WO2004076534A1 - カチオン硬化性含ケイ素化合物の製造方法 - Google Patents
カチオン硬化性含ケイ素化合物の製造方法 Download PDFInfo
- Publication number
- WO2004076534A1 WO2004076534A1 PCT/JP2004/002285 JP2004002285W WO2004076534A1 WO 2004076534 A1 WO2004076534 A1 WO 2004076534A1 JP 2004002285 W JP2004002285 W JP 2004002285W WO 2004076534 A1 WO2004076534 A1 WO 2004076534A1
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- WIPO (PCT)
- Prior art keywords
- group
- compound
- represented
- siloxane bond
- following formula
- Prior art date
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- 150000003377 silicon compounds Chemical class 0.000 title claims abstract description 24
- 238000000034 method Methods 0.000 title claims abstract description 22
- 125000003566 oxetanyl group Chemical group 0.000 claims abstract description 30
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 17
- 125000000524 functional group Chemical group 0.000 claims abstract description 14
- 125000003118 aryl group Chemical group 0.000 claims abstract description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 11
- 230000003301 hydrolyzing effect Effects 0.000 claims abstract description 11
- 238000009835 boiling Methods 0.000 claims abstract description 5
- 238000004519 manufacturing process Methods 0.000 claims description 29
- 239000002210 silicon-based material Substances 0.000 claims description 19
- 239000003054 catalyst Substances 0.000 claims description 18
- 150000003961 organosilicon compounds Chemical class 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 230000002378 acidificating effect Effects 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 238000009833 condensation Methods 0.000 abstract description 14
- 239000003377 acid catalyst Substances 0.000 abstract description 9
- 230000005494 condensation Effects 0.000 abstract description 6
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 35
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
- 150000001875 compounds Chemical class 0.000 description 32
- 238000006460 hydrolysis reaction Methods 0.000 description 28
- 239000000047 product Substances 0.000 description 28
- 230000007062 hydrolysis Effects 0.000 description 27
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- 239000002994 raw material Substances 0.000 description 14
- 238000006482 condensation reaction Methods 0.000 description 10
- 150000002894 organic compounds Chemical class 0.000 description 10
- 239000012298 atmosphere Substances 0.000 description 9
- 238000005227 gel permeation chromatography Methods 0.000 description 8
- 239000011342 resin composition Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 125000003545 alkoxy group Chemical group 0.000 description 7
- -1 siloxane, siloxane skeleton Chemical group 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 229920001296 polysiloxane Polymers 0.000 description 6
- 238000003860 storage Methods 0.000 description 6
- 125000002091 cationic group Chemical group 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 5
- 125000004104 aryloxy group Chemical group 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 125000003700 epoxy group Chemical group 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 3
