DE3301807A1 - Verfahren zur herstellung von silanen mit sic-gebundener bernsteinsaeureanhydridgruppe und silane mit derartiger gruppe - Google Patents
Verfahren zur herstellung von silanen mit sic-gebundener bernsteinsaeureanhydridgruppe und silane mit derartiger gruppeInfo
- Publication number
- DE3301807A1 DE3301807A1 DE19833301807 DE3301807A DE3301807A1 DE 3301807 A1 DE3301807 A1 DE 3301807A1 DE 19833301807 DE19833301807 DE 19833301807 DE 3301807 A DE3301807 A DE 3301807A DE 3301807 A1 DE3301807 A1 DE 3301807A1
- Authority
- DE
- Germany
- Prior art keywords
- silanes
- sic
- succinic anhydride
- group
- bonded
- 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.)
- Withdrawn
Links
- 150000004756 silanes Chemical class 0.000 title claims description 14
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 150000008065 acid anhydrides Chemical group 0.000 title 1
- 239000003054 catalyst Substances 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 13
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical group O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- 150000008064 anhydrides Chemical class 0.000 claims description 7
- 230000001737 promoting effect Effects 0.000 claims description 6
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 5
- 229910000077 silane Inorganic materials 0.000 claims description 5
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 229940014800 succinic anhydride Drugs 0.000 claims description 2
- -1 alkyl radicals Chemical class 0.000 description 13
- 150000003254 radicals Chemical class 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 4
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- CLSUSRZJUQMOHH-UHFFFAOYSA-L platinum dichloride Chemical compound Cl[Pt]Cl CLSUSRZJUQMOHH-UHFFFAOYSA-L 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- FBEIPJNQGITEBL-UHFFFAOYSA-J tetrachloroplatinum Chemical compound Cl[Pt](Cl)(Cl)Cl FBEIPJNQGITEBL-UHFFFAOYSA-J 0.000 description 2
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- RTVBWUXFULQISX-UHFFFAOYSA-N 2-(3-dimethoxysilylpropyl)-3-methylbutanedioic acid Chemical compound CC(C(C(=O)O)CCC[SiH](OC)OC)C(=O)O RTVBWUXFULQISX-UHFFFAOYSA-N 0.000 description 1
- KDBDBZBZEXGFEC-UHFFFAOYSA-N 3-(2-triethoxysilylethyl)oxolane-2,5-dione Chemical compound CCO[Si](OCC)(OCC)CCC1CC(=O)OC1=O KDBDBZBZEXGFEC-UHFFFAOYSA-N 0.000 description 1
- ZADOWCXTUZWAKL-UHFFFAOYSA-N 3-(3-trimethoxysilylpropyl)oxolane-2,5-dione Chemical compound CO[Si](OC)(OC)CCCC1CC(=O)OC1=O ZADOWCXTUZWAKL-UHFFFAOYSA-N 0.000 description 1
- WUMMIJWEUDHZCL-UHFFFAOYSA-N 3-prop-2-enyloxolane-2,5-dione Chemical compound C=CCC1CC(=O)OC1=O WUMMIJWEUDHZCL-UHFFFAOYSA-N 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- DSVRVHYFPPQFTI-UHFFFAOYSA-N bis(ethenyl)-methyl-trimethylsilyloxysilane;platinum Chemical class [Pt].C[Si](C)(C)O[Si](C)(C=C)C=C DSVRVHYFPPQFTI-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001723 carbon free-radicals Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- AJSWTYBRTBDKJF-UHFFFAOYSA-L dichloroplatinum;2-(3-pyridin-2-ylpropyl)pyridine Chemical compound Cl[Pt]Cl.C=1C=CC=NC=1CCCC1=CC=CC=N1 AJSWTYBRTBDKJF-UHFFFAOYSA-L 0.000 description 1
- GAURFLBIDLSLQU-UHFFFAOYSA-N diethoxy(methyl)silicon Chemical compound CCO[Si](C)OCC GAURFLBIDLSLQU-UHFFFAOYSA-N 0.000 description 1
- PKTOVQRKCNPVKY-UHFFFAOYSA-N dimethoxy(methyl)silicon Chemical compound CO[Si](C)OC PKTOVQRKCNPVKY-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- DRUOQOFQRYFQGB-UHFFFAOYSA-N ethoxy(dimethyl)silicon Chemical compound CCO[Si](C)C DRUOQOFQRYFQGB-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 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
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Reinforced Plastic Materials (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19833301807 DE3301807A1 (de) | 1983-01-20 | 1983-01-20 | Verfahren zur herstellung von silanen mit sic-gebundener bernsteinsaeureanhydridgruppe und silane mit derartiger gruppe |
| JP59002760A JPS59137493A (ja) | 1983-01-20 | 1984-01-12 | ＳｉＣ‐結合した無水コハク酸基を有するシランの製法 |
