TW202016122A - 環狀胺基有機氧矽烷化合物及其製造方法 - Google Patents
環狀胺基有機氧矽烷化合物及其製造方法 Download PDFInfo
- Publication number
- TW202016122A TW202016122A TW108121268A TW108121268A TW202016122A TW 202016122 A TW202016122 A TW 202016122A TW 108121268 A TW108121268 A TW 108121268A TW 108121268 A TW108121268 A TW 108121268A TW 202016122 A TW202016122 A TW 202016122A
- Authority
- TW
- Taiwan
- Prior art keywords
- aza
- oxa
- compound
- substituted
- hydrocarbon group
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 49
- 125000004122 cyclic group Chemical group 0.000 title claims abstract description 7
- 238000000034 method Methods 0.000 title description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 16
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 8
- 239000003054 catalyst Substances 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 239000003377 acid catalyst Substances 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 150000002927 oxygen compounds Chemical class 0.000 claims description 2
- -1 cyclic amine Chemical class 0.000 description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 150000002430 hydrocarbons Chemical group 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 239000000654 additive Substances 0.000 description 14
- 239000002904 solvent Substances 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 230000000996 additive effect Effects 0.000 description 10
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 8
- 125000003277 amino group Chemical group 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
- 239000006087 Silane Coupling Agent Substances 0.000 description 7
- 239000000853 adhesive Substances 0.000 description 7
- 230000001070 adhesive effect Effects 0.000 description 7
- 238000002329 infrared spectrum Methods 0.000 description 7
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- 239000012756 surface treatment agent Substances 0.000 description 7
- TZZGHGKTHXIOMN-UHFFFAOYSA-N 3-trimethoxysilyl-n-(3-trimethoxysilylpropyl)propan-1-amine Chemical compound CO[Si](OC)(OC)CCCNCCC[Si](OC)(OC)OC TZZGHGKTHXIOMN-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
- 229910000077 silane Inorganic materials 0.000 description 6
- 239000012295 chemical reaction liquid Substances 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 239000003973 paint Substances 0.000 description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 238000001819 mass spectrum Methods 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 150000004756 silanes Chemical class 0.000 description 3
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- VWDYLHIOWPIFJQ-UHFFFAOYSA-N 3-[8-(butoxymethyl)-2,2-dimethoxy-1,6,2-oxazasilocan-6-yl]propyl-trimethoxysilane Chemical compound CO[Si]1(OC(CN(CCC1)CCC[Si](OC)(OC)OC)COCCCC)OC VWDYLHIOWPIFJQ-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- HPEUJPJOZXNMSJ-UHFFFAOYSA-N Methyl stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC HPEUJPJOZXNMSJ-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 239000005456 alcohol based solvent Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 239000003759 ester based solvent Substances 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- CBFCDTFDPHXCNY-UHFFFAOYSA-N icosane Chemical compound CCCCCCCCCCCCCCCCCCCC CBFCDTFDPHXCNY-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RZJRJXONCZWCBN-UHFFFAOYSA-N octadecane Chemical compound CCCCCCCCCCCCCCCCCC RZJRJXONCZWCBN-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 150000003335 secondary amines Chemical group 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 125000005369 trialkoxysilyl group Chemical group 0.000 description 2
