JPH0328701B2 - - Google Patents
Info
- Publication number
- JPH0328701B2 JPH0328701B2 JP12384482A JP12384482A JPH0328701B2 JP H0328701 B2 JPH0328701 B2 JP H0328701B2 JP 12384482 A JP12384482 A JP 12384482A JP 12384482 A JP12384482 A JP 12384482A JP H0328701 B2 JPH0328701 B2 JP H0328701B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- general formula
- photosensitive
- naphthoquinone
- compound represented
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000000203 mixture Substances 0.000 claims description 33
- 150000001875 compounds Chemical class 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000003107 substituted aryl group Chemical group 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 150000001340 alkali metals Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 238000007639 printing Methods 0.000 description 18
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 17
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 16
- -1 quinonediazide compound Chemical class 0.000 description 14
- 230000035945 sensitivity Effects 0.000 description 14
- 238000000576 coating method Methods 0.000 description 12
- 239000011248 coating agent Substances 0.000 description 11
- 230000000694 effects Effects 0.000 description 11
- 239000000975 dye Substances 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 229940074391 gallic acid Drugs 0.000 description 9
- 235000004515 gallic acid Nutrition 0.000 description 9
- 239000000463 material Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- 238000007645 offset printing Methods 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- MJVAVZPDRWSRRC-UHFFFAOYSA-N Menadione Chemical compound C1=CC=C2C(=O)C(C)=CC(=O)C2=C1 MJVAVZPDRWSRRC-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- VFPFQHQNJCMNBZ-UHFFFAOYSA-N ethyl gallate Chemical compound CCOC(=O)C1=CC(O)=C(O)C(O)=C1 VFPFQHQNJCMNBZ-UHFFFAOYSA-N 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 229920003986 novolac Polymers 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 239000000654 additive Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- FBSFWRHWHYMIOG-UHFFFAOYSA-N methyl 3,4,5-trihydroxybenzoate Chemical compound COC(=O)C1=CC(O)=C(O)C(O)=C1 FBSFWRHWHYMIOG-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 3
- WTQZSMDDRMKJRI-UHFFFAOYSA-N 4-diazoniophenolate Chemical compound [O-]C1=CC=C([N+]#N)C=C1 WTQZSMDDRMKJRI-UHFFFAOYSA-N 0.000 description 3
- IUSVMAFWJQCDHC-UHFFFAOYSA-N 6-chloronaphthalene-1,4-dione Chemical compound O=C1C=CC(=O)C2=CC(Cl)=CC=C21 IUSVMAFWJQCDHC-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000004262 Ethyl gallate Substances 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 235000019277 ethyl gallate Nutrition 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- ZRUOTKQBVMWMDK-UHFFFAOYSA-N 2-hydroxy-6-methylbenzaldehyde Chemical compound CC1=CC=CC(O)=C1C=O ZRUOTKQBVMWMDK-UHFFFAOYSA-N 0.000 description 2
- OBGBGHKYJAOXRR-UHFFFAOYSA-N 2-methoxy-1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C(OC)=CC(=O)C2=C1 OBGBGHKYJAOXRR-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
- 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 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 206010034972 Photosensitivity reaction Diseases 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
- 239000012670 alkaline solution Substances 0.000 description 2
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 2
- 239000000981 basic dye Substances 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 229930003836 cresol Natural products 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
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- VOOLKNUJNPZAHE-UHFFFAOYSA-N formaldehyde;2-methylphenol Chemical compound O=C.CC1=CC=CC=C1O VOOLKNUJNPZAHE-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910001507 metal halide Inorganic materials 0.000 description 2
- IBKQQKPQRYUGBJ-UHFFFAOYSA-N methyl gallate Natural products CC(=O)C1=CC(O)=C(O)C(O)=C1 IBKQQKPQRYUGBJ-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000005561 phenanthryl group Chemical group 0.000 description 2
- 229920001568 phenolic resin Polymers 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 230000036211 photosensitivity Effects 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 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
- 239000007787 solid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- TUSDEZXZIZRFGC-UHFFFAOYSA-N 1-O-galloyl-3,6-(R)-HHDP-beta-D-glucose Natural products OC1C(O2)COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC1C(O)C2OC(=O)C1=CC(O)=C(O)C(O)=C1 TUSDEZXZIZRFGC-UHFFFAOYSA-N 0.000 description 1
