JP4411369B2 - 有機シラン化合物及びそれを用いて得られる有機シリカ - Google Patents
有機シラン化合物及びそれを用いて得られる有機シリカ Download PDFInfo
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- JP4411369B2 JP4411369B2 JP2007057342A JP2007057342A JP4411369B2 JP 4411369 B2 JP4411369 B2 JP 4411369B2 JP 2007057342 A JP2007057342 A JP 2007057342A JP 2007057342 A JP2007057342 A JP 2007057342A JP 4411369 B2 JP4411369 B2 JP 4411369B2
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- -1 Organosilane compound Chemical class 0.000 title claims description 93
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 144
- 239000000377 silicon dioxide Substances 0.000 claims description 67
- 125000001424 substituent group Chemical group 0.000 claims description 31
- 125000000962 organic group Chemical group 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 25
- 125000005843 halogen group Chemical group 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
- 125000004957 naphthylene group Chemical group 0.000 claims description 12
- 125000005551 pyridylene group Chemical group 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 125000003638 stannyl group Chemical group [H][Sn]([H])([H])* 0.000 claims description 10
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 claims description 9
- 125000001300 boranyl group Chemical group [H]B([H])[*] 0.000 claims description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([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
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 7
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 7
- 230000000379 polymerizing effect Effects 0.000 claims description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- 125000005577 anthracene group Chemical group 0.000 claims description 6
- 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 6
- 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 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 239000011777 magnesium Substances 0.000 claims description 5
- 229910052749 magnesium Inorganic materials 0.000 claims description 5
- 229910052725 zinc Inorganic materials 0.000 claims description 5
- 239000011701 zinc Substances 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 81
- 150000001875 compounds Chemical class 0.000 description 60
- 238000000034 method Methods 0.000 description 45
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 42
- 239000012043 crude product Substances 0.000 description 37
- 239000000243 solution Substances 0.000 description 36
- 239000011541 reaction mixture Substances 0.000 description 32
- 239000011148 porous material Substances 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 29
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 28
- 239000012044 organic layer Substances 0.000 description 25
- 230000015572 biosynthetic process Effects 0.000 description 24
- 239000004094 surface-active agent Substances 0.000 description 24
- 239000000203 mixture Substances 0.000 description 23
- 239000012299 nitrogen atmosphere Substances 0.000 description 23
- 229920001451 polypropylene glycol Polymers 0.000 description 23
- 238000003786 synthesis reaction Methods 0.000 description 23
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 22
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- 239000002904 solvent Substances 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 18
- 238000003756 stirring Methods 0.000 description 17
- 239000002243 precursor Substances 0.000 description 16
- 235000019439 ethyl acetate Nutrition 0.000 description 14
- 238000004519 manufacturing process Methods 0.000 description 14
- 239000000843 powder Substances 0.000 description 13
