JP5437765B2 - Rubber composition for tire and studless tire - Google Patents
Rubber composition for tire and studless tire Download PDFInfo
- Publication number
- JP5437765B2 JP5437765B2 JP2009234570A JP2009234570A JP5437765B2 JP 5437765 B2 JP5437765 B2 JP 5437765B2 JP 2009234570 A JP2009234570 A JP 2009234570A JP 2009234570 A JP2009234570 A JP 2009234570A JP 5437765 B2 JP5437765 B2 JP 5437765B2
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- JP
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- Prior art keywords
- group
- rubber
- mass
- epoxidized
- polymer
- 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.)
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- 229920001971 elastomer Polymers 0.000 title claims description 48
- 239000005060 rubber Substances 0.000 title claims description 48
- 239000000203 mixture Substances 0.000 title claims description 28
- -1 diene compound Chemical class 0.000 claims description 77
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 54
- 229920000642 polymer Polymers 0.000 claims description 52
- 229920003244 diene elastomer Polymers 0.000 claims description 43
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 26
- 239000000377 silicon dioxide Substances 0.000 claims description 26
- 229910052757 nitrogen Inorganic materials 0.000 claims description 25
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 20
- 239000005062 Polybutadiene Substances 0.000 claims description 20
- 238000006735 epoxidation reaction Methods 0.000 claims description 20
- 229920002857 polybutadiene Polymers 0.000 claims description 20
- 244000043261 Hevea brasiliensis Species 0.000 claims description 19
- 229920003052 natural elastomer Polymers 0.000 claims description 19
- 229920001194 natural rubber Polymers 0.000 claims description 19
- 239000003607 modifier Substances 0.000 claims description 16
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 14
- 239000006229 carbon black Substances 0.000 claims description 14
- 229920002554 vinyl polymer Polymers 0.000 claims description 11
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 10
- 239000003505 polymerization initiator Substances 0.000 claims description 10
- 238000006116 polymerization reaction Methods 0.000 claims description 10
- 125000000524 functional group Chemical group 0.000 claims description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 150000001340 alkali metals Chemical class 0.000 claims description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 229910052710 silicon Inorganic materials 0.000 claims description 5
- 239000010703 silicon Substances 0.000 claims description 5
- 230000004048 modification Effects 0.000 claims description 4
- 238000012986 modification Methods 0.000 claims description 4
- 150000003440 styrenes Chemical class 0.000 claims description 4
- 241000872198 Serjania polyphylla Species 0.000 claims 1
- 238000000034 method Methods 0.000 description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 23
- 239000000243 solution Substances 0.000 description 23
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 20
- 238000004519 manufacturing process Methods 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 13
- 125000003277 amino group Chemical group 0.000 description 13
- 238000011191 terminal modification Methods 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 12
- 125000000217 alkyl group Chemical group 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- 239000000945 filler Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 125000003545 alkoxy group Chemical group 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 150000004292 cyclic ethers Chemical group 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 239000000178 monomer Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- 239000006087 Silane Coupling Agent Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000001179 sorption measurement Methods 0.000 description 5
- 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 5
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 5
- 239000004636 vulcanized rubber Substances 0.000 description 5
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical class C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 125000004036 acetal group Chemical group 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 125000002897 diene group Chemical group 0.000 description 4
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 4
- 229920003049 isoprene rubber Polymers 0.000 description 4
- 229910052744 lithium Inorganic materials 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229920003048 styrene butadiene rubber Polymers 0.000 description 4
- 238000004073 vulcanization Methods 0.000 description 4
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- 229920000459 Nitrile rubber Polymers 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 230000003712 anti-aging effect Effects 0.000 description 3
- 229920005549 butyl rubber Polymers 0.000 description 3
- 239000004205 dimethyl polysiloxane Substances 0.000 description 3
- 125000003700 epoxy group Chemical group 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- QOSATHPSBFQAML-UHFFFAOYSA-N hydrogen peroxide;hydrate Chemical compound O.OO QOSATHPSBFQAML-UHFFFAOYSA-N 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 150000002642 lithium compounds Chemical class 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- AQIQPUUNTCVHBS-UHFFFAOYSA-N n,n-dimethyl-3-triethoxysilylpropan-1-amine Chemical compound CCO[Si](OCC)(OCC)CCCN(C)C AQIQPUUNTCVHBS-UHFFFAOYSA-N 0.000 description 3
- 229920006173 natural rubber latex Polymers 0.000 description 3
- 125000000466 oxiranyl group Chemical group 0.000 description 3
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 3
- 230000003014 reinforcing effect Effects 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 description 3
- 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
- XLOUXCBUKZRSQG-UHFFFAOYSA-N 2-oxo-n-(3-trimethoxysilylpropyl)azepane-1-carboxamide Chemical compound CO[Si](OC)(OC)CCCNC(=O)N1CCCCCC1=O XLOUXCBUKZRSQG-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 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 2
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 2
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 2
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 229920002943 EPDM rubber Polymers 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 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
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 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
- 235000021355 Stearic acid Nutrition 0.000 description 2
- 239000002174 Styrene-butadiene Substances 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000005370 alkoxysilyl group Chemical group 0.000 description 2
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 125000000000 cycloalkoxy group Chemical group 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 125000001033 ether group Chemical group 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- ZLDHYRXZZNDOKU-UHFFFAOYSA-N n,n-diethyl-3-trimethoxysilylpropan-1-amine Chemical compound CCN(CC)CCC[Si](OC)(OC)OC ZLDHYRXZZNDOKU-UHFFFAOYSA-N 0.000 description 2
- DVYVMJLSUSGYMH-UHFFFAOYSA-N n-methyl-3-trimethoxysilylpropan-1-amine Chemical compound CNCCC[Si](OC)(OC)OC DVYVMJLSUSGYMH-UHFFFAOYSA-N 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
- 150000004967 organic peroxy acids Chemical class 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
- 150000004965 peroxy acids Chemical class 0.000 description 2
- QKFJKGMPGYROCL-UHFFFAOYSA-N phenyl isothiocyanate Chemical compound S=C=NC1=CC=CC=C1 QKFJKGMPGYROCL-UHFFFAOYSA-N 0.000 description 2
- 229920001084 poly(chloroprene) Polymers 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000012744 reinforcing agent Substances 0.000 description 2
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 239000008117 stearic acid Substances 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
- XVZMLSWFBPLMEA-UHFFFAOYSA-N trimethoxy(2-pyridin-2-ylethyl)silane Chemical compound CO[Si](OC)(OC)CCC1=CC=CC=N1 XVZMLSWFBPLMEA-UHFFFAOYSA-N 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 2
- MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical compound NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 description 1
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- AHAREKHAZNPPMI-AATRIKPKSA-N (3e)-hexa-1,3-diene Chemical compound CC\C=C\C=C AHAREKHAZNPPMI-AATRIKPKSA-N 0.000 description 1
- CGCQHMFVCNWSOV-UHFFFAOYSA-N (4-morpholin-4-ylphenyl)-phenylmethanone Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C1=CC=CC=C1 CGCQHMFVCNWSOV-UHFFFAOYSA-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
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
- ONILJRYQYWLXQU-UHFFFAOYSA-N 1,1-dioctyl-3-(3-triethoxysilylpropyl)urea Chemical compound CCCCCCCCN(CCCCCCCC)C(=O)NCCC[Si](OCC)(OCC)OCC ONILJRYQYWLXQU-UHFFFAOYSA-N 0.000 description 1
- SOAWOGBXWCCNFB-UHFFFAOYSA-N 1,1-dioctyl-3-(3-trimethoxysilylpropyl)urea Chemical compound CCCCCCCCN(CCCCCCCC)C(=O)NCCC[Si](OC)(OC)OC SOAWOGBXWCCNFB-UHFFFAOYSA-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
- CORMBJOFDGICKF-UHFFFAOYSA-N 1,3,5-trimethoxy 2-vinyl benzene Natural products COC1=CC(OC)=C(C=C)C(OC)=C1 CORMBJOFDGICKF-UHFFFAOYSA-N 0.000 description 1
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical group C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
- HOBIHBQJHORMMP-UHFFFAOYSA-N 1,3-bis(3-triethoxysilylpropyl)urea Chemical compound CCO[Si](OCC)(OCC)CCCNC(=O)NCCC[Si](OCC)(OCC)OCC HOBIHBQJHORMMP-UHFFFAOYSA-N 0.000 description 1
- HSDGFGSXXVWDET-UHFFFAOYSA-N 1,3-bis(3-trimethoxysilylpropyl)urea Chemical compound CO[Si](OC)(OC)CCCNC(=O)NCCC[Si](OC)(OC)OC HSDGFGSXXVWDET-UHFFFAOYSA-N 0.000 description 1
- ZWAVGZYKJNOTPX-UHFFFAOYSA-N 1,3-diethylurea Chemical compound CCNC(=O)NCC ZWAVGZYKJNOTPX-UHFFFAOYSA-N 0.000 description 1
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- UMXXGDJOCQSQBV-UHFFFAOYSA-N n-ethyl-n-(triethoxysilylmethyl)ethanamine Chemical compound CCO[Si](OCC)(OCC)CN(CC)CC UMXXGDJOCQSQBV-UHFFFAOYSA-N 0.000 description 1
- KPIIDEIURMTGCD-UHFFFAOYSA-N n-ethyl-n-(trimethoxysilylmethyl)ethanamine Chemical compound CCN(CC)C[Si](OC)(OC)OC KPIIDEIURMTGCD-UHFFFAOYSA-N 0.000 description 1
- DTPZJXALAREFEY-UHFFFAOYSA-N n-methyl-3-triethoxysilylpropan-1-amine Chemical compound CCO[Si](OCC)(OCC)CCCNC DTPZJXALAREFEY-UHFFFAOYSA-N 0.000 description 1
- 229940032017 n-oxydiethylene-2-benzothiazole sulfenamide Drugs 0.000 description 1
- UBVMBXTYMSRUDX-UHFFFAOYSA-N n-prop-2-enyl-3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCNCC=C UBVMBXTYMSRUDX-UHFFFAOYSA-N 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002900 organolithium compounds Chemical class 0.000 description 1
- 150000003961 organosilicon compounds Chemical class 0.000 description 1
- 125000003551 oxepanyl group Chemical group 0.000 description 1
- 125000003566 oxetanyl group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- GNWXVOQHLPBSSR-UHFFFAOYSA-N oxolane;toluene Chemical compound C1CCOC1.CC1=CC=CC=C1 GNWXVOQHLPBSSR-UHFFFAOYSA-N 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 229940117953 phenylisothiocyanate Drugs 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- ZRLVQFQTCMUIRM-UHFFFAOYSA-N potassium;2-methylbutan-2-olate Chemical compound [K+].CCC(C)(C)[O-] ZRLVQFQTCMUIRM-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000005767 propoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])[#8]C([H])([H])* 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 125000005372 silanol group Chemical group 0.000 description 1
- 239000005049 silicon tetrachloride Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- CGRKYEALWSRNJS-UHFFFAOYSA-N sodium;2-methylbutan-2-olate Chemical compound [Na+].CCC(C)(C)[O-] CGRKYEALWSRNJS-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229940035044 sorbitan monolaurate Drugs 0.000 description 1
- 229960000391 sorbitan trioleate Drugs 0.000 description 1
- 235000019337 sorbitan trioleate Nutrition 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000010059 sulfur vulcanization Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 1
- ADLSSRLDGACTEX-UHFFFAOYSA-N tetraphenyl silicate Chemical compound C=1C=CC=CC=1O[Si](OC=1C=CC=CC=1)(OC=1C=CC=CC=1)OC1=CC=CC=C1 ADLSSRLDGACTEX-UHFFFAOYSA-N 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 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
- WDVUXWDZTPZIIE-UHFFFAOYSA-N trichloro(2-trichlorosilylethyl)silane Chemical compound Cl[Si](Cl)(Cl)CC[Si](Cl)(Cl)Cl WDVUXWDZTPZIIE-UHFFFAOYSA-N 0.000 description 1
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 description 1
- LFBSOUVFURPMCL-UHFFFAOYSA-N triethoxy(3-pyrrol-1-ylpropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN1C=CC=C1 LFBSOUVFURPMCL-UHFFFAOYSA-N 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- 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
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- HPEPIADELDNCED-UHFFFAOYSA-N triethoxysilylmethanol Chemical compound CCO[Si](CO)(OCC)OCC HPEPIADELDNCED-UHFFFAOYSA-N 0.000 description 1
- FTDRQHXSYGDMNJ-UHFFFAOYSA-N trimethoxy(3-pyrrol-1-ylpropyl)silane Chemical compound CO[Si](OC)(OC)CCCN1C=CC=C1 FTDRQHXSYGDMNJ-UHFFFAOYSA-N 0.000 description 1
- QLNOVKKVHFRGMA-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical group [CH2]CC[Si](OC)(OC)OC QLNOVKKVHFRGMA-UHFFFAOYSA-N 0.000 description 1
- MQGPKQPSPLQBBD-UHFFFAOYSA-N trimethoxy-[2-(2-pyridin-4-ylethylsulfanyl)propyl]silane Chemical compound CO[Si](OC)(OC)CC(C)SCCC1=CC=NC=C1 MQGPKQPSPLQBBD-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
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-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
- FPKMSRRUOFZBQR-UHFFFAOYSA-N triphenoxymethylsilane Chemical compound O(C1=CC=CC=C1)C(OC1=CC=CC=C1)(OC1=CC=CC=C1)[SiH3] FPKMSRRUOFZBQR-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-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
Landscapes
- Tires In General (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
本発明は、タイヤ用ゴム組成物、及びそれを用いたスタッドレスタイヤに関する。 The present invention relates to a rubber composition for tires and a studless tire using the same.
氷雪路走行に使用される空気入りタイヤは、従来のスパイクタイヤに代わりスタッドレスタイヤが多く使用されるようになり、氷上性能の向上が一段と要求されてきている。氷雪上性能を向上させるためには、ガラス転移点(Tg)を下げ、低温(ここで、低温とは、氷雪上走行時の温度であり、−20〜0℃程度である)での弾性率を低く設定したものが多い。しかしながら、一般に、低温での弾性率を下げると、高温での弾性率も低下する傾向があるため、従来のスタッドレスタイヤは、ドライ路面を走行する際には、操縦安定性が低いという問題があった。 As pneumatic tires used for running on icy and snowy roads, studless tires are often used instead of conventional spike tires, and further improvement in performance on ice has been required. In order to improve the performance on ice and snow, the glass transition point (Tg) is lowered, and the elastic modulus at a low temperature (here, the low temperature is a temperature during running on ice and snow, which is about −20 to 0 ° C.). Many are set low. However, in general, when the elastic modulus at low temperature is lowered, the elastic modulus at high temperature also tends to decrease. Therefore, the conventional studless tire has a problem that the driving stability is low when traveling on a dry road surface. It was.
上記の問題に対し、シリカを配合したゴム組成物において、ゴム成分に特定の極性基を導入する試みが提案されている。この試みによれば、シリカに対する親和性をゴム成分に持たせることができ、シリカの分散性を向上することができる。したがって、低温時の弾性率を低く設定した場合であっても、高温時の弾性率の低下を抑制することが可能となる。 In order to solve the above problems, attempts have been made to introduce a specific polar group into a rubber component in a rubber composition containing silica. According to this attempt, the rubber component can have affinity for silica, and the dispersibility of silica can be improved. Therefore, even when the elastic modulus at a low temperature is set low, it is possible to suppress a decrease in the elastic modulus at a high temperature.
