DE3616577C2 - Neue Organosilanverbindungen - Google Patents
Neue OrganosilanverbindungenInfo
- Publication number
- DE3616577C2 DE3616577C2 DE3616577A DE3616577A DE3616577C2 DE 3616577 C2 DE3616577 C2 DE 3616577C2 DE 3616577 A DE3616577 A DE 3616577A DE 3616577 A DE3616577 A DE 3616577A DE 3616577 C2 DE3616577 C2 DE 3616577C2
- Authority
- DE
- Germany
- Prior art keywords
- organosilane compound
- silane
- trifluoroethoxy
- tris
- formula
- 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.)
- Expired - Fee Related
Links
- -1 organosilane compounds Chemical class 0.000 title claims description 38
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- JXUAUKKYXQMOHO-UHFFFAOYSA-N tris(2,2,2-trifluoroethoxy)silane Chemical compound FC(F)(F)CO[SiH](OCC(F)(F)F)OCC(F)(F)F JXUAUKKYXQMOHO-UHFFFAOYSA-N 0.000 claims description 6
- WMZLKCRFWKWZBG-UHFFFAOYSA-N 3-chloropropyl-tris(2,2,2-trifluoroethoxy)silane Chemical compound FC(F)(F)CO[Si](CCCCl)(OCC(F)(F)F)OCC(F)(F)F WMZLKCRFWKWZBG-UHFFFAOYSA-N 0.000 claims description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 150000001282 organosilanes Chemical class 0.000 claims description 4
- WHNBYXIQCQDGIB-UHFFFAOYSA-N phenyl-tris(2,2,2-trifluoroethoxy)silane Chemical compound FC(F)(F)CO[Si](OCC(F)(F)F)(OCC(F)(F)F)C1=CC=CC=C1 WHNBYXIQCQDGIB-UHFFFAOYSA-N 0.000 claims description 4
- 229910052710 silicon Inorganic materials 0.000 claims description 4
- DTKITZJXWKHEPV-UHFFFAOYSA-N 3-(oxiran-2-ylmethoxy)propyl-tris(2,2,2-trifluoroethoxy)silane Chemical compound FC(F)(F)CO[Si](OCC(F)(F)F)(OCC(F)(F)F)CCCOCC1CO1 DTKITZJXWKHEPV-UHFFFAOYSA-N 0.000 claims description 3
- WMPFAZFUSPXUDU-UHFFFAOYSA-N 3-[tris(2,2,2-trifluoroethoxy)silyl]propane-1-thiol Chemical compound FC(F)(F)CO[Si](CCCS)(OCC(F)(F)F)OCC(F)(F)F WMPFAZFUSPXUDU-UHFFFAOYSA-N 0.000 claims description 3
- SMOHMYMJCYHZTL-UHFFFAOYSA-N 3-[tris(2,2,2-trifluoroethoxy)silyl]propanenitrile Chemical compound FC(F)(F)CO[Si](CCC#N)(OCC(F)(F)F)OCC(F)(F)F SMOHMYMJCYHZTL-UHFFFAOYSA-N 0.000 claims description 3
- 150000005840 aryl radicals Chemical class 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- KMCCIBWNKXHGIE-UHFFFAOYSA-N tris(2,2,2-trifluoroethoxy)-(3,3,3-trifluoropropyl)silane Chemical compound FC(F)(F)CC[Si](OCC(F)(F)F)(OCC(F)(F)F)OCC(F)(F)F KMCCIBWNKXHGIE-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- KJYQHPHBKOSZLO-UHFFFAOYSA-N ethenyl-tris(2,2,2-trifluoroethoxy)silane Chemical compound FC(F)(F)CO[Si](OCC(F)(F)F)(OCC(F)(F)F)C=C KJYQHPHBKOSZLO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 17
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 15
- 238000004458 analytical method Methods 0.000 description 12
- 238000002329 infrared spectrum Methods 0.000 description 11
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 238000009835 boiling Methods 0.000 description 9
- 238000000921 elemental analysis Methods 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 239000011737 fluorine Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000005052 trichlorosilane Substances 0.000 description 4
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 3
- 239000004971 Cross linker Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 229920002313 fluoropolymer Polymers 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000005060 rubber Substances 0.000 description 3
- 229910000077 silane Inorganic materials 0.000 description 3
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 3
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 3
- AOZBRIRMKXPAQJ-UHFFFAOYSA-N 3-[tris(2,2,2-trifluoroethoxy)silyl]propyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC[Si](OCC(F)(F)F)(OCC(F)(F)F)OCC(F)(F)F AOZBRIRMKXPAQJ-UHFFFAOYSA-N 0.000 description 2
- OLBGECWYBGXCNV-UHFFFAOYSA-N 3-trichlorosilylpropanenitrile Chemical compound Cl[Si](Cl)(Cl)CCC#N OLBGECWYBGXCNV-UHFFFAOYSA-N 0.000 description 2
- DOGMJCPBZJUYGB-UHFFFAOYSA-N 3-trichlorosilylpropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC[Si](Cl)(Cl)Cl DOGMJCPBZJUYGB-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229920005560 fluorosilicone rubber Polymers 0.000 description 2
- 239000005054 phenyltrichlorosilane Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- WEUBQNJHVBMUMD-UHFFFAOYSA-N trichloro(3,3,3-trifluoropropyl)silane Chemical compound FC(F)(F)CC[Si](Cl)(Cl)Cl WEUBQNJHVBMUMD-UHFFFAOYSA-N 0.000 description 2
- OOXSLJBUMMHDKW-UHFFFAOYSA-N trichloro(3-chloropropyl)silane Chemical compound ClCCC[Si](Cl)(Cl)Cl OOXSLJBUMMHDKW-UHFFFAOYSA-N 0.000 description 2
- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 description 2
