JP5088510B2 - アミノ基を有するビニルシラン化合物及びその製造方法 - Google Patents
アミノ基を有するビニルシラン化合物及びその製造方法 Download PDFInfo
- Publication number
- JP5088510B2 JP5088510B2 JP2009142049A JP2009142049A JP5088510B2 JP 5088510 B2 JP5088510 B2 JP 5088510B2 JP 2009142049 A JP2009142049 A JP 2009142049A JP 2009142049 A JP2009142049 A JP 2009142049A JP 5088510 B2 JP5088510 B2 JP 5088510B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- general formula
- butyl
- following general
- 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.)
- Active
Links
- -1 Vinylsilane compound Chemical class 0.000 title claims description 119
- 125000003277 amino group Chemical group 0.000 title claims description 13
- 238000000034 method Methods 0.000 title description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 7
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 claims description 7
- 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 claims description 7
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 7
- 125000002757 morpholinyl group Chemical group 0.000 claims description 6
- 125000003386 piperidinyl group Chemical group 0.000 claims description 6
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 4
- 150000001875 compounds Chemical class 0.000 description 14
- 229920000642 polymer Polymers 0.000 description 12
- 150000002430 hydrocarbons Chemical group 0.000 description 10
- 239000002904 solvent Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000002329 infrared spectrum Methods 0.000 description 6
- 229920000098 polyolefin Polymers 0.000 description 6
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 6
- SHTUYIQXGYBGGQ-UHFFFAOYSA-N N,N-diethyl-3-(2-methylprop-1-enylsilyl)propan-1-amine Chemical compound C(C)N(CCC[SiH2]C=C(C)C)CC SHTUYIQXGYBGGQ-UHFFFAOYSA-N 0.000 description 5
- 230000004048 modification Effects 0.000 description 5
- 238000012986 modification Methods 0.000 description 5
- UIYUGSOEJNHBFF-UHFFFAOYSA-N 3-chloropropyl(2-methylprop-1-enyl)silane Chemical compound ClCCC[SiH2]C=C(C)C UIYUGSOEJNHBFF-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-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
- 238000009835 boiling Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 238000001819 mass spectrum Methods 0.000 description 4
- 239000003607 modifier Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- NNCDNYXEOCAPFI-UHFFFAOYSA-N 3-(1-methylpiperazin-2-yl)propyl-(2-methylprop-1-enyl)silane Chemical compound CN1CCNCC1CCC[SiH2]C=C(C)C NNCDNYXEOCAPFI-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 2
- AFOVZRKWLMSDSL-UHFFFAOYSA-N 3-[chloro(dimethyl)silyl]-n,n-bis(trimethylsilyl)propan-1-amine Chemical compound C[Si](C)(C)N([Si](C)(C)C)CCC[Si](C)(C)Cl AFOVZRKWLMSDSL-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 239000000806 elastomer Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical compound [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 2
- AXPSULVQZOSGEP-UHFFFAOYSA-N (1-ethylpiperazin-2-yl)methyl-(2-methylprop-1-enyl)silane Chemical compound CCN1CCNCC1C[SiH2]C=C(C)C AXPSULVQZOSGEP-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- QHBDLCZLXSDJMW-UHFFFAOYSA-N 1-(2-methylprop-1-enylsilyl)-N,N-bis(trimethylsilyl)methanamine Chemical compound C[Si](N([Si](C)(C)C)C[SiH2]C=C(C)C)(C)C QHBDLCZLXSDJMW-UHFFFAOYSA-N 0.000 description 1
- IZFVZIZZYSSEER-UHFFFAOYSA-N 1-(2-methylprop-1-enylsilyl)-N-(triethylsilylmethyl)methanamine Chemical compound C(C)[Si](CC)(CC)CNC[SiH2]C=C(C)C IZFVZIZZYSSEER-UHFFFAOYSA-N 0.000 description 1
- HTUWYGNBBCVFMA-UHFFFAOYSA-N 1-(2-methylprop-1-enylsilyl)-N-(trimethylsilylmethyl)methanamine Chemical compound C[Si](C)(C)CNC[SiH2]C=C(C)C HTUWYGNBBCVFMA-UHFFFAOYSA-N 0.000 description 1
- SOPYUVQMRJOSQD-UHFFFAOYSA-N 2-(1-ethylpiperazin-2-yl)ethyl-(2-methylprop-1-enyl)silane Chemical compound CCN1CCNCC1CC[SiH2]C=C(C)C SOPYUVQMRJOSQD-UHFFFAOYSA-N 0.000 description 1
- DJQKIQOQAICQKS-UHFFFAOYSA-N 2-(2-methylprop-1-enylsilyl)-N,N-bis(trimethylsilyl)ethanamine Chemical compound C[Si](N([Si](C)(C)C)CC[SiH2]C=C(C)C)(C)C DJQKIQOQAICQKS-UHFFFAOYSA-N 0.000 description 1
- OZIPSVHITFINFD-UHFFFAOYSA-N 2-(2-methylprop-1-enylsilyl)-N-(2-triethylsilylethyl)ethanamine Chemical compound C(C)[Si](CC)(CC)CCNCC[SiH2]C=C(C)C OZIPSVHITFINFD-UHFFFAOYSA-N 0.000 description 1
- CXKURKVCQLLOJH-UHFFFAOYSA-N 2-(2-methylprop-1-enylsilyl)-N-(2-trimethylsilylethyl)ethanamine Chemical compound C[Si](C)(C)CCNCC[SiH2]C=C(C)C CXKURKVCQLLOJH-UHFFFAOYSA-N 0.000 description 1
- ONWMPIHAWJPKKT-UHFFFAOYSA-N 2-(2-methylprop-1-enylsilyl)-N-(triethylsilylmethyl)ethanamine Chemical compound C(C)[Si](CC)(CC)CNCC[SiH2]C=C(C)C ONWMPIHAWJPKKT-UHFFFAOYSA-N 0.000 description 1
- SEZTUYJFWGKCTC-UHFFFAOYSA-N 2-(2-methylprop-1-enylsilyl)-N-(trimethylsilylmethyl)ethanamine Chemical compound C[Si](C)(C)CNCC[SiH2]C=C(C)C SEZTUYJFWGKCTC-UHFFFAOYSA-N 0.000 description 1
