WO2022196794A1 - エチレン-(メタ)アクリレート系エラストマーおよびその製造法 - Google Patents
エチレン-(メタ)アクリレート系エラストマーおよびその製造法 Download PDFInfo
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- WO2022196794A1 WO2022196794A1 PCT/JP2022/012516 JP2022012516W WO2022196794A1 WO 2022196794 A1 WO2022196794 A1 WO 2022196794A1 JP 2022012516 W JP2022012516 W JP 2022012516W WO 2022196794 A1 WO2022196794 A1 WO 2022196794A1
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- Prior art keywords
- meth
- acrylate
- ethylene
- ring
- mol
- Prior art date
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- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 title claims abstract description 71
- 229920001971 elastomer Polymers 0.000 title claims abstract description 37
- 239000000806 elastomer Substances 0.000 title claims abstract description 32
- 238000004519 manufacturing process Methods 0.000 title claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 17
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000005977 Ethylene Substances 0.000 claims abstract description 14
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 8
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
- 239000000155 melt Substances 0.000 claims abstract description 6
- 238000007142 ring opening reaction Methods 0.000 claims description 61
- 229920001577 copolymer Polymers 0.000 claims description 37
- -1 unsaturated dicarboxylic acid compound Chemical group 0.000 claims description 34
- 239000003054 catalyst Substances 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 24
- 239000003795 chemical substances by application Substances 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 17
- 238000004898 kneading Methods 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 12
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical group COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 11
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 11
- 230000032683 aging Effects 0.000 claims description 10
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 9
- 239000011976 maleic acid Substances 0.000 claims description 9
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical group O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 7
- 238000000465 moulding Methods 0.000 claims description 7
- 150000008065 acid anhydrides Chemical class 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 4
- 150000007514 bases Chemical group 0.000 claims 1
- 125000001142 dicarboxylic acid group Chemical group 0.000 claims 1
- 238000002156 mixing Methods 0.000 claims 1
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 abstract 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 description 41
- 229920001897 terpolymer Polymers 0.000 description 37
- 239000000047 product Substances 0.000 description 19
- 238000004073 vulcanization Methods 0.000 description 17
- 239000003921 oil Substances 0.000 description 13
- 230000000052 comparative effect Effects 0.000 description 11
- 239000000178 monomer Substances 0.000 description 11
- 239000003963 antioxidant agent Substances 0.000 description 10
- 238000000034 method Methods 0.000 description 10
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 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 7
- 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 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
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- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
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- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
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- 239000000377 silicon dioxide Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical class O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000006057 Non-nutritive feed additive Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 230000006835 compression Effects 0.000 description 3
- 238000007906 compression Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 229920003192 poly(bis maleimide) Polymers 0.000 description 3
- 239000012744 reinforcing agent Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 3
- 229960002447 thiram Drugs 0.000 description 3
- 238000004448 titration Methods 0.000 description 3
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-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
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 2
- OPNUROKCUBTKLF-UHFFFAOYSA-N 1,2-bis(2-methylphenyl)guanidine Chemical compound CC1=CC=CC=C1N\C(N)=N\C1=CC=CC=C1C OPNUROKCUBTKLF-UHFFFAOYSA-N 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- 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 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
- 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 2
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-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
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 description 2
- HDIHOAXFFROQHR-UHFFFAOYSA-N 6-aminohexylcarbamic acid Chemical compound NCCCCCCNC(O)=O HDIHOAXFFROQHR-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
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- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 239000004129 EU approved improving agent Substances 0.000 description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-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
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- 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
- 229910019142 PO4 Inorganic materials 0.000 description 2
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- 238000002835 absorbance Methods 0.000 description 2
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- 125000002723 alicyclic group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 230000003712 anti-aging effect Effects 0.000 description 2
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- 238000011088 calibration curve Methods 0.000 description 2
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- 238000004925 denaturation Methods 0.000 description 2
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- 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
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- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
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- ATPFMBHTMKBVLS-UHFFFAOYSA-N n-[6-(cinnamylideneamino)hexyl]-3-phenylprop-2-en-1-imine Chemical compound C=1C=CC=CC=1C=CC=NCCCCCCN=CC=CC1=CC=CC=C1 ATPFMBHTMKBVLS-UHFFFAOYSA-N 0.000 description 2
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
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- 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
- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 description 1
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 1
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- BEQKKZICTDFVMG-UHFFFAOYSA-N 1,2,3,4,6-pentaoxepane-5,7-dione Chemical compound O=C1OOOOC(=O)O1 BEQKKZICTDFVMG-UHFFFAOYSA-N 0.000 description 1
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- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- 150000003022 phthalic acids Chemical class 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 238000003918 potentiometric titration Methods 0.000 description 1
- 239000010734 process oil Substances 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- BNMCQIRVFUGISV-UHFFFAOYSA-N propan-2-one;prop-2-enamide Chemical compound CC(C)=O.NC(=O)C=C BNMCQIRVFUGISV-UHFFFAOYSA-N 0.000 description 1
- BWJUFXUULUEGMA-UHFFFAOYSA-N propan-2-yl propan-2-yloxycarbonyloxy carbonate Chemical compound CC(C)OC(=O)OOC(=O)OC(C)C BWJUFXUULUEGMA-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 239000012763 reinforcing filler Substances 0.000 description 1
- 239000012779 reinforcing material Substances 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 229940037312 stearamide Drugs 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- JZFHXRUVMKEOFG-UHFFFAOYSA-N tert-butyl dodecaneperoxoate Chemical compound CCCCCCCCCCCC(=O)OOC(C)(C)C JZFHXRUVMKEOFG-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 238000001721 transfer moulding Methods 0.000 description 1
- QEDNBHNWMHJNAB-UHFFFAOYSA-N tris(8-methylnonyl) phosphite Chemical compound CC(C)CCCCCCCOP(OCCCCCCCC(C)C)OCCCCCCCC(C)C QEDNBHNWMHJNAB-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
- 239000010456 wollastonite Substances 0.000 description 1
- 229910052882 wollastonite Inorganic materials 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/12—Esters of monohydric alcohols or phenols
- C08F20/14—Methyl esters, e.g. methyl (meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/12—Hydrolysis
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2500/00—Characteristics or properties of obtained polyolefins; Use thereof
- C08F2500/27—Amount of comonomer in wt% or mol%
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2800/00—Copolymer characterised by the proportions of the comonomers expressed
- C08F2800/10—Copolymer characterised by the proportions of the comonomers expressed as molar percentages
Definitions
- the present invention relates to an ethylene-(meth)acrylate elastomer and a method for producing the same. More particularly, it relates to an ethylene-(meth)acrylate elastomer that gives a vulcanizate excellent in heat resistance, oil resistance and moldability, and a method for producing the same.
- Patent Documents 1 and 2 propose the following copolymers as copolymers that give vulcanizates having excellent oil and heat resistance.
- Patent Document 1 A random copolymer containing ethylene, methyl or ethyl acrylate and 1,4-butenedioic acid monoalkyl ester as monomers is described. Such a copolymer is produced by high-pressure polymerization, but due to the corrosiveness of 1,4-butenedionic acid monoalkyl ester, corrosion-resistant high-pressure equipment is required.
- Patent Document 2 An amine-crosslinkable rubber composition comprising a copolymer containing ethylene, acrylate and maleic anhydride as monomers and a primary or secondary polyamine is described. Such a composition has a problem that the scorch time is short because the crosslinking reaction rate is too fast, and it is difficult to mold rubber parts and the like.
