JP2013253139A - タイヤ用ゴム組成物及び空気入りタイヤ - Google Patents
タイヤ用ゴム組成物及び空気入りタイヤ Download PDFInfo
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- JP2013253139A JP2013253139A JP2012128304A JP2012128304A JP2013253139A JP 2013253139 A JP2013253139 A JP 2013253139A JP 2012128304 A JP2012128304 A JP 2012128304A JP 2012128304 A JP2012128304 A JP 2012128304A JP 2013253139 A JP2013253139 A JP 2013253139A
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- 239000000203 mixture Substances 0.000 title claims abstract description 103
- 229920001971 elastomer Polymers 0.000 title claims abstract description 64
- 239000005060 rubber Substances 0.000 title claims abstract description 64
- 229920000642 polymer Polymers 0.000 claims abstract description 117
- -1 diene compound Chemical class 0.000 claims abstract description 56
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 53
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 36
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 32
- 239000000377 silicon dioxide Substances 0.000 claims abstract description 26
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 18
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 16
- 238000002156 mixing Methods 0.000 claims abstract description 13
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 42
- 238000006116 polymerization reaction Methods 0.000 claims description 27
- 229920003048 styrene butadiene rubber Polymers 0.000 claims description 16
- 229920001577 copolymer Polymers 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 7
- 238000005096 rolling process Methods 0.000 abstract description 33
- 125000004432 carbon atom Chemical group C* 0.000 description 37
- 238000000034 method Methods 0.000 description 34
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 19
- 238000004519 manufacturing process Methods 0.000 description 17
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 12
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 12
- 239000005062 Polybutadiene Substances 0.000 description 11
- 229920002857 polybutadiene Polymers 0.000 description 11
- 239000006229 carbon black Substances 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- 150000004985 diamines Chemical class 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 9
- 239000000178 monomer Substances 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 244000043261 Hevea brasiliensis Species 0.000 description 8
- 238000005299 abrasion Methods 0.000 description 8
- 229920003052 natural elastomer Polymers 0.000 description 8
- 229920001194 natural rubber Polymers 0.000 description 8
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- 239000000126 substance Substances 0.000 description 7
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000002174 Styrene-butadiene Substances 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 230000000052 comparative effect Effects 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
- 230000000694 effects Effects 0.000 description 6
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- 238000001035 drying Methods 0.000 description 5
- 238000005984 hydrogenation reaction Methods 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 230000000379 polymerizing effect Effects 0.000 description 5
- 238000004073 vulcanization Methods 0.000 description 5
- 239000004636 vulcanized rubber Substances 0.000 description 5
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 4
