JPS6155666B2 - - Google Patents
Info
- Publication number
- JPS6155666B2 JPS6155666B2 JP54074258A JP7425879A JPS6155666B2 JP S6155666 B2 JPS6155666 B2 JP S6155666B2 JP 54074258 A JP54074258 A JP 54074258A JP 7425879 A JP7425879 A JP 7425879A JP S6155666 B2 JPS6155666 B2 JP S6155666B2
- Authority
- JP
- Japan
- Prior art keywords
- photosensitive
- resin
- layer
- acid
- silver halide
- 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
Links
- -1 silver halide Chemical class 0.000 claims description 70
- 229920005989 resin Polymers 0.000 claims description 61
- 239000011347 resin Substances 0.000 claims description 61
- 229910052709 silver Inorganic materials 0.000 claims description 55
- 239000004332 silver Substances 0.000 claims description 55
- 239000000839 emulsion Substances 0.000 claims description 28
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 19
- 239000000084 colloidal system Substances 0.000 claims description 15
- 239000010419 fine particle Substances 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 230000005660 hydrophilic surface Effects 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 238000006068 polycondensation reaction Methods 0.000 claims description 2
- 239000000203 mixture Substances 0.000 description 33
- 229920000642 polymer Polymers 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 17
- 238000000034 method Methods 0.000 description 16
- 238000011282 treatment Methods 0.000 description 16
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 15
- 239000011230 binding agent Substances 0.000 description 15
- 229910052782 aluminium Inorganic materials 0.000 description 14
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 14
- 239000007864 aqueous solution Substances 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- 229920001568 phenolic resin Polymers 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- 108010010803 Gelatin Proteins 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 229920000159 gelatin Polymers 0.000 description 9
- 239000008273 gelatin Substances 0.000 description 9
- 235000019322 gelatine Nutrition 0.000 description 9
- 235000011852 gelatine desserts Nutrition 0.000 description 9
- 229920002554 vinyl polymer Polymers 0.000 description 9
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 238000000576 coating method Methods 0.000 description 8
- 229920001577 copolymer Polymers 0.000 description 8
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000000975 dye Substances 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
- 239000002245 particle Substances 0.000 description 7
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 6
- XLLXMBCBJGATSP-UHFFFAOYSA-N 2-phenylethenol Chemical class OC=CC1=CC=CC=C1 XLLXMBCBJGATSP-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000004115 Sodium Silicate Substances 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000005011 phenolic resin Substances 0.000 description 6
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 6
- 229910052911 sodium silicate Inorganic materials 0.000 description 6
- 239000004793 Polystyrene Substances 0.000 description 5
- 229920002678 cellulose Polymers 0.000 description 5
- 235000010980 cellulose Nutrition 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 239000000049 pigment Substances 0.000 description 5
- 239000004014 plasticizer Substances 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
- 239000004372 Polyvinyl alcohol Substances 0.000 description 4
- 206010070834 Sensitisation Diseases 0.000 description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 4
- 239000001913 cellulose Substances 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 239000003350 kerosene Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- JESXATFQYMPTNL-UHFFFAOYSA-N mono-hydroxyphenyl-ethylene Natural products OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 229920002451 polyvinyl alcohol Polymers 0.000 description 4
- 230000001681 protective effect Effects 0.000 description 4
- 230000008313 sensitization Effects 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- 238000004381 surface treatment Methods 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- 206010012442 Dermatitis contact Diseases 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 229920002125 Sokalan® Polymers 0.000 description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 150000001408 amides Chemical group 0.000 description 3
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 description 3
- 230000007547 defect Effects 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 208000028659 discharge Diseases 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 229920001519 homopolymer Polymers 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229920003986 novolac Polymers 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 239000004584 polyacrylic acid Substances 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 229940079877 pyrogallol Drugs 0.000 description 3
- 239000011342 resin composition Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- ZRUOTKQBVMWMDK-UHFFFAOYSA-N 2-hydroxy-6-methylbenzaldehyde Chemical compound CC1=CC=CC(O)=C1C=O ZRUOTKQBVMWMDK-UHFFFAOYSA-N 0.000 description 2
- XOUQAVYLRNOXDO-UHFFFAOYSA-N 2-tert-butyl-5-methylphenol Chemical compound CC1=CC=C(C(C)(C)C)C(O)=C1 XOUQAVYLRNOXDO-UHFFFAOYSA-N 0.000 description 2
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- SJOOOZPMQAWAOP-UHFFFAOYSA-N [Ag].BrCl Chemical compound [Ag].BrCl SJOOOZPMQAWAOP-UHFFFAOYSA-N 0.000 description 2
- 239000011354 acetal resin Substances 0.000 description 2
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 150000005215 alkyl ethers Chemical class 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 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 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229930003836 cresol Natural products 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 150000008049 diazo compounds Chemical class 0.000 description 2
- JQCXWCOOWVGKMT-UHFFFAOYSA-N diheptyl phthalate Chemical compound CCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC JQCXWCOOWVGKMT-UHFFFAOYSA-N 0.000 description 2
- KPVWDKBJLIDKEP-UHFFFAOYSA-L dihydroxy(dioxo)chromium;sulfuric acid Chemical compound OS(O)(=O)=O.O[Cr](O)(=O)=O KPVWDKBJLIDKEP-UHFFFAOYSA-L 0.000 description 2
- 239000003792 electrolyte Substances 0.000 description 2
- VOOLKNUJNPZAHE-UHFFFAOYSA-N formaldehyde;2-methylphenol Chemical compound O=C.CC1=CC=CC=C1O VOOLKNUJNPZAHE-UHFFFAOYSA-N 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 229920000578 graft copolymer Polymers 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920002006 poly(N-vinylimidazole) polymer Polymers 0.000 description 2
- 229920006122 polyamide resin Polymers 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920006324 polyoxymethylene Polymers 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 229920005749 polyurethane resin Polymers 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 2
- 235000010265 sodium sulphite Nutrition 0.000 description 2
- 229940124530 sulfonamide Drugs 0.000 description 2
- 150000003456 sulfonamides Chemical group 0.000 description 2
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical class [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- MSQIQUAYMZPGGV-UHFFFAOYSA-N (2,4-diazidophenyl)-(4-ethoxyphenyl)diazene Chemical compound C1=CC(OCC)=CC=C1N=NC1=CC=C(N=[N+]=[N-])C=C1N=[N+]=[N-] MSQIQUAYMZPGGV-UHFFFAOYSA-N 0.000 description 1
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- VEBYREQAKIGEQI-UHFFFAOYSA-N 1,2-dibromo-2-phenylethenol Chemical compound OC(Br)=C(Br)C1=CC=CC=C1 VEBYREQAKIGEQI-UHFFFAOYSA-N 0.000 description 1
- KETQAJRQOHHATG-UHFFFAOYSA-N 1,2-naphthoquinone Chemical compound C1=CC=C2C(=O)C(=O)C=CC2=C1 KETQAJRQOHHATG-UHFFFAOYSA-N 0.000 description 1
- BLYXNIHKOMELAP-UHFFFAOYSA-N 1,8-Dinitropyrene Chemical compound C1=C2C([N+](=O)[O-])=CC=C(C=C3)C2=C2C3=CC=C([N+]([O-])=O)C2=C1 BLYXNIHKOMELAP-UHFFFAOYSA-N 0.000 description 1
- UTTBWXAPRWIJHV-UHFFFAOYSA-N 1-(4-azidophenyl)-3-(4-nitrophenyl)prop-2-en-1-one Chemical compound C1=CC([N+](=O)[O-])=CC=C1C=CC(=O)C1=CC=C(N=[N+]=[N-])C=C1 UTTBWXAPRWIJHV-UHFFFAOYSA-N 0.000 description 1
- GJNOFSPNXSSWLA-UHFFFAOYSA-N 1-(4-azidophenyl)-3-[4-(dimethylamino)phenyl]propan-1-one Chemical compound C1=CC(N(C)C)=CC=C1CCC(=O)C1=CC=C(N=[N+]=[N-])C=C1 GJNOFSPNXSSWLA-UHFFFAOYSA-N 0.000 description 1
