JPH01139605A - Vulcanizable blended rubber composition - Google Patents
Vulcanizable blended rubber compositionInfo
- Publication number
- JPH01139605A JPH01139605A JP29746287A JP29746287A JPH01139605A JP H01139605 A JPH01139605 A JP H01139605A JP 29746287 A JP29746287 A JP 29746287A JP 29746287 A JP29746287 A JP 29746287A JP H01139605 A JPH01139605 A JP H01139605A
- Authority
- JP
- Japan
- Prior art keywords
- ethylene
- acrylate
- acrylic elastomer
- parts
- ethyl acrylate
- 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.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 24
- 229920001971 elastomer Polymers 0.000 title claims abstract description 20
- 229920000800 acrylic rubber Polymers 0.000 claims abstract description 27
- 229920000058 polyacrylate Polymers 0.000 claims abstract description 27
- 239000000178 monomer Substances 0.000 claims abstract description 18
- 229920006244 ethylene-ethyl acrylate Polymers 0.000 claims abstract description 13
- 150000001451 organic peroxides Chemical class 0.000 claims abstract description 11
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 abstract description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 abstract description 4
- 238000002156 mixing Methods 0.000 abstract description 4
- IPJGAEWUPXWFPL-UHFFFAOYSA-N 1-[3-(2,5-dioxopyrrol-1-yl)phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC(N2C(C=CC2=O)=O)=C1 IPJGAEWUPXWFPL-UHFFFAOYSA-N 0.000 abstract description 2
- BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 abstract description 2
- 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 abstract description 2
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 abstract description 2
- 239000004342 Benzoyl peroxide Substances 0.000 abstract description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 abstract description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 abstract description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 1
- 239000005977 Ethylene Substances 0.000 abstract 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 11
- -1 acrylic ester Chemical class 0.000 description 7
- 239000006229 carbon black Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 6
- 238000004073 vulcanization Methods 0.000 description 6
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 4
- HFCUBKYHMMPGBY-UHFFFAOYSA-N 2-methoxyethyl prop-2-enoate Chemical compound COCCOC(=O)C=C HFCUBKYHMMPGBY-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 235000021355 Stearic acid Nutrition 0.000 description 3
- 230000003712 anti-aging effect Effects 0.000 description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 3
- 239000008117 stearic acid Substances 0.000 description 3
- OJOWICOBYCXEKR-KRXBUXKQSA-N (5e)-5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(=C/C)/CC1C=C2 OJOWICOBYCXEKR-KRXBUXKQSA-N 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- FWWXYLGCHHIKNY-UHFFFAOYSA-N 2-ethoxyethyl prop-2-enoate Chemical compound CCOCCOC(=O)C=C FWWXYLGCHHIKNY-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WRXCBRHBHGNNQA-UHFFFAOYSA-N (2,4-dichlorobenzoyl) 2,4-dichlorobenzenecarboperoxoate Chemical compound ClC1=CC(Cl)=CC=C1C(=O)OOC(=O)C1=CC=C(Cl)C=C1Cl WRXCBRHBHGNNQA-UHFFFAOYSA-N 0.000 description 1
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- NALFRYPTRXKZPN-UHFFFAOYSA-N 1,1-bis(tert-butylperoxy)-3,3,5-trimethylcyclohexane Chemical compound CC1CC(C)(C)CC(OOC(C)(C)C)(OOC(C)(C)C)C1 NALFRYPTRXKZPN-UHFFFAOYSA-N 0.000 description 1
- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 description 1
