JPH0371443B2 - - Google Patents
Info
- Publication number
- JPH0371443B2 JPH0371443B2 JP28439587A JP28439587A JPH0371443B2 JP H0371443 B2 JPH0371443 B2 JP H0371443B2 JP 28439587 A JP28439587 A JP 28439587A JP 28439587 A JP28439587 A JP 28439587A JP H0371443 B2 JPH0371443 B2 JP H0371443B2
- Authority
- JP
- Japan
- Prior art keywords
- composition
- alkyl ester
- carbonylbis
- diethylaminocoumarin
- triphenylimidazolyl dimer
- 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 54
- 150000001875 compounds Chemical class 0.000 claims description 27
- -1 2,4,5 - triphenylimidazolyl Chemical class 0.000 claims description 24
- 239000000539 dimer Substances 0.000 claims description 23
- SANIRTQDABNCHF-UHFFFAOYSA-N 7-(diethylamino)-3-[7-(diethylamino)-2-oxochromene-3-carbonyl]chromen-2-one Chemical compound C1=C(N(CC)CC)C=C2OC(=O)C(C(=O)C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=CC2=C1 SANIRTQDABNCHF-UHFFFAOYSA-N 0.000 claims description 21
- VNQXSTWCDUXYEZ-UHFFFAOYSA-N 1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione Chemical class C1CC2(C)C(=O)C(=O)C1C2(C)C VNQXSTWCDUXYEZ-UHFFFAOYSA-N 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 19
- 229930006711 bornane-2,3-dione Natural products 0.000 claims description 19
- 125000005907 alkyl ester group Chemical group 0.000 claims description 18
- 229920002120 photoresistant polymer Polymers 0.000 claims description 17
- 230000005855 radiation Effects 0.000 claims description 16
- 230000000977 initiatory effect Effects 0.000 claims description 15
- 238000006116 polymerization reaction Methods 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- 239000000463 material Substances 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- XPKFLEVLLPKCIW-UHFFFAOYSA-N ethyl 4-(diethylamino)benzoate Chemical compound CCOC(=O)C1=CC=C(N(CC)CC)C=C1 XPKFLEVLLPKCIW-UHFFFAOYSA-N 0.000 claims description 4
- 238000005406 washing Methods 0.000 claims description 4
- 239000000178 monomer Substances 0.000 claims description 3
- DVZGSAUNAZEWAI-UHFFFAOYSA-N 2-(2-methoxyphenyl)-2-[2-(2-methoxyphenyl)-4,5-diphenylimidazol-2-yl]-4,5-diphenylimidazole Chemical group COC1=CC=CC=C1C1(C2(N=C(C(=N2)C=2C=CC=CC=2)C=2C=CC=CC=2)C=2C(=CC=CC=2)OC)N=C(C=2C=CC=CC=2)C(C=2C=CC=CC=2)=N1 DVZGSAUNAZEWAI-UHFFFAOYSA-N 0.000 claims 1
- 230000001235 sensitizing effect Effects 0.000 claims 1
- HCLJOFJIQIJXHS-UHFFFAOYSA-N 2-[2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOCCOC(=O)C=C HCLJOFJIQIJXHS-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 4
- 239000003504 photosensitizing agent Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 230000002195 synergetic effect Effects 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 239000002318 adhesion promoter Substances 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- GBOJZXLCJZDBKO-UHFFFAOYSA-N 2-(2-chlorophenyl)-2-[2-(2-chlorophenyl)-4,5-diphenylimidazol-2-yl]-4,5-diphenylimidazole Chemical compound ClC1=CC=CC=C1C1(C2(N=C(C(=N2)C=2C=CC=CC=2)C=2C=CC=CC=2)C=2C(=CC=CC=2)Cl)N=C(C=2C=CC=CC=2)C(C=2C=CC=CC=2)=N1 GBOJZXLCJZDBKO-UHFFFAOYSA-N 0.000 description 2
- CDSULTPOCMWJCM-UHFFFAOYSA-N 4h-chromene-2,3-dione Chemical class C1=CC=C2OC(=O)C(=O)CC2=C1 CDSULTPOCMWJCM-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000012190 activator Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 150000001728 carbonyl compounds Chemical class 0.000 description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- MXWGELSDNRFWFD-UHFFFAOYSA-N 2,4,5,6-tetraphenyl-1h-benzimidazole Chemical compound C1=CC=CC=C1C(NC1=CC(=C2C=3C=CC=CC=3)C=3C=CC=CC=3)=NC1=C2C1=CC=CC=C1 MXWGELSDNRFWFD-UHFFFAOYSA-N 0.000 description 1
- WOSJKENLZHUUMC-UHFFFAOYSA-N 2-(1-methylindol-2-yl)acetic acid Chemical compound C1=CC=C2N(C)C(CC(O)=O)=CC2=C1 WOSJKENLZHUUMC-UHFFFAOYSA-N 0.000 description 1
- RPVVMXMIPQHORV-UHFFFAOYSA-N 2-(dimethylamino)-3-ethylbenzoic acid Chemical compound CCC1=CC=CC(C(O)=O)=C1N(C)C RPVVMXMIPQHORV-UHFFFAOYSA-N 0.000 description 1
- LXCJXYYYOPFEDH-UHFFFAOYSA-N 3-(2-oxochromene-3-carbonyl)chromen-2-one Chemical compound C1=CC=C2OC(=O)C(C(C=3C(OC4=CC=CC=C4C=3)=O)=O)=CC2=C1 LXCJXYYYOPFEDH-UHFFFAOYSA-N 0.000 description 1
- HYORIVUCOQKMOC-UHFFFAOYSA-N 3-benzoyl-7-methoxychromen-2-one Chemical compound O=C1OC2=CC(OC)=CC=C2C=C1C(=O)C1=CC=CC=C1 HYORIVUCOQKMOC-UHFFFAOYSA-N 0.000 description 1
