DE60018476T2 - Fluorosulfoneelastomere mit niedrigem tg basierend auf vinylidenfluorit - Google Patents
Fluorosulfoneelastomere mit niedrigem tg basierend auf vinylidenfluorit Download PDFInfo
- Publication number
- DE60018476T2 DE60018476T2 DE60018476T DE60018476T DE60018476T2 DE 60018476 T2 DE60018476 T2 DE 60018476T2 DE 60018476 T DE60018476 T DE 60018476T DE 60018476 T DE60018476 T DE 60018476T DE 60018476 T2 DE60018476 T2 DE 60018476T2
- Authority
- DE
- Germany
- Prior art keywords
- vinyl ether
- fluorinated
- perfluoro
- vdf
- copolymerization
- 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.)
- Expired - Lifetime
Links
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 claims abstract description 60
- 229920001971 elastomer Polymers 0.000 claims abstract description 48
- 239000000806 elastomer Substances 0.000 claims abstract description 48
- GAZFDPSEEIVCEX-UHFFFAOYSA-N dimethyl 2-(2-methylpropyl)propanedioate Chemical compound COC(=O)C(CC(C)C)C(=O)OC GAZFDPSEEIVCEX-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000000446 fuel Substances 0.000 claims abstract description 8
- 239000003999 initiator Substances 0.000 claims abstract description 7
- 230000009477 glass transition Effects 0.000 claims abstract description 6
- 229920001577 copolymer Polymers 0.000 claims description 38
- 238000000034 method Methods 0.000 claims description 38
- -1 Trifluoroethylene, chlorotrifluoroethylene, bromotrifluoroethylene Chemical group 0.000 claims description 31
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 claims description 21
- 238000007334 copolymerization reaction Methods 0.000 claims description 20
- 239000000178 monomer Substances 0.000 claims description 19
- 239000002904 solvent Substances 0.000 claims description 18
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 16
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- BLTXWCKMNMYXEA-UHFFFAOYSA-N 1,1,2-trifluoro-2-(trifluoromethoxy)ethene Chemical compound FC(F)=C(F)OC(F)(F)F BLTXWCKMNMYXEA-UHFFFAOYSA-N 0.000 claims description 9
- 150000001336 alkenes Chemical class 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 9
- 239000012528 membrane Substances 0.000 claims description 8
- 239000000839 emulsion Substances 0.000 claims description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 5
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 5
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 5
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical compound FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 claims description 4
- 239000003208 petroleum Substances 0.000 claims description 4
- 239000004094 surface-active agent Substances 0.000 claims description 4
- WUMVZXWBOFOYAW-UHFFFAOYSA-N 1,2,3,3,4,4,4-heptafluoro-1-(1,2,3,3,4,4,4-heptafluorobut-1-enoxy)but-1-ene Chemical compound FC(F)(F)C(F)(F)C(F)=C(F)OC(F)=C(F)C(F)(F)C(F)(F)F WUMVZXWBOFOYAW-UHFFFAOYSA-N 0.000 claims description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 3
- QMIWYOZFFSLIAK-UHFFFAOYSA-N 3,3,3-trifluoro-2-(trifluoromethyl)prop-1-ene Chemical group FC(F)(F)C(=C)C(F)(F)F QMIWYOZFFSLIAK-UHFFFAOYSA-N 0.000 claims description 3
- FDMFUZHCIRHGRG-UHFFFAOYSA-N 3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C=C FDMFUZHCIRHGRG-UHFFFAOYSA-N 0.000 claims description 3