- 238000010898 silica gel chromatography Methods 0.000 description 13
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 12
- 238000000695 excitation spectrum Methods 0.000 description 12
- 238000002189 fluorescence spectrum Methods 0.000 description 12
- 229910000077 silane Inorganic materials 0.000 description 11
- 239000011780 sodium chloride Substances 0.000 description 11
- 239000000463 material Substances 0.000 description 10
- GRJHONXDTNBDTC-UHFFFAOYSA-N phenyl trifluoromethanesulfonate Chemical compound FC(F)(F)S(=O)(=O)OC1=CC=CC=C1 GRJHONXDTNBDTC-UHFFFAOYSA-N 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- 238000006460 hydrolysis reaction Methods 0.000 description 9
- 230000031700 light absorption Effects 0.000 description 9
- 230000000737 periodic effect Effects 0.000 description 9
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 8
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 8
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 7
- 230000007062 hydrolysis Effects 0.000 description 7
- 239000013335 mesoporous material Substances 0.000 description 7
- 238000006068 polycondensation reaction Methods 0.000 description 7
- 238000001179 sorption measurement Methods 0.000 description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- 235000010290 biphenyl Nutrition 0.000 description 6
- 239000004305 biphenyl Substances 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 239000010409 thin film Substances 0.000 description 5
- VOAAEKKFGLPLLU-UHFFFAOYSA-N (4-methoxyphenyl)boronic acid Chemical compound COC1=CC=C(B(O)O)C=C1 VOAAEKKFGLPLLU-UHFFFAOYSA-N 0.000 description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- 238000002441 X-ray diffraction Methods 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- WFCOFJPSLQOEPV-UHFFFAOYSA-N hydroxy-(4-iodophenyl)-bis(prop-2-enyl)silane Chemical compound C=CC[Si](O)(CC=C)C1=CC=C(I)C=C1 WFCOFJPSLQOEPV-UHFFFAOYSA-N 0.000 description 4
- 239000011259 mixed solution Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 238000000967 suction filtration Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 229920000428 triblock copolymer Polymers 0.000 description 4
- JDFAKXJDRCOWOZ-UHFFFAOYSA-N triethoxy-(4-iodophenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=C(I)C=C1 JDFAKXJDRCOWOZ-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 3
- VBIIFPGSPJYLRR-UHFFFAOYSA-M Stearyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)C VBIIFPGSPJYLRR-UHFFFAOYSA-M 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000006482 condensation reaction Methods 0.000 description 3
- 229910001873 dinitrogen Inorganic materials 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 150000002367 halogens Chemical group 0.000 description 3
- JEVCGRVVEMKVRL-UHFFFAOYSA-N hydroxy-[4-(4-methoxyphenyl)phenyl]-bis(prop-2-enyl)silane Chemical group C1=CC(OC)=CC=C1C1=CC=C([Si](O)(CC=C)CC=C)C=C1 JEVCGRVVEMKVRL-UHFFFAOYSA-N 0.000 description 3
- DQEUYIQDSMINEY-UHFFFAOYSA-M magnesium;prop-1-ene;bromide Chemical compound [Mg+2].[Br-].[CH2-]C=C DQEUYIQDSMINEY-UHFFFAOYSA-M 0.000 description 3
- IUYHWZFSGMZEOG-UHFFFAOYSA-M magnesium;propane;chloride Chemical compound [Mg+2].[Cl-].C[CH-]C IUYHWZFSGMZEOG-UHFFFAOYSA-M 0.000 description 3
- 239000002736 nonionic surfactant Substances 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- COHOGNZHAUOXPA-UHFFFAOYSA-N trimethyl(phenyl)stannane Chemical compound C[Sn](C)(C)C1=CC=CC=C1 COHOGNZHAUOXPA-UHFFFAOYSA-N 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 0 C*S(CC=C)(CC=C)c(cc1)ccc1I Chemical compound C*S(CC=C)(CC=C)c(cc1)ccc1I 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 239000003929 acidic solution Substances 0.000 description 2
- 125000005211 alkyl trimethyl ammonium group Chemical group 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 2
- 125000005620 boronic acid group Chemical group 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 229920000359 diblock copolymer Polymers 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- IWCVDCOJSPWGRW-UHFFFAOYSA-M magnesium;benzene;chloride Chemical compound [Mg+2].[Cl-].C1=CC=[C-]C=C1 IWCVDCOJSPWGRW-UHFFFAOYSA-M 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 150000004756 silanes Chemical class 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 2
- PIILXFBHQILWPS-UHFFFAOYSA-N tributyltin Chemical group CCCC[Sn](CCCC)CCCC PIILXFBHQILWPS-UHFFFAOYSA-N 0.000 description 2
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 2
- CPRPKIMXLHBUGA-UHFFFAOYSA-N triethyltin Chemical group CC[Sn](CC)CC CPRPKIMXLHBUGA-UHFFFAOYSA-N 0.000 description 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
- LYRCQNDYYRPFMF-UHFFFAOYSA-N trimethyltin Chemical group C[Sn](C)C LYRCQNDYYRPFMF-UHFFFAOYSA-N 0.000 description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- BOHFWWWQMGFMPJ-UHFFFAOYSA-N 1,2,3,4-tetraphenylpyrene Chemical group C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C(C=2C=CC=CC=2)=C2C=3C=CC=CC=3)=CC3=CC=CC4=CC=C2C1=C34 BOHFWWWQMGFMPJ-UHFFFAOYSA-N 0.000 description 1
- CHBDXRNMDNRJJC-UHFFFAOYSA-N 1,2,3-triphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 CHBDXRNMDNRJJC-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- LFMWZTSOMGDDJU-UHFFFAOYSA-N 1,4-diiodobenzene Chemical compound IC1=CC=C(I)C=C1 LFMWZTSOMGDDJU-UHFFFAOYSA-N 0.000 description 1
- UCCUXODGPMAHRL-UHFFFAOYSA-N 1-bromo-4-iodobenzene Chemical compound BrC1=CC=C(I)C=C1 UCCUXODGPMAHRL-UHFFFAOYSA-N 0.000 description 1
- NLWCWEGVNJVLAX-UHFFFAOYSA-N 1-methoxy-2-phenylbenzene Chemical group COC1=CC=CC=C1C1=CC=CC=C1 NLWCWEGVNJVLAX-UHFFFAOYSA-N 0.000 description 1
- KQDJTBPASNJQFQ-UHFFFAOYSA-N 2-iodophenol Chemical compound OC1=CC=CC=C1I KQDJTBPASNJQFQ-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- MRWWWZLJWNIEEJ-UHFFFAOYSA-N 4,4,5,5-tetramethyl-2-propan-2-yloxy-1,3,2-dioxaborolane Chemical compound CC(C)OB1OC(C)(C)C(C)(C)O1 MRWWWZLJWNIEEJ-UHFFFAOYSA-N 0.000 description 1
- VSMDINRNYYEDRN-UHFFFAOYSA-N 4-iodophenol Chemical compound OC1=CC=C(I)C=C1 VSMDINRNYYEDRN-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- FEJUGLKDZJDVFY-UHFFFAOYSA-N 9-borabicyclo(3.3.1)nonane Chemical group C1CCC2CCCC1B2 FEJUGLKDZJDVFY-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 238000005937 allylation reaction Methods 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- YSJGOMATDFSEED-UHFFFAOYSA-M behentrimonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCCCCCC[N+](C)(C)C YSJGOMATDFSEED-UHFFFAOYSA-M 0.000 description 1
- WGQKYBSKWIADBV-UHFFFAOYSA-O benzylaminium Chemical compound [NH3+]CC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-O 0.000 description 1
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- WOWHHFRSBJGXCM-UHFFFAOYSA-M cetyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)C WOWHHFRSBJGXCM-UHFFFAOYSA-M 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- KWTSZCJMWHGPOS-UHFFFAOYSA-M chloro(trimethyl)stannane Chemical compound C[Sn](C)(C)Cl KWTSZCJMWHGPOS-UHFFFAOYSA-M 0.000 description 1
- 238000009694 cold isostatic pressing Methods 0.000 description 1
- TUFGVZMNGTYAQD-UHFFFAOYSA-N comins' reagent Chemical compound FC(F)(F)S(=O)(=O)N(S(=O)(=O)C(F)(F)F)C1=CC=C(Cl)C=N1 TUFGVZMNGTYAQD-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- PLMFYJJFUUUCRZ-UHFFFAOYSA-M decyltrimethylammonium bromide Chemical compound [Br-].CCCCCCCCCC[N+](C)(C)C PLMFYJJFUUUCRZ-UHFFFAOYSA-M 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- XJWSAJYUBXQQDR-UHFFFAOYSA-M dodecyltrimethylammonium bromide Chemical compound [Br-].CCCCCCCCCCCC[N+](C)(C)C XJWSAJYUBXQQDR-UHFFFAOYSA-M 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 1
