KR101128245B1 - 트리아릴술포늄 및 아릴술피네이트 이온을 갖는 광개시제 - Google Patents
트리아릴술포늄 및 아릴술피네이트 이온을 갖는 광개시제 Download PDFInfo
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- KR101128245B1 KR101128245B1 KR1020067007943A KR20067007943A KR101128245B1 KR 101128245 B1 KR101128245 B1 KR 101128245B1 KR 1020067007943 A KR1020067007943 A KR 1020067007943A KR 20067007943 A KR20067007943 A KR 20067007943A KR 101128245 B1 KR101128245 B1 KR 101128245B1
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- triarylsulfonium
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- 125000005409 triarylsulfonium group Chemical group 0.000 title claims abstract description 70
- 150000002500 ions Chemical class 0.000 title abstract description 24
- 239000000203 mixture Substances 0.000 claims abstract description 93
- 150000003839 salts Chemical class 0.000 claims abstract description 68
- 125000003118 aryl group Chemical group 0.000 claims description 96
- 125000000217 alkyl group Chemical group 0.000 claims description 77
- 239000000178 monomer Substances 0.000 claims description 37
- 150000001768 cations Chemical class 0.000 claims description 27
- 150000001450 anions Chemical class 0.000 claims description 23
- 239000001257 hydrogen Substances 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 230000005855 radiation Effects 0.000 claims description 16
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 13
- ICYDASAGOZFWIC-UHFFFAOYSA-N naphthalene-1-sulfinic acid Chemical compound C1=CC=C2C(S(=O)O)=CC=CC2=C1 ICYDASAGOZFWIC-UHFFFAOYSA-N 0.000 claims description 10
- LTSBKUWFXANFCU-UHFFFAOYSA-N naphthalene-2-sulfinic acid Chemical compound C1=CC=CC2=CC(S(=O)O)=CC=C21 LTSBKUWFXANFCU-UHFFFAOYSA-N 0.000 claims description 9
- IXGVZDQAFNJLNE-UHFFFAOYSA-N 4-cyanobenzenesulfinic acid Chemical compound OS(=O)C1=CC=C(C#N)C=C1 IXGVZDQAFNJLNE-UHFFFAOYSA-N 0.000 claims description 8
- AOQYAMDZQAEDLO-UHFFFAOYSA-M 4-chlorobenzenesulfinate Chemical compound [O-]S(=O)C1=CC=C(Cl)C=C1 AOQYAMDZQAEDLO-UHFFFAOYSA-M 0.000 claims description 5
- XHUBUXUUHKUCCC-UHFFFAOYSA-N 4-ethoxycarbonylbenzenesulfinic acid Chemical compound CCOC(=O)C1=CC=C(S(O)=O)C=C1 XHUBUXUUHKUCCC-UHFFFAOYSA-N 0.000 claims description 5
- BERBFBIGYCTRGE-UHFFFAOYSA-N 3-(trifluoromethyl)benzenesulfinic acid Chemical compound OS(=O)C1=CC=CC(C(F)(F)F)=C1 BERBFBIGYCTRGE-UHFFFAOYSA-N 0.000 claims description 3
- JIUIHDUXMVJNKD-UHFFFAOYSA-N 4-(trifluoromethyl)benzenesulfinic acid Chemical compound OS(=O)C1=CC=C(C(F)(F)F)C=C1 JIUIHDUXMVJNKD-UHFFFAOYSA-N 0.000 claims description 3
- UWXCCBKRJAVWST-UHFFFAOYSA-N 9,10-dioxoanthracene-1-sulfinic acid Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2S(=O)O UWXCCBKRJAVWST-UHFFFAOYSA-N 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 3
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- -1 triarylsulfonium ions Chemical class 0.000 abstract description 173
- 238000010526 radical polymerization reaction Methods 0.000 abstract description 19
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
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- RSIZHSFCPFZAJC-UHFFFAOYSA-N naphthalen-1-yl(diphenyl)sulfanium Chemical compound C1=CC=CC=C1[S+](C=1C2=CC=CC=C2C=CC=1)C1=CC=CC=C1 RSIZHSFCPFZAJC-UHFFFAOYSA-N 0.000 description 1
- DASJFYAPNPUBGG-UHFFFAOYSA-N naphthalene-1-sulfonyl chloride Chemical compound C1=CC=C2C(S(=O)(=O)Cl)=CC=CC2=C1 DASJFYAPNPUBGG-UHFFFAOYSA-N 0.000 description 1
