JPH0513304B2 - - Google Patents
Info
- Publication number
- JPH0513304B2 JPH0513304B2 JP59089342A JP8934284A JPH0513304B2 JP H0513304 B2 JPH0513304 B2 JP H0513304B2 JP 59089342 A JP59089342 A JP 59089342A JP 8934284 A JP8934284 A JP 8934284A JP H0513304 B2 JPH0513304 B2 JP H0513304B2
- Authority
- JP
- Japan
- Prior art keywords
- photosensitive
- water
- organic solvent
- acid
- aqueous dispersion
- 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 - Fee Related
Links
- 239000006185 dispersion Substances 0.000 claims description 44
- 239000003960 organic solvent Substances 0.000 claims description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
- 239000007788 liquid Substances 0.000 claims description 21
- 238000007639 printing Methods 0.000 claims description 17
- 229910052709 silver Inorganic materials 0.000 claims description 14
- 239000004332 silver Substances 0.000 claims description 14
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- 229920003176 water-insoluble polymer Polymers 0.000 claims description 11
- 230000001804 emulsifying effect Effects 0.000 claims description 8
- 239000010419 fine particle Substances 0.000 claims description 4
- -1 5-sulfonic acid Chemical class 0.000 description 46
- 239000000243 solution Substances 0.000 description 26
- 229920005989 resin Polymers 0.000 description 21
- 239000011347 resin Substances 0.000 description 21
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 18
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 13
- 229910052782 aluminium Inorganic materials 0.000 description 12
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 12
- 239000011230 binding agent Substances 0.000 description 11
- 238000001035 drying Methods 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 9
- 238000005299 abrasion Methods 0.000 description 8
- 239000011248 coating agent Substances 0.000 description 8
- 238000000576 coating method Methods 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 6
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 239000000123 paper Substances 0.000 description 6
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 5
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 229920001568 phenolic resin Polymers 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
- 108010010803 Gelatin Proteins 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 239000008273 gelatin Substances 0.000 description 4
- 229920000159 gelatin Polymers 0.000 description 4
- 235000019322 gelatine Nutrition 0.000 description 4
- 235000011852 gelatine desserts Nutrition 0.000 description 4
- 239000005011 phenolic resin Substances 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000004677 Nylon Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000084 colloidal system Substances 0.000 description 3
- 230000005611 electricity Effects 0.000 description 3
- VOOLKNUJNPZAHE-UHFFFAOYSA-N formaldehyde;2-methylphenol Chemical compound O=C.CC1=CC=CC=C1O VOOLKNUJNPZAHE-UHFFFAOYSA-N 0.000 description 3
- 229920001778 nylon Polymers 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- UTWVENOYOROSRG-UHFFFAOYSA-N 1,4-didodecoxy-1,4-dioxobutane-2-sulfonic acid;sodium Chemical compound [Na].CCCCCCCCCCCCOC(=O)CC(S(O)(=O)=O)C(=O)OCCCCCCCCCCCC UTWVENOYOROSRG-UHFFFAOYSA-N 0.000 description 2
- 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 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-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
- FUGYGGDSWSUORM-UHFFFAOYSA-N 4-hydroxystyrene Chemical compound OC1=CC=C(C=C)C=C1 FUGYGGDSWSUORM-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 229930040373 Paraformaldehyde Natural products 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 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
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000004115 Sodium Silicate Substances 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000005215 alkyl ethers Chemical class 0.000 description 2
- 150000001408 amides Chemical group 0.000 description 2
- 239000003945 anionic surfactant Substances 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 235000019445 benzyl alcohol Nutrition 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
- 238000009835 boiling Methods 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- 239000003093 cationic surfactant Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 235000010980 cellulose Nutrition 0.000 description 2
- 229920002301 cellulose acetate Polymers 0.000 description 2
- 229930003836 cresol Natural products 0.000 description 2
- 238000004945 emulsification Methods 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- 238000007645 offset printing Methods 0.000 description 2
- 229920002866 paraformaldehyde Polymers 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- 239000002985 plastic film Substances 0.000 description 2
- 229920006255 plastic film Polymers 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 229920000915 polyvinyl chloride Polymers 0.000 description 2
- 239000004800 polyvinyl chloride Substances 0.000 description 2
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 2
- 229910052911 sodium silicate Inorganic materials 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
- 239000000126 substance Substances 0.000 description 2
- 229940124530 sulfonamide Drugs 0.000 description 2
- 150000003456 sulfonamides Chemical group 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
- BSHCHXDUHUNQGW-UHFFFAOYSA-N 1-(4-azidophenyl)-3-(furan-2-yl)prop-2-en-1-one Chemical compound C1=CC(N=[N+]=[N-])=CC=C1C(=O)C=CC1=CC=CO1 BSHCHXDUHUNQGW-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
- 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
- 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
- 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
- MJFRJVWTRNRXIF-UHFFFAOYSA-N 2,5-diazido-3,6-dichlorocyclohexa-2,5-diene-1,4-dione Chemical compound ClC1=C(N=[N+]=[N-])C(=O)C(Cl)=C(N=[N+]=[N-])C1=O MJFRJVWTRNRXIF-UHFFFAOYSA-N 0.000 description 1
- MADGGJXZXKOPDW-UHFFFAOYSA-N 2,5-dimethoxy-4-morpholin-4-ylbenzenediazonium Chemical compound C1=C([N+]#N)C(OC)=CC(N2CCOCC2)=C1OC MADGGJXZXKOPDW-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
- IJXPXNZUSXLSTF-UHFFFAOYSA-N 2-[2-(4-butoxyphenyl)ethenyl]-5-(trichloromethyl)-1,3,4-oxadiazole Chemical compound C1=CC(OCCCC)=CC=C1C=CC1=NN=C(C(Cl)(Cl)Cl)O1 IJXPXNZUSXLSTF-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- GNTARUIZNIWBCN-UHFFFAOYSA-N 2-chloro-5-nitrobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC([N+]([O-])=O)=CC=C1Cl GNTARUIZNIWBCN-UHFFFAOYSA-N 0.000 description 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
- DYNFCHNNOHNJFG-UHFFFAOYSA-N 2-formylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C=O DYNFCHNNOHNJFG-UHFFFAOYSA-N 0.000 description 1
- ZRUOTKQBVMWMDK-UHFFFAOYSA-N 2-hydroxy-6-methylbenzaldehyde Chemical compound CC1=CC=CC(O)=C1C=O ZRUOTKQBVMWMDK-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical group 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
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- CVEPFOUZABPRMK-UHFFFAOYSA-N 2-methylprop-2-enoic acid;styrene Chemical compound CC(=C)C(O)=O.C=CC1=CC=CC=C1 CVEPFOUZABPRMK-UHFFFAOYSA-N 0.000 description 1
- UOBYKYZJUGYBDK-UHFFFAOYSA-N 2-naphthoic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CC=C21 UOBYKYZJUGYBDK-UHFFFAOYSA-N 0.000 description 1
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
- PYSRRFNXTXNWCD-UHFFFAOYSA-N 3-(2-phenylethenyl)furan-2,5-dione Chemical compound O=C1OC(=O)C(C=CC=2C=CC=CC=2)=C1 PYSRRFNXTXNWCD-UHFFFAOYSA-N 0.000 description 1
- UDGHVRJYOAZFLV-UHFFFAOYSA-N 3-(4-azidophenyl)-1-thiophen-2-ylprop-2-en-1-one Chemical compound C1=CC(N=[N+]=[N-])=CC=C1C=CC(=O)C1=CC=CS1 UDGHVRJYOAZFLV-UHFFFAOYSA-N 0.000 description 1
