JP2015504418A5 - - Google Patents
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- Publication number
- JP2015504418A5 JP2015504418A5 JP2014540033A JP2014540033A JP2015504418A5 JP 2015504418 A5 JP2015504418 A5 JP 2015504418A5 JP 2014540033 A JP2014540033 A JP 2014540033A JP 2014540033 A JP2014540033 A JP 2014540033A JP 2015504418 A5 JP2015504418 A5 JP 2015504418A5
- Authority
- JP
- Japan
- Prior art keywords
- process according
- formula
- product
- noble metal
- allyl
- 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
- 238000000034 method Methods 0.000 claims description 68
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 33
- 229910000510 noble metal Inorganic materials 0.000 claims description 32
- 239000003054 catalyst Substances 0.000 claims description 23
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 claims description 22
- 150000003377 silicon compounds Chemical class 0.000 claims description 18
- 238000006459 hydrosilylation reaction Methods 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 12
- 229910052697 platinum Inorganic materials 0.000 claims description 12
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 9
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 claims description 8
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 claims description 8
- 239000002245 particle Substances 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 238000004821 distillation Methods 0.000 claims description 6
- -1 polyoxyethylene Polymers 0.000 claims description 5
- 238000011084 recovery Methods 0.000 claims description 5
- 239000000377 silicon dioxide Substances 0.000 claims description 5
- 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 description 4
- XAYDWGMOPRHLEP-UHFFFAOYSA-N 6-ethenyl-7-oxabicyclo[4.1.0]heptane Chemical compound C1CCCC2OC21C=C XAYDWGMOPRHLEP-UHFFFAOYSA-N 0.000 claims description 4
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 4
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 claims description 4
- 239000005770 Eugenol Substances 0.000 claims description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 4
- UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 claims description 4
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 4
- 229960002217 eugenol Drugs 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 4
- 229910000077 silane Inorganic materials 0.000 claims description 4
- 238000010923 batch production Methods 0.000 claims description 3
- 150000001282 organosilanes Chemical group 0.000 claims description 3
- 125000005375 organosiloxane group Chemical group 0.000 claims description 3
- QOQTULDKYFWBLQ-UHFFFAOYSA-N 3-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]prop-1-ene Chemical compound COCCOCCOCCOCC=C QOQTULDKYFWBLQ-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 2
- 229920005830 Polyurethane Foam Polymers 0.000 claims description 2
- 229910004298 SiO 2 Inorganic materials 0.000 claims description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 2
- 229910021536 Zeolite Inorganic materials 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 238000010908 decantation Methods 0.000 claims description 2
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 229910052741 iridium Inorganic materials 0.000 claims description 2
- 239000002105 nanoparticle Substances 0.000 claims description 2
- 125000000962 organic group Chemical group 0.000 claims description 2
- 229920000620 organic polymer Polymers 0.000 claims description 2
- 229910052762 osmium Inorganic materials 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 239000004597 plastic additive Substances 0.000 claims description 2