- 125000004665 trialkylsilyl group Chemical group 0.000 description 2
- IIYFAKIEWZDVMP-UHFFFAOYSA-N tridecane Chemical compound CCCCCCCCCCCCC IIYFAKIEWZDVMP-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 description 1
- IXXVBQADWKMFNM-UHFFFAOYSA-N 1,6,2-oxazasilocane Chemical compound [SiH2]1OCCNCCC1 IXXVBQADWKMFNM-UHFFFAOYSA-N 0.000 description 1
- FPJORUPSZCUHTP-UHFFFAOYSA-N 1-(diethoxymethylsilyl)-N-(diethoxymethylsilylmethyl)methanamine Chemical compound CCOC(OCC)[SiH2]CNC[SiH2]C(OCC)OCC FPJORUPSZCUHTP-UHFFFAOYSA-N 0.000 description 1
- SKSIZVCLPCSRBE-UHFFFAOYSA-N 1-(dimethoxymethylsilyl)-N-(dimethoxymethylsilylmethyl)methanamine Chemical compound COC(OC)[SiH2]CNC[SiH2]C(OC)OC SKSIZVCLPCSRBE-UHFFFAOYSA-N 0.000 description 1
- 239000005968 1-Decanol Substances 0.000 description 1
- UQWZCMQMNCPNIZ-UHFFFAOYSA-N 1-dimethylsilyl-N-[dimethylsilyl(ethoxy)methyl]-1-ethoxymethanamine Chemical compound C(C)OC([SiH](C)C)NC(OCC)[SiH](C)C UQWZCMQMNCPNIZ-UHFFFAOYSA-N 0.000 description 1
- OYWKBIVCHPPAOQ-UHFFFAOYSA-N 1-triethoxysilyl-n-(triethoxysilylmethyl)methanamine Chemical compound CCO[Si](OCC)(OCC)CNC[Si](OCC)(OCC)OCC OYWKBIVCHPPAOQ-UHFFFAOYSA-N 0.000 description 1
- PRVIBJDSXWYIIO-UHFFFAOYSA-N 1-trimethoxysilyl-n-(trimethoxysilylmethyl)methanamine Chemical compound CO[Si](OC)(OC)CNC[Si](OC)(OC)OC PRVIBJDSXWYIIO-UHFFFAOYSA-N 0.000 description 1
- XULHFMYCBKQGEE-MRXNPFEDSA-N 2-Hexyl-1-decanol Natural products CCCCCCCC[C@H](CO)CCCCCC XULHFMYCBKQGEE-MRXNPFEDSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 1
- XULHFMYCBKQGEE-UHFFFAOYSA-N 2-hexyl-1-Decanol Chemical compound CCCCCCCCC(CO)CCCCCC XULHFMYCBKQGEE-UHFFFAOYSA-N 0.000 description 1
- YKQFFWZLUJYSEF-UHFFFAOYSA-N 3-(diethoxymethylsilyl)-N-[3-(diethoxymethylsilyl)propyl]propan-1-amine Chemical compound CCOC(OCC)[SiH2]CCCNCCC[SiH2]C(OCC)OCC YKQFFWZLUJYSEF-UHFFFAOYSA-N 0.000 description 1
- HABPAQBWFBTKLG-UHFFFAOYSA-N 3-[2,2-diethoxy-8-(phenoxymethyl)-1,6,2-oxazasilocan-6-yl]propyl-triethoxysilane Chemical compound C(C)O[Si]1(OC(CN(CCC1)CCC[Si](OCC)(OCC)OCC)COC1=CC=CC=C1)OCC HABPAQBWFBTKLG-UHFFFAOYSA-N 0.000 description 1
- FHPGQDOMJBMGJV-UHFFFAOYSA-N 3-[2,2-dimethoxy-8-(methoxymethyl)-1,6,2-oxazasilocan-6-yl]propyl-trimethoxysilane Chemical compound CO[Si]1(OC(CN(CCC1)CCC[Si](OC)(OC)OC)COC)OC FHPGQDOMJBMGJV-UHFFFAOYSA-N 0.000 description 1
- COVCYFCUXGDUQX-UHFFFAOYSA-N 3-[2,2-dimethoxy-8-(phenoxymethyl)-1,6,2-oxazasilocan-6-yl]propyl-trimethoxysilane Chemical compound CO[Si]1(OC(CN(CCC1)CCC[Si](OC)(OC)OC)COC1=CC=CC=C1)OC COVCYFCUXGDUQX-UHFFFAOYSA-N 0.000 description 1
- LACFTRKBGCCSNH-UHFFFAOYSA-N 3-[8-(butoxymethyl)-2,2-diethoxy-1,6,2-oxazasilocan-6-yl]propyl-triethoxysilane Chemical compound C(C)O[Si]1(OC(CN(CCC1)CCC[Si](OCC)(OCC)OCC)COCCCC)OCC LACFTRKBGCCSNH-UHFFFAOYSA-N 0.000 description 1
- ZJSWNHUDWMIHOT-UHFFFAOYSA-N 3-dimethylsilyl-N-(3-dimethylsilyl-3-ethoxypropyl)-3-ethoxypropan-1-amine Chemical compound C(C)OC(CCNCCC(OCC)[SiH](C)C)[SiH](C)C ZJSWNHUDWMIHOT-UHFFFAOYSA-N 0.000 description 1