- MGVDSBGNZUMFRD-UHFFFAOYSA-N 3-benzoylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 MGVDSBGNZUMFRD-UHFFFAOYSA-N 0.000 description 1
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- IQOJIHIRSVQTJJ-UHFFFAOYSA-N 3-chlorobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC(Cl)=C1 IQOJIHIRSVQTJJ-UHFFFAOYSA-N 0.000 description 1
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- G03F7/023—Macromolecular quinonediazides; Macromolecular additives, e.g. binders
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- 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
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- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
Description
〔産業上の利用分野〕
本発明は、感光性画像形成材料に関し、更に詳
細には、皮膜の耐摩耗性がすぐれかつ水系現像液
で現像可能な感光性画像形成材料に関する。
〔従来技術〕
従来、皮膜の耐摩耗性を改良する感光性組成物
については多くのものが知られている。例えば感
光性ジアゾ樹脂にバインダーとして米国特許第
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、ビスフエノールＡとエピクロルニド
リンから縮合されたエポキシ樹脂、セルロースア
ルキルエーテル、酢酸セルロース、セルロースア
セテートフタレート等のセルロース類等を加えた
感光性組成物が知られている。更にｏ−キノンジ
アジド化合物にバインダーとして付加的に米国特
許第2826501号に示されているナイロン、特公昭
46−42448号公報に記されているポリウレタン、
ポリ塩化ビニル、エポキシ樹脂 特公昭46−
16049号公報に記されているポリビニルエーテル
等を加えた感光性組成物が知られている。しかし
ながらこれらのものは水を主体とする水系現像液
では耐摩耗性を向上させるほど前記ポリマーを添
加すると充分に現像ができないという欠点があつ
た。水系現像液を用いれば、無臭、非燃焼性、無
毒性、廃液処理の容易性等非常に好ましいにもか
かわらず、耐摩耗性のすぐれた水系現像液で現像
可能な感光性組成物は見い出されていない。
〔発明の目的〕
従つて本発明の目的は、耐摩耗性がすぐれかつ
水系現像液で現像可能な非銀感光性平版印刷版を
提供することにある。
〔発明の構成〕
本発明の目的は、支持体上に２層の非銀感光層
を有し、上層の感光性層中に親油性水不溶性ポリ
マーの微粒子分散物を含有することを特徴とする
非銀感光性平版印刷版によつて達成される。
更に、本発明の目的は支持体上に下層として水
系現像液で現像可能な感光性成分を塗設し、上層
に水系現像液で現像可能な非銀感光性成分を有機
溶解に溶解し該有機溶剤溶液を水中で乳化分散し
た液と親油性水不溶性ポリマーを有機溶剤に溶解
し、該有機溶剤を水中で乳化分散した液を混合し
て得た水系現像液で現像可能な感光性組成物を塗
設した２層からなる非銀感光性平版印刷版によつ
て達成される。
以下本発明を更に詳細に説明する。
（非銀感光材組成物）
本発明に有用な非銀感光性成分には、次のよう
なものが含まれる。
(1) ジアゾ樹脂からなる感光性成分
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
−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−モルホリノベンゼンジアゾニウムとホル
ム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、英国特許第1074392号
明細書に記されているフエノール樹脂等が包含さ
れる。
バインダーの含有量は、感光性レジスト形成性
成分中に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成分には、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感光性成
分
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共に
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ビト
樹脂、ｏ−クレゾールホルムアルデヒド樹脂、ｍ
−クレゾールホルムアルデビト樹脂などが含まれ
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成分の全
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成分
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感光性成分
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があ
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ビト樹脂などの
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−無水マイレン酸共重合体など
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
ヒドなどのアルデビト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。
バインダーは、感光性アジド化合物からなる組
成物の全重量に対して約10重量％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成分には、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
[Industrial Application Field] The present invention relates to a photosensitive image forming material, and more particularly to a photosensitive image forming material whose film has excellent abrasion resistance and can be developed with an aqueous developer. [Prior Art] Many photosensitive compositions that improve the abrasion resistance of films are known. For example, as a binder for photosensitive diazo resin, the US patent
Polyamide resin described in specification No. 3751257,
Polyvinyl formal resins as described in British Patent No. 1,074,392, polyvinyl acetal resins such as polyvinyl butyral resins, linear polyurethane resins as described in US Pat. No. 3,660,097, bisphenol A and epi- Photosensitive compositions containing epoxy resin condensed from chlornidoline, celluloses such as cellulose alkyl ether, cellulose acetate, and cellulose acetate phthalate are known. Furthermore, the o-quinonediazide compound may be additionally used as a binder, such as the nylon shown in U.S. Pat. No. 2,826,501,
Polyurethane described in Publication No. 46-42448,
Polyvinyl chloride, epoxy resin
A photosensitive composition containing polyvinyl ether and the like is known as described in Japanese Patent No. 16049. However, these materials have the disadvantage that sufficient development cannot be achieved with an aqueous developer mainly composed of water if the polymer is added to the extent that the abrasion resistance is improved. Although the use of an aqueous developer is highly desirable, as it is odorless, non-flammable, non-toxic, and easy to dispose of waste liquid, no photosensitive composition that can be developed with an aqueous developer with excellent abrasion resistance has been found. Not yet. [Object of the Invention] Therefore, an object of the present invention is to provide a non-silver photosensitive lithographic printing plate which has excellent abrasion resistance and can be developed with an aqueous developer. [Structure of the Invention] The object of the present invention is to have two non-silver photosensitive layers on a support, and the upper photosensitive layer contains a fine particle dispersion of a lipophilic water-insoluble polymer. Achieved by a non-silver photosensitive lithographic printing plate. Furthermore, the object of the present invention is to coat a photosensitive component that can be developed with an aqueous developer as a lower layer on a support, and to form a non-silver photosensitive component that can be developed with an aqueous developer as an upper layer by dissolving it in an organic solution. A photosensitive composition that can be developed with an aqueous developer obtained by mixing a liquid obtained by emulsifying and dispersing a solvent solution in water and a liquid obtained by dissolving a lipophilic water-insoluble polymer in an organic solvent and emulsifying and dispersing the organic solvent in water. This is achieved by a non-silver sensitive lithographic printing plate consisting of two coated layers. The present invention will be explained in more detail below. (Non-silver photosensitive material composition) Non-silver photosensitive components useful in the present invention include the following. (1) Photosensitive component 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 those soluble in common organic solvents are used. Particularly preferred diazo compounds include salts of condensates of p-diazophenylamine and formaldehyde or acetaldehyde;
For example, phenolic salts, fluorocaprates, and triisopropylnaphthalenesulfonic acid, 4,
4-biphenyldisulfonic acid, 5-nitroortho-toluenesulfonic 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 2,5-dimethoxy-4 containing the above salts.
-p-Tolylmercaptone Condensates of benzenediazonium and formaldehyde, and condensates of 2,5-dimethoxy-4-morpholinobenzenediazonium 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 polymeric compounds can be used as such binders, but those containing groups such as hydroxy, amino, 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. Included are polymers containing ethyl methacrylate units as a main repeating unit, phenolic resins described in British Patent No. 1074392, and the like. The content of the binder is suitably 40 to 95% by weight in the photosensitive resist-forming component. 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 component. (2) Photosensitive component consisting of an o-quinonediazide compound A particularly preferred o-quinonediazide compound is an o-quinonediazide compound.
Naphthoquinonediazide compounds, such as U.S. Patent No. 2766118, U.S. Patent No. 2767092, U.S. Patent No. 2772972
No. 2859112, No. 2907665, No. 2907665, No. 2859112, No. 2907665, No.
