WO2011162004A1 - アクリルゴム組成物、加硫物、ホース部品、シール部品 - Google Patents
アクリルゴム組成物、加硫物、ホース部品、シール部品 Download PDFInfo
- Publication number
- WO2011162004A1 WO2011162004A1 PCT/JP2011/058261 JP2011058261W WO2011162004A1 WO 2011162004 A1 WO2011162004 A1 WO 2011162004A1 JP 2011058261 W JP2011058261 W JP 2011058261W WO 2011162004 A1 WO2011162004 A1 WO 2011162004A1
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- WO
- WIPO (PCT)
- Prior art keywords
- acrylic rubber
- group
- parts
- rubber composition
- mass
- Prior art date
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- 229920000800 acrylic rubber Polymers 0.000 title claims abstract description 105
- 229920000058 polyacrylate Polymers 0.000 title claims abstract description 105
- 239000000203 mixture Substances 0.000 title claims abstract description 72
- 238000007789 sealing Methods 0.000 title description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 69
- -1 imidazole compound Chemical class 0.000 claims abstract description 50
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims abstract description 49
- 239000000377 silicon dioxide Substances 0.000 claims abstract description 34
- 239000006087 Silane Coupling Agent Substances 0.000 claims abstract description 27
- 125000003700 epoxy group Chemical group 0.000 claims abstract description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000005805 dimethoxy phenyl group Chemical group 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims 1
- 238000004073 vulcanization Methods 0.000 abstract description 34
- 238000007906 compression Methods 0.000 abstract description 21
- 230000006835 compression Effects 0.000 abstract description 21
- 238000012545 processing Methods 0.000 abstract description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 30
- 229920001971 elastomer Polymers 0.000 description 22
- 239000005060 rubber Substances 0.000 description 22
- WHGNXNCOTZPEEK-UHFFFAOYSA-N dimethoxy-methyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical group CO[Si](C)(OC)CCCOCC1CO1 WHGNXNCOTZPEEK-UHFFFAOYSA-N 0.000 description 17
- 230000000052 comparative effect Effects 0.000 description 12
- 239000000178 monomer Substances 0.000 description 12
- SESYNEDUKZDRJL-UHFFFAOYSA-N 3-(2-methylimidazol-1-yl)propanenitrile Chemical compound CC1=NC=CN1CCC#N SESYNEDUKZDRJL-UHFFFAOYSA-N 0.000 description 11
- 239000000047 product Substances 0.000 description 10
- 239000003921 oil Substances 0.000 description 9
- 239000004014 plasticizer Substances 0.000 description 9
- 239000006229 carbon black Substances 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 230000003712 anti-aging effect Effects 0.000 description 6
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 5
- 239000005977 Ethylene Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
- 229920000459 Nitrile rubber Polymers 0.000 description 4
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 4
- GIWQSPITLQVMSG-UHFFFAOYSA-N 1,2-dimethylimidazole Chemical compound CC1=NC=CN1C GIWQSPITLQVMSG-UHFFFAOYSA-N 0.000 description 3
- OQJQPIWVCBJVAZ-UHFFFAOYSA-N 1-methyl-2-phenylimidazole Chemical compound CN1C=CN=C1C1=CC=CC=C1 OQJQPIWVCBJVAZ-UHFFFAOYSA-N 0.000 description 3
- KYWMCFOWDYFYLV-UHFFFAOYSA-N 1h-imidazole-2-carboxylic acid Chemical compound OC(=O)C1=NC=CN1 KYWMCFOWDYFYLV-UHFFFAOYSA-N 0.000 description 3
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 3
- HYZAAPVEBKCHKQ-UHFFFAOYSA-N 4,4-dimethoxybutyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound C(C1CO1)OCCC[SiH2]CCCC(OC)OC HYZAAPVEBKCHKQ-UHFFFAOYSA-N 0.000 description 3
- VRGWNMQXSXRSTC-UHFFFAOYSA-N 4,5-dimethyl-2-phenyl-1h-imidazole Chemical compound N1C(C)=C(C)N=C1C1=CC=CC=C1 VRGWNMQXSXRSTC-UHFFFAOYSA-N 0.000 description 3
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 3
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- XQUUZTVNJCLMIA-UHFFFAOYSA-N dimethoxy-(4-methylphenyl)-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound C=1C=C(C)C=CC=1[Si](OC)(OC)CCCOCC1CO1 XQUUZTVNJCLMIA-UHFFFAOYSA-N 0.000 description 3
- KQBOHBAJKBCCOA-UHFFFAOYSA-N dimethoxy-[3-(oxiran-2-ylmethoxy)propyl]-propan-2-ylsilane Chemical compound CO[Si](C(C)C)(OC)CCCOCC1CO1 KQBOHBAJKBCCOA-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 3
- 229920001084 poly(chloroprene) Polymers 0.000 description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- 239000012744 reinforcing agent Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 3
- VNTPGSZQKARKHG-UHFFFAOYSA-N trimethyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound C[Si](C)(C)CCCOCC1CO1 VNTPGSZQKARKHG-UHFFFAOYSA-N 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 2
- VLZDYNDUVLBNLD-UHFFFAOYSA-N 3-(dimethoxymethylsilyl)propyl 2-methylprop-2-enoate Chemical compound COC(OC)[SiH2]CCCOC(=O)C(C)=C VLZDYNDUVLBNLD-UHFFFAOYSA-N 0.000 description 2
- KNTKCYKJRSMRMZ-UHFFFAOYSA-N 3-chloropropyl-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)CCCCl KNTKCYKJRSMRMZ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229920002943 EPDM rubber Polymers 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 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
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- GENZKBJGWAAVIE-UHFFFAOYSA-N diethoxy-[3-(oxiran-2-ylmethoxy)propyl]-phenylsilane Chemical compound C=1C=CC=CC=1[Si](OCC)(OCC)CCCOCC1CO1 GENZKBJGWAAVIE-UHFFFAOYSA-N 0.000 description 2
