenyl esters with other copolymerisable Monomers (in particular with (meth) acrylonitrile, vinyl chloride, Vinylidene chloride, styrene and / or butadiene), poly
- binders which Contain carboxy groups, particularly suitable. That's in particular Copolymers containing units of ⁇ , ⁇ -unsaturated carboxylic acids or Dicarboxylic acids (preferably acrylic acid, methacrylic acid, crotonic acid, Vinylacetic acid, maleic acid or itaconic acid).
- copolymers with units of (meth) acrylic acid and Units of alkyl (meth) acrylates, allyl methacrylates and / or (Meth) acrylonitrile, as well as copolymers with units of Crotonic acid and units of alkyl (meth) acrylates and / or (Meth) acrylonitrile, and finally vinylacetic acid / alkyl (meth) acrylate copolymers.
- copolymers with Units of maleic anhydride or maleic acid monoalkyl esters are also suitable.
- copolymers with units Maleic anhydride and styrene, substituted styrenes, unsaturated ethers or esters or unsaturated aliphatic ones Hydrocarbons, as well as those obtainable from such copolymers Esterification.
- products from the Reaction of hydroxyl-containing polymers with intramolecular Dicarboxylic anhydrides arise.
- copolymers here are polymers with units of at least 2 different Monomers are understood, including terpolymers and higher Copolymers. Also useful are polymers in which groups with acidic hydrogen atoms occur, part or all of them with activated isocyanates is reacted.
- (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 have in general, a mean molecular weight Mw of 600 to 200,000, preferably 1,000 to 100,000. Preference is furthermore given to polymers which an acid number between 10 and 250, preferably from 20 to 200, or a hydroxyl number of 50 to 750, preferably 100 to 500, exhibit.
- the proportion of binder (s) is generally 10 to 90 wt .-%, preferably 20 to 80 wt .-%, each based on the total weight the non-volatile components of the radiation-sensitive Mixture.
- the radically polymerizable acrylate or methacrylate compound with at least one photooxidizable group For example, a connection with a primary, secondary and in particular tertiary amino group.
- urea group is meant in context with the present invention, a group of the formula> N-CO-N ⁇ be understood, in which the valencies on the nitrogen atoms with Hydrogen atoms or hydrocarbon radicals are saturated (It should not have more than one valence on each of them Nitrogen atoms are saturated with a hydrogen atom). It is but also possible that a valence on a nitrogen atom the Binding to a carbamoyl group (i.e., a -CO-NH group) producing a biuret structure.
- Aryl radicals R are generally mono- or binuclear, but preferably mononuclear. They may be substituted by (C 1 -C 5 ) alkyl or (C 1 -C 5 ) alkoxy groups. When R 1 and R 2 are alkyl or alkoxy groups, 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 having preferably 4 to 10 carbon atoms.
- X 2 comprises in a preferred embodiment 2 to 15 carbon atoms.
- X 2 is a saturated, straight-chain or branched aliphatic and / or cycloaliphatic radical having this number of carbon atoms. Up to 5 methylene groups in these radicals may be replaced by oxygen atoms.
- X 2 consists of pure hydrocarbon chains, the radical generally comprises 2 to 12, preferably 2 to 6 carbon atoms. X 2 may also be a cycloaliphatic group having 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 preferably a piperazine and the radical derived therefrom is a piperazine-1,4-diyl radical.
- the moiety E in a preferred embodiment is an alkanediyl group, usually comprising about 2 to 6 carbon atoms.
- the bivalent 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 polymerisable group, in particular only one (meth) acryloyloxy group.
- Hydroxyalkylamines are diethanolamine, triethanolamine, tris- (2-hydroxy-propyl) -amine, Tris (2-hydroxybutyl) amine and alkyl bishydroxyalkyl amines.
