CN1738856A - 用于轮胎胎面的橡胶化合物及其制备方法 - Google Patents
用于轮胎胎面的橡胶化合物及其制备方法 Download PDFInfo
- Publication number
- CN1738856A CN1738856A CN200480002469.3A CN200480002469A CN1738856A CN 1738856 A CN1738856 A CN 1738856A CN 200480002469 A CN200480002469 A CN 200480002469A CN 1738856 A CN1738856 A CN 1738856A
- Authority
- CN
- China
- Prior art keywords
- initiator
- crosslinkable
- rubber combination
- crosslinked rubber
- mol
- 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 59
- 239000005060 rubber Substances 0.000 title claims abstract description 40
- 238000000034 method Methods 0.000 title claims description 36
- 238000002360 preparation method Methods 0.000 title claims description 18
- 150000001875 compounds Chemical class 0.000 title abstract description 7
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 54
- 239000003999 initiator Substances 0.000 claims abstract description 38
- 239000000178 monomer Substances 0.000 claims abstract description 38
- 229920003244 diene elastomer Polymers 0.000 claims abstract description 35
- 239000012763 reinforcing filler Substances 0.000 claims abstract description 31
- 150000001993 dienes Chemical class 0.000 claims abstract description 22
- 239000000806 elastomer Substances 0.000 claims abstract description 19
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 10
- 239000002904 solvent Substances 0.000 claims abstract description 10
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 9
- 238000006243 chemical reaction Methods 0.000 claims abstract description 9
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 9
- 239000000203 mixture Substances 0.000 claims description 86
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 71
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 38
- 229920002554 vinyl polymer Polymers 0.000 claims description 37
- 239000000377 silicon dioxide Substances 0.000 claims description 32
- -1 phosphorous acid ester Chemical class 0.000 claims description 30
- 239000003054 catalyst Substances 0.000 claims description 29
- 229960001866 silicon dioxide Drugs 0.000 claims description 28
- 235000012239 silicon dioxide Nutrition 0.000 claims description 28
- 150000003839 salts Chemical class 0.000 claims description 18
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical group CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 claims description 16
- 238000006116 polymerization reaction Methods 0.000 claims description 16
- 125000001931 aliphatic group Chemical group 0.000 claims description 15
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 claims description 12
- 239000003153 chemical reaction reagent Substances 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- 229910052744 lithium Inorganic materials 0.000 claims description 11
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 10
- 125000002723 alicyclic group Chemical group 0.000 claims description 10
- 229910052708 sodium Inorganic materials 0.000 claims description 9
- 239000011734 sodium Substances 0.000 claims description 9
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 8
- 229910052783 alkali metal Inorganic materials 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 150000004985 diamines Chemical class 0.000 claims description 2
- 150000002191 fatty alcohols Chemical class 0.000 claims description 2
- 238000010539 anionic addition polymerization reaction Methods 0.000 claims 2
