TWI364425B - Process for the manufacture of blocked mercaptosilanes - Google Patents
Process for the manufacture of blocked mercaptosilanes Download PDFInfo
- Publication number
- TWI364425B TWI364425B TW093105548A TW93105548A TWI364425B TW I364425 B TWI364425 B TW I364425B TW 093105548 A TW093105548 A TW 093105548A TW 93105548 A TW93105548 A TW 93105548A TW I364425 B TWI364425 B TW I364425B
- Authority
- TW
- Taiwan
- Prior art keywords
- thioacetate
- decyl
- ester
- propyl
- group
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 23
- 238000004519 manufacturing process Methods 0.000 title 1
- TXDNPSYEJHXKMK-UHFFFAOYSA-N sulfanylsilane Chemical class S[SiH3] TXDNPSYEJHXKMK-UHFFFAOYSA-N 0.000 title 1
- -1 mercapto halide Chemical class 0.000 claims description 45
- KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 claims description 13
- 229910052751 metal Inorganic materials 0.000 claims description 11
- 239000002184 metal Substances 0.000 claims description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 11
- 229910000057 polysulfane Inorganic materials 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- DUYAAUVXQSMXQP-UHFFFAOYSA-M thioacetate Chemical compound CC([S-])=O DUYAAUVXQSMXQP-UHFFFAOYSA-M 0.000 claims description 6
- OATSQCXMYKYFQO-UHFFFAOYSA-N S-methyl ethanethioic acid ester Natural products CSC(C)=O OATSQCXMYKYFQO-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- CBFCDTFDPHXCNY-UHFFFAOYSA-N icosane Chemical compound CCCCCCCCCCCCCCCCCCCC CBFCDTFDPHXCNY-UHFFFAOYSA-N 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 4
- 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 3
- 239000002253 acid Substances 0.000 claims description 3
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- CWERGRDVMFNCDR-UHFFFAOYSA-N alpha-mercaptoacetic acid Natural products OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 claims description 2
- 230000000903 blocking effect Effects 0.000 claims description 2
- 150000003304 ruthenium compounds Chemical class 0.000 claims description 2
- 239000002585 base Substances 0.000 claims 8
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- 229920001021 polysulfide Polymers 0.000 claims 6
- 239000005077 polysulfide Substances 0.000 claims 6
- 150000008117 polysulfides Polymers 0.000 claims 6
