CN117321101A - 含腈基共聚物橡胶、橡胶组合物和橡胶交联物 - Google Patents
含腈基共聚物橡胶、橡胶组合物和橡胶交联物 Download PDFInfo
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- CN117321101A CN117321101A CN202280035100.0A CN202280035100A CN117321101A CN 117321101 A CN117321101 A CN 117321101A CN 202280035100 A CN202280035100 A CN 202280035100A CN 117321101 A CN117321101 A CN 117321101A
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- Prior art keywords
- acrylonitrile
- rubber
- ethylenically unsaturated
- unit
- containing copolymer
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- 229920001971 elastomer Polymers 0.000 title claims abstract description 199
- 239000005060 rubber Substances 0.000 title claims abstract description 199
- 229920001577 copolymer Polymers 0.000 title claims abstract description 106
- 125000002560 nitrile group Chemical group 0.000 title claims abstract description 92
- 239000000203 mixture Substances 0.000 title claims description 48
- 239000000178 monomer Substances 0.000 claims abstract description 164
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical group C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims abstract description 105
- 150000002825 nitriles Chemical class 0.000 claims abstract description 50
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000011630 iodine Substances 0.000 claims abstract description 22
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 22
- 150000001993 dienes Chemical class 0.000 claims abstract description 16
- 239000003431 cross linking reagent Substances 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 238000004132 cross linking Methods 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 239000003921 oil Substances 0.000 description 77
- -1 polycyclic aromatic compound Chemical class 0.000 description 64
- 238000012360 testing method Methods 0.000 description 39
- 230000008859 change Effects 0.000 description 33
- 238000005984 hydrogenation reaction Methods 0.000 description 33
- 238000010438 heat treatment Methods 0.000 description 31
- 238000000034 method Methods 0.000 description 28
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 27
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 18
- 239000006087 Silane Coupling Agent Substances 0.000 description 17
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 17
- 239000003054 catalyst Substances 0.000 description 16
- 239000011243 crosslinked material Substances 0.000 description 16
- 239000000295 fuel oil Substances 0.000 description 15
- 230000009477 glass transition Effects 0.000 description 15
- 239000004816 latex Substances 0.000 description 15
- 229920000126 latex Polymers 0.000 description 15
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 14
- 230000000704 physical effect Effects 0.000 description 14
- HFCUBKYHMMPGBY-UHFFFAOYSA-N 2-methoxyethyl prop-2-enoate Chemical compound COCCOC(=O)C=C HFCUBKYHMMPGBY-UHFFFAOYSA-N 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 13
- 239000011256 inorganic filler Substances 0.000 description 13
- 229910003475 inorganic filler Inorganic materials 0.000 description 13
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 12
- 229920000642 polymer Polymers 0.000 description 12
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 11
- 239000000377 silicon dioxide Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 238000006116 polymerization reaction Methods 0.000 description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 229910052763 palladium Inorganic materials 0.000 description 9
- 229910052717 sulfur Inorganic materials 0.000 description 9
- 239000011593 sulfur Substances 0.000 description 9
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 8
- 239000003505 polymerization initiator Substances 0.000 description 8
- 238000003860 storage Methods 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 239000003995 emulsifying agent Substances 0.000 description 7
