JP4571125B2 - ブロックトメルカプトシランの製造方法 - Google Patents
ブロックトメルカプトシランの製造方法 Download PDFInfo
- Publication number
- JP4571125B2 JP4571125B2 JP2006509016A JP2006509016A JP4571125B2 JP 4571125 B2 JP4571125 B2 JP 4571125B2 JP 2006509016 A JP2006509016 A JP 2006509016A JP 2006509016 A JP2006509016 A JP 2006509016A JP 4571125 B2 JP4571125 B2 JP 4571125B2
- Authority
- JP
- Japan
- Prior art keywords
- triethoxysilyl
- polysulfane
- chloride
- metal
- alkaline earth
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 238000000034 method Methods 0.000 title claims description 34
- TXDNPSYEJHXKMK-UHFFFAOYSA-N sulfanylsilane Chemical compound S[SiH3] TXDNPSYEJHXKMK-UHFFFAOYSA-N 0.000 title claims description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 65
- 229910000057 polysulfane Inorganic materials 0.000 claims description 42
- 150000003961 organosilicon compounds Chemical class 0.000 claims description 36
- 238000006243 chemical reaction Methods 0.000 claims description 31
- 150000003839 salts Chemical class 0.000 claims description 30
- 229910052751 metal Inorganic materials 0.000 claims description 28
- 239000002184 metal Substances 0.000 claims description 28
- 229910052783 alkali metal Inorganic materials 0.000 claims description 26
- 150000001340 alkali metals Chemical class 0.000 claims description 26
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 21
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 21
- -1 methoxy, ethoxy Chemical group 0.000 claims description 19
- 229910052708 sodium Inorganic materials 0.000 claims description 16
- 239000011734 sodium Substances 0.000 claims description 16
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 15
- 150000001266 acyl halides Chemical class 0.000 claims description 13
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 13
- REEZZSHJLXOIHL-UHFFFAOYSA-N octanoyl chloride Chemical compound CCCCCCCC(Cl)=O REEZZSHJLXOIHL-UHFFFAOYSA-N 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 10
- 239000007788 liquid Substances 0.000 claims description 9
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 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
- PZJJKWKADRNWSW-UHFFFAOYSA-N trimethoxysilicon Chemical group CO[Si](OC)OC PZJJKWKADRNWSW-UHFFFAOYSA-N 0.000 claims description 3
- MLQBTMWHIOYKKC-KTKRTIGZSA-N (z)-octadec-9-enoyl chloride Chemical compound CCCCCCCC\C=C/CCCCCCCC(Cl)=O MLQBTMWHIOYKKC-KTKRTIGZSA-N 0.000 claims description 2
- WFSGQBNCVASPMW-UHFFFAOYSA-N 2-ethylhexanoyl chloride Chemical compound CCCCC(CC)C(Cl)=O WFSGQBNCVASPMW-UHFFFAOYSA-N 0.000 claims description 2
- HGTWZCDAFFNNGN-UHFFFAOYSA-N 3,3-dimethyl-5-triethoxysilylpentanethioic S-acid Chemical compound CCO[Si](OCC)(OCC)CCC(C)(C)CC(S)=O HGTWZCDAFFNNGN-UHFFFAOYSA-N 0.000 claims description 2
- XHNGORVETGDZTH-UHFFFAOYSA-N 3-methyl-5-triethoxysilylpentanethioic s-acid Chemical compound CCO[Si](OCC)(OCC)CCC(C)CC(S)=O XHNGORVETGDZTH-UHFFFAOYSA-N 0.000 claims description 2
- RJVOFVDYOUKVJM-UHFFFAOYSA-N 3-methyl-9-trimethoxysilylnonanethioic S-acid Chemical compound CO[Si](OC)(OC)CCCCCCC(C)CC(S)=O RJVOFVDYOUKVJM-UHFFFAOYSA-N 0.000 claims description 2