- OTARVPUIYXHRRB-UHFFFAOYSA-N diethoxy-methyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](C)(OCC)CCCOCC1CO1 OTARVPUIYXHRRB-UHFFFAOYSA-N 0.000 description 2
- JAPXJEHHGIVARY-UHFFFAOYSA-N diethoxymethyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCOC(OCC)[SiH2]CCCOCC1CO1 JAPXJEHHGIVARY-UHFFFAOYSA-N 0.000 description 2
- 229920005558 epichlorohydrin rubber Polymers 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 238000004898 kneading Methods 0.000 description 2
- FBNXYLDLGARYKQ-UHFFFAOYSA-N methoxy-dimethyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](C)(C)CCCOCC1CO1 FBNXYLDLGARYKQ-UHFFFAOYSA-N 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920002857 polybutadiene Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 229920003051 synthetic elastomer Polymers 0.000 description 2
- 239000005061 synthetic rubber Substances 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
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 1
- SILNNFMWIMZVEQ-UHFFFAOYSA-N 1,3-dihydrobenzimidazol-2-one Chemical compound C1=CC=C2NC(O)=NC2=C1 SILNNFMWIMZVEQ-UHFFFAOYSA-N 0.000 description 1
- YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 description 1
- OXFSTTJBVAAALW-UHFFFAOYSA-N 1,3-dihydroimidazole-2-thione Chemical compound SC1=NC=CN1 OXFSTTJBVAAALW-UHFFFAOYSA-N 0.000 description 1
- RPUYMGRFOKMRSB-UHFFFAOYSA-N 1,5-dicyclohexylimidazole Chemical compound C1CCCCC1C1=CN=CN1C1CCCCC1 RPUYMGRFOKMRSB-UHFFFAOYSA-N 0.000 description 1
- AGGRGODMKWLSDE-UHFFFAOYSA-N 1-[2,4,6-tri(propan-2-yl)phenyl]sulfonylimidazole Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1S(=O)(=O)N1C=NC=C1 AGGRGODMKWLSDE-UHFFFAOYSA-N 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
- NKWCGTOZTHZDHB-UHFFFAOYSA-N 1h-imidazol-1-ium-4-carboxylate Chemical compound OC(=O)C1=CNC=N1 NKWCGTOZTHZDHB-UHFFFAOYSA-N 0.000 description 1
- XYHKNCXZYYTLRG-UHFFFAOYSA-N 1h-imidazole-2-carbaldehyde Chemical compound O=CC1=NC=CN1 XYHKNCXZYYTLRG-UHFFFAOYSA-N 0.000 description 1
- XGDRLCRGKUCBQL-UHFFFAOYSA-N 1h-imidazole-4,5-dicarbonitrile Chemical compound N#CC=1N=CNC=1C#N XGDRLCRGKUCBQL-UHFFFAOYSA-N 0.000 description 1
- UUKFQKOPXUZHHW-UHFFFAOYSA-N 1h-imidazole-5-carbothioic s-acid Chemical compound SC(=O)C1=CN=CN1 UUKFQKOPXUZHHW-UHFFFAOYSA-N 0.000 description 1
- SINBGNJPYWNUQI-UHFFFAOYSA-N 2,2,2-trifluoro-1-imidazol-1-ylethanone Chemical compound FC(F)(F)C(=O)N1C=CN=C1 SINBGNJPYWNUQI-UHFFFAOYSA-N 0.000 description 1
- JCGGPCDDFXIVQB-UHFFFAOYSA-N 2,4,5-tribromo-1h-imidazole Chemical compound BrC1=NC(Br)=C(Br)N1 JCGGPCDDFXIVQB-UHFFFAOYSA-N 0.000 description 1
- RNIPJYFZGXJSDD-UHFFFAOYSA-N 2,4,5-triphenyl-1h-imidazole Chemical compound C1=CC=CC=C1C1=NC(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)N1 RNIPJYFZGXJSDD-UHFFFAOYSA-N 0.000 description 1
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- LQZDDWKUQKQXGC-UHFFFAOYSA-N 2-(2-methylprop-2-enoxymethyl)oxirane Chemical compound CC(=C)COCC1CO1 LQZDDWKUQKQXGC-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- NIOPLOPPKJTSGQ-UHFFFAOYSA-N 2-(4-fluorophenyl)-1-methylbenzimidazole Chemical compound N=1C2=CC=CC=C2N(C)C=1C1=CC=C(F)C=C1 NIOPLOPPKJTSGQ-UHFFFAOYSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- FFYTTYVSDVWNMY-UHFFFAOYSA-N 2-Methyl-5-nitroimidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1 FFYTTYVSDVWNMY-UHFFFAOYSA-N 0.000 description 1
- KWIPUXXIFQQMKN-UHFFFAOYSA-N 2-azaniumyl-3-(4-cyanophenyl)propanoate Chemical compound OC(=O)C(N)CC1=CC=C(C#N)C=C1 KWIPUXXIFQQMKN-UHFFFAOYSA-N 0.000 description 1
- SBYMUDUGTIKLCR-UHFFFAOYSA-N 2-chloroethenylbenzene Chemical compound ClC=CC1=CC=CC=C1 SBYMUDUGTIKLCR-UHFFFAOYSA-N 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- FWWXYLGCHHIKNY-UHFFFAOYSA-N 2-ethoxyethyl prop-2-enoate Chemical compound CCOCCOC(=O)C=C FWWXYLGCHHIKNY-UHFFFAOYSA-N 0.000 description 1
- PQAMFDRRWURCFQ-UHFFFAOYSA-N 2-ethyl-1h-imidazole Chemical compound CCC1=NC=CN1 PQAMFDRRWURCFQ-UHFFFAOYSA-N 0.000 description 1
- HFCUBKYHMMPGBY-UHFFFAOYSA-N 2-methoxyethyl prop-2-enoate Chemical compound COCCOC(=O)C=C HFCUBKYHMMPGBY-UHFFFAOYSA-N 0.000 description 1
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
- YZEUHQHUFTYLPH-UHFFFAOYSA-N 2-nitroimidazole Chemical compound [O-][N+](=O)C1=NC=CN1 YZEUHQHUFTYLPH-UHFFFAOYSA-N 0.000 description 1
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 description 1
- JHJHDEZWUNCTQO-UHFFFAOYSA-N 2-prop-2-enylsulfanyl-1h-benzimidazole Chemical compound C1=CC=C2NC(SCC=C)=NC2=C1 JHJHDEZWUNCTQO-UHFFFAOYSA-N 0.000 description 1
- YNFBMDWHEHETJW-UHFFFAOYSA-N 2-pyridin-2-yl-1h-benzimidazole Chemical compound N1=CC=CC=C1C1=NC2=CC=CC=C2N1 YNFBMDWHEHETJW-UHFFFAOYSA-N 0.000 description 1
- LLEASVZEQBICSN-UHFFFAOYSA-N 2-undecyl-1h-imidazole Chemical compound CCCCCCCCCCCC1=NC=CN1 LLEASVZEQBICSN-UHFFFAOYSA-N 0.000 description 1
- UIDDPPKZYZTEGS-UHFFFAOYSA-N 3-(2-ethyl-4-methylimidazol-1-yl)propanenitrile Chemical compound CCC1=NC(C)=CN1CCC#N UIDDPPKZYZTEGS-UHFFFAOYSA-N 0.000 description 1
- BVYPJEBKDLFIDL-UHFFFAOYSA-N 3-(2-phenylimidazol-1-yl)propanenitrile Chemical compound N#CCCN1C=CN=C1C1=CC=CC=C1 BVYPJEBKDLFIDL-UHFFFAOYSA-N 0.000 description 1
- SZUPZARBRLCVCB-UHFFFAOYSA-N 3-(2-undecylimidazol-1-yl)propanenitrile Chemical compound CCCCCCCCCCCC1=NC=CN1CCC#N SZUPZARBRLCVCB-UHFFFAOYSA-N 0.000 description 1
- CTDOEUILFMNOBC-UHFFFAOYSA-N 3-chloropropyl(2,2-dimethoxyethyl)silane Chemical compound ClCCC[SiH2]CC(OC)OC CTDOEUILFMNOBC-UHFFFAOYSA-N 0.000 description 1
