JP5487541B2 - ニトリルゴム、ニトリルゴム組成物および架橋物 - Google Patents
ニトリルゴム、ニトリルゴム組成物および架橋物 Download PDFInfo
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- JP5487541B2 JP5487541B2 JP2007542624A JP2007542624A JP5487541B2 JP 5487541 B2 JP5487541 B2 JP 5487541B2 JP 2007542624 A JP2007542624 A JP 2007542624A JP 2007542624 A JP2007542624 A JP 2007542624A JP 5487541 B2 JP5487541 B2 JP 5487541B2
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- Prior art keywords
- nitrile rubber
- rubber composition
- weight
- nitrile
- coagulant
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 229920000459 Nitrile rubber Polymers 0.000 title claims description 127
- 239000000203 mixture Substances 0.000 title claims description 58
- 239000000178 monomer Substances 0.000 claims description 68
- 229920001971 elastomer Polymers 0.000 claims description 52
- 239000005060 rubber Substances 0.000 claims description 51
- -1 amine compound Chemical class 0.000 claims description 41
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 39
- 239000000701 coagulant Substances 0.000 claims description 31
- 229920000126 latex Polymers 0.000 claims description 28
- 238000004132 cross linking Methods 0.000 claims description 24
- 239000004816 latex Substances 0.000 claims description 24
- 229920001577 copolymer Polymers 0.000 claims description 21
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 18
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 18
- 239000007864 aqueous solution Substances 0.000 claims description 18
- 239000011575 calcium Substances 0.000 claims description 18
- 229910052791 calcium Inorganic materials 0.000 claims description 18
- 239000011777 magnesium Substances 0.000 claims description 18
- 229910052749 magnesium Inorganic materials 0.000 claims description 18
- 229910052782 aluminium Inorganic materials 0.000 claims description 16
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 16
- 150000001993 dienes Chemical class 0.000 claims description 16
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 14
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 13
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 claims description 13
- 229910052740 iodine Inorganic materials 0.000 claims description 13
- 239000011630 iodine Substances 0.000 claims description 13
- 230000015271 coagulation Effects 0.000 claims description 12
- 238000005345 coagulation Methods 0.000 claims description 12
- 150000002825 nitriles Chemical class 0.000 claims description 12
- 239000004711 α-olefin Substances 0.000 claims description 12
- 238000007789 sealing Methods 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 8