- OPECTNGATDYLSS-UHFFFAOYSA-N naphthalene-2-sulfonyl chloride Chemical compound C1=CC=CC2=CC(S(=O)(=O)Cl)=CC=C21 OPECTNGATDYLSS-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 125000005003 perfluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
- 125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- ZJIGVNMWBLBMKC-UHFFFAOYSA-M potassium;4-ethoxycarbonylbenzenesulfonate Chemical compound [K+].CCOC(=O)C1=CC=C(S([O-])(=O)=O)C=C1 ZJIGVNMWBLBMKC-UHFFFAOYSA-M 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- QTECDUFMBMSHKR-UHFFFAOYSA-N prop-2-enyl prop-2-enoate Chemical compound C=CCOC(=O)C=C QTECDUFMBMSHKR-UHFFFAOYSA-N 0.000 description 1
- BOQSSGDQNWEFSX-UHFFFAOYSA-N propan-2-yl 2-methylprop-2-enoate Chemical compound CC(C)OC(=O)C(C)=C BOQSSGDQNWEFSX-UHFFFAOYSA-N 0.000 description 1
- LYBIZMNPXTXVMV-UHFFFAOYSA-N propan-2-yl prop-2-enoate Chemical compound CC(C)OC(=O)C=C LYBIZMNPXTXVMV-UHFFFAOYSA-N 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 150000005838 radical anions Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- WNRREQPZEBZGFA-UHFFFAOYSA-M sodium;4-cyanobenzenesulfinate Chemical compound [Na+].[O-]S(=O)C1=CC=C(C#N)C=C1 WNRREQPZEBZGFA-UHFFFAOYSA-M 0.000 description 1
- NUERUBQHXIQIOB-UHFFFAOYSA-M sodium;4-sulfobenzoate Chemical compound [Na+].OS(=O)(=O)C1=CC=C(C([O-])=O)C=C1 NUERUBQHXIQIOB-UHFFFAOYSA-M 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical compound [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- ZLTMZEOAWYZKCY-UHFFFAOYSA-M tetrabutylazanium;4-(trifluoromethyl)benzenesulfinate Chemical class [O-]S(=O)C1=CC=C(C(F)(F)F)C=C1.CCCC[N+](CCCC)(CCCC)CCCC ZLTMZEOAWYZKCY-UHFFFAOYSA-M 0.000 description 1
- USFPINLPPFWTJW-UHFFFAOYSA-N tetraphenylphosphonium Chemical compound C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 USFPINLPPFWTJW-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000003396 thiol group Chemical class [H]S* 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- DLYKUGXVBXYBGA-UHFFFAOYSA-N trifluoromethyl benzenesulfinate Chemical compound FC(F)(F)OS(=O)C1=CC=CC=C1 DLYKUGXVBXYBGA-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- UAXOELSVPTZZQG-UHFFFAOYSA-N trimethyl acrylic acid Chemical compound CC(C)=C(C)C(O)=O UAXOELSVPTZZQG-UHFFFAOYSA-N 0.000 description 1
- ISJCSCLGELKMCR-UHFFFAOYSA-N tris(4-phenoxyphenyl)sulfanium Chemical compound C=1C=C([S+](C=2C=CC(OC=3C=CC=CC=3)=CC=2)C=2C=CC(OC=3C=CC=CC=3)=CC=2)C=CC=1OC1=CC=CC=C1 ISJCSCLGELKMCR-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 238000004078 waterproofing Methods 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
Classifications
-
- 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
-
- 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
- A61K6/60—Preparations for dentistry comprising organic or organo-metallic additives
- A61K6/62—Photochemical radical initiators
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C313/00—Sulfinic acids; Sulfenic acids; Halides, esters or anhydrides thereof; Amides of sulfinic or sulfenic acids, i.e. compounds having singly-bound oxygen atoms of sulfinic or sulfenic groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C313/02—Sulfinic acids; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
- C07C381/12—Sulfonium compounds
-
- 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
-
- 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
