JP6329063B2 - ゴム組成物及び該ゴム組成物を用いて作製したトレッドを有する空気入りタイヤ - Google Patents
ゴム組成物及び該ゴム組成物を用いて作製したトレッドを有する空気入りタイヤ Download PDFInfo
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- JP6329063B2 JP6329063B2 JP2014250994A JP2014250994A JP6329063B2 JP 6329063 B2 JP6329063 B2 JP 6329063B2 JP 2014250994 A JP2014250994 A JP 2014250994A JP 2014250994 A JP2014250994 A JP 2014250994A JP 6329063 B2 JP6329063 B2 JP 6329063B2
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- 229920001971 elastomer Polymers 0.000 title claims description 35
- 239000005060 rubber Substances 0.000 title claims description 35
- 239000000203 mixture Substances 0.000 title claims description 33
- 125000004432 carbon atom Chemical group C* 0.000 claims description 74
- 229920001577 copolymer Polymers 0.000 claims description 67
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 47
- 239000000178 monomer Substances 0.000 claims description 33
- 150000001875 compounds Chemical class 0.000 claims description 27
- 239000000377 silicon dioxide Substances 0.000 claims description 23
- 125000002015 acyclic group Chemical group 0.000 claims description 19
- 239000006229 carbon black Substances 0.000 claims description 19
- 150000001993 dienes Chemical class 0.000 claims description 19
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 239000012986 chain transfer agent Substances 0.000 claims description 12
- 150000002430 hydrocarbons Chemical group 0.000 claims description 12
- 238000007720 emulsion polymerization reaction Methods 0.000 claims description 11
- 239000000945 filler Substances 0.000 claims description 10
- 125000000524 functional group Chemical group 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 238000009826 distribution Methods 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 5
- 125000002723 alicyclic group Chemical group 0.000 claims description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 54
- 238000004519 manufacturing process Methods 0.000 description 45
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 38
- -1 2-ethylhexyl group Chemical group 0.000 description 33
- 238000000034 method Methods 0.000 description 27
- 239000000446 fuel Substances 0.000 description 24
- YAJYJWXEWKRTPO-UHFFFAOYSA-N 2,3,3,4,4,5-hexamethylhexane-2-thiol Chemical compound CC(C)C(C)(C)C(C)(C)C(C)(C)S YAJYJWXEWKRTPO-UHFFFAOYSA-N 0.000 description 21
- 239000000126 substance Substances 0.000 description 19
- 235000019241 carbon black Nutrition 0.000 description 18
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 15
- 125000000217 alkyl group Chemical group 0.000 description 12
- 230000000694 effects Effects 0.000 description 11
- 229920000642 polymer Polymers 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 8
- DCQBZYNUSLHVJC-UHFFFAOYSA-N 3-triethoxysilylpropane-1-thiol Chemical compound CCO[Si](OCC)(OCC)CCCS DCQBZYNUSLHVJC-UHFFFAOYSA-N 0.000 description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
