JP5543136B2 - ゴム組成物 - Google Patents
ゴム組成物 Download PDFInfo
- Publication number
- JP5543136B2 JP5543136B2 JP2009133418A JP2009133418A JP5543136B2 JP 5543136 B2 JP5543136 B2 JP 5543136B2 JP 2009133418 A JP2009133418 A JP 2009133418A JP 2009133418 A JP2009133418 A JP 2009133418A JP 5543136 B2 JP5543136 B2 JP 5543136B2
- Authority
- JP
- Japan
- Prior art keywords
- rubber
- sulfenamide
- group
- mass
- cobalt
- 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 72
- 239000005060 rubber Substances 0.000 title claims description 72
- 239000000203 mixture Substances 0.000 title claims description 31
- 238000004073 vulcanization Methods 0.000 claims description 56
- 239000010941 cobalt Substances 0.000 claims description 30
- 229910017052 cobalt Inorganic materials 0.000 claims description 30
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 30
- QAZLUNIWYYOJPC-UHFFFAOYSA-M sulfenamide Chemical compound [Cl-].COC1=C(C)C=[N+]2C3=NC4=CC=C(OC)C=C4N3SCC2=C1C QAZLUNIWYYOJPC-UHFFFAOYSA-M 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 12
- 239000011593 sulfur Substances 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 229920001194 natural rubber Polymers 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 8
- 244000043261 Hevea brasiliensis Species 0.000 claims description 7
- 229920003052 natural elastomer Polymers 0.000 claims description 7
- 150000007524 organic acids Chemical class 0.000 claims description 7
- 150000001868 cobalt Chemical class 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- -1 1,3-dimethylbutyl group Chemical group 0.000 description 34
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
- 229910052751 metal Inorganic materials 0.000 description 13
- 239000002184 metal Substances 0.000 description 13
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 12
- 238000000034 method Methods 0.000 description 9
- CMAUJSNXENPPOF-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)-n-cyclohexylcyclohexanamine Chemical compound C1CCCCC1N(C1CCCCC1)SC1=NC2=CC=CC=C2S1 CMAUJSNXENPPOF-UHFFFAOYSA-N 0.000 description 9
- 239000000377 silicon dioxide Substances 0.000 description 9
- 241001441571 Hiodontidae Species 0.000 description 8
- 229910000831 Steel Inorganic materials 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- 239000010959 steel Substances 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000012779 reinforcing material Substances 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000011256 inorganic filler Substances 0.000 description 5
- 229910003475 inorganic filler Inorganic materials 0.000 description 5
- 238000004898 kneading Methods 0.000 description 5
- 239000011777 magnesium Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- XKIDASBNXGXGLR-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)-2,4,4-trimethylpentan-2-amine Chemical compound C1=CC=C2SC(SNC(C)(C)CC(C)(C)C)=NC2=C1 XKIDASBNXGXGLR-UHFFFAOYSA-N 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000002585 base Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000013329 compounding Methods 0.000 description 4
- 239000007822 coupling agent Substances 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 230000003014 reinforcing effect Effects 0.000 description 4
- 229920003051 synthetic elastomer Polymers 0.000 description 4
- 239000005061 synthetic rubber Substances 0.000 description 4
