WO2022202406A1 - アクリルゴム、ゴム組成物およびゴム架橋物 - Google Patents
アクリルゴム、ゴム組成物およびゴム架橋物 Download PDFInfo
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- WO2022202406A1 WO2022202406A1 PCT/JP2022/010946 JP2022010946W WO2022202406A1 WO 2022202406 A1 WO2022202406 A1 WO 2022202406A1 JP 2022010946 W JP2022010946 W JP 2022010946W WO 2022202406 A1 WO2022202406 A1 WO 2022202406A1
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- rubber
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- acrylic rubber
- meth
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- 229920000800 acrylic rubber Polymers 0.000 title claims abstract description 147
- 229920000058 polyacrylate Polymers 0.000 title claims abstract description 147
- 229920001971 elastomer Polymers 0.000 title claims description 85
- 239000005060 rubber Substances 0.000 title claims description 78
- 239000000203 mixture Substances 0.000 title claims description 55
- 239000000178 monomer Substances 0.000 claims abstract description 166
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical group NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims abstract description 37
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 17
- 125000003700 epoxy group Chemical group 0.000 claims abstract description 14
- 125000005843 halogen group Chemical group 0.000 claims abstract description 14
- 238000004132 cross linking Methods 0.000 claims description 22
- 239000003431 cross linking reagent Substances 0.000 claims description 14
- -1 (meth)acrylic acid alkoxyalkyl ester Chemical class 0.000 description 115
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 65
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 49
- 239000003795 chemical substances by application Substances 0.000 description 48
- 238000007720 emulsion polymerization reaction Methods 0.000 description 48
- 238000000034 method Methods 0.000 description 48
- 229910019142 PO4 Inorganic materials 0.000 description 39
- 230000003712 anti-aging effect Effects 0.000 description 39
- 235000021317 phosphate Nutrition 0.000 description 39
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 37
- 125000004432 carbon atom Chemical group C* 0.000 description 37
- 239000010452 phosphate Substances 0.000 description 37
- 239000003995 emulsifying agent Substances 0.000 description 35
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 31
- 238000006116 polymerization reaction Methods 0.000 description 31
- 239000007788 liquid Substances 0.000 description 27
- 239000002530 phenolic antioxidant Substances 0.000 description 27
- 150000001875 compounds Chemical class 0.000 description 26
- 150000003839 salts Chemical class 0.000 description 22
- 239000003963 antioxidant agent Substances 0.000 description 21
- 235000006708 antioxidants Nutrition 0.000 description 21
- 238000005406 washing Methods 0.000 description 20
- 239000007864 aqueous solution Substances 0.000 description 19
- 239000000701 coagulant Substances 0.000 description 19
- 230000015271 coagulation Effects 0.000 description 19
- 238000005345 coagulation Methods 0.000 description 19
- 125000006353 oxyethylene group Chemical group 0.000 description 19
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 16
- 125000000217 alkyl group Chemical group 0.000 description 14
- 238000001035 drying Methods 0.000 description 14
- 150000002148 esters Chemical class 0.000 description 14
- 238000002844 melting Methods 0.000 description 14
- 230000008018 melting Effects 0.000 description 14
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 14
- 238000003756 stirring Methods 0.000 description 14
- 125000001931 aliphatic group Chemical group 0.000 description 13
- 230000003078 antioxidant effect Effects 0.000 description 13
- 239000006185 dispersion Substances 0.000 description 13
- 238000002156 mixing Methods 0.000 description 13
- 239000003638 chemical reducing agent Substances 0.000 description 12
- 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 11
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 11
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 11
- 229910052751 metal Inorganic materials 0.000 description 11
- 239000002184 metal Substances 0.000 description 11
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 10
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- 230000006835 compression Effects 0.000 description 10
- 238000007906 compression Methods 0.000 description 10
- 238000010438 heat treatment Methods 0.000 description 10
- 229910021645 metal ion Inorganic materials 0.000 description 10
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 229910052736 halogen Inorganic materials 0.000 description 9
- 150000002367 halogens Chemical class 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 8
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 7
- 235000010323 ascorbic acid Nutrition 0.000 description 7
- 239000011668 ascorbic acid Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 150000001993 dienes Chemical class 0.000 description 7
- 239000000806 elastomer Substances 0.000 description 7
- 235000003891 ferrous sulphate Nutrition 0.000 description 7
- 239000011790 ferrous sulphate Substances 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 7
- 238000004898 kneading Methods 0.000 description 7
- 229920000768 polyamine Polymers 0.000 description 7
- XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 7
- 229910052717 sulfur Inorganic materials 0.000 description 7
- 239000011593 sulfur Substances 0.000 description 7
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- 239000012874 anionic emulsifier Substances 0.000 description 6
- 150000002170 ethers Chemical class 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 5
- 229960005070 ascorbic acid Drugs 0.000 description 5
- 238000013329 compounding Methods 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 239000000945 filler Substances 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000000465 moulding Methods 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 150000002978 peroxides Chemical class 0.000 description 5
- 239000002685 polymerization catalyst Substances 0.000 description 5
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 239000012763 reinforcing filler Substances 0.000 description 5
- 239000011734 sodium Substances 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
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 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 4
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 125000005907 alkyl ester group Chemical group 0.000 description 4
- 125000000129 anionic group Chemical group 0.000 description 4
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- 150000002357 guanidines Chemical class 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000012875 nonionic emulsifier Substances 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- 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 3
- 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 3
- KWIPUXXIFQQMKN-UHFFFAOYSA-N 2-azaniumyl-3-(4-cyanophenyl)propanoate Chemical compound OC(=O)C(N)CC1=CC=C(C#N)C=C1 KWIPUXXIFQQMKN-UHFFFAOYSA-N 0.000 description 3
- XYPHEDNABNFRBL-UHFFFAOYSA-N 2-chloroethenyl acetate Chemical compound CC(=O)OC=CCl XYPHEDNABNFRBL-UHFFFAOYSA-N 0.000 description 3
- VSAWBBYYMBQKIK-UHFFFAOYSA-N 4-[[3,5-bis[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-2,4,6-trimethylphenyl]methyl]-2,6-ditert-butylphenol Chemical group CC1=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C1CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 VSAWBBYYMBQKIK-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- ACIAHEMYLLBZOI-ZZXKWVIFSA-N Unsaturated alcohol Chemical class CC\C(CO)=C/C ACIAHEMYLLBZOI-ZZXKWVIFSA-N 0.000 description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 3
- 150000005215 alkyl ethers Chemical class 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 3
- 229940090948 ammonium benzoate Drugs 0.000 description 3
- 235000019400 benzoyl peroxide Nutrition 0.000 description 3
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 3
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 230000018044 dehydration Effects 0.000 description 3
- 238000006297 dehydration reaction Methods 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 238000007599 discharging Methods 0.000 description 3
- 230000001804 emulsifying effect Effects 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 150000002460 imidazoles Chemical class 0.000 description 3
- 159000000003 magnesium salts Chemical class 0.000 description 3
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 3
- 238000000569 multi-angle light scattering Methods 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- ZMQWRASVUXJXGM-SREVYHEPSA-N (z)-4-cyclohexyloxy-4-oxobut-2-enoic acid Chemical compound OC(=O)\C=C/C(=O)OC1CCCCC1 ZMQWRASVUXJXGM-SREVYHEPSA-N 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- OPNUROKCUBTKLF-UHFFFAOYSA-N 1,2-bis(2-methylphenyl)guanidine Chemical compound CC1=CC=CC=C1N\C(N)=N\C1=CC=CC=C1C OPNUROKCUBTKLF-UHFFFAOYSA-N 0.000 description 2
- 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
- VNQNXQYZMPJLQX-UHFFFAOYSA-N 1,3,5-tris[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-1,3,5-triazinane-2,4,6-trione Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CN2C(N(CC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)C(=O)N(CC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)C2=O)=O)=C1 VNQNXQYZMPJLQX-UHFFFAOYSA-N 0.000 description 2
- XYXJKPCGSGVSBO-UHFFFAOYSA-N 1,3,5-tris[(4-tert-butyl-3-hydroxy-2,6-dimethylphenyl)methyl]-1,3,5-triazinane-2,4,6-trione Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C)=C1CN1C(=O)N(CC=2C(=C(O)C(=CC=2C)C(C)(C)C)C)C(=O)N(CC=2C(=C(O)C(=CC=2C)C(C)(C)C)C)C1=O XYXJKPCGSGVSBO-UHFFFAOYSA-N 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 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 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 2
- QSRJVOOOWGXUDY-UHFFFAOYSA-N 2-[2-[2-[3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propanoyloxy]ethoxy]ethoxy]ethyl 3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C)=CC(CCC(=O)OCCOCCOCCOC(=O)CCC=2C=C(C(O)=C(C)C=2)C(C)(C)C)=C1 QSRJVOOOWGXUDY-UHFFFAOYSA-N 0.000 description 2
- VFBJXXJYHWLXRM-UHFFFAOYSA-N 2-[2-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]ethylsulfanyl]ethyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCCSCCOC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 VFBJXXJYHWLXRM-UHFFFAOYSA-N 0.000 description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 2
- RTEZVHMDMFEURJ-UHFFFAOYSA-N 2-methylpentan-2-yl 2,2-dimethylpropaneperoxoate Chemical compound CCCC(C)(C)OOC(=O)C(C)(C)C RTEZVHMDMFEURJ-UHFFFAOYSA-N 0.000 description 2
- HXIQYSLFEXIOAV-UHFFFAOYSA-N 2-tert-butyl-4-(5-tert-butyl-4-hydroxy-2-methylphenyl)sulfanyl-5-methylphenol Chemical compound CC1=CC(O)=C(C(C)(C)C)C=C1SC1=CC(C(C)(C)C)=C(O)C=C1C HXIQYSLFEXIOAV-UHFFFAOYSA-N 0.000 description 2
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 2
- HCILJBJJZALOAL-UHFFFAOYSA-N 3-(3,5-ditert-butyl-4-hydroxyphenyl)-n'-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyl]propanehydrazide Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)NNC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 HCILJBJJZALOAL-UHFFFAOYSA-N 0.000 description 2
- QRLSTWVLSWCGBT-UHFFFAOYSA-N 4-((4,6-bis(octylthio)-1,3,5-triazin-2-yl)amino)-2,6-di-tert-butylphenol Chemical compound CCCCCCCCSC1=NC(SCCCCCCCC)=NC(NC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=N1 QRLSTWVLSWCGBT-UHFFFAOYSA-N 0.000 description 2
- ZVVFVKJZNVSANF-UHFFFAOYSA-N 6-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]hexyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCCCCCCOC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 ZVVFVKJZNVSANF-UHFFFAOYSA-N 0.000 description 2
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- PZFYOFFTIYJCEW-UHFFFAOYSA-N n-tridecyltridecan-1-amine Chemical compound CCCCCCCCCCCCCNCCCCCCCCCCCCC PZFYOFFTIYJCEW-UHFFFAOYSA-N 0.000 description 1
- 125000005609 naphthenate group Chemical group 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
- LGQLOGILCSXPEA-UHFFFAOYSA-L nickel sulfate Chemical compound [Ni+2].[O-]S([O-])(=O)=O LGQLOGILCSXPEA-UHFFFAOYSA-L 0.000 description 1
- 229910000363 nickel(II) sulfate Inorganic materials 0.000 description 1
- KBJMLQFLOWQJNF-UHFFFAOYSA-N nickel(ii) nitrate Chemical compound [Ni+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O KBJMLQFLOWQJNF-UHFFFAOYSA-N 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- DCKVFVYPWDKYDN-UHFFFAOYSA-L oxygen(2-);titanium(4+);sulfate Chemical compound [O-2].[Ti+4].[O-]S([O-])(=O)=O DCKVFVYPWDKYDN-UHFFFAOYSA-L 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 229920006124 polyolefin elastomer Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- CONVKSGEGAVTMB-RKJRWTFHSA-M potassium (2R)-2-[(1R)-1,2-dihydroxyethyl]-4-hydroxy-5-oxo-2H-furan-3-olate Chemical compound [K+].OC[C@@H](O)[C@H]1OC(=O)C(O)=C1[O-] CONVKSGEGAVTMB-RKJRWTFHSA-M 0.000 description 1
- 235000019275 potassium ascorbate Nutrition 0.000 description 1
- 229940017794 potassium ascorbate Drugs 0.000 description 1
- DJEHXEMURTVAOE-UHFFFAOYSA-M potassium bisulfite Chemical compound [K+].OS([O-])=O DJEHXEMURTVAOE-UHFFFAOYSA-M 0.000 description 1
- 229940099427 potassium bisulfite Drugs 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 235000010259 potassium hydrogen sulphite Nutrition 0.000 description 1
- 235000010333 potassium nitrate Nutrition 0.000 description 1
- 239000004323 potassium nitrate Substances 0.000 description 1
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
- 229910052939 potassium sulfate Inorganic materials 0.000 description 1
- BHZRJJOHZFYXTO-UHFFFAOYSA-L potassium sulfite Chemical compound [K+].[K+].[O-]S([O-])=O BHZRJJOHZFYXTO-UHFFFAOYSA-L 0.000 description 1
- 235000011151 potassium sulphates Nutrition 0.000 description 1
- 235000019252 potassium sulphite Nutrition 0.000 description 1
- CONVKSGEGAVTMB-RXSVEWSESA-M potassium-L-ascorbate Chemical compound [K+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] CONVKSGEGAVTMB-RXSVEWSESA-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