- 229910052943 magnesium sulfate Inorganic materials 0.000 claims description 7
- 235000019341 magnesium sulphate Nutrition 0.000 claims description 7
- UTOVMEACOLCUCK-SNAWJCMRSA-N (e)-4-butoxy-4-oxobut-2-enoic acid Chemical group CCCCOC(=O)\C=C\C(O)=O UTOVMEACOLCUCK-SNAWJCMRSA-N 0.000 claims description 6
- UTOVMEACOLCUCK-PLNGDYQASA-N butyl maleate Chemical compound CCCCOC(=O)\C=C/C(O)=O UTOVMEACOLCUCK-PLNGDYQASA-N 0.000 claims description 5
- 230000001112 coagulating effect Effects 0.000 claims description 5
- 230000007935 neutral effect Effects 0.000 claims description 3
- 239000003792 electrolyte Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 36
- 238000012360 testing method Methods 0.000 description 26
- 239000003431 cross linking reagent Substances 0.000 description 23
- 238000000034 method Methods 0.000 description 22
- 238000007906 compression Methods 0.000 description 20
- 230000006835 compression Effects 0.000 description 20
- 125000002560 nitrile group Chemical group 0.000 description 18
- 229920006395 saturated elastomer Polymers 0.000 description 17
- 239000004593 Epoxy Substances 0.000 description 16
- 230000020169 heat generation Effects 0.000 description 14
- 238000004519 manufacturing process Methods 0.000 description 14
- 229910052751 metal Inorganic materials 0.000 description 14
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical group C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 11
- 239000002184 metal Substances 0.000 description 11
- 150000002148 esters Chemical class 0.000 description 9
- 238000005984 hydrogenation reaction Methods 0.000 description 9
- 238000006116 polymerization reaction Methods 0.000 description 9
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 230000032683 aging Effects 0.000 description 6
- 230000003712 anti-aging effect Effects 0.000 description 6
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 238000004898 kneading Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- 238000007334 copolymerization reaction Methods 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- NKHAVTQWNUWKEO-UHFFFAOYSA-N fumaric acid monomethyl ester Natural products COC(=O)C=CC(O)=O NKHAVTQWNUWKEO-UHFFFAOYSA-N 0.000 description 5
- 238000000465 moulding Methods 0.000 description 5
- 150000001451 organic peroxides Chemical class 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 229920005862 polyol Polymers 0.000 description 4
- 150000003077 polyols Chemical class 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 4
- ZMQWRASVUXJXGM-VOTSOKGWSA-N (e)-4-cyclohexyloxy-4-oxobut-2-enoic acid Chemical class 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
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical group CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 3
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- XLYMOEINVGRTEX-UHFFFAOYSA-N fumaric acid monoethyl ester Natural products CCOC(=O)C=CC(O)=O XLYMOEINVGRTEX-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- 239000011976 maleic acid Substances 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
- NKHAVTQWNUWKEO-NSCUHMNNSA-N monomethyl fumarate Chemical compound COC(=O)\C=C\C(O)=O NKHAVTQWNUWKEO-NSCUHMNNSA-N 0.000 description 3
- 229940005650 monomethyl fumarate Drugs 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000012856 packing Methods 0.000 description 3
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 2
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-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
- YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-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
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 2
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 2
- UJAWGGOCYUPCPS-UHFFFAOYSA-N 4-(2-phenylpropan-2-yl)-n-[4-(2-phenylpropan-2-yl)phenyl]aniline Chemical compound C=1C=C(NC=2C=CC(=CC=2)C(C)(C)C=2C=CC=CC=2)C=CC=1C(C)(C)C1=CC=CC=C1 UJAWGGOCYUPCPS-UHFFFAOYSA-N 0.000 description 2
- KHYXYOGWAIYVBD-UHFFFAOYSA-N 4-(4-propylphenoxy)aniline Chemical compound C1=CC(CCC)=CC=C1OC1=CC=C(N)C=C1 KHYXYOGWAIYVBD-UHFFFAOYSA-N 0.000 description 2
- VVAAYFMMXYRORI-UHFFFAOYSA-N 4-butoxy-2-methylidene-4-oxobutanoic acid Chemical compound CCCCOC(=O)CC(=C)C(O)=O VVAAYFMMXYRORI-UHFFFAOYSA-N 0.000 description 2
- OIYTYGOUZOARSH-UHFFFAOYSA-N 4-methoxy-2-methylidene-4-oxobutanoic acid Chemical compound COC(=O)CC(=C)C(O)=O OIYTYGOUZOARSH-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
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 2
- XLYMOEINVGRTEX-ARJAWSKDSA-N Ethyl hydrogen fumarate Chemical compound CCOC(=O)\C=C/C(O)=O XLYMOEINVGRTEX-ARJAWSKDSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 125000005396 acrylic acid ester group Chemical group 0.000 description 2
- 238000012644 addition polymerization Methods 0.000 description 2
- IBVAQQYNSHJXBV-UHFFFAOYSA-N adipic acid dihydrazide Chemical compound NNC(=O)CCCCC(=O)NN IBVAQQYNSHJXBV-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 229910001038 basic metal oxide Inorganic materials 0.000 description 2
- UTTHLMXOSUFZCQ-UHFFFAOYSA-N benzene-1,3-dicarbohydrazide Chemical compound NNC(=O)C1=CC=CC(C(=O)NN)=C1 UTTHLMXOSUFZCQ-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical class [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 description 2