- ODINCKMPIJJUCX-UHFFFAOYSA-N Calcium oxide Chemical compound [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000002411 adverse Effects 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 239000006229 carbon black Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- AFZSMODLJJCVPP-UHFFFAOYSA-N dibenzothiazol-2-yl disulfide Chemical compound C1=CC=C2SC(SSC=3SC4=CC=CC=C4N=3)=NC2=C1 AFZSMODLJJCVPP-UHFFFAOYSA-N 0.000 description 3
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- DEQZTKGFXNUBJL-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)cyclohexanamine Chemical compound C1CCCCC1NSC1=NC2=CC=CC=C2S1 DEQZTKGFXNUBJL-UHFFFAOYSA-N 0.000 description 3
- 239000012763 reinforcing filler Substances 0.000 description 3
- 239000004636 vulcanized rubber Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 229910004283 SiO 4 Inorganic materials 0.000 description 2
- 239000006087 Silane Coupling Agent Substances 0.000 description 2
- 239000005708 Sodium hypochlorite Substances 0.000 description 2
- 229910010413 TiO 2 Inorganic materials 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
- 239000000395 magnesium oxide Substances 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- 229910052901 montmorillonite Inorganic materials 0.000 description 2
- ORNPDRMNXQVYPM-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)-2-methylhexan-2-amine Chemical compound C1=CC=C2SC(SNC(C)(C)CCCC)=NC2=C1 ORNPDRMNXQVYPM-UHFFFAOYSA-N 0.000 description 2
- IUJLOAKJZQBENM-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)-2-methylpropan-2-amine Chemical compound C1=CC=C2SC(SNC(C)(C)C)=NC2=C1 IUJLOAKJZQBENM-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 229910052903 pyrophyllite Inorganic materials 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 150000003839 salts Chemical class 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
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- QIJIUJYANDSEKG-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-amine Chemical compound CC(C)(C)CC(C)(C)N QIJIUJYANDSEKG-UHFFFAOYSA-N 0.000 description 1
- PWKJAOHGWASASX-UHFFFAOYSA-N 2-methyl-n-[(4-methyl-1,3-benzothiazol-2-yl)sulfanyl]butan-2-amine Chemical compound C1=CC=C2SC(SNC(C)(C)CC)=NC2=C1C PWKJAOHGWASASX-UHFFFAOYSA-N 0.000 description 1
- HZKLVOHTSRPVEH-UHFFFAOYSA-N 2-methyl-n-[(4-methyl-1,3-benzothiazol-2-yl)sulfanyl]hexan-2-amine Chemical compound C1=CC=C2SC(SNC(C)(C)CCCC)=NC2=C1C HZKLVOHTSRPVEH-UHFFFAOYSA-N 0.000 description 1
- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- HRQJMFRZRHCHQQ-UHFFFAOYSA-N 3-triethoxysilylpropane-1-thiol;3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS.CCO[Si](OCC)(OCC)CCCS HRQJMFRZRHCHQQ-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
- TYWQCXCGSWSCFC-UHFFFAOYSA-N 4,6-dimethylhept-2-ene Chemical compound CC=CC(C)CC(C)C TYWQCXCGSWSCFC-UHFFFAOYSA-N 0.000 description 1
- YKBYBYAFEAREKR-UHFFFAOYSA-N 4-(3-dimethoxysilylbutyltetrasulfanyl)butan-2-yl-dimethoxysilane Chemical compound CO[SiH](OC)C(C)CCSSSSCCC(C)[SiH](OC)OC YKBYBYAFEAREKR-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 229910001369 Brass Inorganic materials 0.000 description 1
- GGVWVCMVONJVJU-UHFFFAOYSA-N C(CC(C)C)NSC=1SC2=C(N1)C(=CC=C2)C Chemical compound C(CC(C)C)NSC=1SC2=C(N1)C(=CC=C2)C GGVWVCMVONJVJU-UHFFFAOYSA-N 0.000 description 1
