JP2016520083A5 - - Google Patents
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- Publication number
- JP2016520083A5 JP2016520083A5 JP2016514070A JP2016514070A JP2016520083A5 JP 2016520083 A5 JP2016520083 A5 JP 2016520083A5 JP 2016514070 A JP2016514070 A JP 2016514070A JP 2016514070 A JP2016514070 A JP 2016514070A JP 2016520083 A5 JP2016520083 A5 JP 2016520083A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- unsaturated
- group
- metal complex
- silylhydride
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 claims 28
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims 20
- 150000001875 compounds Chemical class 0.000 claims 15
- 150000004696 coordination complex Chemical class 0.000 claims 11
- 238000006459 hydrosilylation reaction Methods 0.000 claims 7
- 230000004913 activation Effects 0.000 claims 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 5
- 229920002554 vinyl polymer Polymers 0.000 claims 5
- -1 MgCl 2 Inorganic materials 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 229920000570 polyether Polymers 0.000 claims 4
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 claims 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical group COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims 2
- 239000004721 Polyphenylene oxide Substances 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 229910004298 SiO 2 Inorganic materials 0.000 claims 2
- 229910004283 SiO 4 Inorganic materials 0.000 claims 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims 2
- 150000001336 alkenes Chemical class 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 150000001450 anions Chemical class 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 229930195733 hydrocarbon Natural products 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- PARWUHTVGZSQPD-UHFFFAOYSA-N phenylsilane Chemical compound [SiH3]C1=CC=CC=C1 PARWUHTVGZSQPD-UHFFFAOYSA-N 0.000 claims 2
- 229920001296 polysiloxane Polymers 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 229910000077 silane Inorganic materials 0.000 claims 2
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 claims 2
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 claims 1
- BEZVGIHGZPLGBL-UHFFFAOYSA-N 2,6-diacetylpyridine Chemical compound CC(=O)C1=CC=CC(C(C)=O)=N1 BEZVGIHGZPLGBL-UHFFFAOYSA-N 0.000 claims 1
- UWRZIZXBOLBCON-UHFFFAOYSA-N 2-phenylethenamine Chemical compound NC=CC1=CC=CC=C1 UWRZIZXBOLBCON-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 claims 1
- 239000004698 Polyethylene Substances 0.000 claims 1
- 239000004743 Polypropylene Substances 0.000 claims 1
- 239000004793 Polystyrene Substances 0.000 claims 1
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 claims 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000001252 acrylic acid derivatives Chemical group 0.000 claims 1
- 230000003213 activating effect Effects 0.000 claims 1
- 150000001345 alkine derivatives Chemical class 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 150000008378 aryl ethers Chemical class 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical group C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 150000001924 cycloalkanes Chemical class 0.000 claims 1
- 239000000412 dendrimer Substances 0.000 claims 1
- 229920000736 dendritic polymer Polymers 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 150000002170 ethers Chemical class 0.000 claims 1
- 125000000524 functional group Chemical group 0.000 claims 1
- 150000008282 halocarbons Chemical class 0.000 claims 1
- 150000004678 hydrides Chemical class 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 150000002466 imines Chemical class 0.000 claims 1
- 229910052742 iron Inorganic materials 0.000 claims 1
- FRVCGRDGKAINSV-UHFFFAOYSA-L iron(2+);octadecanoate Chemical compound [Fe+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O FRVCGRDGKAINSV-UHFFFAOYSA-L 0.000 claims 1
- 239000003446 ligand Substances 0.000 claims 1
- 229910052748 manganese Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 125000005394 methallyl group Chemical group 0.000 claims 1
- 229910052759 nickel Inorganic materials 0.000 claims 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 1
- 150000002894 organic compounds Chemical class 0.000 claims 1
- 125000000962 organic group Chemical group 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 229920000573 polyethylene Polymers 0.000 claims 1