- 238000007720 emulsion polymerization reaction Methods 0.000 description 7
- 239000000446 fuel Substances 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 7
- 229920000768 polyamine Polymers 0.000 description 7
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 6
- 229940018560 citraconate Drugs 0.000 description 6
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 241001441571 Hiodontidae Species 0.000 description 5
- 150000001491 aromatic compounds Chemical class 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000005345 coagulation Methods 0.000 description 5
- 230000015271 coagulation Effects 0.000 description 5
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000010687 lubricating oil Substances 0.000 description 5
- 229910052751 metal Chemical class 0.000 description 5
- 239000002184 metal Chemical class 0.000 description 5
- 150000001451 organic peroxides Chemical class 0.000 description 5
- 125000003367 polycyclic group Chemical group 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- 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 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- RJOPPIKQXNSFGS-UHFFFAOYSA-N [NH4+].[NH4+].[NH4+].[NH4+].[NH4+].[NH4+].[Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Cl-] Chemical compound [NH4+].[NH4+].[NH4+].[NH4+].[NH4+].[NH4+].[Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Cl-] RJOPPIKQXNSFGS-UHFFFAOYSA-N 0.000 description 4
- 239000006229 carbon black Substances 0.000 description 4
- 239000003638 chemical reducing agent Substances 0.000 description 4
- 239000004927 clay Substances 0.000 description 4
- 238000013329 compounding Methods 0.000 description 4
- 239000007822 coupling agent Substances 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 4
- 125000005395 methacrylic acid group Chemical group 0.000 description 4
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 4
- 238000000465 moulding Methods 0.000 description 4
- 239000004014 plasticizer Substances 0.000 description 4
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 4
- 238000007711 solidification Methods 0.000 description 4
- 230000008023 solidification Effects 0.000 description 4
- 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
- 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 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- 229920000459 Nitrile rubber Polymers 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 125000005907 alkyl ester group Chemical group 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
- 238000005185 salting out Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- UBRWPVTUQDJKCC-UHFFFAOYSA-N 1,3-bis(2-tert-butylperoxypropan-2-yl)benzene Chemical compound CC(C)(C)OOC(C)(C)C1=CC=CC(C(C)(C)OOC(C)(C)C)=C1 UBRWPVTUQDJKCC-UHFFFAOYSA-N 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
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- IEKHISJGRIEHRE-UHFFFAOYSA-N 16-methylheptadecanoic acid;propan-2-ol;titanium Chemical compound [Ti].CC(C)O.CC(C)CCCCCCCCCCCCCCC(O)=O.CC(C)CCCCCCCCCCCCCCC(O)=O.CC(C)CCCCCCCCCCCCCCC(O)=O IEKHISJGRIEHRE-UHFFFAOYSA-N 0.000 description 2
- YAJYJWXEWKRTPO-UHFFFAOYSA-N 2,3,3,4,4,5-hexamethylhexane-2-thiol Chemical compound CC(C)C(C)(C)C(C)(C)C(C)(C)S YAJYJWXEWKRTPO-UHFFFAOYSA-N 0.000 description 2
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
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- KMKWGXGSGPYISJ-UHFFFAOYSA-N 4-[4-[2-[4-(4-aminophenoxy)phenyl]propan-2-yl]phenoxy]aniline Chemical compound C=1C=C(OC=2C=CC(N)=CC=2)C=CC=1C(C)(C)C(C=C1)=CC=C1OC1=CC=C(N)C=C1 KMKWGXGSGPYISJ-UHFFFAOYSA-N 0.000 description 2
- DIVUSAVKQOLTNR-UHFFFAOYSA-N 4-methoxybutyl 2-methylprop-2-enoate Chemical compound COCCCCOC(=O)C(C)=C DIVUSAVKQOLTNR-UHFFFAOYSA-N 0.000 description 2
- GAKWESOCALHOKH-UHFFFAOYSA-N 4-methoxybutyl prop-2-enoate Chemical compound COCCCCOC(=O)C=C GAKWESOCALHOKH-UHFFFAOYSA-N 0.000 description 2
