JP2001520759A - エポキシ/ポリオール樹脂組成物を硬化させるための3成分光開始剤系 - Google Patents
エポキシ/ポリオール樹脂組成物を硬化させるための3成分光開始剤系Info
- Publication number
- JP2001520759A JP2001520759A JP54388598A JP54388598A JP2001520759A JP 2001520759 A JP2001520759 A JP 2001520759A JP 54388598 A JP54388598 A JP 54388598A JP 54388598 A JP54388598 A JP 54388598A JP 2001520759 A JP2001520759 A JP 2001520759A
- Authority
- JP
- Japan
- Prior art keywords
- group
- composition
- alkyl
- groups
- substituted
- 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.)
- Granted
Links
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- 229920005862 polyol Polymers 0.000 title description 22
- 150000003077 polyols Chemical class 0.000 title description 21
- 239000011342 resin composition Substances 0.000 title description 5
- 239000000203 mixture Substances 0.000 claims abstract description 142
- -1 hexafluoroantimonate Chemical compound 0.000 claims abstract description 84
- 150000001875 compounds Chemical class 0.000 claims abstract description 50
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 43
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 36
- 239000003822 epoxy resin Substances 0.000 claims abstract description 33
- 239000000126 substance Substances 0.000 claims abstract description 33
- VNQXSTWCDUXYEZ-UHFFFAOYSA-N 1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione Chemical compound C1CC2(C)C(=O)C(=O)C1C2(C)C VNQXSTWCDUXYEZ-UHFFFAOYSA-N 0.000 claims abstract description 32
- 229930006711 bornane-2,3-dione Natural products 0.000 claims abstract description 32
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000012086 standard solution Substances 0.000 claims abstract description 15
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims abstract description 10
- OZLBDYMWFAHSOQ-UHFFFAOYSA-N diphenyliodanium Chemical compound C=1C=CC=CC=1[I+]C1=CC=CC=C1 OZLBDYMWFAHSOQ-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000003479 dental cement Substances 0.000 claims abstract 3
- 239000011350 dental composite resin Substances 0.000 claims abstract 2
- 239000000463 material Substances 0.000 claims description 62
- 125000003118 aryl group Chemical group 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 239000000499 gel Substances 0.000 claims description 16
- 150000002118 epoxides Chemical class 0.000 claims description 14
- 125000006575 electron-withdrawing group Chemical group 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 11
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- NEGFNJRAUMCZMY-UHFFFAOYSA-N 3-(dimethylamino)benzoic acid Chemical compound CN(C)C1=CC=CC(C(O)=O)=C1 NEGFNJRAUMCZMY-UHFFFAOYSA-N 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 150000002576 ketones Chemical class 0.000 claims description 6
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 6