- HKZIWZJVPGDAST-UHFFFAOYSA-N 2-(2-methylprop-1-enylsilyl)ethanamine Chemical compound CC(=C[SiH2]CCN)C HKZIWZJVPGDAST-UHFFFAOYSA-N 0.000 description 1
- AGXWQDVMEYPQLL-UHFFFAOYSA-N 2-[tert-butyl(dimethyl)silyl]-N-(2-methylprop-1-enylsilylmethyl)ethanamine Chemical compound [Si](C)(C)(C(C)(C)C)CCNC[SiH2]C=C(C)C AGXWQDVMEYPQLL-UHFFFAOYSA-N 0.000 description 1
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
- NZSZIRWNGKMTMQ-UHFFFAOYSA-N 2-methyl-N-(2-methylprop-1-enylsilylmethyl)-N-(2-methylpropyl)propan-1-amine Chemical compound C(C(C)C)N(CC(C)C)C[SiH2]C=C(C)C NZSZIRWNGKMTMQ-UHFFFAOYSA-N 0.000 description 1
- SVRQIBPUBOFOTL-UHFFFAOYSA-N 2-methyl-N-[2-(2-methylprop-1-enylsilyl)ethyl]-N-(2-methylpropyl)propan-1-amine Chemical compound C(C(C)C)N(CC(C)C)CC[SiH2]C=C(C)C SVRQIBPUBOFOTL-UHFFFAOYSA-N 0.000 description 1
- HEIHZRFMHQRISM-UHFFFAOYSA-N 2-methyl-N-[3-(2-methylprop-1-enylsilyl)propyl]-N-(2-methylpropyl)propan-1-amine Chemical compound C(C(C)C)N(CC(C)C)CCC[SiH2]C=C(C)C HEIHZRFMHQRISM-UHFFFAOYSA-N 0.000 description 1
- RQPFCROYMXJNRP-UHFFFAOYSA-N 2-methylprop-1-enyl(2-morpholin-4-ylethyl)silane Chemical compound N1(CCOCC1)CC[SiH2]C=C(C)C RQPFCROYMXJNRP-UHFFFAOYSA-N 0.000 description 1
- AEGQVVPXXHYDMY-UHFFFAOYSA-N 2-methylprop-1-enyl(2-piperidin-1-ylethyl)silane Chemical compound N1(CCCCC1)CC[SiH2]C=C(C)C AEGQVVPXXHYDMY-UHFFFAOYSA-N 0.000 description 1
- DVPDZXBJVNGMKC-UHFFFAOYSA-N 2-methylprop-1-enyl(2-pyrrolidin-1-ylethyl)silane Chemical compound N1(CCCC1)CC[SiH2]C=C(C)C DVPDZXBJVNGMKC-UHFFFAOYSA-N 0.000 description 1
- SLFFOMNHQBNDQR-UHFFFAOYSA-N 2-methylprop-1-enyl(3-morpholin-4-ylpropyl)silane Chemical compound N1(CCOCC1)CCC[SiH2]C=C(C)C SLFFOMNHQBNDQR-UHFFFAOYSA-N 0.000 description 1
- ILCQLZXCTFFWJT-UHFFFAOYSA-N 2-methylprop-1-enyl(3-piperidin-1-ylpropyl)silane Chemical compound N1(CCCCC1)CCC[SiH2]C=C(C)C ILCQLZXCTFFWJT-UHFFFAOYSA-N 0.000 description 1
- XSHUDWAUJVFLDM-UHFFFAOYSA-N 2-methylprop-1-enyl(3-pyrrolidin-1-ylpropyl)silane Chemical compound N1(CCCC1)CCC[SiH2]C=C(C)C XSHUDWAUJVFLDM-UHFFFAOYSA-N 0.000 description 1
- BKVBAKKZULRVKW-UHFFFAOYSA-N 2-methylprop-1-enyl(morpholin-4-ylmethyl)silane Chemical compound N1(CCOCC1)C[SiH2]C=C(C)C BKVBAKKZULRVKW-UHFFFAOYSA-N 0.000 description 1
- SQVNXZXLZAQYSC-UHFFFAOYSA-N 3-(1-ethylpiperazin-2-yl)propyl-(2-methylprop-1-enyl)silane Chemical compound CCN1CCNCC1CCC[SiH2]C=C(C)C SQVNXZXLZAQYSC-UHFFFAOYSA-N 0.000 description 1
- UZIDIVYSGDCZJM-UHFFFAOYSA-N 3-(2-methylprop-1-enylsilyl)-N,N-bis(trimethylsilyl)propan-1-amine Chemical compound C[Si](N([Si](C)(C)C)CCC[SiH2]C=C(C)C)(C)C UZIDIVYSGDCZJM-UHFFFAOYSA-N 0.000 description 1
- NOIILDQCRKPVFO-UHFFFAOYSA-N 3-(2-methylprop-1-enylsilyl)-N,N-di(propan-2-yl)propan-1-amine Chemical compound C(C)(C)N(C(C)C)CCC[SiH2]C=C(C)C NOIILDQCRKPVFO-UHFFFAOYSA-N 0.000 description 1
- PANYXCQEKBPKSY-UHFFFAOYSA-N 3-(2-methylprop-1-enylsilyl)-N,N-dipropylpropan-1-amine Chemical compound C(CC)N(CCC[SiH2]C=C(C)C)CCC PANYXCQEKBPKSY-UHFFFAOYSA-N 0.000 description 1
- CKHQWEHFKFSGSV-UHFFFAOYSA-N 3-(2-methylprop-1-enylsilyl)-N-(2-triethylsilylethyl)propan-1-amine Chemical compound C(C)[Si](CC)(CC)CCNCCC[SiH2]C=C(C)C CKHQWEHFKFSGSV-UHFFFAOYSA-N 0.000 description 1
- JEMUSDRVTAYQCV-UHFFFAOYSA-N 3-(2-methylprop-1-enylsilyl)-N-(2-trimethylsilylethyl)propan-1-amine Chemical compound C[Si](C)(C)CCNCCC[SiH2]C=C(C)C JEMUSDRVTAYQCV-UHFFFAOYSA-N 0.000 description 1
- UYGGRYICALTXRP-UHFFFAOYSA-N 3-(2-methylprop-1-enylsilyl)-N-(3-triethylsilylpropyl)propan-1-amine Chemical compound C(C)[Si](CC)(CC)CCCNCCC[SiH2]C=C(C)C UYGGRYICALTXRP-UHFFFAOYSA-N 0.000 description 1
- DQBZVKCTLQDSFD-UHFFFAOYSA-N 3-(2-methylprop-1-enylsilyl)-N-(3-trimethylsilylpropyl)propan-1-amine Chemical compound C[Si](C)(C)CCCNCCC[SiH2]C=C(C)C DQBZVKCTLQDSFD-UHFFFAOYSA-N 0.000 description 1
- NMBJPINWJVFBJA-UHFFFAOYSA-N 3-(2-methylprop-1-enylsilyl)-N-(triethylsilylmethyl)propan-1-amine Chemical compound C(C)[Si](CC)(CC)CNCCC[SiH2]C=C(C)C NMBJPINWJVFBJA-UHFFFAOYSA-N 0.000 description 1
- VMQSBOXNZLAKQX-UHFFFAOYSA-N 3-(2-methylprop-1-enylsilyl)-N-(trimethylsilylmethyl)propan-1-amine Chemical compound C[Si](C)(C)CNCCC[SiH2]C=C(C)C VMQSBOXNZLAKQX-UHFFFAOYSA-N 0.000 description 1
- ORMYGAJQIRHCMA-UHFFFAOYSA-N 3-(2-methylprop-1-enylsilyl)propan-1-amine Chemical compound CC(=C[SiH2]CCCN)C ORMYGAJQIRHCMA-UHFFFAOYSA-N 0.000 description 1
- BPPRGXKIWARBJW-UHFFFAOYSA-N 3-[2-methylprop-1-enyl(triethylsilyl)silyl]-N-propan-2-ylpropan-1-amine Chemical compound CC[Si](CC)(CC)[SiH](C=C(C)C)CCCNC(C)C BPPRGXKIWARBJW-UHFFFAOYSA-N 0.000 description 1
- XCNMXISNMIEBBR-UHFFFAOYSA-N 3-[2-methylprop-1-enyl(trimethylsilyl)silyl]-N-propan-2-ylpropan-1-amine Chemical compound CC(C)NCCC[SiH]([Si](C)(C)C)C=C(C)C XCNMXISNMIEBBR-UHFFFAOYSA-N 0.000 description 1