- SYKLIKUNWVSWSU-UHFFFAOYSA-N 1-(4-azidophenyl)-5-(4-methoxyphenyl)penta-1,4-dien-3-one Chemical compound C1=CC(OC)=CC=C1C=CC(=O)C=CC1=CC=C(N=[N+]=[N-])C=C1 SYKLIKUNWVSWSU-UHFFFAOYSA-N 0.000 description 1
- DMMHRTIICDFJGX-UHFFFAOYSA-N 1-(4-azidophenyl)-5-phenylpenta-1,4-dien-3-one Chemical compound C1=CC(N=[N+]=[N-])=CC=C1C=CC(=O)C=CC1=CC=CC=C1 DMMHRTIICDFJGX-UHFFFAOYSA-N 0.000 description 1
- VHCQLHOGNILZAE-UHFFFAOYSA-N 1-(4-diazonioiminocyclohexa-2,5-dien-1-ylidene)-3-[4-[3-(4-diazonioiminocyclohexa-2,5-dien-1-ylidene)-1-oxidoprop-1-enyl]phenoxy]propan-1-olate Chemical compound C1=CC(=N[N+]#N)C=CC1=C([O-])CCOC(C=C1)=CC=C1C([O-])=CC=C1C=CC(=N[N+]#N)C=C1 VHCQLHOGNILZAE-UHFFFAOYSA-N 0.000 description 1
- FCVUYHQKKWKAGT-UHFFFAOYSA-N 1-(4-diazonioiminocyclohexa-2,5-dien-1-ylidene)-3-naphthalen-1-ylprop-2-en-1-olate Chemical compound C1=CC(N=[N+]=[N-])=CC=C1C(=O)C=CC1=CC=CC2=CC=CC=C12 FCVUYHQKKWKAGT-UHFFFAOYSA-N 0.000 description 1
- ARKQRZXCXIMZHG-UHFFFAOYSA-N 1-azido-4-[(4-azidophenyl)methyl]benzene Chemical compound C1=CC(N=[N+]=[N-])=CC=C1CC1=CC=C(N=[N+]=[N-])C=C1 ARKQRZXCXIMZHG-UHFFFAOYSA-N 0.000 description 1
- FEJNULHBBJVUTJ-UHFFFAOYSA-N 1-azido-4-[1,6-bis[(4-azidophenyl)methoxy]hexan-2-yloxymethyl]benzene Chemical compound C1=CC(N=[N+]=[N-])=CC=C1COCCCCC(OCC=1C=CC(=CC=1)N=[N+]=[N-])COCC1=CC=C(N=[N+]=[N-])C=C1 FEJNULHBBJVUTJ-UHFFFAOYSA-N 0.000 description 1
- COXWNUQPODQHGB-UHFFFAOYSA-N 1-chloro-2-phenylethenol Chemical compound OC(Cl)=CC1=CC=CC=C1 COXWNUQPODQHGB-UHFFFAOYSA-N 0.000 description 1
- KSURUOCVQMGISN-UHFFFAOYSA-N 1-chloropleiadene-7,12-dione Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C3=C2C1=CC=C3Cl KSURUOCVQMGISN-UHFFFAOYSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- ALRLPDGCPYIVHP-UHFFFAOYSA-N 1-nitropyrene Chemical compound C1=C2C([N+](=O)[O-])=CC=C(C=C3)C2=C2C3=CC=CC2=C1 ALRLPDGCPYIVHP-UHFFFAOYSA-N 0.000 description 1
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 1
- RSZXXBTXZJGELH-UHFFFAOYSA-N 2,3,4-tri(propan-2-yl)naphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(C(C)C)C(C(C)C)=C(C(C)C)C(S(O)(=O)=O)=C21 RSZXXBTXZJGELH-UHFFFAOYSA-N 0.000 description 1
- VUPRMJQRIGJKER-UHFFFAOYSA-N 2,5-bis[(4-azidophenyl)methylidene]cyclohexan-1-one Chemical compound C1=CC(N=[N+]=[N-])=CC=C1C=C(CC1)CC(=O)C1=CC1=CC=C(N=[N+]=[N-])C=C1 VUPRMJQRIGJKER-UHFFFAOYSA-N 0.000 description 1
- IRLYGRLEBKCYPY-UHFFFAOYSA-N 2,5-dimethylbenzenesulfonic acid Chemical compound CC1=CC=C(C)C(S(O)(=O)=O)=C1 IRLYGRLEBKCYPY-UHFFFAOYSA-N 0.000 description 1
- MLIWQXBKMZNZNF-UHFFFAOYSA-N 2,6-bis[(4-azidophenyl)methylidene]-4-methylcyclohexan-1-one Chemical compound O=C1C(=CC=2C=CC(=CC=2)N=[N+]=[N-])CC(C)CC1=CC1=CC=C(N=[N+]=[N-])C=C1 MLIWQXBKMZNZNF-UHFFFAOYSA-N 0.000 description 1
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- 229910052742 iron Inorganic materials 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 238000013532 laser treatment Methods 0.000 description 1
- 238000001459 lithography Methods 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000006011 modification reaction Methods 0.000 description 1
- 235000019426 modified starch Nutrition 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- JYKNHMGWUMJFTR-UHFFFAOYSA-N naphthalene-1,4-dione propan-2-one Chemical compound C1(C=CC(C2=CC=CC=C12)=O)=O.CC(=O)C JYKNHMGWUMJFTR-UHFFFAOYSA-N 0.000 description 1
- 239000000025 natural resin Substances 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- KIHUPOKUSVEICJ-UHFFFAOYSA-N nonyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 KIHUPOKUSVEICJ-UHFFFAOYSA-N 0.000 description 1
- 239000010680 novolac-type phenolic resin Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002898 organic sulfur compounds Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 229920006316 polyvinylpyrrolidine Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- AZIQALWHRUQPHV-UHFFFAOYSA-N prop-2-eneperoxoic acid Chemical group OOC(=O)C=C AZIQALWHRUQPHV-UHFFFAOYSA-N 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000001846 repelling effect Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 1
- 229940045105 silver iodide Drugs 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019795 sodium metasilicate Nutrition 0.000 description 1
- DCGXKAUTWZTTNF-UHFFFAOYSA-M sodium;3-[2-[2-(1,3-diethyl-5-oxo-2-sulfanylideneimidazolidin-4-ylidene)ethylidene]-1,3-benzoxazol-3-yl]propane-1-sulfonate Chemical compound [Na+].CCN1C(=S)N(CC)C(=O)C1=CC=C1N(CCCS([O-])(=O)=O)C2=CC=CC=C2O1 DCGXKAUTWZTTNF-UHFFFAOYSA-M 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- CXVGEDCSTKKODG-UHFFFAOYSA-N sulisobenzone Chemical class C1=C(S(O)(=O)=O)C(OC)=CC(O)=C1C(=O)C1=CC=CC=C1 CXVGEDCSTKKODG-UHFFFAOYSA-N 0.000 description 1
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical class NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/095—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having more than one photosensitive layer
- G03F7/0952—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having more than one photosensitive layer comprising silver halide or silver salt based image forming systems, e.g. for camera speed exposure
Description
本発明は、感光性ハロゲン化銀乳剤を含有する
感光層が設けられた感光性平版印刷版に関するも
ので、汚れが少く感脂性が高くとくに画像の再現
性が優れた印刷を一連の自現機処理によつて得る
ことができる感光性平版印刷版に関するものであ
る。
従来、例えば特公昭44−27242号、特公昭48−
16725号、特公昭48−30562号や、特開昭52−
154627号、特開昭53−10422号、また米国特許第
3083097号、同第3161508号、同第3721559号、及
び同第3146104号に記載されているように、ハロ
ゲン化銀を利用した感光性平版印刷版が知られて
いる。しかし、耐刷性が低かつたり、汚れがでや
すかつたり、あるいは感脂性（油性インクを受け
付ける性能）が充分でないなどのいくつかの欠陥
があつた。
一方、特公昭46−26521号、特開昭54−27804
や、西独特許公開（OLS）2517711号、同
2640763号等に記載されている様に、従来用いら
れているPS版（プレ センシタイズト プレー
ト（Pre−Sensitized Plate）を言う。）の感光層
の上にハロゲン化銀含有感光層が設けられている
感光性平版印刷版が知られている。しかし、感光
層とハロゲン化銀含有感光層との密着がわるい、
ハロゲン化銀含有感光層は処理液に浸されたとき
の膜質が弱くきずがつきやすくまた圧力によりカ
ブリが発生しやすいなど非常に多くの欠点があつ
た。この対策として、例えば特公昭47−23721号
や、米国防衛特許公告Ｔ−870022号などの記載に
あるように、中間層を設けることが提案されてい
る。しかし中間層を設けることは、実質上技術的
に困難でありまた製造コストを高くする上に、中
間層に、公知の材料を用いると、多くの場合、耐
刷力を低下させたり、感脂性を低下させたりまた
約１μ以上の厚さの中間層を設けると、画線の再
現性を劣化させる欠点が伴つた。
本発明者等は、上記のような事情に鑑み種々研
究を重ねた結果、本発明をなすに至つたものであ
つて、その要旨は親水性表面を有する支持体上
に、順に、親油性画像を形成し得る非銀感光層お
よび感光性ハロゲン化銀乳剤層を有する感光性平
版印刷版において、該感光性ハロゲン化銀乳剤層
はタンニング現像主薬を含まず、且つ該非銀感光
層上に隣接して設けられた親水性コロイド層が実
質的に水不溶性の親油性樹脂を微細粒子状で分散
含有していることを特徴とする感光性平版印刷版
である。
本発明の特徴は、親水性表面をもつ支持体の上
に、親油性画像を形成しうる非銀感光層を設け、
その上に実質的に水不溶性の固形の感脂性樹脂を
微細粒子として含有させた親水性コロイド層を設
ける点にあり、これにより響くべきことに、これ
ら２つの層間の密着性が著しく改良させることに
ある。また、この実質的に水不溶性の固形の親油
性の樹脂を微細粒子として含有させると親水性コ
ロイドの膜強度例えば傷がつきにくゝなるなど、
べとつき例えば指紋がつきにくくなるとか重ねた
とき接着するトラブル（所謂ブロツキング）がな
くなるなどの特性が著しく改善される。更に、こ
の樹脂を微細粒子として含有させると、ハロゲン
化銀を含有させた感光層は、加圧によるカブリの
発生または静電気の放電によるスタツチマークの
発生が減少する。その他の特長は、感脂性の樹脂
を含有せしめたのにかゝわらず現像の進行が遅れ
たり、汚れの発生が増大したりする有害な作用が
伴わないことにある。
次に本発明の感光性平版印刷版の構成要素につ
いて説明する。本発明に使用される支持体は、親
水性表面をもつ支持体で、平版印刷版として用い
られる何れの支持体でもよい。
かかる支持体としては、紙、プラスチツク、
（例えばポリエチレン、ポリプロピレン、ポリス
チレンなど）がラミネートされた紙、例えばアル
ミニウム（アルミニウム合金も含む。）、亜鉛、
鉄、銅などのような金属の板、例えば二酢酸セル
ロース、三酢酸セルロース、プロピオン酸セルロ
ース、酪酸セルロース、酪酸酢酸セルロース、硝
酸セルロース、ポリエチレンテレフタレート、ポ
リエチレン、ポリスチレン、ポリプロピレン、ポ
リカーボネート、ポリビニルアセタールなどのよ
うなプラスチツクのフイルム、上記の如き金属が
ラミネートもしくは蒸着された紙もしくはプラス
チツクフイルムなどが含まれる。これらの内、好
しくはアルミニウム板またはアルミニウムシート
が結合された複合体シートが用いられる。
これらの支持体は親水性表面をうるために必要
により表面処理または親水層を設けるなどの処理
をしなければならない。このような親水化処理に
は種々のものがある。例えばプラスチツクの表面
を有する支持体の場合には、化学的処理、放電処
理、火焔処理、紫外線処理、高周波処理、グロー
放電処理、活性プラズマ処理、レーザー処理など
の所謂表面処理方法（たとえば米国特許第
2764520号、3497407号、3145242号、3376208号、
3072483号、3475193号、3360448号、英国特許第
788365号明細書など）がある。必要によりこの表
面処理のあと、例えば米国特許第2649373号、特
開昭53−40890号、同53−61643号などに記載の如
く親水性層を設けることができる。
また金属、特にアルミニウムの表面を有する支
持体の場合には、砂目立て処理、珪酸ソーダ、弗
化ジルコニウム酸カリウム、燐酸塩等の水溶液へ
の浸漬処理、あるいは陽極酸化処理などの表面処
理がなされていることが好ましい。また、米国特
許第2714066号明細書に記載されている如く、砂
目立てしたのちに珪酸ナトリウム水溶液に浸漬処
理されたアルミニウム板、米国特許第3181461号
明細書に記載されているようにアルミニウム板を
陽極酸化処理したのちに、アルカリ金属珪酸塩の
水溶液に浸漬処理したものも好適に使用される。
上記陽極酸化処理は、例えば、燐酸、クロム酸、
硫酸、硼酸等の無機酸、若しくは、蓚酸、スルフ
アミン酸等の有機酸またはこれらの塩の水溶液又
は非水溶液の単独又は二種以上を組み合わせた溶
液中で、特に好ましくは、燐酸、硫酸またはこれ
らの混合物の水溶液中でアルミニウム板に電流を
流すことにより実施される。また米国特許第
3658662号明細書に記載されているようなシリケ
ート電着も有効である。更に、英国特許第
1208224号明細書に記載されているように、アル
ミニウム板を塩酸電解液中で交流で電解し、つい
で硫酸電解液中で陽極酸化したアルミニウム板も
好ましい。また、上記の如き行程で陽極酸化され
たアルミニウム板に、米国特許第3860426号明細
書に記されているように亜鉛などの金属の水溶性
塩を含むセルロース系樹脂の下塗り層を設けるこ
とは、印刷時のスカムを防止する上で、好まし
い。
このような支持体上に設けられる、親油性画像
を形成しうる非銀感光層には感光性平版印刷版
（プレ センシタイズド プレート（Pre−
Sensitized Plate）とも云われ、PS版と略称され
ている。）に使用される感光層が含まれる。ここ
で上記の「親油性画像」における親油性とは、印
刷時に使用される湿し水を反撥して、油性インク
を受容することを意味する。このような感光層を
構成する組成物には、次のようなものが含まれ
る。
(1) ジアゾ樹脂からなる組成物