- JGZVUTYDEVUNMK-UHFFFAOYSA-N 5-carboxy-2',7'-dichlorofluorescein Chemical compound C12=CC(Cl)=C(O)C=C2OC2=CC(O)=C(Cl)C=C2C21OC(=O)C1=CC(C(=O)O)=CC=C21 JGZVUTYDEVUNMK-UHFFFAOYSA-N 0.000 claims description 3
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 238000010528 free radical solution polymerization reaction Methods 0.000 claims description 3
- 238000005192 partition Methods 0.000 claims description 3
- FYJQJMIEZVMYSD-UHFFFAOYSA-N perfluoro-2-butyltetrahydrofuran Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C1(F)OC(F)(F)C(F)(F)C1(F)F FYJQJMIEZVMYSD-UHFFFAOYSA-N 0.000 claims description 3
- ZJIJAJXFLBMLCK-UHFFFAOYSA-N perfluorohexane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F ZJIJAJXFLBMLCK-UHFFFAOYSA-N 0.000 claims description 3
- 125000005634 peroxydicarbonate group Chemical group 0.000 claims description 3
- 125000005373 siloxane group Chemical group [SiH2](O*)* 0.000 claims description 3
- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 claims description 3
- 238000012546 transfer Methods 0.000 claims description 3
- WFJINAXLTGKWLB-UHFFFAOYSA-N 1-ethenoxy-1,1,2,2,3,3-hexafluoro-3-(trifluoromethoxy)propane Chemical compound FC(F)(F)OC(F)(F)C(F)(F)C(F)(F)OC=C WFJINAXLTGKWLB-UHFFFAOYSA-N 0.000 claims description 2
- ZLFSOCVJMGQPTE-UHFFFAOYSA-N 1-ethenoxy-1,1,2,2-tetrafluoro-2-(trifluoromethoxy)ethane Chemical compound FC(F)(F)OC(F)(F)C(F)(F)OC=C ZLFSOCVJMGQPTE-UHFFFAOYSA-N 0.000 claims description 2
- ODCNTFOJYJYLPH-UHFFFAOYSA-N 1-ethenoxy-1,1,2,3,3,3-hexafluoro-2-(trifluoromethoxy)propane Chemical compound FC(F)(F)OC(F)(C(F)(F)F)C(F)(F)OC=C ODCNTFOJYJYLPH-UHFFFAOYSA-N 0.000 claims description 2
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 claims description 2
- AQKYLAIZOGOPAW-UHFFFAOYSA-N 2-methylbutan-2-yl 2,2-dimethylpropaneperoxoate Chemical compound CCC(C)(C)OOC(=O)C(C)(C)C AQKYLAIZOGOPAW-UHFFFAOYSA-N 0.000 claims description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 2
- YYXDEKORUCONSJ-UHFFFAOYSA-N C=COCCC(OCCF)S(F)(=O)=O Chemical compound C=COCCC(OCCF)S(F)(=O)=O YYXDEKORUCONSJ-UHFFFAOYSA-N 0.000 claims description 2
- 150000003863 ammonium salts Chemical class 0.000 claims description 2
- 125000000129 anionic group Chemical group 0.000 claims description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 2
- 125000002091 cationic group Chemical group 0.000 claims description 2
- BSVQJWUUZCXSOL-UHFFFAOYSA-N cyclohexylsulfonyl ethaneperoxoate Chemical compound CC(=O)OOS(=O)(=O)C1CCCCC1 BSVQJWUUZCXSOL-UHFFFAOYSA-N 0.000 claims description 2
- 239000004530 micro-emulsion Substances 0.000 claims description 2
- 229920003023 plastic Polymers 0.000 claims description 2
- 239000004033 plastic Substances 0.000 claims description 2
- BWJUFXUULUEGMA-UHFFFAOYSA-N propan-2-yl propan-2-yloxycarbonyloxy carbonate Chemical compound CC(C)OC(=O)OOC(=O)OC(C)C BWJUFXUULUEGMA-UHFFFAOYSA-N 0.000 claims description 2
- 239000000725 suspension Substances 0.000 claims description 2
- UPVJEODAZWTJKZ-OWOJBTEDSA-N (e)-1,2-dichloro-1,2-difluoroethene Chemical group F\C(Cl)=C(\F)Cl UPVJEODAZWTJKZ-OWOJBTEDSA-N 0.000 claims 2
- BZPCMSSQHRAJCC-UHFFFAOYSA-N 1,2,3,3,4,4,5,5,5-nonafluoro-1-(1,2,3,3,4,4,5,5,5-nonafluoropent-1-enoxy)pent-1-ene Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)=C(F)OC(F)=C(F)C(F)(F)C(F)(F)C(F)(F)F BZPCMSSQHRAJCC-UHFFFAOYSA-N 0.000 claims 2
- HTHNTJCVPNKCPZ-UHFFFAOYSA-N 2-chloro-1,1-difluoroethene Chemical group FC(F)=CCl HTHNTJCVPNKCPZ-UHFFFAOYSA-N 0.000 claims 2