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- QBHWPVJPWQGYDS-UHFFFAOYSA-N hexaphenylbenzene Chemical group C1=CC=CC=C1C(C(=C(C=1C=CC=CC=1)C(C=1C=CC=CC=1)=C1C=2C=CC=CC=2)C=2C=CC=CC=2)=C1C1=CC=CC=C1 QBHWPVJPWQGYDS-UHFFFAOYSA-N 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000000693 micelle Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-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
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- XCOHAFVJQZPUKF-UHFFFAOYSA-M octyltrimethylammonium bromide Chemical compound [Br-].CCCCCCCC[N+](C)(C)C XCOHAFVJQZPUKF-UHFFFAOYSA-M 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 150000001282 organosilanes Chemical class 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000012756 surface treatment agent Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000005369 trialkoxysilyl group Chemical group 0.000 description 1
- RNVJQUPAEIQUTC-UHFFFAOYSA-N tricyclohexyltin Chemical group C1CCCCC1[Sn](C1CCCCC1)C1CCCCC1 RNVJQUPAEIQUTC-UHFFFAOYSA-N 0.000 description 1
- CEYYIKYYFSTQRU-UHFFFAOYSA-M trimethyl(tetradecyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCC[N+](C)(C)C CEYYIKYYFSTQRU-UHFFFAOYSA-M 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- SBXWFLISHPUINY-UHFFFAOYSA-N triphenyltin Chemical group C1=CC=CC=C1[Sn](C=1C=CC=CC=1)C1=CC=CC=C1 SBXWFLISHPUINY-UHFFFAOYSA-N 0.000 description 1
- NSPWVJAKNXJHEP-UHFFFAOYSA-N tripropyltin Chemical group CCC[Sn](CCC)CCC NSPWVJAKNXJHEP-UHFFFAOYSA-N 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 System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0836—Compounds with one or more Si-OH or Si-O-metal linkage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- 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
Description
で表されることを特徴とするものである。
で表されることを特徴とするものである。
本発明の第一の有機シラン化合物は、下記一般式(1):
A−Ar−A (3)
(式(3)中、Arはフェニレン基、ビフェニリレン基、ナフチレン基及びピリジレン基からなる群から選択されるいずれか1種の2価の芳香族有機基を示し、Aは同一でも異なっていてもよく、それぞれハロゲン原子を示す。)
で表される原料化合物と、下記一般式(4):
H−Si(OR1)3 (4)
で表される化合物を反応せしめて、下記一般式(5):
A−Ar−Si(OR1)3 (5)
(式(5)中、Arはフェニレン基、ビフェニリレン基、ナフチレン基及びピリジレン基からなる群から選択されるいずれか1種の2価の芳香族有機基を示し、Aはハロゲン原子を示し、R1は水素原子又は炭素数1〜4のアルキル基を示す。)
で表される前駆体化合物を得た後、前記一般式(5)で表される化合物中の式:−OR1で表される置換基のうちの2つをアリル基に置換するように前記前駆体化合物をアリル化することにより、上記一般式(1)中のXがハロゲンである第一の有機シラン化合物を得る方法が挙げられる。
HO−Ar−A (6)
(式(3)中、Arはフェニレン基、ビフェニリレン基、ナフチレン基及びピリジレン基からなる群から選択されるいずれか1種の2価の芳香族有機基を示し、Aは同一でも異なっていてもよく、それぞれハロゲン原子を示す。)
で表される原料化合物と、上記一般式(4)で表される化合物とを反応せしめて、下記一般式(7):
HO−Ar−Si(OR1)3 (7)
(式(7)中、Arはフェニレン基、ビフェニリレン基、ナフチレン基及びピリジレン基からなる群から選択されるいずれか1種の2価の芳香族有機基を示し、Aはハロゲン原子を示し、R1は水素原子又は炭素数1〜4のアルキル基を示す。)
で表される前駆体化合物を得た後、前記一般式(7)で表される前駆体化合物中の式:−OR1で表される置換基のうちの2つをアリル基に置換し、その後、前記化合物中の水酸基と、トリフラート基とを置換することにより、上記一般式(1)中のXがトリフラート基である第一の有機シラン化合物を得る方法が挙げられる。
本発明の第二の有機シラン化合物は、下記一般式(2):
で表されることを特徴とするものである。
で表される化合物とを反応せしめて、上記一般式(1)で表される第一の有機シラン化合物中の式−Xで表される置換基を、上記一般式(8)中の式:−Ar’で表される置換基に置換して、第二の有機シラン化合物を得る方法が挙げられる。
本発明の有機シリカは、上記本発明の第一及び第二の有機シラン化合物のうちの少なくとも1種を重合せしめて得られたものであることを特徴とするものである。
(i)前記周期構造は上記本発明の第一及び第二の有機シラン化合物間に働く相互作用により形成されるため、上記本発明の第一及び第二の有機シラン化合物間の相互作用が大きくなるように、上記本発明の第一及び第二の有機シラン化合物の中でも、Ar及び/又はAr’で表される有機基がより大きな分子量を有する有機基である有機シラン化合物を用いることが好ましい。
(ii)溶液のpHが1〜3(酸性)又は10〜12(塩基性)であることが好ましく、10〜12(塩基性)であることがより好ましい。
以下のようにして、4-bromo-triethoxysiliybenzeneを調製した。
以下のようにして、4-bromo-diallylethoxysilylbenzeneを調製した。
以下のようにして、4-(triethoxysilyl)iodobenzeneを調製した。
1H NMR (CDCl3) δ7.73(dd,J=7.8Hz,1.4Hz,2H),7.39(d,J=7.8Hz,1.4Hz,2H),3.88(q,J=7.3Hz,6H),1.24(t,J=7.3Hz,9H).
13C NMR (CDCl3) δ137.0, 136.3, 130.4, 97.8, 58.8, 18.1.
このようなNMR測定の結果から、得られた化合物は4-(triethoxysilyl)iodobenzeneであることが確認された。
以下のようにして、4-(diallylethoxysilyl)iodobenzeneを調製した。
1H NMR (CDCl3) δ7.72(d,J=8.1Hz,2H),7.29(d,J=8.1Hz,2H),5.87−5.71(m,2H),4.98−−4.89(m,4H),3.75(q,J=6.8Hz,4H),1.91(d,J=8.1Hz,4H),1.20(t,J=6.8Hz,3H).
13C NMR (CDCl3) δ136.9, 135.6, 134.5, 132.7, 115.0, 97.1, 59.4, 21.1, 18.4.
このようなNMR測定の結果から、得られた化合物は4-(diallylethoxysilyl)iodobenzeneであることが確認された。
以下のようにして、4-(diallylethoxysilyl)phenolを調製した。
1H NMR (CDCl3) δ7.46(d,J=8.6Hz,2H),6.85(d,J=8.6Hz,2H),5.90−5.74(m,2H),5.57(br,1H),4.99−4.88(m,4H),3.75(q,J=6.8Hz,4H),1.92(d,J=8.4Hz,4H),1.20(t,J=6.8Hz,3H).
13C NMR (CDCl3) δ157.2, 135.8, 133.2, 125.9, 115.0, 114.7, 59.3, 21.2, 18.3.
このようなNMR測定の結果から、得られた化合物は4-(diallylethoxysilyl)phenolであることが確認された。
以下のようにして、4-(diallylethoxysilyl)phenyltriflateを調製した。
1H NMR (CDCl3) δ7.67(d,J=8.1Hz,2H),7.28(d,J=8.1Hz,2H),5.87−5.71(m,2H),4.99−4.91(m,4H),3.79(q,J=7.0Hz,2H),1.93(d,J=7.8Hz,4H),1.23(t,J=7.0Hz,3H).
13C NMR (CDCl3) δ150.9, 136.5, 136.0, 132.4, 132.4, 120.6, 115.2, 59.4, 21.1, 18.3.
このようなNMR測定の結果から、得られた化合物は4-(diallylethoxysilyl)phenyltriflateであることが確認された。
以下のようにして、4-(diallylethoxysilyl)phenyltriflateを調製した。
1H NMR (CDCl3) δ7.67(d,J=8.1Hz,2H),7.28(d,J=8.1Hz,2H),5.87−5.71(m,2H),4.99−4.91(m,4H),3.79(q,J=7.0Hz,2H),1.93(d,J=7.8Hz,4H),1.23(t,J=7.0Hz,3H).
13C NMR (CDCl3) δ150.9, 136.5, 136.0, 132.4, 132.4, 120.6, 115.2, 59.4, 21.1, 18.3.
このようなNMR測定の結果から、得られた化合物は4-(diallylethoxysilyl)phenyltriflateであることが確認された。
以下のようにして、4-(diallylethoxysilyl)phenyltriflateを調製した。
1H NMR (CDCl3) δ7.67(d,J=8.1Hz,2H),7.28(d,J=8.1Hz,2H),5.87−5.71(m,2H),4.99−4.91(m,4H),3.79(q,J=7.0Hz,2H),1.93(d,J=7.8Hz,4H),1.23(t,J=7.0Hz,3H).