- 229920000570 polyether Polymers 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 claims description 2
- 239000011496 polyurethane foam Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 229910052703 rhodium Inorganic materials 0.000 claims description 2
- 229910052707 ruthenium Inorganic materials 0.000 claims description 2
- 239000000741 silica gel Substances 0.000 claims description 2
- 229910002027 silica gel Inorganic materials 0.000 claims description 2
- 229910052710 silicon Inorganic materials 0.000 claims description 2
- 239000010703 silicon Substances 0.000 claims description 2
- 238000003860 storage Methods 0.000 claims description 2
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000010457 zeolite Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 239000000047 product Substances 0.000 description 31
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000006317 isomerization reaction Methods 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 239000002638 heterogeneous catalyst Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 238000004380 ashing Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000010814 metallic waste Substances 0.000 description 1
- 238000001465 metallisation Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13/285,628 | 2011-10-31 | ||
| US13/285,628 US8497338B2 (en) | 2011-10-31 | 2011-10-31 | Process of manufacturing organosilicon products with improved quality using heterogeneous precious metal catalysts |
| PCT/US2012/062762 WO2013066983A1 (en) | 2011-10-31 | 2012-10-31 | Process of manufacturing organosilicon products with improved quality using heterogeneous precious metal catalysts |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015504418A JP2015504418A (ja) | 2015-02-12 |
| JP2015504418A5 true JP2015504418A5 (enExample) | 2017-01-19 |
| JP6348421B2 JP6348421B2 (ja) | 2018-06-27 |
Family
ID=47178969
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014540033A Active JP6348421B2 (ja) | 2011-10-31 | 2012-10-31 | 不均一系貴金属触媒を用いる、改善された品質を有する有機ケイ素製品の製造プロセス |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US8497338B2 (enExample) |
| EP (1) | EP2773688B1 (enExample) |
| JP (1) | JP6348421B2 (enExample) |
| CN (1) | CN103987759B (enExample) |
| BR (1) | BR112014010001A2 (enExample) |
| ES (1) | ES2756755T3 (enExample) |
| IN (1) | IN2014MN01003A (enExample) |
| WO (1) | WO2013066983A1 (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101827696B1 (ko) | 2012-11-07 | 2018-02-09 | 다우 코닝 도레이 캄파니 리미티드 | 백금 함량이 감소된 페놀-개질된 폴리오르가노실록산, 이의 제조 방법, 및 이를 함유하는 유기 수지용 개질제 |
| EP2980123B1 (en) * | 2013-03-29 | 2019-05-29 | Idemitsu Kosan Co., Ltd | Polyorganosiloxane and polycarbonate-polyorganosiloxane copolymer |
| US20150306009A1 (en) | 2014-03-26 | 2015-10-29 | Momentive Performance Materials Inc. | Use of hydrolysis resistant organomodified silylated surfactants in personal care and home care |
| US11622929B2 (en) | 2016-03-08 | 2023-04-11 | Living Proof, Inc. | Long lasting cosmetic compositions |
| EP3681921A2 (en) | 2017-09-13 | 2020-07-22 | Living Proof, Inc. | Color protectant compositions |
| CN111133023B (zh) | 2017-09-13 | 2022-10-18 | 生活实验公司 | 持久化妆品组合物 |
| CN111356501A (zh) | 2017-11-20 | 2020-06-30 | 生活实验公司 | 实现持久化妆品性能的属性 |
| MX2020010976A (es) | 2018-04-19 | 2020-11-09 | Evonik Operations Gmbh | Siloxanos biocompatibles para formulacion de microorganismos. |
| JP2021522260A (ja) | 2018-04-27 | 2021-08-30 | リビング プルーフ インコーポレイテッド | 長持ちする化粧用組成物 |
| EP3819326B1 (en) * | 2018-07-02 | 2024-11-13 | Shin-Etsu Chemical Co., Ltd. | Method for producing carbinol-modified organosiloxane |
| JP7180315B2 (ja) | 2018-07-02 | 2022-11-30 | 信越化学工業株式会社 | カルビノール変性オルガノシロキサンの製造方法 |
