JPH0466349B2 - - Google Patents
Info
- Publication number
- JPH0466349B2 JPH0466349B2 JP60163001A JP16300185A JPH0466349B2 JP H0466349 B2 JPH0466349 B2 JP H0466349B2 JP 60163001 A JP60163001 A JP 60163001A JP 16300185 A JP16300185 A JP 16300185A JP H0466349 B2 JPH0466349 B2 JP H0466349B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- benzophenone
- general formula
- carbon atoms
- tertiary
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000203 mixture Substances 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical group C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 239000003999 initiator Substances 0.000 claims description 7
- 239000012965 benzophenone Substances 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 230000035945 sensitivity Effects 0.000 description 16
- 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 10
- 230000000052 comparative effect Effects 0.000 description 10
- 239000011347 resin Substances 0.000 description 10
- 229920005989 resin Polymers 0.000 description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 9
- 239000011248 coating agent Substances 0.000 description 9
- 238000000576 coating method Methods 0.000 description 9
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- 238000002156 mixing Methods 0.000 description 5
- 239000000975 dye Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 150000001451 organic peroxides Chemical class 0.000 description 4
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229920002120 photoresistant polymer Polymers 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- YGWAFVKXCAQAGJ-UHFFFAOYSA-N bis(2-methylpentan-2-yl) 4-[3,4-bis(2-methylpentan-2-ylperoxycarbonyl)benzoyl]benzene-1,2-dicarboperoxoate Chemical compound C1=C(C(=O)OOC(C)(C)CCC)C(C(=O)OOC(C)(C)CCC)=CC=C1C(=O)C1=CC=C(C(=O)OOC(C)(C)CCC)C(C(=O)OOC(C)(C)CCC)=C1 YGWAFVKXCAQAGJ-UHFFFAOYSA-N 0.000 description 2
- VYHBFRJRBHMIQZ-UHFFFAOYSA-N bis[4-(diethylamino)phenyl]methanone Chemical compound C1=CC(N(CC)CC)=CC=C1C(=O)C1=CC=C(N(CC)CC)C=C1 VYHBFRJRBHMIQZ-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- JVICFMRAVNKDOE-UHFFFAOYSA-M ethyl violet Chemical compound [Cl-].C1=CC(N(CC)CC)=CC=C1C(C=1C=CC(=CC=1)N(CC)CC)=C1C=CC(=[N+](CC)CC)C=C1 JVICFMRAVNKDOE-UHFFFAOYSA-M 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
- 230000002195 synergetic effect Effects 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- OALHHIHQOFIMEF-UHFFFAOYSA-N 3',6'-dihydroxy-2',4',5',7'-tetraiodo-3h-spiro[2-benzofuran-1,9'-xanthene]-3-one Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC(I)=C(O)C(I)=C1OC1=C(I)C(O)=C(I)C=C21 OALHHIHQOFIMEF-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- IEPRKVQEAMIZSS-UHFFFAOYSA-N Di-Et ester-Fumaric acid Natural products CCOC(=O)C=CC(=O)OCC IEPRKVQEAMIZSS-UHFFFAOYSA-N 0.000 description 1
- IEPRKVQEAMIZSS-WAYWQWQTSA-N Diethyl maleate Chemical compound CCOC(=O)\C=C/C(=O)OCC IEPRKVQEAMIZSS-WAYWQWQTSA-N 0.000 description 1
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 1
- 238000003848 UV Light-Curing Methods 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 235000010724 Wisteria floribunda Nutrition 0.000 description 1
- GAZZTULIUXRAAI-UHFFFAOYSA-N [2,3-bis(diethylamino)phenyl]-phenylmethanone Chemical compound CCN(CC)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1N(CC)CC GAZZTULIUXRAAI-UHFFFAOYSA-N 0.000 description 1
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- NENAMKMSJOINIR-UHFFFAOYSA-N bis(2,4,4-trimethylpentan-2-yl) 4-[3,4-bis(2,4,4-trimethylpentan-2-ylperoxycarbonyl)benzoyl]benzene-1,2-dicarboperoxoate Chemical compound C1=C(C(=O)OOC(C)(C)CC(C)(C)C)C(C(=O)OOC(C)(C)CC(C)(C)C)=CC=C1C(=O)C1=CC=C(C(=O)OOC(C)(C)CC(C)(C)C)C(C(=O)OOC(C)(C)CC(C)(C)C)=C1 NENAMKMSJOINIR-UHFFFAOYSA-N 0.000 description 1
- ITXCLKMRLHBUEP-UHFFFAOYSA-N bis(2-methylbutan-2-yl) 4-[3,4-bis(2-methylbutan-2-ylperoxycarbonyl)benzoyl]benzene-1,2-dicarboperoxoate Chemical compound C1=C(C(=O)OOC(C)(C)CC)C(C(=O)OOC(C)(C)CC)=CC=C1C(=O)C1=CC=C(C(=O)OOC(C)(C)CC)C(C(=O)OOC(C)(C)CC)=C1 ITXCLKMRLHBUEP-UHFFFAOYSA-N 0.000 description 1