- PGRNEGLBSNLPNP-UHFFFAOYSA-N 1,6-dichloro-3-methylhex-1-ene Chemical compound ClC=CC(C)CCCCl PGRNEGLBSNLPNP-UHFFFAOYSA-N 0.000 description 1
- SDRZFSPCVYEJTP-UHFFFAOYSA-N 1-ethenylcyclohexene Chemical compound C=CC1=CCCCC1 SDRZFSPCVYEJTP-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- DMWVYCCGCQPJEA-UHFFFAOYSA-N 2,5-bis(tert-butylperoxy)-2,5-dimethylhexane Chemical compound CC(C)(C)OOC(C)(C)CCC(C)(C)OOC(C)(C)C DMWVYCCGCQPJEA-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
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-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
- JJRUAPNVLBABCN-UHFFFAOYSA-N 2-(ethenoxymethyl)oxirane Chemical compound C=COCC1CO1 JJRUAPNVLBABCN-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
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- AEPWOCLBLLCOGZ-UHFFFAOYSA-N 2-cyanoethyl prop-2-enoate Chemical compound C=CC(=O)OCCC#N AEPWOCLBLLCOGZ-UHFFFAOYSA-N 0.000 description 1
- CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- IWTYTFSSTWXZFU-UHFFFAOYSA-N 3-chloroprop-1-enylbenzene Chemical compound ClCC=CC1=CC=CC=C1 IWTYTFSSTWXZFU-UHFFFAOYSA-N 0.000 description 1
- CJSBUWDGPXGFGA-UHFFFAOYSA-N 4-methylpenta-1,3-diene Chemical compound CC(C)=CC=C CJSBUWDGPXGFGA-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000010556 emulsion polymerization method Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- XJELOQYISYPGDX-UHFFFAOYSA-N ethenyl 2-chloroacetate Chemical compound ClCC(=O)OC=C XJELOQYISYPGDX-UHFFFAOYSA-N 0.000 description 1
- SZPUDSQPVUIVKC-UHFFFAOYSA-N ethoxymethyl prop-2-enoate Chemical compound CCOCOC(=O)C=C SZPUDSQPVUIVKC-UHFFFAOYSA-N 0.000 description 1
- XWNVSPGTJSGNPU-UHFFFAOYSA-N ethyl 4-chloro-1h-indole-2-carboxylate Chemical compound C1=CC=C2NC(C(=O)OCC)=CC2=C1Cl XWNVSPGTJSGNPU-UHFFFAOYSA-N 0.000 description 1
- 239000005042 ethylene-ethyl acrylate Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical compound CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- SINFYWWJOCXYFD-UHFFFAOYSA-N methoxymethyl prop-2-enoate Chemical compound COCOC(=O)C=C SINFYWWJOCXYFD-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000012778 molding material Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 235000015145 nougat Nutrition 0.000 description 1
- ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920003192 poly(bis maleimide) Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229940114930 potassium stearate Drugs 0.000 description 1
- ANBFRLKBEIFNQU-UHFFFAOYSA-M potassium;octadecanoate Chemical compound [K+].CCCCCCCCCCCCCCCCCC([O-])=O ANBFRLKBEIFNQU-UHFFFAOYSA-M 0.000 description 1
- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 description 1
- LYBIZMNPXTXVMV-UHFFFAOYSA-N propan-2-yl prop-2-enoate Chemical compound CC(C)OC(=O)C=C LYBIZMNPXTXVMV-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
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 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
- GRPURDFRFHUDSP-UHFFFAOYSA-N tris(prop-2-enyl) benzene-1,2,4-tricarboxylate Chemical compound C=CCOC(=O)C1=CC=C(C(=O)OCC=C)C(C(=O)OCC=C)=C1 GRPURDFRFHUDSP-UHFFFAOYSA-N 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Graft Or Block Polymers (AREA)
Abstract
Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明は、加硫性ブレンドゴム組成物に関する。[Detailed description of the invention] [Industrial application field] The present invention relates to vulcanizable blend rubber compositions.
更に詳しくは、アクリルエラストマーの耐熱性および耐
寒性を改善せしめる加硫性ブレンドゴム組成物に関する
。More specifically, the present invention relates to a vulcanizable blend rubber composition that improves the heat resistance and cold resistance of acrylic elastomers.