| KR102187370B1 (ko) * | 2018-11-26 | 2020-12-04 | 한국생산기술연구원 | 불균일계 나노촉매를 이용한 스킨케어용 필름의 제조방법 |
| US12264220B2 (en) * | 2020-01-30 | 2025-04-01 | Evonik Operations Gmbh | Process for producing high-purity hydrosilylation products |
| EP4112674A1 (de) | 2021-06-30 | 2023-01-04 | Evonik Operations GmbH | Verfahren zur herstellung hochreiner hydrosilylierungsprodukte |
Family Cites Families (46)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2632013A (en) | 1946-10-09 | 1953-03-17 | Union Carbide & Carbon Corp | Process of producing organosilicon compounds |
| US2637738A (en) | 1949-09-17 | 1953-05-05 | Union Carbide & Carbon Corp | Reaction of silanes with aliphatic unsaturated compounds |
| BE553159A (enExample) | 1955-12-05 | |||
| US2851473A (en) | 1955-12-23 | 1958-09-09 | Union Carbide Corp | Processes for the reaction of silanic hydrogen-bonded compounds with unsaturated hydrocarbons |
| US3220972A (en) | 1962-07-02 | 1965-11-30 | Gen Electric | Organosilicon process using a chloroplatinic acid reaction product as the catalyst |
| US3775452A (en) | 1971-04-28 | 1973-11-27 | Gen Electric | Platinum complexes of unsaturated siloxanes and platinum containing organopolysiloxanes |
| US3879433A (en) * | 1972-12-29 | 1975-04-22 | Union Carbide Corp | Hydroxyalkylsiloxane rigid urethane foam stabilizers |
| US4064154A (en) | 1975-11-06 | 1977-12-20 | Dow Corning Corporation | Catalysts and carriers therefor |
| US4533744A (en) | 1983-08-29 | 1985-08-06 | General Electric Company | Hydrosilylation method, catalyst and method for making |
| US4614812A (en) * | 1985-12-31 | 1986-09-30 | Union Carbide Corporation | Novel process for promoting hydrosilation reactions using a second hydrosilane |
| US4900520A (en) * | 1988-10-31 | 1990-02-13 | Gaf Chemicals Corporation | Process for removal of soluble platinum group metal catalysts from liquid product mixtures |
| US5104647A (en) | 1990-06-22 | 1992-04-14 | Union Carbide Chemicals & Plastics Technology Corporation | Surfactant blend of organosilicone and polyalkylene oxide polymers useful as an agricultural adjuvant |
| GB9126049D0 (en) | 1991-12-07 | 1992-02-05 | Dow Corning | Hydrosilylation process |
| US5250490A (en) | 1991-12-24 | 1993-10-05 | Union Carbide Chemicals & Plastics Technology Corporation | Noble metal supported on a base metal catalyst |
| US5558806A (en) | 1992-07-23 | 1996-09-24 | Osi Specialties, Inc. | Surfactant blend of a polyalkleneoxide polysiloxane and an organic compound having a short chain hydrophobic moiety |
| US5206402A (en) | 1992-09-17 | 1993-04-27 | Dow Corning Corporation | Process for preparation of Ω-alkenylchlorosilanes |
| JPH06262076A (ja) * | 1993-03-09 | 1994-09-20 | Tanaka Kikinzoku Kogyo Kk | ヒドロシリル化用白金担持触媒 |
| EP0641799A3 (en) * | 1993-08-02 | 1997-09-17 | Dow Corning | High purity alkyl siloxanes and process for their preparation. |
| US5674832A (en) | 1995-04-27 | 1997-10-07 | Witco Corporation | Cationic compositions containing diol and/or diol alkoxylate |
| FR2749850B1 (fr) | 1996-06-12 | 1998-09-04 | Rhone Poulenc Chimie | Procede d'hydrosilylation avec des huiles silicones et des motifs contenant au moins un cycle hydrocarbone dans lequel est inclus un atome d'oxygene en presence d'une composition catalytique |
| US5670686A (en) * | 1996-08-13 | 1997-09-23 | Dow Corning Corporation | Alkyl substituted siloxanes and alkyl substituted polyether fluids |
| US6271295B1 (en) | 1996-09-05 | 2001-08-07 | General Electric Company | Emulsions of silicones with non-aqueous hydroxylic solvents |
| US6060546A (en) | 1996-09-05 | 2000-05-09 | General Electric Company | Non-aqueous silicone emulsions |