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 claims description 2
- VWOCJSYXZSVJQY-UHFFFAOYSA-N CC(C)(C[SiH2]OC)C(O)=S Chemical compound CC(C)(C[SiH2]OC)C(O)=S VWOCJSYXZSVJQY-UHFFFAOYSA-N 0.000 claims description 2
- XUUMUAOLWOYCKK-UHFFFAOYSA-N CC(C)O[SiH2]CC(C)(C)C(O)=S Chemical compound CC(C)O[SiH2]CC(C)(C)C(O)=S XUUMUAOLWOYCKK-UHFFFAOYSA-N 0.000 claims description 2
- ROCMTYNCIFIFHG-UHFFFAOYSA-N CO[SiH](OC)C(C)CCOC(C)=S Chemical compound CO[SiH](OC)C(C)CCOC(C)=S ROCMTYNCIFIFHG-UHFFFAOYSA-N 0.000 claims description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 claims description 2
- HFWNIEFOEWMVCF-UHFFFAOYSA-N O-(3-diethoxysilylbutyl) ethanethioate Chemical compound CCO[SiH](OCC)C(C)CCOC(C)=S HFWNIEFOEWMVCF-UHFFFAOYSA-N 0.000 claims description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- ZIRZHZPXSOKIGF-UHFFFAOYSA-N O-methyl 3-diethoxysilylpropanethioate Chemical compound COC(CC[SiH](OCC)OCC)=S ZIRZHZPXSOKIGF-UHFFFAOYSA-N 0.000 claims description 2
- UYKPRDGGENWWDO-UHFFFAOYSA-N O-methyl 3-dimethoxysilylpropanethioate Chemical compound COC(CC[SiH](OC)OC)=S UYKPRDGGENWWDO-UHFFFAOYSA-N 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical group CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims description 2
- 239000012346 acetyl chloride Substances 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical class ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims description 2
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- 239000011575 calcium Substances 0.000 claims description 2
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 claims description 2
- NQGIJDNPUZEBRU-UHFFFAOYSA-N dodecanoyl chloride Chemical compound CCCCCCCCCCCC(Cl)=O NQGIJDNPUZEBRU-UHFFFAOYSA-N 0.000 claims description 2
- UCVODTZQZHMTPN-UHFFFAOYSA-N heptanoyl chloride Chemical compound CCCCCCC(Cl)=O UCVODTZQZHMTPN-UHFFFAOYSA-N 0.000 claims description 2
- YWGHUJQYGPDNKT-UHFFFAOYSA-N hexanoyl chloride Chemical compound CCCCCC(Cl)=O YWGHUJQYGPDNKT-UHFFFAOYSA-N 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- 229910000103 lithium hydride Inorganic materials 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- 239000011777 magnesium Substances 0.000 claims description 2
- 229910012375 magnesium hydride Inorganic materials 0.000 claims description 2
- RVZJJFTUWQGPDM-UHFFFAOYSA-N o-(3-triethoxysilylpropyl) ethanethioate Chemical compound CCO[Si](OCC)(OCC)CCCOC(C)=S RVZJJFTUWQGPDM-UHFFFAOYSA-N 0.000 claims description 2
- QXBLIUBAPLUCFY-UHFFFAOYSA-N o-(triethoxysilylmethyl) ethanethioate Chemical compound CCO[Si](OCC)(OCC)COC(C)=S QXBLIUBAPLUCFY-UHFFFAOYSA-N 0.000 claims description 2
- DUGAFPBTRVNWOH-UHFFFAOYSA-N o-(trimethoxysilylmethyl) ethanethioate Chemical compound CO[Si](OC)(OC)COC(C)=S DUGAFPBTRVNWOH-UHFFFAOYSA-N 0.000 claims description 2
- XLHROWYJKQZJBU-UHFFFAOYSA-N o-[2-[diethoxy(methyl)silyl]ethyl] ethanethioate Chemical compound CCO[Si](C)(OCC)CCOC(C)=S XLHROWYJKQZJBU-UHFFFAOYSA-N 0.000 claims description 2
- YWVJNDNHFJEYCV-UHFFFAOYSA-N o-[2-[dimethyl(propan-2-yloxy)silyl]ethyl] ethanethioate Chemical compound CC(C)O[Si](C)(C)CCOC(C)=S YWVJNDNHFJEYCV-UHFFFAOYSA-N 0.000 claims description 2