- Hydroxy-containing esters 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, instead of from reaction products Hydroxyalkyl acrylates or alkacrylates and diisocyanates the corresponding acrylic acid or alkacrylic acid glycidester 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 in the formula IV have the abovementioned meaning;
- X 2 represents a divalent hydrocarbon group in which up to 5 methylene groups may be replaced by oxygen atoms.
- the running number a in this formula 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 with polyhydric alcohols in which all or part of the Hydroxy groups are esterified with (meth) acrylic acid suitable. Preference is given to products as they result from the implementation of Hydroxyalkyl (meth) acrylates with diisocyanates arise.
- 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, especially methacrylate groups.
- This multifunctional Compounds act as crosslinkers.
- Preferred crosslinkers are (Meth) acrylates of saturated aliphatic or alicyclic, trihydric or polyhydric alcohols, such as alkanediols (especially 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.
- Proportion of crosslinking acrylate and / or Alkacrylate compounds are generally up to 20% by weight, preferably 5 to 15 wt .-%, each based on the total weight of non-volatile constituents of the radiation-sensitive mixture.
- the proportion of all photopolymerizable monomers or oligomers is generally from 10 to 85% by weight, preferably from 20 to 75% by weight, in each case based on the total weight of the non-volatile Components of the radiation-sensitive mixture. There are generally at least 40% by weight of the photopolymerizable monomers and / or oligomers such with photooxidizable groups.
- the proportion of heptamethine cyanine dye is general 0.01 to 10.0 wt .-%, preferably 0.5 to 8.0 wt .-%, each based on the total weight of the nonvolatile constituents of the photopolymerizable mixture.
- Photoinitiators are known per se.
- Well suited are triazine compounds with at least one photocleavable Trihalogenmethyl devis, in particular a trichloro or Tribromomethyl.
- the trihalomethyl groups can thereby directly, via a conjugated double bond or via a chain of conjugated double bonds to an aromatic carbocyclic or heterocyclic ring.
- Such compounds are for example in DE 2 718 259, EP-A 0 137 452 and in EP-A 0 563,925. Basically absorb the used Triazines do not use the radiation used for imaging.
- Trihalogenmethyltriazine can be used, whose Own absorption is below 300 nm. Such materials are particularly preferred, because thereby the photoreactivity towards the usual interior lighting is reduced.
- usable Trihalomethyltriazines are, for example, those which are (saturated) aliphatic substituents or unsaturated substituents with only a few extended mesomeric ⁇ -electron systems contain.
- Proportion of photoinitiator (s) is generally from 0.1 to 20 wt .-%, preferably 1.0 to 10 wt .-%, each based on the total weight the non-volatile constituents of the photopolymerizable Mixture.
- predispersed phthalocyanine pigments serve primarily for coloring the mixture and the layers produced with it. Their share is generally about 1 to 20 wt .-%, preferably about 2 to 14 wt .-%.
- Particularly suitable Pre-dispersed phthalocyanine pigments are described in DE-A 199 15 717 and DE-A 199 33 139 discloses. Preferred are in particular 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 are suitably selected those that do not absorb the imagewise acting radiation.
- the radiation-sensitive mixture is useful in a dissolved or dispersed organic solvent and the solution or Dispersion applied as a thin film on the support.
- the Can be applied by pouring, spraying, dipping, by applying with the help of rollers or similar, known in the art Procedure done. After drying in this way Receive recording material from which, for example Printing forms for high-pressure, planographic, gravure or screen printing let produce. It can also be a material that makes up Relief copies (for example for the production of texts in Braille), single copies, Gerbordinate, Pigmentmul or similar to produce image-structured products.
- the mixture according to the invention is also suitable for the production of ⁇ tmreservagen, for example, in the production of Printed circuit boards or name tags can be used, as well as for molding. However, it is preferably used for Production of photoresist layers and printing plates.
- the present invention is accordingly also a Recording material for the production of printing plates with a Carrier and a layer of the invention photopolymerizable mixture.