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
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- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
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- 150000008065 acid anhydrides Chemical class 0.000 description 2
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- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
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- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
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- AUZONCFQVSMFAP-UHFFFAOYSA-N disulfiram Chemical compound CCN(CC)C(=S)SSC(=S)N(CC)CC AUZONCFQVSMFAP-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 2
- 238000010556 emulsion polymerization method Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 2
- XLYMOEINVGRTEX-UHFFFAOYSA-N fumaric acid monoethyl ester Natural products CCOC(=O)C=CC(O)=O XLYMOEINVGRTEX-UHFFFAOYSA-N 0.000 description 2
- NKHAVTQWNUWKEO-UHFFFAOYSA-N fumaric acid monomethyl ester Natural products COC(=O)C=CC(O)=O NKHAVTQWNUWKEO-UHFFFAOYSA-N 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
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Abstract
本发明提供了一种含腈基共聚物橡胶,其含有丙烯腈单元(a)、除丙烯腈以外的α,β‑烯属不饱和腈单体单元(b)以及共轭二烯单体单元(c),碘值为120以下,在全部单体单元中,上述丙烯腈单元(a)与上述除丙烯腈以外的α,β‑烯属不饱和腈单体单元(b)的合计的含有比例为1~50重量%,上述丙烯腈单元(a)与上述除丙烯腈以外的α,β‑烯属不饱和腈单体单元(b)的含有比例以“上述丙烯腈单元(a)的含量∶上述除丙烯腈以外的α,β‑烯属不饱和腈单体单元(b)的含量”的重量比计为10∶90~90∶10。
Description
技术领域
本发明涉及能够提供耐热性、耐油性以及在加热环境下的耐油中固化性(具体而言,在加热环境下,浸渍在含有多环稠合芳香族化合物的油中时的玻璃化转变温度的变化以及硬度的变化小)优异的橡胶交联物的含腈基共聚物橡胶、以及使用这样的含腈基共聚物橡胶得到的橡胶组合物和橡胶交联物。
背景技术
与丙烯腈-丁二烯共聚物橡胶等主链结构中碳-碳不饱和键多的一般的含腈基共聚物橡胶相比,以氢化丙烯腈-丁二烯共聚物橡胶为代表的含饱和腈基共聚物橡胶的耐热性、耐油性、耐臭氧性等优异,因此优选用作汽车用密封条、软管、管等橡胶部件。另一方面,近年来,对于汽车用的橡胶部件,除耐油性以外,还要求耐油中固化性也优异。
例如,在专利文献1中,公开了一种腈橡胶组合物,其相对于100质量份的以14重量%以上且小于21重量%的比例含有α,β-烯属不饱和腈单体单元且碘值为120以下的含腈基高饱和共聚物橡胶(A),含有50~90重量份的填充剂(B)和0~29.9重量份的己二酸酯系增塑剂和/或醚酯系增塑剂(C)。根据专利文献1中公开的交联性腈橡胶组合物,能够得到耐油中固化性优异的橡胶交联物。另一方面,汽车用的密封条、软管、管等橡胶部件在高温环境中使用的情况也很多,因此,对于这些橡胶部件中所使用的橡胶材料,从能够适用于这些用途的观点出发,有时需要在加热环境下的耐油中固化性优异,更具体而言,需要在加热环境下保存后的耐油中固化性优异。对此,在引用文献1中,对耐油性和耐油中固化性进行了研究,但没有对在加热环境下的耐油中固化性进行研究。
现有技术文献
专利文献
专利文献1:国际公开第2017/047571号。
发明内容
发明要解决的问题
本发明是鉴于这样的实际情况而完成的,本发明的目的在于提供一种含腈基共聚物橡胶,其常态物性良好且能够提供耐热性、耐油性以及在加热环境下的耐油中固化性(具体而言,在加热环境下保存后,浸渍在含有多环稠合芳香族化合物的油中时的玻璃化转变温度的变化以及硬度的变化小)优异的橡胶交联物。
此外,本发明目的还在于提供使用这样的含腈基共聚物橡胶得到的橡胶组合物和橡胶交联物。
用于解决问题的方案
本发明人为了实现上述目的进行了深入研究,结果发现,通过以规定的含有比例含有丙烯腈单元和除丙烯腈以外的α,β-烯属不饱和腈单体单元作为含腈基单体单元且碘值为120以下的含腈基共聚物橡胶,能够实现上述目的,从而完成了本发明。
即根据本发明,可提供一种含腈基共聚物橡胶,其含有丙烯腈单元(a)、除丙烯腈以外的α,β-烯属不饱和腈单体单元(b)以及共轭二烯单体单元(c),碘值为120以下,
在全部单体单元中,上述丙烯腈单元(a)与上述除丙烯腈以外的α,β-烯属不饱和腈单体单元(b)的合计含量为1~50重量%,
上述丙烯腈单元(a)与上述除丙烯腈以外的α,β-烯属不饱和腈单体单元(b)的含有比例以“丙烯腈单元(a)的含量∶除丙烯腈以外的α,β-烯属不饱和腈单体单元(b)的含量”的重量比计为10∶90~90∶10。
在本发明的含腈基共聚物橡胶中,上述除丙烯腈以外的α,β-烯属不饱和腈单体单元(b)中的除氰基以外的碳原子数优选为2~5个。
在本发明的含腈基共聚物橡胶中,在全部单体单元中,上述丙烯腈单元(a)与上述除丙烯腈以外的α,β-烯属不饱和腈单体单元(b)的合计含量优选为10~45重量%。
在本发明的含腈基共聚物橡胶中,碘值优选为80以下。
在本发明的含腈基共聚物橡胶中,上述丙烯腈单元(a)与上述除丙烯腈以外的α,β-烯属不饱和腈单体单元(b)的含有比例以“丙烯腈单元(a)的含量∶除丙烯腈以外的α,β-烯属不饱和腈单体单元(b)的含量”的重量比计优选为20∶80~80∶20。
在本发明的含腈基共聚物橡胶中,上述丙烯腈单元(a)与上述除丙烯腈以外的α,β-烯属不饱和腈单体单元(b)的含有比例以“丙烯腈单元(a)的含量∶除丙烯腈以外的α,β-烯属不饱和腈单体单元(b)的含量”的重量比计优选为25∶75~75∶25。
在本发明的含腈基共聚物橡胶中,上述共轭二烯单体单元(c)的含量优选为10~90重量%。
此外,根据本发明,可提供一种在上述本发明的含腈基共聚物橡胶中配合交联剂而成的橡胶组合物。
进而,根据本发明,可提供一种将上述本发明的橡胶组合物交联而成的橡胶交联物。
发明效果
根据本发明,能够提供常态物性良好且能够形成耐热性、耐油性以及在加热环境下保存后的耐油中固化性(具体而言,在加热环境下保存后,在浸渍在含有多环稠合芳香族化合物的油中时的玻璃化转变温度的变化以及硬度的变化小)优异的橡胶交联物的含腈基共聚物橡胶、以及使用这样的含腈基共聚物橡胶得到的橡胶组合物和橡胶交联物。
具体实施方式
<含腈基共聚物橡胶>
本发明的含腈基共聚物橡胶含有丙烯腈单元(a)、除丙烯腈以外的α,β-烯属不饱和腈单体单元(b)以及共轭二烯单体单元(c),碘值为120以下,
在全部单体单元中,上述丙烯腈单元(a)与上述除丙烯腈以外的α,β-烯属不饱和腈单体单元(b)的合计含量为1~50重量%,
上述丙烯腈单元(a)与上述除丙烯腈以外的α,β-烯属不饱和腈单体单元(b)的含有比例以“丙烯腈单元(a)的含量∶除丙烯腈以外的α,β-烯属不饱和腈单体单元(b)的含量”的重量比计为10∶90~90∶10。
本发明的含腈基共聚物橡胶是包含丙烯腈单元(a)和除丙烯腈以外的α,β-烯属不饱和腈单体单元(b)作为含腈基单体单元的含腈基共聚物橡胶。作为构成除丙烯腈以外的α,β-烯属不饱和腈单体单元(b)的除丙烯腈以外的α,β-烯属不饱和腈单体,只要是具有腈基的α,β-烯属不饱和化合物(除丙烯腈以外)则没有限定,可以举出:α-氯丙烯腈、α-溴丙烯腈等α-卤代丙烯腈;甲基丙烯腈、乙基丙烯腈等α-烷基丙烯腈等。其中,优选除氰基以外的碳原子数为2~5的α,β-烯属不饱和化合物,更优选为α-烷基丙烯腈,特别优选为甲基丙烯腈。作为除丙烯腈以外的α,β-烯属不饱和腈单体,也可以将它们多种并用。
在本发明的含腈基共聚物橡胶中,丙烯腈单元(a)与除丙烯腈以外的α,β-烯属不饱和腈单体单元(b)的合计含量为1~50重量%,优选为10~45重量%,更优选为15~42重量%,进一步优选为20~40重量%,特别优选为26~36重量%。当丙烯腈单元(a)与除丙烯腈以外的α,β-烯属不饱和腈单体单元(b)的合计含量过少时,得到的橡胶交联物会有耐油性差的风险,相反,当过多时,耐油中固化性有可能降低。
此外,在本发明的含腈基共聚物橡胶中,丙烯腈单元(a)与除丙烯腈以外的α,β-烯属不饱和腈单体单元(b)的含有比例以“丙烯腈单元(a)的含量∶上述除丙烯腈以外的α,β-烯属不饱和腈单体单元(b)的含量”的重量比计为10∶90~90∶10,优选为12∶88~88∶12,更优选为15∶85~85∶15,进一步优选为20∶80~80∶20,更进一步优选为25∶75~75∶25,特别优选为30∶70~60∶40。当丙烯腈单元(a)的含有比例过少时,得到的橡胶交联物的拉伸强度以及耐油性差,另一方面,当除丙烯腈以外的α,β-烯属不饱和腈单体单元(b)的含有比例过少时,得到的橡胶交联物的耐油性以及加热环境下的耐油中固化性差。
另外,在本发明的含腈基共聚物橡胶中,丙烯腈单元(a)的含量以与除丙烯腈以外的α,β-烯属不饱和腈单体单元(b)的关系计只要是成为上述范围的量即可,相对于全部单体单元,优选为1~45重量%,更优选为5~40重量%,进一步优选为10~37.5重量%,特别优选为12~25重量%。此外,在本发明的含腈基共聚物橡胶中,除丙烯腈以外的α,β-烯属不饱和腈单体单元(b)的含量以与丙烯腈单元(a)的关系计只要是成为上述范围的量即可,相对于全部单体单元,优选为1~45重量%,更优选为5~40重量%,进一步优选为10~37.5重量%,特别优选为12~25重量%。通过使丙烯腈单元(a)的含量、除丙烯腈以外的α,β-烯属不饱和腈单体单元(b)的含量为上述范围,能够使得到的橡胶交联物的耐热性、耐油性以及在加热环境下的耐油中固化性更加优异。
作为构成共轭二烯单体单元(c)的共轭二烯单体,优选1,3-丁二烯、异戊二烯、2,3-二甲基-1,3-丁二烯、1,3-戊二烯、氯丁二烯等碳原子数为4~6的共轭二烯单体,更优选1,3-丁二烯和异戊二烯,特别优选1,3-丁二烯。共轭二烯单体可以单独使用一种,也可以并用多种。
在本发明的含腈基共聚物橡胶中,共轭二烯单体单元(c)(包含被氢化的部分)的含量相对于全部单体单元优选为10~90重量%,更优选为20~80重量%,进一步优选为30~70重量%,特别优选为35~65重量%,通过使共轭二烯单体单元的含量为上述范围,能够使得到的橡胶交联物在保持良好的耐热性、耐化学稳定性的同时橡胶弹性优异。
此外,本发明的含腈基共聚物橡胶优选除丙烯腈单元(a)、除丙烯腈以外的α,β-烯属不饱和腈单体单元(b)以及共轭二烯单体单元(c)以外,进一步含有含羧基单体单元(d)。通过进一步含有含羧基单体单元(d),能够在本发明的含腈基共聚物橡胶中导入羧基。
作为构成含羧基单体单元(d)的含羧基单体,只要是具有一个以上的没有进行酯化等的未取代的(游离的)羧基的单体则没有特别限定,可以举出例如α,β-烯属不饱和单羧酸单体、α,β-烯属不饱和多元羧酸单体以及α,β-烯属不饱和二羧酸单酯单体等。此外,在含羧基单体中,也包含这些单体的羧基形成为羧酸盐的单体。进而,α,β-烯属不饱和多元羧酸的酸酐由于在共聚后酸酐基团开裂而形成羧基,因此也能够用作含羧基单体。
作为α,β-烯属不饱和单羧酸单体,可以举出丙烯酸、甲基丙烯酸、乙基丙烯酸、巴豆酸、肉桂酸等。
作为α,β-烯属不饱和多元羧酸单体,可以举出:富马酸、马来酸等丁烯二酸;衣康酸;柠康酸;中康酸;戊烯二酸;烯丙基丙二酸;芸康酸等。此外,作为α,β-不饱和多元羧酸的酸酐,可以举出马来酸酐、衣康酸酐、柠康酸酐等。
作为α,β-烯属不饱和二羧酸单酯单体,可以举出:马来酸单甲酯、马来酸单乙酯、马来酸单丙酯、马来酸单正丁酯等马来酸单烷基酯;马来酸单环戊酯、马来酸单环己酯、马来酸单环庚酯等马来酸单环烷基酯;马来酸单甲基环戊酯、马来酸单乙基环己酯等马来酸单烷基环烷基酯;富马酸单甲酯、富马酸单乙酯、富马酸单丙酯、富马酸单正丁酯等富马酸单烷基酯;富马酸单环戊酯、富马酸单环己酯、富马酸单环庚酯等富马酸单环烷基酯;富马酸单甲基环戊酯、富马酸单乙基环己酯等富马酸单烷基环烷基酯;柠康酸单甲酯、柠康酸单乙酯、柠康酸单丙酯、柠康酸单正丁酯等柠康酸单烷基酯;柠康酸单环戊酯、柠康酸单环己酯、柠康酸单环庚酯等柠康酸单环烷基酯;柠康酸单甲基环戊酯、柠康酸单乙基环己酯等柠康酸单烷基环烷基酯;衣康酸单甲酯、衣康酸单乙酯、衣康酸单丙酯、衣康酸单正丁酯等衣康酸单烷基酯;衣康酸单环戊酯、衣康酸单环己酯、衣康酸单环庚酯等衣康酸单环烷基酯;衣康酸单甲基环戊酯、衣康酸单乙基环己酯等衣康酸单烷基环烷基酯等。
含羧基单体可以单独使用一种,也可以并用多种。在这些之中,从使本发明的效果变得更加显著的观点出发,优选α,β-烯属不饱和单羧酸单体,更优选丙烯酸、甲基丙烯酸,特别优选甲基丙烯酸。
在本发明的含腈基共聚物橡胶中,含羧基单体单元(d)的含量相对于全部单体单元优选为0.1~10重量%,更优选为0.5~8重量%,进一步优选为1~5重量%。通过使含羧基单体单元的含量为上述范围,能够使得到的橡胶交联物的机械特性更加良好。
此外,本发明的含腈基共聚物橡胶,除丙烯腈单元(a)、除丙烯腈以外的α,β-烯属不饱和腈单体单元(b)、共轭二烯单体单元(c)以及含羧基单体单元(d)以外,也可以含有α,β-烯属不饱和单羧酸酯单体单元(e)。
作为构成α,β-烯属不饱和单羧酸酯单体单元(e)的α,β-烯属不饱和单羧酸酯单体,没有特别限定,可以举出例如α,β-烯属不饱和单羧酸烷基酯单体、α,β-烯属不饱和单羧酸烷氧基烷基酯单体、α,β-烯属不饱和单羧酸氨基烷基酯单体、α,β-烯属不饱和单羧酸羟基烷基酯单体、α,β-烯属不饱和单羧酸氟代烷基酯单体等。
在这些之中,优选α,β-烯属不饱和单羧酸烷基酯单体或α,β-烯属不饱和单羧酸烷氧基烷基酯单体,更优选α,β-烯属不饱和单羧酸烷氧基烷基酯单体。
通过含有α,β-烯属不饱和单羧酸酯单体单元(e),能够使得到的橡胶交联物的耐寒性提高。
作为α,β-烯属不饱和单羧酸的烷基酯单体,优选具有碳原子数为3~10的烷基作为烷基的单体,更优选具有碳原子数为3~8的烷基作为烷基的单体,进一步优选具有碳原子数为4~6的烷基作为烷基的单体。
作为α,β-烯属不饱和单羧酸烷基酯单体的具体例,可以举出:丙烯酸甲酯、丙烯酸乙酯、丙烯酸丙酯、丙烯酸异丁酯、丙烯酸正丁酯、丙烯酸正戊酯、丙烯酸-2-乙基己酯、丙烯酸正十二烷基酯等丙烯酸烷基酯单体;丙烯酸环戊酯、丙烯酸环己酯等丙烯酸环烷基酯单体;丙烯酸甲基环戊酯、丙烯酸乙基环戊酯、丙烯酸甲基环己酯等丙烯酸烷基环烷基酯单体;甲基丙烯酸甲酯、甲基丙烯酸乙酯、甲基丙烯酸丙酯、甲基丙烯酸正丁酯、甲基丙烯酸正戊酯、甲基丙烯酸正辛酯等甲基丙烯酸烷基酯单体;甲基丙烯酸环戊酯、甲基丙烯酸环己酯等甲基丙烯酸环烷基酯单体;甲基丙烯酸甲基环戊酯、甲基丙烯酸乙基环戊酯、甲基丙烯酸甲基环己酯等甲基丙烯酸烷基环烷基酯单体;巴豆酸丙酯、巴豆酸正丁酯、巴豆酸-2-乙基己酯等巴豆酸烷基酯单体;巴豆酸环戊酯、巴豆酸环己酯、巴豆酸环辛酯等巴豆酸环烷基酯单体;巴豆酸甲基环戊酯、巴豆酸甲基环己酯等巴豆酸烷基环烷基酯单体等。
此外,作为α,β-烯属不饱和单羧酸烷氧基烷基酯单体,优选具有碳原子数为2~8的烷氧基烷基作为烷氧基烷基的单体,更优选具有碳原子数为2~6的烷氧基烷基作为烷氧基烷基的单体,进一步优选具有碳原子数为2~4的烷氧基烷基作为烷氧基烷基的单体。
作为α,β-烯属不饱和单羧酸烷氧基烷基酯单体的具体例,可以举出:丙烯酸甲氧基甲酯、丙烯酸甲氧基乙酯、丙烯酸甲氧基丁酯、丙烯酸乙氧基甲酯、丙烯酸乙氧基乙酯、丙烯酸乙氧基丙酯、丙烯酸乙氧基十二烷基酯、丙烯酸正丙氧基乙酯、丙烯酸异丙氧基乙酯、丙烯酸正丁氧基乙酯、丙烯酸异丁氧基乙酯、丙烯酸叔丁氧基乙酯、丙烯酸甲氧基丙酯、丙烯酸甲氧基丁酯等丙烯酸烷氧基烷基酯单体;甲基丙烯酸甲氧基甲酯、甲基丙烯酸甲氧基乙酯、甲基丙烯酸甲氧基丁酯、甲基丙烯酸乙氧基甲酯、甲基丙烯酸乙氧基乙酯、甲基丙烯酸乙氧基戊酯、甲基丙烯酸正丙氧基乙酯、甲基丙烯酸异丙氧基乙酯、甲基丙烯酸正丁氧基乙酯、甲基丙烯酸异丁氧基乙酯、甲基丙烯酸叔丁氧基乙酯、甲基丙烯酸甲氧基丙酯、甲基丙烯酸甲氧基丁酯、甲氧基-聚乙二醇(甲基)丙烯酸酯等甲基丙烯酸烷氧基烷基酯单体等。
在这些α,β-烯属不饱和单羧酸酯单体中,从能够使本发明的效果更进一步显著的观点出发,优选丙烯酸烷基酯单体、丙烯酸烷氧基烷基酯单体,更优选丙烯酸正丁酯和丙烯酸甲氧基乙酯,特别优选丙烯酸甲氧基乙酯。此外,这些α,β-烯属不饱和单羧酸酯单体能够组合使用两种以上。
在本发明的含腈基共聚物橡胶中,α,β-烯属不饱和单羧酸酯单体单元的含量相对于全部单体单元优选为0~60重量%,更优选为0~50重量%,进一步优选为0~40重量%,更进一步优选为8~30重量%。通过使α,β-烯属不饱和单羧酸酯单体单元的含量为上述范围,能够更适当地提高得到的橡胶交联物的耐寒性。