No. 3046110, No. 3046111, No. 3046115, No. 3046118, No. 3046119, No. 3046120,
Same No. 3046121, Same No. 3046122, Same No. 3046123,
Same No. 3061430, Same No. 3102809, Same No. 3106465,
It is described in numerous publications including the specifications of the same No. 3635709 and the same 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, a condensate of pyrogallol and acetone described in U.S. Pat. No. 3,635,709, which is subjected to an ester reaction with o-naphthoquinonediazide sulfonic acid, and U.S. Pat. No. 4,028,111.
British patent no.
A homopolymer of p-hydroxystyrene or a copolymer with a monomer copolymerizable with the p-hydroxystyrene as described in No. 1494043 is subjected to an ester reaction with o-naphthoquinonediazide sulfonic acid or o-naphthoquinonediazidecarboxylic acid. Things are 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, specifically phenol formaldevit resin, o-cresol formaldehyde resin, m
-Includes cresol formaldevit resin, etc. Further, as described in U.S. Pat. No. 4,123,279, along with the above-mentioned phenolic resin, t
It is even more preferable to use a condensate of formaldehyde and phenol or cresol substituted with an alkyl group having 3 to 8 carbon atoms, such as -butylphenol formaldehyde resin. The alkali-soluble resin is contained in an amount of about 50 to about 85% by weight, more preferably 60 to 80% by weight, based on the total weight of the photosensitive resist-forming components. The photosensitive component made of the o-quinonediazide compound can further contain pigments, dyes, plasticizers, etc., if necessary. (3) Photosensitive component composed of photosensitive azide compound Suitable photosensitive azide compounds include aromatic azide compounds in which the 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, such as 4,4-diazidochalcone,
4-azido-4'-(4-azidobenzoylethoxy)chalcone, N,N-bis-p-azidobenzal-p-phenylenediamine, 1,2,6-tri(4'-azidobenzoxy)hexane, 2-azide -3-chloro-benzoquinone, 2,4-diazide-4'-ethoxyazobenzene, 2,6-di(4'-
azidobenzal)-4-methylcyclohexanone,
4,4'-Diazidobenzophenone, 2,5-diazido-3,6-dichlorobenzoquinone, 2,5-
Bis(4-azidostyryl)-1,3,4-oxadiazole, 2-(4-azidocinnamoyl)
Thiophene, 2,5-di(4'-azidobenzal)
Cyclohexanone, 4,4'-diazidiphenylmethane, 1-(4-azidophenyl)-5-furyl-2-pent-2,4-dien-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-one, 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'-diazide-stilbene-2,
Examples include 2'-disulfonic acid anilide. In addition to these low molecular weight aromatic azide compounds, Japanese Patent Publications No. 44-9047, No. 44-31837, No.
No. 9613, No. 45-24915, No. 45-25713, JP-A-Sho
No. 50-5102, No. 50-84302, No. 50-84303, No. 50-84302, No. 50-84303, No.
The azide group-containing polymers described in Patent Publications 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, novolak-type phenolic resins such as phenol formaldehyde resin, m-cresol formaldehyde resin, and polyacrylic acid, polymethacrylic acid, and methacrylic acid-styrene. Copolymers, homopolymers of unsaturated carboxylic acids such as methacrylic acid-methyl acrylate copolymers, styrene-maleic anhydride copolymers, or copolymers of these with other copolymerizable monomers, polyacetic acid Included are resins obtained by partially or completely saponified vinyl partially acetalized with aldevites such as hydroxybenzaldehyde and carboxybenzaldehyde, and polyhydroxystyrene. The binder is about 10% to about 90% by weight based on the total weight of the composition consisting of the photosensitive azide compound.
The content is preferably within the range of . The component consisting of the photosensitive azide compound further contains dyes and pigments such as phthalic esters, phosphoric esters, aliphatic carboxylic esters, glycols,
Plasticizers such as sulfonamides, such as Michler's ketone, 9-fluorenone, 1-nitropyrene, 1,8-dinitropyrene, 2-chloro-1,
2-Benzanthraquinone, 2-bromo-1,2
- Additives such as sensitizers such as 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感光性成分
重合体主鎖又は側鎖に感光性基として
[Formula] A photosensitive component consisting of a polymer compound containing a group As a photosensitive group in the polymer main chain or side chain
本発明に使用できる支持体としては、適当な表
面処理を施したアルミニウム、紙、プラスチツク
フイルム、及びそれらの積層体があげられる。プ
ラスチツクフイルムの材質は例えば、ポリエチレ
ン、ポリプロピレン等のポリオリフイン、ポリ酢
酸ビニル、ポリ塩化ビニル等のビニル重合体、ポ
リエチレンテレフタレート、ポリエチレン−２，
６−ナフタレート等のポリエステル、セルロース
トリアセテート等のセルロースアセテートがあれ
られる。積層体としては、紙の両側を、表面処理
を施したアルミニウムで被覆したもの、ポリエチ
