JP2014502271A5 - - Google Patents
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- JP2014502271A5 JP2014502271A5 JP2013541003A JP2013541003A JP2014502271A5 JP 2014502271 A5 JP2014502271 A5 JP 2014502271A5 JP 2013541003 A JP2013541003 A JP 2013541003A JP 2013541003 A JP2013541003 A JP 2013541003A JP 2014502271 A5 JP2014502271 A5 JP 2014502271A5
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- JP
- Japan
- Prior art keywords
- formula
- alkyl
- substituted
- independently
- aryl
- 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
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- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 17
- 125000005842 heteroatom Chemical group 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 9
- 125000003107 substituted aryl group Chemical group 0.000 claims description 9
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 8
- 229920006395 saturated elastomer Polymers 0.000 claims description 8
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 229920001296 polysiloxane Polymers 0.000 claims description 3
- 238000006459 hydrosilylation reaction Methods 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 15
- 239000000203 mixture Substances 0.000 claims 8
- 125000000524 functional group Chemical group 0.000 claims 7
- KTRQRAQRHBLCSQ-UHFFFAOYSA-N 1,2,4-tris(ethenyl)cyclohexane Chemical compound C=CC1CCC(C=C)C(C=C)C1 KTRQRAQRHBLCSQ-UHFFFAOYSA-N 0.000 claims 6
- 125000003342 alkenyl group Chemical group 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- NWRZGFYWENINNX-UHFFFAOYSA-N 1,1,2-tris(ethenyl)cyclohexane Chemical compound C=CC1CCCCC1(C=C)C=C NWRZGFYWENINNX-UHFFFAOYSA-N 0.000 claims 5
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 125000000304 alkynyl group Chemical group 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 125000001931 aliphatic group Chemical group 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 229910052710 silicon Inorganic materials 0.000 claims 2
- ZWUBFMWIQJSEQS-UHFFFAOYSA-N 1,1-bis(ethenyl)cyclohexane Chemical compound C=CC1(C=C)CCCCC1 ZWUBFMWIQJSEQS-UHFFFAOYSA-N 0.000 claims 1
- WVAFEFUPWRPQSY-UHFFFAOYSA-N 1,2,3-tris(ethenyl)benzene Chemical compound C=CC1=CC=CC(C=C)=C1C=C WVAFEFUPWRPQSY-UHFFFAOYSA-N 0.000 claims 1
- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 claims 1
- VMAWODUEPLAHOE-UHFFFAOYSA-N 2,4,6,8-tetrakis(ethenyl)-2,4,6,8-tetramethyl-1,3,5,7,2,4,6,8-tetraoxatetrasilocane Chemical compound C=C[Si]1(C)O[Si](C)(C=C)O[Si](C)(C=C)O[Si](C)(C=C)O1 VMAWODUEPLAHOE-UHFFFAOYSA-N 0.000 claims 1
- BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 claims 1
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 229910004298 SiO 2 Inorganic materials 0.000 claims 1
- 229910004283 SiO 4 Inorganic materials 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- -1 aromatic heterocyclic hydrocarbon Chemical class 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 150000002430 hydrocarbons Chemical group 0.000 claims 1
- SWGZAKPJNWCPRY-UHFFFAOYSA-N methyl-bis(trimethylsilyloxy)silicon Chemical group C[Si](C)(C)O[Si](C)O[Si](C)(C)C SWGZAKPJNWCPRY-UHFFFAOYSA-N 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 239000010703 silicon Chemical group 0.000 claims 1
- 125000005401 siloxanyl group Chemical group 0.000 claims 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims 1
- 125000005017 substituted alkenyl group Chemical group 0.000 claims 1
- 125000004426 substituted alkynyl group Chemical group 0.000 claims 1
