CN1481419A - 矿物质填充的弹性体组合物 - Google Patents
矿物质填充的弹性体组合物 Download PDFInfo
- Publication number
- CN1481419A CN1481419A CNA018205798A CN01820579A CN1481419A CN 1481419 A CN1481419 A CN 1481419A CN A018205798 A CNA018205798 A CN A018205798A CN 01820579 A CN01820579 A CN 01820579A CN 1481419 A CN1481419 A CN 1481419A
- Authority
- CN
- China
- Prior art keywords
- triethoxysilyl
- ester
- thioacetic acid
- methyl
- propyl
- 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
Links
- 229920001971 elastomer Polymers 0.000 title claims abstract description 103
- 229910052500 inorganic mineral Inorganic materials 0.000 title description 15
- 239000011707 mineral Substances 0.000 title description 15
- 239000000806 elastomer Substances 0.000 title 1
- 239000000203 mixture Substances 0.000 claims abstract description 168
- 239000005060 rubber Substances 0.000 claims abstract description 101
- 239000000945 filler Substances 0.000 claims abstract description 48
- 239000012190 activator Substances 0.000 claims abstract description 42
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 41
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims abstract description 30
- -1 aromatic vinyl compound Chemical class 0.000 claims description 176
- 229910000077 silane Inorganic materials 0.000 claims description 170
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 167
- MCEBKLYUUDGVMD-UHFFFAOYSA-N [SiH3]S(=O)=O Chemical compound [SiH3]S(=O)=O MCEBKLYUUDGVMD-UHFFFAOYSA-N 0.000 claims description 113
- 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 90
- 238000002156 mixing Methods 0.000 claims description 54
- 238000000034 method Methods 0.000 claims description 40
- 150000002148 esters Chemical class 0.000 claims description 37
- 239000005864 Sulphur Substances 0.000 claims description 33
- 229910052799 carbon Inorganic materials 0.000 claims description 30
- 239000000126 substance Substances 0.000 claims description 29
- 150000002430 hydrocarbons Chemical class 0.000 claims description 24
- 238000002360 preparation method Methods 0.000 claims description 24
- 239000004215 Carbon black (E152) Substances 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 229930195733 hydrocarbon Natural products 0.000 claims description 23
- 238000010059 sulfur vulcanization Methods 0.000 claims description 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
- 229920003052 natural elastomer Polymers 0.000 claims description 21
- 229920001194 natural rubber Polymers 0.000 claims description 21
- 244000043261 Hevea brasiliensis Species 0.000 claims description 20
- 239000000463 material Substances 0.000 claims description 18
- 150000001721 carbon Chemical group 0.000 claims description 17
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- 239000001301 oxygen Substances 0.000 claims description 17
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
- 238000005987 sulfurization reaction Methods 0.000 claims description 15