レンテレフタレートフイルムの両側もしくは片側
を、表面処理を施したアルミニウムで被覆したも
の、ポリプロピレンフイルムの両側もしくは片側
を、表面処理を施したアルミニウムで被覆したも
の等があげられる。
〔感光性組成物水分散液〕
本発明になる感光性組成物の水分散液は一般的
に次のようにして製造する。前記の非銀感光性成
分及び親油性水不溶性ポリマーをそれぞれ適当な
１種または２種以上の別々の有機溶剤に溶解し有
機溶剤溶液とする。好ましい溶剤としては水に対
する溶解度が大きくなく（25℃で40％以下）、沸
点が低い（１気圧で150℃以下）か又は水と共沸
して水より沸点が低く、上記成分を溶解すればど
のうな溶剤でもよい。例えば、エチレンジクロラ
イド、シクロヘキサノン メチルエチルケトン、
エチレングリコールモノメチルエーテル、エチレ
ングリコールモノエチルエーテル、ジメチルホル
ムアミド、ジエチルホルムアミド、トルエン、酢
酸エチル、酢酸ブチル、テトラヒドロフラン、メ
チルセロソルブ、ブチルアルコール、クロロホル
ム、四塩化炭素、トリクロルエタン、ベンゼン、
メチルイソブチルケトン等が挙げられる。有機溶
剤溶液中の溶剤以外の成分の濃度は一般に２〜80
重量％が好ましい。
次いで上記の２種類の有機溶剤溶液をそれぞれ
水中で乳化分散する。乳化分散する際に分散安定
剤として親水性コロイド、界面活性剤を使用する
ことが有利な場合がある。親水性コロイドとして
は、ゼラチン、ゼラチン誘導体（例えばアセチル
化ゼラチン、フタル化ゼラチン等）、アルブミン、
カゼイン等の蛋白質類、コロジオン、アラビアガ
ム、寒天、ポリビニルアルコール、ポリビニルピ
ロリドン、ポリアクリル酸塩、ポリメタアクリル
酸塩等が挙げられる。界面活性剤としてはポリオ
キシエチレンアルキルエーテル類ポリオキシエチ
レンアルキル フエニルエーテル類、ポリオキシ
エチレン脂肪酸エステル類、ソルビタン脂肪酸エ
ステル類、ポリオキシエチレンソルビタン脂肪酸
エステル類、グリセリン脂肪酸エステル類などの
非イオン界面活性剤、例えば脂肪酸塩類、アルキ
ル硫酸エステル塩類、アルキルベンゼンスルホン
酸塩類、アルキルナフタレンスルホン酸塩類、ジ
アルキルスルホこはく酸エステル塩類、アルキル
燐酸エステル塩類、ナフタレンスルホン酸ホルマ
リン縮合物、ポリオキシエチレンアルキル硫酸エ
ステル塩類などのアニオン界面活性剤、及び例え
ばアルキルアミン塩類、第４級アンモニウム塩
類、ポリオキシエチレンアルキルアミン塩類など
のカチオン界面活性剤、フツ素系界面活性剤が挙
げられる。これら分散安定剤は単独で用いても、
２種以上混合して使用してもよい。これら分散安
定剤は有機溶剤溶液または水中のいづれか一方、
あるいは両者に添加して使用する。使用量は有機
溶剤溶液の0.01〜10重量％が好ましい。使用する
水の量は有機溶剤溶液１重量に対して0.2〜20重
量が好ましい。
乳化分散するために使用する乳化装置として
は、処理液に大きな剪断力を与えるものか、又は
高強度の超音波エネルギーを与えるものが適して
いる。特にコロイドミル、ホモジナイザー、毛細
管式乳化装置、液体サイレン、電磁歪式超音波発
生機、ポールマン笛を有する乳化装置が良好な結
果を与えることができる。
好ましくは得られた乳化分散液を攪拌しながら
加熱することによつて使用した有機溶剤を除去す
る。除去する有機溶剤の量は20重量％以上、好ま
しくは50重量％以上である。除去する有機溶剤の
量が少ないと微粒子分散液とし添加した結果が小
さくなる。有機溶剤の除去は減圧下で行なうこと
により低温で効率よく行なえる。感光性成分分散
液及び親油性水不溶ポリマー分散液それぞれ別々
に有機溶剤を除去してから所定の割合に混合して
もよいし、両者を所定の割合に混合してから有機
溶剤を除去してもよい。
本発明の分散物の粒径は、約10mμ以下は調整
困難であり実用的でない。粒径は通常10mμ〜5μ、
好ましくは10mμ〜3μ程度であり、乳化条件を適
当に選んで調整することができる。粒径が大きい
と最終的に得られた画像の解像力が悪くなる。
乳化分散物の水中にしめる割合は２〜70重量％
が適当である。
本発明に係る下層は通常の方法で作られる。す
なわち前記感光性成分を溶剤に溶解し支持体上に
塗布乾燥する。溶剤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、テトラヒドロフラン、トルエ
ン、酢酸エチル、水等がありこれらの溶剤を単独
あるいは混合して使用する。そして固形分濃度は
２〜50重量％が適当である。
〔感光性平版印刷版〕
本発明に係る感光性平版印刷版は下層を塗布・
乾燥後上層を塗布・乾燥して製造するのが一般的
である。下層の塗布量は0.01g／m2〜10g／m2範囲
がよく、より好ましくは0.1g／m2〜3g／m2の範囲
である。塗布量が少ないと上層の耐摩耗性が低下
する。上層の塗布量は0.1g／m2〜10g／m2の範囲
がよく、より好ましくは0.5g／m2〜3g／m2の範囲
である。塗布量が少なくなるにつれて感光膜の物
性は低下する。
本発明に係る下層に通常の感光性成分溶液を設
け、上層に感光性成分と親油性水不溶性ポリマー
のそれぞれの水分散液を塗設すると、上層だけを
直接支持体上に塗設するのに較べ感光膜の耐摩耗
性例えばアルミニウム支持平版印刷版の耐刷性が
改良される理由は定かではないが、アルミニウム
と感光層との接着性が良くなるためと考えられ
る。すなわち水分散液中の分散物はアルミ表面の
凹凸の中に入りこまずしつかりとアルミと接着し
ないために耐刷性が劣つており、通常の感光液を
用いて下層を設けることにより接着性が良化し、
上層の感光層が本来持つている高い耐摩耗性を示
すものと考えられる。
本発明に係る感光性平版印刷版を製造するに
は、グラビアコート、バーコート、リバースロー
ルコート、ホワイラー、スピーナー、カーテン、
エクストル−ジヨンビード、スライスビード等の
塗布装置を用いて塗布し乾燥する。
上記のようにしてつくられた画像形成材料は、
まず活性光線により露光される。活性光線の光源
としては、例えば、水銀灯、メタルハライドラン
プ、キセノンランプ、ケミカルランプ、カーボン
アーク灯などがある。また高密度エネルギービー
ム（レーザービーム又は電子線）による走査露光
も本発明に使用することができる。このようなレ
ーザービームとしてはヘリウム・ネオンレーザ
ー、アルゴンレーザー、クリブトンイオンレーザ
ー、ヘリウム・カドミウムレーザーなどである。
露光後の平版印刷版は、適当な水系現像液に浸
漬して現像する。本発明に係る水系現像液は次の
ようなものが含まれる。PH８〜13.5を有するアル
カリ水溶液。アルカリ性は水溶性の無機塩基化合
物（例えばアルカリ金属の水酸化物、リン酸塩、
硫酸塩、ケイ酸塩、炭酸塩およびこれらの混合
物）、塩基性の水溶性有機化合物、例えばアミン
類、（例えばトリエタノールアミン、ジエチルア
ミン、ジエチルアミノエタノール等）及びこれら
の組合により付与する。水と有機溶媒との混合溶
液で有機溶媒が約20重量％以下含有している溶
液。有機溶媒としては、アルコール（例えば、グ
リセロール、ベンジルアルコール、２−フエノキ
シエタノール、２−ブトキシエタノール、１・２
−プロパンジオール、sec−ブチルアルコール、
アルキレングリコール等）酢酸ブチルのようなエ
ステル、メチルセロソルブのようなエーテル、シ
クロヘキサノン及びアセトンのようなケトン等が
挙げられる。更に界面活性剤を約20重量％以下含
有している溶液。界面活性剤としてはアニオン界
面活性剤、ノニオン界面活性剤、カチオン界面活
性剤、両性界面活性剤を用いることができる。更
にサルチル酸のような酸を含有している溶液。そ
してこれらすべての化合物を１種又は２種以上混
合して用いる。現像の際、スポンジ等の適当な材
料を用いて材料表面を擦接することにより現像を
より効果的に行なうことができる。
〔発明の効果〕
本発明による感光性平版印刷版は耐摩耗性がす
ぐれかつ水系現像液で現像できる。
以下、実施例を挙げて本発明を例証するが、本
発明の実施態様はこれらに限定されない。
実施例 １，２
特開昭56−28893号公報に開示された方法によ
り基板を作製した。即ち、厚さ0.24mmのアルミニ
ウム板をナイロンブラシと400メツシユのパミス
トンの水懸濁液を用い、その表面を砂目立てした
後、よく水で洗浄した。次いで10％水酸化ナトリ
ウムに70℃で60秒間浸漬してエツチングした後、
流水で水洗後20％HNO3で中和洗浄し、水洗し
た。これを陽極時電圧が12.7Vで陽極時電気量に
対する陰極時電気量の比が0.8の条件下で正弦波
の交番波形電流を用いて１％硝酸水溶液中で160
クーロン／ｄm2の電気量で電解粗面化処理を行つ
た。このときの表面粗さを測定したところ0.6μ
（Ra表示）であつた。ひきつづいて30％の硫酸中
に浸漬し55℃で２分間デスマツトした後、20％硫
酸中、電流密度2A／ｄm2において厚さが2.7g／
m2になるように２分間陽極酸化処理した。その後
70℃の珪酸ソーダ2.5％水溶液に１分間浸漬後水
洗乾燥した。このようにして準備された基板の上
に、次のようにして調液した感光液(A)を乾燥後の
皮膜が1.0μになるよう被覆した。つづいて水分散
感光液（＋）を乾燥後の皮膜が2μになるよ
うにして試料を得た。
（感光性成分を含む水分散液）
下記の有機溶剤溶液(A)を調液した。
ポリ（アリルメタアクリレート）／メタクリル
酸（共重合モル比85／15） 32.5
ペンタエリスリトールテトラアクリレート
17.5g
２−トリクロロメチル−５−（ｐ−ｎ−ブトキ
シスチリル）−１，３，４−オキサジアゾール
2g
油溶性青色染料（C.I.42595） 0.8g
ジラウリルスルホこはく酸ナトリウム 3g
エチレンジクロライド 150g
メチルエチルケトン 150g
次いで、該溶液(A)100gに水100gを加えてホモ
ジナイザーを用いて５分間高速攪拌を行ない乳化
分散液を作つた。この乳化分散液を攪拌しながら
85℃に加熱し、有機溶剤を除去した。これに水を
加え固形分濃度を10％に調整し、安定な水分散液
（）を得た。
（親油性水不溶性ポリマー水分散液）
次に下記の有機溶剤溶液(B)を調液した。
ポリメチルメタアクリレート 50g
ジラウリルスルホコハク酸ナトリウム 3g