- 229920002587 poly(1,3-butadiene) polymer Polymers 0.000 claims 1
- 159000000000 sodium salts Chemical class 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract description 8
- 125000000129 anionic group Chemical group 0.000 abstract description 3
- 125000005842 heteroatom Chemical group 0.000 abstract description 2
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 42
- 239000002174 Styrene-butadiene Substances 0.000 description 41
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 23
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 22
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 14
- 239000006229 carbon black Substances 0.000 description 11
- 238000005987 sulfurization reaction Methods 0.000 description 9
- PIZNQHDTOZMVBH-UHFFFAOYSA-N thionylimide Chemical compound N=S=O PIZNQHDTOZMVBH-UHFFFAOYSA-N 0.000 description 9
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 8
- 239000011159 matrix material Substances 0.000 description 8
- 239000012764 mineral filler Substances 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 6
- 239000010692 aromatic oil Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- 239000000945 filler Substances 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- 230000009466 transformation Effects 0.000 description 5
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 239000005864 Sulphur Substances 0.000 description 4
- 230000003064 anti-oxidating effect Effects 0.000 description 4
- 238000013459 approach Methods 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 238000010924 continuous production Methods 0.000 description 4
- 230000008878 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical group C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 4
- 239000005077 polysulfide Substances 0.000 description 4
- 229920001021 polysulfide Polymers 0.000 description 4
- 150000008117 polysulfides Polymers 0.000 description 4
- 230000001105 regulatory effect Effects 0.000 description 4
- 229910000077 silane Inorganic materials 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 235000019587 texture Nutrition 0.000 description 4
- OWRCNXZUPFZXOS-UHFFFAOYSA-N 1,3-diphenylguanidine Chemical compound C=1C=CC=CC=1NC(=N)NC1=CC=CC=C1 OWRCNXZUPFZXOS-UHFFFAOYSA-N 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- 241001441571 Hiodontidae Species 0.000 description 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 3
- 235000021355 Stearic acid Nutrition 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- JLUFWMXJHAVVNN-UHFFFAOYSA-N methyltrichlorosilane Chemical compound C[Si](Cl)(Cl)Cl JLUFWMXJHAVVNN-UHFFFAOYSA-N 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 239000008117 stearic acid Substances 0.000 description 3
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- 238000004073 vulcanization Methods 0.000 description 3
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 2
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- 244000043261 Hevea brasiliensis Species 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000005055 methyl trichlorosilane Substances 0.000 description 2
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 2
- 229920003052 natural elastomer Polymers 0.000 description 2
- 229920001194 natural rubber Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000001103 potassium chloride Substances 0.000 description 2