- FASUFOTUSHAIHG-UHFFFAOYSA-N 3-methoxyprop-1-ene Chemical compound COCC=C FASUFOTUSHAIHG-UHFFFAOYSA-N 0.000 description 1
- LHEKBWMWMVRJMO-UHFFFAOYSA-N 3-methoxypropyl prop-2-enoate Chemical compound COCCCOC(=O)C=C LHEKBWMWMVRJMO-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
- QAJJXHRQPLATMK-UHFFFAOYSA-N 4,5-dichloro-1h-imidazole Chemical compound ClC=1N=CNC=1Cl QAJJXHRQPLATMK-UHFFFAOYSA-N 0.000 description 1
- GMTAWLUJHGIUPU-UHFFFAOYSA-N 4,5-diphenyl-1,3-dihydroimidazole-2-thione Chemical compound N1C(S)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 GMTAWLUJHGIUPU-UHFFFAOYSA-N 0.000 description 1
- RIBVUBSNWKTELT-UHFFFAOYSA-N 4-ethoxybutyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound C(C1CO1)OCCC[SiH2]CCCCOCC RIBVUBSNWKTELT-UHFFFAOYSA-N 0.000 description 1
- GMGPQRGRSUIXKK-UHFFFAOYSA-N 4-methoxybutyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound C(C1CO1)OCCC[SiH2]CCCCOC GMGPQRGRSUIXKK-UHFFFAOYSA-N 0.000 description 1
- DPBQZIHMIPYKHX-UHFFFAOYSA-N 4-nitro-1h-imidazol-5-amine Chemical compound NC=1NC=NC=1[N+]([O-])=O DPBQZIHMIPYKHX-UHFFFAOYSA-N 0.000 description 1
- HHMQTVVHKVDCNX-UHFFFAOYSA-N 4-tert-butyl-1-propan-2-ylimidazole Chemical compound CC(C)N1C=NC(C(C)(C)C)=C1 HHMQTVVHKVDCNX-UHFFFAOYSA-N 0.000 description 1
- NYDGOZPYEABERA-UHFFFAOYSA-N 5-chloro-1-methylimidazole Chemical compound CN1C=NC=C1Cl NYDGOZPYEABERA-UHFFFAOYSA-N 0.000 description 1
- TYOXIFXYEIILLY-UHFFFAOYSA-N 5-methyl-2-phenyl-1h-imidazole Chemical compound N1C(C)=CN=C1C1=CC=CC=C1 TYOXIFXYEIILLY-UHFFFAOYSA-N 0.000 description 1
- VYDWQPKRHOGLPA-UHFFFAOYSA-N 5-nitroimidazole Chemical compound [O-][N+](=O)C1=CN=CN1 VYDWQPKRHOGLPA-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- 239000004709 Chlorinated polyethylene Substances 0.000 description 1
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 229940090948 ammonium benzoate Drugs 0.000 description 1
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 1
- ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- 238000012662 bulk polymerization Methods 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
- CJXAEXPPLWQRFR-UHFFFAOYSA-N clemizole Chemical compound C1=CC(Cl)=CC=C1CN1C2=CC=CC=C2N=C1CN1CCCC1 CJXAEXPPLWQRFR-UHFFFAOYSA-N 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- RAFNCPHFRHZCPS-UHFFFAOYSA-N di(imidazol-1-yl)methanethione Chemical compound C1=CN=CN1C(=S)N1C=CN=C1 RAFNCPHFRHZCPS-UHFFFAOYSA-N 0.000 description 1
- DCUXXZDKIHWAOR-UHFFFAOYSA-N dimethoxy-methyl-[3-(oxiran-2-ylmethoxy)propyl]silane;trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound CO[Si](C)(OC)CCCOCC1CO1.C1C(CC[Si](OC)(OC)OC)CCC2OC21 DCUXXZDKIHWAOR-UHFFFAOYSA-N 0.000 description 1
- DYPVADKXJPHQCY-UHFFFAOYSA-N dimethoxymethyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound COC(OC)[SiH2]CCCOCC1CO1 DYPVADKXJPHQCY-UHFFFAOYSA-N 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005485 electric heating Methods 0.000 description 1
- 238000010292 electrical insulation Methods 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
- HHBOIIOOTUCYQD-UHFFFAOYSA-N ethoxy-dimethyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](C)(C)CCCOCC1CO1 HHBOIIOOTUCYQD-UHFFFAOYSA-N 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 229920001973 fluoroelastomer Polymers 0.000 description 1
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229920002681 hypalon Polymers 0.000 description 1
- QDYTUZCWBJRHKK-UHFFFAOYSA-N imidazole-4-methanol Chemical compound OCC1=CNC=N1 QDYTUZCWBJRHKK-UHFFFAOYSA-N 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000001746 injection moulding Methods 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
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- PMRYVIKBURPHAH-UHFFFAOYSA-N methimazole Chemical compound CN1C=CNC1=S PMRYVIKBURPHAH-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000010705 motor oil Substances 0.000 description 1
- 238000000465 moulding Methods 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
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- FSAJWMJJORKPKS-UHFFFAOYSA-N octadecyl prop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C=C FSAJWMJJORKPKS-UHFFFAOYSA-N 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- 125000005009 perfluoropropyl group Chemical group FC(C(C(F)(F)F)(F)F)(F)* 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229940051841 polyoxyethylene ether Drugs 0.000 description 1
- 229920000056 polyoxyethylene ether Polymers 0.000 description 1
- XYWJNTOURDMTPI-UHFFFAOYSA-N procodazole Chemical compound C1=CC=C2NC(CCC(=O)O)=NC2=C1 XYWJNTOURDMTPI-UHFFFAOYSA-N 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 239000012779 reinforcing material Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-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
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000004636 vulcanized rubber Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/32—Epoxy compounds containing three or more epoxy groups
- C08G59/3209—Epoxy compounds containing three or more epoxy groups obtained by polymerisation of unsaturated mono-epoxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L13/00—Compositions of rubbers containing carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/50—Amines
- C08G59/5046—Amines heterocyclic
- C08G59/5053—Amines heterocyclic containing only nitrogen as a heteroatom