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/672,554 | 2003-09-26 | ||
| US10/672,554 US7026367B2 (en) | 2003-09-26 | 2003-09-26 | Photoiniators having triarylsulfonium and arylsulfinate ions |
| PCT/US2004/025281 WO2005034885A1 (en) | 2003-09-26 | 2004-08-05 | Photoinitiators having triarylsulfonium and arylsulfinate ions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20060093339A KR20060093339A (ko) | 2006-08-24 |
| KR101128245B1 true KR101128245B1 (ko) | 2012-03-28 |
Family
ID=34376395
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020067007943A KR101128245B1 (ko) | 2003-09-26 | 2004-08-05 | 트리아릴술포늄 및 아릴술피네이트 이온을 갖는 광개시제 |
Country Status (6)
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004029037A1 (ja) * | 2002-09-25 | 2004-04-08 | Asahi Denka Co.Ltd. | 新規な芳香族スルホニウム塩化合物、これからなる光酸発生剤およびこれを含む光重合性組成物、光学的立体造形用樹脂組成物並びに光学的立体造形法 |
| US7026367B2 (en) * | 2003-09-26 | 2006-04-11 | 3M Innovative Properties Company | Photoiniators having triarylsulfonium and arylsulfinate ions |
| US7064152B2 (en) * | 2003-09-26 | 2006-06-20 | 3M Innovative Properties Company | Arylsulfinate salts in photoinitiator systems for polymerization reactions |
| US7030169B2 (en) * | 2003-09-26 | 2006-04-18 | 3M Innovative Properties Company | Arylsulfinate salts in initiator systems for polymeric reactions |
| US7250452B2 (en) * | 2003-09-26 | 2007-07-31 | 3M Innovative Properties Company | Dental compositions and methods with arylsulfinate salts |
| JP4505357B2 (ja) * | 2005-03-16 | 2010-07-21 | 富士フイルム株式会社 | 感光性組成物、該感光性組成物に用いる化合物及び該感光性組成物を用いたパターン形成方法 |
| ATE523186T1 (de) * | 2005-12-29 | 2011-09-15 | 3M Innovative Properties Co | Dentalzusammensetzungen mit wasserfänger |
| EP1968528B1 (en) * | 2005-12-29 | 2016-02-17 | 3M Innovative Properties Company | Dental compositions with surface-treated filler for shelf stability |
| WO2007079070A1 (en) * | 2005-12-29 | 2007-07-12 | 3M Innovative Properties Company | Dental compositions and initiator systems with polycyclic aromatic component |
| US7906214B2 (en) * | 2007-01-26 | 2011-03-15 | Transitions Optical, Inc. | Optical elements comprising compatiblizing coatings and methods of making the same |
| EP2133063A1 (en) * | 2008-06-10 | 2009-12-16 | 3M Innovative Properties Company | Initiator system with biphenylene derivates, method of production and use thereof |
| JP5359063B2 (ja) * | 2008-06-30 | 2013-12-04 | 東レ株式会社 | シクロアルカノンオキシムの製造方法 |
| JP5359064B2 (ja) * | 2008-06-30 | 2013-12-04 | 東レ株式会社 | シクロアルカノンオキシムの製造方法および光化学反応装置 |
| GB2491170B (en) * | 2011-05-26 | 2013-11-06 | Henkel Ireland Ltd | Two-part polymerisable compositions |
| AT517626B1 (de) * | 2015-09-02 | 2017-06-15 | Technische Universität Wien | Verwendung neuer Aryliodonium- und Sulfoniumsalze als Photoinitiatoren |
| CN105218708A (zh) * | 2015-10-13 | 2016-01-06 | 浙江理工大学 | 一种引发自由基、阳离子聚合的可见光引发体系 |
| JP6793088B2 (ja) * | 2017-04-28 | 2020-12-02 | 富士フイルム株式会社 | 感活性光線性又は感放射線性組成物、レジスト膜、マスクブランクス、パターン形成方法、及び電子デバイスの製造方法 |
| EP3470048B1 (en) | 2017-10-13 | 2021-11-10 | Dentsply DeTrey GmbH | Photocurable dental composition |
| KR102625644B1 (ko) * | 2017-12-13 | 2024-01-15 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 트라이알킬 보란 착물 개시제 및 광산을 함유하는 광학 투명 접착제 |
| JP2024510459A (ja) * | 2021-03-17 | 2024-03-07 | ボスティク エス アー | （メタ）アクリレートモノマーに基づく組成物 |
| FR3120871A1 (fr) * | 2021-03-17 | 2022-09-23 | Bostik Sa | Composition à base de monomères (méth)acrylate |