ｐ−ジアゾジフエニルアミンとパラホルムア
ルデヒドとの縮合物に代表されるジアゾ樹脂
は、水溶性のものでも、水不溶性のものでも良
いが、好ましくは、水不溶性かつ通常の有機溶
媒に可溶性のものが使用される。特に好ましい
ジアゾ化合物としては、ｐ−ジアゾフエニルア
ミンとホルムアルデヒド又はアセトアルデヒド
との縮合物の塩、例えばフエノール塩、フルオ
ロカプリン酸塩、及びトリイソプロピルナフタ
レンスルホン酸、４・４−ビフエニルジスルホ
ン酸、５−ニトロオルトートルエンスルホン
酸、５−スルホサリチル酸、２・５−ジメチル
ベンゼンスルホン酸、２−ニトロベンゼンスル
ホン酸、３−クロロベンゼンスルホン酸、３−
ブロモベンゼンスルホン酸、２−クロロ−５−
ニトロベンゼンスルホン酸、２−フルオロカプ
リルナフタレンスルホン酸、１−ナフトール−
５−スルホン酸、２−メトキシ−４−ヒドロオ
キシ−５−ベンゾイル−ベンゼンスルホン酸及
びパラトルエンスルホン酸などのスルホン酸の
塩などのように一分子中に２個以上のジアゾ基
を有する化合物である。この他望ましいジアゾ
樹脂としては上記の塩を含む２・５−ジメトキ
シ−４−ｐ−トリルメルカプトンベンゼンジア
ゾニウムとホルムアルデヒドの縮合物、２・５
−ジメトキシ−４−モリホリノベンゼンジアゾ
ニウムとホルルアルデヒドまたはアセトアルデ
ヒドとの縮合物が含まれる。
また、英国特許第1312925号明細書に記載さ
れているジアゾ樹脂も好ましい。
ジアゾ樹脂は、単独でレジストの作成に使用
される感光物となり得るが、好ましくはバイン
ダーと共に使用される。
かかるバインダーとしては、種々の高分子化
合物が使用され得るが、ヒドロキシ、アミノ、
カルボン酸、アミド、スルホンアミド、活性メ
チレン、チオアルコール、エポキシ等の基を含
むものが好ましい。このような好ましいバイン
ダーには、英国特許第1350521号明細書に記さ
れているシエラツク、英国特許第1460978号お
よび米国特許第4123276号の各明細書に記され
ているようなヒドロキシエチルアクリレート単
位またはヒドロキシエチルメタクリレート単位
を主なる繰り返し単位として含むポリマー、米
国特許第3751257号明細書に記されているポリ
アミド樹脂、英国特許第1074392号明細書に記
されているフエノール樹脂および例えばポリビ
ニルフオルマール樹脂、ポリビニルブチラール
樹脂のようなポリビニルアセタール樹脂、米国
特許第3660097号明細書に記されている線状ポ
リウレタン樹脂、ポリビニルアルコールのフタ
レート化樹脂、ビスフエノールＡとエピクロル
ヒドリンから縮合されたエポキシ樹脂、ポリア
ミノスチレンやポリアルキルアミノ（メタ）ア
クリレートのようなアミノ基を含むポリマー、
酢酸セルロース、セルロースアルキルエーテ
ル、セルロースアセテートフタレート等のセル
ロース類等が包含される。
バインダーの含有量は、感光性レジスト形成
性組成物中に40〜95重量％含まれているのが適
当である。バインダーの量が多くなれば（即
ち、ジアゾ樹脂の量が少なくなれば）感光性は
当然大になるが、経時安定性が低下する。最適
のバインダーの量は約70〜90重量％である。
ジアゾ樹脂からなる組成物には、更に、米国
特許第3236646号明細書に記載されている燐
酸、染料や顔料などの添加剤を加えることがで
きる。
(2) ｏ−キノンジアジド化合物からなる組成物
特に好ましいｏ−キノンジアジド化合物はｏ
−ナフトキノンジアジド化合物であり、例えば
米国特許第2766118号、同第2767092号、同第
2772972号、同第2859112号、同第2907665号、
同第3046110号、同第3046111号、同第3046115
号、同第3046118号、同第3046119号、同第
3046120号、同第3046121号、同第3046122号、
同第3046123号、同第3061430号、同第3102809
号、同第3106465号、同第3635709号、同第
3647443号の各明細書をはじめ、多数の刊行物
に記されており、これらは好適に使用すること
ができる。これらの内でも、特に芳香族ヒドロ
キシ化合物のｏ−ナフトキノンジアジドスルホ
ン酸エステルまたはｏ−ナフトキノンジアジド
カルボン酸エステル、および芳香族アミノ化合
物のｏ−ナフトキノンジアジドスルホン酸アミ
ドまたはｏ−ナフトキノンジアジドカルボン酸
アミドが好ましく、特に米国特許第3635709号
明細書に記されているピロガロールとアセトン
との縮合物にｏ−ナフトキノンジアジドスルホ
ン酸をエステル反応させたもの、米国特許第
4028111号明細書に記されている末端にヒドロ
キシ基を有するポリエステルにｏ−ナフトキノ
ンジアジドスルホン酸、またはｏ−ナフトキノ
ンジアジドカルボン酸をエステル反応させたも
の、英国特許第1494043号明細書に記されてい
るようなｐ−ヒドロキシスチレンのホモポリマ
ーまたはこれと他の共重合し得るモノマーとの
共重合体にｏ−ナフトキノンジアジドスルホン
酸またはｏ−ナフトキノンジアジドカルボン酸
をエステル反応させたものは非常にすぐれてい
る。
これらのｏ−キノンジアジド化合物は、単独
で使用することができるが、アルカリ可溶性樹
脂と混合して用いた方が好ましい。好適なアル
カリ可溶性樹脂には、ノボラツク型フエノール
樹脂が含まれ、具体的には、フエノールホルム
アルデヒド樹脂、ｏ−クレゾールホルムアルデ
ヒド樹脂、ｍ−クレゾーホホルムアルデヒド樹
脂などが含まれる。更に米国特許第4123279号
明細書に記されている様に上記のようなフエノ
ール樹脂と共に、ｔ−ブチルフエノールホルム
アルデヒド樹脂のような炭素数３〜８のアルキ
ル基で置換されたフエノールまたはクレゾール
とホルムアルデヒドとの縮合物とを併用する
と、より一層好ましい。アルカリ可溶性樹脂
は、感光性レジスト形成性組成物の全重量を基
準として中に約50〜約85重量、より好ましくは
60〜80重量％、含有させられる。
ｏ−キノンジアジド化合物からなる感光性組
成物には、必要に応じて更に顔料や染料、可塑
剤などを含有させることができる。
(3) 感光性アジド化合物からなる組成物
適当な感光性アジド化合物としてはアジド基
が直接又はカルボニル基又はスルホニル基を介
して芳香環に結合している芳香族アジド化合物
である。これらは光によりアジド基が分解し
て、ナイトレンを生じ、ナイトレンが種々の反
応を起こして不溶化するものである。好ましい
芳香族アジド化合物としては、アジドフエニ
ル、アジドスチリル、アジドベンザル、アジド
ベンゾイル及びアジドシンナモイルの如き基を
１個又はそれ以上含む化合物で、たとえば４・
4′−ジアジドカルコン、４−アジド−4′−（４
−アジドベンゾイルエトキシ）カルコン、Ｎ・
Ｎ−ビス−ｐ−アジドベンザル−ｐ−フエニレ
ンジアミン、１・２・６−トリ（4′−アジドベ
ンゾキシ）ヘキサン、２−アジド−３−クロロ
−ベンゾキノン、２・４−ジアジド−4′−エト
キシアゾベンゼン、２・６−ジ（4′−アジドベ
ンザル）−４−メチルシクロヘキサノン、４・
4′−ジアジドベンゾフエノン、２・５−ジアジ
ド−３・６−ジクロロベンゾキノン、２・５−
ビス（４−アジドスチリル）−１・３・４−オ
キサジアゾール、２−（４−アジドシンナモイ
ル）チオフエン、２・５−ジ（4′−アジドベン
ザル）シクロヘキサノン、４・4′−ジアジドジ
フエニルメタン、１−（４−アジドフエニル）−
５−フリル−２−ペンタ−２・４−ジエン−１
−オン、１−（４−アジドフエニル）−５−（４
−メトキシフエニル）−ペンタ−１・４−ジエ
ン−３−オン、１−（４−アジドフエニル）−３
−（１−ナフチル）プロペン−１−オン、１−
（４−アジドフエニル）−３−（４−ジメチルア
ミノフエニル）−プロパン−１−オン、１−（４
−アジドフエニル）−５−フエニル−１・４−
ペンタジエン−３−オン、１−（４−アジドフ
エニル）−３−（４−ニトロフエニル）−２−プ
ロペン−１−オン、１−（４−アジドフエニ
ル）−３−（２−フリル）−２−プロペン−１−
オン、１・２・６−トリ（4′−アジドベンゾキ
シ）ヘキサン、２・６−ビス−（４−アジドベ
ンジリジン−ｐ−ｔ−ブチル）シクロヘキサノ
ン、４・4′−ジアジドベンザルアセトン、４・
4′−ジアジドスチルベン−２・2′−ジスルホン
酸、4′−アジドベンザルアセトフエノン−２−
スルホン酸、４・4′−ジアジドスチルベン−α
−カルボン酸、ジ−（４−アジド−2′−ヒドロ
キシベンザル）アセトン−２−スルホン酸、４
−アジドベンザルアセトフエノン−２−スルホ
ン酸、２−アジド−１・４−ジベンゼンスルホ
ニルアミノナフタレン、４・4′−ジアジド−ス
チルベン−２・2′−ジスルホン酸アニリド等を
あげることが出来る。
またこれらの低分子量芳香族アジド化合物以
外にも特公昭44−9047号、同44−31837号、同
45−9613号、同45−24915号、同45−25713号、
特開昭50−5102号、同50−84302号、同50−
84303号、同53−12984号の各公報に記載のアジ
ド基含有ポリマーも適当である。
これらの感光性アジド化合物は、好ましくは
バインダーとしての高分子化合物と共に使用さ
れる。好ましいバインダーとしてはアルカリ可
溶性樹脂があり、例えばシエラツク、ロジンな
どの天然樹脂、例えばフエノールホルムアルデ
ヒド樹脂、ｍ−クレゾールホルムアルデヒド樹
脂などのノボラツク型フエノール樹脂、例えば
ポリアクリル酸、ポリメタクリル酸、メタクリ
ル酸−スチレン共重合体、メタクリル酸−アク
リル酸メチル共重合体、スチレン−無水マレイ
ン酸共重合体などの不飽和カルボン酸の単独重
合体またはこれと他の共重合し得るモノマーと
の共重合体、ポリ酢酸ビニルの部分または完全
けん化物を例えばアセトアルデヒド、ベンズア
ルデヒド、ヒドロキシベンズアルデヒド、カル
ボキシベンズアルデヒドなどのアルデヒドで部
分アセタール化した樹脂、ポリヒドロキシスチ
レンなどが含まれる。更に、例えばセルロース
メチルエーテル、セルロースエチルエーテルな
どのセルロースアルキルエーテル類をはじめと
する有機溶媒可溶性樹脂もバインダーとして使
用できる。
バインダーは、感光性アジド化合物からなる
組成物の全重料に対して約10重料％から約90重
量％の範囲で含有させることが好ましい。
感光性アジド化合物からなる組成物には、更
に染料や顔料、例えばフタル酸エステル、燐酸
エステル、脂肪族カルボン酸エステル、グリコ
ール類、スルフオンアミド類などの可塑剤、例
えばミヒラ−ケトン、９−フルオレノン、１−
ニトロピレン、１・８−ジニトロピレン、２−
クロロ−１・２−ベンズアントラキノン、２−
ブロモ−１・２−ベンズアントラキノン、ピレ
ン−１・６−キノン、２−クロロ−１・８−フ
タロイルナフタレン、シアノアクリジンなどの
増感剤などの添加剤を加えることができる。
(4) 重合体の主鎖又は側鎖に
The present invention relates to a photosensitive lithographic printing plate provided with a photosensitive layer containing a photosensitive silver halide emulsion.The present invention relates to a photosensitive planographic printing plate provided with a photosensitive layer containing a photosensitive silver halide emulsion. The present invention relates to a photosensitive lithographic printing plate obtainable by processing. Previously, for example, Special Publication No. 1972-27242, Special Publication No. 48-
No. 16725, Special Publication No. 30562, No. 16725, and Special Publication No. 16725
No. 154627, Japanese Patent Application Publication No. 10422/1983, and U.S. Patent No.
As described in No. 3083097, No. 3161508, No. 3721559, and No. 3146104, photosensitive lithographic printing plates using silver halide are known. However, it had several defects, such as low printing durability, easy staining, and insufficient oil sensitivity (ability to accept oil-based ink). On the other hand, JP-A No. 46-26521, JP-A No. 54-27804
, West German Patent Publication (OLS) No. 2517711,
As described in No. 2640763, etc., a photosensitive plate in which a silver halide-containing photosensitive layer is provided on the photosensitive layer of a conventionally used PS plate (pre-sensitized plate). A lithographic printing plate is known. However, the adhesion between the photosensitive layer and the silver halide-containing photosensitive layer is poor;
The silver halide-containing photosensitive layer had a number of drawbacks, including poor film quality when immersed in a processing solution and being easily scratched and prone to fogging due to pressure. As a countermeasure against this problem, it has been proposed to provide an intermediate layer, as described in, for example, Japanese Patent Publication No. 47-23721 and US Defense Patent Publication No. T-870022. However, providing an intermediate layer is practically technically difficult and increases manufacturing costs.In addition, if known materials are used for the intermediate layer, printing durability may be reduced in many cases, or oil sensitivity may increase. However, if the intermediate layer is provided with a thickness of about 1 .mu.m or more, the reproducibility of the image is deteriorated. The present inventors have conducted various studies in view of the above-mentioned circumstances, and as a result, have come up with the present invention. In a photosensitive lithographic printing plate having a non-silver photosensitive layer and a photosensitive silver halide emulsion layer capable of forming a tanning agent, the photosensitive silver halide emulsion layer does not contain a tanning developing agent and is adjacent to the non-silver photosensitive layer. The photosensitive lithographic printing plate is characterized in that the hydrophilic colloid layer provided thereon contains a substantially water-insoluble lipophilic resin dispersed in the form of fine particles. A feature of the present invention is that a non-silver photosensitive layer capable of forming a lipophilic image is provided on a support having a hydrophilic surface,
On top of that is a hydrophilic colloid layer containing a substantially water-insoluble solid liposensitive resin as fine particles, which should significantly improve the adhesion between these two layers. It is in. In addition, when this substantially water-insoluble solid lipophilic resin is contained in the form of fine particles, the film strength of the hydrophilic colloid increases, for example, it becomes less likely to be scratched.