- GCJXPPXICWUUQP-UHFFFAOYSA-N 3-dimethylsilyl-N-(3-dimethylsilyl-3-methoxypropyl)-3-methoxypropan-1-amine Chemical compound COC(CCNCCC(OC)[SiH](C)C)[SiH](C)C GCJXPPXICWUUQP-UHFFFAOYSA-N 0.000 description 1
- RWLDCNACDPTRMY-UHFFFAOYSA-N 3-triethoxysilyl-n-(3-triethoxysilylpropyl)propan-1-amine Chemical compound CCO[Si](OCC)(OCC)CCCNCCC[Si](OCC)(OCC)OCC RWLDCNACDPTRMY-UHFFFAOYSA-N 0.000 description 1
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 1
- QMULOJQODCVJAF-UHFFFAOYSA-N COC(OC)[SiH2]CCCNCCC[SiH2]C(OC)OC Chemical compound COC(OC)[SiH2]CCCNCCC[SiH2]C(OC)OC QMULOJQODCVJAF-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- QFHMNFAUXJAINK-UHFFFAOYSA-N [1-(carbamoylamino)-2-methylpropyl]urea Chemical group NC(=O)NC(C(C)C)NC(N)=O QFHMNFAUXJAINK-UHFFFAOYSA-N 0.000 description 1
- UBRVKJKARIKHNY-UHFFFAOYSA-N [1-ethoxy-3-[8-(methoxymethyl)-2,2-dimethyl-1,6,2-oxazasilocan-6-yl]propyl]-dimethylsilane Chemical compound C[Si]1(OC(CN(CCC1)CCC(OCC)[SiH](C)C)COC)C UBRVKJKARIKHNY-UHFFFAOYSA-N 0.000 description 1
- ALMLUHQMKDFVDR-UHFFFAOYSA-N [1-methoxy-3-[8-(methoxymethyl)-2,2-dimethyl-1,6,2-oxazasilocan-6-yl]propyl]-dimethylsilane Chemical compound C[Si]1(OC(CN(CCC1)CCC(OC)[SiH](C)C)COC)C ALMLUHQMKDFVDR-UHFFFAOYSA-N 0.000 description 1
- HKVPJMTZUKDTTF-UHFFFAOYSA-N [2,2-dimethoxy-6-(methoxymethyl)-1,4,2-oxazasilinan-4-yl]methyl-trimethoxysilane Chemical compound CO[Si]1(OC(CN(C1)C[Si](OC)(OC)OC)COC)OC HKVPJMTZUKDTTF-UHFFFAOYSA-N 0.000 description 1
- XRQZRKHFUKKSAP-UHFFFAOYSA-N [2,2-dimethoxy-6-(phenoxymethyl)-1,4,2-oxazasilinan-4-yl]methyl-trimethoxysilane Chemical compound CO[Si]1(OC(CN(C1)C[Si](OC)(OC)OC)COC1=CC=CC=C1)OC XRQZRKHFUKKSAP-UHFFFAOYSA-N 0.000 description 1
- BCEVGOVDRKPDMX-UHFFFAOYSA-N [3-[2,2-dimethyl-8-(phenoxymethyl)-1,6,2-oxazasilocan-6-yl]-1-methoxypropyl]-dimethylsilane Chemical compound C[Si]1(OC(CN(CCC1)CCC(OC)[SiH](C)C)COC1=CC=CC=C1)C BCEVGOVDRKPDMX-UHFFFAOYSA-N 0.000 description 1
- SULRPYOKVHRXPV-UHFFFAOYSA-N [3-[8-(butoxymethyl)-2,2-dimethyl-1,6,2-oxazasilocan-6-yl]-1-methoxypropyl]-dimethylsilane Chemical compound C[Si]1(OC(CN(CCC1)CCC(OC)[SiH](C)C)COCCCC)C SULRPYOKVHRXPV-UHFFFAOYSA-N 0.000 description 1
- HNXGBRNRGLRGBM-UHFFFAOYSA-N [6-(butoxymethyl)-2,2-diethoxy-1,4,2-oxazasilinan-4-yl]methyl-triethoxysilane Chemical compound C(C)O[Si]1(OC(CN(C1)C[Si](OCC)(OCC)OCC)COCCCC)OCC HNXGBRNRGLRGBM-UHFFFAOYSA-N 0.000 description 1
- IPGMQYRHMABODY-UHFFFAOYSA-N [6-(butoxymethyl)-2,2-dimethoxy-1,4,2-oxazasilinan-4-yl]methyl-trimethoxysilane Chemical compound CO[Si]1(OC(CN(C1)C[Si](OC)(OC)OC)COCCCC)OC IPGMQYRHMABODY-UHFFFAOYSA-N 0.000 description 1
- NMZDGBAFRNYKFY-UHFFFAOYSA-N [6-(butoxymethyl)-2-ethoxy-2-methyl-1,4,2-oxazasilinan-4-yl]methyl-(diethoxymethyl)silane Chemical compound C(C)O[Si]1(OC(CN(C1)C[SiH2]C(OCC)OCC)COCCCC)C NMZDGBAFRNYKFY-UHFFFAOYSA-N 0.000 description 1
- ZZDNFYILCSYOIN-UHFFFAOYSA-N [6-(butoxymethyl)-2-methoxy-2-methyl-1,4,2-oxazasilinan-4-yl]methyl-(dimethoxymethyl)silane Chemical compound CO[Si]1(OC(CN(C1)C[SiH2]C(OC)OC)COCCCC)C ZZDNFYILCSYOIN-UHFFFAOYSA-N 0.000 description 1
- ZIVLZGARONIHLN-UHFFFAOYSA-N [[2,2-dimethyl-6-(phenoxymethyl)-1,4,2-oxazasilinan-4-yl]-ethoxymethyl]-dimethylsilane Chemical compound C[Si]1(OC(CN(C1)C([SiH](C)C)OCC)COC1=CC=CC=C1)C ZIVLZGARONIHLN-UHFFFAOYSA-N 0.000 description 1