- 125000000000 cycloalkoxy group Chemical group 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- 229920000734 polysilsesquioxane polymer Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 125000005372 silanol group Chemical group 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical group C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000006459 hydrosilylation reaction Methods 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- MDLRQEHNDJOFQN-UHFFFAOYSA-N methoxy(dimethyl)silicon Chemical compound CO[Si](C)C MDLRQEHNDJOFQN-UHFFFAOYSA-N 0.000 description 2
- RSRCJPGCPWEIHN-UHFFFAOYSA-N methoxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[SiH](OC)C1=CC=CC=C1 RSRCJPGCPWEIHN-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 229910052760 oxygen Inorganic materials 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
- 229920000642 polymer Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- KWEKXPWNFQBJAY-UHFFFAOYSA-N (dimethyl-$l^{3}-silanyl)oxy-dimethylsilicon Chemical compound C[Si](C)O[Si](C)C KWEKXPWNFQBJAY-UHFFFAOYSA-N 0.000 description 1
- YQJPWWLJDNCSCN-UHFFFAOYSA-N 1,3-diphenyltetramethyldisiloxane Chemical compound C=1C=CC=CC=1[Si](C)(C)O[Si](C)(C)C1=CC=CC=C1 YQJPWWLJDNCSCN-UHFFFAOYSA-N 0.000 description 1
- GVJSGABMOHZNSD-UHFFFAOYSA-N 1-triphenylsilylethanone Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(C(=O)C)C1=CC=CC=C1 GVJSGABMOHZNSD-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- OMBADDZNTSOLPP-UHFFFAOYSA-N benzhydryloxy(methyl)silane Chemical compound C=1C=CC=CC=1C(O[SiH2]C)C1=CC=CC=C1 OMBADDZNTSOLPP-UHFFFAOYSA-N 0.000 description 1
- SEGBQNJGOCXIGC-FHERZECASA-N benzyl n-[(2s)-1-[(4-hydroxyoxolan-3-yl)amino]-4-methyl-1-oxopentan-2-yl]carbamate Chemical compound N([C@@H](CC(C)C)C(=O)NC1C(COC1)O)C(=O)OCC1=CC=CC=C1 SEGBQNJGOCXIGC-FHERZECASA-N 0.000 description 1
- RFXODRCAZTVEOH-UHFFFAOYSA-N benzyl-ethoxy-dimethylsilane Chemical compound CCO[Si](C)(C)CC1=CC=CC=C1 RFXODRCAZTVEOH-UHFFFAOYSA-N 0.000 description 1
- WCHNCRPGOCEXPK-UHFFFAOYSA-N butyl(trimethoxy)silane;triethoxy(propyl)silane Chemical compound CCCC[Si](OC)(OC)OC.CCC[Si](OCC)(OCC)OCC WCHNCRPGOCEXPK-UHFFFAOYSA-N 0.000 description 1
- 238000012663 cationic photopolymerization Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- ATGKAFZFOALBOF-UHFFFAOYSA-N cyclohexyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C1CCCCC1 ATGKAFZFOALBOF-UHFFFAOYSA-N 0.000 description 1
- MEWFSXFFGFDHGV-UHFFFAOYSA-N cyclohexyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C1CCCCC1 MEWFSXFFGFDHGV-UHFFFAOYSA-N 0.000 description 1
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- JJQZDUKDJDQPMQ-UHFFFAOYSA-N dimethoxy(dimethyl)silane Chemical compound CO[Si](C)(C)OC JJQZDUKDJDQPMQ-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- DRUOQOFQRYFQGB-UHFFFAOYSA-N ethoxy(dimethyl)silicon Chemical compound CCO[Si](C)C DRUOQOFQRYFQGB-UHFFFAOYSA-N 0.000 description 1
- RSIHJDGMBDPTIM-UHFFFAOYSA-N ethoxy(trimethyl)silane Chemical compound CCO[Si](C)(C)C RSIHJDGMBDPTIM-UHFFFAOYSA-N 0.000 description 1
- ZVJXKUWNRVOUTI-UHFFFAOYSA-N ethoxy(triphenyl)silane Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(OCC)C1=CC=CC=C1 ZVJXKUWNRVOUTI-UHFFFAOYSA-N 0.000 description 1
- PQVKZMRAPBTIQM-UHFFFAOYSA-N ethoxy-methoxy-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](OC)(OCC)C1=CC=CC=C1 PQVKZMRAPBTIQM-UHFFFAOYSA-N 0.000 description 1
- ADLWTVQIBZEAGJ-UHFFFAOYSA-N ethoxy-methyl-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](C)(OCC)C1=CC=CC=C1 ADLWTVQIBZEAGJ-UHFFFAOYSA-N 0.000 description 1
- SBRXLTRZCJVAPH-UHFFFAOYSA-N ethyl(trimethoxy)silane Chemical compound CC[Si](OC)(OC)OC SBRXLTRZCJVAPH-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000003999 initiator Substances 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
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- POPACFLNWGUDSR-UHFFFAOYSA-N methoxy(trimethyl)silane Chemical compound CO[Si](C)(C)C POPACFLNWGUDSR-UHFFFAOYSA-N 0.000 description 1
- FUMSHFZKHQOOIX-UHFFFAOYSA-N methoxy(tripropyl)silane Chemical compound CCC[Si](CCC)(CCC)OC FUMSHFZKHQOOIX-UHFFFAOYSA-N 0.000 description 1
- RJMRIDVWCWSWFR-UHFFFAOYSA-N methyl(tripropoxy)silane Chemical compound CCCO[Si](C)(OCCC)OCCC RJMRIDVWCWSWFR-UHFFFAOYSA-N 0.000 description 1
- RFGGTTPASBFBTB-UHFFFAOYSA-N methyl-[methyl(diphenyl)silyl]oxy-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(C)O[Si](C)(C=1C=CC=CC=1)C1=CC=CC=C1 RFGGTTPASBFBTB-UHFFFAOYSA-N 0.000 description 1
- HLXDKGBELJJMHR-UHFFFAOYSA-N methyl-tri(propan-2-yloxy)silane Chemical compound CC(C)O[Si](C)(OC(C)C)OC(C)C HLXDKGBELJJMHR-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- REOJLIXKJWXUGB-UHFFFAOYSA-N mofebutazone Chemical group O=C1C(CCCC)C(=O)NN1C1=CC=CC=C1 REOJLIXKJWXUGB-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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 238000006884 silylation reaction Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 125000001424 substituent group Chemical group 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
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 0.000 description 1
- GAMLUOSQYHLFCT-UHFFFAOYSA-N triethoxy-[3-[(3-ethyloxetan-3-yl)methoxy]propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1(CC)COC1 GAMLUOSQYHLFCT-UHFFFAOYSA-N 0.000 description 1
- HUZZQXYTKNNCOU-UHFFFAOYSA-N triethyl(methoxy)silane Chemical compound CC[Si](CC)(CC)OC HUZZQXYTKNNCOU-UHFFFAOYSA-N 0.000 description 1
- WILBTFWIBAOWLN-UHFFFAOYSA-N triethyl(triethylsilyloxy)silane Chemical compound CC[Si](CC)(CC)O[Si](CC)(CC)CC WILBTFWIBAOWLN-UHFFFAOYSA-N 0.000 description 1
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
- AAPLIUHOKVUFCC-UHFFFAOYSA-N trimethylsilanol Chemical compound C[Si](C)(C)O AAPLIUHOKVUFCC-UHFFFAOYSA-N 0.000 description 1
- QHUNJMXHQHHWQP-UHFFFAOYSA-N trimethylsilyl acetate Chemical compound CC(=O)O[Si](C)(C)C QHUNJMXHQHHWQP-UHFFFAOYSA-N 0.000 description 1
- VFFKJOXNCSJSAQ-UHFFFAOYSA-N trimethylsilyl benzoate Chemical compound C[Si](C)(C)OC(=O)C1=CC=CC=C1 VFFKJOXNCSJSAQ-UHFFFAOYSA-N 0.000 description 1