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Substances C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 description 1
- LGFDNUSAWCHVJN-UHFFFAOYSA-N 2,3-dimethyl-1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C(C)=C(C)C(=O)C2=C1 LGFDNUSAWCHVJN-UHFFFAOYSA-N 0.000 description 1
- FMAJEZFADLOKFJ-UHFFFAOYSA-N 2,5-dimethylnaphthalene-1,4-dione Chemical compound C1=CC=C2C(=O)C(C)=CC(=O)C2=C1C FMAJEZFADLOKFJ-UHFFFAOYSA-N 0.000 description 1
- RIIHJPZVLFBVPJ-UHFFFAOYSA-N 2-(4-methylphenyl)naphthalene-1,4-dione Chemical compound C1=CC(C)=CC=C1C1=CC(=O)C2=CC=CC=C2C1=O RIIHJPZVLFBVPJ-UHFFFAOYSA-N 0.000 description 1
- LKDQLNOZQAMIOG-UHFFFAOYSA-N 2-acetylnaphthalene-1,4-dione Chemical compound C1=CC=C2C(=O)C(C(=O)C)=CC(=O)C2=C1 LKDQLNOZQAMIOG-UHFFFAOYSA-N 0.000 description 1
- CCTJHVLTAJTPBV-UHFFFAOYSA-N 2-chloro-1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C(Cl)=CC(=O)C2=C1 CCTJHVLTAJTPBV-UHFFFAOYSA-N 0.000 description 1
- QBHSRQVIJSKBPX-UHFFFAOYSA-N 2-ethylnaphthalene-1,4-dione Chemical compound C1=CC=C2C(=O)C(CC)=CC(=O)C2=C1 QBHSRQVIJSKBPX-UHFFFAOYSA-N 0.000 description 1
- LMWMTSCFTPQVCJ-UHFFFAOYSA-N 2-methylphenol;phenol Chemical compound OC1=CC=CC=C1.CC1=CC=CC=C1O LMWMTSCFTPQVCJ-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- CIDYIYSNDAJNGX-UHFFFAOYSA-N 2-phenylnaphthalene-1,4-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 CIDYIYSNDAJNGX-UHFFFAOYSA-N 0.000 description 1
- VVFNUTJHHYMHOA-UHFFFAOYSA-N 2-propylnaphthalene-1,4-dione Chemical compound C1=CC=C2C(=O)C(CCC)=CC(=O)C2=C1 VVFNUTJHHYMHOA-UHFFFAOYSA-N 0.000 description 1
- UGWULZWUXSCWPX-UHFFFAOYSA-N 2-sulfanylideneimidazolidin-4-one Chemical compound O=C1CNC(=S)N1 UGWULZWUXSCWPX-UHFFFAOYSA-N 0.000 description 1
- RBTBFTRPCNLSDE-UHFFFAOYSA-N 3,7-bis(dimethylamino)phenothiazin-5-ium Chemical compound C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 RBTBFTRPCNLSDE-UHFFFAOYSA-N 0.000 description 1
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- LZDOYVMSNJBLIM-UHFFFAOYSA-N 4-tert-butylphenol;formaldehyde Chemical compound O=C.CC(C)(C)C1=CC=C(O)C=C1 LZDOYVMSNJBLIM-UHFFFAOYSA-N 0.000 description 1
- WIQOTPPGPMGIBW-UHFFFAOYSA-N 6-bromonaphthalene-1,4-dione Chemical compound O=C1C=CC(=O)C2=CC(Br)=CC=C21 WIQOTPPGPMGIBW-UHFFFAOYSA-N 0.000 description 1
- XDIWXFTZTJQXDE-UHFFFAOYSA-N 6-nitronaphthalene-1,4-dione Chemical compound O=C1C=CC(=O)C2=CC([N+](=O)[O-])=CC=C21 XDIWXFTZTJQXDE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RPWFJAMTCNSJKK-UHFFFAOYSA-N Dodecyl gallate Chemical compound CCCCCCCCCCCCOC(=O)C1=CC(O)=C(O)C(O)=C1 RPWFJAMTCNSJKK-UHFFFAOYSA-N 0.000 description 1
- 239000001263 FEMA 3042 Substances 0.000 description 1
- 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 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 229930192627 Naphthoquinone Natural products 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- LRBQNJMCXXYXIU-PPKXGCFTSA-N Penta-digallate-beta-D-glucose Natural products OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-PPKXGCFTSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000004111 Potassium silicate Substances 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- HPCCQNGKAFBWAU-UHFFFAOYSA-N benzyl 3,4,5-trihydroxybenzoate Chemical compound OC1=C(O)C(O)=CC(C(=O)OCC=2C=CC=CC=2)=C1 HPCCQNGKAFBWAU-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229910000423 chromium oxide Inorganic materials 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- ZXJXZNDDNMQXFV-UHFFFAOYSA-M crystal violet Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1[C+](C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1 ZXJXZNDDNMQXFV-UHFFFAOYSA-M 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 229940061607 dibasic sodium phosphate Drugs 0.000 description 1
- COVFEVWNJUOYRL-UHFFFAOYSA-M digallate Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C([O-])=O)O)=C1 COVFEVWNJUOYRL-UHFFFAOYSA-M 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 235000010386 dodecyl gallate Nutrition 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- IFDFMWBBLAUYIW-UHFFFAOYSA-N ethane-1,2-diol;ethyl acetate Chemical compound OCCO.CCOC(C)=O IFDFMWBBLAUYIW-UHFFFAOYSA-N 0.000 description 1
- DRIIOWCRDBYORK-UHFFFAOYSA-N ethane-1,2-diol;methyl acetate Chemical compound OCCO.COC(C)=O DRIIOWCRDBYORK-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 1
- 229940091173 hydantoin Drugs 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229910052744 lithium Inorganic materials 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