- DVFPJPBCGLKCTQ-UHFFFAOYSA-N [[2,2-dimethyl-6-(phenoxymethyl)-1,4,2-oxazasilinan-4-yl]-methoxymethyl]-dimethylsilane Chemical compound C[Si]1(OC(CN(C1)C([SiH](C)C)OC)COC1=CC=CC=C1)C DVFPJPBCGLKCTQ-UHFFFAOYSA-N 0.000 description 1
- YFYJSEHRHBEJND-UHFFFAOYSA-N [[6-(butoxymethyl)-2,2-dimethyl-1,4,2-oxazasilinan-4-yl]-ethoxymethyl]-dimethylsilane Chemical compound C[Si]1(OC(CN(C1)C([SiH](C)C)OCC)COCCCC)C YFYJSEHRHBEJND-UHFFFAOYSA-N 0.000 description 1
- DWWJJSYSVSFLQZ-UHFFFAOYSA-N [[6-(butoxymethyl)-2,2-dimethyl-1,4,2-oxazasilinan-4-yl]-methoxymethyl]-dimethylsilane Chemical compound C[Si]1(OC(CN(C1)C([SiH](C)C)OC)COCCCC)C DWWJJSYSVSFLQZ-UHFFFAOYSA-N 0.000 description 1
- WISNTFLZDGVJDM-UHFFFAOYSA-N [ethoxy-[6-(methoxymethyl)-2,2-dimethyl-1,4,2-oxazasilinan-4-yl]methyl]-dimethylsilane Chemical compound C[Si]1(OC(CN(C1)C([SiH](C)C)OCC)COC)C WISNTFLZDGVJDM-UHFFFAOYSA-N 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000001204 arachidyl 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])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])[H] 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 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
- AGSFIZDITVHDFK-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.OC.ClC(Cl)Cl AGSFIZDITVHDFK-UHFFFAOYSA-N 0.000 description 1
- SLLGVCUQYRMELA-UHFFFAOYSA-N chlorosilicon Chemical group Cl[Si] SLLGVCUQYRMELA-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- DIOQZVSQGTUSAI-NJFSPNSNSA-N decane Chemical compound CCCCCCCCC[14CH3] DIOQZVSQGTUSAI-NJFSPNSNSA-N 0.000 description 1
- RMJMOWGPJXIZEV-UHFFFAOYSA-N diethoxymethyl-[3-[2-ethoxy-2-methyl-8-(phenoxymethyl)-1,6,2-oxazasilocan-6-yl]propyl]silane Chemical compound C(C)O[Si]1(OC(CN(CCC1)CCC[SiH2]C(OCC)OCC)COC1=CC=CC=C1)C RMJMOWGPJXIZEV-UHFFFAOYSA-N 0.000 description 1
- KGXWJMCNZSSLTJ-UHFFFAOYSA-N diethoxymethyl-[3-[2-ethoxy-8-(methoxymethyl)-2-methyl-1,6,2-oxazasilocan-6-yl]propyl]silane Chemical compound C(C)O[Si]1(OC(CN(CCC1)CCC[SiH2]C(OCC)OCC)COC)C KGXWJMCNZSSLTJ-UHFFFAOYSA-N 0.000 description 1
- YLNFKVCCOBIPEH-UHFFFAOYSA-N dimethoxymethyl-[3-[2-methoxy-2-methyl-8-(phenoxymethyl)-1,6,2-oxazasilocan-6-yl]propyl]silane Chemical compound CO[Si]1(OC(CN(CCC1)CCC[SiH2]C(OC)OC)COC1=CC=CC=C1)C YLNFKVCCOBIPEH-UHFFFAOYSA-N 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
- KWKXNDCHNDYVRT-UHFFFAOYSA-N dodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- QYDYPVFESGNLHU-UHFFFAOYSA-N elaidic acid methyl ester Natural products CCCCCCCCC=CCCCCCCCC(=O)OC QYDYPVFESGNLHU-UHFFFAOYSA-N 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- CAMHHLOGFDZBBG-UHFFFAOYSA-N epoxidized methyl oleate Natural products CCCCCCCCC1OC1CCCCCCCC(=O)OC CAMHHLOGFDZBBG-UHFFFAOYSA-N 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 description 1
- 229940073769 methyl oleate Drugs 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000001421 myristyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QIOYHIUHPGORLS-UHFFFAOYSA-N n,n-dimethyl-3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN(C)C QIOYHIUHPGORLS-UHFFFAOYSA-N 0.000 description 1
- KBJFYLLAMSZSOG-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)aniline Chemical compound CO[Si](OC)(OC)CCCNC1=CC=CC=C1 KBJFYLLAMSZSOG-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- DIOQZVSQGTUSAI-UHFFFAOYSA-N n-butylhexane Natural products CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 1