- 239000000446 fuel Substances 0.000 description 4
- 239000003505 polymerization initiator Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- 229920000459 Nitrile rubber Polymers 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 230000003712 anti-aging effect Effects 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 238000004898 kneading Methods 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 230000003014 reinforcing effect Effects 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 2
- RYPKRALMXUUNKS-UHFFFAOYSA-N 2-Hexene Natural products CCCC=CC RYPKRALMXUUNKS-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-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
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 229920005549 butyl rubber Polymers 0.000 description 2
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 230000020169 heat generation Effects 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
- 229920003049 isoprene rubber Polymers 0.000 description 2
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 2
- JGGQWILNAAODRS-UHFFFAOYSA-N n-methyl-4-[4-(methylamino)phenyl]aniline Chemical compound C1=CC(NC)=CC=C1C1=CC=C(NC)C=C1 JGGQWILNAAODRS-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
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 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
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229920001084 poly(chloroprene) Polymers 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- 230000002787 reinforcement Effects 0.000 description 2
- 238000001226 reprecipitation Methods 0.000 description 2
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 2
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- 238000001179 sorption measurement Methods 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- VTHOKNTVYKTUPI-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyltetrasulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSSSCCC[Si](OCC)(OCC)OCC VTHOKNTVYKTUPI-UHFFFAOYSA-N 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- AHAREKHAZNPPMI-AATRIKPKSA-N (3e)-hexa-1,3-diene Chemical compound CC\C=C\C=C AHAREKHAZNPPMI-AATRIKPKSA-N 0.000 description 1
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- 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
- ACWJKFBBRPYPLL-UHFFFAOYSA-N 3,4-dimethyl-n-phenylaniline Chemical compound C1=C(C)C(C)=CC=C1NC1=CC=CC=C1 ACWJKFBBRPYPLL-UHFFFAOYSA-N 0.000 description 1
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 1
- ZBMISJGHVWNWTE-UHFFFAOYSA-N 3-(4-aminophenoxy)aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=CC(N)=C1 ZBMISJGHVWNWTE-UHFFFAOYSA-N 0.000 description 1
- ZDBWYUOUYNQZBM-UHFFFAOYSA-N 3-(aminomethyl)aniline Chemical compound NCC1=CC=CC(N)=C1 ZDBWYUOUYNQZBM-UHFFFAOYSA-N 0.000 description 1
- OEFAIWKFALHMEY-UHFFFAOYSA-N 3-(aminomethyl)cyclohexan-1-amine Chemical compound NCC1CCCC(N)C1 OEFAIWKFALHMEY-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02T—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO TRANSPORTATION
- Y02T10/00—Road transport of goods or passengers
- Y02T10/80—Technologies aiming to reduce greenhouse gasses emissions common to all road transportation technologies
- Y02T10/86—Optimisation of rolling resistance, e.g. weight reduction
Landscapes
- Tires In General (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
【解決手段】ゴム成分と、重合体組成物と、シリカとを混合して得られ、前記重合体組成物が、共役ジエン化合物及び/又は芳香族ビニル化合物の重合体と、窒素原子を有する有機化合物とを含み、前記重合体の重量平均分子量が1.0×103〜1.0×104、前記重合体組成物100質量%中の前記有機化合物の含有量が0.1〜20質量%であるタイヤ用ゴム組成物に関する。
【選択図】なし
Description
すなわち、本発明は、ゴム成分と、重合体組成物と、シリカとを混合して得られ、上記重合体組成物が、共役ジエン化合物及び/又は芳香族ビニル化合物の重合体と、窒素原子を有する有機化合物とを含み、上記重合体の重量平均分子量が1.0×103〜1.0×104、上記重合体組成物100質量%中の上記有機化合物の含有量が0.1〜20質量%であるタイヤ用ゴム組成物に関する。
また、上記スチレンブタジエン共重合体のスチレン含有量が0.1〜55質量%であることが好ましい。
まず、重合体組成物について説明する。
重合体組成物は、特定の重量平均分子量を有する上記重合体と共に、窒素原子を有する有機化合物を特定量含む点に特徴がある。重合体組成物の製造方法としては、上記重合体の重合反応前、重合反応中、及び/又は重合反応終了後に、上記有機化合物を添加すればよく、例えば、上記重合体を重合した後に上記有機化合物を添加する方法や、重合反応においてランダマイザーとして上記有機化合物を使用して上記重合体を重合し、上記重合体と共に該有機化合物を残留させる方法等が挙げられる。以下において、まず、上記有機化合物、上記重合体について説明する。
窒素原子を有する有機化合物としては、アミン類が好ましい。アミン類としては、モノアミン類、ジアミン類、トリアミン類などが挙げられる。なかでも、下記式(I)で表される化合物が好ましい。
共役ジエン化合物及び/又は芳香族ビニル化合物の重合体としては、良好なグリップ性能(特に、ウェットグリップ性能)、耐摩耗性及び転がり抵抗特性が得られるという理由から、共役ジエン化合物及び芳香族ビニル化合物の共重合体が好ましく、スチレンブタジエン共重合体がより好ましい。
なお、ランダマイザーとして、窒素原子を有する有機化合物を使用する場合であって、重合体組成物中に当該化合物を残留させる場合には、残留させたい量を考慮して、ランダマイザーの使用量を決定すればよい。
なお、本明細書において、重量平均分子量(Mw)は、後述の実施例に記載の方法により測定される。また、Mwは、重合時に使用する重合開始剤の量を変更するなどの方法により適宜調節することができる。
なお、本明細書において、スチレン含有量は、後述の実施例に記載の方法により測定される。
具体的には、重合反応終了後に、再沈殿精製等の精製操作、減圧乾燥により、上記溶媒、ランダマイザー等を除去することにより得られた重合体に対して、窒素原子を有する有機化合物を混合することで重合体組成物を得ることができる。また、ランダマイザーとして、窒素原子を有する有機化合物を使用した場合には、減圧乾燥により、溶媒を除去する(すなわち、残留している窒素原子を有する有機化合物を精製除去しない)ことで、重合体組成物を得ることができる。なお、ランダマイザーは、重合反応前、重合反応中のいずれにおいても添加可能である。
また、該含有量は、20質量%以下、好ましくは18質量%以下、より好ましくは16質量%以下、更に好ましくは12質量%以下、特に好ましくは10質量%以下である。20質量%を超えると、スコーチタイムが短くなる上にコストが高くなる。
なお、本発明のゴム組成物において、上記重合体組成物はゴム成分に含まれない。
なお、シリカのN2SAは、ASTM D3037−93に準じてBET法で測定される値である。
なお、カーボンブラックのN2SAは、JIS K 6217−2:2001によって求められる。
なお、カーボンブラックのDBPは、JIS K6217−4:2001に準拠して測定される。
n−ヘキサン:関東化学(株)製
スチレン:関東化学(株)製
1,3−ブタジエン:東京化成工業(株)製
テトラメチルエチレンジアミン:関東化学(株)製
n−ブチルリチウム:関東化学(株)製の1.6M n−ブチルリチウムヘキサン溶液
2,6−ジ−t−ブチル−p−クレゾール:大内新興化学工業(株)製のノクラック200
十分に窒素置換した耐熱容器にn−ヘキサン36L、スチレン7.3mol、1,3−ブタジエン22mol、テトラメチルエチレンジアミン2.0mol、n−ブチルリチウム 1.5molを加えて、5℃で30分攪拌した。その後、アルコールを加えて反応を止め、反応溶液に2,6−ジ−t−ブチル−p−クレゾール1gを添加後、再沈殿精製、減圧乾燥にて重合体(1)を得た。
表1のレシピにて、製造例1と同様の方法で重合体を合成した。そして、減圧乾燥後、得られた重合体にテトラメチルエチレンジアミンを0.1mol添加して混合し、重合体組成物(1)を得た。
再沈殿精製せずに減圧乾燥する点以外は表1のレシピにて、製造例1と同様の方法で重合体を合成し、重合体組成物(2)を得た。
製造例2のテトラメチルエチレンジアミンを1,2−ジピペリジノエタンに変更した点以外は表1のレシピにて、製造例2と同様の方法で重合体を合成し、重合体組成物(3)を得た。
製造例3のテトラメチルエチレンジアミンを1,2−ジピペリジノエタンに変更した点以外は表1のレシピにて、製造例3と同様の方法で重合体を合成し、重合体組成物(4)を得た。
25℃にてJEOL JNM−A 400NMR装置を用いてH1−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の比からスチレン含有量を決定した。
重合体の重量平均分子量(Mw)は、ゲルパーミエーションクロマトグラフ(GPC)(東ソー(株)製GPC−8000シリーズ、検出器:示差屈折計、カラム:東ソー(株)製のTSKGEL 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。
重合体又は重合体組成物100質量%中のテトラメチルエチレンジアミンの含有量(1,2−ジピペリジノエタン含有量)は、重合体又は重合体組成物の重クロロホルム溶液(40 mg/1mL CDCl3)を調製し、BRUKER社製AV400の装置を用いてピーク面積比より算出した。
以下に、実施例及び比較例で用いた各種薬品について説明する。
NR:RSS#3
BR:宇部興産(株)製のウベポールBR150B(シス含量:97質量%)
SBR:JSR(株)製のSL574(S−SBR、スチレン含有量:15質量%)
重合体(1):上記方法で調製
重合体組成物(1)〜(4):上記方法で調製
シリカ:エボニック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:エボニックデグッサ社製の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)
カーボンブラック:三菱化学(株)製のダイアブラックN339(N2SA:96m2/g、DBP吸収量:124ml/100g)
オイル:(株)ジャパンエナジー製のX−140
老化防止剤:大内新興化学工業(株)製のノクラック6C(N−1,3−ジメチルブチル−N’−フェニル−p−フェニレンジアミン)
ステアリン酸:日油(株)製のステアリン酸
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N
テトラメチルエチレンジアミン:関東化学(株)製
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
得られた加硫ゴム組成物を下記により評価し、結果を表2に示した。
得られた加硫ゴム組成物について、(株)上島製作所製スペクトロメーターを用いて、動的歪振幅1%、周波数10Hz、温度50℃でtanδを測定した。そして、下記計算式により測定結果を指数表示した。指数が大きいほど転がり抵抗が小さく、転がり抵抗特性(低燃費性)に優れることを示す。
(転がり抵抗指数)=(比較例1のtanδ)/(各配合のtanδ)×100