Properties such as stickiness, eg, fingerprints, and adhesion problems (so-called blocking) when stacked are eliminated, are significantly improved. Furthermore, when this resin is contained in the form of fine particles, the silver halide-containing photosensitive layer is less prone to fogging due to pressure or static marks due to electrostatic discharge. Another advantage is that even though it contains an oil-sensitive resin, it does not cause any harmful effects such as delaying the progress of development or increasing the occurrence of stains. Next, the constituent elements of the photosensitive planographic printing plate of the present invention will be explained. The support used in the present invention may be any support having a hydrophilic surface and used as a lithographic printing plate. Such supports include paper, plastic,
Paper laminated with (e.g. polyethylene, polypropylene, polystyrene, etc.), e.g. aluminum (including aluminum alloys), zinc,
Plates of metals such as iron, copper, etc., such as cellulose diacetate, cellulose triacetate, cellulose propionate, cellulose butyrate, cellulose acetate butyrate, cellulose nitrate, polyethylene terephthalate, polyethylene, polystyrene, polypropylene, polycarbonate, polyvinyl acetal, etc. Examples include paper or plastic films laminated or vapor-deposited with metals such as those mentioned above. Among these, preferably an aluminum plate or a composite sheet bonded with aluminum sheets is used. These supports must be subjected to surface treatment or treatment to provide a hydrophilic layer, if necessary, in order to obtain a hydrophilic surface. There are various types of such hydrophilic treatment. For example, in the case of supports with plastic surfaces, so-called surface treatment methods such as chemical treatment, electric discharge treatment, flame treatment, ultraviolet treatment, high frequency treatment, glow discharge treatment, active plasma treatment, laser treatment (for example, US Pat.
No. 2764520, No. 3497407, No. 3145242, No. 3376208,
No. 3072483, No. 3475193, No. 3360448, British Patent No.
788365, etc.). If necessary, after this surface treatment, a hydrophilic layer can be provided as described in, for example, US Pat. In addition, in the case of a support having a metal surface, especially aluminum, surface treatments such as graining treatment, immersion treatment in an aqueous solution of sodium silicate, potassium fluorozirconate, phosphate, etc., or anodization treatment are performed. Preferably. In addition, as described in U.S. Patent No. 2,714,066, an aluminum plate that has been grained and then immersed in a sodium silicate aqueous solution, and as described in U.S. Pat. No. 3,181,461, an aluminum plate can be used as an anode. Those obtained by oxidation treatment and then immersion treatment in an aqueous solution of an alkali metal silicate are also suitably used.
The above anodic oxidation treatment is performed using, for example, phosphoric acid, chromic acid,
Phosphoric acid, sulfuric acid, or a combination of two or more of aqueous or non-aqueous solutions of inorganic acids such as sulfuric acid and boric acid, or organic acids such as oxalic acid and sulfamic acid, or their salts are particularly preferably used. It is carried out by passing an electric current through an aluminum plate in an aqueous solution of the mixture. Also, U.S. Patent No.
Silicate electrodeposition as described in No. 3,658,662 is also effective. Additionally, British Patent No.
Also preferred is an aluminum plate which is electrolyzed with alternating current in a hydrochloric acid electrolyte and then anodized in a sulfuric acid electrolyte, as described in No. 1208224. Additionally, providing an undercoat layer of cellulose resin containing a water-soluble salt of a metal such as zinc on an aluminum plate anodized in the above process as described in U.S. Pat. No. 3,860,426, This is preferable in terms of preventing scum during printing. A photosensitive lithographic printing plate (pre-sensitized plate) is used as a non-silver photosensitive layer provided on such a support and capable of forming a lipophilic image.
It is also called Sensitized Plate and is abbreviated as PS version. ) includes the photosensitive layer used in Here, lipophilicity in the above-mentioned "oleophilic image" means repelling dampening water used during printing and accepting oil-based ink. Compositions constituting such a photosensitive layer include the following. (1) Composition made of diazo resin The diazo resin represented by the condensate of p-diazodiphenylamine and paraformaldehyde may be water-soluble or water-insoluble, but preferably water-insoluble and water-insoluble. Those soluble in common organic solvents are used. Particularly preferred diazo compounds include salts of condensates of p-diazophenylamine and formaldehyde or acetaldehyde, such as phenol salts, fluorocaprates, and triisopropylnaphthalenesulfonic acid, 4,4-biphenyldisulfonic acid, 5 -Nitroorthotoluenesulfonic acid, 5-sulfosalicylic acid, 2,5-dimethylbenzenesulfonic acid, 2-nitrobenzenesulfonic acid, 3-chlorobenzenesulfonic acid, 3-
Bromobenzenesulfonic acid, 2-chloro-5-
Nitrobenzenesulfonic acid, 2-fluorocaprylnaphthalenesulfonic acid, 1-naphthol-
A compound having two or more diazo groups in one molecule, such as salts of sulfonic acids such as 5-sulfonic acid, 2-methoxy-4-hydroxy-5-benzoyl-benzenesulfonic acid, and para-toluenesulfonic acid. . Other desirable diazo resins include a condensate of 2,5-dimethoxy-4-p-tolylmercapton benzenediazonium and formaldehyde containing the above salts, 2,5-dimethoxy-4-p-tolylmercapton, and formaldehyde
Condensates of -dimethoxy-4-morifolinobenzenediazonium and formaldehyde or acetaldehyde are included. Also preferred are the diazo resins described in British Patent No. 1312925. The diazo resin can be used alone as a photoresist for making a resist, but is preferably used in conjunction with a binder. Various polymer compounds can be used as such binders, including hydroxy, amino,
Those containing groups such as carboxylic acid, amide, sulfonamide, active methylene, thioalcohol, and epoxy are preferred. Such preferred binders include sierachiac as described in GB 1350521, hydroxyethyl acrylate units or hydroxyl acrylate units as described in GB 1460978 and US 4123276. Polymers containing ethyl methacrylate units as the main repeat unit, polyamide resins as described in US Pat. No. 3,751,257, phenolic resins as described in British Patent No. 1,074,392 and e.g. polyvinyl formal resins, Polyvinyl acetal resins such as butyral resins, linear polyurethane resins as described in U.S. Pat. No. 3,660,097, phthalated resins of polyvinyl alcohol, epoxy resins condensed from bisphenol A and epichlorohydrin, polyaminostyrenes and polyalkyls. polymers containing amino groups, such as amino (meth)acrylates,
Celluloses such as cellulose acetate, cellulose alkyl ether, and cellulose acetate phthalate are included. The content of the binder in the photosensitive resist-forming composition is suitably 40 to 95% by weight. As the amount of binder increases (ie, as the amount of diazo resin decreases), the photosensitivity naturally increases, but the stability over time decreases. The optimum amount of binder is about 70-90% by weight. Additives such as phosphoric acid, dyes and pigments described in US Pat. No. 3,236,646 can also be added to the diazo resin composition. (2) Composition consisting of an o-quinonediazide compound A particularly preferred o-quinonediazide compound is o-quinonediazide compound.
- Naphthoquinone diazide compounds, such as U.S. Patent Nos. 2766118, 2767092,
No. 2772972, No. 2859112, No. 2907665,
Same No. 3046110, Same No. 3046111, Same No. 3046115
No. 3046118, No. 3046119, No. 3046119, No. 3046118, No. 3046119, No.
No. 3046120, No. 3046121, No. 3046122,
Same No. 3046123, Same No. 3061430, Same No. 3102809
No. 3106465, No. 3635709, No. 3635709, No. 3106465, No. 3635709, No.
It is described in many publications including the specifications of No. 3647443, and these can be suitably used. Among these, o-naphthoquinonediazide sulfonic acid ester or o-naphthoquinonediazidecarboxylic acid ester of an aromatic hydroxy compound, and o-naphthoquinonediazide sulfonic acid amide or o-naphthoquinonediazidecarboxylic acid amide of an aromatic amino compound are particularly preferred. In particular, the condensate of pyrogallol and acetone described in U.S. Pat. No. 3,635,709 is subjected to an ester reaction with o-naphthoquinone diazidesulfonic acid,
Polyester having a hydroxyl group at the terminal described in the specification of No. 4028111 is ester-reacted with o-naphthoquinonediazide sulfonic acid or o-naphthoquinonediazidecarboxylic acid, and described in the specification of British Patent No. 1494043 A homopolymer of p-hydroxystyrene or a copolymer of this and other copolymerizable monomers with o-naphthoquinonediazide sulfonic acid or o-naphthoquinonediazidecarboxylic acid is very good. . Although these o-quinonediazide compounds can be used alone, it is preferable to use them in combination with an alkali-soluble resin. Suitable alkali-soluble resins include novolak type phenolic resins, and specifically include phenol formaldehyde resins, o-cresol formaldehyde resins, m-cresol formaldehyde resins, and the like. Further, as described in U.S. Pat. No. 4,123,279, in addition to the above-mentioned phenol resin, phenol or cresol substituted with an alkyl group having 3 to 8 carbon atoms such as t-butylphenol formaldehyde resin and formaldehyde are used. It is even more preferable to use it in combination with a condensate. The alkali-soluble resin contains about 50 to about 85% by weight, more preferably about 85% by weight based on the total weight of the photosensitive resist-forming composition.
It can be contained in an amount of 60 to 80% by weight. The photosensitive composition made of the o-quinonediazide compound can further contain pigments, dyes, plasticizers, etc., if necessary. (3) Composition comprising a photosensitive azide compound A suitable photosensitive azide compound is an aromatic azide compound in which an azide group is bonded to an aromatic ring directly or via a carbonyl group or a sulfonyl group. In these, the azide group is decomposed by light to produce nitrene, which undergoes various reactions and becomes insolubilized. Preferred aromatic azide compounds include compounds containing one or more groups such as azidophenyl, azidostyryl, azidobenzal, azidobenzoyl and azidocinnamoyl, for example 4.
4'-Diazidochalcone, 4-azido-4'-(4
-azidobenzoylethoxy)chalcone, N.
N-bis-p-azidobenzal-p-phenylenediamine, 1,2,6-tri(4'-azidobenzoxy)hexane, 2-azido-3-chloro-benzoquinone, 2,4-diazido-4'-ethoxyazobenzene , 2,6-di(4'-azidobenzal)-4-methylcyclohexanone, 4.