- 125000003136 n-heptyl 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])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229940038384 octadecane Drugs 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 125000000913 palmityl 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])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
- 229920000642 polymer Polymers 0.000 description 1
- 150000003141 primary amines Chemical group 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000004079 stearyl 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])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])[H] 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
- C07F7/18—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
-
- 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
- C07F7/188—Preparation; Treatments not provided for in C07F7/20 by reactions involving the formation of Si-O linkages
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/60—Additives non-macromolecular
- C09D7/63—Additives non-macromolecular organic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/549—Silicon-containing compounds containing silicon in a ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
本發明關於環狀胺基有機氧矽烷化合物及其製造方法,若更詳述,則關於作為矽烷偶合劑、表面處理劑、樹脂添加劑、塗料添加劑、接著劑等為有用的環狀胺基有機氧矽烷化合物及其製造方法。
具有胺基的矽烷化合物作為矽烷偶合劑、表面處理劑、樹脂添加劑、塗料添加劑、接著劑等為有用,作為這樣的具有胺基的矽烷化合物,已知例如胺基丙基三甲氧基矽烷等之具有1級胺基的有機氧矽烷化合物、N-苯基胺基丙基三甲氧基矽烷等之具有2級胺基的有機氧矽烷化合物、二甲基胺基丙基三甲氧基矽烷等之具有3級胺基的有機氧矽烷化合物等。
然而,此等矽烷化合物由於每1分子僅具有胺基與有機氧矽基各自1個,故作為矽烷偶合劑、表面處理劑、樹脂添加劑、塗料添加劑、接著劑等使用時,有官能基導入所致的效果之展現少的情況。
為了解決上述問題,提案有具有分子內有機氧矽基之3級胺基矽烷化合物(參照專利文獻1、3)或具有分子內有機氧矽基之2級胺基矽烷化合物(參照專利文獻2)等。
此等化合物係藉由與空氣中的水分反應,而除了原本具有的胺基之外,還生成羥基,上述官能基導入所致的效果變高。又,分子內有機氧基部分係在與空氣中的水分反應之際,由於不生成甲醇或乙醇等的低沸點醇,故亦有用作為環境負荷少的化合物。
再者,作為具有複數的有機氧矽基之化合物,提案有具有2個有機氧矽基、1個2級胺基之雙(三甲氧基矽基丙基)胺,已知藉由添加可形成交聯網絡。
[先前技術文獻]
[專利文獻]
[專利文獻1] 日本特開2010-120925號公報
[專利文獻2] 日本特開2010-285406號公報
[專利文獻3] 日本特開2014-001152號公報
[發明所欲解決的課題]
然而,引用文獻1~3之化合物皆在作為每1分子的官能基,僅具有1個胺基、1個與空氣中的水分反應而生成的羥基及1個有機氧矽基。又,於雙(三甲氧基矽基丙基)胺之情況中,雖然具有2個有機氧矽基、1個胺基作為官能基,但是近年來,於矽烷偶合劑、表面處理劑、樹脂添加劑、塗料添加劑、接著劑等中,隨著其使用目的之多樣化,要求添加效果更高的矽烷化合物,使用引用文獻1~3之化合物或雙(三甲氧基矽基丙基)胺時,有添加效果低之情況,未必能得到充分的添加效果。
本發明係鑒於上述情事而完成者,目的在於提供一種矽烷化合物及一種其製造方法,該矽烷化合物係在作為矽烷偶合劑、表面處理劑、樹脂添加劑、塗料添加劑、接著劑等而使用時,添加效果更高,且在使用時低沸點醇的產生減少。
[解決課題的手段]
本發明者為了達成上述目的而重複專心致力的檢討,結果發現特定之環狀胺基有機氧矽烷化合物係在作為矽烷偶合劑、表面處理劑、樹脂添加劑、塗料添加劑、接著劑等而使用時,添加效果更高,且在使用時低沸點醇的產生變更少,而完成本發明。
即,本發明提供:
1.一種下述通式(1)所示的環狀胺基有機氧矽烷化合物,
(式中,R1
表示取代或未取代之碳數1~20的1價烴基,R2
~R5
各自獨立地表示取代或未取代之碳數1~20的1價烴基,R6
~R8
各自獨立地表示氫原子或取代或未取代之碳數1~20的1價烴基,R9
及R10
各自獨立地表示可含有雜原子的取代或未取代之碳數1~20的2價烴基,m為0、1或2,n為0或1)。
2.一種如1之環狀胺基有機氧矽烷化合物之製造方法,其係蒸餾使下述通式(2)所示的胺基有機氧矽烷化合物與下述通式(3)所示的環氧化合物反應而得之反應混合物,
(式中,R2
~R5
、R9
、R10
、m及n表示與前述相同的定義);
(式中,R1
、R6
~R8
表示與前述相同的定義)。
3.如2之環狀胺基有機氧矽烷化合物之製造方法,其中於鹼性觸媒或酸性觸媒之存在下蒸餾反應混合物。
[發明的效果]
與習知的化合物比較下,本發明之環狀胺基有機氧矽烷化合物由於添加效果變高,故作為矽烷偶合劑、表面處理劑、樹脂添加劑、塗料添加劑、接著劑等為有用。
[實施發明的形態]
以下,具體地說明本發明。
本發明之環狀胺基有機氧矽烷化合物係以下述通式(1)表示。
上述式(1)中,R1
表示取代或未取代之碳數1~20的1價烴基,R2
~R5
各自獨立地表示取代或未取代之碳數1~20的1價烴基,R6
~R8
各自獨立地表示氫原子或取代或未取代之碳數1~20的1價烴基,R9
及R10
各自獨立地表示可含有雜原子的取代或未取代之碳數1~20的2價烴基,m為0、1或2,較佳為0,n為0或1,較佳為0。
此處,作為R1
之碳數1~20、較佳碳數1~10、更佳碳數1~5的1價烴基,可舉出直鏈狀、支鏈狀或環狀的烷基、烯基、芳基、芳烷基等。
具體而言,可舉出甲基、乙基、正丙基、正丁基、正戊基、正己基、正庚基、正辛基、正癸基、十二基、十四基、十六基、十八基、二十基等之直鏈狀的烷基;異丙基、異丁基、第二丁基、第三丁基、叔己基(thexyl)、2-乙基己基等之支鏈狀的烷基;環戊基、環己基等之環狀的烷基;乙烯基、烯丙基、丁烯基、戊烯基等之烯基;苯基、甲苯基等之芳基;苄基等之芳烷基等,尤其從原料的取得容易性、生成物的有用性之觀點來看,較佳為甲基、乙基、正丙基、異丙基等之碳數1~3的烷基;烯丙基、丁烯基、戊烯基等之碳數2~5的烯基。
