JP5466475B2 - ゴム組成物およびそれを用いたスタッドレスタイヤ - Google Patents
ゴム組成物およびそれを用いたスタッドレスタイヤ Download PDFInfo
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- JP5466475B2 JP5466475B2 JP2009238515A JP2009238515A JP5466475B2 JP 5466475 B2 JP5466475 B2 JP 5466475B2 JP 2009238515 A JP2009238515 A JP 2009238515A JP 2009238515 A JP2009238515 A JP 2009238515A JP 5466475 B2 JP5466475 B2 JP 5466475B2
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- styrene
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- carbon atoms
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- 229920001971 elastomer Polymers 0.000 title claims description 33
- 239000005060 rubber Substances 0.000 title claims description 33
- 239000000203 mixture Substances 0.000 title claims description 27
- -1 diene compounds Chemical class 0.000 claims description 54
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 47
- 229920000642 polymer Polymers 0.000 claims description 41
- 125000004432 carbon atom Chemical group C* 0.000 claims description 36
- 239000000377 silicon dioxide Substances 0.000 claims description 23
- 239000001257 hydrogen Substances 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000006229 carbon black Substances 0.000 claims description 15
- 125000001931 aliphatic group Chemical group 0.000 claims description 14
- 125000002723 alicyclic group Chemical group 0.000 claims description 10
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 10
- 229920006395 saturated elastomer Polymers 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 238000007334 copolymerization reaction Methods 0.000 claims description 3
- 125000006413 ring segment Chemical group 0.000 claims description 3
- 244000043261 Hevea brasiliensis Species 0.000 claims description 2
- 229920003052 natural elastomer Polymers 0.000 claims description 2
- 229920001194 natural rubber Polymers 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 56
- 229920001084 poly(chloroprene) Polymers 0.000 description 34
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 29
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
- 239000000178 monomer Substances 0.000 description 18
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 15
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 238000013329 compounding Methods 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 9
- 239000006087 Silane Coupling Agent Substances 0.000 description 9
- 239000003607 modifier Substances 0.000 description 9
- 238000006116 polymerization reaction Methods 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 150000002430 hydrocarbons Chemical group 0.000 description 5
- 150000002642 lithium compounds Chemical class 0.000 description 5
- 229920002857 polybutadiene Polymers 0.000 description 5
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 5
- 238000001179 sorption measurement Methods 0.000 description 5
- 239000005062 Polybutadiene Substances 0.000 description 4
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 4
- 239000003505 polymerization initiator Substances 0.000 description 4
- VXEGSRKPIUDPQT-UHFFFAOYSA-N 4-[4-(4-methoxyphenyl)piperazin-1-yl]aniline Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C=CC(N)=CC=2)CC1 VXEGSRKPIUDPQT-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000003712 anti-aging effect Effects 0.000 description 3
- 229920003244 diene elastomer Polymers 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical group 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000005049 silicon tetrachloride Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-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
- RYPKRALMXUUNKS-UHFFFAOYSA-N 2-Hexene Natural products CCCC=CC RYPKRALMXUUNKS-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- 229920000459 Nitrile rubber Polymers 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 125000004036 acetal group Chemical group 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- 229920005549 butyl rubber Polymers 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 125000000000 cycloalkoxy group Chemical group 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 125000006534 ethyl amino methyl group Chemical group [H]N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
- 229920003049 isoprene rubber Polymers 0.000 description 2
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 238000006011 modification reaction Methods 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pentene-2 Natural products CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 2
- 239000012744 reinforcing agent Substances 0.000 description 2
- 230000003014 reinforcing effect Effects 0.000 description 2
- 238000001226 reprecipitation Methods 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 150000003377 silicon compounds Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 229920003048 styrene butadiene rubber Polymers 0.000 description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 2
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 2
- MMZPUXVBQAQQDQ-UHFFFAOYSA-N triethoxy(2-pyridin-4-ylethyl)silane Chemical compound CCO[Si](OCC)(OCC)CCC1=CC=NC=C1 MMZPUXVBQAQQDQ-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
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 2
- 238000004073 vulcanization Methods 0.000 description 2
- AHAREKHAZNPPMI-AATRIKPKSA-N (3e)-hexa-1,3-diene Chemical compound CC\C=C\C=C AHAREKHAZNPPMI-AATRIKPKSA-N 0.000 description 1
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- HIACAHMKXQESOV-UHFFFAOYSA-N 1,2-bis(prop-1-en-2-yl)benzene Chemical compound CC(=C)C1=CC=CC=C1C(C)=C HIACAHMKXQESOV-UHFFFAOYSA-N 0.000 description 1
- WZDBFKKBMMGPTK-UHFFFAOYSA-N 1-[2-(4-ethenylphenyl)ethyl]-2,2,6,6-tetramethylpiperidine Chemical compound CC1(C)CCCC(C)(C)N1CCC1=CC=C(C=C)C=C1 WZDBFKKBMMGPTK-UHFFFAOYSA-N 0.000 description 1
- CHPMVJPDQCNCFY-UHFFFAOYSA-N 1-[2-(4-ethenylphenyl)ethyl]-2,5-dimethylpyrrolidine Chemical compound CC1CCC(C)N1CCC1=CC=C(C=C)C=C1 CHPMVJPDQCNCFY-UHFFFAOYSA-N 0.000 description 1
- RMBKOBKVSZTIDZ-UHFFFAOYSA-N 1-[2-(4-ethenylphenyl)ethyl]-2,6-dimethylpiperidine Chemical compound CC1CCCC(C)N1CCC1=CC=C(C=C)C=C1 RMBKOBKVSZTIDZ-UHFFFAOYSA-N 0.000 description 1
- KEJHIDWLEDKRGI-UHFFFAOYSA-N 1-[2-(4-ethenylphenyl)ethyl]-2-methylpiperidine Chemical compound CC1CCCCN1CCC1=CC=C(C=C)C=C1 KEJHIDWLEDKRGI-UHFFFAOYSA-N 0.000 description 1
- HCJTZFUUMGEKDY-UHFFFAOYSA-N 1-[2-(4-ethenylphenyl)ethyl]-3,3-dimethylpiperidine Chemical compound C1C(C)(C)CCCN1CCC1=CC=C(C=C)C=C1 HCJTZFUUMGEKDY-UHFFFAOYSA-N 0.000 description 1
- AXBHTDXHQFUSLQ-UHFFFAOYSA-N 1-[2-(4-ethenylphenyl)ethyl]-3,5-dimethylpiperidine Chemical compound C1C(C)CC(C)CN1CCC1=CC=C(C=C)C=C1 AXBHTDXHQFUSLQ-UHFFFAOYSA-N 0.000 description 1
- LMQOXXLNYSXRTM-UHFFFAOYSA-N 1-[2-(4-ethenylphenyl)ethyl]-3-methylpiperidine Chemical compound C1C(C)CCCN1CCC1=CC=C(C=C)C=C1 LMQOXXLNYSXRTM-UHFFFAOYSA-N 0.000 description 1
- PZELNDZORCHPLO-UHFFFAOYSA-N 1-[2-(4-ethenylphenyl)ethyl]-4-methylpiperidine Chemical compound C1CC(C)CCN1CCC1=CC=C(C=C)C=C1 PZELNDZORCHPLO-UHFFFAOYSA-N 0.000 description 1
- BQYGINUOHFWTKK-UHFFFAOYSA-N 1-[2-(4-ethenylphenyl)ethyl]-4-piperidin-1-ylpiperidine Chemical compound C1=CC(C=C)=CC=C1CCN1CCC(N2CCCCC2)CC1 BQYGINUOHFWTKK-UHFFFAOYSA-N 0.000 description 1
- HKFLEZPANRHUCD-UHFFFAOYSA-N 1-[2-(4-ethenylphenyl)ethyl]-4-pyrrolidin-1-ylpiperidine Chemical compound C1=CC(C=C)=CC=C1CCN1CCC(N2CCCC2)CC1 HKFLEZPANRHUCD-UHFFFAOYSA-N 0.000 description 1
- YERUMMZWNFPZKH-UHFFFAOYSA-N 1-[2-(4-ethenylphenyl)ethyl]-n,n,2,2,6,6-hexamethylpiperidin-4-amine Chemical compound CC1(C)CC(N(C)C)CC(C)(C)N1CCC1=CC=C(C=C)C=C1 YERUMMZWNFPZKH-UHFFFAOYSA-N 0.000 description 1
- GRVAGTQLVKBPLL-UHFFFAOYSA-N 1-[2-(4-ethenylphenyl)ethyl]azepane Chemical compound C1=CC(C=C)=CC=C1CCN1CCCCCC1 GRVAGTQLVKBPLL-UHFFFAOYSA-N 0.000 description 1
- LMAFWBCYAPNOFK-UHFFFAOYSA-N 1-[2-(4-ethenylphenyl)ethyl]pyrrolidine Chemical compound C1=CC(C=C)=CC=C1CCN1CCCC1 LMAFWBCYAPNOFK-UHFFFAOYSA-N 0.000 description 1
- BIOCRZSYHQYVSG-UHFFFAOYSA-N 2-(4-ethenylphenyl)-n,n-diethylethanamine Chemical compound CCN(CC)CCC1=CC=C(C=C)C=C1 BIOCRZSYHQYVSG-UHFFFAOYSA-N 0.000 description 1
- OHDSHGBRKMRPHC-UHFFFAOYSA-N 2-(4-ethenylphenyl)-n,n-dimethylethanamine Chemical compound CN(C)CCC1=CC=C(C=C)C=C1 OHDSHGBRKMRPHC-UHFFFAOYSA-N 0.000 description 1
- DDDGAIYRCQXPQI-UHFFFAOYSA-N 2-(4-ethenylphenyl)-n-ethyl-n-methylethanamine Chemical compound CCN(C)CCC1=CC=C(C=C)C=C1 DDDGAIYRCQXPQI-UHFFFAOYSA-N 0.000 description 1
- CRWNQZTZTZWPOF-UHFFFAOYSA-N 2-methyl-4-phenylpyridine Chemical compound C1=NC(C)=CC(C=2C=CC=CC=2)=C1 CRWNQZTZTZWPOF-UHFFFAOYSA-N 0.000 description 1
- DVNPFNZTPMWRAX-UHFFFAOYSA-N 2-triethoxysilylethanethiol Chemical compound CCO[Si](CCS)(OCC)OCC DVNPFNZTPMWRAX-UHFFFAOYSA-N 0.000 description 1
- LOSLJXKHQKRRFN-UHFFFAOYSA-N 2-trimethoxysilylethanethiol Chemical compound CO[Si](OC)(OC)CCS LOSLJXKHQKRRFN-UHFFFAOYSA-N 0.000 description 1
- XYKNGYCQUIQASK-UHFFFAOYSA-N 3-(1,3-benzothiazol-2-yl)propyl-(dimethoxymethyl)silane Chemical compound C1=CC=C2SC(CCC[SiH2]C(OC)OC)=NC2=C1 XYKNGYCQUIQASK-UHFFFAOYSA-N 0.000 description 1
- IABJHLPWGMWHLX-UHFFFAOYSA-N 3-(1,3-benzothiazol-2-yl)propyl-trimethoxysilane Chemical compound C1=CC=C2SC(CCC[Si](OC)(OC)OC)=NC2=C1 IABJHLPWGMWHLX-UHFFFAOYSA-N 0.000 description 1
- QPISLCVEROXXQD-UHFFFAOYSA-N 3-(1,3-benzothiazol-2-yltetrasulfanyl)propyl-triethoxysilane Chemical compound C1=CC=C2SC(SSSSCCC[Si](OCC)(OCC)OCC)=NC2=C1 QPISLCVEROXXQD-UHFFFAOYSA-N 0.000 description 1
- HFGLXKZGFFRQAR-UHFFFAOYSA-N 3-(1,3-benzothiazol-2-yltetrasulfanyl)propyl-trimethoxysilane Chemical compound C1=CC=C2SC(SSSSCCC[Si](OC)(OC)OC)=NC2=C1 HFGLXKZGFFRQAR-UHFFFAOYSA-N 0.000 description 1
- WBUSESIMOZDSHU-UHFFFAOYSA-N 3-(4,5-dihydroimidazol-1-yl)propyl-triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN1CCN=C1 WBUSESIMOZDSHU-UHFFFAOYSA-N 0.000 description 1
- LOOUJXUUGIUEBC-UHFFFAOYSA-N 3-(dimethoxymethylsilyl)propane-1-thiol Chemical compound COC(OC)[SiH2]CCCS LOOUJXUUGIUEBC-UHFFFAOYSA-N 0.000 description 1
- DCQBZYNUSLHVJC-UHFFFAOYSA-N 3-triethoxysilylpropane-1-thiol Chemical compound CCO[Si](OCC)(OCC)CCCS DCQBZYNUSLHVJC-UHFFFAOYSA-N 0.000 description 1
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 1
- AKQWHIMDQYDQSR-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylthiirane-2-carboxylate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C1(C)CS1 AKQWHIMDQYDQSR-UHFFFAOYSA-N 0.000 description 1
- AQYONLHMPAMKSC-UHFFFAOYSA-N 4-[2-(4-ethenylphenyl)ethyl]-2,6-dimethylmorpholine Chemical compound C1C(C)OC(C)CN1CCC1=CC=C(C=C)C=C1 AQYONLHMPAMKSC-UHFFFAOYSA-N 0.000 description 1
- WJUHASGUDSZAIJ-UHFFFAOYSA-N 4-[2-(4-ethenylphenyl)ethyl]morpholine Chemical compound C1=CC(C=C)=CC=C1CCN1CCOCC1 WJUHASGUDSZAIJ-UHFFFAOYSA-N 0.000 description 1