- 239000001294 propane Substances 0.000 description 1
- YPVDWEHVCUBACK-UHFFFAOYSA-N propoxycarbonyloxy propyl carbonate Chemical compound CCCOC(=O)OOC(=O)OCCC YPVDWEHVCUBACK-UHFFFAOYSA-N 0.000 description 1
- 238000004080 punching Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 238000010057 rubber processing Methods 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 239000011833 salt mixture Substances 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 235000010352 sodium erythorbate Nutrition 0.000 description 1
- 239000004320 sodium erythorbate Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- RBWSWDPRDBEWCR-RKJRWTFHSA-N sodium;(2r)-2-[(2r)-3,4-dihydroxy-5-oxo-2h-furan-2-yl]-2-hydroxyethanolate Chemical compound [Na+].[O-]C[C@@H](O)[C@H]1OC(=O)C(O)=C1O RBWSWDPRDBEWCR-RKJRWTFHSA-N 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000003760 tallow Substances 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
- RBTVSNLYYIMMKS-UHFFFAOYSA-N tert-butyl 3-aminoazetidine-1-carboxylate;hydrochloride Chemical compound Cl.CC(C)(C)OC(=O)N1CC(N)C1 RBTVSNLYYIMMKS-UHFFFAOYSA-N 0.000 description 1
- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
- 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
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- USNDJVGIYZJHOD-UHFFFAOYSA-N tetrapotassium;dioxidophosphanyl phosphite Chemical compound [K+].[K+].[K+].[K+].[O-]P([O-])OP([O-])[O-] USNDJVGIYZJHOD-UHFFFAOYSA-N 0.000 description 1
- JBEIJRWZSGVYNJ-UHFFFAOYSA-J tetrasodium 2-[6-[bis(carboxylatomethyl)amino]hexyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CCCCCCN(CC([O-])=O)CC([O-])=O)CC([O-])=O JBEIJRWZSGVYNJ-UHFFFAOYSA-J 0.000 description 1
- 239000006234 thermal black Substances 0.000 description 1
- 150000004764 thiosulfuric acid derivatives Chemical class 0.000 description 1
- FAKFSJNVVCGEEI-UHFFFAOYSA-J tin(4+);disulfate Chemical compound [Sn+4].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O FAKFSJNVVCGEEI-UHFFFAOYSA-J 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 229910000348 titanium sulfate Inorganic materials 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- VPYJNCGUESNPMV-UHFFFAOYSA-N triallylamine Chemical compound C=CCN(CC=C)CC=C VPYJNCGUESNPMV-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- OAHWWXAJFXEIPX-UHFFFAOYSA-M tributyl(octadecyl)azanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCCCC[N+](CCCC)(CCCC)CCCC OAHWWXAJFXEIPX-UHFFFAOYSA-M 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- ABVVEAHYODGCLZ-UHFFFAOYSA-N tridecan-1-amine Chemical compound CCCCCCCCCCCCCN ABVVEAHYODGCLZ-UHFFFAOYSA-N 0.000 description 1
- SWZDQOUHBYYPJD-UHFFFAOYSA-N tridodecylamine Chemical compound CCCCCCCCCCCCN(CCCCCCCCCCCC)CCCCCCCCCCCC SWZDQOUHBYYPJD-UHFFFAOYSA-N 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
- YQMWDQQWGKVOSQ-UHFFFAOYSA-N trinitrooxystannyl nitrate Chemical compound [Sn+4].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O YQMWDQQWGKVOSQ-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
- WXAZIUYTQHYBFW-UHFFFAOYSA-N tris(4-methylphenyl)phosphane Chemical compound C1=CC(C)=CC=C1P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 WXAZIUYTQHYBFW-UHFFFAOYSA-N 0.000 description 1
- NCPXQVVMIXIKTN-UHFFFAOYSA-N trisodium;phosphite Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])[O-] NCPXQVVMIXIKTN-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 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
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1802—C2-(meth)acrylate, e.g. ethyl (meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- 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
- C08F2/00—Processes of polymerisation
- C08F2/12—Polymerisation in non-solvents
- C08F2/16—Aqueous medium
- C08F2/22—Emulsion polymerisation
- C08F2/24—Emulsion polymerisation with the aid of emulsifying agents
- C08F2/26—Emulsion polymerisation with the aid of emulsifying agents anionic
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
-
- 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
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
- C08K5/11—Esters; Ether-esters of acyclic polycarboxylic acids
-
- 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
- C08L33/24—Homopolymers or copolymers of amides or imides
- C08L33/26—Homopolymers or copolymers of acrylamide or methacrylamide
-
- 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
- C08F220/22—Esters containing halogen
-
- 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
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/32—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals
- C08F220/325—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals containing glycidyl radical, e.g. glycidyl (meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- 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
- C08F220/52—Amides or imides
- C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F220/56—Acrylamide; Methacrylamide
Definitions
- the present invention relates to an acrylic rubber, a rubber composition and a crosslinked rubber product, and more particularly, an acrylic rubber having excellent processability and capable of providing a crosslinked rubber product excellent in elongation at break and tensile strength, and
- the present invention relates to a rubber composition and a cross-linked rubber obtained using such acrylic rubber.
- Acrylic rubber is a polymer whose main component is units derived from (meth)acrylic acid ester monomers such as (meth)acrylic acid alkyl ester monomers and (meth)acrylic acid alkoxyalkyl ester monomers. It is generally known as a rubber with excellent heat resistance, oil resistance, and ozone resistance, and is widely used in automobile-related fields.
- Such acrylic rubbers are usually monomers mainly composed of (meth)acrylic acid ester monomers such as (meth)acrylic acid alkyl ester monomers and (meth)acrylic acid alkoxyalkyl ester monomers. It is produced by emulsion polymerization of the components, coagulation by adding a coagulant to the obtained emulsion polymerization liquid, and drying the water-containing crumb obtained by coagulation (see, for example, Patent Document 1).
- the present invention has been made in view of such circumstances, and provides an acrylic rubber that has excellent processability and can provide a rubber cross-linked product that is excellent in elongation at break and tensile strength, and such acrylic rubber.
- the object is to provide a rubber composition and a cross-linked rubber obtained using the.
- the present inventors have found that at least In an acrylic rubber containing one type of crosslinkable group-containing monomer units and (meth)acrylamide monomer units, the content of the (meth)acrylamide monomer units in all monomer units
- the present inventors have found that the above object can be achieved by adjusting the content to 0.2 to 17.5% by weight, and have completed the present invention.
- At least one crosslinkable group-containing monomer selected from the group consisting of carboxyl group-containing monomer units, halogen atom-containing monomer units, and epoxy group-containing monomer units.
- An acrylic rubber is provided that is 0.5% by weight.
- the content of the (meth)acrylamide monomer units in all monomer units is preferably 1 to 15% by weight.
- the crosslinkable group-containing monomer unit is preferably the carboxyl group-containing monomer unit.
- a rubber composition containing a rubber component containing the acrylic rubber described above and a cross-linking agent. Further, according to the present invention, there is provided a cross-linked rubber obtained by cross-linking the rubber composition described above.
- an acrylic rubber having excellent processability and capable of providing a rubber crosslinked product excellent in elongation at break and tensile strength, a rubber composition obtained by using such an acrylic rubber, and A rubber crosslinked product can be provided.
- the acrylic rubber of the present invention contains at least one crosslinkable group-containing monomer selected from the group consisting of carboxyl group-containing monomer units, halogen atom-containing monomer units, and epoxy group-containing monomer units. and a (meth)acrylamide monomer unit, wherein the content of the (meth)acrylamide monomer unit in all monomer units is 0.2 to 17.5 It is in the weight percent range.
- a (meth)acrylic acid ester monomer (meth)acrylic acid ester monomer
- It means acrylic acid ester monomer and/or methacrylic acid ester monomer. The same applies to methyl (meth)acrylate and the like below. ] units.
- the (meth)acrylic acid ester monomer forming the (meth)acrylic acid ester monomer unit which is the main component of the acrylic rubber of the present invention is not particularly limited. monomers, and (meth)acrylic acid alkoxyalkyl ester monomers.
- the (meth)acrylic acid alkyl ester monomer is not particularly limited, but an ester of an alkanol having 1 to 12 carbon atoms and (meth)acrylic acid ((meth)acrylic acid having an alkyl group having 1 to 12 carbon atoms Ester) is preferred, more preferably an ester of an alkanol having 1 to 8 carbon atoms and (meth)acrylic acid ((meth)acrylic acid ester having an alkyl group having 1 to 8 carbon atoms), an alkanol having 2 to 6 carbon atoms and (meth)acrylic acid ((meth)acrylic acid ester having an alkyl group having 2 to 6 carbon atoms) is more preferable.
- (meth)acrylic acid alkyl ester monomers include methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, isopropyl (meth)acrylate, and (meth)acrylic acid.
- examples include n-butyl acid, isobutyl (meth)acrylate, n-hexyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, and cyclohexyl (meth)acrylate.
- ethyl (meth)acrylate and n-butyl (meth)acrylate are preferred, and ethyl acrylate and n-butyl acrylate are more preferred.
- These can be used individually by 1 type or in combination of 2 or more types.
- the (meth)acrylic acid alkoxyalkyl ester monomer is not particularly limited, but an ester of an alkoxyalkyl alcohol having 2 to 12 carbon atoms and (meth)acrylic acid (having an alkoxyalkyl group having 2 to 12 carbon atoms ( meth)acrylic acid ester) is preferred, more preferably an ester of alkoxyalkyl alcohol having 2 to 8 carbon atoms and (meth)acrylic acid ((meth)acrylic acid ester having an alkoxyalkyl group having 2 to 8 carbon atoms), Esters of alkoxyalkyl alcohols having 2 to 6 carbon atoms and (meth)acrylic acid ((meth)acrylic acid esters having an alkoxyalkyl group having 2 to 6 carbon atoms) are more preferable.
- (meth)acrylate alkoxyalkyl ester monomers include methoxymethyl (meth)acrylate, ethoxymethyl (meth)acrylate, 2-methoxyethyl (meth)acrylate, and 2-(meth)acrylate. ethoxyethyl, 2-propoxyethyl (meth)acrylate, 2-butoxyethyl (meth)acrylate, 3-methoxypropyl (meth)acrylate, and 4-methoxybutyl (meth)acrylate.
- 2-ethoxyethyl (meth)acrylate and 2-methoxyethyl (meth)acrylate are preferred, and 2-ethoxyethyl acrylate and 2-methoxyethyl acrylate are particularly preferred. These can be used individually by 1 type or in combination of 2 or more types.
- the content of the (meth)acrylic acid ester monomer unit in the total monomer units constituting the acrylic rubber of the present invention is preferably 50% by weight or more, more preferably 60% by weight or more, More preferably 70 to 99.79% by weight, still more preferably 80 to 99.5% by weight, particularly preferably 90 to 99% by weight. If the content of the (meth)acrylic acid ester monomer units is too low, the obtained crosslinked rubber may have reduced weather resistance, heat resistance, and oil resistance.
- the acrylic rubber of the present invention is selected from the group consisting of a (meth)acrylic acid ester monomer unit, a carboxyl group-containing monomer unit, a halogen atom-containing monomer unit, and an epoxy group-containing monomer unit. It contains at least one selected crosslinkable group-containing monomer unit. From the viewpoint of crosslinkability, the crosslinkable group-containing monomer unit is preferably a carboxyl group-containing monomer unit or a halogen atom-containing monomer unit, more preferably a carboxyl group-containing monomer unit.
- the carboxyl group-containing monomer that forms the carboxyl group-containing monomer unit is not particularly limited as long as it is a monomer having a carboxyl group.
- Examples include ⁇ , ⁇ -ethylenically unsaturated monocarboxylic acid, Examples include ⁇ , ⁇ -ethylenically unsaturated dicarboxylic acids and ⁇ , ⁇ -ethylenically unsaturated dicarboxylic acid monoesters.
- the acrylic rubber can be made into a carboxyl group-containing acrylic rubber having a carboxyl group as a cross-linking point. , the compression set resistance can be further enhanced.
- the ⁇ , ⁇ -ethylenically unsaturated monocarboxylic acid is not particularly limited, but ⁇ , ⁇ -ethylenically unsaturated monocarboxylic acids having 3 to 12 carbon atoms are preferable, and specific examples thereof include acrylic acid and methacrylic acid. , ⁇ -ethylacrylic acid, crotonic acid, and cinnamic acid.
- the ⁇ , ⁇ -ethylenically unsaturated dicarboxylic acid is not particularly limited, but is preferably an ⁇ , ⁇ -ethylenically unsaturated dicarboxylic acid having 4 to 12 carbon atoms, and specific examples thereof include fumaric acid, maleic acid, and the like.
- the ⁇ , ⁇ -ethylenically unsaturated dicarboxylic acid monoester is not particularly limited, but a monoester of an ⁇ , ⁇ -ethylenically unsaturated dicarboxylic acid having 4 to 12 carbon atoms and an alkanol having 1 to 12 carbon atoms is preferable.
- ⁇ , ⁇ -ethylenically unsaturated dicarboxylic acid having 4 to 6 carbon atoms and an alkanol having 2 to 8 carbon atoms and a monoester of butenedioic acid having 4 carbon atoms and an alkanol having 2 to 6 carbon atoms.
- Esters are more preferred.
- Specific examples of ⁇ , ⁇ -ethylenically unsaturated dicarboxylic acid monoesters include butenediones such as monomethyl fumarate, monoethyl fumarate, mono-n-butyl fumarate, monomethyl maleate, monoethyl maleate and mono-n-butyl maleate.