作為R2
~R8
之碳數1~20、較佳碳數1~10、更佳碳數1~5的1價烴基,可舉出與在上述R1
所例示的基同樣之基,此時亦尤其從原料的取得容易性、生成物的有用性之觀點來看,作為R2
~R5
,較佳為甲基、乙基、丙基、異丙基等之碳數1~3的烷基、烯丙基、丁烯基、戊烯基等之碳數2~5的烯基,作為R6
~R8
,較佳為氫原子。
還有,上述R1
~R5
的1價烴基係其氫原子的一部分或全部可被其他的取代基所取代,作為如此的取代基之具體例,可舉出甲氧基、乙氧基、(異)丙氧基等之烷氧基;氟原子、氯原子、溴原子、碘原子等之鹵素原子;氰基;胺基;碳數2~10的醯基;三氯矽基;各烷基、各烷氧基分別為碳數1~5的三烷基矽基、二烷基單氯矽基、單烷基二氯矽基、三烷氧基矽基、二烷基單烷氧基矽基或單烷基二烷氧基矽基。此等之取代基亦可組合2種以上來使用,取代位置及取代基數亦沒有特別的限定。
作為R9
及R10
之碳數1~20、較佳碳數1~10、更佳碳數1~5之可含有雜原子的2價烴基之雜原子,可舉出O、S、NH等。
上述2價烴基可為直鏈狀、支鏈狀、環狀之任一者,作為其具體例,可舉出亞甲基、伸乙基、甲基伸乙基(伸丙基)、三亞甲基、甲基三亞甲基、四亞甲基、六亞甲基、八亞甲基、十亞甲基、伸異丁基等之伸烷基;伸苯基、甲基伸苯基等之伸芳基;伸乙基伸苯基、伸乙基伸苯基亞甲基等之伸芳烷基;2-氧雜伸丙基、2-氧雜伸戊基等之氧雜伸烷基等,尤其從原料的取得容易性、生成物的有用性之觀點來看,作為R9
,較佳為亞甲基、伸乙基、三亞甲基等之碳數1~3的伸烷基,作為R10
,較佳為亞甲基、伸乙基、三亞甲基等之碳數1~3的伸烷基;2-氧雜伸丙基。
還有,上述2價烴基係其氫原子的一部分或全部可被其他的取代基所取代,作為如此的取代基之具體例,可舉出氟原子、氯原子、溴原子、碘原子等之鹵素原子;氰基;胺基;碳數2~10的醯基;三氯矽基;各烷基、各烷氧基分別為碳數1~5的三烷基矽基、二烷基單氯矽基、單烷基二氯矽基、三烷氧基矽基、二烷基單烷氧基矽基或單烷基二烷氧基矽基。此等之取代基亦可組合2種以上使用,取代位置及取代基數亦沒有特別的限定。
作為上述通式(1)所示的環狀胺基有機氧矽烷化合物之具體例,可舉出2,2-二甲氧基-6-甲氧基甲基-4-(三甲氧基矽基甲基)-1-氧雜-4-氮雜-2-矽雜環己烷、2-甲氧基-2-甲基-6-甲氧基甲基-4-(二甲氧基甲基矽基甲基)-1-氧雜-4-氮雜-2-矽雜環己烷、2,2-二甲基-6-甲氧基甲基-4-(甲氧基二甲基矽基甲基)-1-氧雜-4-氮雜-2-矽雜環己烷、2,2-二乙氧基-6-甲氧基甲基-4-(三乙氧基矽基甲基)-1-氧雜-4-氮雜-2-矽雜環己烷、2-乙氧基-2-甲基-6-甲氧基甲基-4-(二乙氧基甲基矽基甲基)-1-氧雜-4-氮雜-2-矽雜環己烷、2,2-二甲基-6-甲氧基甲基-4-(乙氧基二甲基矽基甲基)-1-氧雜-4-氮雜-2-矽雜環己烷、2,2-二甲氧基-8-甲氧基甲基-6-(3-三甲氧基矽基丙基)-1-氧雜-6-氮雜-2-矽雜環辛烷、2-甲氧基-2-甲基-8-甲氧基甲基-6-(3-二甲氧基甲基矽基丙基)-1-氧雜-6-氮雜-2-矽雜環辛烷、2,2-二甲基-8-甲氧基甲基-6-(3-甲氧基二甲基矽基丙基)-1-氧雜-6-氮雜-2-矽雜環辛烷、2,2-二乙氧基-8-甲氧基甲基-6-(3-三乙氧基矽基丙基)-1-氧雜-6-氮雜-2-矽雜環辛烷、2-乙氧基-2-甲基-8-甲氧基甲基-6-(3-二乙氧基甲基矽基丙基)-1-氧雜-6-氮雜-2-矽雜環辛烷、2,2-二甲基-8-甲氧基甲基-6-(3-乙氧基二甲基矽基丙基)-1-氧雜-6-氮雜-2-矽雜環辛烷、2,2-二甲氧基-6-烯丙氧基甲基-4-(三甲氧基矽基甲基)-1-氧雜-4-氮雜-2-矽雜環己烷、2-甲氧基-2-甲基-6-烯丙氧基甲基-4-(二甲氧基甲基矽基甲基)-1-氧雜-4-氮雜-2-矽雜環己烷、2,2-二甲基-6-烯丙氧基甲基-4-(甲氧基二甲基矽基甲基)-1-氧雜-4-氮雜-2-矽雜環己烷、2,2-二乙氧基-6-烯丙氧基甲基-4-(三乙氧基矽基甲基)-1-氧雜-4-氮雜-2-矽雜環己烷、2-乙氧基-2-甲基-6-烯丙氧基甲基-4-(二乙氧基甲基矽基甲基)-1-氧雜-4-氮雜-2-矽雜環己烷、2,2-二甲基-6-烯丙氧基甲基-4-(乙氧基二甲基矽基甲基)-1-氧雜-4-氮雜-2-矽雜環己烷、2,2-二甲氧基-8-烯丙氧基甲基-6-(3-三甲氧基矽基丙基)-1-氧雜-6-氮雜-2-矽雜環辛烷、2-甲氧基-2-甲基-8-烯丙氧基甲基-6-(3-二甲氧基甲基矽基丙基)-1-氧雜-6-氮雜-2-矽雜環辛烷、2,2-二甲基-8-烯丙氧基甲基-6-(3-甲氧基二甲基矽基丙基)-1-氧雜-6-氮雜-2-矽雜環辛烷、2,2-二乙氧基-8-烯丙氧基甲基-6-(3-三乙氧基矽基丙基)-1-氧雜-6-氮雜-2-矽雜環辛烷、2-乙氧基-2-甲基-8-烯丙氧基甲基-6-(3-二乙氧基甲基矽基丙基)-1-氧雜-6-氮雜-2-矽雜環辛烷、2,2-二甲基-8-烯丙氧基甲基-6-(3-乙氧基二甲基矽基丙基)-1-氧雜-6-氮雜-2-矽雜環辛烷、2,2-二甲氧基-6-丁氧基甲基-4-(三甲氧基矽基甲基)-1-氧雜-4-氮雜-2-矽雜環己烷、2-甲氧基-2-甲基-6-丁氧基甲基-4-(二甲氧基甲基矽基甲基)-1-氧雜-4-氮雜-2-矽雜環己烷、2,2-二甲基-6-丁氧基甲基-4-(甲氧基二甲基矽基甲基)-1-氧雜-4-氮雜-2-矽雜環己烷、2,2-二乙氧基-6-丁氧基甲基-4-(三乙氧基矽基甲基)-1-氧雜-4-氮雜-2-矽雜環己烷、2-乙氧基-2-甲基-6-丁氧基甲基-4-(二乙氧基甲基矽基甲基)-1-氧雜-4-氮雜-2-矽雜環己烷、2,2-二甲基-6-丁氧基甲基-4-(乙氧基二甲基矽基甲基)-1-氧雜-4-氮雜-2-矽雜環己烷、2,2-二甲氧基-8-丁氧基甲基-6-(3-三甲氧基矽基丙基)-1-氧雜-6-氮雜-2-矽雜環辛烷、2-甲氧基-2-甲基-8-丁氧基甲基-6-(3-二甲氧基甲基矽基丙基)-1-氧雜-6-氮雜-2-矽雜環辛烷、2,2-二甲基-8-丁氧基甲基-6-(3-甲氧基二甲基矽基丙基)-1-氧雜-6-氮雜-2-矽雜環辛烷、2,2-二乙氧基-8-丁氧基甲基-6-(3-三乙氧基矽基丙基)-1-氧雜-6-氮雜-2-矽雜環辛烷、2-乙氧基-2-甲基-8-丁氧基甲基-6-(3-二乙氧基甲基矽基丙基)-1-氧雜-6-氮雜-2-矽雜環辛烷、2,2-二甲基-8-丁氧基甲基-6-(3-乙氧基二甲基矽基丙基)-1-氧雜-6-氮雜-2-矽雜環辛烷、2,2-二甲氧基-6-苯氧基甲基-4-(三甲氧基矽基甲基)-1-氧雜-4-氮雜-2-矽雜環己烷、2-甲氧基-2-甲基-6-苯氧基甲基-4-(二甲氧基甲基矽基甲基)-1-氧雜-4-氮雜-2-矽雜環己烷、2,2-二甲基-6-苯氧基甲基-4-(甲氧基二甲基矽基甲基)-1-氧雜-4-氮雜-2-矽雜環己烷、2.2-二乙氧基-6-苯氧基甲基-4-(三乙氧基矽基甲基)-1-氧雜-4-氮雜-2-矽雜環己烷、2-乙氧基-2-甲基-6-苯氧基甲基-4-(二乙氧基甲基矽基甲基)-1-氧雜-4-氮雜-2-矽雜環己烷、2,2-二甲基-6-苯氧基甲基-4-(乙氧基二甲基矽基甲基)-1-氧雜-4-氮雜-2-矽雜環己烷、2,2-二甲氧基-8-苯氧基甲基-6-(3-三甲氧基矽基丙基)-1-氧雜-6-氮雜-2-矽雜環辛烷、2-甲氧基-2-甲基-8-苯氧基甲基-6-(3-二甲氧基甲基矽基丙基)-1-氧雜-6-氮雜-2-矽雜環辛烷、2,2-二甲基-8-苯氧基甲基-6-(3-甲氧基二甲基矽基丙基)-1-氧雜-6-氮雜-2-矽雜環辛烷、2,2-二乙氧基-8-苯氧基甲基-6-(3-三乙氧基矽基丙基)-1-氧雜-6-氮雜-2-矽雜環辛烷、2-乙氧基-2-甲基-8-苯氧基甲基-6-(3-二乙氧基甲基矽基丙基)-1-氧雜-6-氮雜-2-矽雜環辛烷、2,2-二甲基-8-苯氧基甲基-6-(3-乙氧基二甲基矽基丙基)-1-氧雜-6-氮雜-2-矽雜環辛烷等。