- QDHHCQZDFGDHMP-UHFFFAOYSA-N Chloramine Chemical compound ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 239000006237 Intermediate SAF Substances 0.000 description 1
- 229910017625 MgSiO Inorganic materials 0.000 description 1
- 229920000459 Nitrile rubber Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000004902 Softening Agent 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
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 239000006230 acetylene black Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 229910001680 bayerite Inorganic materials 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 125000005619 boric acid group Chemical group 0.000 description 1
- 239000010951 brass Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- 239000000378 calcium silicate Substances 0.000 description 1
- 229910052918 calcium silicate Inorganic materials 0.000 description 1
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
- YLUIKWVQCKSMCF-UHFFFAOYSA-N calcium;magnesium;oxygen(2-) Chemical compound [O-2].[O-2].[Mg+2].[Ca+2] YLUIKWVQCKSMCF-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000006231 channel black Substances 0.000 description 1
- 238000010073 coating (rubber) Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical class [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 1
- UFMZWBIQTDUYBN-UHFFFAOYSA-N cobalt dinitrate Chemical class [Co+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O UFMZWBIQTDUYBN-UHFFFAOYSA-N 0.000 description 1
- 229910001981 cobalt nitrate Inorganic materials 0.000 description 1
- 229910000152 cobalt phosphate Inorganic materials 0.000 description 1
- 229940044175 cobalt sulfate Drugs 0.000 description 1
- 229910000361 cobalt sulfate Inorganic materials 0.000 description 1
- KTVIXTQDYHMGHF-UHFFFAOYSA-L cobalt(2+) sulfate Chemical class [Co+2].[O-]S([O-])(=O)=O KTVIXTQDYHMGHF-UHFFFAOYSA-L 0.000 description 1
- KDMCQAXHWIEEDE-UHFFFAOYSA-L cobalt(2+);7,7-dimethyloctanoate Chemical compound [Co+2].CC(C)(C)CCCCCC([O-])=O.CC(C)(C)CCCCCC([O-])=O KDMCQAXHWIEEDE-UHFFFAOYSA-L 0.000 description 1
- XTUHPOUJWWTMNC-UHFFFAOYSA-N cobalt(2+);dioxido(dioxo)chromium Chemical class [Co+2].[O-][Cr]([O-])(=O)=O XTUHPOUJWWTMNC-UHFFFAOYSA-N 0.000 description 1
- ZBDSFTZNNQNSQM-UHFFFAOYSA-H cobalt(2+);diphosphate Chemical class [Co+2].[Co+2].[Co+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O ZBDSFTZNNQNSQM-UHFFFAOYSA-H 0.000 description 1
- AMFIJXSMYBKJQV-UHFFFAOYSA-L cobalt(2+);octadecanoate Chemical compound [Co+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O AMFIJXSMYBKJQV-UHFFFAOYSA-L 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- UEZWYKZHXASYJN-UHFFFAOYSA-N cyclohexylthiophthalimide Chemical compound O=C1C2=CC=CC=C2C(=O)N1SC1CCCCC1 UEZWYKZHXASYJN-UHFFFAOYSA-N 0.000 description 1
- UAMZXLIURMNTHD-UHFFFAOYSA-N dialuminum;magnesium;oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[Mg+2].[Al+3].[Al+3] UAMZXLIURMNTHD-UHFFFAOYSA-N 0.000 description 1
- OTARVPUIYXHRRB-UHFFFAOYSA-N diethoxy-methyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](C)(OCC)CCCOCC1CO1 OTARVPUIYXHRRB-UHFFFAOYSA-N 0.000 description 1
- FSBVERYRVPGNGG-UHFFFAOYSA-N dimagnesium dioxido-bis[[oxido(oxo)silyl]oxy]silane hydrate Chemical compound O.[Mg+2].[Mg+2].[O-][Si](=O)O[Si]([O-])([O-])O[Si]([O-])=O FSBVERYRVPGNGG-UHFFFAOYSA-N 0.000 description 1