- 229910052717 sulfur Chemical group 0.000 claims 1
- 239000011593 sulfur Chemical group 0.000 claims 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical group CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 claims 1
- DDJSWKLBKSLAAZ-UHFFFAOYSA-N cyclotetrasiloxane Chemical group O1[SiH2]O[SiH2]O[SiH2]O[SiH2]1 DDJSWKLBKSLAAZ-UHFFFAOYSA-N 0.000 description 1
- JJRDHFIVAPVZJN-UHFFFAOYSA-N cyclotrisiloxane Chemical compound O1[SiH2]O[SiH2]O[SiH2]1 JJRDHFIVAPVZJN-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US41706110P | 2010-11-24 | 2010-11-24 | |
| US61/417,061 | 2010-11-24 | ||
| PCT/US2011/061752 WO2012071360A1 (en) | 2010-11-24 | 2011-11-22 | Metal - catalyzed mono - hydrosilylation of polyunsaturated compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014502271A JP2014502271A (ja) | 2014-01-30 |
| JP2014502271A5 true JP2014502271A5 (enExample) | 2015-01-29 |
| JP6019034B2 JP6019034B2 (ja) | 2016-11-02 |
Family
ID=45319392
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013541003A Active JP6019034B2 (ja) | 2010-11-24 | 2011-11-22 | 多価不飽和化合物の金属触媒モノヒドロシリル化 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US8895770B2 (enExample) |
| EP (1) | EP2643330B1 (enExample) |
| JP (1) | JP6019034B2 (enExample) |
| KR (1) | KR101896423B1 (enExample) |
| CN (1) | CN103732599B (enExample) |
| BR (1) | BR112013012734A2 (enExample) |
| TW (1) | TWI457176B (enExample) |
| WO (1) | WO2012071360A1 (enExample) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2643335B1 (en) * | 2010-11-24 | 2015-03-11 | Momentive Performance Materials Inc. | Hydrosilylation catalyst |
| JP6101695B2 (ja) | 2011-09-20 | 2017-03-22 | ダウ コーニング コーポレーションＤｏｗ Ｃｏｒｎｉｎｇ Ｃｏｒｐｏｒａｔｉｏｎ | ニッケル含有ヒドロシリル化触媒及びその触媒を含有する組成物 |
| WO2013081794A1 (en) | 2011-12-01 | 2013-06-06 | Dow Corning Corporation | Hydrosilylation reaction catalysts and curable compositions and methods for their preparation and use |
| US9782763B2 (en) | 2011-12-14 | 2017-10-10 | Momentive Performance Materials Inc. | Non-precious metal-based hyrdosilylation catalysts exhibiting improved selectivity |
| US9371340B2 (en) | 2012-08-16 | 2016-06-21 | Momentive Performance Materials Inc. | Dehydrogenative silylation, hydrosilylation and crosslinking using cobalt catalysts |
| US9447125B2 (en) | 2012-08-16 | 2016-09-20 | Momentive Performance Materials Inc. | Reusable homogeneous cobalt pyridine diimine catalysts for dehydrogenative silylation and tandem dehydrogenative-silylation-hydrogenation |
| US9890182B2 (en) | 2013-05-06 | 2018-02-13 | Momentive Performance Materials Inc. | Selective 1,2-hydrosilylation of terminally unsaturated 1,3-dienes using iron catalysts |
| US9371339B2 (en) | 2013-05-06 | 2016-06-21 | Momentive Performance Materials Inc. | Saturated and unsaturated silahydrocarbons via iron and cobalt pyridine diimine catalyzed olefin silylation |
| WO2014186513A1 (en) | 2013-05-15 | 2014-11-20 | Momentive Performance Materials Inc. | Activation of metal salts with silylhydrides and their use in hydrosilylation reactions |
| JP6486925B2 (ja) | 2013-11-19 | 2019-03-20 | モメンティブ パフォーマンス マテリアルズ インコーポレイテッド | コバルト触媒並びにヒドロシリル化及び脱水素シリル化のためのその使用 |
| WO2015077344A1 (en) | 2013-11-19 | 2015-05-28 | The Trustees Of Princeton University | Hydroboration and borylation with cobalt catalysts |
| JP6486924B2 (ja) * | 2013-11-19 | 2019-03-20 | モメンティブ パフォーマンス マテリアルズ インコーポレイテッド | コバルト触媒並びにヒドロシリル化及び脱水素シリル化のためのその使用 |