- 125000003107 substituted aryl group Chemical group 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 229920000570 polyether Polymers 0.000 claims description 5
- LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 claims description 4
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 claims description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 4
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 4
- 125000005520 diaryliodonium group Chemical group 0.000 claims description 4
- YDIYEOMDOWUDTJ-UHFFFAOYSA-N 4-(dimethylamino)benzoic acid Chemical compound CN(C)C1=CC=C(C(O)=O)C=C1 YDIYEOMDOWUDTJ-UHFFFAOYSA-N 0.000 claims description 3
- CDSULTPOCMWJCM-UHFFFAOYSA-N 4h-chromene-2,3-dione Chemical group C1=CC=C2OC(=O)C(=O)CC2=C1 CDSULTPOCMWJCM-UHFFFAOYSA-N 0.000 claims description 3
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 3
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 3
- 239000012955 diaryliodonium Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 238000003384 imaging method Methods 0.000 claims description 3
- 230000001678 irradiating effect Effects 0.000 claims description 3
- XAMUDJHXFNRLCY-UHFFFAOYSA-N phenthoate Chemical compound CCOC(=O)C(SP(=S)(OC)OC)C1=CC=CC=C1 XAMUDJHXFNRLCY-UHFFFAOYSA-N 0.000 claims description 3
- 239000000565 sealant Substances 0.000 claims description 3
- 239000000600 sorbitol Substances 0.000 claims description 3
- OAKFFVBGTSPYEG-UHFFFAOYSA-N (4-prop-2-enoyloxycyclohexyl) prop-2-enoate Chemical compound C=CC(=O)OC1CCC(OC(=O)C=C)CC1 OAKFFVBGTSPYEG-UHFFFAOYSA-N 0.000 claims description 2
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 claims description 2
- SOLBSNQBVLAREX-UHFFFAOYSA-N 1-[4-(dimethylamino)phenyl]-2-hydroxy-2-phenylethanone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C(O)C1=CC=CC=C1 SOLBSNQBVLAREX-UHFFFAOYSA-N 0.000 claims description 2
- PUGOMSLRUSTQGV-UHFFFAOYSA-N 2,3-di(prop-2-enoyloxy)propyl prop-2-enoate Chemical compound C=CC(=O)OCC(OC(=O)C=C)COC(=O)C=C PUGOMSLRUSTQGV-UHFFFAOYSA-N 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 2
- HWSSEYVMGDIFMH-UHFFFAOYSA-N 2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOC(=O)C(C)=C HWSSEYVMGDIFMH-UHFFFAOYSA-N 0.000 claims description 2
- GGRBZHPJKWFAFZ-UHFFFAOYSA-N 3,4-bis(2-methylprop-2-enoyloxy)butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC(OC(=O)C(C)=C)COC(=O)C(C)=C GGRBZHPJKWFAFZ-UHFFFAOYSA-N 0.000 claims description 2
- HTWRFCRQSLVESJ-UHFFFAOYSA-N 3-(2-methylprop-2-enoyloxy)propyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCOC(=O)C(C)=C HTWRFCRQSLVESJ-UHFFFAOYSA-N 0.000 claims description 2
- GFLJTEHFZZNCTR-UHFFFAOYSA-N 3-prop-2-enoyloxypropyl prop-2-enoate Chemical compound C=CC(=O)OCCCOC(=O)C=C GFLJTEHFZZNCTR-UHFFFAOYSA-N 0.000 claims description 2
- JYMNQRQQBJIMCV-UHFFFAOYSA-N 4-(dimethylamino)benzonitrile Chemical compound CN(C)C1=CC=C(C#N)C=C1 JYMNQRQQBJIMCV-UHFFFAOYSA-N 0.000 claims description 2