- XNSYTOZFTIEDHZ-UHFFFAOYSA-N o-[2-[methoxy(dimethyl)silyl]ethyl] ethanethioate Chemical compound CO[Si](C)(C)CCOC(C)=S XNSYTOZFTIEDHZ-UHFFFAOYSA-N 0.000 claims description 2
- BRMSZTGNZHLNDG-UHFFFAOYSA-N o-[2-[methyl-di(propan-2-yloxy)silyl]ethyl] ethanethioate Chemical compound CC(C)O[Si](C)(OC(C)C)CCOC(C)=S BRMSZTGNZHLNDG-UHFFFAOYSA-N 0.000 claims description 2
- KRZHJDOXWGZKTG-UHFFFAOYSA-N o-[3-tri(propan-2-yloxy)silylpropyl] ethanethioate Chemical compound CC(C)O[Si](OC(C)C)(OC(C)C)CCCOC(C)=S KRZHJDOXWGZKTG-UHFFFAOYSA-N 0.000 claims description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 2
- XGISHOFUAFNYQF-UHFFFAOYSA-N pentanoyl chloride Chemical compound CCCCC(Cl)=O XGISHOFUAFNYQF-UHFFFAOYSA-N 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 claims description 2
- 229910000105 potassium hydride Inorganic materials 0.000 claims description 2
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 claims description 2
- 239000012312 sodium hydride Substances 0.000 claims description 2
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- CZKIATYJHXKWFK-UHFFFAOYSA-N 3-methyl-11-triethoxysilylundecanethioic S-acid Chemical compound CCO[Si](OCC)(OCC)CCCCCCCCC(C)CC(S)=O CZKIATYJHXKWFK-UHFFFAOYSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- YNKLSJDOPAEPQD-UHFFFAOYSA-N C(CCCCCCC)(=S)OCCC[SiH3] Chemical compound C(CCCCCCC)(=S)OCCC[SiH3] YNKLSJDOPAEPQD-UHFFFAOYSA-N 0.000 claims 1
- COQGTXSRUFWIHS-UHFFFAOYSA-N O-methyl 3-di(propan-2-yloxy)silylpropanethioate Chemical compound COC(CC[SiH](OC(C)C)OC(C)C)=S COQGTXSRUFWIHS-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- MBTWMRKDHFRJMD-UHFFFAOYSA-N o-(3-triethoxysilylpropyl) benzenecarbothioate Chemical compound CCO[Si](OCC)(OCC)CCCOC(=S)C1=CC=CC=C1 MBTWMRKDHFRJMD-UHFFFAOYSA-N 0.000 claims 1
- IGNWXQRLCXZJKB-UHFFFAOYSA-N o-(3-triethoxysilylpropyl) hexadecanethioate Chemical compound CCCCCCCCCCCCCCCC(=S)OCCC[Si](OCC)(OCC)OCC IGNWXQRLCXZJKB-UHFFFAOYSA-N 0.000 claims 1
- HESLUACQQJVBGX-UHFFFAOYSA-N o-(3-triethoxysilylpropyl) octanethioate Chemical compound CCCCCCCC(=S)OCCC[Si](OCC)(OCC)OCC HESLUACQQJVBGX-UHFFFAOYSA-N 0.000 claims 1
- BEJDMJDIMBMTKP-UHFFFAOYSA-N o-(6-triethoxysilylhexan-2-yl) ethanethioate Chemical compound CCO[Si](OCC)(OCC)CCCCC(C)OC(C)=S BEJDMJDIMBMTKP-UHFFFAOYSA-N 0.000 claims 1
- JEZYIWSVSYEPQF-UHFFFAOYSA-N o-(8-triethoxysilyloctan-2-yl) ethanethioate Chemical compound CCO[Si](OCC)(OCC)CCCCCCC(C)OC(C)=S JEZYIWSVSYEPQF-UHFFFAOYSA-N 0.000 claims 1
- KIEVXBZIFOVSNT-UHFFFAOYSA-N o-(8-triethoxysilyloctan-4-yl) ethanethioate Chemical compound CCCC(OC(C)=S)CCCC[Si](OCC)(OCC)OCC KIEVXBZIFOVSNT-UHFFFAOYSA-N 0.000 claims 1
- MYBHWAWTDFWNOU-UHFFFAOYSA-N o-(8-triethoxysilyloctyl) ethanethioate Chemical compound CCO[Si](OCC)(OCC)CCCCCCCCOC(C)=S MYBHWAWTDFWNOU-UHFFFAOYSA-N 0.000 claims 1
- LSCOKICIXSMFCZ-UHFFFAOYSA-N o-[2-[ethoxy(dimethyl)silyl]ethyl] ethanethioate Chemical compound CCO[Si](C)(C)CCOC(C)=S LSCOKICIXSMFCZ-UHFFFAOYSA-N 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 239000000047 product Substances 0.000 description 12
