WO2023021832A1 - 架橋性アクリルゴム組成物 - Google Patents
架橋性アクリルゴム組成物 Download PDFInfo
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- WO2023021832A1 WO2023021832A1 PCT/JP2022/024281 JP2022024281W WO2023021832A1 WO 2023021832 A1 WO2023021832 A1 WO 2023021832A1 JP 2022024281 W JP2022024281 W JP 2022024281W WO 2023021832 A1 WO2023021832 A1 WO 2023021832A1
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- WIPO (PCT)
- Prior art keywords
- acrylic rubber
- group
- weight
- meth
- acrylate
- Prior art date
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- 229920000800 acrylic rubber Polymers 0.000 title claims abstract description 192
- 229920000058 polyacrylate Polymers 0.000 title claims abstract description 192
- 239000000203 mixture Substances 0.000 title claims abstract description 56
- 238000004132 cross linking Methods 0.000 claims abstract description 34
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 31
- 229950000688 phenothiazine Drugs 0.000 claims abstract description 23
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims abstract description 22
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims abstract description 19
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 18
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 15
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 11
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 6
- 239000000178 monomer Substances 0.000 claims description 70
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 60
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 37
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical group CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 36
- 150000007934 α,β-unsaturated carboxylic acids Chemical class 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 5
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 3
- 230000015556 catabolic process Effects 0.000 abstract description 5
- 238000006731 degradation reaction Methods 0.000 abstract description 5
- 125000002252 acyl group Chemical group 0.000 abstract description 3
- -1 bismaleimide compound Chemical class 0.000 description 64
- 238000012360 testing method Methods 0.000 description 58
- 230000032683 aging Effects 0.000 description 46
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
- 230000000052 comparative effect Effects 0.000 description 36
- 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 34
- 230000008859 change Effects 0.000 description 33
- 239000003795 chemical substances by application Substances 0.000 description 31
- 230000006866 deterioration Effects 0.000 description 29
- 230000003712 anti-aging effect Effects 0.000 description 24
- 229920001971 elastomer Polymers 0.000 description 24
- 239000000047 product Substances 0.000 description 24
- 239000005060 rubber Substances 0.000 description 23
- 238000004519 manufacturing process Methods 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 18
- 238000000034 method Methods 0.000 description 18
- 239000002253 acid Substances 0.000 description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 230000003647 oxidation Effects 0.000 description 11
- 238000007254 oxidation reaction Methods 0.000 description 11
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 11
- 230000000704 physical effect Effects 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 241001441571 Hiodontidae Species 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000013078 crystal Substances 0.000 description 8
- 229910001873 dinitrogen Inorganic materials 0.000 description 8
- 239000004816 latex Substances 0.000 description 8
- 229920000126 latex Polymers 0.000 description 8
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000005977 Ethylene Substances 0.000 description 6
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 239000006229 carbon black Substances 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- 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 5
- 239000000470 constituent Substances 0.000 description 5
- 229920001198 elastomeric copolymer Polymers 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 4
- 230000015271 coagulation Effects 0.000 description 4
- 238000005345 coagulation Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 230000001590 oxidative effect Effects 0.000 description 4
- 125000004434 sulfur atom Chemical group 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- 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 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 235000021355 Stearic acid Nutrition 0.000 description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 238000007334 copolymerization reaction Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- QOSATHPSBFQAML-UHFFFAOYSA-N hydrogen peroxide;hydrate Chemical compound O.OO QOSATHPSBFQAML-UHFFFAOYSA-N 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
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- 229910052717 sulfur Inorganic materials 0.000 description 3
- 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
- OWRCNXZUPFZXOS-UHFFFAOYSA-N 1,3-diphenylguanidine Chemical compound C=1C=CC=CC=1NC(=N)NC1=CC=CC=C1 OWRCNXZUPFZXOS-UHFFFAOYSA-N 0.000 description 2
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- 125000004921 3-methyl-3-pentyl group Chemical group CC(CC)(CC)* 0.000 description 2
- UJAWGGOCYUPCPS-UHFFFAOYSA-N 4-(2-phenylpropan-2-yl)-n-[4-(2-phenylpropan-2-yl)phenyl]aniline Chemical compound C=1C=C(NC=2C=CC(=CC=2)C(C)(C)C=2C=CC=CC=2)C=CC=1C(C)(C)C1=CC=CC=C1 UJAWGGOCYUPCPS-UHFFFAOYSA-N 0.000 description 2
- XXSCONYSQQLHTH-UHFFFAOYSA-N 9h-fluoren-9-ylmethanol Chemical compound C1=CC=C2C(CO)C3=CC=CC=C3C2=C1 XXSCONYSQQLHTH-UHFFFAOYSA-N 0.000 description 2
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- 229910019142 PO4 Inorganic materials 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
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- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
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- 125000003545 alkoxy group Chemical group 0.000 description 2
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
- AYJRCSIUFZENHW-UHFFFAOYSA-L barium carbonate Chemical compound [Ba+2].[O-]C([O-])=O AYJRCSIUFZENHW-UHFFFAOYSA-L 0.000 description 2
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- 125000004093 cyano group Chemical group *C#N 0.000 description 2
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- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 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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- HRKQOINLCJTGBK-UHFFFAOYSA-L dioxidosulfate(2-) Chemical compound [O-]S[O-] HRKQOINLCJTGBK-UHFFFAOYSA-L 0.000 description 2
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- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
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- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
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- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- TXEYQDLBPFQVAA-UHFFFAOYSA-N tetrafluoromethane Chemical compound FC(F)(F)F TXEYQDLBPFQVAA-UHFFFAOYSA-N 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
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- 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
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- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
- C07D279/14—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems
- C07D279/18—[b, e]-condensed with two six-membered rings
- C07D279/34—[b, e]-condensed with two six-membered rings with hetero atoms directly attached to the ring sulfur atom
-
- 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
-
- 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
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/45—Heterocyclic compounds having sulfur in the ring
- C08K5/46—Heterocyclic compounds having sulfur in the ring with oxygen or nitrogen in the ring
-
- 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
Definitions
- the present invention relates to a crosslinkable acrylic rubber composition. More particularly, it relates to a crosslinkable acrylic rubber composition capable of minimizing deterioration in mechanical properties of a crosslinked product due to thermal oxidative deterioration.
- the spread of vehicles equipped with a turbocharger system aimed at improving engine fuel efficiency is progressing. Since the air that is led from the turbocharger to the intercooler and the engine is at high temperature and pressure, high heat resistance is required for the rubber hose material that transports this air.
- Phenol-based anti-aging agents and amine-based anti-aging agents are used as representative anti-aging agents for rubber members.
- amine-based anti-aging agents are used for rubber members that are used in higher temperature environments.
- amine-based antioxidants typified by 4,4'-bis( ⁇ , ⁇ -dimethylbenzyl)diphenylamine are used as antioxidants (Patent Documents 1 to 4).
- Patent Document 5 describes that phenothiazine-based antioxidants are effective as antioxidants for rubber materials.
- Patent Document 5 describes (A) a diene-based rubber, (B) a bismaleimide compound and (C) the following as rubber materials that are excellent in vulcanization properties, mechanical properties and heat aging properties and are particularly suitable for use as anti-vibration rubbers. Those containing phenothiazine compounds are described.
- R 1 , R 2 hydrogen atom, C 1 to C 8 alkyl group optionally substituted with an aromatic ring, alkoxy group, Halogen atom, cyano group
- R3 hydrogen atom, C1 - C6 chain or cyclic alkyl group, vinyl group, aromatic group m, n: 0-2
- a phenothiazine compound in which the sulfur atom at the 5-position is —SO 2 — is also known, and is described in Patent Document 6, for example.
- Patent Document 6 describes a condensed heterocyclic compound represented by the following general formula and an organic material composition containing the same, which is suitable for organic materials such as polymers susceptible to oxidative, thermal or light-induced degradation. On the other hand, it is said that it is possible to impart high processing stability, heat resistance, and long life.
- Non-Patent Documents 1 and 2 exemplify anti-aging agents Nocrack G-1 (Ouchi Shinko Kagaku Kogyo Co., Ltd.) and APMA (Seiko Kagaku Kogyo Co., Ltd.) having a polymerizable unsaturated group.
- Patent Document 10 a method of cross-linking acrylic rubber in the presence of 4-aminodiphenylamine is known (Patent Document 10), but there is concern that 4-aminodiphenylamine somewhat inhibits polyamine cross-linking in this method.
- any of the methods of improving the heat resistance of the raw rubber itself, improving the performance of various anti-aging agents, and chemically bonding the anti-aging component to the raw rubber fully satisfies the recent heat resistance requirements. It is not possible.
- JP-A-11-21411 WO 2011/58918 A1 JP 2010-254579 A WO 2006/001299 A1 Japanese Unexamined Patent Application Publication No. 2015-227402
- WO 2011/093443 A1 JP 2009-209268
- JP-A-4-264106 JP-A-5-230132 WO 2020/158132 A1 JP-A-2009-036960
- JP-A-2010-235955 Japanese Patent Application Laid-Open No. 2020-111552
- the present inventors have improved the heat resistance of acrylic rubber by using a crosslinkable acrylic rubber composition comprising an acrylic rubber containing a carbamic acid ether group and a carboxyl group, a phenothiazine anti-aging agent, and a crosslinking accelerator.
- a crosslinkable acrylic rubber composition comprising an acrylic rubber containing a carbamic acid ether group and a carboxyl group, a phenothiazine anti-aging agent, and a crosslinking accelerator.
- the object of the present invention is (A) an acrylic rubber containing a carbamate group and a carboxyl group, (B) a phenothiazine-based antioxidant represented by the following general formula [I]
- R 3 is a hydrogen atom, a monovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, or the following general formula (here, R 4 is a monovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms) and R 5 is an aralkyl group having 7 to 20 carbon atoms]
- the following diagram schematically shows an example of the cross-linking reaction of the acrylic rubber constituting the acrylic rubber composition according to the present invention.