- JTHZUSWLNCPZLX-UHFFFAOYSA-N 6-fluoro-3-methyl-2h-indazole Chemical compound FC1=CC=C2C(C)=NNC2=C1 JTHZUSWLNCPZLX-UHFFFAOYSA-N 0.000 claims description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims 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 claims description 2
- 239000003082 abrasive agent Substances 0.000 claims description 2
- 150000001299 aldehydes Chemical class 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 239000001273 butane Substances 0.000 claims description 2
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 2
- 239000011248 coating agent Substances 0.000 claims description 2
- 238000000576 coating method Methods 0.000 claims description 2
- RSJLWBUYLGJOBD-UHFFFAOYSA-M diphenyliodanium;chloride Chemical group [Cl-].C=1C=CC=CC=1[I+]C1=CC=CC=C1 RSJLWBUYLGJOBD-UHFFFAOYSA-M 0.000 claims description 2
- 239000003205 fragrance Substances 0.000 claims description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 2
- 229920002120 photoresistant polymer Polymers 0.000 claims description 2
- QTECDUFMBMSHKR-UHFFFAOYSA-N prop-2-enyl prop-2-enoate Chemical compound C=CCOC(=O)C=C QTECDUFMBMSHKR-UHFFFAOYSA-N 0.000 claims description 2
- BOQSSGDQNWEFSX-UHFFFAOYSA-N propan-2-yl 2-methylprop-2-enoate Chemical compound CC(C)OC(=O)C(C)=C BOQSSGDQNWEFSX-UHFFFAOYSA-N 0.000 claims description 2
- 229910000679 solder Inorganic materials 0.000 claims description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 2
- 125000004149 thio group Chemical group *S* 0.000 claims description 2
- CRUILBNAQILVHZ-UHFFFAOYSA-N 1,2,3-trimethoxybenzene Chemical compound COC1=CC=CC(OC)=C1OC CRUILBNAQILVHZ-UHFFFAOYSA-N 0.000 claims 2
- LGPAKRMZNPYPMG-UHFFFAOYSA-N (3-hydroxy-2-prop-2-enoyloxypropyl) prop-2-enoate Chemical compound C=CC(=O)OC(CO)COC(=O)C=C LGPAKRMZNPYPMG-UHFFFAOYSA-N 0.000 claims 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 150000001733 carboxylic acid esters Chemical group 0.000 claims 1
- 125000005594 diketone group Chemical group 0.000 claims 1
- LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical compound CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 claims 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 claims 1
- 125000002560 nitrile group Chemical group 0.000 claims 1
- 229940030010 trimethoxybenzene Drugs 0.000 claims 1
- 238000001429 visible spectrum Methods 0.000 abstract description 2
- 239000000386 donor Substances 0.000 description 42
- 239000000523 sample Substances 0.000 description 42
- 239000000243 solution Substances 0.000 description 40
- 239000000945 filler Substances 0.000 description 37
- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 31
- 229920005989 resin Polymers 0.000 description 31
- 239000011347 resin Substances 0.000 description 31
- 238000001723 curing Methods 0.000 description 30
- 239000002131 composite material Substances 0.000 description 27