- carrier material for printing plates are films, tapes or plates made of metal (in particular made of aluminum or an aluminum alloy, steel, zinc or Copper) or plastic (especially polyester - specifically Polyethylene terephthalate or cellulose acetate), for screen printing media also perlon gauze.
- metal in particular made of aluminum or an aluminum alloy, steel, zinc or Copper
- plastic especially polyester - specifically Polyethylene terephthalate or cellulose acetate
- screen printing media also perlon gauze.
- the preferred one Support for offset printing plates is made of aluminum or an Al alloy and is electrochemically roughened on its surface, then anodized, optionally also with a hydrophilicizing agent (for example Polyvinylphosphonic acid).
- the IR laser sources familiar to the person skilled in the art between 700 and 1200 nm are used for imagewise radiation. Preference is given to laser diodes which emit in the NIR range.
- the novel recording material has a particularly high imaging performance and is therefore particularly suitable for digital imaging with NIR laser beams. In the subsequent development process is then differentiated exactly between non-image areas and image locations, so that the dot gain is surprisingly significantly reduced. Even small negative fonts are therefore still clearly reproduced. At the same time, the material has a very high sensitivity in the NIR wavelength range.
- the radiation-sensitive layer It is practically essential to protect the radiation-sensitive layer from atmospheric oxygen during NIR-induced polymerization. This is most easily achieved by a covering layer which is impermeable to oxygen or only slightly permeable ("poorly permeable” means a permeability of not more than 100 cm 3 O 2 / m 2 * d * bar, determined in accordance with DIN 53 380 at 23 ° C. ) applied to the radiation-sensitive layer.
- the cover layer may be self-supporting and be stripped before the subsequent development step. It then consists for example of a laminated polyester film. Also, overcoats of a material that is soluble or dispersible (at least in the uncured areas) in the developer liquid may be used.
- Suitable materials for a cover layer which is completely soluble in aqueous alkaline developers are, for example, polyvinyl alcohol, polyvinylpyrrolidone, polyphosphates, sugars, etc.
- the thickness of the cover layer is generally 0.1 to 10 .mu.m, preferably 1 to 5 .mu.m.
- the printing plate thus obtained was imaged with a CREO Trendsetter 3244T (2400 dpi), heated for 1 min at 100 ° C and then with an aqueous-alkaline developer (Agfa EN 231C) at 28 ° C at a flow rate of 1 m / min. (Agfa VSP85).
- the indicated sensitivity corresponded to that laser energy in the image plane which was required to make a 50% field formed of 1x1 and 8x8 pixels appear bright. The value determined in this way was 18 mJ / cm 2 .
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Claims (20)
- Mélange sensible au rayonnement qui contient un monomère et/ou un oligomère d'acrylate et/ou de méthacrylate apte à une polymérisation radicalaire comprenant au moins deux groupes acrylate et/ou méthacrylate et au moins un groupe photo-oxydable, un photo-initiateur, un colorant absorbant le rayonnement infrarouge et un liant polymère organique, caractérisé en ce que le colorant absorbant l'infrarouge est un colorant d'heptaméthine cyanine, en ce que le mélange manifeste une sensibilité pour le domaine de l'infrarouge proche, le photoinitiateur n'absorbant pas ce rayonnement.
- Mélange selon la revendication 1, caractérisé en ce que 3 atomes de carbone du groupe méthine dans la chaíne heptaméthine du colorant font partie d'un noyau isocyclique ou hétérocyclique pentagonal à heptagonal.
- Mélange selon la revendication 1 ou 2, caractérisé en ce que les deux groupes terminaux aromatiques dans les colorants d'heptaméthine cyanine représentent des groupes indole et/ou indolium auxquels peut être condensé le cas échéant encore au moins un noyau supplémentaire.