- ZHGSDWFXUMBGMW-UHFFFAOYSA-N 3-[[tert-butyl(dimethyl)silyl]-(2-methylprop-1-enyl)silyl]-N-propan-2-ylpropan-1-amine Chemical compound [Si](C)(C)(C(C)(C)C)[SiH](C=C(C)C)CCCNC(C)C ZHGSDWFXUMBGMW-UHFFFAOYSA-N 0.000 description 1
- QTTSZVQKYLVMPP-UHFFFAOYSA-N 3-[tert-butyl(dimethyl)silyl]-N-(2-methylprop-1-enylsilylmethyl)propan-1-amine Chemical compound [Si](C)(C)(C(C)(C)C)CCCNC[SiH2]C=C(C)C QTTSZVQKYLVMPP-UHFFFAOYSA-N 0.000 description 1
- ZJHGZXNEZCBDFL-UHFFFAOYSA-N 3-[tert-butyl(dimethyl)silyl]-N-[2-(2-methylprop-1-enylsilyl)ethyl]propan-1-amine Chemical compound [Si](C)(C)(C(C)(C)C)CCCNCC[SiH2]C=C(C)C ZJHGZXNEZCBDFL-UHFFFAOYSA-N 0.000 description 1
- TXIHXGPOAKWTNH-UHFFFAOYSA-N 4-[tert-butyl(dimethyl)silyl]-N-(2-methylprop-1-enylsilylmethyl)butan-1-amine Chemical compound [Si](C)(C)(C(C)(C)C)CCCCNC[SiH2]C=C(C)C TXIHXGPOAKWTNH-UHFFFAOYSA-N 0.000 description 1
- IRTIHQPOZRTAMB-UHFFFAOYSA-N 4-[tert-butyl(dimethyl)silyl]-N-[2-(2-methylprop-1-enylsilyl)ethyl]butan-1-amine Chemical compound [Si](C)(C)(C(C)(C)C)CCCCNCC[SiH2]C=C(C)C IRTIHQPOZRTAMB-UHFFFAOYSA-N 0.000 description 1
- QEHKMFLDEGHALL-UHFFFAOYSA-N 4-[tert-butyl(dimethyl)silyl]-N-[3-[ethenyl(dimethyl)silyl]propyl]butan-1-amine Chemical compound CC(C)(C)[Si](C)(C)CCCCNCCC[Si](C)(C)C=C QEHKMFLDEGHALL-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- NXSKQRNWSSGYIC-UHFFFAOYSA-N CC(=C[SiH](C)CCCN1CCNCC1)C Chemical compound CC(=C[SiH](C)CCCN1CCNCC1)C NXSKQRNWSSGYIC-UHFFFAOYSA-N 0.000 description 1
- KXQQCOHLMUJKKE-UHFFFAOYSA-N CC(=C[SiH](C)CN1CCNCC1)C Chemical compound CC(=C[SiH](C)CN1CCNCC1)C KXQQCOHLMUJKKE-UHFFFAOYSA-N 0.000 description 1
- WUMGDFBAQRIZFT-UHFFFAOYSA-N CC(=C[SiH](CCC[Si](C)(C)C)CCN)C Chemical compound CC(=C[SiH](CCC[Si](C)(C)C)CCN)C WUMGDFBAQRIZFT-UHFFFAOYSA-N 0.000 description 1
- QLEYLIULLVASFQ-UHFFFAOYSA-N CC(C)[SiH2]CCCNCC[SiH2]C=C(C)C Chemical compound CC(C)[SiH2]CCCNCC[SiH2]C=C(C)C QLEYLIULLVASFQ-UHFFFAOYSA-N 0.000 description 1
- XRGMCEQOQVVAPA-UHFFFAOYSA-N CC(C)[SiH2][SiH](CCCNC1=CC=CC=C1)C=C(C)C Chemical compound CC(C)[SiH2][SiH](CCCNC1=CC=CC=C1)C=C(C)C XRGMCEQOQVVAPA-UHFFFAOYSA-N 0.000 description 1
- OQULRPQJTNRKPI-UHFFFAOYSA-N CCC(C)NC[SiH](C=C(C)C)[SiH3] Chemical compound CCC(C)NC[SiH](C=C(C)C)[SiH3] OQULRPQJTNRKPI-UHFFFAOYSA-N 0.000 description 1
- NWFWWCCVBLCHLJ-UHFFFAOYSA-N CCC(C)[Si](CCN)(C(C)CC)C=C(C)C Chemical compound CCC(C)[Si](CCN)(C(C)CC)C=C(C)C NWFWWCCVBLCHLJ-UHFFFAOYSA-N 0.000 description 1
- WMCLPTTVLFZTAE-UHFFFAOYSA-N CCC(C)[Si](CCN)(C=C(C)C)[Si](C)(C)C(C)(C)C Chemical compound CCC(C)[Si](CCN)(C=C(C)C)[Si](C)(C)C(C)(C)C WMCLPTTVLFZTAE-UHFFFAOYSA-N 0.000 description 1
- RQHODAHMBYKSPX-UHFFFAOYSA-N CCC(C)[Si](CN)(C(C)CC)C=C(C)C Chemical compound CCC(C)[Si](CN)(C(C)CC)C=C(C)C RQHODAHMBYKSPX-UHFFFAOYSA-N 0.000 description 1
- FIVYTAHWOCSXHE-UHFFFAOYSA-N CCC[Si](C=C(C)C)(NC1CCCC1)[Si](C)(C)C Chemical compound CCC[Si](C=C(C)C)(NC1CCCC1)[Si](C)(C)C FIVYTAHWOCSXHE-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 1
- OXQOAQKYCLYANJ-UHFFFAOYSA-N N,N-dibenzyl-2-(2-methylprop-1-enylsilyl)ethanamine Chemical compound C(C1=CC=CC=C1)N(CC1=CC=CC=C1)CC[SiH2]C=C(C)C OXQOAQKYCLYANJ-UHFFFAOYSA-N 0.000 description 1
- JHISVZCTQQNQCC-UHFFFAOYSA-N N,N-dibenzyl-3-(2-methylprop-1-enylsilyl)propan-1-amine Chemical compound C(C1=CC=CC=C1)N(CC1=CC=CC=C1)CCC[SiH2]C=C(C)C JHISVZCTQQNQCC-UHFFFAOYSA-N 0.000 description 1
- KPHUHUPGJWIUCQ-UHFFFAOYSA-N N,N-diethyl-2-(2-methylprop-1-enylsilyl)ethanamine Chemical compound C(C)N(CC[SiH2]C=C(C)C)CC KPHUHUPGJWIUCQ-UHFFFAOYSA-N 0.000 description 1
- NXFLJLNNAZJRNY-UHFFFAOYSA-N N,N-dimethyl-1-(2-methylprop-1-enylsilyl)methanamine Chemical compound CN(C)C[SiH2]C=C(C)C NXFLJLNNAZJRNY-UHFFFAOYSA-N 0.000 description 1
- VDKHJEYGSIPNTI-UHFFFAOYSA-N N,N-dimethyl-2-(2-methylprop-1-enylsilyl)ethanamine Chemical compound CN(CC[SiH2]C=C(C)C)C VDKHJEYGSIPNTI-UHFFFAOYSA-N 0.000 description 1
- RNHBZYRCBNKESQ-UHFFFAOYSA-N N,N-dimethyl-3-(2-methylprop-1-enylsilyl)propan-1-amine Chemical compound CN(CCC[SiH2]C=C(C)C)C RNHBZYRCBNKESQ-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- ZSTSJTXNYVUGAP-UHFFFAOYSA-N N-(2-methylprop-1-enylsilylmethyl)-2-triethylsilylethanamine Chemical compound C(C)[Si](CC)(CC)CCNC[SiH2]C=C(C)C ZSTSJTXNYVUGAP-UHFFFAOYSA-N 0.000 description 1
- KBAXKQNHCYZOQU-UHFFFAOYSA-N N-(2-methylprop-1-enylsilylmethyl)-2-trimethylsilylethanamine Chemical compound C[Si](C)(C)CCNC[SiH2]C=C(C)C KBAXKQNHCYZOQU-UHFFFAOYSA-N 0.000 description 1
- QEQLNZGUYABZAH-UHFFFAOYSA-N N-(2-methylprop-1-enylsilylmethyl)-3-triethylsilylpropan-1-amine Chemical compound C(C)[Si](CC)(CC)CCCNC[SiH2]C=C(C)C QEQLNZGUYABZAH-UHFFFAOYSA-N 0.000 description 1
- BHCOPWOCZUUBNX-UHFFFAOYSA-N N-(2-methylprop-1-enylsilylmethyl)-3-trimethylsilylpropan-1-amine Chemical compound C[Si](C)(C)CCCNC[SiH2]C=C(C)C BHCOPWOCZUUBNX-UHFFFAOYSA-N 0.000 description 1