此外,本发明的含腈基共聚物橡胶,除丙烯腈单元(a)、除丙烯腈以外的α,β-烯属不饱和腈单体单元(b)、共轭二烯单体单元(c)、以及根据需要含有的含羧基单体单元(d)和α,β-烯属不饱和单羧酸酯单体单元(e)以外,也可以含有能够与形成这些单元的单体共聚的其它单体的单元。作为这样的其它单体,可以举出:除上述以外的α,β-烯属不饱和单羧酸酯单体、乙烯、α-烯烃单体、芳香族乙烯基单体、含氟乙烯基单体、共聚性防老剂等。
作为除上述以外的α,β-烯属不饱和单羧酸酯单体,可以举出:丙烯酸α-氰基乙酯、甲基丙烯酸α-氰基乙酯、甲基丙烯酸氰基丁酯等具有碳原子数为2~12的氰基烷基的(甲基)丙烯酸酯;丙烯酸-2-羟基乙酯、丙烯酸-2-羟基丙酯、甲基丙烯酸-2-羟基乙酯等具有碳原子数为1~12的羟基烷基的(甲基)丙烯酸酯;丙烯酸三氟乙酯、甲基丙烯酸四氟丙酯等具有碳原子数为1~12的氟代烷基的(甲基)丙烯酸酯等。
作为α-烯烃单体,优选碳原子数为3~12的单体,可以举出例如丙烯、1-丁烯、4-甲基-1-戊烯、1-己烯、1-辛烯等。
作为芳香族乙烯基单体,可以举出苯乙烯、α-甲基苯乙烯、乙烯基吡啶等。
作为含氟乙烯基单体,可以举出氟乙基乙烯基醚、氟丙基乙烯基醚、邻三氟甲基苯乙烯、五氟苯甲酸乙烯酯、二氟乙烯、四氟乙烯等。
作为共聚性防老剂,可以举出N-(4-苯胺基苯基)丙烯酰胺、N-(4-苯胺基苯基)甲基丙烯酰胺、N-(4-苯胺基苯基)肉桂酰胺、N-(4-苯胺基苯基)巴豆酰胺、N-苯基-4-(3-乙烯基苄氧基)苯胺、N-苯基-4-(4-乙烯基苄氧基)苯胺、4,4'-双(α,α-二甲基苄基)二苯胺等。
这些能够共聚的其它单体也可以并用多种。其它单体的单元的含量相对于构成含腈基共聚物橡胶的全部单体单元优选为50重量%以下,更优选为40重量%以下,进一步优选为10重量%以下。
本发明的含腈基共聚物橡胶的碘值为120以下,优选为80以下,更优选为50以下,进一步优选为30以下,特别优选为20以下,最优选为12以下。当含腈基共聚物橡胶的碘值过高时,得到的橡胶交联物的耐热性和耐臭氧性有可能会降低。
本发明的含腈基共聚物橡胶的聚合物·门尼黏度(ML1+4,100℃)优选为10~200,更优选为15~150,进一步优选为15~100,特别优选为30~80。通过使含腈基共聚物橡胶的聚合物·门尼黏度为上述范围,在制成橡胶组合物时,能够在良好地保持橡胶组合物的加工性的同时进一步提高得到的交联物的机械特性。
本发明的含腈基共聚物橡胶的制造方法没有特别的限定,能够通过将上述单体进行共聚,根据需要将得到的共聚物中的碳-碳双键进行氢化来制造。聚合方法没有特别限定,只要是公知的乳液聚合法、溶液聚合法即可,从工业生产率的观点出发优选乳液聚合法。在乳液聚合时,除乳化剂、聚合引发剂、分子量调节剂以外,还能够使用通常使用的聚合辅助材料。
作为乳化剂没有特别限定,可以举出例如:聚氧乙烯烷基醚、聚氧乙烯烷基酚醚、聚氧乙烯烷基酯、聚氧乙烯山梨糖醇酐烷基酯等非离子性乳化剂;肉豆蔻酸、棕榈酸、油酸及亚麻酸等脂肪酸的盐、十二烷基苯磺酸钠等烷基苯磺酸盐、高级醇硫酸酯盐、烷基磺基琥珀酸盐等阴离子性乳化剂;α,β-不饱和羧酸的磺酸酯、α,β-不饱和羧酸的硫酸酯、磺基烷基芳基醚等共聚性乳化剂等。乳化剂的添加量相对于100重量份的聚合中使用的单体优选为0.1~10重量份,更优选0.5~5重量份。
作为聚合引发剂,只要是自由基引发剂则没有特别限定,能够举出:过硫酸钾、过硫酸钠、过硫酸铵、过磷酸钾、过氧化氢等无机过氧化物;叔丁基过氧化物、氢过氧化枯烯、萜烷过氧化氢、过氧化叔丁基异丙苯、过氧化乙酰、过氧化异丁酰、过氧化辛酰、过氧化二苯甲酰、3,5,5-三甲基己酰基过氧化物、过氧化异丁酸叔丁酯等有机过氧化物;偶氮二异丁腈、偶氮双(2,4-二甲基戊腈)、偶氮双(环己烷甲腈)、偶氮二异丁酸甲酯等偶氮化合物等。这些聚合引发剂能够单独使用或组合使用两种以上。作为聚合引发剂,优选无机或有机的过氧化物。在使用过氧化物作为聚合引发剂的情况下,也能够与还原剂组合,作为氧化还原系聚合引发剂而使用。作为还原剂,没有特别限定,可以举出:硫酸亚铁、环烷酸亚铜等含有处于还原状态金属离子的化合物;羟基甲烷亚磺酸钠等亚磺酸盐;亚硫酸钠、亚硫酸钾、亚硫酸氢钠、醛亚硫酸氢钠、亚硫酸氢钾等亚硫酸盐等。聚合引发剂的添加量相对于100重量份的聚合中使用的单体优选为0.01~2重量份。
作为分子量调节剂,没有特别限定,可以举出:叔十二烷基硫醇、正十二烷基硫醇、辛基硫醇等硫醇类;四氯化碳、二氯甲烷、二溴甲烷等卤代烃;α-甲基苯乙烯二聚体;二硫化四乙基秋兰姆、二硫化双五亚甲基秋兰姆、二硫化二异丙基黄原酸酯等含硫化合物等。这些能够单独使用或组合使用两种以上。
在乳液聚合的介质中,通常使用水。水的量相对于100重量份的聚合中使用的单体优选为80~500重量份,更优选80~300重量份。
在乳液聚合时,能够根据需要进一步使用稳定剂、分散剂、pH调节剂、脱氧剂、粒径调节剂等聚合辅助材料。在使用这些的情况下,其种类、使用量没有特别限定。
此外,对于得到的共聚物,也可以根据需要进行共聚物的氢化(加氢反应)。加氢只要根据公知的方法即可,可以举出:将乳液聚合中得到的共聚物的胶乳凝固后,在油层进行加氢的油层加氢法;将得到的共聚物的胶乳直接进行加氢的水层加氢法等。
在以油层加氢法进行加氢的情况下,优选使通过上述乳液聚合制备的共聚物的胶乳经过利用盐析、醇的凝固并经过过滤分离和干燥,溶解在有机溶剂中。接下来,进行加氢反应(油层加氢法),将得到的氢化物注入大量的水中,进行凝固、过滤分离和干燥,由此能够得到本发明的含腈基共聚物橡胶。
胶乳的利用盐析的凝固中,能够使用氯化钠、氯化钙、硫酸铝等公知的凝固剂。此外,也可以使用甲醇等醇进行凝固来代替利用盐析的凝固。作为油层加氢法的溶剂,只要是溶解通过乳液聚合得到的共聚物的液态有机化合物则没有特别限定,优选使用苯、氯苯、甲苯、二甲苯、己烷、环己烷、四氢呋喃、甲乙酮、乙酸乙酯、环己酮和丙酮等。
作为油层加氢法的催化剂,只要是公知的选择性氢化催化剂则能够没有限定地使用,优选钯系催化剂和铑系催化剂,更优选钯系催化剂(乙酸钯、氯化钯和氢氧化钯等)。这些可以并用两种以上,在这种情况下优选以钯系催化剂作为主要的活性成分。这些催化剂通常负载于载体而使用。作为载体,可举例示出二氧化硅、二氧化硅-氧化铝、氧化铝、硅藻土、活性炭等。相对于共聚物,催化剂使用量优选为10~5000重量ppm,更优选为100~3000重量ppm。
或者,在以水层加氢法进行加氢的情况下,优选根据需要在通过上述乳液聚合制备的共聚物的胶乳中加水稀释,进行加氢反应。水层加氢法可举出:在氢化催化剂存在下的反应体系中供给氢进行氢化的水层直接加氢法;以及在氧化剂、还原剂和活化剂的存在下还原来进行氢化的水层间接加氢法,在这些之中,优选水层直接加氢法。
在水层直接加氢法中,为了防止凝聚,水层中的共聚物的浓度(胶乳状态时的浓度)优选为40重量%以下。氢化催化剂只要是不易在水中分解的化合物,则没有特别限定。作为其具体例,在钯催化剂中,可举出:甲酸、丙酸、月桂酸、琥珀酸、油酸、邻苯二甲酸等羧酸的钯盐;氯化钯、二氯(环辛二烯)钯、二氯(降冰片二烯)钯、六氯化钯(IV)酸铵等钯的氯化物;碘化钯等碘化物;硫酸钯·二水合物等。在这些之中,特别优选羧酸的钯盐、二氯(降冰片二烯)钯和六氯化钯(IV)酸铵。氢化催化剂的使用量适当设定即可,相对于通过聚合得到的共聚物,优选为5~6000重量ppm,更优选为10~4000重量ppm。
在水层直接加氢法中,在加氢反应结束后除去胶乳中的氢化催化剂。作为该方法,能够采用例如添加活性炭、离子交换树脂等吸附剂,在搅拌下使其吸附氢化催化剂,接下来过滤或离心分离胶乳的方法。也能够不除去氢化催化剂,使其残留在胶乳中。
而且,在水层直接加氢法中,对于像这样得到的加氢反应后的胶乳,进行利用和醇的凝固、过滤分离和干燥等,由此能够得到本发明的含腈基共聚物橡胶。在该情况下的凝固后的过滤分离和干燥的工序能够分别按照公知的方法进行。
<橡胶组合物>
本发明的橡胶组合物含有上述本发明的含腈基共聚物橡胶和交联剂。
作为交联剂,没有特别限定,可以举出例如硫系交联剂、有机过氧化物交联剂以及多胺系交联剂。
作为硫系交联剂,可以举出;粉末硫、升华硫、沉降硫、胶体硫、表面处理硫、不溶性硫等硫;氯化硫、二氯化硫、二硫化吗啉、二硫化烷基酚、二硫化二苯并噻唑、N,N'-二硫代-双(六氢-2H-氮杂卓酮-2)、含磷多硫化物、高分子多硫化物等含硫化合物;二硫化四甲基秋兰姆、二甲基二硫代氨基甲酸硒、2-(4'-吗啉基二硫代)苯并噻唑等供硫性化合物等。这些能够单独使用一种或并用多种。
作为有机过氧化物交联剂,可举出二枯基过氧化物、氢过氧化枯烯、叔丁基枯基过氧化物、萜烷过氧化氢、二叔丁基过氧化物、1,3-双(叔丁基过氧化异丙基)苯、1,4-双(叔丁基过氧化异丙基)苯、1,1-二叔丁基过氧化-3,3-三甲基环己烷、4,4-双(叔丁基过氧化)戊酸正丁酯、2,5-二甲基-2,5-二叔丁基过氧化己烷、2,5-二甲基-2,5-二叔丁基过氧化-3-己炔、1,1-二叔丁基过氧化-3,5,5-三甲基环己烷、过氧化对氯苯甲酰、叔丁基过氧化异丙基碳酸酯、过氧化苯甲酸叔丁酯等。这些能够单独使用一种或并用多种。
作为多胺系交联剂,只要是具有两个以上的氨基的化合物或者在交联时成为具有两个以上氨基的化合物的形态的化合物,则没有特别限定,优选脂肪族烃、芳香族烃的多个氢原子被氨基或酰肼结构(-CONHNH2所表示的结构、CO表示羰基)取代的化合物和在交联时成为该化合物的形态的化合物。