| FR3121623B1 (fr) * | 2021-04-09 | 2023-06-16 | S A S 3Dceram Sinto | Composition durcissable pour la fabrication, par stereolithographie, de pieces crues en materiau ceramique ou metallique par voie photo-thermique |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030054288A1 (en) | 2001-05-17 | 2003-03-20 | Fuji Photo Film Co., Ltd. | Photosensitive composition and planographic printing plate precursor |
Family Cites Families (90)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3573922A (en) | 1965-04-23 | 1971-04-06 | Hughes Aircraft Co | Photopolymerizable composition and process |
| US3556794A (en) | 1966-10-03 | 1971-01-19 | Hughes Aircraft Co | Method of inhibiting photopolymerization and products therefor |
| US3531281A (en) | 1966-10-03 | 1970-09-29 | Hughes Aircraft Co | Photopolymer fixation process |
| US3607272A (en) | 1967-02-16 | 1971-09-21 | Hughes Aircraft Co | Photographic polymerization process and product |
| US3708296A (en) | 1968-08-20 | 1973-01-02 | American Can Co | Photopolymerization of epoxy monomers |
| US3627656A (en) | 1969-04-03 | 1971-12-14 | Hughes Aircraft Co | Catalyst systems for photo-chemical polymerization |
| US3623875A (en) * | 1969-11-28 | 1971-11-30 | Plastic Coating Corp | Background coloration inhibition in diazosulfonate photoreproduction |
| US3729313A (en) | 1971-12-06 | 1973-04-24 | Minnesota Mining & Mfg | Novel photosensitive systems comprising diaryliodonium compounds and their use |
| US3808006A (en) | 1971-12-06 | 1974-04-30 | Minnesota Mining & Mfg | Photosensitive material containing a diaryliodium compound, a sensitizer and a color former |
| US3788858A (en) | 1972-10-02 | 1974-01-29 | Hughes Aircraft Co | Photopolymerization systems with tetrazolium salt |
| US3741769A (en) | 1972-10-24 | 1973-06-26 | Minnesota Mining & Mfg | Novel photosensitive polymerizable systems and their use |
| AU497960B2 (en) | 1974-04-11 | 1979-01-25 | Minnesota Mining And Manufacturing Company | Photopolymerizable compositions |
| GB1512982A (en) | 1974-05-02 | 1978-06-01 | Gen Electric | Salts |
| US4250311A (en) | 1974-05-02 | 1981-02-10 | General Electric Company | P, As, and Sb hexafluoride onium salts as photoinitiators |
| US4069054A (en) | 1975-09-02 | 1978-01-17 | Minnesota Mining And Manufacturing Company | Photopolymerizable composition containing a sensitized aromatic sulfonium compound and a cationacally polymerizable monomer |
| GB1569021A (en) | 1976-03-17 | 1980-06-11 | Kuraray Co | Adhesive cementing agents containing partial phosphonic orphosphonic acid esters |
| JPS5330193A (en) * | 1976-08-31 | 1978-03-22 | Kuraray Co | Human body hard tissue adhesive compostion |
| US4216288A (en) | 1978-09-08 | 1980-08-05 | General Electric Company | Heat curable cationically polymerizable compositions and method of curing same with onium salts and reducing agents |
| US4455147A (en) | 1978-10-09 | 1984-06-19 | I.W.S. Nominee Company, Limited | Transfer printing |
| US4250053A (en) | 1979-05-21 | 1981-02-10 | Minnesota Mining And Manufacturing Company | Sensitized aromatic iodonium or aromatic sulfonium salt photoinitiator systems |
| US4257915A (en) | 1979-07-23 | 1981-03-24 | E. I. Du Pont De Nemours And Company | Photopolymer initiator system containing a semiconductor, a reducing agent and an oxidizing agent |
| US4695251A (en) | 1980-04-07 | 1987-09-22 | Minnesota Mining And Manufacturing Company | Orthodontic bracket adhesive and abrasive for removal thereof |
