JPS61129184A - Ｏ‐シリル化されたケテンアセタール類およびエノールエーテル類並びに製造方法 - Google Patents
Ｏ‐シリル化されたケテンアセタール類およびエノールエーテル類並びに製造方法Info
- Publication number
- JPS61129184A JPS61129184A JP60257889A JP25788985A JPS61129184A JP S61129184 A JPS61129184 A JP S61129184A JP 60257889 A JP60257889 A JP 60257889A JP 25788985 A JP25788985 A JP 25788985A JP S61129184 A JPS61129184 A JP S61129184A
- Authority
- JP
- Japan
- Prior art keywords
- methoxy
- dimethyl
- group
- methyl
- compound 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.)
- Granted
Links
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- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 23
- 238000006116 polymerization reaction Methods 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 22
- -1 enols Ethers Chemical class 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 18
- 239000003999 initiator Substances 0.000 claims description 16
- 239000003054 catalyst Substances 0.000 claims description 15
- 239000000126 substance Substances 0.000 claims description 14
- 238000006459 hydrosilylation reaction Methods 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
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- 229910052703 rhodium Inorganic materials 0.000 claims description 8
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- 125000003118 aryl group Chemical group 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
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- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- XAMVPVUIZQYMNU-UHFFFAOYSA-N tritert-butyl 1-methoxyprop-1-enyl silicate Chemical group COC(=CC)O[Si](OC(C)(C)C)(OC(C)(C)C)OC(C)(C)C XAMVPVUIZQYMNU-UHFFFAOYSA-N 0.000 claims description 2
- FFRFWXHFVRCXMF-UHFFFAOYSA-N 1-methoxyprop-1-enyl tripropan-2-yl silicate Chemical group COC(=CC)O[Si](OC(C)C)(OC(C)C)OC(C)C FFRFWXHFVRCXMF-UHFFFAOYSA-N 0.000 claims 1
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- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 14
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- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 10
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- 238000003756 stirring Methods 0.000 description 10
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- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- GIRKRMUMWJFNRI-UHFFFAOYSA-N tris(dimethylamino)silicon Chemical compound CN(C)[Si](N(C)C)N(C)C GIRKRMUMWJFNRI-UHFFFAOYSA-N 0.000 description 8
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 6
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 5
- 238000001819 mass spectrum Methods 0.000 description 5
- 229950000688 phenothiazine Drugs 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 4
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 4
- QCKKBOHAYRLMQP-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]silane Chemical compound CC(C)(C)O[SiH](OC(C)(C)C)OC(C)(C)C QCKKBOHAYRLMQP-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 3
- LZDPMWPKENASIX-UHFFFAOYSA-N bis(trimethylsilyloxy)methylsilicon Chemical compound C[Si](C)(C)OC([Si])O[Si](C)(C)C LZDPMWPKENASIX-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- DRUOQOFQRYFQGB-UHFFFAOYSA-N ethoxy(dimethyl)silicon Chemical compound CCO[Si](C)C DRUOQOFQRYFQGB-UHFFFAOYSA-N 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 3
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 3
- KWEKXPWNFQBJAY-UHFFFAOYSA-N (dimethyl-$l^{3}-silanyl)oxy-dimethylsilicon Chemical compound C[Si](C)O[Si](C)C KWEKXPWNFQBJAY-UHFFFAOYSA-N 0.000 description 2
- LGXAANYJEHLUEM-UHFFFAOYSA-N 1,2,3-tri(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC(C(C)C)=C1C(C)C LGXAANYJEHLUEM-UHFFFAOYSA-N 0.000 description 2
- JLIDVCMBCGBIEY-UHFFFAOYSA-N 1-penten-3-one Chemical compound CCC(=O)C=C JLIDVCMBCGBIEY-UHFFFAOYSA-N 0.000 description 2