- 229910052783 alkali metal Inorganic materials 0.000 claims 5
- 150000001340 alkali metals Chemical class 0.000 claims 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 5
- 150000001342 alkaline earth metals Chemical class 0.000 claims 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 3
- 150000002894 organic compounds Chemical class 0.000 claims 3
- 239000011593 sulfur Substances 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 claims 2
- IFABLCIRROMTAN-MDZDMXLPSA-N (e)-1-chlorooctadec-9-ene Chemical compound CCCCCCCC\C=C\CCCCCCCCCl IFABLCIRROMTAN-MDZDMXLPSA-N 0.000 claims 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims 1
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 claims 1
- MLRVZFYXUZQSRU-UHFFFAOYSA-N 1-chlorohexane Chemical compound CCCCCCCl MLRVZFYXUZQSRU-UHFFFAOYSA-N 0.000 claims 1
- CNDHHGUSRIZDSL-UHFFFAOYSA-N 1-chlorooctane Chemical compound CCCCCCCCCl CNDHHGUSRIZDSL-UHFFFAOYSA-N 0.000 claims 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims 1
- WLVCBAMXYMWGLJ-UHFFFAOYSA-N 3-(chloromethyl)heptane Chemical compound CCCCC(CC)CCl WLVCBAMXYMWGLJ-UHFFFAOYSA-N 0.000 claims 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 claims 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- PWUBONDMIMDOQY-UHFFFAOYSA-N acetonitrile;hydrochloride Chemical compound Cl.CC#N PWUBONDMIMDOQY-UHFFFAOYSA-N 0.000 claims 1
- 125000002877 alkyl aryl group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims 1
- 229910052791 calcium Inorganic materials 0.000 claims 1
- 239000011575 calcium Substances 0.000 claims 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 claims 1
- 125000004494 ethyl ester group Chemical group 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical group 0.000 claims 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 claims 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 229910052744 lithium Inorganic materials 0.000 claims 1
- 229910052749 magnesium Inorganic materials 0.000 claims 1
- 239000011777 magnesium Substances 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000008267 milk Substances 0.000 claims 1
- 210000004080 milk Anatomy 0.000 claims 1
- 235000013336 milk Nutrition 0.000 claims 1
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- WPLYOXXIMHMDDT-UHFFFAOYSA-N o-propyl ethanethioate Chemical compound CCCOC(C)=S WPLYOXXIMHMDDT-UHFFFAOYSA-N 0.000 claims 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims 1
