CN116096761A - 橡胶组合物 - Google Patents
橡胶组合物 Download PDFInfo
- Publication number
- CN116096761A CN116096761A CN202180051975.5A CN202180051975A CN116096761A CN 116096761 A CN116096761 A CN 116096761A CN 202180051975 A CN202180051975 A CN 202180051975A CN 116096761 A CN116096761 A CN 116096761A
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- Prior art keywords
- meth
- acrylate
- rubber composition
- ethylene
- group
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 29
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 33
- 238000004073 vulcanization Methods 0.000 claims abstract description 23
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 22
- 150000001875 compounds Chemical class 0.000 claims abstract description 18
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 15
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 10
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000005977 Ethylene Substances 0.000 claims abstract description 9
- 150000008064 anhydrides Chemical class 0.000 claims abstract description 8
- 125000003118 aryl group Chemical group 0.000 claims abstract description 6
- 125000002723 alicyclic group Chemical group 0.000 claims abstract description 4
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 4
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 4
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000002993 cycloalkylene group Chemical group 0.000 claims abstract description 3
- 125000004427 diamine group Chemical group 0.000 claims abstract description 3
- -1 ester compound Chemical class 0.000 claims description 40
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical group COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 8
- ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 7
- 229920003067 (meth)acrylic acid ester copolymer Polymers 0.000 claims description 5
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 4
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 4
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical group O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 4
- XRAMEHQSATYLEQ-UHFFFAOYSA-N 9h-fluoren-9-ylmethyl n-[6-(9h-fluoren-9-ylmethoxycarbonylamino)hexyl]carbamate Chemical compound C12=CC=CC=C2C2=CC=CC=C2C1COC(=O)NCCCCCCNC(=O)OCC1C2=CC=CC=C2C2=CC=CC=C21 XRAMEHQSATYLEQ-UHFFFAOYSA-N 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
- 229920001577 copolymer Polymers 0.000 abstract description 14
- 238000000465 moulding Methods 0.000 abstract description 8