- 235000011164 potassium chloride Nutrition 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 238000010008 shearing Methods 0.000 description 2
- 238000001542 size-exclusion chromatography Methods 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000003643 water by type Substances 0.000 description 2
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- RYPKRALMXUUNKS-UHFFFAOYSA-N 2-Hexene Natural products CCCC=CC RYPKRALMXUUNKS-UHFFFAOYSA-N 0.000 description 1
- PJXJBPMWCKMWLS-UHFFFAOYSA-N 2-methyl-3-methylidenepent-1-ene Chemical compound CCC(=C)C(C)=C PJXJBPMWCKMWLS-UHFFFAOYSA-N 0.000 description 1
- AIDLAEPHWROGFI-UHFFFAOYSA-N 2-methylbenzene-1,3-dicarboxylic acid Chemical compound CC1=C(C(O)=O)C=CC=C1C(O)=O AIDLAEPHWROGFI-UHFFFAOYSA-N 0.000 description 1
- IKEHOXWJQXIQAG-UHFFFAOYSA-N 2-tert-butyl-4-methylphenol Chemical compound CC1=CC=C(O)C(C(C)(C)C)=C1 IKEHOXWJQXIQAG-UHFFFAOYSA-N 0.000 description 1
- CXURGFRDGROIKG-UHFFFAOYSA-N 3,3-bis(chloromethyl)oxetane Chemical compound ClCC1(CCl)COC1 CXURGFRDGROIKG-UHFFFAOYSA-N 0.000 description 1
- DXIJHCSGLOHNES-UHFFFAOYSA-N 3,3-dimethylbut-1-enylbenzene Chemical compound CC(C)(C)C=CC1=CC=CC=C1 DXIJHCSGLOHNES-UHFFFAOYSA-N 0.000 description 1
- OAOZZYBUAWEDRA-UHFFFAOYSA-N 3,4-dimethylidenehexane Chemical compound CCC(=C)C(=C)CC OAOZZYBUAWEDRA-UHFFFAOYSA-N 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-OUBTZVSYSA-N Carbon-13 Chemical compound [13C] OKTJSMMVPCPJKN-OUBTZVSYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- 239000006237 Intermediate SAF Substances 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 1
- YLFSKHFWQGRUCI-UHFFFAOYSA-N [Li]CCc1ccccc1 Chemical compound [Li]CCc1ccccc1 YLFSKHFWQGRUCI-UHFFFAOYSA-N 0.000 description 1
- MCEBKLYUUDGVMD-UHFFFAOYSA-N [SiH3]S(=O)=O Chemical compound [SiH3]S(=O)=O MCEBKLYUUDGVMD-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910021502 aluminium hydroxide Inorganic materials 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000011805 ball Substances 0.000 description 1
- XZKRXPZXQLARHH-UHFFFAOYSA-N buta-1,3-dienylbenzene Chemical compound C=CC=CC1=CC=CC=C1 XZKRXPZXQLARHH-UHFFFAOYSA-N 0.000 description 1
- NPAXBRSUVYCZGM-UHFFFAOYSA-N carbonic acid;propane-1,2-diol Chemical compound OC(O)=O.CC(O)CO NPAXBRSUVYCZGM-UHFFFAOYSA-N 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- LEKSIJZGSFETSJ-UHFFFAOYSA-N cyclohexane;lithium Chemical compound [Li]C1CCCCC1 LEKSIJZGSFETSJ-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- DPUXQWOMYBMHRN-UHFFFAOYSA-N hexa-2,3-diene Chemical compound CCC=C=CC DPUXQWOMYBMHRN-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical group [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical group [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 1
- XBEREOHJDYAKDA-UHFFFAOYSA-N lithium;propane Chemical group [Li+].CC[CH2-] XBEREOHJDYAKDA-UHFFFAOYSA-N 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- UIUXUFNYAYAMOE-UHFFFAOYSA-N methylsilane Chemical compound [SiH3]C UIUXUFNYAYAMOE-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 150000002900 organolithium compounds Chemical class 0.000 description 1