4'-Diazidobenzophenone, 2,5-diazide-3,6-dichlorobenzoquinone, 2,5-
Bis(4-azidostyryl)-1,3,4-oxadiazole, 2-(4-azidocinnamoyl)thiophene, 2,5-di(4'-azidobenzal)cyclohexanone, 4,4'-diazidodiphenyl Methane, 1-(4-azidophenyl)-
5-furyl-2-penta-2,4-diene-1
-one, 1-(4-azidophenyl)-5-(4
-methoxyphenyl)-penta-1,4-dien-3-one, 1-(4-azidophenyl)-3
-(1-naphthyl)propen-1-one, 1-
(4-azidophenyl)-3-(4-dimethylaminophenyl)-propan-1-one, 1-(4
-azidophenyl)-5-phenyl-1,4-
Pentadien-3-one, 1-(4-azidophenyl)-3-(4-nitrophenyl)-2-propen-1-one, 1-(4-azidophenyl)-3-(2-furyl)-2-propene- 1-
1,2,6-tri(4'-azidobenzoxy)hexane, 2,6-bis-(4-azidobenzylidine-pt-butyl)cyclohexanone, 4,4'-diazidobenzalacetone, 4・
4′-Diazidostilbene-2・2′-disulfonic acid, 4′-azidobenzalacetophenone-2-
Sulfonic acid, 4,4′-diazidostilbene-α
-carboxylic acid, di-(4-azido-2'-hydroxybenzal)acetone-2-sulfonic acid, 4
-azidobenzalacetophenone-2-sulfonic acid, 2-azido-1,4-dibenzenesulfonylaminonaphthalene, 4,4'-diazido-stilbene-2,2'-disulfonic acid anilide, etc. . In addition to these low molecular weight aromatic azide compounds, there are also
No. 45-9613, No. 45-24915, No. 45-25713,
JP-A No. 50-5102, No. 50-84302, No. 50-
The azide group-containing polymers described in Patent Publications No. 84303 and No. 53-12984 are also suitable. These photosensitive azide compounds are preferably used together with a polymer compound as a binder. Preferred binders include alkali-soluble resins, such as natural resins such as silica and rosin, novolac type phenolic resins such as phenol formaldehyde resins and m-cresol formaldehyde resins, and polyacrylic acid, polymethacrylic acid, methacrylic acid-styrene resins, etc. Polymers, homopolymers of unsaturated carboxylic acids such as methacrylic acid-methyl acrylate copolymers, styrene-maleic anhydride copolymers, or copolymers of these with other copolymerizable monomers, polyvinyl acetate Examples include resins obtained by partially or completely saponified products of which are partially acetalized with aldehydes such as acetaldehyde, benzaldehyde, hydroxybenzaldehyde, and carboxybenzaldehyde, and polyhydroxystyrene. Furthermore, organic solvent soluble resins including cellulose alkyl ethers such as cellulose methyl ether and cellulose ethyl ether can also be used as binders. The binder is preferably contained in an amount of about 10% to about 90% by weight based on the total weight of the composition comprising the photosensitive azide compound. The composition comprising the photosensitive azide compound may further contain dyes and pigments, plasticizers such as phthalates, phosphoric esters, aliphatic carboxylic esters, glycols, and sulfonamides, such as Michler's ketone and 9-fluorenone. , 1-
Nitropyrene, 1,8-dinitropyrene, 2-
Chloro-1,2-benzanthraquinone, 2-
Additives such as sensitizers such as bromo-1,2-benzanthraquinone, pyrene-1,6-quinone, 2-chloro-1,8-phthaloylnaphthalene, cyanoacridine, etc. can be added. (4) In the main chain or side chain of the polymer
【式】
基を含む高分子化合物からなる組成物
重合体主鎖又は側鎖に感光性基として
[Formula] A composition consisting of a polymer compound containing a group as a photosensitive group in the main chain or side chain of the polymer.
【式】を含むポリエステル類、ポリ
アミド類、ポリカーボネート類のような感光性重
合体を主成分とするもの（例えば米国特許第
3030208号、同第3707373号及び同第3453237号の
各明細書に記載されているような化合物）；シン
ナミリデンマロン酸等の（２−プロペリデン）マ
ロン酸化合物及び二官能性グリコール類から誘導
される感光性ポリエステル類を主成分としたもの
（例えば米国特許第2956878号及び同第3173787号
の各明細書に記載されているような感光性重合
体）；ポリビニールアルコール、澱粉、セルロー
ス及びその類似物のような水酸基含有重合体のケ
イ皮酸エステル類（例えば米国特許第2690966
号、同第2752372号、同第2732301号等の各明細書
に記載されているような感光性重合体）等が包含
される。これらの組成物中には他に増感剤、安定
化剤、可塑剤、顔料や染料等を含ませることがで
きる。
(5) 付加重合性不飽和化合物からなる光重合性組
成物
この組成物は、好ましくは、(a)少なくとも２
個の末端ビニル基を有するビニル単量体、(b)光
重合開始剤及び(c)バインダーとしての高分子化
合物からなる。
成分(a)のビニル単量体としては、特公昭35−
5093号、特公昭35−14719号、特公昭44−28727
号の各公報等に記載される、ポリオールのアク
リル酸またはメタクリル酸エステル、すなわち
ジエチレングリコールジ（メタ）アクリレー
ト、トリエチレングリコールジ（メタ）アクリ
レート、ペンタエリスリトールトリ（メタ）ア
クリレート、トリメチロールプロパントリ（メ
タ）アクリレート等、あるいはメチレンビス
（メタ）アクリルアミド、エチレンビス（メ
タ）アクリルアミドの様なビス（メタ）アクリ
ルアミド類、あるいはウレタン基を含有する不
飽和単量体、例えばジ−（2′−メタクリロキシ
エチル）−２・４−トリレンジウレタン、ジ−
（2′−アクリロキシエチル）トリメチレンジウ
レタン等の様なジオールモノ（メタ）アクリレ
ートとジイソシアネートとの反応生成物等が掲
げられる。
成分(b)の光重合開始剤としては、例えば、J.
コーサー著「ライト・センシシデイブ・システ
ムズ」第５章に記載されているようなカルボニ
ル化合物、有機硫黄化合物、過硫化物、レドツ
クス系化合物、アゾ並びにジアゾ化合物、ハロ
ゲン化合物、光還元性色素などがある。更に具
体的には英国特許第1459563号明細書の中に開
示されている。
一方、成分(c)のバインダーとしては公知の
種々のポリマーを使用することができる。具体
的なバインダーの詳細は、米国特許第4072527
号明細書に記されている。更に英国特許第
1459563号明細書に記されている塩素化ポリオ
レフインは、特に好ましいバインダーである。
成分(a)と成分(c)は重量非で１：９から６：４
の範囲で組合せ含有される。また成分(b)は成分
(a)を基準として、0.5〜10重量％の範囲で含有
させられる。
光重合性組成物には、更に、熱重合禁止剤、
可塑剤、染料や顔料を含有させることができ
る。
これらの感光層の組成物の内、好ましいものは
(2)、(3)、(4)および(5)の組成物であり、最も好まし
くは(2)の組成物である。これらの組成物は、有機
溶剤にとかして通常用いられている塗布方法で約
0.1ｇないし５ｇ/m2程度の乾燥重量になるように
設けることができる。
本発明の特に好ましい態様においては、上記の
ような非銀感光層の上に、感光性ハロゲン化銀乳
剤層が設けられたものであり、この中に実質的に
水不溶性の固形の親油性樹脂が微細粒子状で分散
含有されている。ここで親油性樹脂とは、所定の
樹脂をある支持体の上に約２μ以上塗布したもの
を試料とし、その試料の樹脂表面の接触角θを測
定する。印刷雑誌第25号10月号（1968年）尾花光
雄著「平版におけるぬれ現象」で示唆しているよ
うに、captive bubble methodにより、24℃で試
料を水につけその表面にケロシンの微粒子（泡）
を接触させて、ゴニオメーターを用いて水中にお
けるケロシンの接触角θｏ／ｗ、試料をケロシン
につけその表面に水の微粒子（泡）を接触させ
て、同様にしてケロシン中における水の接触角θ
ｗ／ｏを測定し、θ＝−〔θｏ／ｗ−θｗ／ｏ〕
がほゞ正であるものを言う。このような実質的に
水に不溶の親油性の樹脂は、前記の非銀感光層に
用いられるバインダーの樹脂として挙げたもの、
例えば、シエラツク、ポリアミド樹脂、フエノー
ル樹脂、ポリビニルアセタール樹脂、線状ポリウ
レタン樹脂、ノボラツク型フエノール樹脂、ポリ
エステル樹脂の他、ポリビニルシンナメート系樹
脂や感光性ポリエステルなどの感光性ポリマーな
どである。これらの内、特に好ましいものは下記
の樹脂Ａ、ＢおよびＣである。
Ａ：下記一般式（）で示される単位を繰り返
し単位とする樹脂。
ここで、Ｚは水素原子、ハロゲン原子、炭素数
１ないし４のアルキル基、炭素原子数１ないし４
のアルコキシ基またはカルボキシル基を表わす。
Ｂ：多価フエノールと炭素原子数３ないし５の
ケトンとの重縮合反応で生成した樹脂。
Ｃ：下記一般式（）で示される単位を繰り返
し単位とする樹脂。
ここで、R1は水素原子、または炭素原子数１
ないし４のアルキル基、Ｘはハロゲン原子、ｎは
１または２をそれぞれ表わす。
樹脂(c)の具体例としては、ヒドロキシスチレ
ン、クロロヒドロキシスチレン、ブロモヒドロキ
シスチレン、ジブロモヒドロキシスチレン、ヒド
ロキシ−α−メチルスチレンなどのヒドロキシス
チレン類の重合体、その他のモノマーとの共重合
体及びこれらの重合体の変性物をあげることがで
きる。
前記ヒドロキシスチレン類と共重合させうるモ
ノマーとして、スチレン、無水マレイン酸、アク
リロニトリル、アクリル酸、メタクリル酸、エチ
ルアクリレート、ブチルアクリレート、メチルメ
タクリレート、ヒドロキシエチルメタクリレート
等を挙げることができる。
ヒドロキシスチレン類の重合体または共重合体
の変性物として、水酸基への、酸無水物あるいは
酸ハロゲン化物（例えば無水酢酸、プロピオニル
クロリド、ピバロイルクロリド、ベンゾイルクロ
リド等）によるエステル化変性物、エポキシ化合
物（例えばグリシジルブチルエーテル、グリシジ
ルトリルエーテル等）によるエーテル化変性物、
イソシアネート化合物（例えばフエニルイソシア
ネート、ヘキサメチレンジイソシアネート等）に
よるウレタン化変性物を挙げることができる。一
般式〔〕の単位は、少くとも50モル％含有して
いることが好しい。この重合体の平均分子量は約
５百ないし５万で好ましくは約１千ないし約２万
である。
これらのヒドロキシスチレン類の重合体は、J.