- Fmoc 9-fluorenylmethyloxycarbonyl group
- the carbamic ester group is decomposed by the action of heat and the nitrogen-containing basic organic compound to liberate the amino group, and then the active site derived from the ⁇ , ⁇ -unsaturated carboxylic acid monomer. react to form complementary crosslinked structures.
- Such a unique crosslinked structure has the effect of suppressing significant softening deterioration in the initial stage of thermal oxidation deterioration of the crosslinked acrylic rubber.
- the phenothiazine-based anti-aging agent that constitutes the composition of the present invention has the effect of suppressing significant curing deterioration in the latter stage of thermooxidative deterioration of the acrylic rubber crosslinked product having the unique crosslinked structure shown above.
- crosslinkable composition it is possible to crosslink without adding an aromatic or aliphatic polyamine crosslinker. Incidental effects can also be expected, such as eliminating the risk of poor dispersion.
- Patent Document 11 a (meth)acrylate copolymer containing a carbamate group is described in Patent Document 11 and Non-Patent Documents 3 and 4, and furthermore, a dicarbamate compound can be used to crosslink a carboxyl group-containing acrylic rubber. is described in US Pat. However, nothing is taught or suggested that a crosslinked acrylic rubber having a unique crosslinked structure can be obtained by using these in combination.
- the phenothiazine-based anti-aging agent described in Patent Document 6 is very effective in suppressing curing deterioration in the latter stage of thermal oxidation deterioration of acrylic rubber crosslinked products, but softening deterioration progresses throughout the thermal oxidation deterioration process, resulting in mechanical strength deterioration. can be a challenge.
- the crosslinkable acrylic rubber composition of the present invention is (A) an acrylic rubber containing a carbamate group and a carboxyl group, (B) a phenothiazine-based antioxidant represented by the following general formula [I] [Here, R 3 is a hydrogen atom, a monovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, or the following general formula (here, R 4 is a monovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms) and R 5 is an aralkyl group having 7 to 20 carbon atoms] and (C) Consists of a cross-linking accelerator.
- R 3 is a hydrogen atom, a monovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, or the following general formula (here, R 4 is a monovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms)
- Embodiment (A-1) 90 to 99.8% by weight of alkyl (meth)acrylate and/or alkoxyalkyl (meth)acrylate monomers, 0.1 to 5% by weight of ⁇ , ⁇ -unsaturated carboxylic acid monomers and general formula
- R 1 is a hydrogen atom or a methyl group
- R 2 is a divalent aliphatic hydrocarbon group having 1 to 10 carbon atoms.
- (A-1) composed of a single acrylic rubber contains 99.8 to 90% by weight, preferably 99 to 90% by weight, of an alkyl (meth)acrylate monomer and/or an alkoxyalkyl (meth)acrylate monomer, ⁇ , ⁇ -unsaturated carboxylic acid monomer is 0.1 to 5% by weight, preferably 0.5 to 5% by weight; carbamate group-containing (meth)acrylate monomer is 0.1 to 5% by weight, preferably 0.5 to 5% by weight; Those copolymerized with the comonomer ratio are used.
- w CA Weight fraction of ⁇ , ⁇ -unsaturated carboxylic acid monomer in acrylic rubber Composition
- M CA g/mol
- w NH2 Weight fraction composition of carbamate group-containing (meth)acrylate monomer in acrylic rubber
- M NH2 g/mol
- the acrylic rubber of embodiment (A-1) other than the above includes, for example, ethylene, methyl acrylate, a carbamate group-containing (meth)acrylate monomer and an ⁇ , ⁇ -unsaturated carboxylic acid monomer as main constituents. or an elastomeric copolymer whose main constituents are ethylene, vinyl acetate, carbamate group-containing (meth)acrylate monomers and ⁇ , ⁇ -unsaturated carboxylic acid monomers, etc. can be used.
- Acrylic rubber (i) used in embodiment (A-2) comprising a mixture of acrylic rubbers contains 99.9 to 90% by weight of alkyl (meth)acrylate monomers and/or alkoxyalkyl (meth)acrylate monomers, preferably is 99.5 to 95% by weight, and a carbamate group-containing (meth)acrylate monomer is 0.1 to 10% by weight, preferably 0.5 to 5% by weight.
- the acrylic rubber (ii) contains 99.9 to 90% by weight, preferably 99.5 to 95% by weight, of an alkyl (meth)acrylate monomer and/or an alkoxyalkyl (meth)acrylate monomer, preferably 99.5 to 95% by weight, an ⁇ , ⁇ -unsaturated carboxylic acid Comonomers obtained by copolymerizing acid monomers at a comonomer ratio of 0.1 to 10% by weight, preferably 0.5 to 5% by weight, are used.
- the mixing ratio of the acrylic rubber (i) and the acrylic rubber (ii) is determined by considering the stoichiometric amount of the active site of the carbomic acid ester group and the ⁇ , ⁇ -unsaturated carboxylic acid monomer contained in the mixture. 90 to 10% by weight and 10 to 90% by weight, respectively.
- These ratios can be appropriately adjusted in consideration of factors such as the speed of crosslinking and various physical properties of the crosslinked product.
- the acrylic rubber mixture (A-2) can be easily prepared by mixing acrylic rubber (i) and acrylic rubber (ii) using an open roll, kneader, Banbury mixer, or the like.
- the desired acrylic rubber mixture can be prepared by mixing an aqueous latex of acrylic rubber (i) and an aqueous latex of acrylic rubber (ii) in an arbitrary ratio, followed by coagulation with an aqueous electrolyte solution and drying.
- acrylic rubber (i) other than the above examples include elastomeric copolymers containing ethylene, methyl acrylate and carbamic acid ester group-containing (meth)acrylate monomers as main constituents, or ethylene, vinyl acetate and carbamic acid esters.
- An elastomeric copolymer or the like containing a group-containing (meth)acrylate monomer as a main component can be used.
- acrylic rubber (ii) other than the above examples include elastomeric copolymers containing ethylene, methyl acrylate and ⁇ , ⁇ -unsaturated carboxylic acid monomers as main constituents, or ethylene, vinyl acetate and ⁇ , ⁇ - An elastomeric copolymer or the like containing an unsaturated carboxylic acid monomer as a main component can be used.
- the monomers constituting the single acrylic rubber of embodiment (A-1) and the acrylic rubbers (i) and (ii) of embodiment (A-2) are as follows.
- Alkyl (meth)acrylate monomers and/or alkoxyalkyl (meth)acrylates which are monomer units of the acrylic rubber of embodiment (A-1) and the acrylic rubber of embodiment (A-2) (i) and (ii)
- monomers include alkyl (meth)acrylates having alkyl groups of 1 to 8 carbon atoms, aralkyl (meth)acrylates having aralkyl groups of 7 to 20 carbon atoms, and alkoxy having alkoxyalkyl groups of 2 to 8 carbon atoms. At least one (meth)acrylate selected from alkyl (meth)acrylates is used.
- 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, cyclohexyl (meth)acrylate and the like are used.
- Preferred is ethyl acrylate or a monomer mixture containing it.
- Benzyl (meth)acrylate for example, is used as the aralkyl (meth)acrylate.
- 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.
- the following polymerizable components may optionally be used as secondary components.
- Unsaturated monomers can be used.
- polymerizable unsaturated monomers examples include styrene, ⁇ -methylstyrene, 3-methylstyrene, 4-methylstyrene, 1-vinylnaphthalene, 2-vinylnaphthalene, acrylonitrile, methacrylonitrile, acrylic acid amide, and vinyl acetate. , methyl vinyl ether, ethyl vinyl ether, ethylene, propylene, piperylene, butadiene, isoprene, chloroprene, cyclopentadiene, vinyl chloride, vinylidene chloride and the like.
- the carbamate group-containing (meth)acrylate monomer represented by the general formula [III] is converted to isocyanatoalkyl acrylate or isocyanatoalkyl (meth)acrylate and 9-fluorenylmethanol in the presence of a urethanization reaction catalyst. can be easily produced by reacting
- an organic tin compound an organic titanium compound, an organic zirconium compound, an organic bismuth compound, or the like can be used.
- organic tin compounds examples include dibutyltin dilaurate, tin bis(2-ethylhexanoate), and dibutyltin (2,4-pentanedionate).
- organic titanium compounds examples include titanium diisopropoxybis(ethylacetoacetate).
- organic zirconium compounds examples include zirconium dibutoxybis(ethyl acetate) and zirconium tetra(acetyl acetate).
- organic bismuth compounds examples include bismuth tris (neodecanoate).
- the reaction is carried out in organic solvents such as benzene, toluene, dioxane, methyl ethyl ketone, and cyclohexane at a temperature of 40-80°C.
- organic solvents such as benzene, toluene, dioxane, methyl ethyl ketone, and cyclohexane at a temperature of 40-80°C.
- the ⁇ , ⁇ -unsaturated carboxylic acid monomer which is the monomer unit of the acrylic rubber of embodiment (A-1) and the acrylic rubber (ii) of embodiment (A-2), includes monobasic acid ⁇ , ⁇ - Unsaturated carboxylic acid, dibasic ⁇ , ⁇ -unsaturated carboxylic acid or dibasic ⁇ , ⁇ -unsaturated carboxylic acid monoalkyl ester, preferably dibasic ⁇ , ⁇ -unsaturated carboxylic acid monoalkyl Esters are used.
- Examples of monobasic ⁇ , ⁇ -unsaturated carboxylic acids include acrylic acid and methacrylic acid.
- dibasic ⁇ , ⁇ -unsaturated carboxylic acids include maleic acid, maleic anhydride, fumaric acid, itaconic acid, and citraconic acid.