- Patent Document 3 when modifying an ethylene/(meth)alkyl acrylate/maleic anhydride/maleic acid monoester quaternary copolymer with an unsaturated amine or an unsaturated alcohol, a maleic acid half ester copolymer is obtained by kneading with Laboplastomill.
- the hydrolysis reaction is carried out in an organic solvent in the presence of a catalyst such as a tertiary amine salt.
- a catalyst such as a tertiary amine salt.
- An object of the present invention is to provide an ethylene-(meth)acrylate elastomer that gives a vulcanizate excellent in heat resistance, oil resistance and moldability, and a method for producing the same.
- the object of the present invention is ethylene 40 to 79.9 mol%, alkyl (meth)acrylate having an alkyl group having 1 to 8 carbon atoms and / or alkoxy(meth)acrylate having an alkoxyalkyl group having 2 to 8 carbon atoms 20.0 to 50.0 mol%, 0.001 to 20.0 mol% of unsaturated dicarboxylic acid and 0.05 to 20.0 mol% of unsaturated dicarboxylic acid anhydride are copolymerized. This is achieved by ethylene-(meth)acrylate elastomers having a melt flow rate of 0.01 to 100 g/10 minutes.
- This ethylene-(meth)acrylate elastomer comprises ethylene, an alkyl(meth)acrylate having an alkyl group having 1 to 8 carbon atoms and/or an alkoxy(meth)acrylate having an alkoxyalkyl group having 2 to 8 carbon atoms, and an unsaturated It is produced by copolymerizing a dicarboxylic anhydride and then carrying out ring-opening treatment of the unsaturated dicarboxylic anhydride.
- the vulcanizate obtained from the ethylene-(meth)acrylate elastomer according to the present invention is excellent in heat resistance, oil resistance and molding processability, and is used in transportation equipment such as automobiles, industrial machinery, general equipment, electrical equipment and the like.
- Rubber parts in a wide range of fields such as O-rings, various packings, oil seals, bearing seals, head cover gaskets, plug tube gaskets, engine head cover gaskets, oil filter packings, oil pan gaskets, anti-vibration parts, oil hoses, fuel hoses, air hoses , air duct hoses, turbocharger hoses, PCV hoses, EGR hoses, intercooler hoses, etc.
- (meth)acrylate at least one of an alkyl (meth)acrylate having an alkyl group having 1 to 8 carbon atoms and an alkoxy (meth)acrylate having an alkoxyalkyl group having 2 to 8 carbon atoms is used. They can be used in combination.
- (meth)acrylate refers to acrylate or methacrylate.
- Alkyl (meth)acrylates include, for example, methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, isopropyl (meth)acrylate, n-butyl (meth)acrylate, n-hexyl (meth)acrylate, 2 -Ethylhexyl (meth)acrylate, n-octyl (meth)acrylate and the like are used.
- the longer the chain length of the alkyl group the more advantageous it is in terms of cold resistance, but the less favorable it is in terms of oil resistance.
- alkoxyalkyl (meth)acrylates examples include methoxymethyl (meth)acrylate, methoxyethyl (meth)acrylate, ethoxyethyl (meth)acrylate, n-butoxyethyl (meth)acrylate, ethoxypropyl (meth)acrylate, methoxy Ethoxyethyl (meth)acrylate, ethoxyethoxyethyl (meth)acrylate and the like are used.
- Unsaturated dicarboxylic anhydrides are compounds having one or more radically polymerizable unsaturated bonds and one or more acid anhydride groups in the molecule. Examples thereof include maleic anhydride, citraconic anhydride, itaconic anhydride, Dimethylmaleic anhydride, 2-(2-carboxyethyl)-3-methylmaleic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, phenylmaleic anhydride, 2,3-diphenylmaleic acid anhydride, allylsuccinic anhydride, (2-methyl-2-propenyl)succinic anhydride, 2-buten-1-ylsuccinic anhydride, cis-4-cyclohexene-1,2-dicarboxylic anhydride, 5-norbornene-2,3-dicarboxylic anhydride, bicyclo[2.2.2]oct-5-ene-2,3-dicarboxylic anhydride, preferably maleic anhydride
- polyfunctional (meth)acrylates or oligomers such as ethylene glycol, propylene glycol, 1,4-butanediol, 1,6-hexane for the purpose of improving kneading processability and extrusion processability.
- Di(meth)acrylates of alkylene glycols such as diols and 1,9-nonanediol, di(meth)acrylates such as neopentyl glycol, tetraethylene glycol, tripropylene glycol and polypropylene glycol, bisphenol A/ethylene oxide adduct diacrylates , dimethyloltricyclodecane diacrylate, glycerin methacrylate acrylate, 3-acryloyloxyglycerin monomethacrylate and the like can be further copolymerized and used.
- alkylene glycols such as diols and 1,9-nonanediol
- di(meth)acrylates such as neopentyl glycol, tetraethylene glycol, tripropylene glycol and polypropylene glycol
- bisphenol A/ethylene oxide adduct diacrylates dimethyloltricyclodecane diacrylate, glycerin methacrylate acrylate
- the method for producing the copolymer is not particularly limited, various polymerization methods such as radical solution polymerization (Patent Documents 4 and 5) can be used as appropriate.
- it can be produced using high-pressure low-density polyethylene production equipment and technology, for example, by bulk polymerization at a polymerization pressure of 70 to 350 MPa, preferably 100 to 250 MPa, at 100 to 300 ° C., It is preferably produced by a radical polymerization method at a polymerization temperature of 150-270°C. If the polymerization pressure is less than 70 MPa, the molecular weight of the polymer becomes low, and the moldability and physical properties of the resin composition deteriorate.
- radically polymerizable dicarboxylic acid anhydrides have poor polymerization stability, a high degree of homogenization within the reactor is required.
- a plurality of reactors can be connected in series or in parallel to carry out multi-stage polymerization. Further, by partitioning the interior of the reactor into a plurality of zones, it is possible to perform more precise temperature control. Also, the polymerization reaction rate can be adjusted by adjusting the temperature of the ethylene subjected to the polymerization, and the greater the temperature difference from the polymerization temperature, the higher the polymerization reaction rate.
- the polymerization reaction is carried out in the presence of at least one free radical polymerization initiator.
- the free radical polymerization initiator used in the radical polymerization is selected from compounds that generate free radicals, such as oxygen, dialkyl peroxide such as di-tert-butyl peroxide, tert-butyl cumyl peroxide, dicumyl peroxide, acetyl diacyl peroxide such as peroxide, isobutyl peroxide, octanoyl peroxide; peroxydicarbonate such as diisopropyl peroxydicarbonate, di(2-ethylhexylperoxy) dicarbonate; Peroxy esters such as 3-butyl peroxyneodecanate, tert-butyl peroxypivalate, tert-butyl peroxylaurate, ketone peroxides such as methyl ethyl ketone peroxide and cyclohexanone peroxide, 1,1
- the resulting ethylene-(meth)acrylate copolymer containing an acid anhydride is subjected to a ring-opening treatment using a shear melt-kneading method, preferably an internal kneader or a twin-screw extruder, in which ring-opening treatment is performed under shear conditions. is done.
- a shear melt-kneading method preferably an internal kneader or a twin-screw extruder, in which ring-opening treatment is performed under shear conditions.
- ring-opening treatment by the shear melt kneading method, while shearing the ethylene-(meth)acrylate copolymer containing an acid anhydride using a kneader, about 0.1 to 30 per 100 parts by weight of the copolymer. It is carried out by reacting with water, which is used in parts by weight, preferably about 1 to 20 parts by weight.
- a ring-opening catalyst can also be used to promote ring-opening.