- C08G59/5073—Amines heterocyclic containing only nitrogen as a heteroatom having two nitrogen atoms in the ring
-
- 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
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/34—Silicon-containing compounds
- C08K3/36—Silica
-
- 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
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3442—Heterocyclic compounds having nitrogen in the ring having two nitrogen atoms in the ring
- C08K5/3445—Five-membered rings
-
- 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
- C08K5/54—Silicon-containing compounds
- C08K5/541—Silicon-containing compounds containing oxygen
- C08K5/5435—Silicon-containing compounds containing oxygen containing oxygen in a ring
Definitions
- the present invention relates to an acrylic rubber composition. More specifically, the present invention relates to an acrylic rubber composition excellent in processing safety, compression set and tensile strength balance.
- Vulcanizates of acrylic rubber compositions have excellent physical properties such as heat resistance, oil resistance, mechanical properties, compression set properties, etc., so hose parts, seal parts, vibration-proof rubber parts in the engine room of automobiles Many materials are used.
- Such an acrylic rubber composition is required to give strength to rubber when used for each member related to automobiles.
- a technique of blending a specific amount of silica, aliphatic polyhydric alcohol, guanidine compound, and aromatic diamine compound into a carboxyl group-containing acrylic rubber is known. (For example, see Patent Documents 1 to 3 below).
- the vulcanization method of the acrylic rubber composition varies depending on the use of the vulcanized rubber product.
- secondary vulcanization is performed for several hours in hot air at a temperature of about 140 to 200 ° C. using a gear oven or the like.
- hoses are subjected to steam vulcanization as primary vulcanization after extrusion molding at a temperature of 50 to 130 ° C. Further, depending on the type of hose such as an air duct hose, it is molded by secondary vulcanization by hot air vulcanization after injection vulcanization or press vulcanization. In addition, an acrylic rubber composition capable of exhibiting sufficient mechanical properties that are generally not deformed by primary vulcanization is required for sealing parts such as gaskets.
- the acrylic rubber composition cannot exhibit sufficient mechanical properties and rubber elasticity due to insufficient vulcanization only by primary vulcanization, secondary vulcanization by hot air vulcanization is performed.
- a closed mixer such as a kneader or banbury is often used in addition to an open roll, and processing safety that does not scorch (initial vulcanization before the vulcanization process) during kneading is often used. Sex is required.
- processing safety is also an important characteristic.
- Silica is often used as a white reinforcing material. Silica has characteristics such as excellent elongation, but when used as it is, there are cases where the extrudability is poor, mechanical properties are not sufficient, and compression set is not sufficient.
- a composition containing silica is used for sealing parts such as rubber hoses, air duct hoses, gaskets, etc., there are similar problems, good processing safety, and primary vulcanization (steam vulcanization, press vulcanization, injection vulcanization).
- Acrylic rubber composition is desired which is subjected to secondary vulcanization (hot air vulcanization, etc.) after vulcanization, etc., and is excellent in sufficient mechanical properties and compression set resistance.
- the main object of the present invention is to provide an acrylic rubber composition in which the vulcanizate has sufficient mechanical properties and compression set resistance.
- the present inventors have found an acrylic rubber composition and its vulcanizate that have good processing safety, sufficient mechanical properties, and excellent compression set resistance, and complete the present invention. It came to. That is, the present invention (1) An acrylic rubber composition containing the following (A) to (D).
- R 1 represents a hydrogen atom, an alkyl group, a substituted alkyl group, an aryl group, or a carboxyl group
- R 2 represents a hydrogen atom or an alkyl group
- R 3 represents a hydrogen atom or an alkyl group
- R 4 Represents a hydrogen atom, an alkyl group, a substituted alkyl group, or a carbonyl group.
- (C) Silica having a pH of 5.5 to 9.0
- D Silane coupling agent represented by the following general formula (2) (Wherein R 1 , R 2 and R 3 represent an alkyl group, an aryl group, a substituted aryl group or an alkoxy group, and one or two substituents of R 1 , R 2 and R 3 represent an alkoxy group.
- R 4 represents a glycidoxy group.
- the acrylic rubber composition of the present invention preferably contains 20 to 80 parts by mass of silica with respect to 100 parts by mass of the epoxy group-containing acrylic rubber.
- (3) 0.1 to 5 parts by mass of the imidazole compound represented by the general formula (1) can be contained with respect to 100 parts by mass of the epoxy group-containing acrylic rubber.
- the compound represented by the general formula (2) can be contained in an amount of 0.1 to 2 parts by mass with respect to 100 parts by mass of the epoxy group-containing acrylic rubber.
