JP2012532884A5 - - Google Patents
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- JP2012532884A5 JP2012532884A5 JP2012519752A JP2012519752A JP2012532884A5 JP 2012532884 A5 JP2012532884 A5 JP 2012532884A5 JP 2012519752 A JP2012519752 A JP 2012519752A JP 2012519752 A JP2012519752 A JP 2012519752A JP 2012532884 A5 JP2012532884 A5 JP 2012532884A5
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- 238000000034 method Methods 0.000 claims description 25
- 238000006459 hydrosilylation reaction Methods 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 11
- 229920000570 polyether Polymers 0.000 claims description 11
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 10
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- -1 polyethylene Polymers 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 229910000077 silane Inorganic materials 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 229920001296 polysiloxane Polymers 0.000 claims description 3
- 150000001336 alkenes Chemical class 0.000 claims description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 2
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims 6
- 125000005842 heteroatom Chemical group 0.000 claims 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 6
- 229920002554 vinyl polymer Polymers 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 4
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims 4
- 229920006395 saturated elastomer Polymers 0.000 claims 4
- UWRZIZXBOLBCON-UHFFFAOYSA-N 2-phenylethenamine Chemical compound NC=CC1=CC=CC=C1 UWRZIZXBOLBCON-UHFFFAOYSA-N 0.000 claims 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims 2
- 239000004698 Polyethylene Substances 0.000 claims 2
- 239000004743 Polypropylene Substances 0.000 claims 2
- 239000004793 Polystyrene Substances 0.000 claims 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 239000003638 chemical reducing agent Substances 0.000 claims 2
- 239000000412 dendrimer Substances 0.000 claims 2
- 229920000736 dendritic polymer Polymers 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000000524 functional group Chemical group 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 229920000573 polyethylene Polymers 0.000 claims 2
- 229920000642 polymer Polymers 0.000 claims 2
- 229920001155 polypropylene Polymers 0.000 claims 2
- 229920002223 polystyrene Polymers 0.000 claims 2
- 229920002635 polyurethane Polymers 0.000 claims 2
- 239000004814 polyurethane Substances 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 239000000377 silicon dioxide Substances 0.000 claims 2
- 125000006657 (C1-C10) hydrocarbyl group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 229910004298 SiO 2 Inorganic materials 0.000 claims 1
- 229910004283 SiO 4 Inorganic materials 0.000 claims 1
- 150000001252 acrylic acid derivatives Chemical group 0.000 claims 1
- 150000001345 alkine derivatives Chemical class 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 150000001450 anions Chemical group 0.000 claims 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 1
- 150000008378 aryl ethers Chemical class 0.000 claims 1
- 150000001924 cycloalkanes Chemical class 0.000 claims 1
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 238000007885 magnetic separation Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000000962 organic group Chemical group 0.000 claims 1
- QLUMLEDLZDMGDW-UHFFFAOYSA-N sodium;1h-naphthalen-1-ide Chemical group [Na+].[C-]1=CC=CC2=CC=CC=C21 QLUMLEDLZDMGDW-UHFFFAOYSA-N 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 230000002194 synthesizing effect Effects 0.000 claims 1
- 239000000047 product Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 8
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000006317 isomerization reaction Methods 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 2