〔従来の技術〕および〔発明が解決しようとする問題点
〕アクリルエラストマーは、アクリル酸エステルを主成
分とする共重合体エラストマーであり、−般に耐熱性、
耐油性にすぐれたゴムとして、オイルシール、Oリング
、パツキン、ホースなどの成形材料として用いられてい
る。[Prior Art] and [Problems to be Solved by the Invention] Acrylic elastomers are copolymer elastomers whose main component is acrylic ester, and generally have high heat resistance,
As a rubber with excellent oil resistance, it is used as a molding material for oil seals, O-rings, gaskets, hoses, etc.
しかるに、昨今の機器、オイルなどの高性能化、省資源
化などのため、これ迄以上に耐熱性、耐寒性にすぐれた
材料が望まれるようになってきているのが実情である。However, due to recent improvements in the performance of equipment, oil, etc., and resource conservation, the reality is that materials with superior heat resistance and cold resistance have become more desirable than ever.
そこで1本発明者らは、かかる課題の解決方法を求めて
種々検討を重ねた結果、アクリルエラストマーをエチレ
ン−エチルアクリレート共重合体とブレンドし、多官能
性単量体の存在下に有機過酸化物を用いて共加硫するこ
とによって、かかる課題が効果的に解決されることを見
出した。Therefore, as a result of various studies in search of a solution to this problem, the present inventors blended an acrylic elastomer with an ethylene-ethyl acrylate copolymer and applied organic peroxide in the presence of a polyfunctional monomer. It has been found that such problems can be effectively solved by co-curing with a material.
従って、本発明は加硫性ブレンドゴム組成物に係り、こ
の加硫性ブレンドゴム組成物は、アクリルエラストマー
、エチレン−エチルアクリレ−1へ共重合体、多官能性
単量体および有機過酸化物を含有してなる。Accordingly, the present invention relates to a vulcanizable blend rubber composition, which comprises an acrylic elastomer, ethylene-ethyl acrylate-1, a copolymer, a polyfunctional monomer, and an organic peroxide. Contains.
ブレンドゴムの一方の成分であるアクリルエラストマー
としては、次のようなものが用いられる。As the acrylic elastomer which is one component of the blended rubber, the following is used.
(a)炭素数1〜8のアルキル基を有するアルキルアク
リレートおよび(b)炭素数2〜8のアルコキシアルキ
ル基を有するアルコキシアルキルアクリレートよりなる
群から選ばれた少くとも一種のアクリレート約50〜1
00重量%
例えば、メチルアクリレート、エチルアクリレート、n
−またはイソ−プロピルアクリレート、n−またはイソ
−ブチルアクリレート、ローアミルアクリレート、n−
へキシルアクリレート、2−エチルへキシルアクリレー
ト、n−オクチルアクリレート、2−シアノエチルアク
リレートなどのアルキルアクリレートで、好ましくはエ
チルアクリレートまたはn−ブチルアクリレート、ある
いはメトキシメチルアクリレート、エトキシメチルアク
リレート、2−メトキシエチルアクリレート、2−エト
キシエチルアクリレート、2−ブトキシエチルアクリレ
ートなどのアルコキシアルキルアクリレートで、好まし
くは2−メトキシエチルアクリレート、2−エトキシエ
チルアクリレート
(c)ジエン系単量体約5〜0重量%
例えば、ジビニルベンゼン、ピペリレン、イソプレン、
ペンタジェン、ビニルシクロヘキセン、クロロプレン、
ブタジェン、メチルブタジェン。Approximately 50 to 1 at least one acrylate selected from the group consisting of (a) an alkyl acrylate having an alkyl group having 1 to 8 carbon atoms and (b) an alkoxyalkyl acrylate having an alkoxyalkyl group having 2 to 8 carbon atoms
00% by weight For example, methyl acrylate, ethyl acrylate, n
- or iso-propyl acrylate, n- or iso-butyl acrylate, rhoamyl acrylate, n-
Alkyl acrylates such as hexyl acrylate, 2-ethylhexyl acrylate, n-octyl acrylate, 2-cyanoethyl acrylate, preferably ethyl acrylate or n-butyl acrylate, or methoxymethyl acrylate, ethoxymethyl acrylate, 2-methoxyethyl acrylate , 2-ethoxyethyl acrylate, 2-butoxyethyl acrylate, and other alkoxyalkyl acrylates, preferably 2-methoxyethyl acrylate, 2-ethoxyethyl acrylate (c) about 5 to 0% by weight of a diene monomer, for example, divinylbenzene , piperylene, isoprene,
Pentagene, vinylcyclohexene, chloroprene,
Butadiene, methylbutadiene.
シクロペンタジェン、メチルペンタジェン、エチレング
リコールジ(メタ)アクリレート、プロピレングリコー
ルジ(メタ)アクリレート、エチリデンノルボルネン、
ビニリデンノルボルネン、アリル(メタ)アクリレート
、2−ブテニル(メタ)アクリレート、エチリデンノル
ボルネン(メタ)アクリレート、ジシクロペンタジェン
(メタ)アクリレート(d)架橋性基含有ビニル単量体
約5〜0重量2例えば、アリルグリシジルエーテル、グ
リシジル(メタ)アクリレート、ビニルグリシジルエー
テルなどのエポキシ基含有ビニル単量体、アクリル酸、
メタクリル酸、イタコン酸、マレイン酸、無水マレイン
酸などのカルボキシル基含有ビニル単量体、ヒドロキシ
アルキル(メタ)アクリレート、ヒドロキシアルコキシ
アクリレート、N−メチロールアクリルアミドなどの水
酸基含有ビニル単量体、2−タロルエチルビニルエーテ
ル、モノクロル酢酸、クロルメチルスチレンなどの反応
性ハロゲン含有ビニル単量体
(e)これらの重合性単量体と共重合し得る少くとも一
種の単量体約40〜0重量2
例えば、エチレン、プロピレン、塩化ビニル、塩化ビニ
リデン、アクリロニトリル、スチレン、酢酸ビニル、エ
チルビニルエーテル、ブチルビニルエーテル、アルキル
メタクリレート、アルコキシアルキルメタクリレート
以上の各成分は、任意の重合方法により共重合させるこ
とができるが、好ましくはけん濁重合法または乳化重合
法が用いられる。Cyclopentadiene, methylpentadiene, ethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, ethylidene norbornene,
Vinylidene norbornene, allyl (meth)acrylate, 2-butenyl (meth)acrylate, ethylidenenorbornene (meth)acrylate, dicyclopentadiene (meth)acrylate (d) Vinyl monomer containing crosslinkable group, about 5 to 0 weight 2 e.g. , epoxy group-containing vinyl monomers such as allyl glycidyl ether, glycidyl (meth)acrylate, vinyl glycidyl ether, acrylic acid,
Carboxyl group-containing vinyl monomers such as methacrylic acid, itaconic acid, maleic acid, maleic anhydride, hydroxyl group-containing vinyl monomers such as hydroxyalkyl (meth)acrylate, hydroxyalkoxyacrylate, N-methylolacrylamide, 2-thalol Reactive halogen-containing vinyl monomers such as ethyl vinyl ether, monochloroacetic acid, chloromethylstyrene, etc. (e) At least one monomer copolymerizable with these polymerizable monomers, about 40 to 0% by weight2, for example, ethylene , propylene, vinyl chloride, vinylidene chloride, acrylonitrile, styrene, vinyl acetate, ethyl vinyl ether, butyl vinyl ether, alkyl methacrylate, alkoxyalkyl methacrylate The above components can be copolymerized by any polymerization method, but preferably by A turbidity polymerization method or an emulsion polymerization method is used.
ブレンドゴムの他方の成分であるエチレン−エチルアク
リレート共重合体としては、一般にエチルアクリレート
含有量が約5〜60重量%であるものが用いられる。ま
た、この共重合体は、加圧重合法により製造される。The ethylene-ethyl acrylate copolymer which is the other component of the blended rubber generally has an ethyl acrylate content of about 5 to 60% by weight. Moreover, this copolymer is produced by a pressure polymerization method.
