JPS62183854A - ヒドロシリル化触媒 - Google Patents
ヒドロシリル化触媒Info
- Publication number
- JPS62183854A JPS62183854A JP29910186A JP29910186A JPS62183854A JP S62183854 A JPS62183854 A JP S62183854A JP 29910186 A JP29910186 A JP 29910186A JP 29910186 A JP29910186 A JP 29910186A JP S62183854 A JPS62183854 A JP S62183854A
- Authority
- JP
- Japan
- Prior art keywords
- platinum
- catalyst
- colloidal
- hydride
- complex
- 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
- 239000003054 catalyst Substances 0.000 title claims description 55
- 238000004519 manufacturing process Methods 0.000 title description 4
- 230000033444 hydroxylation Effects 0.000 title 1
- 238000005805 hydroxylation reaction Methods 0.000 title 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 100
- 229910052697 platinum Inorganic materials 0.000 claims description 41
- -1 vinylsiloxane Chemical class 0.000 claims description 29
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 19
- 238000006459 hydrosilylation reaction Methods 0.000 claims description 16
- 229910052990 silicon hydride Inorganic materials 0.000 claims description 16
- 229920002554 vinyl polymer Polymers 0.000 claims description 14
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 10
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 6
- HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 claims description 5
- 239000000010 aprotic solvent Substances 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 239000003446 ligand Substances 0.000 claims description 3
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims 2
- CWAFVXWRGIEBPL-UHFFFAOYSA-N ethoxysilane Chemical group CCO[SiH3] CWAFVXWRGIEBPL-UHFFFAOYSA-N 0.000 claims 1
- 229910052710 silicon Inorganic materials 0.000 claims 1
- 239000010703 silicon Substances 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- 229920001296 polysiloxane Polymers 0.000 description 9
- 239000001257 hydrogen Substances 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 239000000084 colloidal system Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 150000003057 platinum Chemical class 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 150000002430 hydrocarbons Chemical group 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 238000001879 gelation Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 229920001843 polymethylhydrosiloxane Polymers 0.000 description 4
- 229920002545 silicone oil Polymers 0.000 description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 229920003354 Modic® Polymers 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [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
- 239000002253 acid Substances 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- YAJIVAPCZRKADM-UHFFFAOYSA-L cycloocta-1,3-diene;platinum(2+);dichloride Chemical compound Cl[Pt]Cl.C1CCC=CC=CC1 YAJIVAPCZRKADM-UHFFFAOYSA-L 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229910000077 silane Inorganic materials 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 3
- 239000004971 Cross linker Substances 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 229910019032 PtCl2 Inorganic materials 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- XYVWLJNYNZIBHE-UHFFFAOYSA-N [Pt].[SiH3]O[SiH2]C=C Chemical compound [Pt].[SiH3]O[SiH2]C=C XYVWLJNYNZIBHE-UHFFFAOYSA-N 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 239000004205 dimethyl polysiloxane Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
- 229920006158 high molecular weight polymer Polymers 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229920006136 organohydrogenpolysiloxane Polymers 0.000 description 2
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229920002379 silicone rubber Polymers 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- 125000005023 xylyl group Chemical group 0.000 description 2
- 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 description 1
- WZJUBBHODHNQPW-UHFFFAOYSA-N 2,4,6,8-tetramethyl-1,3,5,7,2$l^{3},4$l^{3},6$l^{3},8$l^{3}-tetraoxatetrasilocane Chemical compound C[Si]1O[Si](C)O[Si](C)O[Si](C)O1 WZJUBBHODHNQPW-UHFFFAOYSA-N 0.000 description 1
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 101100274463 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CIT3 gene Proteins 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 125000004966 cyanoalkyl group Chemical group 0.000 description 1
- 229920005565 cyclic polymer Polymers 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- KTQYJQFGNYHXMB-UHFFFAOYSA-N dichloro(methyl)silicon Chemical compound C[Si](Cl)Cl KTQYJQFGNYHXMB-UHFFFAOYSA-N 0.000 description 1