- acid monochain alkyl esters butenedioic acid monoesters having an alicyclic structure such as monocyclopentyl fumarate, monocyclohexyl fumarate, monocyclohexenyl fumarate, monocyclopentyl maleate, monocyclohexyl maleate, monocyclohexenyl maleate; itaconic acid monoesters such as monomethyl itaconate, monoethyl itaconate, mono-n-butyl itaconate, and monocyclohexyl itaconate;
- ⁇ , ⁇ -ethylenically unsaturated dicarboxylic acid monoesters are preferable, butenedionic acid monochain alkyl esters or butenedionic acid monoesters having an alicyclic structure are more preferable, mono-n-butyl fumarate, maleic acid More preferred are mono-n-butyl, monocyclohexyl fumarate, and monocyclohexyl maleate, with mono-n-butyl fumarate being particularly preferred.
- These ⁇ , ⁇ -ethylenically unsaturated carboxylic acid monomers can be used alone or in combination of two or more.
- the dicarboxylic acid includes those present as an anhydride.
- the halogen atom-containing monomer that forms the halogen atom-containing monomer unit is not particularly limited, but examples include unsaturated alcohol esters of halogen-containing saturated carboxylic acids, (meth)acrylic acid haloalkyl esters, (meth)acrylic acid Haloacyloxyalkyl esters, (meth)acrylate (haloacetylcarbamoyloxy)alkyl esters, halogen-containing unsaturated ethers, halogen-containing unsaturated ketones, halomethyl group-containing aromatic vinyl compounds, halogen-containing unsaturated amides, and haloacetyl group-containing unsaturated Examples include saturated monomers. In addition, it is preferable that the monomer having a halogen atom contains a chlorine atom as a halogen atom.
- unsaturated alcohol esters of halogen-containing saturated carboxylic acids include vinyl monochloroacetate, vinyl 2-chloropropionate, and allyl chloroacetate.
- haloalkyl (meth)acrylates include chloromethyl (meth)acrylate, 1-chloroethyl (meth)acrylate, 2-chloroethyl (meth)acrylate, and 1,2-dichloroethyl (meth)acrylate. , 2-chloropropyl (meth)acrylate, 3-chloropropyl (meth)acrylate, and 2,3-dichloropropyl (meth)acrylate.
- (meth)acrylic acid haloacyloxyalkyl esters include 2-(chloroacetoxy)ethyl (meth)acrylate, 2-(chloroacetoxy)propyl (meth)acrylate, 3-(chloro acetoxy)propyl, and 3-(hydroxychloroacetoxy)propyl (meth)acrylate.
- Specific examples of (haloacetylcarbamoyloxy)alkyl (meth)acrylates include 2-(chloroacetylcarbamoyloxy)ethyl (meth)acrylate and 3-(chloroacetylcarbamoyloxy)propyl (meth)acrylate. are mentioned.
- halogen-containing unsaturated ethers include chloromethyl vinyl ether, 2-chloroethyl vinyl ether, 3-chloropropyl vinyl ether, 2-chloroethyl allyl ether, 3-chloropropyl allyl ether, and the like.
- halogen-containing unsaturated ketones include 2-chloroethyl vinyl ketone, 3-chloropropyl vinyl ketone, 2-chloroethyl allyl ketone, and the like.
- halomethyl group-containing aromatic vinyl compounds include p-chloromethylstyrene, m-chloromethylstyrene, o-chloromethylstyrene, and p-chloromethyl- ⁇ -methylstyrene.
- halogen-containing unsaturated amides include N-chloromethyl(meth)acrylamide.
- haloacetyl group-containing unsaturated monomers include 3-(hydroxychloroacetoxy)propyl allyl ether, p-vinylbenzyl chloroacetate and the like.
- halogen atom-containing monomers can be used singly or in combination of two or more.
- unsaturated alcohol esters of halogen-containing saturated carboxylic acids are preferred, and monochlorovinyl acetate is more preferred.
- the epoxy group-containing monomer that forms the epoxy group-containing monomer unit is not particularly limited, but examples include epoxy group-containing (meth)acrylic acid esters such as glycidyl (meth)acrylate; allyl glycidyl ether and vinyl glycidyl epoxy group-containing ethers such as ethers; and the like. These epoxy group-containing monomers can be used singly or in combination of two or more. Among these epoxy group-containing monomers, epoxy group-containing (meth)acrylic acid esters are preferred, and glycidyl methacrylate is more preferred.
- the content of the crosslinkable group-containing monomer units in the total monomer units constituting the acrylic rubber of the present invention is preferably 0.01% by weight or more, more preferably 0.01 to 20% by weight. , more preferably 0.1 to 10% by weight, still more preferably 0.5 to 5% by weight, and particularly preferably 1 to 3% by weight.
- the acrylic rubber of the present invention contains (meth)acrylamide monomer units in addition to (meth)acrylic acid ester monomer units as main components and the crosslinkable group-containing monomer units described above. is.
- the (meth)acrylamide monomer either acrylamide or methacrylamide can be used, but acrylamide is preferred. Also, acrylamide and methacrylamide may be used in combination.
- the content of (meth)acrylamide monomer units in the total monomer units constituting the acrylic rubber of the present invention is 0.2 to 17.5% by weight, preferably 1 to 15% by weight. , more preferably 2 to 10% by weight.
- the content of the (meth)acrylamide monomer unit is 0.2 to 17.5% by weight, preferably 1 to 15% by weight. , more preferably 2 to 10% by weight.
- the cross-linked rubber obtained is inferior in elongation at break and tensile strength.
- the content of the (meth)acrylamide monomer unit is more than the above range, the polymer becomes soluble in water, making it difficult to recover the acrylic rubber by the coagulation operation, or making it water resistant. It may be inferior to
- the acrylic rubber of the present invention includes, in addition to (meth)acrylic acid ester monomer units, crosslinkable group-containing monomer units, and (meth)acrylamide monomer units, may have a monomer unit of
- Such other copolymerizable monomers are not particularly limited, but aromatic vinyl monomers, ⁇ , ⁇ -ethylenically unsaturated nitrile monomers, ⁇ , ⁇ -ethylenically unsaturated dicarboxylic acids Examples include diester monomers, diene monomers, non-conjugated diene monomers, and other olefinic monomers.
- Styrene, ⁇ -methylstyrene, divinylbenzene and the like are examples of aromatic vinyl monomers.
- Examples of ⁇ , ⁇ -ethylenically unsaturated nitrile monomers include acrylonitrile and methacrylonitrile.
- Examples of ⁇ , ⁇ -ethylenically unsaturated dicarboxylic acid diester monomers include dialkyl maleates such as dimethyl maleate and di-n-butyl maleate having alkyl groups of 1 to 18 carbon atoms; fumaric acid; Dialkyl fumarate esters such as dimethyl and di-n-butyl fumarate, in which the alkyl group has 1 to 18 carbon atoms; Dicycloalkyl maleate esters such as dicyclopentyl maleate and dicyclohexyl maleate, which are cycloalkyl dicycloalkyl fumarate esters such as dicyclopentyl fumarate and dicyclohexyl fumarate, in which the cycloalkyl group has 4 to 16 carbon atoms; dimethyl itaconate, di-itaconate Dialky
- diene monomers examples include conjugated diene monomers and non-conjugated diene monomers.
- conjugated diene monomers include 1,3-butadiene, isoprene, piperylene, and the like.
- non-conjugated diene monomers include ethylidenenorbornene, dicyclopentadiene, dicyclopentadienyl (meth)acrylate, and 2-dicyclopentadienylethyl (meth)acrylate.
- styrene, acrylonitrile, methacrylonitrile, ethylene and vinyl acetate are preferred, and acrylonitrile, methacrylonitrile and ethylene are more preferred.
- the other copolymerizable monomers can be used singly or in combination of two or more.
- the content of units of these other copolymerizable monomers in the monomer units constituting the acrylic rubber of the present invention is preferably 49.9% by weight or less, more preferably 29.9% by weight. %, more preferably 15% by weight or less, even more preferably 9% by weight or less, and particularly preferably 4.5% by weight or less.
- the content may be within the above range.
- the content of ethylene units in the monomer units constituting the acrylic rubber of the present invention is preferably 9% by weight or less, more preferably 4.5% by weight or less. preferable.
- the acrylic rubber of the present invention contains acrylonitrile units or methacrylonitrile units
- the total content of acrylonitrile units and methacrylonitrile units is preferably 9% by weight or less. , 4.5% by weight or less.
- the acrylic rubber of the present invention preferably contains a phenol-based anti-aging agent as an anti-aging agent.
- the phenol-based anti-aging agent is not particularly limited as long as it is a compound having a phenol structure (that is, a structure having a benzene ring and an OH group bonded to the benzene ring).
- phenolic antioxidants include double-hindered phenolic antioxidants, semi-hindered phenolic antioxidants, less hindered phenolic antioxidants, and phenolic antioxidants having no hindered groups. be done.
- Both hindered phenol-based antioxidants are phenolic compounds in which both the 2- and 6-positions (that is, two ortho-positions) of the OH groups (phenolic hydroxyl groups) that constitute the phenolic structure are hindered groups.
- the hindered group is not particularly limited as long as it is bulky, and includes substituents having 4 or more carbon atoms.
- hindered groups include tertiary alkyl groups such as t-butyl, t-pentyl and t-hexyl; secondary alkyl groups such as sec-butyl and sec-pentyl; i-butyl, A branched primary alkyl group such as an i-pentyl group; a cycloalkyl group such as a cyclohexyl group and a cyclopentyl group; an octylthio group and an octylthiomethyl group; and alkyl groups.
- tertiary alkyl groups such as t-butyl, t-pentyl and t-hexyl
- secondary alkyl groups such as sec-butyl and sec-pentyl
- i-butyl A branched primary alkyl group such as an i-pentyl group
- a cycloalkyl group such as a cyclohexyl
- both hindered phenol anti-aging agents include pentaerythritol tetrakis [3-(3,5-di-tert-butyl-4-hydroxyphenyl) propionate] (for example, trade name "Irganox 1010", BASF company), 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl) isocyanurate (for example, trade name “Irganox 3114”, manufactured by BASF), 2,4,6 -tris(4-hydroxy-3,5-di-tert-butylbenzyl)mesitylene (for example, trade name "Irganox 1330", manufactured by BASF), 6-(4-hydroxy-3,5-di-tert- Butylanilino)-2,4-bis(octylthio)-1,3,5-triazine (for example, trade name "Irganox 565", manufactured by BASF), 2,2'-thiodiethylbis[3
- either one of the 2- and 6-positions of the OH group (phenolic hydroxyl group) constituting the phenol structure is a hindered group, and the other is a methyl group or the like having 3 or less carbon atoms. It is a phenolic compound that is an alkyl group (preferably a methyl group).
- semi-hindered phenol-based antioxidants include 4,6-bis(octylthiomethyl)-o-cresol (trade name "Irganox 1520L", manufactured by BASF), 1,3,5-tris [ [4-(1,1-dimethylethyl)-3-hydroxy-2,6-dimethylphenyl]methyl]-1,3,5-triazine-2,4,6(1H,3H,5H)-trione (product Name "Irganox 1790", manufactured by BASF), 3,9-bis[2- ⁇ 3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propionyloxy ⁇ -1,1-dimethylethyl] -2,4,8,10-tetraoxaspiro[5,5]undecane (for example, trade name "ADEKA STAB AO-80” manufactured by ADEKA), ethylenebis(oxyethylene)bis[3-(5-tert) -butyl-hydroxy-m-tolyl
- a less hindered phenol-based antioxidant is a phenol-based compound in which either one of the 2- and 6-positions of the OH group (phenolic hydroxyl group) constituting the phenol structure is a hindered group and the other is a hydrogen atom. is.
- resin hindered phenol anti-aging agents include 1,1,3-tris-(2-methyl-4-hydroxy-5-tertiarybutylphenyl)butane (eg, trade name "ADEKA STAB AO-30"). , manufactured by ADEKA), 4,4′-butylidenebis(6-t-butyl-3-methylphenol) (for example, trade name “ADEKA STAB AO-40” manufactured by ADEKA), 4,4′-thiobis(6- t-butyl-3-methylphenol) (for example, trade name "Sumilizer WX-R", manufactured by Sumitomo Chemical Co., Ltd.) and the like.
- the phenol-based antioxidants can be used singly or in combination of two or more.
- phenol-based antioxidants both hindered phenol-based antioxidants and semi-hindered phenol-based antioxidants are preferable. agents are preferred.
- the phenol-based anti-aging agent preferably has a molecular weight of 470 or less, more preferably 100-450, and even more preferably 150-400.
- a phenol-based anti-aging agent having a molecular weight of 500 or less it is possible to more appropriately suppress the generation of coloration and odor.
- the content of the phenolic antioxidant is preferably 0.1 to 5 parts by weight, more preferably 0.2 to 3.0 parts by weight, still more preferably 0.3 parts by weight, per 100 parts by weight of the acrylic rubber component. ⁇ 2.0 parts by weight.
- the Mooney viscosity (ML1+4, 100°C) of the acrylic rubber of the present invention is not particularly limited, but is preferably in the range of 10 to 150, more preferably in the range of 20 to 100, and particularly preferably in the range of 25 to 70. . By setting the Mooney viscosity within the above range, the workability and strength properties of the acrylic rubber can be highly balanced.
- the pH of the acrylic rubber of the present invention is not particularly limited, but is preferably 6 or less, more preferably 2-6, even more preferably 2.5-5.5, and particularly preferably 3-5. By setting the pH within the above range, the storage stability of the acrylic rubber can be further enhanced.