- SNYNNFDVNITLRQ-UHFFFAOYSA-N 2,2,4,4,6,6,8-heptamethyl-1,3,5,7,2,4,6,8$l^{3}-tetraoxatetrasilocane Chemical compound C[Si]1O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 SNYNNFDVNITLRQ-UHFFFAOYSA-N 0.000 description 2
- IGAWKPMXUGZZIH-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOC(=O)C=C IGAWKPMXUGZZIH-UHFFFAOYSA-N 0.000 description 2
- LTVRSJBNXLZFGT-UHFFFAOYSA-N 2-silylethenone Chemical compound [SiH3]C=C=O LTVRSJBNXLZFGT-UHFFFAOYSA-N 0.000 description 2
- WUGOQZFPNUYUOO-UHFFFAOYSA-N 2-trimethylsilyloxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCO[Si](C)(C)C WUGOQZFPNUYUOO-UHFFFAOYSA-N 0.000 description 2
- WIYVVIUBKNTNKG-UHFFFAOYSA-N 6,7-dimethoxy-3,4-dihydronaphthalene-2-carboxylic acid Chemical compound C1CC(C(O)=O)=CC2=C1C=C(OC)C(OC)=C2 WIYVVIUBKNTNKG-UHFFFAOYSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
- 229910002621 H2PtCl6 Inorganic materials 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
- 150000003857 carboxamides Chemical class 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- KZFNONVXCZVHRD-UHFFFAOYSA-N dimethylamino(dimethyl)silicon Chemical compound CN(C)[Si](C)C KZFNONVXCZVHRD-UHFFFAOYSA-N 0.000 description 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 2
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- 238000010438 heat treatment Methods 0.000 description 2
- JTHNLKXLWOXOQK-UHFFFAOYSA-N hex-1-en-3-one Chemical compound CCCC(=O)C=C JTHNLKXLWOXOQK-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- VBYLGQXERITIBP-UHFFFAOYSA-N n-[dimethylamino(methyl)silyl]-n-methylmethanamine Chemical compound CN(C)[SiH](C)N(C)C VBYLGQXERITIBP-UHFFFAOYSA-N 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
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- AECVNJMAOULSMH-UHFFFAOYSA-N triethyl (1-methoxy-2-methylprop-1-enyl) silicate Chemical group CCO[Si](OCC)(OCC)OC(OC)=C(C)C AECVNJMAOULSMH-UHFFFAOYSA-N 0.000 description 2
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- CFLPYZXNRODUHI-UHFFFAOYSA-N (1-methoxy-2-methylprop-1-enyl) tripropan-2-yl silicate Chemical group COC(=C(C)C)O[Si](OC(C)C)(OC(C)C)OC(C)C CFLPYZXNRODUHI-UHFFFAOYSA-N 0.000 description 1
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- UPCHQOGVQKXCNM-UHFFFAOYSA-N C=1C=CC=CC=1N([SiH](C)C)C1=CC=CC=C1 Chemical compound C=1C=CC=CC=1N([SiH](C)C)C1=CC=CC=C1 UPCHQOGVQKXCNM-UHFFFAOYSA-N 0.000 description 1
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- SDOZTEFGBWTEFL-UHFFFAOYSA-N N,N'-dibenzyl-1-silylmethanediamine Chemical compound C=1C=CC=CC=1CNC([SiH3])NCC1=CC=CC=C1 SDOZTEFGBWTEFL-UHFFFAOYSA-N 0.000 description 1
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- QRCQIXDJHXTUJP-UHFFFAOYSA-N N-phenyl-N-(phenylsilylmethyl)aniline Chemical compound C=1C=CC=CC=1N(C=1C=CC=CC=1)C[SiH2]C1=CC=CC=C1 QRCQIXDJHXTUJP-UHFFFAOYSA-N 0.000 description 1
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 1
- 229910021604 Rhodium(III) chloride Inorganic materials 0.000 description 1
- JDJSXFPYSSJJJJ-UHFFFAOYSA-N [(1-methoxy-2-methylprop-1-enoxy)silyl-trimethylsilyloxymethoxy]-trimethylsilane Chemical group COC(=C(C)C)O[SiH2]C(O[Si](C)(C)C)O[Si](C)(C)C JDJSXFPYSSJJJJ-UHFFFAOYSA-N 0.000 description 1
- KTPIYTXZDLZRNV-UHFFFAOYSA-N [1-methoxyprop-1-enoxysilyl(trimethylsilyloxy)methoxy]-trimethylsilane Chemical group COC(=CC)O[SiH2]C(O[Si](C)(C)C)O[Si](C)(C)C KTPIYTXZDLZRNV-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
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- XJLTZAGUXSAJCZ-UHFFFAOYSA-N methyl 3-trimethoxysilylpropanoate Chemical compound COC(=O)CC[Si](OC)(OC)OC XJLTZAGUXSAJCZ-UHFFFAOYSA-N 0.000 description 1
- SWGZAKPJNWCPRY-UHFFFAOYSA-N methyl-bis(trimethylsilyloxy)silicon Chemical compound C[Si](C)(C)O[Si](C)O[Si](C)(C)C SWGZAKPJNWCPRY-UHFFFAOYSA-N 0.000 description 1