- LZZMTLWFWQRJIS-UHFFFAOYSA-N bis[2-(4-propan-2-ylphenyl)propan-2-yl] 4-[3,4-bis[2-(4-propan-2-ylphenyl)propan-2-ylperoxycarbonyl]benzoyl]benzene-1,2-dicarboperoxoate Chemical compound C1=CC(C(C)C)=CC=C1C(C)(C)OOC(=O)C1=CC=C(C(=O)C=2C=C(C(C(=O)OOC(C)(C)C=3C=CC(=CC=3)C(C)C)=CC=2)C(=O)OOC(C)(C)C=2C=CC(=CC=2)C(C)C)C=C1C(=O)OOC(C)(C)C1=CC=C(C(C)C)C=C1 LZZMTLWFWQRJIS-UHFFFAOYSA-N 0.000 description 1
- ARSWOISMYKDULL-UHFFFAOYSA-N bis[4-(2,2-dihydroxyethylamino)phenyl]methanone Chemical compound C1=CC(NCC(O)O)=CC=C1C(=O)C1=CC=C(NCC(O)O)C=C1 ARSWOISMYKDULL-UHFFFAOYSA-N 0.000 description 1
- FGURETDKISOZJH-UHFFFAOYSA-N bis[4-(dicyclohexylamino)phenyl]methanone Chemical compound C=1C=C(N(C2CCCCC2)C2CCCCC2)C=CC=1C(=O)C(C=C1)=CC=C1N(C1CCCCC1)C1CCCCC1 FGURETDKISOZJH-UHFFFAOYSA-N 0.000 description 1
- 229960001506 brilliant green Drugs 0.000 description 1
- HXCILVUBKWANLN-UHFFFAOYSA-N brilliant green cation Chemical compound C1=CC(N(CC)CC)=CC=C1C(C=1C=CC=CC=1)=C1C=CC(=[N+](CC)CC)C=C1 HXCILVUBKWANLN-UHFFFAOYSA-N 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- LDCRTTXIJACKKU-ONEGZZNKSA-N dimethyl fumarate Chemical compound COC(=O)\C=C\C(=O)OC LDCRTTXIJACKKU-ONEGZZNKSA-N 0.000 description 1
- 229960004419 dimethyl fumarate Drugs 0.000 description 1
- LDCRTTXIJACKKU-ARJAWSKDSA-N dimethyl maleate Chemical compound COC(=O)\C=C/C(=O)OC LDCRTTXIJACKKU-ARJAWSKDSA-N 0.000 description 1
- KGGOIDKBHYYNIC-UHFFFAOYSA-N ditert-butyl 4-[3,4-bis(tert-butylperoxycarbonyl)benzoyl]benzene-1,2-dicarboperoxoate Chemical compound C1=C(C(=O)OOC(C)(C)C)C(C(=O)OOC(C)(C)C)=CC=C1C(=O)C1=CC=C(C(=O)OOC(C)(C)C)C(C(=O)OOC(C)(C)C)=C1 KGGOIDKBHYYNIC-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- YQGOJNYOYNNSMM-UHFFFAOYSA-N eosin Chemical compound [Na+].OC(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C(O)=C(Br)C=C21 YQGOJNYOYNNSMM-UHFFFAOYSA-N 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 230000000873 masking effect Effects 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pentâ4âenâ2âone Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000191 poly(N-vinyl pyrrolidone) Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- JIYXDFNAPHIAFH-UHFFFAOYSA-N tert-butyl 3-tert-butylperoxycarbonylbenzoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC(C(=O)OC(C)(C)C)=C1 JIYXDFNAPHIAFH-UHFFFAOYSA-N 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Polymerisation Methods In General (AREA)
Description
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[Industrial Application Field] The present invention relates to a highly sensitive photopolymerizable composition. By applying this composition to various substrates, it has a wide range of uses as an image forming material such as printing plate materials, contact films for plate making, masking films, proof papers, recording films, and photoresists. [Prior Art] Conventionally, as a means of increasing the sensitivity of photopolymerizable compositions to light, there has been a method of adding 4,4'-bis(dimethylamino)benzophenone (common name: Michler's ketone) to benzophenone (for example, Kiyomi Kato, Shoji Nakahara, "Introduction to UV Curing Technology," p. 65, Kobunshi Publishing Co., Ltd. (1984)) and a method of adding an organic peroxide to this method (Japanese Patent Application Laid-open No. 60-35725), which certainly have an effect on the polymerization rate. However, the sensitivity obtained with the former is not sufficient for use in photoresists and other applications, and with the latter, when the amount of organic peroxide required to obtain high sensitivity is used, the photosensitive resin liquid and coating The stability over time (hereinafter simply referred to as stability), including thermal stability, of the resulting film is not sufficient. Furthermore, JP-A-60-76503 describes a photoinitiator composition that uses a special organic peroxide and an organic dye compound, but this also has high sensitivity but is not as stable as above. Not enough. [Problems to be solved by the invention] Sensitivity is the most important characteristic of photopolymerizable compositions, and even when work efficiency is taken into account, the appearance of products with higher sensitivity is currently awaited. . In addition, if the stability of the photopolymerizable composition is insufficient, when the drying temperature after applying the photosensitive liquid is high,