- the weight average molecular weight (Mw) of the acrylic rubber of the present invention is not particularly limited, but is preferably 800,000 or more, more preferably 800, from the viewpoint of improving mechanical strength and workability. ,000 to 2,600,000, more preferably 900,000 to 2,300,000, and particularly preferably 1,000,000 to 2,000,000.
- the molecular weight distribution of the acrylic rubber is not particularly limited, but the Mw/Mn value is preferably 1.50 to 10.0, more preferably 1.70 to 8.00, and still more preferably 2.00. ⁇ 6.00, and the value of Mz / Mw is preferably 1.30 to 3.00, more preferably 1.45 to 2.70, still more preferably 1.60 to 2.50 be.
- the weight average molecular weight and molecular weight distribution of the acrylic rubber can be determined, for example, by the GPC-MALS method using a GPC (Gel Permeation Chromatography) device incorporating a multi-angle laser light scattering photometer (MALS).
- GPC-MALS Gel Permeation Chromatography
- MALS multi-angle laser light scattering photometer
- the method for producing the acrylic rubber of the present invention is not particularly limited, and any method may be adopted.
- the following method is suitable. That is, a monomer component containing a (meth)acrylic acid ester monomer, a crosslinkable group-containing monomer and a (meth)acrylamide monomer, which forms an acrylic rubber, is subjected to emulsion polymerization in the presence of a polymerization catalyst. It can be manufactured by
- Examples of monomer components used in emulsion polymerization include the above-described monomers, and suitable monomers are also as described above. Moreover, the amount of each monomer to be used may be appropriately selected so as to achieve the composition range described above.
- emulsion polymerization method a conventional method may be used, and an emulsifier, a polymerization initiator, a polymerization terminator, etc. may be used according to the standard method.
- the emulsifier is not particularly limited, but a phosphate ester salt can be preferably used.
- a phosphate ester salt a compound represented by the following general formula (1) is preferable.
- R 1 represents a linear or branched alkyl group having 4 to 20 carbon atoms, an alkylphenyl group, or an unsaturated alkyl group having 4 to 20 carbon atoms
- R 2 represents a 2 or 3 linear or branched alkylene groups
- M represents an alkali metal
- m is an integer of 1 to 20
- p is 1 or 2
- n+p is 3.
- R 1 represents a linear or branched alkyl group having 4 to 20 carbon atoms, an alkylphenyl group, or an unsaturated alkyl group having 4 to 20 carbon atoms.
- R 1 preferably has 4 or more and 18 or less carbon atoms, more preferably 5 or more and 16 or less carbon atoms, and even more preferably 6 or more and 14 or less carbon atoms.
- R 1 examples include n-octyl group, n-decyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, isooctyl group, isotridecyl group, n-octadecyl group, nonylphenyl group and the like. be done.
- R 2 represents a linear or branched alkylene group having 2 or 3 carbon atoms.
- R 2 include an ethylene group, a propylene group, and the like, and among these, an ethylene group is more preferable.
- M represents an alkali metal, and specific examples of M include sodium, potassium, lithium, rubidium, and cesium. Among these, as M, sodium and potassium are preferable.
- m is an integer of 1 to 20, preferably an integer of 2 or more and 15 or less, more preferably an integer of 2 or more and 13 or less, and 2 or more and 11 or less. is more preferably an integer of
- R 2 may have a plurality of different groups. That is, for example, R 2 may have both an ethylene group and a propylene group.
- n is 1 or 2, preferably 1.
- p is 1 or 2, preferably 2. Note that n+p is 3.
- phosphate ester salts can be used singly, or in combination of two or more with different n numbers, or in combination of two or more with different ester types. Among these combinations, a mixture of n different phosphate ester salts is preferable, and a mixture of n different phosphate ester salts with the same ester species is more preferable.
- the mixing ratio in the phosphate ester salt mixture with different n numbers is not particularly limited.
- the amount of the phosphate ester used is preferably 0.01 to 10 parts by weight, more preferably 0.1 to 5 parts by weight, and still more preferably 1 to 3 parts by weight, based on 100 parts by weight of the monomer component used for polymerization. weight part.
- Examples of the phosphate represented by the general formula (1) include octyloxydi(oxyethylene) phosphate, dodecyloxydi(oxyethylene) phosphate, tridecyloxytri(oxyethylene) phosphorus, acid ester, hexyloxytetra(oxyethylene) phosphate, heptylhexaoxytetra(oxyethylene) phosphate, octyloxytetra(oxyethylene) phosphate, nonyloxytetra(oxyethylene) phosphate, decyl Oxytetra(oxyethylene) phosphate, Decyloxytetra(oxyethylene) phosphate, Octadecyloxytetra(oxyethylene) phosphate, Nonylphenyloxytetra(oxyethylene) phosphate, Tridecyloxytetra(oxy ethylene) phosphate, octyloxyhexa(oxyethylene) phosphate, decyloxyhexa(oxyethylene) phosphate
- an emulsifier other than the phosphate ester salt can be used together with the phosphate ester salt or in place of the phosphate ester salt.
- emulsifiers other than phosphate ester salts include anionic emulsifiers other than phosphate ester salts, cationic emulsifiers, and nonionic emulsifiers.
- anionic emulsifiers other than phosphate ester salts and nonionic emulsifiers are preferable, and it is preferable to use a combination of anionic emulsifiers other than phosphate ester salts and nonionic emulsifiers.
- anionic emulsifiers other than phosphate ester salts include, but are not limited to, fatty acid salts such as myristic acid, palmitic acid, oleic acid, and linolenic acid; alkylbenzene sulfonates such as sodium dodecylbenzene sulfonate; lauryl sulfate; sulfuric ester salts such as sodium; alkyl sulfosuccinates; and the like.
- cationic emulsifiers include, but are not limited to, alkyltrimethylammonium chloride, dialkylammonium chloride, and benzylammonium chloride.
- nonionic emulsifiers include, but are not limited to, polyoxyalkylene fatty acid esters such as polyoxyethylene stearate; polyoxyalkylene alkyl ethers such as polyoxyethylene dodecyl ether; polyoxyethylenes such as polyoxyethylene nonylphenyl ether; alkylene alkylphenol ether; polyoxyethylene sorbitan alkyl ester; and the like.
- polyoxyalkylene alkyl ethers and polyoxyalkylene alkylphenol ethers are preferred, and polyoxyethylene alkyl ethers and polyoxyethylene alkylphenol ethers are more preferred.
- Emulsifiers other than phosphate ester salts can be used singly or in combination of two or more.
- the amount of the emulsifier used is preferably 0.01 to 10 parts by weight, more preferably 0.1 to 5 parts by weight, still more preferably 1 to 10 parts by weight, based on 100 parts by weight of the monomer component used for polymerization. 3 parts by weight.
- the amount of the nonionic emulsifier used is more than 0 parts by weight with respect to 100 parts by weight of the monomer used for polymerization.
- 4 parts by weight or less preferably 0.1 to 3 parts by weight, more preferably 0.5 to 2 parts by weight, still more preferably 0.7 to 1.7 parts by weight, an anionic emulsifier other than a phosphate ester salt
- the amount used is more than 0 parts by weight, 4 parts by weight or less, preferably 0.1 to 3 parts by weight, more preferably 0.5 to 2 parts by weight, with respect to 100 parts by weight of the monomer used for polymerization. It is preferably 0.35 to 0.75 parts by weight.
- the ratio of use is 1/99 to 99 in the weight ratio of the nonionic emulsifier/anionic emulsifier other than the phosphate ester salt. /1 is preferred, 10/90 to 80/20 is more preferred, 25/75 to 75/25 is even more preferred, 50/50 to 75/25 is even more preferred, and 65/35 to 75/25 is particularly preferred.
- a monomer component containing a (meth)acrylic acid ester as a main component is pre-emulsified using water and an emulsifier to obtain an emulsion, and the obtained emulsion is treated with a polymerization catalyst.
- Emulsion polymerization in the presence is preferred.
- the method of emulsifying the monomer component mainly composed of (meth)acrylic acid ester using water and an emulsifier is not particularly limited, but the monomer component, water, and an emulsifier is preferable, and a method of stirring the monomer component, water, and emulsifier using a stirrer such as a homogenizer or a disk turbine is more preferable.
- the amount of water used when emulsifying the monomer component is preferably 5 to 500 parts by weight, more preferably 10 to 300 parts by weight, and still more preferably 100 parts by weight of the monomer component used for polymerization. 20 to 200 parts by weight.
- the polymerization catalyst is not particularly limited, and those commonly used in emulsion polymerization can be used without limitation.
- a redox catalyst comprising a radical generator and a reducing agent can be used.
- radical generators examples include peroxides and azo compounds, among which peroxides are preferred.
- peroxide either an inorganic peroxide or an organic peroxide may be used.
- inorganic peroxides examples include sodium persulfate, potassium persulfate, hydrogen peroxide, and ammonium persulfate.
- potassium persulfate, hydrogen peroxide and ammonium persulfate are preferred, and potassium persulfate is particularly preferred.
- organic peroxides examples include 2,2-di(4,4-di-(t-butylperoxy)cyclohexyl)propane, 1-di-(t-hexylperoxy)cyclohexane, 1,1- Di-(t-butylperoxy)cyclohexane, 4,4-di-(t-butylperoxy)n-butyl valerate, 2,2-di-(t-butylperoxy)butane, t-butylhydroperoxy oxide, cumene hydroperoxide, diisopropylbenzene hydroperoxide, paramenthane hydroperoxide, benzoyl peroxide, 1,1,3,3-tetraethylbutyl hydroperoxide, t-butylcumyl peroxide, di-t-butylperoxide oxide, di-t-hexyl peroxide, di(2-t-butylperoxyisopropyl)benzene, dicumyl
- azo compounds include azobisisobutyronitrile, 4,4′-azobis(4-cyanovaleric acid), 2,2′-azobis[2-(2-imidazolin-2-yl)propane, 2, 2′-azobis (propane-2-carbamidine), 2,2′-azobis[N-(2-carboxyethyl)-2-methylpropanamide], 2,2′-azobis ⁇ 2-[1-(2 -hydroxyethyl)-2-imidazolin-2-yl]propane ⁇ , 2,2′-azobis(1-imino-1-pyrrolidino-2-methylpropane), 2,2′-azobis ⁇ 2-methyl-N- [1,1-bis(hydroxymethyl)-2-hydroxyethyl]propanamide ⁇ and the like.
- radical generators can be used singly or in combination of two or more.
- the amount of the radical generator used is preferably 0.0001 to 5 parts by weight, more preferably 0.0005 to 1 part by weight, still more preferably 0.001 to 1 part by weight, based on 100 parts by weight of the monomer component used for polymerization. 0.5 part by weight.
- any reducing agent that can be used as a redox catalyst for emulsion polymerization can be used without limitation.
- the reducing agent it is preferable to use at least two kinds of reducing agents. Among them, a combination of a metal ion compound in a reduced state and another reducing agent is preferable.
- the metal ion compound in a reduced state is not particularly limited, but examples thereof include ferrous sulfate, ferrous sodium hexamethylenediaminetetraacetate, and cuprous naphthenate. Among these, ferrous sulfate is preferred.
- the metal ion compounds in a reduced state can be used singly or in combination of two or more.
- the amount of the metal ion compound in a reduced state to be used is preferably 0.000001 to 0.01 parts by weight, more preferably 0.00001 to 0.001 parts by weight, per 100 parts by weight of the monomer component used for polymerization. and more preferably in the range of 0.00005 to 0.0005 parts by weight.
- the reducing agent other than the metal ion compound in a reduced state is not particularly limited, but for example, ascorbic acid or salts thereof such as ascorbic acid, sodium ascorbate, potassium ascorbate; erythorbic acid, sodium erythorbate, potassium erythorbate, etc.
- sulfinates such as sodium hydroxymethanesulfinate (sodium formaldehyde sulfoxylate); sulfites of sodium sulfite, potassium sulfite, sodium bisulfite, aldehyde sodium bisulfite, potassium bisulfite; sodium pyrosulfite , potassium pyrosulfite, sodium pyrosulfite, and potassium pyrosulfite; thiosulfates such as sodium thiosulfate and potassium thiosulfate; phosphorous acid, sodium phosphite, potassium phosphite, sodium hydrogen phosphite, Phosphorous acid of potassium hydrogen phosphate or its salt; Pyrophosphorous acid or its salt such as pyrophosphorous acid, sodium pyrophosphite, potassium pyrophosphite, sodium pyrophosphite, potassium hydrogen pyrophosphit
- Reducing agents other than metal ion compounds in a reduced state can be used singly or in combination of two or more.
- the amount of the reducing agent other than the metal ion compound in a reduced state to be used is preferably 0.001 to 1 part by weight, more preferably 0.005 to 0.5 part by weight, with respect to 100 parts by weight of the monomer component used for polymerization. parts by weight, more preferably 0.01 to 0.3 parts by weight.
- Preferred combinations of the metal ion compound in a reduced state and a reducing agent other than the metal ion compound in a reduced state include ferrous sulfate, ascorbic acid or a salt thereof and/or sodium hydroxymethanesulfinate (sodium formaldehyde sulfonate). oxylate), more preferably a combination of ferrous sulfate with ascorbate and/or sodium hydroxymethanesulfinate (sodium formaldehyde sulfoxylate), ferrous sulfate and ascorbate A combination with is particularly preferred.