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 abstract description 7
- 238000006116 polymerization reaction Methods 0.000 description 24
- 239000003921 oil Substances 0.000 description 13
- 229920001897 terpolymer Polymers 0.000 description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 9
- 239000000178 monomer Substances 0.000 description 8
- XSQHUYDRSDBCHN-UHFFFAOYSA-N 2,3-dimethyl-2-propan-2-ylbutanenitrile Chemical compound CC(C)C(C)(C#N)C(C)C XSQHUYDRSDBCHN-UHFFFAOYSA-N 0.000 description 7
- HDIHOAXFFROQHR-UHFFFAOYSA-N 6-aminohexylcarbamic acid Chemical compound NCCCCCCNC(O)=O HDIHOAXFFROQHR-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 239000003963 antioxidant agent Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 230000003712 anti-aging effect Effects 0.000 description 5
- 239000006229 carbon black Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000012744 reinforcing agent Substances 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 239000006057 Non-nutritive feed additive Substances 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000006835 compression Effects 0.000 description 3
- 238000007906 compression Methods 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000004898 kneading Methods 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 description 2
- ZACVGCNKGYYQHA-UHFFFAOYSA-N 2-ethylhexoxycarbonyloxy 2-ethylhexyl carbonate Chemical compound CCCCC(CC)COC(=O)OOC(=O)OCC(CC)CCCC ZACVGCNKGYYQHA-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- AYKYXWQEBUNJCN-UHFFFAOYSA-N 3-methylfuran-2,5-dione Chemical compound CC1=CC(=O)OC1=O AYKYXWQEBUNJCN-UHFFFAOYSA-N 0.000 description 2
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-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
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
- SQSPRWMERUQXNE-UHFFFAOYSA-N Guanylurea Chemical compound NC(=N)NC(N)=O SQSPRWMERUQXNE-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- AYJRCSIUFZENHW-UHFFFAOYSA-L barium carbonate Chemical compound [Ba+2].[O-]C([O-])=O AYJRCSIUFZENHW-UHFFFAOYSA-L 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N butenedioic acid Chemical compound OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 238000011088 calibration curve Methods 0.000 description 2
- 239000011280 coal tar Substances 0.000 description 2
- ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 2
- 125000004386 diacrylate group Chemical group 0.000 description 2
