JPS5919581B2 - オニウム塩混合物 - Google Patents
オニウム塩混合物Info
- Publication number
- JPS5919581B2 JPS5919581B2 JP55080991A JP8099180A JPS5919581B2 JP S5919581 B2 JPS5919581 B2 JP S5919581B2 JP 55080991 A JP55080991 A JP 55080991A JP 8099180 A JP8099180 A JP 8099180A JP S5919581 B2 JPS5919581 B2 JP S5919581B2
- Authority
- JP
- Japan
- Prior art keywords
- salt
- weight
- triphenylsulfonium
- photoinitiator mixture
- mixture according
- 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
- 239000011833 salt mixture Substances 0.000 title 1
- -1 triphenylsulfonium hexafluoroantimonate Chemical group 0.000 claims description 34
- 239000000203 mixture Substances 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 25
- 239000003822 epoxy resin Substances 0.000 claims description 14
- 229920000647 polyepoxide Polymers 0.000 claims description 14
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 claims description 8
- VUBUXALTYMBEQO-UHFFFAOYSA-N 2,2,3,3,3-pentafluoro-1-phenylpropan-1-one Chemical group FC(F)(F)C(F)(F)C(=O)C1=CC=CC=C1 VUBUXALTYMBEQO-UHFFFAOYSA-N 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 claims description 3
- 229910052787 antimony Inorganic materials 0.000 claims description 3
- 229910052785 arsenic Inorganic materials 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical group C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 claims description 3
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000000962 organic group Chemical group 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 229910052711 selenium Inorganic materials 0.000 claims description 2
- 239000011669 selenium Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims 2
- 150000005676 cyclic carbonates Chemical class 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 238000006116 polymerization reaction Methods 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- YEOCHZFPBYUXMC-UHFFFAOYSA-L copper benzoate Chemical compound [Cu+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 YEOCHZFPBYUXMC-UHFFFAOYSA-L 0.000 description 12
- 238000000034 method Methods 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 6
- 239000011877 solvent mixture Substances 0.000 description 5
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 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 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000012954 diazonium Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000012266 salt solution Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001241 acetals Chemical class 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 150000004292 cyclic ethers Chemical class 0.000 description 2
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 2
- YWXYYJSYQOXTPL-SLPGGIOYSA-N isosorbide mononitrate Chemical compound [O-][N+](=O)O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 YWXYYJSYQOXTPL-SLPGGIOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- VYQVAVNKQCPAOF-UHFFFAOYSA-M triphenylselanium;chloride Chemical compound [Cl-].C1=CC=CC=C1[Se+](C=1C=CC=CC=1)C1=CC=CC=C1 VYQVAVNKQCPAOF-UHFFFAOYSA-M 0.000 description 2
- RIWCVHOPSGGAMT-UHFFFAOYSA-N (1,4,5,5,6,6-hexafluorocyclohex-2-en-1-yl)-diphenylsulfanium Chemical compound FC1C(C(C(C=C1)([S+](C1=CC=CC=C1)C1=CC=CC=C1)F)(F)F)(F)F RIWCVHOPSGGAMT-UHFFFAOYSA-N 0.000 description 1
- GCBVPKBGZVPJFV-UHFFFAOYSA-N 1-cyclohex-3-en-1-yl-2,6,6-trimethylbicyclo[3.1.1]heptane Chemical compound C12(C(CCC(C1(C)C)C2)C)C2CC=CCC2 GCBVPKBGZVPJFV-UHFFFAOYSA-N 0.000 description 1
- QGHDLJAZIIFENW-UHFFFAOYSA-N 4-[1,1,1,3,3,3-hexafluoro-2-(4-hydroxy-3-prop-2-enylphenyl)propan-2-yl]-2-prop-2-enylphenol Chemical group C1=C(CC=C)C(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C(CC=C)=C1 QGHDLJAZIIFENW-UHFFFAOYSA-N 0.000 description 1