- the amount of ferrous sulfate used is preferably 0.000001 to 0.01 parts by weight, more preferably 0.00001 to 0.001 parts by weight, relative to 100 parts by weight of the monomer component used for polymerization. parts, more preferably 0.00005 to 0.0005 parts by weight. It is preferably 0.001 to 1 part by weight, more preferably 0.005 to 0.5 part by weight, still more preferably 0.01 to 0.3 part by weight.
- the amount of water used in the emulsion polymerization is preferably 10 to 1000 parts by weight, more preferably 50 to 800 parts by weight, and still more preferably 80 to 600 parts by weight with respect to 100 parts by weight of the monomer component used for polymerization. parts, particularly preferably 100 to 400 parts by weight.
- the amount of water used in the emulsion polymerization may be adjusted so that the amount of water used for emulsifying the monomer components is within the above range.
- the emulsion polymerization may be carried out using only the water used, or the emulsion polymerization may be carried out after adding water.
- secondary polymerization materials such as molecular weight modifiers, particle size modifiers, chelating agents, and oxygen scavengers can be used.
- Emulsion polymerization may be carried out by any of batch, semi-batch, and continuous methods, but the semi-batch method is preferred.
- the polymerization temperature and polymerization time are not particularly limited, and may be appropriately selected according to the type of polymerization catalyst to be used. is between 10 and 50°C. Moreover, the polymerization time is preferably 0.5 to 100 hours, more preferably 1 to 10 hours.
- the polymerization conversion rate is not particularly limited, but is preferably 80% by weight or more, more preferably 90% by weight or more, and still more preferably 95% by weight or more.
- a polymerization terminator can be used when terminating the polymerization reaction.
- the polymerization terminator include hydroxylamine, hydroxylamine sulfate, diethylhydroxyamine, hydroxylaminesulfonic acid and alkali metal salts thereof, sodium dimethyldithiocarbamate, and hydroquinone.
- the amount of the polymerization terminator used is not particularly limited, but is preferably 0.1 to 2 parts by weight with respect to 100 parts by weight of the monomer component used for polymerization.
- a phenol-based anti-aging agent to the emulsion polymerization solution of acrylic rubber obtained by emulsion polymerization.
- a phenol-based anti-aging agent to the emulsion polymerization liquid for acrylic rubber, it is preferable to employ either the following addition method (1) or addition method (2).
- Addition method (1) A method of adding a phenolic antioxidant to an emulsion polymerization solution of acrylic rubber under a temperature condition equal to or higher than the melting point of the phenolic antioxidant
- Addition method (2) A phenolic antioxidant A dispersion is obtained by contacting with an aqueous solution of an emulsifier at a temperature above the melting point of the phenolic antioxidant, and the phenolic antioxidant is added to the emulsion polymerization liquid of the acrylic rubber in the state of the dispersion.
- the phenol-based antioxidant When the phenol-based antioxidant is added to the emulsion polymerization solution of the acrylic rubber, the phenol-based antioxidant can be emulsion-polymerized by adopting either the addition method (1) or the addition method (2). To be able to disperse uniformly in a liquid, and as a result, to uniformly disperse the phenol-based anti-aging agent in the acrylic rubber after coagulation, thereby making the addition effect sufficient. is possible.
- the phenol-based antioxidant is not particularly limited as a specific addition method when adding to the emulsion polymerization solution of the acrylic rubber under a temperature condition equal to or higher than the melting point of the phenol-based antioxidant.
- a preferred method is to add the phenolic antioxidant to the emulsion polymerization solution while keeping the emulsion polymerization solution at a temperature equal to or higher than the melting point of the phenolic antioxidant.
- the amount of the phenolic antioxidant added to the emulsion polymerization liquid is usually very small. The above temperature is convenient and suitable.
- the temperature condition may be the melting point or higher of the phenolic antioxidant used. It is more preferable to carry out the addition under the temperature condition of melting point +10°C or higher, and it is further preferable to carry out addition under the temperature condition of melting point +15°C or higher of the phenolic antiaging agent to be used.
- the phenol-based antioxidant is brought into contact with an aqueous solution of the emulsifier under a temperature condition equal to or higher than the melting point of the phenol-based antioxidant, thereby obtaining a dispersion of the phenol-based antioxidant.
- the emulsifier is not particularly limited, but from the viewpoint of dispersibility when the dispersion of the phenolic anti-aging agent is added to the emulsion polymerization liquid, it is possible to use the same emulsifier as the emulsifier used in the emulsion polymerization described above. preferable. Moreover, when two or more emulsifiers are used in the emulsion polymerization described above, it is preferable to use at least one of the two or more emulsifiers.
- the amount of the emulsifier to be used is preferably such that the concentration of the emulsifier in the dispersion of the phenolic anti-aging agent is 0.5 to 20% by weight, more preferably 1.0 to 15% by weight. is more preferable, and an amount of 2.0 to 10% by weight is even more preferable.
- the phenolic antioxidant can be sufficiently dispersed in the dispersion of the phenolic antioxidant.
- the phenol-based anti-aging agent can be dispersed more uniformly.
- the method of contacting the phenol-based antioxidant with the aqueous solution of the emulsifier under a temperature condition of the melting point or higher of the phenol-based antioxidant is not particularly limited.
- a preferred method is to add the phenolic antioxidant to an aqueous solution of the emulsifier while the temperature is maintained at a temperature equal to or higher than the melting point of the antioxidant.
- the temperature condition may be the melting point or higher of the phenolic antioxidant used. It is more preferable to carry out the addition under the temperature condition of +10°C or higher than the melting point of the agent, and it is further preferable to carry out the addition under the condition of +15°C or higher of the melting point of the phenolic anti-aging agent used.
- the content of the phenolic antioxidant in the phenolic antioxidant dispersion is not particularly limited, but it is preferable that the concentration of the phenolic antioxidant is 10 to 80% by weight. It is more preferable to set the amount to 75% by weight, more preferably 30 to 70% by weight. By setting the content of the phenolic antioxidant within the above range, the phenolic antioxidant can be more uniformly dispersed when the phenolic antioxidant dispersion is added to the emulsion polymerization liquid. .
- the amount of the phenol-based anti-aging agent to be added to the emulsion polymerization solution may be an amount such that the content in the acrylic rubber is within the above range. , preferably 0.1 to 5 parts by weight, more preferably 0.2 to 3 parts by weight, still more preferably 0.3 to 2 parts by weight, per 100 parts by weight of the acrylic rubber component contained in the emulsion polymerization liquid. is.
- Phenolic anti-aging agents usually remain in the acrylic rubber after solidification even after the coagulation operation described later. You just have to decide.
- a coagulant is brought into contact with the emulsion polymerization liquid to which the phenol-based anti-aging agent has been added to coagulate and generate water-containing crumbs.
- the coagulant is not particularly limited, but includes, for example, monovalent to trivalent metal salts.
- the monovalent to trivalent metal salt is a salt containing a metal that becomes a monovalent to trivalent metal ion when dissolved in water, and is not particularly limited.
- an inorganic acid selected from hydrochloric acid, nitric acid, sulfuric acid, etc. or acetic acid with a metal selected from sodium, potassium, lithium, magnesium, calcium, zinc, titanium, manganese, iron, cobalt, nickel, aluminum and tin. Hydroxides of these metals can also be used.
- monovalent to trivalent metal salts include sodium chloride, potassium chloride, lithium chloride, magnesium chloride, calcium chloride, zinc chloride, titanium chloride, manganese chloride, iron chloride, cobalt chloride, nickel chloride, aluminum chloride, chloride Metal chlorides such as tin; nitrates such as sodium nitrate, potassium nitrate, lithium nitrate, magnesium nitrate, calcium nitrate, zinc nitrate, titanium nitrate, manganese nitrate, iron nitrate, cobalt nitrate, nickel nitrate, aluminum nitrate, tin nitrate; sodium sulfate , potassium sulfate, lithium sulfate, magnesium sulfate, calcium sulfate, zinc sulfate, titanium sulfate, manganese sulfate, iron sulfate, cobalt sulfate, nickel sulfate, aluminum sulfate,
- monovalent or divalent metal salts are preferred, divalent metal salts are more preferred, magnesium salts are more preferred, inorganic magnesium salts are more preferred, and magnesium sulfate is particularly preferred.
- these can be used individually by 1 type or in combination of multiple types.
- the amount of the coagulant used is preferably 0.01 to 100 parts by weight, more preferably 0.1 to 50 parts by weight, and still more preferably 1 to 30 parts by weight, based on 100 parts by weight of the monomer component used in the polymerization. is.
- the method for contacting the emulsion polymerization liquid and the coagulant is not particularly limited. Examples include a method of adding a liquid and a method of adding an aqueous solution containing a coagulant to the emulsion polymerization liquid being stirred while the emulsion polymerization liquid is being stirred. Alternatively, a method of simply adding an emulsion polymerization liquid to an aqueous solution containing a coagulant without stirring, or a method of adding an aqueous solution containing a coagulant to an emulsion polymerization liquid may be employed.
- the method of adding the emulsion polymerization liquid to the stirred aqueous solution containing the coagulant while stirring the aqueous solution containing the coagulant is preferable, and the coagulation operation is performed by adopting such a method.
- the concentration of the magnesium salt in the aqueous solution containing the coagulant is not particularly limited, but is preferably 0.1 to 20% by weight, more preferably 0.1 to 20% by weight, from the viewpoint of more suitably controlling the particle size of the hydrous crumbs produced by coagulation. is 0.5 to 10% by weight, more preferably 1 to 5% by weight.
- the temperature of the aqueous solution containing the coagulant (that is, the coagulation temperature) is not particularly limited, but is preferably 40° C. or higher, more preferably 40° C. or higher, from the viewpoint of more suitably controlling the particle size of the water-containing crumbs produced by coagulation. is 50-90°C.
- the stirring method for stirring the aqueous solution containing the coagulant is not particularly limited, but examples include a method using a stirring device that stirs with a stirring blade.
- the coagulant is added to the stirring vessel. It is preferable to employ a method of adding the emulsion polymerization liquid while the aqueous solution containing the coagulant is added to the aqueous solution containing the coagulant while stirring the aqueous solution containing the coagulant in a stirring vessel.
- the solid content concentration of the emulsion polymerization liquid used for coagulation is not particularly limited, and it may be used as it is in the state obtained by performing emulsion polymerization and adding an anti-aging agent. From the viewpoint of more suitably controlling the particle size of the crumbs, it is preferable to adjust the solid content concentration in the range of 5 to 50% by weight, more preferably 10 to 45% by weight, and 20 to 40% by weight. It is particularly preferred to adjust the weight percent range.
- the washing method is not particularly limited, but includes, for example, a method of washing the water-containing crumbs obtained by the coagulation operation with water, preferably a method of mixing the water-containing crumbs obtained by the coagulation operation with water. etc.
- the temperature for washing with water is not particularly limited, but is preferably 5 to 60° C., more preferably 10 to 50° C., and the mixing time is 1 to 60 minutes, more preferably 2 to 30 minutes.
- the amount of water to be mixed with the water-containing crumbs when washing with water is not particularly limited.
- the amount is preferably 50 to 15,000 parts by weight, more preferably 100 to 10,000 parts by weight, and particularly preferably 500 to 5,000 parts by weight.
- the washing time is not particularly limited, but is preferably 1 to 120 minutes, more preferably 2 to 60 minutes, still more preferably 3 to 30 minutes.
- the number of washings is not particularly limited, and is preferably 1 to 10 times, more preferably 1 to 5 times, still more preferably 1 to 3 times.
- the number of washings means the operation of adding water to the wet crumbs, mixing for a predetermined time, and then separating the wet crumbs from the water used for washing. It is the number of times when That is, for example, washing with water twice means adding water to the wet crumbs, mixing for a predetermined time, and then separating the wet crumbs from the water used for washing. Furthermore, water is added to the water-containing crumbs, and after mixing for a predetermined time, the water-containing crumbs are separated from the water used for washing.
- the number of washings is two or more, the water temperature, the amount of water, and the washing time used for washing may be the same or different.
- acid washing may be further performed using an acid as a washing liquid. It is preferable to wash with water after acid washing, and the conditions for washing with water may be the same as those described above.
- the washed wet crumbs may be dried.
- the method for drying the water-containing crumbs is not particularly limited, and it may be performed according to a conventional method. and methods to do so.
- the temperature for drying the water-containing crumbs is not particularly limited, but is preferably 80 to 250°C, more preferably 100 to 200°C.
- the method of dehydrating the water-containing crumbs is not particularly limited, but includes a method of discharging water from the water-containing crumbs using a dehydrator such as a centrifugal separator, a squeezer, or a screw-type extruder. From the viewpoint that the water content of the water-containing crumbs can be further reduced, a method using a squeezer and a screw extruder is preferable, and a method using a screw extruder is particularly preferable. Dewatering and drying of the crumbs can be done in a continuous process, which can increase productivity.
- a twin-screw extruder having a barrel unit consisting of a plurality of barrel blocks and a pair of screws rotatably arranged inside the barrel unit can be suitably used.
- the barrel unit includes, in order from the feed side of the water-containing crumb, a feed barrel section consisting of one or two or more feed barrel blocks, a dewatering barrel section consisting of one or two or more dewatering barrel blocks, and one or two or more drying barrels.
- a drying barrel section consisting of blocks may be provided.
- a die for extruding the dehydrated and dried acrylic rubber into a sheet is connected to the downstream side of the drying barrel.
- the supply barrel part is the area where the wet crumb is supplied to the inside of the barrel unit.
- the dewatering barrel section is a region for separating and discharging a liquid (cerum water) containing a coagulant and the like from the water-containing crumb. with a slit for discharging the
- the drying barrel section is a region for drying the dehydrated crumbs dehydrated by the dewatering barrel section.