- PPQREHKVAOVYBT-UHFFFAOYSA-H dialuminum;tricarbonate Chemical compound [Al+3].[Al+3].[O-]C([O-])=O.[O-]C([O-])=O.[O-]C([O-])=O PPQREHKVAOVYBT-UHFFFAOYSA-H 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- IRXSLJNXXZKURP-UHFFFAOYSA-N fluorenylmethyloxycarbonyl chloride Chemical class C1=CC=C2C(COC(=O)Cl)C3=CC=CC=C3C2=C1 IRXSLJNXXZKURP-UHFFFAOYSA-N 0.000 description 2
- 150000002357 guanidines Chemical class 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- 229920001684 low density polyethylene Polymers 0.000 description 2
- 239000004702 low-density polyethylene Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- LYRFLYHAGKPMFH-UHFFFAOYSA-N octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(N)=O LYRFLYHAGKPMFH-UHFFFAOYSA-N 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 239000010734 process oil Substances 0.000 description 2
- 239000007870 radical polymerization initiator Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- 235000014692 zinc oxide Nutrition 0.000 description 2
- MYMHEWOMPUIBKB-UHFFFAOYSA-N (2-hydroxy-3-prop-2-enoylperoxypropyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)COOC(=O)C=C MYMHEWOMPUIBKB-UHFFFAOYSA-N 0.000 description 1
- ZCUBIPKXZDFIFT-UHFFFAOYSA-N (3-hydroxy-2-prop-2-enoyloxypropyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(CO)OC(=O)C=C ZCUBIPKXZDFIFT-UHFFFAOYSA-N 0.000 description 1
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 1
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- MJYFYGVCLHNRKB-UHFFFAOYSA-N 1,1,2-trifluoroethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(F)(F)CF MJYFYGVCLHNRKB-UHFFFAOYSA-N 0.000 description 1
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 1
- HSLFISVKRDQEBY-UHFFFAOYSA-N 1,1-bis(tert-butylperoxy)cyclohexane Chemical compound CC(C)(C)OOC1(OOC(C)(C)C)CCCCC1 HSLFISVKRDQEBY-UHFFFAOYSA-N 0.000 description 1
- FUPAJKKAHDLPAZ-UHFFFAOYSA-N 1,2,3-triphenylguanidine Chemical compound C=1C=CC=CC=1NC(=NC=1C=CC=CC=1)NC1=CC=CC=C1 FUPAJKKAHDLPAZ-UHFFFAOYSA-N 0.000 description 1
- TUPIWWRTTIRPDS-UHFFFAOYSA-N 1,2-bis(hydroxymethyl)guanidine Chemical compound OCNC(=N)NCO TUPIWWRTTIRPDS-UHFFFAOYSA-N 0.000 description 1
- QTYUSOHYEPOHLV-FNORWQNLSA-N 1,3-Octadiene Chemical compound CCCC\C=C\C=C QTYUSOHYEPOHLV-FNORWQNLSA-N 0.000 description 1
- OWRCNXZUPFZXOS-UHFFFAOYSA-N 1,3-diphenylguanidine Chemical compound C=1C=CC=CC=1NC(=N)NC1=CC=CC=C1 OWRCNXZUPFZXOS-UHFFFAOYSA-N 0.000 description 1
- SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 1
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 1