- 239000000725 suspension Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- FBBATURSCRIBHN-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyldisulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSCCC[Si](OCC)(OCC)OCC FBBATURSCRIBHN-UHFFFAOYSA-N 0.000 description 10
- 229910001507 metal halide Inorganic materials 0.000 description 9
- 238000011084 recovery Methods 0.000 description 7
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 238000004817 gas chromatography Methods 0.000 description 6
- 150000005309 metal halides Chemical class 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 239000008367 deionised water Substances 0.000 description 5
- 229910021641 deionized water Inorganic materials 0.000 description 5
- 239000002699 waste material Substances 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- 150000003377 silicon compounds Chemical class 0.000 description 4
- 239000007822 coupling agent Substances 0.000 description 3
- 230000007613 environmental effect Effects 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- SIXNTGDWLSRMIC-UHFFFAOYSA-N sodium;toluene Chemical compound [Na].CC1=CC=CC=C1 SIXNTGDWLSRMIC-UHFFFAOYSA-N 0.000 description 3
- 239000005046 Chlorosilane Substances 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 229910052728 basic metal Chemical class 0.000 description 2
- 150000003818 basic metals Chemical class 0.000 description 2
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 229910052987 metal hydride Inorganic materials 0.000 description 2
- 150000004681 metal hydrides Chemical class 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 150000003003 phosphines Chemical class 0.000 description 2
- 150000004756 silanes Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- DEILIWSHLDNQRR-UHFFFAOYSA-N 1-(2-triethoxysilyl-4-bicyclo[2.2.1]hept-2-enyl)ethanethione Chemical compound C1CC2C([Si](OCC)(OCC)OCC)=CC1(C(C)=S)C2 DEILIWSHLDNQRR-UHFFFAOYSA-N 0.000 description 1
- BEINZVXQFFJBGC-UHFFFAOYSA-N 1-(2-triethoxysilyl-5-bicyclo[2.2.1]hept-2-enyl)ethanethione Chemical compound C1C2C([Si](OCC)(OCC)OCC)=CC1C(C(C)=S)C2 BEINZVXQFFJBGC-UHFFFAOYSA-N 0.000 description 1
- ZVFSAUUMYMGGCR-UHFFFAOYSA-N 1-[2-(2-triethoxysilylethyl)-4-bicyclo[2.2.1]hept-2-enyl]ethanethione Chemical compound C1CC2C(CC[Si](OCC)(OCC)OCC)=CC1(C(C)=S)C2 ZVFSAUUMYMGGCR-UHFFFAOYSA-N 0.000 description 1
- RYTALXFKQSSDOL-UHFFFAOYSA-N 1-[2-(2-triethoxysilylethyl)-5-bicyclo[2.2.1]hept-2-enyl]ethanethione Chemical compound C1C2C(CC[Si](OCC)(OCC)OCC)=CC1C(C(C)=S)C2 RYTALXFKQSSDOL-UHFFFAOYSA-N 0.000 description 1
- AVLPDYQOOBNGLR-UHFFFAOYSA-N 1-[3-(2-triethoxysilylethyl)cyclohexyl]ethanethione Chemical compound CCO[Si](OCC)(OCC)CCC1CCCC(C(C)=S)C1 AVLPDYQOOBNGLR-UHFFFAOYSA-N 0.000 description 1
- VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 description 1
- DAYRVMQCDGKGGD-UHFFFAOYSA-N 3-methyl-7-triethoxysilylheptanethioic S-acid Chemical compound CCO[Si](OCC)(OCC)CCCCC(C)CC(S)=O DAYRVMQCDGKGGD-UHFFFAOYSA-N 0.000 description 1
- ZQFSFGBBEVOFFB-UHFFFAOYSA-N 3-methyl-9-triethoxysilylnonanethioic S-acid Chemical compound CCO[Si](OCC)(OCC)CCCCCCC(C)CC(S)=O ZQFSFGBBEVOFFB-UHFFFAOYSA-N 0.000 description 1
- JPSSZFVPDCJVFL-UHFFFAOYSA-N 3-propyl-7-triethoxysilylheptanethioic S-acid Chemical compound CCCC(CC(S)=O)CCCC[Si](OCC)(OCC)OCC JPSSZFVPDCJVFL-UHFFFAOYSA-N 0.000 description 1