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- UDEWPOVQBGFNGE-UHFFFAOYSA-N propyl benzoate Chemical compound CCCOC(=O)C1=CC=CC=C1 UDEWPOVQBGFNGE-UHFFFAOYSA-N 0.000 claims 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 claims 1
- 235000021419 vinegar Nutrition 0.000 claims 1
- 239000000052 vinegar Substances 0.000 claims 1
- 239000008096 xylene Substances 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000007789 gas Substances 0.000 description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 229910052987 metal hydride Inorganic materials 0.000 description 2
- 150000004681 metal hydrides Chemical class 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 125000003396 thiol group Chemical class [H]S* 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- XRNDMACZMJPCRX-UHFFFAOYSA-N C(CC)C(C(OCC)(OCC)OCC)CCCCCCCC Chemical compound C(CC)C(C(OCC)(OCC)OCC)CCCCCCCC XRNDMACZMJPCRX-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 1
- KRWKYUMVNGWTNM-UHFFFAOYSA-N SCCCC(C(OCC)(OCC)OCC)CCCCCCCC Chemical compound SCCCC(C(OCC)(OCC)OCC)CCCCCCCC KRWKYUMVNGWTNM-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 1
- AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical group [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- VTXVGVNLYGSIAR-UHFFFAOYSA-N decane-1-thiol Chemical compound CCCCCCCCCCS VTXVGVNLYGSIAR-UHFFFAOYSA-N 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000010436 fluorite Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
1364425 會導致産物降解及/或得到不期望之混合物，致使該方法仍 然不夠理想。 先前所用之另一種方法係以一種酸受體如三級胺就地中 和該氣化氫，詳見2002年丨丨月4日申請之美國臨時專利號 60/423,577，但是#方法需要化學計量值之胺，降低了批次 產率（batch yield)’並導致大量不期望得到之鹽，該鹽必須 在隨後步驟除去，參見美國專利6,229,〇36。衆所周知，由 於三級胺鹽之溶解度使其難以被除去，且習知_方法係 機械地集中（mechanically mtensive)，並常導致低產率。此 外，濾餅之進一步加工亦增加了附加成本，例如三級胺和 氣化氫本身之處理，造成嚴重之環境問題。 已經顯不，含鲼基之有機矽化合物之金屬鹽與醯基鹵反 應可生成所需之經封阻巯基矽烷以及金屬齒鹽，參見美國 專利6,414,06卜該專利之内容以引用方式併入本文；但是 除了先前.提到之困難以外，含疏基之有機石夕化合物價格高 叩使其廣泛應用受到限制》因而，需要開發一種成本低廉 而且不會導致上述化學以及環境問題之方法製造經封阻巯 基石夕烷。已知許多方法可斷裂硫-硫鍵，例如利用諸如胺、 金屬氰化物 '金屬氫化物以及驗金屬等驗類，但是膦 以及金屬氫化物價格昂貴，金屬氰化物則會導致安全之考 慮。 【發明内容】 含有聚硫烷之矽化合物，除了普及性以外，其價格低廉 且來源廣泛，且金屬鹵化物副產物不會與産物經封阻疏基 9l73l.doc 1364425 二醢基氣。 由前述方法所得之經封阻巯基矽烷符合結構通式r2c(〇) SGSiR 3 ’其_ ’ r1、r2與g之定義如前所述。