| WO2015171881A1 (en) * | 2014-05-08 | 2015-11-12 | Momentive Performance Materials Inc. | Dialkyl cobalt catalysts and their use for hydrosilylation and dehydrogenative silylation |
| JP2015231965A (ja) * | 2014-06-10 | 2015-12-24 | 国立研究開発法人産業技術総合研究所 | 有機ケイ素化合物の製造方法及び触媒組成物 |
| EP3195932B1 (en) | 2014-08-12 | 2024-08-21 | Kyushu University, National University Corporation | Hydrosilylation reaction catalyst |
| EP3181226B1 (en) | 2014-08-12 | 2024-08-07 | Kyushu University, National University Corporation | Hydrosilylation reaction catalyst |
| 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 |
| US20180200703A1 (en) | 2015-07-14 | 2018-07-19 | Kyushu University, National University Corporation | Hydrosilylation reaction catalyst |
| JP6846423B2 (ja) * | 2015-07-24 | 2021-03-24 | モメンティブ パフォーマンス マテリアルズ インコーポレイテッドＭｏｍｅｎｔｉｖｅ Ｐｅｒｆｏｒｍａｎｃｅ Ｍａｔｅｒｉａｌｓ Ｉｎｃ． | ピリジンジイミンコバルトカルボキシレート触媒を用いた脱水素シリル化、ヒドロシリル化および架橋 |
| KR101728308B1 (ko) | 2015-09-14 | 2017-04-19 | 기초과학연구원 | 비전이금속 촉매법 수소규소화 반응을 이용한 규소 고분자 제조방법 |
| CN108473514B (zh) | 2016-01-22 | 2021-08-31 | 信越化学工业株式会社 | 新型异腈化合物和氢化硅烷化反应催化剂 |
| WO2018159595A1 (ja) | 2017-02-28 | 2018-09-07 | 国立大学法人九州大学 | ヒドロシリル化反応、水素化反応およびヒドロシラン還元反応用触媒 |
| JP2019064950A (ja) | 2017-09-29 | 2019-04-25 | 国立大学法人九州大学 | コバルト錯体、その製造方法およびヒドロシリル化反応用触媒 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2641785B1 (fr) | 1989-01-19 | 1992-07-31 | Essilor Int | Composition de polymeres transparents pour lentilles de contact de type rigide, permeables a l'oxygene |
| US5691435A (en) * | 1996-01-25 | 1997-11-25 | Wacker-Chemie Gmbh | Crosslinkable compositions |
| US5756795A (en) * | 1996-12-30 | 1998-05-26 | Dow Corning Corporation | Unsaturated accelerators for hydrosilation |
| US5986022A (en) * | 1998-04-01 | 1999-11-16 | Witco Corporation | Continuous manufacture of silicone coploymers |
| GB9819847D0 (en) | 1998-09-12 | 1998-11-04 | Bp Chem Int Ltd | Novel compounds |
| DE19856115A1 (de) | 1998-12-04 | 2000-06-21 | Wacker Chemie Gmbh | Alkenylgruppen aufweisende Siloxancopolymere |
| US6278011B1 (en) | 1999-08-30 | 2001-08-21 | The University Of Dayton | Polysilahydrocarbons as lubricants for aerospace application |
| US7429672B2 (en) | 2006-06-09 | 2008-09-30 | Momentive Performance Materials Inc. | Process for the direct synthesis of trialkoxysilane |
| US7696269B2 (en) | 2006-12-28 | 2010-04-13 | Momentive Performance Materials Inc. | Silated core polysulfides, their preparation and use in filled elastomer compositions |
| US8236915B2 (en) | 2009-07-10 | 2012-08-07 | Momentive Performance Materials Inc. | Hydrosilylation catalysts |
| US8415443B2 (en) * | 2009-07-10 | 2013-04-09 | Momentive Performance Materials Inc. | Hydrosilylation catalysts |
| WO2012071358A2 (en) * | 2010-11-24 | 2012-05-31 | Momentive Performance Materials Inc. | In-situ activation of metal complexes containing terdentate nitrogen ligands used as hydrosilylation catalysts |
-
2011
- 2011-11-22 WO PCT/US2011/061752 patent/WO2012071360A1/en not_active Ceased
- 2011-11-22 KR KR1020137016391A patent/KR101896423B1/ko active Active
- 2011-11-22 JP JP2013541003A patent/JP6019034B2/ja active Active
- 2011-11-22 US US13/302,506 patent/US8895770B2/en active Active
- 2011-11-22 BR BR112013012734A patent/BR112013012734A2/pt not_active Application Discontinuation
- 2011-11-22 EP EP11794591.5A patent/EP2643330B1/en active Active
- 2011-11-22 CN CN201180065872.0A patent/CN103732599B/zh active Active
- 2011-11-23 TW TW100142961A patent/TWI457176B/zh active
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