- LDUNNUKQPKEIJR-UHFFFAOYSA-N 4,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione Chemical compound C1CC2(C)C(=O)C(=O)C1C2(C)C.C1CC2(C)C(=O)C(=O)C1C2(C)C LDUNNUKQPKEIJR-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- NPKSPKHJBVJUKB-UHFFFAOYSA-N N-phenylglycine Chemical compound OC(=O)CNC1=CC=CC=C1 NPKSPKHJBVJUKB-UHFFFAOYSA-N 0.000 description 1
- WYWZRNAHINYAEF-UHFFFAOYSA-N Padimate O Chemical compound CCCCC(CC)COC(=O)C1=CC=C(N(C)C)C=C1 WYWZRNAHINYAEF-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 238000012644 addition polymerization Methods 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229960004050 aminobenzoic acid Drugs 0.000 description 1
- 229910000074 antimony hydride Inorganic materials 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- RBFQJDQYXXHULB-UHFFFAOYSA-N arsane Chemical compound [AsH3] RBFQJDQYXXHULB-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
- JQMZFDMFXIPUSL-UHFFFAOYSA-N bis(2-phenylphenyl)methanone Chemical compound C=1C=CC=C(C=2C=CC=CC=2)C=1C(=O)C1=CC=CC=C1C1=CC=CC=C1 JQMZFDMFXIPUSL-UHFFFAOYSA-N 0.000 description 1
- 229910000072 bismuth hydride Inorganic materials 0.000 description 1
- BPBOBPIKWGUSQG-UHFFFAOYSA-N bismuthane Chemical compound [BiH3] BPBOBPIKWGUSQG-UHFFFAOYSA-N 0.000 description 1
- TUZBYYLVVXPEMA-UHFFFAOYSA-N butyl prop-2-enoate;styrene Chemical compound C=CC1=CC=CC=C1.CCCCOC(=O)C=C TUZBYYLVVXPEMA-UHFFFAOYSA-N 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229960000956 coumarin Drugs 0.000 description 1
- 235000001671 coumarin Nutrition 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 230000009545 invasion Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920005596 polymer binder Polymers 0.000 description 1
- 239000002491 polymer binding agent Substances 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 229940071182 stannate Drugs 0.000 description 1
- OUULRIDHGPHMNQ-UHFFFAOYSA-N stibane Chemical compound [SbH3] OUULRIDHGPHMNQ-UHFFFAOYSA-N 0.000 description 1
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 description 1
- 150000003453 sulfinic acid esters Chemical class 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
Landscapes
- Polymerisation Methods In General (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US93068686A | 1986-11-12 | 1986-11-12 | |
| US930686 | 1986-11-12 | ||
| US043054 | 1987-04-27 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63152605A JPS63152605A (ja) | 1988-06-25 |
| JPH0371443B2 true JPH0371443B2 (pt) | 1991-11-13 |
Family
ID=25459612
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP28439587A Granted JPS63152605A (ja) | 1986-11-12 | 1987-11-12 | 光開始剤組成物 |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS63152605A (pt) |
| ZA (1) | ZA878064B (pt) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6202683B2 (ja) * | 2014-04-16 | 2017-09-27 | 日本化薬株式会社 | 液晶滴下工法用液晶シール剤及びそれを用いた液晶表示セル |
-
1987
- 1987-10-27 ZA ZA878064A patent/ZA878064B/xx unknown
- 1987-11-12 JP JP28439587A patent/JPS63152605A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS63152605A (ja) | 1988-06-25 |
| ZA878064B (en) | 1988-07-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4239850A (en) | Photopolymerizable composition | |
| US3885964A (en) | Photoimaging process using nitroso dimer | |
| KR960016468B1 (ko) | 중합성 화합물 | |
| US4258121A (en) | Photopolymerizable compositions | |
| US4983498A (en) | Photopolymerizable mixture and recording material produced therefrom | |
| RU1792538C (ru) | Фотополимеризующийс состав | |
| JPH0697339B2 (ja) | 光重合性組成物 | |
| EP0341720A2 (en) | Light-sensitive compositions | |
| JPH06308727A (ja) | 光重合性組成物 | |
| US5645974A (en) | Process for the production of printing plates | |
| JPH08305018A (ja) | 改良された光重合性組成物 | |
| JPS6310811B2 (pt) | ||
| JPS6088005A (ja) | 光硬化樹脂組成物 | |
| JPS6212801B2 (pt) | ||
| US4894314A (en) | Photoinitiator composition containing bis ketocoumarin dialkylamino benzoate, camphorquinone and/or a triphenylimidazolyl dimer | |
| US3901705A (en) | Method of using variable depth photopolymerization imaging systems | |
| JPH01126302A (ja) | 光重合性組成物 | |
| JPH0371443B2 (pt) | ||
| JP3644731B2 (ja) | 新規な光硬化性樹脂組成物 | |
| JP2990831B2 (ja) | 光重合性組成物 | |
| AU602541B2 (en) | Photoinitiator composition | |
| JPS6076735A (ja) | 光硬化樹脂組成物 | |
| JPS6332541A (ja) | 光重合性組成物 | |
| JP2003186183A (ja) | 感光性樹脂組成物及び積層体 | |
| JPH0588244B2 (pt) |