- dibasic acid ⁇ , ⁇ -unsaturated carboxylic acid monoalkyl esters include monoalkyl esters of maleic acid, fumaric acid, itaconic acid, and citraconic acid. Specific examples include monomethyl maleate, monoethyl maleate, mono-n-propyl maleate, mono-isopropyl maleate, mono-n-butyl maleate, mono-isobutyl maleate, mono-n-hexyl maleate, monocyclohexyl maleate, fumar monomethyl fumarate, monoethyl fumarate, mono-n-propyl fumarate, mono-isopropyl fumarate, mono-n-butyl fumarate, mono-isobutyl fumarate, mono-n-hexyl fumarate, mono-cyclohexyl fumarate and the like.
- the acrylic rubber of embodiment (A-1) and the acrylic rubbers (i) and (ii) of embodiment (A-2) are produced by a general acrylic rubber polymerization method.
- the copolymerization reaction can be carried out by any method such as emulsion polymerization, suspension polymerization, solution polymerization, and bulk polymerization. , preferably at a temperature of about 5-80°C.
- organic peroxides or hydroperoxides such as benzoyl peroxide, dicumyl peroxide, tert-butyl hydroperoxide, cumyl hydroperoxide, p-methylene hydroperoxide, azobisisobutyl Diazo compounds such as lonitrile and azobisisobutylamidine, ammonium salts represented by ammonium persulfate, peroxide salts such as sodium salts and potassium salts, and the like are used alone or as a redox system.
- organic peroxides or hydroperoxides such as benzoyl peroxide, dicumyl peroxide, tert-butyl hydroperoxide, cumyl hydroperoxide, p-methylene hydroperoxide, azobisisobutyl Diazo compounds such as lonitrile and azobisisobutylamidine, ammonium salts represented by ammonium persulfate, peroxide salts such as sodium salts and potassium
- an anionic or nonionic surfactant is used as an aqueous solution, etc., in which the pH is adjusted with an acid or base as necessary, and an inorganic salt is used as a buffer solution.
- the polymerization reaction is continued until the conversion of the monomer mixture reaches 90% or more.
- the resulting water-based latex can be prepared by a salt-acid coagulation method, a method using a salt such as calcium chloride, magnesium sulfate, sodium sulfate or ammonium sulfate, a method using a boron compound such as boric acid or borax, a heat coagulation method, or a freeze coagulation method.
- the resulting copolymer is thoroughly washed with water and dried.
- This acrylic rubber has a Mooney viscosity PML 1+4 (100° C.) of about 5-100, preferably about 20-80.
- a phenothiazine anti-aging agent represented by general formula [I] is used as component (B), which is a constituent of the composition of the present invention.
- R 3 is a hydrogen atom, a monovalent aliphatic hydrocarbon group with 1 to 20 carbon atoms, an aralkyl group with 7 to 20 carbon atoms, or the general formula is an acyl group represented by (here, R 4 is a monovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms), and R 5 is an aralkyl group having 7 to 20 carbon atoms.
- R 3 is an aliphatic hydrocarbon group having 1 to 20 carbon atoms
- R 3 is an aliphatic hydrocarbon group having 1 to 20 carbon atoms
- R 3 isopropyl group, 2-butyl group, 2-pentyl group, 3-pentyl group, 2-hexyl group , 3-hexyl group, 2-heptyl group, 3-heptyl group, 4-heptyl group, 2-octyl group, 3-octyl group, 4-octyl group, tert-butyl group, 1,1-dimethyl-1-propyl 1,1-dimethyl-1-butyl group, 1,1-
- R 3 being an aralkyl group having 7 to 20 carbon atoms include a benzyl group, an ⁇ -methylbenzyl group, a 9-fluorenylmethyl group and the like.
- R 4 is a monovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms. Specific examples of the aliphatic hydrocarbon group having 1 to 20 carbon atoms are the same as those for R 3 .
- monovalent aliphatic hydrocarbon groups having 4 to 20 carbon atoms and having a tertiary carbon at the ⁇ -position relative to the carbonyl group, such as tert-butyl, 1,1-dimethylpropyl, 1,1-dimethyl-1-butyl group, 1,1-dimethyl-1-pentyl group, 1,1-dimethyl-1-hexyl group, 3-methyl-3-pentyl group, 3-ethyl-3-pentyl group , 3-methyl-3-hexyl group, 1-methyl-1-cyclopentyl group, 1-methyl-1-cyclohexyl group, 1-adamantyl group and the like are preferred.
- the aralkyl group represented by R 5 includes benzyl group, ⁇ -methylbenzyl group and ⁇ , ⁇ -dimethylbenzyl group, with ⁇ , ⁇ -dimethylbenzyl group being particularly preferred.
- a phenothiazine anti-aging agent in which R 3 is a hydrogen atom can be produced by the method described in Patent Document 6.
- phenothiazine is reacted with ⁇ -methylstyrene in the presence of an acidic catalyst to form 3,7-bis( ⁇ , ⁇ -dimethylbenzyl)-10H-phenothiazine (hereinafter abbreviated as CD-S), and then treated with an oxidizing agent.
- CD-S 3,7-bis( ⁇ , ⁇ -dimethylbenzyl)-10H-phenothiazine-5,5-dioxide
- CD-S is treated with a base and then N- After alkylation, the desired phenothiazine antioxidant can be produced by oxidation of the sulfur atom.
- the CD-SO 2 obtained in Patent Document 6 may be reacted with a base and then with a halide of an aliphatic hydrocarbon having 1 to 20 carbon atoms.
- R 3 is an acyl group represented by general formula [II], it can be produced by the method described in Patent Document 13. Specifically, CD-S is N-acylated with an acyl halide in the presence of a basic organic compound or a basic inorganic compound, and then sulfur atoms are oxidized to produce the desired phenothiazine antioxidant. can be done.
- phenothiazine anti-aging agent represented by formula [I] include: 3,7-bis( ⁇ , ⁇ -dimethylbenzyl)-10H-phenothiazine-5,5-dioxide 10-methyl-3,7-bis( ⁇ , ⁇ -dimethylbenzyl)-10H-phenothiazine-5,5-dioxide 10-n-propyl-3,7-bis( ⁇ , ⁇ -dimethylbenzyl)-10H-phenothiazine-5,5-dioxide 10-isopropyl-3,7-bis( ⁇ , ⁇ -dimethylbenzyl)-10H-phenothiazine-5,5-dioxide 10-benzyl-3,7-bis( ⁇ , ⁇ -dimethylbenzyl)-10H-phenothiazine-5,5-dioxide 10-pivaloyl-3,7-bis( ⁇ , ⁇ -dimethylbenzyl)-10H-phenothiazine-5,5-dioxide 10-(2,2-
- the (B) component phenothiazine anti-aging agent is used in an amount of about 0.01 to 5 parts by weight, preferably about 0.1 to 5 parts by weight, per 100 parts by weight of the (A) component acrylic rubber. If the anti-aging agent is less than this, the acrylic rubber after cross-linking will suffer from thermal oxidative deterioration, resulting in significant deterioration in mechanical properties. In particular, it is difficult to suppress significant hardening deterioration in the latter stage of thermal oxidation deterioration.
- component (C) cross-linking accelerators examples include cross-linking accelerators such as guanidine compounds, diazabicycloalkene compounds, and organic acid salts thereof.
- Guanidine compounds include tetramethylguanidine, tetraethylguanidine, 1,3-diphenylguanidine, 1,3-di-o-tolylguanidine and the like. Preferred are 1,3-diphenylguanidine, 1,3-di-o-tolylguanidine and combinations thereof.
- diazabicycloalkene compound 1,8-diazabicyclo[5.4.0]-7-undecene is preferable.
- organic acid salt of the diazabicycloalkene compound an organic acid salt of 1,8-diazabicyclo[5.4.0]-7-undecene is preferable.
- Examples of the organic acid used for the organic acid salt of 1,8-diazabicyclo[5.4.0]-7-undecene include organic monobasic acids and organic dibasic acids.
- organic monobasic acids examples include n-hexanoic acid, n-heptanoic acid, n-octanoic acid, 2-ethylhexanoic acid, n-capric acid, n-lauric acid, p-toluenesulfonic acid, and phenol.
- organic dibasic acids include adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, undecanedioic acid, dodecanedioic acid, terephthalic acid, orthophthalic acid, and phthalic acid. Carboxylic acids or dicarboxylic acids are preferred.
- the (C) component cross-linking accelerator is used in an amount of about 0.1 to 5 parts by weight, preferably about 0.3 to 3 parts by weight, per 100 parts by weight of the (A) component acrylic rubber. If the amount of the cross-linking accelerator is less than this range, the speed of cross-linking may be remarkably lowered, the mechanical properties of the acrylic rubber after cross-linking may be lowered, and the mechanical properties of the acrylic rubber after heat aging may be lowered. On the other hand, if it is used in a larger amount than this, there is a possibility that the acrylic rubber may deteriorate in thermal oxidation deterioration or in compression set resistance.
- the crosslinkable acrylic rubber composition of the present invention may optionally contain, for example, fillers, processing aids, plasticizers, softeners, colorants, stabilizers, adhesion aids, release agents, and conductivity imparting agents. , thermal conductivity imparting agent, surface non-adhesive agent, tackifier, flexibility imparting agent, heat resistance improving agent, flame retardant, UV absorber, oil resistance improving agent, anti-scorch agent, lubricant, etc. can do.