- the set temperature in the dehydration barrel is preferably 60 to 150°C, more preferably 70 to 140°C, still more preferably 80 to 130°C.
- the set temperature in the drying barrel is preferably 100 to 250°C, more preferably 110 to 200°C, still more preferably 120 to 180°C.
- the screw length (L) of the pair of screws arranged inside the barrel unit constituting the screw-type extruder is not particularly limited, but is preferably 3000 to 15000 mm, more preferably 4000 to 10000 mm, more preferably 4500. ⁇ 8000 mm.
- the screw diameter (D) of the screw is not particularly limited, but is preferably 50 to 250 mm, more preferably 100 to 200 mm, still more preferably 120 to 160 mm.
- the ratio (L/D) of the screw length (L) to the screw diameter (D) of the screw is not particularly limited, but is preferably 10 to 100, more preferably 20 to 80, and still more preferably 30 to is 60.
- the operating conditions of the screw-type extruder when dehydrating and drying the water-containing crumbs using the screw-type extruder are not particularly limited, but include, for example, the following conditions. That is, the rotation speed N [rpm] of the pair of screws arranged inside the barrel unit is preferably 10 to 1000 rpm, and from the viewpoint that the water content and gel amount of the acrylic rubber can be efficiently reduced, It is more preferably 50 to 750 rpm, still more preferably 100 to 500 rpm, and particularly preferably 120 to 300 rpm.
- the throughput Q [kg/hr] of the acrylic rubber dried per unit time by the screw type extruder is preferably 100 to 1500 kg/hr, more preferably 300 to 1200 kg/hr, still more preferably 400 to 1000 kg. /hr, particularly preferably 500 to 800 kg/hr.
- the ratio (Q/N) between the amount Q of the acrylic rubber to be dried per unit time and the number of rotations N of the screw is not particularly limited, but is preferably 1 to 20, more preferably 2 to 2. 10, more preferably 3-8, and particularly preferably 4-6.
- the rubber pressure (resin pressure or discharge pressure) in the die connected to the downstream side of the drying barrel is not particularly limited, but from the viewpoint of achieving high productivity while effectively suppressing entrainment of air, It is preferably 0.1 to 10 MPa, more preferably 0.5 to 5 MPa, still more preferably 1 to 3 MPa.
- the temperature of the water-containing crumbs supplied to the screw-type extruder is not particularly limited, but from the viewpoint that the dehydration and drying efficiency can be improved, and the water resistance of the resulting acrylic rubber can be further improved, it is 60 ° C. or higher. It is preferable to
- acrylic rubber can be produced as described above.
- acrylic rubber may be obtained in the form of crumbs, or may be obtained as veiled rubber, that is, acrylic rubber veil (acrylic rubber made into lumps of a predetermined shape).
- the rubber composition of the present invention comprises a rubber component containing the above-described acrylic rubber of the present invention, and a cross-linking agent.
- the content of the acrylic rubber component of the present invention in the rubber component may be appropriately selected according to the purpose of use, but is preferably 30% by weight or more, more preferably 50% by weight or more, and still more preferably 70% by weight. % or more, particularly preferably 100% by weight (that is, an embodiment using a rubber component substantially consisting only of an acrylic rubber component).
- the rubber other than the acrylic rubber of the present invention that constitutes the rubber component is not particularly limited, but acrylic rubber other than the acrylic rubber of the present invention, natural rubber, polybutadiene rubber, polyisoprene rubber, styrene-butadiene rubber, acrylonitrile-butadiene rubber. , silicone rubber, fluororubber, olefin-based elastomer, styrene-based elastomer, vinyl chloride-based elastomer, polyester-based elastomer, polyamide-based elastomer, polyurethane-based elastomer, polysiloxane-based elastomer, and the like.
- the rubbers other than the acrylic rubber of the present invention can be used singly or in combination of two or more.
- the shape of the acrylic rubber of the present invention and the shape of the rubber other than the acrylic rubber of the present invention are not particularly limited, but may be any shape such as veil, sheet, or powder.
- the cross-linking agent is not particularly limited, but for example, polyamine compounds such as diamine compounds, and carbonates thereof; sulfur; sulfur donors; triazinethiol compounds; polyepoxy compounds; organic carboxylic acid ammonium salts; dithiocarbamic acid metal salt; polyvalent carboxylic acid; quaternary onium salt; imidazole compound; isocyanuric acid compound;
- These cross-linking agents can be used alone or in combination of two or more. It is preferable to appropriately select the cross-linking agent according to the type of the cross-linkable group-containing monomer unit.
- the acrylic rubber of the present invention has a carboxyl group-containing monomer unit as the crosslinkable group-containing monomer unit, a polyvalent amine compound and its carbonate are used as the cross-linking agent. is preferred.
- polyvalent amine compound and its carbonate are not particularly limited, a polyvalent amine compound having 4 to 30 carbon atoms and its carbonate are preferable.
- examples of such polyamine compounds and carbonates thereof include aliphatic polyamine compounds and carbonates thereof, aromatic polyamine compounds, and the like.
- the aliphatic polyvalent amine compound and its carbonate are not particularly limited, but include, for example, hexamethylenediamine, hexamethylenediamine carbamate, and N,N'-dicinnamylidene-1,6-hexanediamine. Among these, hexamethylenediamine carbamate is preferred.
- aromatic polyvalent amine compounds include, but are not limited to, 4,4'-methylenedianiline, p-phenylenediamine, m-phenylenediamine, 4,4'-diaminodiphenyl ether, and 3,4'-diaminodiphenyl ether.
- the acrylic rubber of the present invention has a halogen atom-containing monomer unit as a crosslinkable group-containing monomer unit
- sulfur, a sulfur donor, a triazinethiol compound, a polyvalent amine compound can be used as a cross-linking agent.
- a carbonate of a polyvalent amine compound is preferably used.
- sulfur donors include dipentamethylenethiuram hexasulfide and triethylthiuram disulfide.
- Triazine compounds include, for example, 2,4,6-trimercapto-s-triazine, 2-anilino-4,6-dithiol-s-triazine, 2-dibutylamino-4,6-dithiol-s-triazine, 1 -hexylamino-3,5-dimercaptotriazine and the like. Among these, 2,4,6-trimercapto-s-triazine is preferred.
- the polyvalent amine compound and the carbonate of the polyvalent amine compound for example, those described above can be used.
- the content of the cross-linking agent in the rubber composition of the present invention is preferably 0.001 to 20 parts by weight, more preferably 0.1 to 10 parts by weight, per 100 parts by weight of the rubber component containing the acrylic rubber of the present invention. parts by weight, more preferably 0.1 to 5 parts by weight, particularly preferably 0.2 to 4 parts by weight.
- the cross-linking agent may be a polyamine compound, a polyamine compound, or a polyamine compound.
- polyvalent amine compound and the carbonate of the polyvalent amine compound for example, those described above can be used.
- carboxylate ammonium salts and dithiocarbamate metal salts are preferred, and ammonium benzoate is more preferred.
- the rubber composition of the present invention preferably further contains a cross-linking accelerator.
- the cross-linking accelerator is not particularly limited, but when the acrylic rubber of the present invention has a carboxyl group as a cross-linkable group and the cross-linking agent is a polyvalent amine compound or its carbonate, , guanidine compounds, diazabicycloalkene compounds, imidazole compounds, quaternary onium salts, tertiary phosphine compounds, aliphatic monovalent secondary amine compounds, and aliphatic monovalent tertiary amine compounds.
- guanidine compounds, diazabicycloalkene compounds, and aliphatic monovalent secondary amine compounds are preferred, and guanidine compounds and diazabicycloalkene compounds are particularly preferred.
- These basic cross-linking accelerators can be used alone or in combination of two or more.
- guanidine compounds include 1,3-di-o-tolylguanidine and 1,3-diphenylguanidine.
- diazabicycloalkene compounds include 1,8-diazabicyclo[5.4.0]undec-7-ene, 1,5-diazabicyclo[4.3.0]no-5-ene and the like.
- imidazole compounds include 2-methylimidazole and 2-phenylimidazole.
- quaternary onium salts include tetra-n-butylammonium bromide and octadecyltri-n-butylammonium bromide.
- tertiary phosphine compounds include triphenylphosphine and tri-p-tolylphosphine.
- An aliphatic monovalent secondary amine compound is a compound in which two hydrogen atoms of ammonia are substituted with an aliphatic hydrocarbon group.
- the aliphatic hydrocarbon group that replaces the hydrogen atom preferably has 1 to 30 carbon atoms.
- aliphatic monovalent secondary amine compounds include dimethylamine, diethylamine, dipropylamine, diallylamine, diisopropylamine, di-n-butylamine, di-t-butylamine, di-sec-butylamine, dihexylamine, di- heptylamine, dioctylamine, dinonylamine, didecylamine, diundecylamine, didodecylamine, ditridecylamine, ditetradecylamine, dipentadecylamine, dicetylamine, di-2-ethylhexylamine, dioctadecylamine, and the like.
- An aliphatic monovalent tertiary amine compound is a compound in which all three hydrogen atoms of ammonia are substituted with aliphatic hydrocarbon groups.
- the aliphatic hydrocarbon group that replaces the hydrogen atom preferably has 1 to 30 carbon atoms.
- Specific examples of aliphatic monovalent tertiary amine compounds include trimethylamine, triethylamine, tripropylamine, triallylamine, triisopropylamine, tri-n-butylamine, tri-t-butylamine, tri-sec-butylamine and trihexylamine. , triheptylamine, trioctylamine, trinonylamine, tridecylamine, triundecylamine, and tridodecylamine.
- the content of the cross-linking accelerator in the rubber composition of the present invention is preferably 0.1 to 10 parts by weight, more preferably 0.1 to 10 parts by weight, per 100 parts by weight of the rubber component containing the acrylic rubber of the present invention. 5 to 7.5 parts by weight, particularly preferably 1 to 5 parts by weight.
- the rubber composition of the present invention may further contain a filler.
- the filler is not particularly limited, but includes reinforcing fillers, non-reinforcing fillers, etc. Among these, reinforcing fillers are preferred.
- reinforcing fillers examples include carbon black such as furnace black, acetylene black, thermal black, channel black and graphite; silica such as wet silica, dry silica and colloidal silica; Non-reinforcing fillers include quartz powder, clay such as diatomaceous earth, zinc oxide, basic magnesium carbonate, activated calcium carbonate, magnesium silicate, aluminum silicate, titanium dioxide, talc, aluminum sulfate, calcium sulfate, barium sulfate and the like.
- the content of the filler in the rubber composition of the present invention is not particularly limited, but is preferably 1 to 200 parts by weight, more preferably 10 parts by weight, per 100 parts by weight of the rubber component containing the acrylic rubber of the present invention. 150 parts by weight, more preferably 20 to 100 parts by weight.
- the rubber composition of the present invention may be blended with an anti-aging agent as necessary. That is, in addition to the phenol-based anti-aging agent optionally contained in the acrylic rubber, an anti-aging agent may be additionally added.
- the anti-aging agent is not particularly limited, but the phenol-based anti-aging agents described above; tris(nonylphenyl)phosphite, diphenylisodecylphosphite, tetraphenyldipropylene glycol diphosphite, and other phosphite-based anti-aging agents; Sulfur ester anti-aging agents such as dilauryl thiodipropionate; benzyl)diphenylamine, N,N-diphenyl-p-phenylenediamine, N-isopropyl-N'-phenyl-p-phenylenediamine, butyraldehyde-aniline condensates; amine antioxidants; 2-mercaptobenzimidazole, etc
- imidazole-based anti-aging agents such as 6-ethoxy-2,2,4-trimethyl-1,2-dihydroquinoline
- hydroquinone-based anti-aging agents such as 2,5-di-(t-amyl) hydroquinone agent; and the like.
- the anti-aging agents can be used singly or in combination of two or more.
- the content of the antioxidant in the rubber composition of the present invention is not particularly limited, but is preferably 0.01 to 15 parts by weight, more than 100 parts by weight of the rubber component containing the acrylic rubber of the present invention. It is preferably 0.05 to 10 parts by weight, more preferably 0.1 to 5 parts by weight.
- the rubber composition of the present invention may contain compounding agents commonly used in the field of rubber processing.
- compounding agents include, for example, light stabilizers; anti-scorch agents; plasticizers; processing aids; pressure-sensitive adhesives; lubricants; ; and the like.
- the blending amount of these compounding agents is not particularly limited as long as it does not impair the object and effect of the present invention, and the amount can be appropriately blended according to the blending purpose.
- the rubber composition of the present invention is prepared by blending a rubber component containing the acrylic rubber of the present invention described above with a cross-linking agent and other various compounding agents that are used as necessary, and mixing with an open roll, Banbury mixer, various kneaders, etc. , kneading, and then further kneading using kneading rolls.
- each component is mixed, but after thoroughly mixing the components that are difficult to react or decompose with heat, add a cross-linking agent, which is a component that easily reacts or decomposes with heat, at a temperature where no reaction or decomposition occurs. Mixing for a short time is preferred.
- the rubber cross-linked product of the present invention is obtained by cross-linking the rubber composition of the present invention described above.
- the rubber cross-linked product of the present invention can be obtained by molding the acrylic rubber composition of the present invention into a desired shape using a molding machine such as an extruder, an injection molding machine, a compressor, and a roll, followed by heating. It can be produced by performing a cross-linking reaction with and fixing the shape as a rubber cross-linked product. In this case, the cross-linking may be performed after pre-molding, or the cross-linking may be performed at the same time as the molding.
- the molding temperature is usually 10-200°C, preferably 25-120°C.
- the cross-linking temperature is generally 130-220° C., preferably 150-190° C.
- the cross-linking time is generally 2 minutes-10 hours, preferably 3 minutes-5 hours.
- a method used for cross-linking rubber such as press heating, steam heating, oven heating, and hot air heating, may be appropriately selected.
- the crosslinked rubber product of the present invention may be further heated for secondary crosslinking.
- the secondary cross-linking is preferably carried out for 1 to 48 hours, although it varies depending on the heating method, cross-linking temperature, shape and the like. A heating method and a heating temperature may be appropriately selected.
- the rubber cross-linked product of the present invention thus obtained can be used for O-rings, packings, diaphragms, oil seals, shaft seals, bearing sheaths, mechanical seals, well head seals, seals for electrical and electronic equipment, and air compression equipment.
- Sealing materials such as seals for cylinders; cylinder head gaskets attached to the connection between the cylinder block and the cylinder head, rocker cover gaskets attached to the connection between the rocker cover and the cylinder head, oil pan and cylinder head or transmission case
- gaskets such as an oil pan gasket attached to the connection part of the fuel cell separator gasket attached between a pair of housings sandwiching a unit cell with a positive electrode, an electrolyte plate and a negative electrode, and a hard disk drive top cover gasket; It is suitably used as cushioning materials, vibration-proof materials, electric wire covering materials, industrial belts, tubes and hoses, sheets, and the like.
- the cross-linked rubber product of the present invention can also be used as extrusion-molded products and cross-linked products for use in automobiles, such as fuel hoses, filler neck hoses, vent hoses, vapor hoses, and fuel tanks such as oil hoses. It is suitably used for various hoses such as air hoses such as hoses, turbo air hoses, mission control hoses, radiator hoses, heater hoses, brake hoses and air conditioner hoses.
- air hoses such as hoses, turbo air hoses, mission control hoses, radiator hoses, heater hoses, brake hoses and air conditioner hoses.
- the monomer composition of the acrylic rubber was calculated from the amount of each monomer used in the polymerization reaction and the polymerization conversion rate. Specifically, in the emulsion polymerization reaction in each example and comparative example, none of the unreacted monomers could be confirmed, and the polymerization conversion rate was approximately 100%. The amount of the monomer used was assumed to be the same as the content of each monomer unit constituting the acrylic rubber.
- Mooney viscosity (ML1+4, 100°C) Mooney viscosity (Polymer Mooney) of acrylic rubber was measured according to JISK6300:2013.
- part (about half) of the rubber composition stuck to the roll is peeled off from the roll, and the peeled rubber composition piece is transferred to the other rubber composition piece stuck to the roll.
- It is a kneading operation in which the operation of stacking the mixture on top and passing it through the rolls again in the stacked state is repeated.
- the gap between the rolls is minimized, and in the thickness direction of the sheet-like rubber composition, the long side of the rubber composition is in the axial direction of the roll.
- It is a kneading operation in which the operation of passing the rubber composition through the rolls again is repeated so that the rubber composition intersects perpendicularly with the rollers.
- Example 1 Manufacture of acrylic rubber (A-1) 46.294 parts of ion-exchanged water, 46.8 parts of ethyl acrylate, 46.8 parts of n-butyl acrylate, 5 parts of acrylamide, and mono-n fumarate as monomer components were placed in a mixing vessel equipped with a homomixer. -Butyl 1.4 parts and tridecyloxyhexa(oxyethylene) phosphate sodium salt (anionic emulsifier) 1.8 parts as an emulsifier were charged and stirred to obtain a monomer emulsion.
- anionic emulsifier anionic emulsifier
- the resulting mixture was transferred to a roll at 50° C., and 0.5 parts of hexamethylenediamine carbamate (trade name “Diak #1”, manufactured by DuPont Dow Elastomers) per 100 parts of acrylic rubber (A-1), and 2 parts of 1,3-di-o-tolylguanidine (trade name “Noccellar DT”, manufactured by Ouchi Shinko Kagaku Kogyo Co., Ltd.) were blended and kneaded with a roll to obtain an acrylic rubber composition.
- Noccellar DT 1,3-di-o-tolylguanidine
- Example 2 The amount of each monomer component used was changed to 48.8 parts of ethyl acrylate, 48.8 parts of n-butyl acrylate, 1 part of acrylamide, and 1.4 parts of mono-n-butyl fumarate.
- An acrylic rubber (A-2) was obtained in the same manner as in Example 1. Further, an acrylic rubber composition was prepared in the same manner as in Example 1 except that the obtained acrylic rubber (A-2) was used, and these were evaluated in the same manner as in Example 1. Table 1 shows the results.
- Example 3 The amount of each monomer component used was changed to 41.8 parts of ethyl acrylate, 41.8 parts of n-butyl acrylate, 15 parts of acrylamide, and 1.4 parts of mono-n-butyl fumarate.
- An acrylic rubber (A-3) was obtained in the same manner as in Example 1. Further, an acrylic rubber composition was prepared in the same manner as in Example 1 except that the obtained acrylic rubber (A-3) was used, and these were evaluated in the same manner as in Example 1. Table 1 shows the results.
- Example 4 Ethyl acrylate is not used as a monomer component, and the amount of other monomer components used is changed to 93.6 parts of n-butyl acrylate, 5 parts of acrylamide, and 1.4 parts of mono n-butyl fumarate.
- Acrylic rubber (A-4) was obtained in the same manner as in Example 1, except that Further, an acrylic rubber composition was prepared in the same manner as in Example 1 except that the obtained acrylic rubber (A-4) was used, and these were evaluated in the same manner as in Example 1. Table 1 shows the results.
- Example 5 (Manufacture of acrylic rubber (A-5)) Acrylic rubber (A-5) was prepared in the same manner as in Example 1, except that 1.4 parts of monocyclohexyl fumarate was used as the monomer component instead of 1.4 parts of mono-n-butyl fumarate. Obtained. Further, an acrylic rubber composition was prepared in the same manner as in Example 1 except that the obtained acrylic rubber (A-5) was used, and these were evaluated in the same manner as in Example 1. Table 1 shows the results.
- Example 6 (Manufacture of acrylic rubber (A-6)) Acrylic rubber (A-6) was obtained in the same manner as in Example 1, except that 1.4 parts of glycidyl methacrylate was used as the monomer component instead of 1.4 parts of mono-n-butyl fumarate. rice field. The obtained acrylic rubber (A-6) was evaluated in the same manner as in Example 1. Table 1 shows the results.
- Example 7 (Manufacture of acrylic rubber (A-7)) Monochlorovinyl acetate was used instead of mono-n-butyl fumarate as the monomer component, and the amount of each monomer component used was 46.2 parts of ethyl acrylate, 46.2 parts of n-butyl acrylate, An acrylic rubber (A-7) was obtained in the same manner as in Example 1, except that 5 parts of acrylamide and 2.6 parts of monochlorovinyl acetate were used. The obtained acrylic rubber (A-7) was evaluated in the same manner as in Example 1. Table 1 shows the results.
- Acrylic rubber (A-10) was prepared in the same manner as in Example 1, except that ethyl acrylate and acrylamide were not used as monomer components and the amount of n-butyl acrylate used was changed to 98.6 parts. Obtained. Further, an acrylic rubber composition was prepared in the same manner as in Example 1 except that the obtained acrylic rubber (A-10) was used, and these were evaluated in the same manner as in Example 1. Table 1 shows the results.
- At least one crosslinkable group selected from the group consisting of carboxyl group-containing monomer units, halogen atom-containing monomer units, and epoxy group-containing monomer units Contains a monomer unit and a (meth)acrylamide monomer unit, and the content of the (meth)acrylamide monomer unit in all monomer units is 0.2 to 17.5% by weight
- the acrylic rubber the adhesion to the roll is suppressed and the workability is excellent, and the cross-linked rubber obtained has a high elongation at break and a high tensile strength (implementation Examples 1-8).
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Abstract
Description
本発明のアクリルゴムにおいて、全単量体単位中における、前記(メタ)アクリルアミド単量体単位の含有量が1~15重量%であることが好ましい。
本発明のアクリルゴムにおいて、前記架橋性基含有単量体単位が前記カルボキシル基含有単量体単位であることが好ましい。
また、本発明によれば、上記に記載のゴム組成物を架橋してなるゴム架橋物が提供される。