| EP84100413A EP0114636A3 (de) | 1983-01-20 | 1984-01-17 | Verfahren zur Herstellung von Silanen mit SiC-gebundener Bernsteinsäureanhydridgruppe und Silane mit derartiger Gruppe |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19833301807 DE3301807A1 (de) | 1983-01-20 | 1983-01-20 | Verfahren zur herstellung von silanen mit sic-gebundener bernsteinsaeureanhydridgruppe und silane mit derartiger gruppe |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3301807A1 true DE3301807A1 (de) | 1984-07-26 |
Family
ID=6188755
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19833301807 Withdrawn DE3301807A1 (de) | 1983-01-20 | 1983-01-20 | Verfahren zur herstellung von silanen mit sic-gebundener bernsteinsaeureanhydridgruppe und silane mit derartiger gruppe |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP0114636A3 (enExample) |
| JP (1) | JPS59137493A (enExample) |
| DE (1) | DE3301807A1 (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4837339A (en) * | 1984-09-25 | 1989-06-06 | Nissan Chemical Industries, Ltd. | 4-Substituted-1,2,3,6-tetrahydrophthalic acid anhydride |
| EP0855372A1 (de) * | 1997-01-23 | 1998-07-29 | Fraunhofer-Gesellschaft Zur Förderung Der Angewandten Forschung E.V. | Verfahren zur Hydrophilierung von Glassubstraten und deren Verwendung |
| EP2519528A1 (en) * | 2009-12-28 | 2012-11-07 | Dow Corning Toray Co., Ltd. | Organosilicon compound, method for producing thereof, and curable silicone composition containing the same |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4863978A (en) * | 1988-06-03 | 1989-09-05 | Dow Corning Corporation | Ionomeric silane coupling agents |
| DE4233396A1 (de) * | 1992-10-05 | 1994-04-07 | Merck Patent Gmbh | Oberflächenmodifizierte Oxidpartikel und ihre Anwendung als Füll- und Modifizierungsmittel in Polymermaterialien |
| DE4211256A1 (de) * | 1992-04-03 | 1993-10-07 | Wacker Chemie Gmbh | Vernetzbare Zusammensetzung auf Aminosiliconbasis |
| WO1994007945A1 (de) * | 1992-10-05 | 1994-04-14 | Hoechst Aktiengesellschaft | Formkörper aus polyester, die kovalent eingebundene oxidpartikel enthalten |
| JP4070515B2 (ja) * | 2002-06-05 | 2008-04-02 | 旭化成エレクトロニクス株式会社 | 耐熱性樹脂前駆体組成物 |
| JP2006022158A (ja) * | 2004-07-06 | 2006-01-26 | Yokohama Rubber Co Ltd:The | 硬化性樹脂組成物 |
| JP4817710B2 (ja) * | 2005-05-16 | 2011-11-16 | 旭化成イーマテリアルズ株式会社 | シランカップリング剤 |
| JP2011246667A (ja) * | 2010-05-31 | 2011-12-08 | Sumitomo Chemical Co Ltd | ガラスクロス含浸基材の製造方法およびプリント配線板 |
| JP2011256394A (ja) * | 2011-08-09 | 2011-12-22 | Asahi Kasei E-Materials Corp | 感光性耐熱性樹脂前駆体組成物 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3355425A (en) * | 1964-08-06 | 1967-11-28 | Dow Corning | Organopolysiloxanes |
| US3403169A (en) * | 1963-08-23 | 1968-09-24 | Koppers Co Inc | Addition of organometallic compounds to activated olefins |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2809874A1 (de) * | 1978-03-08 | 1979-09-13 | Consortium Elektrochem Ind | Organosiloxane mit sic-gebundenen estergruppen, verfahren zu ihrer herstellung und ihre verwendung |
-
1983
- 1983-01-20 DE DE19833301807 patent/DE3301807A1/de not_active Withdrawn
-
1984
- 1984-01-12 JP JP59002760A patent/JPS59137493A/ja active Granted
- 1984-01-17 EP EP84100413A patent/EP0114636A3/de not_active Withdrawn
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3403169A (en) * | 1963-08-23 | 1968-09-24 | Koppers Co Inc | Addition of organometallic compounds to activated olefins |
| US3355425A (en) * | 1964-08-06 | 1967-11-28 | Dow Corning | Organopolysiloxanes |
Non-Patent Citations (1)
| Title |
|---|
| Chemie u. Technologie d. Silicone, W. Noll, Verlag Chemie, Weinheim, 1968, S.44 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4837339A (en) * | 1984-09-25 | 1989-06-06 | Nissan Chemical Industries, Ltd. | 4-Substituted-1,2,3,6-tetrahydrophthalic acid anhydride |
| EP0855372A1 (de) * | 1997-01-23 | 1998-07-29 | Fraunhofer-Gesellschaft Zur Förderung Der Angewandten Forschung E.V. | Verfahren zur Hydrophilierung von Glassubstraten und deren Verwendung |
| EP2519528A1 (en) * | 2009-12-28 | 2012-11-07 | Dow Corning Toray Co., Ltd. | Organosilicon compound, method for producing thereof, and curable silicone composition containing the same |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0114636A3 (de) | 1985-10-02 |
| EP0114636A2 (de) | 1984-08-01 |
| JPS59137493A (ja) | 1984-08-07 |
| JPS6337119B2 (enExample) | 1988-07-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8130 | Withdrawal |