- CBYABTHXYJJUTO-UHFFFAOYSA-N (1-tert-butylcyclohexyl) carboxyoxy carbonate Chemical compound OC(=O)OOC(=O)OC1(C(C)(C)C)CCCCC1 CBYABTHXYJJUTO-UHFFFAOYSA-N 0.000 claims 1
- 239000003792 electrolyte Substances 0.000 claims 1
- CWINGZLCRSDKCL-UHFFFAOYSA-N ethoxycarbonyloxy ethyl carbonate Chemical compound CCOC(=O)OOC(=O)OCC CWINGZLCRSDKCL-UHFFFAOYSA-N 0.000 claims 1
- 229920000554 ionomer Polymers 0.000 claims 1
- 238000005065 mining Methods 0.000 claims 1
- CSJWOWRPMBXQLD-UHFFFAOYSA-N perfluoromethylvinylether group Chemical group FC(=C(C(F)(F)F)F)OC(=C(F)C(F)(F)F)F CSJWOWRPMBXQLD-UHFFFAOYSA-N 0.000 claims 1
- 150000003871 sulfonates Chemical class 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 abstract description 8
- 230000015572 biosynthetic process Effects 0.000 abstract description 6
- 150000002978 peroxides Chemical class 0.000 abstract description 4
- 150000008049 diazo compounds Chemical class 0.000 abstract description 2
- 239000003921 oil Substances 0.000 abstract description 2
- 150000002976 peresters Chemical class 0.000 abstract description 2
- 239000002585 base Substances 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 239000007788 liquid Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 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
- 239000007789 gas Substances 0.000 description 6
- 229920001897 terpolymer Polymers 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 229920002449 FKM Polymers 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 238000007720 emulsion polymerization reaction Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 238000002411 thermogravimetry Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- RRZIJNVZMJUGTK-UHFFFAOYSA-N 1,1,2-trifluoro-2-(1,2,2-trifluoroethenoxy)ethene Chemical compound FC(F)=C(F)OC(F)=C(F)F RRZIJNVZMJUGTK-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 238000010526 radical polymerization reaction Methods 0.000 description 3
- 238000010557 suspension polymerization reaction Methods 0.000 description 3
- 229920003934 Aciplex® Polymers 0.000 description 2
- 229920003935 Flemion® Polymers 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 229920000557 Nafion® Polymers 0.000 description 2
- 229910006095 SO2F Inorganic materials 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 150000007942 carboxylates Chemical group 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 description 2
- 238000007872 degassing Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 239000001307 helium Substances 0.000 description 2
- 229910052734 helium Inorganic materials 0.000 description 2
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 2
- 230000010354 integration Effects 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 210000002023 somite Anatomy 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229920003249 vinylidene fluoride hexafluoropropylene elastomer Polymers 0.000 description 2
- KHXKESCWFMPTFT-UHFFFAOYSA-N 1,1,1,2,2,3,3-heptafluoro-3-(1,2,2-trifluoroethenoxy)propane Chemical compound FC(F)=C(F)OC(F)(F)C(F)(F)C(F)(F)F KHXKESCWFMPTFT-UHFFFAOYSA-N 0.000 description 1
- AYCANDRGVPTASA-UHFFFAOYSA-N 1-bromo-1,2,2-trifluoroethene Chemical group FC(F)=C(F)Br AYCANDRGVPTASA-UHFFFAOYSA-N 0.000 description 1
- 238000004293 19F NMR spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- DMWVYCCGCQPJEA-UHFFFAOYSA-N 2,5-bis(tert-butylperoxy)-2,5-dimethylhexane Chemical compound CC(C)(C)OOC(C)(C)CCC(C)(C)OOC(C)(C)C DMWVYCCGCQPJEA-UHFFFAOYSA-N 0.000 description 1