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 1
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000010433 feldspar Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000006232 furnace black Substances 0.000 description 1
- 229910001679 gibbsite Inorganic materials 0.000 description 1
- 229920005555 halobutyl Polymers 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 229910052919 magnesium silicate Inorganic materials 0.000 description 1
- 235000019792 magnesium silicate Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000002905 metal composite material Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 1
- JTSLLDFBJGZEMB-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)-10-methylundecan-1-amine Chemical compound C1=CC=C2SC(SNCCCCCCCCCC(C)C)=NC2=C1 JTSLLDFBJGZEMB-UHFFFAOYSA-N 0.000 description 1
- WVVKGODKQODIJB-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)-2-methylbutan-2-amine Chemical compound C1=CC=C2SC(SNC(C)(C)CC)=NC2=C1 WVVKGODKQODIJB-UHFFFAOYSA-N 0.000 description 1
- UIAUHCVSWRMESA-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)-2-methylpentan-2-amine Chemical compound C1=CC=C2SC(SNC(C)(C)CCC)=NC2=C1 UIAUHCVSWRMESA-UHFFFAOYSA-N 0.000 description 1
- NTEWYQKBQJDYJG-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)-3-methylbutan-1-amine Chemical compound C1=CC=C2SC(SNCCC(C)C)=NC2=C1 NTEWYQKBQJDYJG-UHFFFAOYSA-N 0.000 description 1
- OTFJJUZXDPASLI-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)-4-methylpentan-1-amine Chemical compound C1=CC=C2SC(SNCCCC(C)C)=NC2=C1 OTFJJUZXDPASLI-UHFFFAOYSA-N 0.000 description 1
- GMLUBLPMOKLYPW-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)-5-methylhexan-1-amine Chemical compound C1=CC=C2SC(SNCCCCC(C)C)=NC2=C1 GMLUBLPMOKLYPW-UHFFFAOYSA-N 0.000 description 1
- FUWKDBQBFGEIJC-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)-6-methylheptan-1-amine Chemical compound C1=CC=C2SC(SNCCCCCC(C)C)=NC2=C1 FUWKDBQBFGEIJC-UHFFFAOYSA-N 0.000 description 1
- UCAVTFWBNOIWJM-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)-8-methylnonan-1-amine Chemical compound C1=CC=C2SC(SNCCCCCCCC(C)C)=NC2=C1 UCAVTFWBNOIWJM-UHFFFAOYSA-N 0.000 description 1
- KDXHRXRXDVELFM-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)-9-methyldecan-1-amine Chemical compound C1=CC=C2SC(SNCCCCCCCCC(C)C)=NC2=C1 KDXHRXRXDVELFM-UHFFFAOYSA-N 0.000 description 1
- LZRIGRGBIJWTSZ-UHFFFAOYSA-N n-[(4,6-dimethoxy-1,3-benzothiazol-2-yl)sulfanyl]-2-methylbutan-2-amine Chemical compound C1=C(OC)C=C2SC(SNC(C)(C)CC)=NC2=C1OC LZRIGRGBIJWTSZ-UHFFFAOYSA-N 0.000 description 1
- GXWDDEQRSHYMPA-UHFFFAOYSA-N n-[(4,6-dimethoxy-1,3-benzothiazol-2-yl)sulfanyl]-2-methylhexan-2-amine Chemical compound C1=C(OC)C=C2SC(SNC(C)(C)CCCC)=NC2=C1OC GXWDDEQRSHYMPA-UHFFFAOYSA-N 0.000 description 1
- ZLDQYNDVEOOKLU-UHFFFAOYSA-N n-[(4,6-dimethoxy-1,3-benzothiazol-2-yl)sulfanyl]-3-methylbutan-1-amine Chemical compound COC1=CC(OC)=C2N=C(SNCCC(C)C)SC2=C1 ZLDQYNDVEOOKLU-UHFFFAOYSA-N 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl 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])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 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
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- HBACTRZJLWXFBM-UHFFFAOYSA-N s-[[methyl(4-trimethoxysilylbutyl)carbamoyl]trisulfanyl] n-methyl-n-(4-trimethoxysilylbutyl)carbamothioate Chemical compound CO[Si](OC)(OC)CCCCN(C)C(=O)SSSSC(=O)N(C)CCCC[Si](OC)(OC)OC HBACTRZJLWXFBM-UHFFFAOYSA-N 0.000 description 1