- the ring-opening treatment can be performed without using a solvent, a small amount of solvent can also be used for the purpose of adjusting fluidity.
- a kneader that can be used for the ring-opening process
- a single screw extruder, a twin screw extruder, a kneader, a roll type kneader, a Banbury mixer, a Brabender, a reciprocating kneader (BUSS KNEADER), etc. can be used without limitation.
- a twin-screw extruder is used from the viewpoint of versatility.
- an acid catalyst it is possible to use either an acid catalyst or a base catalyst.
- Organic acids Mineral acids such as hydrochloric acid, nitric acid, sulfuric acid, and phosphoric acid; Heteropolyacids such as heteropolyacids and heteropolyacid salts; Inorganic bases, aliphatic or aromatic organic bases, fatty acid salts of alkali metals or alkaline earth metals, and the like can be used, and organic bases are preferably used.
- organic bases include 1,8-diazabicyclo[5.4.0]undecene-7 or 1,5-diazabicyclo[4.3.0]nonene-5 and salts thereof, amine compounds such as tertiary amines, and imidazole.
- the ring-opening catalyst is used in an amount of about 0.01 to 10 parts by weight, preferably about 0.1 to 5 parts by weight, per 100 parts by weight of the ethylene-(meth)acrylate copolymer containing the acid anhydride.
- the copolymerized dicarboxylic acid anhydride becomes a structure in which dicarboxylic acid compounds such as maleic acid, fumaric acid, itaconic acid, citraconic acid, mesaconic acid, and glutaconic acid are copolymerized, and copolymerized unsaturated
- An ethylene-(meth)acrylate elastomer is obtained in which the unsaturated dicarboxylic acid compound structure accounts for 20 to 99.9 mol % of the total amount of the dicarboxylic acid anhydride and its ring-opened dicarboxylic acid compound structure.
- the preferred ring-opening rate is about 70-98% after 1 day at 23°C.
- Patent Document 3 in Claim 1, the total amount of the unsaturated dicarboxylic acid and its acid anhydride in the ethylene-alkyl (meth)acrylate copolymer is said to be 0.1 to 5.0 mol%,
- the ring-opening products disclosed in the examples are only products with a ring-opening rate of 100%, and copolymers containing unsaturated dicarboxylic acids and their acid anhydrides as monomers are not disclosed. It is also different from the present invention in that the ring-opening treatment by hydrolysis is carried out by a solvent method in which the copolymer is dissolved in a solvent. Furthermore, what is disclosed in this document is only an intermediate for modification treatment, and the properties of a composition using this are not disclosed.
- aging treatment is preferably performed to improve the ring-opening rate.
- the aging temperature is about 0 to 100°C, and the aging time is appropriately set according to the aging temperature. For example, at a room temperature of 23°C, the aging time is set to one day or more, and if the aging temperature rises, the aging time can be shortened accordingly, but from the viewpoint of economy, aging at room temperature is adopted. be.
- ring-opening treated ethylene-(meth)acrylate elastomers from the viewpoint of obtaining a vulcanizate excellent in heat resistance, oil resistance and molding processability, 40 to 79.9 mol% of ethylene and 1 to 8 carbon atoms.
- Amine-based vulcanizing agents and organic peroxide cross-linking agents can be used as vulcanizing agents for ethylene-(meth)acrylate-based elastomers.
- Amine vulcanizing agents include hexamethylenediamine, hexamethylenediamine carbamate, N,N'-dicinnamylidene-1,6-hexanediamine, 4,4'-bis(aminocyclohexyl)methane, ethylenediamine, ethylenediaminecarbamate, and cyclohexanediamine.
- R 1 is a C 1 to C 20 linear or branched divalent aliphatic alkylene group, divalent alicyclic hydrocarbon group or divalent aromatic group
- R 2 is a group that can decompose under the action of a basic vulcanization accelerator to generate a diamine when formed into a carbamate structure, and is a C 1 to C 20 alkyl group, alkoxyl group, phenoxy group, haloalkyl group, olefin group , an aryl group or an aralkyl group, a fluorenyl-containing group, an S-containing group, a Si-containing group, an N-containing group or a P-containing group, wherein the S-containing group or N-containing group is an aromatic or alicyclic heterocyclic group
- Such a polyamine compound vulcanizing agent is used in a proportion of about 0.1 to 5 parts by weight, preferably about 0.5 to 2 parts by weight, per 100 parts by weight of the ethylene-(meth)acrylate elastomer. If the amount of the vulcanizing agent is less than this range, the vulcanization will be insufficient, resulting in a decrease in the mechanical properties of the vulcanizate and a decrease in the vulcanization speed. If the amount of the vulcanizing agent is more than this, the vulcanization proceeds excessively and the elasticity of the vulcanizate may decrease.
- the basic vulcanization accelerator, the thiuram-based cross-linking accelerator, and the thiourea-based cross-linking accelerator are added in an amount of about 0.5 to 5 parts by weight, preferably about 0.5 to 5 parts by weight, per 100 parts by weight of the ethylene-(meth)acrylate elastomer. It is desirable to use them together at a ratio of 3 parts by weight.
- Basic vulcanization accelerators include guanidine compounds, diazabicycloalkene compounds such as 1,8-diazabicyclo[5.4.0]undecene-7, 1,5-diazabicyclo[4.3.0]nonene-5, and organic acids thereof. Salts and inorganic acid salts are used, and 1,8-diazabicyclo[5.4.0]undecene-7[DBU] is preferably used from the viewpoint of higher addition effects.
- a mixture of 1,8-diazabicyclo[5.4.0]undecene-7 and silica can also be used, and in practice Vulcofac ACT55, a product of Safic Alcan, etc. is used.
- Examples of compounds that form organic acid salts or inorganic acid salts of diazabicycloalkene compounds include hydrochloric acid, sulfuric acid, carboxylic acid, sulfonic acid, and phenol.
- Examples of carboxylic acids include octylic acid, oleic acid, formic acid, orthophthalic acid and adipic acid, and examples of sulfonic acids include benzenesulfonic acid, toluenesulfonic acid, dodecylbenzenesulfonic acid and naphthalenesulfonic acid. These can be used alone or in combination of two or more.
- Guanidine compounds include guanidine and its substituted compounds such as aminoguanidine, 1,1,3,3-tetramethylguanidine, n-dodecylguanidine, methylolguanidine, dimethylolguanidine, 1-phenylguanidine and 1,3-diphenylguanidine. , 1,3-di-o-tolylguanidine, triphenylguanidine, 1-benzyl-2,3-dimethylguanidine, cyanoguanidine, etc. are used, as well as 1,6-guanidinohexane, guanylurea, biguanide, 1- o-Tolylbiguanide and the like are also used.
- thiuram-based compounds include tetramethylthiuram disulfide, and examples of thiourea-based compounds include N,N'-diphenylthiourea.
- organic peroxides include di-tert-butyl peroxide, dicumyl peroxide, di-tert-butylcumyl peroxide, 1,1-di(tert-butylperoxy)-3,3,5-trimethylcyclohexane, 2,5-dimethyl-2,5-di(tertiary-butylperoxy)hexane, 2,5-dimethyl-2,5-di(tertiary-butylperoxy)hexyne-3, 1,3-di(tertiary Butylperoxydiisopropyl)benzene, 2,5-dimethyl-2,5-di(benzoylperoxy)hexane, tert-butyl peroxybenzoate, tert-butylperoxyisopropyl carbonate, n-butyl-4,4-di( Tert-butylperoxy)valerate and the like are used in a proportion of about 0.2 to 10 parts
- the peroxide crosslinkable composition is preferably used in combination with a peroxide crosslinkable cross-linking aid comprising a polyfunctional unsaturated compound.