- XRYWSOJOSFWGLH-UHFFFAOYSA-N 2-(3-ethenoxy-1,1,2,2,3,3-hexafluoropropoxy)-1,1,1,2,3,3,3-heptafluoropropane Chemical compound FC(F)(F)C(F)(C(F)(F)F)OC(F)(F)C(F)(F)C(F)(F)OC=C XRYWSOJOSFWGLH-UHFFFAOYSA-N 0.000 description 1
- ZMXDDKWLCZADIW-YYWVXINBSA-N DMF-d7 Substances [2H]C(=O)N(C([2H])([2H])[2H])C([2H])([2H])[2H] ZMXDDKWLCZADIW-YYWVXINBSA-N 0.000 description 1
- 101100049616 Drosophila melanogaster Strump gene Proteins 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000012662 bulk polymerization Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 238000009795 derivation Methods 0.000 description 1
- CSCPPACGZOOCGX-WFGJKAKNSA-N deuterated acetone Substances [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 229920001198 elastomeric copolymer Polymers 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000000806 fluorine-19 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 229920001973 fluoroelastomer Polymers 0.000 description 1
- 229920002313 fluoropolymer Polymers 0.000 description 1
- 239000004811 fluoropolymer Substances 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 229910000856 hastalloy Inorganic materials 0.000 description 1
- PGFXOWRDDHCDTE-UHFFFAOYSA-N hexafluoropropylene oxide Chemical group FC(F)(F)C1(F)OC1(F)F PGFXOWRDDHCDTE-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000004377 microelectronic Methods 0.000 description 1
- 238000012703 microemulsion polymerization Methods 0.000 description 1
- 239000010705 motor oil Substances 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical compound FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000003797 telogen phase Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010257 thawing Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- 238000005303 weighing Methods 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
- C08F214/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
- C08F214/18—Monomers containing fluorine
- C08F214/22—Vinylidene fluoride
- C08F214/222—Vinylidene fluoride with fluorinated vinyl ethers
-
- 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
- C08F14/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
- C08F14/18—Monomers containing fluorine
- C08F14/22—Vinylidene fluoride
-
- 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
- C08F216/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical
- C08F216/12—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical by an ether radical
- C08F216/14—Monomers containing only one unsaturated aliphatic radical
- C08F216/1408—Monomers containing halogen
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/13—Hollow or container type article [e.g., tube, vase, etc.]
- Y10T428/1352—Polymer or resin containing [i.e., natural or synthetic]
- Y10T428/139—Open-ended, self-supporting conduit, cylinder, or tube-type article
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Dental Preparations (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Glass Compositions (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA2293846 | 1999-12-29 | ||
| CA 2293846 CA2293846A1 (fr) | 1999-12-29 | 1999-12-29 | Elastomeres fluorosulfones a faible tg a base de fluorure de vinylidene et ne contenant ni du tetrafluoroethylene, ni de l'hexafluoropropene, ni de groupement siloxane |
| CA2299622 | 2000-02-24 | ||