- 125000005920 sec-butoxy group Chemical group 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000006234 thermal black Substances 0.000 description 1
- 235000010215 titanium dioxide Nutrition 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
- 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 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
- NQRACKNXKKOCJY-UHFFFAOYSA-N trimethoxy-[3-(3-trimethoxysilylpropyldisulfanyl)propyl]silane Chemical compound CO[Si](OC)(OC)CCCSSCCC[Si](OC)(OC)OC NQRACKNXKKOCJY-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
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- 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
- C08K5/45—Heterocyclic compounds having sulfur in the ring
- C08K5/46—Heterocyclic compounds having sulfur in the ring with oxygen or nitrogen in the ring
- C08K5/47—Thiazoles
-
- 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
- C08K5/04—Oxygen-containing compounds
- C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
- C08K5/098—Metal salts of carboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
このゴム−金属複合材料が高い補強効果を発揮して信頼性を得るためには、ゴム−金属補強材間に安定した経時変化の少ない接着が必要である。
すなわち、本発明のゴム組成物は、ゴム成分、式(I)で表されるスルフェンアミド系加硫促進剤および硫黄を含有してなることを特徴とする。
さらに、前記式(I)中、R2〜R5がすべて水素原子であるのが好ましく、R1が炭素数5〜8の直鎖アルキル基または分岐アルキル基であるのが好ましい。
また、前記コバルト系成分の含有量は、コバルト量として前記ゴム成分100質量部に対し、0.03〜1質量部の量であるのが好ましく、前記コバルトを含有する化合物は、有機酸のコバルト塩であるのが好ましい。
前記ゴム成分は、天然ゴムおよびポリイソプレンゴムの少なくとも一方を含むのが望ましく、前記ゴム成分100質量%中、天然ゴムを50質量%以上の量で含むのが望ましい。
したがって、本発明のゴム組成物は、スチールコードを補強材としたタイヤやコンベアベルト等のゴム物品に好適に使用することができる。
本発明のゴム組成物は、ゴム成分、式(I)で表されるスルフェンアミド系加硫促進剤および硫黄を含有してなることを特徴とする。
本製造方法に用いる溶媒としては、アルコールが望ましく、特にメタノールが望ましい。
これらのコバルト量の含有量が0.03質量部未満では、さらなる接着性を発揮することができず、一方、1質量部を越えると、老化物性が大きく低下し、好ましくない。
mM1・xSiOy・zH2O ・・・(Y)
(式(Y)中、M1は、アルミニウム、マグネシウム、チタン、カルシウムからなる群から選ばれる金属、これらの金属の酸化物または水酸化物、およびそれらの水和物から選ばれる少なくとも一種であり、m、x、yおよびzは、それぞれ1〜5の整数、0〜10の整数、2〜5の整数、および0〜10の整数である)。さらに、カリウム、ナトリウム、鉄、マグネシウムなどの金属や、フッ素などの元素、およびNH4−などの基を含有していてもよい。
Al2O3・nH2O(但し、式中nは0〜3である。) ・・・(Z)
クレー類では、クレー(Al2O3・2SiO2)、カオリン(Al2O3・2SiO2・2H2O)、パイロフィライト(Al2O3・4SiO2・H2O)、ベントナイト(Al2O3・4SiO2・2H2O)、モンモリロナイト等が挙げられる。
1000mL四つ口フラスコにDM−P(133.0g、0.4mol)、ノイゲンET(200mg)、水200mLを加え、10℃に冷却した。tert−オクチルアミン(113.7g、0.88mol)を1時間かけて滴下後、40℃に昇温し、1時間攪拌した。トルエン50mLを加え、35%過酸化水素水溶液(42.8g、0.44mol)を40分かけて滴下し、1時間攪拌した。その後、12%次亜塩素酸ソーダ水溶液(273g、0.44mol)を1時間かけて滴下した。トルエン200mLを加えて分液し、上層を減圧下ロータリーエバポレーターで濃縮した(240.1g)。続いてアセトン450mLを加え、50℃に加熱し、熱濾過した。室温まで冷却し、析出した結晶を濾過した。40℃で12時間熱風乾燥し、白色結晶の目的物である下記式で表されるN−(1,1,3,3−テトラメチルブチル)ベンゾチアゾール−2−スルフェンアミド(加硫促進剤1)(183.7g、0.62mol、収率78%、融点103.7〜104.4℃)を得た。
1H−NMR(CDCl3)d(ppm):7.70−7.80(m,2H)、7.38(t,1H,7.6Hz)、7.25(t,1H,7.6Hz)、3.52(s,1H)、1.59(s,2H)、1.32(s,6H)、1.07(s,9H).
ゴム成分、加硫促進剤、硫黄、その他の配合剤を表1に示す配合処方で混練り混合して、未加硫のゴム組成物を調製し、以下の方法にしたがって評価した。結果を表1に示す。
JIS K 6300−1:2001に準拠して行った。
なお、評価は、比較例1の値を100として指数表示した。ムーニー粘度は、値が小さいほど混練時の作業性が良好であることを示し、ムーニースコーチタイムは、値が大きいほど混練後の作業性が良好であることを示す。
黄銅めっき(Cu:63質量%、Zu:37質量%)したスチールコード(外径0.5mm×長さ300mm)3本を10mm間隔で平行に並べ、このスチールコードを上下両側から各ゴム組成物でコーティングして、これを160℃、20分間の条件で加硫し、サンプルを作製した。
得られた各サンプルの各耐熱接着性について、ASTM−D−2229に準拠して、各サンプルを100℃のギヤオーブンに15日、30日間放置した後にスチールコードを引き抜き、ゴムの被覆状態を目視で観察し、0〜100%で表示して各耐熱接着性の指標とした。数値が大きいほど、耐熱接着性に優れることを示す。
※2:N,N’−ジシクロヘキシル−2−ベンゾチアジルスルフェンアミド(ノクセラーDZ、大内新興化学工業(株)製)