- Fillers include silica such as basic silica and acidic silica; metal oxides such as zinc oxide, calcium oxide, titanium oxide and aluminum oxide; metal hydroxides such as magnesium hydroxide, aluminum hydroxide and calcium hydroxide; carbonates such as magnesium carbonate, aluminum carbonate, calcium carbonate and barium carbonate; silicates such as magnesium silicate, calcium silicate, sodium silicate and aluminum silicate; sulfates such as aluminum sulfate, calcium sulfate and barium sulfate; Metal sulfides such as molybdenum disulfide, iron sulfide, copper sulfide; synthetic hydrotalcite, diatomaceous earth, asbestos, lithopone (zinc sulfide/barium sulfide), graphite, carbon black (MT carbon black, SRF carbon black, FEF carbon black, etc.), carbon fluoride, calcium fluoride, coke, fine quartz powder, zinc white, talc, mica powder, wollastonite, carbon fiber,
- 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 oleic acid amide; higher fatty acid esters such as ethyl; higher aliphatic amines such as stearylamine and oleylamine; petroleum waxes such as carnauba wax and ceresin wax; polyglycols such as ethylene glycol, glycerin and diethylene glycol; Silicone oils, silicone polymers, low molecular weight 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
- plasticizers include epoxy resins, phthalic acid derivatives, and sebacic acid derivatives.
- softeners include lubricating oils, process oils, coal tar, castor oil, and calcium stearate.
- antioxidants include phenylene. diamines, phosphates, quinolines, cresols, phenols, dithiocarbamate metal salts and the like.
- crosslinkable acrylic rubber composition of the present invention comprising an acrylic rubber, a phenothiazine anti-aging agent and a crosslinking accelerator, and mixed in a Banbury mixer, a pressure kneader, an open roll, or the like. is blended using Crosslinking of the obtained crosslinkable admixture is performed by primary crosslinking at about 120 to 250°C for about 1 to 60 minutes and optionally oven crosslinking (secondary crosslinking) at about 120 to 200°C for about 1 to 20 hours. done.
- This highly viscous liquid was dissolved in 250 ml of toluene and put into a 1000 ml three-necked flask equipped with a magnetic stirrer, thermometer and reflux condenser. Then, 80 g of acetic acid and 107 g of 30% hydrogen peroxide water were added in order and reacted at 90° C. for 2 hours.
- the obtained acrylic rubber (a) had a Mooney viscosity PML 1+4 (100° C.) of 46.
- aqueous latex (b-1) and the aqueous latex (b-2) of the same weight are mixed, coagulated with a 10% by weight sodium sulfate aqueous solution, washed with water and dried to give acrylic rubber (b-1). ) and (b-2) were both 50% by weight to obtain acrylic rubber (b).
- the obtained acrylic rubber mixture had a Mooney viscosity PML 1+4 (100° C.) of 39.
- Acrylic rubber 100 parts by weight FEF carbon black (Tokai carbon product sheet GSO) 60 ⁇ Stearic acid (Miyoshi oil products TST) 1 ⁇ Polyoxyethylene stearyl ether phosphate 0.5 ⁇ (Toho Chemical Industry product Phosphanol RL-210) Crosslinking accelerator (Safic-Alcan product Vulcofac ACT55) 1 ⁇ CD-SO 2 2 ⁇
- acrylic rubber (a), FEF carbon black, stearic acid and polyoxyethylene stearyl ether phosphate were mixed in a Banbury mixer. The resulting mixture and the remaining components were mixed using an open roll to obtain a crosslinkable acrylic rubber composition.
- the crosslinkability of the acrylic elastomer composition and the physical properties of the crosslinked product were measured as follows.
- Mooney scorch test JIS K6300-1 compliant (125°C) corresponding to ISO 289-1 Minimum Mooney Viscosity (ML min) and scorch time (t5) are measured using Mooney Viscometer AM-3 manufactured by Toyo Seiki Seisakusho.
- Example 2 In Example 1, 2 parts by weight of CD- SO2 -PIV were used instead of CD- SO2 .
- Example 3 In Example 1, 2 parts by weight of CD- SO2 -Bn were used instead of CD- SO2 .
- Example 4 In Example 1, 2 parts by weight of CD- SO2 -Pr were used instead of CD- SO2 .
- Comparative example 1 In Example 1, 2 parts by weight of 4,4'-bis( ⁇ , ⁇ -dimethylbenzyl)diphenylamine (Ouchi Shinko Kagaku Kogyo product Nocrack CD) was used instead of CD- SO2 .
- Example 5 In Example 1, acrylic rubber (b) was used instead of acrylic rubber (a).
- Example 6 In Example 2, acrylic rubber (b) was used instead of acrylic rubber (a).
- Example 7 In Example 3, acrylic rubber (b) was used instead of acrylic rubber (a).
- Example 8 In Example 4, acrylic rubber (b) was used instead of acrylic rubber (a).
- Comparative example 2 In Comparative Example 1, acrylic rubber (b) was used instead of acrylic rubber (a).
- Comparative example 3 In Example 1, acrylic rubber (b-2) was used instead of acrylic rubber (a), and 0.6 parts by weight of hexamethylenediamine carbamate (Unimatec Cheminox AC6F) was added.
- Comparative example 4 In Example 2, acrylic rubber (b-2) was used instead of acrylic rubber (a), and 0.6 parts by weight of hexamethylenediamine carbamate (Cheminox AC6F) was added.
- Comparative example 5 In Example 3, acrylic rubber (b-2) was used instead of acrylic rubber (a), and 0.6 parts by weight of hexamethylenediamine carbamate (Cheminox AC6F) was added.