| CA002299622A CA2299622A1 (fr) | 2000-02-24 | 2000-02-24 | Elastomeres fluorosulfones a faible tg a base de fluorure de vinylidene et ne contenant ni du tetrafluoroethylene, ni de l'hexafluoropropene, ni de groupement siloxane |
| PCT/CA2000/001585 WO2001049757A1 (fr) | 1999-12-29 | 2000-12-29 | Elastomeres fluorosulfones a faible tg a base de fluorure de vinylidene |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60018476D1 DE60018476D1 (de) | 2005-04-07 |
| DE60018476T2 true DE60018476T2 (de) | 2006-02-16 |
Family
ID=25681440
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60018476T Expired - Lifetime DE60018476T2 (de) | 1999-12-29 | 2000-12-29 | Fluorosulfoneelastomere mit niedrigem tg basierend auf vinylidenfluorit |
Country Status (7)
| Country | Link |
|---|---|
| US (4) | US20030148158A1 (https=) |
| EP (1) | EP1252205B1 (https=) |
| JP (1) | JP2003519259A (https=) |
| AT (1) | ATE290026T1 (https=) |
| AU (1) | AU2496101A (https=) |
| DE (1) | DE60018476T2 (https=) |
| WO (1) | WO2001049757A1 (https=) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001049760A1 (fr) * | 1999-12-29 | 2001-07-12 | HYDRO-QUéBEC | ELASTOMERES FLUOROSULFONES A FAIBLE Tg A BASE D'HEXAFLUOROPROPENE ET NE CONTENANT NI DU TETRAFLUOROETHYLENE, NI DE GROUPEMENT SILOXANE |
| US20030148158A1 (en) * | 1999-12-29 | 2003-08-07 | Ameduri Bruno Michel | Fluorosulphonated elastomers with low glass transition based on vinylidene fluoride |
| CA2312194A1 (fr) * | 2000-06-13 | 2001-12-13 | Mario Boucher | Elastomeres reticulables fluores bromosulfones a faible tg a base de fluorure de vinylidene et ne contenant ni du tetrafluoroethylene ni de groupement siloxane |
| IT1318594B1 (it) * | 2000-06-23 | 2003-08-27 | Ausimont Spa | Processo di polimerizzazione di monomeri solfonici. |
| CA2328433A1 (fr) * | 2000-12-20 | 2002-06-20 | Hydro-Quebec | Elastomeres nitriles fluorosulfones reticulables a faible tg a base de fluorure de vinylidene et ne contenant ni du tetrafluoroethylene ni de groupement siloxane |
| US6777515B2 (en) * | 2001-07-13 | 2004-08-17 | I. Du Pont De Nemours And Company | Functional fluorine-containing polymers and ionomers derived therefrom |
| US7094851B2 (en) * | 2001-12-06 | 2006-08-22 | Gore Enterprise Holdings, Inc. | Low equivalent weight ionomer |
| US7425601B2 (en) | 2002-12-20 | 2008-09-16 | Exxonmobil Chemical Patents Inc. | Polymers with new sequence distributions |
| US7332554B2 (en) | 2002-12-20 | 2008-02-19 | Exxonmobil Chemical Patents Inc. | Polymers with new sequence distributions |
| CA2510860C (en) | 2002-12-20 | 2012-10-09 | Exxonmobil Chemical Patents Inc. | Polymerization process utilizing hydrofluorocarbons as diluents |
| WO2006009942A1 (en) | 2004-06-21 | 2006-01-26 | Exxonmobil Chemical Patents Inc. | Polymerization process |
| US20070100101A1 (en) * | 2005-10-28 | 2007-05-03 | Ming-Hong Hung | Fluoroelastomers containing copolymerized units of vinyl esters |
| EP2046430B1 (en) * | 2006-07-28 | 2016-04-20 | ResMed Ltd. | Delivery of respiratory therapy |
| JP4720734B2 (ja) * | 2006-12-08 | 2011-07-13 | ダイキン工業株式会社 | フルオロモノマーの回収方法 |
| WO2011051168A1 (en) * | 2009-10-29 | 2011-05-05 | Solvay Solexis S.P.A. | Process for the isolation of sulfonyl fluoride polymers and polymers obtained therefrom |
| US11059922B2 (en) * | 2016-10-28 | 2021-07-13 | Solvay Specialty Polymers Italy S.P.A. | Method for cross-linking polymers |