- OYQPNXYAJQJYDT-UHFFFAOYSA-N 4-benzyl-1-[2-(4-ethenylphenyl)ethyl]piperidine Chemical compound C1=CC(C=C)=CC=C1CCN1CCC(CC=2C=CC=CC=2)CC1 OYQPNXYAJQJYDT-UHFFFAOYSA-N 0.000 description 1
- ZZMVLMVFYMGSMY-UHFFFAOYSA-N 4-n-(4-methylpentan-2-yl)-1-n-phenylbenzene-1,4-diamine Chemical compound C1=CC(NC(C)CC(C)C)=CC=C1NC1=CC=CC=C1 ZZMVLMVFYMGSMY-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- FRZMXHJATKYFLG-UHFFFAOYSA-N C(=C)C1=C(C=CC=C1)C=C.N1CCCC1 Chemical compound C(=C)C1=C(C=CC=C1)C=C.N1CCCC1 FRZMXHJATKYFLG-UHFFFAOYSA-N 0.000 description 1
- RFVYQWYNYFCXQL-UHFFFAOYSA-N C1=CC=CC2=CC([Li])=CC=C21 Chemical compound C1=CC=CC2=CC([Li])=CC=C21 RFVYQWYNYFCXQL-UHFFFAOYSA-N 0.000 description 1
- JFXOPTVXAREMCX-UHFFFAOYSA-N C=CC=C.C1CCCCC1 Chemical compound C=CC=C.C1CCCCC1 JFXOPTVXAREMCX-UHFFFAOYSA-N 0.000 description 1
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- FBBATURSCRIBHN-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyldisulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSCCC[Si](OCC)(OCC)OCC FBBATURSCRIBHN-UHFFFAOYSA-N 0.000 description 1
- KLFNHRIZTXWZHT-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyltrisulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSSCCC[Si](OCC)(OCC)OCC KLFNHRIZTXWZHT-UHFFFAOYSA-N 0.000 description 1
- JSXKIRYGYMKWSK-UHFFFAOYSA-N trimethoxy-[2-(2-trimethoxysilylethyltetrasulfanyl)ethyl]silane Chemical compound CO[Si](OC)(OC)CCSSSSCC[Si](OC)(OC)OC JSXKIRYGYMKWSK-UHFFFAOYSA-N 0.000 description 1
- JTTSZDBCLAKKAY-UHFFFAOYSA-N trimethoxy-[3-(3-trimethoxysilylpropyltetrasulfanyl)propyl]silane Chemical compound CO[Si](OC)(OC)CCCSSSSCCC[Si](OC)(OC)OC JTTSZDBCLAKKAY-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
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- Compositions Of Macromolecular Compounds (AREA)
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Description
で表される窒素含有化合物とを共重合して得られた重合体を含むゴム成分および、該ゴム成分100質量部に対して、カーボンブラックを1〜20質量部、シリカを20〜120質量部含有するゴム組成物に関する。
で表される窒素含有化合物とを共重合して得られた重合体を含むゴム成分および、該ゴム成分100質量部に対して、カーボンブラックを1〜20質量部、シリカを20〜120質量部含有する。
また、R0及びR8〜R14は、水素又は炭素数1〜2の脂肪族炭化水素基であることが好ましい。
また、R4〜R7は、脂肪族炭化水素基、芳香族炭化水素基又は複素環基であることが好ましく、脂肪族炭化水素基であることがより好ましい。
Qa−M−(OR15)b
(式中、Qはハロゲン又は水素を表す。Mは金属、炭素又はケイ素を表す。R15は炭素数1〜10の脂肪族炭化水素基又は脂環族炭化水素基を表す。a及びbはa+b=4の関係を満たす整数を表す。)
シクロヘキサン:関東化学(株)のシクロヘキサン
ピロリジン:関東化学(株)製のピロリジン
ジビニルベンゼン:シグマアルドリッチ社製のジビニルベンゼン
チオモルホリン:東京化成工業(株)製のチオモルホリン
4−モルホリノピペリジン:シグマアルドリッチ社製の4−モルホリノピペリジン
4−ジメチルアミノピペリジン:シグマアルドリッチ社製の4−ジメチルアミノピペリジン
ジプロピルアミン:シグマアルドリッチ社製のジプロピルアミン
1.6M n−ブチルリチウムヘキサン溶液:関東化学(株)製の1.6M n−ブチルリチウムヘキサン溶液
イソプロパノール:関東化学(株)製のイソプロパノール
十分に窒素置換した100ml容器に、シクロヘキサン50ml、ピロリジン50mmol、ジビニルベンゼン6.5gを加え、0℃にて1.6M n−ブチルリチウムヘキサン溶液0.7ml(1.1mmol)を加えて攪拌した。1時間後、イソプロパノールを加えて反応を停止させ、抽出・精製を行うことでモノマー(1)を得た。