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- 125000002769 thiazolinyl group Chemical group 0.000 claims description 13
- LJSQFQKUNVCTIA-UHFFFAOYSA-N diethyl sulfide Chemical compound CCSCC LJSQFQKUNVCTIA-UHFFFAOYSA-N 0.000 claims description 12
- 125000005574 norbornylene group Chemical group 0.000 claims description 12
- 229920002554 vinyl polymer Polymers 0.000 claims description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 10
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims description 9
- 239000012634 fragment Substances 0.000 claims description 9
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 claims description 9
- 150000001993 dienes Chemical class 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- VDTIMXCBOXBHER-UHFFFAOYSA-N hydroxy-bis(sulfanyl)-sulfanylidene-$l^{5}-phosphane Chemical compound OP(S)(S)=S VDTIMXCBOXBHER-UHFFFAOYSA-N 0.000 claims description 7
- ZZUUPTIYZCXZBR-UHFFFAOYSA-N CCSP(O)=S Chemical compound CCSP(O)=S ZZUUPTIYZCXZBR-UHFFFAOYSA-N 0.000 claims description 6
- CGXXUGKJQXYOBH-UHFFFAOYSA-N CSP(O)=S Chemical compound CSP(O)=S CGXXUGKJQXYOBH-UHFFFAOYSA-N 0.000 claims description 6
- YWHLKYXPLRWGSE-UHFFFAOYSA-N Dimethyl trisulfide Chemical compound CSSSC YWHLKYXPLRWGSE-UHFFFAOYSA-N 0.000 claims description 6
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
- 150000004702 methyl esters Chemical class 0.000 claims description 6
- 229910052698 phosphorus Inorganic materials 0.000 claims description 6
- 239000011574 phosphorus Substances 0.000 claims description 6
- 238000006884 silylation reaction Methods 0.000 claims description 6
- 229920001897 terpolymer Polymers 0.000 claims description 6
- ITRFOBBKTCNNFN-UHFFFAOYSA-N tris(sulfanyl)-sulfanylidene-$l^{5}-phosphane Chemical compound SP(S)(S)=S ITRFOBBKTCNNFN-UHFFFAOYSA-N 0.000 claims description 5
- 229920001577 copolymer Polymers 0.000 claims description 4
- KGCOCRLKKXDJLC-UHFFFAOYSA-N C(C)O[Si](CCCOC(C(CCCCCCCCCCCCCC)S(=O)(=O)O)=O)(OCC)OCC Chemical compound C(C)O[Si](CCCOC(C(CCCCCCCCCCCCCC)S(=O)(=O)O)=O)(OCC)OCC KGCOCRLKKXDJLC-UHFFFAOYSA-N 0.000 claims description 3
- TVRWWPVVWDNZDW-UHFFFAOYSA-N CCCCC(CC)(C(=O)OCCC[Si](OCC)(OCC)OCC)S(=O)(=O)O Chemical compound CCCCC(CC)(C(=O)OCCC[Si](OCC)(OCC)OCC)S(=O)(=O)O TVRWWPVVWDNZDW-UHFFFAOYSA-N 0.000 claims description 3
- RKEZYTBJAAZWFL-UHFFFAOYSA-N CCOOOC.C(C)(=S)O Chemical compound CCOOOC.C(C)(=S)O RKEZYTBJAAZWFL-UHFFFAOYSA-N 0.000 claims description 3
- CETBSQOFQKLHHZ-UHFFFAOYSA-N Diethyl disulfide Chemical group CCSSCC CETBSQOFQKLHHZ-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 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
- 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
- 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 group 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
- 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 description 3
- RVZJJFTUWQGPDM-UHFFFAOYSA-N o-(3-triethoxysilylpropyl) ethanethioate Chemical compound CCO[Si](OCC)(OCC)CCCOC(C)=S RVZJJFTUWQGPDM-UHFFFAOYSA-N 0.000 claims description 3