Polym.Sci.、Ａ−１、７ 2175（1969）、特開昭
50−113305号、同53−61643号、丸善石油技術報
告21 １（1976）に記載の方法あるいは類似の方
法で合成できる。また、一部のものについては市
販品を入手することができる。
樹脂(B)の具体例として次のようなフエノールケ
トン樹脂をあげることができる。
有用な多価フエノールとしてレゾルシン、カテ
コール、ピロガロールを、脂肪族ケトンとしてア
セトン、メチルエチルケトンを挙げることができ
る。
これらの重合体はInd.Eng.Chem.、52 324
（1960）や特公昭43−28403号に記載の方法または
類似の方法で合成でき、平均分子量は約５百〜約
５千である。
また、フエノール・ケトン樹脂の場合も、その
水酸基にヒドロキシスチレン類の重合体の場合と
同様な変性反応を行つた変性物も有効である。こ
の場合、変性前のフエノール・ケトン樹脂の水酸
基数の約50％が残存することが望ましい。
樹脂(A)は、例えば、ノボラツク型のフエノール
樹脂、クレゾール樹脂が含まれ、よく知られた方
法によつて合成することができる。
これらの樹脂の内でも特に樹脂Ａが好ましい。
これらの樹脂は、感光性ハロゲン化銀乳剤の中
に微細粒子として含有される。微細粒子として、
含有させるのに、例えば水に対する溶解度が10重
量％以下の有機溶剤にとかし、アニオン型界面活
性剤例えばアルキルベンゼンスルホン酸ナトリー
ム、タウリン誘導体やロート油などの助けを借り
て親水性コロイド中に分散される。用いられる親
水性コロイドは、ポリビニールピロリドン、ポリ
ビニールイミダゾール、ポリビニールアルコー
ル、ポリアクリル酸アミド、それらの共重合体、
とくに、ゼラチンまたはゼラチン誘導体例えば米
国特許第2614928号、同第2763639号、同第
3118766号、同第3132945号や特公昭39−5514号、
同42−26845号などに記載されているものであ
る。この中にトリクレジルホスフエート、ジオク
チルブチレート、ドデシルこはく酸エステルなど
高沸点可塑剤を併用できる。
親油性樹脂は、0.01μから10μの粒径で親水性
コロイド中に分散されていることが好ましい。
これらの樹脂は、感光性ハロゲン化銀乳剤中に
親水性コロイド10重量部に対して約0.1重量部な
いし約20重量部を用いることが出来る、好しくは
親水性コロイド10重量部に対して１ないし10重量
部とくに好しくは２ないし５重量部である。
感光性ハロゲン化銀乳剤は、ネガ型の通常の乳
剤、直接ポジ型の乳剤でもよい。ハロゲン化銀
は、通常用いられる塩化銀、臭化銀、よう化銀ま
たはその混合ハロゲン化銀を使用できる。その平
均粒子径は約0.01ないし径５μが好ましい。この
粒子は、適切な感度になるよう例えば硫黄増感、
還元増感、Ir、Rh、Ptなどの貴金属の塩による
増感などの化学増感、増感色素による分光増感を
ほどこすことができる。表面潜像型や内部潜像型
の潜像分布をもついずれの粒子でもよい。これに
通常用いられる添加剤を加えることができる。し
かし、感光性ハロゲン化銀乳剤層には、タンニン
グ現像主薬は含有されない。この点について、特
願昭53−59796号には感光性ハロゲン化銀乳剤層
にタンニング現像主薬を含有させておくことによ
り、この層を画像露光および現像して得られた銀
画像部は、その下に隣接して設けられた感光性樹
脂組成物層と強固に密着する旨開示されている
が、本発明においてはタンニング現像主薬を用い
ずに、単に親油性樹脂を分散含有させた感光性ハ
ロゲン化銀乳剤層を用いることにより、下層の非
銀感光層との強固な密着が計られており、この点
が本発明の特徴の１つでもある。そして、このよ
うな親油性樹脂を含有する感光性ハロゲン化銀乳
剤を前記の非銀感光層上へ直接塗布、乾燥した場
合においてもその乾燥工程で起りうるハロゲン化
銀感光層の剥離によるトラブルを回避することが
できる。
これらの感光性ハロゲン化銀乳剤層は、約１な
いし10ｇ/m2好ましくは２ないし６ｇ/m2の乾燥量
で塗布することができる。塗布はデイツプ、エア
ーナイフ、カーテンなどの塗布法また例えば米国
特許第2681294号に記載のホツパー塗布法、エク
ストルージヨン塗布法を適用できる。
また、非銀感光層の上に、次のような特別な組
成の中間層を設けてその上にハロゲン化銀乳剤を
含有する感光層を設けることもできる。特別な組
成とは下記に示すような親水性保護コロイドの中
に、前記の親油性樹脂を分散されたものである。
この中間層に用いられる親水性保護コロイド
は、ハロゲン化銀乳剤に用いる親水性高分子化合
物が用いられる。ゼラチン、ゼラチン誘導体その
他の高分子とのグラフトポリマー、カゼイン、ア
ルブミンなどの蛋白質、ヒドロキシエチルセルロ
ーズ、カルボキシメチルセルローズなどのセルロ
ーズ誘導体、アルギン酸ナトリウム、澱粉誘導
体、ポリビニールアルコール部分アセタール化
物、ポリ−Ｎ−ビニールピロリドン、ポリアクリ
ル酸、ポリアクリルアミド、ポリビニールイミダ
ゾール、ポリビニールピラゾールなどのホモある
いはコポリマーなどを用いることができる。ゼラ
チン誘導体には、例えば米国特許第2614928号、
同2763639号、同3132945号、同3118766号、同
3186846号、同3312553号、特公昭39−5514号、同
42−26845号などに記載されたイソシアネート、
酸ハライド、酸無水物、アクリロニトリルエポキ
シ化合物、ビニルスルホンアミドなどの反応物、
例えば米国特許第2763625号、同2831767号、同
2956884号などのゼラチン、グラフトポリマーな
どである。
かかる親水性保護コロイドよりなる層には、前
記の感光層ハロゲン化銀乳剤層を非銀感光層の上
に直接設けた場合と同様に、親油性樹脂を親水性
保護コロイド10重量部に対して、好しくは0.1な
いし20重量部を用いることができる。これによつ
て非銀感光層の上に中間層を均一に塗布すること
もできその上に感光性ハロゲン化銀乳剤層を設け
ることができる。これにより、耐刷性、感脂性を
劣化させることなしに良好な印刷物を与える平版
印刷版をうることができる。この場合、感光性ハ
ロゲン化銀乳剤層には親油性樹脂を含有させなく
てもよい。
本発明による感光性平版印刷版を用いて平版印
刷版を作る方法及び処理は次のようである。先づ
像露光し、ハロゲン化銀を含有する感光層中のハ
ロゲン化銀に潜像を形成せしめる。次にハロゲン
化銀の現像（第１現像）を行い、直ちにまたは定
着液で処理するかの何れかの工程を経て紫外線を
含む活性光線に曝光させ、次いで第２現像に送ら
れ非銀感光層の、非画線部のみ溶解除去して支持
体の親水性表面を露出させ刷版をうる工程であ
る。この場合第２現像に使用される処理液は非銀
感光層の非画線部のみ撰択的に溶解するような処
理液が必要で、とくに通常PS版の現像に用いら
れている現像液またはそれに類似の現像液の中か
ら撰ぶことができる。例えば、非銀感光層がｏ−
キノンジアジド化合物からなる層である場合に
は、珪酸ナトリウムの水溶液や、米国特許第
4141733号に記されているような現像液が使用さ
れる。
また、別法として、前記の如く紫外線に曝光さ
せたのち全面または非画線部のみ第１層の上にあ
る感光性ハロゲン化銀乳剤層を洗い出す工程を入
れることができる、次に第２現像液に接しさせて
非画線部のみ撰択的に溶解除去する工程である。
本発明において親油性樹脂を含まない感光性ハ
ロゲン化銀乳剤層を用いた場合には、かゝる処理
工程でキズがつきやすい欠陥をもつている。
以下実施例によつて本発明の内容を具体的に説
明する。なお％は重量％を示す。
実施例 １
特開昭48−33911号の方法により機械的な砂目
立てされた2S材アルミニウム板を40℃に保たれ
た２％の水酸化ナトリウム水溶液に１分間浸漬し
表面の一部を腐蝕した。水洗後、硫酸−クロム酸
溶液に約１分間浸漬して純アルミニウムの表面を
露呈した。30℃に保たれた20％硫酸に浸漬し、直
流電圧1.5V、電流密度３A/dm2の条件下で２分間
陽極酸化処理を行つた後、水洗、乾燥した。次に
下記組成の感光液を乾燥重量が２ｇ/m2位になる
ようロールコーターを用いて連続的に塗布し、非
銀感光層を設けた。
アセトン−ピロガロール樹脂のナフトキノン−
１・２−ジアジド(2)−５−スルホン酸エステル
（合成法は米国特許第3635709号明細書実施例１の
方法による） 2.5ｇ
ヒタノール＃3110（日立化成工業(株)製クレゾール
−ホルムアルデヒド樹脂） 5.0ｇ
メチルエチルケトン 75ｇ
シクロヘキサノン 60ｇ
次に、下記組成の感光液を乾燥重量が4.5ｇ/m2
位になるように連続塗布し最終温度が110℃の熱
風で乾燥した。この試料をNo.1とする。
フエノールホルムアルデヒド樹脂MP120HH
（群栄化学工業(株)製）の45ｇを酢酸エチル330ｇと
メチルエチルケトン120ｇとの混液にとかしゼラ
チン10％、水溶液600ml中に、
ノニールベンゼンスルホン酸ナトリウム10％溶液
を60mlとロート油の10％メタノール溶液の150ml
を混えた溶液に分散した乳化物 ………1300ｇ
塩臭化銀ゼラチン乳剤（Cl-70モル％、Br-30モ
ル％の塩臭化銀、平均粒子径 ………0.28μ
乳剤１Kg当りゼラチン55ｇ、ハロゲン化銀0.85モ
ル含有） ………2000ｇ
１・３−ジエチル−５−〔２−｛３−（３−スルホ
プロピル）ベンズオキサゾール−２−イリデン｝
エチリデン〕チオヒダントインナトリウム塩の
0.1％メタノール溶液 ………100ml
４−ヒドロキシ−６−メチル−１・３・3a・７−
テトラザインデンの0.5％アルカリ水溶液
………200ml
２・４−ジクロロ−６−ヒドロキシ−ｓ−トリア
ジンの２％水溶液 ………70ml
他方、フエノールホルムアルデヒド樹脂の分散
物を含まない他は、前記の組成と同じ処方の感光
液を、ハロゲン化銀の塗布量が実質的に同じよう
になるように塗布し最終温度が90℃の熱風で乾燥
した。しかし、本発明による試料No.1が均一に
むらなく塗布されたのに、比較のためのこの塗布
では乾燥温度を低くしたのにも拘らず、ハロゲン
化銀を含有する感光層は膜はがれを部分的におこ
し均一な塗布された試料がえられなかつた。この
試料ａとする。
試料No.1及び試料ａを室温に一週間放置した
のち次のように製版した。約1/5に縮合されて、
文字画線を撮影されてえた透明ネガフイルムを、
300ルツクスの光源をもつ引伸し機を用いて、５
倍拡大で10秒試料１及びａに露光した。次に自現
機を用いて次の処理を施した。下記の組成の現像
液（）を32℃で20秒間とおし、下記の定着液
（）を20℃で10秒間とおした。続いてレフレク
ター型水銀灯３ケからなる紫外線曝光部を15秒間
かけてとおし、洗い出し部で40〜45℃の温湯につ
けてブラシでこすり、スクイズローラーを経て、
下記の組成の現像液（）で30℃で30秒間とお
し、富士写真フイルム(株)製ガムコーター800Gを
用い、GP−１を塗り刷版をえた。
現像液（）の組成
水 ………700ml
メトール ………3.0ｇ
亜硫酸ナトリウム ………45.0ｇ
ハイドロキノン ………12.0ｇ
炭酸ナトリウム（１水塩） ………80.0ｇ
臭化カリウム ………２ｇ
水を加えて １とする
この原液を水で（１：２）に希釈して用いる。
現像液（）
JIS1号珪酸ナトリウム ………100ｇ
メタ珪酸ナトリウム ………50ｇ
純 水 ………1800ml
定着液（）
水 ………700ml
チオ硫酸アンモニウム ………224ｇ
亜硫酸ナトリウム ………20ｇ
水を加えて 1000mlとする
ハイデルKOR印刷機を用いて印刷し試料No.1
は刷り出し枚数５枚で良好な印刷物を約11万部え
た。試料ａは、スリキズによる画線の欠損が多か
つた。また、生の試料ａの裁断のときに生ずる淵
カブリによる汚れがでた。
実施例 ２
特開昭48−33911号公報に記されている方法に
より機械的に砂目立てされた2S材アルミニウム
板を40℃に保たれた２％の水酸化ナトリウム水溶
液に１分間浸漬して表面を一部腐蝕した。水洗
後、硫酸−クロム酸混液に約１分間浸漬して純ア
ルミニウムの表面を露呈した後、30℃に保たれた
20％硫酸溶液に浸漬し、直流電圧15V電流密度３
A/dm2の条件下で２分間陽極酸化処理を行つた。
水洗後、50℃、10％燐酸溶液に30秒間浸漬した
後、再度水洗し、次に70℃の２％珪酸ナトリウム
（JIS3号規格品）溶液に２分間浸漬し、水洗、加
熱乾燥した。乾燥後、室温まで冷却したアルミニ
ウム板に下記組成の下塗液をロールコーターを用
いて塗布した。
ポリビニルピロリドンＫ−90（Badische Anilin
and soda Fabrik社製品） 2.5ｇ
メチルアルコール 1000ml
塗布後100℃で２分間乾燥し、引続いて次の組
成の感光液を塗布し、非銀感光層を設けた。
ｐ−フエニレンジエトキシアクリレートと等モル
の１・４−β−ヒドロキシエトキシクロヘキサン
との縮合で作られたポリエステル 115ｇ
２−ベンゾイルメチレン−３−メチル−β−ナフ
トチアゾリン 5.7ｇ
ジヘプチルフタレート 48ｇ
４・4′−チオビス（３−メチル−６−ターシヤリ
−ブチルフエノール） 2.5ｇ
フタロシアニンブルー（C.I.Pigment Blue＃15）
25ｇ
モノクロルベンゼン 1880ｇ
エチレンジクロライド 1220ｇ
乾燥は100℃、２分間行つた。乾燥後の塗布重
量は1.2ｇ/m2であつた。
次に実施例１で示した組成の中、フエノールホ
ルムアルデヒド樹脂の45ｇに替えるに、当該樹脂
60ｇを用いた他は実施例１で示したと同じ組成の
感光液を乾燥重量が4.0ｇ/m2になるように塗布
し、最終温度が90℃の熱風で乾燥した。この試料
をNo.2とする。
試料No.2を室温に10日間放置したのち、約1/4
に縮小されて、文字を撮影されている透明ポジフ
イルムを300ルツクスの光源をもつ引伸し機を用
いて４倍拡大で露光し以下実施例１に準じて製版
した。但し用いた第２現像液は現像液（）に替
つて、90％乳酸水溶液を用いた。30秒間現像して
GP−１を塗布して刷版をえた。
ローランドの印刷機を用いて印刷し、上質紙で
１万枚の印刷物をえた。印刷インキの付き方、非
画像部の水上がりの状態、文字画線の調子再現性
とも良好であつた。Those whose main component is a photosensitive polymer such as polyesters, polyamides, and polycarbonates containing [Formula] (for example, U.S. Patent No.