- QABJMCUIZVKWCF-UHFFFAOYSA-N methyl-di(propan-2-yloxy)silicon Chemical compound CC(C)O[Si](C)OC(C)C QABJMCUIZVKWCF-UHFFFAOYSA-N 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 description 1
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 description 1
- NCAKWMZPHTZJOT-UHFFFAOYSA-N n-[bis(diethylamino)silyl]-n-ethylethanamine Chemical compound CCN(CC)[SiH](N(CC)CC)N(CC)CC NCAKWMZPHTZJOT-UHFFFAOYSA-N 0.000 description 1
- FUCHEZKCNWQACR-UHFFFAOYSA-N n-[bis(dimethylamino)-(1-methoxy-2-methylprop-1-enoxy)silyl]-n-methylmethanamine Chemical group COC(=C(C)C)O[Si](N(C)C)(N(C)C)N(C)C FUCHEZKCNWQACR-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 150000001282 organosilanes Chemical class 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-UHFFFAOYSA-N 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000058 polyacrylate Polymers 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
- 238000012552 review Methods 0.000 description 1
- SONJTKJMTWTJCT-UHFFFAOYSA-K rhodium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Rh+3] SONJTKJMTWTJCT-UHFFFAOYSA-K 0.000 description 1
- QBERHIJABFXGRZ-UHFFFAOYSA-M rhodium;triphenylphosphane;chloride Chemical compound [Cl-].[Rh].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QBERHIJABFXGRZ-UHFFFAOYSA-M 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- CQDJUAPLVNTUHG-UHFFFAOYSA-N tri(piperidin-1-yl)silane Chemical compound C1CCCCN1[SiH](N1CCCCC1)N1CCCCC1 CQDJUAPLVNTUHG-UHFFFAOYSA-N 0.000 description 1
- VNDGPYDYCKRJDY-UHFFFAOYSA-N triethyl 1-methoxyprop-1-enyl silicate Chemical group CCO[Si](OCC)(OCC)OC(OC)=CC VNDGPYDYCKRJDY-UHFFFAOYSA-N 0.000 description 1
- KZVPFSJPLBOVLO-UHFFFAOYSA-N trimethyl(2-methylprop-1-enoxy)silane Chemical compound CC(C)=CO[Si](C)(C)C KZVPFSJPLBOVLO-UHFFFAOYSA-N 0.000 description 1
- XJCUDULXCZBGBX-UHFFFAOYSA-N tritert-butyl (1-methoxy-2-methylprop-1-enyl) silicate Chemical group COC(=C(C)C)O[Si](OC(C)(C)C)(OC(C)(C)C)OC(C)(C)C XJCUDULXCZBGBX-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Polymerization Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US67328584A | 1984-11-20 | 1984-11-20 | |
| US741832 | 1985-06-06 | ||
| US673285 | 1991-03-21 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61129184A true JPS61129184A (ja) | 1986-06-17 |
| JPH0242836B2 JPH0242836B2 (enrdf_load_stackoverflow) | 1990-09-26 |
Family
ID=24702020
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60257889A Granted JPS61129184A (ja) | 1984-11-20 | 1985-11-19 | Ｏ‐シリル化されたケテンアセタール類およびエノールエーテル類並びに製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61129184A (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2016060723A (ja) * | 2014-09-19 | 2016-04-25 | 信越化学工業株式会社 | 有機ケイ素化合物 |
| JP2019001885A (ja) * | 2017-06-14 | 2019-01-10 | 信越化学工業株式会社 | 自己接着性シリコーンゲル組成物及びその硬化物 |
| WO2020026760A1 (ja) * | 2018-08-03 | 2020-02-06 | 信越化学工業株式会社 | シリコーンゲル組成物及びその硬化物並びにパワーモジュール |
-
1985
- 1985-11-19 JP JP60257889A patent/JPS61129184A/ja active Granted
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2016060723A (ja) * | 2014-09-19 | 2016-04-25 | 信越化学工業株式会社 | 有機ケイ素化合物 |
| JP2019001885A (ja) * | 2017-06-14 | 2019-01-10 | 信越化学工業株式会社 | 自己接着性シリコーンゲル組成物及びその硬化物 |
| WO2020026760A1 (ja) * | 2018-08-03 | 2020-02-06 | 信越化学工業株式会社 | シリコーンゲル組成物及びその硬化物並びにパワーモジュール |
| JPWO2020026760A1 (ja) * | 2018-08-03 | 2021-08-19 | 信越化学工業株式会社 | シリコーンゲル組成物及びその硬化物並びにパワーモジュール |
| US11884820B2 (en) | 2018-08-03 | 2024-01-30 | Shin-Etsu Chemical Co., Ltd. | Silicone gel composition and cured product thereof, and power module |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0242836B2 (enrdf_load_stackoverflow) | 1990-09-26 |
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