KR930023406A - 에폭시실리콘의 개선된 합성방법 - Google Patents
에폭시실리콘의 개선된 합성방법 Download PDFInfo
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- KR930023406A KR930023406A KR1019930008411A KR930008411A KR930023406A KR 930023406 A KR930023406 A KR 930023406A KR 1019930008411 A KR1019930008411 A KR 1019930008411A KR 930008411 A KR930008411 A KR 930008411A KR 930023406 A KR930023406 A KR 930023406A
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- Prior art keywords
- sih
- tertiary amine
- siloxane
- monooxide
- hydrosilylation
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- 239000004593 Epoxy Substances 0.000 title claims 2
- 229920001296 polysiloxane Polymers 0.000 title abstract 2
- 230000015572 biosynthetic process Effects 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- 238000006459 hydrosilylation reaction Methods 0.000 claims abstract 9
- 150000003512 tertiary amines Chemical class 0.000 claims abstract 9
- 238000000034 method Methods 0.000 claims abstract 8
- -1 siloxanes Chemical class 0.000 claims abstract 8
- 239000000203 mixture Substances 0.000 claims abstract 7
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract 6
- 239000003054 catalyst Substances 0.000 claims abstract 5
- 238000007259 addition reaction Methods 0.000 claims abstract 3
- 238000004519 manufacturing process Methods 0.000 claims abstract 2
- 229910052703 rhodium Inorganic materials 0.000 claims abstract 2
- 239000010948 rhodium Substances 0.000 claims abstract 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims abstract 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims 4
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims 4
- 229910000077 silane Inorganic materials 0.000 claims 4
- CCEFMUBVSUDRLG-KXUCPTDWSA-N (4R)-limonene 1,2-epoxide Natural products C1[C@H](C(=C)C)CC[C@@]2(C)O[C@H]21 CCEFMUBVSUDRLG-KXUCPTDWSA-N 0.000 claims 2
- 125000000549 (4R)-limonene 1,2-epoxide group Chemical group 0.000 claims 2
- WEEGYLXZBRQIMU-UHFFFAOYSA-N 1,8-cineole Natural products C1CC2CCC1(C)OC2(C)C WEEGYLXZBRQIMU-UHFFFAOYSA-N 0.000 claims 2
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 claims 2
- SLJFKNONPLNAPF-UHFFFAOYSA-N 3-Vinyl-7-oxabicyclo[4.1.0]heptane Chemical compound C1C(C=C)CCC2OC21 SLJFKNONPLNAPF-UHFFFAOYSA-N 0.000 claims 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000005270 trialkylamine group Chemical group 0.000 claims 2
- INYHZQLKOKTDAI-UHFFFAOYSA-N 5-ethenylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(C=C)CC1C=C2 INYHZQLKOKTDAI-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
- 150000003974 aralkylamines Chemical class 0.000 claims 1
- 150000004696 coordination complex Chemical class 0.000 claims 1
- 238000004132 cross linking Methods 0.000 claims 1
- 230000000977 initiatory effect Effects 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- JOKPITBUODAHEN-UHFFFAOYSA-N sulfanylideneplatinum Chemical compound [Pt]=S JOKPITBUODAHEN-UHFFFAOYSA-N 0.000 claims 1
- VPYJNCGUESNPMV-UHFFFAOYSA-N triallylamine Chemical compound C=CCN(CC=C)CC=C VPYJNCGUESNPMV-UHFFFAOYSA-N 0.000 claims 1
- 125000005259 triarylamine group Chemical group 0.000 claims 1
- 150000004756 silanes Chemical class 0.000 abstract 2
- 239000003381 stabilizer Substances 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 230000000087 stabilizing effect Effects 0.000 abstract 1
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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
- C08G77/06—Preparatory processes
- C08G77/08—Preparatory processes characterised by the catalysts used
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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
- C08G77/38—Polysiloxanes modified by chemical after-treatment
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- 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
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- 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
- B01J23/46—Ruthenium, rhodium, osmium or iridium
- B01J23/464—Rhodium
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- 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
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- 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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- 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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- 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
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- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
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Abstract
본 발명은 3차 아민 안정화제 존재하에 로듐 금속착화합물이 촉매 작용하는 SiH-함유 실란 또는 실록산과 올레핀 에폭사이드사이의 하이드로실릴화 반응에 의해 에폭시-작용성 실리콘을 제조하는 방법을 제공한다. 본 발명을 수행시,RhCl3〔(CH2(CH2)3)2S〕3또는 PtCl2〔(CH3CH2)2S〕2가 적당한 하이드로실릴화 촉매이고, 메틸디코코아민, CH3(CH16H37)2N이 적당한 안정화제이다. 또한, 본 발명은 하이드로실릴화 부가 반응 도중 겔화되기 어려운, SiH-작용성 실란 또는 실록산 및 3차 아민을 포함하는 조성물을 제공한다.본 발명은 에폭시실리콘 제조에 사용된 하이드로실릴화 부가 반응 도중과 반응 후 에폭시실리콘을 안정화시키키 위한 방법을 또한 제공한다.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (9)
- (a) SiH-함유 실란 또는 실록산, 3차 아민 및 하이드로실릴화 촉매를 포함한는 혼합물을 제조하는 단계. 및 (b) 올레핀 에폭사이드를 단계 (a)의 혼합물과 반응시켜 에폭시실리콘을 제조하는 단계를 포함하는 에폭시실리콘의 제조방법.