- silane coupling agent a diethoxyethyl group-containing silane coupling agent, a dimethoxyphenyl group-containing silane coupling agent, a dimethoxymethyl group-containing silane coupling agent, and a dimethoxybutyl group-containing silane coupling agent Any one or more selected from the group consisting of can be used.
- the silane coupling agent is preferably contained in an amount of 0.1 to 2 parts by mass with respect to 100 parts by mass of the epoxy group-containing acrylic rubber.
- the acrylic rubber composition can be vulcanized to obtain a vulcanized product.
- a hose part or a seal part can be obtained using the vulcanized product.
- the symbol “ ⁇ ” means “above” and “below”.
- the description “A to B” means greater than A and less than B.
- the present invention provides an acrylic rubber composition having good processing safety, sufficient mechanical properties after secondary vulcanization (hot air vulcanization), and excellent compression set resistance, and a vulcanized product thereof. it can.
- Acrylic rubber is a rubber obtained by copolymerizing an unsaturated monomer such as alkyl (meth) acrylate and a monomer that can be co-assembled therewith.
- the (meth) acrylic acid alkyl ester means both an acrylic acid alkyl ester (acrylate) and a methacrylic acid alkyl ester (methacrylate).
- the unsaturated monomer of the (meth) acrylic acid alkyl ester can adjust the basic properties such as normal physical properties, cold resistance and oil resistance of the resulting acrylic rubber composition by selecting the kind thereof.
- the unsaturated monomer of the (meth) acrylic acid alkyl ester is not particularly limited.
- An alkoxyalkyl ester of acrylic acid may be copolymerized.
- the copolymerizable monomer is not particularly limited, but alkyl vinyl ketone such as methyl vinyl ketone, vinyl and ether such as vinyl ethyl ether and allyl methyl ether, styrene, ⁇ -methyl styrene, chlorostyrene, Vinyl aromatic compounds such as vinyl toluene and vinyl naphthalene, vinyl nitriles such as acrylonitrile and methacrylonitrile, acrylamide, vinyl acetate, ethylene, propylene, butadiene, isoprene, pentadiene, vinyl chloride, vinylidene chloride, vinyl fluoride, vinylidene fluoride And ethylenically unsaturated compounds such as vinyl propionate and alkyl fumarate.
- alkyl vinyl ketone such as methyl vinyl ketone
- vinyl and ether such as vinyl ethyl ether and allyl methyl ether
- styrene ⁇ -methyl
- the acrylic rubber composition can improve the cold resistance of the resulting vulcanizate by copolymerizing ethylene or propylene.
- the copolymerization amount of ethylene or propylene is 15 parts by mass or less, preferably 10 parts by mass or less with respect to 100 parts by mass of the acrylic rubber. If the copolymerization amount of ethylene or propylene is within this range, not only the cold resistance of the vulcanizate can be improved, but also its oil resistance can be maintained.
- an epoxy group-containing acrylic rubber obtained by copolymerizing the above (meth) acrylic acid alkyl ester with a crosslinkable monomer is used.
- the crosslinkable monomer include those containing an epoxy group such as glycidyl acrylate, glycidyl methacrylate, allyl glycidyl ether, and methallyl glycidyl ether.
- the acrylic rubber in the present invention desirably contains 0 to 10% by weight, preferably 0.1 to 5% by weight, particularly preferably 0.5 to 3% by weight of these crosslinkable monomer units.
- the epoxy group-containing acrylic rubber can be obtained by copolymerizing the above monomers by a known method such as emulsion polymerization, suspension polymerization, solution polymerization, bulk polymerization and the like.
- a good vulcanized product such as a rubber hose and a seal part can be obtained.
- Silica preferably has a pH in the range of 5.5 to 9.0, and more preferably in the range of 7.0 to 8.0.
- examples of such silica include nip seal ER and nip seal VN3 made by Tosoh silica.
- Silica having a pH of less than 5.5 has a short scorch time, resulting in poor processing safety, and silica having a pH of more than 9.0 is not preferable because the vulcanization rate is low and the tensile strength is insufficient.
- the pH of silica in the present invention is a value measured by a room temperature extraction method (JIS K5101-17-2).
- the room temperature extraction method is a method of measuring the pH of a sample (silica) suspension.
- the suspension is made by adding the sample to water.
- the sample concentration of the suspension is 10% by mass.
- the pH is measured after the suspension is vigorously shaken for 1 minute in a glass container and allowed to stand for 5 minutes.
- the amount of silica added is preferably 20 to 80 parts by mass, more preferably 25 to 70 parts by mass with respect to 100 parts by mass of acrylic rubber.
- the addition amount of silica is less than 20 parts by mass, it is necessary to add carbon in order to supplement hardness and tensile strength.
- a preferable characteristic of silica is electrical insulation.
- carbon is added, the resistance value of the entire composition becomes insufficient at 10 7 ⁇ ⁇ cm or less as a volume resistivity.
- the addition amount of silica exceeds 80 mass parts, since the viscosity of the whole composition will raise remarkably and workability will be impaired, it is unpreferable.
- the addition amount of the imidazole compound is preferably 0.1 to 5 parts by mass, more preferably 0.3 to 4 parts by mass with respect to 100 parts by mass of the acrylic rubber.
- the amount of the imidazole compound added is less than 0.1 parts by mass, the vulcanization reaction is not sufficiently performed, and when it exceeds 5 parts by mass, the vulcanization reaction is excessively vulcanized and compression set at a high temperature is deteriorated.
- the imidazole compound is not particularly limited, and examples thereof include 2- (4-fluorophenyl) -1-methylbenzimidazole, 1-methyl-2-phenylimidazole, butylcarbamoyl-2-benzimidazole, and 1-decyl.
- Imidazole 1,5-dicyclohexylimidazole, 1- (2,4,6-triisopropylbenzenesulfonyl) -imidazole, 2,2-dithiobis (4-tert-butyl-1-isopropylimidazole), 1-cyanoethyl-2- Methylimidazole, 1-cyanoethyl-2-phenylimidazole, 1-cyanoethyl-2-ethyl-4-methylimidazole, 1-cyanoethyl-2-undecylimidazole, 1-cyanoethyl-2-methylimidazole trimellitate, 1-cyanoethyl - 2-phenylimidazole trimellitate, 1-cyanoethyl-2-ethyl-4-methylimidazole trimellitate, 1-cyanoethyl-2-undecyl-imidazole trimellitate, 5-chloro-1-methylimidazole, 2-mercapto- 1-methyl
- the addition amount of the silane coupling agent is preferably 0.1 to 2 parts by mass with respect to 100 parts by mass of the acrylic rubber. If the amount is less than 0.1 parts by mass, the tensile strength and compression set are inferior. If the amount exceeds 2 parts by mass, the elongation decreases.