- PNCAVGSYYCLTML-UHFFFAOYSA-N N-(2-methylprop-1-enylsilylmethyl)-4-triethylsilylbutan-1-amine Chemical compound C(C)[Si](CC)(CC)CCCCNC[SiH2]C=C(C)C PNCAVGSYYCLTML-UHFFFAOYSA-N 0.000 description 1
- REEGIICCJLWMCO-UHFFFAOYSA-N N-(2-methylprop-1-enylsilylmethyl)-4-trimethylsilylbutan-1-amine Chemical compound C[Si](C)(C)CCCCNC[SiH2]C=C(C)C REEGIICCJLWMCO-UHFFFAOYSA-N 0.000 description 1
- ZFSGKNGSDIMGOS-UHFFFAOYSA-N N-(2-methylprop-1-enylsilylmethyl)-N-phenylaniline Chemical compound C1(=CC=CC=C1)N(C1=CC=CC=C1)C[SiH2]C=C(C)C ZFSGKNGSDIMGOS-UHFFFAOYSA-N 0.000 description 1
- RKTOXNCVEMGWIP-UHFFFAOYSA-N N-(2-methylprop-1-enylsilylmethyl)-N-propan-2-ylpropan-2-amine Chemical compound C(C)(C)N(C(C)C)C[SiH2]C=C(C)C RKTOXNCVEMGWIP-UHFFFAOYSA-N 0.000 description 1
- JDJMEBXBKAVUKK-UHFFFAOYSA-N N-(2-methylprop-1-enylsilylmethyl)-N-propylpropan-1-amine Chemical compound C(CC)N(CCC)C[SiH2]C=C(C)C JDJMEBXBKAVUKK-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- NWFWIGLXTMKCDO-UHFFFAOYSA-N N-[2-(2-methylprop-1-enylsilyl)ethyl]-3-triethylsilylpropan-1-amine Chemical compound C(C)[Si](CC)(CC)CCCNCC[SiH2]C=C(C)C NWFWIGLXTMKCDO-UHFFFAOYSA-N 0.000 description 1
- RZCDEOLMNCZWQC-UHFFFAOYSA-N N-[2-(2-methylprop-1-enylsilyl)ethyl]-4-triethylsilylbutan-1-amine Chemical compound C(C)[Si](CC)(CC)CCCCNCC[SiH2]C=C(C)C RZCDEOLMNCZWQC-UHFFFAOYSA-N 0.000 description 1
- IYPFSHYHSXHLDC-UHFFFAOYSA-N N-[2-(2-methylprop-1-enylsilyl)ethyl]-4-trimethylsilylbutan-1-amine Chemical compound C[Si](C)(C)CCCCNCC[SiH2]C=C(C)C IYPFSHYHSXHLDC-UHFFFAOYSA-N 0.000 description 1
- UXMAHKWAOOMLPK-UHFFFAOYSA-N N-[2-(2-methylprop-1-enylsilyl)ethyl]-N-phenylaniline Chemical compound C1(=CC=CC=C1)N(C1=CC=CC=C1)CC[SiH2]C=C(C)C UXMAHKWAOOMLPK-UHFFFAOYSA-N 0.000 description 1
- FXASQEQAWNRPMR-UHFFFAOYSA-N N-[2-(2-methylprop-1-enylsilyl)ethyl]-N-propan-2-ylpropan-2-amine Chemical compound C(C)(C)N(C(C)C)CC[SiH2]C=C(C)C FXASQEQAWNRPMR-UHFFFAOYSA-N 0.000 description 1
- SFNRTBAPWAGXNB-UHFFFAOYSA-N N-[2-(2-methylprop-1-enylsilyl)ethyl]-N-propylpropan-1-amine Chemical compound C(CC)N(CC[SiH2]C=C(C)C)CCC SFNRTBAPWAGXNB-UHFFFAOYSA-N 0.000 description 1
- ZEWRINZNINIZHR-UHFFFAOYSA-N N-[2-[2-methylprop-1-enyl(triethylsilyl)silyl]ethyl]aniline Chemical compound C(C)[Si](CC)(CC)[SiH](C=C(C)C)CCNC1=CC=CC=C1 ZEWRINZNINIZHR-UHFFFAOYSA-N 0.000 description 1
- BDXGKHPAKAKUQV-UHFFFAOYSA-N N-[2-[2-methylprop-1-enyl(triethylsilyl)silyl]ethyl]butan-2-amine Chemical compound CCC(C)NCC[SiH](C=C(C)C)[Si](CC)(CC)CC BDXGKHPAKAKUQV-UHFFFAOYSA-N 0.000 description 1
- UFOGTUYUXNGNLV-UHFFFAOYSA-N N-[2-[2-methylprop-1-enyl(triethylsilyl)silyl]ethyl]cyclohexanamine Chemical compound C(C)[Si](CC)(CC)[SiH](C=C(C)C)CCNC1CCCCC1 UFOGTUYUXNGNLV-UHFFFAOYSA-N 0.000 description 1
- UPOSBZUWWRFHAB-UHFFFAOYSA-N N-[2-[2-methylprop-1-enyl(triethylsilyl)silyl]ethyl]cyclopentanamine Chemical compound C(C)[Si](CC)(CC)[SiH](C=C(C)C)CCNC1CCCC1 UPOSBZUWWRFHAB-UHFFFAOYSA-N 0.000 description 1
- KNWJCNYSDHBDAS-UHFFFAOYSA-N N-[2-[2-methylprop-1-enyl(triethylsilyl)silyl]ethyl]propan-2-amine Chemical compound CC[Si](CC)(CC)[SiH](C=C(C)C)CCNC(C)C KNWJCNYSDHBDAS-UHFFFAOYSA-N 0.000 description 1
- NJSQHFXSAMMEGN-UHFFFAOYSA-N N-[2-[2-methylprop-1-enyl(trimethylsilyl)silyl]ethyl]aniline Chemical compound C[Si](C)(C)[SiH](C=C(C)C)CCNC1=CC=CC=C1 NJSQHFXSAMMEGN-UHFFFAOYSA-N 0.000 description 1
- BVJAMKBDBFRZPG-UHFFFAOYSA-N N-[2-[2-methylprop-1-enyl(trimethylsilyl)silyl]ethyl]butan-2-amine Chemical compound CCC(C)NCC[SiH]([Si](C)(C)C)C=C(C)C BVJAMKBDBFRZPG-UHFFFAOYSA-N 0.000 description 1
- MLHMDAPFODPHGW-UHFFFAOYSA-N N-[2-[2-methylprop-1-enyl(trimethylsilyl)silyl]ethyl]cyclopentanamine Chemical compound C[Si](C)(C)[SiH](C=C(C)C)CCNC1CCCC1 MLHMDAPFODPHGW-UHFFFAOYSA-N 0.000 description 1
- PZUGDXAYTSKQSS-UHFFFAOYSA-N N-[2-[2-methylprop-1-enyl(trimethylsilyl)silyl]ethyl]propan-2-amine Chemical compound CC(C)NCC[SiH]([Si](C)(C)C)C=C(C)C PZUGDXAYTSKQSS-UHFFFAOYSA-N 0.000 description 1
- LPWLEGREAOPSHB-UHFFFAOYSA-N N-[2-[[tert-butyl(dimethyl)silyl]-(2-methylprop-1-enyl)silyl]ethyl]aniline Chemical compound [Si](C)(C)(C(C)(C)C)[SiH](C=C(C)C)CCNC1=CC=CC=C1 LPWLEGREAOPSHB-UHFFFAOYSA-N 0.000 description 1
- XNTMFYXEOKVLEC-UHFFFAOYSA-N N-[2-[[tert-butyl(dimethyl)silyl]-(2-methylprop-1-enyl)silyl]ethyl]cyclohexanamine Chemical compound [Si](C)(C)(C(C)(C)C)[SiH](C=C(C)C)CCNC1CCCCC1 XNTMFYXEOKVLEC-UHFFFAOYSA-N 0.000 description 1
- XCIRXTWMOXYPSQ-UHFFFAOYSA-N N-[2-[[tert-butyl(dimethyl)silyl]-(2-methylprop-1-enyl)silyl]ethyl]cyclopentanamine Chemical compound [Si](C)(C)(C(C)(C)C)[SiH](C=C(C)C)CCNC1CCCC1 XCIRXTWMOXYPSQ-UHFFFAOYSA-N 0.000 description 1