- 제1항에 있어서, 단계 (a) 에서 상기 3차 아민이 치환되거나 또는 비치환된 트리알킬아민, 트리아릴아민, 알크아릴아민, 아르알킬아민 및 상기 치환제중 하나 이상을 포함하는 혼합된 3차 아민으로 이루어진 군중에서 선택되는 방버.
- 제1항에 있어서, 단계 (a) 에서 상기 하이드로실릴화 촉매가 로륨 또는 백금 설파이드 착화합물을 포함하는 방법.
- 제3항에 있어서, 단계 (a) 에서 상기 하이드로실릴화 촉매가 하기 일반식을 갖는 금속 착화합물인 방법 :RhX3(R1 2S)3또는 PtX2(R1 2S)2상기식에서,X가 F-이외의 할로겐이고, R1그룹은 각각 독립적으로 C(1-30)알킬, 아릴, 알크아릴, 또는 아르알킬이고 치환하거나 또는 비치환될 수 있다.
- 제1항에 있어서, 단계 (b)에서, 상기 올레핀 에폭사이드가 리모넨옥사이드, 4-비닐사이클로헥센 옥사이드, 알릴글리시딜에테르, 글리시딜아크릴레이트, 7-에폭시-1-옥텐, 비닐노르보넨 모노옥사이드 및 디사이클로펜틸디엔 모노옥사이드로 이루어진 군중에서 선택되는 방법.
- 제1항에 있어서, 단계 (a) 에서, 상기 3차 아민이 트리알킬아민, 트리알릴아민, 알크아릴아민, 아르알칼아민 및 상기 치환제중 하나 이상을 포함하는 혼합된 3차 아민으로 이루어진 군중에서 선택되고, 상기 하이드로실릴화 촉매가 일반식 RhX3(R1 2S)3또는 PtX2(R1 2S)2(여기서, X는 F-이외의 할로겐이고 R1그룹은 각각 독립적으로 C(1-30)알킬, 아릴, 알크아릴, 또는 아르알킬이고 치환하거나 또는 비치환될 수 있다)을 갖고, 단계 (b)에서, 상기 올레핀 에폭사이드가 리모넨옥사이드, 4-비닐사이클로헥센옥사이드, 알릴글리시딜에테르, 글리시딜아크릴레이트, 7-에폭시-1-옥텐, 비닐노르보넨 모노옥사이드 및 디사이클로펜틸디엔 모노옥사이드로 이루어진 군중에서 선택되는 방법.
- SiH-함유 실란 또는 실록산 및 3차 아민을 포함하는 조성물.
- 제7항에 있어서,올레핀 에폭사이드를 또한 포함하는 조성물.
