JP6813031B2 - アクリルゴム、アクリルゴム組成物、アクリルゴム架橋物、及びアクリルゴムの製造方法 - Google Patents
アクリルゴム、アクリルゴム組成物、アクリルゴム架橋物、及びアクリルゴムの製造方法 Download PDFInfo
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- JP6813031B2 JP6813031B2 JP2018557969A JP2018557969A JP6813031B2 JP 6813031 B2 JP6813031 B2 JP 6813031B2 JP 2018557969 A JP2018557969 A JP 2018557969A JP 2018557969 A JP2018557969 A JP 2018557969A JP 6813031 B2 JP6813031 B2 JP 6813031B2
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- Prior art keywords
- acrylic rubber
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- unsubstituted
- acrylic
- molecular weight
- Prior art date
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- 229920000800 acrylic rubber Polymers 0.000 title claims description 212
- 229920000058 polyacrylate Polymers 0.000 title claims description 212
- 238000004519 manufacturing process Methods 0.000 title claims description 75
- 239000000203 mixture Substances 0.000 title claims description 47
- -1 acrylic ester Chemical class 0.000 claims description 112
- 239000000178 monomer Substances 0.000 claims description 110
- 238000004132 cross linking Methods 0.000 claims description 33
- 238000010526 radical polymerization reaction Methods 0.000 claims description 24
- 238000009826 distribution Methods 0.000 claims description 22
- 239000003431 cross linking reagent Substances 0.000 claims description 20
- 125000005396 acrylic acid ester group Chemical group 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 14
- 125000003107 substituted aryl group Chemical group 0.000 claims description 13
- 150000003498 tellurium compounds Chemical class 0.000 claims description 12
- 239000007870 radical polymerization initiator Substances 0.000 claims description 11
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 125000003700 epoxy group Chemical group 0.000 claims description 8
- 238000007720 emulsion polymerization reaction Methods 0.000 claims description 7
- 238000010557 suspension polymerization reaction Methods 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims 1
- 239000000470 constituent Substances 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 123
- 239000000047 product Substances 0.000 description 56
- 238000006116 polymerization reaction Methods 0.000 description 41
- 125000004432 carbon atom Chemical group C* 0.000 description 33
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- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 27
- 238000000034 method Methods 0.000 description 15
- 239000004014 plasticizer Substances 0.000 description 15
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- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 13
- 239000002253 acid Substances 0.000 description 13