- FSRSZAZIZDCHLY-UHFFFAOYSA-N N-[2-[[tert-butyl(dimethyl)silyl]-(2-methylprop-1-enyl)silyl]ethyl]propan-2-amine Chemical compound [Si](C)(C)(C(C)(C)C)[SiH](C=C(C)C)CCNC(C)C FSRSZAZIZDCHLY-UHFFFAOYSA-N 0.000 description 1
- VXBNCLIXYUWHQG-UHFFFAOYSA-N N-[2-[tert-butyl(dimethyl)silyl]ethyl]-3-(2-methylprop-1-enylsilyl)propan-1-amine Chemical compound [Si](C)(C)(C(C)(C)C)CCNCCC[SiH2]C=C(C)C VXBNCLIXYUWHQG-UHFFFAOYSA-N 0.000 description 1
- ZZQDATACJKBIJQ-UHFFFAOYSA-N N-[3-(2-methylprop-1-enylsilyl)propyl]-4-triethylsilylbutan-1-amine Chemical compound C(C)[Si](CC)(CC)CCCCNCCC[SiH2]C=C(C)C ZZQDATACJKBIJQ-UHFFFAOYSA-N 0.000 description 1
- PYJKRHTWKDWGKG-UHFFFAOYSA-N N-[3-(2-methylprop-1-enylsilyl)propyl]-4-trimethylsilylbutan-1-amine Chemical compound C[Si](C)(C)CCCCNCCC[SiH2]C=C(C)C PYJKRHTWKDWGKG-UHFFFAOYSA-N 0.000 description 1
- FPVKQBJKNKHPIA-UHFFFAOYSA-N N-[3-(2-methylprop-1-enylsilyl)propyl]-N-phenylaniline Chemical compound C1(=CC=CC=C1)N(C1=CC=CC=C1)CCC[SiH2]C=C(C)C FPVKQBJKNKHPIA-UHFFFAOYSA-N 0.000 description 1
- NWFVECZFIIQZQJ-UHFFFAOYSA-N N-[3-[2-methylprop-1-enyl(triethylsilyl)silyl]propyl]aniline Chemical compound C(C)[Si](CC)(CC)[SiH](C=C(C)C)CCCNC1=CC=CC=C1 NWFVECZFIIQZQJ-UHFFFAOYSA-N 0.000 description 1
- HQHOKDCVAYWGOC-UHFFFAOYSA-N N-[3-[2-methylprop-1-enyl(triethylsilyl)silyl]propyl]butan-2-amine Chemical compound CCC(C)NCCC[SiH](C=C(C)C)[Si](CC)(CC)CC HQHOKDCVAYWGOC-UHFFFAOYSA-N 0.000 description 1
- IOROABLPSCWOMI-UHFFFAOYSA-N N-[3-[2-methylprop-1-enyl(triethylsilyl)silyl]propyl]cyclohexanamine Chemical compound C(C)[Si](CC)(CC)[SiH](C=C(C)C)CCCNC1CCCCC1 IOROABLPSCWOMI-UHFFFAOYSA-N 0.000 description 1
- CNWWDWRRQSOFCR-UHFFFAOYSA-N N-[3-[2-methylprop-1-enyl(triethylsilyl)silyl]propyl]cyclopentanamine Chemical compound C(C)[Si](CC)(CC)[SiH](C=C(C)C)CCCNC1CCCC1 CNWWDWRRQSOFCR-UHFFFAOYSA-N 0.000 description 1
- UEPHJVLRPRXIPM-UHFFFAOYSA-N N-[3-[2-methylprop-1-enyl(trimethylsilyl)silyl]propyl]aniline Chemical compound C[Si](C)(C)[SiH](C=C(C)C)CCCNC1=CC=CC=C1 UEPHJVLRPRXIPM-UHFFFAOYSA-N 0.000 description 1
- FRTXWUJKNNARIM-UHFFFAOYSA-N N-[3-[2-methylprop-1-enyl(trimethylsilyl)silyl]propyl]butan-2-amine Chemical compound CCC(C)NCCC[SiH]([Si](C)(C)C)C=C(C)C FRTXWUJKNNARIM-UHFFFAOYSA-N 0.000 description 1
- ZZHLIUOTJYJQQP-UHFFFAOYSA-N N-[3-[2-methylprop-1-enyl(trimethylsilyl)silyl]propyl]cyclohexanamine Chemical compound C[Si](C)(C)[SiH](C=C(C)C)CCCNC1CCCCC1 ZZHLIUOTJYJQQP-UHFFFAOYSA-N 0.000 description 1
- RYUAHVJFAWOXLC-UHFFFAOYSA-N N-[3-[[tert-butyl(dimethyl)silyl]-(2-methylprop-1-enyl)silyl]propyl]aniline Chemical compound [Si](C)(C)(C(C)(C)C)[SiH](C=C(C)C)CCCNC1=CC=CC=C1 RYUAHVJFAWOXLC-UHFFFAOYSA-N 0.000 description 1
- PAJHSNCQZZWMTB-UHFFFAOYSA-N N-[3-[[tert-butyl(dimethyl)silyl]-(2-methylprop-1-enyl)silyl]propyl]butan-2-amine Chemical compound [Si](C)(C)(C(C)(C)C)[SiH](C=C(C)C)CCCNC(C)CC PAJHSNCQZZWMTB-UHFFFAOYSA-N 0.000 description 1
- QMAKZOLWSPMRER-UHFFFAOYSA-N N-[3-[[tert-butyl(dimethyl)silyl]-(2-methylprop-1-enyl)silyl]propyl]cyclohexanamine Chemical compound [Si](C)(C)(C(C)(C)C)[SiH](C=C(C)C)CCCNC1CCCCC1 QMAKZOLWSPMRER-UHFFFAOYSA-N 0.000 description 1
- CXXVGEZUUVUTGE-UHFFFAOYSA-N N-[3-[[tert-butyl(dimethyl)silyl]-(2-methylprop-1-enyl)silyl]propyl]cyclopentanamine Chemical compound [Si](C)(C)(C(C)(C)C)[SiH](C=C(C)C)CCCNC1CCCC1 CXXVGEZUUVUTGE-UHFFFAOYSA-N 0.000 description 1
- NMBPHFIRMVMTIP-UHFFFAOYSA-N N-[3-[tert-butyl(dimethyl)silyl]propyl]-3-(2-methylprop-1-enylsilyl)propan-1-amine Chemical compound [Si](C)(C)(C(C)(C)C)CCCNCCC[SiH2]C=C(C)C NMBPHFIRMVMTIP-UHFFFAOYSA-N 0.000 description 1
- YGOKWYUHCHBYIV-UHFFFAOYSA-N N-[[2-methylprop-1-enyl(triethylsilyl)silyl]methyl]aniline Chemical compound C(C)[Si](CC)(CC)[SiH](C=C(C)C)CNC1=CC=CC=C1 YGOKWYUHCHBYIV-UHFFFAOYSA-N 0.000 description 1
- HCTQMCJIQAQZFH-UHFFFAOYSA-N N-[[2-methylprop-1-enyl(triethylsilyl)silyl]methyl]cyclohexanamine Chemical compound C(C)[Si](CC)(CC)[SiH](C=C(C)C)CNC1CCCCC1 HCTQMCJIQAQZFH-UHFFFAOYSA-N 0.000 description 1
- QRXITPYWNRAPPL-UHFFFAOYSA-N N-[[2-methylprop-1-enyl(triethylsilyl)silyl]methyl]cyclopentanamine Chemical compound C(C)[Si](CC)(CC)[SiH](C=C(C)C)CNC1CCCC1 QRXITPYWNRAPPL-UHFFFAOYSA-N 0.000 description 1
- ITIZHSUJBBVPNU-UHFFFAOYSA-N N-[[2-methylprop-1-enyl(triethylsilyl)silyl]methyl]propan-2-amine Chemical compound CC[Si](CC)(CC)[SiH](C=C(C)C)CNC(C)C ITIZHSUJBBVPNU-UHFFFAOYSA-N 0.000 description 1
- DIJHZUJMVAFXJX-UHFFFAOYSA-N N-[[2-methylprop-1-enyl(trimethylsilyl)silyl]methyl]aniline Chemical compound C[Si](C)(C)[SiH](C=C(C)C)CNC1=CC=CC=C1 DIJHZUJMVAFXJX-UHFFFAOYSA-N 0.000 description 1
- FMLTWPWDXOJMFN-UHFFFAOYSA-N N-[[2-methylprop-1-enyl(trimethylsilyl)silyl]methyl]butan-2-amine Chemical compound CCC(C)NC[SiH]([Si](C)(C)C)C=C(C)C FMLTWPWDXOJMFN-UHFFFAOYSA-N 0.000 description 1
- KAZHQNUQSKNILU-UHFFFAOYSA-N N-[[2-methylprop-1-enyl(trimethylsilyl)silyl]methyl]cyclohexanamine Chemical compound C[Si](C)(C)[SiH](C=C(C)C)CNC1CCCCC1 KAZHQNUQSKNILU-UHFFFAOYSA-N 0.000 description 1