| US6545115B2 (en) * | 1996-12-11 | 2003-04-08 | Rhodia Chimie | Process for preparing a stable silicone oil containing SiH groups and hydrosilylable functions |
| US6221811B1 (en) | 1997-03-06 | 2001-04-24 | Crompton Corporation | Siloxane nonionic blends useful in agriculture |
| JP4306824B2 (ja) * | 1998-01-30 | 2009-08-05 | 東レ・ダウコーニング株式会社 | 有機官能性オルガノペンタシロキサンの製造方法、有機樹脂改質剤および有機樹脂 |
| DE19805083A1 (de) | 1998-02-09 | 1999-08-12 | Huels Chemische Werke Ag | Verfahren zur Herstellung von 3-Glycidyloxypropyltrialkoxysilanen |
| DE19816921A1 (de) | 1998-04-16 | 1999-10-21 | Wacker Chemie Gmbh | Verfahren für kontinuierliche polymeranaloge Umsetzungen |
| US6083901A (en) | 1998-08-28 | 2000-07-04 | General Electric Company | Emulsions of fragrance releasing silicon compounds |
| US6054547A (en) | 1998-08-28 | 2000-04-25 | General Electric Company | Fragrance releasing non-volatile polymeric-siloxanes |
| US6075111A (en) | 1998-08-28 | 2000-06-13 | General Electric Company | Fragrance releasing non-volatile polymeric siloxanes |
| US6046156A (en) | 1998-08-28 | 2000-04-04 | General Electric Company | Fragrance releasing olefinic silanes |
| US6365141B2 (en) * | 1998-11-06 | 2002-04-02 | General Electric Company | Method of using an aralkylsiloxane |
| US6087523A (en) * | 1999-07-23 | 2000-07-11 | Dow Corning Corporation | Platinum catalyst for hydrosilations |
| WO2001009259A1 (en) * | 1999-07-30 | 2001-02-08 | Ppg Industries Ohio, Inc. | Coating compositions having improved scratch resistance, coated substrates and methods related thereto |
| US6177585B1 (en) | 2000-05-19 | 2001-01-23 | Dow Corning Corporation | Bimetallic platinum catalysts for hydrosilations |
| JP2004169015A (ja) * | 2002-11-01 | 2004-06-17 | Shin Etsu Chem Co Ltd | 粉体組成物及び油中粉体分散物.並びにそれらを有する化粧料 |
| JP4875312B2 (ja) * | 2005-03-15 | 2012-02-15 | 東レ・ダウコーニング株式会社 | オルガノトリシロキサン、その製造方法、それを含む硬化性樹脂組成物、およびその硬化物 |
| JP4656307B2 (ja) * | 2005-05-20 | 2011-03-23 | 信越化学工業株式会社 | 含フッ素有機ケイ素化合物及び含フッ素界面活性剤 |
| RU2008140179A (ru) * | 2006-03-10 | 2010-04-20 | Ппг Индастриз Огайо, Инк. (Us) | Гетерогенные катализаторы гидросилилирования, способы получения полимеров и композиции покрытий |
| NZ579452A (en) * | 2007-03-08 | 2012-01-12 | Momentive Performance Mat Inc | Hydrolysis resistant organomodified trisiloxane surfactants |
| EP2449879A1 (en) * | 2007-03-08 | 2012-05-09 | Momentive Performance Materials Inc. | Hydrolysis resistant organomodified trisiloxane surfactants |
| US7872053B2 (en) * | 2007-03-26 | 2011-01-18 | Momentive Performance Materials GmbH & Co., KG | Surface active organosilicone compounds |
| US7507849B2 (en) * | 2007-06-22 | 2009-03-24 | 3M Innovative Properties Company | Cyclic silazanes containing an oxamido ester group and methods of making these compounds |
| US8481775B2 (en) * | 2008-12-01 | 2013-07-09 | Dsm Ip Assets B.V. | Method for improving the color index of organopolysiloxanes |
| ATE523547T1 (de) * | 2008-12-01 | 2011-09-15 | Dsm Ip Assets Bv | Neues verfahren |
-
2011
- 2011-10-31 US US13/285,628 patent/US8497338B2/en not_active Expired - Fee Related
-
2012
- 2012-10-31 EP EP12787284.4A patent/EP2773688B1/en active Active
- 2012-10-31 WO PCT/US2012/062762 patent/WO2013066983A1/en not_active Ceased
- 2012-10-31 CN CN201280061218.7A patent/CN103987759B/zh active Active
- 2012-10-31 ES ES12787284T patent/ES2756755T3/es active Active
- 2012-10-31 IN IN1003MUN2014 patent/IN2014MN01003A/en unknown
- 2012-10-31 BR BR112014010001A patent/BR112014010001A2/pt not_active Application Discontinuation
- 2012-10-31 JP JP2014540033A patent/JP6348421B2/ja active Active
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