CN1242774A - 用于填充橡胶的封端巯基硅烷偶联剂 - Google Patents
用于填充橡胶的封端巯基硅烷偶联剂 Download PDFInfo
- Publication number
- CN1242774A CN1242774A CN98801562A CN98801562A CN1242774A CN 1242774 A CN1242774 A CN 1242774A CN 98801562 A CN98801562 A CN 98801562A CN 98801562 A CN98801562 A CN 98801562A CN 1242774 A CN1242774 A CN 1242774A
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- CN
- China
- Prior art keywords
- ester
- triethoxysilyl
- acid
- methyl
- silane
- 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.)
- Granted
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- 229920001971 elastomer Polymers 0.000 title claims abstract description 87
- 239000005060 rubber Substances 0.000 title claims abstract description 87
- TXDNPSYEJHXKMK-UHFFFAOYSA-N sulfanylsilane Chemical compound S[SiH3] TXDNPSYEJHXKMK-UHFFFAOYSA-N 0.000 title abstract description 6
- 239000007822 coupling agent Substances 0.000 title description 10
- 238000000034 method Methods 0.000 claims abstract description 48
- 239000000945 filler Substances 0.000 claims abstract description 34
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 29
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 23
- 229920000620 organic polymer Polymers 0.000 claims abstract description 13
- 150000002148 esters Chemical class 0.000 claims description 200
- -1 isobutyl- Chemical group 0.000 claims description 200
- 229910000077 silane Inorganic materials 0.000 claims description 140
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 127
- MCEBKLYUUDGVMD-UHFFFAOYSA-N [SiH3]S(=O)=O Chemical compound [SiH3]S(=O)=O MCEBKLYUUDGVMD-UHFFFAOYSA-N 0.000 claims description 99
- 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 94
- 239000000203 mixture Substances 0.000 claims description 69
- 239000002253 acid Substances 0.000 claims description 62
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 54
- 239000002585 base Substances 0.000 claims description 37
- 229910052799 carbon Inorganic materials 0.000 claims description 36
- 150000001721 carbon Chemical group 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 239000005864 Sulphur Substances 0.000 claims description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 22
- 125000002769 thiazolinyl group Chemical group 0.000 claims description 22
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 21
- 229910052783 alkali metal Inorganic materials 0.000 claims description 20
- 150000008065 acid anhydrides Chemical class 0.000 claims description 19
- 239000011203 carbon fibre reinforced carbon Chemical group 0.000 claims description 17
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 16
- 238000005809 transesterification reaction Methods 0.000 claims description 16
- 150000007513 acids Chemical class 0.000 claims description 15
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
- 150000007970 thio esters Chemical group 0.000 claims description 15
- GWIKYPMLNBTJHR-UHFFFAOYSA-M thiosulfonate group Chemical group S(=S)(=O)[O-] GWIKYPMLNBTJHR-UHFFFAOYSA-M 0.000 claims description 14
- 125000004437 phosphorous atom Chemical group 0.000 claims description 13
- 229910052698 phosphorus Inorganic materials 0.000 claims description 13
- 150000001336 alkenes Chemical group 0.000 claims description 12
- 239000003153 chemical reaction reagent Substances 0.000 claims description 12
- 125000005574 norbornylene group Chemical group 0.000 claims description 12
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 12
