CN1292794A - 烷基(氨基)二烷氧基硅烷的制备 - Google Patents
烷基(氨基)二烷氧基硅烷的制备 Download PDFInfo
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- CN1292794A CN1292794A CN998037028A CN99803702A CN1292794A CN 1292794 A CN1292794 A CN 1292794A CN 998037028 A CN998037028 A CN 998037028A CN 99803702 A CN99803702 A CN 99803702A CN 1292794 A CN1292794 A CN 1292794A
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- CN
- China
- Prior art keywords
- alkyl
- reaction
- amino
- dialkoxysilanes
- aprotic solvent
- 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
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- 125000000217 alkyl group Chemical group 0.000 title claims abstract description 36
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 title claims abstract description 25
- 238000002360 preparation method Methods 0.000 title claims description 11
- 238000000034 method Methods 0.000 claims abstract description 34
- 238000006243 chemical reaction Methods 0.000 claims abstract description 29
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 20
- -1 alkylamino magnesium chloride Chemical compound 0.000 claims abstract description 12
- 125000003118 aryl group Chemical group 0.000 claims abstract description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000000010 aprotic solvent Substances 0.000 claims abstract description 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 239000006227 byproduct Substances 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 150000004791 alkyl magnesium halides Chemical class 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 239000003054 catalyst Substances 0.000 abstract description 6
- 150000004795 grignard reagents Chemical class 0.000 abstract description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract description 3
- 239000007818 Grignard reagent Substances 0.000 abstract description 3
- 238000011065 in-situ storage Methods 0.000 abstract description 3
- 150000003973 alkyl amines Chemical class 0.000 abstract description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L magnesium chloride Substances [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 abstract description 2
- 229910001629 magnesium chloride Inorganic materials 0.000 abstract description 2
- 125000001424 substituent group Chemical group 0.000 abstract description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- 150000001875 compounds Chemical class 0.000 description 11
- 239000007788 liquid Substances 0.000 description 10
- IUYHWZFSGMZEOG-UHFFFAOYSA-M magnesium;propane;chloride Chemical compound [Mg+2].[Cl-].C[CH-]C IUYHWZFSGMZEOG-UHFFFAOYSA-M 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- YQGOWXYZDLJBFL-UHFFFAOYSA-N dimethoxysilane Chemical compound CO[SiH2]OC YQGOWXYZDLJBFL-UHFFFAOYSA-N 0.000 description 5
- ZFMKNHGCDMUEBA-UHFFFAOYSA-N n-[dimethoxy(2-methylpropyl)silyl]-n-ethylethanamine Chemical compound CCN(CC)[Si](OC)(OC)CC(C)C ZFMKNHGCDMUEBA-UHFFFAOYSA-N 0.000 description 5
- WUPWVMRJOBHGBD-UHFFFAOYSA-N n-[dimethoxy(methyl)silyl]-2-methylpropan-2-amine Chemical compound CO[Si](C)(OC)NC(C)(C)C WUPWVMRJOBHGBD-UHFFFAOYSA-N 0.000 description 5