(株)上島製作所製フラットベルト式摩擦試験機(FR5010型)を用いてウェットグリップ性能を評価した。上記加硫ゴム組成物からなる幅20mm、直径100mmの円筒形のゴム試験片をサンプルとして用い、速度20km/時間、荷重4kgf、路面温度20℃の条件で、路面に対するサンプルのスリップ率を0〜70%まで変化させ、その際に検出される摩擦係数の最大値を読みとった。そして、下記計算式により測定結果を指数表示した。指数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。
(ウェットグリップ性能指数)=(各配合の摩擦係数の最大値)/(比較例1の摩擦係数の最大値)×100
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ランボーン摩耗量を測定した。測定したランボーン摩耗量から容積損失量を計算し、比較例1の容積損失量を100として、各配合の容積損失量を下記
計算式により指数表示した。指数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の容積損失量)/(各配合の容積損失量)×100
Claims (8)
- ゴム成分と、重合体組成物と、シリカとを混合して得られ、
前記重合体組成物が、共役ジエン化合物及び/又は芳香族ビニル化合物の重合体と、窒素原子を有する有機化合物とを含み、前記重合体の重量平均分子量が1.0×103〜1.0×104、前記重合体組成物100質量%中の前記有機化合物の含有量が0.1〜20質量%である
タイヤ用ゴム組成物。 - 前記有機化合物が、アミン類である請求項1に記載のタイヤ用ゴム組成物。
- 前記重合体組成物が、重合反応前、重合反応中、及び/又は重合反応終了後に、前記有機化合物を添加することにより得られたものである請求項1又は2に記載のタイヤ用ゴム組成物。
- 前記重合体が、共役ジエン化合物及び芳香族ビニル化合物の共重合体である請求項1〜3のいずれかに記載のタイヤ用ゴム組成物。
- 前記重合体が、スチレンブタジエン共重合体である請求項1〜3のいずれかに記載のタイヤ用ゴム組成物。
- 前記スチレンブタジエン共重合体のスチレン含有量が0.1〜55質量%である請求項5に記載のタイヤ用ゴム組成物。
- ゴム成分100質量部に対して、前記重合体組成物の含有量が3〜40質量部であり、前記シリカの含有量が5〜150質量部である請求項1〜6のいずれかに記載のタイヤ用ゴム組成物。
- 請求項1〜7のいずれかに記載のゴム組成物を用いて作製した空気入りタイヤ。
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP3006227A1 (en) * | 2014-10-06 | 2016-04-13 | Sumitomo Rubber Industries, Ltd. | Rubber composition and pneumatic tire |
EP3006493A1 (en) * | 2014-10-06 | 2016-04-13 | Sumitomo Rubber Industries, Ltd. | Rubber composition and pneumatic tire |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH09194640A (ja) * | 1996-01-18 | 1997-07-29 | Bridgestone Corp | ゴム組成物 |
WO2008029814A1 (fr) * | 2006-09-04 | 2008-03-13 | Bridgestone Corporation | Composition de caoutchouc et bandage pneumatique utilisant celle-ci |
JP2008184517A (ja) * | 2007-01-29 | 2008-08-14 | Bridgestone Corp | ゴム組成物及びそれを用いた空気入りタイヤ |
JP2008201957A (ja) * | 2007-02-21 | 2008-09-04 | Bridgestone Corp | 老化防止剤含有ウェットマスターバッチの製造方法、ゴム組成物及びタイヤ |
WO2011003983A1 (fr) * | 2009-07-10 | 2011-01-13 | Societe De Technologie Michelin | Composition a base de caoutchouc naturel et d'un compose poly-amine |
JP2012102240A (ja) * | 2010-11-10 | 2012-05-31 | Sumitomo Rubber Ind Ltd | タイヤ用ゴム組成物及び空気入りタイヤ |
-
2012
- 2012-06-05 JP JP2012128304A patent/JP6144464B2/ja active Active
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH09194640A (ja) * | 1996-01-18 | 1997-07-29 | Bridgestone Corp | ゴム組成物 |
WO2008029814A1 (fr) * | 2006-09-04 | 2008-03-13 | Bridgestone Corporation | Composition de caoutchouc et bandage pneumatique utilisant celle-ci |
JP2008184517A (ja) * | 2007-01-29 | 2008-08-14 | Bridgestone Corp | ゴム組成物及びそれを用いた空気入りタイヤ |
JP2008201957A (ja) * | 2007-02-21 | 2008-09-04 | Bridgestone Corp | 老化防止剤含有ウェットマスターバッチの製造方法、ゴム組成物及びタイヤ |
WO2011003983A1 (fr) * | 2009-07-10 | 2011-01-13 | Societe De Technologie Michelin | Composition a base de caoutchouc naturel et d'un compose poly-amine |
JP2012102240A (ja) * | 2010-11-10 | 2012-05-31 | Sumitomo Rubber Ind Ltd | タイヤ用ゴム組成物及び空気入りタイヤ |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP3006227A1 (en) * | 2014-10-06 | 2016-04-13 | Sumitomo Rubber Industries, Ltd. | Rubber composition and pneumatic tire |
EP3006493A1 (en) * | 2014-10-06 | 2016-04-13 | Sumitomo Rubber Industries, Ltd. | Rubber composition and pneumatic tire |
JP2016074880A (ja) * | 2014-10-06 | 2016-05-12 | 住友ゴム工業株式会社 | ゴム組成物および空気入りタイヤ |
JP2016074881A (ja) * | 2014-10-06 | 2016-05-12 | 住友ゴム工業株式会社 | ゴム組成物および空気入りタイヤ |
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