- APEJMQOBVMLION-UHFFFAOYSA-N cinnamamide Chemical compound NC(=O)C=CC1=CC=CC=C1 APEJMQOBVMLION-UHFFFAOYSA-N 0.000 description 2
- 229930003836 cresol Natural products 0.000 description 2
- 239000011243 crosslinked material Substances 0.000 description 2
- 239000012933 diacyl peroxide Substances 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
- 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
- 230000000694 effects Effects 0.000 description 2
- 238000010556 emulsion polymerization method Methods 0.000 description 2
- 238000007720 emulsion polymerization reaction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 125000003709 fluoroalkyl group Chemical group 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- NKHAVTQWNUWKEO-IHWYPQMZSA-N methyl hydrogen fumarate Chemical compound COC(=O)\C=C/C(O)=O NKHAVTQWNUWKEO-IHWYPQMZSA-N 0.000 description 2
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- 239000011787 zinc oxide Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- FYGDTMLNYKFZSV-BYLHFPJWSA-N β-1,4-galactotrioside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@H](CO)O[C@@H](O[C@@H]2[C@@H](O[C@@H](O)[C@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O FYGDTMLNYKFZSV-BYLHFPJWSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C1/00—Treatment of rubber latex
- C08C1/14—Coagulation
- C08C1/15—Coagulation characterised by the coagulants used
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L13/00—Compositions of rubbers containing carboxyl groups
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
架橋剤(B)と、
を含有してなるニトリルゴム組成物が提供される。
好ましくは、カルボキシル基が、前記ニトリルゴム(A)の構成単位であるエチレン性不飽和ジカルボン酸モノエステル単量体に由来するものである。
好ましくは、前記α,β−エチレン性不飽和ニトリル単量体単位が、アクリロニトリル単位及び/又はメタクリロニトリル単位である。
好ましくは、前記ニトリルゴム(A)は、ジエン単量体単位及び/又はα−オレフィン単量体単位をさらに有する。
好ましくは、前記ジエン単量体単位が、1,3−ブタジエン単位である。
好ましくは、前記ニトリルゴム(A)中における、前記ジエン単量体単位及び/又はα−オレフィン単量体単位の含有量が、25〜85重量%である。
好ましくは、前記架橋剤(B)が、多価アミン化合物、多価ヒドラジド化合物及び有機過酸化物から選択される少なくとも1種である。
好ましくは、前記架橋剤(B)の含有量が、前記カルボキシル基含有ニトリルゴム(A)100重量部に対して、0.1〜20重量部である。
また、本発明のニトリルゴム組成物は、前記カルボキシル基含有ニトリルゴム(A)と、架橋剤(B)と、を含有してなるものである。
カルボキシル基含有ニトリルゴム(A)(以下、「ニトリルゴム(A)」と記すことがある。)中のマグネシウム、カルシウム及びアルミニウムの合計含有量は、これらの金属元素換算で、ニトリルゴム(A)全体に対して、2,000重量ppm以下であり、好ましくは1,000重量ppm以下、より好ましくは500重量ppm以下、さらに好ましくは100重量ppm以下、特に好ましくは50重量ppm以下である。マグネシウム、カルシウム及びアルミニウムの合計含有量が多過ぎると、架橋物の圧縮永久ひずみ及び動的発熱が大きくなる。
これらのなかでも、イタコン酸モノメチル、イタコン酸モノn−ブチル、フマル酸モノメチル、フマル酸モノn−ブチル、フマル酸モノシクロヘキシル、マレイン酸モノメチル、マレイン酸モノエチル及びマレイン酸モノn−ブチルが好ましく、フマル酸モノn−ブチルおよびマレイン酸モノn−ブチルが特に好ましい。
α,β−エチレン性不飽和多価カルボン酸としては、イタコン酸、フマル酸、マレイン酸などが挙げられる。
α,β−エチレン性不飽和多価カルボン酸無水物としては、無水マレイン酸などが挙げられる。