本発明のアクリルゴムは、カルボキシル基含有単量体単位、ハロゲン原子含有単量体単位、および、エポキシ基含有単量体単位からなる群から選択される少なくとも1種の架橋性基含有単量体単位と、(メタ)アクリルアミド単量体単位と、を含有するアクリルゴムであって、全単量体単位中における、前記(メタ)アクリルアミド単量体単位の含有量が0.2~17.5重量%の範囲にあるものである。
α,β-エチレン性不飽和ジカルボン酸としては、特に限定されないが、炭素数4~12のα,β-エチレン性不飽和ジカルボン酸が好ましく、その具体例としては、フマル酸、マレイン酸などのブテンジオン酸;イタコン酸;シトラコン酸;クロロマレイン酸;などが挙げられる。
α,β-エチレン性不飽和ジカルボン酸モノエステルとしては、特に限定されないが、炭素数4~12のα,β-エチレン性不飽和ジカルボン酸と炭素数1~12のアルカノールとのモノエステルが好ましく、炭素数4~6のα,β-エチレン性不飽和ジカルボン酸と炭素数2~8のアルカノールとのモノエステルがより好ましく、炭素数4のブテンジオン酸と炭素数2~6のアルカノールとのモノエステルがさらに好ましい。α,β-エチレン性不飽和ジカルボン酸モノエステルの具体例としては、フマル酸モノメチル、フマル酸モノエチル、フマル酸モノn-ブチル、マレイン酸モノメチル、マレイン酸モノエチル、マレイン酸モノn-ブチルなどのブテンジオン酸モノ鎖状アルキルエステル;フマル酸モノシクロペンチル、フマル酸モノシクロヘキシル、フマル酸モノシクロヘキセニル、マレイン酸モノシクロペンチル、マレイン酸モノシクロヘキシル、マレイン酸モノシクロヘキセニルなどの脂環構造を有するブテンジオン酸モノエステル;イタコン酸モノメチル、イタコン酸モノエチル、イタコン酸モノn-ブチル、イタコン酸モノシクロヘキシルなどのイタコン酸モノエステル;などが挙げられる。
(メタ)アクリル酸ハロアルキルエステルの具体例としては、(メタ)アクリル酸クロロメチル、(メタ)アクリル酸1-クロロエチル、(メタ)アクリル酸2-クロロエチル、(メタ)アクリル酸1,2-ジクロロエチル、(メタ)アクリル酸2-クロロプロピル、(メタ)アクリル酸3-クロロプロピル、および(メタ)アクリル酸2,3-ジクロロプロピルなどが挙げられる。
(メタ)アクリル酸ハロアシロキシアルキルエステルの具体例としては、(メタ)アクリル酸2-(クロロアセトキシ)エチル、(メタ)アクリル酸2-(クロロアセトキシ)プロピル、(メタ)アクリル酸3-(クロロアセトキシ)プロピル、および(メタ)アクリル酸3-(ヒドロキシクロロアセトキシ)プロピルなどが挙げられる。
(メタ)アクリル酸(ハロアセチルカルバモイルオキシ)アルキルエステルの具体例としては、(メタ)アクリル酸2-(クロロアセチルカルバモイルオキシ)エチル、および(メタ)アクリル酸3-(クロロアセチルカルバモイルオキシ)プロピルなどが挙げられる。
ハロゲン含有不飽和ケトンの具体例としては、2-クロロエチルビニルケトン、3-クロロプロピルビニルケトン、および2-クロロエチルアリルケトンなどが挙げられる。
ハロメチル基含有芳香族ビニル化合物の具体例としては、p-クロロメチルスチレン、m-クロロメチルスチレン、o-クロロメチルスチレン、およびp-クロロメチル-α-メチルスチレンなどが挙げられる。
ハロアセチル基含有不飽和単量体の具体例としては、3-(ヒドロキシクロロアセトキシ)プロピルアリルエーテル、p-ビニルベンジルクロロ酢酸エステルなどが挙げられる。
α,β-エチレン性不飽和ジカルボン酸ジエステル単量体としては、マレイン酸ジメチル、マレイン酸ジn-ブチルなどのマレイン酸ジアルキルエステルであってアルキル基の炭素数が1~18のもの;フマル酸ジメチル、フマル酸ジn-ブチルなどのフマル酸ジアルキルエステルであってアルキル基の炭素数が1~18のもの;マレイン酸ジシクロペンチル、マレイン酸ジシクロヘキシルなどのマレイン酸ジシクロアルキルエステルであってシクロアルキル基の炭素数が4~16のもの;フマル酸ジシクロペンチル、フマル酸ジシクロヘキシルなどのフマル酸ジシクロアルキルエステルであってシクロアルキル基の炭素数が4~16のもの;イタコン酸ジメチル、イタコン酸ジn-ブチルなどのイタコン酸ジアルキルエステルであってアルキル基の炭素数が1~18のもの:イタコン酸ジシクロヘキシルなどのイタコン酸ジシクロアルキルエステルであってシクロアルキル基の炭素数が4~16のもの;などが挙げられる。
その他のオレフィン系単量体としては、エチレン、プロピレン、塩化ビニル、塩化ビニリデン、酢酸ビニル、エチルビニルエーテル、ブチルビニルエーテルなどが挙げられる。
共役ジエン単量体の具体例としては、1,3-ブタジエン、イソプレン、およびピペリレンなどが挙げられる。
非共役ジエン単量体の具体例としては、エチリデンノルボルネン、ジシクロペンタジエン、(メタ)アクリル酸ジシクロペンタジエニル、および(メタ)アクリル酸2-ジシクロペンタジエニルエチルなどが挙げられる。
添加方法(1):フェノール系老化防止剤を、フェノール系老化防止剤の融点以上の温度条件下で、アクリルゴムの乳化重合液に添加する方法
添加方法(2):フェノール系老化防止剤を、フェノール系老化防止剤の融点以上の温度条件下で、乳化剤の水溶液と接触させることで分散液を得て、分散液の状態で、フェノール系老化防止剤を、アクリルゴムの乳化重合液に添加する方法
すなわち、バレルユニットの内部に配置された一対のスクリューの回転数N[rpm]は、好ましくは10~1000rpmであり、アクリルゴムの含水率およびゲル量を効率よく低減することができるという観点より、より好ましくは50~750rpmであり、さらに好ましくは100~500rpm、特に好ましくは120~300rpmである。
スクリュー型押出機で単位時間当たりに乾燥されるアクリルゴムの処理量Q[kg/hr]は、好ましくは100~1500kg/hrであり、より好ましくは300~1200kg/hr、さらに好ましくは400~1000kg/hr、特に好ましくは500~800kg/hrである。
また、乾燥バレル部の下流側に接続されたダイにおけるゴム圧(樹脂圧あるいは排出圧力)は、特に限定されないが、空気の巻き込みを有効に抑制しながら、高い生産性を実現できるという観点より、好ましくは0.1~10MPaであり、より好ましくは0.5~5MPa、さらに好ましくは1~3MPaである。
なお、本発明においては、アクリルゴムはクラムの状態にて得てもよいし、ベール化されたゴム、すなわち、アクリルゴムベール(所定形状の塊とされたアクリルゴム)として得てもよい。
本発明のゴム組成物は、上記した本発明のアクリルゴムを含むゴム成分と、架橋剤とを含む。
ゴム成分中における、本発明のアクリルゴム成分の含有割合は、使用目的に応じて適宜選択すればよいが、好ましくは30重量%以上であり、より好ましくは50重量%以上、さらに好ましくは70重量%以上、特に好ましくは100重量%(すなわち、ゴム成分として、実質的にアクリルゴム成分のみからなるものを用いた態様)である。
硫黄供与体としては、たとえば、ジペンタメチレンチウラムヘキササルファイド、トリエチルチウラムジサルファイドなどが挙げられる。
トリアジン化合物としては、たとえば、2,4,6-トリメルカプト-s-トリアジン、2-アニリノ-4,6-ジチオール-s-トリアジン、2-ジブチルアミノ-4,6-ジチオール-s-トリアジン、1-ヘキシルアミノ-3,5-ジメルカプトトリアジンなどが挙げられる。これらの中でも、2,4,6-トリメルカプト-s-トリアジンが好ましい。
多価アミン化合物、多価アミン化合物の炭酸塩としては、たとえば、上述したものを用いることができる。
本発明のゴム架橋物は、上述した本発明のゴム組成物を架橋してなるものである。
本発明のゴム架橋物は、本発明のアクリルゴム組成物を用い、所望の形状に対応した成形機、たとえば、押出機、射出成形機、圧縮機、およびロールなどにより成形を行い、加熱することにより架橋反応を行い、ゴム架橋物として形状を固定化することにより製造することができる。この場合においては、予め成形した後に架橋しても、成形と同時に架橋を行ってもよい。成形温度は、通常、10~200℃、好ましくは25~120℃である。架橋温度は、通常、130~220℃、好ましくは150~190℃であり、架橋時間は、通常、2分~10時間、好ましくは3分~5時間である。加熱方法としては、プレス加熱、蒸気加熱、オーブン加熱、および熱風加熱などのゴムの架橋に用いられる方法を適宜選択すればよい。
各種の物性については、以下の方法に従って評価した。
アクリルゴムの単量体組成は、重合反応に用いた各単量体の使用量および重合転化率から算出した。具体的には、各実施例、比較例における乳化重合反応においては、未反応の単量体がいずれも確認できず、重合転化率が略100%であったことから、重合反応に用いた各単量体の使用量を、アクリルゴムを構成する各単量体単位の含有割合と同一であるとした。
アクリルゴムのムーニー粘度(ポリマームーニー)をJISK6300:2013に従って測定した。
ロールにより、アクリルゴム組成物を調製した際におけるロールへの粘着性を下記の基準で評価した。下記基準においては、点数が高いほど、加工性に優れる。
◎:ロール面への粘着が無く、操作性が良好であった。
〇:ロール面への粘着が若干発生したが、切返し可能であり、うす通しも可能であった。
△:ロール面への粘着が顕著に発生し、切返しも、うす通しも不可能であった。
×:ロール面への粘着が顕著に発生し、かつ、ロールの前後両側にゴムが張り付いてしまい、混練不可能であった。
なお、切返し操作は、ロールに張り付いた状態のゴム組成物の一部(約半分)をロールから剥がし、剥がしたゴム組成物片を、ロールに張り付いた状態の他方のゴム組成物片の上に重ねた後、重ねた状態のまま、再度ロールへ通すという操作を繰り返し行う混練操作である。
また、うす通し操作は、切返し操作を行った後に、ロール間の間隙を最小にした状態にて、シート状のゴム組成物の厚み方向において、当該ゴム組成物の長辺がロールの軸方向に対して垂直に交わるように、当該ゴム組成物を再度ロールに通過させるという操作を繰り返し行う混練操作である。
アクリルゴム組成物を、縦15cm、横15cm、深さ0.2cmの金型に入れ、10MPaで加圧しながら170℃で20分間圧縮することにより一次架橋し、次いで、得られた一次架橋物を、ギヤー式オーブンにて、さらに170℃、4時間の条件で加熱して二次架橋させることにより、シート状のゴム架橋物を得た。得られたゴム架橋物を三号形ダンベル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 K6251:2017に従い、引張強度および破断伸びを測定した。
アクリルゴム組成物を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、150℃にて4時間加熱して二次架橋させた。JIS K6262:2006に準じて、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、150℃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、耐圧縮永久歪み性に優れることを示す。
(アクリルゴム(A-1)の製造)
ホモミキサーを備えた混合容器に、イオン交換水46.294部、単量体成分としてアクリル酸エチル46.8部、アクリル酸n-ブチル46.8部、アクリルアミド5部、および、フマル酸モノn-ブチル1.4部、ならびに、乳化剤としてトリデシルオキシヘキサ(オキシエチレン)リン酸エステルナトリウム塩(アニオン性乳化剤)1.8部を仕込み、攪拌することで単量体乳化液を得た。
バンバリーミキサーを用いて、上記にて得られたアクリルゴム(A-1)100部に、カーボンブラック(商品名「シーストSO」、東海カーボン社製)60部、ステアリン酸1部、エステル系ワックス(商品名「グレック8205」、DIC社製)1部、および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)2部を添加して、50℃で5分間混合した。得られた混合物を50℃のロールに移して、アクリルゴム(A-1)100部に対し、ヘキサメチレンジアミンカーバメート(商品名「Diak#1」、デュポンダウエラストマー社製)0.5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)2部を配合して、ロールにて混練することにより、アクリルゴム組成物を得た。なお、ロールにて混練する際に、上記した基準にしたがって、ロール粘着性の評価を行った。そして、得られたアクリルゴム組成物を用いて、引張強度および破断伸びの測定ならびに圧縮永久歪み試験を行った。結果を表1に示す。
各単量体成分の使用量を、アクリル酸エチル48.8部、アクリル酸n-ブチル48.8部、アクリルアミド1部、フマル酸モノn-ブチル1.4部にそれぞれ変更した以外は、実施例1と同様にして、アクリルゴム(A-2)を得た。また、得られたアクリルゴム(A-2)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、これらについて、実施例1と同様に評価を行った。結果を表1に示す。
各単量体成分の使用量を、アクリル酸エチル41.8部、アクリル酸n-ブチル41.8部、アクリルアミド15部、フマル酸モノn-ブチル1.4部にそれぞれ変更した以外は、実施例1と同様にして、アクリルゴム(A-3)を得た。また、得られたアクリルゴム(A-3)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、これらについて、実施例1と同様に評価を行った。結果を表1に示す。
単量体成分としてアクリル酸エチルを使用せず、その他の単量体成分の使用量をアクリル酸n-ブチル93.6部、アクリルアミド5部、フマル酸モノn-ブチル1.4部それぞれに変更した以外は、実施例1と同様にして、アクリルゴム(A-4)を得た。また、得られたアクリルゴム(A-4)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、これらについて、実施例1と同様に評価を行った。結果を表1に示す。
(アクリルゴム(A-5)の製造)
単量体成分として、フマル酸モノn-ブチル1.4部に代えて、フマル酸モノシクロヘキシル1.4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(A-5)を得た。また、得られたアクリルゴム(A-5)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、これらについて、実施例1と同様に評価を行った。結果を表1に示す。
(アクリルゴム(A-6)の製造)
単量体成分として、フマル酸モノn-ブチル1.4部に代えて、メタクリル酸グリシジル1.4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(A-6)を得た。得られたアクリルゴム(A-6)について、実施例1と同様に評価を行った。結果を表1に示す。
また、上記にて得られたアクリルゴム(A-6)を使用したこと、ヘキサメチレンジアミンカーバメートおよび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」、大内新興化学工業株式会社製)1.5部を使用したこと以外は、実施例1と同様にして、アクリルゴム組成物を調製して、同様に評価を行った。結果を表1に示す。
(アクリルゴム(A-7)の製造)
単量体成分として、フマル酸モノn-ブチルに代えてモノクロロ酢酸ビニルを使用し、各単量体成分の使用量を、アクリル酸エチル46.2部、アクリル酸n-ブチル46.2部、アクリルアミド5部、モノクロロ酢酸ビニル2.6部にそれぞれ変更した以外は、実施例1と同様にして、アクリルゴム(A-7)を得た。得られたアクリルゴム(A-7)について、実施例1と同様に評価を行った。結果を表1に示す。
また、上記にて得られたアクリルゴム(A-7)を使用し、ヘキサメチレンジアミンカーバメートおよび1,3-ジ-o-トリルグアニジンに代えて、半硬化牛脂脂肪酸ソーダ石けん(商品名「NSソープ」、花王社製)3.0部、ステアリン酸(商品名「ノンサールSK-1」、日油社製)0.5部、および硫黄(商品名「サルファックスPMC」、鶴見化学工業社製)0.3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て、同様に評価を行った。結果を表1に示す。
単量体成分としてアクリルアミドを使用せず、その他の単量体成分の使用量をアクリル酸エチル49.8部、アクリル酸n-ブチル49.8部、フマル酸モノn-ブチル1.4部にそれぞれ変更した以外は、実施例1と同様にして、アクリルゴム(A-8)を得た。また、得られたアクリルゴム(A-8)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、これらについて、実施例1と同様に評価を行った。結果を表1に示す。
各単量体成分の使用量を、アクリル酸エチル38.8部、アクリル酸n-ブチル38.8部、アクリルアミド20部、フマル酸モノn-ブチル1.4部にそれぞれ変更した以外は、実施例1と同様にして、乳化重合を行ったところ、得られた重合体は水に可溶なものとなり、そのため、凝固操作により回収することができなかった。
単量体成分としてアクリル酸エチルおよびアクリルアミドを使用せず、アクリル酸n-ブチルの使用量を98.6部に変更した以外は、実施例1と同様にして、アクリルゴム(A-10)を得た。また、得られたアクリルゴム(A-10)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、これらについて、実施例1と同様に評価を行った。結果を表1に示す。
また、アクリルアミド単量体単位の含有量を20重量%とした場合は、得られる重合体は水に可溶なものとなり、そのため、凝固操作により回収することができないものであった(比較例2)。
Claims (5)
- カルボキシル基含有単量体単位、ハロゲン原子含有単量体単位、および、エポキシ基含有単量体単位からなる群から選択される少なくとも1種の架橋性基含有単量体単位と、
(メタ)アクリルアミド単量体単位と、を含有するアクリルゴムであって、
全単量体単位中における、前記(メタ)アクリルアミド単量体単位の含有量が0.2~17.5重量%であるアクリルゴム。 - 全単量体単位中における、前記(メタ)アクリルアミド単量体単位の含有量が1~15重量%である請求項1に記載のアクリルゴム。
- 前記架橋性基含有単量体単位が前記カルボキシル基含有単量体単位である請求項1または2に記載のアクリルゴム。
- 請求項1~3のいずれかに記載のアクリルゴムを含むゴム成分と、架橋剤とを含有するゴム組成物。
- 請求項4に記載のゴム組成物を架橋してなるゴム架橋物。
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CN107502246A (zh) * | 2017-08-25 | 2017-12-22 | 无锡海特新材料研究院有限公司 | 美纹纸用溶剂型丙烯酸酯压敏胶及其制备方法 |
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JPH07145291A (ja) | 1993-11-24 | 1995-06-06 | Nisshin Chem Ind Co Ltd | アクリルゴム組成物 |
JPH11199825A (ja) * | 1998-01-08 | 1999-07-27 | Chuo Rika Kogyo Corp | 水性シーラー組成物 |
JP2005116610A (ja) * | 2003-10-03 | 2005-04-28 | Nitto Denko Corp | 半導体ウエハの加工方法および半導体ウエハ加工用粘着シート |
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