KR940005716A - 에폭시실리콘 단량체 및 중합체의 합성을 위한 선택적 촉매 - Google Patents
에폭시실리콘 단량체 및 중합체의 합성을 위한 선택적 촉매 Download PDFInfo
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- KR940005716A KR940005716A KR1019930010555A KR930010555A KR940005716A KR 940005716 A KR940005716 A KR 940005716A KR 1019930010555 A KR1019930010555 A KR 1019930010555A KR 930010555 A KR930010555 A KR 930010555A KR 940005716 A KR940005716 A KR 940005716A
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- ethylenically unsaturated
- asonium
- mixture
- phosphonium
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- 239000003054 catalyst Substances 0.000 title claims 5
- 230000015572 biosynthetic process Effects 0.000 title claims 3
- 239000000178 monomer Substances 0.000 title 1
- 229920000642 polymer Polymers 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- 239000000203 mixture Substances 0.000 claims abstract 8
- 238000000034 method Methods 0.000 claims abstract 7
- 238000006459 hydrosilylation reaction Methods 0.000 claims abstract 5
- 125000001453 quaternary ammonium group Chemical group 0.000 claims abstract 5
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 claims abstract 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims abstract 2
- 150000002118 epoxides Chemical class 0.000 claims 7
- 125000003118 aryl group Chemical group 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 2
- 238000007259 addition reaction Methods 0.000 claims 2
- 239000000084 colloidal system Substances 0.000 claims 2
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 claims 2
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 claims 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 2
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 claims 1
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical group CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 claims 1
- NECLBWVMNKCXFG-UHFFFAOYSA-N 2-methyl-3-pent-4-enyloxirane Chemical compound CC1OC1CCCC=C NECLBWVMNKCXFG-UHFFFAOYSA-N 0.000 claims 1
- KCCIMXJIZJBZPX-UHFFFAOYSA-N 2-pent-4-enyloxirane Chemical compound C=CCCCC1CO1 KCCIMXJIZJBZPX-UHFFFAOYSA-N 0.000 claims 1
- SLJFKNONPLNAPF-UHFFFAOYSA-N 3-Vinyl-7-oxabicyclo[4.1.0]heptane Chemical compound C1C(C=C)CCC2OC21 SLJFKNONPLNAPF-UHFFFAOYSA-N 0.000 claims 1
- SPGMNSDVDPWYIS-UHFFFAOYSA-N 3-ethenyl-3,6-dimethyl-7-oxabicyclo[4.1.0]heptane Chemical compound C1CC(C)(C=C)CC2OC21C SPGMNSDVDPWYIS-UHFFFAOYSA-N 0.000 claims 1
- CVKMDAZAUGXUFX-UHFFFAOYSA-N C1C2(C=C)CCC1C1C2O1 Chemical compound C1C2(C=C)CCC1C1C2O1 CVKMDAZAUGXUFX-UHFFFAOYSA-N 0.000 claims 1
- GXBYFVGCMPJVJX-UHFFFAOYSA-N Epoxybutene Chemical compound C=CC1CO1 GXBYFVGCMPJVJX-UHFFFAOYSA-N 0.000 claims 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 229910052785 arsenic Chemical group 0.000 claims 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical group [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000002091 cationic group Chemical group 0.000 claims 1
- 229920001577 copolymer Polymers 0.000 claims 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- XWRLQRLQUKZEEU-UHFFFAOYSA-N ethyl(hydroxy)silicon Chemical compound CC[Si]O XWRLQRLQUKZEEU-UHFFFAOYSA-N 0.000 claims 1
- KCWYOFZQRFCIIE-UHFFFAOYSA-N ethylsilane Chemical compound CC[SiH3] KCWYOFZQRFCIIE-UHFFFAOYSA-N 0.000 claims 1
- 235000013332 fish product Nutrition 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 150000004714 phosphonium salts Chemical class 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000011574 phosphorus Chemical group 0.000 claims 1
- 229910052697 platinum Inorganic materials 0.000 claims 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims 1