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 20
- 150000003839 salts Chemical class 0.000 description 18
- 239000003999 initiator Substances 0.000 description 16
- 239000005548 dental material Substances 0.000 description 15
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 239000003607 modifier Substances 0.000 description 12
- 125000002091 cationic group Chemical group 0.000 description 11
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 11
- 229920000642 polymer Polymers 0.000 description 11
- 229920000909 polytetrahydrofuran Polymers 0.000 description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 10
- 239000011521 glass Substances 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 239000004809 Teflon Substances 0.000 description 9
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- 239000000975 dye Substances 0.000 description 9
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- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 8
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- KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- MGFYSGNNHQQTJW-UHFFFAOYSA-N iodonium Chemical compound [IH2+] MGFYSGNNHQQTJW-UHFFFAOYSA-N 0.000 description 7
- 229920001451 polypropylene glycol Polymers 0.000 description 7
- 239000012085 test solution Substances 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical compound CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 6
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- 238000001879 gelation Methods 0.000 description 6
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- LBCCPKFTHIBIKU-UHFFFAOYSA-N 3,4-Heptanedione Chemical compound CCCC(=O)C(=O)CC LBCCPKFTHIBIKU-UHFFFAOYSA-N 0.000 description 4
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- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 4
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- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
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- 230000007062 hydrolysis Effects 0.000 description 3
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- 229910052740 iodine Inorganic materials 0.000 description 3
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- 150000002500 ions Chemical class 0.000 description 3
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- 230000008439 repair process Effects 0.000 description 3
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- 239000011135 tin Substances 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 2
- AGIQIOSHSMJYJP-UHFFFAOYSA-N 1,2,4-Trimethoxybenzene Chemical compound COC1=CC=C(OC)C(OC)=C1 AGIQIOSHSMJYJP-UHFFFAOYSA-N 0.000 description 2
- OHBQPCCCRFSCAX-UHFFFAOYSA-N 1,4-Dimethoxybenzene Chemical compound COC1=CC=C(OC)C=C1 OHBQPCCCRFSCAX-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/029—Inorganic compounds; Onium compounds; Organic compounds having hetero atoms other than oxygen, nitrogen or sulfur