- 239000003795 chemical substances by application Substances 0.000 description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 13
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 13
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 12
- 229920000642 polymer Polymers 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 11
- 150000003839 salts Chemical class 0.000 description 11
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- JPIIVHIVGGOMMV-UHFFFAOYSA-N ditellurium Chemical compound [Te]=[Te] JPIIVHIVGGOMMV-UHFFFAOYSA-N 0.000 description 10
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- 125000001424 substituent group Chemical group 0.000 description 10
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 9
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- 229910052751 metal Inorganic materials 0.000 description 9
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- 150000003254 radicals Chemical class 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 8
- 239000006229 carbon black Substances 0.000 description 8
- 229910052736 halogen Inorganic materials 0.000 description 8
- 150000002367 halogens Chemical class 0.000 description 8
- 229910052717 sulfur Inorganic materials 0.000 description 8
- 239000011593 sulfur Substances 0.000 description 8
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 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
- 125000003118 aryl group Chemical group 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 238000005227 gel permeation chromatography Methods 0.000 description 7
- 239000003112 inhibitor Substances 0.000 description 7
- 238000005259 measurement Methods 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- 239000003505 polymerization initiator Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 239000001993 wax Substances 0.000 description 7
- UTOVMEACOLCUCK-SNAWJCMRSA-N (e)-4-butoxy-4-oxobut-2-enoic acid Chemical compound CCCCOC(=O)\C=C\C(O)=O UTOVMEACOLCUCK-SNAWJCMRSA-N 0.000 description 6
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- 239000000945 filler Substances 0.000 description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 230000003712 anti-aging effect Effects 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 5
- 125000000753 cycloalkyl group Chemical group 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 5
- 229910052753 mercury Inorganic materials 0.000 description 5
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 5
- SFLRURCEBYIKSS-UHFFFAOYSA-N n-butyl-2-[[1-(butylamino)-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound CCCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCCC SFLRURCEBYIKSS-UHFFFAOYSA-N 0.000 description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 150000002978 peroxides Chemical class 0.000 description 5