- ORVMIVQULIKXCP-UHFFFAOYSA-N trichloro(phenyl)silane Chemical compound Cl[Si](Cl)(Cl)C1=CC=CC=C1 ORVMIVQULIKXCP-UHFFFAOYSA-N 0.000 description 2
- 239000005050 vinyl trichlorosilane Substances 0.000 description 2
- 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 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- BTHCBXJLLCHNMS-UHFFFAOYSA-N acetyloxysilicon Chemical compound CC(=O)O[Si] BTHCBXJLLCHNMS-UHFFFAOYSA-N 0.000 description 1
- 238000004026 adhesive bonding Methods 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- SLLGVCUQYRMELA-UHFFFAOYSA-N chlorosilicon Chemical compound Cl[Si] SLLGVCUQYRMELA-UHFFFAOYSA-N 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- WEMXRTXQKRXSIO-UHFFFAOYSA-N propanenitrile Chemical compound [CH2]CC#N WEMXRTXQKRXSIO-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 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
- C07F7/025—Silicon compounds without C-silicon linkages
-
- 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)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60104627A JPS61263986A (ja) | 1985-05-16 | 1985-05-16 | 有機けい素化合物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3616577A1 DE3616577A1 (de) | 1987-01-08 |
| DE3616577C2 true DE3616577C2 (de) | 1994-09-08 |
Family
ID=14385674
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3616577A Expired - Fee Related DE3616577C2 (de) | 1985-05-16 | 1986-05-16 | Neue Organosilanverbindungen |
Country Status (3)
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5237082A (en) * | 1989-09-22 | 1993-08-17 | Minnesota Mining And Manufacturing Company | Radiation-curable silicone elastomers and pressure sensitive adhesives |
| NL9302042A (nl) * | 1993-11-25 | 1995-06-16 | Tno | Nieuwe siloxanen en werkwijzen voor de bereiding hiervan, de toepassing van deze siloxanen in bekledingssamenstellingen, de aldus verkregen bekledingssamenstellingen, en de toepassing van deze bekledingssamenstellingen bij het bekleden van substraten of voortbrengselen, alsmede de aldus verkregen beklede substraten en voortbrengselen. |
| US5459198A (en) * | 1994-07-29 | 1995-10-17 | E. I. Du Pont De Nemours And Company | Fluoroinfused composites, articles of manufacture formed therefrom, and processes for the preparation thereof |
| US5798430A (en) * | 1995-06-28 | 1998-08-25 | E. I. Du Pont De Nemours And Compnay | Molecular and oligomeric silane precursors to network materials |
| US5726247A (en) * | 1996-06-14 | 1998-03-10 | E. I. Du Pont De Nemours And Company | Fluoropolymer nanocomposites |
| US20050124976A1 (en) * | 2003-12-04 | 2005-06-09 | Devens Douglas A.Jr. | Medical devices |
| US7914809B2 (en) * | 2005-08-26 | 2011-03-29 | Boston Scientific Scimed, Inc. | Lubricious composites for medical devices |
| KR100791887B1 (ko) | 2006-11-03 | 2008-01-07 | 한국과학기술연구원 | 반 연속식 공정을 이용한 함불소알콕시트리알킬실란의제조방법 |
| US20090306769A1 (en) * | 2008-06-06 | 2009-12-10 | Boston Scientific Scimed, Inc. | Medical balloon made with hybrid polymer-ceramic material and method of making and using the same |
| CN103012462A (zh) * | 2013-01-16 | 2013-04-03 | 甘肃省化工研究院 | 乙烯基三（2,2,2-三氟）乙氧基硅烷化合物的制备方法 |
| JP2018065946A (ja) * | 2016-10-20 | 2018-04-26 | キヤノン株式会社 | コーティング用材料およびその製造方法 |
| CN110684045B (zh) * | 2019-01-08 | 2022-08-30 | 浙江开化合成材料有限公司 | 一种乙烯基三(2，2，2-三氟乙氧基)硅烷的制备方法 |
| CN116694274B (zh) * | 2023-06-25 | 2024-04-16 | 浙江安益新材料有限公司 | 一种脲醛乳液胶粘剂及其制备方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2892859A (en) * | 1955-05-20 | 1959-06-30 | Research Corp | Fluorine-containing alkoxyalkylsilanes |
| US2928857A (en) * | 1955-08-22 | 1960-03-15 | Du Pont | Selected tetrasubstituted monosilanes |
| US3394162A (en) * | 1964-11-25 | 1968-07-23 | Du Pont | Novel compounds and polymers |
| US3536744A (en) * | 1968-01-05 | 1970-10-27 | Allied Chem | Haloalkoxysilanes |
| US3687606A (en) * | 1969-10-04 | 1972-08-29 | Bayer Ag | Permanent hair waving by artificially shaping with an epoxy-organo-silane |
| US4069368A (en) * | 1976-10-01 | 1978-01-17 | Minnesota Mining And Manufacturing Company | Workable and curable epoxy-terminated silane films |
-
1985
- 1985-05-16 JP JP60104627A patent/JPS61263986A/ja active Granted
-
1986
- 1986-05-13 US US06/862,676 patent/US4652663A/en not_active Expired - Fee Related
- 1986-05-16 DE DE3616577A patent/DE3616577C2/de not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61263986A (ja) | 1986-11-21 |
| JPH0132227B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1989-06-29 |
| DE3616577A1 (de) | 1987-01-08 |
| US4652663A (en) | 1987-03-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |