CA2238941C - Fluorinated onium salts, curable compositions containing same, and method of curing using same - Google Patents
Fluorinated onium salts, curable compositions containing same, and method of curing using same Download PDFInfo
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- CA2238941C CA2238941C CA002238941A CA2238941A CA2238941C CA 2238941 C CA2238941 C CA 2238941C CA 002238941 A CA002238941 A CA 002238941A CA 2238941 A CA2238941 A CA 2238941A CA 2238941 C CA2238941 C CA 2238941C
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- cure accelerator
- cure
- fluorinated
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- 239000000203 mixture Substances 0.000 title claims abstract description 69
- 238000000034 method Methods 0.000 title claims abstract description 17
- 150000003839 salts Chemical class 0.000 title description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 32
- 229920000642 polymer Polymers 0.000 claims abstract description 27
- 125000003118 aryl group Chemical group 0.000 claims abstract description 16
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 claims abstract description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 12
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical group [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 claims abstract description 9
- 150000004010 onium ions Chemical group 0.000 claims abstract description 8
- 125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 6
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims abstract description 6
- 239000008896 Opium Substances 0.000 claims description 18
- 229960001027 opium Drugs 0.000 claims description 18
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 14
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 claims description 9
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 7
- 239000006082 mold release agent Substances 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 3
- 125000001033 ether group Chemical group 0.000 claims description 3
- 150000002500 ions Chemical class 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 23
- 125000006850 spacer group Chemical group 0.000 abstract description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 63
- -1 sulfonium compound Chemical class 0.000 description 37
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 32
- 239000000047 product Substances 0.000 description 26
- 239000000243 solution Substances 0.000 description 22
- 230000000052 comparative effect Effects 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 19
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
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- LREAZWJEBORMTB-UHFFFAOYSA-N bis(2-methylpropyl)phosphane Chemical compound CC(C)CPCC(C)C LREAZWJEBORMTB-UHFFFAOYSA-N 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 14
- ZFVMWEVVKGLCIJ-UHFFFAOYSA-N bisphenol AF Chemical compound C1=CC(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C=C1 ZFVMWEVVKGLCIJ-UHFFFAOYSA-N 0.000 description 11
- 239000000370 acceptor Substances 0.000 description 10
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- 238000001746 injection moulding Methods 0.000 description 9
- 230000000704 physical effect Effects 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 229910052731 fluorine Inorganic materials 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 229920001897 terpolymer Polymers 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 7
- 239000011737 fluorine Substances 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 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 6
- 229920002313 fluoropolymer Polymers 0.000 description 6
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- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
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- 229920001577 copolymer Polymers 0.000 description 5
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 4