- (a) SiH-함유 실란 또는 실록산을 포함하는 제1조성물을 제조하는 단계, 및 (b) 상기 SiH-함유 실란 또는 실록산과 올레핀 에폭사이드간의 하이드로실릴화 부가 반응이 개시되기 건에 3차 아민을 상기 제1조성물에 가하는 단계를 포함하는 하이드로실릴화 부가 반응에서 에폭시실리콘 제조시 에폭시-매개된 가교결합을 방지하는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US885,095 | 1992-05-18 | ||
US07/885,095 US5258480A (en) | 1992-05-18 | 1992-05-18 | Syntheses of epoxysilicones |
Publications (1)
Publication Number | Publication Date |
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KR930023406A true KR930023406A (ko) | 1993-12-18 |
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Application Number | Title | Priority Date | Filing Date |
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KR1019930008411A KR930023406A (ko) | 1992-05-18 | 1993-05-17 | 에폭시실리콘의 개선된 합성방법 |
Country Status (9)
Country | Link |
---|---|
US (2) | US5258480A (ko) |
EP (1) | EP0578354B1 (ko) |
JP (1) | JP3529808B2 (ko) |
KR (1) | KR930023406A (ko) |
CN (1) | CN1080927A (ko) |
CA (1) | CA2092475A1 (ko) |
DE (1) | DE69327427T2 (ko) |
ES (1) | ES2140439T3 (ko) |
FI (1) | FI932230A (ko) |
Families Citing this family (37)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5387698A (en) * | 1992-06-11 | 1995-02-07 | General Electric Company | Rhodium containing selective catalysts for the synthesis of epoxysiloxane/epoxysilicone monomers and polymers |
US5258480A (en) * | 1992-05-18 | 1993-11-02 | General Electric Company | Syntheses of epoxysilicones |
GB9223335D0 (en) * | 1992-11-06 | 1992-12-23 | Dow Corning | Hydrosilylation process |
JPH07133351A (ja) * | 1993-11-08 | 1995-05-23 | Shin Etsu Chem Co Ltd | エポキシ変性シリコーンの製造方法 |
US5650453A (en) * | 1995-04-28 | 1997-07-22 | General Electric Company | UV curable epoxysilicone blend compositions |
US5500300A (en) * | 1995-05-18 | 1996-03-19 | General Electric Company | Silicone fluids having chloroalkyl and epoxy groups and photocurable silicone coating compositions |
US5747172A (en) * | 1995-08-30 | 1998-05-05 | General Electric Company | Ultraviolet and electron beam curable propenyl-ether silicone release compositions |
US5583195A (en) * | 1995-09-29 | 1996-12-10 | General Electric Company | Photocurable epoxy silicones functionalized with fluorescent or photosensitizing marker dyes |
US5721290A (en) * | 1996-11-26 | 1998-02-24 | General Electric Company | Oxo-acid modified epoxy silicone compositions |
US5942557A (en) * | 1997-09-19 | 1999-08-24 | General Electric Company | Low coefficient of friction silicone release formulations |
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-
1992
- 1992-05-18 US US07/885,095 patent/US5258480A/en not_active Expired - Lifetime
-
1993
- 1993-03-25 CA CA002092475A patent/CA2092475A1/en not_active Abandoned
- 1993-05-12 DE DE69327427T patent/DE69327427T2/de not_active Expired - Lifetime
- 1993-05-12 EP EP93303672A patent/EP0578354B1/en not_active Expired - Lifetime
- 1993-05-12 ES ES93303672T patent/ES2140439T3/es not_active Expired - Lifetime
- 1993-05-13 JP JP11084793A patent/JP3529808B2/ja not_active Expired - Lifetime
- 1993-05-17 KR KR1019930008411A patent/KR930023406A/ko not_active Application Discontinuation
- 1993-05-17 FI FI932230A patent/FI932230A/fi not_active Application Discontinuation
- 1993-05-18 CN CN93106016A patent/CN1080927A/zh active Pending
- 1993-10-29 US US08/145,451 patent/US5391676A/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
EP0578354B1 (en) | 1999-12-29 |
EP0578354A3 (ko) | 1994-03-16 |
US5258480A (en) | 1993-11-02 |
EP0578354A2 (en) | 1994-01-12 |
JP3529808B2 (ja) | 2004-05-24 |
JPH0632906A (ja) | 1994-02-08 |
US5391676A (en) | 1995-02-21 |
CA2092475A1 (en) | 1993-11-19 |
ES2140439T3 (es) | 2000-03-01 |
CN1080927A (zh) | 1994-01-19 |
DE69327427D1 (de) | 2000-02-03 |
DE69327427T2 (de) | 2000-07-20 |
FI932230A0 (fi) | 1993-05-17 |
FI932230A (fi) | 1993-11-19 |
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