- QDFFFDHNDDVFCN-UHFFFAOYSA-N o-(3-trimethoxysilylpropyl) ethanethioate Chemical compound CO[Si](OC)(OC)CCCOC(C)=S QDFFFDHNDDVFCN-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
- 150000003008 phosphonic acid esters Chemical class 0.000 claims description 3
- 238000007493 shaping process Methods 0.000 claims description 3
- NSGHUDWCQOAIDA-UHFFFAOYSA-N triethyl methoxysulfonothioyl silicate Chemical class S(=S)(=O)(O[Si](OCC)(OCC)OCC)OC NSGHUDWCQOAIDA-UHFFFAOYSA-N 0.000 claims description 3
- NYCKABUOCAKNGX-UHFFFAOYSA-N 10-triethoxysilyldecane-1-thiol Chemical compound CCO[Si](OCC)(OCC)CCCCCCCCCCS NYCKABUOCAKNGX-UHFFFAOYSA-N 0.000 claims description 2
- ROYRUMBLNWJMGV-UHFFFAOYSA-N 10-trimethoxysilyldecane-1-thiol Chemical compound CO[Si](OC)(OC)CCCCCCCCCCS ROYRUMBLNWJMGV-UHFFFAOYSA-N 0.000 claims description 2
- DVNPFNZTPMWRAX-UHFFFAOYSA-N 2-triethoxysilylethanethiol Chemical compound CCO[Si](CCS)(OCC)OCC DVNPFNZTPMWRAX-UHFFFAOYSA-N 0.000 claims description 2
- LOSLJXKHQKRRFN-UHFFFAOYSA-N 2-trimethoxysilylethanethiol Chemical compound CO[Si](OC)(OC)CCS LOSLJXKHQKRRFN-UHFFFAOYSA-N 0.000 claims description 2
- UFUVFHZSNVNSER-UHFFFAOYSA-N 4-dimethylsilyloxybutane-1-thiol Chemical compound SCCCCO[SiH](C)C UFUVFHZSNVNSER-UHFFFAOYSA-N 0.000 claims description 2
- QSQQQWNVBDSGDO-UHFFFAOYSA-N 4-dimethylsilyloxypentane-1-thiol Chemical compound SCCCC(C)O[SiH](C)C QSQQQWNVBDSGDO-UHFFFAOYSA-N 0.000 claims description 2
- PZFQJXXCFIHFMI-UHFFFAOYSA-N 8-triethoxysilyloctane-1-thiol Chemical compound CCO[Si](OCC)(OCC)CCCCCCCCS PZFQJXXCFIHFMI-UHFFFAOYSA-N 0.000 claims description 2
- GEVFNCLQTVOUIL-UHFFFAOYSA-N SCCO[Si](OCC)(OCC)C Chemical compound SCCO[Si](OCC)(OCC)C GEVFNCLQTVOUIL-UHFFFAOYSA-N 0.000 claims description 2
- RPCGDCYHXWVDNM-UHFFFAOYSA-N [dimethoxy(methyl)silyl]oxymethanethiol Chemical compound CO[Si](C)(OC)OCS RPCGDCYHXWVDNM-UHFFFAOYSA-N 0.000 claims description 2
- ZZHNUBIHHLQNHX-UHFFFAOYSA-N butoxysilane Chemical class CCCCO[SiH3] ZZHNUBIHHLQNHX-UHFFFAOYSA-N 0.000 claims description 2
- GAURFLBIDLSLQU-UHFFFAOYSA-N diethoxy(methyl)silicon Chemical compound CCO[Si](C)OCC GAURFLBIDLSLQU-UHFFFAOYSA-N 0.000 claims description 2
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- 238000002203 pretreatment Methods 0.000 claims description 2
- HCOKJWUULRTBRS-UHFFFAOYSA-N propan-2-yloxysilane Chemical compound CC(C)O[SiH3] HCOKJWUULRTBRS-UHFFFAOYSA-N 0.000 claims description 2
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- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000032696 parturition Effects 0.000 description 1
- 229940059574 pentaerithrityl Drugs 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- KNBRWWCHBRQLNY-UHFFFAOYSA-N piperidine-1-carbothioylsulfanyl piperidine-1-carbodithioate Chemical compound C1CCCCN1C(=S)SSC(=S)N1CCCCC1 KNBRWWCHBRQLNY-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 238000002459 porosimetry Methods 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229910052704 radon Inorganic materials 0.000 description 1