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- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 4
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- SNXRKUDPXIYDNQ-UHFFFAOYSA-N 3-[bis(2-methylpropyl)phosphanyl]propan-1-amine Chemical compound CC(C)CP(CC(C)C)CCCN SNXRKUDPXIYDNQ-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000002671 adjuvant Substances 0.000 description 3
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 3
- 229940073608 benzyl chloride Drugs 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 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 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000000806 elastomer Substances 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical compound FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 3
- UWNADWZGEHDQAB-UHFFFAOYSA-N i-Pr2C2H4i-Pr2 Natural products CC(C)CCC(C)C UWNADWZGEHDQAB-UHFFFAOYSA-N 0.000 description 3
- 239000000395 magnesium oxide Substances 0.000 description 3
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
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- 150000004714 phosphonium salts Chemical group 0.000 description 3
- 238000010926 purge Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 229940124530 sulfonamide Drugs 0.000 description 3
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- OWLGMGLVCDLDNG-UHFFFAOYSA-N 2-[3-[bis(2-methylpropyl)phosphanyl]propyl]phenol Chemical compound CC(C)CP(CC(C)C)CCCC1=CC=CC=C1O OWLGMGLVCDLDNG-UHFFFAOYSA-N 0.000 description 2
- TXBIZRLVIDXDGB-UHFFFAOYSA-N 2-methylpropylphosphane Chemical compound CC(C)CP TXBIZRLVIDXDGB-UHFFFAOYSA-N 0.000 description 2
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 2
- 238000004679 31P NMR spectroscopy Methods 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-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
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 2
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- 238000012512 characterization method Methods 0.000 description 2
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
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- 229910021641 deionized water Inorganic materials 0.000 description 2
- RGLYKWWBQGJZGM-ISLYRVAYSA-N diethylstilbestrol Chemical compound C=1C=C(O)C=CC=1C(/CC)=C(\CC)C1=CC=C(O)C=C1 RGLYKWWBQGJZGM-ISLYRVAYSA-N 0.000 description 2
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- SNGREZUHAYWORS-UHFFFAOYSA-M 2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctanoate Chemical compound [O-]C(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F SNGREZUHAYWORS-UHFFFAOYSA-M 0.000 description 1
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- IILRWDAJGJROQW-UHFFFAOYSA-N 2-sulfanyl-3h-1,3-benzothiazole-2-carboxylic acid Chemical compound C1=CC=C2SC(C(=O)O)(S)NC2=C1 IILRWDAJGJROQW-UHFFFAOYSA-N 0.000 description 1
- KVOWYXYBDGNJJF-UHFFFAOYSA-N 3,3-dibutylheptyl(methoxy)phosphanium chloride Chemical compound [Cl-].C(CCC)C(CC[PH2+]OC)(CCCC)CCCC KVOWYXYBDGNJJF-UHFFFAOYSA-N 0.000 description 1
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- 229910002651 NO3 Inorganic materials 0.000 description 1
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- BHFJBHMTEDLICO-UHFFFAOYSA-N Perfluorooctylsulfonyl fluoride Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)S(F)(=O)=O BHFJBHMTEDLICO-UHFFFAOYSA-N 0.000 description 1
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 1
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- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
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- 239000003518 caustics Substances 0.000 description 1
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- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 1
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- 150000004820 halides Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