- NLSXASIDNWDYMI-UHFFFAOYSA-N triphenylsilanol Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(O)C1=CC=CC=C1 NLSXASIDNWDYMI-UHFFFAOYSA-N 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/06—Preparatory processes
-
- 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
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
- C09D183/06—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/06—Preparatory processes
- C08G77/08—Preparatory processes characterised by the catalysts used
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Silicon Polymers (AREA)
Description
Claims
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP04714889A EP1598389A4 (en) | 2003-02-27 | 2004-02-26 | METHOD FOR PRODUCING A CATIONICALLY HARDENABLE SILICONE COMPOUND |
JP2005502929A JPWO2004076534A1 (ja) | 2003-02-27 | 2004-02-26 | カチオン硬化性含ケイ素化合物の製造方法 |
US10/547,429 US20070055034A1 (en) | 2003-02-27 | 2004-02-26 | Process for producing cation-curable silicon compound |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2003052029 | 2003-02-27 | ||
JP2003052030 | 2003-02-27 | ||
JP2003-052030 | 2003-02-27 | ||
JP2003-052029 | 2003-02-27 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2004076534A1 true WO2004076534A1 (ja) | 2004-09-10 |
Family
ID=32929658
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2004/002285 WO2004076534A1 (ja) | 2003-02-27 | 2004-02-26 | カチオン硬化性含ケイ素化合物の製造方法 |
Country Status (5)
Country | Link |
---|---|
US (1) | US20070055034A1 (ja) |
EP (1) | EP1598389A4 (ja) |
JP (1) | JPWO2004076534A1 (ja) |
KR (1) | KR20050106458A (ja) |
WO (1) | WO2004076534A1 (ja) |
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2006111556A (ja) * | 2004-10-13 | 2006-04-27 | Shin Etsu Chem Co Ltd | かご状オリゴシロキサンの製造方法 |
JP2006131849A (ja) * | 2004-11-09 | 2006-05-25 | Toagosei Co Ltd | 二液型硬化性組成物 |
JP2006131848A (ja) * | 2004-11-09 | 2006-05-25 | Toagosei Co Ltd | ポリオルガノシロキサン及びその製造方法、並びにポリオルガノシロキサンを含有する硬化性組成物 |
JP2007084799A (ja) * | 2005-08-24 | 2007-04-05 | Toray Fine Chemicals Co Ltd | オキセタニル基を有するシリコーン共重合体 |
WO2009090916A1 (ja) * | 2008-01-15 | 2009-07-23 | Toagosei Co., Ltd. | オキセタニル基を有する有機ケイ素化合物およびその製造方法ならびに硬化性組成物 |
JP2009191259A (ja) * | 2008-01-15 | 2009-08-27 | Toagosei Co Ltd | オキセタニル基を有するケイ素化合物の製造方法 |
JP2009209358A (ja) * | 2008-02-06 | 2009-09-17 | Toagosei Co Ltd | カチオン硬化性組成物 |
WO2009131038A1 (ja) | 2008-04-22 | 2009-10-29 | 東亞合成株式会社 | 硬化性組成物及び有機ケイ素化合物の製造方法 |
WO2010073933A1 (ja) * | 2008-12-26 | 2010-07-01 | 東亞合成株式会社 | オキセタニル基を有するケイ素化合物の製造方法 |
JP5311091B2 (ja) * | 2005-04-08 | 2013-10-09 | 東亞合成株式会社 | ポリカルボシラン及びその製造方法 |
WO2022168804A1 (ja) | 2021-02-05 | 2022-08-11 | 東亞合成株式会社 | 無機物質層積層用アンダーコート剤組成物、その硬化物及びその製造方法 |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR101766942B1 (ko) * | 2010-12-28 | 2017-08-09 | 도아고세이가부시키가이샤 | 용제 가용형 반응성 폴리실록산의 제조 방법 |
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JPH1129640A (ja) * | 1997-07-07 | 1999-02-02 | Toagosei Co Ltd | 光カチオン硬化性組成物の製造方法及び光カチオン硬化性ハードコート剤組成物 |
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- 2004-02-26 EP EP04714889A patent/EP1598389A4/en not_active Withdrawn
- 2004-02-26 JP JP2005502929A patent/JPWO2004076534A1/ja active Pending