- 125000002947 alkylene group Chemical group 0.000 description 6
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 6
- 239000003995 emulsifying agent Substances 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 description 6
- 239000011593 sulfur Substances 0.000 description 6
- SUODCTNNAKSRHB-UHFFFAOYSA-N 2-ethylhexyl 3-sulfanylpropanoate Chemical compound CCCCC(CC)COC(=O)CCS SUODCTNNAKSRHB-UHFFFAOYSA-N 0.000 description 5
- 239000006087 Silane Coupling Agent Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 230000009477 glass transition Effects 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 239000004636 vulcanized rubber Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
- 238000005299 abrasion Methods 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 125000005370 alkoxysilyl group Chemical group 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 230000003014 reinforcing effect Effects 0.000 description 4
- 239000000344 soap Substances 0.000 description 4
- 238000004073 vulcanization Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 3
- 229920001174 Diethylhydroxylamine Polymers 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- FVCOIAYSJZGECG-UHFFFAOYSA-N diethylhydroxylamine Chemical compound CCN(O)CC FVCOIAYSJZGECG-UHFFFAOYSA-N 0.000 description 3
- 125000004185 ester group Chemical group 0.000 description 3
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 125000003944 tolyl group Chemical group 0.000 description 3
- 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 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 125000004642 (C1-C12) alkoxy group Chemical group 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
- ROGIWVXWXZRRMZ-UHFFFAOYSA-N 2-methylbuta-1,3-diene;styrene Chemical compound CC(=C)C=C.C=CC1=CC=CC=C1 ROGIWVXWXZRRMZ-UHFFFAOYSA-N 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- KXYAVSFOJVUIHT-UHFFFAOYSA-N 2-vinylnaphthalene Chemical compound C1=CC=CC2=CC(C=C)=CC=C21 KXYAVSFOJVUIHT-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
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
- 229920002943 EPDM rubber Polymers 0.000 description 2
- 244000043261 Hevea brasiliensis Species 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-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
- 229920000459 Nitrile rubber Polymers 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 229920005683 SIBR Polymers 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- RSWGJHLUYNHPMX-ONCXSQPRSA-N abietic acid Chemical class C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 0.000 description 2
- 125000004450 alkenylene group Chemical group 0.000 description 2
- 125000004419 alkynylene group Chemical group 0.000 description 2
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 2
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
- 230000003712 anti-aging effect Effects 0.000 description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 2
- 125000000732 arylene group Chemical group 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 229920005549 butyl rubber Polymers 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000001804 emulsifying effect Effects 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 229920006158 high molecular weight polymer Polymers 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 229920003049 isoprene rubber Polymers 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 2
- 229920003052 natural elastomer Polymers 0.000 description 2
- 229920001194 natural rubber Polymers 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
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229920001084 poly(chloroprene) Polymers 0.000 description 2
- 229920002857 polybutadiene Polymers 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000001103 potassium chloride Substances 0.000 description 2
- 235000011164 potassium chloride Nutrition 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000007870 radical polymerization initiator Substances 0.000 description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 239000012763 reinforcing filler 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
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 125000005023 xylyl group Chemical group 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 1
- OBDUMNZXAIUUTH-HWKANZROSA-N (e)-tetradec-2-ene Chemical group CCCCCCCCCCC\C=C\C OBDUMNZXAIUUTH-HWKANZROSA-N 0.000 description 1
- OWRCNXZUPFZXOS-UHFFFAOYSA-N 1,3-diphenylguanidine Chemical compound C=1C=CC=CC=1NC(=N)NC1=CC=CC=C1 OWRCNXZUPFZXOS-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- OEVVKKAVYQFQNV-UHFFFAOYSA-N 1-ethenyl-2,4-dimethylbenzene Chemical compound CC1=CC=C(C=C)C(C)=C1 OEVVKKAVYQFQNV-UHFFFAOYSA-N 0.000 description 1
- NVZWEEGUWXZOKI-UHFFFAOYSA-N 1-ethenyl-2-methylbenzene Chemical compound CC1=CC=CC=C1C=C NVZWEEGUWXZOKI-UHFFFAOYSA-N 0.000 description 1
- JZHGRUMIRATHIU-UHFFFAOYSA-N 1-ethenyl-3-methylbenzene Chemical compound CC1=CC=CC(C=C)=C1 JZHGRUMIRATHIU-UHFFFAOYSA-N 0.000 description 1
- 125000006039 1-hexenyl group Chemical group 0.000 description 1
- WAEOXIOXMKNFLQ-UHFFFAOYSA-N 1-methyl-4-prop-2-enylbenzene Chemical group CC1=CC=C(CC=C)C=C1 WAEOXIOXMKNFLQ-UHFFFAOYSA-N 0.000 description 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical group CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- 125000006023 1-pentenyl group Chemical group 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- TWJNQYPJQDRXPH-UHFFFAOYSA-N 2-cyanobenzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1C#N TWJNQYPJQDRXPH-UHFFFAOYSA-N 0.000 description 1
- OWHSTLLOZWTNTQ-UHFFFAOYSA-N 2-ethylhexyl 2-sulfanylacetate Chemical compound CCCCC(CC)COC(=O)CS OWHSTLLOZWTNTQ-UHFFFAOYSA-N 0.000 description 1
- 125000006040 2-hexenyl group Chemical group 0.000 description 1
- 125000006024 2-pentenyl group Chemical group 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- YDLAHBBJAGGIJZ-UHFFFAOYSA-N 2-sulfanylethyl acetate Chemical compound CC(=O)OCCS YDLAHBBJAGGIJZ-UHFFFAOYSA-N 0.000 description 1
- DLZYFIFYWZEAEM-UHFFFAOYSA-N 2-sulfanylethyl butanoate Chemical compound CCCC(=O)OCCS DLZYFIFYWZEAEM-UHFFFAOYSA-N 0.000 description 1
- UAEQUXKDKOVLOU-UHFFFAOYSA-N 2-sulfanylethyl formate Chemical compound SCCOC=O UAEQUXKDKOVLOU-UHFFFAOYSA-N 0.000 description 1
- RAQXZZCIQKGGNI-UHFFFAOYSA-N 2-sulfanylethyl heptanoate Chemical compound CCCCCCC(=O)OCCS RAQXZZCIQKGGNI-UHFFFAOYSA-N 0.000 description 1
- LSZCIZOHKPPEJD-UHFFFAOYSA-N 2-sulfanylethyl hexanoate Chemical compound CCCCCC(=O)OCCS LSZCIZOHKPPEJD-UHFFFAOYSA-N 0.000 description 1
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- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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- C08F236/06—Butadiene
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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- C08F236/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F236/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
- C08F236/14—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated containing elements other than carbon and hydrogen
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- B60C1/00—Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
- B60C1/0025—Compositions of the sidewalls
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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Landscapes
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- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
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- Mechanical Engineering (AREA)
- Tires In General (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
なお、連鎖移動剤とは、ポリマー生長末端に作用してポリマーの生長を停止するとともに、新たな重合開始ラジカルを発生することができるラジカル重合の制御剤である。これにより、ポリマーの分子量、分子量分布の制御(低分子量化、狭分子量分布化)や、ポリマー末端構造の制御などが可能となる。
R31〜R33は、本発明の効果がより良好に得られるという点から、更に少なくとも1つが−O−(R35−O)z−R36で表される基であることが好ましく、残りの2つが−O−(R35−O)z−R36で表される基であることがより好ましい。
また、R31〜R33全てが分岐若しくは非分岐の炭素数1〜12(好ましくは炭素数1〜5、より好ましくは炭素数1〜3)のアルコキシ基であることも好ましい。
該炭化水素基としては、例えば、分岐若しくは非分岐の炭素数1〜30のアルキレン基、分岐若しくは非分岐の炭素数2〜30のアルケニレン基、分岐若しくは非分岐の炭素数2〜30のアルキニレン基、炭素数6〜30のアリーレン基などがあげられる。中でも、分岐若しくは非分岐の炭素数1〜30のアルキレン基が好ましい。
なお、Mw及びMnは、ゲルパーミエーションクロマトグラフ(GPC)を用い、標準ポリスチレンより換算した値である。
なお、Tgは、JIS−K7121:1987に従い、ティー・エイ・インスツルメント・ジャパン社製の示差走査熱量計(Q200)を用いて、昇温速度10℃/分の条件で測定した値である。
なお、ムーニー粘度(ML1+4、130℃)は、JIS−K6300に従い、130℃でムーニー粘度を測定することにより得られる値である。
なお、カーボンブラックのN2SAは、JIS−K6217−2:2001に準拠して測定できる。
なお、カーボンブラックのDBPは、JIS−K6217−4:2001に準拠して測定できる。
なお、シリカのN2SAは、ASTM D3037−81に準拠して測定できる。
シランカップリング剤としては、ゴム工業において、従来からシリカと併用される任意のシランカップリング剤を使用することができ、例えば、ビス(3−トリエトキシシリルプロピル)テトラスルフィド等のスルフィド系、3−メルカプトプロピルトリメトキシシランなどのメルカプト系、ビニルトリエトキシシランなどのビニル系、3−アミノプロピルトリエトキシシランなどのアミノ系、γ−グリシドキシプロピルトリエトキシシランのグリシドキシ系、3−ニトロプロピルトリメトキシシランなどのニトロ系、3−クロロプロピルトリメトキシシランなどのクロロ系等が挙げられる。なかでも、スルフィド系が好ましく、ビス(3−トリエトキシシリルプロピル)テトラスルフィドがより好ましい。
すなわち、上記成分を配合したゴム組成物を、未加硫の段階でトレッドなどのタイヤ用部材の形状にあわせて押出し加工し、他のタイヤ部材とともに、タイヤ成型機上にて通常の方法で成形することにより、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することによりタイヤを得る。
イオン交換水:自社製
ロジン酸カリウム石鹸:ハリマ化成(株)製
脂肪酸ナトリウム石鹸:和光純薬工業(株)製
塩化カリウム:和光純薬工業(株)製
ナフタレンスルホン酸ソーダホルマリン縮合物:花王(株)製
1,3−ブタジエン:高千穂商事(株)製の1,3−ブタジエン
スチレン:和光純薬工業(株)製のスチレン(式(2)で表される化合物)
t−ドデシルメルカプタン:和光純薬工業(株)製のtert−ドデシルメルカプタン(連鎖移動剤)
Si363:デグッサ社製の3−[エトキシビス(3,6,9,12,15−ペンタオキサオクタコサン−1−イルオキシ)シリル]−1−プロパンチオール(連鎖移動剤、下記式で表される化合物、式(3)で表される化合物)
3−メルカプトプロピオン酸2−エチルヘキシル:東京化成工業(株)製(連鎖移動剤)
オクタン酸2−メルカプトエチル:東京化成工業(株)製(連鎖移動剤)
ハイドロサルファイドナトリウム:和光純薬工業(株)製
FeSO4:和光純薬工業(株)製の硫酸第二鉄
EDTA:和光純薬工業(株)製のエチレンジアミン四酢酸ナトリウム
ロンガリット:和光純薬工業(株)製のソディウム・ホルムアルデヒド・スルホキシレート
重合開始剤:日油(株)製のパーメンタH(パラメンタンヒドロペルオキシド)
N,N−ジエチルヒドロキシルアミン:和光純薬工業(株)製
2,6−ジ−t−ブチル−p−クレゾール:住友化学(株)製のスミライザーBHT
メタクリル酸メチル:東京化成工業(株)製
アクリル酸メチル:東京化成工業(株)製
イオン交換水9356g、ロジン酸カリウム石鹸1152g、脂肪酸ナトリウム石鹸331g、塩化カリウム51g、ナフタレンスルホン酸ソーダホルマリン縮合物30gを添加し70℃で2時間撹拌、乳化剤を調製した。
内容積50リットルのステンレス製重合反応機を洗浄、乾燥し、乾燥窒素で置換した後に1,3−ブタジエン3500g、スチレン1500g、t−ドデシルメルカプタン5.74g、上記乳化剤9688g、ハイドロサルファイドナトリウム6.3ml(1.8M)、活性剤(FeSO4/EDTA/ロンガリット)各6.3ml、重合開始剤6.3ml(2.3M)を添加し、攪拌下に10℃で3時間重合を行った。重合完了後、N,N−ジエチルヒドロキシルアミン2.9gを添加し、30分反応させ重合反応容器の内容物を取り出し、10gの2,6−ジ−t−ブチル−p−クレゾールを加え、水の大部分を蒸発させた後、55℃で12時間減圧乾燥し、共重合体1を得た。
上記製造例1のスチレン1500gをメタクリル酸メチル1500gに変更した以外は同様の方法で製造し、共重合体2を得た。
上記製造例1のスチレン1500gをアクリル酸メチル1500gに変更した以外は同様の方法で製造し、共重合体3を得た。
上記製造例1のスチレン1500gをメタクリル酸メチル1500g、t−ドデシルメルカプタン5.74gを3−メルカプトプロピルトリエトキシシラン1.48gに変更した以外は同様の方法で製造し、共重合体4を得た。
上記製造例1のスチレン1500gをアクリル酸メチル1500g、t−ドデシルメルカプタン5.74gを3−メルカプトプロピルトリエトキシシラン1.48gに変更した以外は同様の方法で製造し、共重合体5を得た。
上記製造例1のスチレン1500gをメタクリル酸メチル1500g、t−ドデシルメルカプタン5.74gをSi363 6.11gに変更した以外は同様の方法で製造し、共重合体6を得た。
上記製造例1のスチレン1500gをアクリル酸メチル1500g、t−ドデシルメルカプタン5.74gをSi363 6.11gに変更した以外は同様の方法で製造し、共重合体7を得た。
上記製造例1のスチレン1500g中、750gをメタクリル酸メチル750gに変更した以外は同様の方法で製造し、共重合体8を得た。
上記製造例1のスチレン1500g中、750gをアクリル酸メチル750gに変更した以外は同様の方法で製造し、共重合体9を得た。
上記製造例1のスチレン1500g中、750gをメタクリル酸メチル750g、t−ドデシルメルカプタン5.74gをSi363 6.11gに変更した以外は同様の方法で製造し、共重合体10を得た。
上記製造例1のスチレン1500g中、750gをアクリル酸メチル750g、t−ドデシルメルカプタン5.74gをSi363 6.11gに変更した以外は同様の方法で製造し、共重合体11を得た。
上記製造例1のスチレン1500g中、750gをメタクリル酸メチル750g、t−ドデシルメルカプタン5.74gを3−メルカプトプロピルトリエトキシシラン1.48gに変更した以外は同様の方法で製造し、共重合体12を得た。
上記製造例1のスチレン1500g中、750gをアクリル酸メチル750g、t−ドデシルメルカプタン5.74gを3−メルカプトプロピルトリエトキシシラン1.48gに変更した以外は同様の方法で製造し、共重合体13を得た。
上記製造例1のスチレン1500gをメタクリル酸メチル1500g、t−ドデシルメルカプタン5.74gを3−メルカプトプロピオン酸2−エチルヘキシル1.35gに変更した以外は同様の方法で製造し、共重合体14を得た。
上記製造例1のスチレン1500gをアクリル酸メチル1500g、t−ドデシルメルカプタン5.74gを3−メルカプトプロピオン酸2−エチルヘキシル1.35gに変更した以外は同様の方法で製造し、共重合体15を得た。
上記製造例1のスチレン1500gをメタクリル酸メチル1500g、t−ドデシルメルカプタン5.74gをオクタン酸2−メルカプトエチル1.26gに変更した以外は同様の方法で製造し、共重合体16を得た。
上記製造例1のスチレン1500gをアクリル酸メチル1500g、t−ドデシルメルカプタン5.74gをオクタン酸2−メルカプトエチル1.26gに変更した以外は同様の方法で製造し、共重合体17を得た。
上記製造例1のスチレン1500g中、750gをメタクリル酸メチル750g、t−ドデシルメルカプタン5.74gを3−メルカプトプロピオン酸2−エチルヘキシル1.35gに変更した以外は同様の方法で製造し、共重合体18を得た。
上記製造例1のスチレン1500g中、750gをアクリル酸メチル750g、t−ドデシルメルカプタン5.74gを3−メルカプトプロピオン酸2−エチルヘキシル1.35gに変更した以外は同様の方法で製造し、共重合体19を得た。
上記製造例1のスチレン1500g中、750gをメタクリル酸メチル750g、t−ドデシルメルカプタン5.74gをオクタン酸2−メルカプトエチル1.26gに変更した以外は同様の方法で製造し、共重合体20を得た。
上記製造例1のスチレン1500g中、750gをアクリル酸メチル750g、t−ドデシルメルカプタン5.74gをオクタン酸2−メルカプトエチル1.26gに変更した以外は同様の方法で製造し、共重合体21を得た。
25℃にてJEOL JNM−A 400NMR装置を用いて1H−NMRを測定し、そのスペクトルより求めた6.5〜7.2ppmのスチレン単位に基づくフェニルプロトンと、4.9〜5.4ppmのブタジエン単位に基づくビニルプロトンと、3.6〜4.6ppmの上記式(1)で表される不飽和非環式モノエステル類単位に基づくエステル部位のプロトンの比から各単量体単位の含有量を決定した。
共重合体の重量平均分子量(Mw)及び数平均分子量(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 SUPERMULTIPORE HZ−M)による測定値を基に標準ポリスチレン換算により求めた。
ガラス転移温度(Tg)は、JIS K 7121に従い、ティー・エイ・インスツルメント・ジャパン社製の示差走査熱量計(Q200)を用いて昇温速度10℃/分で昇温しながら測定することにより、ガラス転移開始温度として求めた。
JIS−K6300に従い、(株)島津製作所製のムーニー粘度計(SMV−200)を使用して、130℃で1分間予熱したのち、4分間測定してゴムのムーニー粘度(ML1+4、130℃)を測定した。
ゴム成分:上記製造例1〜21で製造された共重合体1〜21
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:111m2/g、DBP:115ml/100g)
シリカ:デ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:デグッサ社製の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)
亜鉛華:三井金属鉱業(株)製の亜鉛華1号
ステアリン酸:日油(株)製のステアリン酸
老化防止剤:大内新興化学工業(株)製のノクラック6C(N−1,3−ジメチルブチル−N’−フェニル−p−フェニレンジアミン)
ワックス:大内新興化学工業(株)製のサンノックワックス
加硫促進剤1:大内新興化学工業(株)製のノクセラーCZ(N−シクロヘキシル−2−ベンゾチアゾリルスルフェンアミド)
加硫促進剤2:大内新興化学工業(株)製のノクセラーD(N,N’−ジフェニルグアニジン)
硫黄:鶴見化学工業(株)製の粉末硫黄
表2及び3に示す配合内容に従い、硫黄および加硫促進剤を除く各種薬品を、バンバリーミキサーにて、150℃で5分間混練りした。得られた混練物に、硫黄及び加硫促進剤を添加して、オープンロールを用いて、170℃で12分間混練りし、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分間プレス加硫し、加硫ゴム組成物を得た。
各未加硫ゴム組成物について、JIS−K6300に準拠したムーニー粘度の測定方法に従い、100℃で測定した。数値が小さいほど、加工性に優れる。
粘弾性スペクトロメーターVES((株)岩本製作所製)を用いて、温度60℃、初期歪み10%、動歪み2%の条件下で各加硫ゴム組成物のtanδを測定した。tanδが小さいほど低燃費性に優れることを示す。
各加硫ゴム組成物から調製した試験片について、レオメトリックス・サイエンティフィック社製の粘弾性試験機(ARES)を使用して、ねじりモードで、粘弾性パラメータを測定した。0℃において周波数10Hz、ひずみ1%でtanδを測定した。tanδが大きいほどウェットグリップ性能に優れることを示す。
ランボーン型摩耗試験機を用いて、室温、負荷荷重1.0kgf、スリップ率30%の条件で上記加硫ゴム組成物の摩耗量を測定し、下記計算式により指数表示した。数値が大きいほど耐摩耗性に優れることを示す。
(耐摩耗性指数)=(比較例1の摩耗量)/(各配合の摩耗量)×100
Claims (8)
- 前記共重合体は、構成単位100質量%中、前記共役ジエン系単量体単位の含有量が5〜95質量%、前記不飽和非環式モノエステル類単位の含有量が5〜95質量%である請求項1記載の空気入りタイヤ。
- 前記共重合体は、乳化重合して合成され、重量平均分子量5,000〜2,000,000、分子量分布2.1〜11である請求項1又は2記載の空気入りタイヤ。
- 前記R1が水素原子又はメチル基であり、前記R2がメチル基である請求項1〜3のいずれかに記載の空気入りタイヤ。
- 前記共役ジエン系単量体が1,3−ブタジエンである請求項1〜4のいずれかに記載の空気入りタイヤ。
- 前記共重合体は、連鎖移動剤として、フィラーと親和性のある官能基及びメルカプト基を有する化合物を用いて合成されるものである請求項1〜6のいずれかに記載の空気入りタイヤ。
- 前記ゴム組成物を用いて作製したトレッドを有する請求項1〜7のいずれかに記載の空気入りタイヤ。
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KR101152673B1 (ko) | 2009-10-22 | 2012-06-15 | 금호석유화학 주식회사 | 기능성 스티렌-부타디엔 공중합체 |
KR101152672B1 (ko) | 2009-11-30 | 2012-06-15 | 금호석유화학 주식회사 | 친수성 티오 에테르기로 말단변성된 스티렌-부타디엔 공중합체 및 이의 실리카 복합재 |
KR101402285B1 (ko) | 2010-12-27 | 2014-06-02 | 금호석유화학 주식회사 | 반응성 유화제를 이용한 스티렌-부타디엔 공중합체의 제조방법 및 그에 의해 제조된 스티렌-부타디엔 공중합체 |
JP5825819B2 (ja) * | 2011-04-13 | 2015-12-02 | 住友ゴム工業株式会社 | ジエン系重合体及びその製造方法 |
JP5559234B2 (ja) * | 2011-08-09 | 2014-07-23 | 住友ゴム工業株式会社 | タイヤ用ゴム組成物及び空気入りタイヤ |
US8759451B2 (en) * | 2011-12-21 | 2014-06-24 | The Goodyear Tire & Rubber Company | Method of making a graft copolymer |
EP2814881A1 (en) * | 2012-02-16 | 2014-12-24 | Synthos S.A. | Functionalized-esbr with acrylate functional base group |
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