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- 238000002329 infrared spectrum Methods 0.000 description 1
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- UMKARVFXJJITLN-UHFFFAOYSA-N lead;phosphorous acid Chemical compound [Pb].OP(O)O UMKARVFXJJITLN-UHFFFAOYSA-N 0.000 description 1
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- UHNWOJJPXCYKCG-UHFFFAOYSA-L magnesium oxalate Chemical compound [Mg+2].[O-]C(=O)C([O-])=O UHNWOJJPXCYKCG-UHFFFAOYSA-L 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- XOCNYZFAMHDXJK-UHFFFAOYSA-N methyl 2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctanoate Chemical compound COC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F XOCNYZFAMHDXJK-UHFFFAOYSA-N 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 150000002891 organic anions Chemical class 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- RRRXPPIDPYTNJG-UHFFFAOYSA-N perfluorooctanesulfonamide Chemical compound NS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F RRRXPPIDPYTNJG-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
- REJGOFYVRVIODZ-UHFFFAOYSA-N phosphanium;chloride Chemical class P.Cl REJGOFYVRVIODZ-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 238000001394 phosphorus-31 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- UNYWISZSMFIKJI-UHFFFAOYSA-N prop-2-ene-1-sulfonamide Chemical compound NS(=O)(=O)CC=C UNYWISZSMFIKJI-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 239000003340 retarding agent Substances 0.000 description 1
- 238000010074 rubber mixing Methods 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- UUCCCPNEFXQJEL-UHFFFAOYSA-L strontium dihydroxide Chemical compound [OH-].[OH-].[Sr+2] UUCCCPNEFXQJEL-UHFFFAOYSA-L 0.000 description 1
- 229910001866 strontium hydroxide Inorganic materials 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical group FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- 238000007056 transamidation reaction Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000011787 zinc oxide Substances 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
- C08F8/00—Chemical modification by after-treatment
-
- 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
- C08F2800/00—Copolymer characterised by the proportions of the comonomers expressed
- C08F2800/20—Copolymer characterised by the proportions of the comonomers expressed as weight or mass percentages
Landscapes
- Chemical & Material Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/576,097 US5591804A (en) | 1995-12-21 | 1995-12-21 | Fluorinated onium salts, curable compositions containing same, and method of curing using same |
| US08/576097 | 1995-12-21 | ||
| PCT/US1996/018936 WO1997023556A1 (en) | 1995-12-21 | 1996-11-26 | Fluorinated onium salts, curable compositions containing same, and method of curing using same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2238941A1 CA2238941A1 (en) | 1997-07-03 |
| CA2238941C true CA2238941C (en) | 2006-10-03 |
Family
ID=24302974
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002238941A Expired - Fee Related CA2238941C (en) | 1995-12-21 | 1996-11-26 | Fluorinated onium salts, curable compositions containing same, and method of curing using same |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US5591804A (enExample) |
| EP (1) | EP0868477B1 (enExample) |
| JP (1) | JP3723221B2 (enExample) |
| AU (1) | AU1061797A (enExample) |
| CA (1) | CA2238941C (enExample) |
| DE (1) | DE69633135T2 (enExample) |
| WO (1) | WO1997023556A1 (enExample) |
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| JP4712977B2 (ja) | 1999-03-02 | 2011-06-29 | スリーエム イノベイティブ プロパティズ カンパニー | 非弗素化ポリマーにフルオロポリマーを接着させるための組成物 |
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| US20040114772A1 (en) * | 2002-03-21 | 2004-06-17 | David Zlotnick | Method and system for transmitting and/or receiving audio signals with a desired direction |