具體之經封 阻巯基矽烷包括，例如’硫代乙酸2_三乙氧基甲矽烷基_ i _ 乙基酯；硫代乙酸2-三甲氧基甲矽烷基_ 1 -乙基酯；硫代乙 酸2-(甲基二曱氧基甲矽烷基）_ι·乙基酯；硫代乙酸3 _三曱氧 基曱石夕烧基-1-丙基酯；硫代乙酸三乙氧基甲矽院基曱基 酯；硫代乙酸三曱氧基曱矽烷基甲基酯；硫代乙酸三異丙 氧基曱矽烷基甲基酯；硫代乙酸曱基二乙氧基甲矽烷基甲 基酯；硫代乙酸甲基二甲氧基曱矽烷基曱基酯；硫代乙酸 曱基二異丙氧基甲矽烷基甲基酯；硫代乙酸二甲基乙氧基 甲矽烷基甲基酯；硫代乙酸二甲基曱氧基曱矽烷基甲基 酯；硫代乙酸二甲基異丙氧基曱矽烷基甲基酯；硫代乙酸 2- 三異丙氧基甲矽烷基-1-乙基酯；硫代乙酸2-(曱基二乙氧 基甲矽烷基）-1-乙基酯；硫代乙酸2-(甲基二異丙氧基甲矽 烷基）-1-乙基酯；硫代乙酸2-(二曱基乙氧基甲矽烷基）-1-乙 基酯；硫代乙酸2-(二甲基曱氧基曱矽烷基）-1-乙基酯；硫 代乙酸2-(二甲基異丙氧基甲矽烷基）-卜乙基酯；硫代乙酸 3- 三乙氧基甲矽烷基-1-丙基酯；硫代乙酸3_三異丙氧基甲 矽烷基-1-丙基酯；硫代乙酸3_甲基二乙氧基甲矽烷基-1-丙 基酯；硫代乙酸3-甲基二甲氧基甲矽烷基-1 -丙基酯；硫代 乙酸3 -曱基二異丙氧基曱石夕烧基丙基酯；1_(2 -三乙氧基 曱石夕炫基乙基）-4 -硫代乙酿基壤己炫’ 1-(2 -三乙氧基甲 矽烷基-1-乙基硫代乙醯基環己烧；2_三乙氧基曱矽烷基 9173l.doc -11 - 1364425 (wt/wt)表示，且其由GC實驗室使用Hewlett-Packard 5890 Π系列氣相色譜法獲得。下列縮寫與商標名（及其說明）將出 現於實例中： 細寫 說明 CPTES 氣丙基三乙氧基矽烷 MPTES 巯基丙基三乙氧基矽烷 經封阻巯基矽烷 3-(辛醯基硫代）-1-丙基三乙氧基矽烷 S,-BTESPS 雙（三乙氧基甲矽烷基）丙基硫烷 s2-btesps 雙（三乙氧基曱矽烷基）丙基二硫烷 s3-btesps 雙（三乙氧基甲矽烷基）丙基三硫烷 2Si 巯基矽烷S-硫代曱酸酯之二矽氧烷 溶離重$ 2Si與所有2Si之後溶出之化合物總量 Solvent®140 平均分子量爲140且在C12-Cl4範圍内 之非芳烴之混合物 比較實例-1 周圍溫度下，以25.00g鈉（1.076莫耳）處理515.20 g甲苯， 並且加熱至約105°C。該熔化狀態之鈉·甲苯懸浮液以265.21 g MPTES(1.076莫耳）處理，30分鐘過程中，導致氫氣釋出。 MPTES加入完畢後，所得之澄清無色溶液冷卻至約45。匸， 再以164.75 g辛醯基氣（0.982莫耳）處理。辛醯基氣之加入導 致放熱反應，並且生成鹽。辛醢基氣在一小時内加入，同 日守反應溫度緩慢升至6 2 °C。一旦反應冷卻至5 〇 ，加入 215.0 g去離子水使鹽類溶解並且形成兩層。除去水層，甲 苯亦在真空狀態下移除，回收5〇4·72 g曱苯（98%回收率）。 9173l.doc -14-
Claims (1)
- I 1364425 公告本 第093105^48號專利申請案 中文申請專利範圍替換本(100年8月）> 拾、申請專利範圍： 娜B: 1 · 一種經封阻毓基矽烷之製法，包含： (a) 使至少一種下式之含聚硫烷之有機矽化合物： (R13SiG)2Sn 其中各R1獨立為甲氧基、乙氧基或含1-6個碳原子之烷 基，但條件為至少一個R1基為甲氧基或乙氧基，G爲含 1-12個碳原子之伸烷基，η爲2-8，與至少一種鹼金屬或鹼 土金屬反應’以獲得含硫烷之有機矽化合物之對應金屬 鹽類；以及 (b) 使該含硫烷之有機矽化合物之對應金屬鹽類與醯基 鹵或羰基二鹵反應，以獲得經封阻酼基矽烷。 根據申清專利範圍第1項之方法，其中所述之含聚硫烧之 有機石夕化合物係選自由雙[(三乙氧基甲矽烷基）丙基]聚 硫烷、雙[(甲基二乙氧基甲矽烷基）丙基]聚硫烷、雙[(三 乙氧基甲梦烧基）異丁基]聚硫烧、雙[(曱基二乙氧基曱石夕 烷基）異丁基]聚硫烷、雙[(三曱氧基甲矽烷基）丙基]聚硫 烷 '雙[(曱基二曱氧基曱矽烷基）丙基]聚硫烷、雙[(三曱 氧基甲矽烷基）異丁基]聚硫烷以及雙[(甲基二曱氧基曱 石夕烧基）異丁基]聚硫烧所組成之群。 3. 根據申請專利範圍第1項之方法，其中鹼金屬及鹼土金屬 係選自由鋰、鈉、鉀、鎂、鈣及其混合物組成之群。 4. 根據申請專利範圍第i項之方法’其中醯基函有以下結構 通式： R2C(0)X 91731-1000811.doc 1364425… 其中R2爲含至多18個碳原子之院基、烯基1基、烧芳 基或芳烷基，X爲鹵素。根據申請專利範圍第4項之方法，其中醯基齒爲乙醯基 氯:丙酿基氯、丁酿基氯、戊喊氣、己醯基氯、庚酿 基乳、辛酿基氯、2-乙基己醒基氯、十二炫醯基氯、油酿 基氯、氯曱酸辛醋、己二酿基氣 '苯乙酿基氯、苯甲酿 基氯、對苯二醯基氯以及氯甲酸苯酯。 根據申請專利範圍第丨項之方法，其中羰基二函爲光氣或 乙二醯基氯。 根據申請專利範圍第4項之方法，其中經封阻酼基矽烷産 物具有如下結構通式： R2C(0)SGSiR13 其中，R1獨立為甲氧基、乙氧基或含1-6個碳原子之烷 基’但條件為至少一個Rl基為甲氧基或乙氧基；R2爲含 至多18個碳原子之烷基、烯基、芳基、烷芳基或芳烷基； 且G爲含1-12個碳原子之伸烷基。 8.