- Comparative example 7 In Comparative Example 1, acrylic rubber (b-2) was used instead of acrylic rubber (a), and 0.6 parts by weight of hexamethylenediamine carbamate (Cheminox AC6F) was added.
- Example 9 In Example 1, acrylic rubber (c) was used instead of acrylic rubber (a).
- Example 10 In Example 2, acrylic rubber (c) was used instead of acrylic rubber (a).
- Example 11 In Example 3, acrylic rubber (c) was used instead of acrylic rubber (a).
- Comparative example 8 In Comparative Example 1, acrylic rubber (c) was used instead of acrylic rubber (a).
- Comparative example 9 In Comparative Example 3, acrylic rubber (d) was used instead of acrylic rubber (b-2).
- Comparative example 10 In Comparative Example 4, acrylic rubber (d) was used instead of acrylic rubber (b-2).
- Comparative example 11 In Comparative Example 5, acrylic rubber (d) was used instead of acrylic rubber (b-2).
- Comparative example 12 In Comparative Example 7, acrylic rubber (d) was used instead of acrylic rubber (b-2).
- Example 12 In Example 2, acrylic rubber (e) was used instead of acrylic rubber (a).
- Comparative example 13 In Comparative Example 1, acrylic rubber (e) was used instead of acrylic rubber (a).
- Comparative example 14 In Comparative Example 4, acrylic rubber (f) was used instead of acrylic rubber (b-2).
- Comparative example 15 In Comparative Example 7, acrylic rubber (f) was used instead of acrylic rubber (b-2).
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Abstract
Description
R1、R2:水素原子、芳香族環で置換されてもよい
C1~C8のアルキル基、アルコキシ基、
ハロゲン原子、シアノ基
R3:水素原子、C1~C6の鎖状または環状の
アルキル基、ビニル基、芳香族基
m、n:0~2
5位の硫黄原子が-SO2-のフェノチアジン化合物も知られており、例えば特許文献6に記載されている。
Y:化学的な単結合、-S(=O)-、-SO2-
Ra、Rb:置換基を有してもよいC1~C30有機基
Za、Zb:化学的な単結合、-SO2-
X1、X2:水素原子、ハロゲン原子、アルキル基、
シアノ基、ニトロ基、-OR1、-O-CO-R1、
-CO-OR1、-O-CO-OR1、-NR2R3、-NR2-CO-R1、
-CO-NR2R3、-O-CO-NR2R3
n、m:0~2、ただしいずれか一方は0ではない
Fmoc:9-フルオレニルメチルオキシカルボニル基
アクリルゴム組成物の架橋に際し、熱および含窒素塩基性有機化合物の作用によりカルバミンエステル基が分解してアミノ基を遊離し、次いでα,β-不飽和カルボン酸単量体に由来する活性部位と反応し、相補的な架橋構造が形成される。かかる固有の架橋構造は、アクリルゴム架橋物の熱酸化劣化初期において顕著な軟化劣化を抑制する効果を奏する。
また、上記記載の架橋構造を有するアクリルゴム架橋物に対するフェノチアジン系老化防止剤の有効性については、何ら記載されていない。
(A) カルバミン酸エステル基およびカルボキシル基を含有するアクリルゴム、
(B) 下記一般式〔I〕で表されるフェノチアジン系老化防止剤
〔ここで、R3は水素原子、炭素数1~20の一価の脂肪族炭化水素基、炭素数7~20のアラルキル基または下記一般式
で表されるアシル基(ここで、R4は炭素数1~20の一価の脂肪族炭化水素基である)であり、R5は炭素数7~20のアラルキル基である〕
および
(C) 架橋促進剤
から構成される。
態様(A-1):アルキル(メタ)アクリレートおよび/またはアルコキシアルキル(メタ)アクリレート単量体 90~99.8重量%、α,β-不飽和カルボン酸単量体 0.1~5重量%および一般式
(ここで、R1は水素原子またはメチル基であり、R2は炭素数1~10の二価の脂肪族炭化水素基である)で表されるカルバミン酸エステル基含有(メタ)アクリレート単量体 0.1~5重量%の共単量体割合で共重合されたアクリルゴム
または
態様(A-2):アルキル(メタ)アクリレートおよび/またはアルコキシアルキル(メタ)アクリレート単量体 90~99.9重量%と一般式〔III〕で表されるカルバミン酸エステル基含有(メタ)アクリレート単量体 0.1~10重量%との共単量体割合で共重合されたアクリルゴム(i)
および
アルキル(メタ)アクリレートおよび/またはアルコキシアルキル(メタ)アクリレート単量体 90~99.9重量%とα,β-不飽和カルボン酸単量体 0.1~10重量%との共単量体割合で共重合体されたアクリルゴム(ii)
の混合物であって、それぞれの成分の重量比が90~10重量%、10~90重量%である
のいずれかが用いられる。ここで、(メタ)アクリレートはアクリレートまたはメタクリレートを指している。
wCA(wt%):アクリルゴムのα,β-不飽和カルボン酸単量体の重量分率
組成
MCA(g/mol):α,β-不飽和カルボン酸単量体の分子量
wNH2(wt%):アクリルゴムのカルバミン酸エステル基含有(メタ)アクリレ
ート単量体の重量分率組成
MNH2 (g/mol):カルバミン酸エステル基含有(メタ)アクリレート単量体の
分子量
W(i)(重量部):アクリルゴム(i)の重量
w(i)NH2(wt%):アクリルゴム(i)のカルバミン酸エステル基含有(メタ)
アクリレート単量体の重量分率組成
M(i)NH2(g/mol):カルバミン酸エステル基含有(メタ)アクリレート単量体
の分子量
W(ii)(重量部):アクリルゴム(ii)の重量
w(ii)CA(wt%):アクリルゴム(ii)のα,β-不飽和カルボン酸単量体の重量
分率組成
M(ii)CA(g/mol):α,β-不飽和カルボン酸単量体の分子量
等が挙げられ、好ましくは製造の容易さから
が用いられる。
ここで、R3は水素原子、炭素数1~20の一価の脂肪族炭化水素基、炭素数7~20のアラルキル基または一般式
で表されるアシル基(ここで、R4は炭素数1~20の一価の脂肪族炭化水素基である)であり、R5は炭素数7~20のアラルキル基である。
3,7-ビス(α,α-ジメチルベンジル)-10H-フェノチアジン-5,5-ジオキサイド
10-メチル-3,7-ビス(α,α-ジメチルベンジル)-10H-フェノチアジン-5,5-ジオキサイド
10-n-プロピル-3,7-ビス(α,α-ジメチルベンジル)-10H-フェノチアジン-5,5-ジオキサイド
10-イソプロピル-3,7-ビス(α,α-ジメチルベンジル)-10H-フェノチアジン-5,5-ジオキサイド
10-ベンジル-3,7-ビス(α,α-ジメチルベンジル)-10H-フェノチアジン-5,5-ジオキサイド
10-ピバロイル-3,7-ビス(α,α-ジメチルベンジル)-10H-フェノチアジン-5,5-ジオキサイド
10-(2,2-ジメチル-ブタノイル)-3,7-ビス(α,α-ジメチルベンジル)-10H-フェノチアジン-5,5-ジオキサイド
10-(1-アダマンタンカルボニル)-3,7-ビス(α,α-ジメチルベンジル)-10H-フェノチアジン-5,5-ジオキサイド
等が挙げられる。
3,7-ビス(α,α-ジメチルベンジル)-10H-フェノチアジン-5,5-ジオキサイド〔CD-SO2〕の製造
マグネット攪拌子、温度計、窒素ガス導入口と排出口および還流冷却管を備えた容量500mlの四口フラスコに、フェノチアジン 24.9g(0.125モル)、p-トルエンスルホン酸 0.6gおよびトルエン 115mlを投入し、80℃に昇温した後、α-メチルスチレン 29.5g(0.25モル)を加え、窒素ガス雰囲気下で1時間反応させた。
10-ピバロイル-3,7-ビス(α,α-ジメチルベンジル)-10H-フェノチアジン-5,5-ジオキサイド〔CD-SO2-PIV〕の製造
マグネット攪拌子、温度計、窒素ガス導入口と排出口および還流冷却管を備えた容量1000mlの四口フラスコに、フェノチアジン 119.6g(0.6モル)、p-トルエンスルホン酸 2.88gおよびトルエン 480mlを投入し、80℃に昇温した後、α-メチルスチレン 141.9g(1.2モル)を加え、窒素ガス雰囲気下で1時間反応させた。
1H NMR(300MHz、CDCl3、δ ppm):1.22 (s、9H、-C(CH 3)3)
1.71 (s、12H、-C(CH 3)2-)
7.19~7.30 (m、12H)
7.42 (d、J=9.0Hz、2H)
8.03 (d、J=1.8Hz、2H)
10-ベンジル-3,7-ビス(α,α-ジメチルベンジル)-10H-フェノチアジン-5,5-ジオキシド〔CD-SO2-Bn〕の製造
マグネット攪拌子、温度計、ガス導入管および還流冷却管を備えた容量1000mlの四口フラスコに、精製CD-S 43.6g (100ミリモル)およびN,N-ジメチルホルムアミド250mlを投入し、窒素雰囲気下5℃以下に冷却した。系内の温度を10℃以下に保ちながら水素化ナトリウム 3.6g(150ミリモル)を加え、1時間反応させた。塩化ベンジル16.4g(130ミリモル)を加えた後、70℃で1時間反応させた。得られた反応混合物を室温まで冷却した後、飽和塩化ナトリウム水溶液に注いだ。生成物をジクロロメタンで抽出し、有機層を無水硫酸マグネシウムで乾燥した。硫酸マグネシウムをろ別した後、ろ液から揮発性成分を減圧留去し、僅かに黄色みをおびた固体として粗製10-ベンジル-3,7-ビス(α,α-ジメチルベンジル)-10H-フェノチアジン〔CD-S-Bn〕を55.1g得た。
1H NMR(400MHz、Acetone d6、δ ppm):
1.74 (s、12H、-C(CH 3)2-)
5.56 (s、2H、N-CH 2-Ar)
7.15~7.37 (m、17H、Ar)
7.42(dd、J=8.8Hz、2.8Hz、2H、Ar)
7.92 (d、J=2.8Hz、2H、Ar)
10-プロピル-3,7-ビス(α,α-ジメチルベンジル)-10H-フェノチアジン-5,5-ジオキシド〔CD-SO2-Pr〕の製造
マグネット攪拌子、温度計、ガス導入管および還流冷却管を備えた容量500mlの四口フラスコに、精製CD-S 21.8g (50ミリモル)およびN,N-ジメチルホルムアミド160mlを投入し、窒素雰囲気下5℃以下に冷却した。系内の温度を10℃以下に保ちながら水素化ナトリウム 1.8g(75ミリモル)を加え、1時間反応させた。次いで臭化プロピル8.0g(65ミリモル)を加えた後、70℃で1時間反応させた。得られた反応混合物を室温まで冷却した後、飽和塩化ナトリウム水溶液に注いだ。生成物を酢酸エチルで抽出し、有機層を無水硫酸マグネシウムで乾燥した。不溶物をろ別した後、ろ液から揮発性成分を減圧留去し、僅かに黄色みを帯びた固体として粗製10-プロピル-3,7-ビス(α,α-ジメチルベンジル)-10H-フェノチアジン〔CD-S-Pr〕を24.9g得た。
1H NMR(400MHz、Chloroform-d)、δ ppm(TMS):
1.01 (t、J=7.2Hz、3H、-CH2CH2CH 3)
1.73 (s、12H、-C(CH 3)2-)
1.89 (sext、J=7.6Hz、2H、-CH2CH 2CH3)
4.03 (t、J=8.0Hz、2H、-CH 2CH2CH3)
7.14~7.32 (m、14H、Ar)
8.13 (d、J=2.4Hz、2H、Ar)
9FMMの製造
マグネット攪拌子、温度計、窒素ガス導入口と排出口および還流冷却管を備えた容量1000mlの四口フラスコに、9-フルオレニルメタノール 16.4g(135ミリモル)、2-イソシアナトエチルメタクリレート 25.1g(162ミリモル)、ジラウリン酸ジブチルスズ1.1gおよびベンゼン 440mlを投入し、窒素ガス雰囲気下80℃で2時間反応させた。
1H-NMR(400MHz、Acetone d6、δ ppm):
1.91 (s, 3H, CH2=C(CH 3)-C(=O)-O-)
3.47 (q, J=5.6Hz, 2H, -O-CH2CH 2-NH-C(C=O)-)
4.21 (t, J=5.6Hz, 2H, -O-CH 2CH2-NH-C(C=O)-)
4.23 (t, J=7.2Hz, 1H, -C(=O)-OCH2-CH-Ar2)
4.35 (d, J=7.2Hz, 2H, -C(=O)-OCH 2-CH-Ar2)
5.62 (s, 1H, カルボニル基に対して
trans-CH 2=C(CH3)-C(=O)-O-)
6.10 (s, 1H,カルボニル基に対して
cis-CH 2=C(CH3)-C(=O)-O-)
6.73 (brs, 1H, -O-CH2CH2-NH-C(C=O)-
7.32 (t, J=7.6Hz, 2H, Ar)
7.41 (t, J=7.6Hz, 2H, Ar)
7.68 (d, J=7.6Hz, 2H, Ar)
7.86 (d, J=7.6Hz, 2H, Ar)
〔アクリルゴム(a)の製造〕
温度計、撹拌機、窒素ガス導入管およびジムロート冷却管を備えたセパラブルフラスコ内に、
水 187重量部
ラウリル硫酸ナトリウム 2 〃
ポリオキシエチレンラウリルエーテル 2 〃
仕込み単量体混合物
アクリル酸エチル〔EA〕 97.8 〃
フマル酸モノn-ブチル〔MBF〕 0.8 〃
9FMM 1.4 〃
を仕込み、窒素ガス置換を行って系内の酸素を十分に除去した後、
ナトリウムホルムアルデヒド 0.008重量部
スルホキシレート
(富士フィルム和光純薬工業製品ロンガリット)
第3ブチルハイドロパーオキサイド 0.0047 〃
(日油製品パーブチルH69)
を加えて、室温条件下で重合反応を開始させ、重合転化率が90%以上になる迄反応を継続した。得られた水性ラテックスを、10重量%硫酸ナトリウム水溶液で凝析させた後、水洗、乾燥してアクリルゴム(a)を得た。
α:6.4-8.1ppmのシグナルの積分値
β:3.2-5.0ppmのシグナルの積分値
9FMM(mol%)=200×α/(9β-5α)
EA+MBF(mol%)=100-9FMM(mol%)
また、近似的な重量分率組成を下式より求めたところ、9FMMは1.4重量%、EA+MBFは98.6重量%であった。
9FMM(wt%)=(9FMM(mol%)×351.4×100)/
〔9FMM(mol%)×351.4+(EA+MBF(mol%))×100.5)〕
EA+MBF(wt%)=100-9FMM(wt%)
さらに、アクリルゴム(a)の酸価測定することにより、MBF(wt%)を求めたところ、0.6重量%であった。
〔アクリルゴム(b)の製造〕
-アクリルゴム(b-1)の製造-
参考例6のアクリルゴム(a)の製造において、仕込み単量体混合物として
アクリル酸エチル〔EA〕 97.2重量部
9FMM 2.8 〃
を用い、重合反応の開始剤として
ナトリウムホルムアルデヒド 0.008重量部
スルホキシレート(ロンガリット)
第3ブチルハイドロパーオキサイド 0.0047 〃
(パーブチルH69)
酢酸 0.67 〃
が用いられ、水性ラテックス(b-1)(ゴム固形分32重量%)およびアクリルゴムb-1を得た。得られたアクリルゴム(b-1)のムーニー粘度 PML1+4(100℃)は、47であった。
9FMM(wt%)=(9FMM(mol%)×351.4×100)/
〔9FMM(mol%)×351.4+(EA(mol%))×100.1)〕
EA(wt%)=100-9FMM(wt%)
参考例6のアクリルゴム(a)の製造において、仕込み単量体混合物として
アクリル酸エチル〔EA〕 98.4重量部
フマル酸モノn-ブチル〔MBF〕 1.6 〃
を用い、アクリルゴム(a)の製造と同様に行い、水性ラテックス(b-2)(ゴム固形分32重量%)およびアクリルゴム(b-2)を得た。得られたアクリルゴム(b-2)のムーニー粘度 PML1+4(100℃)は、36であった。また、アクリルゴム(b-2)の酸価を測定することにより、MBF含量(wt%)を求めたところ1.2重量%であった。
〔アクリルゴム(c)の製造〕
参考例6のアクリルゴム(a)の製造において、仕込み単量体混合物として
アクリル酸エチル〔EA〕 57.8重量部
アクリル酸n-ブチル〔BA〕 40.0 〃
フマル酸モノn-ブチル〔MBF〕 0.8 〃
9FMM 1.4 〃
を用い、アクリルゴム(c)を得た。得られたアクリルゴム(c)のムーニー粘度 PML1+4(100℃)は、33であった。また、アクリルゴム(c)の酸価を測定することにより、MBF含量(wt%)を求めたところ0.6重量%であった。
また、モル分率組成を1H-NMR(400MHz、CD3C(=O)CD3、δ ppm)より下記式を用いて求めたところ、9FMMは0.43モル%、EA+BA+MBFは99.57モル%であった。
α:6.4-8.1ppmのシグナルの積分値
β:3.2-5.0ppmのシグナルの積分値
9FMM(mol%)=200×α/(9β-5α)
EA+BA+MBF(mol%)=100-9FMM(mol%)
また、近似的な重量分率組成を下記式より求めたところ、9FMMは1.4重量%、EA+BA+MBFは98.6重量%であった。
9FMM(wt%)=(9FMM(mol%)×351.4×100)/
〔9FMM(mol%)×351.4+(EA+BA+MBF(mol%))×110.3)〕
EA+BA+MBF(wt%)=100-9FMM(wt%)
〔アクリルゴム(d)の製造〕
参考例6のアクリルゴム(a)の製造において、仕込み単量体混合物として
アクリル酸エチル〔EA〕 58.4重量部
アクリル酸n-ブチル〔BA〕 40.0 〃
フマル酸モノn-ブチル〔MBF〕 1.6 〃
を用い、アクリルゴム(d)を得た。得られたアクリルゴム(d)のムーニー粘度 PML1+4(100℃)は、24であった。また、アクリルゴム(d)の酸価を測定することにより、MBF含量(wt%)を求めたところ1.2重量%であった。
〔アクリルゴム(e)の製造〕
参考例6のアクリルゴム(a)の製造において、仕込み単量体混合物として
アクリル酸エチル〔EA〕 52.8重量部
アクリル酸n-ブチル〔BA〕 40.0 〃
メタクリル酸メチル〔MMA〕 5.0 〃
フマル酸モノn-ブチル〔MBF〕 0.8 〃
9FMM 1.4 〃
を用い、アクリルゴム(e)を得た。得られたアクリルゴム(e)のムーニー粘度 PML1+4(100℃)は、40であった。また、アクリルゴム(e)の酸価を測定することにより、MBF含量(wt%)を求めたところ0.6重量%であった。
また、モル分率組成を1H-NMR(400MHz、CD3C(=O)CD3、δ ppm)より下記式を用いて求めたところ、9FMMは0.44モル%、EA+BA+MMA+MBFは99.56モル%であった。
α:6.4-8.1ppmのシグナルの積分値
β:3.2-5.0ppmのシグナルの積分値からγを引いた値
γ:3.4-3.6ppmのシグナルの積分値
9FMM(mol%)=600×α/(27β-13α+18γ)
EA+BA+MMA+MBF(mol%)=100-9FMM(mol%)
また、近似的な重量分率組成を下式より求めたところ、9FMMは1.4重量%、EA+BA+MMA+MBFは98.6重量%であった。
9FMM(wt%)=(9FMM(mol%)×351.4×100)/
〔9FMM(mol%)×351.4+(EA+BA+MMA+MBF(mol%))×110.3)〕
EA+BA+MMA+MBF(wt%)=100-9FMM(wt%)
〔アクリルゴム(f)の製造〕
参考例6のアクリルゴム(a)の製造において、仕込み単量体混合物として
アクリル酸エチル〔EA〕 53.4重量部
アクリル酸n-ブチル〔BA〕 40.0 〃
メタクリル酸メチル〔MMA〕 5.0 〃
フマル酸モノn-ブチル〔MBF〕 1.6 〃
を用い、アクリルゴム(f)を得た。得られたアクリルゴム(f)のムーニー粘度 PML1+4(100℃)は、31であった。また、アクリルゴム(f)の酸価を測定することにより、MBF含量(wt%)を求めたところ1.2重量%であった。
アクリルゴム(a) 100重量部
FEFカーボンブラック(東海カーボン製品シーストGSO) 60 〃
ステアリン酸(ミヨシ油脂製品TST) 1 〃
ポリオキシエチレンステアリルエーテルリン酸 0.5 〃
(東邦化学工業製品フォスファノールRL-210)
架橋促進剤(Safic-Alcan社製品Vulcofac ACT55) 1 〃
CD-SO2 2 〃
以上の各成分の内、アクリルゴム(a)、FEFカーボンブラック、ステアリン酸およびポリオキシエチレンステアリルエーテルリン酸を、バンバリーミキサで混和した。得られた混和物と残りの各成分とをオープンロールを用いて混和し、架橋性アクリルゴム組成物を得た。
ムーニースコーチ試験:ISO 289-1に対応するJIS K6300-1準拠(125℃)
東洋精機製作所製ムーニービスコメーターAM-3を用い、最
小ムーニー粘度(ML min)とスコーチ時間(t5)の値を測定
架橋試験:ISO 6502に対応するJIS K6300-2準拠(180℃、12分間)
東洋精機製作所製ロータレス・レオメータRLR-3使を用い、
ML、MH、tc(10)およびtc(90)の値を測定
ML:最小トルク
MH:最大トルク
tc(10):架橋トルクがML+(MH-ML)×0.1に達するまでに要
する時間
tc(90):架橋トルクがML+(MH-ML)×0.9に達するまでに要
する時間
常態物性:ISO 37に対応するJIS K6251、ISO 7619-1に対応する
JIS K6253準拠し、ポストキュアシートについて測定
空気加熱老化試験:ISO 188に対応するJIS K6257準拠し、ポストキュ
アシートについて測定
(190℃:100時間、200時間、300時間、400時間、
500時間)
(175℃:250時間、500時間、750時間、1000時間)
実施例1において、CD-SO2の代わりにCD-SO2-PIVが2重量部用いられた。
実施例1において、CD-SO2の代わりにCD-SO2-Bnが2重量部用いられた。
実施例1において、CD-SO2の代わりにCD-SO2-Prが2重量部用いられた。
実施例1において、CD-SO2の代わりに4,4′-ビス(α,α-ジメチルベンジル)ジフェニルアミン(大内新興化学工業製品ノクラックCD)が2重量部用いられた。
実施例1において、アクリルゴム(a)の代わりにアクリルゴム(b)が用いられた。
実施例2において、アクリルゴム(a)の代わりにアクリルゴム(b)が用いられた。
実施例3において、アクリルゴム(a)の代わりにアクリルゴム(b)が用いられた。
実施例4において、アクリルゴム(a)の代わりにアクリルゴム(b)が用いられた。
比較例1において、アクリルゴム(a)の代わりにアクリルゴム(b)が用いられた。
実施例1において、アクリルゴム(a)の代わりにアクリルゴム(b-2)が用いられ、さらにヘキサメチレンジアミンカーバメート(ユニマテック製品ケミノックスAC6F)が0.6重量部添加された。
実施例2において、アクリルゴム(a)の代わりにアクリルゴム(b-2)が用いられ、さらにヘキサメチレンジアミンカーバメート(ケミノックスAC6F)が0.6重量部添加された。
実施例3において、アクリルゴム(a)の代わりにアクリルゴム(b-2)が用いられ、さらにヘキサメチレンジアミンカーバメート(ケミノックスAC6F)が0.6重量部添加された。
実施例4において、アクリルゴム(a)の代わりにアクリルゴム(b-2)が用いられ、さらにヘキサメチレンジアミンカーバメート(ケミノックスAC6F)が0.6重量部添加された。
比較例1において、アクリルゴム(a)の代わりにアクリルゴム(b-2)が用いられ、さらにヘキサメチレンジアミンカーバメート(ケミノックスAC6F)が0.6重量部添加された。
実施例1において、アクリルゴム(a)の代わりにアクリルゴム(c)が用いられた。
実施例2において、アクリルゴム(a)の代わりにアクリルゴム(c)が用いられた。
実施例3において、アクリルゴム(a)の代わりにアクリルゴム(c)が用いられた。
比較例1において、アクリルゴム(a)の代わりにアクリルゴム(c)が用いられた。
比較例3において、アクリルゴム(b-2)の代わりにアクリルゴム(d)が用いられた。
比較例4において、アクリルゴム(b-2)の代わりにアクリルゴム(d)が用いられた。
比較例5において、アクリルゴム(b-2)の代わりにアクリルゴム(d)が用いられた。
比較例7において、アクリルゴム(b-2)の代わりにアクリルゴム(d)が用いられた。
実施例2において、アクリルゴム(a)の代わりにアクリルゴム(e)が用いられた。
比較例1において、アクリルゴム(a)の代わりにアクリルゴム(e)が用いられた。
比較例4において、アクリルゴム(b-2)の代わりにアクリルゴム(f)が用いられた。
比較例7において、アクリルゴム(b-2)の代わりにアクリルゴム(f)が用いられた。
表1
測定結果 実1 実2 実3 実4 比1
ムーニースコーチ試験(125℃)
ML min (pts) 72 76 78 76 72
t5 (分) 3.8 3.3 3.3 3.4 3.1
架橋試験(180℃)
tc(10) (分) 0.60 0.54 0.56 0.56 0.53
tc(90) (分) 6.41 5.85 5.97 5.93 5.91
ML (N・m) 0.26 0.26 0.26 0.26 0.25
MH (N・m) 0.89 0.90 0.91 0.89 0.91
常態物性(ポストキュア)
硬度 (Duro A) 63 65 64 68 64
100%モジュラス (MPa) 6.7 6.7 6.9 7.1 6.6
破断時強度 (MPa) 16.8 17.5 17.8 18.2 17.1
破断時伸び (%) 210 210 210 220 220
熱老化試験(190℃、100時間)
硬度 (Duro A) 73 73 73 74 73
100%モジュラス (MPa) 6.1 6.3 6.7 6.6 5.5
破断時強度 (MPa) 12.9 13.3 14.0 14.0 12.5
破断時伸び (%) 210 200 200 210 230
熱老化試験(190℃、200時間)
硬度 (Duro A) 76 76 77 76 77
100%モジュラス (MPa) 4.7 4.7 5.1 5.3 4.6
破断時強度 (MPa) 9.5 9.9 10.2 10.4 9.0
破断時伸び (%) 230 230 220 220 230
熱老化試験(190℃、300時間)
硬度 (Duro A) 81 82 83 81 83
100%モジュラス (MPa) 3.8 3.9 4.0 4.5 4.7
破断時強度 (MPa) 6.7 7.0 7.0 7.6 7.0
破断時伸び (%) 240 250 240 230 200
熱老化試験(190℃、400時間)
硬度変化 (Duro A) 89 88 89 89 90
100%モジュラス (MPa) 4.2 4.6 4.7 5.0
破断時強度 (MPa) 4.7 5.3 5.2 5.7 6.8
破断時伸び (%) 180 190 170 160 70
熱老化試験(190℃、500時間)
硬度変化 (Duro A) 93 94 95 96 95
100%モジュラス (MPa)
破断時強度 (MPa) 6.6 6.5 6.6 7.2 12.2
破断時伸び (%) 70 60 60 60 20
熱老化試験(175℃、500時間)
硬度変化 (Duro A) 76 76 76 75 73
100%モジュラス (MPa) 4.8 4.9 5.4 5.6 4.8
破断時強度 (MPa) 9.9 10.3 10.5 10.7 9.6
破断時伸び (%) 230 230 220 220 240
熱老化試験(175℃、1000時間)
硬度変化 (Duro A) 89 90 90 91 91
100%モジュラス (MPa) 5.5 5.3 5.4 5.8 6.2
破断時強度 (MPa) 6.7 6.7 6.8 7.3 7.2
破断時伸び (%) 180 220 200 200 170
表2
測定結果 実5 実6 実7 実8 比2
ムーニースコーチ試験(125℃)
ML min (pts) 68 69 69 68 67
t5 (分) 3.0 3.0 3.2 3.4 2.5
架橋試験(180℃)
tc(10) (分) 0.62 0.55 0.58 0.57 0.57
tc(90) (分) 6.35 5.87 5.95 5.94 5.91
ML (N・m) 0.26 0.26 0.27 0.27 0.25
MH (N・m) 0.82 0.80 0.84 0.84 0.82
常態物性(ポストキュア)
硬度 (Duro A) 66 66 67 70 66
100%モジュラス (MPa) 7.0 8.1 7.5 7.9 6.9
破断時強度 (MPa) 15.0 16.3 16.2 17.0 16.0
破断時伸び (%) 200 200 200 210 230
熱老化試験(190℃、100時間)
硬度 (Duro A) 74 76 75 72 72
100%モジュラス (MPa) 6.2 6.6 6.5 6.6 5.4
破断時強度 (MPa) 11.9 12.1 11.8 12.4 10.8
破断時伸び (%) 210 210 200 210 220
熱老化試験(190℃、200時間)
硬度 (Duro A) 75 76 78 77 76
100%モジュラス (MPa) 4.4 4.7 5.0 5.3 4.3
破断時強度 (MPa) 7.9 8.5 8.7 8.7 7.0
破断時伸び (%) 220 220 210 210 220
熱老化試験(190℃、300時間)
硬度 (Duro A) 82 84 82 82 83
100%モジュラス (MPa) 3.7 3.8 4.0 4.6 4.4
破断時強度 (MPa) 5.6 5.9 6.1 6.5 5.8
破断時伸び (%) 230 240 230 210 200
熱老化試験(190℃、400時間)
硬度 (Duro A) 87 88 89 91 92
100%モジュラス (MPa) 4.1 4.1 4.2 4.8
破断時強度 (MPa) 4.3 4.3 4.4 5.1 6.7
破断時伸び (%) 190 180 170 130 50
熱老化試験(190℃、500時間)
硬度 (Duro A) 93 93 93 96 95
100%モジュラス (MPa)
破断時強度 (MPa) 6.3 6.1 6.5 7.4 12.0
破断時伸び (%) 70 70 70 60 10
熱老化試験(175℃、500時間)
硬度変化 (Duro A) 78 76 76 78 76
100%モジュラス (MPa) 4.6 4.7 5.0 5.3 4.1
破断時強度 (MPa) 8.5 8.7 9.0 9.4 7.5
破断時伸び (%) 220 220 220 220 240
熱老化試験(175℃、1000時間)
硬度変化 (Duro A) 89 89 89 90 91
100%モジュラス (MPa) 4.9 4.7 5.2 5.6 6.0
破断時強度 (MPa) 5.6 5.7 5.9 6.2 6.3
破断時伸び (%) 190 210 180 190 160
表3
測定結果 比3 比4 比5 比6 比7
ムーニースコーチ試験(125℃)
ML min (pts) 63 67 67 66 65
t5 (分) 3.1 3.3 3.2 3.2 2.8
架橋試験(180℃)
tc(10) (分) 0.53 0.51 0.51 0.51 0.51
tc(90) (分) 5.45 5.15 5.30 5.22 4.84
ML (N・m) 0.28 0.27 0.28 0.29 0.26
MH (N・m) 1.02 1.00 1.01 1.03 1.01
常態物性(ポストキュア)
硬度 (Duro A) 67 67 66 70 65
100%モジュラス (MPa) 4.9 4.8 5.9 6.0 5.5
破断時強度 (MPa) 15.7 16.6 16.8 16.8 16.6
破断時伸び (%) 220 230 230 240 250
熱老化試験(190℃、100時間)
硬度変化 (Duro A) 74 73 74 72 69
100%モジュラス (MPa) 3.4 3.7 4.1 3.7 2.9
破断時強度 (MPa) 10.2 10.8 11.1 11.2 9.2
破断時伸び (%) 320 300 290 310 360
熱老化試験(190℃、200時間)
硬度 (Duro A) 79 77 78 76 73
100%モジュラス (MPa) 2.8 2.9 3.2 3.5 2.7
破断時強度 (MPa) 6.4 7.1 7.0 7.4 5.4
破断時伸び (%) 350 340 320 310 350
熱老化試験(190℃、300時間)
硬度 (Duro A) 84 83 84 85 80
100%モジュラス (MPa) 2.6 2.7 2.9 3.4 3.5
破断時強度 (MPa) 3.8 4.3 4.4 5.0 4.5
破断時伸び (%) 380 380 330 320 250
熱老化試験(190℃、400時間)
硬度 (Duro A) 89 89 88 91 93
100%モジュラス変化 (MPa) 3.4 3.5 3.7 4.4
破断時強度 (MPa) 3.2 3.5 3.9 4.5 6.5
破断時伸び (%) 210 180 170 130 50
熱老化試験(190℃、500時間)
硬度 (Duro A) 93 93 95 96 97
100%モジュラス (MPa)