- 238000006116 polymerization reaction Methods 0.000 claims 1
- 229920001843 polymethylhydrosiloxane Polymers 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 claims 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 150000002924 oxiranes Chemical class 0.000 abstract 2
- 229920001296 polysiloxane Polymers 0.000 abstract 2
- 239000004593 Epoxy Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000007142 ring opening reaction Methods 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
Classifications
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- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/06—Preparatory processes
- C08G77/08—Preparatory processes characterised by the catalysts used
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/0825—Preparations of compounds not comprising Si-Si or Si-cyano linkages
- C07F7/0827—Syntheses with formation of a Si-C bond
- C07F7/0829—Hydrosilylation reactions
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
- B01J23/42—Platinum
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0838—Compounds with one or more Si-O-Si sequences
- C07F7/0872—Preparation and treatment thereof
- C07F7/0876—Reactions involving the formation of bonds to a Si atom of a Si-O-Si sequence other than a bond of the Si-O-Si linkage
- C07F7/0878—Si-C bond
- C07F7/0879—Hydrosilylation reactions
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- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/1876—Preparation; Treatments not provided for in C07F7/20 by reactions involving the formation of Si-C linkages
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- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/12—Polysiloxanes containing silicon bound to hydrogen
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- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/38—Polysiloxanes modified by chemical after-treatment
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- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Silicon Polymers (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
본 발명은 에폭시실리콘 생성물을 제조하기 위한 에틸렌형 불포화 에폭사이드와 SiH-함유 실리콘간의 하이드로실릴화 반응에서 에틸렌형 불포화 에폭사이드 개시 화합물 또는 에폭시실리콘 생성물의 옥시란 개환 반응을 촉진시키지 않는 4급 암모늄, 포스포늄 또는 아소늄 헥사할로플라티네이트가 촉매작용하여 경화성 에폭시실리콘 화합물을 제조하는 방법을 제공한다. 또한 본 발명은 상기 방법에 의해 제조된 경화성 에폭시실리콘 조성물을 제공한다.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (10)
- (ⅰ) (A) 약 1중량부의 에틸렌형 불포화 에폭사이드; (B)(A)를 기준으로 약 0.5 내지 약 400 중량부의 유기수소실란 또는 유기수소실로산; 및 (C) 약 1 내지 약 5000 ppm의 하기 일반식을 갖는 4급 비스(오늄)할로플라티네이트:(R4M2)2RtX6
- 제1항에 있어서, 단계(ⅰ)에서 상기 에틸렌형 불포화 에폭사이드가 알릴 글리시딜 에테르, 메트알릴 글리시딜 에테르, 1-메틸-4-이소프로페닐 사이클로헥션 옥사이드, 2,6-디메틸-2,3-에폭시-7-옥텐, 1,4-디메틸-4-비닐사이클로헥센 옥사이드, 4-비닐사이클로헥센 옥사이드, 비닐노르보넨 모노옥사이드, 디사이클로펜타디엔 모노옥사이드, 1,2-에폭시-6-헵텐, 및 1,2-에폭시-3-부텐으로 이루어진 군중에서 선택되는 방법.
- 제1항에 있어서, 단계(ⅰ)에서 상기 유기수소실록산이 폴리(디메틸 실록산)-폴리(메틸수소 실록산) 공중 합체인 방법.
- 제1항에 있어서, 단계(Ⅰ)에서 4급 암모늄 아소늄 또는 포스포늄 염 및 할로플라틴산의 염을 상기 혼합물에 가함으로써 상기 4급 비스(오늄) 할로 플라티네이트가 상기 혼합물중에 생성되는 방법.
- 제1항에 있어서, 단계(ⅰ)에서 상기 4급 비스(오늄) 할로프라티네이트의 그룹 R이 독립적으로 메틸,에틸, 프로필, 부틸, n-펜틸, n-헥실, n-헵틸, n-옥틸, 스테아릴, 톨릴, 벤질 및 페닐 라디칼로 이루어진 군중에서 선택된 유기 라디칼인 방법.
- 제1항에 있어서, 단계(ⅱ)가 약 25℃ 내지 약 120℃의 온도에서 상기 단계(ⅰ)의 혼합물을 반응시킴을 포함하는 방법.
- 에폭시실란 또는 에폭시실록산 및 4급 암모늄, 포스포늄 또는 아소늄 할로플라틴이트를 포함하는 경화성 조성물.
- 제7항에 있어서, 상기 에폭시실란이 (사이클로헥센 옥사이드)에틸 실란이거나 또는 상기 에폭시실록산이(사이클로헥센 옥사이드)에틸 실록산인 조성물.
- (ⅰ) 에틸형 불포화 에폭사이드, 유기수소실란 또는 유기수소실록산 및 4급 암모늄, 포스포늄 또는 아소늄할로플라티네이트를 포함하는 혼합물을 제공하는 단계; 및 (ⅱ) 에폭시실리콘 생선물을 생성하는 상기 에틸렌형 불포화 에폭사이드와 상기 유기수소실란 또는 유기 수소실록산간의 하이드로 실릴화 부가반응을 촉진시키거나 상기 에틸레형 불포화 에폭사이드 또는 상기 에폭시실리콘 생성물의 에폭사이드 개환 중합 반응 촉진시키지 않는 조건하에 상기 단계(ⅰ)의 혼합물을 반응시키는 단계를 포함하는, 에틸렌형 불포화 에폭사이드와 유기수소실란 또는 유기수소실록산간의 하이드로실릴화 부가반응중 옥시란 개환 중합을 억제하는 방법.