エチレンジクロライド 150g
メチルエチルケトン 150g
次いで該溶液(B)100gに水100gに加えてホモジ
ナイザーを用いて５分間高速攪拌を行ない乳化分
散液を作つた。この乳化分散液を攪拌しながら85
℃に加熱し、有機溶剤を除去した。これに水を加
え、固形分濃度を10％に調整し、安定な水分散液
（）を得た。前記支持体に感光液(A)を塗布乾燥
しつづいて水分散液（）を60重量部と水分散液
（）を40重量部とを混合し水分散液（＋）
を得て上層として、塗布しサンプル（Ｐ）を得
た。比較のために水分散液感光液（＋）を前
記支持体に塗布し比較試料（Ｑ）を得た。乾燥後
の皮膜は3.0μであつた。
これらのサンプル(P)および(Q)の上にネガ画像フ
イルムを重ねて米国バーキテクニカル社製バーキ
−プリンタ−（アイコーアダルツクス2KW）で露
光し、次に示す現像液に室温で50秒間浸漬し脱脂
綿で表面を軽くこすり現像し印刷版を得た。
亜硫酸ナトリウム 5g
ベンジルアルコール 30g
炭酸ナトリウム 5g
イソプロピルナフタレンスルホン酸ナトリウム
12g
水 1000g
サンプル(P)は非画像部が完全に除去でき、枚葉
オフセツト印刷機にかけて上質紙に印刷したとこ
ろ７万枚以上の良好な印刷物が得られた。一方比
較サンプル(Q)は非画像部は完全に除去できたが同
じように印刷したところ５万枚の印刷物しか得ら
れなかつた。
実施例 ２
実施例１と同じ基板の上に、次にようにして調
液した感光液(C)を乾燥後の皮膜が1.0μになるよう
被覆しつづいて水分散感光液（＋）を乾燥後
の皮膜が1.5μになるように被覆して試料を得た。
（感光性成分を含む水分散液）
下記の有機溶剤溶液(C)を調液した。
２ヒドロキシエチルメタアクリレート共重合体
（米国特許第4123276号明細書中の実施例１に記
載されているもの） 97g
ｐ−ジアゾジフエニルアミンとパラホルムアル
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 10g
オイルブルー＃603（オリエント化学工業(株)製）
3g
３−カルボキシ−４−ヒドロオキシナフタレン
スルホン酸ソーダー 2g
ポリオキシエチレンソルビタンモノオレート
4g
エチレンジクロライド 500g
２−メトキシエタノール 250g
上記有機溶媒溶液(C)を用い実施例１と同じ方法
で水分散液（）を得た。前記支持体に感光液(C)
を塗布、乾燥し、つづいて水分散液（）を70重
量部と水分散液（）30重量部とを混合し、水分
散感光液（＋）を得て上層として塗布しサン
プル(R)を得た。比較のために水分散感光液（＋
）を前記支持体に塗布し、比較試料(S)を得た。
これらのサンプル(R)および(S)の上にネガ画像フイ
ルムを重ねバーキープリンターで露光し、次に現
像液に室温で60秒間浸漬し脱脂綿で表面を軽くこ
すり現像し、印刷版を得た。
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
10g
亜硫酸ナトリウム 2g
ニトリロトリ酢酸ナトリウム 0.5g
水 950g
サンプル(R)は非画像部が完全に除去でき、枚葉
オフセツト印刷機にかけて上質紙に印刷したとこ
ろ５万枚以上の良好な印刷物が得られた。一方比
較サンプル(S)は非画像部は完全に除去できたが同
じように印刷したところ４万枚の印刷物しか得ら
れなかった。
実施例 ３
厚さ0.24mmのISアルミニウム板を80℃に保つた
第３燐酸ナトリウムの10％水溶液に３分間浸漬し
て脱脂し、ナイロンブラシで砂目立てした後、ア
ルミン酸ナトリウムの25％（NaOHとして）水
溶液で約10秒間エツチングして、硫酸水素ナトリ
ウム３％水溶液でデスマツト処理を行つた。この
アルミニウム板を20％硫酸中で電流密度2A／ｄ
m2において２分間陽極酸化を行いアルミニウム板
を作つた。このようにして準備された基板の上
に、次のようにして調液した感光液(D)を乾燥後の
皮膜が0.5μになるよう被覆し、つづいて水分散感
光液（＋）を乾燥後の皮膜が2.5μになるよう
にして試料を得た。
（感光性成分を含む水分散液）
下記の有機溶剤溶液(D)を調液した。
１，２−ナフトキノン−２−ジアジド−５−ス
ルホニルクロライドとクレゾール−ホルムアル
デヒド樹脂との縮合物（米国特許第3046120号
の方法により合成した） 18g
クレゾールホルムアルデヒド樹脂（ヒタノール
＃3110（日立化成(株)製） 38g
油溶性染料（CI 42595） 0.6g
メガフアツクＦ−120（大日本インキ化学(株)製）
2g
メチルエチルケトン 300g
次いで、該溶液(D)100gに水150gを加えて、実
施例１と同様にして10％水分散液（）を得た。
（親油性水不溶性ポリマー水分散液）
次に下記の有機溶剤溶液(E)を調液した。
ｐ−tirt−ブチルフエノール−ホルムアルデヒ
ド樹脂 50g
メガフアツクＦ−120（大日本インキ化学(株)製）
3g
メチルエチルケトン 300g
該溶液(E)100gに水150gを加え実施例１と同じ
方法で水分散液（）を得た。
水分散液（）85重量部と水分散液（）15重
量部とを混合し、水分散液感光液（＋）を得
て上層として塗布しサンプル(T)を得た。比較のた
めに水分散感光液（＋）を前記支持体に塗布
し、比較試料(U)を得た。乾燥後の皮膜は3.0μであ
つた。これらのサンプル(T)および(U)の上にポジ画
像フイルムを重ねてバーキープリンターで露光
し、現像液（SiO2／Na2Ｏ＝1.2（モル比）でSiO2
の含量が1.5％の珪酸ナトリウム水溶液に室温で
30秒間浸漬し脱脂綿で表面を軽くこすり現像し、
印刷版を得た。サンプル(T)は非画像部が完全に除
去でき枚葉オフセツト印刷機にかけて上質紙に印
刷したところ６万枚以上の良好な印刷物が得られ
た。一方比較サンプル(U)は非画像部は除去できた
が、同じように印刷したところ３万枚の印刷物し
か得られなかつた。
実施例 ４
実施例３と同じ基板の上に実施例３の感光液(D)
を乾燥後の皮膜が1.0μになるように被覆し、つづ
いて次のようにして調液した水分散感光液（＋
）を乾燥後の皮膜が2.0μになるように被覆して
試料を得た。
（親油性水不溶性ポリマー水分散液）
下記の有機溶剤溶液(F)を調液した。
ポリビニルホルマール12／85T（モンサント社
製） 50g
メガフアツクＦ−120（大日本インキ化学(株)）
3g
エチレンジクロライド 150g
メチルエチルケトン 150g
該溶液(F)100gに水150gを加え実施例１と同じ
方法で水分散液（）を得た。実施例３の水分散
液（）80重量部と水分散液（）20重量部を混
合し、水分散感光液（＋）を得て上層として
塗布しサンプル(W)を得た。
比較のために水分散感光液（＋）を前記支
持体に塗布し比較試料(X)を得た、乾燥後の皮膜は
3.0μであつた。これらのサンプル(W)および(X)の上
にポジ画像フイルムを重ねバーキープリンターで
露光し、実施例３と同様に現像し、印刷版を得
た。サンプル(W)は非画像部が完全に除去でき、枚
葉オフセツト印刷機にかけて上質紙に印刷したと
ころ６万枚以上の良好な印刷物が得られた。一方
比較サンプル(X)は非画像部は除去できたが、同じ
ように印刷したところ４万枚の印刷物しか得られ
なかつた。
Supports that can be used in the present invention include aluminum, paper, plastic film, and laminates thereof that have been subjected to appropriate surface treatment. Examples of plastic film materials include polyolefins such as polyethylene and polypropylene, vinyl polymers such as polyvinyl acetate and polyvinyl chloride, polyethylene terephthalate, polyethylene-2,
Polyesters such as 6-naphthalate and cellulose acetates such as cellulose triacetate can be used. Examples of laminates include paper coated on both sides with surface-treated aluminum, polyethylene terephthalate film coated with surface-treated aluminum on both sides or one side, and polypropylene film coated with both sides or one side coated with surface-treated aluminum. Examples include those coated with treated aluminum. [Aqueous dispersion of photosensitive composition] The aqueous dispersion of the photosensitive composition of the present invention is generally produced as follows. The non-silver photosensitive component and the lipophilic water-insoluble polymer are each dissolved in one or more appropriate organic solvents to form an organic solvent solution. Preferred solvents include those that do not have high solubility in water (40% or less at 25°C), have a low boiling point (150°C or less at 1 atm), or have an azeotropic boiling point with water, and that dissolve the above components. Any solvent may be used. For example, ethylene dichloride, cyclohexanone methyl ethyl ketone,
Ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, dimethyl formamide, diethyl formamide, toluene, ethyl acetate, butyl acetate, tetrahydrofuran, methyl cellosolve, butyl alcohol, chloroform, carbon tetrachloride, trichloroethane, benzene,
Examples include methyl isobutyl ketone. The concentration of components other than the solvent in an organic solvent solution is generally 2 to 80
Weight percent is preferred. Next, the above two types of organic solvent solutions are each emulsified and dispersed in water. It may be advantageous to use a hydrophilic colloid or a surfactant as a dispersion stabilizer during emulsification and dispersion. Hydrophilic colloids include gelatin, gelatin derivatives (e.g. acetylated gelatin, phthalated gelatin, etc.), albumin,
Examples include proteins such as casein, collodion, gum arabic, agar, polyvinyl alcohol, polyvinylpyrrolidone, polyacrylates, polymethacrylates, and the like. Examples of surfactants include nonionic surfactants such as polyoxyethylene alkyl ethers, polyoxyethylene alkyl phenyl ethers, polyoxyethylene fatty acid esters, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, and glycerin fatty acid esters. agents, such as fatty acid salts, alkyl sulfate ester salts, alkylbenzene sulfonate salts, alkylnaphthalene sulfonate salts, dialkyl sulfosuccinate ester salts, alkyl phosphate ester salts, naphthalene sulfonic acid formalin condensate, polyoxyethylene alkyl sulfate ester salts, etc. Examples include anionic surfactants, cationic surfactants such as alkylamine salts, quaternary ammonium salts, polyoxyethylene alkylamine salts, and fluorine-based surfactants. Even if these dispersion stabilizers are used alone,
Two or more types may be mixed and used. These dispersion stabilizers can be used either in organic solvent solution or in water.
Alternatively, it can be used by adding it to both. The amount used is preferably 0.01 to 10% by weight of the organic solvent solution. The amount of water used is preferably 0.2 to 20% by weight per 1 weight of the organic solvent solution. As the emulsifying device used for emulsifying and dispersing, one that applies a large shearing force to the processing liquid or one that applies high-intensity ultrasonic energy is suitable. In particular, emulsifying devices having a colloid mill, a homogenizer, a capillary emulsifying device, a liquid siren, an electromagnetic strain ultrasonic generator, and a Pohlmann whistle can give good results. The used organic solvent is preferably removed by heating the obtained emulsified dispersion while stirring. The amount of organic solvent removed is at least 20% by weight, preferably at least 50% by weight. If the amount of organic solvent removed is small, the result of adding it as a fine particle dispersion will be small. The organic solvent can be efficiently removed at low temperature by performing it under reduced pressure. The photosensitive component dispersion and the lipophilic water-insoluble polymer dispersion may be mixed in a predetermined ratio after removing the organic solvent separately, or they may be mixed in a predetermined ratio and then the organic solvent removed. Good too. When the particle size of the dispersion of the present invention is about 10 mμ or less, it is difficult to control and is not practical. Particle size is usually 10mμ~5μ,
It is preferably about 10 mμ to 3μ, and can be adjusted by appropriately selecting emulsification conditions. If the particle size is large, the resolution of the final image will be poor. The proportion of the emulsified dispersion in water is 2 to 70% by weight.
is appropriate. The underlayer according to the invention is made in a conventional manner. That is, the photosensitive component is dissolved in a solvent, coated on a support and dried. Methyl cellosolve as a solvent,
Ethyl cellosolve, methyl cellosolve acetate, acetone, methyl ethyl ketone, methanol, dimethyl formamide, dimethyl sulfoxide, ethylene dichloride, cyclohexanone, dioxane, tetrahydrofuran, toluene, ethyl acetate, water, etc. These solvents can be used alone or in combination. do. The appropriate solid content concentration is 2 to 50% by weight. [Photosensitive planographic printing plate] The photosensitive planographic printing plate according to the present invention is coated with a lower layer.
