JPH0322617B2 - - Google Patents
Info
- Publication number
- JPH0322617B2 JPH0322617B2 JP59172958A JP17295884A JPH0322617B2 JP H0322617 B2 JPH0322617 B2 JP H0322617B2 JP 59172958 A JP59172958 A JP 59172958A JP 17295884 A JP17295884 A JP 17295884A JP H0322617 B2 JPH0322617 B2 JP H0322617B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- weight
- photosensitive
- diazo resin
- printing plate
- 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
Links
- 229920005989 resin Polymers 0.000 claims description 25
- 239000011347 resin Substances 0.000 claims description 25
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 23
- -1 heterocyclic carboxylic acid Chemical class 0.000 claims description 20
- 229910052782 aluminium Inorganic materials 0.000 claims description 15
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 9
- 239000003960 organic solvent Substances 0.000 claims description 6
- 229920000620 organic polymer Polymers 0.000 claims description 5
- WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 claims description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 15
- 239000002253 acid Substances 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 10
- 229920001577 copolymer Polymers 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 239000000975 dye Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 7
- 229940044192 2-hydroxyethyl methacrylate Drugs 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- 230000018109 developmental process Effects 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- KSOWMDCLEHRQPH-UHFFFAOYSA-N 4-diazocyclohexa-1,5-dien-1-amine Chemical compound NC1=CCC(=[N+]=[N-])C=C1 KSOWMDCLEHRQPH-UHFFFAOYSA-N 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000010306 acid treatment Methods 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 229940081066 picolinic acid Drugs 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 3
- 239000004677 Nylon Substances 0.000 description 3
- 239000004115 Sodium Silicate Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 239000003945 anionic surfactant Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000002131 composite material Substances 0.000 description 3
- 239000012954 diazonium Substances 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- 229920001778 nylon Polymers 0.000 description 3
- 235000006408 oxalic acid Nutrition 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 229920000193 polymethacrylate Polymers 0.000 description 3
- 239000008262 pumice Substances 0.000 description 3
- GJAWHXHKYYXBSV-UHFFFAOYSA-N quinolinic acid Chemical compound OC(=O)C1=CC=CN=C1C(O)=O GJAWHXHKYYXBSV-UHFFFAOYSA-N 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 3
- 229910052911 sodium silicate Inorganic materials 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000010186 staining Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- CXVGEDCSTKKODG-UHFFFAOYSA-N sulisobenzone Chemical compound C1=C(S(O)(=O)=O)C(OC)=CC(O)=C1C(=O)C1=CC=CC=C1 CXVGEDCSTKKODG-UHFFFAOYSA-N 0.000 description 3
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 2
- 229930040373 Paraformaldehyde Natural products 0.000 description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 2
- 239000004111 Potassium silicate Substances 0.000 description 2
- 229920002125 Sokalan® Polymers 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- 238000005299 abrasion Methods 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
- 239000004327 boric acid Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- XTEGVFVZDVNBPF-UHFFFAOYSA-N naphthalene-1,5-disulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 229920002866 paraformaldehyde Polymers 0.000 description 2
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 2
- 239000004584 polyacrylic acid Substances 0.000 description 2
- NNHHDJVEYQHLHG-UHFFFAOYSA-N potassium silicate Chemical compound [K+].[K+].[O-][Si]([O-])=O NNHHDJVEYQHLHG-UHFFFAOYSA-N 0.000 description 2
- 229910052913 potassium silicate Inorganic materials 0.000 description 2
- 235000019353 potassium silicate Nutrition 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 235000010265 sodium sulphite Nutrition 0.000 description 2
- FGDMJJQHQDFUCP-UHFFFAOYSA-M sodium;2-propan-2-ylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=CC2=C(S([O-])(=O)=O)C(C(C)C)=CC=C21 FGDMJJQHQDFUCP-UHFFFAOYSA-M 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 2
- ROVRRJSRRSGUOL-UHFFFAOYSA-N victoria blue bo Chemical compound [Cl-].C12=CC=CC=C2C(NCC)=CC=C1C(C=1C=CC(=CC=1)N(CC)CC)=C1C=CC(=[N+](CC)CC)C=C1 ROVRRJSRRSGUOL-UHFFFAOYSA-N 0.000 description 2
- ODXVNGGVVIDEPQ-UHFFFAOYSA-N (4-chlorophenoxy)methylphosphonic acid Chemical compound OP(O)(=O)COC1=CC=C(Cl)C=C1 ODXVNGGVVIDEPQ-UHFFFAOYSA-N 0.000 description 1
- OQCOEVHYCWVHTP-UHFFFAOYSA-N (4-hydroxy-4-oxo-1,3,2,4lambda5-dioxazaphosphetidin-2-ium-2-ylidene)azanide Chemical compound [N-]=[N+]1OP(=O)(O1)O OQCOEVHYCWVHTP-UHFFFAOYSA-N 0.000 description 1
- FPDWEIACOORPNF-UHFFFAOYSA-N (5-nitronaphthalen-1-yl)phosphonic acid Chemical compound C1=CC=C2C(P(O)(=O)O)=CC=CC2=C1[N+]([O-])=O FPDWEIACOORPNF-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ILBBNQMSDGAAPF-UHFFFAOYSA-N 1-(6-hydroxy-6-methylcyclohexa-2,4-dien-1-yl)propan-1-one Chemical compound CCC(=O)C1C=CC=CC1(C)O ILBBNQMSDGAAPF-UHFFFAOYSA-N 0.000 description 1
- DTJDPHTWZYVDFZ-UHFFFAOYSA-N 1-hydroxyethane-1,1-disulfonic acid Chemical compound OS(=O)(=O)C(O)(C)S(O)(=O)=O DTJDPHTWZYVDFZ-UHFFFAOYSA-N 0.000 description 1
- IRLYGRLEBKCYPY-UHFFFAOYSA-M 2,5-dimethylbenzenesulfonate Chemical compound CC1=CC=C(C)C(S([O-])(=O)=O)=C1 IRLYGRLEBKCYPY-UHFFFAOYSA-M 0.000 description 1
- GCZFLYDNPNANCP-UHFFFAOYSA-N 2,6-ditert-butyl-1h-naphthalene-1,2-disulfonic acid Chemical compound OS(=O)(=O)C1C(S(O)(=O)=O)(C(C)(C)C)C=CC2=CC(C(C)(C)C)=CC=C21 GCZFLYDNPNANCP-UHFFFAOYSA-N 0.000 description 1
- YEVQZPWSVWZAOB-UHFFFAOYSA-N 2-(bromomethyl)-1-iodo-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(I)C(CBr)=C1 YEVQZPWSVWZAOB-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- GNTARUIZNIWBCN-UHFFFAOYSA-M 2-chloro-5-nitrobenzenesulfonate Chemical compound [O-][N+](=O)C1=CC=C(Cl)C(S([O-])(=O)=O)=C1 GNTARUIZNIWBCN-UHFFFAOYSA-M 0.000 description 1
- TUXAJHDLJHMOQB-UHFFFAOYSA-N 2-diazonio-4-sulfonaphthalen-1-olate Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC([N+]#N)=C([O-])C2=C1 TUXAJHDLJHMOQB-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- GAGMRFSMMBYWQZ-UHFFFAOYSA-N 2-hydroxy-1h-pyridine-2-carboxylic acid Chemical compound OC(=O)C1(O)NC=CC=C1 GAGMRFSMMBYWQZ-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- XCSZUHHAYFILGO-UHFFFAOYSA-N 2-methyl-4-nitrobenzenesulfonic acid Chemical compound CC1=CC([N+]([O-])=O)=CC=C1S(O)(=O)=O XCSZUHHAYFILGO-UHFFFAOYSA-N 0.000 description 1