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/20—Protective coatings for natural or artificial teeth, e.g. sealings, dye coatings or varnish
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/30—Compositions for temporarily or permanently fixing teeth or palates, e.g. primers for dental adhesives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/80—Preparations for artificial teeth, for filling teeth or for capping teeth
- A61K6/884—Preparations for artificial teeth, for filling teeth or for capping teeth comprising natural or synthetic resins
- A61K6/887—Compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/80—Preparations for artificial teeth, for filling teeth or for capping teeth
- A61K6/884—Preparations for artificial teeth, for filling teeth or for capping teeth comprising natural or synthetic resins
- A61K6/891—Compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/0037—Production of three-dimensional images
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
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- 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
- G03F7/075—Silicon-containing compounds
- G03F7/0757—Macromolecular compounds containing Si-O, Si-C or Si-N bonds
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S522/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S522/908—Dental utility
Landscapes
- Health & Medical Sciences (AREA)
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Abstract
Description
Claims (1)
- 【特許請求の範囲】 1.(a)エポキシ樹脂と、 (b)ヒドロキシル含有物質と、 (c)(i)ヨードニウム塩、 (ii)可視光増感剤、および (iii)電子供与体化合物、 を含有する光開始剤系と、 を含み、 該光開始剤系が、2.9×10-5モル/gのジフェニルヨードニウムヘキサフルオロ アンチモネートと1.5×10-5モル/gのカンファーキノンとを含有する2-ブタノン 標準溶液中において、3-ジメチルアミノ安息香酸の光誘起電位よりも大きいかま たはそれに等しい光誘起電位を有する、光重合性組成物。 2.前記供与体化合物が、次の構造式: 〔式中、R1は、独立して、H基、C1 〜18アルキル基(場合により、1個以上のハ ロゲン基、-CN基、-OH基、-SH基、C1 〜18アルコキシ基、C1 〜18アルキルチオ基 、C3 〜18シクロアルキル基、アリール基、COOH基、COOC1 〜18アルキル基、(C1 〜18 アルキル)0 〜1-CO-C1 〜18アルキル基、SO3H基、CN基、もしくはハロゲン基 で置換されている)、またはアリール基(場合により、1個以上の電子求引性基 で置換されている){式中、R2は、H基、C1 〜18アルキル基(場合により、1個以 上のハロゲン基、-CN基、-OH基、-SH基、C1 〜18アルコキシ基、C1 〜18アルキル チオ基、C3 〜18シクロアルキル基、 アリール基、COOH基、COOC1 〜18アルキル基、(C1 〜18アルキル)0 〜1-CO-C1 〜1 8 アルキル基、SO3H基、CN基、もしくはハロゲン基で置換されている)、またはア リール基(場合により、1個以上の電子求引性基で置換されている)である}で あるか、あるいはこれらのR1基は、一緒になって環を形成してもよく、Arは、1 個以上の電子求引性基で置換されたアリール基である〕 で表される、請求項1記載の組成物。 3.前記アリール基が、1個以上のカルボン酸基、カルボン酸エステル基、ケ トン基、アルデヒド基、スルホン酸基、スルホネート基、またはニトリル基で置 換されている、請求項2記載の組成物。 4.前記アリール基が、-COOH基、-COOC1 〜18アルキル基、-SO3R2基、-CN基、 -CO-C1 〜18アルキル基、および-C(O)H基〔式中、R2は、H基、C1 〜18アルキル基 (場合により、1個以上のハロゲン基、-CN基、-OH基、-SH基、C1 〜18アルコキシ 基、C1 〜18アルキルチオ基、C3 〜18シクロアルキル基、アリール基、COOH基、CO OC1 〜18アルキル基、(C1 〜18アルキル)0 〜1-CO-C1 〜18アルキル基、SO3H基、C N基、もしくはハロゲン基で置換されている)、またはアリール基(場合により、 1個以上の電子求引性基で置換されている)である〕からなる群より選ばれた1 個以上の部分で置換されている、請求項2記載の組成物。 5.