- OECTYKWYRCHAKR-UHFFFAOYSA-N 4-vinylcyclohexene dioxide Chemical compound C1OC1C1CC2OC2CC1 OECTYKWYRCHAKR-UHFFFAOYSA-N 0.000 description 1
- WGDYTLFJZZPJNS-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptane-6-carboxylic acid Chemical compound C1CCCC2OC21C(=O)O WGDYTLFJZZPJNS-UHFFFAOYSA-N 0.000 description 1
- DJHGAFSJWGLOIV-UHFFFAOYSA-K Arsenate3- Chemical compound [O-][As]([O-])([O-])=O DJHGAFSJWGLOIV-UHFFFAOYSA-K 0.000 description 1
- YPWFISCTZQNZAU-UHFFFAOYSA-N Thiane Chemical compound C1CCSCC1 YPWFISCTZQNZAU-UHFFFAOYSA-N 0.000 description 1
- 239000011354 acetal resin Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229940000489 arsenate Drugs 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000011951 cationic catalyst Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical class [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- MBAKFIZHTUAVJN-UHFFFAOYSA-I hexafluoroantimony(1-);hydron Chemical compound F.F[Sb](F)(F)(F)F MBAKFIZHTUAVJN-UHFFFAOYSA-I 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- ORQWTLCYLDRDHK-UHFFFAOYSA-N phenylselanylbenzene Chemical compound C=1C=CC=CC=1[Se]C1=CC=CC=C1 ORQWTLCYLDRDHK-UHFFFAOYSA-N 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- SPVXKVOXSXTJOY-UHFFFAOYSA-O selenonium Chemical compound [SeH3+] SPVXKVOXSXTJOY-UHFFFAOYSA-O 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910001495 sodium tetrafluoroborate Inorganic materials 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- DSLBDAPZIGYINM-UHFFFAOYSA-N sulfanium;chloride Chemical class S.Cl DSLBDAPZIGYINM-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical class [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- ZFEAYIKULRXTAR-UHFFFAOYSA-M triphenylsulfanium;chloride Chemical compound [Cl-].C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 ZFEAYIKULRXTAR-UHFFFAOYSA-M 0.000 description 1
- UMMDHBOKYMYITP-UHFFFAOYSA-N tris(4-hydroxy-3,5-dimethylphenyl)sulfanium;chloride Chemical compound [Cl-].CC1=C(O)C(C)=CC([S+](C=2C=C(C)C(O)=C(C)C=2)C=2C=C(C)C(O)=C(C)C=2)=C1 UMMDHBOKYMYITP-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
- C08G59/687—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used containing sulfur
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G85/00—General processes for preparing compounds provided for in this subclass
-
- 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
-
- 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
- Y10S502/00—Catalyst, solid sorbent, or support therefor: product or process of making
- Y10S502/522—Radiant or wave energy activated
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Physics & Mathematics (AREA)
- Inorganic Chemistry (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Epoxy Resins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polymerization Catalysts (AREA)
- Polymerisation Methods In General (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/049,296 US4273668A (en) | 1977-09-14 | 1979-06-18 | Arylsulfonium salt-solvent mixtures |
| US49296 | 1979-06-18 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5615261A JPS5615261A (en) | 1981-02-14 |
| JPS5919581B2 true JPS5919581B2 (ja) | 1984-05-07 |
Family
ID=21959084
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP55080991A Expired JPS5919581B2 (ja) | 1979-06-18 | 1980-06-17 | オニウム塩混合物 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4273668A (cg-RX-API-DMAC10.html) |
| JP (1) | JPS5919581B2 (cg-RX-API-DMAC10.html) |
| DE (1) | DE3022686C2 (cg-RX-API-DMAC10.html) |