- 125000004212 difluorophenyl group Chemical group 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- GCSJLQSCSDMKTP-UHFFFAOYSA-N ethenyl(trimethyl)silane Chemical compound C[Si](C)(C)C=C GCSJLQSCSDMKTP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- MRRXLWNSVYPSRB-UHFFFAOYSA-N ethenyl-dimethyl-trimethylsilyloxysilane Chemical compound C[Si](C)(C)O[Si](C)(C)C=C MRRXLWNSVYPSRB-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000005394 methallyl group Chemical group 0.000 description 1
- 239000005048 methyldichlorosilane Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- NDBYXKQCPYUOMI-UHFFFAOYSA-N platinum(4+) Chemical compound [Pt+4] NDBYXKQCPYUOMI-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002210 silicon-based material Substances 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0801—General processes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0086—Platinum compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Catalysts (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Paints Or Removers (AREA)
- Silicon Polymers (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US81062985A | 1985-12-19 | 1985-12-19 | |
| US810629 | 1985-12-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62183854A true JPS62183854A (ja) | 1987-08-12 |
| JPH053343B2 JPH053343B2 (enrdf_load_stackoverflow) | 1993-01-14 |
Family
ID=25204288
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP29910186A Granted JPS62183854A (ja) | 1985-12-19 | 1986-12-17 | ヒドロシリル化触媒 |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS62183854A (enrdf_load_stackoverflow) |
| BE (1) | BE905991A (enrdf_load_stackoverflow) |
| DE (1) | DE3642058C2 (enrdf_load_stackoverflow) |
| FR (1) | FR2591916B1 (enrdf_load_stackoverflow) |
| GB (1) | GB2184727B (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH10309470A (ja) * | 1997-05-09 | 1998-11-24 | Shin Etsu Chem Co Ltd | 白金錯体触媒 |
| JP2010037555A (ja) * | 2008-07-11 | 2010-02-18 | Mitsui Chemicals Inc | シリル化ポリオレフィンの製造方法および該シリル化ポリオレフィンを含む添加剤 |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0763632B2 (ja) * | 1986-06-17 | 1995-07-12 | 東レ・ダウコ−ニング・シリコ−ン株式会社 | 白金アルケニルシロキサン錯体触媒組成物 |
| JPH07107137B2 (ja) * | 1986-09-19 | 1995-11-15 | 東レ・ダウコ−ニング・シリコ−ン株式会社 | 液状シリコ−ンゴム用オルガノポリシロキサン組成物 |
| CA1340871C (en) * | 1988-12-28 | 2000-01-04 | Robert W. Epperly | Method for reducing emissions from or increasing the utilizable energy of fuel for powering internal combustion engines |
| US5025073A (en) * | 1989-10-19 | 1991-06-18 | General Electric Company | One part heat curable organopolysiloxane compositions |
| US5189131A (en) * | 1991-04-26 | 1993-02-23 | General Electric Company | Hydrosilylation method |
| US5364922A (en) * | 1993-09-07 | 1994-11-15 | Dow Corning Corporation | Curable compositions containing an anaerobically inactive hydrosilation catalyst and method for preparing said compositions |
| US6562470B2 (en) * | 2001-01-10 | 2003-05-13 | General Electric Company | Method for making coated substrates and articles made thereby |
| JP5234389B2 (ja) * | 2007-08-02 | 2013-07-10 | 地方独立行政法人山口県産業技術センター | 金属ナノ粒子の製造方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3336239A (en) * | 1962-09-25 | 1967-08-15 | Union Carbide Corp | Activated hydrogenation catalysts |
| FR1480409A (fr) * | 1965-05-17 | 1967-05-12 | Dow Corning | Nouveaux types de catalyseurs pour la réaction de groupes hydrogénés de silicium contenant trois liaisons, avec des composés organiques contenant une liaison non saturée aliphatique |
| GB1211699A (en) * | 1966-12-01 | 1970-11-11 | Gen Electric | Organosilicon materials and process for their preparation |
| US3576027A (en) * | 1968-07-31 | 1971-04-20 | Texas Instruments Inc | Hydrosilation of olefins |
| US3715334A (en) * | 1970-11-27 | 1973-02-06 | Gen Electric | Platinum-vinylsiloxanes |
| US3989666A (en) * | 1974-12-02 | 1976-11-02 | Dow Corning Corporation | Crosslinker-platinum catalyst-inhibitor and method of preparation thereof |
-
1986
- 1986-09-17 GB GB8622351A patent/GB2184727B/en not_active Expired - Lifetime
- 1986-12-09 DE DE19863642058 patent/DE3642058C2/de not_active Expired - Fee Related
- 1986-12-15 FR FR8617476A patent/FR2591916B1/fr not_active Expired - Fee Related
- 1986-12-17 JP JP29910186A patent/JPS62183854A/ja active Granted
- 1986-12-19 BE BE0/217564A patent/BE905991A/fr not_active IP Right Cessation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH10309470A (ja) * | 1997-05-09 | 1998-11-24 | Shin Etsu Chem Co Ltd | 白金錯体触媒 |
| JP2010037555A (ja) * | 2008-07-11 | 2010-02-18 | Mitsui Chemicals Inc | シリル化ポリオレフィンの製造方法および該シリル化ポリオレフィンを含む添加剤 |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2184727A (en) | 1987-07-01 |
| DE3642058C2 (de) | 1999-02-25 |
| GB2184727B (en) | 1990-05-02 |
| DE3642058A1 (de) | 1987-06-25 |
| BE905991A (fr) | 1987-06-19 |
| JPH053343B2 (enrdf_load_stackoverflow) | 1993-01-14 |
| GB8622351D0 (en) | 1986-10-22 |
| FR2591916A1 (fr) | 1987-06-26 |
| FR2591916B1 (fr) | 1993-11-05 |
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