※3:N−シクロヘキシル−2−ベンゾチアジルスルフェンアミド(ノクセラーCZ、大内新興化学工業(株)製)
※4:製品名:マノボンドC22.5、OMG社製、コバルト含有量:22.5質量%
Claims (8)
- 前記ゴム成分100質量部に対し、前記スルフェンアミド系加硫促進剤を0.1〜10質量部の量で含有してなることを特徴とする請求項1に記載のゴム組成物。
- 前記ゴム成分100質量部に対し、前記硫黄を0.3〜10質量部の量で含有してなることを特徴とする請求項1または2に記載のゴム組成物。
- 前記式(I)中、R2〜R5がすべて水素原子であることを特徴とする請求項1〜3のいずれかに記載のゴム組成物。
- 前記コバルト系成分の含有量が、コバルト量として前記ゴム成分100質量部に対し、0.03〜1質量部の量であることを特徴とする請求項1に記載のゴム組成物。
- 前記コバルトを含有する化合物が、有機酸のコバルト塩であることを特徴とする請求項1〜5のいずれかに記載のゴム組成物。
- 前記ゴム成分が、天然ゴムおよびポリイソプレンゴムの少なくとも一方を含む請求項1〜6のいずれかに記載のゴム組成物。
- 前記ゴム成分100質量%中、天然ゴムを50質量%以上の量で含む請求項7に記載のゴム組成物。
Priority Applications (5)
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JP2009133418A JP5543136B2 (ja) | 2009-06-02 | 2009-06-02 | ゴム組成物 |
US13/375,675 US20120136102A1 (en) | 2009-06-02 | 2010-06-02 | Rubber composition |
CN201080033915.2A CN102803372A (zh) | 2009-06-02 | 2010-06-02 | 橡胶组合物 |
EP10783152.1A EP2439236B1 (en) | 2009-06-02 | 2010-06-02 | Rubber composition |
PCT/JP2010/003694 WO2010140364A1 (ja) | 2009-06-02 | 2010-06-02 | ゴム組成物 |
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JP2009133418A JP5543136B2 (ja) | 2009-06-02 | 2009-06-02 | ゴム組成物 |
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JP2010280764A JP2010280764A (ja) | 2010-12-16 |
JP5543136B2 true JP5543136B2 (ja) | 2014-07-09 |
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US (1) | US20120136102A1 (ja) |
EP (1) | EP2439236B1 (ja) |
JP (1) | JP5543136B2 (ja) |
CN (1) | CN102803372A (ja) |
WO (1) | WO2010140364A1 (ja) |
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US2367827A (en) * | 1941-10-30 | 1945-01-23 | Firestone Tire & Rubber Co | Accelerator for vulcanization of rubber |
US3038888A (en) * | 1958-06-16 | 1962-06-12 | Firestone Tire & Rubber Co | New nitrogenous organic compounds |
US4267079A (en) * | 1979-11-13 | 1981-05-12 | The Firestone Tire & Rubber Company | Cured rubber skim compositions exhibiting better humidity aged metal adhesion and metal adhesion retention |
JPS6028858B2 (ja) * | 1981-11-24 | 1985-07-06 | 横浜ゴム株式会社 | ゴム組成物 |
US6077874A (en) * | 1998-07-15 | 2000-06-20 | The Goodyear Tire & Rubber Company | Process for improving the properties of ground recycled rubber |
JP2005139239A (ja) | 2003-11-04 | 2005-06-02 | Sanshin Chem Ind Co Ltd | 天然油脂由来のアミンを使用した加硫促進剤およびゴム組成物 |
JP2005139082A (ja) | 2003-11-04 | 2005-06-02 | Sanshin Chem Ind Co Ltd | スルフェンアミド化合物 |
JP4171434B2 (ja) * | 2004-02-26 | 2008-10-22 | 住友ゴム工業株式会社 | ベルト層スチールコード用ゴム組成物およびそれにより被覆されたスチールコード |
JP5009572B2 (ja) * | 2006-09-11 | 2012-08-22 | 株式会社ブリヂストン | 重荷重用ラジアルタイヤ |
KR20100103853A (ko) * | 2007-12-27 | 2010-09-28 | 가부시키가이샤 브리지스톤 | 고무 조성물 |
-
2009
- 2009-06-02 JP JP2009133418A patent/JP5543136B2/ja active Active
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2010
- 2010-06-02 US US13/375,675 patent/US20120136102A1/en not_active Abandoned
- 2010-06-02 WO PCT/JP2010/003694 patent/WO2010140364A1/ja active Application Filing
- 2010-06-02 CN CN201080033915.2A patent/CN102803372A/zh active Pending
- 2010-06-02 EP EP10783152.1A patent/EP2439236B1/en active Active
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EP2439236A1 (en) | 2012-04-11 |
CN102803372A (zh) | 2012-11-28 |
WO2010140364A1 (ja) | 2010-12-09 |
JP2010280764A (ja) | 2010-12-16 |
US20120136102A1 (en) | 2012-05-31 |
EP2439236A4 (en) | 2012-12-05 |
EP2439236B1 (en) | 2014-10-01 |
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