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- WYGWHHGCAGTUCH-UHFFFAOYSA-N 2-[(2-cyano-4-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)C WYGWHHGCAGTUCH-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000005977 Ethylene Substances 0.000 description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- KYIKRXIYLAGAKQ-UHFFFAOYSA-N abcn Chemical compound C1CCCCC1(C#N)N=NC1(C#N)CCCCC1 KYIKRXIYLAGAKQ-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 230000003078 antioxidant effect Effects 0.000 description 4
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 4
- 238000013329 compounding Methods 0.000 description 4
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 229910002804 graphite Inorganic materials 0.000 description 4
- 239000010439 graphite Substances 0.000 description 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 4
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 239000000314 lubricant Substances 0.000 description 4
- 239000011591 potassium Substances 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- AVTLBBWTUPQRAY-UHFFFAOYSA-N 2-(2-cyanobutan-2-yldiazenyl)-2-methylbutanenitrile Chemical compound CCC(C)(C#N)N=NC(C)(CC)C#N AVTLBBWTUPQRAY-UHFFFAOYSA-N 0.000 description 3
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 3
- RFVNOJDQRGSOEL-UHFFFAOYSA-N 2-hydroxyethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCO RFVNOJDQRGSOEL-UHFFFAOYSA-N 0.000 description 3
- HFCUBKYHMMPGBY-UHFFFAOYSA-N 2-methoxyethyl prop-2-enoate Chemical compound COCCOC(=O)C=C HFCUBKYHMMPGBY-UHFFFAOYSA-N 0.000 description 3
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 3
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 239000004971 Cross linker Substances 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
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- 150000001336 alkenes Chemical class 0.000 description 3
- ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 3
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- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
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- XJELOQYISYPGDX-UHFFFAOYSA-N ethenyl 2-chloroacetate Chemical compound ClCC(=O)OC=C XJELOQYISYPGDX-UHFFFAOYSA-N 0.000 description 3
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- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 3
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- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
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- ZMQWRASVUXJXGM-VOTSOKGWSA-N (e)-4-cyclohexyloxy-4-oxobut-2-enoic acid Chemical compound OC(=O)\C=C\C(=O)OC1CCCCC1 ZMQWRASVUXJXGM-VOTSOKGWSA-N 0.000 description 2
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- 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