- polyfunctional unsaturated compounds include ethylene glycol di(meth)acrylate , propylene glycol di(meth)acrylate, triallyl(iso)cyanurate, trimethylolpropane tri(meth)acrylate, triallyl trimellitate, bismaleimide compounds (e.g., N,N′-m-phenylenebismaleimide, N,N ′-p-phenylenebismaleimide, N,N′-p-phenylene-(1-methyl)bismaleimide, N,N′-2,7-naphthalenebismaleimide, N,N′-m-phenylene-4-methyl Bismaleimide, N,N'-m-phenylene(4-ethyl)bismaleimide and the like are used, preferably N,N'-m-phenylenedimaleimide is used in
- ethylene-(meth)acrylate elastomers for ethylene-(meth)acrylate elastomers, reinforcing agents, fillers, processing aids, plasticizers, softeners, anti-aging agents, coloring agents, stabilizers, adhesion aids, release agents, conductive
- Various additives such as property imparting agents, thermal conductivity imparting agents, surface non-adhesive agents, tackifiers, softening agents, heat resistance improving agents, flame retardants, ultraviolet absorbers, oil resistance improving agents, anti-scorch agents, lubricants, etc. Agents are appropriately blended and used.
- reinforcing materials/fillers include silica such as basic silica and acidic silica; metal oxides such as magnesium oxide, zinc oxide, calcium oxide, titanium oxide and aluminum oxide; magnesium hydroxide, aluminum hydroxide and calcium hydroxide.
- metal hydroxides such as; magnesium carbonate, aluminum carbonate, calcium carbonate, metal carbonates such as barium carbonate; silicates such as magnesium silicate, calcium silicate, sodium silicate, aluminum silicate; aluminum sulfate, calcium sulfate , Sulfates such as barium sulfate; Synthetic hydrotalcite; Molybdenum disulfide, iron sulfide, metal sulfides such as copper sulfide; black, SRF carbon black, FEF carbon black, HAF carbon black, etc.), fluorinated carbon, calcium fluoride, coke, fine quartz powder, zinc oxide, talc, mica powder, wollastonite, carbon fiber, aramid fiber, various whiskers , glass fibers, organic reinforc
- antioxidants include phenyl- ⁇ -naphthylamine, phenyl- ⁇ -naphthylamine, p-(p-toluenesulfonylamido)-diphenylamine, 4,4′-( ⁇ , ⁇ -dimethylbenzyl)diphenylamine, N,N- Amine antioxidants such as diphenyl-p-phenylenediamine, N-isopropyl-N'-phenyl-p-phenylenediamine, butyraldehyde-aniline condensates; 2,6-di-tert-butylphenol, butylhydroxyanisole, 2, 6-di-tert-butyl- ⁇ -dimethylamino-p-cresol, octadecyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate, mono-, di- or tri-( ⁇ -methylbenzyl)phenol, etc.
- processing aids include higher fatty acids such as stearic acid, oleic acid, palmitic acid and lauric acid; higher fatty acid salts such as sodium stearate and zinc stearate; higher fatty acid amides such as stearamide and oleamide; Higher fatty acid esters such as ethyl acetate; petroleum waxes such as carnauba wax and ceresin wax; polyglycols such as ethylene glycol, glycerin and diethylene glycol; aliphatic hydrocarbons such as petrolatum and paraffin; polyethylene, phthalates, phosphates, rosin, (halogenated) dialkylamines, (halogenated) dialkylsulfones, surfactants and the like.
- higher fatty acids such as stearic acid, oleic acid, palmitic acid and lauric acid
- higher fatty acid salts such as sodium stearate and zinc stearate
- higher fatty acid amides such as
- plasticizers include epoxy resins, derivatives of phthalic acid and sebacic acid
- softeners include lubricating oils, process oils, coal tar, castor oil, and calcium stearate.
- the composition is prepared by adding a reinforcing agent, a stabilizer, a processing aid, etc. to an ethylene-(meth)acrylate elastomer using an open roll or internal kneader, and then adding a vulcanizing agent and a vulcanization accelerator. It is prepared by adding Vulcanization molding involves primary vulcanization at about 150-200°C for about 1-30 minutes, followed by oven vulcanization (secondary vulcanization) at about 150-200°C for about 1-16 hours if necessary. is done. For molding, known methods such as press molding, transfer molding, injection molding, and extrusion molding can be applied depending on the product.
- Polymerization Examples 1-16 Polymerization Example 1 uses the equipment of a high-pressure low-density polyethylene plant with a 5 L volume autoclave, and the monomer composition at the reactor inlet is ethylene 91.2 wt%, methyl acrylate 8.7 wt%, and maleic anhydride 0.11 wt%. was injected into the reactor. Using di-2-ethylhexylperoxydicarbonate as a reaction initiator, polymerization was carried out at a polymerization temperature of 165°C and a polymerization pressure of 165 MPa. Other production examples were also produced by adjusting the monomer composition, polymerization temperature, and polymerization pressure, and the copolymers shown in Table 1 were obtained. The copolymer composition in the produced terpolymer was calculated from the main monomer composition ratio (MA/E) described later and the MAH content.
- MA/E main monomer composition ratio
- Example 1 (1) Ternary copolymer obtained in Polymerization Example 5 100 parts by weight Ion-exchanged water 18 ⁇ 1,8-Diazabicyclo[5.4.0]-7-undecene ⁇ DBU ⁇ 1 Same as above (San-Apro product) Each of the above components was subjected to ring-opening treatment using Moriyama's 1L kneader (DS1-5MHB-E). First, the kneader was preheated to 80-90° C., the polymer and catalyst were charged, and mastication was carried out for 2 minutes at a rotation speed of 30 rpm.
- Moriyama's 1L kneader DS1-5MHB-E
- Cold resistance of the resulting ring-opened copolymer was measured using MFR (melt flow rate; conforming to JIS K-7210 corresponding to ISO 1133, 190°C, 2.16 kg) and DSC.
- MFR melt flow rate; conforming to JIS K-7210 corresponding to ISO 1133, 190°C, 2.16 kg
- DSC DSC6220 manufactured by SII was used, and the temperature was raised from -100°C to 100°C at a heating rate of 10°C per minute, and the temperature giving the differential peak of the DSC curve was defined as Tg.
- the composition (mol%) of the terpolymer was calculated from the main monomer composition ratio (MA/E) and the MAH content. ⁇ The main monomer composition ratio (mol%) was measured by IR.
- baselines were drawn at 4600 cm -1 and 3500 cm -1 and the height of the 4254 cm -1 peak derived from ethylene was measured.
- a one-point baseline was drawn at 3510 cm -1 and the 3457 cm -1 peak height derived from MA was measured.
- the peak ratio (A3457/A4254) was calculated, and the main monomer composition ratio (mol%) was calculated using a calibration curve of the MA content and the IR absorbance ratio prepared separately using NMR. ⁇ MAH content (mol%) was measured by IR.
- a one-point baseline was drawn at 4600 cm -1 and the 4254 cm -1 peak height derived from ethylene was measured.
- the MAH content was calculated from the peak ratio (A1855/A4254) using a calibration curve of the MAH content and the IR absorbance ratio prepared separately by a titration method.
- the ring-opening ratio of the ring-opening copolymer (23 ° C, 1 day and 2 days later (when measuring rubber physical properties)) is the sum of MAH content and maleic acid content (mol%) and MAH content (mol% ) was used and calculated by the following formula.