表1に示す処方に従って、モノマー(1)と同様の処方にてモノマー(2)〜(5)を得た。
シクロヘキサン:関東化学(株)製のシクロヘキサン
ブタジエン:高千穂化学工業(株)製の1,3−ブタジエン
テトラヒドロフラン:関東化学(株)製のテトラヒドロフラン(THF)
開始剤溶液:関東化学(株)製の1.6M n−ブチルリチウムヘキサン溶液
末端変性剤:アヅマックス社製の3−(N,N−ジメチルアミノプロピル)トリメトキシシラン
イソプロパノール:関東化学(株)製のイソプロパノール
十分に窒素置換した1000ml耐圧製容器に、シクロヘキサン650ml、ブタジエン1mol、THF1mmolを加え、40℃で1.6M n−ブチルリチウムヘキサン溶液0.4ml(0.64mmol)を加えて撹拌した。3時間後、イソプロパノール3mlを加えて重合を停止させた。反応溶液に2,6−tert−ブチル−p−クレゾール1gを添加後、メタノールで再沈殿処理を行い、加熱乾燥させて重合体(1)を得た。
十分に窒素置換した1000ml耐圧製容器に、シクロヘキサン650ml、ブタジエン1mol、THF1mmolを加え、40℃で1.6M n−ブチルリチウムヘキサン溶液0.4ml(0.64mmol)を加えて撹拌した。3時間後、3−(N,N―ジメチルアミノプロピル)トリメトキシシランを1mmol添加した。さらに30分撹拌させた後、イソプロパノール3mlを加えて重合を停止させた。反応溶液に2,6−tert−ブチル−p−クレゾール1gを添加後、メタノールで再沈殿処理を行い、加熱乾燥させて重合体(2)を得た。
十分に窒素置換した1000ml耐圧製容器に、シクロヘキサン650ml、ブタジエン1mol、モノマー(1)0.3mmol、THF1mmolを加え、40℃で1.6M n−ブチルリチウムヘキサン溶液0.4ml(0.64mmol)を加えて3時間撹拌した。さらに、3−(N,N−ジメチルアミノプロピル)トリメトキシシラン1mmol添加し30分攪拌後、イソプロパノール3mlを加えて重合を停止させた。反応溶液に2,6−tert−ブチル−p−クレゾール1gを添加後、メタノールで再沈殿処理を行い、加熱乾燥させて重合体(3)を得た。
十分に窒素置換した1000ml耐圧製容器に、シクロヘキサン650ml、ブタジエン1mol、モノマー(1)3.4mmol、THF1mmolを加え、40℃で1.6M n−ブチルリチウムヘキサン溶液0.4ml(0.64mmol)を加えて撹拌した。3時間後、イソプロパノール3mlを加えて重合を停止させた。反応溶液に2,6−tert−ブチル−p−クレゾール1gを添加後、メタノールで再沈殿処理を行い、加熱乾燥させて重合体(4)を得た。
十分に窒素置換した1000ml耐圧製容器に、シクロヘキサン650ml、ブタジエン1mol、モノマー(1)3.4mmol、THF1mmolを加え、40℃で1.6M n−ブチルリチウムヘキサン溶液0.4ml(0.64mmol)を加えて撹拌した。3時間後、3−(N,N―ジメチルアミノプロピル)トリメトキシシランを1mmol添加した。さらに30分撹拌させた後、イソプロパノール3mlを加えて重合を停止させた。反応溶液に2,6−tert−ブチル−p−クレゾール1gを添加後、メタノールで再沈殿処理を行い、加熱乾燥させて重合体(5)を得た。
表2の配合で、製造例10と同様の方法で、それぞれの重合体を合成した。
重量平均分子量Mwは、ゲルパーミエーションクロマトグラフ(GPC)(東ソー(株)製GPC−8000シリーズ、検出器:示差屈折計、カラム:東ソー(株)製のTSKGEL SUPERMALTPORE HZ−M)を用いて測定した。校正は、標準ポリスチレンによって行った。
重合体中の窒素含有化合物誘導体モノマー量は、日本電子(株)製JNM−ECAシリーズの装置を用いて測定した。
以下に、実施例および比較例で用いた各種薬品について説明する。
NR:RSS#3
BR:宇部興産(株)製のハイシスBR150B
カーボンブラック:キャボットジャパン(株)製のショウブラックN220(チッ素吸着比表面積(N2SA):125m2/g)
シリカ:デグッサ社製のウルトラシルVN3(チッ素吸着比表面積(N2SA):210m2/g)
シランカップリング剤:デグッサ社製のSi69
老化防止剤:大内新興化学工業(株)製のノクラック6C(N−1,3−ジメチルブチル−N’−フェニル−p−フェニレンジアミン)
ステアリン酸:日油(株)製のステアリン酸
オイル:出光興産(株)製のミネラルオイルPW−380
酸化亜鉛:三井金属鉱業(株)製の亜鉛華1号
ワックス:大内新興化学工業(株)製のサンノックワックス
硫黄:鶴見化学(株)製の粉末硫黄
加硫促進剤(1):大内新興化学工業(株)製のノクセラーCZ
加硫促進剤(2):大内新興化学工業(株)製のノクセラーD
ティ・エス・インスツルメント(株)製の粘弾性測定試験機を用いて、温度0℃、周波数5Hz、振幅0.1%における弾性率(0.1%G*)、および振幅40%における弾性率(40%G*)から0.1%G*を引いた値(ΔG*)を測定した。
s=(ΔG*)÷(0.1%G*)
で表される指数sを用い(sは0<s<1の値である)、標準品(BR150Bを使用した比較例6)のsを100とした相対値sを指標とした。sが0に近いほど、氷上性能と操縦安定性のバランスが良いことを示す。
Claims (4)
- 共役ジエン化合物と、下記一般式
で表される窒素含有化合物とを共重合して得られた重合体及び天然ゴムを含むゴム成分を含有し、該ゴム成分100質量部に対して、カーボンブラックを1〜20質量部、シリカを20〜120質量部含有するゴム組成物。 - 前記重合体における窒素含有化合物の含有量が0.1〜30質量%である請求項1記載のゴム組成物。
- ゴム成分100質量%中に、前記重合体を5質量%以上70質量%以下含む請求項1または2記載のゴム組成物。
- 請求項1〜3のいずれかに記載のゴム組成物を用いて作製したスタッドレスタイヤ。
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