- GLULCKCBVYGUDD-UHFFFAOYSA-N 2-phosphonobutane-1,1,1-tricarboxylic acid Chemical compound CCC(P(O)(O)=O)C(C(O)=O)(C(O)=O)C(O)=O GLULCKCBVYGUDD-UHFFFAOYSA-N 0.000 description 1
- IQOJIHIRSVQTJJ-UHFFFAOYSA-N 3-chlorobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC(Cl)=C1 IQOJIHIRSVQTJJ-UHFFFAOYSA-N 0.000 description 1
- XFKRPUUIHKVIDM-UHFFFAOYSA-N 4,5-dinitronaphthalene-2,7-disulfonic acid Chemical compound [O-][N+](=O)C1=CC(S(O)(=O)=O)=CC2=CC(S(=O)(=O)O)=CC([N+]([O-])=O)=C21 XFKRPUUIHKVIDM-UHFFFAOYSA-N 0.000 description 1
- ABSXMLODUTXQDJ-UHFFFAOYSA-L 4-(4-sulfonatophenyl)benzenesulfonate Chemical compound C1=CC(S(=O)(=O)[O-])=CC=C1C1=CC=C(S([O-])(=O)=O)C=C1 ABSXMLODUTXQDJ-UHFFFAOYSA-L 0.000 description 1
- AXDJCCTWPBKUKL-UHFFFAOYSA-N 4-[(4-aminophenyl)-(4-imino-3-methylcyclohexa-2,5-dien-1-ylidene)methyl]aniline;hydron;chloride Chemical compound Cl.C1=CC(=N)C(C)=CC1=C(C=1C=CC(N)=CC=1)C1=CC=C(N)C=C1 AXDJCCTWPBKUKL-UHFFFAOYSA-N 0.000 description 1
- XTLJJHGQACAZMS-UHFFFAOYSA-N 4-oxo-1h-pyridine-2,6-dicarboxylic acid Chemical compound OC(=O)C1=CC(=O)C=C(C(O)=O)N1 XTLJJHGQACAZMS-UHFFFAOYSA-N 0.000 description 1
- MXXLHBCSVDDTIX-UHFFFAOYSA-N 4-oxo-1h-pyridine-2-carboxylic acid Chemical compound OC(=O)C1=CC(O)=CC=N1 MXXLHBCSVDDTIX-UHFFFAOYSA-N 0.000 description 1
- YLKCHWCYYNKADS-UHFFFAOYSA-N 5-hydroxynaphthalene-1-sulfonic acid Chemical class C1=CC=C2C(O)=CC=CC2=C1S(O)(=O)=O YLKCHWCYYNKADS-UHFFFAOYSA-N 0.000 description 1
- YCPXWRQRBFJBPZ-UHFFFAOYSA-N 5-sulfosalicylic acid Chemical compound OC(=O)C1=CC(S(O)(=O)=O)=CC=C1O YCPXWRQRBFJBPZ-UHFFFAOYSA-N 0.000 description 1
- ZRDSGWXWQNSQAN-UHFFFAOYSA-N 6-diazo-n-phenylcyclohexa-2,4-dien-1-amine Chemical compound [N-]=[N+]=C1C=CC=CC1NC1=CC=CC=C1 ZRDSGWXWQNSQAN-UHFFFAOYSA-N 0.000 description 1
- BLHCMGRVFXRYRN-UHFFFAOYSA-N 6-hydroxynicotinic acid Chemical compound OC(=O)C1=CC=C(O)N=C1 BLHCMGRVFXRYRN-UHFFFAOYSA-N 0.000 description 1
- HWTDMFJYBAURQR-UHFFFAOYSA-N 80-82-0 Chemical compound OS(=O)(=O)C1=CC=CC=C1[N+]([O-])=O HWTDMFJYBAURQR-UHFFFAOYSA-N 0.000 description 1
- MMNWSHJJPDXKCH-UHFFFAOYSA-N 9,10-dioxoanthracene-2-sulfonic acid Chemical compound C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 MMNWSHJJPDXKCH-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- RGCKGOZRHPZPFP-UHFFFAOYSA-N Alizarin Natural products C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- SGHZXLIDFTYFHQ-UHFFFAOYSA-L Brilliant Blue Chemical compound [Na+].[Na+].C=1C=C(C(=C2C=CC(C=C2)=[N+](CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=2C(=CC=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1 SGHZXLIDFTYFHQ-UHFFFAOYSA-L 0.000 description 1
- PLFWKEBYFVGLME-UHFFFAOYSA-N C1(=CC=CC=C1)C1=C(C(N=N1)=O)C.[Na] Chemical compound C1(=CC=CC=C1)C1=C(C(N=N1)=O)C.[Na] PLFWKEBYFVGLME-UHFFFAOYSA-N 0.000 description 1
- BITYZXVUVWKCEB-UHFFFAOYSA-L C=1(C(=CC=C2C=CC=CC12)S(=O)(=O)[O-])S(=O)(=O)OCOS(=O)(=O)C=1C(=CC=C2C=CC=CC12)S(=O)(=O)[O-].[Na+].[Na+] Chemical compound C=1(C(=CC=C2C=CC=CC12)S(=O)(=O)[O-])S(=O)(=O)OCOS(=O)(=O)C=1C(=CC=C2C=CC=CC12)S(=O)(=O)[O-].[Na+].[Na+] BITYZXVUVWKCEB-UHFFFAOYSA-L 0.000 description 1
- JUQPZRLQQYSMEQ-UHFFFAOYSA-N CI Basic red 9 Chemical compound [Cl-].C1=CC(N)=CC=C1C(C=1C=CC(N)=CC=1)=C1C=CC(=[NH2+])C=C1 JUQPZRLQQYSMEQ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- IMQLKJBTEOYOSI-GPIVLXJGSA-N Inositol-hexakisphosphate Chemical compound OP(O)(=O)O[C@H]1[C@H](OP(O)(O)=O)[C@@H](OP(O)(O)=O)[C@H](OP(O)(O)=O)[C@H](OP(O)(O)=O)[C@@H]1OP(O)(O)=O IMQLKJBTEOYOSI-GPIVLXJGSA-N 0.000 description 1
- WWKGVZASJYXZKN-UHFFFAOYSA-N Methyl violet 2B Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1C(C=1C=CC(N)=CC=1)=C1C=CC(=[N+](C)C)C=C1 WWKGVZASJYXZKN-UHFFFAOYSA-N 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- IMQLKJBTEOYOSI-UHFFFAOYSA-N Phytic acid Natural products OP(O)(=O)OC1C(OP(O)(O)=O)C(OP(O)(O)=O)C(OP(O)(O)=O)C(OP(O)(O)=O)C1OP(O)(O)=O IMQLKJBTEOYOSI-UHFFFAOYSA-N 0.000 description 1
- 240000007320 Pinus strobus Species 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical class OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 239000000999 acridine dye Substances 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 230000003679 aging effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- HFVAFDPGUJEFBQ-UHFFFAOYSA-M alizarin red S Chemical compound [Na+].O=C1C2=CC=CC=C2C(=O)C2=C1C=C(S([O-])(=O)=O)C(O)=C2O HFVAFDPGUJEFBQ-UHFFFAOYSA-M 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- ANBBXQWFNXMHLD-UHFFFAOYSA-N aluminum;sodium;oxygen(2-) Chemical compound [O-2].[O-2].[Na+].[Al+3] ANBBXQWFNXMHLD-UHFFFAOYSA-N 0.000 description 1
- 238000002048 anodisation reaction Methods 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- MSSUFHMGCXOVBZ-UHFFFAOYSA-N anthraquinone-2,6-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 MSSUFHMGCXOVBZ-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000005228 aryl sulfonate group Chemical group 0.000 description 1
- VGPYEHKOIGNJKV-UHFFFAOYSA-N asulam Chemical compound COC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 VGPYEHKOIGNJKV-UHFFFAOYSA-N 0.000 description 1
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 235000010338 boric acid Nutrition 0.000 description 1
- 229960001506 brilliant green Drugs 0.000 description 1
- HXCILVUBKWANLN-UHFFFAOYSA-N brilliant green cation Chemical compound C1=CC(N(CC)CC)=CC=C1C(C=1C=CC=CC=1)=C1C=CC(=[N+](CC)CC)C=C1 HXCILVUBKWANLN-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
- MUYSADWCWFFZKR-UHFFFAOYSA-N cinchomeronic acid Chemical compound OC(=O)C1=CC=NC=C1C(O)=O MUYSADWCWFFZKR-UHFFFAOYSA-N 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- WBEBQCINXJDZCX-UHFFFAOYSA-N dibunic acid Chemical compound OS(=O)(=O)C1=C(C(C)(C)C)C=CC2=CC(C(C)(C)C)=CC=C21 WBEBQCINXJDZCX-UHFFFAOYSA-N 0.000 description 1
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 1
- 229960001826 dimethylphthalate Drugs 0.000 description 1
- MPFLRYZEEAQMLQ-UHFFFAOYSA-N dinicotinic acid Chemical compound OC(=O)C1=CN=CC(C(O)=O)=C1 MPFLRYZEEAQMLQ-UHFFFAOYSA-N 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 description 1
- BJZIJOLEWHWTJO-UHFFFAOYSA-H dipotassium;hexafluorozirconium(2-) Chemical compound [F-].[F-].[F-].[F-].[F-].[F-].[K+].[K+].[Zr+4] BJZIJOLEWHWTJO-UHFFFAOYSA-H 0.000 description 1
- 238000004070 electrodeposition Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 229940107698 malachite green Drugs 0.000 description 1
- FDZZZRQASAIRJF-UHFFFAOYSA-M malachite green Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1C(C=1C=CC=CC=1)=C1C=CC(=[N+](C)C)C=C1 FDZZZRQASAIRJF-UHFFFAOYSA-M 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 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