前記供与体化合物が、4-ジメチルアミノ安息香酸、4-ジメチルアミノ安息 香酸エチル、3-ジメチルアミノ安息香酸、4-ジメチルアミノベンゾイン、4-ジメ チルアミノベンズアルデヒド、4-ジメチルアミノベンゾニトリル、および1,2,4- トリメトキシベンゼンからなる群より選ばれる、請求項1記載の組成物。 6.前記供与体化合物が、アルキルアリールポリエーテルである、請求項1記 載の組成物。 7.前記供与体化合物が、構造式: 〔式中、n=1〜3であり、各R3は、独立して、H基またはC1 〜18アルキル基(場 合により、1個以上のハロゲン基、-CN基、-OH基、-SH基、C1 〜18アルコキシ基 、C1 〜18アルキルチオ基、C3 〜18シクロアルキル基、アリール基、置換アリール 基、-COOH基、-COOC1 〜18アルキル基、-(C1 〜18アルキル)0 〜1-COH基、-(C1 〜18 アルキル)0 〜1-CO-C1 〜18アルキル基、-CO-C1 〜18アルキル基、-C(O)H基、 もしくはC2 〜18アルケニル基で置換されている)であるか、あるいはこれらのR3 基は、一緒になって環を形成してもよく、各R4は、C1 〜18アルキル基(場合によ り、1個以上のハロゲン基、-CN基、-OH基、-SH基、C1 〜18アルコキシ基、C1 〜1 8 アルキルチオ基、C3 〜18シクロアルキル基、アリール基、置換アリール基、-CO OH基、-COOC1 〜18アルキル基、-(C1 〜18アルキル)0 〜1-COH基、-(C1 〜18アル キル)0 〜1-CO-C1 〜18アルキル基、-CO-C1 〜18アルキル基、-C(O)H基、もしくは C2 〜18アルケニル基で置換されている)であることができる〕 を有するアルキルアリールポリエーテルである、請求項1記載の組成物。 8.前記ヨードニウム塩がアリールヨードニウム塩である、請求項1記載の組 成物。 9.前記ヨードニウム塩が、ジフェニルヨードニウムクロリド、ジフェニルヨ ードニウムヘキサフルオロホスフェート、ジフェニルヨードニウムヘキサフルオ ロアンチモネート、ジフェニルヨードニ ウムテトラフルオロボレート、またはそれらの混合物を含む、請求項1記載の組 成物。 10.前記増感剤がケトンを含む、請求項1記載の組成物。 11.前記増感剤がαジケトンを含む、請求項1記載の組成物。 12.前記増感剤が、ケトクマリン、アミノアリールケトン、またはパラ置換 アミノスチリルケトン化合物を含む、請求項1記載の組成物。 13.前記増感剤がカンファーキノンを含む、請求項1記載の組成物。 14.可視光に暴露した後60秒以内に硬化して不粘着性ゲルになる、請求項1 記載の組成物。 15.前記エポキシ樹脂が脂環式エポキシドまたはジエポキシドを含む、請求 項1記載の組成物。 16.前記エポキシ樹脂がビスフェノールAジエポキシドを含む、請求項1記 載の組成物。 17.前記エポキシ樹脂がエチレン性不飽和を含む、請求項1記載の組成物。 18.エチレン性不飽和化合物を更に含む、請求項1記載の組成物。 19.前記エチレン性不飽和化合物がアクリル酸またはメタクリル酸のエステ ルである、請求項16記載の組成物。 20.前記エチレン性不飽和化合物が、メチルアクリレート、メチルメタクリ レート、エチルアクリレート、イソプロピルメタクリレート、n-ヘキシルアクリ レート、ステアリルアクリレート、アリルアクリレート、グルセロールジアクリ レート、グルセロールトリアクリレート、エチレングリコールジアクリレート、 ジエチレングリコールジアクリレート、トリエチレングリコールジメタクリレー ト、1,3-プロパンジオールジアクリレート、1,3-プロパンジオールジメタクリレ ート、トリメチロールプロパントリアクリレート、1,2,4-ブタントリオールトリ メタクリレート、1,4-シクロヘキサンジオールジアクリレート、ペンタエリトリ トールトリアクリレート、ペンタエリトリトールテトラアクリレート、ペンタエ リトリトールテトラメタクリレート、ソルビトールヘキサアクリレート、または それらの混合物を含む、請求項16記載の組成物。 21.(a)エポキシ樹脂と、 (b)ヒドロキシル含有物質と、 (c)(i)ジアリールヨードニウムヘキサフルオロアンチモネートまたはジアリ ールヨードニウムヘキサフルオロホスフェート、 (ii)カンファーキノン、および (iii)次の構造式: 〔式中、R1は、独立して、H基、C1 〜18アルキル基(場合により、1個以上 のハロゲン基、-CN基、-OH基、-SH基、C1 〜18アルコキシ基、C1 〜18アルキルチ オ基、C3 〜18シクロアルキル基、アリール基、COOH基、COOC1 〜18アルキル基、 (C1 〜18アルキル)0 〜1-CO-C1 〜18アルキル基、SO3H基、CN基、もしくはハロゲ ン基で置換されている)、またはアリール基(場合により、1個以上の電子求引 性基で置換されている){式中、R2は、H基、C1 〜18アルキル基(場合により、1 個以上のハロゲン基、-CN基、-OH基、-SH基、C1 〜18アルコキシ基、C1 〜18アル キルチオ基、C3 〜18シクロアルキル基、アリ ール基、COOH基、COOC1 〜18アルキル基、(C1 〜18アルキル)0 〜1-CO-C1 〜18ア ルキル基、SO3H基、CN基、もしくはハロゲン基で置換されている)、またはアリ ール基(場合により、1個以上の電子求引性基で置換されている)である}であ るか、あるいはこれらのR1基は、一緒になって環を形成してもよく、Arは、1個 以上の電子求引性基で置換されたアリール基である〕 で表される電子供与体、 を含有する光開始剤系と、 を含む光重合性組成物。 22.(a)エポキシ樹脂と、 (b)ヒドロキシル含有物質と、 (c)(i)ジアリールヨードニウムヘキサフルオロアンチモネートまたはジアリ ールヨードニウムヘキサフルオロホスフェート、 (ii)カンファーキノン、および (iii)次の構造式: 〔式中、n=1〜3であり、各R3は、独立して、H基またはC1 〜18アルキル基( 場合により、1個以上のハロゲン基、-CN基、-OH基、-SH基、C1 〜18アルコキシ 基、C1 〜18アルキルチオ基、C3 〜18シクロアルキル基、アリール基、置換アリー ル基、-COOH基、-COOC1 〜18アルキル基、-(C1 〜18アルキル)0 〜1-COH基、-(C1 〜18 アルキル)0 〜1-CO-C1 〜18アルキル基、-CO-C1 〜18ア ルキル基、-C(O)H基、もしくはC2 〜18アルケニル基で置換されている)であるか 、あるいはこれらのR3基は、一緒になって環を形成してもよく、各R4は、C1 〜18 アルキル基(場合により、1個以上のハロゲン基、-CN基、-OH基、-SH基、C1 〜1 8 アルコキシ基、C1 〜18アルキルチオ基、C3 〜18シクロアルキル基、アリール基 、置換アリール基、-COOH基、-COOC1 〜18アルキル基、-(C1 〜18アルキル)0 〜1 -COH基、-(C1 〜18アルキル)0 〜1-CO-C1 〜18アルキル基、-CO-C1 〜18アルキ ル基、-C(O)H基、もしくはC2 〜18アルケニル基で置換されている)であることが できる〕 で表される電子供与体、 を含有する光開始剤系と、 を含む光重合性組成物。 