- 239000012528 membrane Substances 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
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 229960000907 methylthioninium chloride Drugs 0.000 description 1
- UJNDLBGVCUUPLX-UHFFFAOYSA-N n-(benzylideneamino)-3-methylaniline Chemical compound CC1=CC=CC(NN=CC=2C=CC=CC=2)=C1 UJNDLBGVCUUPLX-UHFFFAOYSA-N 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- 231100000989 no adverse effect Toxicity 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- BRNPAEUKZMBRLQ-UHFFFAOYSA-N octadecyl 3,4,5-trihydroxybenzoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C1=CC(O)=C(O)C(O)=C1 BRNPAEUKZMBRLQ-UHFFFAOYSA-N 0.000 description 1
- HBZMQFJTPHSKNH-UHFFFAOYSA-N phenyl 3,4,5-trihydroxybenzoate Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C=CC=CC=2)=C1 HBZMQFJTPHSKNH-UHFFFAOYSA-N 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- BXHMEGGWXNNSDW-UHFFFAOYSA-M potassium 3,4,5-trihydroxybenzoate Chemical compound [K+].OC1=CC(C([O-])=O)=CC(O)=C1O BXHMEGGWXNNSDW-UHFFFAOYSA-M 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229940093956 potassium carbonate Drugs 0.000 description 1
- CHWRSCGUEQEHOH-UHFFFAOYSA-N potassium oxide Chemical compound [O-2].[K+].[K+] CHWRSCGUEQEHOH-UHFFFAOYSA-N 0.000 description 1
- 229910001950 potassium oxide Inorganic materials 0.000 description 1
- NNHHDJVEYQHLHG-UHFFFAOYSA-N potassium silicate Chemical compound [K+].[K+].[O-][Si]([O-])=O NNHHDJVEYQHLHG-UHFFFAOYSA-N 0.000 description 1
- 229910052913 potassium silicate Inorganic materials 0.000 description 1
- 235000019353 potassium silicate Nutrition 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000473 propyl gallate Substances 0.000 description 1
- 229940075579 propyl gallate Drugs 0.000 description 1
- 150000003246 quinazolines Chemical class 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
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229940001593 sodium carbonate Drugs 0.000 description 1
- 235000019795 sodium metasilicate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- LRBQNJMCXXYXIU-NRMVVENXSA-N tannic acid Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-NRMVVENXSA-N 0.000 description 1
- 235000015523 tannic acid Nutrition 0.000 description 1
- 229940033123 tannic acid Drugs 0.000 description 1
- 229920002258 tannic acid Polymers 0.000 description 1
- FYFPJTIURCOBGQ-UHFFFAOYSA-N tert-butyl 3,4,5-trihydroxybenzoate Chemical compound CC(C)(C)OC(=O)C1=CC(O)=C(O)C(O)=C1 FYFPJTIURCOBGQ-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 229940001496 tribasic sodium phosphate Drugs 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
- FKVXIGHJGBQFIH-UHFFFAOYSA-K trisodium 5-amino-3-[[4-[4-[(7-amino-1-hydroxy-3-sulfonatonaphthalen-2-yl)diazenyl]phenyl]phenyl]diazenyl]-4-hydroxynaphthalene-2,7-disulfonate Chemical compound C1=CC(=CC=C1C2=CC=C(C=C2)N=NC3=C(C=C4C=CC(=CC4=C3[O-])N)S(=O)(=O)O)N=NC5=C(C6=C(C=C(C=C6C=C5S(=O)(=O)O)S(=O)(=O)[O-])N)[O-].[Na+].[Na+].[Na+] FKVXIGHJGBQFIH-UHFFFAOYSA-K 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- XNRPVPHNDQHWLJ-PMACEKPBSA-N tryprostatin A Chemical compound N1C(=O)[C@@H]2CCCN2C(=O)[C@@H]1CC1=C(CC=C(C)C)NC2=CC(OC)=CC=C21 XNRPVPHNDQHWLJ-PMACEKPBSA-N 0.000 description 1
- AODQPPLFAXTBJS-UHFFFAOYSA-M victoria blue 4R 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=[N+](C)C1=CC=CC=C1 AODQPPLFAXTBJS-UHFFFAOYSA-M 0.000 description 1
- 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 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910001868 water Inorganic materials 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
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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
- G03F7/022—Quinonediazides
- G03F7/0226—Quinonediazides characterised by the non-macromolecular additives
Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
Description
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æ§çµæç©ã«é¢ãããDETAILED DESCRIPTION OF THE INVENTION The present invention relates to a positive-working photosensitive composition suitable for manufacturing lithographic printing plates, IC circuits, and photomasks used in lithographic printing machines, lithographic printing proofing machines, etc. A photosensitive composition containing a compound and a specific compound that increases sensitivity without adversely affecting development acceptability,
The present invention also relates to a positive-working photosensitive composition capable of adjusting halftone dot reproducibility (controlling dot reduction effect).
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æããŠããã Photosensitive compositions containing o-quinonediazide compounds have been used industrially as excellent positive-working photosensitive compositions in the production of lithographic printing plates and as photoresists. Hitherto, various proposals have been made regarding methods for increasing the photosensitivity of this o-quinonediazide-based positive photosensitive composition, but none have been satisfactory. For example, if the amount of the quinonediazide compound is reduced, the sensitivity will naturally increase, but this will result in a narrowing of the development tolerance (the time range in which optimum development is obtained; hereinafter the same shall apply), making it impractical. arise.
Furthermore, a system in which an o-quinonediazide compound is combined with a binder resin having high solubility in aqueous alkaline solutions increases the apparent sensitivity, but has the same disadvantage as the above case of narrowing development tolerance. .
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ç¹ãæããŠããã®ãçŸç¶ã§ããã In addition, a technique has been proposed in which a non-photosensitive compound (sensitizer) is added to a photosensitive composition containing an o-quinonediazide compound to increase sensitivity.
At present, none of these methods has achieved sufficient effects and has various drawbacks.
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ãããªãã For example, as described in U.S. Pat. No. 3,661,582, certain heterocyclic compounds such as 2-azacyclononan-2-one, indole,
The sensitivity can be increased by adding quinazolines and tetrazoles, but in this case, too, the development latitude is only extremely narrow, as in the case described above.
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ããŠé¡èãªäœçšãæããªãã Japanese Patent Publication No. 46-42449 describes various additives for increasing photographic sensitivity, such as triphenylmethane dyes, benzaldehyde-m-tolylhydrazone, halogenated hydrocarbons, and azo dyes. These compounds do not have a significant effect on increasing sensitivity.
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ã°ãªããªãã Also, for the same purpose, o-benzoic acid sulfimide,
The addition of hydantoin and its derivatives, thiohydantoin and its derivatives has been proposed (JP-A-Sho
See Publication No. 50-36203. ). Additionally, cyclic acid anhydride additives have been proposed for the same purpose (Japanese Patent Laid-Open No. 52
-See Publication No. 30022. ). In these cases as well, if the amount added is such that an increase in sensitivity is observed, the development tolerance during development is extremely narrow and is not practical. Furthermore, a photosensitive copying material containing polyhydroxybenzophenone has also been proposed (see Japanese Patent Laid-Open No. 52-54503), but this compound is added to improve adhesion to the support. Related to this, it is a technology that increases sensitivity, but there is no noticeable increase in sensitivity.
Furthermore, for the purpose of increasing sensitivity, it has been proposed to add a condensation product of hydroxybenzophenone and formaldehyde (see JP-A-55-73045); As in the case of the compound in the publication, a considerable amount is required for a clear increase in sensitivity to be observed, and a decrease in development tolerance and chemical resistance must be accepted.
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çºãæãŸããŠããã Further, positive-working photosensitive compositions containing o-quinonediazide compounds are widely used, including lithographic printing plates, and various performances are required depending on each use. For example, a lithographic printing machine and a lithographic printing proofing machine have very different image reproducibility on printed matter, and the halftone dots for this machine are reproduced relatively small on the printing plate (the dot reduction effect is On the other hand, for proofing machines, it is desired that the halftone dots are not reproduced very small on the printing plate (the dot reduction effect is small). It is desired to develop a technique that can provide excellent positive-working photosensitive compositions having suitability for these various uses by simple means.
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æ§çµæç©ãæäŸããã«ããã Therefore, it is an object of the present invention to improve o
- It is an object of the present invention to provide a positive-working photosensitive composition containing a quinone diazide type photosensitive substance, which has improved sensitivity and is capable of controlling halftone dot reproducibility to a desired degree (controlling dot reduction effect).
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ã€ãŠæããã§ãããã Other objects of the invention will become apparent from the description herein.
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æãããã The above object of the present invention is to obtain (a) an o-quinonediazide compound, (b) a compound represented by the following general formula [], and
(c) This is achieved by a positive-working photosensitive composition characterized by containing a compound represented by the following general formula [].
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瀺ãã General formula [] In the above general formula [], R represents a hydrogen atom, an alkyl group, an aralkyl group, an aryl group, a substituted aryl group, a cycloalkyl group, or an alkali metal atom.
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ãããªããã®ãšããã General formula [] In the general formula [ ], R 1 , R 2 , R 3 are each a hydrogen atom, an alkyl group, an alkoxy group, an aryl group,
Indicates a substituted aryl group, acyl group, halogeno group, nitro group or hydroxyl group. However, each R 3 shall consist of the same group or atom or a combination of different types.