3030208, 3707373 and 3453237); derived from (2-properidene) malonic acid compounds such as cinnamylidene malonic acid and difunctional glycols; Polyvinyl alcohol, starch, cellulose, and similar materials; Cinnamate esters of hydroxyl-containing polymers such as
2752372, 2732301, etc.). These compositions may also contain sensitizers, stabilizers, plasticizers, pigments, dyes, and the like. (5) Photopolymerizable composition comprising an addition polymerizable unsaturated compound This composition preferably comprises (a) at least 2
It consists of a vinyl monomer having five terminal vinyl groups, (b) a photopolymerization initiator, and (c) a polymer compound as a binder. As the vinyl monomer of component (a),
No. 5093, Special Publication No. 14719, Special Publication No. 1971-28727
Acrylic or methacrylic esters of polyols, such as diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, pentaerythritol tri(meth)acrylate, trimethylolpropane tri(meth)acrylate, etc. ) acrylates, etc., or bis(meth)acrylamides such as methylene bis(meth)acrylamide and ethylene bis(meth)acrylamide, or unsaturated monomers containing urethane groups, such as di-(2'-methacryloxyethyl) -2,4-tolylene diurethane, di-
Examples include reaction products of diol mono(meth)acrylates and diisocyanates, such as (2'-acryloxyethyl)trimethylene diurethane. As the photopolymerization initiator for component (b), for example, J.
Examples include carbonyl compounds, organic sulfur compounds, persulfides, redox compounds, azo and diazo compounds, halogen compounds, photoreducible dyes, etc., as described in Chapter 5 of "Light Sensitive Systems" by Kosar. More specifically, it is disclosed in British Patent No. 1459563. On the other hand, various known polymers can be used as the binder for component (c). Specific binder details can be found in U.S. Patent No. 4,072,527
It is stated in the specification of the No. Furthermore, British patent no.
The chlorinated polyolefins described in US Pat. No. 1,459,563 are particularly preferred binders. Component (a) and component (c) are 1:9 to 6:4 by weight.
Contained in combination within the range. In addition, component (b) is the component
It is contained in a range of 0.5 to 10% by weight based on (a). The photopolymerizable composition further includes a thermal polymerization inhibitor,
It can contain plasticizers, dyes and pigments. Among these photosensitive layer compositions, preferred are
Compositions (2), (3), (4) and (5) are preferred, and composition (2) is most preferred. These compositions can be dissolved in organic solvents and applied by conventional application methods.
It can be provided to have a dry weight of about 0.1 g to 5 g/m 2 . In a particularly preferred embodiment of the present invention, a photosensitive silver halide emulsion layer is provided on the non-silver photosensitive layer as described above, in which a substantially water-insoluble solid lipophilic resin is provided. is contained dispersed in the form of fine particles. Here, the lipophilic resin refers to a sample obtained by coating a predetermined resin on a support of approximately 2 μm or more, and measuring the contact angle θ of the resin surface of the sample. As suggested in Mitsuo Obana's ``Wetting Phenomenon in Lithography'' in Print Magazine No. 25, October issue (1968), using the captive bubble method, a sample is immersed in water at 24°C and kerosene particles (bubbles) are formed on its surface.
The contact angle of kerosene in water, θo/w, is measured using a goniometer.The contact angle of water in kerosene, θo/w, is determined by dipping the sample into kerosene and bringing water particles (bubbles) into contact with its surface.
Measure w/o, θ=-[θo/w-θw/o]
Say something that is almost true. Such lipophilic resins that are substantially insoluble in water include those mentioned above as binder resins used in the non-silver photosensitive layer;
Examples include photosensitive polymers such as silicone resin, polyamide resin, phenolic resin, polyvinyl acetal resin, linear polyurethane resin, novolak type phenolic resin, polyester resin, and polyvinyl cinnamate resin and photosensitive polyester. Among these, particularly preferred are the following resins A, B and C. A: A resin whose repeating units are units represented by the following general formula (). Here, Z is a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms, or a C 1 to 4 alkyl group.
represents an alkoxy group or carboxyl group. B: A resin produced by a polycondensation reaction between a polyhydric phenol and a ketone having 3 to 5 carbon atoms. C: A resin whose repeating units are units represented by the following general formula (). Here, R 1 is a hydrogen atom or has 1 carbon atom
to 4 alkyl groups, X represents a halogen atom, and n represents 1 or 2, respectively. Specific examples of the resin (c) include polymers of hydroxystyrenes such as hydroxystyrene, chlorohydroxystyrene, bromohydroxystyrene, dibromohydroxystyrene, and hydroxy-α-methylstyrene, copolymers with other monomers, and copolymers of these. Examples include modified polymers of Examples of monomers that can be copolymerized with the hydroxystyrenes include styrene, maleic anhydride, acrylonitrile, acrylic acid, methacrylic acid, ethyl acrylate, butyl acrylate, methyl methacrylate, and hydroxyethyl methacrylate. Modified products of hydroxystyrene polymers or copolymers include esterification products of hydroxyl groups with acid anhydrides or acid halides (e.g. acetic anhydride, propionyl chloride, pivaloyl chloride, benzoyl chloride, etc.), epoxy etherified modified products with compounds (e.g. glycidyl butyl ether, glycidyl tolyl ether, etc.);
Examples include urethane-modified products using isocyanate compounds (eg, phenyl isocyanate, hexamethylene diisocyanate, etc.). It is preferable that the unit of general formula [] is contained in an amount of at least 50 mol%. The average molecular weight of this polymer is about 500 to 50,000, preferably about 1,000 to about 20,000. These hydroxystyrene polymers were developed by J.
Polym.Sci., A-1, 7 2175 (1969), JP-A-Sho
It can be synthesized by the method described in No. 50-113305, No. 53-61643, Maruzen Sekiyu Technical Report 21 1 (1976) or a similar method. In addition, some of them are commercially available. Specific examples of resin (B) include the following phenol ketone resins. Useful polyhydric phenols include resorcinol, catechol, and pyrogallol, and useful aliphatic ketones include acetone and methyl ethyl ketone. These polymers are Ind.Eng.Chem., 52 324
(1960), Japanese Patent Publication No. 43-28403, or a similar method, and has an average molecular weight of about 500 to about 5,000. Also, in the case of phenol-ketone resins, modified products in which the hydroxyl groups are subjected to the same modification reaction as in the case of hydroxystyrene polymers are also effective. In this case, it is desirable that about 50% of the number of hydroxyl groups in the phenol-ketone resin before modification remain. The resin (A) includes, for example, novolak type phenolic resin and cresol resin, and can be synthesized by a well-known method. Among these resins, resin A is particularly preferred. These resins are contained in the photosensitive silver halide emulsion as fine particles. As fine particles,
For example, it is dissolved in an organic solvent with a water solubility of 10% by weight or less, and dispersed in a hydrophilic colloid with the help of anionic surfactants such as sodium alkylbenzenesulfonate, taurine derivatives, funnel oil, etc. . The hydrophilic colloids used are polyvinyl pyrrolidone, polyvinyl imidazole, polyvinyl alcohol, polyacrylic acid amide, copolymers thereof,
In particular, gelatin or gelatin derivatives such as U.S. Pat.
No. 3118766, No. 3132945 and Special Publication No. 39-5514,
This is described in No. 42-26845, etc. High boiling point plasticizers such as tricresyl phosphate, dioctyl butyrate, and dodecyl succinate can be used in combination. Preferably, the lipophilic resin is dispersed in the hydrophilic colloid with a particle size of 0.01μ to 10μ. These resins can be used in the photosensitive silver halide emulsion in an amount of about 0.1 to about 20 parts by weight per 10 parts by weight of the hydrophilic colloid, preferably 1 part by weight per 10 parts by weight of the hydrophilic colloid. The amount is preferably from 2 to 10 parts by weight, particularly preferably from 2 to 5 parts by weight. The light-sensitive silver halide emulsion may be a normal negative-working emulsion or a direct positive-working emulsion. As the silver halide, commonly used silver chloride, silver bromide, silver iodide, or mixed silver halide thereof can be used. The average particle size is preferably about 0.01 to 5μ. The particles may be sensitized by e.g. sulfur to achieve appropriate sensitivity.
Chemical sensitization such as reduction sensitization, sensitization with salts of noble metals such as Ir, Rh, and Pt, and spectral sensitization using sensitizing dyes can be performed. Any particle having a surface latent image type or internal latent image type latent image distribution may be used. Commonly used additives can be added to this. However, the photosensitive silver halide emulsion layer does not contain a tanning developing agent. Regarding this point, Japanese Patent Application No. 53-59796 discloses that by incorporating a tanning developing agent in the photosensitive silver halide emulsion layer, the silver image area obtained by imagewise exposure and development of this layer is Although it is disclosed that the photosensitive resin composition layer adheres firmly to the photosensitive resin composition layer provided adjacently below, in the present invention, the photosensitive halogen is simply dispersed with a lipophilic resin without using a tanning developing agent. By using the silver oxide emulsion layer, strong adhesion with the underlying non-silver photosensitive layer is achieved, and this point is also one of the features of the present invention. Even when a photosensitive silver halide emulsion containing such a lipophilic resin is directly coated onto the non-silver photosensitive layer and dried, troubles due to peeling of the silver halide photosensitive layer that may occur during the drying process can be avoided. can be avoided. These light-sensitive silver halide emulsion layers can be coated in a dry weight of about 1 to 10 g/m 2 , preferably 2 to 6 g/m 2 . For coating, dip, air knife, curtain, or other coating methods can be used, as well as the hopper coating method and extrusion coating method described in US Pat. No. 2,681,294. Further, it is also possible to provide an intermediate layer having the following special composition on the non-silver photosensitive layer, and provide a photosensitive layer containing a silver halide emulsion thereon. The special composition is one in which the above lipophilic resin is dispersed in a hydrophilic protective colloid as shown below. The hydrophilic protective colloid used in this intermediate layer is a hydrophilic polymer compound used in silver halide emulsions. Gelatin, graft polymers with gelatin derivatives and other polymers, proteins such as casein and albumin, cellulose derivatives such as hydroxyethyl cellulose and carboxymethyl cellulose, sodium alginate, starch derivatives, partially acetalized polyvinyl alcohol, poly-N-vinyl Homo or copolymers such as pyrrolidone, polyacrylic acid, polyacrylamide, polyvinyl imidazole, and polyvinyl pyrazole can be used. Gelatin derivatives include, for example, US Pat. No. 2,614,928;
Same No. 2763639, No. 3132945, No. 3118766, Same No.
No. 3186846, No. 3312553, Special Publication No. 39-5514, No.
Isocyanates described in No. 42-26845, etc.
Reactants such as acid halides, acid anhydrides, acrylonitrile epoxy compounds, vinyl sulfonamides,
For example, US Patent No. 2763625, US Patent No. 2831767, US Patent No.
Gelatin such as No. 2956884, graft polymer, etc. In the layer made of such a hydrophilic protective colloid, a lipophilic resin is added to 10 parts by weight of the hydrophilic protective colloid, as in the case where the silver halide emulsion layer of the photosensitive layer is provided directly on the non-silver photosensitive layer. , preferably 0.1 to 20 parts by weight. This allows an intermediate layer to be uniformly coated on the non-silver photosensitive layer and a photosensitive silver halide emulsion layer to be provided thereon. Thereby, a lithographic printing plate that gives good printed matter without deteriorating printing durability or oil sensitivity can be obtained. In this case, the photosensitive silver halide emulsion layer does not need to contain a lipophilic resin. The method and process for making a lithographic printing plate using the photosensitive lithographic printing plate according to the present invention are as follows. First, it is imagewise exposed to form a latent image on the silver halide in the photosensitive layer containing silver halide. Next, the silver halide is developed (first development), and exposed to actinic light including ultraviolet rays either immediately or after treatment with a fixer, and then sent to second development to form a non-silver photosensitive layer. In this step, only the non-image areas are dissolved and removed to expose the hydrophilic surface of the support to obtain a printing plate. In this case, the processing solution used for the second development must be one that selectively dissolves only the non-image areas of the non-silver photosensitive layer, especially the developer normally used for developing PS plates or You can choose from similar developers. For example, if the non-silver photosensitive layer is o-
In the case of a layer consisting of a quinonediazide compound, an aqueous solution of sodium silicate or US Pat.