23.約400〜1000ナノメートルの波長を有する光を光重合性組成物に該組成 物がゲル化または硬化するまで照射するステップを含む光重合方法であって、 該組成物が、 (a)エポキシ樹脂と、 (b)ヒドロキシル含有物質と、 (c)(i)ヨードニウム塩、 (ii)可視光増感剤、および (iii)電子供与体化合物、 を含有する光開始剤系と、 を含み、 該光開始剤系が、2.9×10-5モル毎グラムのジフェニルヨードニウムヘキサフ ルオロアンチモネートと1.5×10-5モル毎gのカンファーキノンとを含有する2-ブ タノン標準溶液を基準にして少なく とも約100mVの光誘起電位を有する、光重合方法。 24.前記組成物がエチレン性不飽和化合物を更に含む、請求項23記載の方 法。 25.(a)エポキシ樹脂と、 (b)ヒドロキシル含有物質と、 (c)(i)ヨードニウム塩、 (ii)可視光増感剤、および (iii)電子供与体化合物、 を含有する光開始剤系と、 を含み、 該光開始剤系が、2.9×10-5モル/gのジフェニルヨードニウムヘキサフルオロ アンチモネートと1.5×10-5モル/gのカンファーキノンとを含有する2-ブタノン 標準溶液を基準にして少なくとも約100mVの光誘起電位を有する、光重合性歯科 用組成物。 26.歯科用接着剤である、請求項25記載の組成物。 27.歯科用複合材料である、請求項25記載の組成物。 28.歯科用シーラントである、請求項25記載の組成物。 29.歯科矯正用接着剤である、請求項25記載の組成物。 30.グラフィックアート用イメージング組成物である、請求項1記載の組成 物。 31.フォトレジスト、ソルダマスク、電子部品相似被覆材、被覆研磨材、お よび磁気媒体組成物からなる群より選ばれる、請求項1記載の組成物。
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US08/840,093 | 1997-04-11 | ||
US08/840,093 US5998495A (en) | 1997-04-11 | 1997-04-11 | Ternary photoinitiator system for curing of epoxy/polyol resin compositions |
PCT/US1998/004458 WO1998047047A1 (en) | 1997-04-11 | 1998-03-06 | Ternary photoinitiator system for curing of epoxy/polyol resin compositions |
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JP2001520759A5 JP2001520759A5 (ja) | 2005-10-06 |
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EP (1) | EP0974078B1 (ja) |
JP (1) | JP4009754B2 (ja) |
KR (1) | KR20010006281A (ja) |
CN (1) | CN1252137A (ja) |
AU (1) | AU744316B2 (ja) |
BR (1) | BR9807971A (ja) |
CA (1) | CA2285317C (ja) |
DE (1) | DE69815520T2 (ja) |
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WO2008032850A1 (fr) | 2006-09-14 | 2008-03-20 | Three Bond Co., Ltd. | Composition photopolymérisable |
JP2017508760A (ja) * | 2014-03-27 | 2017-03-30 | デンツプライ デトレイ ゲー.エム.ベー.ハー. | 歯科用組成物 |
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US4642126A (en) * | 1985-02-11 | 1987-02-10 | Norton Company | Coated abrasives with rapidly curable adhesives and controllable curvature |
US4652274A (en) * | 1985-08-07 | 1987-03-24 | Minnesota Mining And Manufacturing Company | Coated abrasive product having radiation curable binder |
CA1323949C (en) * | 1987-04-02 | 1993-11-02 | Michael C. Palazzotto | Ternary photoinitiator system for addition polymerization |
US5639802A (en) * | 1991-05-20 | 1997-06-17 | Spectra Group Limited, Inc. | Cationic polymerization |
AU3971895A (en) * | 1994-10-31 | 1996-05-23 | Minnesota Mining And Manufacturing Company | Visible-light curable epoxy system with enhanced depth of cure |
US5808108A (en) * | 1997-01-15 | 1998-09-15 | Chappelow; Cecil C. | Polymeric compositions and composites prepared from spiroorthocarbonates and epoxy monomers |