Exposure time is not constant, which causes variations in quality and makes it impossible to obtain clear images with good reproducibility.
A so-called "fogging" phenomenon occurs. An object of the present invention is to obtain a photopolymerizable composition which is highly sensitive and has improved stability of a photosensitive solution and a coated film. [Means for Solving the Problems] The present inventors have achieved photopolymerization with high sensitivity and excellent stability by using a combination of a specific organic peroxide and a photosensitizer as a photopolymerization initiator. The inventors have discovered that a sexual composition can be obtained, leading to the present invention. That is, the present invention relates to a compound having an ethylenically unsaturated double bond, a benzophenone group-containing polyhydric peroxyester represented by the following general formula (), and a 4,4'-bis(dialkylamino) represented by the general formula (). The present invention provides a highly sensitive photopolymerizable composition containing a photopolymerization initiator consisting of benzophenone. General formula () [In the formula, R 1 and Râ² 1 each have a carbon number of 4 to 8
tertiary alkyl group, or a tertiary alkyl group having 9 to 12 carbon atoms
The aralkyl groups R 2 and R' 2 each represent a hydrogen atom, a tertiary alkoxy group having 4 to 8 carbon atoms, or a tertiary aralkyloxy group having 9 to 12 carbon atoms. ] General formula () [However, R represents an alkyl group, a cycloalkyl group, or a hydroxyalkyl group having 1 to 6 carbon atoms. ] The compound having an ethylenically unsaturated double bond used in the present invention may be any compound that can be polymerized with a photopolymerization initiator, such as acrylic acid, methacrylic acid, itaconic acid, maleic acid and its anhydride, phthalate, etc. Acids and their anhydrides, unsaturated acids such as fumaric acid, methyl (meth)acrylate, ethyl (meth)acrylate, butyl (meth)acrylate, glycidyl (meth)acrylate, hydroxyethyl (meth)acrylate, Unsaturated acid esters such as dimethyl maleate, diethyl maleate, dimethyl fumarate, pentaerythritol tri(meth)acrylate, trimethylolpropane tri(meth)acrylate, ethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, etc. and styrene, acrylamide, acrylonitrile, N-vinylpyrrolidone, vinyl acetate, and various unsaturated polyesters, unsaturated polyethers, unsaturated polyurethanes, and (meth)acrylate compounds having epoxy groups. In addition, the general formula () used as a photopolymerization initiator in the present invention [In the formula, R 1 and Râ² 1 each have a carbon number of 4 to 8
tertiary alkyl group, or a tertiary alkyl group having 9 to 12 carbon atoms
The aralkyl groups R 2 and R' 2 each represent a hydrogen atom, a tertiary alkoxy group having 4 to 8 carbon atoms, or a tertiary aralkyloxy group having 9 to 12 carbon atoms. ] Examples of benzophenone group-containing polyhydric peroxyesters include 3,3',4,4'-tetra-(tert-butylperoxycarbonyl)benzophenone, 3,3',4,4'-tetra-( tertiary amylperoxycarbonyl)benzophenone, 3,
3',4,4'-tetra(tertiary hexylperoxycarbonyl)benzophenone, 3,3',4,4'-tetra(tertiary octylperoxycarbonyl)benzophenone, 3,3',4,4'-tetra( cumylperoxycarbonyl)benzophenone, 3,3â²,
4,4'-tetra(p-isopropylcumylperoxycarbonyl)benzophenone, and the like. General formula () used in the present invention [However, R represents an alkyl group, a cycloalkyl group, or a hydroxyalkyl group having 1 to 6 carbon atoms. ] Examples of the compounds represented by include 4,4'-bis(dimethylamino)benzophenone, 4,4'-bis(diethylamino)benzophenone, 4,4'-bis(dicyclohexylamino)benzophenone,
Examples include 4,4'-bis(dihydroxyethylamino)benzophenone. Among these, 4,4'-bis(dimethylamino)benzophenone and 4,4'-
Particularly preferred is bis(diethylamino)benzophenone. The blending ratio of each of the above components is 0.01 to 0.01 to 100 parts by weight of the compound having an ethylenically unsaturated double bond, and the benzophenone group-containing polyhydric peroxyester represented by the general formula () and the compound represented by the general formula (), respectively. 100 parts by weight, preferably 0.1 to 30 parts by weight, particularly preferably 1 to 30 parts by weight. The compounding ratio of compound (a) represented by general formula () and compound (b) represented by general formula () is a:b in weight ratio.
is preferably 1:10 to 10:1. A photopolymerizable composition with excellent performance cannot be obtained outside the range of the above-mentioned blending amount and blending ratio. The photopolymerizable composition of the present invention has as an essential component a compound having an ethylenically unsaturated double bond that is polymerizable with the photopolymerization initiator, but may optionally include a binder resin, a polymerization inhibitor, a dye, etc. can be used by appropriately blending them. Binder resin is used as a coating film forming aid for printing plate materials and photoresists for the purpose of improving physical properties, and is usually used in an amount of 50 to 500 parts by weight per 100 parts by weight of a compound having an ethylenically unsaturated double bond. It is preferable to use it in moderation. Examples of the binder resin include (meth)acrylate resin, vinylpyrrolidone resin, and vinyl alcohol resin, and the resin may or may not contain a polymeric group. Examples of polymerization inhibitors include p-methoxyphenol and hydroquinone, and examples of dyes include brilliant green, ethyl violet, eosin, and erythrosin B. The photopolymerizable composition of the present invention is used as a photosensitive resin sheet by coating on various substrates,
At this time, the photopolymerizable composition is methyl ethyl ketone,
Dilute it approximately 5 to 100 times with a solvent such as isopropanol or methyl cellosolve, and apply it on the substrate using a method such as spin coating, roll coating, or bar coating.
It is used by applying it evenly to a thickness of 0.5 to 50 ÎŒm. The thus obtained photosensitive resin sheet undergoes a photopolymerization reaction by being irradiated with actinic light such as ultraviolet rays, and a predetermined image is obtained by developing the sheet. [Effects of the Invention] The photopolymerizable composition of the present invention uses a combination of the compound represented by the general formula () and the compound represented by the general formula () as a photopolymerization initiator. It has significantly higher sensitivity than other compositions, and also has superior stability. Therefore,
It can be used in many photopolymerization reactions, and can be applied to a wide variety of fields such as various image forming materials, photocurable resins, paints, and printing inks. [Examples] The present invention will be explained in more detail below using Examples and Comparative Examples. Parts in the examples indicate parts by weight. Examples 1 to 2 and Comparative Examples 1 to 3 A photosensitive liquid was prepared by uniformly mixing photopolymerizable compositions having the following composition. These photosensitive solutions were applied onto a grained anodized aluminum plate using a whirler so that the dry film thickness was 2 Όm, and dried at 40° C. for 5 minutes to obtain a photosensitive substrate. - 100 parts of epoxy acrylate (EA-800 manufactured by Shin-Nakamura Chemical Co., Ltd.) - 100 parts of poly(butyl acrylate/ethyl acrylate/methacrylic acid) (mole ratio 50/40/10, molecular weight 100,000) - 3,3',4,4'-tetra-(tert-butylperoxycarbonyl)benzophenone (hereinafter
Parts shown in Table 1: 4,4'-bis(diethylamino)benzophenone (hereinafter referred to as EMK) Parts: Benzophenone (hereinafter referred to as BP) Parts: Di-tert-butylperoxyisophthalate (hereinafter referred to as PBIF) 1,800 parts of methyl cellosolve A step tablet (No. 2 manufactured by Kodaku Corporation) was placed on top of this photosensitive substrate and adhered in vacuum, and exposed for 1.5 seconds with a 2K.W. ultra-high pressure mercury lamp from a distance of 60cm.
Commercially available alkaline developer (manufactured by Fuji Photo Film Co., Ltd.)
Development was carried out with DN-3C (water-diluted product), and after drying, the number of steps in the exposed area by the step tablet obtained was determined by visual judgment, and this was taken as the initial sensitivity. The results are shown in Table 1. The higher the number of steps, the higher the sensitivity.If there is a difference of 2 steps, the sensitivity will be 2.
Double. Next, place the photosensitive substrate before exposure in a heat insulator at 55â.
After standing still for 48 hours, post-exposure development was performed in the same manner as above to examine stability. The results are shown in Table 1. In addition,
Here, "normal" indicates that normal development is possible after exposure, and "impossible" indicates that "fogging" occurs and normal development is impossible.
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ããããªããæ¬çºæã¯BTTBãšEMKã®çžä¹å¹æ
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ã§ããããããã«ãå®æœäŸïŒã«ãããŠãEMK5éš
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ã·åºãšãæããBTTBãïŒéšãšããå°éçšãã
ããšã§ãæ¯èŒäŸïŒã«ãããŠBPãšPBIFãå¥ã
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ãïŒ100ïŒäžã«ãããŒã³ãŒã¿ãŒãçšããŠä¹Ÿç¥å¡è
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ããŠãçŸåã«æ°Žãçšãã以å€ã¯å®æœäŸïŒãšåæ§ã«
ããŠãåææ床ããã³å®å®æ§ã調ã¹ãããããã®
çµæãè¡šïŒã«ç€ºãã
ã» ãã³ã¿ãšãªã¹ãªããŒã«ããªã¢ã¯ãªã¬ãŒã
100éš
ã» ããªââããã«ãããªãã³ïŒååé36äžïŒ
100éš
ã» BTTB è¡šïŒã«ç€ºãã
ã» ïŒïŒ4â²âãã¹ïŒãžã¡ãã«ã¢ããïŒãã³ãŸããš
ãã³ïŒä»¥äžMKãšããïŒ ã ã
ã» BP ã ã
ã» PBIF ã ã
ã» ã¡ãã«ã»ããœã«ã 5000ã[Table] *Image cannot be taken. **Not exposed to light at all.
As is clear from the results in Table 1, BTTB and
All of the products of the present invention that are used in combination with EMK have higher sensitivity and better stability than those of comparative examples. It is clear from Comparative Examples 1 and 2 that the present invention is based on the synergistic effect of BTTB and EMK, but in addition, in Example 1, 5 parts of EMK have a benzophenone group and a peroxy group in the same molecule. The excellent synergistic effect is also recognized by the fact that by using a small amount of 8 parts of BTTB, a significantly superior performance is obtained than when 34 parts of BP and PBIF were used separately in Comparative Example 3. Example 3 and Comparative Examples 4 to 5 A photosensitive solution having the following composition was prepared according to Example 1, and coated on coated paper (Pearl Coat #100, manufactured by Mitsubishi Paper Mills Co., Ltd.) using a bar coater. A photosensitive sheet was obtained by uniformly applying the film to a dry film thickness of 1 ÎŒm and drying. Using this photosensitive sheet, the initial sensitivity and stability were examined in the same manner as in Example 1 except that water was used for development. The results are shown in Table 2.ã»Pentaerythritol triacrylate
100 parts/Poly-N-vinylpyrrolidone (molecular weight 360,000)
100 parts ã» BTTB Shown in Table 2 ã» 4,4'-bis(dimethylamino)benzophenone (hereinafter referred to as MK) ã ã ã» BP ã ã ã» PBIF ã ã ã» Methyl cellosolve 5000ã
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補ãããããé¡é¢ã«è¿ãç 磚ããé
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ãããã«å·¥æ¥(æ ª)補ãJISH3100ïŒC1100PïŒïŒäžã«ã
å転å¡åžæ©ãçšããŠä¹Ÿç¥å¡èåã5ÎŒmã«ãªããã
ã«åäžã«å¡åžãã也ç¥ãè¡ãªã€ãŠæå
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ããŒã«ïŒæ°ŽïŒééæ¯50ïŒ50ïŒãçšãã以å€ã¯å®æœ
äŸïŒãšåæ§ã«ããŠãåææ床ããã³å®å®æ§ã調ã¹
ãããããã®çµæãè¡šïŒã«ç€ºãã
ã» ããªã¡ãããŒã«ãããã³ããªã¢ã¯ãªã¬ãŒã
50éš
ã» ããªïŒã¡ãã«ã¡ã¿ã¯ãªã¬ãŒãïŒã¡ã¿ã¯ãªã«
é
žïŒïŒã¢ã«æ¯50ïŒ50ãååéïŒäžïŒ 150éš
ã» ïŒïŒ3â²ïŒïŒïŒ4â²âããã©ïŒç¬¬ïŒããã·ã«ãã«
ãªãã·ã«ã«ããã«ïŒãã³ãŸããšãã³ïŒä»¥äž
BTTHãšããïŒ è¡šïŒã«ç€ºãéš
ã» EMK ã ã
ã» BP ã ã
ã» PBIF ã ã
ã» ïŒïŒïŒïŒïŒâããªïŒïŒâã¡ããã·ããšãã«ïŒ
ãã¢ããªãªãŠã ãã«ãªããã¬ãŒãïŒä»¥äžMTF
ãšããïŒ è¡šïŒã«ç€ºãéš
ã» ãšãã«ãã€ãªã¬ãã ïŒã
㻠âã¡ããã·ããšããŒã« 0.1ã
ã» ã¡ãã«ãšãã«ã±ãã³ 500ã
ã» ã€ãœãããããŒã« 500ã[Table] From the results in Table 2, it is clear that the samples of the present invention have higher sensitivity and better stability than those of the comparative examples. Example 4 and Comparative Examples 6 to 7 A photosensitive solution having the following composition was prepared according to Example 1, and it was coated on a copper plate (JISH3100 (C1100P) manufactured by Japan Test Panel Industry Co., Ltd.) polished to a near mirror surface. To,
The coating was applied uniformly using a rotary coating machine so that the dry coating thickness was 5 ÎŒm, and the coating was dried to obtain a photosensitive copper plate. Using this photosensitive copper plate, the initial sensitivity and stability were examined in the same manner as in Example 1, except that isopropanol/water (weight ratio 50/50) was used for development. The results are shown in Table 3.ã»Trimethylolpropane triacrylate
50 parts Poly(methyl methacrylate/methacrylic acid) (mole ratio 50/50, molecular weight 80,000) 150 parts 3,3',4,4'-tetra(tertiary hexylperoxycarbonyl)benzophenone (hereinafter
BTTH) The parts shown in Table 3 EMK ã ã ã» BP ã ã ã» PBIF ã ã ã» 2,4,6-tri(4-methoxyphenyl)
Thiapyrylium fluoroborate (MTF)
) Ethyl violet 2ã ã» P-methoxyphenol 0.1ã ã» Methyl ethyl ketone 500ã ã» Isopropanol 500ã
ãè¡šã
è¡šïŒã®çµæãããæ¬çºæã®ãã®ã¯æ¯èŒäŸïŒãã
ã³EMKã®ä»£ããã«ç¹æ®ãªææ©ææãçšããæ¯èŒ
äŸïŒã®ãã®ããé«æ床ã§å®å®æ§ãåªããŠããããš
ãæããã§ããã[Table] From the results in Table 3, it is clear that the product of the present invention has higher sensitivity and better stability than Comparative Example 6 and Comparative Example 7 in which a special organic dye was used instead of EMK.
Claims (1)
äžèšäžè¬åŒïŒïŒã§ç€ºããããã³ãŸããšãã³åºå«
æå€äŸ¡ãã«ãªãã·ãšã¹ãã«åã³äžè¬åŒïŒïŒã§ç€º
ãããïŒïŒ4â²âãã¹ïŒãžã¢ã«ãã«ã¢ããïŒãã³ãŸ
ããšãã³ãããªãå éåéå§å€ãšãå«æããé«æ
床å éåæ§çµæç©ã äžè¬åŒ ãåŒäžR1ããã³Râ²1ã¯ããããççŽ æ°ïŒããïŒ
ã®ç¬¬ïŒã¢ã«ãã«åºããŸãã¯ççŽ æ°ïŒãã12ã®ç¬¬ïŒ
ã¢ã©ã«ãã«åºãR2ããã³Râ²2ã¯ããããæ°ŽçŽ åå
ãŸãã¯ççŽ æ°ïŒããïŒã®ç¬¬ïŒã¢ã«ã³ãã·åºãŸãã¯
ççŽ æ°ïŒãã12ã®ç¬¬ïŒã¢ã©ã«ãã«ãªãã·åºãè¡šã
ããã äžè¬åŒ ãäœããã¯ççŽ æ°ïŒããïŒã®ã¢ã«ãã«åºãã·
ã¯ãã¢ã«ãã«åºãŸãã¯ããããã·ã¢ã«ãã«åºãè¡š
ãããã[Scope of Claims] 1. A compound having an ethylenically unsaturated double bond, a benzophenone group-containing polyhydric peroxyester represented by the following general formula (), and a 4,4'-bis(dialkylamino) represented by the general formula (). ) A highly sensitive photopolymerizable composition containing a photopolymerization initiator consisting of benzophenone. general formula [In the formula, R 1 and Râ² 1 each have a carbon number of 4 to 8
tertiary alkyl group, or a tertiary alkyl group having 9 to 12 carbon atoms
The aralkyl groups R 2 and R' 2 each represent a hydrogen atom, a tertiary alkoxy group having 4 to 8 carbon atoms, or a tertiary aralkyloxy group having 9 to 12 carbon atoms. ] General formula [However, R represents an alkyl group, a cycloalkyl group, or a hydroxyalkyl group having 1 to 6 carbon atoms. ]
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP16300185A JPS6224240A (en) | 1985-07-25 | 1985-07-25 | Photopolymerizable composition having high sensitivity |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP16300185A JPS6224240A (en) | 1985-07-25 | 1985-07-25 | Photopolymerizable composition having high sensitivity |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS6224240A JPS6224240A (en) | 1987-02-02 |
JPH0466349B2 true JPH0466349B2 (en) | 1992-10-22 |
Family
ID=15765310
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP16300185A Granted JPS6224240A (en) | 1985-07-25 | 1985-07-25 | Photopolymerizable composition having high sensitivity |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS6224240A (en) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS63206741A (en) * | 1987-02-24 | 1988-08-26 | Mitsubishi Gas Chem Co Inc | Photosensitive polymer composition |
US5184027A (en) * | 1987-03-20 | 1993-02-02 | Hitachi, Ltd. | Clock signal supply system |
JP2751453B2 (en) * | 1989-09-05 | 1998-05-18 | æ¥æ¬æ²¹èæ ªåŒäŒç€Ÿ | Photopolymerization initiator |
JP3860340B2 (en) * | 1998-06-08 | 2006-12-20 | æ°æ¥éµååŠæ ªåŒäŒç€Ÿ | Photopolymerizable resin composition |
KR100349600B1 (en) * | 1998-08-18 | 2002-11-18 | 죌ìíì¬ ìì§íí | Triazine compound containing benzophenone group and photoinitiator containing the same |
JPWO2023282045A1 (en) * | 2021-07-05 | 2023-01-12 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6035725A (en) * | 1983-08-09 | 1985-02-23 | Fuji Photo Film Co Ltd | Photopolymerizable composition |
-
1985
- 1985-07-25 JP JP16300185A patent/JPS6224240A/en active Granted
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6035725A (en) * | 1983-08-09 | 1985-02-23 | Fuji Photo Film Co Ltd | Photopolymerizable composition |
Also Published As
Publication number | Publication date |
---|---|
JPS6224240A (en) | 1987-02-02 |
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