作为多胺系交联剂的具体例,可举出:六亚甲基二胺、六亚甲基二胺氨基甲酸酯、N,N-二亚肉桂基-1,6-己二胺、四亚甲基五胺、六亚甲基二胺肉桂醛加成物等脂肪族多元胺类;4,4-亚甲基二苯胺、间苯二胺、4,4-二氨基二苯基醚、3,4-二氨基二苯基醚、4,4-(间亚苯基二异亚丙基)二苯胺、4,4-(对亚苯基二异亚丙基)二苯胺、2,2-双[4-(4-氨基苯氧基)苯基]丙烷、4,4-二氨基苯甲酰苯胺、4,4-双(4-氨基苯氧基)联苯、间苯二甲胺、对苯二甲胺、1,3,5-苯三胺等芳香族多元胺类;间苯二甲酸二酰肼、对苯二甲酸二酰肼、邻苯二甲酸二酰肼、2,6-萘二甲酸二酰肼、萘酸二酰肼、草酸二酰肼、丙二酸二酰肼、琥珀酸二酰肼、谷氨酸二酰肼、己二酸二酰肼、庚二酸二酰肼、辛二酸二酰肼、壬二酸二酰肼、癸二酸二酰肼、十三烷二酸二酰肼、十二烷二酸二酰肼、丙酮二羧酸二酰肼、富马酸二酰肼、马来酸二酰肼、衣康酸二酰肼、偏苯三酸二酰肼、1,3,5-苯三羧酸二酰肼、乌头酸二酰肼、均苯四酸二酰肼等多元酰肼类。在这些之中,从能够使本发明的效果更进一步显著的方面出发,优选脂肪族多元胺类和芳香族多元胺类,更优选六亚甲基二胺氨基甲酸酯和2,2-双[4-(4-氨基苯氧基)苯基]丙烷,特别优选六亚甲基二胺氨基甲酸酯。
本发明的橡胶组合物中的交联剂的含量没有特别限定,相对于100重量份的含腈基共聚物橡胶,优选为0.1~20重量份,更优选为0.2~15重量份,进一步优选为0.5~10重量份。通过使交联剂的含量为上述范围,能够使得到的橡胶交联物的机械特性更加良好。
此外,从能够进一步提高得到的橡胶交联物的机械特性的观点出发,本发明的橡胶组合物优选含有填充剂。作为填充剂,只要是在橡胶领域中通常使用的填充剂则没有特别限定,能够使用有机填充剂和无机填充剂中的任意一种,从其配合效果高的观点出发,优选无机填充剂。
作为无机填充剂,只要是在橡胶的配合中通常使用的无机填充剂即可,可以举出例如炭黑、二氧化硅、黏土、氧化铝、氢氧化铝、氧化镁、氢氧化镁、氧化钙、氢氧化钙、氧化铝镁、氧化钛、高岭土、叶蜡石、膨润土、滑石、绿坡缕石(Attapulgite)、硅酸镁钙、硅酸铝、硅酸镁、硅酸钙、结晶硅铝酸盐等。在这些之中,优选使用炭黑、二氧化硅、黏土,从使得到的橡胶交联物能够在加热环境下的耐油中固化性优异的观点出发,更优选二氧化硅、黏土,特别优选二氧化硅。无机填充剂能够单独使用一种或并用多种。
作为炭黑,只要是在橡胶的配合中通常使用的炭黑即可,可以举出例如炉法炭黑、乙炔黑、热裂炭黑、槽法炭黑以及石墨等。
作为二氧化硅,没有特别限定,可以举出:石英粉末、硅石粉末等天然二氧化硅;无水硅酸(硅胶,气凝胶等)、含水硅酸等合成二氧化硅等,在这些之中,优选合成二氧化硅。
作为黏土,只要是以含水硅酸铝为主成分的天然矿物即可,没有特别限定,可以举出蒙脱土、叶腊石、高岭石、埃洛石以及绢云母等。
作为无机填充剂,可以使用通过硅烷偶联剂、铝系偶联剂、钛系偶联剂等实施偶联处理的无机填充剂,以及通过高级脂肪酸或其金属盐、酯或酰胺等高级脂肪酸衍生物、表面活性剂等实施表面改性处理的无机填充剂。此时,作为无机填充剂,可以使用预先进行了表面改性处理的无机填充剂,或者,也可以采用在制备橡胶组合物时,通过将偶联处理等的表面改性剂与无机填充剂一起配合,进行无机填充剂的表面改性处理的方式。
作为硅烷偶联剂没有特别限定,可以举出:γ-巯丙基三甲氧基硅烷、γ-巯甲基三甲氧基硅烷、γ-巯甲基三乙氧基硅烷、双(3-三乙氧基甲硅烷基丙基)四硫化物、双(3-三乙氧基甲硅烷基丙基)二硫化物等含硫的硅烷偶联剂;γ-缩水甘油醚氧基丙基三甲氧基硅烷、γ-缩水甘油醚氧基丙基甲基二甲氧基硅烷、β-(3,4-环氧环己基)乙基三甲氧基硅烷、γ-巯丙基三甲氧基硅烷、γ-缩水甘油醚氧基丙基甲基二乙氧基硅烷等含环氧基的硅烷偶联剂;N-(β-氨基乙基)-γ-氨基丙基三甲氧基硅烷、γ-氨基丙基三甲氧基硅烷、γ-氨基丙基三乙氧基硅烷、N-2-(氨基乙基)-3-氨基丙基三甲氧基硅烷、N-2-(氨基乙基)-3-氨基丙基三乙氧基硅烷、3-三乙氧基甲硅烷基-N-(1,3-二甲基-亚丁基)丙基胺、N-苯基-3-氨基丙基三甲氧基硅烷等含氨基的硅烷偶联剂;γ-甲基丙烯酰氧基丙基三甲氧基硅烷、γ-甲基丙烯酰氧基丙基三(β-甲氧基乙氧基)硅烷、γ-甲基丙烯酰氧基丙基甲基二甲氧基硅烷、γ-甲基丙烯酰氧基丙基甲基二乙氧基硅烷、γ-甲基丙烯酰氧基丙基三乙氧基硅烷、γ-丙烯酰氧基丙基三甲氧基硅烷等含(甲基)丙烯酰氧基的硅烷偶联剂;乙烯基三甲氧基硅烷、乙烯基三乙氧基硅烷、乙烯基三(β-甲氧基乙氧基)硅烷、乙烯基三氯硅烷、乙烯基三乙酰氧基硅烷等含乙烯基的硅烷偶联剂;3-氯丙基三甲氧基硅烷等含氯丙基的硅烷偶联剂;3-异氰酸酯基丙基三乙氧基硅烷等含异氰酸酯基的硅烷偶联剂;对苯乙烯基三甲氧基硅烷等含苯乙烯基的硅烷偶联剂;3-脲基丙基三乙氧基硅烷等含脲基的硅烷偶联剂;二烯丙基二甲基硅烷等含烯丙基的硅烷偶联剂;四乙氧基硅烷等含烷氧基的硅烷偶联剂;二苯基二甲氧基硅烷等含苯基的硅烷偶联剂;三氟丙基三甲氧基硅烷等含氟基的硅烷偶联剂;异丁基三甲氧基硅烷、环己基甲基二甲氧基硅烷等含烷基的硅烷偶联剂等。
作为铝系偶联剂,可以举出例如乙酰烷氧基铝二异丙酯、乙酰乙酸二异丙氧基单乙酯铝、乙酰乙酸三乙酯铝、三乙酰基丙酮铝等。
作为钛酸酯系偶联剂,可以举出异丙基三异硬脂酰基钛酸酯、异丙基三(二辛基焦磷酸酰氧基)钛酸酯、异丙基三(N-氨乙基-氨乙基)钛酸酯、四辛基双[二(十三烷基)亚磷酸酰氧基]钛酸酯、四(2,2-二烯丙氧基甲基-1-丁基)双[二(十三烷基)]亚磷酸酰氧基钛酸酯、双(二辛基焦磷酸酰氧基)氧基乙酸酯钛酸酯、双(二辛基焦磷酸酰氧基)乙撑钛酸酯、四异丙基双(二辛基焦磷酸酰氧基)钛酸酯、异丙基三异硬脂酰基钛酸酯等。
这些能够使用一种或并用多种。
本发明的橡胶组合物中的无机填充剂的含量没有特别限定,相对于100重量份的含腈基共聚物橡胶,优选为1~200重量份,更优选为5~150重量份,进一步优选为10~100重量份,特别优选为20~50重量份。通过使无机填充剂的含量为上述范围,能够使得到的橡胶交联物在加热环境下的耐油中固化性更加优异。
此外,在本发明的橡胶组合物中,除上述以外,还能够配合在橡胶领域中通常使用的配合剂,例如:氧化锌、氧化镁等金属氧化物;甲基丙烯酸锌、丙烯酸锌等α,β-烯属不饱和羧酸金属盐;增塑剂;共交联剂;交联助剂;交联延迟剂;防老剂;抗氧化剂;光稳定剂;伯胺等防焦化剂;二甘醇等活化剂;加工助剂;滑剂;黏合剂;润滑剂;阻燃剂;防霉剂;酸性中和剂;抗静电剂;颜料;发泡剂等。这些配合剂的配合量只要在不阻碍本发明的目的、效果的范围则没有特别限定,能够配合与配合目的相应的量。
进而,在本发明的橡胶组合物中,也可以在不阻碍本发明的效果的范围配合除上述本发明的含腈基共聚物橡胶以外的橡胶。作为除本发明的含腈基共聚物橡胶以外的橡胶,能够举出丙烯酸橡胶、乙烯-丙烯酸共聚物橡胶、氟橡胶、苯乙烯-丁二烯共聚物橡胶、聚丁二烯橡胶、乙烯-丙烯共聚物橡胶、乙烯-丙烯-二烯三元共聚物橡胶、表氯醇橡胶、聚氨酯橡胶、氯丁二烯橡胶、硅橡胶、氟硅橡胶、氯磺化聚乙烯橡胶、天然橡胶及聚异戊二烯橡胶等。在配合除本发明的含腈基共聚物橡胶以外的橡胶的情况下,其配合量相对于100重量份的本发明的含腈基共聚物橡胶优选为30重量份以下,更优选为20重量份以下,特别优选为10重量份以下。
本发明的橡胶组合物优选将上述各成分在非水体系中进行混合来制备。制备本发明的橡胶组合物的方法没有限定,通常能够通过如下方法制备:将除了交联剂、遇热不稳定的成分(例如,交联助剂等)以外的成分使用班伯里混炼机、密炼机、捏合机等混合机进行一次混炼后,转移到辊等中,加入交联剂、遇热不稳定的成分等进行二次混炼。
<橡胶交联物>
本发明的橡胶交联物是将上述的本发明的交联性腈橡胶组合物交联形成的。
本发明的橡胶交联物能够通过如下方法制造:使用本发明的交联性橡胶组合物,通过与期望的形状对应的成型机例如挤出机、注射成型机、压缩机、辊等进行成型,通过加热进行交联反应,将形状固定化而制成交联物。在这种情况下,可以在预先成型后进行交联,也可以在成型的同时进行交联。成型温度通常为10~200℃,优选为25~120℃。交联温度通常为100~200℃,优选为130~190℃,交联时间通常为1分钟~24小时,优选为2分钟~1小时。
此外,根据交联物的形状、大小等,存在即使表面已经交联也没有充分交联至内部的情况,因此也可以进一步加热进行二次交联。
作为加热方法,适当选择压制加热、蒸汽加热、烘箱加热、热风加热等橡胶的交联中通常使用的方法即可。
像这样得到的本发明的橡胶交联物是使用上述本发明的橡胶组合物而得到的,常态物性良好且耐热性、耐油性以及在加热环境下的耐油中固化性(具体而言,在加热环境下保存后,浸渍在含有多环稠合芳香族化合物的油中时的玻璃化转变温度的变化以及硬度的变化小)优异。特别地,根据本发明,对于在加热环境下的耐油中固化性,在加热环境下保存后,即使在浸渍在耐油中固化相对显著地容易发生的含有多环稠合芳香族化合物的油中时,也能够有效地抑制油中固化的发生。