- SYUHGPGVQRZVTB-UHFFFAOYSA-N radon atom Chemical compound [Rn] SYUHGPGVQRZVTB-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 229920003987 resole Polymers 0.000 description 1
- 239000003340 retarding agent Substances 0.000 description 1
- 238000010057 rubber processing Methods 0.000 description 1
- WHALSQRTWNBBCV-UHFFFAOYSA-N s-aminosulfanylthiohydroxylamine Chemical compound NSSN WHALSQRTWNBBCV-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 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
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 229920005613 synthetic organic polymer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000007669 thermal treatment Methods 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229920006031 tri-component-copolymer Polymers 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 239000012991 xanthate Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 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
- AUMBZPPBWALQRO-UHFFFAOYSA-L zinc;n,n-dibenzylcarbamodithioate Chemical compound [Zn+2].C=1C=CC=CC=1CN(C(=S)[S-])CC1=CC=CC=C1.C=1C=CC=CC=1CN(C(=S)[S-])CC1=CC=CC=C1 AUMBZPPBWALQRO-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
- B60C1/00—Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
- B60C1/00—Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
- B60C1/0016—Compositions of the tread
-
- 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
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/37—Thiols
-
- 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
-
- 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
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L23/16—Elastomeric ethene-propene or ethene-propene-diene copolymers, e.g. EPR and EPDM rubbers
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Tires In General (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
Abstract
Description
门尼粘度和焦烧 | ASTM D1646 |
圆盘振荡流变仪 | ASTM D2084 |
测试片的硫化 | ASTM D3182 |
应力-应变性能 | ASTM D412 |
磨耗 | DIN 53516 |
生热 | ASTM D623 |
基本配方 | |||
份数 | 成分 | 产品名称 | 提供商 |
75 | 溶液SBR | SOLFLEX 1216 | Goodyear |
25 | 聚丁二烯 | BUDENE 1207 | Goodyear |
80 | 二氧化硅 | ZEOSIL 1165MP | Rhodia |
32.5 | 加工油 | SUNDEX 8125 | Sun Oil |
2.5 | 氧化锌 | KADOX 720C | Zinc Corp. |
1.0 | 硬脂酸 | F-300 | Harwick |
2.0 | 6PPD抗氧剂 | FLEXZONE 7P | Uniroyal Chemical |
1.5 | 微蜡 | SUNPROOFIMPROVED | Uniroyal Chemical |
3.0 | 炭黑 | N-330 | Engineered Carbons |
1.4 | 硫 | Rubbermakers 104 | Harwick |
1.7 | CBS | DELAC-5 | Uniroyal Chemical |
2.0 | DPG | DPG | Uniroyal Chemical |
变量 | 硅烷 | 各种 | OSi Specialties |
命名 | 化学名称 |
SilquestA-1289 | 四硫化双(3-三乙氧基甲硅烷基-1-丙基) |
Silquest A-1589 | 二硫化双(3-三乙氧基甲硅烷基-1-丙基) |
Silquest A-1891 | 3-巯基丙基三乙氧基硅烷 |
Silane A | 3-辛酰基硫代-1-丙基三乙氧基硅烷 |
Silane B | 3-乙酰基硫代-1-丙基三乙氧基硅烷 |
Silane C | 3-巯基-1-丙基三甲氧基硅烷 |
1BA-12892遍160℃ | 2BA-15892遍160℃ | 3B硅烷A2遍160℃ | 6AB硅烷A1遍160℃ | |