| US4366228A (en) | 1980-09-05 | 1982-12-28 | Eastman Kodak Company | Photopolymerizable compositions featuring novel co-initiators |
| US5304585A (en) | 1981-02-13 | 1994-04-19 | Minnesota Mining And Manufacturing | Dentin and enamel adhesive |
| US4356296A (en) | 1981-02-25 | 1982-10-26 | The United States Of America As Represented By The Secretary Of The Navy | Fluorinated diacrylic esters and polymers therefrom |
| US4539382A (en) | 1981-07-29 | 1985-09-03 | Kuraray Co., Ltd. | Adhesive composition |
| JPS59135272A (ja) | 1983-01-21 | 1984-08-03 | Kuraray Co Ltd | 接着剤 |
| US4503169A (en) | 1984-04-19 | 1985-03-05 | Minnesota Mining And Manufacturing Company | Radiopaque, low visual opacity dental composites containing non-vitreous microparticles |
| US4650913A (en) | 1984-11-29 | 1987-03-17 | E. I. Du Pont De Nemours And Company | Sulfinate-initiated addition of perfluorinated iodides to olefins |
| US4966934A (en) | 1984-11-29 | 1990-10-30 | Dentsply Research & Development Corp. | Biological compatible adhesive containing a phosphorous adhesion promoter and accelerator |
| US4642126A (en) | 1985-02-11 | 1987-02-10 | Norton Company | Coated abrasives with rapidly curable adhesives and controllable curvature |
| DE3516256A1 (de) | 1985-05-07 | 1986-11-13 | Bayer Ag, 5090 Leverkusen | (meth)-acrylsaeureester und ihre verwendung |
| DE3516257A1 (de) | 1985-05-07 | 1986-11-13 | Bayer Ag, 5090 Leverkusen | (meth)-acrylsaeureester und ihre verwendung |
| DE3670076D1 (de) | 1985-06-24 | 1990-05-10 | Tokuyama Soda Kk | Acrylatverbindung und diese enthaltende zusammensetzung. |
| US4652274A (en) | 1985-08-07 | 1987-03-24 | Minnesota Mining And Manufacturing Company | Coated abrasive product having radiation curable binder |
| DE3536076A1 (de) | 1985-10-09 | 1987-04-09 | Muehlbauer Ernst Kg | Polymerisierbare zementmischungen |
| AU590671B2 (en) | 1986-02-28 | 1989-11-09 | Minnesota Mining And Manufacturing Company | One-part visible light-curable dentin and enamel adhesive |
| CA1323949C (en) | 1987-04-02 | 1993-11-02 | Michael C. Palazzotto | Ternary photoinitiator system for addition polymerization |
| US4908227A (en) | 1987-10-16 | 1990-03-13 | Gaf Chemicals Corporation | Divinyl epoxy ethers |
| US4959297A (en) | 1987-12-09 | 1990-09-25 | Minnesota Mining And Manufacturing Company | Ternary photoinitiator system for addition polymerization |
| AU618772B2 (en) | 1987-12-30 | 1992-01-09 | Minnesota Mining And Manufacturing Company | Photocurable ionomer cement systems |
| US4859572A (en) | 1988-05-02 | 1989-08-22 | Eastman Kodak Company | Dye sensitized photographic imaging system |
| JPH024891A (ja) | 1988-06-21 | 1990-01-09 | Mitsubishi Rayon Co Ltd | 歯科用接着剤組成物 |
| US4871786A (en) | 1988-10-03 | 1989-10-03 | Minnesota Mining And Manufacturing Company | Organic fluoride sources |
| US4971892A (en) | 1988-11-23 | 1990-11-20 | Minnesota Mining And Manufacturing Company | High sensitivity photopolymerizable composition |
| DE3841617C1 (US07297724-20071120-C00005.png) | 1988-12-10 | 1990-05-10 | Th. Goldschmidt Ag, 4300 Essen, De | |
| US5076844A (en) | 1988-12-10 | 1991-12-31 | Goldschmidt AG & GDF Gesellschaft fur Dentale Forschung u. Innovationen GmbH | Perfluoroalkyl group-containing (meth-)acrylate esters, their synthesis and use in dental technology |
| US4954416A (en) * | 1988-12-21 | 1990-09-04 | Minnesota Mining And Manufacturing Company | Tethered sulfonium salt photoinitiators for free radical polymerization |
| US5105006A (en) | 1989-05-25 | 1992-04-14 | The Dow Chemical Company | Phosphonium salts |
| JP2604472B2 (ja) * | 1989-07-12 | 1997-04-30 | 株式会社クラレ | 重合性組成物 |
| US5124417A (en) | 1990-02-12 | 1992-06-23 | Minnesota Mining And Manufacturing Company | Initiators for cationic polymerization |
| US5084586A (en) | 1990-02-12 | 1992-01-28 | Minnesota Mining And Manufacturing Company | Novel initiators for cationic polymerization |
| US5089374A (en) | 1990-08-20 | 1992-02-18 | Eastman Kodak Company | Novel bis-onium salts and the use thereof as photoinitiators |
| US5154762A (en) | 1991-05-31 | 1992-10-13 | Minnesota Mining And Manufacturing Company | Universal water-based medical and dental cement |
| US5256447A (en) | 1991-12-31 | 1993-10-26 | Minnesota Mining And Manufacturing Company | Adhesive composition and method |
| US5530038A (en) | 1993-08-02 | 1996-06-25 | Sun Medical Co., Ltd. | Primer composition and curable composition |
| US6312668B2 (en) | 1993-12-06 | 2001-11-06 | 3M Innovative Properties Company | Optionally crosslinkable coatings, compositions and methods of use |
| US5888491A (en) | 1993-12-06 | 1999-03-30 | Minnesota Mining And Manufacturing Company | Optionally crosslinkable coatings, compositions and methods of use |
| JP3465753B2 (ja) | 1993-12-28 | 2003-11-10 | 株式会社トクヤマ | 歯科用組成物 |
| US5501727A (en) | 1994-02-28 | 1996-03-26 | Minnesota Mining And Manufacturing Company | Color stability of dental compositions containing metal complexed ascorbic acid |
| EP0712622B1 (en) | 1994-11-21 | 1999-09-01 | Tokuyama Corporation | Dental composition and kit |
| US5662887A (en) | 1994-12-01 | 1997-09-02 | Minnesota Mining And Manufacturing Company | Fluorocarbon containing coatings, compositions and methods of use |
| US5607663A (en) | 1994-12-01 | 1997-03-04 | Minnesota Mining And Manufacturing Company | Hydrocarbyl containing coatings, compositions and methods of use |
| US5546676A (en) * | 1995-05-17 | 1996-08-20 | Mallinckrodt Medical, Inc. | Aggressive convective drying in an agitated pan type dryer |
| JPH0934110A (ja) * | 1995-07-17 | 1997-02-07 | Konica Corp | 光重合性組成物、ラジカル発生方法、平版印刷版作成用感光材料及びそれを用いた平版印刷版の作成方法 |
| JPH09268204A (ja) * | 1996-02-01 | 1997-10-14 | Tokuyama Corp | 可視光線重合開始剤および可視光線重合性組成物 |
| US5998495A (en) | 1997-04-11 | 1999-12-07 | 3M Innovative Properties Company | Ternary photoinitiator system for curing of epoxy/polyol resin compositions |
| US6030606A (en) | 1998-06-22 | 2000-02-29 | 3M Innovative Properties Company | Dental restoratives comprising Bis-EMA6 |
| US6331080B1 (en) | 1998-07-15 | 2001-12-18 | 3M Innovative Properties Company | Optical fiber connector using colored photocurable adhesive |
| US6204302B1 (en) | 1998-11-20 | 2001-03-20 | Bisco, Inc. | Photosensitizers for free radical polymerization initiation resins and method of making the same |
| DE19860361A1 (de) | 1998-12-24 | 2000-06-29 | Espe Dental Ag | Vernetzbare Monomere auf Cyclosiloxanbasis, deren Herstellung und deren Verwendung in polymerisierbaren Massen |
| DE19860364C2 (de) | 1998-12-24 | 2001-12-13 | 3M Espe Ag | Polymerisierbare Dentalmassen auf der Basis von zur Aushärtung befähigten Siloxanverbindungen, deren Verwendung und Herstellung |
| AU764607B2 (en) | 1999-03-31 | 2003-08-28 | Kuraray Medical, Inc. | Organophosphorus compounds for dental polymerizable compositions |