13C NMR (CDCl3) δ150.9, 136.5, 136.0, 132.4, 132.4, 120.6, 115.2, 59.4, 21.1, 18.3.
このようなNMR測定の結果から、得られた化合物は4-(diallylethoxysilyl)phenyltriflateであることが確認された。
以下のようにして、1-(diallylethoxysilyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzeneを調製した。
1H NMR (CDCl3) δ7.81(d,J=8.4Hz,2H),7.58(d,J=8.4Hz,2H),5.89−5.73(m,2H),4.98−4.87(m,4H),3.75(q,J=7.0Hz,2H),1.94(d,J=7.8Hz,4H),1.34(s,12H),1.20(t,J=7.0Hz,3H).
13C NMR (CDCl3) δ138.5, 133.8, 133.2, 132.9, 127.7, 114.8, 83.8, 59.3, 24.8, 21.1, 18.3.
このようなNMR測定の結果から、得られた化合物は1-(diallylethoxysilyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzeneであることが確認された。
以下のようにして、4-(diallylethoxysilyl)phenyl-trimethyltinを調製した。
1H NMR (CDCl3) δ7.52(d,J=1.62Hz,4H),5.89−5.79(m,2H),5.00−4.89(m,4H),3.76(q,J=6.8Hz,2H),1.93(d,J=8.1Hz,4H),1.21(t,J=6.8Hz,3H),0.29(s,9H,J(Sn−CH3=54.5Hz)).
13C NMR (CDCl3) δ144.6, 135.3, 134.8, 133.4, 133.2, 114.7, 59.3, 21.2, 18.4. −9.63(J(119Sn−CH3)=348.6Hz, J(117Sn−CH3)=333.0Hz).
このようなNMR測定の結果から、得られた化合物は4-(diallylethoxysilyl)phenyl-trimethyltinであることが確認された。
以下のようにして、4-(diallylethoxysilyl)biphenylを調製した。
1H NMR (CDCl3) δ7.68−7.60(m,6H),7.45(t,J=7.0Hz,2H),7.36(t,J=7.0Hz,1H),5.94−5.78(m,2H),5.02−4.91(m,4H),3.80(q,J=6.8Hz,2H),1.97(d,J=7.8Hz,2H),1.23(t,J=6.8Hz,3H).
13C NMR(CDCl3)δ142.4, 140.8, 134.5, 133.7, 133.1, 128.7, 127.4, 127.1, 126.4, 114.8, 59.3, 21.2, 18.4.
このようなNMR測定の結果から、得られた化合物は得られた化合物は上記一般式(2)中のAr’がフェニル基である4-(diallylethoxysilyl)biphenylであることが確認された。
以下のようにして、4-(diallylethoxysilyl)biphenylの調製した。
1H NMR (CDCl3) δ7.68−7.60(m,6H),7.45(t,J=7.0Hz,2H),7.36(t,J=7.0Hz,1H),5.94−5.78(m,2H),5.02−4.91(m,4H),3.80(q,J=6.8Hz,2H),1.97(d,J=7.8Hz,2H),1.23(t,J=6.8Hz,3H).
13C NMR (CDCl3) δ142.4, 140.8, 134.5, 133.7, 133.1, 128.7, 127.4, 127.1, 126.4, 114.8, 59.3, 21.2, 18.4.
このようなNMR測定の結果から、得られた化合物は上記一般式(2)中のAr’がフェニル基である4-(diallylethoxysilyl)biphenylであることが確認された。
以下のようにして、4-(diallylethoxysilyl)-4’-methoxybiphenylを調製した。
1H NMR (CDCl3) δ7.63(d,J=7.6Hz,2H),7.57(d,J=7.6Hz,2H),7.55(d,J=8.4Hz,2H),6.99(d,J=8.4Hz,2H),5.94−5.78(m,2H),5.02−4.91(m,4H),3.86(s,3H),3.79(q,J=6.8Hz,2H),1.97(d,J=8.1Hz,2H),1.23(t,J=6.8Hz,3H).