- 239000004711 α-olefin Substances 0.000 description 5
- PJSFQEVODHCOOF-UHFFFAOYSA-N (2-ethylpiperidin-1-yl)-dimethoxy-(3,3,3-trifluoropropyl)silane Chemical compound CCC1CCCCN1[Si](CCC(F)(F)F)(OC)OC PJSFQEVODHCOOF-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 239000012230 colorless oil Substances 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- MJGDXIPDIZVYOI-UHFFFAOYSA-N n-[diethoxy(ethyl)silyl]cyclohexanamine Chemical compound CCO[Si](CC)(OCC)NC1CCCCC1 MJGDXIPDIZVYOI-UHFFFAOYSA-N 0.000 description 3
- 229920000098 polyolefin Polymers 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical group N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 238000006136 alcoholysis reaction Methods 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 150000002431 hydrogen Chemical group 0.000 description 2
- ZHLDMBMNKCIBQN-UHFFFAOYSA-M magnesium;methanolate;chloride Chemical compound [Cl-].CO[Mg+] ZHLDMBMNKCIBQN-UHFFFAOYSA-M 0.000 description 2
- WXHREKGXRCMNOT-UHFFFAOYSA-M magnesium;piperidin-1-ide;chloride Chemical class [Cl-].[Mg+]N1CCCCC1 WXHREKGXRCMNOT-UHFFFAOYSA-M 0.000 description 2
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002685 polymerization catalyst Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- QBBKKFZGCDJDQK-UHFFFAOYSA-N 2-ethylpiperidine Chemical compound CCC1CCCCN1 QBBKKFZGCDJDQK-UHFFFAOYSA-N 0.000 description 1
- DAEXGDSKPVNFGH-UHFFFAOYSA-N CO[Mg] Chemical compound CO[Mg] DAEXGDSKPVNFGH-UHFFFAOYSA-N 0.000 description 1
- 101000809257 Homo sapiens Ubiquitin carboxyl-terminal hydrolase 4 Proteins 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 102100038463 Ubiquitin carboxyl-terminal hydrolase 4 Human genes 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical class Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000004122 cyclic group Chemical class 0.000 description 1
- 125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- KRWGJUKYJDCPAP-UHFFFAOYSA-N dimethoxy-methyl-piperidin-1-ylsilane Chemical compound CO[Si](C)(OC)N1CCCCC1 KRWGJUKYJDCPAP-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- FQRPQDOBQMCGOR-UHFFFAOYSA-M magnesium;2-ethylpiperidin-1-ide;chloride Chemical compound [Mg+2].[Cl-].CCC1CCCC[N-]1 FQRPQDOBQMCGOR-UHFFFAOYSA-M 0.000 description 1
- UJYYOEDHUAQIQJ-UHFFFAOYSA-M magnesium;diethylazanide;chloride Chemical class [Cl-].CCN([Mg+])CC UJYYOEDHUAQIQJ-UHFFFAOYSA-M 0.000 description 1
- KRTCPMDBLDWJQY-UHFFFAOYSA-M magnesium;ethanolate;chloride Chemical class [Mg+2].[Cl-].CC[O-] KRTCPMDBLDWJQY-UHFFFAOYSA-M 0.000 description 1
- CFLWDUMQORSZJS-UHFFFAOYSA-N n-[ethyl(dimethoxy)silyl]cyclohexanamine Chemical compound CC[Si](OC)(OC)NC1CCCCC1 CFLWDUMQORSZJS-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical class [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 0.000 description 1
- XYJRNCYWTVGEEG-UHFFFAOYSA-N trimethoxy(2-methylpropyl)silane Chemical compound CO[Si](OC)(OC)CC(C)C XYJRNCYWTVGEEG-UHFFFAOYSA-N 0.000 description 1