- ZPLDJLWIAMTJJW-UHFFFAOYSA-N C(C)(=O)OSC([SiH](OC(C)C)OC(C)C)C Chemical compound C(C)(=O)OSC([SiH](OC(C)C)OC(C)C)C ZPLDJLWIAMTJJW-UHFFFAOYSA-N 0.000 description 1
- FJNUAAGMNLHEJS-UHFFFAOYSA-N CCO[SiH2]CC(C)(C)C(O)=S Chemical compound CCO[SiH2]CC(C)(C)C(O)=S FJNUAAGMNLHEJS-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- PWAXUOGZOSVGBO-UHFFFAOYSA-N adipoyl chloride Chemical compound ClC(=O)CCCCC(Cl)=O PWAXUOGZOSVGBO-UHFFFAOYSA-N 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- HCUYBXPSSCRKRF-UHFFFAOYSA-N diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- WQZUKOYQSSSMBL-UHFFFAOYSA-N o-(10-triethoxysilyldecan-2-yl) ethanethioate Chemical compound CCO[Si](OCC)(OCC)CCCCCCCCC(C)OC(C)=S WQZUKOYQSSSMBL-UHFFFAOYSA-N 0.000 description 1
- VFXVAXFIFHSGNR-UHFFFAOYSA-N octyl carbonochloridate Chemical compound CCCCCCCCOC(Cl)=O VFXVAXFIFHSGNR-UHFFFAOYSA-N 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 1
- 150000003566 thiocarboxylic acids Chemical class 0.000 description 1
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 1
- 238000010977 unit operation Methods 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
-
- 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
- C07F7/1892—Preparation; Treatments not provided for in C07F7/20 by reactions not provided for in C07F7/1876 - C07F7/1888
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Silicon Polymers (AREA)
Description
(a)以下の一般式の1種以上のポリスルファン含有有機ケイ素化合物を、1種以上のアルカリ金属、アルカリ土類金属又はアルカリ金属もしくはアルカリ土類金属の塩基性誘導体と反応させて、対応ポリスルファン含有有機ケイ素化合物の金属塩を得る段階
(R1 3SiG)2Sn
(式中、各R1は、少なくとも1個のR1基がメトキシ又はエトキシであることを条件として、独立にメトキシ、エトキシ又は炭素原子数1〜約6のアルキルであり、Gは炭素原子数1〜約12のアルキレン基であり、nは2〜約8である。)、及び
(b)ポリスルファン含有有機ケイ素化合物の金属塩をアシルハロゲン化物又はカルボニルジハロゲン化物と反応させて、ブロックトメルカプトシランを得る段階
を含んでなる方法を提供する。
金属+(R1 3SiG)2Sn → (R1 3SiG)2S−金属
(R1 3SiG)2S−金属+R2C(O)X → R2C(O)SGSiR1 3+金属−X
周囲温度で、トルエン515.20gをナトリウム25.00g(1.076モル)で処理し、約105℃に加温した。溶融したナトリウム−トルエン懸濁液を、265.21gのMPTES(1.079モル)で30分間処理したところ、水素が発生した。MPTESの添加完了後、得られた無色透明の溶液を約45℃に冷却し、塩化オクタノイル164.75g(0.982モル)で処理した。塩化オクタノイルの添加によって、発熱反応が生じ、塩が生成した。塩化オクタノイルを1時間にわたって添加したところ、反応温度がゆっくりと62℃まで上昇した。反応系を50℃に冷却したところで、脱イオン水215.0gを添加した。その結果、塩が溶解し、二層を形成した。水層を除去し、トルエンを真空除去してトルエン504.72gを回収した(回収率98%)。ブロックトメルカプトシラン387.59gが無色透明の液体として回収され、そのGC組成は以下の通りであった(効率98%)。
周囲温度で、50L反応器にトルエン45.0lb(20.4kg)を仕込んだ後、ナトリウム2.4lb(1015g、43.7モル)を仕込んだ。この懸濁液を約105℃に加温し、得られた溶融ナトリウムを24.3lbのMPTES(11.0kg、44.8モル)で1時間22分処理したところ、水素が発生した。MPTESの添加完了後、透明な溶液を周囲温度に冷却し、次いで塩化オクタノイル15.5lb(7.0kg、42.8モル)で1時間35分処理したところ、反応温度が58℃に達した。得られた混合物を32℃に冷却し、次いで脱イオン水19.0lb(8.6kg)を添加した。その結果、塩が溶解し、二層を形成した。水層を除去して水性廃棄物25.4lb(11.5kg)を回収し、トルエンを真空除去してトルエン46.1lb(20.9kg、回収率102%)を回収した。生成物を、5ミクロンのフィルターパッドを用いたKunoフィルターで濾過し、ブロックトメルカプトシラン31.0lb(14.0kg)が黄色透明な液体として回収され、そのGC分析結果は以下の通りであった(効率85%)。
周囲温度で、トルエン526.82gをナトリウム29.28g(1.261モル)で処理し、約110℃に加温した。溶融ナトリウム−トルエン懸濁液を、Silquest(登録商標)A−1589 299.15g(0.590モル)で45分間処理した。Silquest(登録商標)A−1589の添加で発熱が起こり、濃赤紫色の不透明な溶液を生じた。Silquest(登録商標)A−1589の添加完了後、反応混合物を約45℃に冷却し、塩化オクタノイル189.26g(1.152モル)を1時間にわたって添加したところ、粘稠な塩懸濁液が得られ、反応系は60℃に達した。約45℃で反応系を水278.42gで処理すると、塩が溶解し、透明な黄橙色のトルエン層と、暗色で不透明な水層とが得られ、水層を除去した。水性廃棄物382.62gが回収された。トルエンを真空ストリッピングしてトルエン576.93gを回収した(回収率106%、水分を含んでいた)。ブロックトメルカプトシラン373.53gが透明な濃橙色の液体として回収され、そのGC分析結果は以下の通りであった(効率87%)。