- 101150065749 Churc1 gene Proteins 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 102100038239 Protein Churchill Human genes 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- BITPLIXHRASDQB-UHFFFAOYSA-N ethenyl-[ethenyl(dimethyl)silyl]oxy-dimethylsilane Chemical compound C=C[Si](C)(C)O[Si](C)(C)C=C BITPLIXHRASDQB-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 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 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US22459809P | 2009-07-10 | 2009-07-10 | |
| US61/224,598 | 2009-07-10 | ||
| US12/832,627 | 2010-07-08 | ||
| US12/832,627 US8236915B2 (en) | 2009-07-10 | 2010-07-08 | Hydrosilylation catalysts |
| PCT/US2010/041487 WO2011006044A2 (en) | 2009-07-10 | 2010-07-09 | Hydrosilylation catalysts |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016215022A Division JP6389220B2 (ja) | 2009-07-10 | 2016-11-02 | ヒドロシリル化触媒 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012532884A JP2012532884A (ja) | 2012-12-20 |
| JP2012532884A5 true JP2012532884A5 (enExample) | 2016-12-22 |
| JP6059987B2 JP6059987B2 (ja) | 2017-01-11 |
Family
ID=43427966
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012519752A Active JP6059987B2 (ja) | 2009-07-10 | 2010-07-09 | ヒドロシリル化触媒 |
| JP2016215022A Active JP6389220B2 (ja) | 2009-07-10 | 2016-11-02 | ヒドロシリル化触媒 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016215022A Active JP6389220B2 (ja) | 2009-07-10 | 2016-11-02 | ヒドロシリル化触媒 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US8236915B2 (enExample) |
| EP (1) | EP2451820B1 (enExample) |
| JP (2) | JP6059987B2 (enExample) |
| KR (2) | KR20120023149A (enExample) |
| CN (3) | CN105085580B (enExample) |
| BR (1) | BR112012000169A2 (enExample) |
| TW (1) | TWI492789B (enExample) |
| WO (1) | WO2011006044A2 (enExample) |
Families Citing this family (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR112013012734A2 (pt) | 2010-11-24 | 2016-09-13 | Univ Cornell | mono-hidrossililação catalisada por metal não-precioso seletivo de compostos polinsaturados |
| JP2014503507A (ja) * | 2010-11-24 | 2014-02-13 | 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 | ヒドロシリル化触媒 |
| JP5991981B2 (ja) * | 2010-11-24 | 2016-09-14 | 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 | ヒドロシリル化触媒として使用される三座窒素配位子を有する金属錯体のｉｎ−ｓｉｔｕ活性化 |
| US9394325B2 (en) * | 2011-08-19 | 2016-07-19 | The Trustees Of Princeton University | Enantiopure base-metal catalysts for asymmetric catalysis and bis(imino)pyridine iron alkyl complexes for catalysis |
| EP2758415A2 (en) * | 2011-09-20 | 2014-07-30 | Dow Corning Corporation | Iron containing hydrosilylation catalysts and compositions containing the catalysts |
| 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 |
| US9156948B2 (en) * | 2011-10-04 | 2015-10-13 | Dow Corning Corporation | Iron(II) containing complex and condensation reaction catalysts, methods for preparing the catalysts, and compositions containing the catalysts |
| US9139699B2 (en) | 2012-10-04 | 2015-09-22 | Dow Corning Corporation | Metal containing condensation reaction catalysts, methods for preparing the catalysts, and compositions containing the catalysts |
| JP6117233B2 (ja) * | 2011-12-01 | 2017-04-19 | ダウ コーニング コーポレーションＤｏｗ Ｃｏｒｎｉｎｇ Ｃｏｒｐｏｒａｔｉｏｎ | ヒドロシリル化反応触媒及び硬化性組成物並びにこれらの調製及び使用方法 |
| 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 |
| JP6125222B2 (ja) * | 2012-08-16 | 2017-05-10 | 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 | コバルト触媒を用いる脱水素シリル化および架橋 |
| FR3000069B1 (fr) | 2012-12-21 | 2015-02-06 | Bluestar Silicones France | Procede d'hydrosilylation d'un siloxane photocatalyse par un compose polyoxometallate |
| 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 |
| US9708355B2 (en) | 2013-06-12 | 2017-07-18 | Arizona Board Of Regents On Behalf Of Arizona State University | First-row transition metal hydrogenation and hydrosilylation catalysts |
| WO2015023328A1 (en) | 2013-08-14 | 2015-02-19 | Momentive Performance Materials Inc. | Reusable homogeneous cobalt pyridine dimine catalysts for dehydrogenative silylation and tandem dehydrogenative-silylation-hydrogenation |