- 2004-02-26 KR KR1020057015939A patent/KR20050106458A/ko not_active Application Discontinuation
- 2004-02-26 WO PCT/JP2004/002285 patent/WO2004076534A1/ja not_active Application Discontinuation
- 2004-02-26 US US10/547,429 patent/US20070055034A1/en not_active Abandoned
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JPH1087834A (ja) * | 1996-09-10 | 1998-04-07 | Showa Denko Kk | ポリオルガノシルセスキオキサン、その製造方法並びに該化合物を含有する樹脂組成物 |
JPH10330485A (ja) * | 1997-03-25 | 1998-12-15 | Ivoclar Ag | 加水分解可能でかつ重合可能なオキセタンシラン |
JPH1129640A (ja) * | 1997-07-07 | 1999-02-02 | Toagosei Co Ltd | 光カチオン硬化性組成物の製造方法及び光カチオン硬化性ハードコート剤組成物 |
JPH11116682A (ja) * | 1997-08-11 | 1999-04-27 | Toagosei Co Ltd | 光カチオン硬化性樹脂組成物 |
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JP4524602B2 (ja) * | 2004-10-13 | 2010-08-18 | 信越化学工業株式会社 | かご状オリゴシロキサンの製造方法 |
JP2006111556A (ja) * | 2004-10-13 | 2006-04-27 | Shin Etsu Chem Co Ltd | かご状オリゴシロキサンの製造方法 |
JP2006131849A (ja) * | 2004-11-09 | 2006-05-25 | Toagosei Co Ltd | 二液型硬化性組成物 |
JP2006131848A (ja) * | 2004-11-09 | 2006-05-25 | Toagosei Co Ltd | ポリオルガノシロキサン及びその製造方法、並びにポリオルガノシロキサンを含有する硬化性組成物 |
JP5311091B2 (ja) * | 2005-04-08 | 2013-10-09 | 東亞合成株式会社 | ポリカルボシラン及びその製造方法 |
JP2007084799A (ja) * | 2005-08-24 | 2007-04-05 | Toray Fine Chemicals Co Ltd | オキセタニル基を有するシリコーン共重合体 |
JP2009191259A (ja) * | 2008-01-15 | 2009-08-27 | Toagosei Co Ltd | オキセタニル基を有するケイ素化合物の製造方法 |
US8329774B2 (en) | 2008-01-15 | 2012-12-11 | Toagosei Co., Ltd. | Organosilicon compounds which have oxetanyl groups, and a method for the production and curable compositions of the same |
KR101587297B1 (ko) | 2008-01-15 | 2016-01-20 | 도아고세이가부시키가이샤 | 옥세타닐기를 갖는 유기 규소 화합물 및 그의 제조 방법 및 경화성 조성물 |
KR20100120288A (ko) * | 2008-01-15 | 2010-11-15 | 도아고세이가부시키가이샤 | 옥세타닐기를 갖는 유기 규소 화합물 및 그의 제조 방법 및 경화성 조성물 |
WO2009090916A1 (ja) * | 2008-01-15 | 2009-07-23 | Toagosei Co., Ltd. | オキセタニル基を有する有機ケイ素化合物およびその製造方法ならびに硬化性組成物 |
JP2009209358A (ja) * | 2008-02-06 | 2009-09-17 | Toagosei Co Ltd | カチオン硬化性組成物 |
EP2565217A1 (en) | 2008-04-22 | 2013-03-06 | Toagosei Co., Ltd. | Curable composition and process for production of organosilicon compound |
WO2009131038A1 (ja) | 2008-04-22 | 2009-10-29 | 東亞合成株式会社 | 硬化性組成物及び有機ケイ素化合物の製造方法 |
KR101516037B1 (ko) | 2008-04-22 | 2015-04-29 | 도아고세이가부시키가이샤 | 경화성 조성물 및 유기 규소 화합물의 제조 방법 |
CN102264801B (zh) * | 2008-12-26 | 2013-05-01 | 东亚合成株式会社 | 具有氧杂环丁烷基的硅化合物的制备方法 |
US8110613B2 (en) | 2008-12-26 | 2012-02-07 | Toagosei Co., Ltd. | Process for producing silicon compound having oxetanyl group |
JP5382000B2 (ja) * | 2008-12-26 | 2014-01-08 | 東亞合成株式会社 | オキセタニル基を有するケイ素化合物の製造方法 |
WO2010073933A1 (ja) * | 2008-12-26 | 2010-07-01 | 東亞合成株式会社 | オキセタニル基を有するケイ素化合物の製造方法 |
KR101621576B1 (ko) | 2008-12-26 | 2016-05-16 | 도아고세이가부시키가이샤 | 옥세타닐기를 갖는 규소 화합물의 제조 방법 |
WO2022168804A1 (ja) | 2021-02-05 | 2022-08-11 | 東亞合成株式会社 | 無機物質層積層用アンダーコート剤組成物、その硬化物及びその製造方法 |
Also Published As
Publication number | Publication date |
---|---|
EP1598389A1 (en) | 2005-11-23 |
JPWO2004076534A1 (ja) | 2006-06-01 |
US20070055034A1 (en) | 2007-03-08 |
EP1598389A4 (en) | 2006-06-21 |
KR20050106458A (ko) | 2005-11-09 |
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