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| EP1634895B1 (en) * | 2004-09-09 | 2008-11-05 | 3M Innovative Properties Company | Fluoropolymer for making a fluoroelastomer |
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| JP5584123B2 (ja) * | 2007-09-14 | 2014-09-03 | スリーエム イノベイティブ プロパティズ カンパニー | 超低粘度ヨウ素含有非晶質フルオロポリマー |
| US20100069554A1 (en) * | 2008-09-18 | 2010-03-18 | Dupont Performance Elastomers L.L.C. | Curable fluoropolymer compositions |
| US7964001B2 (en) | 2009-04-14 | 2011-06-21 | Dupont Performance Elastomers L.L.C. | Fuel management systems having a fluororubber article in contact with biodiesel fuel |
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| TWI523900B (zh) | 2010-07-20 | 2016-03-01 | 首威索勒希斯股份有限公司 | 氟彈性體組合物 |
| US8309641B2 (en) | 2010-08-13 | 2012-11-13 | E I Du Pont De Nemours And Company | Curable fluoroelastomer compositions |
| US8227535B2 (en) | 2010-12-07 | 2012-07-24 | E I Du Pont De Nemours And Company | Polyhydroxy curable fluoroelastomer compositions |
| GB201108963D0 (en) | 2011-05-27 | 2011-07-13 | 3M Innovative Properties Co | Composite materials comprising polyamides and fluoroelastomers |
| EP2557109B1 (en) | 2011-08-11 | 2019-01-23 | 3M Innovative Properties Company | Method of bonding a fluoroelastomer compound to a metal substrate using low molecular weight functional hydrocarbons as bonding promoter |
| US9074074B2 (en) | 2011-12-15 | 2015-07-07 | The Chemours Company Fc, Llc | Polyhydroxy curable fluoroelastomer compositions |
| WO2014099454A1 (en) | 2012-12-18 | 2014-06-26 | E. I. Du Pont De Nemours And Company | Laminates of fluoroelastomer and heat-resistant acrylate elastomer |
| US9540496B2 (en) | 2013-02-07 | 2017-01-10 | The Chemours Company Fc, Llc | Polyhydroxy curable fluoroelastomer composition |
| CN110168002A (zh) | 2016-12-28 | 2019-08-23 | 3M创新有限公司 | 含硅卤化弹性体 |
| WO2019126298A1 (en) | 2017-12-22 | 2019-06-27 | 3M Innovative Properties Company | Peroxide-cured halogenated elastomers having a silicon-containing superficial layer |
| WO2019159066A1 (en) | 2018-02-19 | 2019-08-22 | 3M Innovative Properties Company | Blends of crosslinking agents for fluoroelastomers |
| CN111757906A (zh) | 2018-02-19 | 2020-10-09 | 3M创新有限公司 | 可固化含氟弹性体组合物 |
| CN111757908A (zh) | 2018-02-19 | 2020-10-09 | 3M创新有限公司 | 可固化含氟弹性体组合物 |
| US20210155774A1 (en) | 2018-04-10 | 2021-05-27 | 3M Innovative Properties Company | Blends of crosslinking agents for fluoroelastomers |
| WO2019239288A1 (en) | 2018-06-12 | 2019-12-19 | 3M Innovative Properties Company | Fluorinated polymer coating compositions and articles therefrom |
| US11859074B2 (en) | 2018-06-13 | 2024-01-02 | 3M Innovative Properties Company | Curable fluoroelastomer composition |
| EP3837309A1 (en) | 2018-08-13 | 2021-06-23 | 3M Innovative Properties Company | Curable fluoroelastomer composition |
| US11492457B2 (en) | 2019-06-06 | 2022-11-08 | 3M Innovative Properties Company | Curable fluoropolymer compositions comprising a compound containing a phthalonitrile and a nucleophilic functional group and cured articles therefrom |
| EP3990438B1 (en) | 2019-06-28 | 2023-11-15 | 3M Innovative Properties Company | Hydroxy-functionalized triazine compounds. curable fluoropolymer compositions comprising such compounds and cured articles therefrom |
| EP4021967B1 (en) | 2019-08-27 | 2023-03-01 | 3M Innovative Properties Company | Curable fluoropolymer compositions comprising metal fluoride particles and articles therefrom |
| KR20250070605A (ko) | 2022-09-20 | 2025-05-20 | 더 케무어스 컴퍼니 에프씨, 엘엘씨 | 플루오로엘라스토머용 경화제로서의 비-플루오린화된 레소르시놀 및 히드로퀴논 유사체 |
| EP4590762A1 (en) | 2022-09-20 | 2025-07-30 | The Chemours Company FC, LLC | Fluorinated resorcinol and hydroquinone analogs as curing agents for fluoroelastomers |
| KR20250080894A (ko) | 2022-10-12 | 2025-06-05 | 더 케무어스 컴퍼니 에프씨, 엘엘씨 | 경화성 플루오로엘라스토머 조성물 및 이로부터 형성된 저마찰의 경화된 플루오로엘라스토머(fkM) |
| WO2025193781A1 (en) | 2024-03-13 | 2025-09-18 | The Chemours Company Fc, Llc | Fluorinated resorcinol and hydroquinone analogs as curing agents for fluoroelastomers |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3442664A (en) * | 1966-04-26 | 1969-05-06 | Minnesota Mining & Mfg | Treating composition,method of treating and treated surfaces |
| US3518292A (en) * | 1967-03-27 | 1970-06-30 | Dow Corning | Quaternary phosphonium silicon complexes |
| US4094911A (en) * | 1969-03-10 | 1978-06-13 | Minnesota Mining And Manufacturing Company | Poly(perfluoroalkylene oxide) derivatives |
| US3876654A (en) * | 1970-12-23 | 1975-04-08 | Du Pont | Fluoroelastomer composition |
| USB493537I5 (enExample) * | 1973-10-16 | 1976-03-23 | ||
| NL189567C (nl) * | 1977-12-14 | 1993-05-17 | Montedison Spa | Vulcaniseerbare mengsels op basis van elastomere copolymeren van vinylideenfluoride, werkwijze om deze te vulcaniseren en voorwerpen geheel of gedeeltelijk bestaande uit de zo verkregen gevulcaniseerde mengsels. |
| US4233421A (en) * | 1979-02-26 | 1980-11-11 | Minnesota Mining And Manufacturing Company | Fluoroelastomer composition containing sulfonium curing agents |
| US5086123A (en) * | 1984-02-27 | 1992-02-04 | Minnesota Mining And Manufacturing Company | Fluoroelastomer compositions containing fluoroaliphatic sulfonamides as curing agents |
| US4535184A (en) * | 1984-06-08 | 1985-08-13 | E. I. Du Pont De Nemours And Company | Tris(disubstituted amino)sulfonium perfluorocarbanion salts |
| JPS6121149A (ja) * | 1984-07-09 | 1986-01-29 | Daikin Ind Ltd | 加硫成形用組成物 |
| US4927887A (en) * | 1984-09-21 | 1990-05-22 | Bridgestone/Firestone, Inc. | Modified rubber compositions containing aromatic six-membered heterocyclic nitrogen-containing groups |
| US4828923A (en) * | 1987-04-10 | 1989-05-09 | Nippon Zeon Co., Ltd. | Rubber laminates of fluororubber and nitrile rubber |
| CA1328533C (en) * | 1988-04-01 | 1994-04-12 | Werner Marie Aschille Grootaert | Fluoroelastomer composition |
| US4882390A (en) * | 1988-04-01 | 1989-11-21 | Minnesota Mining And Manufacturing Company | Fluoroelastomer composition with organo-onium compounds |
| US4912171A (en) * | 1988-04-01 | 1990-03-27 | Minnesota Mining And Manufacturing Company | Fluoroelastomer curing process with phosphonium compound |
| JP2583444B2 (ja) * | 1988-06-23 | 1997-02-19 | 日本ゼオン株式会社 | ゴム積層体の製造方法 |
| US5322904A (en) * | 1988-09-28 | 1994-06-21 | Exfluor Research Corporation | Liquid-phase fluorination |
| US5384374A (en) * | 1991-01-11 | 1995-01-24 | Minnesota Mining And Manufacturing Company | Curing fluorocarbon elastomers |
| JPH05339536A (ja) * | 1992-06-11 | 1993-12-21 | Minnesota Mining & Mfg Co <3M> | フッ素ゴム塗布用組成物 |
| US5262490A (en) * | 1992-08-24 | 1993-11-16 | Minnesota Mining And Manufacturing Company | Fluoroelastomer composition with organo-onium compounds |
| US5274159A (en) * | 1993-02-18 | 1993-12-28 | Minnesota Mining And Manufacturing Company | Destructable fluorinated alkoxysilane surfactants and repellent coatings derived therefrom |
-
1995
- 1995-12-21 US US08/576,097 patent/US5591804A/en not_active Expired - Fee Related
-
1996
- 1996-11-26 DE DE69633135T patent/DE69633135T2/de not_active Expired - Fee Related
- 1996-11-26 WO PCT/US1996/018936 patent/WO1997023556A1/en not_active Ceased
- 1996-11-26 AU AU10617/97A patent/AU1061797A/en not_active Abandoned
- 1996-11-26 JP JP52364697A patent/JP3723221B2/ja not_active Expired - Fee Related
- 1996-11-26 EP EP96941490A patent/EP0868477B1/en not_active Expired - Lifetime
- 1996-11-26 CA CA002238941A patent/CA2238941C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP3723221B2 (ja) | 2005-12-07 |
| EP0868477B1 (en) | 2004-08-11 |
| EP0868477A1 (en) | 1998-10-07 |
| JP2000502389A (ja) | 2000-02-29 |
| US5591804A (en) | 1997-01-07 |
| CA2238941A1 (en) | 1997-07-03 |
| DE69633135D1 (de) | 2004-09-16 |
| WO1997023556A1 (en) | 1997-07-03 |
| DE69633135T2 (de) | 2005-09-08 |
| AU1061797A (en) | 1997-07-17 |
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