| US20160297928A1 (en) * | 2013-10-02 | 2016-10-13 | Basf Se | Use Of Poly(Oxyalkylene)Oxy- And/Or Poly(Oxyalkylene)Aminoalkyltrialkoxysilanes As Dispersants |
| WO2015077306A1 (en) | 2013-11-19 | 2015-05-28 | Momentive Performance Materials Inc. | Cobalt catalysts and their use for hydrosilylation and dehydrogenative silylation |
| 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 |
| TW201524604A (zh) | 2013-11-19 | 2015-07-01 | Momentive Performance Mat Inc | 使用鈷觸媒之脫氫甲矽烷化、矽氫化及交聯 |
| EP3071585B1 (en) * | 2013-11-19 | 2018-11-07 | Momentive Performance Materials Inc. | Cobalt catalysts and their use for hydrosilylation and dehydrogenative silylation |
| US20170190722A1 (en) * | 2014-05-08 | 2017-07-06 | Momentive Performance Materials Inc. | Dialkyl cobalt catalysts and their use for hydrosilylation and dehydrogenative silylation |
| JP6327426B2 (ja) | 2014-08-12 | 2018-05-23 | 国立大学法人九州大学 | ヒドロシリル化反応触媒 |
| 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 |
| CN104478919B (zh) * | 2014-11-18 | 2018-02-02 | 浙江大学 | 一种合成手性硅烷化合物的方法 |
| WO2016099727A2 (en) | 2014-12-19 | 2016-06-23 | Dow Corning Corporation | Ligand components, associated reaction products, activated reaction products, hydrosilylation catalysts and hydrosilylation curable compositions including the ligand components, and associated methods for preparing same |
| KR102564637B1 (ko) | 2015-07-14 | 2023-08-08 | 고쿠리쓰다이가쿠호진 규슈다이가쿠 | 하이드로실릴화 반응 촉매 |
| 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 |
| US10280265B2 (en) * | 2015-12-07 | 2019-05-07 | Dow Corning Corporation | Method and composition for hydrosilylation of carboxylic acid alkenyl esters and hydrogen terminated organosiloxane oligomers with an iridium complex catalyst |
| EP3406616B1 (en) | 2016-01-22 | 2022-06-29 | Shin-Etsu Chemical Co., Ltd. | Novel isocyanide compound and hydrosilylation reaction catalyst |
| 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 |
| CN110366449B (zh) | 2017-02-28 | 2022-10-21 | 国立大学法人九州大学 | 氢化硅烷化反应、氢化反应和氢硅烷还原反应用催化剂 |
| FR3068699B1 (fr) * | 2017-07-05 | 2019-08-16 | Elkem Silicones France Sas | Compose du fer utile comme catalyseur d'hydrosilylation, de silylation deshydrogenante et de reticulation de compositions silicones |
| 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 |
| US11273432B2 (en) | 2018-05-31 | 2022-03-15 | Arizona Board Of Regents On Behalf Of Arizona State University | Beta-diketiminate manganese catalysts for hydrosilylation, hydroboration, and dehydrogenative pnictogen-silicon and pnictogen-boron bond formation |
| CN109046463B (zh) * | 2018-08-16 | 2021-05-04 | 中山大学 | 双齿氮杂卡宾锰催化剂及其制备方法和烷基化合成应用 |
| KR102807413B1 (ko) | 2018-09-13 | 2025-05-13 | 모멘티브 퍼포먼스 머티리얼즈 게엠베하 | 기능성 폴리실록산 |
| JP6806299B2 (ja) * | 2019-02-15 | 2021-01-06 | 国立大学法人九州大学 | ヒドロシリル化鉄触媒の調製方法 |
| EP3915995B1 (en) | 2020-05-29 | 2025-11-26 | Momentive Performance Materials Inc. | Process for the stepwise synthesis of silahydrocarbons |
| CN114015055B (zh) * | 2021-11-17 | 2023-04-14 | 江西晨光新材料股份有限公司 | 一种功能硅烷封端聚硅氧烷的合成方法及应用 |
| CN119751516B (zh) * | 2024-12-27 | 2025-11-28 | 南京杰运医药科技有限公司 | 一种用于制备甲酚曲唑三硅氧烷的pdi催化剂、制备方法及甲酚曲唑三硅氧烷的制备方法 |
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| DE60211884T2 (de) | 2001-04-30 | 2006-11-23 | Ciba Speciality Chemicals Holding Inc. | Verwendung von metallkomplexverbindungen als oxidationskatalysatoren |
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-
2010
- 2010-07-08 US US12/832,627 patent/US8236915B2/en active Active
- 2010-07-09 CN CN201510530811.7A patent/CN105085580B/zh active Active
- 2010-07-09 CN CN201080030539.1A patent/CN102471358B/zh active Active
- 2010-07-09 JP JP2012519752A patent/JP6059987B2/ja active Active
- 2010-07-09 BR BR112012000169A patent/BR112012000169A2/pt not_active Application Discontinuation
- 2010-07-09 KR KR1020117031667A patent/KR20120023149A/ko not_active Ceased
- 2010-07-09 EP EP10744762.5A patent/EP2451820B1/en active Active
- 2010-07-09 KR KR1020147035506A patent/KR101710043B1/ko active Active
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