- the silane coupling agent is not particularly limited.
- 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropyldimethylmethoxysilane, 3-glycidoxypropyldimethylethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 3-aminopropyltrimethoxysilane, 3-glycidoxypropyldimethoxyisopropylsilane, 3-glycidoxypropyldimethoxybutylsilane, 3-glycidoxypropylethoxy-2-methyl-4-phenylsilane, 3-glycidoxy-propyldimethoxy-4-methyl- Phenylsilane, 3-glycidoxypropylethoxybut
- dialkoxysilane having two alkoxy groups such as 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 3-glycidoxypropyldimethylmethoxysilane, 3-glycid Monoalkoxysilane having one alkoxy group such as xylpropyldimethylethoxysilane is preferable.
- a silane coupling agent having a dialkoxy group is added to 100 parts by mass of the epoxy group-containing acrylic rubber.
- the silane coupling agent having a dialkoxy group include a diethoxyethyl group-containing silane coupling agent, a dimethoxyphenyl group-containing silane coupling agent, a dimethoxymethyl group-containing silane coupling agent, and a dimethoxybutyl group-containing silane coupling agent. is there.
- the acrylic rubber composition of the present invention When the acrylic rubber composition of the present invention is put into practical use, it can be molded and vulcanized by adding fillers, plasticizers, anti-aging agents, stabilizers, lubricants, reinforcing agents, etc. according to the purpose. it can. Furthermore, for the purpose of adjusting vulcanization, other vulcanizing agents can be added in addition to the (B) imidazole compound of the present invention.
- Fillers other than silica such as carbon black and surface-treated calcium carbonate, and reinforcing agents can be used in combination of two or more types because of the required rubber properties.
- the total amount of these fillers and reinforcing agents (including silica) added is preferably 30 to 200 parts by mass with respect to 100 parts by mass of the acrylic rubber.
- plasticizer those usually used for rubber can be added.
- examples include ester plasticizers, ether plasticizers such as polyoxyethylene ether, and ether / ester plasticizers, but are not limited to the above, and various plasticizers can be used.
- the plasticizer can be added up to about 50 parts by mass with respect to 100 parts by mass of the acrylic rubber.
- anti-aging agent examples include amines, carbamic acid metal salts, phenols, and waxes, and amine-based anti-aging agents are preferable.
- the anti-aging agent can be added in an amount of 0.5 to 10 parts by mass with respect to 100 parts by mass of the acrylic rubber.
- the rubber component in the acrylic rubber composition used in the present invention is mainly composed of acrylic rubber.
- IIR isobutylene / isoprene
- BR butadiene rubber
- NBR nitrile rubber
- HNBR hydrogenated nitrile rubber
- CR chloroprene rubber
- EPDM ethylene propylene diene rubber
- FKM fluoro rubber
- Q silicone rubber
- CSM chlorosulfonated polyethylene rubber
- CO epichlorohydrin rubber
- ECO epichlorohydrin-ethylene oxide copolymer
- CM chlorinated polyethylene
- acrylic rubber acrylic rubber composition and vulcanized product of the present invention
- those usually used in the rubber industry can be used.
- the acrylic rubber, acrylic rubber composition and vulcanized product thereof according to the present invention are particularly used as seal parts such as rubber hoses, gaskets and packings.
- rubber hoses mainly for automobiles with high demands for high durability, transmission oil cooler hoses, engine oil cooler hoses, turbo intercooler hoses, turbo air duct hoses, power steering hoses, hot air hoses, It is used for hoses used in radiator hoses, other industrial machines, oil systems including high pressure systems of construction machines, fuel hoses and drain hoses.
- seal parts include engine head cover gaskets, oil pan gaskets, oil seals, lip seal packings, O-rings, transmission seal gaskets, crankshaft and camshaft seal gaskets, typical power supplies for automobiles, Steering seal belt cover seal, CVJ, and R & P boot material.
- the acrylic rubber, acrylic rubber composition and vulcanized product thereof according to the present invention are excellent in cold resistance, oil resistance, and heat resistance in addition to excellent mechanical properties. It is very suitably used as sealing parts such as automobile rubber hoses and gaskets which are becoming harsh.
- a composite hose in which a base rubber, fluorine-modified acrylic rubber, hydrin rubber, CSM, CR, NBR, HNBR, ethylene / propylene rubber or the like is combined as an inner layer, an intermediate layer, or an outer layer.
- a reinforcing thread or a wire can be provided in the middle of the hose or in the outermost layer of the rubber hose.
- the temperature in the tank was maintained at 55 ° C., and the reaction was completed in 9 hours.
- a sodium borate aqueous solution was added to the produced polymerization solution to solidify the polymer, followed by dehydration and drying to obtain an acrylic rubber.
- the resulting acrylic rubber had a copolymer composition of 80 parts by mass of n-butyl acrylate monomer unit, 15 parts by mass of vinyl acetate, 3 parts by mass of ethylene, and 2 parts by mass of glycidyl methacrylate.
- a nuclear magnetic resonance spectrum was collected and each component was quantified.
- An acrylic rubber composition was obtained in the same manner as in Example 2 except that 1-cyanoethyl-2-methylimidazole was not added.
- Example 2 to 19 and Comparative Examples 1 to 8 were vulcanized under the same conditions as in Example 1 (electrically heated hot press 170 ° C. ⁇ 20 minutes, gear oven 170 ° C. ⁇ 4 hours). A vulcanizate was obtained.
- the vulcanizates of Examples 1 to 19 and Comparative Examples 1 to 8 were evaluated for tensile strength, elongation at break, hardness and compression set resistance by the following “Measuring method”.
- the tensile strength and elongation at break are measured according to JIS K6251. That is, the tensile strength is the maximum tensile force (MPa) when the test piece breaks.
- the elongation at break (elongation at break) is the elongation when the test piece is broken, and is expressed as a ratio (%) to the initial value.