根據申請專利範圍第7項之方法，其中經封阻酼基矽烷産 物係選自由硫代乙酸2-三乙氧基甲矽烷基-1-乙基酯；硫 代乙酸2-三曱氧基曱矽烷基_丨-乙基酯；硫代乙酸2_(甲基 二甲氧基曱矽烷基）-1-乙基酯；硫代乙酸3-三曱氧基甲矽 烷基-1-丙基酯；硫代乙酸三乙氧基甲矽烷基曱基酯；硫 代乙酸三甲氧基曱矽烷基甲基酯；硫代乙酸三異丙氧基 曱矽烷基甲基酯；硫代乙酸甲基二乙氧基曱矽烷基甲基 酯；硫代乙酸曱基二甲氧基曱矽烷基曱基酯；硫代乙酸 9173M000811.doc 1364425 甲基二異丙氧基甲矽烷基甲基酯；硫代乙酸二甲基乙氧 基甲矽烷基甲基酯；硫代乙酸二曱基甲氧基甲矽烷基甲 基酯；硫代乙酸二甲基異丙氧基曱矽烷基曱基酯；硫代 乙酸2-三異丙氧基甲矽烷基-1-乙基酯；硫代乙酸2-(甲基 二乙氧基f矽烷基）-1-乙基酯；硫代乙酸2-(曱基二異丙氧 基甲矽烷基）-1-乙基酯；硫代乙酸2-(二甲基乙氧基甲矽烷 基）-1-乙基酯；硫代乙酸2-(二曱基甲氧基甲矽烷基）-1-乙 基酯；硫代乙酸2·(二曱基異丙氧基甲矽烷基）-1-乙基酯； 硫代乙酸3-三乙氧基曱矽烷基-1-丙基酯；硫代乙酸3-三 異丙氧基f矽烷基-1-丙基酯；硫代乙酸3-曱基二乙氧基 甲矽烷基-1-丙基酯；硫代乙酸3-甲基二曱氧基甲矽烷基 -1-丙基酯；硫代乙酸3-曱基二異丙氧基甲矽烷基-1-丙基 3旨，1-(2 -三乙氧基甲碎烧基-1-乙基）-4-硫代己酿基環己 烷；1-(2-三乙氧基甲矽烷基-1-乙基）-3-硫代乙醯基環己 烷；2-三乙氧基甲矽烷基-5-硫代乙醯基降冰片烯；2-三 乙氧基甲矽烷基-4-硫代乙醯基降冰片烯；2-(2-三乙氧基 甲矽烷基-1-乙基）-5-硫代乙醯基降冰片烯；2-(2-三乙氧基 曱矽烷基-1-乙基）-4·硫代乙醯基降冰片烯；硫代乙酸6-三乙氧基曱矽烷基-1-己基酯；硫代乙酸1-三乙氧基曱矽 烷基-5-己基酯；硫代乙酸8-三乙氧基曱矽烷基-1_辛基 酯；硫代乙酸1-三乙氧基甲矽烷基-7-辛基酯；硫代乙酸 6-三乙氧基曱矽烷基-1-己基酯；硫代乙酸1-三乙氧基曱 矽烷基-5-辛基酯；硫代乙酸8-三甲氧基曱矽烷基_丨-辛基 酯；硫代乙酸1-三甲氧基甲矽烷基-7-辛基酯；硫代乙酸 9173M000811.doc 1364425 : . * t > • 10-三乙氧基甲矽烷基-1-癸基酯；硫代乙酸1-三乙氧基甲 矽烷基-9-癸基酯；硫代乙酸1-三乙氧基甲矽烷基-2-丁基 酯；硫代乙酸1-三乙氧基甲矽烷基-3-丁基酯；硫代乙酸 1-三乙氧基甲矽烷基-3-曱基-2-丁基酯；硫代乙酸1-三乙 氧基曱矽烷基-3-曱基-3丁基酯；硫代辛酸3-三曱氧基曱 矽烧基-1-丙基酯；硫代十六烧棕櫚酸3 -三乙氧基曱矽烧 基-1 -丙基酯；硫代辛酸3 -三乙氧基甲石夕烧基_ 1 _丙基酯； 硫代苯甲酸3-三乙氧基曱矽烷基_ 1 _丙基酯；及硫代_2_乙 基己酸3 -二乙氧基节攻院基-i_丙基g旨組成之群。 9. 根據申請專利範圍第1項之方法，其中鹼金屬或鹼土金屬 相對於含聚硫烧之有機石夕化合物之莫耳當量範圍爲1 : 1 至10 : 1 。 10. 根據申清專利範圍第1項之方法，其中含硫燒之有機石夕化 合物之金屬鹽類相對於醯基鹵之莫耳當量範圍爲125: 1 至1: 1’或其與藏基二鹵之莫耳當量範圍爲2 25 : 1至2 : 1 ° 籲11.根據申請專利範圍第1項之方法，其中含聚硫烧之有機硬 * 化合物與鹼金屬或鹼土金屬之間之反應係在金屬或金屬 衍生物處於液態之溫度下進行。 12.根據中請專利範圍第1之方法，其中含硫烧之有機石夕化 合物之金屬冑類與酿基齒或幾基二齒之間之反應係在溫 度範圍10°C至50°C内進行。 13 ·根據申請專利範圍第丨瑁夕 固乐之方法，係在溶劑中進行者。 14.根據申請專利範圍第13箱 J现国矛項之方法，其中所述溶劑係選自 9173M000811.doc 1364425 由曱苯、苯、二甲苯、己烷、庚烷、異辛烷以及辛烷組 成之群。 15.根據申請專利範圍第9項之方法，其中鹼金屬或鹼土金屬 相對於含聚硫烷之有機矽化合物之莫耳當量範圍爲2 : 1 至 2.5 : 1 。 91731-1000811.doc
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| EP1298163B1 (de) * | 2001-09-26 | 2005-07-06 | Degussa AG | Geblockte Mercaptosilane, Verfahren zu deren Herstellung und die enthaltenden Kautschukmischungen |
| US7531588B2 (en) * | 2004-07-30 | 2009-05-12 | Momentive Performance Materials Inc. | Silane compositions, processes for their preparation and rubber compositions containing same |
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| US7528273B2 (en) | 2005-04-14 | 2009-05-05 | Momentive Performance Materials Inc. | Aqueous catalytic process for the preparation of thiocarboxylate silane |
| DE102005037690A1 (de) * | 2005-08-10 | 2007-02-15 | Degussa Ag | Verfahren zur Herstellung von Organosiliciumverbindungen |
| PL1963110T3 (pl) | 2005-10-19 | 2010-01-29 | Trinseo Europe Gmbh | Elastomeryczne polimery modyfikowane silano-sulfidowymi końcami łańcucha |
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| US7560513B2 (en) * | 2005-12-16 | 2009-07-14 | Continental Ag | Polyorganosiloxane composition for use in unsaturated elastomer, article made therefrom, and associated method |
| US7919650B2 (en) * | 2006-02-21 | 2011-04-05 | Momentive Performance Materials Inc. | Organofunctional silanes and their mixtures |
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| US8097744B2 (en) * | 2006-08-14 | 2012-01-17 | Momentive Performance Materials Inc. | Free flowing filler composition comprising mercapto-functional silane |
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| US3922436A (en) | 1974-09-13 | 1975-11-25 | Owens Corning Fiberglass Corp | Silanes useful as coupling agents and flame retardants |
| DE2508931A1 (de) | 1975-03-01 | 1976-09-09 | Dynamit Nobel Ag | Schwefelorganische silicium-verbindungen - verfahren zu deren herstellung und verwendung als haftvermittler |
| US5489701A (en) | 1994-09-28 | 1996-02-06 | Osi Specialties, Inc. | Process for the preparation of silane polysulfides |
| US5596116A (en) | 1995-09-11 | 1997-01-21 | Osi Specialties, Inc. | Process for the preparation of silane polysulfides |
| DE19541404A1 (de) | 1995-11-07 | 1997-05-15 | Degussa | Verfahren zur selektiven Synthese von Silylalkyldisulfiden |
| FR2743564A1 (fr) * | 1996-01-11 | 1997-07-18 | Michelin & Cie | Compositions de caoutchouc pour enveloppes de pneumatiques a base de silices contenant un additif de renforcement a base d'un polyorganosiloxane fonctionnalise et d'un compose organosilane . |
| BR9806096B1 (pt) * | 1997-08-21 | 2009-01-13 | mercaptosilano bloqueado; processo para a manufatura de uma borracha com carga; processo para a manufatura de um mercaptosilano bloqueado; composiÇço de borracha; e silano. | |
| DE19844607A1 (de) | 1998-09-29 | 2000-03-30 | Degussa | Sulfanylsilane |
| DE19860439C1 (de) * | 1998-12-28 | 2000-07-06 | Degussa | Verfahren zur Herstellung von Silylalkylthiolen |
| US6294683B1 (en) | 1999-01-19 | 2001-09-25 | The Goodyear Tire & Rubber Company | Solid/liquid phase transfer system |
| US6384255B1 (en) | 2001-06-29 | 2002-05-07 | Dow Corning Corporation | Process for the preparation of sulfur-containing organosilicon compounds |
-
2003
- 2003-03-03 US US10/378,184 patent/US6777569B1/en not_active Expired - Lifetime
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2004
- 2004-03-03 KR KR1020057016270A patent/KR101052958B1/ko active IP Right Grant
- 2004-03-03 CL CL200400421A patent/CL2004000421A1/es unknown
- 2004-03-03 MX MXPA05009376A patent/MXPA05009376A/es unknown
- 2004-03-03 BR BRPI0408662A patent/BRPI0408662B1/pt not_active IP Right Cessation
- 2004-03-03 CN CNB200480012021XA patent/CN100422192C/zh not_active Expired - Lifetime
- 2004-03-03 RU RU2005130488/04A patent/RU2005130488A/ru not_active Application Discontinuation
- 2004-03-03 RS YUP-2005/0678A patent/RS20050678A/sr unknown
- 2004-03-03 CA CA002517875A patent/CA2517875A1/en not_active Abandoned
- 2004-03-03 AR ARP040100667A patent/AR043461A1/es not_active Application Discontinuation
- 2004-03-03 AU AU2004217886A patent/AU2004217886A1/en not_active Abandoned
- 2004-03-03 EP EP04716878A patent/EP1603925A2/en not_active Withdrawn
- 2004-03-03 WO PCT/US2004/006422 patent/WO2004078813A2/en not_active Application Discontinuation
- 2004-03-03 JP JP2006509016A patent/JP4571125B2/ja not_active Expired - Fee Related
- 2004-03-03 TW TW093105548A patent/TWI364425B/zh not_active IP Right Cessation
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|---|---|
| RU2005130488A (ru) | 2006-03-10 |
| ZA200507438B (en) | 2006-09-27 |
| CN100422192C (zh) | 2008-10-01 |
| BRPI0408662B1 (pt) | 2015-09-15 |
| EP1603925A2 (en) | 2005-12-14 |
| CN1784412A (zh) | 2006-06-07 |
| WO2004078813A2 (en) | 2004-09-16 |
| CA2517875A1 (en) | 2004-09-16 |
| KR20050107596A (ko) | 2005-11-14 |
| AU2004217886A1 (en) | 2004-09-16 |
| AR043461A1 (es) | 2005-07-27 |
| WO2004078813A3 (en) | 2004-10-21 |
| TW200500371A (en) | 2005-01-01 |
| MXPA05009376A (es) | 2005-12-05 |
| NO20054516L (no) | 2005-09-29 |
| RS20050678A (en) | 2007-08-03 |
| US6777569B1 (en) | 2004-08-17 |
| CL2004000421A1 (es) | 2005-01-28 |
| KR101052958B1 (ko) | 2011-07-29 |
| JP4571125B2 (ja) | 2010-10-27 |
| JP2006519864A (ja) | 2006-08-31 |
| BRPI0408662A (pt) | 2006-03-28 |
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