- VAMISMCTBQRGPH-UHFFFAOYSA-N N-[[2-methylprop-1-enyl(trimethylsilyl)silyl]methyl]propan-2-amine Chemical compound CC(C)NC[SiH]([Si](C)(C)C)C=C(C)C VAMISMCTBQRGPH-UHFFFAOYSA-N 0.000 description 1
- DQYHKILKZRDIAS-UHFFFAOYSA-N N-[[[tert-butyl(dimethyl)silyl]-(2-methylprop-1-enyl)silyl]methyl]aniline Chemical compound [Si](C)(C)(C(C)(C)C)[SiH](C=C(C)C)CNC1=CC=CC=C1 DQYHKILKZRDIAS-UHFFFAOYSA-N 0.000 description 1
- XGYBDKVIOINVSQ-UHFFFAOYSA-N N-[[[tert-butyl(dimethyl)silyl]-(2-methylprop-1-enyl)silyl]methyl]cyclohexanamine Chemical compound [Si](C)(C)(C(C)(C)C)[SiH](C=C(C)C)CNC1CCCCC1 XGYBDKVIOINVSQ-UHFFFAOYSA-N 0.000 description 1
- PBGUASUYWPNGKD-UHFFFAOYSA-N N-[[[tert-butyl(dimethyl)silyl]-(2-methylprop-1-enyl)silyl]methyl]cyclopentanamine Chemical compound [Si](C)(C)(C(C)(C)C)[SiH](C=C(C)C)CNC1CCCC1 PBGUASUYWPNGKD-UHFFFAOYSA-N 0.000 description 1
- PCXUSZICYGVWQK-UHFFFAOYSA-N N-[[[tert-butyl(dimethyl)silyl]-(2-methylprop-1-enyl)silyl]methyl]propan-2-amine Chemical compound [Si](C)(C)(C(C)(C)C)[SiH](C=C(C)C)CNC(C)C PCXUSZICYGVWQK-UHFFFAOYSA-N 0.000 description 1
- HSNLCVISXYJKLD-UHFFFAOYSA-N N-[[tert-butyl(dimethyl)silyl]methyl]-1-(2-methylprop-1-enylsilyl)methanamine Chemical compound [Si](C)(C)(C(C)(C)C)CNC[SiH2]C=C(C)C HSNLCVISXYJKLD-UHFFFAOYSA-N 0.000 description 1
- CTSFKJARDKDXBD-UHFFFAOYSA-N N-[[tert-butyl(dimethyl)silyl]methyl]-2-(2-methylprop-1-enylsilyl)ethanamine Chemical compound [Si](C)(C)(C(C)(C)C)CNCC[SiH2]C=C(C)C CTSFKJARDKDXBD-UHFFFAOYSA-N 0.000 description 1
- AEPVRCUDBCSOOY-UHFFFAOYSA-N N-benzyl-N-(2-methylprop-1-enylsilylmethyl)-1-phenylmethanamine Chemical compound C(C1=CC=CC=C1)N(CC1=CC=CC=C1)C[SiH2]C=C(C)C AEPVRCUDBCSOOY-UHFFFAOYSA-N 0.000 description 1
- YOULXRNAYOOYSV-UHFFFAOYSA-N N-cyclohexyl-N-(2-methylprop-1-enylsilylmethyl)cyclohexanamine Chemical compound C1(CCCCC1)N(C1CCCCC1)C[SiH2]C=C(C)C YOULXRNAYOOYSV-UHFFFAOYSA-N 0.000 description 1
- OLUFJMVCCBIRSY-UHFFFAOYSA-N N-cyclohexyl-N-[2-(2-methylprop-1-enylsilyl)ethyl]cyclohexanamine Chemical compound C1(CCCCC1)N(C1CCCCC1)CC[SiH2]C=C(C)C OLUFJMVCCBIRSY-UHFFFAOYSA-N 0.000 description 1
- VCYYXTFBBYCIMB-UHFFFAOYSA-N N-cyclohexyl-N-[3-(2-methylprop-1-enylsilyl)propyl]cyclohexanamine Chemical compound C1(CCCCC1)N(C1CCCCC1)CCC[SiH2]C=C(C)C VCYYXTFBBYCIMB-UHFFFAOYSA-N 0.000 description 1
- CSFPMIIKMSIJMU-UHFFFAOYSA-N N-cyclopentyl-N-(2-methylprop-1-enylsilylmethyl)cyclopentanamine Chemical compound C1(CCCC1)N(C1CCCC1)C[SiH2]C=C(C)C CSFPMIIKMSIJMU-UHFFFAOYSA-N 0.000 description 1
- SDMZOWMBLQZESM-UHFFFAOYSA-N N-cyclopentyl-N-[2-(2-methylprop-1-enylsilyl)ethyl]cyclopentanamine Chemical compound C1(CCCC1)N(C1CCCC1)CC[SiH2]C=C(C)C SDMZOWMBLQZESM-UHFFFAOYSA-N 0.000 description 1
- ZNUBLZMIBSDBOO-UHFFFAOYSA-N N-cyclopentyl-N-[3-(2-methylprop-1-enylsilyl)propyl]cyclopentanamine Chemical compound C1(CCCC1)N(C1CCCC1)CCC[SiH2]C=C(C)C ZNUBLZMIBSDBOO-UHFFFAOYSA-N 0.000 description 1
- CODRYWATXNLOKU-UHFFFAOYSA-N N-ethyl-N-(2-methylprop-1-enylsilylmethyl)ethanamine Chemical compound C(C)N(CC)C[SiH2]C=C(C)C CODRYWATXNLOKU-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- KMRDNKFDMXCDHO-UHFFFAOYSA-N [2-[3-(2-methylprop-1-enylsilyl)propyl]piperazin-1-yl]-tri(propan-2-yl)silane Chemical compound CC(C)[Si](C(C)C)(C(C)C)N1CCNCC1CCC[SiH2]C=C(C)C KMRDNKFDMXCDHO-UHFFFAOYSA-N 0.000 description 1
- 239000005456 alcohol based solvent Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- QABCGOSYZHCPGN-UHFFFAOYSA-N chloro(dimethyl)silicon Chemical compound C[Si](C)Cl QABCGOSYZHCPGN-UHFFFAOYSA-N 0.000 description 1
- BJLJNLUARMMMLW-UHFFFAOYSA-N chloro-(3-chloropropyl)-dimethylsilane Chemical compound C[Si](C)(Cl)CCCCl BJLJNLUARMMMLW-UHFFFAOYSA-N 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000002704 decyl 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])* 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 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
- 239000003759 ester based solvent Substances 0.000 description 1
- RCNRJBWHLARWRP-UHFFFAOYSA-N ethenyl-[ethenyl(dimethyl)silyl]oxy-dimethylsilane;platinum Chemical compound [Pt].C=C[Si](C)(C)O[Si](C)(C)C=C RCNRJBWHLARWRP-UHFFFAOYSA-N 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- IJMWREDHKRHWQI-UHFFFAOYSA-M magnesium;ethene;chloride Chemical compound [Mg+2].[Cl-].[CH-]=C IJMWREDHKRHWQI-UHFFFAOYSA-M 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N methylimidazole Natural products CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl 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])C([H])([H])[H] 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229920002725 thermoplastic elastomer Polymers 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 125000002306 tributylsilyl group Chemical group C(CCC)[Si](CCCC)(CCCC)* 0.000 description 1