次いで、(α)乳化重合後の、又は乳化重合に続いて水素添加反応を行った後の共重合体ゴムのラテックスを、凝固剤水溶液により、pHが1〜6、好ましくは2〜5の条件下で凝固し(以下、「凝固工程」と略す。)、濾過し、水を加えて繰り返し洗浄し、遠心脱水機で脱水後に乾燥してニトリルゴム(A)を得る方法、及び(β)乳化重合後、共重合体ゴムのラテックスを凝固剤水溶液によりpHが1〜6、好ましくは2〜5の条件下で凝固し、濾過、繰り返し洗浄し、遠心脱水機で脱水後に乾燥して得た固体の共重合ゴムを溶剤に溶解し、水素添加反応を行ってニトリルゴム(A)を得る方法、等により製造することができる。
なお、凝固工程後の濾過及び乾燥の方法は公知の方法が適用される。
共重合して得られた共重合体ゴムのヨウ素価が、前記の範囲より高くなる場合には、重合後、水素化(水素添加反応)を行うと良い。水素化の方法は特に限定されず、公知の方法が採用される。
本発明のニトリルゴム組成物は、上記ニトリルゴム(A)と、架橋物を形成するための架橋剤(B)と、を含有してなるものである。架橋剤(B)としては、有機過酸化物、硫黄系架橋剤、樹脂架橋剤、多価アミン化合物、多価ヒドラジド化合物、多価エポキシ化合物、多価イソシアナート化合物、多価アルコール化合物、アジリジン化合物、塩基性金属酸化物、有機金属ハロゲン化物などが挙げられる。また、これらの架橋剤を複数併用してもよい。
シールとしては、回転用、揺動用、往復運動用などの運動用シールと固定用シールが挙げられる。運動用シールとしては、オイルシール、ピストンシール、メカニカルシール、プラター、BOPなどの油田用シール、CVJブーツ、プロペラシャフトブーツなどの各種ブーツ、ダストカバー、ダイアフラムなどが挙げられる。固定用シールとしては、O−リング、インテークマニホールドガスケットなどの各種ガスケット、各種パッキンなどが挙げられる。
ニトリルゴムのカルボキシル基含有量の測定は、水酸化カリウムの0.02N含水エタノール溶液を用いて、室温にて、チモールフタレインを指示薬とする滴定により、ゴム100グラムに対するカルボキシル基のモル数を求めることにより行った。単位はephrである。
ニトリルゴムのムーニー粘度は、JIS K 6300に従って測定した。
ニトリルゴム組成物中の金属(マグネシウム、カルシウム及びアルミニウム)含有量は、ニトリルゴム組成物試料に硫酸、硝酸を添加して加熱し、湿式分解し、次いで、これを適宜希釈して、ICP−AES(SPS−5000:セイコーインスツルメント社製)を使用して、内標準検量線法で測定した。
ニトリルゴム組成物を縦15cm、横15cm、深さ0.2cmの金型に入れ、加圧しながら170℃で20分間プレス成形した後、170℃のオーブンに4時間置いて、シート状ゴム架橋物を得た。得られたシート状ゴム架橋物を3号形ダンベルで打ち抜き、試験片を作製した。そして、これらの試験片を用いて、JIS K 6251に従い、架橋物の引張強さ及び伸びを測定した。
上記(4)と同様にして得たシート状ゴム架橋物の試験片について、JIS K 6253に従い、デュロメータ硬さ試験機タイプAを用いて架橋物の硬さを測定した。
上記(4)と同様にて得たシート状ゴム架橋物の試験片について、JIS K 6257(ノーマルオーブン法)に従い、150℃、168時間後の伸びの変化率(%)及び硬さの差(ポイント)を求めた。
ニトリルゴム組成物を内径29mm、深さ12.5mmの円柱状金型に入れ、170℃で20分間、10MPaの圧力でプレスして架橋した後、170℃で4時間二次架橋を行い、圧縮永久ひずみ試験用試験片を得た。圧縮永久ひずみは、これらの試験片を用いて150℃、25%圧縮状態で168時間保持した後、JIS K6262に従って測定した。
動的発熱性は、ASTM D 623−78で規定されるフレクソメータ試験で評価した。先ず、直径17.8±0.1mm、高さ25±0.15mmの円柱状のゴム片を、170℃で20分間架橋した後、さらに170℃で4時間二次架橋を行うことにより、フレクソメータ試験用試験片を得た。試験は、グッドリッチフレクソメータを用いて、試験温度100℃、初期荷重25ポンド(11.34kg)、動的変位4.45mmの条件で25分間動的変位を加えて行い、HBU(発熱量:測定された試験片の温度と雰囲気温度100℃との差を発熱温度とした。)を測定した。HBUは小さいほど動的発熱が小さく、動的発熱性が優れている。
ニトリルゴム(架橋剤及び他の配合剤を添加しない状態)について、表面温度50℃のロール混練機で混練作業を行うことにより、加工性を評価した。ロール表面に粘着する場合は加工性が悪いと評価し(表1中、記号:×で示した。)、粘着しない場合は加工性が良いと評価した(表1中、記号:○で示した。)。
金属製ボトルに、イオン交換水225部、濃度10重量%のドデシルベンゼンスルホン酸ナトリウム水溶液25部、アクリロニトリル37部、フマル酸モノn−ブチル4部、t−ドデシルメルカプタン(分子量調整剤)0.5部の順に仕込み、内部の気体を窒素で3回置換した後、ブタジエン59部を仕込んだ。金属製ボトルを5℃に保ち、クメンハイドロパーオキサイド(重合開始剤)0.1部を仕込み、金属製ボトルを回転させながら16時間重合反応を行った。そして、濃度10重量%のハイドロキノン水溶液(重合停止剤)0.1部を加えて重合反応を停止した後、水温60℃のロータリーエバポレータを用いて残留単量体を除去し、アクリロニトリル単量体単位34重量%、ブタジエン単量体単位62.5重量%およびフマル酸モノ−n−ブチル単量体単位3.5重量%を有するアクリロニトリル−ブタジエン−α,β−エチレン性不飽和ジカルボン酸モノアルキルエステル共重合体ゴムのラテックス(固形分濃度約30重量%)を得た。
製造例1において、フマル酸モノ−n−ブチルに代えてマレイン酸モノ−n−ブチル(製造例2)又はフマル酸モノシクロヘキシル(製造例3)をそれぞれ使用した他は、製造例1と同様に重合及び水素添加を行って、それぞれニトリル基含有高飽和共重合体ゴムのラテックスb(製造例2:pHは6)及びラテックスc(製造例3:pHは6)を得た。