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- ZXRDVSMSMOZCPT-UHFFFAOYSA-N phosphorodithious acid Chemical compound OP(S)S ZXRDVSMSMOZCPT-UHFFFAOYSA-N 0.000 claims description 9
- 150000003566 thiocarboxylic acids Chemical class 0.000 claims description 9
- SMDVDXOWTRMZKF-UHFFFAOYSA-N C1C[SiH2]SC1 Chemical compound C1C[SiH2]SC1 SMDVDXOWTRMZKF-UHFFFAOYSA-N 0.000 claims description 8
- 150000001263 acyl chlorides Chemical class 0.000 claims description 8
- 150000001266 acyl halides Chemical class 0.000 claims description 7
- 239000012764 mineral filler Substances 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- KYLIZBIRMBGUOP-UHFFFAOYSA-N Anetholtrithion Chemical group C1=CC(OC)=CC=C1C1=CC(=S)SS1 KYLIZBIRMBGUOP-UHFFFAOYSA-N 0.000 claims description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 6
- QPLUSKXLDQLASM-UHFFFAOYSA-N SP(S)=S Chemical compound SP(S)=S QPLUSKXLDQLASM-UHFFFAOYSA-N 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 239000003999 initiator Substances 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 6
- KPQYZHFYHGSRMA-UHFFFAOYSA-N o-(6-triethoxysilylhexyl) ethanethioate Chemical compound CCO[Si](OCC)(OCC)CCCCCCOC(C)=S KPQYZHFYHGSRMA-UHFFFAOYSA-N 0.000 claims description 6
- 238000006884 silylation reaction Methods 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 5
- 229920001296 polysiloxane Polymers 0.000 claims description 5
- 239000000376 reactant Substances 0.000 claims description 5
- IFVMAGPISVKRAR-UHFFFAOYSA-N 1-ethylcyclohexene Chemical compound CCC1=CCCCC1 IFVMAGPISVKRAR-UHFFFAOYSA-N 0.000 claims description 3
- COZRTRJJVRJPMD-UHFFFAOYSA-N 2-ethyl-2-sulfohexanoic acid Chemical compound C(C)C(C(=O)O)(CCCC)S(=O)(=O)O COZRTRJJVRJPMD-UHFFFAOYSA-N 0.000 claims description 3
- CJAJEZSCULAKCB-UHFFFAOYSA-N 2-sulfohexadecanoic acid Chemical compound CCCCCCCCCCCCCCC(C(O)=O)S(O)(=O)=O CJAJEZSCULAKCB-UHFFFAOYSA-N 0.000 claims description 3
- WXOFQPMQHAHBKI-UHFFFAOYSA-N 4-ethylbicyclo[2.2.1]hept-2-ene Chemical compound C1CC2C=CC1(CC)C2 WXOFQPMQHAHBKI-UHFFFAOYSA-N 0.000 claims description 3
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 3
- UQICZBQBJAQZAX-UHFFFAOYSA-N S(=S)(=O)O.C(C)O[Si](C=1C=C(C=CC1)CCC)(OCC)OCC Chemical class S(=S)(=O)O.C(C)O[Si](C=1C=C(C=CC1)CCC)(OCC)OCC UQICZBQBJAQZAX-UHFFFAOYSA-N 0.000 claims description 3
- WZWCDTRLAITSBV-UHFFFAOYSA-N S(=S)(=O)O.C(C)O[Si](C=1CC(C)(C=CC1)CCC)(OCC)OCC Chemical class S(=S)(=O)O.C(C)O[Si](C=1CC(C)(C=CC1)CCC)(OCC)OCC WZWCDTRLAITSBV-UHFFFAOYSA-N 0.000 claims description 3
- XDCFZTSIQRJWOT-UHFFFAOYSA-N S(=S)(=O)O.C(C)O[Si](OCC)(OCC)C(C)C Chemical class S(=S)(=O)O.C(C)O[Si](OCC)(OCC)C(C)C XDCFZTSIQRJWOT-UHFFFAOYSA-N 0.000 claims description 3
- NUDIMLOHNGNUKG-UHFFFAOYSA-N S(=S)(=O)O.C(C)O[Si](OCC)(OCC)C(C1=CC=CC=C1)C Chemical class S(=S)(=O)O.C(C)O[Si](OCC)(OCC)C(C1=CC=CC=C1)C NUDIMLOHNGNUKG-UHFFFAOYSA-N 0.000 claims description 3
- RMKTWHQPUCYRCH-UHFFFAOYSA-N S(=S)(=O)O.C(C)O[Si](OCC)(OCC)C1=C(C2=CC=CC=C2C=C1)C Chemical class S(=S)(=O)O.C(C)O[Si](OCC)(OCC)C1=C(C2=CC=CC=C2C=C1)C RMKTWHQPUCYRCH-UHFFFAOYSA-N 0.000 claims description 3
- XPGNMZZADTWNGA-UHFFFAOYSA-N S(=S)(=O)O.C(C)O[Si](OCC)(OCC)C1=C(C=CC=C1)C Chemical class S(=S)(=O)O.C(C)O[Si](OCC)(OCC)C1=C(C=CC=C1)C XPGNMZZADTWNGA-UHFFFAOYSA-N 0.000 claims description 3
- SVLRJMVELYIDIO-UHFFFAOYSA-N S(=S)(=O)O.C(C)O[Si](OCC)(OCC)CC Chemical class S(=S)(=O)O.C(C)O[Si](OCC)(OCC)CC SVLRJMVELYIDIO-UHFFFAOYSA-N 0.000 claims description 3
- 238000007259 addition reaction Methods 0.000 claims description 3