- 150000001282 organosilanes Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 229920003192 poly(bis maleimide) Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- OSFBJERFMQCEQY-UHFFFAOYSA-N propylidene Chemical group [CH]CC OSFBJERFMQCEQY-UHFFFAOYSA-N 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000010057 rubber processing Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 125000005353 silylalkyl group Chemical group 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- NESLVXDUKMNMOG-UHFFFAOYSA-N triethoxy-(propyltetrasulfanyl)silane Chemical compound CCCSSSS[Si](OCC)(OCC)OCC NESLVXDUKMNMOG-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F36/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F36/02—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F36/04—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
-
- 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
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
- C08C19/30—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule
- C08C19/42—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule reacting with metals or metal-containing groups
- C08C19/44—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule reacting with metals or metal-containing groups of polymers containing metal atoms exclusively at one or both ends of the skeleton
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F297/00—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer
- C08F297/02—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer using a catalyst of the anionic type
- C08F297/04—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer using a catalyst of the anionic type polymerising vinyl aromatic monomers and conjugated dienes
- C08F297/044—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer using a catalyst of the anionic type polymerising vinyl aromatic monomers and conjugated dienes using a coupling agent
-
- 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
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)
- Inorganic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Description
化学位移 | 指定的结构-观察的碳数目 |
145-140.6116.6-113.2126.5-124.9132.9-126.9145-140.6147.1-145113.2-111 | V-3,VCP-6V-4S-6S-4,S-5,S-7,S-8C-2,C-3,T-2,T-3V-3,VCP-6S-3VCP-7 |
组合物 | 1(“对照物”) | 2(本发明) |
ML(1+4)在100℃下“橡胶” | 67 | 55 |
非硫化状态下的性能: | ||
ML(1+4)在100℃下“混合物” | 97 | 82 |
硫化状态下的性能: | ||
Shore | 65 | 65 |
ME10 | 5.6 | 5.8 |
ME100 | 1.8 | 1.9 |
ME300 | 2.3 | 2.5 |
ME300/ME100 | 1.3 | 1.3 |
在60℃下的损失 | 24.3 | 27.3 |
作为形变函数的动态性能 | ||
在23℃下的δG* | 3.11 | 3.54 |
在23℃下的Tanδmax. | 0.347 | 0.415 |
作为温度函数的动态性能 | ||
动态Tg(℃) | -16 | -11 |
在Tg下的Tanδ | 0.75 | 0.77 |
组合物 | 1(“对照物”) | 3(本发明) |
ML(1+4)在100℃下“像胶” | 67 | 48 |
非硫化状态下的性能: | ||
ML(1+4)在100℃下“混合物” | 97 | 71 |
硫化状态下的性能: | ||
Shore | 65 | 65 |
ME10 | 5.6 | 5.8 |
ME100 | 1.8 | 1.9 |
ME300 | 2.3 | 2.5 |
ME300/ME100 | 1.3 | 1.3 |
在60℃下的损失 | 24.3 | 27.0 |
作为形变函数的动态性能 | ||
在23℃下的δG* | 3.11 | 3.59 |
在23℃下的Tanδmax. | 0.347 | 0.405 |
作为温度函数的动态性能 | ||
动态Tg(℃) | -16 | -13 |
在Tg下的Tanδ | 0.75 | 0.72 |
组合物 | 4(本发明) | 5(“对照物”) |
ML(1+4)在100℃下“橡胶” | 43 | 43 |
非硫化状态下的性能: | ||
ML(1+4)在100℃下“混合物” | 61 | 55 |
硫化状态下的性能: | ||
Shore | 59.3 | 59.1 |
ME10 | 4.8 | 4.5 |
ME100 | 1.5 | 1.4 |
ME300 | 1.5 | 1.5 |
ME300/ME 100 | 1.0 | 1.08 |
在60℃下的损失 | 35.0 | 35.1 |
作为形变函数的动态性能 | ||
在23℃下的δG* | 1.45 | 1.15 |
在23℃下的Tanδmax. | 0.257 | 0.238 |
作为温度函数的动态性能 | ||
动态Tg(℃) | -15 | -15 |
在Tg下的Tanδ | 1.11 | 1.19 |
以MPa计在50℃下的E’ | 5.5 | 5.7 |
以MPa计在50℃下的E” | 0.83 | 0.86 |
Claims (28)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0300743 | 2003-01-20 | ||
FR0300743 | 2003-01-20 | ||
PCT/EP2004/000280 WO2004065478A1 (fr) | 2003-01-20 | 2004-01-16 | Composition de caoutchouc pour bande de roulement de pneumatique et procede de preparation |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1738856A true CN1738856A (zh) | 2006-02-22 |
