JP6125323B2 - ゴム組成物及び空気入りタイヤ - Google Patents
ゴム組成物及び空気入りタイヤ Download PDFInfo
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- JP6125323B2 JP6125323B2 JP2013105174A JP2013105174A JP6125323B2 JP 6125323 B2 JP6125323 B2 JP 6125323B2 JP 2013105174 A JP2013105174 A JP 2013105174A JP 2013105174 A JP2013105174 A JP 2013105174A JP 6125323 B2 JP6125323 B2 JP 6125323B2
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- azo compound
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- 229920001971 elastomer Polymers 0.000 title claims description 43
- 239000005060 rubber Substances 0.000 title claims description 43
- 239000000203 mixture Substances 0.000 title claims description 29
- -1 azo compound Chemical class 0.000 claims description 45
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 25
- 239000006087 Silane Coupling Agent Substances 0.000 description 14
- 125000005370 alkoxysilyl group Chemical group 0.000 description 14
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 13
- 239000000377 silicon dioxide Substances 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 229910052717 sulfur Inorganic materials 0.000 description 7
- 239000011593 sulfur Substances 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000006229 carbon black Substances 0.000 description 5
- 230000020169 heat generation Effects 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 230000003014 reinforcing effect Effects 0.000 description 5
- 239000012763 reinforcing filler Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 230000006866 deterioration Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 238000004073 vulcanization Methods 0.000 description 4
- PFHOSZAOXCYAGJ-UHFFFAOYSA-N 2-[(2-cyano-4-methoxy-4-methylpentan-2-yl)diazenyl]-4-methoxy-2,4-dimethylpentanenitrile Chemical compound COC(C)(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)(C)OC PFHOSZAOXCYAGJ-UHFFFAOYSA-N 0.000 description 3
- 229940126062 Compound A Drugs 0.000 description 3
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 235000002597 Solanum melongena Nutrition 0.000 description 3
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
- 230000002787 reinforcement Effects 0.000 description 3
- 229920003048 styrene butadiene rubber Polymers 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- LYPGJGCIPQYQBW-UHFFFAOYSA-N 2-methyl-2-[[2-methyl-1-oxo-1-(prop-2-enylamino)propan-2-yl]diazenyl]-n-prop-2-enylpropanamide Chemical compound C=CCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCC=C LYPGJGCIPQYQBW-UHFFFAOYSA-N 0.000 description 2
- DCQBZYNUSLHVJC-UHFFFAOYSA-N 3-triethoxysilylpropane-1-thiol Chemical compound CCO[Si](OCC)(OCC)CCCS DCQBZYNUSLHVJC-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 244000043261 Hevea brasiliensis Species 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 150000004703 alkoxides Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000003712 anti-aging effect Effects 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 150000001723 carbon free-radicals Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- ZQMHJBXHRFJKOT-UHFFFAOYSA-N methyl 2-[(1-methoxy-2-methyl-1-oxopropan-2-yl)diazenyl]-2-methylpropanoate Chemical compound COC(=O)C(C)(C)N=NC(C)(C)C(=O)OC ZQMHJBXHRFJKOT-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 2
- 229920003052 natural elastomer Polymers 0.000 description 2
- 229920001194 natural rubber Polymers 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 229920002857 polybutadiene Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 238000005987 sulfurization reaction Methods 0.000 description 2
- 230000001629 suppression Effects 0.000 description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- WYGWHHGCAGTUCH-UHFFFAOYSA-N 2-[(2-cyano-4-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)C WYGWHHGCAGTUCH-UHFFFAOYSA-N 0.000 description 1
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 1
- 0 CC(C)(**(NC[*+])=O)N=N* Chemical compound CC(C)(**(NC[*+])=O)N=N* 0.000 description 1
- 241001441571 Hiodontidae Species 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 241000872198 Serjania polyphylla Species 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 239000002174 Styrene-butadiene Substances 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 239000007877 V-601 Substances 0.000 description 1
- 239000007874 V-70 Substances 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 229920003244 diene elastomer Polymers 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical compound CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000005065 mining Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 229940080818 propionamide Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- TXDNPSYEJHXKMK-UHFFFAOYSA-N sulfanylsilane Chemical compound S[SiH3] TXDNPSYEJHXKMK-UHFFFAOYSA-N 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-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
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Landscapes
- Tires In General (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
下記表1,2にそれぞれ示した配合(特に示した以外は質量部)に従い、まず硫黄及び加硫促進剤を除く成分を混合し、次いで硫黄と加硫促進剤を添加混合して、タイヤ用ゴム組成物を調製した。表1,2中の各配合物の詳細は、以下の通りである。
・SBR2:JSR(株)製「SBR0122」
・カーボンブラック:東海カーボン製「シースト3」
・シリカ:エボニック社製「Ultrasil VN3」
・シランカップリング剤:エボニック・デグサ社製「Si75」
・アゾ化合物A:次式で表される2,2’−アゾビス[N−(2−プロペニル)−2−メチルプロピオンアミド](和光純薬工業(株)製)
・アゾ化合物C:下記合成例2により得られたアルコキシシリル基含有アゾ化合物
・オイル:昭和シェル石油(株)製「エキストラクト4号S」
・亜鉛華:三井金属鉱業(株)製「亜鉛華1号」
・ステアリン酸:花王(株)製「ルナックS20」
・老化防止剤:大内新興化学工業(株)製「ノクラック6C」
・ワックス:日本精蝋(株)製「OZOACE0355」
・硫黄:鶴見化学工業(株)製「粉末硫黄」
・加硫促進剤1:住友化学(株)製「ソクシノールCZ」
・加硫促進剤2:大内新興化学工業(株)製「ノクセラーD」
ナスフラスコに、2,2’−アゾビス(イソ酪酸メチル)(和光純薬工業(株)製、商品名V−601、10時間半減期温度66℃)230g、3−アミノプロピルトリメトキシシラン(信越化学工業(株)製、信越シリコーン)358g及び触媒としてのナトリウムメトキシド粉末10.8gを仕込んだ。続いて、ナスフラスコを常温(23℃)の水浴上に移し、減圧しながら撹拌を開始し、1時間半、減圧、撹拌を続けた。次に、水浴の温度を35℃に設定し、減圧、撹拌を6時間続けた後、常温で16時間放置し、再度35℃の水浴上で減圧、撹拌を8時間行った後、再び常温で16時間放置した。次いで精製操作として、乾燥させたクロロホルム29.8gをフラスコ内容物に加え、常温で撹拌しながらナトリウムメトキシドとの反応を行った。2時間後、予め乾燥させておいたトルエン450gを加え、ガラスフィルターで減圧濾過し、得られた溶液をナスフラスコに取り、減圧乾燥した。精製後の反応物につき、1H−NMR及び13C−NMR解析を行い、次式で表される2,2’−アゾビス[N−(3−トリメトキシシリルプロピル)イソ酪酸アミド](アゾ化合物B)であることを確認した。
ナスフラスコに2,2’−アゾビス[N−(2−プロペニル)−2−メチルプロピオンアミド](和光純薬工業(株)製、商品名VF−096、10時間半減期温度96℃)20gと、3−メルカプトプロピルトリエトキシシラン(東京化成工業(株)製)34.5gと、2,2’−アゾビス(4−メトキシ−2,4−ジメチルバレロニトリル)(和光純薬工業(株)製、商品名V−70、10時間半減期温度30℃)0.66gと、トルエン55gを入れ、マグネチックスターラーにて撹拌しながら20分間窒素置換し、密栓した。次いで、反応溶液を35℃に保持した水浴中に入れ、撹拌しながら2時間反応させた。得られた反応物につき、エバポレーターにて濃縮を行い、カラムクロマトグラフィーにて精製を行った。精製後の反応物につき、1H−NMR及び13C−NMR解析を行い、次式で表される2,2’−アゾビス[2−メチル−N−(3−(3−(トリエトキシシリル)プロピルチオ)プロピル)プロピオンアミド](化合物C)であることを確認した。
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JP2013105174A JP6125323B2 (ja) | 2012-12-13 | 2013-05-17 | ゴム組成物及び空気入りタイヤ |
US14/070,878 US8741994B1 (en) | 2012-12-13 | 2013-11-04 | Alkoxysilyl group-containing azo compound and rubber composition using the same |
DE102013019004.5A DE102013019004B4 (de) | 2012-12-13 | 2013-11-13 | Alkoxysilylgruppe enthaltende Azoverbindung und Gummizusammensetzung unter Verwendung derselben |
CN201310674890.XA CN103864836B (zh) | 2012-12-13 | 2013-12-11 | 含有烷氧基甲硅烷基的偶氮化合物以及使用该偶氮化合物的橡胶组合物 |
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JP2788076B2 (ja) * | 1988-10-20 | 1998-08-20 | 鐘淵化学工業株式会社 | 加水分解性シリル基含有アゾ系化合物 |
JP2510345B2 (ja) * | 1990-08-30 | 1996-06-26 | 積水化学工業株式会社 | アルコキシシリル基含有アゾ化合物及びその製造方法 |
FR2973384B1 (fr) * | 2011-04-01 | 2014-08-22 | Michelin Soc Tech | Composition de caoutchouc pour pneumatique comportant un agent de couplage azosilane. |
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