It is generally manufactured by applying and drying the upper layer after drying. The coating amount of the lower layer is preferably in the range of 0.01 g/m 2 to 10 g/m 2 , more preferably in the range of 0.1 g/m 2 to 3 g/m 2 . If the coating amount is small, the wear resistance of the upper layer will decrease. The coating amount of the upper layer is preferably in the range of 0.1 g/m 2 to 10 g/m 2 , more preferably in the range of 0.5 g/m 2 to 3 g/m 2 . As the coating amount decreases, the physical properties of the photosensitive film deteriorate. According to the present invention, if a normal photosensitive component solution is provided in the lower layer and an aqueous dispersion of the photosensitive component and a lipophilic water-insoluble polymer is applied to the upper layer, it is possible to coat only the upper layer directly onto the support. The reason why the abrasion resistance of the photosensitive film, for example the printing durability of the aluminum-supported lithographic printing plate, is improved is not clear, but it is thought to be due to improved adhesion between the aluminum and the photosensitive layer. In other words, the dispersion in the aqueous dispersion does not penetrate into the unevenness of the aluminum surface and does not firmly adhere to the aluminum, resulting in poor printing durability. improved,
This is thought to be due to the high abrasion resistance inherent to the upper photosensitive layer. In order to produce the photosensitive lithographic printing plate according to the present invention, gravure coating, bar coating, reverse roll coating, whiler, spinner, curtain,
It is applied using a coating device such as an extrusion bead or a slicing bead and dried. The image forming material produced as described above is
First, it is exposed to actinic light. Examples of active light sources include mercury lamps, metal halide lamps, xenon lamps, chemical lamps, and carbon arc lamps. Scanning exposure with a high-density energy beam (laser beam or electron beam) can also be used in the present invention. Such laser beams include helium-neon lasers, argon lasers, krybton ion lasers, helium-cadmium lasers, and the like. The exposed planographic printing plate is developed by immersing it in a suitable aqueous developer. The aqueous developer according to the present invention includes the following. Alkaline aqueous solution with pH 8-13.5. Alkalinity refers to water-soluble inorganic base compounds (e.g. alkali metal hydroxides, phosphates,
sulfates, silicates, carbonates and mixtures thereof), basic water-soluble organic compounds such as amines (such as triethanolamine, diethylamine, diethylaminoethanol, etc.), and combinations thereof. A mixed solution of water and an organic solvent that contains approximately 20% by weight or less of the organic solvent. Examples of organic solvents include alcohols (e.g., glycerol, benzyl alcohol, 2-phenoxyethanol, 2-butoxyethanol, 1.2
-propanediol, sec-butyl alcohol,
alkylene glycols, etc.) esters such as butyl acetate, ethers such as methyl cellosolve, ketones such as cyclohexanone and acetone, and the like. A solution further containing about 20% by weight or less of a surfactant. As the surfactant, anionic surfactants, nonionic surfactants, cationic surfactants, and amphoteric surfactants can be used. Additionally, solutions containing acids such as salicylic acid. All of these compounds may be used alone or in combination of two or more. During development, the development can be carried out more effectively by rubbing the surface of the material using a suitable material such as a sponge. [Effects of the Invention] The photosensitive lithographic printing plate according to the present invention has excellent abrasion resistance and can be developed with an aqueous developer. The present invention will be illustrated below with reference to examples, but the embodiments of the present invention are not limited thereto. Examples 1 and 2 A substrate was produced by the method disclosed in Japanese Patent Application Laid-Open No. 56-28893. That is, the surface of an aluminum plate having a thickness of 0.24 mm was grained using a nylon brush and 400 mesh of a water suspension of pumice stone, and then thoroughly washed with water. After etching by dipping in 10% sodium hydroxide at 70°C for 60 seconds,
After washing with running water, it was neutralized with 20% HNO 3 and washed with water. This was heated to 160 V in a 1% nitric acid aqueous solution using a sinusoidal alternating waveform current under the conditions that the voltage at the anode was 12.7 V and the ratio of the amount of electricity at the anode to the amount of electricity at the cathode was 0.8.
Electrolytic surface roughening treatment was performed with an amount of electricity of coulomb/dm 2 . The surface roughness measured at this time was 0.6μ.
(Ra display). After subsequent immersion in 30% sulfuric acid and desmatting at 55°C for 2 minutes, the thickness was 2.7 g/dm at a current density of 2 A/dm 2 in 20% sulfuric acid.
It was anodized for 2 minutes so that the thickness was 2 m2. after that
It was immersed in a 2.5% sodium silicate aqueous solution at 70°C for 1 minute, then washed with water and dried. The thus prepared substrate was coated with a photosensitive solution (A) prepared in the following manner so that the dry film had a thickness of 1.0 μm. Subsequently, a sample was obtained by drying a water-dispersed photosensitive liquid (+) so that the film had a thickness of 2 μm. (Aqueous dispersion containing photosensitive component) The following organic solvent solution (A) was prepared. Poly(allyl methacrylate)/methacrylic acid (copolymerization molar ratio 85/15) 32.5 Pentaerythritol tetraacrylate
17.5g 2-trichloromethyl-5-(p-n-butoxystyryl)-1,3,4-oxadiazole
2g Oil-soluble blue dye (CI42595) 0.8g Sodium dilauryl sulfosuccinate 3g Ethylene dichloride 150g Methyl ethyl ketone 150g Next, add 100g of water to 100g of the solution (A) and stir at high speed for 5 minutes using a homogenizer to form an emulsified dispersion. I made it. While stirring this emulsified dispersion,
The organic solvent was removed by heating to 85°C. Water was added to this to adjust the solid content concentration to 10% to obtain a stable aqueous dispersion (). (Aqueous dispersion of lipophilic water-insoluble polymer) Next, the following organic solvent solution (B) was prepared. Polymethyl methacrylate 50g Sodium dilauryl sulfosuccinate 3g Ethylene dichloride 150g Methyl ethyl ketone 150g Next, 100g of the solution (B) was added to 100g of water and stirred at high speed for 5 minutes using a homogenizer to prepare an emulsified dispersion. While stirring this emulsified dispersion,
The organic solvent was removed. Water was added to this to adjust the solid content concentration to 10% to obtain a stable aqueous dispersion (). After coating the photosensitive liquid (A) on the support and drying it, 60 parts by weight of the aqueous dispersion () and 40 parts by weight of the aqueous dispersion (2) were mixed to form an aqueous dispersion (+).
This was applied as an upper layer to obtain a sample (P). For comparison, an aqueous dispersion photosensitive liquid (+) was applied to the support to obtain a comparative sample (Q). The film after drying had a thickness of 3.0μ. A negative image film was layered on top of these samples (P) and (Q) and exposed using a Burki printer (Iko Adalx 2KW) manufactured by Burki Technical Co., USA, and immersed in the following developer for 50 seconds at room temperature. The surface was lightly rubbed with absorbent cotton and developed to obtain a printing plate. Sodium sulfite 5g Benzyl alcohol 30g Sodium carbonate 5g Sodium isopropylnaphthalene sulfonate
12g water 1000g The non-image area of sample (P) was completely removed, and when printed on high-quality paper using a sheet-fed offset printer, more than 70,000 good prints were obtained. On the other hand, in the comparative sample (Q), the non-image area could be completely removed, but when printed in the same manner, only 50,000 prints were obtained. Example 2 On the same substrate as in Example 1, the photosensitive liquid (C) prepared as follows was coated so that the film after drying was 1.0μ, and then the water-dispersed photosensitive liquid (+) was dried. A sample was obtained by coating so that the thickness of the subsequent film was 1.5μ. (Aqueous dispersion containing photosensitive component) The following organic solvent solution (C) was prepared. 2-hydroxyethyl methacrylate copolymer (as described in Example 1 in U.S. Pat. No. 4,123,276) 97 g 2-methoxy-4-hydroxy condensate of p-diazodiphenylamine and paraformaldehyde 5-benzoylbenzenesulfonate 10g Oil Blue #603 (manufactured by Orient Chemical Industry Co., Ltd.)
3g Sodium 3-carboxy-4-hydroxynaphthalenesulfonate 2g Polyoxyethylene sorbitan monooleate
4g Ethylene dichloride 500g 2-methoxyethanol 250g An aqueous dispersion () was obtained in the same manner as in Example 1 using the above organic solvent solution (C). Apply photosensitive liquid (C) to the support.
Then, 70 parts by weight of the aqueous dispersion () and 30 parts by weight of the aqueous dispersion () were mixed to obtain a water-dispersed photosensitive liquid (+), which was applied as an upper layer to form the sample (R). Obtained. For comparison, water-dispersed photosensitive liquid (+
) was applied to the support to obtain a comparative sample (S).
A negative image film was placed on top of these samples (R) and (S) and exposed using a Berkey printer, and then immersed in a developer for 60 seconds at room temperature and developed by rubbing the surface lightly with absorbent cotton to obtain a printing plate. Benzyl alcohol 30g Triethanolamine 10g Sodium isopropylnaphthalene sulfonate
10g Sodium sulfite 2g Sodium nitrilotriacetate 0.5g Water 950g The non-image area of Sample (R) could be completely removed, and when printed on high-quality paper using a sheet-fed offset printer, more than 50,000 good prints were obtained. On the other hand, in the comparative sample (S), the non-image area could be completely removed, but when printed in the same manner, only 40,000 prints were obtained. Example 3 An IS 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 then grained with a nylon brush. The film was etched with an aqueous solution for about 10 seconds, and desmatted with a 3% aqueous solution of sodium hydrogen sulfate. This aluminum plate was heated in 20% sulfuric acid at a current density of 2A/d.