- UIJGNTRUPZPVNG-UHFFFAOYSA-N benzenecarbothioic s-acid Chemical compound SC(=O)C1=CC=CC=C1 UIJGNTRUPZPVNG-UHFFFAOYSA-N 0.000 claims description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 238000006555 catalytic reaction Methods 0.000 claims description 3
- 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 3
- NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical compound OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- YACCECLVHQLZQK-UHFFFAOYSA-N methoxyperoxyethane Chemical compound CCOOOC YACCECLVHQLZQK-UHFFFAOYSA-N 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 claims description 3
- XNJGLSDTGOHPBZ-UHFFFAOYSA-N o-(1-triethoxysilylbutan-2-yl) ethanethioate Chemical compound CCO[Si](OCC)(OCC)CC(CC)OC(C)=S XNJGLSDTGOHPBZ-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 3
- BQXZKHYBQNQQHL-UHFFFAOYSA-N o-(10-triethoxysilyldecyl) ethanethioate Chemical compound CCO[Si](OCC)(OCC)CCCCCCCCCCOC(C)=S BQXZKHYBQNQQHL-UHFFFAOYSA-N 0.000 claims description 3
- LNEPUQCXRWFYJZ-UHFFFAOYSA-N o-(2-methyl-4-triethoxysilylbutan-2-yl) ethanethioate Chemical compound CCO[Si](OCC)(OCC)CCC(C)(C)OC(C)=S LNEPUQCXRWFYJZ-UHFFFAOYSA-N 0.000 claims description 3
- VRLXDBAWJNGTSJ-UHFFFAOYSA-N o-(2-triethoxysilylethyl) ethanethioate Chemical compound CCO[Si](OCC)(OCC)CCOC(C)=S VRLXDBAWJNGTSJ-UHFFFAOYSA-N 0.000 claims description 3
- XESGARYTTVPVGI-UHFFFAOYSA-N o-(2-trimethoxysilylethyl) ethanethioate Chemical compound CO[Si](OC)(OC)CCOC(C)=S XESGARYTTVPVGI-UHFFFAOYSA-N 0.000 claims description 3
- VMARVBIRPYNUAP-UHFFFAOYSA-N o-(3-methyl-1-triethoxysilylbutan-2-yl) ethanethioate Chemical compound CCO[Si](OCC)(OCC)CC(OC(C)=S)C(C)C VMARVBIRPYNUAP-UHFFFAOYSA-N 0.000 claims description 3
- HTMRUFPADNOKKQ-UHFFFAOYSA-N o-(4-triethoxysilylbutan-2-yl) ethanethioate Chemical compound CCO[Si](OCC)(OCC)CCC(C)OC(C)=S HTMRUFPADNOKKQ-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 3
- QXBLIUBAPLUCFY-UHFFFAOYSA-N o-(triethoxysilylmethyl) ethanethioate Chemical compound CCO[Si](OCC)(OCC)COC(C)=S QXBLIUBAPLUCFY-UHFFFAOYSA-N 0.000 claims description 3
- DUGAFPBTRVNWOH-UHFFFAOYSA-N o-(trimethoxysilylmethyl) ethanethioate Chemical compound CO[Si](OC)(OC)COC(C)=S DUGAFPBTRVNWOH-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- 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 3
- 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 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 238000007342 radical addition reaction Methods 0.000 claims description 3
- 150000003254 radicals Chemical class 0.000 claims description 3
- DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 claims description 3
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- 230000007246 mechanism Effects 0.000 claims description 2
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- 229920000642 polymer Polymers 0.000 abstract description 4
- WTGIOQMHIHCSPZ-UHFFFAOYSA-N sulfanylsilicon Chemical class S[Si] WTGIOQMHIHCSPZ-UHFFFAOYSA-N 0.000 abstract 2
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- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 1
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- BLORRZQTHNGFTI-ZZMNMWMASA-L calcium-L-ascorbate Chemical compound [Ca+2].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] BLORRZQTHNGFTI-ZZMNMWMASA-L 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
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- ZDOBWJOCPDIBRZ-UHFFFAOYSA-N chloromethyl(triethoxy)silane Chemical class CCO[Si](CCl)(OCC)OCC ZDOBWJOCPDIBRZ-UHFFFAOYSA-N 0.000 description 1
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- NAGJZTKCGNOGPW-UHFFFAOYSA-K dioxido-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [O-]P([O-])([S-])=S NAGJZTKCGNOGPW-UHFFFAOYSA-K 0.000 description 1