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ã«ããžãŠã çããããããã Among these, in the general formula [], the alkyl group represented by R preferably has 1 to 18 carbon atoms, particularly preferably 1 to 4 carbon atoms. Further, these may be linear or branched, and specific examples of this alkyl group include methyl,
Examples include groups such as ethyl, i-propyl, t-butyl, i-amyl, n-hexyl, n-octyl, lauryl, cetyl and stearyl. R
Examples of the aralkyl group represented by the formula include benzyl, phenethyl, 3-phenylpropyl, and 2-naphthylmethyl. The aryl group represented by R and the substituted aryl group include phenyl, naphthyl, anthryl,
Examples include various groups such as phenanthryl. As substituents to the aryl group in the substituted aryl group,
Lower alkyl group (1 to 4 carbon atoms), alkoxy group (1 to 4 carbon atoms), acyl group (2 to 4 carbon atoms), halogeno group (chloro, brome, etc.),
Examples include a nitro group, a hydroxyl group, and a carboxyl group, and two or more of the above substituents may be included or a combination thereof may be used. Examples of the cycloalkyl group include cyclopropyl, cyclopentyl, and cyclohexyl groups. And, as alkali metal atoms, lithium, sodium, potassium,
Examples include rubidium.
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ãç°ãªã€ãŠãè¯ããçµåãã¯ä»»æã«ãšããã In the general formula [], the alkyl group represented by R 1 , R 2 or R 3 preferably has 1 carbon atom.
-18, particularly preferably those having 1 to 4 carbon atoms, which may be linear or branched; examples of the base of this alkyl group include:
Methyl, ethyl, i-propyl, t-butyl, i
Examples include groups such as -amyl, n-hexyl, n-octyl, lauryl, cetyl and stearyl. Examples of the alkoxy group represented by R 1 , R 2 or R 3 include methoxy, ethoxy, i-propoxy, t-butoxy and the like, among which methoxy and ethoxy are preferred. R1 ,
Examples of the aryl group and substituted aryl group represented by R 2 or R 3 include phenyl, naphthyl, anthryl, and phenanthryl groups. Substituents for the aryl group in the substituted aryl group include lower alkyl (1 to 4 carbon atoms), alkoxy group (1 to 4 carbon atoms), acyl group (2 to 4 carbon atoms), halogeno group (chloro , bromine, etc.), nitro groups, and hydroxyl groups. Examples of the acyl group represented by R 1 , R 2 or R 3 include acetyl, propionyl, butyryl, benzoyl and the like. R1 , R2
Alternatively, the halogeno group represented by R 3 includes fluoro, chloro, bromo, iodo, etc.
Preferred are chlor and brome. Further, in the general formula [], R 1 , R 2 , and R 3 may be the same or different, and may be the same substituent, or each substituent may be different, and any combination thereof may be taken.
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ãŠãããã®ããããããšãã§ããã As the quinonediazide compound used in the present invention, conventionally known compounds can be used.
Ester of 1,2-diazobenzononesulfonic acid chloride and polyhydroxyphenyl or 1,2-diazonaphthoquinonesulfonic acid chloride and resorcinol-binzaldehyde as described in No. 1044 and No. 56-1045 Most preferred are esters with resins. Other suitable quinonediazide compounds include U.S. Pat.
There are esters of 1,2-diazobenzoquinone sulfonic acid chloride or 1,2-diazonaphthoquinone sulfonic acid chloride and phenol-formaldehyde resin described in the specifications of 3046120 and 3188210. Other useful quinonediazide compounds have been reported in numerous patent publications and are known. For example, JP-A No. 47-4303, JP-A No. 48-63802, JP-A No. 48-63803,
No. 48-96575, No. 48-13354, No. 49-38701,
Special Publication No. 41-11222, No. 43-28403, No. 45-9610
No. 49-17481, U.S. Patent No. 2797213
No. 3454400, No. 3544323, No. 3544323, No. 3454400, No. 3544323, No.
British Patent No. 3573917, British Patent No. 3674495, British Patent No. 3785825, British Patent No. 1227602, British Patent No. 1251345, British Patent No.
Examples include those described in specifications such as German Patent No. 1267005, German Patent No. 1329888, German Patent No. 1330932, and German Patent No. 854890.
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ã³æš¹èãªã©ã代衚äŸãšããŠãããããšãã§ããã Moreover, a binder component can be added to the positive photosensitive composition according to the present invention, if necessary. For example, suitable examples include novolak resins that are soluble or sparingly soluble in aqueous alkaline solutions. Representative examples of such novolac resins include phenol-formaldehyde resin, cresol formaldehyde resin, p-tert-butylphenol formaldehyde resin, and phenol-modified xylene resin.
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50% by weight is preferred, more preferably 20-40% by weight.
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ã§ããã Representative examples of the compound represented by the general formula [] used in combination with the quinonediazide compound in the present invention include the following. Namely, gallic acid, methyl gallate, ethyl gallate, i-propyl gallate, t-butyl gallate, lauryl gallate, stearyl gallate, benzyl gallate, phenyl gallate, cyclohexyl gallate, tannic acid, digallate. There are acids, potassium gallate, etc. Among these compounds, particularly preferred compounds in the present invention are gallic acid, methyl gallate, and ethyl gallate.