因此,本发明的橡胶交联物有效利用这样的特性,能够在以下广泛的用途中使用:O型环、填料、隔膜、油封、轴封、轴承密封件、井口密封件、减震器密封件、空气压缩机用密封件、空调的冷却装置、空调装置的制冷机用压缩机所使用的氟利昂或氟代烃或者二氧化碳的密封用密封件、精密洗涤的洗涤介质所使用的超临界二氧化碳或亚临界二氧化碳的密封用密封件、转动装置(滚动轴承、汽车用轮毂单元、汽车用水泵、直线导轨装置和滚珠丝杠等)用的密封件、阀和阀座、防喷器(BOP,Blow Out Preventer)、密封盘片等各种密封材料;进气歧管与汽缸盖的连接部所安装的进气歧管衬垫、汽缸体与汽缸盖的连接部所安装的汽缸盖衬垫、摇臂罩与汽缸盖的连接部所安装的摇臂罩衬垫、油底壳与汽缸体或变速器壳体的连接部所安装的油底壳衬垫、包夹具有正极、电解质板和负极的单元电池的一对外壳间所安装的燃料电池间隔件用衬垫、硬盘驱动器的顶罩用衬垫等各种衬垫;印刷用辊、制铁用辊、造纸用辊、工业用辊、办公设备用辊等各种辊;平带(膜核心平带(film core flatbelt)、线平带(cord flat belt)、层叠式平带、单体式平带等)、V带(包布V带、切边V带等)、V型多楔带(单V型多楔带、双V型多楔带、包布V型多楔带、背面橡胶V型多楔带、上齿V型多楔带等)、CVT用带、同步带、齿形带、传送带等各种带;燃料管、涡轮空气管、油管、散热器管、加热器管、水管、真空制动器管、控制管、空调管、制动器管、动力转向管、空气管、海上输油管、立管、流送管等各种管;CVJ护罩、螺旋轴护罩、等速万向节护罩、齿条齿轮传动装置(rackand pinion)护罩等各种护罩;缓冲材料、动态阻尼器、橡胶联轴器、空气悬架、防振材料、离合器衬片材料等阻尼材料橡胶部件;防尘罩、汽车内装部件、摩擦材料、轮胎、包覆电缆、鞋底、电磁波屏蔽体、柔性印刷基板用黏合剂等黏合剂、燃料电池间隔件,除此之外,还能够用于电子领域等。除此以外,本发明的橡胶交联物在加热环境下的耐油中固化性(具体而言,在加热环境下保存后,浸渍在含有多环稠合芳香族化合物的油中时的玻璃化转变温度的变化以及硬度的变化小)优异,因此能够特别优选在高温环境下与含有多环稠合芳香族化合物的燃料油接触使用的用途中使用。
实施例
以下,举出实施例和比较例,对本发明进行更具体地说明,但本发明并不限定于该实施例。以下,只要没有特别说明,“份”为重量基准。物性和特性的试验或评价方法如下所述。
<橡胶组成>
构成含腈基共聚物橡胶的各单体单元的含有比例通过以下方法进行测定。
即,甲基丙烯酸单元的含有比例通过以下方法算出:在0.2g的2mm见方的含腈基共聚物橡胶中,加入100mL的2-丁酮,搅拌16小时后,加入20mL的乙醇和10mL的水,一边搅拌一边使用氢氧化钾的0.02N的含水乙醇溶液,在室温以百里酚酞为指示剂进行滴定,由此求出相对于100g的含腈基共聚物橡胶的羧基的摩尔数,将求出的摩尔数换算成甲基丙烯酸单元的量。
1,3-丁二烯单元和饱和化丁二烯单元的含有比例通过使用含腈基共聚物橡胶测定加氢反应前和加氢反应后的碘值(根据JIS K 6235:2006)来算出。
甲基丙烯腈单元和丙烯腈单元的含有比例,根据JIS K6451-1:2016,通过杜马法测定含腈基共聚物橡胶中的氮元素含量,并且使用热解气相色谱法分别确定甲基丙烯腈单元以及丙烯腈单元,由此算出。
丙烯酸-2-甲氧基乙酯单元的含有比例由上述出得的甲基丙烯酸单元、1,3-丁二烯单元、饱和化丁二烯单元、甲基丙烯腈单元以及丙烯腈单元的含有比例通过计算求出。
<碘值>
含腈基共聚物橡胶的碘值基于JIS K 6235:2006进行测定。
<门尼黏度(聚合物·门尼)>
含腈基共聚物橡胶的门尼黏度(聚合物·门尼)根据JIS K6300:2013进行测定[单位为(ML1+4,100℃)]。
<常态物性(拉伸强度、伸长率、硬度)>
将橡胶组合物放入长15cm、宽15cm、深0.2cm的模具中,一边以10MPa压制压进行加压,一边在170℃压制成型20分钟,得到片状的橡胶交联物。接着,将得到的橡胶交联物转移到吉尔式烘箱中,在170℃二次交联4小时,将得到的片状的橡胶交联物使用JIS3号哑铃冲压,制作试验片。然后,使用得到的试验片,分别根据JIS K6251:2017测定橡胶交联物的拉伸强度以及断裂时的伸长率,或者,根据JIS K6253:2012使用硬度计硬度试验机(A型)测定橡胶交联物的硬度。
<耐热性试验>
与上述常态物性的评价同样地使用得到的片状交联物,根据JIS K6257:2017进行耐热试验。具体而言,将得到的片状橡胶交联物在温度150℃、504小时的条件下保持在吉尔式烘箱内后,与上述常态物性同样地进行拉伸强度和断裂时的伸长率的测定,求出拉伸强度的变化率和耐热试验后的伸长率。拉伸强度的变化率的值越大,或者耐热试验后的伸长率越大,则能够判断耐热性越优异。另外,拉伸强度的变化率由下述式算出。
拉伸强度的变化率(%)={(耐热试验后的拉伸强度-耐热试验前的拉伸强度)/耐热试验前的拉伸强度}×100
<耐油性试验(IRM903)>
与上述常态物性的评价同样地使用得到的片状交联物,根据JIS K6258:2016,通过在温度150℃、504小时的条件下浸渍在试验用润滑油No.3油(商品名“IRM903”,日本太阳石油株式会社制)中进行耐油试验。然后,测定在试验用润滑油中浸渍前后的橡胶交联物的体积,算出耐油试验后的体积变化率,并且与上述常态物性同样地进行断裂时的伸长率的测定,求出耐油试验后的伸长率。耐油试验后的体积变化率越小,或者,耐油试验后的伸长率越大,则能够判断耐油性越优异。另外,耐油试验后的体积变化率由下述式算出。
耐油试验后的体积变化率(%)={(耐油试验后的体积-耐油试验前的体积)/耐油试验前的体积}×100
<耐燃料油试验>
与上述常态物性的评价同样地使用得到的片状交联物,根据JIS K6258:2016,通过将得到的片状橡胶交联物在调节至150℃的试验燃料油(Fuel B:乙醇=74:26(体积比率)(Fuel B为异辛烷:甲苯=70:30(体积比率)的混合物)中浸渍168小时,进行耐燃料油试验。然后,对于进行了耐燃料油试验的橡胶交联物,与上述常态物性同样地进行拉伸强度和断裂时的伸长率的测定,求出拉伸强度的变化率和耐燃料油试验后的伸长率。拉伸强度的变化率的值越大,或者,耐燃料油试验后的伸长率越大,则能够判断耐油性(耐燃料油性)越优异。另外,拉伸强度的变化率由下述式算出。
拉伸强度的变化率(%)={(耐燃料油试验后的拉伸强度-耐燃料油试验前的拉伸强度)/耐燃料油试验前的拉伸强度}×100
<加热环境下的耐油中固化性试验(浸渍在含有多环稠合芳香族化合物的燃料油中时的玻璃化转变温度的变化以及硬度变化)>
通过向Fuel C(异辛烷∶甲苯=50∶50(体积比率)的混合物)与乙醇的混合液(FuelC∶乙醇=80∶20(体积比率))中溶解10重量%的菲,制备含菲试验燃料油。此外,与上述常态物性的评价同样地使用得到的片状交联物,进行玻璃化转变温度的测定。玻璃化转变温度根据JIS K7121:2012使用热流型差示扫描量热仪(设备:精工电子纳米科技(SIINanotechnology)株式会社制,X-DSC7000)以20℃/分钟的升温速度进行测定。然后,使用片状交联物,根据JIS K6257:2017通过在温度150℃、504小时的条件下保持在吉尔式烘箱中进行加热后,将加热后的橡胶交联物在上述制备的含菲试验燃料油中在60℃浸渍70小时后,将橡胶交联物从含菲试验燃料油中取出,在120℃干燥3小时,进一步在室温条件下静置24小时后,分别与上述同样地测定玻璃化转变温度,此外,与上述常态物性同样地测定硬度,由下述式分别求出玻璃化转变温度的变化以及硬度变化。玻璃化转变温度的变化越小,或者,硬度变化越小,则能够判断在加热环境下的耐油中固化性越优异。
玻璃化转变温度的变化(℃)=耐油中固化试验后的玻璃化转变温度-耐油中固化试验前的玻璃化转变温度
硬度变化=耐油中固化试验后的硬度-耐油中固化试验前的硬度
<实施例1>
在金属制瓶中,依次加入180份的离子交换水、25份的浓度10重量%的十二烷基苯磺酸钠水溶液、7份的甲基丙烯腈、21份的丙烯腈、30份的丙烯酸-2-甲氧基乙酯、2份的甲基丙烯酸以及0.5份的叔十二烷基硫醇(分子量调节剂),将内部气体用氮置换3次后,加入40份的1,3-丁二烯。将金属制瓶保持在5℃,加入0.1份的氢过氧化枯烯(聚合引发剂)、适量加入还原剂以及螯合剂,一边使金属制瓶旋转一边进行16小时聚合反应。加入0.1份的浓度1重量%的氢醌水溶液(聚合终止剂)终止聚合反应后,使用水温60℃的旋转蒸发仪除去残留单体,得到共聚物橡胶的胶乳(固体成分浓度约30重量%)。
然后,向高压釜中添加共聚物橡胶的胶乳和钯催化剂(混合有1重量%的氯化钯水溶液和等重量的离子交换水的溶液),以使得上述得到的共聚物橡胶的胶乳中的钯含量相对于该共聚物橡胶的干燥重量为3500重量ppm,在氢压3.0MPa、温度50℃进行7小时的加氢反应,得到含腈基共聚物橡胶(A-1)的胶乳。
接着,在得到的胶乳中加入2倍体积的甲醇,在凝固后,在60℃进行12小时的真空干燥,由此得到含腈基共聚物橡胶(A-1)。得到的含腈基共聚物橡胶(A-1)的各单体单元的组成为:8重量%的甲基丙烯腈单元、21重量%的丙烯腈单元、22重量%的丙烯酸-2-甲氧基乙酯单元、2.1重量%的甲基丙烯酸单元、46.9重量%的1,3-丁二烯单元(包含被氢化的部分),碘值为8,聚合物·门尼黏度[ML1+4,100℃]为60。