US6025406A (en) * | 1997-04-11 | 2000-02-15 | 3M Innovative Properties Company | Ternary photoinitiator system for curing of epoxy resins |
US5998495A (en) * | 1997-04-11 | 1999-12-07 | 3M Innovative Properties Company | Ternary photoinitiator system for curing of epoxy/polyol resin compositions |
-
1997
- 1997-04-11 US US08/840,093 patent/US5998495A/en not_active Expired - Lifetime
-
1998
- 1998-03-06 BR BR9807971-9A patent/BR9807971A/pt not_active IP Right Cessation
- 1998-03-06 KR KR1019997009365A patent/KR20010006281A/ko not_active Application Discontinuation
- 1998-03-06 CA CA002285317A patent/CA2285317C/en not_active Expired - Fee Related
- 1998-03-06 JP JP54388598A patent/JP4009754B2/ja not_active Expired - Fee Related
- 1998-03-06 DE DE69815520T patent/DE69815520T2/de not_active Expired - Lifetime
- 1998-03-06 CN CN98804068A patent/CN1252137A/zh active Pending
- 1998-03-06 WO PCT/US1998/004458 patent/WO1998047047A1/en active IP Right Grant
- 1998-03-06 AU AU66903/98A patent/AU744316B2/en not_active Ceased
- 1998-03-06 EP EP98909015A patent/EP0974078B1/en not_active Expired - Lifetime
-
1999
- 1999-07-28 US US09/362,621 patent/US6187833B1/en not_active Expired - Lifetime
- 1999-10-11 NO NO19994955A patent/NO314041B1/no not_active IP Right Cessation
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
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JP2003327785A (ja) * | 2002-05-08 | 2003-11-19 | Henkel Loctite Corp | 光カチオン硬化型エポキシ樹脂組成物 |
JP2005187724A (ja) * | 2003-12-26 | 2005-07-14 | Konica Minolta Medical & Graphic Inc | 活性光線硬化型インクジェットインク組成物、活性光線硬化型インクジェットインクセットと、それを用いた画像形成方法及びインクジェット記録装置 |
JP4581401B2 (ja) * | 2003-12-26 | 2010-11-17 | コニカミノルタエムジー株式会社 | 活性光線硬化型インクジェットインク組成物、活性光線硬化型インクジェットインクセットと、それを用いた画像形成方法及びインクジェット記録装置 |
WO2008032850A1 (fr) | 2006-09-14 | 2008-03-20 | Three Bond Co., Ltd. | Composition photopolymérisable |
JP2017508760A (ja) * | 2014-03-27 | 2017-03-30 | デンツプライ デトレイ ゲー.エム.ベー.ハー. | 歯科用組成物 |
WO2022030276A1 (ja) * | 2020-08-07 | 2022-02-10 | 株式会社トクヤマデンタル | 光カチオン硬化性組成物および歯科用硬化性組成物 |
JP7473996B2 (ja) | 2020-08-07 | 2024-04-24 | 株式会社トクヤマデンタル | 歯科用硬化性組成物 |
Also Published As
Publication number | Publication date |
---|---|
CA2285317C (en) | 2009-09-08 |
US5998495A (en) | 1999-12-07 |
JP4009754B2 (ja) | 2007-11-21 |
NO994955D0 (no) | 1999-10-11 |
AU6690398A (en) | 1998-11-11 |
US6187833B1 (en) | 2001-02-13 |
WO1998047047A1 (en) | 1998-10-22 |
DE69815520T2 (de) | 2004-04-29 |
CA2285317A1 (en) | 1998-10-22 |
NO314041B1 (no) | 2003-01-20 |
EP0974078A1 (en) | 2000-01-26 |
CN1252137A (zh) | 2000-05-03 |
NO994955L (no) | 1999-10-11 |
BR9807971A (pt) | 2000-03-08 |
AU744316B2 (en) | 2002-02-21 |
EP0974078B1 (en) | 2003-06-11 |
KR20010006281A (ko) | 2001-01-26 |
DE69815520D1 (de) | 2003-07-17 |
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