| ES (1) | ES8104314A1 (cg-RX-API-DMAC10.html) |
| FR (1) | FR2459265A1 (cg-RX-API-DMAC10.html) |
| GB (1) | GB2051071B (cg-RX-API-DMAC10.html) |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0094915B1 (de) * | 1982-05-19 | 1987-01-21 | Ciba-Geigy Ag | Härtbare, Metallocenkomplexe enthaltende Zusammensetzungen, daraus erhältliche aktivierte Vorstufen und deren Verwendung |
| US4491628A (en) * | 1982-08-23 | 1985-01-01 | International Business Machines Corporation | Positive- and negative-working resist compositions with acid generating photoinitiator and polymer with acid labile groups pendant from polymer backbone |
| JPS5945303A (ja) * | 1982-09-07 | 1984-03-14 | Nippon Oil & Fats Co Ltd | 高感度光開始剤組成物 |
| US5073476A (en) * | 1983-05-18 | 1991-12-17 | Ciba-Geigy Corporation | Curable composition and the use thereof |
| US4946817A (en) * | 1984-07-17 | 1990-08-07 | The Dow Chemical Company | Latent catalysts for epoxy-containing compounds |
| US4594291A (en) * | 1984-07-17 | 1986-06-10 | The Dow Chemical Company | Curable, partially advanced epoxy resins |
| US5503937A (en) * | 1984-07-17 | 1996-04-02 | The Dow Chemical Company | Curable composition which comprises adducts of heterocyclic compounds |
| US4677137A (en) * | 1985-05-31 | 1987-06-30 | Minnesota Mining And Manufacturing Company | Supported photoinitiator |
| US4882245A (en) * | 1985-10-28 | 1989-11-21 | International Business Machines Corporation | Photoresist composition and printed circuit boards and packages made therewith |
| US4897180A (en) * | 1988-02-05 | 1990-01-30 | Uop | Catalytic composite and process for mercaptan sweetening |
| US4824818A (en) * | 1988-02-05 | 1989-04-25 | Uop Inc. | Catalytic composite and process for mercaptan sweetening |
| US5399596A (en) * | 1988-03-03 | 1995-03-21 | Sanshin Kagaku Kogyo Co., Ltd. | Polyfluoride sulfonium compounds and polymerization initiator thereof |
| US4954346A (en) * | 1988-06-08 | 1990-09-04 | Ciba-Geigy Corporation | Orally administrable nifedipine solution in a solid light resistant dosage form |
| US5262449A (en) * | 1990-09-10 | 1993-11-16 | Isp Investments Inc. | Radiation curable coating compositions |
| US5358977A (en) * | 1990-10-23 | 1994-10-25 | Daubert Coated Products, Inc. | Stabilized paper substrate for release liners using aromatic and aliphatic primers, and novel primer coat |
| JPH0662692B2 (ja) * | 1991-10-30 | 1994-08-17 | オーテックス株式会社 | 光重合反応開始剤 |
| US5342734A (en) * | 1992-02-25 | 1994-08-30 | Morton International, Inc. | Deep UV sensitive photoresist resistant to latent image decay |
| US5314782A (en) * | 1993-03-05 | 1994-05-24 | Morton International, Inc. | Deep UV sensitive resistant to latent image decay comprising a diazonaphthoquinone sulfonate of a nitrobenzyl derivative |
| US5502083A (en) * | 1993-06-18 | 1996-03-26 | Nippon Kayaku Kabushiki Kaisha | Onium salt, photopolymerization initiator, energy ray-curing composition containing the initiator, and cured product |
| US5612445A (en) * | 1995-02-15 | 1997-03-18 | Arizona Chemical Co. | Ultraviolet curable epoxidized alkyds |
| US5648196A (en) * | 1995-07-14 | 1997-07-15 | Cornell Research Foundation, Inc. | Water-soluble photoinitiators |
| JP2004091698A (ja) * | 2002-09-02 | 2004-03-25 | Konica Minolta Holdings Inc | 活性光線硬化型組成物、活性光線硬化型インク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 |
| GB2423519A (en) * | 2005-02-25 | 2006-08-30 | Sun Chemical Ltd | Energy-curable coating composition |
| GB2423520A (en) * | 2005-02-25 | 2006-08-30 | Sun Chemical Ltd | Energy-curable coating composition |
| JP4667945B2 (ja) * | 2005-04-20 | 2011-04-13 | 東京応化工業株式会社 | ポジ型レジスト組成物およびレジストパターン形成方法 |