- PEIANZNHTIDHQE-UHFFFAOYSA-N trimethyl(3,3,3-trifluoropropyl)silane Chemical compound C[Si](C)(C)CCC(F)(F)F PEIANZNHTIDHQE-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
-
- 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
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/1888—Preparation; Treatments not provided for in C07F7/20 by reactions involving the formation of other Si-linkages, e.g. Si-N
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
Abstract
Description
化合物 | 1H-NMR-L(CDCl3) | 13C-NMR L(CDCl3) | 外观 | 纯度 | 沸点 | 产率(分离后) |
(3-甲基丁基)(2-乙基哌啶子基)二甲氧基硅烷 | 3.5(s,3H),3.1-2.8(m,3H)1.7-1.2(m,11H),0.9-0.8(m,9H),0.6(m,2H) | 51.9,50.3,38.7,32.1,30.929.5,27.8,23.4,22.4,20.0,11.7,84 | 无色液体 | 97% | 96℃/0.8mm | 83% |
(3,3,3-三氟丙基)(2-三甲基-甲硅烷基哌啶子基)二甲氧基硅烷 | 3.5(s,6H),3.1-2.9(m,1H),2.8-2.6(m,2H),2.2-2.0(m,2H),1.8-1.35(m,5H),1.32-1.15(m,1H),0.9-0.7(m,2H),0.1(s,9H) | 127.7(四重峰J=275Hz),50.1,42,6,42.2,28.0(四重峰J=30Hz),27.8,23.4,3.0,0.2,-4.2 | 无色液体 | 99% | 91℃/0.8mm | 85% |
(3,3,3-三氟丙基)(2-三甲基甲硅烷基吡咯烷基)二甲氧基硅烷 | 3.50(s,3H),3.45(s,3H),3.25-3.10(m,1H),2.90-2.80(m,1H),2.80-2.65(m,1H),2.20-1.50(m,6H),0.85-0.75(m,2H),-0.05(s,9H) | 129.6(四重峰J=275),50.1(由于环异构体产生的两个峰),49(由于环异构体产生的两个峰),47.6-46.7,28 2(四重峰J=30),28 0,27.5,2.9,-2.7 | 无色液体 | 98% | 71℃/0.3mm | 91% |
正丙基(顺-2,6-二甲基-哌啶子基)二甲氧基硅烷 | 3.4(s,6H),3.3(m,2H),1.8-1.2(m,8H),1.1(d,6H),0.9(t,3H),0.5(m,2H) | 50.1,44.1,31.6,24.6,18.0,16.8,14.5,13.3 | 无色液体 | 96% | 69℃/0.4mm | 86% |
(3,3,3-三氟丙基)(十氢喹啉基)二甲氧基硅烷 | 3.5(s,6H),3.1-2.7(m,3H),2.2-1.9(m,3H),1.8-1.1(m,12H),0.9-0.7(m,2H) | 127.9(四重峰,J=275Hz),52.6,50.4,38.2,36.9,29.0,28.5,27.8(四重峰,J=30Hz),26.4,26.3,20.5,3.1 | 无色液体 | 98% | 105(℃/1.0mm | 82% |
无色液体 | 95% | 200℃/1.4mm | 83% | |||
(3,3,3-三氟丙基)(双2-乙基-己基氨基)二甲氧基硅烷 | 3.5(s,6H),2.6-2.4(dJ,4H),2.2-2.0(m,2H),1.6-1.1(m,18H),1.0-0.7(m,14H) | 128(四重峰,J=275Hz),50.4,48.5.39.4,36.9,30.8,29.1,28.2(四重峰,J=30Hz),23.2,14.2,10.3,3.2 | ||||
(3,3,3-三氟丙基)(2-乙基哌啶基)二甲氧基硅烷 | 3.49(s,6H),3.08-2.97(m.1H),2.93-2.89(m.2H),2.2-2 0(m,2H),1.76-1.43(m,7H),1.43-1.25(m,lH),0.87(t,311),0.82-0.75(m,2H) | 127.2(四重峰J=276Hz),52.238.8,29.9.28.8(四重峰,J=30Hz),28,23.5,20.1,11.6,3.59 | 无色液体 | 98% | 70℃/0.1mm | 88% |
(2-甲基丙基)(二乙基氨基)二甲氧基硅烷 | 3.47(s,6H),2.87(q,4H),1.88-1.74(m.1H),1.03(t,6H),0.96(d,6H),0.59(d,2H) | 49.9,28.7,26.1,24.2,21.2,15.5 | 无色液体 | 98% | 104℃/30mm | 79% |
甲基(叔丁基氨基)二甲氧基硅烷 | 3.45(s,6H),1.17(s,9H),1.05(s,1H),0.05(s,3H) | 49.2,48.1,33.0,-5.0 | ||||
无色液体 | 98.5% | 107℃/135mm | 82% | |||
乙基(环已基氨基)二甲氧基硅烷 | 2.76-2.65(m,1H),1.90-1.50(m,5H),1.37-0.79(m,6H),1.18(t,4H),0.96(t,3H),0.54(q,2H) | 57.4,49.2,38.3,24.6,25.4,18.0,6.5,3.7 | ||||
无色液体 | 98.2% | 68℃/0.5mm | 83% | |||
Claims (10)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/US1999/000947 WO2000042049A1 (en) | 1999-01-13 | 1999-01-13 | Preparation of alkyl (amino) dialkoxysilanes |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1292794A true CN1292794A (zh) | 2001-04-25 |
CN1125074C CN1125074C (zh) | 2003-10-22 |
Family
ID=22272005
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN99803702A Expired - Fee Related CN1125074C (zh) | 1999-01-13 | 1999-01-13 | 烷基(氨基)二烷氧基硅烷的制备 |
Country Status (7)
Country | Link |
---|---|