周囲温度で、50L反応器にトルエン46.0lb(20.9kg)を仕込んだ後、ナトリウム2.3 bl(164g、45.8モル)を添加し、約110℃に加温した。溶融ナトリウムを、Silquest(登録商標)A−1589 22.7lb(10.3kg)で69分間処理したところ、発熱反応が生じた。Silquest(登録商標)A−1589の添加完了後、得られた暗色の懸濁液を約38℃に冷却し、次いで塩化オクタノイル13.8lb(6.3kg、38.1モル)で2時間処理したところ、反応温度は48℃に達した。得られた懸濁液を周囲温度に冷却し、次いで脱イオン水22.0lb(10.0kg)で処理した。5℃の発熱が観察され、塩が溶解して、二層を生じた。暗色で不透明な水層を除去し、水性廃棄物31.4lb(14.2kg)を回収した。トルエンをストリッピングし、43.9lb(19.9kg、回収率95%)を回収した。生成物を、5ミクロンのフィルターパッドを用いたKunoフィルターで濾過し、ブロックトメルカプトシラン31.0lb(14.1kg)が透明で黄色の液体として得られ、そのGC分析結果は以下の通りであった(効率92%)。
周囲温度で、トルエン509.88gをナトリウム30.04g(1.299モル)で処理し、約110℃に加温した。溶融ナトリウム−トルエン懸濁液を、Silquest(登録商標)Y−15304 300.97g(0.590モル)で45分間処理した。Silquest(登録商標)Y−15304を添加すると発熱し、濃赤紫色の不透明な溶液を生じた。Silquest(登録商標)Y−15304の添加完了後、反応混合物を約45℃に冷却し、塩化オクタノイル196.01g(1.169モル)を1時間にわたって添加したところ、粘稠な塩懸濁液が得られ、このときの反応は60℃に達した。約45℃で、反応を水270.72gで処理した結果、塩が溶解し、透明な黄橙色のトルエン層と暗色で不透明の水層とが得られ、水層を除去した。水性廃棄物330.89gを回収した。トルエンを真空ストリッピングし、トルエン382.98gを回収した(回収率75%)。ブロックトメルカプトシラン433.06gが透明な濃黄色の液体として回収され、そのGC分析結果は以下の通りであった(効率95%)。
周囲温度で、50L反応器にトルエン45.0lb(20.4kg)及びナトリウム 2.34lb(1061g、45.7モル)を仕込み、110℃に加温した。溶融したナトリウムを、Silquest(登録商標)Y−15304 22.8lb(10.3kg)で69分間処理したところ、発熱反応が生じた。Silquest(登録商標)Y−15304の添加完了後、得られた暗色不透明の懸濁液を35℃に冷却し、塩化オクタノイル13.6lb(6.2kg、37.6モル)を1時間49分にわたって添加したところ、発熱反応が起こり反応温度は約50℃に達した。塩化オクタノイルの添加完了後、得られた懸濁液を脱イオン水22.2lb(10.1kg)で処理すると、塩が溶解して、二層を形成した。得られた暗色の水層を除去し、30.0lb(13.7kg)回収した。トルエンを真空除去し、45.7lb(20.7kg、回収率102%)回収した。生成物を5ミクロンのフィルターパッドを用いたKunoフィルターに通し、ブロックトメルカプトシラン30.6lb(13.9kg)が透明で濃黄色の液体として回収され、そのGC分析結果は以下の通りであった(効率92%)。
周囲温度で、Solvent(登録商標)140 160gをナトリウム11g(0.478モル)で処理して、約110℃に加温した。溶融ナトリウム−Solvent(登録商標)140懸濁液を、Silquest(登録商標)A−1289 63g(0.117モル)で45分間処理した。Silquest(登録商標)A−1289を添加すると発熱が起こり、濃赤紫色の不透明な溶液を生じた。Silquest(登録商標)A−1289の添加完了後、反応混合物を約45℃に冷却し、塩化オクタノイル76g(0.468モル)を1時間にわたって添加したところ、粘稠な塩懸濁液が得られ、このときの反応温度は104℃に達した。約45℃で反応系を水175gで処理すると、塩が溶解して、透明な黄橙色のSolvent(登録商標)140層と、暗色で不透明な層とが得られ、不透明層を除去した。水性廃棄物236gを回収した。トルエンを真空ストリッピングし、Solvent(登録商標)140 155gを回収した(回収率97%)。ブロックトメルカプトシラン110gが透明な濃黄色の液体として回収され、そのGC分析結果は以下の通りであった(効率89%)。
Claims (15)
- ブロックトメルカプトシランの製造方法であって、
(a)以下の一般式の1種以上のポリスルファン含有有機ケイ素化合物を、1種以上のアルカリ金属、アルカリ土類金属又はアルカリ金属もしくはアルカリ土類金属の塩基性誘導体と反応させて、対応ポリスルファン含有有機ケイ素化合物の金属塩を得る段階
(R1 3SiG)2Sn
(式中、各R1は、少なくとも1個のR1基がメトキシ又はエトキシであることを条件として、独立にメトキシ、エトキシ又は炭素原子数1〜6のアルキルであり、Gは炭素原子数1〜12のアルキレン基であり、nは2〜8である。)、及び
(b)ポリスルファン含有有機ケイ素化合物の金属塩をアシルハロゲン化物又はカルボニルジハロゲン化物と反応させて、ブロックトメルカプトシランを得る段階を含んでなる方法。 - 前記ポリスルファン含有有機ケイ素化合物が、ビス[(トリエトキシシリル)プロピル]ポリスルファン、ビス[(メチルジエトキシシリル)プロピル]ポリスルファン、ビス[(トリメトキシシリル)プロピル]ポリスルファン、及びビス[(メチルジメトキシシリル)プロピル]ポリスルファンからなる群から選択される、請求項1記載の方法。
- アルカリ金属、アルカリ土類金属及びアルカリ金属又はアルカリ土類金属の塩基性誘導体が、リチウム、ナトリウム、カリウム、マグネシウム、カルシウム、水素化リチウム、水素化ナトリウム、水素化カリウム、水素化マグネシウム、水素化カルシウム及びこれらの混合物からなる群から選択される、請求項1記載の方法。
- 前記アシルハロゲン化物又はカルボニルジハロゲン化物が以下の一般式のものである、請求項1記載の方法。
R2C(O)X
式中、R2は、ハロゲン又は炭素原子数18以下のアルキル、アルケニル、アリール、アルカリールもしくはアラルキルであり、Xはハロゲンである。 - 前記アシルハロゲン化物が、塩化アセチル、塩化プロパノイル、塩化ブタノイル、塩化ペンタノイル、塩化ヘキサノイル、塩化ヘプタノイル、塩化オクタノイル、塩化2−エチルヘキサノイル、塩化ラウロイル、塩化オレオイル、塩化フェニルアセチル、及び塩化ベンゾイルである、請求項4記載の方法。
- 前記カルボニルジハロゲン化物がホスゲンである、請求項4記載の方法。
- 前記ブロックトメルカプトシラン生成物が以下の一般式のものである、請求項4記載の方法。
R2C(O)SGSiR1 3