13C NMR (CDCl3) δ159.3, 142.0, 134.4, 133.3, 133.1, 132.9, 128.1, 126.0, 114.7, 114.2, 59.3, 55.2, 21.2, 18.4.
このようなNMR測定の結果から、得られた化合物は上記一般式(2)中のAr’がメトキシフェニル基である4-(diallylethoxysilyl)-4’-methoxybiphenylであることが確認された。
以下のようにして、4-(diallylethoxysilyl)-4’-methoxybiphenylを調製した。
1H NMR (CDCl3) δ7.63(d,J=7.6Hz,2H),7.57(d,J=7.6Hz,2H),7.55(d,J=8.4Hz,2H),6.99(d,J=8.4Hz,2H),5.94−5.78(m,2H),5.02−4.91(m,4H),3.86(s,3H),3.79(q,J=6.8Hz,2H),1.97(d,J=8.1Hz,2H),1.23(t,J=6.8Hz,3H).
13C NMR (CDCl3) δ159.3, 142.0, 134.4, 133.3, 133.1, 132.9, 128.1, 126.0, 114.7, 114.2, 59.3, 55.2, 21.2, 18.4.
このようなNMR測定の結果から、得られた化合物は上記一般式(2)中のAr’がメトキシフェニル基である4-(diallylethoxysilyl)-4’-methoxybiphenylであることが確認された。
以下のようにして、4-(diallylethoxysilyl)-4’-methoxybiphenylを調製した。
1H NMR (CDCl3) δ7.63(d,J=7.6Hz,2H),7.57(d,J=7.6Hz,2H),7.55(d,J=8.4Hz,2H),6.99(d,J=8.4Hz,2H),5.94−5.78(m,2H),5.02−4.91(m,4H),3.86(s,3H),3.79(q,J=6.8Hz,2H),1.97(d,J=8.1Hz,2H),1.23(t,J=6.8Hz,3H).
13C NMR (CDCl3) δ159.3, 142.0, 134.4, 133.3, 133.1, 132.9, 128.1, 126.0, 114.7, 114.2, 59.3, 55.2, 21.2, 18.4.
このようなNMR測定の結果から、得られた化合物は上記一般式(2)中のAr’がメトキシフェニル基である4-(diallylethoxysilyl)-4’-methoxybiphenylであることが確認された。
以下のようにして、有機シリカを合成した。
以下のようにして、有機シリカを合成した。
以下のようにして、有機シリカを合成した。
以下のようにして、有機シリカを合成した。
以下のようにして、4-(diallylhydroxysilyl)iodobenzeneを調製した。
1H NMR (CDCl3) δ1.89(d,J=7.8Hz,4H),2.19(s,1H),4.92−4.99(m,4H),5.78(ddt,J=16.2Hz,10.3Hz,7.8Hz,2H),7.30(d,J=8.1Hz,2H),7.73(d,J=8.1Hz,2H).
このようなNMR測定の結果から、得られた化合物は4-(diallylhydroxysilyl)iodobenzeneであることが確認された。
以下のようにして、4-(diallylhydroxysilyl)-4’-methoxybiphenylを調製した(シラノールヨード体を用いた鈴木カップリング反応)。
1H NMR (CDCl3) δ1.97(d,J=8.1Hz,4H),2.18(s,1H),3.85(s,3H),4.95(dd,J=9.5Hz,1.6Hz,2H),5.00(dd,J=16.5Hz,1.6Hz,2H),5.85(ddt,J=16.5Hz,9.5Hz,8.1Hz,2H),6.98(d,J=8.9Hz,2H),7.55(d,J=8.9Hz,2H),7.57(d,J=8.1Hz,2H),7.64(d,J=8.1Hz,2H)。
このようなNMR測定の結果から、得られた化合物は4-(diallylhydroxysilyl)-4’-methoxybiphenylであることが確認された。
Claims (3)
- 下記一般式(1):
で表されることを特徴とする有機シラン化合物。 - 下記一般式(2):
で表されることを特徴とする有機シラン化合物。 - 請求項2に記載の有機シラン化合物のうちの少なくとも1種を重合せしめて得られたものであることを特徴とする有機シリカ。
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