- BVHVIOLPJMKTSW-UHFFFAOYSA-N triethyl-[2-(2-methylprop-1-enylsilylmethyl)piperazin-1-yl]silane Chemical compound CC[Si](CC)(CC)N1CCNCC1C[SiH2]C=C(C)C BVHVIOLPJMKTSW-UHFFFAOYSA-N 0.000 description 1
- RBZKOCOBMHSKBS-UHFFFAOYSA-N triethyl-[2-[2-(2-methylprop-1-enylsilyl)ethyl]piperazin-1-yl]silane Chemical compound CC[Si](CC)(CC)N1CCNCC1CC[SiH2]C=C(C)C RBZKOCOBMHSKBS-UHFFFAOYSA-N 0.000 description 1
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
- NHLKFWGIEIHVHT-UHFFFAOYSA-N trimethyl-[2-(2-methylprop-1-enylsilylmethyl)piperazin-1-yl]silane Chemical compound CC(C)=C[SiH2]CC1CNCCN1[Si](C)(C)C NHLKFWGIEIHVHT-UHFFFAOYSA-N 0.000 description 1
- UBQZTEJTPCQRPX-UHFFFAOYSA-N trimethyl-[2-[2-(2-methylprop-1-enylsilyl)ethyl]piperazin-1-yl]silane Chemical compound CC(C)=C[SiH2]CCC1CNCCN1[Si](C)(C)C UBQZTEJTPCQRPX-UHFFFAOYSA-N 0.000 description 1
- GAOLINVIQCVVAM-UHFFFAOYSA-N trimethyl-[2-[3-(2-methylprop-1-enylsilyl)propyl]piperazin-1-yl]silane Chemical compound CC(C)=C[SiH2]CCCC1CNCCN1[Si](C)(C)C GAOLINVIQCVVAM-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Images
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
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
請求項1:
下記一般式(1)
で示される基並びにピロリジニル基、ピペリジニル基、N−メチルピペラジニル基、N−エチルピペラジニル基、モルホリニル基、N−トリメチルシリルピペラジニル基、N−トリエチルシリルピペラジニル基、N−t−ブチルジメチルシリルピペラジニル基及びN−トリイソプロピルシリルピペラジニル基から選ばれる基であり、nは3〜10の整数である。]
で示されるアミノ基を有するビニルシラン化合物。
請求項2:
下記一般式(4)
で示される基並びにピロリジニル基、ピペリジニル基、N−メチルピペラジニル基、N−エチルピペラジニル基、モルホリニル基、N−トリメチルシリルピペラジニル基、N−トリエチルシリルピペラジニル基、N−t−ブチルジメチルシリルピペラジニル基及びN−トリイソプロピルシリルピペラジニル基から選ばれる基である。]
で示されるアミン化合物0.5〜5.0モルを−20〜200℃において反応させることを特徴とする、請求項1記載のアミノ基を有するビニルシラン化合物の製造方法。
で示される基並びにピロリジニル基、ピペリジニル基、N−メチルピペラジニル基、N−エチルピペラジニル基、モルホリニル基、N−トリメチルシリルピペラジニル基、N−トリエチルシリルピペラジニル基、N−t−ブチルジメチルシリルピペラジニル基及びN−トリイソプロピルシリルピペラジニル基から選ばれる基であり、nは3〜10の整数である。]
で示される化合物である。
で示されるビニルシラン化合物と、下記一般式(5)
で示される基並びにピロリジニル基、ピペリジニル基、N−メチルピペラジニル基、N−エチルピペラジニル基、モルホリニル基、N−トリメチルシリルピペラジニル基、N−トリエチルシリルピペラジニル基、N−t−ブチルジメチルシリルピペラジニル基及びN−トリイソプロピルシリルピペラジニル基から選ばれる基である。]
で示されるアミン化合物を反応させて製造する方法が挙げられる。
ここで、上記一般式(4)で示されるビニルシラン化合物と上記一般式(5)で示されるアミン化合物との配合比は特に限定されないが、反応性、生産性の点から、上記一般式(5)で示されるアミン化合物自身を塩基として捕捉する場合には、ビニルシラン化合物1モルに対し、アミン化合物0.5〜5.0モル、特に0.8〜3.0モルの範囲が好ましく、他のアミン化合物を塩基として捕捉する場合には、0.2〜2.0モル、特に0.3〜1.5モルの範囲が好ましい。
撹拌機、還流冷却器、滴下ロート及び温度計を備えたフラスコに、ビニルマグネシウムクロライドの1.46Mテトラヒドロフラン溶液(500mL、0.73mol)を仕込み、クロロプロピルジメチルクロロシラン(119.8g、0.7mol)を内温25〜50℃で2時間かけて滴下し、その後2時間撹拌した。生じた塩を濾過により除去した後、蒸留した。クロロプロピルジメチルビニルシランを沸点82℃/5kPaの留分として104.4g得た(収率92%)。
撹拌機、還流冷却器、滴下ロート及び温度計を備えたフラスコに、クロロプロピルジメチルビニルシラン(32.5g、0.2mol)を仕込み、130℃に加熱した。内温が安定した後、ジエチルアミン(30.0g、0.41mol)を18時間かけて滴下し、その後10時間撹拌した。生じた塩酸塩を濾過により除去した後、蒸留した。沸点81℃/1kPaの留分を29.7g得た。
質量スペクトル
m/z 199,184,112,86,59
1H−NMRスペクトル(重クロロホルム溶媒)
図1にチャートで示す。
IRスペクトル
図2にチャートで示す。
以上の結果より、得られた化合物はジエチルアミノプロピルジメチルビニルシランであることが確認された。
撹拌機、還流冷却器、滴下ロート及び温度計を備えたフラスコに、N−メチルピペラジン(34.6g、0.345mol)を仕込み、120℃に加熱した。内温が安定した後、クロロプロピルジメチルビニルシラン(24.4g、0.15mol)を2時間かけて滴下し、その後6時間撹拌した。生じた塩酸塩を濾過により除去した後、蒸留した。沸点106℃/0.4kPaの留分を28.4g得た。
質量スペクトル
m/z 226,211,113,70,42
1H−NMRスペクトル(重クロロホルム溶媒)
図3にチャートで示す。
IRスペクトル
図4にチャートで示す。
以上の結果より、得られた化合物はN−メチルピペラジニルプロピルジメチルビニルシランであることが確認された。
撹拌機、還流冷却器、滴下ロート及び温度計を備えたフラスコに、ビストリメチルシリルアリルアミン201.5g(1.0mol)、白金−1,3−ジビニル−1,1,3,3−テトラメチルジシロキサン錯体のトルエン溶液(白金含量3wt%)0.7gを仕込み、ジメチルクロロシラン99.3g(1.05mol)を内温60〜70℃で2時間かけて滴下し、その温度で1時間撹拌した。反応液を蒸留し、ビストリメチルシリルアミノプロピルジメチルクロロシランを沸点68℃/30Paの留分として268.0g得た(収率91%)。
Claims (2)
- 下記一般式(1)
で示される基並びにピロリジニル基、ピペリジニル基、N−メチルピペラジニル基、N−エチルピペラジニル基、モルホリニル基、N−トリメチルシリルピペラジニル基、N−トリエチルシリルピペラジニル基、N−t−ブチルジメチルシリルピペラジニル基及びN−トリイソプロピルシリルピペラジニル基から選ばれる基であり、nは3〜10の整数である。]
で示されるアミノ基を有するビニルシラン化合物。 - 下記一般式(4)
で示される基並びにピロリジニル基、ピペリジニル基、N−メチルピペラジニル基、N−エチルピペラジニル基、モルホリニル基、N−トリメチルシリルピペラジニル基、N−トリエチルシリルピペラジニル基、N−t−ブチルジメチルシリルピペラジニル基及びN−トリイソプロピルシリルピペラジニル基から選ばれる基である。]
で示されるアミン化合物0.5〜5.0モルを−20〜200℃において反応させることを特徴とする、請求項1記載のアミノ基を有するビニルシラン化合物の製造方法。
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2009142049A JP5088510B2 (ja) | 2009-06-15 | 2009-06-15 | アミノ基を有するビニルシラン化合物及びその製造方法 |
US12/797,721 US8436166B2 (en) | 2009-06-15 | 2010-06-10 | Amino-containing vinylsilane compounds and making method |
EP10006144.9A EP2287170B1 (en) | 2009-06-15 | 2010-06-14 | Amino-containing vinylsilane compounds and method of making the same |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2009142049A JP5088510B2 (ja) | 2009-06-15 | 2009-06-15 | アミノ基を有するビニルシラン化合物及びその製造方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2010285405A JP2010285405A (ja) | 2010-12-24 |
JP5088510B2 true JP5088510B2 (ja) | 2012-12-05 |
Family
ID=43216721
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2009142049A Active JP5088510B2 (ja) | 2009-06-15 | 2009-06-15 | アミノ基を有するビニルシラン化合物及びその製造方法 |
Country Status (3)
Country | Link |
---|---|
US (1) | US8436166B2 (ja) |
EP (1) | EP2287170B1 (ja) |