EP (1) | EP1062220B1 (zh) |
JP (1) | JP3569680B2 (zh) |
KR (1) | KR100371312B1 (zh) |
CN (1) | CN1125074C (zh) |
CA (1) | CA2322648C (zh) |
DE (1) | DE69930733T2 (zh) |
WO (1) | WO2000042049A1 (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103224510A (zh) * | 2012-01-27 | 2013-07-31 | 气体产品与化学公司 | 烷氧基氨基硅烷化合物及其应用 |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
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JP4768589B2 (ja) * | 2006-11-29 | 2011-09-07 | 東邦チタニウム株式会社 | アミノアルコキシシラン化合物の合成方法 |
US9677178B2 (en) | 2012-01-27 | 2017-06-13 | Versum Materials Us, Llc | Alkoxyaminosilane compounds and applications thereof |
US10421766B2 (en) | 2015-02-13 | 2019-09-24 | Versum Materials Us, Llc | Bisaminoalkoxysilane compounds and methods for using same to deposit silicon-containing films |
KR102151405B1 (ko) | 2019-12-12 | 2020-09-03 | 이명직 | 가변형 골프 연습 장치 |
KR102224710B1 (ko) | 2020-06-15 | 2021-03-05 | 이명직 | 확장 가능한 가변형 골프 연습 장치 및 이를 제어하는 방법 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4491669A (en) * | 1980-11-12 | 1985-01-01 | Petrarch Systems Inc. | Mixed alkoxyaminosilanes, methods of making same and vulcanizing silicons prepared therefrom |
CA1336596C (en) * | 1989-07-26 | 1995-08-08 | Constantine A. Stewart | Organosilane compounds |
US5102842A (en) * | 1990-08-23 | 1992-04-07 | Himont Incorporated | Catalyst for the polymerization of alpha-olefins containing trifluoropropyl substituted silane compounds |
JPH0940714A (ja) * | 1995-07-28 | 1997-02-10 | Ube Ind Ltd | アミノアルコキシシラン |
US6130180A (en) * | 1997-12-23 | 2000-10-10 | Montell North America Inc. | Catalyst for the polymerization of alpha-olefins containing substituted amino silane compounds |
-
1999
- 1999-01-13 CA CA002322648A patent/CA2322648C/en not_active Expired - Fee Related
- 1999-01-13 DE DE69930733T patent/DE69930733T2/de not_active Expired - Lifetime
- 1999-01-13 WO PCT/US1999/000947 patent/WO2000042049A1/en active IP Right Grant
- 1999-01-13 CN CN99803702A patent/CN1125074C/zh not_active Expired - Fee Related
- 1999-01-13 KR KR10-2000-7010035A patent/KR100371312B1/ko not_active IP Right Cessation
- 1999-01-13 EP EP99902311A patent/EP1062220B1/en not_active Expired - Lifetime
- 1999-01-13 JP JP2000593616A patent/JP3569680B2/ja not_active Expired - Fee Related
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103224510A (zh) * | 2012-01-27 | 2013-07-31 | 气体产品与化学公司 | 烷氧基氨基硅烷化合物及其应用 |
CN103224510B (zh) * | 2012-01-27 | 2016-08-03 | 气体产品与化学公司 | 烷氧基氨基硅烷化合物及其应用 |
Also Published As
Publication number | Publication date |
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KR20010052205A (ko) | 2001-06-25 |
JP3569680B2 (ja) | 2004-09-22 |
JP2002534527A (ja) | 2002-10-15 |
EP1062220B1 (en) | 2006-04-05 |
DE69930733T2 (de) | 2006-08-31 |
CA2322648C (en) | 2004-11-30 |
DE69930733D1 (de) | 2006-05-18 |
CN1125074C (zh) | 2003-10-22 |
WO2000042049A1 (en) | 2000-07-20 |
KR100371312B1 (ko) | 2003-02-07 |
CA2322648A1 (en) | 2000-07-20 |
EP1062220A4 (en) | 2002-04-24 |
EP1062220A1 (en) | 2000-12-27 |
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