CA1310330C - Methode pour la preparation d'organosilanes et d'organosilicones contenant des groupes methacryloxy et acryloxy - Google Patents

Methode pour la preparation d'organosilanes et d'organosilicones contenant des groupes methacryloxy et acryloxy

Info

Publication number: CA1310330C
Authority: CA; Canada
Prior art keywords: methacryloxy; acryloxy; platinum; alkoxysilane; group
Prior art date: 1986-05-20
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.): Expired - Lifetime

Application number

CA000615839A

Other languages

English (en)

Inventor

Nan S. Chu

Bernard Kanner

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Union Carbide Chemicals and Plastics Technology LLC

Union Carbide Corp

Original Assignee

Union Carbide Chemicals and Plastics Technology LLC

Union Carbide Corp

Priority date (The priority date 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 date listed.)

1986-05-20

Filing date

1990-08-17

Publication date

1992-11-17

1986-05-20 Priority claimed from US06/865,009 external-priority patent/US4709067A/en

1990-08-17 Application filed by Union Carbide Chemicals and Plastics Technology LLC, Union Carbide Corp filed Critical Union Carbide Chemicals and Plastics Technology LLC

1992-11-17 Application granted granted Critical

1992-11-17 Publication of CA1310330C publication Critical patent/CA1310330C/fr

2007-04-30 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

-1 methacryloxy Chemical group 0.000 title claims abstract description 86
238000000034 method Methods 0.000 title claims abstract description 49
150000001282 organosilanes Chemical class 0.000 title claims description 7
238000002360 preparation method Methods 0.000 title description 16
230000008569 process Effects 0.000 claims abstract description 35
238000006116 polymerization reaction Methods 0.000 claims abstract description 18
150000003961 organosilicon compounds Chemical class 0.000 claims abstract description 14
238000004519 manufacturing process Methods 0.000 claims abstract description 8
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 74
150000001875 compounds Chemical class 0.000 claims description 44
229910052697 platinum Inorganic materials 0.000 claims description 37
238000006243 chemical reaction Methods 0.000 claims description 34
239000003112 inhibitor Substances 0.000 claims description 34
239000003054 catalyst Substances 0.000 claims description 28
239000000047 product Substances 0.000 claims description 23
125000000217 alkyl group Chemical group 0.000 claims description 15
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 15
238000006459 hydrosilylation reaction Methods 0.000 claims description 14
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 13
238000010438 heat treatment Methods 0.000 claims description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 12
239000007795 chemical reaction product Substances 0.000 claims description 10
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical group COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 8
239000002904 solvent Substances 0.000 claims description 8
125000003118 aryl group Chemical group 0.000 claims description 7
RCYUVMCXOQTZOZ-FHQKDBNESA-N (z)-but-2-enedioic acid;2-[2-[2-[4-[(4-chlorophenyl)-phenylmethyl]piperazin-1-yl]ethoxy]ethoxy]ethanol;2-methyl-3-(2-methylphenyl)quinazolin-4-one Chemical compound OC(=O)\C=C/C(O)=O.OC(=O)\C=C/C(O)=O.CC1=CC=CC=C1N1C(=O)C2=CC=CC=C2N=C1C.C1CN(CCOCCOCCO)CCN1C(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 RCYUVMCXOQTZOZ-FHQKDBNESA-N 0.000 claims description 6
NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 claims description 6
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
239000002253 acid Substances 0.000 claims description 5
150000003057 platinum Chemical class 0.000 claims description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
NSWGBUVHSQEDRN-UHFFFAOYSA-L acetonitrile;platinum(2+);dichloride Chemical compound [Cl-].[Cl-].[Pt+2].CC#N.CC#N NSWGBUVHSQEDRN-UHFFFAOYSA-L 0.000 claims description 4
WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims description 3
239000005977 Ethylene Substances 0.000 claims description 3
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 3
150000004982 aromatic amines Chemical class 0.000 claims description 3
239000003610 charcoal Substances 0.000 claims description 3
229950000688 phenothiazine Drugs 0.000 claims description 3
XAFJSPPHVXDRIE-UHFFFAOYSA-L platinum(2+);triphenylphosphane;dichloride Chemical compound [Cl-].[Cl-].[Pt+2].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 XAFJSPPHVXDRIE-UHFFFAOYSA-L 0.000 claims description 3
229910052799 carbon Inorganic materials 0.000 claims description 2
HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims 3
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].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.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims 2
ZOYFWHYSNMFSJQ-UHFFFAOYSA-N platinum;tetraphenyl-$l^{5}-phosphane Chemical compound [Pt].C1=CC=CC=C1P(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 ZOYFWHYSNMFSJQ-UHFFFAOYSA-N 0.000 claims 2
USFPINLPPFWTJW-UHFFFAOYSA-N tetraphenylphosphonium Chemical compound C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 USFPINLPPFWTJW-UHFFFAOYSA-N 0.000 claims 2
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims 2
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
UTGQNNCQYDRXCH-UHFFFAOYSA-N N,N'-diphenyl-1,4-phenylenediamine Chemical group C=1C=C(NC=2C=CC=CC=2)C=CC=1NC1=CC=CC=C1 UTGQNNCQYDRXCH-UHFFFAOYSA-N 0.000 claims 1
230000003197 catalytic effect Effects 0.000 claims 1
239000003381 stabilizer Substances 0.000 abstract description 10
125000005594 diketone group Chemical group 0.000 abstract description 7
YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 25
239000000203 mixture Substances 0.000 description 22
239000011541 reaction mixture Substances 0.000 description 16
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
238000011282 treatment Methods 0.000 description 13
239000012043 crude product Substances 0.000 description 12
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 11
229920001296 polysiloxane Polymers 0.000 description 11
230000000052 comparative effect Effects 0.000 description 10
FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 description 10
CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
238000004821 distillation Methods 0.000 description 9
YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 8
238000002474 experimental method Methods 0.000 description 7
150000002500 ions Chemical class 0.000 description 7
238000010924 continuous production Methods 0.000 description 6
229910000077 silane Inorganic materials 0.000 description 6
BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical class [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 5
238000004458 analytical method Methods 0.000 description 5
239000003921 oil Substances 0.000 description 5
239000000376 reactant Substances 0.000 description 5
238000005292 vacuum distillation Methods 0.000 description 5
238000004817 gas chromatography Methods 0.000 description 4
DXCHWXWXYPEZKM-UHFFFAOYSA-N 2,4-ditert-butyl-6-[1-(3,5-ditert-butyl-2-hydroxyphenyl)ethyl]phenol Chemical compound C=1C(C(C)(C)C)=CC(C(C)(C)C)=C(O)C=1C(C)C1=CC(C(C)(C)C)=CC(C(C)(C)C)=C1O DXCHWXWXYPEZKM-UHFFFAOYSA-N 0.000 description 3
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
239000007789 gas Substances 0.000 description 3
238000000746 purification Methods 0.000 description 3
238000003860 storage Methods 0.000 description 3
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
230000000694 effects Effects 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 2
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
230000000087 stabilizing effect Effects 0.000 description 2
BHMLFPOTZYRDKA-IRXDYDNUSA-N (2s)-2-[(s)-(2-iodophenoxy)-phenylmethyl]morpholine Chemical compound IC1=CC=CC=C1O[C@@H](C=1C=CC=CC=1)[C@H]1OCCNC1 BHMLFPOTZYRDKA-IRXDYDNUSA-N 0.000 description 1
OZXIZRZFGJZWBF-UHFFFAOYSA-N 1,3,5-trimethyl-2-(2,4,6-trimethylphenoxy)benzene Chemical compound CC1=CC(C)=CC(C)=C1OC1=C(C)C=C(C)C=C1C OZXIZRZFGJZWBF-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
241000257303 Hymenoptera Species 0.000 description 1
229930194542 Keto Natural products 0.000 description 1
RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 1
WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 1
125000003158 alcohol group Chemical group 0.000 description 1
125000005399 allylmethacrylate group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
238000010923 batch production Methods 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
230000008859 change Effects 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
239000012467 final product Substances 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
230000006872 improvement Effects 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
SHOJXDKTYKFBRD-UHFFFAOYSA-N mesityl oxide Natural products CC(C)=CC(C)=O SHOJXDKTYKFBRD-UHFFFAOYSA-N 0.000 description 1
ARYZCSRUUPFYMY-UHFFFAOYSA-N methoxysilane Chemical compound CO[SiH3] ARYZCSRUUPFYMY-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
229940017219 methyl propionate Drugs 0.000 description 1
125000000962 organic group Chemical group 0.000 description 1
SYKXNRFLNZUGAJ-UHFFFAOYSA-N platinum;triphenylphosphane Chemical compound [Pt].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.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 SYKXNRFLNZUGAJ-UHFFFAOYSA-N 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
238000005086 pumping Methods 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 description 1
150000004756 silanes Chemical class 0.000 description 1
ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 1
239000005052 trichlorosilane Substances 0.000 description 1
239000011800 void material Substances 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

CA000615839A 1986-05-20 1990-08-17 Methode pour la preparation d'organosilanes et d'organosilicones contenant des groupes methacryloxy et acryloxy Expired - Lifetime CA1310330C (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US865,009		1986-05-20
US06/865,009 US4709067A (en)	1986-05-20	1986-05-20	Method for preparing methacryloxy and acryloxy containing organosilanes and organosilicones
CA000536060A CA1301773C (fr)	1986-05-20	1987-04-30	Methode pour la preparation de derives methacryloxy et acryloxy contenant des organosilanes et des organosilicones

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000536060A Division CA1301773C (fr)	1986-05-20	1987-04-30	Methode pour la preparation de derives methacryloxy et acryloxy contenant des organosilanes et des organosilicones

Publications (1)

Publication Number	Publication Date
CA1310330C true CA1310330C (fr)	1992-11-17

Family

ID=25671327

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000615839A Expired - Lifetime CA1310330C (fr)	1986-05-20	1990-08-17	Methode pour la preparation d'organosilanes et d'organosilicones contenant des groupes methacryloxy et acryloxy

Country Status (1)

Country	Link
CA (1)	CA1310330C (fr)

1990
- 1990-08-17 CA CA000615839A patent/CA1310330C/fr not_active Expired - Lifetime

Legal Events

Date	Code	Title	Description
1995-05-17	MKLA	Lapsed

Publication	Publication Date	Title
CA1301773C (fr)	1992-05-26	Methode pour la preparation de derives methacryloxy et acryloxy contenant des organosilanes et des organosilicones
US5290901A (en)	1994-03-01	Method for preparation of carbinol-functional siloxanes
US3933880A (en)	1976-01-20	Method of preparing a platinum catalyst inhibitor
US10047108B2 (en)	2018-08-14	Platinum (II) diene complexes with chelating dianionic ligands and their use in hydrosilylation reactions
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JP2837190B2 (ja)	1998-12-14	メタクリルオキシ基またはアクリルオキシ基を有するオルガノシランの安定化法
FR2576309A1 (fr)	1986-07-25	Procede de fabrication de compositions de silicones a fonction acrylique
JP3108427B2 (ja)	2000-11-13	カルビノール基含有オルガノポリシロキサンの製造方法
EP3819301B1 (fr)	2025-08-06	Préparation d'un composé d'organosilicone ayant un groupe (méth)acryloyloxy
US20080234441A1 (en)	2008-09-25	Process for producing bis-(aminoalkyl)-polysiloxanes
WO2015192029A1 (fr)	2015-12-17	Réactions d'hydrosilylation catalysée par le platine utilisant des additifs cyclodiène
JP2012504572A (ja)	2012-02-23	（メタ）アクリルシランの製造方法
EP0228095A2 (fr)	1987-07-08	Procédé pour la préparation de silanes et de siloxanes oliféniques
EP0516143B1 (fr)	1995-12-27	Procédé pour la préparation d'organopolysiloxane
FR2735135A1 (fr)	1996-12-13	Fluides silicone substitues par des groupes aryle presentant des indices de refraction eleves et leur procede de fabrication
FR2645156A1 (fr)	1990-10-05	Compose organosilicie a groupes hydroxyles
US3933882A (en)	1976-01-20	Tube method for the preparation of olefinic siloxane compounds
EP2099809B1 (fr)	2013-03-06	Procédé de préparation de composés organiques du silane ayant un groupe bêta-cyano ester
US5357016A (en)	1994-10-18	Preparation and processing of polydiorganosiloxanes
JP3555645B2 (ja)	2004-08-18	アクリロキシ基又はメタクリロキシ基含有クロロシランの製造方法
JP4009340B2 (ja)	2007-11-14	アクリロキシ基もしくはメタクリロキシ基含有有機ケイ素化合物の製造方法
EP0423686A2 (fr)	1991-04-24	Silacyclobutanes et leur procédé de préparation
WO2022046360A1 (fr)	2022-03-03	Procédé d'hydrosilylation d'un nitrile oléfinique
EP0845465A2 (fr)	1998-06-03	Procédé pour la préparation de composés organosiliciques comportant des groupes acryloxy ou méthacryloxy
FR2709757A1 (fr)	1995-03-17	Procédé de préparation de polyorganosiloxanes à fonctions insaturées par déshydrogénocondensation en présence de complexes de métaux du groupe IV.