- 229920000642 polymer Polymers 0.000 claims 1
- 229920001155 polypropylene Polymers 0.000 claims 1
- 229920002223 polystyrene Polymers 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 229910052707 ruthenium Inorganic materials 0.000 claims 1
- 239000000377 silicon dioxide Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 claims 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361823599P | 2013-05-15 | 2013-05-15 | |
| US61/823,599 | 2013-05-15 | ||
| PCT/US2014/038082 WO2014186513A1 (en) | 2013-05-15 | 2014-05-15 | Activation of metal salts with silylhydrides and their use in hydrosilylation reactions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2016520083A JP2016520083A (ja) | 2016-07-11 |
| JP2016520083A5 true JP2016520083A5 (OSRAM) | 2017-06-22 |
Family
ID=50942347
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016514070A Pending JP2016520083A (ja) | 2013-05-15 | 2014-05-15 | シリルヒドリドによる金属塩の活性化およびヒドロシリル化反応におけるその使用 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US9440999B2 (OSRAM) |
| EP (1) | EP2996804B1 (OSRAM) |
| JP (1) | JP2016520083A (OSRAM) |
| CN (1) | CN105228744B (OSRAM) |
| TW (1) | TWI623544B (OSRAM) |
| WO (1) | WO2014186513A1 (OSRAM) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9371340B2 (en) | 2012-08-16 | 2016-06-21 | Momentive Performance Materials Inc. | Dehydrogenative silylation, hydrosilylation and crosslinking using cobalt catalysts |
| 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 |
| CN105228744B (zh) | 2013-05-15 | 2021-04-06 | 莫门蒂夫性能材料股份有限公司 | 用甲硅烷基氢化物活化金属盐及其在氢化硅烷化反应中的应用 |
| TW201538510A (zh) | 2013-11-19 | 2015-10-16 | Momentive Performance Mat Inc | 鈷觸媒及其於矽氫化與脫氫甲矽烷化之用途 |
| EP3071585B1 (en) | 2013-11-19 | 2018-11-07 | Momentive Performance Materials Inc. | Cobalt catalysts and their use for hydrosilylation and dehydrogenative silylation |
| WO2015077306A1 (en) | 2013-11-19 | 2015-05-28 | Momentive Performance Materials Inc. | Cobalt catalysts and their use for hydrosilylation and dehydrogenative silylation |
| CN105814142A (zh) * | 2013-12-16 | 2016-07-27 | 迈图高新材料日本合同公司 | 加成固化型硅酮组合物 |
| CN108026126B (zh) * | 2015-07-24 | 2021-04-20 | 莫门蒂夫性能材料股份有限公司 | 使用吡啶二亚胺羧酸钴催化剂的脱氢硅烷化、氢化硅烷化和交联 |
| JP6933835B2 (ja) * | 2017-01-25 | 2021-09-08 | 公立大学法人大阪 | 鉄錯体触媒を用いたカルボニル化合物のヒドロシリル化反応によるアルコキシシランの製造方法 |
| JP7430311B2 (ja) * | 2019-02-18 | 2024-02-13 | 学校法人 関西大学 | コバルトナノ粒子触媒によるヒドロシリル化反応 |
| CN112169840A (zh) * | 2020-10-09 | 2021-01-05 | 顺德职业技术学院 | 三齿配体修饰的硅胶固载含铂硅氢加成催化剂及其制备方法 |
| WO2025216228A1 (ja) * | 2024-04-09 | 2025-10-16 | 信越化学工業株式会社 | 化粧料 |
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| CN103814040B (zh) * | 2011-09-20 | 2016-08-31 | 道康宁公司 | 含镍硅氢加成催化剂及含有该催化剂的组合物 |
| CN103946228A (zh) | 2011-09-20 | 2014-07-23 | 道康宁公司 | 含钴硅氢加成催化剂及含有该催化剂的组合物 |
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| CN104024264A (zh) | 2011-09-20 | 2014-09-03 | 道康宁公司 | 含金属的硅氢加成催化剂以及含该催化剂的组合物 |
| US9782763B2 (en) | 2011-12-14 | 2017-10-10 | Momentive Performance Materials Inc. | Non-precious metal-based hyrdosilylation catalysts exhibiting improved selectivity |
| 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 |
| US9371340B2 (en) | 2012-08-16 | 2016-06-21 | Momentive Performance Materials Inc. | Dehydrogenative silylation, hydrosilylation and crosslinking using cobalt catalysts |
| US8927674B2 (en) | 2012-08-16 | 2015-01-06 | Princeton University | Dehydrogenative silylation and crosslinking using cobalt 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 |
| 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 |
| CN105228744B (zh) | 2013-05-15 | 2021-04-06 | 莫门蒂夫性能材料股份有限公司 | 用甲硅烷基氢化物活化金属盐及其在氢化硅烷化反应中的应用 |
| TW201538510A (zh) | 2013-11-19 | 2015-10-16 | Momentive Performance Mat Inc | 鈷觸媒及其於矽氫化與脫氫甲矽烷化之用途 |
-
2014
- 2014-05-15 CN CN201480028559.3A patent/CN105228744B/zh not_active Expired - Fee Related
- 2014-05-15 TW TW103117208A patent/TWI623544B/zh not_active IP Right Cessation
- 2014-05-15 EP EP14730037.0A patent/EP2996804B1/en not_active Not-in-force
- 2014-05-15 US US14/278,099 patent/US9440999B2/en not_active Expired - Fee Related
- 2014-05-15 JP JP2016514070A patent/JP2016520083A/ja active Pending
- 2014-05-15 WO PCT/US2014/038082 patent/WO2014186513A1/en not_active Ceased
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