硫化状态中的性能非线性(0-10%)G′初始(MPa)ΔG′(MPa)G″最大(MPa)tanδ最大大应变滞后35%DSA增强M10(MPa)M100(MPa)M300(MPa)M300/M100断裂应力(MPa)断裂伸长率(%) | 3.31.650.390.1820.1295.54.0315.43.8227.5470 | 31.40.380.190.15353.0710.23.3128.5610 | 3.620.410.170.1315.133.3292.7122.5662 | 4.52.80.550.20.1455.793.519.152.620.11754 |
3B硅烷A2遍160℃ | 5AB硅烷A1遍180℃ | 5AB硅烷A1遍170℃ | 4AB硅烷A1遍180℃ | |
硫化状态中的性能非线性(0-10%)G′初始(MPa)ΔG′(MPa)G″最大(MPa)tanδ最大大应变滞后35%DSA增强M10(MPa)M100(MPa)M300(MPa)M300/M100断裂应力(MPa)断裂伸长率(%) | 3.620.410.170.1315.133.3292.7122.5662 | 4.52.80.550.20.1455.783.519.152.620.11754 | 4.12.40.4750.1850.145.573.4639.12.6325.9750 | 3.72.050.430.180.1335.23.49.472.7925.5700 |
6AB硅烷A1遍160℃50/50二氧化硅 | 9AB硅烷A1遍160℃75/25二氧化硅 | 10AB硅烷A1遍160℃90/10二氧化硅 | |
在第一阶段二氧化硅加入之后的kwh在第二阶段二氧化硅加入之后的kwh在硅烷化期间的kwh硫化状态中的性能非线性(0-10%)G′初始(MPa)ΔG′(MPa)G″最大(MPa)tanδ最大大应变滞后35%DSA增强M10(MPa)M100(MPa)M300(MPa)M300/M100断裂应力(MPa)断裂伸长率(%) | 0.221.11104.52.80.550.20.1455.793.519.152.620.11754 | 1.021.068.594.42.650.510.1850.1365.653.589.22.5727.13776 | 1.330.918.154.52.70.5450.190.13763.69.52.6426.2740 |
6AB硅烷A1遍160℃0.67FF50/50二氧化硅 | 11AB硅烷A1遍160℃0.72FF50/50二氧化硅 | 12AB硅烷A1遍160℃0.76FF50/50二氧化硅 | 13AB硅烷A1遍150℃0.72FF90/10二氧化硅 | |
硫化状态中的性能非线性(0-10%)G′初始(MPa)ΔG′(MPa)G″最大(MPa)tanδ最大大应变滞后35%DSA增强M10(MPa)M100(MPa)M300(MPa)M300/M100断裂应力(MPa)断裂伸长率(%) | 4.52.80.550.20.1455.793.519.152.620.11754 | 5.253.350.6150.20.145.83.79.622.5926740 | 5.23.30.620.20.14163.589.12.5425.5720 | 4.52.70.530.190.1396.23.79.562.5825.8720 |
4AB硅烷A1遍180℃ | 13AB硅烷A1遍160℃0.72FF90/10二氧化硅 | 15AB硅烷A1遍,170℃3%硅烷C0.72FF90/10二氧化硅 | 16AB硅烷A1遍170℃6%硅烷C0.72FF90/10二氧化硅 | |
硫化状态中的性能非线性(0-10%)G′初始(MPa)ΔG′(MPa)G″最大(MPa)tanδ最大大应变滞后35%DSA增强M10(MPa)M100(MPa)M300(MPa)M300/M100断裂应力(MPa)断裂伸长率(%) | 3.72.050.430.180.1335.23.49.472.7925.5700 | 4.52.70.530.190.1395.23.79.562.5825.8720 | 4.12.350.4750.180.1315.413.7110.012.6925880 | 4.162.50.470.190.1354.933.449.852.8627725 |
4AB硅烷A1遍180℃ | 13AB硅烷A1遍180℃0.72FF90/10二氧化硅 | 17AB硅烷A1遍170℃2phr DPG0.72FF90/10二氧化硅 | 21AB硅烷A1遍180℃2phr DPG0.72FF90/10二氧化硅 | |
硫化状态中的性能非线性(0-10%)G′初始(MPa)ΔG′(MPa)G″最大(MPa)tanδ最大大应变滞后35%DSA增强M10(MPa)M100(MPa)M300(MPa)M300/M100断裂应力(MPa)断裂伸长率(%) | 3.72.050.430.180.1335.23.49.472.7925.5700 | 4.52.70.530.190.1396.23.79.582.5825.8720 | 4.152.40.490.190.1315.553.9211.52.9327680 | 3.31.70.40.1770.1245.523.911.62.9827670 |
6AB硅烷A1遍160℃0.67FF50/50二氧化硅 | 17AB硅烷A1遍170℃2phrDPG0.72FF90/10二氧化硅 | 22AB硅烷A(75%装载)160℃0.72FF90/10二氧化硅 | 23AB硅烷A(75%装载)170℃2phrDPG0.72FF90/10二氧化硅 | |
硫化状态中的性能非线性(0-10%)G′初始(MPa)ΔG′(MPa)G″最大(MPa)tanδ最大大应变滞后35%DSA增强M10(MPa)M100(MPa)M300(MPa)M300/M100断裂应力(MPa)断裂伸长率(%) | 4.52.80.550.20.1455.793.519.152.620.11754 | 4.152.40.490.190.1315.553.9211.52.8327680 | 4.42.750.520.20.1456.53.6589.52.5925.5710 | 53.20.5750.20.1386.64.0411.542.85626640 |
1ABA-12892遍160℃ | 2ABA-15892遍160℃ | 4AB硅烷A1遍180℃ | 16AB硅烷A1遍170℃6%硅烷C0.72FF90/0二氧化硅 | 21AB硅烷A1遍180℃2phrDPG0.72FF90/10二氧化硅 | 20AB硅烷A1遍170℃3%硅烷C2phrDPG0.72FF90/10二氧化硅 | |