製造例1において、フマル酸モノn−ブチルに代えてフマル酸モノメチルを使用して同様に重合を行った後、水素添加を行わずに、ニトリル基含有共重合体ゴムのラテックスd(pHは6)を得た。
製造例1で得たニトリル基含有高飽和共重合体ゴムのラテックスa100部に、硫酸マグネシウム5重量%水溶液(硫酸マグネシウムの量が、共重合体ゴムに対して30重量%となる量であり、微量の硫酸を加えることにより、pHを4に調整した。)を加えて、ニトリル基含有高飽和共重合体ゴムを凝固した後、得られたゴムを濾過し、水を加えて洗浄した。この濾過及び洗浄操作を3回繰り返した後、遠心脱水機にかけてゴム中に含まれる硫酸マグネシウム水溶液を除去した。次いで、60℃で12時間真空乾燥してニトリルゴム(1)を得た。ニトリルゴム(1)のアクリロニトリル単量体単位の含有量は34重量%、ヨウ素価は9、カルボキシル基含有量は2×10−2ephr、ムーニー粘度〔ML1+4、100℃〕は85であった。
実施例1において、ニトリル基含有高飽和共重合体ゴムのラテックスaに代えてラテックスbを使用した他は、実施例1と同様に行ってニトリルゴム(2)を得た。ニトリルゴム(2)のアクリロニトリル単量体単位の含有量は34重量%、ヨウ素価は9、カルボキシル基含有量は1×10−2ephr、ムーニー粘度〔ML1+4、100℃〕 は80であった。
ニトリルゴム(2)につき実施例1と同様にしてニトリルゴム組成物を調製し、実施例1と同様の試験、評価を行った結果を表1に記す。
実施例1において、ニトリル基含有高飽和共重合体ゴムのラテックスaに代えてラテックスcを使用した他は、実施例1と同様に行ってニトリルゴム(3)を得た。ニトリルゴム(3)のアクリロニトリル単量体単位の含有量は34重量%、ヨウ素価は9、カルボキシル基含有量は2×10−2ephr、ムーニー粘度〔ML1+4、100℃〕は85であった。
ニトリルゴム(3)につき実施例1と同様にしてニトリルゴム組成物を調製し、実施例1と同様の試験、評価を行った結果を表1に記す。
実施例1において、ラテックスa100部に対する凝固剤として、硫酸マグネシウム5重量%水溶液に代えて、塩化カルシウム2重量%の水溶液(塩化カルシウムの量が、共重合体ゴムに対して12重量%となる量)を使用し、凝固剤水溶液のpHを7にした他は、実施例1と同様に行ってニトリルゴム(4)を得た。ニトリルゴム(4)のアクリロニトリル単量体単位の含有量は34重量%、ヨウ素価は9、カルボキシル基含有量は2×10−2ephr、ムーニー粘度〔ML1+4、100℃〕は90であった。
ニトリルゴム(4)につき実施例1と同様にしてニトリルゴム組成物を調製し、実施例1と同様の試験、評価を行った結果を表1に記す。
実施例1において、ニトリル基含有高飽和共重合体ゴムのラテックスaに代えてラテックスdを使用した他は、実施例1と同様に行ってニトリルゴム(5)を得た。ニトリルゴム(5)のアクリロニトリル単量体単位の含有量は34重量%、ヨウ素価は200以上、カルボキシル基含有量は2×10−2ephr、ムーニー粘度〔ML1+4、100℃〕は40であった。
ニトリルゴム(5)につき実施例1と同様にしてニトリルゴム組成物を調製し、実施例1と同様の試験、評価を行った結果を表1に記す。
製造例1で得たニトリル基含有高飽和共重合体ゴムのラテックスaに、その2倍容量のメタノールを加えてニトリル基含有高飽和共重合体ゴムを凝固した後、60℃で12時間真空乾燥し、ニトリルゴム(6)を得た。ニトリルゴム(6)のアクリロニトリル単量体単位含有量は34重量%、ヨウ素価は9、カルボキシル基含有量は2×10−2ephr、ムーニー粘度〔ML1+4、100℃〕は85であった。
また、ラテックスdを水素添加せずに用いた場合には、ニトリルゴム組成物を調製する際に、実施例1と同様に凝固させても、ニトリルゴムのヨウ素価が高すぎるため、これにより、架橋物は耐熱性に劣り、また、圧縮永久ひずみが大きくなる結果となった(比較例2)。
さらに、実施例1と同じ原料ラテックスを用いても、メタノールで凝固すると、得られるニトリルゴムは加工性の悪いものであった(比較例3)。
Claims (8)
- 共重合体ゴムのラテックスを、水溶性の電解質である凝固剤の水溶液により凝固する工程を経て得られ、α,β−エチレン性不飽和ニトリル単量体単位の含有量が10〜60重量%であり、α,β−エチレン性不飽和ジカルボン酸モノエステル単量体単位を含有し、ヨウ素価が120以下であり、かつ、マグネシウム、カルシウム及びアルミニウムの合計含有量が2,000重量ppm以下であるカルボキシル基含有ニトリルゴム、および多価アミン化合物を含有してなるシール用ニトリルゴム組成物。
- 前記凝固剤が、アルミニウム含有凝固剤、マグネシウム含有凝固剤、又は、カルシウム含有凝固剤である請求項1に記載のシール用ニトリルゴム組成物。
- 前記凝固工程に用いる凝固剤が、硫酸マグネシウムである請求項1に記載のシール用ニトリルゴム組成物。
- 前記カルボキシル基含有ニトリルゴムが、凝固工程のpHを1〜6に設定して得られたものである、請求項1〜3のいずれか1項に記載のシール用ニトリルゴム組成物。
- 前記凝固工程に用いる凝固剤水溶液が、中性凝固剤の水溶液に酸を加え、pHを1〜6に調製したものである請求項4に記載のシール用ニトリルゴム組成物。
- 前記カルボキシル基含有ニトリルゴムが、ジエン単量体単位及び/又はα−オレフィン単量体単位をさらに有し、
前記カルボキシル基含有ニトリルゴム中における、前記ジエン単量体単位及び/又はα−オレフィン単量体単位の含有量が、25〜85重量%である請求項1〜5のいずれか1項に記載のシール用ニトリルゴム組成物。 - 前記α,β−エチレン性不飽和ジカルボン酸モノエステル単量体単位が、フマル酸モノ−n−ブチル、又は、マレイン酸モノ−n−ブチルである請求項1
〜6のいずれか1項に記載のシール用ニトリルゴム組成物。 - 請求項1〜7のいずれか1項に記載のシール用ニトリルゴム組成物を架橋してなるシール用架橋物。
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