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- QFVDKARCPMTZCS-UHFFFAOYSA-N methylrosaniline Chemical compound C1=CC(N(C)C)=CC=C1C(O)(C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1 QFVDKARCPMTZCS-UHFFFAOYSA-N 0.000 description 1
- 229960003926 methylrosaniline Drugs 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
- SHXOKQKTZJXHHR-UHFFFAOYSA-N n,n-diethyl-5-iminobenzo[a]phenoxazin-9-amine;hydrochloride Chemical compound [Cl-].C1=CC=C2C3=NC4=CC=C(N(CC)CC)C=C4OC3=CC(=[NH2+])C2=C1 SHXOKQKTZJXHHR-UHFFFAOYSA-N 0.000 description 1
- XZSZONUJSGDIFI-UHFFFAOYSA-N n-(4-hydroxyphenyl)-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NC1=CC=C(O)C=C1 XZSZONUJSGDIFI-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
- PGSADBUBUOPOJS-UHFFFAOYSA-N neutral red Chemical compound Cl.C1=C(C)C(N)=CC2=NC3=CC(N(C)C)=CC=C3N=C21 PGSADBUBUOPOJS-UHFFFAOYSA-N 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 238000006303 photolysis reaction Methods 0.000 description 1
- 239000001007 phthalocyanine dye Substances 0.000 description 1
- 229940068041 phytic acid Drugs 0.000 description 1
- 235000002949 phytic acid Nutrition 0.000 description 1
- 239000000467 phytic acid Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- ZUCRGHABDDWQPY-UHFFFAOYSA-N pyrazine-2,3-dicarboxylic acid Chemical compound OC(=O)C1=NC=CN=C1C(O)=O ZUCRGHABDDWQPY-UHFFFAOYSA-N 0.000 description 1
- NIPZZXUFJPQHNH-UHFFFAOYSA-N pyrazine-2-carboxylic acid Chemical compound OC(=O)C1=CN=CC=N1 NIPZZXUFJPQHNH-UHFFFAOYSA-N 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 229940005657 pyrophosphoric acid Drugs 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 229940043267 rhodamine b Drugs 0.000 description 1
- 229910001388 sodium aluminate Inorganic materials 0.000 description 1
- DZCAZXAJPZCSCU-UHFFFAOYSA-K sodium nitrilotriacetate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CC([O-])=O DZCAZXAJPZCSCU-UHFFFAOYSA-K 0.000 description 1
- HIEHAIZHJZLEPQ-UHFFFAOYSA-M sodium;naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 HIEHAIZHJZLEPQ-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- RSEHMVDVWGHIAQ-UHFFFAOYSA-N tert-butyl naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)OC(C)(C)C)=CC=CC2=C1 RSEHMVDVWGHIAQ-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 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
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- LLWJPGAKXJBKKA-UHFFFAOYSA-N victoria blue B Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1C(C=1C=CC(=CC=1)N(C)C)=C(C=C1)C2=CC=CC=C2C1=[NH+]C1=CC=CC=C1 LLWJPGAKXJBKKA-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 230000003313 weakening effect Effects 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-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
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
Description
【発明の詳細な説明】
〔発明の分野〕
本発明は感光性平版印刷版に関するものであ
る。更に詳しくは安定化され現像性が改良され製
造後に経時にともなう地汚れの発生し難い感光性
平版印刷版に関するものである。DETAILED DESCRIPTION OF THE INVENTION Field of the Invention The present invention relates to photosensitive lithographic printing plates. More specifically, the present invention relates to a photosensitive lithographic printing plate that is stabilized, has improved developability, and is less prone to scumming over time after production.
従来、高分子化合物と水不溶性ジアゾ樹脂から
なる感光性組成物を感光性平版印刷版の感光層と
して用いた場合、印刷インキ受容性に優れた平版
印刷版が得られることが知られている（特公昭47
−1167号、特開昭48−9804号、同47−24404号、
同47−38302号、同50−30604号、同50−118802
号、同53−120903号参照）。
Conventionally, it has been known that when a photosensitive composition comprising a polymer compound and a water-insoluble diazo resin is used as the photosensitive layer of a photosensitive lithographic printing plate, a lithographic printing plate with excellent printing ink receptivity can be obtained ( Special Public Service 1977
-1167, JP-A-48-9804, JP-A-47-24404,
No. 47-38302, No. 50-30604, No. 50-118802
No. 53-120903).
しかし高分子化合物と水不溶性ジアゾ樹脂から
なる感光層を親水化処理したアルミニウム板上に
塗布した感光性平版印刷版は経時によつて現像不
良が発生し、印刷時非画像部がインキによつて汚
れるという欠点を有していた。この欠点を改良す
るために種々の安定化剤の添加が試みられてい
る。たとえば特開昭54−151023号公報に記載され
ている亜りん酸、特開昭53−3216号公報に記載さ
れている蓚酸、特開昭50−36207号公報に記載さ
れているハロゲン含有有機りん酸エステル化合
物、特開昭51−143405号公報に記載されている複
素環式ジアゾニウム塩やその他米国特許3679419
号明細書６欄69行目から７欄７行目に記載されて
いるりん酸、硫酸、有機スルホン酸、ポリアクリ
ル酸、ポリビニルホスホン酸やポリビニルスルホ
ン酸を前記感光層に添加することによつて経時性
は改良されることが認められている。しかしなが
らこれらの添加剤の改良効果は必ずしも十分では
なかつた。 However, with photosensitive lithographic printing plates in which a photosensitive layer made of a polymer compound and a water-insoluble diazo resin is coated on an aluminum plate that has been made hydrophilic, poor development occurs over time, and non-image areas are affected by ink during printing. It had the disadvantage of getting dirty. In order to improve this drawback, attempts have been made to add various stabilizers. For example, phosphorous acid described in JP-A-54-151023, oxalic acid described in JP-A-53-3216, and halogen-containing organic phosphorus described in JP-A-50-36207. Acid ester compounds, heterocyclic diazonium salts described in JP-A-51-143405, and other U.S. Patent No. 3679419
By adding phosphoric acid, sulfuric acid, organic sulfonic acid, polyacrylic acid, polyvinylphosphonic acid, or polyvinylsulfonic acid described in column 6, line 69 to column 7, line 7 of the specification of the No. It has been observed that the aging properties are improved. However, the improvement effects of these additives were not necessarily sufficient.
本発明の目的は経時による現像不良に起因する
と考えられる印刷時の非画像部の汚れを誘発させ
ない感光性平版印刷版を提供することにある。そ
の他の目的は露光部が光によつて容易に硬化し、
優れたインキ受容性を示し、未露光部が現像液に
よつて容易に溶出する感光性平版印刷版を提供す
ることにある。
An object of the present invention is to provide a photosensitive lithographic printing plate that does not cause staining of non-image areas during printing, which is thought to be caused by poor development over time. The other purpose is that the exposed area is easily hardened by light.
The object of the present invention is to provide a photosensitive lithographic printing plate which exhibits excellent ink receptivity and whose unexposed areas are easily eluted by a developer.
本発明者らは前記目的を達成すべく鋭意研究を
重ねた結果、親水化処理したアルミニウム板上
に、有機溶媒に可溶で実質的に水不溶性のジアゾ
樹脂と実質的に水不溶性で皮膜形成能を有する有
機高分子化合物からなる感光性平版印刷版の当該
感光層に、ジピコリン酸（塩）を添加することを
見い出し先願した（特願昭58−111672号）が、更
に検討したところ、同族のＮ−ヘテロ環カルボン
酸を添加することによつて、同様の効果が得られ
ることを見い出した。
As a result of intensive research to achieve the above object, the inventors of the present invention formed a film on a hydrophilized aluminum plate with a diazo resin that is soluble in organic solvents and is substantially water-insoluble. It was discovered that dipicolinic acid (salt) could be added to the photosensitive layer of a photosensitive lithographic printing plate made of an organic polymer compound having the above-mentioned properties. It has been found that similar effects can be obtained by adding a homologous N-heterocyclic carboxylic acid.