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- DECIPOUIJURFOJ-UHFFFAOYSA-N ethoxyquin Chemical compound N1C(C)(C)C=C(C)C2=CC(OCC)=CC=C21 DECIPOUIJURFOJ-UHFFFAOYSA-N 0.000 description 1
- CWAFVXWRGIEBPL-UHFFFAOYSA-N ethoxysilane Chemical compound CCO[SiH3] CWAFVXWRGIEBPL-UHFFFAOYSA-N 0.000 description 1
- SBRXLTRZCJVAPH-UHFFFAOYSA-N ethyl(trimethoxy)silane Chemical compound CC[Si](OC)(OC)OC SBRXLTRZCJVAPH-UHFFFAOYSA-N 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N ferric oxide Chemical compound O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
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- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
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- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 239000000413 hydrolysate Substances 0.000 description 1
- VDTIMXCBOXBHER-UHFFFAOYSA-N hydroxy-bis(sulfanyl)-sulfanylidene-$l^{5}-phosphane Chemical compound OP(S)(S)=S VDTIMXCBOXBHER-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 229920003049 isoprene rubber Polymers 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 150000002680 magnesium Chemical class 0.000 description 1
- 239000002075 main ingredient Substances 0.000 description 1
- BAXLBXFAUKGCDY-UHFFFAOYSA-N mebendazole Chemical compound [CH]1C2=NC(NC(=O)OC)=NC2=CC=C1C(=O)C1=CC=CC=C1 BAXLBXFAUKGCDY-UHFFFAOYSA-N 0.000 description 1
- 229960003439 mebendazole Drugs 0.000 description 1
- 150000002730 mercury Chemical class 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 150000002780 morpholines Chemical class 0.000 description 1
- DEQZTKGFXNUBJL-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)cyclohexanamine Chemical compound C1CCCCC1NSC1=NC2=CC=CC=C2S1 DEQZTKGFXNUBJL-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- RFPMGSKVEAUNMZ-UHFFFAOYSA-N pentylidene Chemical group [CH2+]CCC[CH-] RFPMGSKVEAUNMZ-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- XCRBXWCUXJNEFX-UHFFFAOYSA-N peroxybenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1 XCRBXWCUXJNEFX-UHFFFAOYSA-N 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- RGCLLPNLLBQHPF-HJWRWDBZSA-N phosphamidon Chemical compound CCN(CC)C(=O)C(\Cl)=C(/C)OP(=O)(OC)OC RGCLLPNLLBQHPF-HJWRWDBZSA-N 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 1
- 230000001698 pyrogenic effect Effects 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000012763 reinforcing filler Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000010057 rubber processing Methods 0.000 description 1
- FPQLAGZIFPNCND-UHFFFAOYSA-N s-(2-triethoxysilylethyl) ethanethioate Chemical compound CCO[Si](OCC)(OCC)CCSC(C)=O FPQLAGZIFPNCND-UHFFFAOYSA-N 0.000 description 1
- WHALSQRTWNBBCV-UHFFFAOYSA-N s-aminosulfanylthiohydroxylamine Chemical compound NSSN WHALSQRTWNBBCV-UHFFFAOYSA-N 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 150000003376 silicon Chemical class 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
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- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- VKHQYTLHHOQKSC-UHFFFAOYSA-N sulfosulfamic acid Chemical compound OS(=O)(=O)NS(O)(=O)=O VKHQYTLHHOQKSC-UHFFFAOYSA-N 0.000 description 1
- 150000003463 sulfur Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 1
- 238000007669 thermal treatment Methods 0.000 description 1