- WZRRRFSJFQTGGB-UHFFFAOYSA-N 1,3,5-triazinane-2,4,6-trithione Chemical compound S=C1NC(=S)NC(=S)N1 WZRRRFSJFQTGGB-UHFFFAOYSA-N 0.000 description 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 2
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- VFXXTYGQYWRHJP-UHFFFAOYSA-N 4,4'-azobis(4-cyanopentanoic acid) Chemical compound OC(=O)CCC(C)(C#N)N=NC(C)(CCC(O)=O)C#N VFXXTYGQYWRHJP-UHFFFAOYSA-N 0.000 description 2
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- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
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- 229940096992 potassium oleate Drugs 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- MLICVSDCCDDWMD-KVVVOXFISA-M potassium;(z)-octadec-9-enoate Chemical compound [K+].CCCCCCCC\C=C/CCCCCCCC([O-])=O MLICVSDCCDDWMD-KVVVOXFISA-M 0.000 description 1
- PYJBVGYZXWPIKK-UHFFFAOYSA-M potassium;tetradecanoate Chemical compound [K+].CCCCCCCCCCCCCC([O-])=O PYJBVGYZXWPIKK-UHFFFAOYSA-M 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- VMBJJCDVORDOCF-UHFFFAOYSA-N prop-2-enyl 2-chloroacetate Chemical compound ClCC(=O)OCC=C VMBJJCDVORDOCF-UHFFFAOYSA-N 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-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
- 238000000746 purification Methods 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 1
- 238000010057 rubber processing Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- BTURAGWYSMTVOW-UHFFFAOYSA-M sodium dodecanoate Chemical compound [Na+].CCCCCCCCCCCC([O-])=O BTURAGWYSMTVOW-UHFFFAOYSA-M 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 229940082004 sodium laurate Drugs 0.000 description 1
- 229940045870 sodium palmitate Drugs 0.000 description 1
- UNZSHUCNBUBSGW-IFNWOZJISA-M sodium;(9z,12z,15z)-octadeca-9,12,15-trienoate Chemical compound [Na+].CC\C=C/C\C=C/C\C=C/CCCCCCCC([O-])=O UNZSHUCNBUBSGW-IFNWOZJISA-M 0.000 description 1
- RLJSXMVTLMHXJS-UHFFFAOYSA-M sodium;4-decylbenzenesulfonate Chemical compound [Na+].CCCCCCCCCCC1=CC=C(S([O-])(=O)=O)C=C1 RLJSXMVTLMHXJS-UHFFFAOYSA-M 0.000 description 1
- GGXKEBACDBNFAF-UHFFFAOYSA-M sodium;hexadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCC([O-])=O GGXKEBACDBNFAF-UHFFFAOYSA-M 0.000 description 1
- 239000001587 sorbitan monostearate Substances 0.000 description 1
- 235000011076 sorbitan monostearate Nutrition 0.000 description 1
- 229940035048 sorbitan monostearate Drugs 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000006234 thermal black Substances 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 238000009849 vacuum degassing Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- BOXSVZNGTQTENJ-UHFFFAOYSA-L zinc dibutyldithiocarbamate Chemical compound [Zn+2].CCCCN(C([S-])=S)CCCC.CCCCN(C([S-])=S)CCCC BOXSVZNGTQTENJ-UHFFFAOYSA-L 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
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
- C08F220/00—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
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
-
- 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
- C08F4/00—Polymerisation catalysts
- C08F4/40—Redox systems
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or 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 of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polymerization Catalysts (AREA)
Description
本発明の実施形態に係るアクリルゴムは、アクリル酸エステル単量体単位と、架橋性単量体由来の構成単位とを有し、重量平均分子量が1,000,000〜4,000,000であり、オリゴマー量が5%以下のアクリルゴムである。
本実施形態に係るアクリルゴムの製造方法は、アクリル酸エステル単量体と側鎖に架橋性基を有する架橋性単量体とを、リビングラジカル重合開始剤の存在下で、乳化重合または懸濁重合により共重合(リビングラジカル重合)するものである。
本実施形態に係るアクリルゴム組成物は、アクリルゴムと架橋剤とを含有する。
本実施形態に係るアクリルゴム架橋物は、上述のアクリルゴム組成物を架橋してなる。
ゲル・パーミエーション・クロマトグラフィー(GPC)により、アクリルゴムの重量平均分子量(Mw)および数平均分子量(Mn)を測定した。GPCによる測定では、測定装置として東ソー社製の「HLC−8320」と、カラムとして東ソー社製の「supermultipore HZ−H」を直列に4本接続したものを用いた。また、GPCによる測定は、カラムサイズ:4.6mmID×15cm、溶離液:テトラヒドロフラン、カラム温度:40℃の条件で行った。また、GPCによる測定では、検出器として、示差屈折計(東ソー社製、RI−8320)を用いた。なお、重量平均分子量(Mw)、数平均分子量(Mn)は、ポリスチレン換算値として測定した。
上述の重量平均分子量(Mw)、数平均分子量(Mn)から、アクリルゴムの分子量分布(Mw/Mn)を算出した。
オリゴマー量は、アクリルゴム中のオリゴマーを含む分子量が100,000以下の組成物の含有割合(%)として測定した。
アクリルゴム組成物を、縦15cm、横15cm、深さ0.2cmの金型に入れ、プレス圧10MPaで加圧しながら、170℃で20分間プレスすることによりシート状のアクリルゴム架橋物を得た。次いで、得られたシート状のアクリルゴム架橋物を、ギヤー式オーブンに入れ、170℃で4時間熱処理を行った。熱処理後のシート状のアクリルゴム架橋物をダンベル型3号形で打ち抜いて試験片を作製した。次に、この試験片を用いて、JIS K6251に従い、引張強さ(MPa)および伸び(%)を、また、JIS K6253に従い、デュロメーター硬さ試験機(タイプA)を用いて硬さを、それぞれ測定した。
アクリルゴム架橋物を170℃、20分間のプレスによって成型、架橋して、直径29mm、厚さ12.5mmの円柱型試験片を作製し、さらに、170℃にて4時間加熱して二次架橋させた。JIS K6262に従い、上記にて得られた二次架橋後の試験片を25%圧縮させたまま、175℃の環境下で70時間放置した後、圧縮を解放して圧縮永久歪率を測定した。圧縮永久歪率の値が小さいほど、耐圧縮永久歪性に優れることを示す。
(合成例1)エチル2−メチル−2−フェニルテラニルプロピオネートの合成
窒素雰囲気下、300mLの三口フラスコ内で、金属テルル(Aldrich社製、以下同じ)11.48g(90mmol)をTHF86mlに懸濁させた。得られた懸濁液を撹拌しながら0℃に冷却した。懸濁液の撹拌と冷却を続けながら、この懸濁液に、フェニルリチウム(0.98Mシクロヘキサン−ジエチルエーテル溶液、関東化学社製、以下同じ)96.4ml(94.5mmol)を、10分かけて滴下した。滴下終了後、三口フラスコ内の内容物を、室温(25℃)で20分撹拌することで、金属テルルが完全に消失した反応溶液を得た。
1H−NMR(500MHz,CDCl3,TMS,δppm)1.18(t,J=7.2Hz、3H),1.73(s,6H),4.07(q,J=7.2Hz,2H),7.26−7.30(m,2H),7.39−7.43(m,1H),7.88−7.90(m,2H)。
フェニルリチウムの代わりにメチルリチウム(1.10Mジエチルエーテル溶液、関東化学社製、以下同じ)86.0ml(94.5mmol)を用いたこと、及びエチル−2−ブロモイソブチレートの代わりに臭化アリル(東京化成工業社製、以下同じ)11.4g(94.5mmol)を用いたこと以外は、合成例1と同様に反応・精製を行い、黄色油状物として3−メチルテラニル−1−プロペン6.55g(収率40%)を得た。
1H−NMR(500MHz,CDCl3,TMS,δppm)1.85(s,3H),3.31(d,J=8.5Hz,2H),4.80(d,J=9.0Hz,1H),4.85(d,J=17.0Hz,1H),5.90−5.99(m,1H)。
(製造例1)アクリルゴムAの製造
温度計、攪拌装置を備えた重合反応器に、水200部、ドデシル硫酸ナトリウム(東京化成工業社製)2部、アクリル酸エチル98.3部、フマル酸モノn−ブチル1.7部を仕込み、減圧脱気及び窒素置換を3度行って酸素を十分に除去した。その後、アゾビス(イソブチロニトリル)0.016部およびエチル−2−メチル−2−フェニルテラニルプロピオネート(合成例1)0.021部を加えて常圧下、温度50℃で懸濁重合を開始し、13時間反応させ、重合転化率89%に達するまで重合した。得られた懸濁重合液を塩化カルシウム溶液で凝固させ、水洗、乾燥してアクリルゴムAを得た。得られたアクリルゴムAの重量平均分子量(Mw)は1,303,000、分子量分布(Mw/Mn)は1.49であった。また、オリゴマー量(%)は1.0%であった。
アゾビス(イソブチロニトリル)0.016部の代わり0.0083部、エチル−2−メチル−2−フェニルテラニルプロピオネート0.021部の代わりに0.0089部を使用し、17時間反応させ、重合転化率83%に達するまで重合した以外は、製造例1と同様にして、アクリルゴムBを得た。得られたアクリルゴムBの重量平均分子量(Mw)は2,360,000、分子量分布(Mw/Mn)は2.08であった。また、オリゴマー量は0.9%であった。
アゾビス(イソブチロニトリル)0.016部の代わり0.0064部、エチル−2−メチル−2−フェニルテラニルプロピオネート0.021部の代わりに0.0070部を使用し、19時間反応させ、重合転化率89%に達するまで重合した以外は、製造例1と同様にして、アクリルゴムCを得た。得られたアクリルゴムCの重量平均分子量(Mw)は3,505,000、分子量分布(Mw/Mn)は2.54であった。また、オリゴマー量は1.6%であった。
アクリル酸エチル98.3部の代わりにアクリル酸エチル48.3部及びアクリル酸n−ブチル50部、アゾビス(イソブチロニトリル)0.016部の代わり0.0071部、エチル−2−メチル−2−フェニルテラニルプロピオネート0.021部の代わりに0.0070部を使用し、21時間反応させ、重合転化率80%に達するまで重合した以外は、製造例1と同様にして、アクリルゴムDを得た。得られたアクリルゴムDの重量平均分子量(Mw)は3,098,000、分子量分布(Mw/Mn)は2.46であった。また、オリゴマー量は1.2%であった。
アクリル酸エチル98.3部の代わりに98.5部、フマル酸モノn−ブチル1.7部の代わりにメタクリル酸グリシジル1.5部、アゾビス(イソブチロニトリル)0.016部の代わり0.0051部、エチル−2−メチル−2−フェニルテラニルプロピオネート0.021部の代わりに3−メチルテラニル−1−プロペン(合成例2)0.0051部を使用し、18時間反応させ、重合転化率78%に達するまで重合した以外は、製造例1と同様にして、アクリルゴムEを得た。得られたアクリルゴムEの重量平均分子量(Mw)は1,930,000、分子量分布(Mw/Mn)は1.61であった。また、オリゴマー量は2.2%であった。
アクリル酸エチル98.3部の代わりにアクリル酸エチル48.3部、アクリル酸n−ブチル30部、及びアクリル酸2−メトキシエチル20部、フマル酸モノn−ブチル1.7部の代わりにビニルクロロアセテート1.7部、アゾビス(イソブチロニトリル)0.016部の代わりに4,4‘−アゾビス(4−シアノバレリアン酸)0.0062部、エチル−2−メチル−2−フェニルテラニルプロピオネート0.021部の代わりに3−メチルテラニル−1−プロペン(合成例2)0.0020部とメタクリル酸0.029部を予め1時間室温で反応させたマクロ開始剤を使用し、20時間反応させ、重合転化率85%に達するまで重合した以外は、製造例1と同様にして、アクリルゴムFを得た。得られたアクリルゴムFの重量平均分子量(Mw)は2,682,000、分子量分布(Mw/Mn)は2.39であった。また、オリゴマー量は2.4%であった。
温度計、攪拌装置を備えた重合反応器に、水200部、ドデシル硫酸ナトリウム2部、アクリル酸エチル98.3部、フマル酸モノn−ブチル1.7部を仕込み、減圧脱気及び窒素置換を2度行って酸素を十分に除去した。その後、クメンハイドロパーオキサイド0.005部およびホルムアルデヒドスルホキシル酸ナトリウム0.002部を加えて常圧下、温度20℃で乳化重合を開始し、5時間反応させ、重合転化率95%に達するまで重合した。得られた懸濁重合液を製造例1と同様にして、アクリルゴムGを得た。得られたアクリルゴムGの重量平均分子量(Mw)は849,000、分子量分布(Mw/Mn)は3.18であった。また、オリゴマー量は6.8%であった。
アゾビス(イソブチロニトリル)0.016部の代わり0.035部、エチル−2−メチル−2−フェニルテラニルプロピオネート0.021部の代わりに0.045部を使用し、6時間反応させ、重合転化率81%に達するまで重合した以外は、製造例1と同様にして、アクリルゴムHを得た。得られたアクリルゴムHの重量平均分子量(Mw)は638,000、分子量分布(Mw/Mn)は1.29であった。また、オリゴマー量は0.6%であった。
アクリル酸エチル98.3部の代わりにアクリル酸エチル48.3部及びアクリル酸n−ブチル50部を使用した以外は、製造例7と同様にして、アクリルゴムIを得た。得られたアクリルゴムIの重量平均分子量(Mw)は1,145,000、分子量分布(Mw/Mn)は2.93であった。また、オリゴマー量は5.3%であった。
アクリル酸エチル98.3部の代わりに98.5部、フマル酸モノn−ブチル1.7部の代わりにメタクリル酸グリシジル1.5部を使用した以外は、製造例7と同様にして、アクリルゴムJを得た。得られたアクリルゴムJの重量平均分子量(Mw)は704,000、分子量分布(Mw/Mn)は2.38であった。また、オリゴマー量は6.1%であった。
アクリル酸エチル98.3部の代わりにアクリル酸エチル48.3部、アクリル酸n−ブチル30部及びアクリル酸2−メトキシエチル20部、フマル酸モノn−ブチル1.7部の代わりにビニルクロロアセテート1.7部を使用した以外は、製造例7と同様にして、アクリルゴムKを得た。得られたアクリルゴムKの重量平均分子量(Mw)は1,253,000、分子量分布(Mw/Mn)は3.15であった。また、オリゴマー量は8.4%であった。
(実施例1)
バンバリーミキサーを用いて、製造例1で得られたアクリルゴムA100部に、FEFカーボンブラック(商品名「シーストSO」、東海カーボン社製、充填剤、「シースト」は登録商標)50部、ステアリン酸2部、エステル系ワックス(商品名「グレッグG−8205」、大日本インキ化学工業社製、滑剤)1部、4,4'−ビス(α,α−ジメチルベンジル)ジフェニルアミン(商品名:ノクラックCD、大内新興化学工業社製、老化防止剤、「ノクラック」は登録商標)2部を添加して、80℃で5分間混合した。次いで、得られた混合物を50℃のロールに移して、ヘキサメチレンジアミンカルバメート(商品名:Diak#1、デュポンエラストマー社製、架橋剤)0.78部、および1,3−ジ−o−トリルグアニジン(商品名:ノクセラーDT、大内新興化学工業社製、架橋促進剤、「ノクセラー」は登録商標、以下同様)2部を配合して、混練することにより、架橋性ゴム組成物(アクリルゴム組成物)を得た。得られたアクリルゴム組成物を用いて、上述した方法により試験片(アクリルゴム架橋物)を得て、常態物性(引張強さ、伸び、硬さ)および圧縮永久歪率を測定し、評価を行った。その結果を表1Aに示す。
アクリルゴムAに代えて製造例2で得られたアクリルゴムBを使用した以外は、実施例1と同様にして、アクリルゴム組成物を調製し、アクリルゴム架橋物を得て、同様に測定、評価を行った。結果を表1Aに示す。
アクリルゴムAに代えて製造例3で得られたアクリルゴムCを使用した以外は、実施例1と同様にして、アクリルゴム組成物を調製し、アクリルゴム架橋物を得て、同様に測定、評価を行った。結果を表1Aに示す。
アクリルゴムAに代えて製造例4で得られたアクリルゴムDを使用し、FEFカーボンブラックの添加量を60部とし、ヘキサメチレンジアミンカルバメートの添加量を0.6部とした以外は、実施例1と同様にして、アクリルゴム組成物を調製し、アクリルゴム架橋物を得て、同様に測定、評価を行った。結果を表1Aに示す。
アクリルゴムAに代えて製造例5で得られたアクリルゴムEを使用し、ヘキサメチレンジアミンカルバメートおよび1,3−ジ−o−トリルグアニジンに代えて安息香酸アンモニウム(商品名:バルノックAB−S、大内新興化学工業社製、架橋剤、「バルノック」は登録商標)1.1部を使用し、エステル系ワックスを使用しなかった以外は、実施例1と同様にして、アクリルゴム組成物を調製し、アクリルゴム架橋物を得て、同様に測定、評価を行った。結果を表1Bに示す。
アクリルゴムAに代えて製造例6で得られたアクリルゴムFを使用し、FEFカーボンブラックの添加量を60部とし、ヘキサメチレンジアミンカルバメートおよび1,3−ジ−o−トリルグアニジンに代えて1,3,5−トリアジントリチオール(商品名:ZISNET−F、三洋化成社製、架橋剤、「ZISNET」は登録商標)0.5部、ジブチルジチオカルバミン酸亜鉛(商品名:ノクセラーBZ、大内新興化学工業社製、架橋促進剤)1.5部、ジエチルチオ尿素(商品名:ノクセラーEUR、大内新興化学工業社製、架橋促進剤)0.3部、およびN−(シクロヘキシルチオ)フタルイミド(商品名:リターダーCTP、大内新興化学工業社製、スコーチ防止剤)0.2部を使用した以外は、実施例1と同様にして、アクリルゴム組成物を調製し、アクリルゴム架橋物を得て、同様に測定、評価を行った。結果を表1Bに示す。
FEFカーボンブラックの添加量を80部とし、ポリエーテルエステル系可塑剤(商品名:アデカサイザーRS735、アデカ社製、可塑剤)20部をさらに使用した以外は、実施例4と同様にして、アクリルゴム組成物を調製し、アクリルゴム架橋物を得て、同様に測定、評価を行った。結果を表1Bに示す。
製造例1で得られたアクリルゴムAに代えて製造例7で得られたアクリルゴムGを使用した以外は、実施例1と同様にして、アクリルゴム組成物を調製し、アクリルゴム架橋物を得て、同様に測定、評価を行った。結果を表1Aに示す。
製造例1で得られたアクリルゴムAに代えて製造例8で得られたアクリルゴムHを使用した以外は、実施例1と同様にして、アクリルゴム組成物を調製し、アクリルゴム架橋物を得て、同様に測定、評価を行った。結果を表1Aに示す。
製造例4で得られたアクリルゴムDに代えて製造例9で得られたアクリルゴムIを使用した以外は、実施例4と同様にして、アクリルゴム組成物を調製し、アクリルゴム架橋物を得て、同様に測定、評価を行った。結果を表1Aに示す。
製造例5で得られたアクリルゴムEに代えて製造例10で得られたアクリルゴムJを使用した以外は、実施例5と同様にして、アクリルゴム組成物を調製し、アクリルゴム架橋物を得て、同様に測定、評価を行った。結果を表1Bに示す。
製造例6で得られたアクリルゴムFに代えて製造例11で得られたアクリルゴムKを使用した以外は、実施例6と同様にして、アクリルゴム組成物を調製し、アクリルゴム架橋物を得て、同様に測定、評価を行った。結果を表1Bに示す。
製造例4で得られたアクリルゴムDに代えて製造例9で得られたアクリルゴムIを使用した以外は、実施例7と同様にして、アクリルゴム組成物を調製し、アクリルゴム架橋物を得て、同様に測定、評価を行った。結果を表1Bに示す。
Claims (9)
- アクリル酸エステル単量体単位と、架橋性単量体由来の構成単位とを有し、
重量平均分子量が1,000,000〜4,000,000であり、
分子量が100,000以下の組成物の含有割合が5%以下であり、
分子量分布が1.3〜3.0であるアクリルゴム。 - 前記架橋性単量体由来の構成単位が、側鎖にエポキシ基、ハロゲン基、およびカルボキシル基のいずれか1種または2種以上の架橋性基を有する請求項1に記載のアクリルゴム。
- 請求項1または2に記載のアクリルゴムと架橋剤とを含有するアクリルゴム組成物。
- 請求項3に記載のアクリルゴム組成物を架橋してなるアクリルゴム架橋物。
- アクリル酸エステル単量体と架橋性基を有する架橋性単量体とを、リビングラジカル重合開始剤の存在下で、乳化重合または懸濁重合により共重合するアクリルゴムの製造方法。
- 前記リビングラジカル重合開始剤が有機テルル化合物である請求項5に記載のアクリルゴムの製造方法。
- 前記有機テルル化合物が、下記一般式(1)で表される請求項6に記載のアクリルゴムの製造方法。
- さらに、ラジカル発生剤または下記一般式(2)で表される化合物の存在下で、前記乳化重合または前記懸濁重合を行う請求項5乃至7のいずれか1項に記載のアクリルゴムの製造方法。
- 前記架橋性基を有する架橋性単量体が、エポキシ基、ハロゲン基、およびカルボキシル基のいずれか1種または2種以上の架橋性基を有する架橋性単量体である請求項5乃至8のいずれか1項に記載のアクリルゴムの製造方法。
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