破断時強度 (MPa) 6.4 6.0 6.7 8.2 12.6
破断時伸び (%) 60 80 50 40 20
熱老化試験(175℃、500時間)
硬度変化 (Duro A) 80 79 77 80 75
100%モジュラス (MPa) 2.9 3.0 3.4 3.4 2.7
破断時強度 (MPa) 6.9 7.4 7.8 7.7 5.9
破断時伸び (%) 370 350 320 320 380
熱老化試験(175℃、1000時間)
硬度変化 (Duro A) 89 90 92 88 89
100%モジュラス (MPa) 4.1 4.4 4.5 5.0 5.7
破断時強度 (MPa) 4.2 4.8 4.7 5.1 5.8
破断時伸び (%) 200 290 240 230 160
表4
測定結果 実9 実10 実11 比8
ムーニースコーチ試験(125℃)
ML min (pts) 58 61 60 57
t5 (分) 3.6 3.0 3.1 3.3
架橋試験(180℃)
tc(10) (分) 0.62 0.56 0.56 0.58
tc(90) (分) 6.56 6.09 6.14 6.18
ML (N・m) 0.21 0.22 0.21 0.21
MH (N・m) 0.79 0.82 0.80 0.78
常態物性(ポストキュア)
硬度 (Duro A) 63 62 62 62
100%モジュラス (MPa) 7.3 7.6 7.2 7.4
破断時強度 (MPa) 13.8 14.1 14.3 13.0
破断時伸び (%) 160 160 170 160
熱老化試験(190℃、100時間)
硬度 (Duro A) 69 68 70 67
100%モジュラス (MPa) 6.4 6.9 7.1 6.0
破断時強度 (MPa) 11.3 11.9 11.9 11.1
破断時伸び (%) 160 160 160 180
熱老化試験(190℃、200時間)
硬度 (Duro A) 70 70 72 69
100%モジュラス (MPa) 5.5 6.1 5.7 5.3
破断時強度 (MPa) 9.1 9.9 9.9 9.3
破断時伸び (%) 160 160 170 170
熱老化試験(190℃、300時間)
硬度 (Duro A) 73 75 75 74
100%モジュラス (MPa) 4.7 4.9 5.4 5.5
破断時強度 (MPa) 7.6 8.3 8.6 8.6
破断時伸び (%) 160 170 170 160
熱老化試験(190℃、400時間)
硬度変化 (Duro A) 78 78 79 81
100%モジュラス (MPa) 4.5 5.0 5.1 7.4
破断時強度 (MPa) 6.7 7.5 7.4 8.6
破断時伸び (%) 170 160 160 120
熱老化試験(190℃、500時間)
硬度変化 (Duro A) 85 83 84 87
100%モジュラス (MPa) 5.0 5.3 5.8
破断時強度 (MPa) 5.9 6.4 6.6 8.7
破断時伸び (%) 130 130 120 80
熱老化試験(175℃、250時間)
硬度変化 (Duro A) 69 69 69 68
100%モジュラス (MPa) 6.9 7.2 7.6 5.8
破断時強度 (MPa) 11.5 12.2 12.4 10.9
破断時伸び (%) 160 160 150 180
熱老化試験(175℃、500時間)
硬度変化 (Duro A) 67 72 71 64
100%モジュラス (MPa) 5.2 5.5 5.8 4.9
破断時強度 (MPa) 8.9 9.0 10.0 9.0
破断時伸び (%) 170 160 170 180
熱老化試験(175℃、750時間)
硬度変化 (Duro A) 74 74 74 74
100%モジュラス (MPa) 5.2 5.5 5.9 5.5
破断時強度 (MPa) 8.6 8.9 9.1 8.8
破断時伸び (%) 180 170 160 170
熱老化試験(175℃、1000時間)
硬度変化 (Duro A) 79 82 82 84
100%モジュラス (MPa) 5.5 5.7 6.0 7.8
破断時強度 (MPa) 7.7 7.9 8.2 9.2
破断時伸び (%) 160 160 150 130
表5
測定結果 比9 比10 比11 比12
ムーニースコーチ試験(125℃)
ML min (pts) 51 51 52 50
t5 (分) 3.6 3.6 3.5 3.0
架橋試験(180℃)
tc(10) (分) 0.53 0.50 0.51 0.51
tc(90) (分) 6.00 5.70 5.73 5.98
ML (N・m) 0.24 0.24 0.24 0.23
MH (N・m) 0.90 0.89 0.90 0.89
常態物性(ポストキュア)
硬度 (Duro A) 63 62 62 62
100%モジュラス (MPa) 5.2 5.4 5.3 4.8
破断時強度 (MPa) 13.2 13.9 13.5 13.6
破断時伸び (%) 200 200 190 210
熱老化試験(190℃、100時間)
硬度 (Duro A) 65 65 65 63
100%モジュラス (MPa) 3.3 3.6 3.9 2.6
破断時強度 (MPa) 9.2 10.2 10.5 8.4
破断時伸び (%) 240 240 240 290
熱老化試験(190℃、200時間)
硬度 (Duro A) 68 68 69 68
100%モジュラス (MPa) 2.8 3.0 3.2 2.4
破断時強度 (MPa) 7.0 7.4 7.7 6.2
破断時伸び (%) 250 250 240 280
熱老化試験(190℃、300時間)
硬度 (Duro A) 73 72 72 75
100%モジュラス (MPa) 2.5 2.6 2.8 3.0
破断時強度 (MPa) 5.6 5.9 6.2 5.8
破断時伸び (%) 240 260 240 220
熱老化試験(190℃、400時間)
硬度変化 (Duro A) 76 77 80 79
100%モジュラス (MPa) 2.5 2.7 2.9 5.1
破断時強度 (MPa) 4.0 4.3 4.5 6.2
破断時伸び (%) 230 220 210 130
熱老化試験(190℃、500時間)
硬度変化 (Duro A) 81 81 82 85
100%モジュラス (MPa) 3.0 3.1 3.6
破断時強度 (MPa) 3.7 4.0 4.3 7.7
破断時伸び (%) 160 170 150 80
熱老化試験(175℃、250時間)
硬度変化 (Duro A) 64 64 65 59
100%モジュラス (MPa) 3.5 3.7 4.0 2.6
破断時強度 (MPa) 9.4 9.9 10.6 8.3
破断時伸び (%) 230 230 230 270
熱老化試験(175℃、500時間)
硬度変化 (Duro A) 63 65 63 62
100%モジュラス (MPa) 2.8 2.8 3.2 2.5
破断時強度 (MPa) 7.2 7.2 8.1 6.3
破断時伸び (%) 240 260 240 250
熱老化試験(175℃、750時間)
硬度変化 (Duro A) 69 69 71 72
100%モジュラス (MPa) 2.7 2.9 3.3 3.0
破断時強度 (MPa) 5.8 6.5 6.8 6.2
破断時伸び (%) 270 250 250 240
熱老化試験(175℃、1000時間)
硬度変化 (Duro A) 78 80 79 83
100%モジュラス (MPa) 3.1 3.3 3.6 5.5
破断時強度 (MPa) 4.9 5.3 5.6 6.5
破断時伸び (%) 210 210 220 130
表6
測定結果 実12 比13 比14 比15
ムーニースコーチ試験(125℃)
ML min (pts) 60 57 57 56
t5 (分) 2.9 3.0 3.4 3.2
架橋試験(180℃)
tc(10) (分) 0.59 0.58 0.54 0.53
tc(90) (分) 6.39 6.40 5.90 6.02
ML (N・m) 0.21 0.21 0.23 0.23
MH (N・m) 0.80 0.80 0.87 0.87
常態物性(ポストキュア)
硬度 (Duro A) 64 63 65 65
100%モジュラス (MPa) 7.6 7.5 5.3 4.4
破断時強度 (MPa) 14.3 14.3 14.3 13.1
破断時伸び (%) 170 180 210 230
熱老化試験(190℃、100時間)
硬度 (Duro A) 73 69 70 66
100%モジュラス (MPa) 6.6 6.0 3.9 2.7
破断時強度 (MPa) 11.7 11.2 10.7 8.3
破断時伸び (%) 180 180 250 300
熱老化試験(190℃、200時間)
硬度 (Duro A) 73 72 67 63
100%モジュラス (MPa) 5.7 5.1 2.9 2.4
破断時強度 (MPa) 9.9 9.4 7.8 6.1
破断時伸び (%) 180 190 270 300
熱老化試験(190℃、300時間)
硬度 (Duro A) 75 77 73 76
100%モジュラス (MPa) 4.9 4.9 2.3 2.6
破断時強度 (MPa) 7.9 7.9 5.2 4.7
破断時伸び (%) 170 180 290 280
熱老化試験(190℃、400時間)
硬度変化 (Duro A) 80 79 77 79
100%モジュラス (MPa) 4.7 5.8 2.4 3.4
破断時強度 (MPa) 7.3 7.9 4.4 5.3
破断時伸び (%) 180 150 280 210
熱老化試験(190℃、500時間)
硬度変化 (Duro A) 85 85 80 85
100%モジュラス (MPa) 4.8 7.7 2.6 5.3
破断時強度 (MPa) 6.1 8.3 3.7 6.1
破断時伸び (%) 150 110 240 140
Claims (5)
- (A)成分が、
アルキル(メタ)アクリレートおよび/またはアルコキシアルキル(メタ)アクリレート単量体 90~99.9重量%と一般式〔III〕で表されるカルバミン酸エステル基含有(メタ)アクリレート単量体 0.1~10重量%との共単量体割合で共重合されたアクリルゴム
および
アルキル(メタ)アクリレートおよび/またはアルコキシアルキル(メタ)アクリレート単量体 90~99.9重量%とα,β-不飽和カルボン単量体 0.1~10重量%との共単量体割合で共重合体されたアクリルゴム
の混合物であって、それぞれの成分の重量比が90~10重量%、10~90重量%である請求項1記載の架橋性アクリルゴム組成物。 - アルキル(メタ)アクリレートがアクリル酸エチルまたはそれを含有する単量体混合物である請求項2または3記載の架橋性アクリルゴム組成物。
- α,β-不飽和カルボン酸単量体が二塩基酸α,β-不飽和カルボン酸モノアルキルエステルである請求項2または3記載の架橋性アクリルゴム組成物。
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WO2022049958A1 (ja) * | 2020-09-02 | 2022-03-10 | ユニマテック株式会社 | アクリルエラストマー共重合体およびその架橋性組成物 |
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WO2023223643A1 (ja) * | 2022-05-19 | 2023-11-23 | ユニマテック株式会社 | 架橋性アクリルゴム組成物 |
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