- Mélange selon une ou plusieurs des revendications 1 à 3, caractérisé en ce que le colorant d'heptaméthine cyanine répond à la formule V dans laquelle
R1 = R2 = H ou R1 et R2 représentent ensemble un groupe -CH=CH-CH=CH- où R1 forme, ensemble avec R2 un noyau hexagonal condensé ;
R3 représente un groupe méthyle, un groupe éthyle, un groupe propyle ou un groupe butyle ;
X représente un groupe -(CH2)3- ou un groupe -(CH2)2- ;
Y représente ou bien répond à la formule VI dans laquelle
R1 = R2 = H ou R1 et R2 représentent ensemble un groupe -CH=CH-CH=CH- où R1 forme, ensemble avec R2 un noyau hexagonal condensé ;
R3 représente un groupe méthyle, un groupe éthyle, un groupe propyle ou un groupe butyle ;
R4 représente un atome d'hydrogène, un atome de chloré, X représente un groupe -(CH2)3- ou un groupe -(CH2)2- ;
Y représente un groupe Br-, un groupe Cl-, un groupe I-, un groupe pTosO-, un groupe ClO4 -, un groupe BF4 - ou un groupe PF6 -. - Mélange selon une ou plusieurs des revendications 1 à 4, caractérisé en ce que la fraction du colorant d'heptaméthine cyanine représente de 0,01 à 10 % en poids, de préférence de 0,5 à 8,0 % en poids, chaque fois rapportés au poids total des constituants non volatils du mélange.
- Mélange selon une ou plusieurs des revendications 1 à 5, caractérisé en ce que le monomère d'acrylate ou de méthacrylate apte à une polymérisation radicalaire contient deux groupes acrylate ou méthacrylate.
- Mélange selon revendication 6, caractérisé en ce que le groupe photo-oxydable dans le monomère ou le oligomère d'acrylate ou de méthacrylate apte à une polymérisation radicalaire est un groupe amino primaire, secondaire ou tertiaire, un groupe urée, un groupe thio et/ou un groupe uréthane.
- Mélange selon une ou plusieurs des revendications 1 à 7, caractérisé en ce que la fraction de tous les monomères ou de tous les oligomères photopolymérisables représente en général de 10 à 85 % en poids, de préférence de 20 à 75 % en poids, chaque fois rapportés au poids total des constituants non volatils du mélange.
- Mélange selon la revendication 8, caractérisé en ce que la fraction des monomères ou des oligomères photopolymérisables contenant des groupes photo-oxydables représente au moins 40 % en poids, rapportés au poids total de tous les monomères et/ou de tous les oligomères photopolymérisables.
- Mélange selon une ou plusieurs des revendications 1 à 9, caractérisé en ce que le photo-initiateur contient un composé de triazine comprenant au moins un groupe trihalogénométhyle apte à être clivé par voie photolytique, en particulier un groupe trichlorométhyle ou un groupe tribromométhyle.
- Mélange selon une ou plusieurs des revendications 1 à 10, caractérisé en ce que la fraction du ou des photo-initiateurs représente en général de 0,1 à 20 % en poids, de préférence de 1,0 à 10 % en poids, chaque fois rapportés au poids total des constituants non volatils du mélange.
- Mélange selon une ou plusieurs des revendications 1 à 11, caractérisé en ce qu'on met en oeuvre, à titre de liant, des polyalkylènes chlorés (en particulier du polyéthylène chloré et du polypropylène chloré), des esters alkyliques ou des esters alcényliques d'acide poly(méth)acrylique (en particulier le poly(méth)acrylate de méthyle, le poly(méth)acrylate d'éthyle, le poly(méth)acrylate de butyle, le poly(méth)acrylate d'isobutyle, le poly(méth)acrylate d'hexyle, le poly(méth)acrylate de 2-éthylhexyle et le poly(méth)acrylate d'allyle), des copolymères de (méth)acrylate d'alkyle/acide (méth)acrylique, des copolymères d'esters alkyliques ou d'esters alcényliques d'acide (méth)acrylique avec d'autres monomères copolymérisables (en particulier avec le (méth) acrylonitrile, le chlorure de vinyle, le chlorure de vinylidène, le styrène et/ou le butadiène), le chlorure de polyvinyle (PVC), des copolymères de chlorure de vinyle/acrylonitrile, le chlorure de polyvinylidène (PVDC), des copolymères de chlorure de vinylidène/acrylonitrile, l'acétate de polyvinyle, l'alcool polyvinylique, le polyacrylonitrile, des copolymères d'acrylonitrile/styrène, des copolymères de (méth)acrylamide/-(méth)acrylate d'alkyle, des terpolymères d'acrylonitrile/butadiène/-styrène (ABS), du poly-α-méthylstyrène, des polyamides, des polyuréthanes, des polyesters, de la méthylcellulose, de méthylcellulose, de l'acétylcellulose, du polystyrène, des hydroxy(alkyl en C1-C4)celluloses, de la carboxyméthylcellulose, du polyvinylformal et/ou du polyvinylbutyral, ainsi que des acides carboxyliques ou dicarboxyliques à insaturation α,β.
- Mélange selon une ou plusieurs des revendications 1 à 12, caractérisé en ce que le liant présente un poids moléculaire moyen Mw de 600 à 200.000, de préférence de 1000 à 100.000, et un indice d'acide entre 10 et 250, de préférence de 20 à 200, ou un indice d'hydroxyle de 50 à 750, de préférence de 100 à 500.
- Mélange selon une ou plusieurs des revendications 1 à 13, caractérisé en ce que la fraction du liant, respectivement des liants représente en général de 10 à 90 % en poids, de préférence de 20 à 80 % en poids, chaque fois rapportés au poids total des constituants non volatils du mélange.
- Matériau d'enregistrement pour la fabrication de clichés d'impression comprenant un support et une couche constituée du mélange photo-polymérisable selon une ou plusieurs de revendications 1 à 14.
- Matériau d'enregistrement selon la revendication 15, caractérisé en ce que le support est une feuille, une bande ou une plaque en matière synthétique ou en métal, de préférence en aluminium ou en un alliage d'aluminium comprenant une surface le cas échéant soumise à un traitement préalable de type mécanique, chimique et/ou électrochimique.
- Matériau d'enregistrement selon la revendication 15, caractérisé en ce que, sur la couche sensible au rayonnement, est disposé une couche de recouvrement imperméable ou seulement légèrement perméable à l'oxygène.
- Matériau d'enregistrement selon la revendication 17, caractérisé en ce que la couche de recouvrement est constituée d'alcool polyvinylique, de polyvinylpyrrolidone, de polyphosphates ou d'un sucre.
- Matériau d'enregistrement selon la revendication 17, caractérisé en ce que la couche de recouvrement présente une épaisseur de 0,1 à 10 µm, de préférence de 1 à 5 µm.
- Procédé pour la fabrication d'un cliché d'impression constitué du matériau d'enregistrement selon une ou plusieurs des revendications 15 à 19, caractérisé en ce qu'on expose le matériau d'enregistrement en forme d'image à des rayons laser infrarouge d'une longueur d'onde entre 700 et 1200 nm, avant de développer avec un solvant organique ou un mélange de solvants organiques ou avec une solution aqueuse-alcaline.