Anodizing was performed for 2 minutes at m 2 to produce an aluminum plate. On the substrate thus prepared, a photosensitive liquid (D) prepared as follows is coated so that the film after drying has a thickness of 0.5μ, and then a water-dispersed photosensitive liquid (+) is dried. A sample was obtained so that the thickness of the subsequent film was 2.5μ. (Aqueous dispersion containing photosensitive component) The following organic solvent solution (D) was prepared. Condensate of 1,2-naphthoquinone-2-diazido-5-sulfonyl chloride and cresol-formaldehyde resin (synthesized by the method of U.S. Pat. No. 3,046,120) 18 g Cresol-formaldehyde resin (hytanol #3110 (manufactured by Hitachi Chemical Co., Ltd.) ) 38g Oil-soluble dye (CI 42595) 0.6g Megafuck F-120 (manufactured by Dainippon Ink Chemical Co., Ltd.)
2g Methyl ethyl ketone 300g Next, 150g of water was added to 100g of the solution (D) to obtain a 10% aqueous dispersion () in the same manner as in Example 1. (Aqueous dispersion of lipophilic water-insoluble polymer) Next, the following organic solvent solution (E) was prepared. p-tirt-butylphenol-formaldehyde resin 50g Megafuck F-120 (manufactured by Dainippon Ink Chemical Co., Ltd.)
3g Methyl ethyl ketone 300g 150g of water was added to 100g of the solution (E) to obtain an aqueous dispersion () in the same manner as in Example 1. 85 parts by weight of the aqueous dispersion () and 15 parts by weight of the aqueous dispersion () were mixed to obtain an aqueous dispersion photosensitive liquid (+), which was coated as an upper layer to obtain a sample (T). For comparison, a water-dispersed photosensitive liquid (+) was applied to the support to obtain a comparative sample (U). The film after drying had a thickness of 3.0μ. A positive image film was placed on top of these samples (T) and (U), exposed using a Berkey printer, and SiO 2
in an aqueous sodium silicate solution with a content of 1.5% at room temperature.
Dip for 30 seconds, rub the surface lightly with absorbent cotton and develop.
Got the print version. Sample (T) had the non-image area completely removed, and when printed on high-quality paper using a sheet-fed offset printing machine, more than 60,000 good prints were obtained. On the other hand, in comparison sample (U), the non-image area could be removed, but when printed in the same manner, only 30,000 prints were obtained. Example 4 Photosensitive liquid (D) of Example 3 was placed on the same substrate as Example 3.
was coated so that the film thickness after drying was 1.0μ, and then a water-dispersed photosensitive solution (+
) was coated so that the film after drying had a thickness of 2.0 μm to obtain a sample. (Lipophilic water-insoluble polymer aqueous dispersion) The following organic solvent solution (F) was prepared. Polyvinyl formal 12/85T (manufactured by Monsanto) 50g Megafutsuku F-120 (Dainippon Ink Chemical Co., Ltd.)
3g Ethylene dichloride 150g Methyl ethyl ketone 150g 150g of water was added to 100g of the solution (F) to obtain an aqueous dispersion () in the same manner as in Example 1. 80 parts by weight of the aqueous dispersion ( ) of Example 3 and 20 parts by weight of the aqueous dispersion ( ) were mixed to obtain a water-dispersed photosensitive liquid (+), which was coated as an upper layer to obtain a sample (W). For comparison, a water-dispersed photosensitive liquid (+) was applied to the support to obtain a comparative sample (X). After drying, the film was
It was 3.0μ. A positive image film was placed on top of these samples (W) and (X), exposed using a Berkey printer, and developed in the same manner as in Example 3 to obtain a printing plate. The non-image area of sample (W) could be completely removed, and when printed on high-quality paper using a sheet-fed offset printing machine, more than 60,000 good-quality prints were obtained. On the other hand, in comparison sample (X), the non-image area could be removed, but when printed in the same manner, only 40,000 prints were obtained.
Claims (1)
層の非銀感光性層中に親油性水不溶性ポリマーの
微粒子分散物を含有することを特徴とする非銀感
光性平版印刷版。 ２ 上層の親油性水不溶性ポリマーの微粒子分散
物が、水系現像液で現像可能な非銀感光成分を有
機溶剤に溶解し該有機溶剤溶液を水中で乳化分散
した液と、親油性水不溶性ポリマーを有機溶剤に
溶解し該有機溶剤溶液を水中で乳化分散した液と
の混合物である特許請求の範囲第１項に記載の非
銀感光性平版印刷版。 ３ 下層が水系現像液で現像可能な感光性成分よ
りなる特許請求の範囲第１項に記載の非銀感光性
平版印刷版。[Scope of Claims] 1. It has two non-silver photosensitive layers on a support, and the upper non-silver photosensitive layer contains a fine particle dispersion of a lipophilic water-insoluble polymer. Non-silver photosensitive lithographic printing plate. 2. The fine particle dispersion of the lipophilic water-insoluble polymer in the upper layer is formed by dissolving a non-silver photosensitive component that can be developed in an aqueous developer in an organic solvent and emulsifying and dispersing the organic solvent solution in water, and the lipophilic water-insoluble polymer. The non-silver photosensitive lithographic printing plate according to claim 1, which is a mixture of a liquid obtained by dissolving in an organic solvent and emulsifying and dispersing the organic solvent solution in water. 3. The non-silver photosensitive lithographic printing plate according to claim 1, wherein the lower layer comprises a photosensitive component that can be developed with an aqueous developer.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8934284A JPS60233645A (en) | 1984-05-07 | 1984-05-07 | Nonsilver photosensitive image forming material |
| DE19853516387 DE3516387A1 (en) | 1984-05-07 | 1985-05-07 | Light-sensitive compositions and recording materials |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8934284A JPS60233645A (en) | 1984-05-07 | 1984-05-07 | Nonsilver photosensitive image forming material |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60233645A JPS60233645A (en) | 1985-11-20 |
| JPH0513304B2 true JPH0513304B2 (en) | 1993-02-22 |
Family
ID=13968021
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8934284A Granted JPS60233645A (en) | 1984-05-07 | 1984-05-07 | Nonsilver photosensitive image forming material |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60233645A (en) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS53145706A (en) * | 1977-05-19 | 1978-12-19 | Polychrome Corp | Lithographic printing plate capable of developing with water with double photosensitive layer |
| JPS55527A (en) * | 1978-06-16 | 1980-01-05 | Fuji Photo Film Co Ltd | Photosensitive planographic plate |
| JPS56159640A (en) * | 1980-05-13 | 1981-12-09 | Konishiroku Photo Ind Co Ltd | Electrophotographic sensitive material |
| JPS5714835A (en) * | 1980-07-01 | 1982-01-26 | Fuji Photo Film Co Ltd | Photographic sensitive silver halide material |
-
1984
- 1984-05-07 JP JP8934284A patent/JPS60233645A/en active Granted
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS53145706A (en) * | 1977-05-19 | 1978-12-19 | Polychrome Corp | Lithographic printing plate capable of developing with water with double photosensitive layer |
| JPS55527A (en) * | 1978-06-16 | 1980-01-05 | Fuji Photo Film Co Ltd | Photosensitive planographic plate |
| JPS56159640A (en) * | 1980-05-13 | 1981-12-09 | Konishiroku Photo Ind Co Ltd | Electrophotographic sensitive material |
| JPS5714835A (en) * | 1980-07-01 | 1982-01-26 | Fuji Photo Film Co Ltd | Photographic sensitive silver halide material |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60233645A (en) | 1985-11-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |