JP2001505225A - 充填材含有ゴム用保護化メルカプトシラン・カップリング剤 - Google Patents
充填材含有ゴム用保護化メルカプトシラン・カップリング剤Info
- Publication number
- JP2001505225A JP2001505225A JP51363999A JP51363999A JP2001505225A JP 2001505225 A JP2001505225 A JP 2001505225A JP 51363999 A JP51363999 A JP 51363999A JP 51363999 A JP51363999 A JP 51363999A JP 2001505225 A JP2001505225 A JP 2001505225A
- Authority
- JP
- Japan
- Prior art keywords
- triethoxysilyl
- group
- silane
- mercaptosilane
- reaction
- 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.)
- Withdrawn
Links
- 239000005060 rubber Substances 0.000 title claims abstract description 89
- 229920001971 elastomer Polymers 0.000 title claims abstract description 88
- TXDNPSYEJHXKMK-UHFFFAOYSA-N sulfanylsilane Chemical compound S[SiH3] TXDNPSYEJHXKMK-UHFFFAOYSA-N 0.000 title claims abstract description 81
- 239000000945 filler Substances 0.000 title claims abstract description 37
- 239000007822 coupling agent Substances 0.000 title description 9
- 238000000034 method Methods 0.000 claims abstract description 53
- 238000002156 mixing Methods 0.000 claims abstract description 35
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 15
- 229920000620 organic polymer Polymers 0.000 claims abstract description 12
- 239000012351 deprotecting agent Substances 0.000 claims abstract description 8
- 125000003396 thiol group Chemical group [H]S* 0.000 claims abstract description 8
- 238000006243 chemical reaction Methods 0.000 claims description 111
- 229910000077 silane Inorganic materials 0.000 claims description 97
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 92
- -1 ethylnorbornyl Chemical group 0.000 claims description 85
- 239000000203 mixture Substances 0.000 claims description 83
- 150000002148 esters Chemical class 0.000 claims description 59
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 48
- 229910052717 sulfur Inorganic materials 0.000 claims description 47
- 239000011593 sulfur Substances 0.000 claims description 47
- 239000002253 acid Substances 0.000 claims description 37
- 150000004756 silanes Chemical class 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 229910052783 alkali metal Inorganic materials 0.000 claims description 19
- 125000003342 alkenyl group Chemical group 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 239000003153 chemical reaction reagent Substances 0.000 claims description 14
- 150000008065 acid anhydrides Chemical class 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 150000007970 thio esters Chemical group 0.000 claims description 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 10
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 10
- 229910052698 phosphorus Inorganic materials 0.000 claims description 10
- 238000005809 transesterification reaction Methods 0.000 claims description 10
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 9
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 9
- 239000011574 phosphorus Substances 0.000 claims description 9
- 125000004122 cyclic group Chemical group 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- SMDVDXOWTRMZKF-UHFFFAOYSA-N C1C[SiH2]SC1 Chemical compound C1C[SiH2]SC1 SMDVDXOWTRMZKF-UHFFFAOYSA-N 0.000 claims description 6
- 239000003999 initiator Substances 0.000 claims description 6
- 239000011256 inorganic filler Substances 0.000 claims description 6
- 229910003475 inorganic filler Inorganic materials 0.000 claims description 6
- 238000006467 substitution reaction Methods 0.000 claims description 6
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 6
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 6
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 229910052710 silicon Inorganic materials 0.000 claims description 4
- 150000003566 thiocarboxylic acids Chemical class 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 238000007342 radical addition reaction Methods 0.000 claims description 3
- 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 claims description 2
- FSLUHJNPNRHGBF-UHFFFAOYSA-N 1-[4-(2-triethoxysilylethyl)cyclohexyl]ethanethione Chemical compound CCO[Si](OCC)(OCC)CCC1CCC(C(C)=S)CC1 FSLUHJNPNRHGBF-UHFFFAOYSA-N 0.000 claims description 2
- MRFMYANPSJUQPW-UHFFFAOYSA-N 1-propyl-5-triethoxysilylcyclohexa-2,4-diene-1-carbothioic S-acid Chemical compound CCCC1(C(S)=O)CC([Si](OCC)(OCC)OCC)=CC=C1 MRFMYANPSJUQPW-UHFFFAOYSA-N 0.000 claims description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 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
- 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 description 2
- 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 claims description 2
- 239000005711 Benzoic acid Substances 0.000 claims description 2
- FDJLHMMBYKZDOF-UHFFFAOYSA-N C(C)O[Si](OCC)(OCC)COS(=O)(=S)CC1=CC=CC=C1 Chemical compound C(C)O[Si](OCC)(OCC)COS(=O)(=S)CC1=CC=CC=C1 FDJLHMMBYKZDOF-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
- OYTKFCGHGKKNHQ-UHFFFAOYSA-N CCO[SiH](CC(C)(C)C(O)=S)OCC Chemical compound CCO[SiH](CC(C)(C)C(O)=S)OCC OYTKFCGHGKKNHQ-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
- 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
- ZIRZHZPXSOKIGF-UHFFFAOYSA-N O-methyl 3-diethoxysilylpropanethioate Chemical compound COC(CC[SiH](OCC)OCC)=S ZIRZHZPXSOKIGF-UHFFFAOYSA-N 0.000 claims description 2
- 235000010233 benzoic acid Nutrition 0.000 claims 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 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- ZYMSCYXVIBFLNS-UHFFFAOYSA-N methyl-bis(sulfanyl)-sulfanylidene-$l^{5}-phosphane Chemical compound CP(S)(S)=S ZYMSCYXVIBFLNS-UHFFFAOYSA-N 0.000 claims description 2
- 125000003518 norbornenyl group Chemical group C12(C=CC(CC1)C2)* 0.000 claims description 2
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 claims description 2
- QXBLIUBAPLUCFY-UHFFFAOYSA-N o-(triethoxysilylmethyl) ethanethioate Chemical compound CCO[Si](OCC)(OCC)COC(C)=S QXBLIUBAPLUCFY-UHFFFAOYSA-N 0.000 claims description 2
- DUGAFPBTRVNWOH-UHFFFAOYSA-N o-(trimethoxysilylmethyl) ethanethioate Chemical compound CO[Si](OC)(OC)COC(C)=S DUGAFPBTRVNWOH-UHFFFAOYSA-N 0.000 claims description 2
- XLHROWYJKQZJBU-UHFFFAOYSA-N o-[2-[diethoxy(methyl)silyl]ethyl] ethanethioate Chemical compound CCO[Si](C)(OCC)CCOC(C)=S XLHROWYJKQZJBU-UHFFFAOYSA-N 0.000 claims description 2
- YWVJNDNHFJEYCV-UHFFFAOYSA-N o-[2-[dimethyl(propan-2-yloxy)silyl]ethyl] ethanethioate Chemical compound CC(C)O[Si](C)(C)CCOC(C)=S YWVJNDNHFJEYCV-UHFFFAOYSA-N 0.000 claims description 2
- BRMSZTGNZHLNDG-UHFFFAOYSA-N o-[2-[methyl-di(propan-2-yloxy)silyl]ethyl] ethanethioate Chemical compound CC(C)O[Si](C)(OC(C)C)CCOC(C)=S BRMSZTGNZHLNDG-UHFFFAOYSA-N 0.000 claims description 2
- SOWBFZRMHSNYGE-UHFFFAOYSA-N oxamic acid Chemical group NC(=O)C(O)=O SOWBFZRMHSNYGE-UHFFFAOYSA-N 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- VGGJNLGZARHOQV-UHFFFAOYSA-N sulfanylidene-tris(3-triethoxysilylpropylsulfanyl)-$l^{5}-phosphane Chemical compound CCO[Si](OCC)(OCC)CCCSP(=S)(SCCC[Si](OCC)(OCC)OCC)SCCC[Si](OCC)(OCC)OCC VGGJNLGZARHOQV-UHFFFAOYSA-N 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims 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 claims 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 claims 1
- YSRUGGVNBXSYMN-UHFFFAOYSA-N 3-dimethoxysilylbutoxy-(3-dimethoxysilylbutylsulfanyl)-methyl-sulfanylidene-lambda5-phosphane Chemical compound CO[SiH](OC)C(C)CCOP(C)(=S)SCCC(C)[SiH](OC)OC YSRUGGVNBXSYMN-UHFFFAOYSA-N 0.000 claims 1
- XCOFOOGNWJLSDM-UHFFFAOYSA-N 3-dimethoxysilylbutoxy-bis(3-dimethoxysilylbutylsulfanyl)-sulfanylidene-lambda5-phosphane Chemical compound CO[SiH](OC)C(C)CCOP(=S)(SCCC(C)[SiH](OC)OC)SCCC(C)[SiH](OC)OC XCOFOOGNWJLSDM-UHFFFAOYSA-N 0.000 claims 1
- FDRBWJKQOFYNGV-UHFFFAOYSA-N 3-methyl-2-triethoxysilylpentanethioic S-acid Chemical compound CCC(C)C(C(=O)S)[Si](OCC)(OCC)OCC FDRBWJKQOFYNGV-UHFFFAOYSA-N 0.000 claims 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 claims 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 claims 1
- 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 1
- MTWYFDSOPUZYOU-UHFFFAOYSA-N CCCC1(C=CC=C(C1C)[Si](OCC)(OCC)OCC)C Chemical group CCCC1(C=CC=C(C1C)[Si](OCC)(OCC)OCC)C MTWYFDSOPUZYOU-UHFFFAOYSA-N 0.000 claims 1
- DFVVUQQSIRKQBX-UHFFFAOYSA-N CCO[Si](CCCSP(=S)(CC)SCCC[Si](OCC)(OCC)OCC)(OCC)OCC Chemical compound CCO[Si](CCCSP(=S)(CC)SCCC[Si](OCC)(OCC)OCC)(OCC)OCC DFVVUQQSIRKQBX-UHFFFAOYSA-N 0.000 claims 1
- SQQJRWSRLMYALI-UHFFFAOYSA-N COS(=O)(=S)C1=CC=CC=C1 Chemical compound COS(=O)(=S)C1=CC=CC=C1 SQQJRWSRLMYALI-UHFFFAOYSA-N 0.000 claims 1
- JBEMNVVWWYPNAR-UHFFFAOYSA-N O-(silylmethyl) ethanethioate Chemical compound C(C)(=S)OC[SiH3] JBEMNVVWWYPNAR-UHFFFAOYSA-N 0.000 claims 1
- UYKPRDGGENWWDO-UHFFFAOYSA-N O-methyl 3-dimethoxysilylpropanethioate Chemical compound COC(CC[SiH](OC)OC)=S UYKPRDGGENWWDO-UHFFFAOYSA-N 0.000 claims 1
- XDCFZTSIQRJWOT-UHFFFAOYSA-N S(=S)(=O)O.C(C)O[Si](OCC)(OCC)C(C)C Chemical compound S(=S)(=O)O.C(C)O[Si](OCC)(OCC)C(C)C XDCFZTSIQRJWOT-UHFFFAOYSA-N 0.000 claims 1
- SVLRJMVELYIDIO-UHFFFAOYSA-N S(=S)(=O)O.C(C)O[Si](OCC)(OCC)CC Chemical compound S(=S)(=O)O.C(C)O[Si](OCC)(OCC)CC SVLRJMVELYIDIO-UHFFFAOYSA-N 0.000 claims 1
- RVZJJFTUWQGPDM-UHFFFAOYSA-N o-(3-triethoxysilylpropyl) ethanethioate Chemical compound CCO[Si](OCC)(OCC)CCCOC(C)=S RVZJJFTUWQGPDM-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- KHTZKHQMYLOHFT-UHFFFAOYSA-N sulfanylidene-(3-triethoxysilylpropoxy)-bis(3-triethoxysilylpropylsulfanyl)-$l^{5}-phosphane Chemical compound CCO[Si](OCC)(OCC)CCCOP(=S)(SCCC[Si](OCC)(OCC)OCC)SCCC[Si](OCC)(OCC)OCC KHTZKHQMYLOHFT-UHFFFAOYSA-N 0.000 claims 1
- 235000012976 tarts Nutrition 0.000 claims 1
- RBDAXWQGOZWYFH-UHFFFAOYSA-N triethoxy(4-hydroxysulfonothioylpentyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCC(C)S(O)(=O)=S RBDAXWQGOZWYFH-UHFFFAOYSA-N 0.000 claims 1
- QZZJETYSMIUUEA-UHFFFAOYSA-N triethoxy-(4-propylnaphthalen-2-yl)silane Chemical compound CCCC1=CC(=CC2=CC=CC=C21)[Si](OCC)(OCC)OCC QZZJETYSMIUUEA-UHFFFAOYSA-N 0.000 claims 1
- XGCGZQRQPNUUPB-UHFFFAOYSA-N triethoxy-(5-hydroxysulfonothioyl-5-propylcyclohexa-1,3-dien-1-yl)silane Chemical compound CCCC1(S(O)(=O)=S)CC([Si](OCC)(OCC)OCC)=CC=C1 XGCGZQRQPNUUPB-UHFFFAOYSA-N 0.000 claims 1
- FVCAMBAGVUGJHH-UHFFFAOYSA-N triethoxy-[5-(hydroxysulfonothioylmethyl)-5-propylcyclohexa-1,3-dien-1-yl]silane Chemical compound CCCC1(CC(=CC=C1)[Si](OCC)(OCC)OCC)CS(=O)(=S)O FVCAMBAGVUGJHH-UHFFFAOYSA-N 0.000 claims 1
- 230000008569 process Effects 0.000 abstract description 17
- 238000005859 coupling reaction Methods 0.000 abstract description 5
- 230000008878 coupling Effects 0.000 abstract description 4
- 238000010168 coupling process Methods 0.000 abstract description 4
- 238000002360 preparation method Methods 0.000 abstract description 2
- WTGIOQMHIHCSPZ-UHFFFAOYSA-N sulfanylsilicon Chemical class S[Si] WTGIOQMHIHCSPZ-UHFFFAOYSA-N 0.000 abstract 2
- 230000001960 triggered effect Effects 0.000 abstract 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 54
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 51
- 239000000047 product Substances 0.000 description 50
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- 238000007792 addition Methods 0.000 description 38
- 238000004821 distillation Methods 0.000 description 34
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 27
- 239000003054 catalyst Substances 0.000 description 27
- 238000001723 curing Methods 0.000 description 27
- 239000000377 silicon dioxide Substances 0.000 description 26
- 239000002904 solvent Substances 0.000 description 26
- 238000010992 reflux Methods 0.000 description 25
- 150000003839 salts Chemical class 0.000 description 24
- 239000000243 solution Substances 0.000 description 24
- 125000000524 functional group Chemical group 0.000 description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 21
- 239000007788 liquid Substances 0.000 description 19
- 125000006239 protecting group Chemical group 0.000 description 17
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 16
- 238000003756 stirring Methods 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 238000010438 heat treatment Methods 0.000 description 15
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- 230000015572 biosynthetic process Effects 0.000 description 13
- DUYAAUVXQSMXQP-UHFFFAOYSA-N ethanethioic S-acid Chemical compound CC(S)=O DUYAAUVXQSMXQP-UHFFFAOYSA-N 0.000 description 13
- 238000003786 synthesis reaction Methods 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 239000002585 base Substances 0.000 description 12
- 239000006229 carbon black Substances 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 11
- 238000004817 gas chromatography Methods 0.000 description 11
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 10
- 150000001340 alkali metals Chemical class 0.000 description 10
- 238000009835 boiling Methods 0.000 description 10
- 238000004898 kneading Methods 0.000 description 10
- 229920003052 natural elastomer Polymers 0.000 description 10
- 229920001194 natural rubber Polymers 0.000 description 10
- 239000008096 xylene Substances 0.000 description 10
- 244000043261 Hevea brasiliensis Species 0.000 description 9
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 9
- 150000001412 amines Chemical group 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 238000012545 processing Methods 0.000 description 9
- 239000004594 Masterbatch (MB) Substances 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- 239000005062 Polybutadiene Substances 0.000 description 7
- 150000001408 amides Chemical class 0.000 description 7
- 239000003963 antioxidant agent Substances 0.000 description 7
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 238000005096 rolling process Methods 0.000 description 7
- 229920003048 styrene butadiene rubber Polymers 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
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- VTHOKNTVYKTUPI-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyltetrasulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSSSCCC[Si](OCC)(OCC)OCC VTHOKNTVYKTUPI-UHFFFAOYSA-N 0.000 description 1
- PZJJKWKADRNWSW-UHFFFAOYSA-N trimethoxysilicon Chemical group CO[Si](OC)OC PZJJKWKADRNWSW-UHFFFAOYSA-N 0.000 description 1
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- NEYNBSGIXOOZGZ-UHFFFAOYSA-L zinc;butoxymethanedithioate Chemical compound [Zn+2].CCCCOC([S-])=S.CCCCOC([S-])=S NEYNBSGIXOOZGZ-UHFFFAOYSA-L 0.000 description 1
- MBBWTVUFIXOUBE-UHFFFAOYSA-L zinc;dicarbamodithioate Chemical compound [Zn+2].NC([S-])=S.NC([S-])=S MBBWTVUFIXOUBE-UHFFFAOYSA-L 0.000 description 1
Classifications
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- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4075—Esters with hydroxyalkyl compounds
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/1651—Esters of thiophosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/20—Compounding polymers with additives, e.g. colouring
- C08J3/203—Solid polymers with solid and/or liquid additives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/34—Silicon-containing compounds
- C08K3/36—Silica
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/5406—Silicon-containing compounds containing elements other than oxygen or nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/548—Silicon-containing compounds containing sulfur
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L21/00—Compositions of unspecified rubbers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L9/00—Compositions of homopolymers or copolymers of conjugated diene hydrocarbons
- C08L9/06—Copolymers with styrene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2321/00—Characterised by the use of unspecified rubbers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
- C08K3/013—Fillers, pigments or reinforcing additives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0025—Crosslinking or vulcanising agents; including accelerators
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L9/00—Compositions of homopolymers or copolymers of conjugated diene hydrocarbons
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- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Compositions Of Macromolecular Compounds (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US5656697P | 1997-08-21 | 1997-08-21 | |
| US60/056,566 | 1997-08-21 | ||
| PCT/US1998/017391 WO1999009036A1 (en) | 1997-08-21 | 1998-08-21 | Blocked mercaptosilane coupling agents for filled rubbers |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008020843A Division JP5340605B2 (ja) | 1997-08-21 | 2008-01-31 | 充填材含有ゴム用保護化メルカプトシラン・カップリング剤 |
Publications (2)
| Publication Number | Publication Date |
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| JP2001505225A true JP2001505225A (ja) | 2001-04-17 |
| JP2001505225A5 JP2001505225A5 (enExample) | 2004-12-09 |
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| Application Number | Title | Priority Date | Filing Date |
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| JP51363999A Withdrawn JP2001505225A (ja) | 1997-08-21 | 1998-08-21 | 充填材含有ゴム用保護化メルカプトシラン・カップリング剤 |
| JP2008020843A Expired - Lifetime JP5340605B2 (ja) | 1997-08-21 | 2008-01-31 | 充填材含有ゴム用保護化メルカプトシラン・カップリング剤 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008020843A Expired - Lifetime JP5340605B2 (ja) | 1997-08-21 | 2008-01-31 | 充填材含有ゴム用保護化メルカプトシラン・カップリング剤 |
Country Status (12)
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| US (12) | US6414061B1 (enExample) |
| EP (3) | EP1270581B1 (enExample) |
| JP (2) | JP2001505225A (enExample) |
| KR (2) | KR100825539B1 (enExample) |
| CN (2) | CN101139355A (enExample) |
| AT (1) | ATE239737T1 (enExample) |
| AU (1) | AU8917998A (enExample) |
| BR (1) | BR9806096B1 (enExample) |
| DE (1) | DE69814353T3 (enExample) |
| ES (2) | ES2199454T5 (enExample) |
| PT (1) | PT958298E (enExample) |
| WO (1) | WO1999009036A1 (enExample) |
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