作為本發明之上述通式(1)所示的環狀胺基有機氧矽烷化合物之製造方法,例如可舉出蒸餾使下述通式(2)所示的胺基有機氧矽烷化合物(以下簡稱化合物(2))與下述通式(3)所示的環氧化合物(以下簡稱化合物(3))反應而得之反應混合物的方法。
更具體而言,如下述流程所示,認為於第1階段中,化合物(2)與化合物(3)反應而生成具有羥基的胺基有機氧矽烷化合物,於第2階段中,在將含有該具有羥基的胺基有機氧矽烷化合物之反應液予以蒸餾之步驟中,藉由分子內脫醇環化而生成作為目的之環狀胺基有機氧矽烷化合物。
作為上述化合物(2)之具體例,可舉出雙(三甲氧基矽基甲基)胺、雙(二甲氧基甲基矽基甲基)胺、雙(甲氧基二甲基矽基甲基)胺、雙(三乙氧基矽基甲基)胺、雙(二乙氧基甲基矽基甲基)胺、雙(乙氧基二甲基矽基甲基)胺、雙(3-三甲氧基矽基丙基)胺、雙(3-二甲氧基甲基矽基丙基)胺、雙(3-甲氧基二甲基矽基丙基)胺、雙(3-三乙氧基矽基丙基)胺、雙(3-二乙氧基甲基矽基丙基)胺、雙(3-乙氧基二甲基矽基丙基)胺等。
作為上述化合物(3)之具體例,可舉出環氧丙基甲基醚、烯丙基環氧丙基醚、丁基環氧丙基醚、環氧丙基苯基醚等。
上述化合物(2)與化合物(3)之摻合比係沒有特別的限定,但從反應性、生產性之點來看,相對於化合物(2)1莫耳,化合物(3)較佳為0.2~5.0莫耳,更佳為0.5~2.0莫耳。
上述第1階段之反應係即使無觸媒亦進行,但以提高反應速度之目的,也可使用鹼性觸媒或酸觸媒。
作為鹼性觸媒之具體例,可舉出氫氧化鈉、氫氧化鉀、甲氧化鈉、乙氧化鈉、甲氧化鈉之甲醇溶液、乙氧化鈉之乙醇溶液等。
另一方面,作為酸性觸媒之具體例,可舉出硫酸、鹽酸、硝酸等之無機酸;甲磺酸、苯磺酸、甲苯磺酸、十二基苯磺酸、三氟甲磺酸等之磺酸化合物及此等之鹽等。
觸媒之使用量係沒有特別的限定,但從反應性、生產性之點來看,相對於化合物(2)1莫耳,較佳為0.0001~0.2莫耳,更佳為0.001~0.1莫耳。
還有,上述第1階段之反應係即使無溶劑亦進行,但也可使用溶劑。作為所用的溶劑,可舉出戊烷、己烷、環己烷、庚烷、異辛烷、苯、甲苯、二甲苯等之烴系溶劑;二乙基醚、四氫呋喃、二噁烷等之醚系溶劑;乙酸乙酯、乙酸丁酯等之酯系溶劑;乙腈、N,N-二甲基甲醯胺、N-甲基吡咯啶酮等之非質子性極性溶劑;二氯甲烷、氯仿等之氯化烴系溶劑;甲醇、乙醇、1-丙醇、2-丙醇等之醇系溶劑等,此等溶劑係可單獨使用1種,也可混合2種以上使用。
上述第2階段之蒸餾方法係可使用通常的蒸餾方法,但為了促進脫醇反應之反應速度,或為了裂解反應液中存在的於分子間進行脫醇縮合之高分子化合物而轉化至作為目的之環狀胺基有機氧矽烷化合物,較佳為在鹼性觸媒或酸性觸媒之存在下進行蒸餾。
作為此時的鹼性觸媒及酸性觸媒,可使用與上述同樣者。
觸媒之使用量係沒有特別的限定,但從反應性、生產性之點來看,相對於化合物(3)1莫耳,較佳為0.0001~0.2莫耳,更佳為0.001~0.1莫耳。
還有,於第2階段中,可將第1階段所得之反應液直接蒸餾,也可在該反應液中更添加溶劑,進行蒸餾。
又,作為此時之溶劑,可舉出戊烷、己烷、環己烷、庚烷、異辛烷、癸烷、十三烷、十八烷、二十烷、苯、甲苯、二甲苯、十二基苯等之烴系溶劑;二乙基醚、四氫呋喃、二噁烷、二苯基醚等之醚系溶劑;乙酸乙酯、乙酸丁酯、硬脂酸甲酯、油酸甲酯等之酯系溶劑;乙腈、N,N-二甲基甲醯胺、N-甲基吡咯啶酮等之非質子性極性溶劑;二氯甲烷、氯仿等之氯化烴系溶劑;甲醇、乙醇、1-丙醇、2-丙醇、1-癸醇、1-十八醇、2-己基-1-癸醇、油醇、1-二十二醇等之醇系溶劑等,此等溶劑係可單獨使用1種,也可混合2種以上使用。
[實施例]
以下,舉出實施例更具體地說明本發明,惟本發明不受下述的實施例所限制。
還有,1
H-NMR光譜係藉由600MHz、重氯仿溶劑測定,IR光譜係藉由D-ATR測定。
[實施例1]
於具備攪拌機、回流器、滴液漏斗及溫度計的燒瓶中,加入雙(3-三甲氧基矽基丙基)胺102.5g (0.3 mol)、甲醇19.2g,加熱至60℃。於內溫安定後,費1小時滴下環氧丙基甲基醚29.1g (0.33 mol),在該溫度下攪拌2小時。
攪拌結束後,於反應液中添加28質量%甲氧化鈉的甲醇溶液0.6g,進行蒸餾,得到沸點174-176℃/0.3kPa之餾分83.6g。
測定所得之餾分的質譜、1
H-NMR光譜、IR光譜。圖1中顯示1
H-NMR光譜,圖2中顯示IR光譜。
質譜
m/z 397, 366, 248, 160, 121, 91
由此等之結果來看,確認所得之化合物為2,2-二甲氧基-8-甲氧基甲基-6-(3-三甲氧基矽基丙基)-1-氧雜-6-氮雜-2-矽雜環辛烷。
[實施例2]
於具備攪拌機、回流器、滴液漏斗及溫度計的燒瓶中,加入雙(3-三甲氧基矽基丙基)胺136.6g (0.4 mol)、甲醇25.6g,加熱至60℃。於內溫安定後,費1小時滴下丁基環氧丙基醚57.3g (0.44 mol),在該溫度下攪拌2小時。
攪拌結束後,於反應液中添加28質量%甲氧化鈉的甲醇溶液0.8g,進行蒸餾,得到沸點179-182℃/0.2kPa之餾分146.7g。
測定所得之餾分的質譜、1
H-NMR光譜、IR光譜。圖3中顯示1
H-NMR光譜,圖4中顯示IR光譜。
質譜
m/z 439, 408, 366, 290, 160, 121, 91
由此等之結果來看,確認所得之化合物為2,2-二甲氧基-8-丁氧基甲基-6-(3-三甲氧基矽基丙基)-1-氧雜-6-氮雜-2-矽雜環辛烷。
圖1係實施例1所得之化合物的1
H-NMR光譜圖。
圖2係實施例1所得之化合物的IR光譜圖。
圖3係實施例2所得之化合物的1
H-NMR光譜圖。
圖4係實施例2所得之化合物的IR光譜圖。
Claims (3)
- 如請求項2之環狀胺基有機氧矽烷化合物之製造方法,其中於鹼性觸媒或酸性觸媒之存在下蒸餾反應混合物。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2018116813A JP6939717B2 (ja) | 2018-06-20 | 2018-06-20 | 環状アミノオルガノキシシラン化合物およびその製造方法 |
JP2018-116813 | 2018-06-20 |
Publications (2)
Publication Number | Publication Date |
---|---|
TW202016122A true TW202016122A (zh) | 2020-05-01 |
TWI801610B TWI801610B (zh) | 2023-05-11 |
Family
ID=66912674
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
TW108121268A TWI801610B (zh) | 2018-06-20 | 2019-06-19 | 環狀胺基有機氧矽烷化合物及其製造方法 |
Country Status (6)
Country | Link |
---|---|
US (1) | US11466039B2 (zh) |
EP (1) | EP3584248B1 (zh) |
JP (1) | JP6939717B2 (zh) |
KR (1) | KR20190143384A (zh) |
CN (1) | CN110615810A (zh) |
TW (1) | TWI801610B (zh) |