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ãã In the present invention, the following compounds are representative examples of the compound represented by the general formula [] used in combination with the quinonediazide compound together with the compound represented by the general formula []. That is, 1,4-naphthoquinone, 2-methyl-1,4-naphthoquinone, 2-ethyl-1,
4-naphthoquinone, 2-propyl-1,4-naphthoquinone, 2,3-dimethyl-1,4-naphthoquinone, 2,5-dimethyl-1,4-naphthoquinone, 2-methoxy-1,4-naphthoquinone, 2-
Phenyl-1,4-naphthoquinone, 2-(p-tolyl)-1,4-naphthoquinone, 2-acetyl-
1,4-naphthoquinone, 3-chloro-1,4-naphthoquinone, 6-chloro-1,4-naphthoquinone, 6-bromo-1,4-naphthoquinone, 6-nitro-1,4-naphthoquinone, 2-hydroxy-
Examples include 1,4-naphthoquinone. Among these compounds, particularly preferred compounds are 1,4-
They are naphthoquinone, 2-methyl-1,4-naphthoquinone and 6-chloro-1,4-naphthoquinone.
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ããŠããŠãããã The positive photosensitive composition according to the present invention only needs to contain at least one compound represented by the above general formula [] and at least one compound represented by the general formula [], and two or more kinds of one or both. May contain.
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ãïŒïŒïŒã®ç¯å²ã§ããã The total amount of the compounds represented by the above general formulas [ ] and [ ] is preferably 0.5 to 20% by weight, more preferably 1 to 10% by weight in the composition.
In addition, the weight ratio of the compound represented by the general formula [] and the compound represented by the general formula [] is 1:10 ~
A range of 10:1 is preferred, more preferably 1:5
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ååŠå·¥æ¥è£œïŒçã®æ²¹æº¶æ§ææããããããã The positive photosensitive composition according to the present invention may further contain fillers, pigments, dyes, pigments, photodegradable acid generators, surfactants for improving coating properties, and other commonly used materials. It may contain additives and auxiliaries. These additives vary depending on their type, but in general, the amount added is preferably 0.01 to 20% by weight based on the total composition, and particularly preferably
0.05-10% by weight is suitable. Dyes preferably used in the present invention include basic dyes and oil-soluble dyes. Specifically, Victoria
Pure Blue BOH, Victoria Blue
BH, Methyl Violet, Eisen Malachite Green (manufactured by Hodogaya Chemical Industries), Batent Pure Blue VX, Rhodamine
B, methylene blue (manufactured by Sumitomo Chemical)
Basic dyes such as Sudan Blue,
Victoria Blue F4R (manufactured by BASF),
Oil Blue #603, Oil Blue
Examples include oil-soluble dyes such as BOS and Oil Blue N (manufactured by Orient Chemical Industries).
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ãããã The photosensitive composition according to the present invention can be applied to aluminum plates, zinc plates, copper plates, chrome-plated iron plates, plastic films, paper, such as bimetals, tri-metals, copper/plastic plates for printed wiring, chromium oxide vapor-deposited glass. It is used for various purposes by coating on a suitable support such as a laminate plate. At this time, the support may be surface-treated electrically, mechanically, or chemically to improve adhesion.
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ã®ããããå¡åžæè¡ãçšããããšãã§ããã The photosensitive composition according to the present invention is used after being dissolved in various organic solvents when applied. Examples of the solvent used here include ethylene dichloride, cyclohexanone, methyl ethyl ketone, ethylene glycol monomethyl ether, and ethylene dichloride. Examples include glycol monoethyl ether, ethylene glycol monomethyl acetate, ethylene glycol monoethyl acetate, dioxane, ethyl acetate, and dimethylformamide, and these can be used alone or in combination.
The solid content concentration in the above coating liquid components is 1 to 50% by weight.
A range of is desirable. In addition, the coating amount varies depending on the application, but generally it is 0.5 to 3.0 g/m 2 as a solid content.
is appropriate. Further, as a coating method, any conventionally known coating technique can be used.
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Conventionally used methods can be applied, for example, by exposing a transparent original having a line image, halftone image, etc. in close contact with a photosensitive image, and then developing this with an alkaline aqueous solution, the original image is A positive relief image is obtained. Suitable light sources for exposure include mercury lamps, metal halide lamps, xenon lamps, chemical lamps, and carbon arc lamps, and alkaline aqueous solutions used for development include sodium silicate, potassium silicate, sodium hydroxide, and water. There are alkaline aqueous solutions such as aqueous solutions of potassium oxide, tribasic sodium phosphate, dibasic sodium phosphate, sodium carbonate, potassium carbonate, and the like. The concentration of the alkaline aqueous solution at this time varies depending on the photosensitive composition and the type of alkali, but in general, a range of 0.1 to 10% by weight is appropriate. It is also possible to add organic solvents such as
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ãã§ããã A photosensitive material using the photosensitive composition according to the present invention,
In particular, lithographic printing plates have higher sensitivity than those made using conventional positive-working photosensitive compositions, and therefore can shorten exposure time and improve workability. By varying the ratio of the compound represented by the general formula [], the halftone dot reproducibility (dot reduction effect) of the light-sensitive material can be adjusted in various ways. For example, by increasing the ratio of the compound represented by the general formula [] in the photosensitive composition, the halftone area ratio on the photosensitive material can be compared to when the compounds represented by the general formulas [] and [] are not added. (the dot reduction effect increases), and conversely, by increasing the ratio of the compound represented by the general formula [], the dot area ratio of the photosensitive material can be reduced by the compounds represented by the general formulas [] and []. can be made larger (suppressing the point reduction effect) compared to the case without adding. These techniques are very important for the purpose of providing photosensitive compositions suitable for various uses, and the present invention enables, for example, a photosensitive composition with a relatively large dot reduction effect to be used in offset printing plates for this machine. On the other hand, a photosensitive composition having a small dot reduction effect can be provided for an offset printing plate for proofing by simply changing the ratio of the compounds represented by the general formulas [] and [].
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城ããä»äžããããšãã§ããã As described above, photosensitive materials, especially lithographic printing plates, using the photosensitive composition according to the present invention are extremely useful.
It is also possible to impart characteristics that cannot be obtained when using other photosensitive compositions.
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ãã«ããæ¬çºæãéå®ããããã®ã§ã¯ãªãã The present invention will be illustrated below with reference to examples, but the present invention is not limited thereto.
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ãã®ä¹Ÿç¥åŸã®èééã¯2.5ïœïŒm2ã§ãã€ããExample 1 1,2- of resorcin-benzaldehyde resin
Naphthoquinone-2-diazide-5-sulfonic acid ester (described in JP-A-56-1044, Example 1) 3.00g Cresol-formaldehyde resin 9.00g Gallic acid 0.27g 1,4-naphthoquinone 0.09g Victoria Piure Blue BOH (manufactured by Hodogaya Chemical Co., Ltd., dye) 0.12g Ethylene glycol monomethyl ether 100g The photosensitive coating solution with the above composition was applied to an aluminum plate that had been electrolytically polished and further anodized.After drying at this time, The membrane weight was 2.5 g/m 2 .
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ã§ãã€ãã The positive transparent original image was brought into close contact with the surface of the photosensitive plate prepared in this way, and exposed to light from a distance of 70 cm using a 2KW metal halide lamp for 60 seconds, which is the optimum exposure time.
Developing was performed for seconds. The optimum exposure time at this time was determined to be the point at which the 5th step was completely clear in a gray scale (Sakura Step Tablet Type TPS-A) with a density difference of 0.15. At this time, exposure was simultaneously carried out through a 150 line/inch dot scale (Sakura Step Tablet Type TPS-B).
The reproducibility of the halftone dot area on the printing plate (hereinafter referred to as halftone dot reproducibility) was examined. When we measured the area ratio on the printing board corresponding to the halftone dots with an original area ratio of 49% using a halftone dot analyzer (Sakura Area Datuku 1000),
It was 38.7%.
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ã§ãã€ãã Further, the time required for the change in the number of clear steps in the above gray scale to be within one step (hereinafter referred to as development acceptability) at 25° C. with a 2% sodium metasilicate aqueous solution was within 6 minutes.
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æ¿ãåŸããExample 2 The same photosensitive coating liquid as in Example 1 except that the amount of gallic acid added was changed from 0.27g to 0.09g, and the amount of 1,4-naphthoquinone added was changed from 0.09g to 0.27g. A photosensitive plate was obtained using the following.
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ã§ãã€ãã As a result, the optimum exposure time was 62 seconds, and the development tolerance was within 6 minutes. Furthermore, when the dot reproducibility was measured, it was 41.4%.
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æ¿ãã€ãã€ããComparative Example 1 In the photosensitive coating liquid used in Example 1 above,
A photosensitive plate was prepared in the same manner as in Example 1, except that gallic acid and 1,4-naphthoquinone were omitted.
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The optimum exposure time, halftone dot reproducibility, and development acceptability were investigated using the same method as above.
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ã§ãã€ãã Optimum exposure time is 125 seconds, halftone reproducibility is 40.2%,
Development acceptability was within 6 minutes.
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It can be seen that the photosensitivity can be increased approximately twice, and that the dot reproducibility can be adjusted by changing the ratio of gallic acid and 1,4-naphthoquinone.
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0.14 g Ethylene glycol monoethyl ether 100 g The photosensitive coating liquid having the above composition was applied to the same electrolytically polished and anodized aluminum plate as in Example 1 so that the film weight after drying was 2.3 g/m 2 .
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It was %.
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èééã¯2.1ïœïŒm2ã§ãã€ããExample 4 Naphthoquinone-1,2-diazide-5-sulfonic acid ester of m-cresol-formaldehyde resin (as described in Example 3 of Japanese Patent Publication No. 1983-9610) 4.20 g Cresol phenol novolac resin 7.80 g Gallic acid Acid 0.10g 2-Methyl-1,4-naphthoquinone 0.26g Oil Blue #603 (manufactured by Orient Chemical Industry Co., Ltd., dye) 0.07g Crystal Violet (manufactured by BASF, dye)
0.07 g Ethylene glycol monoethyl ether 100 g A photosensitive coating solution having the above composition was applied to a mechanically roughened and anodized aluminum plate using a nylon brush. The weight of the film after drying at this time was 2.1 g/m 2 .
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ã§ãã€ãã The optimum exposure time, development tolerance and halftone dot reproducibility of the thus obtained photosensitive plate were examined in the same manner as in Example 1. As a result, the optimum exposure time was 65 seconds, development tolerance was within 6 minutes, and halftone dot reproducibility was 41.0.
It was %.
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ããã When the printing plate obtained in the above manner was printed using an offset printing machine, a large number of printed matter with good sharpness and contrast were obtained.
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ã¯ã¬ãŸãŒã«ããã©ãã¯æš¹è 9.70ïœ
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žãšãã« 0.20ïœ
ïŒïŒïŒâãããããã³ 0.20ïœ
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åŠå·¥æ¥æ ªåŒäŒç€Ÿè£œãææïŒ 0.14ïœ
ãšãã¬ã³ã°ãªã³ãŒã«ã¢ãã¡ãã«ãšãŒãã« 100ïœ
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ã§ãã€ããExample 5 Pyrogallol-naphthoquinone in acetone resin-
1,2-diazide-5-sulfonic acid ester (as described in U.S. Pat. No. 3,635,709, Example 1) 3.00 g Cresol novolac resin 9.70 g Ethyl gallate 0.20 g 1,4-naphthoquinone 0.20 g Blue BOH (manufactured by Hodogaya Chemical Co., Ltd., dye) 0.14 g Ethylene glycol monomethyl ether 100 g A photosensitive coating liquid having the above composition was applied to an electrochemically roughened and anodized aluminum plate. The weight of the film after drying at this time is 2.0g/m 2
It was hot.
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ã§ãã€ãã The optimum exposure time, development tolerance and halftone dot reproducibility of the thus obtained photosensitive plate were examined in the same manner as in Example 1. As a result, the optimal exposure time is 60 seconds, development tolerance is within 6 minutes, and halftone reproducibility is 40.1
It was %.
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ç©ãå€æ°æåŸãããã When the printing plate obtained as described above was printed using an offset printing machine, a large number of printed matter with good images were obtained.
Claims (1)
ã§ç€ºãããååç©ããã³(c)äžèšäžè¬åŒïŒ»ïŒœ
ã§ç€ºãããååç©ãå«æããããšãç¹åŸŽãšããã
ãžåæå æ§çµæç©ã äžè¬åŒïŒ»ïŒœ ïŒäžè¬åŒïŒ»ïŒœäžãã¯æ°ŽçŽ ååãã¢ã«ãã«
åºãã¢ã©ã«ãã«åºãã¢ãªãŒã«åºã眮æã¢ãªãŒã«
åºãã·ã¯ãã¢ã«ãã«åºãŸãã¯ã¢ã«ã«ãªéå±ååã
瀺ããïŒ äžè¬åŒïŒ»ïŒœ ïŒäžè¬åŒïŒ»ïŒœäžãR1ïŒR2ããã³R3ã¯ããã
ãæ°ŽçŽ ååãã¢ã«ãã«åºãã¢ã«ã³ãã·åºãã¢ãªãŒ
ã«åºã眮æã¢ãªãŒã«åºãã¢ã·ã«åºãããã²ãåºã
ãããåºãŸãã¯æ°Žé žåºã瀺ããäœããR3ã¯ãã
ããåäžã®åºãããã¯ååãŸãã¯ç°ãªã€ãçš®é¡ã®
çµåããããªããã®ãšãããïŒ[Scope of Claims] 1 (a) an o-quinonediazide compound, (b) a compound represented by the following general formula [], and (c) a compound represented by the following general formula []
A positive photosensitive composition comprising a compound represented by: General formula [] (In the general formula [], R represents a hydrogen atom, an alkyl group, an aralkyl group, an aryl group, a substituted aryl group, a cycloalkyl group, or an alkali metal atom.) General formula [] (In the general formula [], R 1 , R 2 and R 3 are each a hydrogen atom, an alkyl group, an alkoxy group, an aryl group, a substituted aryl group, an acyl group, a halogeno group,
Indicates a nitro group or a hydroxyl group. However, each R 3 shall consist of the same group or atom or a combination of different types. )
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12384482A JPS5915244A (en) | 1982-07-15 | 1982-07-15 | Positive type photosensitive composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12384482A JPS5915244A (en) | 1982-07-15 | 1982-07-15 | Positive type photosensitive composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5915244A JPS5915244A (en) | 1984-01-26 |
| JPH0328701B2 true JPH0328701B2 (en) | 1991-04-19 |
Family
ID=14870785
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12384482A Granted JPS5915244A (en) | 1982-07-15 | 1982-07-15 | Positive type photosensitive composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5915244A (en) |
-
1982
- 1982-07-15 JP JP12384482A patent/JPS5915244A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5915244A (en) | 1984-01-26 |
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