本発明において使用される有機溶媒に可溶で実
質的に水不溶性のジアゾ樹脂としては、芳香族ジ
アゾニウム塩と例えば活性カルボニル含有化合
物、殊にホルムアルデヒドとの縮合物で代表され
るジアゾ樹脂が有用である。ジアゾ樹脂としては
例えば特公昭39−17602号や特開昭54−98613の各
公報に記載されているｐ−ジアゾフエニルアミン
とホルムアルデヒドまたはアセトアルデヒドの縮
合物のヘキサフルオロ燐酸塩、テトラフルオロホ
ウ酸塩等のルイス酸塩、特開昭41−6813号や同48
−9804号の各公報に記載されているｐ−ジアゾフ
エニルアミンとホルムアルデヒドの縮合物のアニ
オン界面活性剤の塩、米国特許第3300309号、特
開昭47−38302号や米国特許第4123276号各明細書
中に記載されているｐ−ジアゾフエニルアミンと
ホルムアルデヒドの縮合物のフエノール塩、フル
オロカプリン酸塩やスルホン酸塩（トルイソプロ
ピルナフタレンスルホン酸酸、４，4′−ビフエニ
ルジスルホン酸塩、５−ニトロオルト−トルエン
スルホン酸塩、５−スルホサリチル酸、２，５−
ジメチルベンゼンスルホン酸塩、２−ニトロベン
ゼンスルホン酸塩、３−クロロベンゼンスルホン
酸塩、２−クロロ−５−ニトロベンゼンスルホン
酸塩、２−フルオロカプリルナフタレンスルホン
酸塩、１−ナフト−ル−５−スルホン酸塩、２−
メトキシ−４−ヒドロオキシ−５−ベンゾイルベ
ンゼンスルホン酸塩、パラトルエンスルホン酸）、
米国特許第3404003号明細書に記載されているｐ
−ジアゾジフエニルアミンとホルムアルデヒドの
縮合物の有機ホスホン酸塩、特公昭45−28594号
公報に記載されているｐ−ジアゾフエニルアミン
とホルムアルデヒドの縮合物の芳香族カルボン酸
塩、その他ｐ−ジアゾフエニアミンとホルムアル
デヒドの縮合物にりん酸塩や蓚酸塩がある。その
他有用なジアゾ樹脂としては米国特許第3679419
号明細書に記載されている置換又は無置換のジフ
エニルアミン−４−ジアゾニウム塩とエーテル化
合物との縮合物がある。一般的に芳香族ジアゾニ
ウム化合物と活性カルボニル化合物や活性エーテ
ル化合物の縮合物のルイス酸塩や有機酸塩が有機
溶媒に可溶で実質的に水不溶性であるので本発明
に用いるジアゾ樹脂として適している。なお本発
明のジアゾ樹脂で実質的に水不溶性とは水に対す
る常温での溶解度が約１重量％以下であることを
さす。 As the organic solvent-soluble, substantially water-insoluble diazo resin used in the present invention, diazo resins represented by condensates of aromatic diazonium salts and, for example, active carbonyl-containing compounds, particularly formaldehyde, are useful. be. Examples of diazo resins include hexafluorophosphates and tetrafluoroborates of condensates of p-diazophenylamine and formaldehyde or acetaldehyde, which are described in Japanese Patent Publication No. 39-17602 and Japanese Patent Application Laid-open No. 54-98613. Lewis acid salts such as JP-A-41-6813 and JP-A-48
-9804, anionic surfactant salts of condensates of p-diazophenylamine and formaldehyde, U.S. Pat. Phenol salts, fluorocaprates and sulfonates of condensates of p-diazophenylamine and formaldehyde described in the specification (toluisopropylnaphthalenesulfonic acid, 4,4'-biphenyl disulfonate, 5-nitroortho-toluenesulfonate, 5-sulfosalicylic acid, 2,5-
Dimethylbenzenesulfonate, 2-nitrobenzenesulfonate, 3-chlorobenzenesulfonate, 2-chloro-5-nitrobenzenesulfonate, 2-fluorocaprylnaphthalenesulfonate, 1-naphthol-5-sulfonic acid salt, 2-
methoxy-4-hydroxy-5-benzoylbenzenesulfonate, para-toluenesulfonic acid),
p described in U.S. Patent No. 3,404,003
- Organic phosphonates of condensates of diazodiphenylamine and formaldehyde, aromatic carboxylates of condensates of p-diazophenylamine and formaldehyde described in Japanese Patent Publication No. 45-28594, and other p-diazo Phosphate and oxalate are condensates of pheniamine and formaldehyde. Other useful diazo resins include U.S. Patent No. 3679419.
There is a condensate of a substituted or unsubstituted diphenylamine-4-diazonium salt and an ether compound described in the above specification. In general, Lewis acid salts and organic acid salts of condensates of aromatic diazonium compounds and active carbonyl compounds or active ether compounds are soluble in organic solvents and substantially water-insoluble, so they are suitable as the diazo resin used in the present invention. There is. In the diazo resin of the present invention, "substantially water-insoluble" means that the solubility in water at room temperature is about 1% by weight or less.
本発明において使用される実質的に水不溶性で
皮膜形成能を有する有機高分子化合物としてはジ
アゾ樹脂と相溶性がよく親油性で耐摩耗性に優れ
た樹脂が好適である。具体的にはポリスチレン、
ポリ塩化ビニル、ポリ（メタ）アクリレート、ポ
リエステル、ポリアミド、ポリウレタン、ポリカ
ーボネート、エポキシ樹脂、ポリビニルホルマー
ル、ポリビニルブチラール、アルキルフエノール
ホルムアルデヒド樹脂があるが、これらの中の酸
価10−200を有するポリ（メタ）アクリレートが
好適である。特に好適な酸価10−200を有するポ
リ（メタ）アクリレートとしてはアクリル酸、メ
タクリル酸、クロトン酸またはマレイン酸を必須
成分として含む共重合体、例えば特開昭50−
118802号公報に記載されている様な２−ヒドロキ
シエチルアクリレートまたは２−ヒドロキシエチ
ルメタアクリレートとアクリロニトリルまたはメ
タクリロニトリル、アクリル酸またはメタクリル
酸と必要に応じて他の共重合可能のモノマーとの
多元共重合体、特開昭53−120903号公報に記載さ
れている様な末端がヒドロキシ基であり、かつジ
カルボン酸エステル残基を含む基でエステル化さ
れたアクリル酸またはメタクリル酸、アクリル酸
またはメタクリル酸と必要に応じて他の共重合可
能のモノマーとの多元共重合体、特開昭54−
98614号公報に記載されている様な芳香族性水酸
基を末端に有する単量体（例えばＮ−（４−ヒド
ロキシフエニル）メタクリルアミドなど）とアク
リル酸またはメタクリル酸と必要に応じて他の共
重合可能のモノマーとの多元共重合体、特開昭56
−4144号公報に記載されている様なアルキルアク
リレートまたはメタクリレート、アクロニトリル
またはメタクロニトリルおよび不飽和カルボン酸
よりなる多元共重合体をあげることが出来る。ま
たこの他酸性ポリビニルアルコール誘導体や酸性
セルロース誘導体も有用である。なお本発明での
実質的な水不溶性の有機高分子化合物とは水に対
する常温での溶解度が約１重量％以下のものをさ
す。 As the organic polymer compound that is substantially water-insoluble and has a film-forming ability used in the present invention, a resin that is highly compatible with the diazo resin, is lipophilic, and has excellent abrasion resistance is suitable. Specifically, polystyrene,
Among these are polyvinyl chloride, poly(meth)acrylate, polyester, polyamide, polyurethane, polycarbonate, epoxy resin, polyvinyl formal, polyvinyl butyral, and alkylphenol formaldehyde resin, poly(meth) having an acid value of 10-200. Acrylates are preferred. Particularly suitable poly(meth)acrylates having an acid value of 10-200 include copolymers containing acrylic acid, methacrylic acid, crotonic acid, or maleic acid as an essential component, such as JP-A-1986-1000-1.
A multicomponent copolymer of 2-hydroxyethyl acrylate or 2-hydroxyethyl methacrylate, acrylonitrile or methacrylonitrile, acrylic acid or methacrylic acid, and other copolymerizable monomers as required, as described in Japanese Patent No. 118802. Polymers, acrylic acid or methacrylic acid, acrylic acid or methacrylic acid, which has a hydroxyl group at the end and is esterified with a group containing a dicarboxylic acid ester residue, as described in JP-A-53-120903. Multi-component copolymer with other copolymerizable monomers as necessary, JP-A-1988-
A monomer having an aromatic hydroxyl group at the end (for example, N-(4-hydroxyphenyl) methacrylamide, etc.) as described in Publication No. 98614, acrylic acid or methacrylic acid, and other compounds as necessary. Multi-component copolymer with polymerizable monomers, JP-A-1988
Examples include multi-component copolymers of alkyl acrylates or methacrylates, acronitrile or methachronitrile, and unsaturated carboxylic acids as described in Japanese Patent No. 4144. In addition, acidic polyvinyl alcohol derivatives and acidic cellulose derivatives are also useful. In the present invention, the term "substantially water-insoluble organic polymer compound" refers to one having a solubility in water of about 1% by weight or less at room temperature.
感光層中におけるこれらのジアゾ樹脂と高分子
化合物の含有量は両者の総重量に対してジアゾ樹
脂３〜30重量％で高分子化合物は97〜70重量％で
ある。より好ましい範囲はジアゾ樹脂５〜20重量
％で高分子化合物95〜80重量％である。ジアゾ樹
脂の含有量は少ない方が感度は高いが、３重量％
より少なくなると高分子化合物を光硬化させるた
めには不十分となり現像時に光硬化膜が現像液に
よつて膨潤し膜が弱くなる。逆にジアゾ樹脂の含
有量が30重量％より多くなると感度が低くなり実
用的ではなくなる。 The contents of the diazo resin and the polymer compound in the photosensitive layer are 3 to 30% by weight of the diazo resin and 97 to 70% by weight of the polymer compound, based on the total weight of both. A more preferred range is 5 to 20% by weight of the diazo resin and 95 to 80% by weight of the polymer compound. The lower the diazo resin content, the higher the sensitivity, but 3% by weight
If the amount is less, it will be insufficient to photocure the polymer compound, and the photocured film will swell with the developer during development, weakening the film. On the other hand, if the content of the diazo resin exceeds 30% by weight, the sensitivity becomes low and becomes impractical.
本発明に用いられるＮ−ヘテロ環カルボン酸
は、少なくとも１つのカルボキシル基を有するＮ
−ヘテロ環化合物であつて、有機溶剤可溶性のも
のが好ましいＮ−ヘテロ環としては少なくとも１
個の窒素原子を含む５員環または６員環のもの、
例えば、ピリジン環、キノリン環、ピラジン環、
ピロール環などである。具体的なＮ−ヘテロ環カ
ルボン酸には、ピコリン酸、ニコチン酸、イソニ
コチン酸、キノリン酸、ルチジン酸、ジニコチン
酸、イソシンコメロン酸、シンコメロン酸、キナ
ルジン酸、４−ヒドロキシピコリン酸、２−ヒド
ロキシピコリン酸、２−ピラジンカルボン酸、
２・３−ピラジンジカルボン酸、ピロール−２−
カルボン酸、６−ヒドロキシニコチン酸、ケリダ
ム酸などが含まれている。 The N-heterocyclic carboxylic acid used in the present invention is an N-heterocyclic carboxylic acid having at least one carboxyl group.
- A heterocyclic compound, preferably one soluble in an organic solvent, has at least one N-heterocyclic ring.
5- or 6-membered rings containing nitrogen atoms,
For example, pyridine ring, quinoline ring, pyrazine ring,
Such as pyrrole ring. Specific N-heterocyclic carboxylic acids include picolinic acid, nicotinic acid, isonicotinic acid, quinolinic acid, lutidic acid, dinicotinic acid, isocincomeronic acid, cinchomeronic acid, quinaldic acid, 4-hydroxypicolinic acid, 2- Hydroxypicolinic acid, 2-pyrazinecarboxylic acid,
2,3-pyrazinedicarboxylic acid, pyrrole-2-
Contains carboxylic acid, 6-hydroxynicotinic acid, chelidamic acid, etc.
これらの化合物は、単独または２以上組み合わ
せて使用され、その添加量はジアゾ樹脂に対して
１〜100重量％、より好ましくは10〜50重量％で
ある。添加量が１重量％より少なくなると汚れを
防止する能力が十分でなくなる。また100重量％
より多くなると感光層の皮膜強度が低下し耐刷が
劣化する傾向がみられる。 These compounds may be used alone or in combination of two or more, and the amount added is 1 to 100% by weight, more preferably 10 to 50% by weight, based on the diazo resin. If the amount added is less than 1% by weight, the ability to prevent staining will not be sufficient. Also 100% by weight
When the amount increases, the film strength of the photosensitive layer tends to decrease and printing durability tends to deteriorate.
上述の如き感光層には、種々の添加剤を加える
ことが出来る。例えば塗布性を改良するためのア
ルキルエーテル類（たとえばエチルセルロース、
メチルセルロース）や弗素系界面活性剤、塗膜の
柔軟性、耐磨耗性を付与するための可塑剤（たと
えばトリクレシジルホスフエート、ジメチルフタ
レート、ジブチルフタレート、りん酸トリオクチ
ル、りん酸トリブチル、くえん酸トリブチル、ポ
リエチレングリコール、ポリプロピレングリコー
ルがある。また画像を可視画化するための着色物
質としてアクリジン染料、シアニン染料、スチリ
ル染料、トリフエニルメタン染料やフタロシアニ
ンなどの顔料、特にこれらの中でも焼出し性を付
与させる塩形成能力のある染料、たとえばクリス
タルバイオレツト（CI42555）、メチルバイオレ
ツト2B（CI42535）、マラカイトグリーン
（CI42000）、フクシン（CI42510）、クリスタルバ
イオレツト−カルビノールベース（CI42555：
１）、パラフクシン（CI42500）、スーダンブルー
Ｇ（CI61520）、アシランブリリアントブルー5B
（CI42740）、アシランバイオレツトS4BN
（CI42640）、アストラジアマントグリーンGX
（CI42040）、ローダミンＢ（CI45170）、サマロン
ブルGSL（（CI62500）、ビクトリアブルーＢ
（CI44045）、アリザリンダイレクトブルー
（CI62055）、ビクトリアピユアブルーBOD
（CI42595）、ブリリアントグリーン（CI42040）、
ナイルブルーBX（CI51185）、ニユートラルレツ
ド（CI50040）、ロージユリンピユアブルー3G
（CI51004）、ビクトリアピユアブルーBODのロジ
ン樹脂酸塩、ビクトリアピユアブルーBODのパ
ラトルエンスルホン酸、クリスタルバイオレツト
のパラトルエンスルホン酸塩等が好適である。 Various additives can be added to the photosensitive layer as described above. For example, alkyl ethers (e.g. ethyl cellulose,
methylcellulose), fluorine-based surfactants, plasticizers to impart flexibility and abrasion resistance to coatings (e.g. tricresidyl phosphate, dimethyl phthalate, dibutyl phthalate, trioctyl phosphate, tributyl phosphate, citric acid) These include tributyl, polyethylene glycol, and polypropylene glycol.Additionally, pigments such as acridine dyes, cyanine dyes, styryl dyes, triphenylmethane dyes, and phthalocyanine dyes are used as coloring substances to visualize images, and among these pigments, especially those that impart print-out properties. dyes with the ability to form salts, such as crystal violet (CI42555), methyl violet 2B (CI42535), malachite green (CI42000), fuchsin (CI42510), crystal violet-carbinol-based (CI42555):
1), Parafuchsin (CI42500), Sudan Blue G (CI61520), Acilan Brilliant Blue 5B
(CI42740), Asilan Violet S4BN
(CI42640), Astrasia Cloak Green GX
(CI42040), Rhodamine B (CI45170), Summer Blue GSL ((CI62500), Victoria Blue B
(CI44045), Alizarin Direct Blue (CI62055), Victoria Piyua Blue BOD
(CI42595), brilliant green (CI42040),
Nile Blue BX (CI51185), Neutral Red (CI50040), Rose Lily Blue 3G
(CI51004), rosin resinate of Victoria Pure Blue BOD, paratoluenesulfonic acid of Victoria Pure Blue BOD, paratoluenesulfonic acid of Crystal Violet, etc. are suitable.
これらの染料や顔料の添加量はジアゾ樹脂に対
して５〜100重量％で好ましくは10〜40重量％で
ある。塩形成能を有する染料をジアゾ樹脂ととも
に用いるとジアゾ樹脂の光分解に伴う酸がこれら
の染料と塩形成を行い染料が退色したり発色した
りして焼出し性を有する画像を提供する。 The amount of these dyes and pigments added is 5 to 100% by weight, preferably 10 to 40% by weight, based on the diazo resin. When a dye having salt-forming ability is used together with a diazo resin, the acid accompanying the photodecomposition of the diazo resin forms a salt with these dyes, causing the dye to fade or develop color, thereby providing an image with print-out properties.
その他ジアゾ樹脂の一般的な安定化剤としてり
ん酸、亜りん酸、ピロりん酸、ポリりん酸、蓚
酸、硼酸、酒石酸、トルエンスルホン酸、パラー
クロスルホン酸、イソプロピルナフタレンスルホ
ン酸ナトリウム、ｔ−ブチルナフタレンスルホン
酸ナトリウム、メチレンジナフタレンジスルホン
酸ジナトリウム、スルホン化アルキルジフエニル
オキサイドのナトリウム塩、縮合アリールスルホ
ネートのナトリウム塩、ナフタレンアルキルスル
ホン酸ナトリウム等のアニオン界面活性剤、ナフ
タレン−１−スルホン酸、ナフタレン−２−スル
ホン酸、２，６−ジ−ｔ−ブチルナフタレンスル
ホン酸、２，６−ジ−ｔ−ブチルナフタレンジス
ルホン酸、１，８−ジニトロ−ナフタレン−３，
６−ジスルホン酸、２−ジアゾ−１−ナフトール
−４−スルホン酸、４，4′−ジアゾスチルベン−
３，3′−ジスルホン酸、ナフタレン−１，５−ジ
スルホン酸、アンスラキノン−２−スルホン酸、
アンスラキノン−２，６−ジスルホン酸等のナフ
タレンやアンスラキノン等の多核芳香族スルホン
酸およびその塩、２−メトキシ−４−ヒドロキシ
−５−ベンゾイルベンゼンスルホン酸やその塩、
５−ニトロナフタレン−１−ホスホン酸、４−ク
ロロフエノキシメチルホスホン酸、ナトリウムフ
エニル−メチル−ピラゾロンスルホネート、２−
ホスホノブタントリカルボン酸−１，２，４，１
−ホスホノエタントリカルボン酸−１，２，２，
１−ヒドロキシエタン−１，１−ジスルホン酸を
添加することが出来る。これらの添加剤の添加量
はその使用対象目的によつて異なるが、一般には
全固形分に対して0.5〜30重量％である。 Other common stabilizers for diazo resins include phosphoric acid, phosphorous acid, pyrophosphoric acid, polyphosphoric acid, oxalic acid, boric acid, tartaric acid, toluenesulfonic acid, parachlorosulfonic acid, sodium isopropylnaphthalenesulfonate, and t-butyl. Anionic surfactants such as sodium naphthalene sulfonate, disodium methylene dinaphthalenedisulfonate, sodium salt of sulfonated alkyl diphenyl oxide, sodium salt of condensed aryl sulfonate, sodium naphthalene alkyl sulfonate, naphthalene-1-sulfonic acid, naphthalene -2-sulfonic acid, 2,6-di-t-butylnaphthalenesulfonic acid, 2,6-di-t-butylnaphthalene disulfonic acid, 1,8-dinitro-naphthalene-3,
6-disulfonic acid, 2-diazo-1-naphthol-4-sulfonic acid, 4,4'-diazostilbene-
3,3'-disulfonic acid, naphthalene-1,5-disulfonic acid, anthraquinone-2-sulfonic acid,
Polynuclear aromatic sulfonic acids such as naphthalene and anthraquinone such as anthraquinone-2,6-disulfonic acid and their salts, 2-methoxy-4-hydroxy-5-benzoylbenzenesulfonic acid and its salts,
5-nitronaphthalene-1-phosphonic acid, 4-chlorophenoxymethylphosphonic acid, sodium phenyl-methyl-pyrazolone sulfonate, 2-
Phosphonobutanetricarboxylic acid-1,2,4,1
-phosphonoethanetricarboxylic acid-1,2,2,
1-Hydroxyethane-1,1-disulfonic acid can be added. The amount of these additives added varies depending on the purpose for which they are used, but is generally 0.5 to 30% by weight based on the total solid content.
本発明の上述の如き感光性組成物は有機溶媒に
溶解し親水化処理したアルミニウム板に乾燥塗布
重量が0.5〜５ｇ／m2になる様に塗布するのが適
当である。塗布する際の感光性組成物の濃度は１
〜50重量％の範囲とすることが望ましく、使用さ
れる塗布溶媒としてはメチルセロソルブ、エチル
セロソルブ、メチルセロソルブアセテート、アセ
トン、メチルエチルケトン、メタノール、ジメチ
ルフオルムアミド、ジメチルスルフオキサイド、
エチレンジクロライド、シクロヘキサノン、ジオ
キサン、テトラビドロフラン、これらの混合溶媒
またはこれらの溶媒や混合溶媒に少量の水やトル
エン等のジアゾ樹脂や高分子化合物を溶解させな
い溶媒を添加した混合溶媒が適当である。これら
の溶媒に溶解させた感光液を親水化処理したアル
ミニウム板に塗布し乾燥させる場合50℃〜120℃
で乾燥させることが望ましい。乾燥方法は始め温
度を低くして予測乾燥後高温で乾燥させてもよい
が、適当な溶媒と濃度を選ぶことによつても直接
高温で乾燥させてもよい。 The photosensitive composition of the present invention as described above is suitably dissolved in an organic solvent and applied to a hydrophilized aluminum plate at a dry coating weight of 0.5 to 5 g/m 2 . The concentration of the photosensitive composition during application is 1
It is desirable that the amount is in the range of ~50% by weight, and the coating solvents used include methyl cellosolve, ethyl cellosolve, methyl cellosolve acetate, acetone, methyl ethyl ketone, methanol, dimethyl formamide, dimethyl sulfoxide,
Ethylene dichloride, cyclohexanone, dioxane, tetrahydrofuran, a mixed solvent thereof, or a mixed solvent prepared by adding a small amount of water, toluene, or other solvent that does not dissolve the diazo resin or polymer compound to these solvents or mixed solvents are suitable. When applying a photosensitive liquid dissolved in these solvents to a hydrophilized aluminum plate and drying it, the temperature is 50℃ to 120℃.
It is preferable to dry it. The drying method may be performed by starting at a low temperature and then drying at a high temperature after predicted drying, or by selecting an appropriate solvent and concentration, or by directly drying at a high temperature.
かくして得られた感光性平版印刷版は画像露光
後、弱アルカリ水よりなる現像液で現像すること
により原画に対してネガのレリーフ像が得られ
る。露光に好適な光源としては、カーボンアーク
灯、水銀灯、キセノンランプ、メタルハライドラ
ンプ、ストロボ、紫外線レーザ光線などをあげら
れる。未露光部を除去するための現像液としては
感光層を溶解させるものであればどの様なもので
も構わないが、特に酸価10〜200を有するポリ
（メタ）アクリレートをバインダーとして用いた
感光層の現像液としては特開昭51−77401号、特
開昭51−80228号、特開昭53−44202号や特開昭55
−52054号の各公報に記載されている様な、水に
対する溶解度が小さい有機溶媒、アリカリ剤、ア
ニオン界面活性剤（芳香族スルホン酸塩、ジアル
キルスルホコハク酸塩、ナフタレンアルキルスル
ホン酸塩、ナフトールのエチレンオキサイド付加
物の硫酸エステル塩、分枝アルキル硫酸エステル
塩）及び水から弱アルカリ水溶液が好適である。 After the imagewise exposure of the photosensitive lithographic printing plate thus obtained, a negative relief image can be obtained with respect to the original image by developing it with a developer consisting of weakly alkaline water. Suitable light sources for exposure include carbon arc lamps, mercury lamps, xenon lamps, metal halide lamps, strobes, ultraviolet laser beams, and the like. Any developer can be used to remove the unexposed areas as long as it dissolves the photosensitive layer, but in particular, a photosensitive layer using poly(meth)acrylate as a binder with an acid value of 10 to 200 can be used. Examples of developing solutions include JP-A-51-77401, JP-A-51-80228, JP-A-53-44202 and JP-A-55.
Organic solvents with low solubility in water, alkaline agents, anionic surfactants (aromatic sulfonates, dialkyl sulfosuccinates, naphthalene alkyl sulfonates, naphthalene ethylene Sulfate ester salts of oxide adducts, branched alkyl sulfate ester salts) and water to weakly alkaline aqueous solutions are suitable.
本発明の感光性組成物が塗布される親水化処理
したアルミニウム板としてはワイヤブラシグレイ
ン、パミスのスラリーを研磨剤としてナイロンブ
ラシで砂目立てするブラシグレイン、ボールグレ
イン、ケミカルグレイン、電解グレインやこれら
のグレインを複合させて行つた複合グレインによ
つて表面を砂目立てした後、必要に応じて硫酸、
りん酸、蓚酸、ホウ酸、クロム酸、スルフアミン
酸またはこれらの混酸中で直流又は交流電源にて
陽極酸化を行いアルミニウ表面に強固な不働態皮
膜を設けたものが好ましい。この様な不働態皮膜
自体でアルミニウム表面は親水化されてしまう
が、更に必要に応じて米国特許2714066号明細書
や米国特許3181461号明細書に記載されているケ
イ酸塩処理（ケイ酸ナトリウム、ケイ酸カリウ
ム）、米国特許2946638号明細書に記載されている
弗化ジルコニウム酸カリウム処理、米国特許
3201247号明細書に記載されているホスホモリブ
デード処理、独国特許1091433号明細書に記載さ
れているポリアクリル酸処理、独国特許1134093
号明細書や英国特許1230447号明細書に記載され
ているポリビニルホスホン酸処理、特公昭44−
6409号明細書に記載されているホスホン酸処理、
米国特許3307951号明細書に記載されているフイ
チン酸処理、特開昭58−16893号明細書や特開昭
58−18291号明細書に記載されている親水性有機
高分子化合物と２価の金属よりなる複合処理やそ
の他スルホン酸基を有する水溶性重合体の下塗に
よつて親水化処理を行つたものも好ましい、その
他の親水化処理方法としては米国特許3658662号
明細書に記載されているシリケート電着をもあげ
ることが出来る。 Examples of the hydrophilic aluminum plate to which the photosensitive composition of the present invention is applied include wire brush grain, brush grain grained with a nylon brush using pumice slurry as an abrasive, ball grain, chemical grain, electrolytic grain, and these. After graining the surface with a composite grain, add sulfuric acid as needed.
Preferably, a strong passive film is formed on the aluminum surface by anodic oxidation in phosphoric acid, oxalic acid, boric acid, chromic acid, sulfamic acid, or a mixed acid thereof using a direct current or alternating current power source. Such a passive film itself makes the aluminum surface hydrophilic, but if necessary, silicate treatment (sodium silicate, sodium silicate, potassium silicate), potassium fluorozirconate treatment as described in U.S. Pat. No. 2,946,638, U.S. Pat.
3201247, polyacrylic acid treatment as described in German Patent No. 1091433, German Patent No. 1134093.
The polyvinylphosphonic acid treatment described in the patent specification and British Patent No. 1230447,
Phosphonic acid treatment as described in No. 6409;
The phytic acid treatment described in US Pat.
58-18291, as well as those subjected to hydrophilic treatment by a composite treatment consisting of a hydrophilic organic polymer compound and a divalent metal, or by undercoating with a water-soluble polymer having a sulfonic acid group. Other preferred hydrophilic treatment methods include silicate electrodeposition described in US Pat. No. 3,658,662.
以下、本発明を実施例に基づいて更に詳細に説
明する。なお％は重量％を示すものとする。
Hereinafter, the present invention will be explained in more detail based on examples. Note that % indicates weight %.
実施例 １
厚さ0.24mmの1Sアルミニウム板を80℃に保たれ
た第３りん酸ナトリウムの10％水溶液に３分間浸
漬して脱脂し、ナイロンブラシとパミススラリー
で砂目立て後、60℃のアルミン酸ナトリウム３％
水溶液でデスマツトした。このアルミニウム板を
更に希硝酸中で電解グレインを行い複合砂目立て
を行つた後、20％硫酸中で2A／ｄm2の電流密度
で２分間陽極酸化し、その後70℃の珪酸ナトリウ
ムの2.5％水溶液で１分間処理した。Example 1 A 1S aluminum plate with a thickness of 0.24 mm was degreased by immersing it in a 10% aqueous solution of tertiary sodium phosphate kept at 80°C for 3 minutes, and after graining with a nylon brush and pumice slurry, it was soaked in aluminum at 60°C. Sodium acid 3%
It was desmatted with an aqueous solution. This aluminum plate was further subjected to electrolytic graining in dilute nitric acid to perform composite graining, and then anodized in 20% sulfuric acid at a current density of 2 A/dm 2 for 2 minutes, followed by a 2.5% aqueous solution of sodium silicate at 70°C. for 1 minute.
このアルミニウム板につぎの感光液を塗布し
100℃で２分間乾燥塗布重量2.5ｇ／m2の感光性平
版印刷版を得た。 Apply the following photosensitive liquid to this aluminum plate.
A photosensitive lithographic printing plate having a coating weight of 2.5 g/m 2 was obtained by drying at 100° C. for 2 minutes.
２−ヒドロキシエチルメタクリ 0.87ｇ
レート共重合体（米国特許第
4123276号明細書中
の 中の実施例１に記載されている
もの）
ｐ−ジアゾジフエニアミンと 0.10ｇ
パラホルムアルデヒドの縮
合物の２−メトキシ−４−
ヒドロキシ−５−ベンゾイ
ルベンゼンスルホン酸塩
オイルブル−＃603 0.03ｇ
（オリエント化学工業(株)製）
ピコリン酸 0.01ｇ
エチレングリコールモノメチル 100ｇ
エーテル
メタノール 30ｇ
メチルエチルケトン 60ｇ
水 ２ｇ
この感光性平版印刷版を45℃、75％湿度の強制
条件下に５日間放置した後に画像露光し、ベンジ
ルアルコール30ｇ、トリエタノールアミン10ｇ、
イソプロピルナフタレンスルホン酸ナトリウム10
ｇ、亜硫酸ナトリウム２ｇ、ニトリロトリ酢酸ナ
トリウム0.5ｇおよび水道水950ｇよりなる現像液
で皿現像法により25℃、60秒間現像した後、水洗
しアラビアガムからなる保護ガムを塗布した。こ
の製版した印刷版を印刷機に取付けて非画像部の
汚れを調べたが、まつたく汚れは認められなかつ
た。比較として前記処方の中からピコリン酸を除
去した感光性平版印刷版を作り強制経時における
非画像部の汚れを調べたが、全面に印刷インキが
付着し満足する印刷物が得られなかつた。 2-Hydroxyethyl methacrylate 0.87 g 2-hydroxyethyl methacrylate copolymer (as described in Example 1 in U.S. Pat. No. 4,123,276) Condensate of p-diazodipheniamine and 0.10 g paraformaldehyde 2 -Methoxy-4-Hydroxy-5-benzoylbenzenesulfonate Oil Blue-#603 0.03g (manufactured by Orient Chemical Industry Co., Ltd.) Picolinic acid 0.01g Ethylene glycol monomethyl 100g Ether Methanol 30g Methyl ethyl ketone 60g Water 2g This photosensitive lithographic printing After leaving the plate under forced conditions of 45°C and 75% humidity for 5 days, it was image-exposed and treated with 30 g of benzyl alcohol, 10 g of triethanolamine,
Sodium Isopropyl Naphthalene Sulfonate 10
After developing for 60 seconds at 25° C. using a dish development method using a developer consisting of 2 g of sodium sulfite, 2 g of sodium nitrilotriacetate, and 950 g of tap water, the film was washed with water and a protective gum made of gum arabic was applied. This plate-made printing plate was mounted on a printing press and the non-image area was examined for stains, but no stains were observed. As a comparison, a photosensitive lithographic printing plate was made from the above formulation in which picolinic acid was removed and the staining of the non-image areas was examined after forced aging, but printing ink adhered to the entire surface and satisfactory printed matter could not be obtained.