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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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US7316891B2 (en) | 2002-03-06 | 2008-01-08 | Agfa Graphics Nv | Method of developing a heat-sensitive lithographic printing plate precursor with a gum solution |
DE102004011347A1 (de) | 2004-03-05 | 2005-09-29 | Basf Ag | Druckfarben für den Offset- und/oder Hochdruck mit NIR-Absorbern sowie in Offset- und/oder Hochdruckfarben lösliche NIR-Absorber |
ATE533089T1 (de) | 2004-05-19 | 2011-11-15 | Agfa Graphics Nv | Verfahren zur herstellung einer fotopolymer- druckplatte |
EP1614541A3 (fr) | 2004-07-08 | 2006-06-07 | Agfa-Gevaert | Procédé pour la fabrication d'une plaque d'impression lithographique |
DE102004058584A1 (de) * | 2004-12-03 | 2006-06-08 | Basf Ag | Strahlungshärtbare Beschichtungsmassen |
DE602005012630D1 (de) | 2005-11-18 | 2009-03-19 | Agfa Graphics Nv | Verfahren zur Herstellung einer Lithografiedruckform |
ATE497192T1 (de) | 2005-11-18 | 2011-02-15 | Agfa Graphics Nv | Verfahren zur herstellung einer lithografiedruckform |
EP1788429B1 (fr) | 2005-11-18 | 2009-03-18 | Agfa Graphics N.V. | Procédé de fabrication d'une plaque d'impression lithographique |
EP1788431B1 (fr) | 2005-11-18 | 2009-01-28 | Agfa Graphics N.V. | Procédé de fabrication d'une plaque d'impression lithographique |
EP1788442B1 (fr) | 2005-11-18 | 2010-07-28 | Agfa Graphics N.V. | Procédé de fabrication d'une plaque d'impression lithographique |
DE602005013536D1 (de) | 2005-11-18 | 2009-05-07 | Agfa Graphics Nv | Verfahren zur Herstellung einer Lithografiedruckform |
PL1788443T3 (pl) | 2005-11-18 | 2014-12-31 | Agfa Nv | Sposób wytwarzania litograficznej płyty drukowej |
EP1788435B1 (fr) | 2005-11-21 | 2013-05-01 | Agfa Graphics N.V. | Procédé de fabrication d'une plaque d'impression lithographique |
ES2324542T3 (es) | 2005-11-21 | 2009-08-10 | Agfa Graphics N.V. | Metodo para fabricar una plancha de impresion litografica. |
EP1788449A1 (fr) | 2005-11-21 | 2007-05-23 | Agfa Graphics N.V. | Procédé de fabrication d'une plaque d'impression lithographique |
ES2382371T3 (es) | 2008-10-23 | 2012-06-07 | Agfa Graphics N.V. | Plancha de impresión litográfica |
JP5541913B2 (ja) | 2009-12-25 | 2014-07-09 | 富士フイルム株式会社 | 平版印刷版の作製方法 |
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CN102834779B (zh) | 2010-03-31 | 2015-07-08 | 富士胶片株式会社 | 用于处理平版印刷版原版的显影液,通过使用显影液制备平版印刷版的方法和印刷方法 |
EP2383118B1 (fr) | 2010-04-30 | 2013-10-16 | Fujifilm Corporation | Précurseur de plaque d'impression lithographique et procédé de fabrication de plaque correspondant |
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DE2718259C2 (de) | 1977-04-25 | 1982-11-25 | Hoechst Ag, 6000 Frankfurt | Strahlungsempfindliches Gemisch |
DE3337024A1 (de) | 1983-10-12 | 1985-04-25 | Hoechst Ag, 6230 Frankfurt | Lichtempfindliche, trichlormethylgruppen aufweisende verbindungen, verfahren zu ihrer herstellung und diese verbindungen enthaltendes lichtempfindliches gemisch |
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JPH05281728A (ja) | 1992-04-01 | 1993-10-29 | Fuji Photo Film Co Ltd | 光重合性組成物 |
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JP4156784B2 (ja) * | 2000-07-25 | 2008-09-24 | 富士フイルム株式会社 | ネガ型画像記録材料及び画像形成方法 |
JP4253432B2 (ja) * | 2000-11-01 | 2009-04-15 | 富士フイルム株式会社 | 平版印刷版用原版 |
JP4319363B2 (ja) * | 2001-01-15 | 2009-08-26 | 富士フイルム株式会社 | ネガ型画像記録材料 |
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JP2003344997A (ja) | 2003-12-03 |
DE50204080D1 (de) | 2005-10-06 |
EP1359008A1 (fr) | 2003-11-05 |
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