然后,向100份的得到的含腈基共聚物橡胶(A-1)中,配合30份的二氧化硅(商品名“CARPLEX1120”,赢创公司制)、5份的偏苯三酸三-2-乙基己酯(商品名“ADK CIZER-C-8”,ADEKA株式会社制,增塑剂)、1份的聚氧乙烯烷基醚磷酸酯(商品名“Phosphanol RL210”,东邦化学工业株式会社制,乳化剂)、1份的硬脂酸、1.5份的4,4'-双(α,α-二甲基苄基)二苯胺(商品名“NOCRAC CD”,大内新兴化学工业株式会社制,防老剂)、1.5份的2-巯基苯并咪唑的锌盐(商品名“NOCRAC MBZ”,大内新兴化学工业株式会社制,防老剂)、1.5份的硅烷偶联剂(商品名“Silanogran HVS”,Kettlitz公司制)以及7份的二丙烯酸锌(商品名“Dymalink633”,Cray Valley公司制),在50℃混合5分钟。接着,将得到的混合物转移到50℃的辊中,配合10份的1,3-双(叔丁基过氧化异丙基)苯(商品名“Vulcup40KE”,HERCULES公司制,有机过氧化物交联剂,40%品)进行混炼,由此得到橡胶组合物。
然后,使用得到的橡胶组合物,根据上述方法进行常态物性(拉伸强度、伸长率、硬度)的测定以及耐热性试验、耐油性试验(IRM903)、耐燃料油试验和在加热环境下的耐油中固化性试验。结果示于表1。
<实施例2~4>
将甲基丙烯腈、丙烯腈、丙烯酸-2-甲氧基乙酯、甲基丙烯酸以及1,3-丁二烯的使用量设为表1所示的量,除此以外,与实施例1同样地进行,得到含腈基共聚物橡胶(A-2)、(A-3)、(A-4),同样地制备橡胶组合物,同样地进行评价。结果示于表1。另外,含腈基共聚物橡胶(A-2)、(A-3)、(A-4)的单体组成、碘值以及聚合物·门尼黏度[ML1+4,100℃]如表1所示。
<实施例5~7>
将甲基丙烯腈、丙烯腈、甲基丙烯酸以及1,3-丁二烯的使用量设为表1所示的量,不使用丙烯酸-2-甲氧基乙酯,除此以外,与实施例1同样地进行,得到含腈基共聚物橡胶(A-5)、(A-6)、(A-7),同样地制备橡胶组合物,同样地进行评价。结果示于表1。另外,含腈基共聚物橡胶(A-5)、(A-6)、(A-7)的单体组成、碘值以及聚合物·门尼黏度[ML1+4,100℃]如表1所示。
<实施例8>
将甲基丙烯腈、丙烯腈以及1,3-丁二烯的使用量设为表1所示的量,不使用甲基丙烯酸以及丙烯酸-2-甲氧基乙酯,除此以外,与实施例1同样地进行,得到含腈基共聚物橡胶(A-8),同样地制备橡胶组合物,同样地进行评价。结果示于表1。另外,含腈基共聚物橡胶(A-8)的单体组成、碘值以及聚合物·门尼黏度[ML1+4,100℃]如表1所示。
<比较例1>
将甲基丙烯腈、丙烯酸-2-甲氧基乙酯、甲基丙烯酸以及1,3-丁二烯的使用量设为表1所示的量,不使用丙烯腈,除此以外,与实施例1同样地进行,得到含腈基共聚物橡胶(A'-9),同样地制备橡胶组合物,同样地进行评价。结果示于表1。另外,含腈基共聚物橡胶(A'-9)的单体组成、碘值以及聚合物·门尼黏度[ML1+4,100℃]如表1所示。
<比较例2>
将丙烯腈、丙烯酸-2-甲氧基乙酯、甲基丙烯酸以及1,3-丁二烯的使用量设为表1所示的量,不使用甲基丙烯腈,除此以外,与实施例1同样地进行,得到含腈基共聚物橡胶(A'-10),同样地制备橡胶组合物,同样地进行评价。结果示于表1。另外,含腈基共聚物橡胶(A'-10)的单体组成、碘值以及聚合物·门尼黏度[ML1+4,100℃]如表1所示。
<比较例3、4>
将甲基丙烯腈、丙烯腈、丙烯酸-2-甲氧基乙酯、甲基丙烯酸以及1,3-丁二烯的使用量设为表1所示的量,除此以外,与实施例1同样地进行,得到含腈基共聚物橡胶(A'-11)、(A'-12),同样地制备橡胶组合物,同样地进行评价。结果示于表1。另外,含腈基共聚物橡胶(A'-11)、(A'-12)的单体组成、碘值以及聚合物·门尼黏度[ML1+4,100℃]如表1所示。
<比较例5>
将丙烯腈以及1,3-丁二烯的使用量设为表1所示的量,不使用丙烯酸-2-甲氧基乙酯、甲基丙烯腈、甲基丙烯酸,除此以外,与实施例1同样地进行,得到含腈基共聚物橡胶(A'-13),同样地制备橡胶组合物,同样地进行评价。结果示于表1。另外,含腈基共聚物橡胶(A'-13)的单体组成、碘值以及聚合物·门尼黏度[ML1+4,100℃]如表1所示。
[表1]
如表1所示,根据含有丙烯腈单元(a)、除丙烯腈以外的α,β-烯属不饱和腈单体单元(b)以及共轭二烯单体单元(c)且碘值为120以下、丙烯腈单元(a)与除丙烯腈以外的α,β-烯属不饱和腈单体单元(b)的含有比例处于特定的范围的含腈基共聚物橡胶,使用其得到的橡胶交联物的常态物性良好,具有优异的耐热性,在使用试验用润滑油IRM903的情况下和使用燃料油的情况下均表现出优异的耐油性,并且在加热环境下的耐油中固化性(具体而言,在加热环境下保存后,浸渍在含有多环稠合芳香族化合物的油中时的玻璃化转变温度的变化以及硬度变化小)优异(实施例1~8)。
另一方面,在含腈基共聚物橡胶不含有丙烯腈单元(a)的情况下,使用其得到的橡胶交联物的常态的拉伸强度低,此外,在浸渍在试验用润滑油IRM903中时的体积变化率大,耐油性不充分,进而,在加热环境下保存后,浸渍在含有多环稠合芳香族化合物的油中时,硬度变化大,在加热环境下的耐油中固化性差(比较例1)。
此外,在含腈基共聚物橡胶不含有除丙烯腈以外的α,β-烯属不饱和腈单体单元(b)的情况下和除丙烯腈以外的α,β-烯属不饱和腈单体单元(b)的量过少的情况下,使用其得到的橡胶交联物在加热环境下保存后,浸渍在含有多环稠合芳香族化合物的油中时的玻璃化转变温度的变化以及硬度变化特别大,在加热环境下的耐油中固化性特别差(比较例2、4、5)。
在含腈基共聚物橡胶中的丙烯腈单元(a)的量过少的情况下,使用其得到的橡胶交联物的常态的拉伸强度低,此外,在浸渍在试验用润滑油IRM903时的体积变化率大,耐油性不充分(比较例3)。
Claims (9)
1.一种含腈基共聚物橡胶,其含有丙烯腈单元(a)、除丙烯腈以外的α,β-烯属不饱和腈单体单元(b)以及共轭二烯单体单元(c),碘值为120以下,
在全部单体单元中,所述丙烯腈单元(a)与所述除丙烯腈以外的α,β-烯属不饱和腈单体单元(b)的合计含量为1~50重量%,
所述丙烯腈单元(a)与所述除丙烯腈以外的α,β-烯属不饱和腈单体单元(b)的含有比例以“丙烯腈单元(a)的含量∶除丙烯腈以外的α,β-烯属不饱和腈单体单元(b)的含量”的重量比计为10∶90~90∶10。
2.根据权利要求1所述的含腈基共聚物橡胶,其特征在于,构成所述除丙烯腈以外的α,β-烯属不饱和腈单体单元(b)的除丙烯腈以外的α,β-烯属不饱和腈单体中的除氰基以外的碳原子数为2~5个。
3.根据权利要求1或2所述的含腈基共聚物橡胶,其特征在于,在全部单体单元中,所述丙烯腈单元(a)与所述除丙烯腈以外的α,β-烯属不饱和腈单体单元(b)的合计含量为10~45重量%。
4.根据权利要求1~3中任一项所述的含腈基共聚物橡胶,其特征在于,碘值为80以下。
5.根据权利要求1~4中任一项所述的含腈基共聚物橡胶,其中,所述丙烯腈单元(a)与所述除丙烯腈以外的α,β-烯属不饱和腈单体单元(b)的含有比例以“丙烯腈单元(a)的含量∶除丙烯腈以外的α,β-烯属不饱和腈单体单元(b)的含量”的重量比计为20∶80~80∶20。
6.根据权利要求1~5中任一项所述的含腈基共聚物橡胶,其中,所述丙烯腈单元(a)与所述除丙烯腈以外的α,β-烯属不饱和腈单体单元(b)的含有比例以“丙烯腈单元(a)的含量∶除丙烯腈以外的α,β-烯属不饱和腈单体单元(b)的含量”的重量比计为25∶75~75∶25。
7.根据权利要求1~6中任一项所述的含腈基共聚物橡胶,其特征在于,所述共轭二烯单体单元(c)的含量为10~90重量%。
8.一种橡胶组合物,其是在权利要求1~7中任一项所述的含腈基共聚物橡胶中配合交联剂而成的。
9.一种橡胶交联物,其是将权利要求8所述的橡胶组合物交联而成的。
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US3753959A (en) * | 1969-09-17 | 1973-08-21 | Synthetic Rubber Co Ltd | Alternating copolymers |
US3697489A (en) * | 1970-08-05 | 1972-10-10 | Borg Warner | High temperature nitrile elastomer |
JPS62156144A (ja) * | 1985-12-28 | 1987-07-11 | Japan Synthetic Rubber Co Ltd | 加硫可能なゴム組成物 |
JPS62230837A (ja) * | 1986-03-31 | 1987-10-09 | Nippon Zeon Co Ltd | シ−ル用ゴム組成物 |
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