ブレンドゴムを形成するアクリルエラストーマーとエチ
レン−エチルアクリレート共重合体とは、一般に約30
/70〜9515の重量比で用いられる。アクリルエラ
ストマーがこれより多い割合で用いられると所期の改質
効果が得られなくなり、一方これより少ない割合ではゴ
ム状を呈さないようになる。The acrylic elastomer and ethylene-ethyl acrylate copolymer that form the blended rubber generally have a
/70 to 9515 by weight. If the acrylic elastomer is used in a proportion greater than this, the desired modification effect will not be obtained, while if the proportion is less than this, it will no longer exhibit a rubber-like appearance.
これらのゴム両成分は、有機過酸化物、例えばベンゾイ
ルパーオキシド、2,4−ジクロル−ベンゾイルパーオ
キシド、1,1−ジ(第3ブチルパーオキシ)−3,3
,5−トリメチルシクロヘキサン、n−ブチル−4゜4
−ビス(第3ブチルパーオキシ)バレレート、ジクミル
パーオキシド、ジ第3ブチルパーオキシ−ジイソプロピ
ルベンゼン、2,5−ジメチル−2,5−ジ(第3ブチ
ルパーオキシ)ヘキサン、2,5−ジメチル−2,5−
ジ(第3ブチルパーオキシ)ヘキシン−3などを用いて
共加硫される。Both of these rubber components are organic peroxides such as benzoyl peroxide, 2,4-dichloro-benzoyl peroxide, 1,1-di(tert-butylperoxy)-3,3
, 5-trimethylcyclohexane, n-butyl-4゜4
-Bis(tert-butylperoxy)valerate, dicumyl peroxide, ditert-butylperoxy-diisopropylbenzene, 2,5-dimethyl-2,5-di(tert-butylperoxy)hexane, 2,5- dimethyl-2,5-
Co-vulcanization is performed using di(tert-butylperoxy)hexyne-3 or the like.
これらの有機過酸化物は、ブレンドゴム100重量部当
り約0.1〜IO重量部、好ましくは約0.5〜5重量
部の割合で用いられる。これ以下の使用割合では、加硫
が不モ分で満足すべき引張強度を有する加硫物が得られ
ず、一方有機過酸化物をこれ以上の割合で用いると、加
硫物の伸びの低下が大きくなる。These organic peroxides are used in an amount of about 0.1 to IO parts by weight, preferably about 0.5 to 5 parts by weight, per 100 parts by weight of the blended rubber. If the proportion of organic peroxide used is lower than this, the vulcanizate will not have sufficient tensile strength due to the inorganic content, while if the proportion of organic peroxide is higher than this, the elongation of the vulcanizate will decrease. becomes larger.
ブレンドゴムを有機過酸化物で共加硫する際、多官能性
単量体を共存させる。多官能性単量体としては、例えば
トリアリルシアヌレート、トリアリルイソシアヌレート
、トリアリルトリメリテート、トリメチロールプロパン
トリメタクリレート、ポリエチレングリコールジ(メタ
)アクリレート、−フェニレンビスマレイミドなどが、
ブレンドゴム100重量部当り約0.1〜20重量部、
好ましくは約1〜lO重量部の割合で用いられる。これ
以下の使用割合では常態物性中100%モジュラスおよ
び引張強さが著しく低下し、一方これより多く多官能性
単量体を用いると、加硫物の伸びの低下が大きくなる。When co-vulcanizing the blended rubber with an organic peroxide, a polyfunctional monomer is allowed to coexist. Examples of polyfunctional monomers include triallyl cyanurate, triallyl isocyanurate, triallyl trimellitate, trimethylolpropane trimethacrylate, polyethylene glycol di(meth)acrylate, -phenylene bismaleimide, and the like.
Approximately 0.1 to 20 parts by weight per 100 parts by weight of blended rubber,
Preferably, it is used in a proportion of about 1 to 10 parts by weight. If the proportion used is less than this, the 100% modulus and tensile strength among normal physical properties will be significantly reduced, while if the polyfunctional monomer is used in a larger amount than this, the elongation of the vulcanizate will be greatly reduced.