- UICXTANXZJJIBC-UHFFFAOYSA-N 1-(1-hydroperoxycyclohexyl)peroxycyclohexan-1-ol Chemical compound C1CCCCC1(O)OOC1(OO)CCCCC1 UICXTANXZJJIBC-UHFFFAOYSA-N 0.000 description 1
- AYMDJPGTQFHDSA-UHFFFAOYSA-N 1-(2-ethenoxyethoxy)-2-ethoxyethane Chemical compound CCOCCOCCOC=C AYMDJPGTQFHDSA-UHFFFAOYSA-N 0.000 description 1
- DNJRKFKAFWSXSE-UHFFFAOYSA-N 1-chloro-2-ethenoxyethane Chemical compound ClCCOC=C DNJRKFKAFWSXSE-UHFFFAOYSA-N 0.000 description 1
- HILAYQUKKYWPJW-UHFFFAOYSA-N 1-dodecylguanidine Chemical compound CCCCCCCCCCCCN=C(N)N HILAYQUKKYWPJW-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
- 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
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2,2'-azo-bis-isobutyronitrile Substances N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
- JPOUDZAPLMMUES-UHFFFAOYSA-N 2,2-bis(tert-butylperoxy)octane Chemical compound CCCCCCC(C)(OOC(C)(C)C)OOC(C)(C)C JPOUDZAPLMMUES-UHFFFAOYSA-N 0.000 description 1
- MFGALGYVFGDXIX-UHFFFAOYSA-N 2,3-Dimethylmaleic anhydride Chemical compound CC1=C(C)C(=O)OC1=O MFGALGYVFGDXIX-UHFFFAOYSA-N 0.000 description 1
- VMZVBRIIHDRYGK-UHFFFAOYSA-N 2,6-ditert-butyl-4-[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 VMZVBRIIHDRYGK-UHFFFAOYSA-N 0.000 description 1
- VVFVRTNNLLZXAL-UHFFFAOYSA-N 2-(2-methylphenyl)guanidine Chemical compound CC1=CC=CC=C1N=C(N)N VVFVRTNNLLZXAL-UHFFFAOYSA-N 0.000 description 1
- 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 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
- ZILVNHNSYBNLSZ-UHFFFAOYSA-N 2-(diaminomethylideneamino)guanidine Chemical compound NC(N)=NNC(N)=N ZILVNHNSYBNLSZ-UHFFFAOYSA-N 0.000 description 1
- MBEVSMZJMIQVBG-UHFFFAOYSA-N 2-(hydroxymethyl)guanidine Chemical compound NC(N)=NCO MBEVSMZJMIQVBG-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- XQTPCGDEYXTYJX-UHFFFAOYSA-N 2-[benzyl-(3-chloro-2-hydroxypropyl)amino]-n-(4-phenylmethoxyphenyl)acetamide Chemical compound C=1C=CC=CC=1CN(CC(CCl)O)CC(=O)NC(C=C1)=CC=C1OCC1=CC=CC=C1 XQTPCGDEYXTYJX-UHFFFAOYSA-N 0.000 description 1
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/02—Ethene
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L23/04—Homopolymers or copolymers of ethene
- C08L23/08—Copolymers of ethene
- C08L23/0846—Copolymers of ethene with unsaturated hydrocarbons containing other atoms than carbon or hydrogen atoms
- C08L23/0869—Acids or derivatives thereof
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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)
Abstract
本发明提供一种橡胶组合物,其是在乙烯‑(甲基)丙烯酸酯类共聚物中含有作为硫化剂的二氨基甲酸酯化合物和碱性硫化促进剂而成的,所述乙烯‑(甲基)丙烯酸酯类共聚物是以乙烯40摩尔%~79.9摩尔%、具有碳原子数1~8的烷基的(甲基)丙烯酸烷基酯和/或具有碳原子数2~8的烷氧基烷基的(甲基)丙烯酸烷氧基烷基酯20.0摩尔%~50.0摩尔%、不饱和二羧酸酐0.05摩尔%~20.0摩尔%的比例共聚而成的,所述二氨基甲酸酯化合物由通式R2(SO2)m(CH2)nOCONH‑R1‑NHCOO(CH2)n(SO2)mR2表示(式中,R1为C1~C20的直链状或支链状的二价脂肪族亚烷基、二价脂环式亚环烷基或二价芳香族基团,R2为在形成氨基甲酸酯结构时可通过碱性硫化促进剂的作用发生分解并产生二胺的基团,n为0、1或2,m为0或1)。该橡胶组合物可获得耐热性、耐油性和成型加工性优异的硫化物。
Description
技术领域
本发明涉及一种橡胶组合物。更详细地,涉及一种可获得耐热性、耐油性和成型加工性优异的硫化物的橡胶组合物。
背景技术
作为获得耐油耐热性优异的硫化物的共聚物,专利文献1中提出了一种含有乙烯、丙烯酸甲酯或丙烯酸乙酯、和1,4-丁烯二酸单烷基酯作为单体的无规共聚物。上述共聚物是在高压下进行聚合而制造的,由于1,4-丁烯二酸单烷基酯的腐蚀性,因此需要耐蚀性的高压设备。
现有技术文献
专利文献
专利文献1:日本特开昭50-49389号公报
专利文献2:日本特开平8-25586号公报
专利文献3:日本特公平7-94486号公报
专利文献4:日本特开2010-235955号公报
发明内容
发明要解决的课题
本发明的目的在于提供一种可获得耐热性、耐油性和成型加工性优异的硫化物的橡胶组合物。
用于解决课题的技术手段
上述本发明的目的可通过如下橡胶组合物来实现,所述橡胶组合物是在乙烯-(甲基)丙烯酸酯类共聚物中含有作为硫化剂的二氨基甲酸酯化合物和碱性硫化促进剂而成的,所述乙烯-(甲基)丙烯酸酯类共聚物是以乙烯40摩尔%~79.9摩尔%、具有碳原子数1~8的烷基的(甲基)丙烯酸烷基酯和/或具有碳原子数2~8的烷氧基烷基的(甲基)丙烯酸烷氧基烷基酯20.0摩尔%~50.0摩尔%、不饱和二羧酸酐0.05摩尔%~20.0摩尔%的比例共聚而成的,所述二氨基甲酸酯化合物由下述通式表示。
R2(SO2)m(CH2)nOCONH-R1-NHCOO(CH2)n(SO2)mR2
(式中,R1为C1~C20的直链状或支链状的二价脂肪族亚烷基、二价脂环式亚环烷基或二价芳香族基团,R2为在形成氨基甲酸酯结构时可通过碱性硫化促进剂的作用发生分解并产生二胺的基团,n为0、1或2,m为0或1)
发明效果
对于由本发明涉及的橡胶组合物得到的硫化物,由于耐热性、耐油性和成型加工性优异,因此可有效用作汽车等运输设备、产业机械、通用设备、电气设备等广泛领域中的橡胶构件,例如O型圈、各种衬垫、油封、轴承密封、端盖垫圈、塞管垫圈、发动机盖垫圈、机油滤清器衬垫、油底壳垫圈、防振构件、输油软管、燃料软管、空气软管、风道软管、涡轮增压器软管、PCV软管、EGR软管、中冷器软管等密封件、垫圈(gasket)、软管等。
具体实施方式
作为(甲基)丙烯酸酯,可使用具有碳原子数1~8的烷基的(甲基)丙烯酸烷基酯和具有碳原子数2~8的烷氧基烷基的(甲基)丙烯酸烷氧基烷基酯中的至少一种,它们可以单独使用或组合使用。这里,(甲基)丙烯酸酯是指丙烯酸酯或甲基丙烯酸酯。
作为(甲基)丙烯酸烷基酯,可使用例如(甲基)丙烯酸甲酯、(甲基)丙烯酸乙酯、(甲基)丙烯酸丙酯、(甲基)丙烯酸异丙酯、(甲基)丙烯酸正丁酯、(甲基)丙烯酸正己酯、(甲基)丙烯酸2-乙基己酯、(甲基)丙烯酸正辛酯等。通常情况下,若烷基的链长变长,则在耐寒性方面有利,但在耐油性方面不利,若烷基的链长短,则出现与其相反的趋势,从耐油性、耐寒性的均衡上考虑,优选使用丙烯酸甲酯、丙烯酸乙酯、丙烯酸正丁酯。进一步优选使用丙烯酸甲酯。
另外,作为(甲基)丙烯酸烷氧基烷基酯,可使用例如(甲基)丙烯酸甲氧基甲酯、(甲基)丙烯酸甲氧基乙酯、(甲基)丙烯酸乙氧基乙酯、(甲基)丙烯酸正丁氧基乙酯、(甲基)丙烯酸乙氧基丙酯、(甲基)丙烯酸甲氧基乙氧基乙酯、(甲基)丙烯酸乙氧基乙氧基乙酯等。
不饱和二羧酸酐是分子中具有一个以上可自由基聚合的不饱和键和一个以上酸酐基的化合物,可举出例如马来酸酐、柠康酸酐、衣康酸酐、2,3-二甲基马来酸酐、2-(2-羧乙基)-3-甲基马来酸酐、3,4,5,6-四氢邻苯二甲酸酐、苯基马来酸酐、2,3-二苯基马来酸酐、烯丙基琥珀酸酐、(2-甲基-2-丙烯基)琥珀酸酐、2-丁烯-1-基琥珀酸酐、顺式-4-环己烯-1,2-二甲酸酐、5-降冰片烯-2,3-二甲酸酐、双环[2.2.2]辛-5-烯-2,3-二甲酸酐等,优选使用马来酸酐、衣康酸酐、柠康酸酐。这些不饱和二羧酸酐可以单独使用或组合两种以上来使用。
除了以上单体以外,也可以根据需要在不损害其特性的范围内使用其他可共聚的单体,例如:苯乙烯、乙烯基甲苯、α-甲基苯乙烯、乙烯基萘、丙烯腈、甲基丙烯腈、丙酮丙烯酰胺、丙烯酸2-羟乙酯、丙烯酸4-羟丁酯、(甲基)丙烯酸2-羟基-3-氯丙酯、氯乙烯、偏二氯乙烯、氟乙烯、偏二氟乙烯、氯乙基乙烯基醚、羟乙基乙烯基醚、羟丁基乙烯基醚、(甲基)丙烯酸五氟丙酯、(甲基)丙烯酸三氟乙酯等乙烯基化合物;异戊二烯、戊二烯、丁二烯等二烯化合物;丙烯、1-丁烯、1-己烯、1-辛烯等α-烯烃。
另外,也可以出于改善混炼加工性、挤出加工性等的目的而进一步共聚使用多官能性(甲基)丙烯酸酯或低聚物,例如:乙二醇、丙二醇、1,4-丁二醇、1,6-己二醇、1,9-壬二醇等亚烷基二醇的二(甲基)丙烯酸酯;新戊二醇、四乙二醇、三丙二醇、聚丙二醇等的二(甲基)丙烯酸酯;双酚A·环氧乙烷加成物二丙烯酸酯、二羟甲基三环癸烷二丙烯酸酯、丙三醇甲基丙烯酸酯丙烯酸酯、3-丙烯酰氧基丙三醇单甲基丙烯酸酯等。
共聚物的制造方法没有特别限定,可以适当使用自由基溶液聚合法等(专利文献2~3)各种聚合方法。通常情况下,可以利用高压法低密度聚乙烯的制造设备及其技术来制造,例如,利用本体聚合法,在70MPa~350MPa、优选100MPa~250MPa的聚合压力下,且在100℃~300℃、优选130℃~270℃的聚合温度下,通过自由基聚合法来制造。如果聚合压力低于70MPa,则聚合物的分子量变低,成型性、树脂组合物的树脂物性变差。另一方面,若聚合压力超过350MPa,则只会提高制造成本,没有实质意义。另外,如果聚合温度低于100℃,则聚合反应不稳定,向共聚物的转化率降低,在经济上存在问题。另一方面,若聚合温度超过300℃,则共聚物的分子量下降,同时有发生失控反应(runaway reaction)的危险。
由于自由基聚合性二羧酸酐缺乏聚合稳定性,因此需要高度的反应器内的均质化。另外,也可以根据需要将多个反应器串联或并联而进行多级聚合。进而,也可以通过将反应器内部划分为多个区域来进行更精确的温度控制。另外,可以通过调节供于聚合的乙烯的温度来调节聚合反应速度,与聚合温度的温差越大,聚合反应速度越高。
聚合反应在至少一种自由基聚合引发剂的存在下进行。自由基聚合所使用的自由基聚合引发剂可选择产生游离基的化合物,可举出例如:氧、二叔丁基过氧化物、叔丁基枯基过氧化物、二枯基过氧化物等二烷基过氧化物;过氧化乙酰、过氧化异丁酰、过氧化辛酰等二酰基过氧化物;过氧化二碳酸二异丙基酯、过氧化二碳酸二(2-乙基己基)酯等过氧化二碳酸酯;过氧化异丁酸叔丁酯、过氧化新癸酸叔丁酯、过氧化新戊酸叔丁酯、过氧化月桂酸叔丁酯等过氧化酯;过氧化甲乙酮、过氧化环己酮等过氧化酮;1,1-双叔丁基过氧基环己烷、2,2-双叔丁基过氧基辛烷等过氧化缩酮;叔丁基过氧化氢、异丙苯基过氧化氢等氢过氧化物;2,2-偶氮二异丁腈等偶氮化合物等。
在所得到的乙烯-(甲基)丙烯酸酯类共聚物中,从得到耐热性和成型加工性优异的硫化物的观点考虑,选择以乙烯40摩尔%~79.9摩尔%(优选60摩尔%~79.9摩尔%)、具有碳原子数1~8的烷基的(甲基)丙烯酸烷基酯和/或具有碳原子数2~8的烷氧基烷基的(甲基)丙烯酸烷氧基烷基酯15.0摩尔%~50.0摩尔%(优选20.0摩尔%~35.0摩尔%)、不饱和二羧酸酐0.05摩尔%~20.0摩尔%(优选0.10摩尔%~1.50摩尔%)的比例共聚而成的共聚物来进行橡胶组合物的制备。
作为乙烯-(甲基)丙烯酸酯类共聚物的硫化剂,可使用专利文献4等中公开的、由下述通式表示的二氨基甲酸酯化合物。
R2(SO2)m(CH2)nOCONH-R1-NHCOO(CH2)n(SO2)mR2
(式中,R1为C1~C20的直链状或支链状的二价脂肪族亚烷基、二价脂环式烃基或二价芳香族基团,R2为在形成氨基甲酸酯结构时可通过碱性硫化促进剂的作用发生分解并产生二胺的基团,例如为C1~C20的烷基、烷氧基、苯氧基、卤代烷基、链烯基、芳基或芳烷基、含芴基的基团、含S基团、含Si基团、含N基团或含P基团,含S基团或含N基团为芳香族或脂环式的杂环式基团,n为0、1或2,m为0或1)
优选使用由通式H2N(CH2)LNH2(L=4~6)表示的亚烷基二胺的氨基被两个9-芴甲基氯甲酸酯置换而成的二氨基甲酸酯化合物,进一步优选使用六亚甲基二胺(L=6)的氨基被两个9-芴甲基氯甲酸酯置换而成的二氨基甲酸酯化合物即1,6-己烷双氨基甲酸双(9-芴甲基)酯、
或1,6-己烷双氨基甲酸双[1-甲基-1-(4-甲基苯基)乙基]酯。
这种多胺化合物硫化剂以每100重量份的共聚橡胶为约0.1重量份~10重量份、优选0.5重量份~5重量份的比例来使用。若硫化剂的配合量少于该比例,则硫化不充分,会导致硫化物的机械物性下降,硫化速度下降。若硫化剂的配合量多于该比例,则存在硫化过度进行、硫化物的弹性下降的情况。另外,在使用除此以外的硫化剂时,即使使用了胺类硫化剂,也会发生坯料烧焦。在硫化时,碱性硫化促进剂以每100重量份的共聚橡胶为约0.01重量份~5重量份、优选0.5重量份~3重量份的比例来使用。
作为碱性硫化促进剂,使用胍化合物或1,8-二氮杂双环[5.4.0]-7-十一碳烯、1,5-二氮杂双环[4.3.0]-5-壬烯等二氮杂双环烯烃化合物或其有机酸盐、无机酸盐,从其添加效果更高的观点考虑,优选使用1,8-二氮杂双环[5.4.0]-7-十一碳烯[DBU]。另外,也可以使用1,8-二氮杂双环[5.4.0]-7-十一碳烯与二氧化硅的混合物,在实际中可使用SaficAlcan公司产品Vulcofac ACT55等。
作为形成二氮杂双环烯烃化合物的有机酸盐或无机酸盐的化合物,可举出盐酸、硫酸、羧酸、磺酸、苯酚等。作为羧酸,可举出例如辛酸、油酸、甲酸、邻苯二甲酸、己二酸等,另外,作为磺酸,可举出例如苯磺酸、甲苯磺酸、十二烷基苯磺酸、萘磺酸等。这些化合物可以单独使用或并用两种以上。
作为胍化合物,可使用胍或其取代物,例如:氨基胍、1,1,3,3-四甲基胍、正十二烷基胍、羟甲基胍、二羟甲基胍、1-苯基胍、1,3-二苯基胍、1,3-二邻甲苯胍、三苯基胍、1-苄基-2,3-二甲基胍、氰基胍等,此外,还可以使用1,6-胍基己烷、氨基甲酰基胍(guanylurea)、双胍、1-邻甲苯双胍等。
在含有以上成分的橡胶组合物中,可以根据需要适当配合使用增强剂、填充剂、加工助剂、增塑剂、软化剂、抗老化剂、着色剂、稳定剂、粘接助剂、脱模剂、导电性赋予剂、导热性赋予剂、表面非粘合剂、增粘剂、柔韧性赋予剂、耐热性改善剂、阻燃剂、紫外线吸收剂、耐油性改进剂、防焦剂、润滑剂等各种添加剂。
作为增强剂·填充剂,可举出例如:碱性二氧化硅、酸性二氧化硅等二氧化硅;氧化镁、氧化锌、氧化钙、氧化钛、氧化铝等金属氧化物;氢氧化镁、氢氧化铝、氢氧化钙等金属氢氧化物;碳酸镁、碳酸铝、碳酸钙、碳酸钡等金属碳酸盐;硅酸镁、硅酸钙、硅酸钠、硅酸铝等硅酸盐;硫酸铝、硫酸钙、硫酸钡等硫酸盐;合成水滑石;二硫化钼、硫化铁、硫化铜等金属硫化物;硅藻土、石棉、立德粉(Lithopone;硫化锌/硫化钡)、石墨、炭黑(MT炭黑、SRF炭黑、FEF炭黑、HAF炭黑等)、氟化碳、氟化钙、焦炭、石英微粉末、锌白、滑石、云母粉末、硅灰石、碳纤维、芳纶纤维、各种晶须、玻璃纤维、有机增强剂、有机填充剂等。
作为抗老化剂,可举出例如:苯基-α-萘胺、苯基-β-萘胺、对-(对-甲苯磺酰胺)-二苯基胺、4,4'-(α,α-二甲基苄基)二苯基胺、N,N-二苯基-对苯二胺、N-异丙基-N'-苯基-对苯二胺、丁醛-苯胺缩合物等胺类抗老化剂;2,6-二叔丁基苯酚、丁基羟基苯甲醚、2,6-二叔丁基-α-二甲基氨基-对甲酚、十八烷基-3-(3,5-二叔丁基-4-羟基苯基)丙酸酯、单(或二、三)(α-甲基苄基)苯酚、2,2'-亚甲基-双(6-α-甲基苄基-对甲酚)、4,4'-亚甲基双(2,6-二叔丁基苯酚)、2,2'-亚甲基双(4-甲基-6-叔丁基苯酚)、烷基化双酚、对甲酚与双环戊二烯的丁基化反应产物、1,3,5-三(3',5'-二叔丁基-4'-羟基苄基)异氰脲酸酯、1,1,3-三(2-甲基-4-羟基-5-叔丁基苯基)丁烷、亚丁基双(甲基-丁基苯酚)、3-(4'-羟基-3',5'-二叔丁基苯基)丙酸正十八烷基酯、季戊四醇四[3-(3',5'-二叔丁基-4'-羟基苯基)丙酸酯]、2,2'-二甲基-2,2'-(2,4,8,10-四氧杂螺[5.5]十一烷-3,9-二基)二丙烷-1,1'-二基双[3-(3-叔丁基-4-羟基-5-甲基苯基)丙酸酯]、1,3,5-三甲基-2,4,6-三(3,5-二叔丁基-4-羟基苄基)苯、2,6-二叔丁基-4-甲基苯酚等酚类抗老化剂;3,9-双十八烷-1-基-2,4,8,10-四氧杂-3,9-二磷杂螺[5.5]十一烷、3,9-双(2,6-二叔丁基-4-甲基苯氧基)-2,4,8,10-四氧杂-3,9-二磷杂螺[5.5]十一烷、2,4,8,10-四叔丁基-6-[(2-乙基己烷-1-基)氧基-12H-二苯并[d,g][1,3,2]二氧杂磷杂环辛二烯(dioxaphosphocin)、三(2,4-二叔丁基苯基)亚磷酸酯、三(壬基苯基)亚磷酸酯、2-乙基己基二苯基亚磷酸酯、二苯基异癸基亚磷酸酯、三异癸基亚磷酸酯、三苯基亚磷酸酯等亚磷酸酯类抗老化剂;其他苯硫酚类抗老化剂、硫酯类抗老化剂、咪唑类抗老化剂、喹啉类抗老化剂、对苯二酚类抗老化剂等。这些抗老化剂可以分别单独使用或组合两种以上来使用。
作为加工助剂,可举出例如:硬脂酸、油酸、棕榈酸、月桂酸等高级脂肪酸;硬脂酸钠、硬脂酸锌等高级脂肪酸盐;硬脂酰胺、油酰胺等高级脂肪酸酰胺;油酸乙酯等高级脂肪酸酯;巴西棕榈蜡、地蜡(ceresine wax)等石油类蜡;乙二醇、丙三醇、二乙二醇等聚乙二醇;凡士林、石蜡等脂肪族烃;硅酮类油、硅酮类聚合物、低分子量聚乙烯、邻苯二甲酸酯类、磷酸酯类、松香、(卤化)二烷基胺、(卤化)二烷基砜、表面活性剂等。
作为增塑剂,可举出例如环氧树脂、邻苯二甲酸或癸二酸的衍生物等,作为软化剂,可举出例如润滑油、工艺油(process oil)、煤焦油(coal tar)、蓖麻油、硬脂酸钙等。
组合物的制备通过以下方式来进行,即,使用开放辊或者密闭式混炼机向乙烯-(甲基)丙烯酸酯类共聚物中添加增强剂、稳定剂、加工助剂等,进而添加硫化剂和硫化促进剂。对于硫化成型,进行约150℃~200℃、约1分钟~30分钟的一次硫化后,根据需要进行约150℃~200℃、约1小时~16小时的二次硫化(二次硫化)。成型可以根据产品而应用加压成型、传递模塑成型、注射成型、挤出成型等公知的方法。
实施例
下面,针对实施例来说明本发明。
聚合例1~7
在聚合例1中,使用具有容积为5L的高压釜的高压法低密度聚乙烯工厂的设备,以使反应器入口的单体组成为乙烯[E]93.96wt%、丙烯酸甲酯[MA]5.87wt%、马来酸酐[MAH]0.17wt%的方式向反应器中注入各成分。使用过氧化二碳酸二(2-乙基己基)酯作为反应引发剂,在聚合温度140℃、聚合压力165MPa的条件下进行了聚合。其他聚合例也通过调节单体组成、聚合温度、聚合压力来进行制造,得到表1的各种共聚物。共聚组成比率表示所得到的三元共聚物中的单体组成。
表1
实施例1
使用以上各成分,用森山制造的1L捏合机(DS1-5MHB-E)进行了混炼。
接着,使用大竹机械工业制造的8英寸辊,相对于1L捏合混炼坯料156重量份,配合4重量份的1,6-己烷双氨基甲酸双(9-芴甲基)酯和2重量份的DBU-十二烷二盐酸盐(70%产物),制作橡胶物性评价用组合物。针对所得到的混炼组合物,进行180℃、10分钟的一次硫化和175℃、4小时的烘箱硫化(二次硫化),成型硫化片和依据JIS的压缩永久变形测定用块体。
针对所得到的组合物和成型物,测定了以下的各项目。
MFR:依据对应于ISO 1133的JIS K 7210
测定条件:测定在190℃、2.16kg的条件下的熔体流动速率。
耐寒性:型号:SII DSC6220
测定条件:将在-100℃~100℃、升温速率10℃/min的条件下得到DSC曲线的微分峰的温度设为Tg。
耐油性:依据对应于ISO 1817的JIS K 6258
评价在150℃/70hrs的条件下在试验油IRM 903中的溶胀。
·主要单体组成比(MA/E):通过IR测定(mol%),
·在4600cm-1和3500cm-1处绘制基线,测定源于乙烯的4254cm-1峰高,
·在3510cm-1处绘制1点基线,测定源于MA的3457cm-1峰高,
·计算A3457/A4254峰比,由另外通过NMR测定MA含量而制作的校正曲线来计算。
·MAH含量:通过IR测定(mol%),
·在4600cm-1处绘制1点基线,测定源于乙烯的4254cm-1峰高,
·在1875cm-1和1825cm-1处绘制基线,测定源于MAH的1855cm-1峰高,
·使用基于滴定法的MAH含量和IR吸光度比的校正曲线,由A1855/A4254计算MAH含量。
·以乙烯-(甲基)丙烯酸酯-酸酐为共聚单体的共聚物的组成(mol%)
·由主要单体组成比(MA/E)和MAH含量来计算。
门尼粘度焦烧:依据对应于ISO 289的JIS K 6300
型号:AM-4(东洋精机制造)125℃
常态值:依据对应于ISO 37的JIS K 6253、对应于ISO 37的JIS K 6251。
耐热老化性:依据对应于ISO 188的JIS K 6257
评价在175℃/70hrs的条件下的硬度变化。
压缩永久变形:依据对应于ISO 815-1的JIS K 6262
175℃/70hrs、压缩25%
实施例2
在实施例1中,作为三元共聚物,使用了相同量(100重量份)的、聚合例2中所得到的三元共聚物。
实施例3
在实施例1中,作为三元共聚物,使用了相同量(100重量份)的、聚合例3中所得到的三元共聚物。
比较例1
在实施例1中,作为硫化剂,使用了1.25重量份的六亚甲基二胺氨基甲酸酯(Unimatec产品CHEMINOX AC-6)代替1,6-己烷双氨基甲酸双(9-芴甲基)酯。
比较例2
在比较例1中,作为硫化剂,使用了5重量份的2,2-双[4-(4-氨基苯氧基)苯基]丙烷50%母料(Unimatec产品CHEMINOX CLP5250)代替六亚甲基二胺氨基甲酸酯。
实施例4
在实施例3中,使用KOBELCO制造的MIXTRON BB 3.6L代替1L捏合机,进行了混炼。
比较例3
在实施例4中,使用了1.25重量份的六亚甲基二胺氨基甲酸酯(CHEMINOX AC-6)代替1,6-己烷双氨基甲酸双(9-芴甲基)酯。
实施例5
在实施例4中,作为三元共聚物,使用了相同量(100重量份)的、聚合例4中所得到的三元共聚物。
比较例4
在实施例5中,使用了1.25重量份的六亚甲基二胺氨基甲酸酯(CHEMINOX AC-6)代替1,6-己烷双氨基甲酸双(9-芴甲基)酯。
实施例6
在实施例4中,作为三元共聚物,使用了相同量(100重量份)的、聚合例5中所得到的三元共聚物。
比较例5
在实施例6中,使用了1.25重量份的六亚甲基二胺氨基甲酸酯(CHEMINOX AC-6)代替1,6-己烷双氨基甲酸双(9-芴甲基)酯。
实施例7
在实施例4中,作为三元共聚物,使用了相同量(100重量份)的、聚合例6中所得到的三元共聚物。
比较例6
在实施例7中,使用了1.25重量份的六亚甲基二胺氨基甲酸酯(CHEMINOX AC-6)代替1,6-己烷双氨基甲酸双(9-芴甲基)酯。
实施例8
在实施例4中,作为三元共聚物,使用了相同量(100重量份)的、聚合例7中所得到的三元共聚物。
实施例9
在实施例8中,使用了4重量份的二邻甲苯胍(大内新兴化学产品Noxeller DT)代替DBU-十二烷二盐酸盐。
实施例10
在实施例8中,作为硫化剂,使用了3.34重量份的1,6-己烷双氨基甲酸双[1-甲基-1-(4-甲基苯基)乙基]酯代替1,6-己烷双氨基甲酸双(9-芴甲基)酯。
比较例7
在实施例8中,使用了1.25重量份的六亚甲基二胺氨基甲酸酯(CHEMINOX AC-6)代替1,6-己烷双氨基甲酸双(9-芴甲基)酯。
以上的各实施例中所得到的结果示于下面的表2中。需要说明的是,所有比较例在混炼时均发生坯料烧焦,无法测定特性。
表2
Claims (6)
1.一种橡胶组合物,其是在乙烯-(甲基)丙烯酸酯类共聚物中含有作为硫化剂的二氨基甲酸酯化合物和碱性硫化促进剂而成的,
所述乙烯-(甲基)丙烯酸酯类共聚物是以乙烯40摩尔%~79.9摩尔%、具有碳原子数1~8的烷基的(甲基)丙烯酸烷基酯和/或具有碳原子数2~8的烷氧基烷基的(甲基)丙烯酸烷氧基烷基酯20.0摩尔%~50.0摩尔%、不饱和二羧酸酐0.05摩尔%~20.0摩尔%的比例共聚而成的,
所述二氨基甲酸酯化合物由下述通式表示,
R2(SO2)m(CH2)nOCONH-R1-NHCOO(CH2)n(SO2)mR2
式中,R1为C1~C20的直链状或支链状的二价脂肪族亚烷基、二价脂环式亚环烷基或二价芳香族基团,R2为在形成氨基甲酸酯结构时可通过碱性硫化促进剂的作用发生分解并产生二胺的基团,n为0、1或2,m为0或1。
3.根据权利要求1所述的橡胶组合物,其中,(甲基)丙烯酸烷基酯为丙烯酸甲酯。
4.根据权利要求1所述的橡胶组合物,其中,不饱和二羧酸酐为马来酸酐。
5.根据权利要求1所述的橡胶组合物,其中,每100重量份的乙烯-(甲基)丙烯酸酯类共聚物,以0.1重量份~10重量份的比例使用作为硫化剂的二氨基甲酸酯化合物,以0.01重量份~5重量份的比例使用作为碱性硫化促进剂的胍化合物。
6.一种硫化成型物,其为权利要求1所述的橡胶组合物的硫化成型物。
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CN101932556A (zh) * | 2008-01-30 | 2010-12-29 | 优迈特株式会社 | 新型二氨基甲酸酯化合物、其制造方法及含有其的丙烯酸橡胶组合物 |
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JPH0794486B2 (ja) | 1987-12-14 | 1995-10-11 | 昭和電工株式会社 | エチレン系共重合体の製造方法 |
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WO2019003917A1 (ja) * | 2017-06-29 | 2019-01-03 | Nok株式会社 | 架橋アクリルゴム成形体の製造方法、アクリルゴム組成物およびシール材 |
CN112955429B (zh) * | 2018-11-20 | 2022-01-07 | 优迈特株式会社 | 新型氨基甲酸酯化合物和含有该化合物的丙烯酸类橡胶组合物 |
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CN1852928A (zh) * | 2003-07-24 | 2006-10-25 | 纳幕尔杜邦公司 | 具有改善低温性能的乙烯/丙烯酸烷基酯无规共聚物及其混炼胶和弹性体组合物 |
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