- (ⅰ) 할로플라티네이트 하이드로실릴화 촉매를 제공하는 단계; 및 (ⅱ) 상기 단계(ⅰ)의 촉매와 일반식 MR4 +(여기서, M은 질소, 인 또는 비소이고, 그룹 R은 독립적으로 치환되거나 비치환된 C1-30선형 알킬, 또는 아릴, 알크아릴 또는 아르알킬 라디칼을 포함하는 유기 라디칼이다)의 양이온 종을 함유하는, 4급 암모늄, 포스포늄 또는 아소늄 염을 혼합하여 상기 염이 상기 촉매의 콜로이드 형성을 방지하도록 하는 단계를 할로플라티네이트 하이드로실릴화 촉매에 의해 콜로이드 형성을 방지하는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US89693592A | 1992-06-11 | 1992-06-11 | |
| US896,935 | 1992-06-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR940005716A true KR940005716A (ko) | 1994-03-22 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019930010555A KR940005716A (ko) | 1992-06-11 | 1993-06-10 | 에폭시실리콘 단량체 및 중합체의 합성을 위한 선택적 촉매 |
Country Status (2)
| Country | Link |
|---|---|
| US (2) | US6124418A (ko) |
| KR (1) | KR940005716A (ko) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6054501A (en) * | 1996-06-12 | 2000-04-25 | Nippon Kayaku Kabushiki Kaisha | Photopolymerization initiator and energy ray curable composition containing the same |
| FR2749850B1 (fr) * | 1996-06-12 | 1998-09-04 | Rhone Poulenc Chimie | Procede d'hydrosilylation avec des huiles silicones et des motifs contenant au moins un cycle hydrocarbone dans lequel est inclus un atome d'oxygene en presence d'une composition catalytique |
| US6545115B2 (en) | 1996-12-11 | 2003-04-08 | Rhodia Chimie | Process for preparing a stable silicone oil containing SiH groups and hydrosilylable functions |
| DE19805083A1 (de) * | 1998-02-09 | 1999-08-12 | Huels Chemische Werke Ag | Verfahren zur Herstellung von 3-Glycidyloxypropyltrialkoxysilanen |
| US6365696B1 (en) | 1999-12-17 | 2002-04-02 | Crompton Corporation | Process for producing epoxyorganosilicon compounds |
| FR2813081B1 (fr) * | 2000-08-17 | 2005-12-23 | Rhodia Chimie Sa | Procede de preparation d'huiles silicones par hydrosilylation de synthons contenant au moins un cycle hydrocarbone dans lequel est inclus un atome d'oxygene en presence d'un complexe metallique catalytique |
| US6706840B1 (en) | 2002-10-07 | 2004-03-16 | General Electric Company | Method for preparing oxirane-containing organosilicon compositions |
| US7122290B2 (en) * | 2004-06-15 | 2006-10-17 | General Electric Company | Holographic storage medium |
| US7897296B2 (en) | 2004-09-30 | 2011-03-01 | General Electric Company | Method for holographic storage |
| US20060078802A1 (en) * | 2004-10-13 | 2006-04-13 | Chan Kwok P | Holographic storage medium |
| WO2007079240A2 (en) * | 2005-12-29 | 2007-07-12 | The University Of Akron | Photocurable polymers for ophthalmic applications |
| US20090018301A1 (en) * | 2006-03-10 | 2009-01-15 | Thomas Stephen J | Heterogeneous hydrosilylation catalysts, polymers formed therewith, and related coating compositions |
| EP3195932A4 (en) | 2014-08-12 | 2018-04-11 | Kyushu University, National University Corporation | Hydrosilylation reaction catalyst |
| CN106660031A (zh) | 2014-08-12 | 2017-05-10 | 国立大学法人九州大学 | 氢化硅烷化反应催化剂 |
| JP6761997B2 (ja) | 2014-08-19 | 2020-09-30 | 国立大学法人九州大学 | ヒドロシリル化鉄触媒 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4083856A (en) * | 1969-08-18 | 1978-04-11 | Union Carbide Corporation | Addition of unsaturated epoxy monomer to Si-H with chloroplatinic acid and HCl-acceptor |
| JPS585407B2 (ja) * | 1980-01-22 | 1983-01-31 | 工業技術院長 | 赤外用光フアイバ− |
| US4617238A (en) * | 1982-04-01 | 1986-10-14 | General Electric Company | Vinyloxy-functional organopolysiloxane compositions |
| JPH0788394B2 (ja) * | 1987-04-22 | 1995-09-27 | 東燃株式会社 | エポキシ基含有シラン化合物の製造方法 |
| US5128431A (en) * | 1989-09-01 | 1992-07-07 | General Electric Company | Platinum catalyzed heterocyclic compound compositions |
-
1993
- 1993-06-10 KR KR1019930010555A patent/KR940005716A/ko not_active Application Discontinuation
-
1994
- 1994-02-14 US US08/195,897 patent/US6124418A/en not_active Expired - Lifetime
- 1994-02-14 US US08/195,792 patent/US5583194A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US6124418A (en) | 2000-09-26 |
| US5583194A (en) | 1996-12-10 |
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