- the hardness (hardness) is measured using a durometer hardness meter in accordance with JIS K6253.
- the compression set is measured in accordance with JIS K6262. That is, compression set is the amount (%) of deformation remaining after compression deformation at 150 ° C. for 70 hours and removing the force that causes compression deformation.
- the anti-aging agent A is Nocrak CD manufactured by Ouchi Shinsei Chemical Co.
- the carbon black is a seast 116 manufactured by Tokai Carbon Co.
- silica (1) is a nip seal ER (pH: 7. 5 to 9.0)
- silica (2) is NIPSEAL VN-3 (pH: 5.5 to 6.5) manufactured by Tosoh Silica
- silica (3) is Carplex # 1120 (pH) manufactured by Shionogi & Co. 10.4 to 10.9)
- Farmin 80 manufactured by Kao Corporation was used.
- As the plasticizer “Adekaiser RS-735” manufactured by ADEKA was used. Commercially available products were used for the other materials.
- Imidazole (1) is 1-cyanoethyl-2-methylimidazole
- Imidazole (2) is 1-methyl-2-phenylimidazole
- Imidazole (3) is 1,2-dimethylimidazole
- Imidazole (4) is 2-imidazolecarboxylic acid
- Imidazole (5) is 4,5-dimethyl-2-phenylimidazole
- A is 3-glycidoxypropyldimethoxymethylsilane
- B is 3-glycidoxypropyldiethoxymethylsilane
- C is 3-glycidoxypropyldimethoxyisopropylsilane
- D is 3-glycidoxypropyldimethoxybutylsilane
- E is 3-glycidoxypropyldiethoxyphenylsilane
- F is 3-glycidoxypropyldimethoxy 4-methyl-phenylsilane
- G is 3-glycidoxypropyltrimethoxysilane
- H is 3-
- the acrylic rubber composition of the present invention has normal properties (tensile strength, elongation, hardness), compression set, when vulcanized. Is good. Focusing on the amount of carbon black, it can be seen that the examples of the present application have sufficient hardness and tensile strength even when the amount of carbon black added is less than 25 parts by mass with respect to 100 parts by mass of acrylic rubber.
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- 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)
- Rigid Pipes And Flexible Pipes (AREA)
- Sealing Material Composition (AREA)
Abstract
Description
すなわち、本発明は、
(1)下記(A)~(D)を含有してなるアクリルゴム組成物である。
(A)エポキシ基含有アクリルゴム
(B)下記一般式(1)で示されるイミダゾール化合物
(C)pH5.5~9.0のシリカ
(D)下記一般式(2)で示されるシランカップリング剤
(2)本発明のアクリルゴム組成物は、エポキシ基含有アクリルゴム100質量部に対して、シリカを20~80質量部含有するものが望ましい。
(3)エポキシ基含有アクリルゴム100質量部に対して、一般式(1)で示されるイミダゾール化合物を0.1~5質量部含有させることもできる。
(4)エポキシ基含有アクリルゴム100質量部に対して、一般式(2)で示される化合物を0.1~2質量部含有させることもできる。
(5)シランカップリング剤としては、ジエトキシエチル基含有シランカップリング剤と、ジメトキシフェニル基含有シランカップリング剤と、ジメトキシメチル基含有シランカップリング剤と、ジメトキシブチル基含有シランカップリング剤とからなる群より選択されるいずれか1種以上からなるものを用いることができる。そのシランカップリング剤は、エポキシ基含有アクリルゴム100質量部に対して、0.1~2質量部含有させることが望ましい。
(6)上記のアクリルゴム組成物を加硫して加硫物を得ることもできる。
(7)更に、上記加硫物を用いて、ホース部品やシール部品を得ることもできる。
耐圧反応容器にアクリル酸ブチル8.8kg、酢酸ビニル3.0kg、部分ケン化ビニルアルコール4質量%の水溶液16kg、酢酸ナトリウム23g、グリシジルメタクリレート0.4kgを投入し、攪拌機であらかじめよく混合し、均一懸濁液を作製した。槽内上部の空気を窒素で置換した後、エチレンを槽内上部に圧入し、圧力を4.3MPaに調整した。攪拌を続行し、槽内を55℃に保持した後、別途注入口より過硫酸アンモニウム水溶液を圧入して重合を開始させた。反応中槽内温度は55℃に保ち、9時間で反応を終了させた。生成した重合液に、ホウ酸ナトリウム水溶液を配合して重合体を固化し、脱水および乾燥を行って、アクリルゴムを得た。得られたアクリルゴムは、n-ブチルアクリレート単量体単位80質量部と、酢酸ビニル15質量部と、エチレン3質量部、グリシジルメタクリレート2質量部の共重合体組成であった。単量体単位成分は核磁気共鳴スペクトルを採取し、各成分を定量した。
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[比較例8]
引張強度、破断時伸びは、JIS K6251に準拠して測定したものである。すなわち、引張強度は、試験片が破断する時の最大引張力(MPa)である。破断時伸び(切断時伸び)は、試験片が破断した時の伸びであり、初期に対する比率(%)で表す。また、硬さ(硬度)は、JIS K6253に準拠してデュロメータ硬さ計を用いて測定したものである。圧縮永久歪みはJIS K6262に準拠して測定したものである。すなわち、圧縮永久歪みは、150℃で70時間圧縮変形させ、圧縮変形を起こす力を取り除いた後に残存する変形の量(%)である。
イミダゾール(1)は1-シアノエチル-2-メチルイミダゾール、
イミダゾール(2)は1-メチル-2-フェニルイミダゾール、
イミダゾール(3)は1,2-ジメチルイミダゾール、
イミダゾール(4)は2-イミダゾールカルボン酸、
イミダゾール(5)は4、5-ジメチル-2-フェニルイミダゾール、
Aは3-グリシドキシプロピルジメトキシメチルシラン、
Bは3-グリシドキシプロピルジエトキシメチルシラン、
Cは3-グリシドキシプロピルジメトキシイソプロピルシラン、
Dは3-グリシドキシプロピルジメトキシブチルシラン、
Eは3-グリシドキシプロピルジエトキシフェニルシラン、
Fは3-グリシドキシプロピルジメトキシ4-メチル-フェニルシラン、
Gは3-グリシドキシプロピルトリメトキシシラン、
Hは3-グリシドキシプロピルトリメチルシラン、
Iは3-メタクリロキシプロピルジメトキシメチルシラン、
Jはビス(トリエトキシシリルプロピル)テトラスルフィド、