JP (1) | JP5088510B2 (ja) |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP5316459B2 (ja) * | 2010-03-30 | 2013-10-16 | 住友化学株式会社 | 共役ジエン系重合体、共役ジエン系重合体組成物、及び、共役ジエン系重合体の製造方法 |
DE102011109823B4 (de) * | 2010-08-11 | 2023-10-12 | Sumitomo Chemical Company, Limited | Polymer auf Basis von konjugiertem Dien, Polymerzusammensetzung auf Basis von konjugiertem Dien und Verfahren zur Herstellung von Polymer auf Basis von konjugiertem Dien |
DE102011109827A1 (de) * | 2010-08-11 | 2012-02-16 | Sumitomo Chemical Company, Ltd. | Polymer auf Basis von konjugiertem Dien, Polymerzusammensetzung auf Basis von konjugiertem Dien und Verfahren zur Herstellung von Polymer auf Basis von konjugiertem Dien |
JP2013209462A (ja) * | 2012-03-30 | 2013-10-10 | Sumitomo Chemical Co Ltd | 共役ジエン系重合体、重合体組成物、及び、共役ジエン系重合体の製造方法 |
US9790359B2 (en) | 2012-06-08 | 2017-10-17 | Sumitomo Rubber Industries, Ltd. | Tread rubber composition and pneumatic tire |
JP6702136B2 (ja) * | 2016-10-28 | 2020-05-27 | 信越化学工業株式会社 | ビスシリルアミノ基を有するシラン化合物の製造方法 |
JP6720913B2 (ja) * | 2017-04-18 | 2020-07-08 | 信越化学工業株式会社 | 不飽和結合含有ビスシリル化合物およびその製造方法 |
JP7476777B2 (ja) | 2020-11-30 | 2024-05-01 | 信越化学工業株式会社 | 含窒素オルガノキシシラン化合物の製造方法 |
EP4186911A1 (en) | 2021-11-30 | 2023-05-31 | Trinseo Europe GmbH | Amine-containing vinyldisiloxanes in the manufacture of elastomeric polymers |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3853994A (en) * | 1971-12-09 | 1974-12-10 | Sandoz Ag | Diphenyl(3-di alkylaminopropyl)silanes as therapeutics |
JPS6058760B2 (ja) * | 1977-12-29 | 1985-12-21 | 東レ株式会社 | ビニルシリル基を有するアミンおよびその塩 |
JPH0739427B2 (ja) * | 1987-04-03 | 1995-05-01 | 信越化学工業株式会社 | モノアルコキシシラン化合物の製造方法 |
JPH02270889A (ja) * | 1989-04-12 | 1990-11-05 | Rikagaku Kenkyusho | 有機けい素化合物及びその製造方法 |
JPH04149183A (ja) * | 1990-10-15 | 1992-05-22 | Rikagaku Kenkyusho | 殺菌性シラン化合物とその製造方法、菌類による病気の抑制剤及び菌類による病気の抑制方法 |
JPH0525184A (ja) | 1991-07-23 | 1993-02-02 | Rikagaku Kenkyusho | 新規なシラン化合物、その製造方法、及びそれを含有する植物生長調節剤 |
JP3368651B2 (ja) | 1994-02-18 | 2003-01-20 | 昭和電工株式会社 | 変性ポリオレフィン系樹脂組成物 |
JP3972162B2 (ja) * | 1998-12-16 | 2007-09-05 | 信越化学工業株式会社 | イソシアナト基含有有機ケイ素化合物類の製造方法 |
JP2003073503A (ja) | 2001-08-31 | 2003-03-12 | Sumitomo Chem Co Ltd | 熱可塑性エラストマー組成物 |
JP4172971B2 (ja) | 2002-09-04 | 2008-10-29 | 株式会社プライムポリマー | 変性ポリプロピレン系樹脂組成物及びその製造方法 |
-
2009
- 2009-06-15 JP JP2009142049A patent/JP5088510B2/ja active Active
-
2010
- 2010-06-10 US US12/797,721 patent/US8436166B2/en active Active
- 2010-06-14 EP EP10006144.9A patent/EP2287170B1/en active Active
Also Published As
Publication number | Publication date |
---|---|
US20100317852A1 (en) | 2010-12-16 |
US8436166B2 (en) | 2013-05-07 |
EP2287170B1 (en) | 2014-04-02 |
EP2287170A1 (en) | 2011-02-23 |
JP2010285405A (ja) | 2010-12-24 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5088510B2 (ja) | アミノ基を有するビニルシラン化合物及びその製造方法 | |
JP5407825B2 (ja) | 2以上のアミノ基を有するシラン化合物及びその製造方法 | |
CN102146091B (zh) | 双硅烷偶联剂及其制备方法 | |
JP5115729B2 (ja) | トリアルキルシリル基で保護されたアセト酢酸エステル基含有有機ケイ素化合物及びその製造方法 | |
JP6264309B2 (ja) | シロキシ基を有するビスシリルエタン化合物及びその製造方法 | |
JP2013231009A (ja) | シリル基で保護された2級アミノ基を有するオルガノキシシラン化合物及びその製造方法 | |
KR101888691B1 (ko) | 아미노산 변성 실란 화합물 및 그의 제조 방법 | |
JP6942459B2 (ja) | カルボン酸シリルエステル基含有アルコキシシラン化合物およびその製造方法 | |
JP5359185B2 (ja) | アミノ基と保護された水酸基を有する有機ケイ素化合物及びその製造方法 | |
JP6044361B2 (ja) | ジクロロモノヒドロシラン化合物の製造方法 | |
JP6303982B2 (ja) | 新規ビスアルコキシアミノシラン化合物及びその製造方法 | |
JP4344936B2 (ja) | 両末端アミノ基含有有機ケイ素化合物の製造方法 | |
JP5699990B2 (ja) | ピペラジニル基を有するオルガノキシシラン化合物の製造方法及びピペラジン化合物 | |
JP7416927B2 (ja) | ヒドリドシリコン化合物からのシロキサンの調製方法 | |
JP4662042B2 (ja) | シリル基で保護されたアミノ基を有するビスオルガノキシシラン化合物及びその製造方法 | |
JP6690598B2 (ja) | イミン構造含有環状有機ケイ素化合物およびその製造方法 | |
JP5644515B2 (ja) | 不飽和結合含有シリル基保護アミノ酸化合物及びその製造方法 | |
TW201533113A (zh) | 包含含氮有機氧矽烷化合物的組成物及其製造方法 | |
JP6020410B2 (ja) | [3−(2−ノルボルニル)−2−ノルボルニル]シラン化合物及びその製造方法 | |
JP6207287B2 (ja) | シリル基含有ノルボルネン化合物及びその製造方法 | |
JP2020147588A (ja) | カルボン酸シリルエステル基含有アルコキシシラン化合物およびその製造方法 | |
JP6201957B2 (ja) | N−シリルピペラジンの製造方法 | |
JPH02300192A (ja) | 3―[n―(2―アミノエチル)]アミノプロピルアルコキシシランの製造方法 | |
JP2014009110A (ja) | 2−トリクロロシリルノルボルナンの製造方法 | |
TW201843163A (zh) | 含有不飽和鍵結之雙甲矽烷基化合物及其製造方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20110527 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20111109 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20120106 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20120704 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20120725 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20120815 |
|
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20120828 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20150921 Year of fee payment: 3 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 5088510 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 Free format text: JAPANESE INTERMEDIATE CODE: R150 |