上記試みの例として、特許文献1では、アミノ基及びアルコキシ基を含有する有機ケイ素化合物で変性されたジエン系ゴムが開示され、特許文献2では、スズ変性ブタジエンゴムが開示され、特許文献3及び4では、エポキシ化天然ゴムが開示され、特許文献5では、エポキシ化された共役ジエン系共重合体が開示されている。しかしながら、これらの方法によっても、シリカの分散性については必ずしも充分なものではなく、氷上性能と、ドライ路面での操縦安定性(ドライ操縦安定性)とをバランスよく改善する方法が要望されていた。 As an example of the above attempt, Patent Document 1 discloses a diene rubber modified with an organosilicon compound containing an amino group and an alkoxy group, and Patent Document 2 discloses a tin-modified butadiene rubber. 4 discloses an epoxidized natural rubber, and Patent Document 5 discloses an epoxidized conjugated diene copolymer. However, even with these methods, the dispersibility of silica is not always sufficient, and a method for improving the performance on ice and the handling stability on the dry road surface (dry handling stability) in a well-balanced manner has been demanded. .
本発明は、前記課題を解決し、耐摩耗性を維持しつつ、氷上性能及びドライ操縦安定性を両立したタイヤ用ゴム組成物と、それを用いたスタッドレスタイヤとを提供することを目的とする。 An object of the present invention is to solve the above-mentioned problems, and to provide a rubber composition for a tire that achieves both on-ice performance and dry handling stability while maintaining wear resistance, and a studless tire using the same. .
本発明者らは、上記課題を解決するために鋭意検討を重ねた結果、ゴム成分として、シリカに対する親和性を持たせた特定の重合体と、エポキシ化ジエン系ゴムとを組み合わせて用いることにより、シリカが特定の重合体中に偏在して分散されることを防止し、全体としてシリカの分散が向上し、耐摩耗性を維持しつつ、氷上性能及びドライ操縦安定性をバランスよく改善できることを見出した。
すなわち本発明は、共役ジエン化合物または共役ジエン化合物と芳香族ビニル化合物を、アルカリ金属を含む重合開始剤を用いて重合し、重合終了後に窒素、酸素、およびケイ素からなる群より選択される少なくとも1種の原子を含む官能基を含有する変性剤で変性して得られる重合体と、エポキシ化率が0.5〜50モル%のエポキシ化ジエン系ゴムとを含むゴム成分と、シリカとを含むタイヤ用ゴム組成物に関する。
As a result of intensive studies to solve the above problems, the present inventors have used a specific polymer having an affinity for silica as a rubber component in combination with an epoxidized diene rubber. , Preventing the silica from being unevenly distributed in a specific polymer, improving the dispersion of the silica as a whole, maintaining the wear resistance, and improving the on-ice performance and the dry handling stability in a balanced manner. I found it.
That is, the present invention polymerizes a conjugated diene compound or a conjugated diene compound and an aromatic vinyl compound using a polymerization initiator containing an alkali metal, and at least one selected from the group consisting of nitrogen, oxygen, and silicon after completion of the polymerization. A rubber component containing a polymer obtained by modification with a modifier containing a functional group containing a seed atom, an epoxidized diene rubber having an epoxidation rate of 0.5 to 50 mol%, and silica. The present invention relates to a tire rubber composition.
また、上記重合体の重量平均分子量が5×104〜1×106であることが好ましい。 Moreover, it is preferable that the weight average molecular weights of the said polymer are 5 * 10 < 4 > -1 * 10 < 6 >.
また、上記共役ジエン化合物がブタジエンおよび/またはイソプレンであり、上記芳香族ビニル化合物がスチレンおよび/またはアルキル置換スチレンであることが好ましい。 The conjugated diene compound is preferably butadiene and / or isoprene, and the aromatic vinyl compound is preferably styrene and / or alkyl-substituted styrene.
また、ゴム成分100質量%中の上記重合体の含有量が10〜70質量%であることが好ましい。 Moreover, it is preferable that content of the said polymer in 100 mass% of rubber components is 10-70 mass%.
また、ゴム成分100質量%中の上記エポキシ化ジエン系ゴムの含有量が10〜30質量%であることが好ましい。 Moreover, it is preferable that content of the said epoxidized diene rubber in 100 mass% of rubber components is 10-30 mass%.
また、上記エポキシ化ジエン系ゴムが、エポキシ化天然ゴムまたはエポキシ化ブタジエンゴムであることが好ましい。 The epoxidized diene rubber is preferably epoxidized natural rubber or epoxidized butadiene rubber.
また、ゴム成分100質量部に対してカーボンブラックを5〜150質量部含むことが好ましい。 Moreover, it is preferable that 5-150 mass parts of carbon black is included with respect to 100 mass parts of rubber components.
本発明はまた、上記タイヤ用ゴム組成物を用いて作製したスタッドレスタイヤに関する。 The present invention also relates to a studless tire manufactured using the tire rubber composition.
本発明によれば、ゴム成分として、共役ジエン化合物または共役ジエン化合物と芳香族ビニル化合物を、アルカリ金属を含む重合開始剤を用いて重合し、重合終了後に窒素、酸素、およびケイ素からなる群より選択される少なくとも1種の原子を含む官能基を含有する変性剤で変性して得られる重合体と、特定のエポキシ化率のエポキシ化ジエン系ゴムと、シリカとを組み合わせることで、シリカの分散性が改善されたタイヤ用ゴム組成物が得られるため、耐摩耗性を維持しつつ、氷上性能及びドライ操縦安定性をバランスよく改善できる。該タイヤ用ゴム組成物は、タイヤの各部材に好適に適用でき、耐摩耗性を維持しつつ、氷上性能及びドライ操縦安定性をバランスよく改善したスタッドレスタイヤを提供できる。 According to the present invention, as a rubber component, a conjugated diene compound or a conjugated diene compound and an aromatic vinyl compound are polymerized using a polymerization initiator containing an alkali metal, and after completion of the polymerization, from the group consisting of nitrogen, oxygen, and silicon Dispersion of silica by combining a polymer obtained by modification with a modifier containing a functional group containing at least one selected atom, an epoxidized diene rubber having a specific epoxidation rate, and silica. Therefore, the performance on ice and the stability of dry handling can be improved in a well-balanced manner while maintaining the wear resistance. The rubber composition for a tire can be suitably applied to each member of the tire, and can provide a studless tire having improved performance on ice and dry steering stability in a well-balanced manner while maintaining wear resistance.
本発明の重合体は、共役ジエン化合物または共役ジエン化合物と芳香族ビニル化合物を、アルカリ金属を含む重合開始剤を用いて重合し、重合終了後に、窒素、酸素、およびケイ素からなる群より選択される少なくとも1種の原子を含む官能基を含有する変性剤で変性して得られる重合体である。 The polymer of the present invention is a conjugated diene compound or a conjugated diene compound and an aromatic vinyl compound, polymerized using a polymerization initiator containing an alkali metal, and selected from the group consisting of nitrogen, oxygen, and silicon after completion of the polymerization. A polymer obtained by modification with a modifier containing a functional group containing at least one kind of atom.
共役ジエン化合物としては、例えば1,3−ブタジエン、イソプレン、1,3−ペンタジエン、2,3−ジメチルブタジエン、2−フェニル−1,3−ブタジエン、1,3−ヘキサジエンなどが挙げられる。これらは単独で用いてもよく、二種以上を組み合わせて用いてもよい。なかでも、モノマー入手の容易性など、実用面の観点から1,3−ブタジエン、イソプレンが好ましい。 Examples of the conjugated diene compound include 1,3-butadiene, isoprene, 1,3-pentadiene, 2,3-dimethylbutadiene, 2-phenyl-1,3-butadiene, 1,3-hexadiene, and the like. These may be used alone or in combination of two or more. Of these, 1,3-butadiene and isoprene are preferred from the viewpoint of practical use such as easy availability of monomers.
芳香族ビニル化合物としては、例えばα−メチルスチレン、α−エチルスチレン、4−シクロヘキシルスチレン、2,4,6−トリメチルスチレン、t−ブチルスチレン等のアルキル置換スチレン、スチレン、ジビニルベンゼン、1−ビニルナフタレン、3−ビニルトルエンなどが挙げられる。これらは単独で用いてもよく、2種以上を組み合わせても用いてもよい。なかでも、モノマー入手の容易性など、実用面の観点からアルキル置換スチレン、スチレンが好ましい。なお、共役ジエン化合物と、芳香族ビニル化合物を組み合わせて用いてもよい。 Examples of the aromatic vinyl compound include α-methylstyrene, α-ethylstyrene, 4-cyclohexylstyrene, 2,4,6-trimethylstyrene, t-butylstyrene and other alkyl-substituted styrene, styrene, divinylbenzene, 1-vinyl. Naphthalene, 3-vinyltoluene and the like can be mentioned. These may be used alone or in combination of two or more. Of these, alkyl-substituted styrene and styrene are preferable from the viewpoint of practical use such as availability of monomers. A conjugated diene compound and an aromatic vinyl compound may be used in combination.
重合開始剤に含まれるアルカリ金属としては、リチウム、ナトリウム、カリウム等が挙げられる。なかでも、リチウムが好ましい。
リチウムを含む重合開始剤としては、リチウムアミド化合物、ヒドロカルビルリチウム等の有機リチウム化合物が好ましく用いられる。有機リチウム化合物のなかでも、炭素数2〜20のアルキル基を有するものが好ましく、例えばエチルリチウム、n−プロピルリチウム、イソプロピルリチウム、n−ブチルリチウム、sec−ブチルリチウム、tert−ブチルリチウム、tert−オクチルリチウム、n−デシルリチウム、フェニルリチウム、2−ナフチルリチウム、2−ブチル−フェニルリチウム、4−フェニル−ブチルリチウム、シクロヘキシルリチウム、シクロペンチルリチウム、ジイソプロペニルベンゼンとブチルリチウムとの反応生成物などが挙げられるが、これらの中で、入手容易性、安全性等の観点からn−ブチルリチウムまたはsec−ブチルリチウムが好ましい。
Examples of the alkali metal contained in the polymerization initiator include lithium, sodium, and potassium. Of these, lithium is preferable.
As the polymerization initiator containing lithium, an organic lithium compound such as a lithium amide compound or hydrocarbyl lithium is preferably used. Among the organic lithium compounds, those having an alkyl group having 2 to 20 carbon atoms are preferable. For example, ethyl lithium, n-propyl lithium, isopropyl lithium, n-butyl lithium, sec-butyl lithium, tert-butyl lithium, tert- Octyl lithium, n-decyl lithium, phenyl lithium, 2-naphthyl lithium, 2-butyl-phenyl lithium, 4-phenyl-butyl lithium, cyclohexyl lithium, cyclopentyl lithium, reaction products of diisopropenylbenzene and butyl lithium, etc. Among these, n-butyllithium or sec-butyllithium is preferable from the viewpoints of availability, safety, and the like.
アルカリ金属を含む重合開始剤(例えば、有機リチウム化合物)を用い、アニオン重合によって重合体を製造する方法としては、特に制限はなく、従来公知の方法を用いることができる。
具体的には、反応に不活性な有機溶剤、例えば脂肪族、脂環族、芳香族炭化水素化合物などの炭化水素系溶剤中において、共役ジエン化合物または共役ジエン化合物と芳香族ビニル化合物を、アルカリ金属を含む重合開始剤(例えば、有機リチウム化合物)を用い、必要に応じてランダマイザーの存在下でアニオン重合させることにより、目的の重合体が得られる。
There is no restriction | limiting in particular as a method of manufacturing a polymer by anionic polymerization using the polymerization initiator (for example, organolithium compound) containing an alkali metal, A conventionally well-known method can be used.
Specifically, a conjugated diene compound or a conjugated diene compound and an aromatic vinyl compound in an organic solvent inert to the reaction, for example, a hydrocarbon solvent such as an aliphatic, alicyclic or aromatic hydrocarbon compound, A target polymer is obtained by anionic polymerization using a polymerization initiator (for example, an organic lithium compound) containing a metal in the presence of a randomizer as necessary.
炭化水素系溶剤としては、炭素数3〜8のものが好ましく、例えばプロパン、n−ブタン、イソブタン、n−ペンタン、イソペンタン、n−ヘキサン、シクロヘキサン、プロペン、1−ブテン、イソブテン、トランス−2−ブテン、シス−2−ブテン、1−ペンテン、2−ペンテン、1−ヘキセン、2−ヘキセン、ベンゼン、トルエン、キシレン、エチルベンゼンなどを挙げることができる。これらは単独で用いてもよく、2種以上を混合して用いてもよい。 The hydrocarbon solvent is preferably one having 3 to 8 carbon atoms, for example, propane, n-butane, isobutane, n-pentane, isopentane, n-hexane, cyclohexane, propene, 1-butene, isobutene, trans-2- Examples include butene, cis-2-butene, 1-pentene, 2-pentene, 1-hexene, 2-hexene, benzene, toluene, xylene, and ethylbenzene. These may be used alone or in combination of two or more.
溶媒中のモノマー(共役ジエン化合物及び芳香族ビニル化合物の合計)濃度は、5質量%以上が好ましく、10質量%以上がより好ましい。溶液中のモノマー濃度が5質量%未満では、得られる重合体の量が少なく、コストが高くなる傾向がある。また、溶媒中のモノマー濃度は50質量%以下が好ましく、30質量%以下がより好ましい。溶媒中のモノマー濃度が50質量%をこえると、溶液粘度が高くなりすぎて撹拌が困難となり、重合しにくくなる傾向がある。 The monomer (total of conjugated diene compound and aromatic vinyl compound) concentration in the solvent is preferably 5% by mass or more, and more preferably 10% by mass or more. When the monomer concentration in the solution is less than 5% by mass, the amount of the obtained polymer is small and the cost tends to be high. The monomer concentration in the solvent is preferably 50% by mass or less, and more preferably 30% by mass or less. When the monomer concentration in the solvent exceeds 50% by mass, the solution viscosity becomes too high, stirring becomes difficult, and polymerization tends to be difficult.
また、前記ランダマイザーとは、重合体中の共役ジエン部分のミクロ構造制御、例えばブタジエンにおける1、2−結合、イソプレンにおける3、4−結合の増加など、あるいは重合体におけるモノマー単位の組成分布の制御、例えばブタジエン−スチレン共重合体におけるブタジエン単位、スチレン単位のランダム化などの作用を有する化合物のことである。 The randomizer is a microstructure control of a conjugated diene moiety in a polymer, for example, an increase in 1,2-bond in butadiene, an increase in 3,4-bond in isoprene, or a composition distribution of monomer units in the polymer. It is a compound having control, for example, randomization of butadiene units and styrene units in a butadiene-styrene copolymer.
ランダマイザーとしては、特に制限はなく、従来ランダマイザーとして一般に使用されている公知の化合物の中から任意のものを用いることができる。例えば、ジメトキシベンゼン、テトラヒドロフラン、ジエチルエーテル、ジメトキシエタン、ジエチレングリコールジブチルエーテル、ジエチレングリコールジメチルエーテル、ビステトラヒドロフリルプロパン、トリエチルアミン、ピリジン、N−メチルモルホリン、N,N,N’,N’−テトラメチルエチレンジアミン、1,2−ジピペリジノエタンなどのエーテル類及び第三級アミン類などを挙げることができる。また、カリウム−t−アミレート、カリウム−t−ブトキシドなどのカリウム塩、ナトリウム−t−アミレートなどのナトリウム塩類も用いることができる。これらのランダマイザーは、1種を単独で用いてもよく、2種以上を組み合わせて用いてもよい。なかでも、入手や取り扱いの容易性などの理由から、テトラヒドロフラン、N,N,N’,N’−テトラメチルエチレンジアミンが好ましい。 There is no restriction | limiting in particular as a randomizer, Arbitrary things can be used from the well-known compound generally used as a conventional randomizer. For example, dimethoxybenzene, tetrahydrofuran, diethyl ether, dimethoxyethane, diethylene glycol dibutyl ether, diethylene glycol dimethyl ether, bistetrahydrofurylpropane, triethylamine, pyridine, N-methylmorpholine, N, N, N ′, N′-tetramethylethylenediamine, 1, Examples include ethers such as 2-dipiperidinoethane and tertiary amines. Further, potassium salts such as potassium-t-amylate and potassium-t-butoxide, and sodium salts such as sodium-t-amylate can also be used. These randomizers may be used individually by 1 type, and may be used in combination of 2 or more type. Of these, tetrahydrofuran, N, N, N ′, N′-tetramethylethylenediamine is preferred for reasons such as availability and ease of handling.
ランダマイザーの使用量は、重合開始剤1モルに対して、0.01モル以上が好ましく、0.05モル以上がより好ましい。ランダマイザーの使用量が0.01モル未満では、添加効果が小さく、ランダム化しにくい傾向がある。また、ランダマイザーの使用量は、重合開始剤1モルに対して、1000モル以下が好ましく、500モル以下がより好ましい。ランダマイザーの使用量が1000モルをこえると、モノマーの反応速度が大きく変化してしまい、逆にランダム化しにくくなる傾向がある。 The amount of the randomizer used is preferably 0.01 mol or more, more preferably 0.05 mol or more, relative to 1 mol of the polymerization initiator. When the amount of the randomizer used is less than 0.01 mol, the effect of addition is small and it tends to be difficult to randomize. Moreover, 1000 mol or less is preferable with respect to 1 mol of polymerization initiators, and, as for the usage-amount of a randomizer, 500 mol or less is more preferable. When the amount of the randomizer used exceeds 1000 mol, the reaction rate of the monomer changes greatly, and conversely, it tends to be difficult to randomize.
本発明で使用する変性剤は、窒素、酸素、およびケイ素からなる群より選択される少なくとも1種の原子を含む官能基を有する化合物である。該変性剤は、少なくとも重合体の活性末端と反応することによりポリマーと結合し、かつ、フィラーとの相互作用もある化合物である。
官能基としては、例えばアミノ基、アミド基、アルコキシシリル基、イソシアネート基、イミノ基、イミダゾール基、ウレア基、エーテル基、カルボニル基、カルボキシル基、ヒドロキシ基、エポキシ基、ニトリル基、ピリジル基等があげられる。なお、これらの官能基は、置換基を有していてもよい。なかでも、入手や取り扱いが容易であることや、ポリマーと良好に結合するなどの理由から、アミノ基(アルキル置換アミノ基)、アルコキシシリル基、エーテル基、エポキシ基が好ましい。
The modifier used in the present invention is a compound having a functional group containing at least one atom selected from the group consisting of nitrogen, oxygen, and silicon. The modifier is a compound that binds to the polymer by reacting at least with the active terminal of the polymer and also has an interaction with the filler.
Examples of functional groups include amino groups, amide groups, alkoxysilyl groups, isocyanate groups, imino groups, imidazole groups, urea groups, ether groups, carbonyl groups, carboxyl groups, hydroxy groups, epoxy groups, nitrile groups, and pyridyl groups. can give. These functional groups may have a substituent. Among these, an amino group (alkyl-substituted amino group), an alkoxysilyl group, an ether group, and an epoxy group are preferable because they are easily available and handled and are well bonded to the polymer.
変性剤としては、例えば3−グリシドキシプロピルトリメトキシシラン、(3−トリエトキシシリルプロピル)テトラスルフィド、1−(4−N,N−ジメチルアミノフェニル)−1−フェニルエチレン、1,1−ジメトキシトリメチルアミン、1,2−ビス(トリクロロシリル)エタン、1,3,5−トリス(3−トリエトキシシリルプロピル)イソシアヌレート、1,3,5−トリス(3−トリメトキシシリルプロピル)イソシアヌレート、1,3−ジメチル−2−イミダゾリジノン、1,3−プロパンジアミン、1,4−ジアミノブタン、1−[3−(トリエトキシシリル)プロピル]−4,5−ジヒドロイミダゾール、1−グリシジル−4−(2−ピリジル)ピペラジン、1−グリシジル−4−フェニルピペラジン、1−グリシジル−4−メチルピペラジン、1−グリシジル−4−メチルホモピペラジン、1−グリシジルヘキサメチレンイミン、11−アミノウンデシルトリエトキシシラン、11−アミノウンデシルトリメトキシシラン、1−ベンジル−4−グリシジルピペラジン、2−(3,4−エポキシシクロヘキシル)エチルトリメトキシシラン、2−(4−モルフォリノジチオ)ベンゾチアゾール、2−(6−アミノエチル)−3−アミノプロピルトリメトキシシラン、2−(トリエトキシシリルエチル)ピリジン、2−(トリメトキシシリルエチル)ピリジン、2−(2−ピリジルエチル)チオプロピルトリメトキシシラン、2−(4−ピリジルエチル)チオプロピルトリメトキシシラン、2,2−ジエトキシ−1,6−ジアザ−2−シラシクロオクタン、2,2−ジメトキシ−1,6−ジアザ−2−シラシクロオクタン、2,3−ジクロロ−1,4−ナフトキノン、2,4−ジニトロベンゼンスルホニルクロライド、2,4−トリレンジイソシアナート、2−(4−ピリジルエチル)トリエトキシシラン、2−(4−ピリジルエチル)トリメトキシシラン、2−シアノエチルトリエトキシシラン、2−トリブチルスタニル−1,3−ブタジエン、2−(トリメトキシシリルエチル)ピリジン、2−ビニルピリジン、2−(4−ピリジルエチル)トリエトキシシラン、2−(4−ピリジルエチル)トリメトキシシラン、2−ラウリルチオエチルフェニルケトン、3−(1−ヘキサメチレンイミノ)プロピル(トリエトキシ)シラン、3−(1,3−ジメチルブチリデン)アミノプロピルトリエトキシシラン、3−(1,3−ジメチルブチリデン)アミノプロピルトリメトキシシラン、3−(2−アミノエチルアミノプロピル)トリメトキシシラン、3−(m−アミノフェノキシ)プロピルトリメトキシシラン、3−(N,N−ジメチルアミノ)プロピルトリエトキシシラン、3−(N,N−ジメチルアミノ)プロピルトリメトキシシラン、3−(N−メチルアミノ)プロピルトリエトキシシラン、3−(N−メチルアミノ)プロピルトリメトキシシラン、3−(N−アリルアミノ)プロピルトリメトキシシラン、3,4−ジアミノ安息香酸、3−アミノプロピルジメチルエトキシシラン、3−アミノプロピルトリエトキシシラン、3−アミノプロピルトリメトキシシラン、3−アミノプロピルトリス(メトキシジエトキシ)シラン、3−アミノプロピルジイソプロピルエトキシシラン、3−イソシアネートプロピルトリエトキシシラン、3−グリシドキシプロピルトリエトキシシラン、3−グリシドキシプロピルトリメトキシシラン、3−グリシドキシプロピルメチルジメトキシシラン、3−ジエチルアミノプロピルトリメトキシシラン、3−ジエトキシ(メチル)シリルプロピル無水コハク酸、3−(N,N−ジエチルアミノプロピル)トリエトキシシラン、3−(N,N−ジエチルアミノプロピル)トリメトキシシラン、3−(N,N−ジメチルアミノプロピル)ジエトキシメチルシラン、3−(N,N−ジメチルアミノプロピル)トリエトキシシラン、3−(N,N−ジメチルアミノプロピル)トリメトキシシラン、3−トリエトキシシリルプロピル無水コハク酸、3−トリエトキシシリルプロピル無水酢酸、3−トリフェノキシシリルプロピル無水コハク酸、3−トリフェノキシシリルプロピル無水酢酸、3−トリメトキシシリルプロピルベンゾチアゾールテトラスルフィド、3−ヘキサメチレンイミノプロピルトリエトキシシラン、3−メルカプトプロピルトリメトキシシラン、(3−トリエトキシシリルプロピル)ジエチレントリアミン、(3−トリメトキシシリルプロピル)ジエチレントリアミン、4,4’−ビス(ジエチルアミノ)ベンゾフェノン、4,4’−ビス(ジメチルアミノ)ベンゾフェノン、4’−(イミダゾール−1−イル)−アセトフェノン、4−〔3−(N,N−ジグリシジルアミノ)プロピル〕モルホリン、4−グリシジル−2,2,6,6−テトラメチルピぺリジニルオキシ、4−アミノブチルトリエトキシシラン、4−ビニルピリジン、4−モルホリノアセトフェノン、4−モルホリノベンゾフェノン、m−アミノフェニルトリメトキシシラン、N−(1,3−ジメチルブチリデン)−3−(トリエトキシシリル)−1−プロパンアミン、N−(1,3−ジメチルブチリデン)−3−(トリメトキシシリル)−1−プロパンアミン、N−(1−メチルエチリデン)−3−(トリエトキシシリル)−1−プロパンアミン、N−(2−アミノエチル)−3−アミノプロピルメチルジエトキシシラン、N−(2−アミノエチル)−3−アミノプロピルメチルジメトキシシラン、N−(2−アミノエチル)−3−アミノプロピルトリエトキシシラン、N−(2−アミノエチル)−3−アミノプロピルトリメトキシシラン、N−(2−アミノエチル)−11−アミノウンデシルトリエトキシシラン、N−(2−アミノエチル)−11−アミノウンデシルトリメトキシシラン、N−(2−アミノエチル)−3−アミノイソブチルメチルジエトキシシラン、N−(2−アミノエチル)−3−アミノイソブチルメチルジメトキシシラン、N−(3−ジエトキシメチルシリルプロピル)サクシンイミド、N−(3−トリエトキシシリルプロピル)−4,5−ジヒドロイミダゾール、N−(3−トリエトキシシリルプロピル)ピロール、N−(3−トリメトキシシリルプロピル)ピロール、N−3−[アミノ(ポリプロピレンオキシ)]アミノプロピルトリメトキシシラン、N−[5−(トリエトキシシリル)−2−アザ−1−オキソペンチル]カプロラクタム、N−[5−(トリメトキシシリル)−2−アザ−1−オキソペンチル]カプロラクタム、N−(6−アミノヘキシル)アミノメチルトリエトキシシラン、N−(6−アミノヘキシル)アミノメチルトリメトキシシラン、N−アリル−アザ−2,2−ジエトキシシラシクロペンタン、N−アリル−アザ−2,2−ジメトキシシラシクロペンタン、N−(シクロヘキシルチオ)フタルイミド、N−n−ブチル−アザ−2,2−ジエトキシシラシクロペンタン、N−n−ブチル−アザ−2,2−ジメトキシシラシクロペンタン、N,N,N’,N’−テトラエチルアミノベンゾフェノン、N,N,N’,N’−テトラメチルチオ尿素、N,N,N’,N’−テトラメチル尿素、N,N’−エチレン尿素、N,N’−ジエチルアミノベンゾフェノン、N,N’−ジエチルアミノベンゾフェノン、N,N’−ジエチルアミノベンゾフラン、N,N’−ジエチルカルバミン酸メチル、N,N’−ジエチル尿素、(N,N−ジエチル−3−アミノプロピル)トリエトキシシラン、(N,N−ジエチル−3−アミノプロピル)トリメトキシシラン、N,N−ジオクチル−N’−トリエトキシシリルプロピルウレア、N,N−ジオクチル−N’−トリメトキシシリルプロピルウレア、N,N−ジエチルカルバミン酸メチル、N,N−ジグリシジルシクロヘキシルアミン、N,N−ジメチル−o−トルイジン、N,N−ジメチルアミノスチレン、N,N−ジエチルアミノプロピルアクリルアミド、N,N−ジメチルアミノプロピルアクリルアミド、N−エチルアミノイソブチルトリエトキシシラン、N−エチルアミノイソブチルトリメトキシシラン、N−エチルアミノイソブチルメチルジエトキシシラン、N−オキシジエチレン−2−ベンゾチアゾールスルフェンアミド、N−シクロヘキシルアミノプロピルトリエトキシシラン、N−シクロヘキシルアミノプロピルトリメトキシシラン、N−メチルアミノプロピルメチルジメトキシシラン、N−メチルアミノプロピルメチルジエトキシシラン、N−ビニルベンジルアザシクロヘプタン、N−フェニルピロリドン、N−フェニルアミノプロピルトリエトキシシラン、N−フェニルアミノプロピルトリメトキシシラン、N−フェニルアミノメチルトリエトキシシラン、N−フェニルアミノメチルトリメトキシシラン、n−ブチルアミノプロピルトリエトキシシラン、n−ブチルアミノプロピルトリメトキシシラン、N−メチルアミノプロピルトリエトキシシラン、N−メチルアミノプロピルトリメトキシシラン、N−メチル−2−ピペリドン、N−メチル−2−ピロリドン、N−メチル−ε−カプロラクタム、N−メチルインドリノン、N−メチルピロリドン、p−(2−ジメチルアミノエチル)スチレン、p−アミノフェニルトリメトキシシラン、γ−グリシドキシプロピルトリメトキシシラン、γ−メタクリロキシプロピルトリメトキシシラン、(アミノエチルアミノ)−3−イソブチルジエトキシシラン、(アミノエチルアミノ)−3−イソブチルジメトキシシラン、(アミノエチルアミノメチル)フェネチルトリエトキシシラン、(アミノエチルアミノメチル)フェネチルトリメトキシシラン、アクリル酸、アジピン酸ジエチル、アセタミドプロピルトリメトキシシラン、アミノフェニルトリメトキシシラン、アミノベンゾフェノン、ウレイドプロピルトリエトキシシラン、ウレイドプロピルトリメトキシシラン、エチレンオキシド、オクタデシルジメチル(3−トリメトキシシリルプロピル)アンモニウムクロリド、グリシドキシプロピルトリエトキシシラン、グリシドキシプロピルトリメトキシシラン、グリセロールトリステアレート、クロロトリエトキシシラン、クロロプロピルトリエトキシシラン、クロロポリジメチルシロキサン、クロロメチルジフェノキシシラン、ジアリルジフェニルスズ、ジエチルアミノメチルトリエトキシシラン、ジエチルアミノメチルトリメトキシシラン、ジエチル(グリシジル)アミン、ジエチル、ジチオカルバミン酸2−ベンゾチアゾイルエステル、ジエトキシジクロロシラン、(シクロヘキシルアミノメチル)トリエトキシシラン、(シクロヘキシルアミノメチル)トリメトキシシラン、ジグリシジルポリシロキサン、ジクロロジフェノキシシラン、ジシクロヘキシルカルボジイミド、ジビニルベンゼン、ジフェニルカルボジイミド、ジフェニルシアナミド、ジフェニルメタンジイソシアネート、ジフェノキシメチルクロロシラン、ジブチルジクロロスズ、ジメチル(アセトキシ−メチルシロキサン)ポリジメチルシロキサン、ジメチルアミノメチルトリエトキシシラン、ジメチルアミノメチルトリメトキシシラン、ジメチル(メトキシ−メチルシロキサン)ポリジメチルシロキサン、ジメチルイミダゾリジノン、ジメチルエチレン尿素、ジメチルジクロロシラン、ジメチルスルホモイルクロライド、シルセスキオキサン、ソルビタントリオレイン酸エステル、ソルビタンモノラウリン酸エステル、チタンテトラキス(2−エチルヘキシオキシド)、テトラエトキシシラン、テトラグリシジル−1、3−ビスアミノメチルシクロヘキサン、テトラフェノキシシラン、テトラメチルチウラムジスルフィド、テトラメトキシシラン、トリエトキシビニルシラン、トリス(3−トリメトキシシリルプロピル)シアヌレート、トリフェニルホスフェート、トリフェノキシクロロシラン、トリフェノキシメチルケイ素、トリフェノキシメチルシラン、二酸化炭素、ビス(トリエトキシシリルプロピル)アミン、ビス(トリメトキシシリルプロピル)アミン、ビス[3−(トリエトキシシリル)プロピル]エチレンジアミン、ビス[3−(トリメトキシシリル)プロピル]エチレンジアミン、ビス[3−(トリエトキシシリル)プロピル]ウレア、ビス[(トリメトキシシリル)プロピル]ウレア、ビス(2−ヒドロキシメチル)−3−アミノプロピルトリエトキシシラン、ビス(2−ヒドロキシメチル)−3−ア
ミノプロピルトリメトキシシラン、ビス(2−エチルヘキサノエート)スズ、ビス(2−メチルブトキシ)メチルクロロシラン、ビス(3−トリエトキシシリルプロピル)テトラスルフィド、ビスジエチルアミノベンゾフェノン、ビスフェノールAジグリシジルエーテル、ビスフェノキシエタノールフルオレンジグリシジルエーテル、ビス(メチルジエトキシシリルプロピル)アミン、ビス(メチルジメトキシシリルプロピル)−N−メチルアミン、ヒドロキシメチルトリエトキシシラン、ビニルトリス(2−エチルヘキシルオキシ)シラン、ビニルベンジルジエチルアミン、ビニルベンジルジメチルアミン、ビニルベンジルトリブチルスズ、ビニルベンジルピペリジン、ビニルベンジルピロリジン、ピロリジン、フェニルイソシアナート、フェニルイソチオシアナート、(フェニルアミノメチル)メチルジメトキシシラン、(フェニルアミノメチル)メチルジエトキシシラン、フタル酸アミド、ヘキサメチレンジイソシアナート、ベンジリデンアニリン、ポリジフェニルメタンジイソシアネート、ポリジメチルシロキサン、メチル−4−ピリジルケトン、メチルカプロラクタム、メチルトリエトキシシラン、メチルトリフェノキシシラン、ラウリルチオプロピオン酸メチル、四塩化ケイ素等があげられる。
Examples of the modifier include 3-glycidoxypropyltrimethoxysilane, (3-triethoxysilylpropyl) tetrasulfide, 1- (4-N, N-dimethylaminophenyl) -1-phenylethylene, 1,1- Dimethoxytrimethylamine, 1,2-bis (trichlorosilyl) ethane, 1,3,5-tris (3-triethoxysilylpropyl) isocyanurate, 1,3,5-tris (3-trimethoxysilylpropyl) isocyanurate, 1,3-dimethyl-2-imidazolidinone, 1,3-propanediamine, 1,4-diaminobutane, 1- [3- (triethoxysilyl) propyl] -4,5-dihydroimidazole, 1-glycidyl- 4- (2-pyridyl) piperazine, 1-glycidyl-4-phenylpiperazine, 1-glycidyl 4-methylpiperazine, 1-glycidyl-4-methylhomopiperazine, 1-glycidylhexamethyleneimine, 11-aminoundecyltriethoxysilane, 11-aminoundecyltrimethoxysilane, 1-benzyl-4-glycidylpiperazine, 2 -(3,4-epoxycyclohexyl) ethyltrimethoxysilane, 2- (4-morpholinodithio) benzothiazole, 2- (6-aminoethyl) -3-aminopropyltrimethoxysilane, 2- (triethoxysilylethyl) ) Pyridine, 2- (trimethoxysilylethyl) pyridine, 2- (2-pyridylethyl) thiopropyltrimethoxysilane, 2- (4-pyridylethyl) thiopropyltrimethoxysilane, 2,2-diethoxy-1,6 -Diaza-2-silacyclooctane, 2, -Dimethoxy-1,6-diaza-2-silacyclooctane, 2,3-dichloro-1,4-naphthoquinone, 2,4-dinitrobenzenesulfonyl chloride, 2,4-tolylene diisocyanate, 2- (4- Pyridylethyl) triethoxysilane, 2- (4-pyridylethyl) trimethoxysilane, 2-cyanoethyltriethoxysilane, 2-tributylstannyl-1,3-butadiene, 2- (trimethoxysilylethyl) pyridine, 2- Vinylpyridine, 2- (4-pyridylethyl) triethoxysilane, 2- (4-pyridylethyl) trimethoxysilane, 2-laurylthioethylphenylketone, 3- (1-hexamethyleneimino) propyl (triethoxy) silane, 3- (1,3-Dimethylbutylidene) aminopropyltriethoxysila 3- (1,3-dimethylbutylidene) aminopropyltrimethoxysilane, 3- (2-aminoethylaminopropyl) trimethoxysilane, 3- (m-aminophenoxy) propyltrimethoxysilane, 3- (N , N-dimethylamino) propyltriethoxysilane, 3- (N, N-dimethylamino) propyltrimethoxysilane, 3- (N-methylamino) propyltriethoxysilane, 3- (N-methylamino) propyltrimethoxy Silane, 3- (N-allylamino) propyltrimethoxysilane, 3,4-diaminobenzoic acid, 3-aminopropyldimethylethoxysilane, 3-aminopropyltriethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyl Tris (methoxydiethoxy) silane, 3-amino Lopyldiisopropylethoxysilane, 3-isocyanatopropyltriethoxysilane, 3-glycidoxypropyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-diethylaminopropyltrimethoxy Silane, 3-diethoxy (methyl) silylpropyl succinic anhydride, 3- (N, N-diethylaminopropyl) triethoxysilane, 3- (N, N-diethylaminopropyl) trimethoxysilane, 3- (N, N-dimethyl) Aminopropyl) diethoxymethylsilane, 3- (N, N-dimethylaminopropyl) triethoxysilane, 3- (N, N-dimethylaminopropyl) trimethoxysilane, 3-triethoxysilylpropyl succinic anhydride, 3- Trier Xylsilylpropylacetic anhydride, 3-triphenoxysilylpropyl succinic anhydride, 3-triphenoxysilylpropyl acetic anhydride, 3-trimethoxysilylpropylbenzothiazole tetrasulfide, 3-hexamethyleneiminopropyltriethoxysilane, 3-mercaptopropyl Trimethoxysilane, (3-triethoxysilylpropyl) diethylenetriamine, (3-trimethoxysilylpropyl) diethylenetriamine, 4,4′-bis (diethylamino) benzophenone, 4,4′-bis (dimethylamino) benzophenone, 4′- (Imidazol-1-yl) -acetophenone, 4- [3- (N, N-diglycidylamino) propyl] morpholine, 4-glycidyl-2,2,6,6-tetramethylpiperidinyloxy, 4-aminobutyl Tiltlyethoxysilane, 4-vinylpyridine, 4-morpholinoacetophenone, 4-morpholinobenzophenone, m-aminophenyltrimethoxysilane, N- (1,3-dimethylbutylidene) -3- (triethoxysilyl) -1- Propanamine, N- (1,3-dimethylbutylidene) -3- (trimethoxysilyl) -1-propanamine, N- (1-methylethylidene) -3- (triethoxysilyl) -1-propanamine, N- (2-aminoethyl) -3-aminopropylmethyldiethoxysilane, N- (2-aminoethyl) -3-aminopropylmethyldimethoxysilane, N- (2-aminoethyl) -3-aminopropyltriethoxy Silane, N- (2-aminoethyl) -3-aminopropyltrimethoxysilane, N- (2-amino Ethyl) -11-aminoundecyltriethoxysilane, N- (2-aminoethyl) -11-aminoundecyltrimethoxysilane, N- (2-aminoethyl) -3-aminoisobutylmethyldiethoxysilane, N- (2-aminoethyl) -3-aminoisobutylmethyldimethoxysilane, N- (3-diethoxymethylsilylpropyl) succinimide, N- (3-triethoxysilylpropyl) -4,5-dihydroimidazole, N- (3 -Triethoxysilylpropyl) pyrrole, N- (3-trimethoxysilylpropyl) pyrrole, N-3- [amino (polypropyleneoxy)] aminopropyltrimethoxysilane, N- [5- (triethoxysilyl) -2- Aza-1-oxopentyl] caprolactam, N- [5- (trimethoxy Ryl) -2-aza-1-oxopentyl] caprolactam, N- (6-aminohexyl) aminomethyltriethoxysilane, N- (6-aminohexyl) aminomethyltrimethoxysilane, N-allyl-aza-2, 2-diethoxysilacyclopentane, N-allyl-aza-2,2-dimethoxysilacyclopentane, N- (cyclohexylthio) phthalimide, Nn-butyl-aza-2,2-diethoxysilacyclopentane, N -N-butyl-aza-2,2-dimethoxysilacyclopentane, N, N, N ', N'-tetraethylaminobenzophenone, N, N, N', N'-tetramethylthiourea, N, N, N ' , N′-tetramethylurea, N, N′-ethyleneurea, N, N′-diethylaminobenzophenone, N, N′-diethylaminobenzophenone N, N′-diethylaminobenzofuran, methyl N, N′-diethylcarbamate, N, N′-diethylurea, (N, N-diethyl-3-aminopropyl) triethoxysilane, (N, N-diethyl- 3-aminopropyl) trimethoxysilane, N, N-dioctyl-N′-triethoxysilylpropylurea, N, N-dioctyl-N′-trimethoxysilylpropylurea, methyl N, N-diethylcarbamate, N, N-diglycidylcyclohexylamine, N, N-dimethyl-o-toluidine, N, N-dimethylaminostyrene, N, N-diethylaminopropylacrylamide, N, N-dimethylaminopropylacrylamide, N-ethylaminoisobutyltriethoxysilane N-ethylaminoisobutyltrimethoxysilane, N Ethylaminoisobutylmethyldiethoxysilane, N-oxydiethylene-2-benzothiazolesulfenamide, N-cyclohexylaminopropyltriethoxysilane, N-cyclohexylaminopropyltrimethoxysilane, N-methylaminopropylmethyldimethoxysilane, N- Methylaminopropylmethyldiethoxysilane, N-vinylbenzylazacycloheptane, N-phenylpyrrolidone, N-phenylaminopropyltriethoxysilane, N-phenylaminopropyltrimethoxysilane, N-phenylaminomethyltriethoxysilane, N- Phenylaminomethyltrimethoxysilane, n-butylaminopropyltriethoxysilane, n-butylaminopropyltrimethoxysilane, N-methylaminopropyltrie Toxisilane, N-methylaminopropyltrimethoxysilane, N-methyl-2-piperidone, N-methyl-2-pyrrolidone, N-methyl-ε-caprolactam, N-methylindolinone, N-methylpyrrolidone, p- (2 -Dimethylaminoethyl) styrene, p-aminophenyltrimethoxysilane, γ-glycidoxypropyltrimethoxysilane, γ-methacryloxypropyltrimethoxysilane, (aminoethylamino) -3-isobutyldiethoxysilane, (aminoethyl) Amino) -3-isobutyldimethoxysilane, (aminoethylaminomethyl) phenethyltriethoxysilane, (aminoethylaminomethyl) phenethyltrimethoxysilane, acrylic acid, diethyl adipate, acetamidopropyltrimethoxysilane, aminophen Nyltrimethoxysilane, aminobenzophenone, ureidopropyltriethoxysilane, ureidopropyltrimethoxysilane, ethylene oxide, octadecyldimethyl (3-trimethoxysilylpropyl) ammonium chloride, glycidoxypropyltriethoxysilane, glycidoxypropyltrimethoxysilane , Glycerol tristearate, chlorotriethoxysilane, chloropropyltriethoxysilane, chloropolydimethylsiloxane, chloromethyldiphenoxysilane, diallyldiphenyltin, diethylaminomethyltriethoxysilane, diethylaminomethyltrimethoxysilane, diethyl (glycidyl) amine, diethyl , Dithiocarbamic acid 2-benzothiazoyl ester, diethoxydichlorosilane, ( (Cyclohexylaminomethyl) triethoxysilane, (cyclohexylaminomethyl) trimethoxysilane, diglycidylpolysiloxane, dichlorodiphenoxysilane, dicyclohexylcarbodiimide, divinylbenzene, diphenylcarbodiimide, diphenylcyanamide, diphenylmethane diisocyanate, diphenoxymethylchlorosilane, dibutyldichloro Tin, dimethyl (acetoxy-methylsiloxane) polydimethylsiloxane, dimethylaminomethyltriethoxysilane, dimethylaminomethyltrimethoxysilane, dimethyl (methoxy-methylsiloxane) polydimethylsiloxane, dimethylimidazolidinone, dimethylethyleneurea, dimethyldichlorosilane , Dimethylsulfoyl chloride, silsesquioxane , Sorbitan trioleate, sorbitan monolaurate, titanium tetrakis (2-ethylhexoxide), tetraethoxysilane, tetraglycidyl-1, 3-bisaminomethylcyclohexane, tetraphenoxysilane, tetramethylthiuram disulfide, tetramethoxy Silane, triethoxyvinylsilane, tris (3-trimethoxysilylpropyl) cyanurate, triphenyl phosphate, triphenoxychlorosilane, triphenoxymethylsilicon, triphenoxymethylsilane, carbon dioxide, bis (triethoxysilylpropyl) amine, bis (tri Methoxysilylpropyl) amine, bis [3- (triethoxysilyl) propyl] ethylenediamine, bis [3- (trimethoxysilyl) propyl] Range amine, bis [3- (triethoxysilyl) propyl] urea, bis [(trimethoxysilyl) propyl] urea, bis (2-hydroxymethyl) -3-aminopropyltriethoxysilane, bis (2-hydroxymethyl) -3-aminopropyltrimethoxysilane, bis (2-ethylhexanoate) tin, bis (2-methylbutoxy) methylchlorosilane, bis (3-triethoxysilylpropyl) tetrasulfide, bisdiethylaminobenzophenone, bisphenol A diglycidyl Ether, bisphenoxyethanol fluorenediglycidyl ether, bis (methyldiethoxysilylpropyl) amine, bis (methyldimethoxysilylpropyl) -N-methylamine, hydroxymethyltriethoxysilane, vinyltri (2-ethylhexyloxy) silane, vinylbenzyldiethylamine, vinylbenzyldimethylamine, vinylbenzyltributyltin, vinylbenzylpiperidine, vinylbenzylpyrrolidine, pyrrolidine, phenyl isocyanate, phenylisothiocyanate, (phenylaminomethyl) methyldimethoxysilane, ( Phenylaminomethyl) methyldiethoxysilane, phthalic acid amide, hexamethylene diisocyanate, benzylidene aniline, polydiphenylmethane diisocyanate, polydimethylsiloxane, methyl-4-pyridyl ketone, methylcaprolactam, methyltriethoxysilane, methyltriphenoxysilane, Examples include methyl lauryl thiopropionate and silicon tetrachloride.
上記変性剤のなかでも、ポリマーとの結合性がよい、フィラーとの親和性が高いという理由から、下記一般式(I)、(II)で表される化合物が好ましい。 Among the above modifiers, the compounds represented by the following general formulas (I) and (II) are preferable because they have good polymer binding properties and high affinity with fillers.
上記式(I)で表される化合物において、R1、R2及びR3は、同一若しくは異なって、アルキル基、アルコキシ基、シリルオキシ基、アセタール基、カルボキシル基(−COOH)、アルキル置換アミノ基、メルカプト基(−SH)又はこれらの誘導体を表す。上記アルキル基としては、例えば、メチル基、エチル基、n−プロピル基、イソプロピル基、n−ブチル基、t−ブチル基等の炭素数1〜4のアルキル基(好ましくは炭素数1〜3)等が挙げられる。上記アルコキシ基としては、例えば、メトキシ基、エトキシ基、n−プロポキシ基、イソプロポキシ基、n−ブトキシ基、t−ブトキシ基等の炭素数1〜8のアルコキシ基(好ましくは炭素数1〜6、より好ましくは炭素数1〜4)等が挙げられる。なお、アルコキシ基には、シクロアルコキシ基(シクロヘキシルオキシ基等の炭素数5〜8のシクロアルコキシ基等)、アリールオキシ基(フェノキシ基、ベンジルオキシ基等の炭素数6〜8のアリールオキシ基等)も含まれる。 In the compound represented by the above formula (I), R 1 , R 2 and R 3 are the same or different and are an alkyl group, an alkoxy group, a silyloxy group, an acetal group, a carboxyl group (—COOH), an alkyl-substituted amino group. Represents a mercapto group (—SH) or a derivative thereof. Examples of the alkyl group include an alkyl group having 1 to 4 carbon atoms (preferably having 1 to 3 carbon atoms) such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, and a t-butyl group. Etc. Examples of the alkoxy group include alkoxy groups having 1 to 8 carbon atoms such as methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group and t-butoxy group (preferably having 1 to 6 carbon atoms). More preferably, C1-C4) etc. are mentioned. The alkoxy group includes a cycloalkoxy group (cycloalkoxy group having 5 to 8 carbon atoms such as cyclohexyloxy group) and an aryloxy group (aryloxy group having 6 to 8 carbon atoms such as phenoxy group and benzyloxy group). ) Is also included.
上記シリルオキシ基としては、例えば、炭素数1〜20の脂肪族基、芳香族基が置換したシリルオキシ基(トリメチルシリルオキシ基、トリエチルシリルオキシ基、トリイソプロピルシリルオキシ基、ジエチルイソプロピルシリルオキシ基、t−ブチルジメチルシリルオキシ基、t−ブチルジフェニルシリルオキシ基、トリベンジルシリルオキシ基、トリフェニルシリルオキシ基、トリ−p−キシリルシリルオキシ基等)等が挙げられる。 Examples of the silyloxy group include a silyloxy group substituted with an aliphatic group having 1 to 20 carbon atoms and an aromatic group (trimethylsilyloxy group, triethylsilyloxy group, triisopropylsilyloxy group, diethylisopropylsilyloxy group, t- Butyldimethylsilyloxy group, t-butyldiphenylsilyloxy group, tribenzylsilyloxy group, triphenylsilyloxy group, tri-p-xylylsilyloxy group, etc.).
上記アセタール基としては、例えば、−C(RR′)−OR″、−O−C(RR′)−OR″で表される基を挙げることができる。前者としては、メトキシメチル基、エトキシメチル基、プロポキシメチル基、ブトキシメチル基、イソプロポキシメチル基、t−ブトキシメチル基、ネオペンチルオキシメチル基等が挙げられ、後者としては、メトキシメトキシ基、エトキシメトキシ基、プロポキシメトキシ基、i−プロポキシメトキシ基、n−ブトキシメトキシ基、t−ブトキシメトキシ基、n−ペンチルオキシメトキシ基、n−ヘキシルオキシメトキシ基、シクロペンチルオキシメトキシ基、シクロヘキシルオキシメトキシ基等を挙げることができる。 Examples of the acetal group include groups represented by -C (RR ')-OR "and -O-C (RR')-OR". Examples of the former include a methoxymethyl group, an ethoxymethyl group, a propoxymethyl group, a butoxymethyl group, an isopropoxymethyl group, a t-butoxymethyl group, and a neopentyloxymethyl group. The latter includes a methoxymethoxy group, an ethoxy group, and the like. Methoxy group, propoxymethoxy group, i-propoxymethoxy group, n-butoxymethoxy group, t-butoxymethoxy group, n-pentyloxymethoxy group, n-hexyloxymethoxy group, cyclopentyloxymethoxy group, cyclohexyloxymethoxy group, etc. Can be mentioned.
上記アルキル置換アミノ基とは、アミノ基に含まれる水素原子がすべてアルキル基により置換されたアミノ基をいう。置換されるアミノ基としては、例えば、上記R1、R2及びR3のアルキル基と同様の基を挙げることができる。アルキル置換アミノ基としては、例えば、ジメチルアミノ基、ジエチルアミノ基、N−メチル−n−プロピルアミノ基、ジ−n−プロピルアミノ基、ジイソプロピルアミノ基、ジ−n−ブチルアミノ基、ジ−イソブチルアミノ基、ジ−sec−ブチルアミノ基、ジ−tert−ブチルアミノ基、1−ピロリジニル基、ピペロジノ基、パーヒドロアジピニル基等が挙げられる。 The alkyl-substituted amino group refers to an amino group in which all hydrogen atoms contained in the amino group are substituted with alkyl groups. Examples of the amino group to be substituted include the same groups as the alkyl groups of R 1 , R 2 and R 3 described above. Examples of the alkyl-substituted amino group include dimethylamino group, diethylamino group, N-methyl-n-propylamino group, di-n-propylamino group, diisopropylamino group, di-n-butylamino group, di-isobutylamino. Group, di-sec-butylamino group, di-tert-butylamino group, 1-pyrrolidinyl group, piperidino group, perhydroadipynyl group and the like.
R1、R2及びR3としては、フィラーとの結合性がよい、又はフィラーとの親和性が高い、入手が容易であるという理由から、アルコキシ基、アルキル置換アミノ基が好ましい。 As R 1 , R 2, and R 3 , an alkoxy group and an alkyl-substituted amino group are preferable because they have good binding properties with fillers, high affinity with fillers, and easy availability.
上記式(I)で表される化合物において、R4及びR5のアルキル基としては、例えば、上記R1、R2及びR3のアルキル基と同様の基を挙げることができる。 In the compound represented by the above formula (I), examples of the alkyl group of R 4 and R 5 include the same groups as the alkyl groups of R 1 , R 2 and R 3 .
r(整数)としては、入手の容易性という理由から1〜5が好ましい。更には、rは2〜4がより好ましく、3が最も好ましい。rが0であると−NR4R5が脱離するためフィラーとの親和性が低くなる傾向があり、rが6以上であると入手が困難な場合や高価であることが多い。 As r (integer), 1 to 5 are preferable because of availability. Furthermore, r is more preferably from 2 to 4, and most preferably 3. When r is 0, —NR 4 R 5 is eliminated, so that the affinity with the filler tends to be low. When r is 6 or more, it is often difficult to obtain or expensive.
上記式(I)で表される化合物の具体例としては、上記変性剤として例示した3−(N,N−ジメチルアミノ)プロピルトリエトキシシラン、3−(N,N−ジメチルアミノ)プロピルトリメトキシシラン等が挙げられる。なかでも、3−(N,N−ジメチルアミノ)プロピルトリエトキシシランが好ましい。 Specific examples of the compound represented by the formula (I) include 3- (N, N-dimethylamino) propyltriethoxysilane and 3- (N, N-dimethylamino) propyltrimethoxy exemplified as the modifier. Silane etc. are mentioned. Of these, 3- (N, N-dimethylamino) propyltriethoxysilane is preferable.
上記式(II)で表される化合物において、R6、R7及びR8は、上記式(I)で表される化合物におけるR1、R2及びR3と同様である。 In the compound represented by the above formula (II), R 6 , R 7 and R 8 are the same as R 1 , R 2 and R 3 in the compound represented by the above formula (I).
上記式(II)で表される化合物において、R9の環状エーテル基としては、例えば、オキシラン基、オキセタン基、オキソラン基、オキサン基、オキセパン基、オキソカン基、オキソナン基、オキセカン基、オキセト基、オキソール基等のエーテル結合を1つ有する環状エーテル基、ジオキソラン基、ジオキサン基、ジオキセパン基、ジオキセカン基等のエーテル結合を2つ有する環状エーテル基、トリオキサン基等のエーテル結合を3つ有する環状エーテル基等が挙げられる。なかでも、エーテル結合を1つ有する炭素数2〜7の環状エーテル基が好ましく、エーテル結合を1つ有する炭素数2〜4の環状エーテル基がより好ましく、オキシラン基が更に好ましい。また、環状エーテル基は環骨格内に不飽和結合を有していないことが好ましい。 In the compound represented by the above formula (II), examples of the cyclic ether group of R 9 include an oxirane group, an oxetane group, an oxolane group, an oxane group, an oxepane group, an oxocan group, an oxonan group, an oxecan group, an oxet group, A cyclic ether group having one ether bond such as an oxol group, a cyclic ether group having two ether bonds such as a dioxolane group, a dioxane group, a dioxepane group and a dioxecan group, and a cyclic ether group having three ether bonds such as a trioxane group Etc. Among these, a C2-C7 cyclic ether group having one ether bond is preferable, a C2-C4 cyclic ether group having one ether bond is more preferable, and an oxirane group is still more preferable. The cyclic ether group preferably has no unsaturated bond in the ring skeleton.
p(整数)としては、入手の容易性という理由から1〜5が好ましい。更には、pは2〜4がより好ましく、3が最も好ましい。pが0であると、−O−(CH2)q−R9が脱離するためフィラーとの親和性が低くなる傾向があり、pが6以上であると入手が困難な場合や高価であることが多い。 As p (integer), 1-5 are preferable from the reason of availability. Further, p is more preferably from 2 to 4, and most preferably 3. When p is 0, —O— (CH 2 ) q —R 9 is desorbed, so the affinity with the filler tends to be low, and when p is 6 or more, it is difficult to obtain or expensive. There are often.
q(整数)としては、入手が容易という理由から0〜6が好ましい。更には、qは0〜3がより好ましく、1が最も好ましい。qが7以上であると入手が困難な場合や高価であることが多い。 q (integer) is preferably 0 to 6 because it is easily available. Furthermore, q is more preferably 0 to 3, and most preferably 1. When q is 7 or more, it is often difficult to obtain or expensive.
上記式(II)で表される化合物の具体例としては、上記変性剤として例示した3−グリシドキシプロピルトリメトキシシラン、3−グリシドキシプロピルトリエトキシシラン等が挙げられる。なかでも、3−グリシドキシプロピルトリエトキシシランが好ましい。 Specific examples of the compound represented by the formula (II) include 3-glycidoxypropyltrimethoxysilane and 3-glycidoxypropyltriethoxysilane exemplified as the modifier. Of these, 3-glycidoxypropyltriethoxysilane is preferable.
変性剤による重合体の変性方法としては、特公平6−53768号公報、特公平6−57767号公報等に記載されている方法等、従来公知の手法を用いることができる。例えば、重合体と変性剤とを接触させればよく、調製した重合体溶液中に変性剤を添加して反応させる方法等が挙げられる。 As a method for modifying a polymer with a modifier, conventionally known methods such as those described in JP-B-6-53768 and JP-B-6-57767 can be used. For example, a polymer and a modifier may be brought into contact with each other, and a method in which a modifier is added to the prepared polymer solution to cause a reaction may be mentioned.
本発明においては、重合体と変性剤とを反応させた後に、必要に応じて、公知の老化防止剤や重合反応を停止する目的でアルコールなどを加えてもよい。 In the present invention, after reacting the polymer and the modifier, if necessary, a known anti-aging agent or alcohol may be added for the purpose of stopping the polymerization reaction.
重合体の重量平均分子量(Mw)は、5×104〜1×106が好ましく、上限は7×105がさらに好ましい。Mwが5×104未満ではヒステリシスロスが大きく十分な低燃費性が得られにくいだけでなく、耐摩耗性も低下する傾向がある。一方、Mwが1.0×106を越えると加工性が低下する傾向がある。
なお、重量平均分子量は、後述の実施例に記載の方法により測定した値である。
The weight average molecular weight (Mw) of the polymer is preferably 5 × 10 4 to 1 × 10 6 and the upper limit is more preferably 7 × 10 5 . If Mw is less than 5 × 10 4 , not only is the hysteresis loss large and sufficient fuel economy is difficult to obtain, but the wear resistance also tends to decrease. On the other hand, when Mw exceeds 1.0 × 10 6 , workability tends to decrease.
In addition, a weight average molecular weight is the value measured by the method as described in the below-mentioned Example.
重合体の重合末端の変性率(末端変性率)は5%以上が好ましく、30%以上がより好ましく、80%以上が更に好ましい。末端変性率が5%未満では、フィラーとの親和性が低くなる傾向がある。また、該末端変性率の上限は、特に限定されない。
なお、末端変性率は、後述の実施例に記載の方法により測定した値である。
The polymerization terminal modification rate (terminal modification rate) of the polymer is preferably 5% or more, more preferably 30% or more, and still more preferably 80% or more. If the terminal modification rate is less than 5%, the affinity with the filler tends to be low. Further, the upper limit of the terminal modification rate is not particularly limited.
The terminal modification rate is a value measured by the method described in Examples below.
ゴム成分100質量%中の重合体の含有量は、好ましくは8質量%以上、より好ましくは10質量%以上、更に好ましくは20質量%以上である。8質量%未満であると、氷上性能とドライ操縦安定性の改善効果が得られにくくなる傾向がある。該重合体の含有量は、好ましくは70質量%以下、より好ましくは60質量%以下、更に好ましくは50質量%以下である。70質量%を超えると、破壊強度が極端に悪化する傾向がある。 The content of the polymer in 100% by mass of the rubber component is preferably 8% by mass or more, more preferably 10% by mass or more, and further preferably 20% by mass or more. If it is less than 8% by mass, the effect of improving the performance on ice and the stability of dry handling tends to be difficult to obtain. The content of the polymer is preferably 70% by mass or less, more preferably 60% by mass or less, and still more preferably 50% by mass or less. When it exceeds 70 mass%, there exists a tendency for fracture strength to deteriorate extremely.
エポキシ化ジエン系ゴムとしては、例えば、エポキシ化天然ゴム、エポキシ化イソプレンゴム、エボキシ化ブタジエンゴム、エポキシ化ブタジエンアクリロニトリルゴム、エポキシ化スチレンブタジエンゴム、エポキシ化イソプレンブタジエンゴムなどが挙げられる。これらは単独で用いてもよく、二種類以上を組み合わせてもよいが、これらの中で、入手が容易であるなどの実用面での観点からエポキシ化天然ゴム、エポキシ化ブタジエンゴムが好ましい。 Examples of the epoxidized diene rubber include epoxidized natural rubber, epoxidized isoprene rubber, epoxidized butadiene rubber, epoxidized butadiene acrylonitrile rubber, epoxidized styrene butadiene rubber, and epoxidized isoprene butadiene rubber. These may be used alone or in combination of two or more. Among them, epoxidized natural rubber and epoxidized butadiene rubber are preferred from the viewpoint of practical use such as availability.
上記エポキシ化ジエン系ゴムは、市販のエポキシ化ジエン系ゴムを使用しても、ジエン系ゴム(例えば、天然ゴム(NR)、ブタジエンゴム(BR)、イソプレンゴム等)をエポキシ化したものを使用してもよい。ジエン系ゴムをエポキシ化する方法は、特に限定されず、クロルヒドリン法、直接酸化法、過酸化水素法、アルキルヒドロペルオキシド法、過酸法などがあげられる(特公平4−26617号公報、特開平2−110182号公報、英国特許第2113692号明細書等)。過酸法としては例えば、ジエン系ゴムに過酢酸や過ギ酸などの有機過酸を反応させる方法などがあげられる。なお、有機過酸の量や反応時間を調整することにより、様々なエポキシ化率のエポキシ化ジエン系ゴムを調製することができる。 The epoxidized diene rubber may be a epoxidized diene rubber (for example, natural rubber (NR), butadiene rubber (BR), isoprene rubber, etc.) even if a commercially available epoxidized diene rubber is used. May be. The method for epoxidizing the diene rubber is not particularly limited, and examples thereof include a chlorohydrin method, a direct oxidation method, a hydrogen peroxide method, an alkyl hydroperoxide method, a peracid method, and the like (Japanese Patent Publication No. 4-26617, Japanese Patent Application Laid-Open No. Hei. No. 2-110182, British Patent No. 2113692, etc.). Examples of the peracid method include a method of reacting a diene rubber with an organic peracid such as peracetic acid or performic acid. It should be noted that epoxidized diene rubbers with various epoxidation rates can be prepared by adjusting the amount of organic peracid and the reaction time.
エポキシ化されるNRとしては、特に限定されず、例えば、SIR20、RSS♯3、TSR20、脱タンパク質天然ゴム(DPNR)、高純度天然ゴム(HPNR)等、タイヤ工業において一般的なものを使用できる。
エポキシ化されるBRとしては、特に限定されず、例えば、日本ゼオン(株)製のBR1220、宇部興産(株)製のBR130B、BR150B等の高シス含有量のBR、宇部興産(株)製のVCR412、VCR617等のシンジオタクチックポリブタジエン結晶を含有するBR等を使用できる。なかでも、耐摩耗性が良好であるという理由から、シス含量が90質量%以上のものが好ましい。
The NR to be epoxidized is not particularly limited. For example, SIR20, RSS # 3, TSR20, deproteinized natural rubber (DPNR), high-purity natural rubber (HPNR), etc., which are common in the tire industry can be used. .
The BR to be epoxidized is not particularly limited. For example, BR1220 manufactured by Nippon Zeon Co., Ltd., BR130B manufactured by Ube Industries, Ltd., BR150B and other high cis content BR, manufactured by Ube Industries, Ltd. BR containing syndiotactic polybutadiene crystals such as VCR 412 and VCR 617 can be used. Of these, those having a cis content of 90% by mass or more are preferred because of their good wear resistance.
エポキシ化ジエン系ゴムのエポキシ化率は、0.5モル%以上、好ましくは1.0モル%以上、より好ましくは2.0モル%以上である。エポキシ化率が0.5モル%未満では、フィラーとの親和性が低いため、フィラーが前述の末端変性重合体側に偏在する傾向があり、耐摩耗性、走行安定性(特に、ドライ路面での走行安定性)の改善効果が充分に得られない傾向がある。また、エポキシ化率は、50モル%以下、好ましくは40モル%以下、より好ましくは30モル%以下である。エポキシ化率が50モル%をこえると、ゴムの硬度が上がるため、充分な氷上性能が得られにくくなる傾向がある。
なお、本発明において、エポキシ化率とは、エポキシ化される前のゴム中の二重結合の総数に対するエポキシ化された二重結合の数の割合(モル%)のことである。
また、エポキシ化率は、後述の実施例に記載の方法により測定した値である。
The epoxidation rate of the epoxidized diene rubber is 0.5 mol% or more, preferably 1.0 mol% or more, more preferably 2.0 mol% or more. When the epoxidation rate is less than 0.5 mol%, since the affinity with the filler is low, the filler tends to be unevenly distributed on the terminal-modified polymer side, and wear resistance, running stability (especially on a dry road surface) There is a tendency that the effect of improving the driving stability is not sufficiently obtained. The epoxidation rate is 50 mol% or less, preferably 40 mol% or less, more preferably 30 mol% or less. When the epoxidation rate exceeds 50 mol%, the hardness of the rubber increases, and thus sufficient on-ice performance tends to be difficult to obtain.
In the present invention, the epoxidation rate is the ratio (mol%) of the number of epoxidized double bonds to the total number of double bonds in the rubber before being epoxidized.
Moreover, an epoxidation rate is the value measured by the method as described in the below-mentioned Example.
ゴム成分100質量%中のエポキシ化ジエン系ゴムの含有量は、好ましくは10質量%以上、より好ましくは15質量%以上である。10質量%未満であると、氷上性能とドライ操縦安定性の改善効果が得られにくくなる傾向がある。該エポキシ化ジエン系ゴムの含有量は、好ましくは30質量%以下、より好ましくは25質量%以下である。30質量%を超えると、フィラーがエポキシ化ジエン系ゴム側に偏在する傾向があり、耐摩耗性、走行安定性(特に、ドライ路面での走行安定性)の改善効果が充分に得られない傾向がある。 The content of the epoxidized diene rubber in 100% by mass of the rubber component is preferably 10% by mass or more, more preferably 15% by mass or more. If it is less than 10% by mass, the effect of improving the performance on ice and the stability of dry handling tends to be difficult to obtain. The content of the epoxidized diene rubber is preferably 30% by mass or less, more preferably 25% by mass or less. If it exceeds 30% by mass, the filler tends to be unevenly distributed on the epoxidized diene rubber side, and the effect of improving wear resistance and running stability (especially running stability on dry road surface) tends not to be sufficiently obtained. There is.
上記重合体、エポキシ化ジエン系ゴム以外に使用できるゴム成分としては、例えば、NR、BR、スチレンブタジエンゴム(SBR)、イソプレンゴム(IR)、エチレンプロピレンジエンゴム(EPDM)、クロロプレンゴム(CR)、アクリロニトリルブタジエンゴム(NBR)、ブチルゴム(IIR)、ハロゲン化ブチルゴム(X−IIR)などのジエン系ゴムが挙げられる。なかでも、氷上性能、ドライ操縦安定性、および耐摩耗性をバランスよく示すことから、NR、BR、SBRが好ましい。これらのゴムは単独で用いてもよく、2種以上組み合わせてもよい。NR、BRとしては、上記NR、BRを好適に使用できる。なお、本明細書において、単にジエン系ゴムと記載する場合には、上記重合体、エポキシ化ジエン系ゴムを含まないこととする。 Examples of rubber components that can be used in addition to the polymer and the epoxidized diene rubber include NR, BR, styrene butadiene rubber (SBR), isoprene rubber (IR), ethylene propylene diene rubber (EPDM), and chloroprene rubber (CR). And diene rubbers such as acrylonitrile butadiene rubber (NBR), butyl rubber (IIR), and halogenated butyl rubber (X-IIR). Among these, NR, BR, and SBR are preferable because they exhibit a good balance of on-ice performance, dry handling stability, and wear resistance. These rubbers may be used alone or in combination of two or more. As NR and BR, the above NR and BR can be preferably used. In the present specification, the term “diene rubber” does not include the above polymer and epoxidized diene rubber.
ゴム成分100質量%中のBRの含有量は、好ましくは10質量%以上、より好ましくは20質量%以上である。10質量%未満であると、充分な耐摩耗性が得られない傾向がある。該BRの含有量は、好ましくは70質量%以下、より好ましくは60質量%以下である。70質量%を超えると、充分な耐摩耗性が得られない傾向がある。 The content of BR in 100% by mass of the rubber component is preferably 10% by mass or more, more preferably 20% by mass or more. If it is less than 10% by mass, sufficient wear resistance tends to be not obtained. The BR content is preferably 70% by mass or less, more preferably 60% by mass or less. When it exceeds 70 mass%, there is a tendency that sufficient wear resistance cannot be obtained.
本発明では、氷上グリップ性能向上を目的としてシリカが使用される。これにより、転がり抵抗とウェットグリップ性能のバランスも改善できる。シリカとしては特に限定されず、例えば、乾式法シリカ(無水ケイ酸)、湿式法シリカ(含水ケイ酸)等が挙げられるが、シラノール基が多いという理由から、湿式法シリカが好ましい。シリカは、単独で用いてもよく、2種以上を併用してもよい。 In the present invention, silica is used for the purpose of improving the grip performance on ice. This can also improve the balance between rolling resistance and wet grip performance. The silica is not particularly limited, and examples thereof include dry process silica (anhydrous silicic acid), wet process silica (hydrous silicic acid), and the like, but wet process silica is preferable because of its large number of silanol groups. Silica may be used alone or in combination of two or more.
シリカの窒素吸着比表面積(N2SA)は、好ましくは50m2/g以上、より好ましくは80m2/g以上である。50m2/g未満であると、補強効果が小さく、耐摩耗性が低下する傾向がある。また、シリカのN2SAは、好ましくは300m2/g以下、より好ましくは250m2/g以下である。300m2/gを超えると、分散性が悪く、ヒステリシスロスが増大し、燃費性能が低下する傾向にある。
なお、シリカの窒素吸着比表面積は、ASTM D3037−81に準じてBET法で測定される値である。
The nitrogen adsorption specific surface area (N 2 SA) of silica is preferably 50 m 2 / g or more, more preferably 80 m 2 / g or more. If it is less than 50 m 2 / g, the reinforcing effect is small, and the wear resistance tends to decrease. Further, N 2 SA of silica is preferably 300 m 2 / g or less, more preferably 250 m 2 / g or less. When it exceeds 300 m 2 / g, the dispersibility is poor, the hysteresis loss increases, and the fuel efficiency tends to decrease.
The nitrogen adsorption specific surface area of silica is a value measured by the BET method according to ASTM D3037-81.
シリカの含有量は、ゴム成分100質量部に対して、好ましくは5質量部以上、より好ましくは10質量部以上、更に好ましくは30質量部以上である。5質量部未満では、耐摩耗性の向上効果が充分に得られない傾向がある。該シリカの含有量は、150質量部以下、好ましくは100質量部以下、より好ましくは80質量部以下である。150質量部を超えると、加工性が悪化する傾向がある。 The content of silica is preferably 5 parts by mass or more, more preferably 10 parts by mass or more, and further preferably 30 parts by mass or more with respect to 100 parts by mass of the rubber component. If the amount is less than 5 parts by mass, the effect of improving the wear resistance tends to be insufficient. The content of the silica is 150 parts by mass or less, preferably 100 parts by mass or less, more preferably 80 parts by mass or less. If it exceeds 150 parts by mass, the workability tends to deteriorate.
本発明では、シリカとともにシランカップリング剤を併用しても良い。シランカップリング剤としては、例えば、ビス(3−トリエトキシシリルプロピル)テトラスルフィド、ビス(3−トリエトキシシリルプロピル)トリスルフィド、ビス(3−トリエトキシシリルプロピル)ジスルフィド、ビス(2−トリエトキシシリルエチル)テトラスルフィド、ビス(3−トリメトキシシリルプロピル)テトラスルフィド、ビス(2−トリメトキシシリルエチル)テトラスルフィド、3−メルカプトプロピルトリメトキシシラン、3−メルカプトプロピルトリエトキシシラン、2−メルカプトエチルトリメトキシシラン、2−メルカプトエチルトリエトキシシラン、3−トリメトキシシリルプロピル−N,N−ジメチルチオカルバモイルテトラスルフィド、3−トリエトキシシリルプロピル−N,N−ジメチルチオカルバモイルテトラスルフィド、2−トリエトキシシリルエチル−N,N−ジメチルチオカルバモイルテトラスルフィド、3−トリメトキシシリルプロピルベンゾチアゾールテトラスルフィド、3−トリエトキシシリルプロピルベンゾチアゾリルテトラスルフィド、3−トリエトキシシリルプロピルメタクリレートモノスルフィド、3−トリメトキシシリルプロピルメタクリレートモノスルフィド、ビス(3−ジエトキシメチルシリルプロピル)テトラスルフィド、3−メルカプトプロピルジメトキシメチルシラン、ジメトキシメチルシリルプロピル−N,N−ジメチルチオカルバモイルテトラスルフィド、ジメトキシメチルシリルプロピルベンゾチアゾールテトラスルフィドなどがあげられる。なかでも、補強性改善効果などの点から、ビス(3−トリエトキシシリルプロピル)テトラスルフィドおよび3−トリメトキシシリルプロピルベンゾチアゾリルテトラスルフィドが好ましい。これらのシランカップリング剤は単独で用いてもよく、2種以上を組み合わせて用いてもよい。 In the present invention, a silane coupling agent may be used in combination with silica. Examples of the silane coupling agent include bis (3-triethoxysilylpropyl) tetrasulfide, bis (3-triethoxysilylpropyl) trisulfide, bis (3-triethoxysilylpropyl) disulfide, and bis (2-triethoxy). Silylethyl) tetrasulfide, bis (3-trimethoxysilylpropyl) tetrasulfide, bis (2-trimethoxysilylethyl) tetrasulfide, 3-mercaptopropyltrimethoxysilane, 3-mercaptopropyltriethoxysilane, 2-mercaptoethyl Trimethoxysilane, 2-mercaptoethyltriethoxysilane, 3-trimethoxysilylpropyl-N, N-dimethylthiocarbamoyl tetrasulfide, 3-triethoxysilylpropyl-N, N-dimethylthiocarb Moyl tetrasulfide, 2-triethoxysilylethyl-N, N-dimethylthiocarbamoyl tetrasulfide, 3-trimethoxysilylpropylbenzothiazole tetrasulfide, 3-triethoxysilylpropylbenzothiazolyl tetrasulfide, 3-triethoxysilyl Propyl methacrylate monosulfide, 3-trimethoxysilylpropyl methacrylate monosulfide, bis (3-diethoxymethylsilylpropyl) tetrasulfide, 3-mercaptopropyldimethoxymethylsilane, dimethoxymethylsilylpropyl-N, N-dimethylthiocarbamoyl tetrasulfide And dimethoxymethylsilylpropylbenzothiazole tetrasulfide. Of these, bis (3-triethoxysilylpropyl) tetrasulfide and 3-trimethoxysilylpropylbenzothiazolyl tetrasulfide are preferable from the viewpoint of improving reinforcing properties. These silane coupling agents may be used alone or in combination of two or more.
シランカップリング剤の含有量は、シリカ100質量部に対して、1質量部以上が好ましく、2質量部以上がより好ましい。1質量部未満では、未加硫ゴム組成物の粘度が高く加工性が悪くなる傾向がある。また、該シランカップリング剤の含有量は、20質量部以下が好ましく、15質量部以下がより好ましく、10質量部以下が更に好ましい。20質量部を超えると、その配合量ほどのシランカップリング剤の配合効果が得られず、コストが高くなる傾向がある。 The content of the silane coupling agent is preferably 1 part by mass or more and more preferably 2 parts by mass or more with respect to 100 parts by mass of silica. If it is less than 1 part by mass, the viscosity of the unvulcanized rubber composition tends to be high and the processability tends to deteriorate. Moreover, 20 mass parts or less are preferable, as for content of this silane coupling agent, 15 mass parts or less are more preferable, and 10 mass parts or less are still more preferable. If it exceeds 20 parts by mass, the blending effect of the silane coupling agent as much as the blending amount cannot be obtained, and the cost tends to increase.
本発明のゴム組成物には、カーボンブラック等の補強剤、加硫剤、加硫促進剤、各種オイル、老化防止剤、軟化剤、可塑剤などのタイヤ用または一般のゴム組成物用に配合される各種配合剤および添加剤を配合することができる。また、これらの配合剤、添加剤の含有量も一般的な量とすることができる。 The rubber composition of the present invention is compounded for tires or general rubber compositions such as reinforcing agents such as carbon black, vulcanizing agents, vulcanization accelerators, various oils, anti-aging agents, softeners, and plasticizers. Various additives and additives can be blended. Moreover, the content of these compounding agents and additives can also be set to general amounts.
本発明では、補強剤としてカーボンブラックを含有することが好ましい。カーボンブラックを配合することにより、補強性を高めることができるとともに、耐摩耗性を高めることができる。使用できるカーボンブラックの例としては、GPF、FEF、HAF、ISAF、SAFなどが挙げられるが、特に限定されるものではない。カーボンブラックは単独で用いてもよく、2種以上を組み合わせて用いてもよい。 In the present invention, it is preferable to contain carbon black as a reinforcing agent. By blending carbon black, it is possible to enhance the reinforcing property and the wear resistance. Examples of carbon black that can be used include GPF, FEF, HAF, ISAF, and SAF, but are not particularly limited. Carbon black may be used alone or in combination of two or more.
カーボンブラックのチッ素吸着比表面積(N2SA)は80m2/g以上が好ましく、100m2/g以上がより好ましい。80m2/g未満では、十分な氷上性能(ウェットグリップ性能)が得られず、また耐摩耗性が低下する傾向がある。また、カーボンブラックのチッ素吸着比表面積は280m2/g以下が好ましく、250m2/g以下がより好ましく、175m2/g以下が更に好ましい。280m2/gを超えると、分散性に劣り、耐摩耗性が低下する傾向がある。
なお、カーボンブラックのチッ素吸着比表面積は、JIS K6217のA法によって求められる。
The nitrogen adsorption specific surface area (N 2 SA) of carbon black is preferably 80 m 2 / g or more, and more preferably 100 m 2 / g or more. If it is less than 80 m < 2 > / g, sufficient on-ice performance (wet grip performance) cannot be obtained, and the wear resistance tends to decrease. Further, the nitrogen adsorption specific surface area of the carbon black is preferably at most 280 meters 2 / g, more preferably not more than 250 meters 2 / g, more preferably 175 m 2 / g or less. When it exceeds 280 m 2 / g, the dispersibility is inferior and the wear resistance tends to be lowered.
In addition, the nitrogen adsorption specific surface area of carbon black is calculated | required by A method of JISK6217.
上記ゴム組成物がカーボンブラックを含有する場合、カーボンブラックの含有量は、ゴム成分100質量部に対して、好ましくは5質量部以上、より好ましくは10質量部以上である。5質量部未満では、耐摩耗性が低下する傾向がある。また、該カーボンブラックの含有量は、好ましくは150質量部以下、より好ましくは100質量部以下、更に好ましくは50質量部以下、特に好ましくは30質量部以下である。150質量部を超えると、加工性が悪化する傾向がある。 When the rubber composition contains carbon black, the content of carbon black is preferably 5 parts by mass or more, more preferably 10 parts by mass or more with respect to 100 parts by mass of the rubber component. If it is less than 5 parts by mass, the wear resistance tends to decrease. The carbon black content is preferably 150 parts by mass or less, more preferably 100 parts by mass or less, still more preferably 50 parts by mass or less, and particularly preferably 30 parts by mass or less. If it exceeds 150 parts by mass, the workability tends to deteriorate.
本発明のゴム組成物は、一般的な方法で製造される。すなわち、バンバリーミキサーやニーダー、オープンロールなどで前記各成分を混練りし、その後加硫する方法等により製造できる。 The rubber composition of the present invention is produced by a general method. That is, it can be produced by a method of kneading the above components with a Banbury mixer, a kneader, an open roll or the like and then vulcanizing.
本発明のゴム組成物は、スタッドレスタイヤの各部材(特に、トレッドゴム)に好適に使用できる。 The rubber composition of the present invention can be suitably used for each member (particularly tread rubber) of a studless tire.
本発明のスタッドレスタイヤは、上記ゴム組成物を用いて通常の方法によって製造できる。すなわち、ゴム組成物を未加硫の段階で各部材の形状に合わせて押し出し加工し、タイヤ成型機上にて通常の方法にて成形し、他のタイヤ部材とともに貼り合わせ、未加硫タイヤを形成する。この未加硫タイヤを加硫機中で加熱加圧してタイヤを製造できる。本発明により得られるスタッドレスタイヤは、耐摩耗性を維持しつつ、氷上性能及びドライ操縦安定性をバランスよく改善できる。 The studless tire of the present invention can be produced by a normal method using the rubber composition. That is, the rubber composition is extruded in accordance with the shape of each member at an unvulcanized stage, molded by a normal method on a tire molding machine, and bonded together with other tire members to form an unvulcanized tire. Form. This unvulcanized tire can be heated and pressurized in a vulcanizer to produce a tire. The studless tire obtained by the present invention can improve on-ice performance and dry handling stability in a well-balanced manner while maintaining wear resistance.
実施例に基づいて、本発明を具体的に説明するが、本発明はこれらのみに限定されるものではない。 The present invention will be specifically described based on examples, but the present invention is not limited to these examples.
以下、製造例1〜4(重合体(1)〜(4)の合成)で使用した各種薬品について、まとめて説明する。なお、薬品は必要に応じて定法に従い精製を行った。
シクロヘキサン:関東化学(株)製のシクロヘキサン
スチレン:関東化学(株)製のスチレン
ブタジエン:高千穂化学工業(株)製の1,3−ブタジエン
THF:関東化学(株)製のテトラヒドロフラン
トルエン:関東化学(株)製のトルエン
メタノール:関東化学(株)製のメタノール
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
3−(N,N−ジメチルアミノプロピル)トリエトキシシラン:アヅマックス社製の3−(N,N−ジメチルアミノプロピル)トリエトキシシラン(式(I)において、R1、R2及びR3=エトキシ基、R4及びR5=メチル基、r=3)
3−グリシドキシプロピルトリエトキシシラン:信越化学工業(株)製の3−グリシドキシプロピルトリエトキシシラン(式(II)において、R6、R7及びR8=エトキシ基、R9=オキシラン基、p=3、q=1)
イソプロパノール:関東化学(株)製のイソプロパノール
2,6−tert−ブチル−p−クレゾール:関東化学(株)製の2,6−tert−ブチル−p−クレゾール
Hereinafter, various chemicals used in Production Examples 1 to 4 (synthesis of polymers (1) to (4)) will be described together. In addition, the chemical | medical agent refine | purified according to the usual method as needed.
Cyclohexane: cyclohexane styrene manufactured by Kanto Chemical Co., Ltd .: styrene butadiene manufactured by Kanto Chemical Co., Ltd .: 1,3-butadiene THF manufactured by Takachiho Chemical Industry Co., Ltd .: tetrahydrofuran toluene manufactured by Kanto Chemical Co., Ltd .: Kanto Chemical ( Toluene methanol manufactured by Kanto Chemical Co., Ltd. Methanol 1.6M n-butyllithium hexane solution: 1.6M n-butyllithium hexane solution manufactured by Kanto Chemical Co., Ltd. 3- (N, N-dimethylamino) Propyl) triethoxysilane: 3- (N, N-dimethylaminopropyl) triethoxysilane (in formula (I), R 1 , R 2 and R 3 = ethoxy group, R 4 and R 5 = methyl Group, r = 3)
3-glycidoxypropyltriethoxysilane: 3-glycidoxypropyltriethoxysilane manufactured by Shin-Etsu Chemical Co., Ltd. (in the formula (II), R 6 , R 7 and R 8 = ethoxy group, R 9 = oxirane Group, p = 3, q = 1)
Isopropanol: Isopropanol 2,6-tert-butyl-p-cresol manufactured by Kanto Chemical Co., Ltd .: 2,6-tert-butyl-p-cresol manufactured by Kanto Chemical Co., Ltd.
得られた重合体の分析は以下の方法で行った。 The obtained polymer was analyzed by the following method.
(重量平均分子量(Mw)及び数平均分子量(Mn)の測定)
MwおよびMn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、標準ポリスチレンにより換算して測定した。
(Measurement of weight average molecular weight (Mw) and number average molecular weight (Mn))
Mw and Mn are standard polystyrene using gel permeation chromatograph (GPC) (GPC-8000 series, manufactured by Tosoh Corporation), detector: differential refractometer, column: TSKGE SUPERMALTPORE HZ-M manufactured by Tosoh Corporation. Measured by conversion.
(重合体の重合末端の変性率(末端変性率)の測定)
重合体の末端変性率は、下記式を用いて計算した。
末端変性率(%)=(F−G)/(H/I)×100
(式中、Fは変性剤添加量(mol)、Gは重合終了後の変性剤の残量(mol)、Hは得られた重合体の重量、Iは重合体の数平均分子量を表す。Gは、反応溶液の一部を抜き取りアルコールでゴムを沈殿させた後、溶媒に残留する変性剤の比率を島津製作所(株)製ガスクロマトグラフィーGC2010(FID検出器)を使用し、検量線法を用いて計算した。)
(Measurement of polymer terminal modification rate (terminal modification rate))
The terminal modification rate of the polymer was calculated using the following formula.
Terminal modification rate (%) = (F−G) / (H / I) × 100
(In the formula, F represents the amount of the modifier added (mol), G represents the remaining amount of the modifier after the polymerization (mol), H represents the weight of the polymer obtained, and I represents the number average molecular weight of the polymer. G is a calibration curve method using a gas chromatography GC2010 (FID detector) manufactured by Shimadzu Corporation after extracting a part of the reaction solution and precipitating rubber with alcohol and then using a gas chromatography GC2010 (FID detector) manufactured by Shimadzu Corporation. Calculated using.)
(製造例1)
(重合体(1)の合成)
十分に窒素置換した1000ml耐圧製容器にシクロヘキサン600ml、ブタジエン1mol、THF1mlを加え、40℃に加温後、1.6M n−ブチルリチウムヘキサン溶液0.4ml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)トリエトキシシランを1mmol添加した。さらに30分攪拌した後、イソプロパノール3mlを加えた。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50g得た。重合体(1)のMwは23.5×104、Mnは22.6×104、末端変性率は93%であった。
(Production Example 1)
(Synthesis of polymer (1))
To a 1000 ml pressure-resistant container sufficiently purged with nitrogen, 600 ml of cyclohexane, 1 mol of butadiene and 1 ml of THF were added, heated to 40 ° C., 0.4 ml of 1.6 M n-butyllithium hexane solution was added and stirred. After 3 hours, 1 mmol of 3- (N, N-dimethylaminopropyl) triethoxysilane was added. After stirring for another 30 minutes, 3 ml of isopropanol was added. After adding 1 g of 2,6-tert-butyl-p-cresol to the reaction solution, it was reprecipitated with methanol and dried by heating to obtain 50 g of the polymer (1). Mw of the polymer (1) was 23.5 × 10 4 , Mn was 22.6 × 10 4 , and the terminal modification rate was 93%.
(製造例2)
(重合体(2)の合成)
製造例1において、3−(N,N−ジメチルアミノプロピル)トリエトキシシラン1mmolを3−グリシドキシプロピルトリエトキシシラン1mmolに変えた以外は、製造例1と同様の操作を行い、重合体(2)を52g得た。重合体(2)のMwは23.2×104、Mnは22.3×104、末端変性率は90%であった。
(Production Example 2)
(Synthesis of polymer (2))
In Production Example 1, the same procedure as in Production Example 1 was performed, except that 1 mmol of 3- (N, N-dimethylaminopropyl) triethoxysilane was changed to 1 mmol of 3-glycidoxypropyltriethoxysilane. 52 g of 2) was obtained. Mw of the polymer (2) was 23.2 × 10 4 , Mn was 22.3 × 10 4 , and the terminal modification rate was 90%.
(製造例3)
(重合体(3)の合成)
十分に窒素置換した1000ml耐圧製容器にシクロヘキサン600ml、ブタジエン1mol、スチレン50mmol、THF1mlを加え、40℃に加温後、1.6M n−ブチルリチウムヘキサン溶液0.4ml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)トリエトキシシランを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(3)を54g得た。重合体(3)のMwは27.0×104、Mnは25.7×104、末端変性率は88%であった。
(Production Example 3)
(Synthesis of polymer (3))
Cyclohexane 600 ml, butadiene 1 mol, styrene 50 mmol, and THF 1 ml were added to a 1000 ml pressure-resistant container sufficiently purged with nitrogen, heated to 40 ° C., and 0.4 ml of 1.6 M n-butyllithium hexane solution was added and stirred. After 3 hours, 1 mmol of 3- (N, N-dimethylaminopropyl) triethoxysilane was added. After further stirring for 30 minutes, 3 ml of isopropanol was added to terminate the polymerization. After adding 1 g of 2,6-tert-butyl-p-cresol to the reaction solution, it was reprecipitated with methanol and dried by heating to obtain 54 g of polymer (3). The Mw of the polymer (3) was 27.0 × 10 4 , Mn was 25.7 × 10 4 , and the terminal modification rate was 88%.
(製造例4)
(重合体(4)の合成)
十分に窒素置換した1000ml耐圧製容器にシクロヘキサン600ml、ブタジエン1mol、THF1mlを加え、40℃に加温後、1.6M n−ブチルリチウムヘキサン溶液0.4ml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53g得た。重合体(4)のMwは19.8×104、Mnは18.7×104、末端変性率は0%(未変性)であった。
(Production Example 4)
(Synthesis of polymer (4))
To a 1000 ml pressure-resistant container sufficiently purged with nitrogen, 600 ml of cyclohexane, 1 mol of butadiene and 1 ml of THF were added, heated to 40 ° C., 0.4 ml of 1.6 M n-butyllithium hexane solution was added and stirred. After 3 hours, 3 ml of isopropanol was added to stop the polymerization. After adding 1 g of 2,6-tert-butyl-p-cresol to the reaction solution, reprecipitation treatment was performed with methanol, followed by drying by heating to obtain 53 g of the polymer (4). Mw of the polymer (4) was 19.8 × 10 4 , Mn was 18.7 × 10 4 , and the terminal modification rate was 0% (unmodified).
以下、製造例5〜9(過酢酸溶液(1)、エポキシ化ジエン系ゴム(1)〜(4)の合成)で使用した各種薬品について、まとめて説明する。
天然ゴムラテックス:野村貿易(株)製のHYTEX(固形分60%)
30%過酸化水素水:関東化学(株)製の30%過酸化水素水
氷酢酸:関東化学(株)製の99.7%酢酸
界面活性剤:花王(株)製のエマルゲン120
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
メタノール:関東化学(株)製のメタノール
BR150B:宇部興産(株)製のBR150B(シス含量:98質量%)
トルエン:関東化学(株)製のトルエン
ギ酸:関東化学(株)製のギ酸
2,6−tert−ブチル−p−クレゾール:関東化学(株)製の2,6−tert−ブチル−p−クレゾール
Hereinafter, various chemicals used in Production Examples 5 to 9 (synthesis of peracetic acid solution (1) and epoxidized diene rubbers (1) to (4)) will be described together.
Natural rubber latex: HYTEX (solid content 60%) manufactured by Nomura Trading Co., Ltd.
30% hydrogen peroxide solution: 30% hydrogen peroxide water glacial acetic acid manufactured by Kanto Chemical Co., Ltd .: 99.7% acetic acid surfactant manufactured by Kanto Chemical Co., Ltd .: Emulgen 120 manufactured by Kao Co., Ltd.
1.6M n-butyllithium hexane solution: 1.6M n-butyllithium hexane solution manufactured by Kanto Chemical Co., Inc. Methanol: Methanol BR150B manufactured by Kanto Chemical Co., Ltd. BR150B manufactured by Ube Industries, Ltd. (cis content: 98% by mass)
Toluene: Toluic acid manufactured by Kanto Chemical Co., Ltd .: 2,6-tert-butyl-p-cresol formic acid manufactured by Kanto Chemical Co., Ltd .: 2,6-tert-butyl-p-cresol manufactured by Kanto Chemical Co., Ltd.
得られたエポキシ化ジエン系ゴムの分析は以下の方法で行った。
(エポキシ化率の測定)
得られたエポキシ化ジエン系ゴムを重水素化クロロホルムに溶解し、核磁気共鳴(NMR(日本電子(株)製のJNM−ECAシリーズ))分光分析により、エポキシ化されていないジエンユニット数とエポキシ化されたジエンユニット数の比を求め、以下の算出式を用いて算出した。
(エポキシ化率E%)=(ゴムの主鎖に含まれるエポキシの数)/(ゴムの主鎖に含まれるジエンユニットの数(エポキシ化されたユニットも含む))×100
The obtained epoxidized diene rubber was analyzed by the following method.
(Measurement of epoxidation rate)
The resulting epoxidized diene rubber was dissolved in deuterated chloroform and analyzed by nuclear magnetic resonance (NMR (JNM-ECA series manufactured by JEOL Ltd.)) spectroscopic analysis to determine the number of epoxidized diene units and epoxy. The ratio of the number of diene units converted was calculated and calculated using the following calculation formula.
(Epoxidation rate E%) = (number of epoxies contained in the main chain of rubber) / (number of diene units contained in the main chain of rubber (including epoxidized units)) × 100
(製造例5)
(過酢酸溶液の作成)
300ml三角フラスコに氷酢酸57gと30%過酸化水素水107gを加え、攪拌後、恒温槽で40℃に保ったまま24時間静置し、過酢酸溶液(1)を得た。
(Production Example 5)
(Preparation of peracetic acid solution)
To a 300 ml Erlenmeyer flask, 57 g of glacial acetic acid and 107 g of 30% hydrogen peroxide water were added, and after stirring, the mixture was allowed to stand for 24 hours while being kept at 40 ° C. in a thermostatic bath to obtain a peracetic acid solution (1).
(製造例6)
(エポキシ化ジエン系ゴム(1)の作成)
1Lガラス容器に天然ゴムラテックス300g、蒸留水300g、界面活性剤3.6gを加え10℃に冷却し、攪拌しながら過酢酸溶液(1)164gを10分間かけて滴下した。滴下終了後ラテックス溶液を5分間攪拌し、さらに1Lメタノールにゆっくり注ぎ込み凝集させ、得られた凝集物を1cm程度に粉砕し、2Lの水に入れて一晩放置させた。凝集物を水で数回洗浄し、1日風乾後、減圧乾燥させ、エポキシ化ジエン系ゴム(1)(エポキシ化天然ゴム)176gを得た。エポキシ化ジエン系ゴム(1)のエポキシ化率は10.0モル%であった。
(Production Example 6)
(Creation of epoxidized diene rubber (1))
To a 1 L glass container, 300 g of natural rubber latex, 300 g of distilled water and 3.6 g of a surfactant were added and cooled to 10 ° C., and 164 g of peracetic acid solution (1) was added dropwise over 10 minutes while stirring. After completion of the dropwise addition, the latex solution was stirred for 5 minutes and further poured slowly into 1 L methanol for aggregation, and the resulting aggregate was pulverized to about 1 cm, placed in 2 L of water and allowed to stand overnight. The agglomerate was washed several times with water, air-dried for one day, and then dried under reduced pressure to obtain 176 g of epoxidized diene rubber (1) (epoxidized natural rubber). The epoxidation rate of the epoxidized diene rubber (1) was 10.0 mol%.
(製造例7)
(エポキシ化ジエン系ゴム(2)の作成)
過酢酸溶液(1)の量を9g、滴下時間を20秒にした以外は製造例6と同じ操作を行い、エポキシ化ジエン系ゴム(2)(エポキシ化天然ゴム)175gを得た。エポキシ化ジエン系ゴム(2)のエポキシ化率は0.7モル%であった。
(Production Example 7)
(Creation of epoxidized diene rubber (2))
The same operation as in Production Example 6 was performed except that the amount of the peracetic acid solution (1) was 9 g and the dropping time was 20 seconds to obtain 175 g of an epoxidized diene rubber (2) (epoxidized natural rubber). The epoxidation rate of the epoxidized diene rubber (2) was 0.7 mol%.
(製造例8)
(エポキシ化ジエン系ゴム(3)の作成)
天然ゴムラテックスの量を150g、蒸留水の量を150g、界面活性剤の量を3g、過酢酸溶液(1)の量を492g、滴下時間を30分にした以外は製造例6と同じ操作を行い、エポキシ化ジエン系ゴム(3)(エポキシ化天然ゴム)92gを得た。エポキシ化ジエン系ゴム(3)のエポキシ化率は57.8モル%であった。
(Production Example 8)
(Creation of epoxidized diene rubber (3))
The same operation as in Production Example 6 except that the amount of natural rubber latex was 150 g, the amount of distilled water was 150 g, the amount of surfactant was 3 g, the amount of peracetic acid solution (1) was 492 g, and the dropping time was 30 minutes. And 92 g of epoxidized diene rubber (3) (epoxidized natural rubber) was obtained. The epoxidation rate of the epoxidized diene rubber (3) was 57.8 mol%.
(製造例9)
(エポキシ化ジエン系ゴム(4)の作成)
100gのBR150Bを1粒が、約0.5g程度になる様に細かく切り、ガラス製5L容器中のトルエン1200ml中に添加し、撹拌しながら24時間かけて溶解させた。次に、ギ酸6mlを添加し、ウォーターバス上で50℃に昇温させた。溶液を撹拌しながら、30%過酸化水素水30gを30分間かけて滴下した。滴下終了後、50℃を保持した撹拌を続け、3時間後2,6−tert−ブチル−p−クレゾールを0.3g添加した。室温まで放冷後、5Lのメタノールに反応液を添加してゴム成分を沈殿させた。沈殿物を広いバット上に広げ、24時間風乾させた後、減圧乾燥を行い、エポキシ化ジエン系ゴム(4)(エポキシ化ブタジエンゴム)を99g得た。エポキシ化ジエン系ゴム(4)のエポキシ化率は12.3モル%であった。
(Production Example 9)
(Creation of epoxidized diene rubber (4))
One piece of 100 g of BR150B was finely cut so that about 1 g would be about 0.5 g, added to 1200 ml of toluene in a glass 5 L container, and dissolved over 24 hours with stirring. Next, 6 ml of formic acid was added and the temperature was raised to 50 ° C. on a water bath. While stirring the solution, 30 g of 30% hydrogen peroxide water was added dropwise over 30 minutes. After completion of the dropwise addition, stirring while maintaining 50 ° C. was continued, and after 3 hours, 0.3 g of 2,6-tert-butyl-p-cresol was added. After cooling to room temperature, the reaction solution was added to 5 L of methanol to precipitate the rubber component. The precipitate was spread on a wide vat, air-dried for 24 hours, and then dried under reduced pressure to obtain 99 g of epoxidized diene rubber (4) (epoxidized butadiene rubber). The epoxidation rate of the epoxidized diene rubber (4) was 12.3 mol%.
以下、実施例及び比較例で使用した各種薬品について、まとめて説明する。
NR:TSR20
BR:宇部興産(株)製のBR150B(シス含量:98質量%)
重合体(1)〜(4):製造例(1)〜(4)で調製した重合体(1)〜(4)
エポキシ化ジエン系ゴム(1)〜(4):製造例(6)〜(9)で調製したエポキシ化ジエン系ゴム(1)〜(4)
エポキシ化ジエン系ゴム(5):MRB(マレーシア)社製のエポキシ化天然ゴム(エポキシ化率:25モル%)
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(N2SA:125m2/g)
シリカ:テグッサ社製のウルトラシルVN3(N2SA:175m2/g)
シランカップリング剤:テグッサ社製のSi69(ビス(3−トリエトキシシリルプロピル)テトラスルフィド)
老化防止剤:大内新興化学工業(株)製のノクラック6C
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
Hereinafter, various chemicals used in Examples and Comparative Examples will be described together.
NR: TSR20
BR: BR150B manufactured by Ube Industries, Ltd. (cis content: 98% by mass)
Polymers (1) to (4): Polymers (1) to (4) prepared in Production Examples (1) to (4)
Epoxidized diene rubbers (1) to (4): Epoxidized diene rubbers (1) to (4) prepared in Production Examples (6) to (9)
Epoxidized diene rubber (5): Epoxidized natural rubber (epoxidation rate: 25 mol%) manufactured by MRB (Malaysia)
Carbon Black: Show Black N220 (N 2 SA: 125 m 2 / g) manufactured by Cabot Japan
Silica: Ultrasil VN3 (N 2 SA: 175 m 2 / g) manufactured by Tegusa
Silane coupling agent: Si69 (bis (3-triethoxysilylpropyl) tetrasulfide) manufactured by Tegussa
Anti-aging agent: NOCRACK 6C manufactured by Ouchi Shinsei Chemical Co., Ltd.
Stearic acid: Stearic acid oil manufactured by NOF Corporation: Mineral oil PW-380 manufactured by Idemitsu Kosan Co., Ltd.
Zinc oxide: Zinc Hua No. 1 manufactured by Mitsui Mining & Smelting Co., Ltd. Wax: Sunnock wax manufactured by Ouchi Shinsei Chemical Co., Ltd. Sulfur: Powder sulfur vulcanization accelerator manufactured by Tsurumi Chemical Co., Ltd. (1): Large Noxeller CZ made by Uchishin Chemical Co., Ltd.
Vulcanization accelerator (2): Noxeller D manufactured by Ouchi Shinsei Chemical Industry Co., Ltd.
実施例1〜9及び比較例1〜4
表1に示す配合内容に従い、バンバリーミキサーを用いて、硫黄及び加硫促進剤以外の材料を150℃の条件下で3分間混練りし、混練り物を得た。次に、得られた混練り物に硫黄及び加硫促進剤を添加し、オープンロールを用いて、50℃の条件下で5分間練り込み、未加硫ゴム組成物を得た。得られた未加硫ゴム組成物を170℃で20分間、2.0mm厚の金型でプレス加硫し、加硫ゴム組成物を得た。
Examples 1-9 and Comparative Examples 1-4
According to the formulation shown in Table 1, materials other than sulfur and a vulcanization accelerator were kneaded for 3 minutes at 150 ° C. using a Banbury mixer to obtain a kneaded product. Next, sulfur and a vulcanization accelerator were added to the obtained kneaded product, and kneaded for 5 minutes at 50 ° C. using an open roll to obtain an unvulcanized rubber composition. The obtained unvulcanized rubber composition was press vulcanized with a 2.0 mm thick mold at 170 ° C. for 20 minutes to obtain a vulcanized rubber composition.
得られた加硫ゴム組成物を使用して、下記の評価を行った。それぞれの試験結果を表1に示す。 The following evaluation was performed using the obtained vulcanized rubber composition. Each test result is shown in Table 1.
(動的粘弾性試験)
得られた加硫ゴム組成物について、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。
氷上性能とドライ操縦安定性のバランスの指標として、次式
s=(ΔG*)/(0.1%G*)
で表される指標sを用い(sは0<s<1の値である)、比較例4を100として指数表示した。sが小さいほど、氷上性能とドライ操縦安定性のバランスが良いことを示す。
(Dynamic viscoelasticity test)
About the obtained vulcanized rubber composition, elastic modulus (0.1 at a temperature of 0 ° C., a frequency of 5 Hz, and an amplitude of 0.1% was measured using a viscoelasticity measuring tester manufactured by TS Instruments Co., Ltd. % G *) and a value obtained by subtracting 0.1% G * from an elastic modulus of 40% G * at an amplitude of 40% (ΔG *).
As an index of the balance between on-ice performance and dry handling stability, the following formula s = (ΔG *) / (0.1% G *)
(S is a value of 0 <s <1), and Comparative Example 4 was set to 100 and displayed as an index. The smaller s, the better the balance between on-ice performance and dry handling stability.
(ランボーン摩擦試験)
ランボーン摩耗試験機(岩本製作所製)を用い温度20℃、試験時間5分、試験表面速度80m/分、落砂量15g/分、加重3.0kgfおよびスリップ率20%の条件にて、各加硫ゴム組成物の容積損失量を測定した。結果を比較例4の容積損失量を100として指数表示した。指数が大きいほど耐摩耗性に優れている。
(Lambourn friction test)
Using a Lambourn abrasion tester (manufactured by Iwamoto Seisakusho) under the conditions of a temperature of 20 ° C., a test time of 5 minutes, a test surface speed of 80 m / min, a sand fall rate of 15 g / min, a load of 3.0 kgf and a slip rate of 20%. The volume loss amount of the vulcanized rubber composition was measured. The results are shown as indexes with the volume loss amount of Comparative Example 4 as 100. The higher the index, the better the wear resistance.
(LAT摩耗試験)
LAT試験機(Laboratory Abration and Skid Tester)を用い、荷重50N、速度20km/h、スリップアングル5°の条件にて、各加硫ゴム組成物の容積損失量を測定した。結果を比較例4の容積損失量を100として指数表示した。指数が大きいほど耐摩耗性に優れている。
(LAT wear test)
Using a LAT tester (Laboratory Abbreviation and Skid Tester), the volume loss of each vulcanized rubber composition was measured under the conditions of a load of 50 N, a speed of 20 km / h, and a slip angle of 5 °. The results are shown as indexes with the volume loss amount of Comparative Example 4 as 100. The higher the index, the better the wear resistance.
表1に示す様に、ゴム成分として、特定の重合体と、特定のエポキシ化率のエポキシ化ジエン系ゴムとを組み合わせ、シリカを含む実施例は、耐摩耗性を維持しつつ、氷上性能とドライ操縦安定性をバランスよく改善できた。
一方、特定の重合体を配合しなかった比較例1、2は、実施例と比較して、氷上性能とドライ操縦安定性のバランスに劣っていた。特定のエポキシ化率よりもエポキシ化率が高いエポキシ化ジエン系ゴムを配合した比較例3では、氷上性能とドライ操縦安定性のバランスの改善は見られたものの、その改善効果も充分ではなく、さらに、耐摩耗性を維持することもできなかった。エポキシ化ジエン系ゴムを配合しなかった比較例4は、実施例と比較して、氷上性能とドライ操縦安定性のバランスに劣っていた。
As shown in Table 1, as a rubber component, a specific polymer and an epoxidized diene-based rubber having a specific epoxidation rate are combined, and examples including silica maintain performance on ice while maintaining wear resistance. The dry handling stability was improved in a well-balanced manner.
On the other hand, Comparative Examples 1 and 2 in which no specific polymer was blended were inferior in balance between on-ice performance and dry handling stability as compared to the Examples. In Comparative Example 3 in which an epoxidized diene rubber having a higher epoxidation rate than a specific epoxidation rate was blended, an improvement in the balance between on-ice performance and dry handling stability was seen, but the improvement effect was not sufficient, Furthermore, the wear resistance could not be maintained. The comparative example 4 which did not mix | blend the epoxidized diene type rubber was inferior to the balance of performance on ice and dry handling stability compared with the Example.
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