| GB2432160A (en) * | 2005-11-14 | 2007-05-16 | Sun Chemical Ltd | Energy curable cyclic carbonate compositions |
| JP5208573B2 (ja) * | 2008-05-06 | 2013-06-12 | サンアプロ株式会社 | スルホニウム塩、光酸発生剤、光硬化性組成物及びこの硬化体 |
| EP2585513A2 (en) | 2010-06-28 | 2013-05-01 | Dow Global Technologies LLC | Curable resin compositions |
| CN102985459A (zh) | 2010-06-28 | 2013-03-20 | 陶氏环球技术有限责任公司 | 可固化树脂组合物 |
| CN104364289A (zh) | 2012-06-15 | 2015-02-18 | 陶氏环球技术有限责任公司 | 可固化组合物 |
| TWI573782B (zh) | 2012-12-07 | 2017-03-11 | Ｄｓｐ五協食品＆化學品股份有限公司 | 新穎鋶鹽化合物、其製造方法及光酸產生劑 |
| US20150060113A1 (en) | 2013-01-22 | 2015-03-05 | Yongcai Wang | Photocurable composition, article, and method of use |
| US9155201B2 (en) | 2013-12-03 | 2015-10-06 | Eastman Kodak Company | Preparation of articles with conductive micro-wire pattern |
| US9207533B2 (en) | 2014-02-07 | 2015-12-08 | Eastman Kodak Company | Photopolymerizable compositions for electroless plating methods |
| WO2015119616A1 (en) | 2014-02-07 | 2015-08-13 | Eastman Kodak Company | Photopolymerizable compositions for electroless plating methods |
| US9188861B2 (en) | 2014-03-05 | 2015-11-17 | Eastman Kodak Company | Photopolymerizable compositions for electroless plating methods |
| CN113286781B (zh) | 2019-01-10 | 2023-08-08 | 三亚普罗股份有限公司 | 锍盐、光产酸剂、固化性组合物和抗蚀剂组合物 |
| JP7594374B2 (ja) | 2020-07-08 | 2024-12-04 | サンアプロ株式会社 | ネガ型感光性樹脂組成物、パターン形成方法及び積層フィルム |
| JP7657062B2 (ja) * | 2021-02-03 | 2025-04-04 | サンアプロ株式会社 | 光酸発生剤及びフォトリソグラフィー用樹脂組成物 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3305527A (en) * | 1964-12-09 | 1967-02-21 | Celanese Coatings Company Inc | Epoxide resin compositions |
| US3542828A (en) * | 1968-02-15 | 1970-11-24 | Koppers Co Inc | Hexafluoroantimonate amine catalysts |
| US4080274A (en) * | 1968-08-20 | 1978-03-21 | American Can Company | Photopolymerization of lactone-epoxide mixtures with aromatic diazonium salts as photocatalyst |
| US3794576A (en) * | 1971-05-18 | 1974-02-26 | American Can Co | Epoxide blend radiation sensitive catalyst precursor |
| US4058401A (en) * | 1974-05-02 | 1977-11-15 | General Electric Company | Photocurable compositions containing group via aromatic onium salts |
| US4058400A (en) * | 1974-05-02 | 1977-11-15 | General Electric Company | Cationically polymerizable compositions containing group VIa onium salts |
| IE42085B1 (en) * | 1974-09-18 | 1980-06-04 | Ici Ltd | Photopolymerisable compositions |
| US4090936A (en) * | 1976-10-28 | 1978-05-23 | Minnesota Mining And Manufacturing Company | Photohardenable compositions |
| US4154872A (en) * | 1978-05-09 | 1979-05-15 | W. R. Grace & Co. | Process for preparing catalytic solutions of sulfonium salts |
| US4156035A (en) * | 1978-05-09 | 1979-05-22 | W. R. Grace & Co. | Photocurable epoxy-acrylate compositions |
-
1979
- 1979-06-18 US US06/049,296 patent/US4273668A/en not_active Expired - Lifetime
-
1980
- 1980-01-09 GB GB8000760A patent/GB2051071B/en not_active Expired
- 1980-03-12 ES ES489473A patent/ES8104314A1/es not_active Expired
- 1980-06-17 FR FR8013414A patent/FR2459265A1/fr active Granted
- 1980-06-17 JP JP55080991A patent/JPS5919581B2/ja not_active Expired
- 1980-06-18 DE DE3022686A patent/DE3022686C2/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB2051071A (en) | 1981-01-14 |
| FR2459265A1 (fr) | 1981-01-09 |
| ES489473A0 (es) | 1981-04-16 |
| US4273668A (en) | 1981-06-16 |
| DE3022686A1 (de) | 1981-02-19 |
| ES8104314A1 (es) | 1981-04-16 |
| DE3022686C2 (de) | 1986-08-21 |
| JPS5615261A (en) | 1981-02-14 |
| GB2051071B (en) | 1984-03-14 |
| FR2459265B1 (cg-RX-API-DMAC10.html) | 1983-05-20 |
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