Family Cites Families (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6172077A (ja) * | 1984-09-14 | 1986-04-14 | Shin Etsu Chem Co Ltd | 接着促進剤 |
US4794192A (en) * | 1987-07-06 | 1988-12-27 | General Electric Company | Cyclic aminoalkylsilanes and their use as adhesion promoters in room temperature vulcanizable polydiorganosiloxane compositions |
WO2003091186A2 (en) * | 2002-04-23 | 2003-11-06 | Gelest, Inc. | Azasilanes and methods for making and using the same |
DE102005011108A1 (de) * | 2005-03-10 | 2006-09-14 | Wacker Chemie Ag | Aminoalkylsilane |
US7745653B2 (en) * | 2007-03-08 | 2010-06-29 | 3M Innovative Properties Company | Fluorochemical compounds having pendent silyl groups |
JP5359585B2 (ja) | 2008-10-22 | 2013-12-04 | 信越化学工業株式会社 | アミノ基を有する有機ケイ素化合物及びその製造方法 |
JP5359584B2 (ja) | 2009-06-15 | 2013-12-04 | 信越化学工業株式会社 | アミノ基を有する有機ケイ素化合物及びその製造方法 |
JP5402699B2 (ja) * | 2010-02-12 | 2014-01-29 | 信越化学工業株式会社 | 環状シラザン化合物の製造方法 |
JP5835116B2 (ja) * | 2012-06-15 | 2015-12-24 | 信越化学工業株式会社 | 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 |
JP6252429B2 (ja) * | 2014-10-14 | 2017-12-27 | 信越化学工業株式会社 | 環状アミノオルガノキシシラン化合物及びその製造方法 |
JP6303982B2 (ja) * | 2014-10-31 | 2018-04-04 | 信越化学工業株式会社 | 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 |
JP6409695B2 (ja) * | 2015-07-03 | 2018-10-24 | 信越化学工業株式会社 | アミノ基を有する有機ケイ素化合物及びその製造方法 |
JP2018116813A (ja) | 2017-01-17 | 2018-07-26 | 株式会社東芝 | 電池モジュールおよび電池装置 |
KR101838565B1 (ko) * | 2017-04-28 | 2018-03-14 | 제이에스아이실리콘주식회사 | 알콕시알킬아미노실란 및 에폭시 화합물의 반응에 의한 2-옥사-5-아자-1-실라사이클로옥탄 및 이의 제조방법 |
JP6885294B2 (ja) * | 2017-10-24 | 2021-06-09 | 信越化学工業株式会社 | 多環式アミノシラン化合物およびその製造方法 |
-
2018
- 2018-06-20 JP JP2018116813A patent/JP6939717B2/ja active Active
-
2019
- 2019-06-17 EP EP19180507.6A patent/EP3584248B1/en active Active
- 2019-06-17 KR KR1020190071252A patent/KR20190143384A/ko active Search and Examination
- 2019-06-19 US US16/446,232 patent/US11466039B2/en active Active
- 2019-06-19 TW TW108121268A patent/TWI801610B/zh active
- 2019-06-20 CN CN201910535166.6A patent/CN110615810A/zh active Pending
Also Published As
Publication number | Publication date |
---|---|
US11466039B2 (en) | 2022-10-11 |
KR20190143384A (ko) | 2019-12-30 |
EP3584248A1 (en) | 2019-12-25 |
CN110615810A (zh) | 2019-12-27 |
TWI801610B (zh) | 2023-05-11 |
US20190389887A1 (en) | 2019-12-26 |
JP6939717B2 (ja) | 2021-09-22 |
EP3584248B1 (en) | 2021-09-29 |
JP2019218299A (ja) | 2019-12-26 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US7053233B2 (en) | Silane compound having at least two protected functional groups and method for preparing the same | |
US9024051B2 (en) | Organoxysilane compounds having silyl-protected secondary amino group and making method | |
JP6052140B2 (ja) | ビスシリル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 | |
JP5601269B2 (ja) | フルオロアルキル基を有するアルコキシシラン化合物及びその製造方法 | |
TWI734939B (zh) | 多環式胺基矽烷化合物及其之製造方法 | |
TW202016122A (zh) | 環狀胺基有機氧矽烷化合物及其製造方法 | |
EP3015471B1 (en) | Novel bisalkoxysilane compound and its production method | |
JP2016040233A (ja) | ビシクロアミノオルガノキシシラン化合物及びその製造方法 | |
JP2013256477A (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 | |
US11312734B2 (en) | Nitrogen-containing cyclic organoxysilane compound and method for producing the same | |
TWI744623B (zh) | 具有甘脲環之有機矽化合物以及其製造方法 | |
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 | |
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 |