硫化状态中的性能非线性(0-10%)G′初始(MPa)ΔG′(MPa)G″最大(MPa)tanδ最大大应变滞后35%DSA增强M10(MPa)M100(MPa)M300(MPa)M300/M100断裂应力(MPa)断裂伸长率(%) | 3.31.650.380.1820.1295.54.0315.43.8227.5470 | 31.40.380.190.15353.0710.23.3125.6610 | 3.72.060.430.180.1335.23.48.472.7825.5700 | 4.152.50.470.190.1354.933.449.892.8027725 | 3.31.70.40.1770.1245.523.911.63.9827570 | 3.41.50.430.190.135.964.10312.22.9728.5680 |
基本配方 | |||
份数 | 成分 | 产品名称 | 提供商 |
75 | 溶液SBR | SOLFLEX 1216 | Goodyear |
25 | 聚丁二烯 | BUDENE 1207 | Goodyear |
80 | 二氧化硅 | ZEOSIL 1165MP | Rhodia |
32.5 | 加工油 | SUNDEX 8125 | Sun Oil |
2.5 | 氧化锌 | KADOX 720C | Zinc Corp. |
1.0 | 硬脂酸 | INDUSTRENE R | Witco |
2.0 | 6PPD抗氧剂 | SANTOFLEX 13 | Flexvs |
1.5 | 微蜡 | M4067 | Moore & Munger |
3.0 | 炭黑 | N-330 | Huber |
1.4 | 硫 | Rubbermakers 104 | Harwick |
1.7 | CBS | SANTOCURE | Flexvs |
2.0 | DPG | PERKACIT DPGC | Flexvs |
9.7 | 硅烷A | -- | OSi Specialties |
活化剂 | 100%模量,MPa | 300%模量,MPa | 300%/100% |
无 | 2.00 | 10.27 | 5.1 |
0.5phr三氨基双丙胺 | 1.41 | 7.58 | 5.4 |
0.5phr二亚乙基三胺 | 1.55 | 8.57 | 5.5 |
0.5phr三亚乙基胺 | 1.59 | 8.76 | 5.5 |
3.0phr甘油 | 1.79 | 10.27 | 5.7 |
9.0phr甘油 | 1.79 | 10.20 | 5.7 |
9.0phr乙二醇 | 1.86 | 10.93 | 5.9 |
9.0phr三羟甲基丙烷 | 1.76 | 9.96 | 5.7 |
DPG,phr | 无 | 1 | 3 | 无 | 1 | 3 |
8分钟 | ||||||
@165℃ | X | X | X | |||
@175℃ | X | X | X | |||
100%模量,MPa | 1.76 | 1.79 | 1.79 | 1.72 | 1.86 | 1.86 |
300%模量,MPa | 9.89 | 10.69 | 10.72 | 9.82 | 11.65 | 11.65 |
300%/100% | 5.6 | 6.0 | 6.0 | 5.7 | 6.3 | 5.9 |
活化剂 | 8分钟@175℃ | 100%模量,MPa | 300%模量,MPa | 300%/100% |
无 | 是 | 1.69 | 9.24 | 5.5 |
1.0 DPG | 是 | 1.79 | 11.10 | 6.2 |
1.0 TBTD | 是 | 2.48 | 12.86 | 5.2 |
1.0 TBTD | 否 | 2.52 | 14.93 | 5.9 |
1.0 ZBDC | 是 | 2.45 | 13.48 | 5.5 |
1.0 ZBDC | 否 | 2.38 | 12.72 | 5.3 |
0.5硅烷C | 是 | 1.76 | 10.48 | 6.0 |
1.0硅烷C | 是 | 1.83 | 11.65 | 6.4 |
试验号 | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 |
硅烷A | 9.7 | 9.7 | 9.7 | 9.7 | 9.7 | 9.7 | 9.7 | 9.7 | 9.7 |
A-1891 | |||||||||
DPG | 2 | 2 | |||||||
三亚乙基四胺 | 2 | 2 | |||||||
二亚乙基三胺 | 2 | 2 | |||||||
3,B′-亚氨基双-1-丙胺 | 2 | 2 | |||||||
甘油 | |||||||||
二甘醇 | |||||||||
三羟甲基丙烷 | |||||||||
热步骤温度℃ | 170 | 160 | 170 | 160 | 170 | 160 | 170 | 160 | 170 |
门尼粘度@100℃ | |||||||||
ML1+4 | 53 | 55 | 55 | 57 | 57 | 56 | 56 | 58 | 61 |
门尼焦烧@135℃ | |||||||||
Mv | 23 | 25 | 26 | 28 | 29 | 28 | 28 | 30 | 31 |
MS1+,t3,分钟 | 8.4 | 5.9 | 6.3 | 4.4 | 4.5 | 3.6 | 3.2 | 2.6 | 2.9 |
MS1+,t18,分钟 | 10.8 | 8.0 | 8.6 | 5.6 | 5.4 | 4.7 | 4.2 | 3.5 | 3.8 |
ODR@149℃,1°弧,30分钟计时器 | |||||||||
ML,in.-lb. | 6.5 | 6.5 | 6.6 | 6.8 | 7.1 | 6.9 | 6.8 | 7.0 | 2.5 |
MH,in.-lb. | 5.9 | 27.3 | 26.5 | 24.9 | 25.1 | 24.5 | 23.0 | 24.0 | 24.9 |
ts1,分钟 | 5.1 | 3.1 | 4.1 | 2.8 | 2.6 | 2.3 | 2.0 | 1.8 | 1.9 |
t90,分钟 | 9.3 | 6.3 | 7.8 | 7.0 | 7.0 | 8.3 | 10.8 | 9.0 | 9.0 |
试验号 | 10 | 11 | 12 | 13 | 14 | 15 | 16 | 17 |
硅烷A | 9.7 | 9.7 | 9.7 | 9.7 | 9.7 | 9.7 | 8.73 | 7.76 |
A1891 | 0.97 | 1.94 | ||||||
DPG | ||||||||
三亚乙基四胺 | ||||||||
二亚乙基三胺 | ||||||||
亚氨基双丙胺 | ||||||||
甘油 | 2 | 2 | ||||||
二甘醇 | 2 | 2 | ||||||
三羟甲基丙烷 | 2 | 2 | ||||||
热步骤温度C | 160 | 170 | 160 | 170 | 160 | 170 | 170 | 170 |
门尼粘度@100℃ | ||||||||
ML1+4 | 57 | 56 | 54 | 55 | 54 | 57 | 58 | 62 |
门尼焦烧@135℃ | ||||||||
Mv | 26 | 28 | 25 | 27 | 25 | 28 | 20 | 35 |