CN1738856B CN1738856B (zh) | 2010-06-23 |
Family
ID=32749534
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN200480002469.3A Expired - Fee Related CN1738856B (zh) | 2003-01-20 | 2004-01-16 | 用于轮胎胎面的橡胶化合物及其制备方法 |
Country Status (5)
Country | Link |
---|---|
US (3) | US7470743B2 (zh) |
EP (1) | EP1587867B1 (zh) |
JP (1) | JP4741457B2 (zh) |
CN (1) | CN1738856B (zh) |
WO (1) | WO2004065478A1 (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106536818A (zh) * | 2014-06-12 | 2017-03-22 | 米其林集团总公司 | 原位橡胶处理并包含含有腐蚀抑制剂的涂胶组合物的缆线 |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP4716756B2 (ja) * | 2005-03-03 | 2011-07-06 | 旭化成ケミカルズ株式会社 | ランダム共重合体の製造方法 |
FR2915202B1 (fr) * | 2007-04-18 | 2009-07-17 | Michelin Soc Tech | Elastomere dienique couple monomodal possedant une fonction silanol en milieu de chaine, son procede d'obtention et composition de caoutchouc le contenant. |
HUE031642T2 (en) * | 2011-03-04 | 2017-07-28 | Trinseo Europe Gmbh | Styrene-butadiene rubber with high styrene and high vinyl content and methods for its production |
WO2020235619A1 (ja) | 2019-05-22 | 2020-11-26 | 株式会社クラレ | ジエン系ゴム及びゴム組成物 |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3301840A (en) * | 1964-09-17 | 1967-01-31 | Phillips Petroleum Co | Preparation of polymers of conjugated dienes using organolithium/polar compound catalyst systems |
US3966691A (en) * | 1973-07-12 | 1976-06-29 | The Firestone Tire & Rubber Company | Polymerization of conjugated dienes with starved lithium, potassium or sodium catalyst |
DE3724870A1 (de) * | 1987-07-28 | 1989-02-09 | Huels Chemische Werke Ag | Verfahren zur herstellung von polymerisaten auf basis von konjugierten dienen und ggf. monovinylaromatischen verbindungen |
CN1044812C (zh) * | 1993-02-17 | 1999-08-25 | 中国科学院长春应用化学研究所 | 环化顺1,4丁戊无规共聚物 |
US5534592A (en) * | 1995-09-22 | 1996-07-09 | The Goodyear Tire & Rubber Company | High performance blend for tire treads |
US5677402A (en) | 1995-09-22 | 1997-10-14 | The Goodyear Tire & Rubber Company | Process for preparing 3,4-polyisoprene rubber |
US6140434A (en) * | 1999-01-08 | 2000-10-31 | The Goodyear Tire & Rubber Company | Synthesis of high vinyl rubber |
EP1423442B1 (fr) * | 2001-07-16 | 2012-09-12 | Compagnie Generale Des Etablissements Michelin | Procédé de préparation en continu d'un élastomère diénique à unités vinyliques cycliques. |
-
2004
- 2004-01-16 JP JP2006500577A patent/JP4741457B2/ja not_active Expired - Fee Related
- 2004-01-16 CN CN200480002469.3A patent/CN1738856B/zh not_active Expired - Fee Related
- 2004-01-16 EP EP04702669A patent/EP1587867B1/fr not_active Expired - Lifetime
- 2004-01-16 WO PCT/EP2004/000280 patent/WO2004065478A1/fr active Application Filing
-
2005
- 2005-07-19 US US11/183,912 patent/US7470743B2/en not_active Expired - Fee Related
-
2008
- 2008-07-07 US US12/216,531 patent/US20080275160A1/en not_active Abandoned
- 2008-07-07 US US12/216,530 patent/US20080275159A1/en not_active Abandoned
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106536818A (zh) * | 2014-06-12 | 2017-03-22 | 米其林集团总公司 | 原位橡胶处理并包含含有腐蚀抑制剂的涂胶组合物的缆线 |
Also Published As
Publication number | Publication date |
---|---|
EP1587867B1 (fr) | 2012-05-23 |
US20080275160A1 (en) | 2008-11-06 |
CN1738856B (zh) | 2010-06-23 |
US20060009568A1 (en) | 2006-01-12 |
US7470743B2 (en) | 2008-12-30 |