- 229950000898 thiambutosine Drugs 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 229920006031 tri-component-copolymer Polymers 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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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- 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
- 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
- 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
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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
- 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
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- 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
-
- 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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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Sealing Material Composition (AREA)
- Organic Insulating Materials (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Silicon Polymers (AREA)
Abstract
Description
Claims (19)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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US5656697P | 1997-08-21 | 1997-08-21 | |
US06/056,566 | 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 |
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CNA2007101424877A Division CN101139355A (zh) | 1997-08-21 | 1998-08-21 | 用于填充橡胶的封端巯基硅烷偶联剂 |
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CN1242774A true CN1242774A (zh) | 2000-01-26 |
CN100376585C CN100376585C (zh) | 2008-03-26 |
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CNB988015625A Expired - Lifetime CN100376585C (zh) | 1997-08-21 | 1998-08-21 | 用于填充橡胶的封端巯基硅烷偶联剂 |
CNA2007101424877A Pending CN101139355A (zh) | 1997-08-21 | 1998-08-21 | 用于填充橡胶的封端巯基硅烷偶联剂 |
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CNA2007101424877A Pending CN101139355A (zh) | 1997-08-21 | 1998-08-21 | 用于填充橡胶的封端巯基硅烷偶联剂 |
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US (12) | US6414061B1 (zh) |
EP (3) | EP1270581B1 (zh) |
JP (2) | JP2001505225A (zh) |
KR (2) | KR100825539B1 (zh) |
CN (2) | CN100376585C (zh) |
AT (1) | ATE239737T1 (zh) |
AU (1) | AU8917998A (zh) |
BR (1) | BR9806096B1 (zh) |
DE (1) | DE69814353T3 (zh) |
ES (2) | ES2199454T5 (zh) |
PT (1) | PT958298E (zh) |
WO (1) | WO1999009036A1 (zh) |
Cited By (18)
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CN100384924C (zh) * | 2004-09-10 | 2008-04-30 | 固特异轮胎和橡胶公司 | 具有橡胶组合物的胎面的轮胎 |
CN100422193C (zh) * | 2003-07-03 | 2008-10-01 | 莫门蒂夫性能材料股份有限公司 | 制备硫代羧酸酯硅烷的方法 |
US7432321B2 (en) | 2002-07-09 | 2008-10-07 | Momentive Performance Materials Inc. | Silica-rubber mixtures having improved hardness |
CN100425255C (zh) * | 2005-10-13 | 2008-10-15 | 同溢堂药业有限公司 | 一种治疗颈椎病的药物及其制备方法 |
CN1789315B (zh) * | 2004-12-18 | 2011-07-20 | 赢创德固赛有限公司 | 橡胶混合物 |
CN102307884A (zh) * | 2008-12-22 | 2012-01-04 | 米其林技术公司 | 封端的巯基硅烷偶联剂 |
CN101622307B (zh) * | 2006-10-06 | 2012-11-21 | 莫门蒂夫性能材料股份有限公司 | 含有巯基官能硅烷的弹性体组合物及其制备方法 |
CN101426800B (zh) * | 2006-02-21 | 2013-04-03 | 莫门蒂夫性能材料股份有限公司 | 含有有机官能硅烷的橡胶组合物 |
CN103119086A (zh) * | 2010-08-13 | 2013-05-22 | Prc-迪索托国际公司 | 通过光化辐射制造固化的密封剂的方法和相关的组合物 |
TWI408167B (zh) * | 2004-08-20 | 2013-09-11 | Momentive Performance Mat Inc | 環狀二醇衍生之嵌段巰基官能性矽烷組合物 |
TWI409272B (zh) * | 2006-08-14 | 2013-09-21 | Momentive Performance Mat Inc | 巰官能性矽烷 |
CN101426799B (zh) * | 2006-02-21 | 2013-10-02 | 莫门蒂夫性能材料股份有限公司 | 制备有机官能的硅烷及其混合物的方法 |
CN101611042B (zh) * | 2006-12-28 | 2014-05-21 | 莫门蒂夫性能材料股份有限公司 | 封端巯基硅烷偶联剂、制备方法及在橡胶组合物中的应用 |
TWI453243B (zh) * | 2007-06-05 | 2014-09-21 | Momentive Performance Mat Inc | 橡膠組成物之製法及由彼製成之物品 |
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