- Ring-opening rate (%) [1-(MAH content) / (MAH content + maleic acid content)] x 100
- the sum of MAH content and maleic acid content (mol%) was measured by neutralization titration method.
- 2 g of a sample was weighed out, dissolved in 80 ml of tetrahydrofuran, and stirred with a magnetic stirrer for 2 hours.
- potentiometric titration was performed with a 0.1 mol/L potassium hydroxide aqueous solution using a composite glass electrode non-aqueous titration electrode C-173 in an automatic potentiometric titrator AT-710M manufactured by Kyoto Electronics Industry Co., Ltd. From the equivalence point, the total content (mol%) of MAH and maleic acid was calculated.
- the MAH content (mol%) was determined by the IR method used when measuring the composition of the terpolymer.
- DBU-dodecane dihydrochloride 70% product; Safic-Alcan product Vulcofac ACT55
- 10 minutes of primary vulcanization and 4 hours of oven vulcanization (secondary vulcanization) at 175° C. to form vulcanized sheets and JIS-compliant compression set blocks.
- Mooney viscosity scorch JIS K 6300 conforming to ISO 289 Model: AM-4 (manufactured by Toyo Seiki) 125°C Normal state value: Complies with JIS K 6253 and JIS K 6251 corresponding to ISO 37 Heat aging resistance: Complies with JIS K 6257 corresponding to ISO 188 Evaluate hardness change at 175°C/70hrs Compression set: JIS K corresponding to ISO 815-1 6262 compliant 175°C/70hrs 25% compression Oil resistance: JIS K 6258 compliant 150°C/70hrs corresponding to ISO 1817 Evaluate swelling with test oil IRM 903
- Example 2 In Example 1, the same amount (100 parts by weight) of the terpolymer obtained in Polymerization Example 6 was used as the terpolymer in step (1).
- Example 3 In Example 2, 2 parts by weight of dimethylstearylamine (Furmin DM8098, Kao product) was used as the ring-opening catalyst in step (1).
- Example 4 In Example 1, the same amount (100 parts by weight) of the terpolymer obtained in Polymerization Example 3 was used as the terpolymer in step (1), and DBU-dodecane dihydrochloride was used as the ring-opening catalyst. (70% product; Vulcofac ACT55) was used at 3.6 parts by weight.
- Example 5 In Example 4, 2 parts by weight of DBU-octylate (U-CAT SA102, manufactured by San-Apro) was used as the ring-opening catalyst in step (1).
- DBU-octylate U-CAT SA102, manufactured by San-Apro
- Example 6 In Example 4, 0.8 parts by weight of triethylenediamine (DABCO, a product of Tokyo Chemical Industry) was used as the ring-opening catalyst in step (1).
- DABCO triethylenediamine
- Example 1 the terpolymer (MFR 40), which was not subjected to the ring-opening treatment of step (1), was vulcanized in step (2). properties could not be measured.
- Example 2 the terpolymer (MFR 9.6), which was not subjected to the ring-opening treatment of step (1), was vulcanized in step (2). properties could not be measured.
- Example 4 the terpolymer (MFR 10.3), which was not subjected to the ring-opening treatment of step (1), was vulcanized in step (2). properties could not be measured.
- Example 7 In Example 1, the same amount (100 parts by weight) of the terpolymer obtained in Polymerization Example 10 was used as the terpolymer in step (1), and DBU-dodecane dihydrochloride was used in step (2). was not used.
- Example 8 In Example 7, the same amount (100 parts by weight) of the terpolymer obtained in Polymerization Example 11 was used as the terpolymer in step (1).
- Example 9 In Example 7, the same amount (100 parts by weight) of the terpolymer obtained in Polymerization Example 12 was used as the terpolymer in step (1).
- Example 10 In Example 7, the same amount (100 parts by weight) of the terpolymer obtained in Polymerization Example 13 was used as the terpolymer in step (1).
- Example 11 In Example 7, the same amount (100 parts by weight) of the terpolymer obtained in Polymerization Example 14 was used as the terpolymer in step (1).
- Comparative example 4 In Example 7, the same amount (100 parts by weight) of the terpolymer obtained in Polymerization Example 1 was used as the terpolymer in step (1).
- Comparative example 5 In Example 7, the same amount (100 parts by weight) of the terpolymer obtained in Polymerization Example 2 was used as the terpolymer in step (1).
- Example 12 In Example 5, where DBU-octylate (Mw 296.4) was used as ring-opening catalyst, instead of the terpolymer of Polymerization Example 3 in step (1), the terpolymer of Polymerization Example 15 was used. The same amount (100 parts by weight) was used.
- Example 13 In Example 12, the same amount (100 parts by weight) of the terpolymer of Polymerization Example 16 was used instead of the terpolymer of Polymerization Example 15 in step (1).
- the copolymer was press-molded at a temperature of 100°C according to JIS K7151, which corresponds to ISO293, and rapidly cooled by cooling method C (60 ⁇ 30 K/min) to create a press sheet with a thickness of 6 mm. was cut into an appropriate width to prepare a terpolymer for supply. Next, this was continuously supplied to a twin-screw extruder and melt-kneaded. A liquid addition nozzle is attached to the midsection of the kneading zone of the twin-screw extruder, and a specified amount of ring-opening agent is continuously injected into the total 100 parts by weight of the copolymer components using a liquid addition device.
- the copolymer was ring-opened by continuing melt-kneading.
- the copolymer extruded in a strand from the twin-screw extruder was passed through a cooling water bath to obtain a ring-opening-treated copolymer.
- the denaturation temperature was 190° C.
- the screw speed was 300 rpm
- the amount of the terpolymer added was 11 kg/hr
- the amount of the ring-opening agent added was 0.66 kg/hr.
- Example 15 In Example 14, the same amount (100 parts by weight) of the terpolymer of Polymerization Example 8 was used instead of the terpolymer of Polymerization Example 7 in step (1).
- Example 16 100 parts by weight of the terpolymer obtained in Polymerization Example 9, 1 part by weight of ion-exchanged water, and 2 parts by weight of DBU-octylate as a ring-opening catalyst were used.
- a feed terpolymer was prepared in the same manner as in Example 14, and continuously charged into a twin-screw extruder together with a predetermined amount of ring-opening catalyst for melt-kneading.
- the ring-opening treatment conditions using a twin-screw extruder were as follows: denaturation temperature of 120°C, screw rotation speed of 300 rpm, modified copolymer discharge rate of 18 kg/hr, ring-opening catalyst input of 0.36 kg/hr, ion exchange The amount of water added was 0.18 kg/hr.
- Example 17 In Example 16, the ring-opening catalyst was changed to 1.5 parts by weight, and the ring-opening catalyst input amount was changed to 0.27 kg/hr.
- Example 18 In Example 16, the ring-opening catalyst in step (1) was changed to 1 part by weight, and the ring-opening catalyst input amount was changed to 0.18 kg/hr. 1.2 parts by weight of AC-6) and 2 parts by weight of DBU-dodecane dihydrochloride (70% grade) were additionally used.
- Example 19 In Example 18, the ring-opening catalyst was changed to 0.5 parts by weight, and the ring-opening catalyst input amount was changed to 0.09 kg/hr.
- Example 20 In Example 18, the ring-opening catalyst was 1 part by weight of 2-methylimidazole, the amount of ring-opening catalyst added was 0.18 kg/hr, and the amount of ion-exchanged water added was 3 parts by weight (the amount of ion-exchanged water added was 0.54 kg/hr. ) respectively.
- Example 21 In Example 18, the ring-opening catalyst was 0.5 parts by weight of 2-methylimidazole, the amount of ring-opening catalyst added was 0.09 kg/hr, and the amount of ion-exchanged water added was 1.5 parts by weight (the amount of ion-exchanged water added was 0.27 kg/hr. ) respectively.
- Example 22 Ternary copolymer obtained in Polymerization Example 11 100 parts by weight Ion-exchanged water 18 ⁇ DBU-octylate 2 ditto Each of the above components was subjected to ring-opening treatment under the same conditions as in Example 1 (1) using a 1 L kneader (DS1-5MHB-E manufactured by Moriyama), MFR: 12.6 dg / min, Tg: -32.0 ° C. A ring-opening modified copolymer was obtained. The dough temperature at the end of kneading was 98°C.
- Example 2 A ring-opening modified copolymer whose composition ratio after 30 days of modification is 29.2 (mol%) of methyl acrylate, 70.2 (mol%) of ethylene, 0.43 (mol%) of maleic acid, and 0.07 (mol%) of maleic anhydride.
- CHEMINOX AC-6 Hexamethylenediamine carbamate
- Example 23 In Example 22(2), an additional 2 parts by weight of DBU-dodecane dihydrochloride (70% product) was used.
- Example 24 In Example 22(2), 4 parts by weight of 1,3-di-o-tolylguanidine (Ouchi Shinko Kagaku Kogyo nokusera DT) was used.
- Example 25 In Example 22(2), 1.9 parts by weight of 4,4'-bis(aminocyclohexyl)methanecarbamate (CHEMINOX AC-9, manufactured by Unimatec) was used instead of hexamethylenediamine carbamate, and DBU-dodecane dihydrochloride ( 70% product) was used in an amount of 2 parts by weight.
- CHEMINOX AC-9 4,4'-bis(aminocyclohexyl)methanecarbamate
- Example 26 In Example 22(2), 2.6 parts by weight of N,N-dicinnamylidene-1,6-hexanediamine (Diak#3, product of Chemours) was used instead of hexamethylenediamine carbamate, and DBU-dodecane dihydrochloride ( 70% product) was used in an amount of 2 parts by weight.
- Diak#3, product of Chemours N,N-dicinnamylidene-1,6-hexanediamine
- DBU-dodecane dihydrochloride 70% product
- Example 27 In Example 22(2), 4 parts by weight of 1,6-bis[(9-fluorenylmethyl)carbamate]hexane was used in place of hexamethylenediamine carbamate, and DBU-dodecane dihydrochloride (70% product) was used at 2 parts by weight.
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Abstract
Description
特許文献1:エチレン、アクリル酸メチルまたはアクリル酸エチルおよび1,4-ブテンジオン酸モノアルキルエステルを単量体として含有するランダム共重合体が記載されている。かかる共重合体は、高圧で重合して製造されるが、1,4-ブテンジオン酸モノアルキルエステルの腐蝕性のため、耐蝕性の高圧設備が必要となる。
特許文献2:エチレン、アクリル酸エステルおよびマレイン酸無水物を単量体として含有する共重合体と第1級または第2級のポリアミンとからなるアミン架橋性ゴム組成物が記載されている。かかる組成物は、架橋反応速度が速すぎるためスコーチタイムが短く、ゴム部品等を成形することが難しいといった課題がある。
R2(SO2)m(CH2)nOCONHR1NHCOO(CH2)n(SO2)mR2
(ここで、R1はC1~C20の直鎖状または分岐状構造の2価の脂肪族アルキレン基、2価の脂環式炭化水素基または2価の芳香族基であり、R2は、カルバメート構造としたとき、塩基性加硫促進剤の作用で分解し、ジアミンを発生させ得る基であって、C1~C20のアルキル基、アルコキシル基、フェノキシ基、ハロアルキル基、オレフィン基、アリール基またはアラルキル基、フルオレニル含有基、S含有基、Si含有基、N含有基またはP含有基であり、S含有基またはN含有基は芳香族または脂環式の複素環式基であり、n:0、1または2であり、m:0または1である)で表わされるジウレタン化合物、好ましくは一般式 H2N(CH2)lNH2(l=4~6)で表わされるアルキレンジアミンのアミノ基を9-フルオレニルメチルクロロホーメート〔Fmoc〕でジ置換したジウレタン化合物、さらに好ましくはヘキサメチレンジアミン(l=6)のアミノ基を〔Fmoc〕でジ置換したジウレタン化合物〔HMDA-Fmoc〕
を用いることもできる。
重合例1は、容積5Lオートクレーブを有する高圧法低密度ポリエチレンプラントの設備を使用し、反応器入口におけるモノマー組成が、エチレン91.2wt%、アクリル酸メチル8.7wt%および無水マレイン酸0.11wt%となるように反応器に注入した。反応開始剤としてジ-2-エチルへキシルパーオキシジカーボネートを使用し、重合温度165℃、重合圧力165MPaの条件下で重合した。その他の製造例も、モノマー組成、重合温度、重合圧力を調整することにより製造し、表1の共重合体を得た。
なお、生成3元共重合体中の共重合組成は、後記主モノマー組成比(MA/E)とMAH含有量とから計算した。
(1) 重合例5で得られた3元共重合体 100重量部
イオン交換水 18 〃
1,8-ジアザビシクロ[5.4.0]-7-ウンデセン〔DBU〕 1 〃
(サンアプロ製品)
以上の各成分を、モリヤマ製1Lニーダー(DS1-5MHB-E)を用いて、開環処理を行った。
はじめに、混練機を80~90℃に予熱し、ポリマーおよび触媒を投入し、素練りを回転速度30rpmで2分間実施した。次に、イオン交換水を規定量投入し、回転速度30rpmで15分間混錬し、排出した。混練終了時の温度は92℃であった。さらに、排出された共重合体を2~3cmの小片に切断し、温度60℃で24時間の減圧乾燥を実施した。この時の圧力は、-0.1MPa(減圧乾燥器の圧力表示)であった。含水量の確認は、ケット水分計を用いて120℃/15minの条件で実施された。
ここで、3元共重合体の組成(mol%)は、主モノマー組成比(MA/E)とMAH含有量から計算された。
・主モノマー組成比(mol%)は、IRで測定された。はじめに、4600cm-1と3500cm-1でベースラインを引き、エチレン由来の4254cm-1ピークの高さを測定した。次に、3510cm-1で1点ベースラインを引き、MA由来の3457cm-1ピーク高さを測定した。さらに、ピーク比(A3457/A4254)を算出し、別途NMRを用いて作成したMA含有量とIR吸光度比の検量線を使用して、主モノマー組成比(mol%)を算出した。
・MAH含有量(mol%)は、IRで測定された。はじめに、4600cm-1で1点ベースラインを引き、エチレン由来の4254cm-1ピーク高さを測定した。次に、1875cm-1と1825cm-1でベースラインを引き、MAH由来の1855cm-1ピークの高さを測定した。さらに、別途作成された滴定法によるMAH含量とIR吸光度比の検量線を使ったピーク比(A1855/A4254)から、MAH含量を算出した。
また、開環共重合体の開環率(23℃、1日後および2日後(ゴム物性測定時))は、MAH含有量およびマレイン酸含有量の合計(mol%)及びMAH含有量(mol%)を用いて、下記の計算式で算出された。
開環率(%)=〔1-(MAH含量)/(MAH含量+マレイン酸含量)〕×100
MAH含有量およびマレイン酸含有量の合計(mol%)は、中和滴定法により測定された。はじめに、サンプルを2g量りとり、80mlのテトラヒドロフランに溶解し、マグネティックスターラで2時間撹拌した。次に、京都電子工業製電位差自動滴定装置AT-710Mにて、複合ガラス電極非水滴定用電極C-173を使用し、0.1mol/Lの水酸化カリウム水溶液で電位差滴定を実施した。当量点から、MAHおよびマレイン酸の合計の含量(mol%)を算出した。MAH含有量(mol%)は3元共重合体の組成測定時に使用されたIR法を用いた。
ステアリン酸 2 〃
アミン系老化防止剤(大内新興化学工業製品ノクラックCD) 2 〃
FEFカーボンブラック(東海カーボン製品シーストGS) 50 〃
リン酸ハーフエステル(東邦化学製品Phosphanol RL210) 1 〃
ステアリルアミン(花王製品ファーミン80) 1 〃
以上の各成分を、モリヤマ製1Lニーダー(DS1-5MHB-E)を用いて混練し、次いで8インチオープンロール(大竹機械工業製)を用いて、ヘキサメチレンジアミンカルバメート(ユニマテック製品CHEMINOX AC-6)1.2重量部およびDBU-ドデカン二塩酸(70%品;Safic-Alcan製品Vulcofac ACT55)2重量部を配合、混練してゴム物性評価用組成物を作製し、得られた混練組成物について、180℃、10分間の一次加硫および175℃、4時間のオーブン加硫(二次加硫)を行い、加硫シートおよびJIS準拠の圧縮永久歪用ブロックを成形した。
ムーニー粘度スコーチ:ISO 289に対応するJIS K 6300準拠
機種:AM-4(東洋精機製) 125℃
常態値:ISO 37に対応するJIS K 6253、JIS K 6251準拠
耐熱老化性:ISO 188に対応するJIS K 6257準拠
175℃/70hrs 硬度変化を評価
圧縮永久歪:ISO 815-1に対応するJIS K 6262準拠
175℃/70hrs 25%圧縮
耐油性:ISO 1817に対応するJIS K 6258準拠
150℃/70hrs 試験油IRM 903での膨潤を評価
実施例1において、工程(1)の3元共重合体として、重合例6で得られた3元共重合体が同量(100重量部)用いられた。
実施例2において、工程(1)の開環触媒としてジメチルステアリルアミン(花王製品ファーミンDM8098)が2重量部用いられた。
実施例1において、工程(1)の3元共重合体として、重合例3で得られた3元共重合体が同量(100重量部)用いられ、また開環触媒としてDBU-ドデカン二塩酸(70%品;Vulcofac ACT55)が3.6重量部用いられた。
実施例4において、工程(1)の開環触媒としてDBU-オクチル酸塩(サンアプロ製品U-CAT SA102)が2重量部用いられた。
実施例4において、工程(1)の開環触媒としてトリエチレンジアミン(東京化成製品DABCO)が0.8重量部用いられた。
実施例1において、工程(1)の開環処理を行わなかった3元共重合体(MFR 40)について工程(2)の加硫を行ったが、混練中スコーチして、加硫物の諸特性を測定することができなかった。
実施例2において、工程(1)の開環処理を行わなかった3元共重合体(MFR 9.6)について工程(2)の加硫を行ったが、混練中スコーチして、加硫物の諸特性を測定することができなかった。
実施例4において、工程(1)の開環処理を行わなかった3元共重合体(MFR 10.3)について工程(2)の加硫を行ったが、混練中スコーチして、加硫物の諸特性を測定することができなかった。
実施例1において、工程(1)の3元共重合体として重合例10で得られた3元共重合体が同量(100重量部)用いられ、また工程(2)においてDBU-ドデカン二塩酸が用いられなかった。
実施例7において、工程(1)の3元共重合体として重合例11で得られた3元共重合体が同量(100重量部)用いられた。
実施例7において、工程(1)の3元共重合体として、重合例12で得られた3元共重合体が同量(100重量部)用いられた。
実施例7において、工程(1)の3元共重合体として、重合例13で得られた3元共重合体が同量(100重量部)用いられた。
実施例7において、工程(1)の3元共重合体として、重合例14で得られた3元共重合体が同量(100重量部)用いられた。
実施例7において、工程(1)の3元共重合体として、重合例1で得られた3元共重合体が同量(100重量部)用いられた。
実施例7において、工程(1)の3元共重合体として、重合例2で得られた3元共重合体が同量(100重量部)用いられた。
開環触媒としてDBU-オクチル酸塩(Mw 296.4)が用いられた実施例5において、工程(1)の重合例3の3元共重合体の代りに、重合例15の3元共重合体が同量(100重量部)用いられた。
実施例12において、工程(1)の重合例15の3元共重合体の代りに、重合例16の3元共重合体が同量(100重量部)用いられた。
実施例12において、工程(1)の重合例15の3元共重合体の代りに、重合例7の3元共重合体が同量(100重量部)用いられ、またDBU-オクチル酸塩として、その33.8重量%水溶液6.04重量部が用いられた。さらに、1Lニーダーに代えて、東芝機械製二軸押出機TEM26SX(スクリュー径:φ26、L/D=64)が使用された。はじめに、共重合体をISO293に対応するJIS K7151に準拠し、温度100℃でプレス成形し、冷却方法C(60±30K/min)で急速冷却し、厚さ6mmのプレスシートを作成し、これを適当な幅に裁断し供給用3元共重合体を作成した。次に、これを二軸押出機に連続的に供給し、溶融混練した。二軸押出機の混練ゾーンの中腹部には液体添加ノズルが取り付けられており、共重合体成分の合計100重量部に対し規定量の開環剤が液体添加装置を用いて連続的に圧入され、さらに溶融混練を継続することによって共重合体が開環処理された。二軸押出機からストランド状に押し出された共重合体は、冷却水槽に通され、開環処理された共重合体が得られた。この時の変性温度は190℃、スクリュー回転数300rpm、3元共重合体の添加量が11kg/hrであり、開環剤の添加量が0.66kg/hrとなっている。
実施例14において、工程(1)の重合例7の3元共重合体の代わりに、重合例8の3元共重合体が同量(100重量部)用いられた。
実施例14において、重合例9で得られた3元共重合体100重量部、イオン交換水 1重量部および開環触媒としてのDBU-オクチル酸塩2重量部が用いられた。実施例14と同様の手順で、供給用3元共重合体を作成し、所定量の開環触媒と一緒に二軸押出機に連続的に投入し、溶融混錬した。二軸混練機の混練ゾーンの中腹部の液体添加ノズルから、共重合体成分の合計100重量部に対し規定量のイオン交換水を液体添加装置を用いて連続的に圧入し、さらに溶融混練を継続することによって共重合体を開環処理し、冷却を実施した。
実施例16において、開環触媒が1.5重量部、開環触媒投入量が0.27kg/hrにそれぞれ変更された。
実施例16において、工程(1)における開環触媒が1重量部、開環触媒投入量が0.18kg/hrにそれぞれ変更され、また工程(2)において、開環触媒としてヘキサメチレンジアミンカルバメート(CHEMINOX AC-6)1.2重量部およびDBU-ドデカン二塩酸(70%品)2重量部がさらに用いられた。
実施例18において、開環触媒が0.5重量部、開環触媒投入量が0.09kg/hrにそれぞれ変更された。
実施例18において、開環触媒が2-メチルイミダゾール 1重量部に、開環触媒投入量が0.18kg/hrに、イオン交換水添加量が3重量部(イオン交換水添加量は0.54Kg/hr)にそれぞれ変更された。
実施例18において、開環触媒が2-メチルイミダゾール 0.5重量部に、開環触媒投入量が0.09kg/hrに、イオン交換水添加量が1.5重量部(イオン交換水添加量は0.27Kg/hr)にそれぞれ変更された。
実施例18において、工程(1)の二軸押出機による開環処理を行わなかったところ、加硫性組成物の混練中スコーチが起こり、諸特性の測定ができなかった。
(1) 重合例11で得られた3元共重合体 100重量部
イオン交換水 18 〃
DBU-オクチル酸塩 2 〃
以上の各成分を、1Lニーダ(モリヤマ製DS1-5MHB-E)を用い、実施例1(1)と同様の条件下で開環処理を行い、MFR:12.6 dg/分、Tg:-32.0℃の開環変性共重合体を得た。なお、混練終了時生地温度は98℃であった。
1Lニーダー混練生地 156重量部
ヘキサメチレンジアミンカルバメート(CHEMINOX AC-6) 1.2 〃
を加えて、180℃、8分間の一次加硫および175℃、4時間のオーブン加硫を行った。
実施例22(2)において、さらにDBU-ドデカン二塩酸(70%品)2重量部が用いられた。
実施例22(2)において、さらに1,3-ジ-o-トリルグアニジン(大内新興化学工業製品ノクセラーDT)が4重量部用いられた。
実施例22(2)において、ヘキサメチレンジアミンカルバメートの代りに、4,4´-ビス(アミノシクロヘキシル)メタンカルバメート(ユニマテック製品CHEMINOX AC-9)が1.9重量部用いられ、さらにDBU-ドデカン二塩酸(70%品)が2重量部用いられた。
実施例22(2)において、ヘキサメチレンジアミンカルバメートの代りに、N,N-ジシンナミリデン-1,6-ヘキサンジアミン(ケマーズ社製品Diak#3)が2.6重量部用いられ、さらにDBU-ドデカン二塩酸(70%品)が2重量部用いられた。
実施例22(2)において、ヘキサメチレンジアミンカルバメートの代りに、1,6-ビス〔カルバミン酸(9-フルオレニルメチル)〕ヘキサンが4重量部用いられ、さらにDBU-ドデカン二塩酸(70%品)が2重量部用いられた。
実施例23~27において、開環処理共重合体の代りに、未処理共重合体がそれぞれ同量(100重量部)用いられた。
Claims (13)
- エチレン40~79.9モル%、炭素数1~8のアルキル基を有するアルキル(メタ)アクリレートおよび/または炭素数2~8のアルコキシアルキル基を有するアルコキシ(メタ)アクリレート20.0~50.0モル%、不飽和ジカルボン酸0.05~20.0モル%および不飽和ジカルボン酸無水物0.001~20.0モル%の割合で共重合された構造を有し、温度190℃、荷重2.16kgの条件下で測定されるメルトフローレートが0.01~100g/10分であるエチレン-(メタ)アクリレート系エラストマー。
- 不飽和ジカルボン酸無水物およびその開環処理物であるジカルボン酸構造の合計量に対する不飽和ジカルボン酸化合物構造の割合が20~99.9モル%である請求項1記載のエチレン-(メタ)アクリレート系エラストマー。
- アルキル(メタ)アクリレートがメチルアクリレートである請求項1記載のエチレン-(メタ)アクリレート系エラストマー。
- 不飽和ジカルボン酸がマレイン酸であり、不飽和ジカルボン酸無水物が無水マレイン酸である請求項1記載のエチレン-(メタ)アクリレート系エラストマー。
- エチレン、炭素数1~8のアルキル基を有するアルキル(メタ)アクリレートおよび/または炭素数2~8のアルコキシアルキル基を有するアルコキシ(メタ)アクリレートおよび不飽和ジカルボン酸無水物の共重合体の酸無水物の開環処理を行うことを特徴とするエチレン-(メタ)アクリレート系エラストマーの製造法。
- 開環処理が、せん断溶融混練法により行われる請求項5記載のエチレン-(メタ)アクリレート系エラストマーの製造法。
- せん断溶融混練法が密閉式混練機または二軸押出機を用いて行われる請求項6記載のエチレン-(メタ)アクリレート系エラストマーの製造法。
- 開環処理が、水を用いて行われる請求項5記載のエチレン-(メタ)アクリレート系エラストマーの製造法。
- 開環処理が、開環触媒を用いて行われる請求項5記載のエチレン-(メタ)アクリレート系エラストマーの製造法。
- 開環触媒が塩基性化合物または有機アミン化合物である請求項9記載のエチレン-(メタ)アクリレート系エラストマーの製造法。
- 開環処理後にエイジング処理が行われる請求項5記載のエチレン-(メタ)アクリレート系エラストマーの製造法。
- 請求項1記載のエチレン-(メタ)アクリレート系エラストマーに加硫剤を配合してなるエチレン-(メタ)アクリレート系エラストマー組成物。
- 請求項12記載のエチレン-(メタ)アクリレート系エラストマー組成物を加硫成形してなる加硫成形物。
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Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5049389A (ja) | 1973-08-09 | 1975-05-02 | ||
JPS60240749A (ja) | 1984-05-16 | 1985-11-29 | Showa Denko Kk | アミン架橋性ゴム組成物 |
JPS61272204A (ja) | 1985-05-28 | 1986-12-02 | Showa Denko Kk | 変性エチレン系共重合体の製造方法 |
JPH01156309A (ja) * | 1987-12-14 | 1989-06-19 | Showa Denko Kk | エチレン系共重合体の製造方法 |
JPH0825586A (ja) | 1994-07-20 | 1996-01-30 | Showa Denko Kk | 多層感熱接着フィルム及び該フィルムを用いる多層構造物 |
JP2003213234A (ja) * | 2002-01-18 | 2003-07-30 | Unitika Ltd | 合成紙用水性接着剤及び積層体 |
JP2010523735A (ja) * | 2007-03-30 | 2010-07-15 | エルジー・ケム・リミテッド | アルケン、アクリレートおよび不飽和有機酸を含む共重合体、およびその製造方法 |
JP2010235955A (ja) | 2008-01-30 | 2010-10-21 | Unimatec Co Ltd | ジウレタン化合物を含有するアクリルゴム組成物 |
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- 2022-03-18 CN CN202280022453.7A patent/CN116997580A/zh active Pending
- 2022-03-18 JP JP2022043304A patent/JP2022145653A/ja active Pending
- 2022-03-18 EP EP22771539.8A patent/EP4310109A1/en active Pending
Patent Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5049389A (ja) | 1973-08-09 | 1975-05-02 | ||
JPS60240749A (ja) | 1984-05-16 | 1985-11-29 | Showa Denko Kk | アミン架橋性ゴム組成物 |
JPS61272204A (ja) | 1985-05-28 | 1986-12-02 | Showa Denko Kk | 変性エチレン系共重合体の製造方法 |
JPH01156309A (ja) * | 1987-12-14 | 1989-06-19 | Showa Denko Kk | エチレン系共重合体の製造方法 |
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 |
JPH0825586A (ja) | 1994-07-20 | 1996-01-30 | Showa Denko Kk | 多層感熱接着フィルム及び該フィルムを用いる多層構造物 |
JP2003213234A (ja) * | 2002-01-18 | 2003-07-30 | Unitika Ltd | 合成紙用水性接着剤及び積層体 |
JP2010523735A (ja) * | 2007-03-30 | 2010-07-15 | エルジー・ケム・リミテッド | アルケン、アクリレートおよび不飽和有機酸を含む共重合体、およびその製造方法 |
JP2010235955A (ja) | 2008-01-30 | 2010-10-21 | Unimatec Co Ltd | ジウレタン化合物を含有するアクリルゴム組成物 |
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