WO2004065478A1 (fr) | 2004-08-05 |
US20080275159A1 (en) | 2008-11-06 |
JP4741457B2 (ja) | 2011-08-03 |
JP2006515897A (ja) | 2006-06-08 |
EP1587867A1 (fr) | 2005-10-26 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN1140570C (zh) | 可用作轮胎胎面的橡胶组合物 | |
CN1249145C (zh) | 橡胶组合物 | |
CN1180009C (zh) | 用于轮胎的橡胶组合物 | |
CN1214069C (zh) | 以聚有机硅氧烷为偶联剂及白色填料增强的二烯橡胶组合物 | |
CN1780859A (zh) | 获得沿链含有官能团的接枝弹性体的方法和橡胶组合物 | |
CN1202164C (zh) | 可硫化的橡胶组合物、含有硫化橡胶组合物的轮胎和由硫化橡胶组合物组成的轮胎胎面 | |
CN1256374C (zh) | 基于多硫化烷氧基硅烷、烯胺和胍衍生物的偶联体系及其应用,包含该偶联体系的橡胶组合物及其应用 | |
CN1051320C (zh) | 含改性环状单体单元的聚合物 | |
CN1239592C (zh) | 含增强无机填料和偶联系统(无机填料/弹性体)的轮胎用橡胶组合物 | |
CN1217985C (zh) | 基于表面固着二氧化硅的炭黑和烷氧基硅烷官能化的二烯聚合物的橡胶组合物 | |
CN1109713C (zh) | 用于外胎的橡胶组合物 | |
CN1263792C (zh) | 包含多官能有机硅烷作为偶联剂的橡胶组合物 | |
CN1656153A (zh) | 共轭二烯类橡胶、其制造方法及橡胶组合物 | |
CN1304433C (zh) | 制备改性聚合物的方法、通过该方法获得的改性聚合物和橡胶组合物 | |
CN1437635A (zh) | 轮胎行驶胎面的组合物以及它的制造方法 | |
CN1599758A (zh) | 改性聚合物的制备方法、利用该方法获得的改性聚合物以及橡胶组合物 | |
CN1578796A (zh) | 轮胎胎面组合物用嵌段共聚物的制备方法,和这样的共聚物 | |
CN1993415A (zh) | 橡胶组合物 | |
CN1592760A (zh) | 共轭二烯聚合物、其制备方法和包含该共轭二烯聚合物的橡胶组合物 | |
CN1414993A (zh) | 用于轮胎的含有通过热制动游离基引发剂而活化的偶联剂(白色填料/二烯弹性体)的橡胶组合物 | |
CN1441821A (zh) | 含有多官能聚有机硅氧烷作为偶联剂的轮胎橡胶组合物 | |
CN1547601A (zh) | 采用具有低比表面积的二氧化硅增强的轮胎胎面 | |
CN1561367A (zh) | 采用具有非常低比表面积的二氧化硅增强的轮胎胎面 | |
CN1639203A (zh) | 纳米颗粒制备和应用 | |
CN1576279A (zh) | 有机硅化合物 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
EE01 | Entry into force of recordation of patent licensing contract |
Assignee: Shanghai Michelin tire Limited by Share Ltd Assignor: Michelin research and technology Limited by Share Ltd|Michelin technology company Contract fulfillment period: 2007.01.31 to 2026.12.13 Contract record no.: 2007990000027 Denomination of invention: Rubber compound for tire tread and preparation method thereof Granted publication date: unauthorized License type: General permission Record date: 20070813 Assignee: Shanghai Michelin tire Limited by Share Ltd Assignor: Michelin research and technology Limited by Share Ltd|Michelin technology company Contract fulfillment period: 2007.01.31 to 2026.12.13 Contract record no.: 2007990000027 Denomination of invention: Rubber compound for tire tread and preparation method thereof Granted publication date: unauthorized License type: General permission Record date: 20070813 |
|
LIC | Patent licence contract for exploitation submitted for record |
Free format text: COMMON LICENCE; TIME LIMIT OF IMPLEMENTING CONTACT: 2007.1.31 TO 2026.12.13 Name of requester: SHANGHAI MIQILIN BOOST TYRE CO., LTD. Effective date: 20070813 |
|
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
ASS | Succession or assignment of patent right |
Owner name: COMPAGNIE GENERALE DES ETABLISSEMENTS MICHELIN Free format text: FORMER OWNER: MICHELIN TECHNIQUE S.A. Effective date: 20121114 |
|
C41 | Transfer of patent application or patent right or utility model | ||
TR01 | Transfer of patent right |
Effective date of registration: 20121114 Address after: French Clermont Ferrand Patentee after: Compagnie General Des Etablissements Michelin Patentee after: Michelin Research & Technology Co., Ltd. Address before: French Clermont Ferrand Patentee before: Michelin Co., Ltd. Patentee before: Michelin Research & Technology Co., Ltd. |
|
CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20100623 Termination date: 20170116 |
|
CF01 | Termination of patent right due to non-payment of annual fee |