A developer such as that described in No. 4141733 is used. As another method, after exposure to ultraviolet rays as described above, a step of washing out the photosensitive silver halide emulsion layer on the first layer on the entire surface or only on the non-image area can be added, and then a second development step can be carried out. This is a process of selectively dissolving and removing only the non-image areas by bringing them into contact with a liquid. When a photosensitive silver halide emulsion layer containing no oleophilic resin is used in the present invention, it has defects that are easily scratched during such processing steps. The content of the present invention will be specifically explained below using Examples. Note that % indicates weight %. Example 1 A 2S aluminum plate mechanically grained by the method of JP-A-48-33911 was immersed in a 2% sodium hydroxide aqueous solution kept at 40°C for 1 minute to corrode a part of the surface. . After washing with water, it was immersed in a sulfuric acid-chromic acid solution for about 1 minute to expose the pure aluminum surface. It was immersed in 20% sulfuric acid kept at 30°C, anodized for 2 minutes at a DC voltage of 1.5V and a current density of 3A/dm 2 , then washed with water and dried. Next, a photosensitive solution having the following composition was continuously coated using a roll coater so that the dry weight was about 2 g/m 2 to provide a non-silver photosensitive layer. Acetone - naphthoquinone of pyrogallol resin -
1,2-diazide(2)-5-sulfonic acid ester (synthesized according to the method described in Example 1 of US Pat. No. 3,635,709) 2.5 g Hytanol #3110 (cresol-formaldehyde resin manufactured by Hitachi Chemical Co., Ltd.) 5.0g Methyl ethyl ketone 75g Cyclohexanone 60g Next, add a photosensitive solution with the following composition to a dry weight of 4.5g/m 2
It was applied continuously so that the final temperature was 110°C and dried with hot air. Let this sample be No.1. Phenol formaldehyde resin MP120HH
(manufactured by Gunei Chemical Industry Co., Ltd.) was dissolved in a mixture of 330 g of ethyl acetate and 120 g of methyl ethyl ketone, 10% gelatin, and 600 ml of an aqueous solution, 60 ml of a 10% solution of sodium nonylbenzenesulfonate and 10% funnel oil. 150ml of methanol solution
Emulsion dispersed in a solution mixed with......1300g Silver chlorobromide gelatin emulsion (Cl - 70 mol%, Br - 30 mol% silver chlorobromide, average particle size......0.28 μ Gelatin 55 g per 1 kg of emulsion , containing 0.85 mol of silver halide) ......2000g 1,3-diethyl-5-[2-{3-(3-sulfopropyl)benzoxazol-2-ylidene}
ethylidene] thiohydantoin sodium salt
0.1% methanol solution ……100ml 4-hydroxy-6-methyl-1,3,3a,7-
0.5% alkaline aqueous solution of tetrazaindene
......200 ml 2% aqueous solution of 2,4-dichloro-6-hydroxy-s-triazine ......70 ml On the other hand, a photosensitive liquid having the same composition as above except that it does not contain the phenol formaldehyde resin dispersion, The coatings were coated so that the amount of silver halide coated was substantially the same, and dried with hot air at a final temperature of 90°C. However, while sample No. 1 according to the present invention was coated uniformly and evenly, in this comparative coating, the photosensitive layer containing silver halide did not peel off despite the lower drying temperature. A uniformly coated sample could not be obtained due to partial agitation. Let this be sample a. Sample No. 1 and sample a were left at room temperature for one week and then plate-made as follows. It is condensed to about 1/5,
Transparent negative film with character lines photographed,
Using an enlarger with a 300 lux light source,
Samples 1 and a were exposed for 10 seconds at double magnification. Next, the following processing was performed using an automatic developing machine. A developer solution () having the composition shown below was run at 32°C for 20 seconds, and a fixer solution () shown below was run at 20°C for 10 seconds. Next, it is passed through an ultraviolet exposure section consisting of three reflector-type mercury lamps for 15 seconds, and at the washing section, it is soaked in warm water of 40 to 45 degrees Celsius, rubbed with a brush, and passed through a squeeze roller.
A printing plate was prepared by applying GP-1 using a Gum Coater 800G manufactured by Fuji Photo Film Co., Ltd., for 30 seconds at 30°C with a developer having the composition shown below. Composition of developer () Water: 700ml Metol: 3.0g Sodium sulfite: 45.0g Hydroquinone: 12.0g Sodium carbonate (monohydrate): 80.0g Potassium bromide: 2g Water Add to make 1. Use this stock solution by diluting it with water (1:2). Developer solution () JIS No. 1 Sodium silicate 100g Sodium metasilicate 50g Pure water 1800ml Fixer () Water 700ml Ammonium thiosulfate 224g Sodium sulfite 20g Add water Print sample No. 1 using Heidel KOR printing machine to make 1000ml.
produced approximately 110,000 copies of prints in good condition with 5 prints. Sample a had many line defects due to scratches. In addition, stains appeared due to edge fog that occurred when cutting the raw sample a. Example 2 A 2S aluminum plate mechanically grained by the method described in JP-A No. 48-33911 was immersed in a 2% sodium hydroxide aqueous solution kept at 40°C for 1 minute. Part of it was corroded. After washing with water, it was immersed in a sulfuric acid-chromic acid mixture for about 1 minute to expose the pure aluminum surface, and then kept at 30℃.
Immersed in 20% sulfuric acid solution, DC voltage 15V current density 3
Anodic oxidation treatment was performed for 2 minutes under A/dm 2 conditions.
After washing with water, it was immersed in a 10% phosphoric acid solution at 50°C for 30 seconds, washed again with water, then immersed in a 2% sodium silicate (JIS No. 3 standard product) solution at 70°C for 2 minutes, washed with water, and dried by heating. After drying, an undercoating liquid having the following composition was applied to the aluminum plate cooled to room temperature using a roll coater. Polyvinylpyrrolidone K-90 (Badische Anilin
and soda Fabrik product) 2.5g Methyl alcohol 1000ml After coating, it was dried at 100°C for 2 minutes, and then a photosensitive solution having the following composition was applied to form a non-silver photosensitive layer. Polyester made by condensation of p-phenylene diethoxy acrylate and equimolar amounts of 1,4-β-hydroxyethoxychlorohexane 115 g 2-benzoylmethylene-3-methyl-β-naphthothiazoline 5.7 g Diheptyl phthalate 48 g 4. 4'-thiobis(3-methyl-6-tert-butylphenol) 2.5g Phthalocyanine Blue (CIPigment Blue#15)
25g Monochlorobenzene 1880g Ethylene dichloride 1220g Drying was performed at 100°C for 2 minutes. The coating weight after drying was 1.2 g/m 2 . Next, in the composition shown in Example 1, in place of 45g of phenol formaldehyde resin, the resin
A photosensitive solution having the same composition as in Example 1 except that 60 g was used was applied to give a dry weight of 4.0 g/m 2 and dried with hot air at a final temperature of 90°C. Let this sample be No. 2. After leaving sample No. 2 at room temperature for 10 days, approximately 1/4
A transparent positive film on which characters had been photographed was exposed at 4 times magnification using an enlarger equipped with a 300 lux light source, and a plate was made in accordance with Example 1. However, the second developer used was a 90% lactic acid aqueous solution instead of the developer (). Develop for 30 seconds
A printing plate was obtained by applying GP-1. It was printed using a Roland printing press and produced 10,000 prints on high-quality paper. The adhesion of printing ink, the water leveling of non-image areas, and the tone reproducibility of character lines were all good.
Claims (1)
性画像を形成し得る非銀感光層および感光性ハロ
ゲン化銀乳剤層を有する感光性平版印刷版におい
て、該感光性ハロゲン化銀乳剤層はタンニング現
像主薬を含まず、且つ該非銀感光層上に隣接して
設けられた親水性コロイド層が実質的に水不溶性
の固形の親油性樹脂を微細粒子状で分散含有して
いることを特徴とする感光性平版印刷版。 ２ 該親水性コロイド層が該感光性ハロゲン化銀
乳剤層であることを特徴とする特許請求の範囲第
１項記載の感光性平版印刷版。 ３ 該親油性樹脂は、下記の樹脂Ａ、ＢおよびＣ
から選ばれた少くとも１つであり、0.01〜10μの
粒径で分散されており、且つ該親水性コロイド10
重量部に対して0.1〜20重量部の範囲で含有され
ていることを特徴とする特許請求の範囲第１項ま
たは第２項記載の感光性平版印刷版。 Ａ：下記一般式（）で示される単位を繰り返
し単位とする樹脂 ここで、Ｚは水素原子、ハロゲン原子、炭素数
１ないし４のアルキル基、炭素原子数１ないし４
のアルコキシ基またはカルボキシル基を表わす。 Ｂ：多価フエノールと炭素原子数３ないし５の
ケトンとの重縮合反応で生成した樹脂。 Ｃ：下記一般式（）で示される単位を繰り返
し単位とする樹脂、 ここで、R1は水素原子、または炭素原子数１
ないし４のアルキル基、Ｘはハロゲン原子、ｎは
１または２をそれぞれ表わす。[Scope of Claims] 1. A photosensitive lithographic printing plate comprising, in order, a non-silver photosensitive layer capable of forming a lipophilic image and a photosensitive silver halide emulsion layer on a support having a hydrophilic surface. The silver halide emulsion layer does not contain a tanning developing agent, and the hydrophilic colloid layer provided adjacent to the non-silver photosensitive layer contains a substantially water-insoluble solid lipophilic resin dispersed in the form of fine particles. A photosensitive lithographic printing plate characterized by: 2. The photosensitive lithographic printing plate according to claim 1, wherein the hydrophilic colloid layer is the photosensitive silver halide emulsion layer. 3 The lipophilic resin is the following resin A, B and C.
at least one hydrophilic colloid selected from
The photosensitive lithographic printing plate according to claim 1 or 2, wherein the content is in the range of 0.1 to 20 parts by weight. A: Resin whose repeating units are units represented by the following general formula () Here, Z is a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms, or a C 1 to 4 alkyl group.
represents an alkoxy group or carboxyl group. B: A resin produced by a polycondensation reaction between a polyhydric phenol and a ketone having 3 to 5 carbon atoms. C: a resin whose repeating unit is a unit represented by the following general formula (), Here, R 1 is a hydrogen atom or has 1 carbon atom
to 4 alkyl groups, X represents a halogen atom, and n represents 1 or 2, respectively.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7425879A JPS55166645A (en) | 1979-06-13 | 1979-06-13 | Photosensitive lithographic plate |
| GB8019106A GB2052084B (en) | 1979-06-13 | 1980-06-11 | Process for preparing photosensitive lithographic printing plate precursor |
| DE19803022254 DE3022254C2 (en) | 1979-06-13 | 1980-06-13 | Process for making photosensitive lithographic printing plates |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7425879A JPS55166645A (en) | 1979-06-13 | 1979-06-13 | Photosensitive lithographic plate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS55166645A JPS55166645A (en) | 1980-12-25 |
| JPS6155666B2 true JPS6155666B2 (en) | 1986-11-28 |
Family
ID=13541934
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7425879A Granted JPS55166645A (en) | 1979-06-13 | 1979-06-13 | Photosensitive lithographic plate |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS55166645A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62196978U (en) * | 1986-06-04 | 1987-12-15 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS513241A (en) * | 1974-05-28 | 1976-01-12 | Xerox Corp | |
| JPS54152502A (en) * | 1978-05-19 | 1979-11-30 | Fuji Photo Film Co Ltd | Photosensitive printing plate material and method of making printing plate from said material |
-
1979
- 1979-06-13 JP JP7425879A patent/JPS55166645A/en active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS513241A (en) * | 1974-05-28 | 1976-01-12 | Xerox Corp | |
| JPS54152502A (en) * | 1978-05-19 | 1979-11-30 | Fuji Photo Film Co Ltd | Photosensitive printing plate material and method of making printing plate from said material |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62196978U (en) * | 1986-06-04 | 1987-12-15 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS55166645A (en) | 1980-12-25 |
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