(式中、各R 1 は、少なくとも1個のR 1 基がメトキシ又はエトキシであることを条件として、独立にメトキシ、エトキシ又は炭素原子数1〜6のアルキルであり、Gは炭素原子数1〜12のアルキレン基であり、R 2 は、ハロゲン又は炭素原子数18以下のアルキル、アルケニル、アリール、アルカリールもしくはアラルキルである。) - 前記ブロックトメルカプトシラン生成物が、2−トリエトキシシリル−1−エチルチオアセテート、2−トリメトキシシリル−1−エチルチオアセテート、2−(メチルジメトキシシリル)−1−エチルチオアセテート、3−トリメトキシシリル−1−プロピルチオアセテート、トリエトキシシリルメチルチオアセテート、トリメトキシシリルメチルチオアセテート、トリイソプロポキシシリルメチルチオアセテート、メチルジエトキシシリルメチルチオアセテート、メチルジメトキシシリルメチルチオアセテート、メチルジイソプロポキシシリルメチルチオアセテート、ジメチルエトキシシリルメチルチオアセテート、ジメチルメトキシシリルメチルチオアセテート、ジメチルイソプロポキシシリルメチルチオアセテート、2−トリイソプロポキシシリル−1−エチルチオアセテート、2−(メチルジエトキシシリル)−1−エチルチオアセテート、2−(メチルジイソプロポキシシリル)−1−エチルチオアセテート、2−(ジメチルエトキシシリル)−1−エチルチオアセテート、2−(ジメチルメトキシシリル)−1−エチルチオアセテート、2−(ジメチルイソプロポキシシリル)−1−エチルチオアセテート、3−トリエトキシシリル−1−プロピルチオアセテート、3−トリイソプロポキシシリル−1−プロピルチオアセテート、3−メチルジエトキシシリル−1−プロピルチオアセテート、3−メチルジメトキシシリル−1−プロピルチオアセテート、3−メチルジイソプロポキシシリル−1−プロピルチオアセテート、6−トリエトキシシリル−1−ヘキシルチオアセテート、1−トリエトキシシリル−5−ヘキシルチオアセテート、8−トリエトキシシリル−1−オクチルチオアセテート、1−トリエトキシシリル−7−オクチルチオアセテート、1−トリエトキシシリル−5−オクチルチオアセテート、8−トリメトキシシリル−1−オクチルチオアセテート、1−トリメトキシシリル−7−オクチルチオアセテート、10−トリエトキシシリル−1−デシルチオアセテート、1−トリエトキシシリル−9−デシルチオアセテート、1−トリエトキシシリル−2−ブチルチオアセテート、1−トリエトキシシリル−3−ブチルチオアセテート、1−トリエトキシシリル−3−メチル−2−ブチルチオアセテート、1−トリエトキシシリル−3−メチル−3−ブチルチオアセテート、3−トリメトキシシリル−1−プロピルチオオクタノエート、3−トリエトキシシリル−1−プロピルチオパルミテート、3−トリエトキシシリル−1−プロピルチオオクタノエート、3−トリエトキシシリル−1−プロピルチオベンゾエート、及び3−トリエトキシシリル−1−プロピルチオ−2−エチルヘキサノエートからなる群から選択される、請求項7記載の方法。
- アルカリ金属、アルカリ土類金属、アルカリ金属又はアルカリ土類金属の塩基性誘導体とポリスルファン含有有機ケイ素化合物とのモル当量の範囲が1:1〜10:1である、請求項1記載の方法。
- アルカリ金属、アルカリ土類金属、アルカリ金属又はアルカリ土類金属の塩基性誘導体とポリスルファン含有有機ケイ素化合物とのモル当量の範囲2:1〜2.5:1である、請求項1記載の方法。
- ポリスルファン含有有機ケイ素化合物の金属塩とアシルハロゲン化物との範囲が1.25:1〜1:1のモル当量であり、又はカルボニルジハロゲン化物との範囲が2.25:1〜2:1のモル当量である、請求項1記載の方法。
- ポリスルファン含有有機ケイ素化合物とアルカリ金属、アルカリ土類金属又はアルカリ金属もしくはアルカリ土類金属の塩基性誘導体との反応を該金属又は金属誘導体が液体状態にある温度で実施する、請求項1記載の方法。
- ポリスルファン含有有機ケイ素化合物の金属塩とアシルハロゲン化物又はカルボニルジハロゲン化物との反応を10〜50℃の温度で実施する、請求項1記載の方法。
- 溶媒中で実施される請求項1記載の方法。
- 前記溶媒がトルエン、ベンゼン、キシレン、ヘキサン、ヘプタン、イソオクタン及びオクタンからなる群から選択される、請求項14記載の方法。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/378,184 US6777569B1 (en) | 2003-03-03 | 2003-03-03 | Process for the manufacture of blocked mercaptosilanes |
PCT/US2004/006422 WO2004078813A2 (en) | 2003-03-03 | 2004-03-03 | Process for the manufacture of blocked mercaptosilanes |
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JP2006519864A JP2006519864A (ja) | 2006-08-31 |
JP4571125B2 true JP4571125B2 (ja) | 2010-10-27 |
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JP2006509016A Expired - Fee Related JP4571125B2 (ja) | 2003-03-03 | 2004-03-03 | ブロックトメルカプトシランの製造方法 |
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US (1) | US6777569B1 (ja) |
EP (1) | EP1603925A2 (ja) |
JP (1) | JP4571125B2 (ja) |
KR (1) | KR101052958B1 (ja) |
CN (1) | CN100422192C (ja) |
AR (1) | AR043461A1 (ja) |
AU (1) | AU2004217886A1 (ja) |
BR (1) | BRPI0408662B1 (ja) |
CA (1) | CA2517875A1 (ja) |
CL (1) | CL2004000421A1 (ja) |
MX (1) | MXPA05009376A (ja) |
NO (1) | NO20054516L (ja) |
RS (1) | RS20050678A (ja) |
RU (1) | RU2005130488A (ja) |
TW (1) | TWI364425B (ja) |
WO (1) | WO2004078813A2 (ja) |
ZA (1) | ZA200507438B (ja) |
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2004
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- 2004-03-03 CL CL200400421A patent/CL2004000421A1/es unknown
- 2004-03-03 KR KR1020057016270A patent/KR101052958B1/ko active IP Right Grant
- 2004-03-03 EP EP04716878A patent/EP1603925A2/en not_active Withdrawn
- 2004-03-03 BR BRPI0408662A patent/BRPI0408662B1/pt not_active IP Right Cessation
- 2004-03-03 MX MXPA05009376A patent/MXPA05009376A/es unknown
- 2004-03-03 CA CA002517875A patent/CA2517875A1/en not_active Abandoned
- 2004-03-03 CN CNB200480012021XA patent/CN100422192C/zh not_active Expired - Lifetime
- 2004-03-03 JP JP2006509016A patent/JP4571125B2/ja not_active Expired - Fee Related
- 2004-03-03 WO PCT/US2004/006422 patent/WO2004078813A2/en not_active Application Discontinuation
- 2004-03-03 TW TW093105548A patent/TWI364425B/zh not_active IP Right Cessation
- 2004-03-03 RS YUP-2005/0678A patent/RS20050678A/sr unknown
- 2004-03-03 RU RU2005130488/04A patent/RU2005130488A/ru not_active Application Discontinuation
- 2004-03-03 AR ARP040100667A patent/AR043461A1/es not_active Application Discontinuation
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2005
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EP2883878A1 (en) | 2013-12-13 | 2015-06-17 | Shin-Etsu Chemical Co., Ltd. | Sulfur-containing organosilicon compound, making method, rubber compounding ingredient, and rubber composition |
US9238664B2 (en) | 2013-12-13 | 2016-01-19 | Shin-Etsu Chemical Co., Ltd. | Sulfur-containing organosilicon compound, making method, rubber compounding ingredient, and rubber composition |
KR20170108980A (ko) | 2015-01-26 | 2017-09-27 | 신에쓰 가가꾸 고교 가부시끼가이샤 | 오가노폴리실록세인, 고무용 배합제, 고무 조성물 및 타이어 |
US11098182B2 (en) | 2016-03-10 | 2021-08-24 | Shin-Etsu Chemical Co., Ltd. | Organic silicon compound, and rubber compounding agent and rubber composition in which same is used |
KR20190009767A (ko) | 2016-05-23 | 2019-01-29 | 신에쓰 가가꾸 고교 가부시끼가이샤 | 유기 규소 화합물, 및 그것을 사용한 고무용 배합제 및 고무 조성물 |
EP3293204A1 (en) | 2016-09-07 | 2018-03-14 | Shin-Etsu Chemical Co., Ltd. | Silane-modified polymer, rubber compounding ingredient, and rubber composition |
KR20180028027A (ko) | 2016-09-07 | 2018-03-15 | 신에쓰 가가꾸 고교 가부시끼가이샤 | 실란 변성 중합체, 및 그것을 사용한 고무용 배합제 및 고무 조성물 |
US10815323B2 (en) | 2016-09-07 | 2020-10-27 | Shin-Etsu Chemical Co., Ltd. | Silane-modified polymer, rubber compounding ingredient, and rubber composition |
WO2021166396A1 (ja) | 2020-02-18 | 2021-08-26 | 信越化学工業株式会社 | オルガノポリシロキサン、ゴム組成物およびタイヤ |
Also Published As
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JP2006519864A (ja) | 2006-08-31 |
CN100422192C (zh) | 2008-10-01 |
AR043461A1 (es) | 2005-07-27 |
EP1603925A2 (en) | 2005-12-14 |
KR101052958B1 (ko) | 2011-07-29 |
TWI364425B (en) | 2012-05-21 |
WO2004078813A2 (en) | 2004-09-16 |
ZA200507438B (en) | 2006-09-27 |
BRPI0408662A (pt) | 2006-03-28 |
KR20050107596A (ko) | 2005-11-14 |
TW200500371A (en) | 2005-01-01 |
US6777569B1 (en) | 2004-08-17 |
CL2004000421A1 (es) | 2005-01-28 |
NO20054516L (no) | 2005-09-29 |
WO2004078813A3 (en) | 2004-10-21 |
CA2517875A1 (en) | 2004-09-16 |
CN1784412A (zh) | 2006-06-07 |
BRPI0408662B1 (pt) | 2015-09-15 |
MXPA05009376A (es) | 2005-12-05 |
RU2005130488A (ru) | 2006-03-10 |
RS20050678A (en) | 2007-08-03 |
AU2004217886A1 (en) | 2004-09-16 |
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