| TWI284540B (en) | 1999-05-13 | 2007-08-01 | Kuraray Co | Bonding composition suitable to tooth tissue |
| DE19934407A1 (de) | 1999-07-22 | 2001-01-25 | Espe Dental Ag | Hydrolysierbare und polymerisierbare Silane mit geringer Viskosität und deren Verwendung |
| US6730156B1 (en) | 1999-10-28 | 2004-05-04 | 3M Innovative Properties Company | Clustered particle dental fillers |
| JP4800535B2 (ja) | 1999-10-28 | 2011-10-26 | スリーエム イノベイティブ プロパティズ カンパニー | ナノサイズシリカ粒子を含有する歯科材料 |
| US6387981B1 (en) | 1999-10-28 | 2002-05-14 | 3M Innovative Properties Company | Radiopaque dental materials with nano-sized particles |
| US6572693B1 (en) | 1999-10-28 | 2003-06-03 | 3M Innovative Properties Company | Aesthetic dental materials |
| US6444725B1 (en) | 2000-01-21 | 2002-09-03 | 3M Innovative Properties Company | Color-changing dental compositions |
| DE10026432A1 (de) | 2000-05-29 | 2002-02-14 | 3M Espe Ag | Präpolymere (Meth)acrylate mit polycyclischen oder aromatischen Segmenten |
| US6528555B1 (en) | 2000-10-12 | 2003-03-04 | 3M Innovative Properties Company | Adhesive for use in the oral environment having color-changing capabilities |
| DE10124028B4 (de) | 2001-05-16 | 2010-02-18 | 3M Espe Ag | Selbstadhäsive Dentalmaterialien |
| JP2002341519A (ja) * | 2001-05-17 | 2002-11-27 | Fuji Photo Film Co Ltd | 感熱性組成物及びそれを用いた平版印刷版原版 |
| JP4759170B2 (ja) * | 2001-06-28 | 2011-08-31 | 株式会社クラレ | 歯科用組成物キット |
| US6777460B2 (en) * | 2002-12-23 | 2004-08-17 | 3M Innovative Properties Company | Curing agents for cationically curable compositions |
| US7030169B2 (en) * | 2003-09-26 | 2006-04-18 | 3M Innovative Properties Company | Arylsulfinate salts in initiator systems for polymeric reactions |
| US7064152B2 (en) * | 2003-09-26 | 2006-06-20 | 3M Innovative Properties Company | Arylsulfinate salts in photoinitiator systems for polymerization reactions |
| US7026367B2 (en) * | 2003-09-26 | 2006-04-11 | 3M Innovative Properties Company | Photoiniators having triarylsulfonium and arylsulfinate ions |
| JP2006276759A (ja) * | 2005-03-30 | 2006-10-12 | Fuji Photo Film Co Ltd | Ｅｕｖ露光用ポジ型レジスト組成物及びそれを用いたパターン形成方法 |
-
2003
- 2003-09-26 US US10/672,554 patent/US7026367B2/en not_active Expired - Lifetime
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2004
- 2004-08-05 JP JP2006527986A patent/JP4546477B2/ja not_active Expired - Fee Related
- 2004-08-05 KR KR1020067007943A patent/KR101128245B1/ko not_active IP Right Cessation
- 2004-08-05 EP EP04780169.1A patent/EP1684698B1/en not_active Not-in-force
- 2004-08-05 CN CN2004800280331A patent/CN1859893B/zh not_active Expired - Fee Related
- 2004-08-05 WO PCT/US2004/025281 patent/WO2005034885A1/en active Search and Examination
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030054288A1 (en) | 2001-05-17 | 2003-03-20 | Fuji Photo Film Co., Ltd. | Photosensitive composition and planographic printing plate precursor |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1859893A (zh) | 2006-11-08 |
| US20050070621A1 (en) | 2005-03-31 |
| JP4546477B2 (ja) | 2010-09-15 |
| US7297724B2 (en) | 2007-11-20 |
| WO2005034885A1 (en) | 2005-04-21 |
| US20060111463A1 (en) | 2006-05-25 |
| EP1684698A1 (en) | 2006-08-02 |
| JP2007506836A (ja) | 2007-03-22 |
| CN1859893B (zh) | 2011-05-25 |
| EP1684698B1 (en) | 2013-10-02 |
| KR20060093339A (ko) | 2006-08-24 |
| US7026367B2 (en) | 2006-04-11 |
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