MS1+,t3,分钟 | 5.4 | 4.7 | 6.6 | 6.6 | 6.9 | 6.8 | 6.8 | 4.5 |
MS1+,t18,分钟 | 7.2 | 6.2 | 8.6 | 8.6 | 8.7 | 8.6 | 8.6 | 5.9 |
ODR@149℃,1°弧,30分钟计时器 | ||||||||
ML,in.-lb. | 6.8 | 6.8 | 6.4 | 6.6 | 6.1 | 6.6 | 7.2 | 7.6 |
MH,in.-lb. | 26.4 | 26.2 | 26.4 | 26.2 | 26.6 | 26.3 | 25.8 | 25.7 |
ts1,分钟 | 3.5 | 3.1 | 4.1 | 4.8 | 4.4 | 4.4 | 4.1 | 3.1 |
t90,分钟 | 6.8 | 6.1 | 7.5 | 7.6 | 7.8 | 7.4 | 8.0 | 6.4 |
试验号 | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 |
物理性能,硫化190@149℃ | |||||||||
硬度,Shore A | 5.3 | 53 | 53 | 50 | 48 | 50 | 47 | 51 | 50 |
伸长率,% | 540 | 560 | 500 | 530 | 500 | 540 | 540 | 570 | 530 |
25%模量,psi | 97 | 105 | 108 | 104 | 104 | 102 | 101 | 106 | 104 |
100%模量,psi | 231 | 246 | 259 | 230 | 236 | 218 | 213 | 225 | 227 |
300%模量,psi | 1392 | 1401 | 1634 | 1403 | 1518 | 1218 | 1304 | 1232 | 1408 |
拉伸,psi | 3520 | 3520 | 3590 | 3610 | 3500 | 3400 | 3450 | 3460 | 3630 |
300%/25% | 14.4 | 13.3 | 15.1 | 13.5 | 14.6 | 11.9 | 12.9 | 11.6 | 13.5 |
300%/100 | 6.0 | 5.7 | 6.3 | 6.1 | 6.4 | 5.6 | 6.1 | 5.5 | 6.2 |
DIN磨耗,mm3 | 97 | 115 | 132 | 137 | 128 | 125 | 157 | 134 | 137 |
生热@212°F,17.5%压缩,143psi,静负荷 | |||||||||
δT,°F | 32 | 27 | 27 | 27 | 27 | 30 | 堆放自 | 堆放自 | 堆放自 |
永久变形,% | 10.0 | 5.4 | 6.3 | 8.4 | 5.3 | 6.5 | 硫化 | 硫化 | 硫化 |
注意:堆放自硫化是在10周老化 | |||||||||
在硫化态的动态性能 | |||||||||
-非线性(0-10%) | |||||||||
G′初始(MPa) | 1.97 | 2.18 | 1.95 | 1.97 | 1.65 | 1.92 | 1.97 | 2.45 | 1.73 |
ΔG′(MPa) | 0.59 | 0.58 | 0.49 | 0.58 | 0.35 | 0.64 | 0.64 | 0.96 | 0.37 |
G″最大(MPa) | 0.192 | 0.191 | 0.168 | 0.178 | 0.143 | 0.185 | 0.204 | 0.137 | 0.146 |
tanδ最大 | 0.119 | 0.18 | 0.1 | 0.108 | 0.096 | 0.115 | 0.117 | 0.271 | 0.097 |
-大应变滞后 | |||||||||
35%DSA | 0.090 | 0.076 | 0.072 | 0.075 | 0.075 | 0.086 | 0.088 | 0.094 | 0.075 |
试验号 | 10 | 11 | 12 | 13 | 14 | 15 | 16 | 17 |
物理性能,硫化190@149℃ | ||||||||
硬度,Shore A | 52 | 52 | 52 | 52 | 53 | 52 | 51 | 52 |
伸长率,% | 530 | 450 | 530 | 460 | 520 | 460 | 450 | 440 |
25%模量,psi | 115 | 112 | 110 | 112 | 114 | 109 | 103 | 105 |
100%模量,psi | 257 | 275 | 254 | 277 | 271 | 269 | 255 | 259 |
300%模量,psi | 1509 | 1784 | 1533 | 1768 | 1579 | 1739 | 1666 | 1753 |
拉伸,psi | 3500 | 3290 | 3630 | 3430 | 3380 | 3390 | 3110 | 3260 |
300%/25% | 13.1 | 15.9 | 13.9 | 15.8 | 13.9 | 16.0 | 16.2 | 16.7 |
300%/100 | 5.9 | 6.5 | 6.0 | 6.4 | 5.8 | 6.5 | 6.5 | 6.8 |
DIN磨耗,mm3 | ||||||||
生热@212°F,17.5%压缩,143psi,静负荷 | ||||||||
δT,°F | 28 | 29 | 29 | 27 | 27 | 26 | 29 | 堆放自 |
永久变形,% | 5.2 | 6.8 | 6.5 | 5.3 | 5.4 | 5.1 | 5.4 | 硫化 |
在硫化态的动态性能 | ||||||||
-非线性(0-10%) | ||||||||
G′初始(MPa) | 1.93 | 1.95 | 2.06 | 1.68 | 2.30 | 1.51 | 1.62 | 2.05 |
ΔG′(MPa) | 0.44 | 0.53 | 0.62 | 0.32 | 0.79 | 0.23 | 0.38 | 0.72 |
G″最大(MPa) | 0.160 | 0.184 | 0.193 | 0.142 | 0.23 | 0.126 | 0.155 | 0.198 |
tanδ最大 | 0.096 | 0.113 | 0.166 | 0.095 | 0.127 | 0.091 | 0.111 | 0.122 |
-大应变滞后 | ||||||||
35%DSA | 0.078 | 0.086 | 0.083 | 0.078 | 0.087 | 0.080 | 0.091 | 0.092 |