Kは3-クロロプロピルジメトキシメチルシラン、
をそれぞれ示している。
Claims (8)
- 下記(A)~(D)を含有してなるアクリルゴム組成物。
(A)エポキシ基含有アクリルゴム
(B)下記一般式(1)で示されるイミダゾール化合物
(C)pH5.5~9.0のシリカ
(D)下記一般式(2)で示されるシランカップリング剤
- エポキシ基含有アクリルゴム100質量部に対して、前記シリカを20~80質量部含有してなる請求項1記載のアクリルゴム組成物。
- エポキシ基含有アクリルゴム100質量部に対して、前記シランカップリング剤を0.1~2質量部含有してなる請求項1又は2項に記載のアクリルゴム組成物。
- エポキシ基含有アクリルゴム100質量部に対して、前記イミダゾール化合物を0.1~5質量部含有してなる請求項1~3のいずれか1項に記載のアクリルゴム組成物。
- 前記シランカップリング剤は、ジエトキシエチル基含有シランカップリング剤と、ジメトキシフェニル基含有シランカップリング剤と、ジメトキシメチル基含有シランカップリング剤と、ジメトキシブチル基含有シランカップリング剤とからなる群より選択されるいずれか1種以上からなり、
エポキシ基含有アクリルゴム100質量部に対して、前記シランカップリング剤を0.1~2質量部含有してなる請求項1~4いずれか1項に記載のアクリルゴム組成物。 - 請求項1~5のいずれか1項に記載のアクリルゴム組成物を加硫してなる加硫物。
- 請求項6に記載した加硫物を用いたホース部品
- 請求項6に記載した加硫物を用いたシール部品。
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
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EP11797892.4A EP2584002B1 (en) | 2010-06-21 | 2011-03-31 | Acrylic rubber composition, vulcanizate, hose part, and sealing part |
CN201180028558.5A CN102959004B (zh) | 2010-06-21 | 2011-03-31 | 丙烯酸类橡胶组合物、硫化物、软管部件、密封部件 |
JP2012521353A JP5785166B2 (ja) | 2010-06-21 | 2011-03-31 | アクリルゴム組成物、加硫物、ホース部品、シール部品 |
US13/704,546 US20130090424A1 (en) | 2010-06-21 | 2011-03-31 | Acrylic rubber composition, vulcanizate, hose part, and sealing part |
ES11797892.4T ES2633848T3 (es) | 2010-06-21 | 2011-03-31 | Composición acrílica de caucho vulcanizado, parte de la manguera, y de sellado |
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JP2010140071 | 2010-06-21 | ||
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US (1) | US20130090424A1 (ja) |
EP (1) | EP2584002B1 (ja) |
JP (1) | JP5785166B2 (ja) |
CN (1) | CN102959004B (ja) |
ES (1) | ES2633848T3 (ja) |
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WO (1) | WO2011162004A1 (ja) |
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EP2612882A1 (de) * | 2012-01-06 | 2013-07-10 | Evonik Industries AG | Kautschukmischungen |
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WO2014084235A1 (ja) * | 2012-11-30 | 2014-06-05 | 日本ゼオン株式会社 | アクリルゴム組成物およびゴム架橋物 |
WO2014112564A1 (ja) * | 2013-01-17 | 2014-07-24 | 電気化学工業株式会社 | タイヤ加硫用ブラダー |
JP2016079094A (ja) * | 2014-10-09 | 2016-05-16 | 信越化学工業株式会社 | オルガノオキシ化合物及びその製造方法 |
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ES2882029T3 (es) * | 2015-02-17 | 2021-12-01 | Osaka Soda Co Ltd | Composición para caucho aislante de la vibración, y objeto entrecruzado obtenido del mismo |
US11760821B2 (en) | 2017-10-16 | 2023-09-19 | Denka Company Limited | Method for producing acrylic rubber, acrylic rubber, acrylic rubber composition, vulcanized substance thereof, and application for vulcanized substance |
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WO2014080948A1 (ja) * | 2012-11-21 | 2014-05-30 | 電気化学工業株式会社 | アクリル系エラストマー、アクリル系エラストマー組成物、積層体、架橋物及び成形部材 |
JPWO2014084235A1 (ja) * | 2012-11-30 | 2017-01-05 | 日本ゼオン株式会社 | アクリルゴム組成物およびゴム架橋物 |
WO2014084235A1 (ja) * | 2012-11-30 | 2014-06-05 | 日本ゼオン株式会社 | アクリルゴム組成物およびゴム架橋物 |
JPWO2014112564A1 (ja) * | 2013-01-17 | 2017-01-19 | デンカ株式会社 | タイヤ加硫用ブラダー |
WO2014112564A1 (ja) * | 2013-01-17 | 2014-07-24 | 電気化学工業株式会社 | タイヤ加硫用ブラダー |
JP2016079094A (ja) * | 2014-10-09 | 2016-05-16 | 信越化学工業株式会社 | オルガノオキシ化合物及びその製造方法 |
WO2018008474A1 (ja) * | 2016-07-05 | 2018-01-11 | デンカ株式会社 | アクリルゴム組成物 |
JPWO2018008474A1 (ja) * | 2016-07-05 | 2019-05-16 | デンカ株式会社 | アクリルゴム組成物 |
JP7043402B2 (ja) | 2016-07-05 | 2022-03-29 | デンカ株式会社 | アクリルゴム組成物 |
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CN102959004A (zh) | 2013-03-06 |
JPWO2011162004A1 (ja) | 2013-08-19 |
EP2584002A1 (en) | 2013-04-24 |
EP2584002A4 (en) | 2014-01-22 |
EP2584002B1 (en) | 2017-05-10 |
TW201202331A (en) | 2012-01-16 |
CN102959004B (zh) | 2015-06-17 |
JP5785166B2 (ja) | 2015-09-24 |
US20130090424A1 (en) | 2013-04-11 |
ES2633848T3 (es) | 2017-09-25 |
TWI545152B (zh) | 2016-08-11 |
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