実施例 ２
実施例１のピコリン酸の代わりにルチジン酸を
用いたが、実施例１と同様に45℃、75％湿度の強
制条件下に５日間放置しても非画像部に汚れのな
い美しい印刷物を得ることが出来た。Example 2 Lutidic acid was used in place of picolinic acid in Example 1, but as in Example 1, even if left for 5 days under the forced conditions of 45°C and 75% humidity, the non-image area remained clean and beautiful. I was able to obtain a printed copy.
実施例 ３
窒素気流下にエチレングリコールモノメチルエ
ーテル1000ｇを100℃に加熱し、この中に２−ヒ
ドロキシエチルメタクリレート23ｇ、アクロニト
リル27.5ｇ、ベンジルメタクリレート43ｇ、メタ
クリル酸6.5ｇ及び過酸化ベンゾイル0.4ｇの混合
液を２時間かけて滴下した。滴下終了15分後にエ
チレングリコールモノメチルエーテル100ｇと過
酸化ベンゾイル0.1ｇを加えて、そのまま４時間
反応させた。反応終了後メタノールで希釈して水
中に投じて共重合体を沈澱させ、70℃で真空乾燥
させた。この２−ヒドロキシエチルメタクリレー
ト共重合の酸化は40であつた。Example 3 1000 g of ethylene glycol monomethyl ether was heated to 100°C under a nitrogen stream, and 23 g of 2-hydroxyethyl methacrylate, 27.5 g of acronitrile, 43 g of benzyl methacrylate, 6.5 g of methacrylic acid, and 0.4 g of benzoyl peroxide were mixed therein. The liquid was added dropwise over 2 hours. 15 minutes after the completion of the dropwise addition, 100 g of ethylene glycol monomethyl ether and 0.1 g of benzoyl peroxide were added, and the mixture was allowed to react for 4 hours. After the reaction was completed, the copolymer was diluted with methanol and poured into water to precipitate the copolymer, followed by vacuum drying at 70°C. The oxidation rate of this 2-hydroxyethyl methacrylate copolymer was 40.
厚さ0.24mmの2Sアルミニウム板を80℃に保たれ
た第３りん酸ナトリウムの10％水溶液に３分間浸
漬して脱脂し、ナイロンブラシとパミススラリー
で砂目立て後、60℃のアルミン酸ナトリウム３％
水溶液でデスマツトした。このアルミニウム板を
20％硫酸中で2A／ｄm2の電流密度で２分間陽極
酸化し、その後70℃の珪酸カリウムの３％水溶液
で１分間処理した。この親水化処理したアルミニ
ウム板につぎに示す感光液を塗布し100℃２分間
乾燥させ、乾燥塗布重量1.5ｇ／m2の感光性平版
印刷版を得た。 A 2S aluminum plate with a thickness of 0.24 mm was degreased by immersing it in a 10% aqueous solution of tertiary sodium phosphate kept at 80℃ for 3 minutes, then grained with a nylon brush and pumice slurry, and then soaked in sodium aluminate 3 at 60℃. %
Desmatted with an aqueous solution. This aluminum plate
Anodization was carried out in 20% sulfuric acid at a current density of 2 A/dm 2 for 2 minutes, followed by treatment with a 3% aqueous solution of potassium silicate at 70° C. for 1 minute. The following photosensitive solution was coated on this hydrophilized aluminum plate and dried at 100°C for 2 minutes to obtain a photosensitive lithographic printing plate with a dry coating weight of 1.5 g/m 2 .
上記の２−ヒドロキシエチルメ 5.0ｇ
タクリレート共重合体
ｐ−ジアゾフエニルアミンと 0.7ｇ
パラホルムアルデヒドの縮合
物のPF6塩（PF6塩置換
率89％）
ビクトリアピユアーブル−BOH 0.1ｇ
（保士谷化学(株)製）
キノリン酸 0.01ｇ
亜りん酸 0.01ｇ
エスレングリコールモノメチル 50ｇ
エーテル
メタノール 16ｇ
メチルエチルケトン 32ｇ
水 １ｇ
この感光性平版印刷版を45℃、75％湿度の強制
条件下に５日間放置した後画像露光しベンジルア
ルコール450ｇ、トリエタノールアミン150ｇ、モ
ノエタノールアミン10ｇ、ｔ−ブチルナフタレン
スルホン酸ナトリウム150ｇ、亜硫酸ナトリウム
30ｇおよびイオン交換水8420ｇよりなる現像液を
市販の自現機で25℃50秒間現像し平版印刷版を得
た。 5.0 g of the above 2-hydroxyethylmethacrylate copolymer PF 6 salt of the condensation product of p-diazophenylamine and 0.7 g of paraformaldehyde (PF 6 salt substitution rate: 89%) Victoria Pour Blue - BOH 0.1 g (preservative) (Manufactured by Shitani Chemical Co., Ltd.) Quinolinic acid 0.01g Phosphorous acid 0.01g Ethlene glycol monomethyl 50g Ether Methanol 16g Methyl ethyl ketone 32g Water 1g This photosensitive lithographic printing plate was left under forced conditions of 45°C and 75% humidity for 5 days. After image exposure, 450 g of benzyl alcohol, 150 g of triethanolamine, 10 g of monoethanolamine, 150 g of sodium t-butylnaphthalenesulfonate, and sodium sulfite were added.
A developing solution consisting of 30 g and 8,420 g of ion-exchanged water was used for development at 25° C. for 50 seconds using a commercially available automatic processor to obtain a lithographic printing plate.
この印刷版を印刷機に取付けて印刷したところ
非画像部に汚れのないきれいな印刷物を得た。尚
この感光性平版印刷版は画像露光の際に鮮明な焼
出し性を有していた。 When this printing plate was attached to a printing machine and printed, a clean printed matter with no stains in the non-image area was obtained. This photosensitive lithographic printing plate had clear printout properties during image exposure.
なお、上記処方からキノリン酸を除いたものは
露光の際鮮明な焼出し性は有していたが、現像後
印刷すると非画像部が汚れ満足する印刷物は得ら
れなかつた。 Note that the formulation obtained by removing quinolinic acid from the above formulation had clear printout properties upon exposure, but when printed after development, the non-image area was smeared and a satisfactory printed matter could not be obtained.
Claims (1)
媒に可溶で実質的に水不溶性のジアゾ樹脂と実質
的に水不溶性で皮膜形成能を有する有機高分子化
合物からなる感光層を設けた感光性平版印刷版に
おいて、該感光層にジピコリン酸（塩）を除くＮ
−ヘテロ環カルボン酸を該ジアゾ樹脂に対して１
〜100重量％含有させたことを特徴とする感光性
平版印刷版。1 A photosensitive lithographic plate in which a photosensitive layer consisting of a diazo resin that is soluble in an organic solvent and substantially water-insoluble and an organic polymer compound that is substantially water-insoluble and has film-forming ability is provided on a hydrophilized aluminum plate. In the printing plate, the photosensitive layer contains N excluding dipicolinic acid (salt).
- 1 heterocyclic carboxylic acid to the diazo resin
A photosensitive lithographic printing plate characterized by containing ~100% by weight.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17295884A JPS6151142A (en) | 1984-08-20 | 1984-08-20 | Photosensitive lithographic plate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17295884A JPS6151142A (en) | 1984-08-20 | 1984-08-20 | Photosensitive lithographic plate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6151142A JPS6151142A (en) | 1986-03-13 |
| JPH0322617B2 true JPH0322617B2 (en) | 1991-03-27 |
Family
ID=15951511
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP17295884A Granted JPS6151142A (en) | 1984-08-20 | 1984-08-20 | Photosensitive lithographic plate |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6151142A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62275243A (en) * | 1986-05-23 | 1987-11-30 | Fuji Photo Film Co Ltd | Production of photosensitive material |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5033769A (en) * | 1973-07-26 | 1975-04-01 | ||
| JPS5344185A (en) * | 1976-10-05 | 1978-04-20 | Toko Inc | Oscillation element |
-
1984
- 1984-08-20 JP JP17295884A patent/JPS6151142A/en active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5033769A (en) * | 1973-07-26 | 1975-04-01 | ||
| JPS5344185A (en) * | 1976-10-05 | 1978-04-20 | Toko Inc | Oscillation element |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6151142A (en) | 1986-03-13 |
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