Claims (20)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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US09/736,301 US6635700B2 (en) | 2000-12-15 | 2000-12-15 | Mineral-filled elastomer compositions |
US09/736,301 | 2000-12-15 |
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CN1247687C CN1247687C (zh) | 2006-03-29 |
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US (1) | US6635700B2 (zh) |
EP (1) | EP1341843B2 (zh) |
KR (1) | KR100914092B1 (zh) |
CN (1) | CN1247687C (zh) |
AT (1) | ATE351887T1 (zh) |
BR (1) | BR0116153B1 (zh) |
CA (1) | CA2430251C (zh) |
CZ (1) | CZ308323B6 (zh) |
DE (1) | DE60126135T3 (zh) |
ES (1) | ES2278816T5 (zh) |
PT (1) | PT1341843E (zh) |
WO (1) | WO2002048256A2 (zh) |
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- 2001-11-14 CA CA2430251A patent/CA2430251C/en not_active Expired - Lifetime
- 2001-11-14 CZ CZ2003-1628A patent/CZ308323B6/cs not_active IP Right Cessation
- 2001-11-14 AT AT01995168T patent/ATE351887T1/de not_active IP Right Cessation
- 2001-11-14 PT PT01995168T patent/PT1341843E/pt unknown
- 2001-11-14 EP EP01995168.0A patent/EP1341843B2/en not_active Expired - Lifetime
- 2001-11-14 BR BRPI0116153-9A patent/BR0116153B1/pt not_active IP Right Cessation
- 2001-11-14 DE DE60126135.6T patent/DE60126135T3/de not_active Expired - Lifetime
- 2001-11-14 ES ES01995168.0T patent/ES2278816T5/es not_active Expired - Lifetime
- 2001-11-14 WO PCT/US2001/043498 patent/WO2002048256A2/en active IP Right Grant
- 2001-11-14 CN CNB018205798A patent/CN1247687C/zh not_active Expired - Lifetime
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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 |
CN101426809B (zh) * | 2006-02-21 | 2013-11-06 | 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 |
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 |
CN102307942A (zh) * | 2008-12-22 | 2012-01-04 | 米其林技术公司 | 含有封端的巯基硅烷偶联剂的橡胶组合物 |
CN102300917B (zh) * | 2008-12-22 | 2013-09-04 | 米其林集团总公司 | 含有封端的巯基硅烷偶联剂的橡胶化合物 |
CN102307884B (zh) * | 2008-12-22 | 2015-01-07 | 米其林集团总公司 | 封端的巯基硅烷偶联剂 |
CN111138471A (zh) * | 2019-12-18 | 2020-05-12 | 怡维怡橡胶研究院有限公司 | 一种硫代酸根封端巯基硅烷偶联剂及其合成方法和应用 |
CN111233916A (zh) * | 2020-02-06 | 2020-06-05 | 南京曙光精细化工有限公司 | 长碳链含硫硅烷偶联剂及其制备方法和应用 |
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ES2278816T3 (es) | 2007-08-16 |
EP1341843B2 (en) | 2016-03-23 |
CA2430251A1 (en) | 2002-06-20 |
DE60126135T2 (de) | 2007-05-16 |
DE60126135T3 (de) | 2016-08-11 |
BR0116153B1 (pt) | 2011-05-03 |
CA2430251C (en) | 2011-05-31 |
ATE351887T1 (de) | 2007-02-15 |
CZ20031628A3 (cs) | 2003-09-17 |
ES2278816T5 (es) | 2016-06-27 |
BR0116153A (pt) | 2004-01-13 |
DE60126135D1 (de) | 2007-03-08 |
WO2002048256A2 (en) | 2002-06-20 |
EP1341843B1 (en) | 2007-01-17 |
EP1341843A2 (en) | 2003-09-10 |
PT1341843E (pt) | 2007-02-28 |
CN1247687C (zh) | 2006-03-29 |
US20020115767A1 (en) | 2002-08-22 |
US6635700B2 (en) | 2003-10-21 |
KR100914092B1 (ko) | 2009-08-27 |
KR20030066708A (ko) | 2003-08-09 |
WO2002048256A3 (en) | 2003-01-30 |
CZ308323B6 (cs) | 2020-05-13 |
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