加硫性ブレンドゴム組成物の調製は、他の公知の配合剤
、例えば補強剤、充填剤、安定剤、可塑剤、滑剤などと
共に、以上の各成分をロール混合法、バンバリー混合法
など通常用いられる方法で混合することにより行われる
。それの加硫は、−般に約150〜190℃、約5〜2
0分間のプレス加硫および約150−180℃、約2〜
15時間の二次加硫によって行われる。The vulcanizable blend rubber composition is prepared by adding the above-mentioned components together with other known compounding agents such as reinforcing agents, fillers, stabilizers, plasticizers, lubricants, etc. using a roll mixing method, Banbury mixing method, etc. This is done by mixing in the manner described. The vulcanization thereof is - generally about 150-190°C, about 5-2
Press vulcanization for 0 minutes and about 150-180℃, about 2~
This is done by secondary vulcanization for 15 hours.
本発明に係る加硫性ブレンドゴム組成物は、エチレン−
エチルアクリレート共重合体をブレンドして用いること
により、アクリルエラストマー単体を用いた場合と比較
して、長時間にわたる耐熱性にすぐれており、このこと
は硬さ変化、引張強さ変化率、伸び変化率などの変化幅
の小さいことによって裏付けられ、また耐寒性の点にお
いてもすぐれている。The vulcanizable blend rubber composition according to the present invention has ethylene-
By using a blend of ethyl acrylate copolymer, it has superior long-term heat resistance compared to the case where acrylic elastomer is used alone. This is supported by the fact that the range of changes in the rate of change is small, and it is also excellent in terms of cold resistance.
次に、実施例について本発明を説明する。 Next, the present invention will be explained with reference to examples.
参考例
温度計、攪拌機、窒素導入管および減圧装置を備えたセ
パラブルフラスコ中に、水150部(重量。Reference Example: 150 parts of water (by weight) was placed in a separable flask equipped with a thermometer, stirrer, nitrogen inlet tube, and pressure reducing device.
以下同じ)、硫酸ナトリウム0.1部、乳化剤(花王製
品エマール10、エマルゲン147、レベノールwZの
1,5 : 2.0 : 2.0混合物)5.5部およ
び下記表1の単量体混合物を合計100部仕込み、脱気
、窒素置換をくり返しつつ系内の酸素を十分に除去した
後。(same below), 0.1 part of sodium sulfate, 5.5 parts of emulsifier (1,5:2.0:2.0 mixture of Kao product Emal 10, Emulgen 147, and Lebenol wZ), and the monomer mixture shown in Table 1 below. After charging a total of 100 parts of the mixture, the oxygen in the system was sufficiently removed by repeating deaeration and nitrogen substitution.
ハイドロサルファイドナトリウム0.06部、ナトリウ
ムホルムアルデヒドスルホキシレート0.06部および
第3ブチルハイドロパーオキシド0.03部を加え、室
温下に重合反応を開始させた。重合転化率が95〜9g
%の範囲内になるように反応を6時間継続した後、反応
混合物を塩析し、十分水洗、乾燥し、アクリルエラスト
マーA−Dを得た。0.06 part of sodium hydrosulfide, 0.06 part of sodium formaldehyde sulfoxylate, and 0.03 part of tert-butyl hydroperoxide were added to initiate a polymerization reaction at room temperature. Polymerization conversion rate is 95-9g
After continuing the reaction for 6 hours so as to keep the amount within the range of 1.5%, the reaction mixture was salted out, thoroughly washed with water, and dried to obtain acrylic elastomers A-D.
表1
エチルアクリレート 95.097.736,
037.7n−ブチルアクリレート
30,030.0メトキシエチルアクリレート30,0
30,0アクリロニトリル 2.0 2.
0 2.0 2.0アリルメタクリレート
0.3 0.3グリシジルメタクリレート
2.0ビニルクロ゛ルアセテート3.0
実施例1
上記アクリルエラストマーA 80部、エチレン−エチ
ルアクリレート共重合体(日本ユニカー製品EEA M
B−870、エチルアクリレート含有量41重量120
部、ステアリン酸1部、HAFカーボンブラック45部
、老化防止剤(シュロイヤル社製品ノーガード445、
置換ジフェニルアミン)2部、m−フェニレンビスマレ
イミド3部およびジ第3ブチルパーオキシ−ジイソプロ
ピルベンゼン1部を冷却下のオープンロールで混合し、
調製された加硫性ブレンドゴム組成物を180℃、10
分間のプレス加硫および150℃、15時間のギアーオ
ーブン中での二次加硫を行なった。Table 1 Ethyl acrylate 95.097.736,
037.7n-butyl acrylate
30,030.0 Methoxyethyl acrylate 30,0
30.0 Acrylonitrile 2.0 2.
0 2.0 2.0 Allyl methacrylate
0.3 0.3 glycidyl methacrylate
2.0 vinyl chloroacetate 3.0 Example 1 80 parts of the above acrylic elastomer A, ethylene-ethyl acrylate copolymer (Nippon Unicar product EEA M
B-870, ethyl acrylate content 41 weight 120
part, stearic acid 1 part, HAF carbon black 45 parts, anti-aging agent (Schroyal product Noguard 445,
2 parts of substituted diphenylamine), 3 parts of m-phenylenebismaleimide and 1 part of ditert-butylperoxy-diisopropylbenzene were mixed on an open roll under cooling,
The prepared vulcanizable blend rubber composition was heated at 180°C for 10
Press vulcanization for 1 minute and secondary vulcanization in a gear oven at 150° C. for 15 hours were carried out.
加硫物について、JIS K−6301に準じてその常
態物性を測定し、また175℃での長期耐熱老化試験を
行ない、硬さ変化、引張強さ変化率および伸び変化率を
それぞれ測定すると共に、耐高熱油性 、(150℃の
ASTM Nα3油中に70時間浸漬した後の体積変化
率)、圧縮永久歪および脆化点の測定も行なった。Regarding the vulcanizate, its normal physical properties were measured according to JIS K-6301, and a long-term heat aging test was conducted at 175°C to measure the change in hardness, rate of change in tensile strength, and rate of change in elongation. High-temperature oil resistance (volume change rate after 70 hours of immersion in ASTM Na3 oil at 150°C), compression set, and embrittlement point were also measured.
実施例2
実施例1において、アクリルエラストマーAの代りに、
同量のアクリルエラストマー8が用いられた。Example 2 In Example 1, instead of acrylic elastomer A,
The same amount of acrylic elastomer 8 was used.
実施例3
実施例1において、アクリルエラストマーAの代りに、
同量のアクリルエラストマーDが用いられ、またHAF
カーボンブラックの配合量が50部に変更された。Example 3 In Example 1, instead of acrylic elastomer A,
The same amount of acrylic elastomer D was used and also HAF
The amount of carbon black added was changed to 50 parts.
実施例4
実施例1において、アクリルエラストマーAの代りに6
0部のアクリルエラストマー〇が用いられ、またエチレ
ン−エチルアクリレート共重合体の配合量が40部に変
更された。Example 4 In Example 1, acrylic elastomer A was replaced with 6
0 parts of acrylic elastomer 〇 was used, and the amount of ethylene-ethyl acrylate copolymer was changed to 40 parts.
実施例5
実施例4において、アクリルエラストマーCの代りに、
同量のアクリルエラストマー〇が用いられた。Example 5 In Example 4, instead of acrylic elastomer C,
The same amount of acrylic elastomer 〇 was used.
比較例1
アクリルエラストマーA 100部、ステアリン酸1部
、HAFカーボンブラック50部、老化防止剤(ノーガ
ート4/15)2部、ステアリン酸ナトリウム2.5部
。Comparative Example 1 100 parts of acrylic elastomer A, 1 part of stearic acid, 50 parts of HAF carbon black, 2 parts of anti-aging agent (Nougat 4/15), 2.5 parts of sodium stearate.
ステアリン酸カリウム0.5部およびイオウ0.3部を
用い、実施例1と同様の操作が行われた。The same operation as in Example 1 was carried out using 0.5 part of potassium stearate and 0.3 part of sulfur.
比較例2
実施例2において、エチレン−エチルアクリレート共重
合体を用いずに、アクリルエラストマーBのみを100
部用い、またHAFカーボンブラックの配合量を50部
に変更した。Comparative Example 2 In Example 2, only acrylic elastomer B was used at 100% without using the ethylene-ethyl acrylate copolymer.
parts, and the amount of HAF carbon black added was changed to 50 parts.
比較例3
アクリルエラストマーC100部、ステアリン酸1部、
HAFカーボンブラック55部、老化防止剤(ノーガー
ド445) 2部およびジメチルジチオカルバミン酸亜
鉛2部を用い、実施例1と同様の操作が行われた。Comparative Example 3 100 parts of acrylic elastomer C, 1 part of stearic acid,
The same procedure as in Example 1 was carried out using 55 parts of HAF carbon black, 2 parts of anti-aging agent (Nogard 445) and 2 parts of zinc dimethyldithiocarbamate.
比較例4
実施例5において、エチレン−エチルアクリレート共重
合体を用いずに、アクリルエラストマー〇のみを100
部用い、またHAFカーボンブラックの配合量を55部
に変更した。Comparative Example 4 In Example 5, only the acrylic elastomer ○ was used at 100% without using the ethylene-ethyl acrylate copolymer.
parts, and the amount of HAF carbon black added was changed to 55 parts.
以上の各実施例および比較例での測定結果は。The measurement results for each of the above examples and comparative examples are as follows.
次の表2に示される。It is shown in Table 2 below.
(以下余白)(Margin below)
Claims (1)
ート共重合体、多官能性単量体および有機過酸化物を含
有してなる加硫性ブレンドゴム組成物。 2、アクリルエラストマーとエチレン−エチルアクリレ
ート共重合体とが約30/70〜95/5の重量比で用
いられた特許請求の範囲第1項記載の加硫性ブレンドゴ
ム組成物。[Claims] 1. A vulcanizable blend rubber composition comprising an acrylic elastomer, an ethylene-ethyl acrylate copolymer, a polyfunctional monomer, and an organic peroxide. 2. The vulcanizable blend rubber composition according to claim 1, wherein the acrylic elastomer and the ethylene-ethyl acrylate copolymer are used in a weight ratio of about 30/70 to 95/5.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP62297462A JP2623266B2 (en) | 1987-11-27 | 1987-11-27 | Vulcanizable blended rubber composition |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP62297462A JP2623266B2 (en) | 1987-11-27 | 1987-11-27 | Vulcanizable blended rubber composition |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH01139605A true JPH01139605A (en) | 1989-06-01 |
JP2623266B2 JP2623266B2 (en) | 1997-06-25 |
Family
ID=17846805
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP62297462A Expired - Lifetime JP2623266B2 (en) | 1987-11-27 | 1987-11-27 | Vulcanizable blended rubber composition |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP2623266B2 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2010174217A (en) * | 2009-02-02 | 2010-08-12 | Denki Kagaku Kogyo Kk | Acrylic rubber composition and use thereof |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5323342A (en) * | 1976-08-17 | 1978-03-03 | Nok Corp | Elastomer composition |
JPS59215347A (en) * | 1983-05-20 | 1984-12-05 | Denki Kagaku Kogyo Kk | Vulcanizable elastomer composition |
-
1987
- 1987-11-27 JP JP62297462A patent/JP2623266B2/en not_active Expired - Lifetime
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5323342A (en) * | 1976-08-17 | 1978-03-03 | Nok Corp | Elastomer composition |
JPS59215347A (en) * | 1983-05-20 | 1984-12-05 | Denki Kagaku Kogyo Kk | Vulcanizable elastomer composition |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2010174217A (en) * | 2009-02-02 | 2010-08-12 | Denki Kagaku Kogyo Kk | Acrylic rubber composition and use thereof |
Also Published As
Publication number | Publication date |
---|---|
JP2623266B2 (en) | 1997-06-25 |
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