| WO2018192368A1 (zh) * | 2017-04-18 | 2018-10-25 | 浙江汉丞科技有限公司 | 一种含氟含氯导电高分子树脂的制备方法及其制备的单面或双面填充复合薄膜和制备方法 |
| WO2022059271A1 (ja) * | 2020-09-17 | 2022-03-24 | ダイキン工業株式会社 | 含フッ素重合体及びその製造方法 |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US367085A (en) * | 1887-07-26 | Wire-barbing machine | ||
| US303082A (en) * | 1884-08-05 | Balanced door for stoves | ||
| US3041317A (en) * | 1960-05-02 | 1962-06-26 | Du Pont | Fluorocarbon sulfonyl fluorides |
| US3282875A (en) * | 1964-07-22 | 1966-11-01 | Du Pont | Fluorocarbon vinyl ether polymers |
| US3291843A (en) * | 1963-10-08 | 1966-12-13 | Du Pont | Fluorinated vinyl ethers and their preparation |
| US3876654A (en) * | 1970-12-23 | 1975-04-08 | Du Pont | Fluoroelastomer composition |
| SE426839B (sv) * | 1977-12-14 | 1983-02-14 | Montedison Spa | Vulkbara kompositioner av vinylidenfluoridelaster samt forfarande for vulkning herav |
| JPS57109810A (en) * | 1980-12-26 | 1982-07-08 | Asahi Glass Co Ltd | Copolymer giving fluorine-containing elastomer with cold and alcohol resistance |
| JPS5837187A (ja) * | 1981-01-16 | 1983-03-04 | イ−・アイ・デユポン・デ・ニモアス・アンド・カンパニ− | 膜 |
| US4604323A (en) * | 1985-02-22 | 1986-08-05 | E. I. Du Pont De Nemours And Company | Multilayer cation exchange membrane |
| IT1189092B (it) * | 1986-04-29 | 1988-01-28 | Ausimont Spa | Processo di polimerizzazione in dispersione acquosa di monomeri fluorurati |
| US4948853A (en) * | 1989-05-19 | 1990-08-14 | E. I. Du Pont De Nemours And Company | Bromo-containing perfluoropolymers having iodine curesites |
| JPH10279634A (ja) * | 1997-04-02 | 1998-10-20 | Toagosei Co Ltd | 含フッ素共重合体の製造方法 |
| WO1999005126A1 (fr) * | 1997-07-25 | 1999-02-04 | Acep Inc. | Composes ioniques perfluorovinyliques et leur utilisation dans des materiaux conducteurs |
| US6025092A (en) * | 1998-02-13 | 2000-02-15 | E. I. Du Pont De Nemours And Company | Fluorinated ionomers and their uses |
| JP4417554B2 (ja) * | 1998-03-03 | 2010-02-17 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 相当にフッ素化されたイオノマー |
| DE69915824T2 (de) * | 1998-05-29 | 2005-02-03 | E.I. Du Pont De Nemours And Co., Wilmington | Färbbare fluorpolymer-fasern |
| KR20010103035A (ko) * | 1999-03-02 | 2001-11-17 | 메리 이. 보울러 | 플루오르화 공중합체를 위한 자유 라디칼 중합 방법 |
| US20030148158A1 (en) * | 1999-12-29 | 2003-08-07 | Ameduri Bruno Michel | Fluorosulphonated elastomers with low glass transition based on vinylidene fluoride |
| WO2001049760A1 (fr) * | 1999-12-29 | 2001-07-12 | HYDRO-QUéBEC | ELASTOMERES FLUOROSULFONES A FAIBLE Tg A BASE D'HEXAFLUOROPROPENE ET NE CONTENANT NI DU TETRAFLUOROETHYLENE, NI DE GROUPEMENT SILOXANE |
| WO2001049758A1 (fr) * | 1999-12-29 | 2001-07-12 | HYDRO-QUéBEC | ELASTOMERES FLUORES A FAIBLE Tg A BASE DE FLUORURE DE VINYLIDENE ET NE CONTENANT NI DU TETRAFLUOROETHYLENE, NI DE GROUPEMENT SILOXANE |
| CA2312194A1 (fr) * | 2000-06-13 | 2001-12-13 | Mario Boucher | Elastomeres reticulables fluores bromosulfones a faible tg a base de fluorure de vinylidene et ne contenant ni du tetrafluoroethylene ni de groupement siloxane |
| CA2328433A1 (fr) * | 2000-12-20 | 2002-06-20 | Hydro-Quebec | Elastomeres nitriles fluorosulfones reticulables a faible tg a base de fluorure de vinylidene et ne contenant ni du tetrafluoroethylene ni de groupement siloxane |
| CA2352417A1 (fr) * | 2001-07-05 | 2003-01-05 | Hydro-Quebec | Procede de synthese de monomeres fluorosulfones et leur copolymerisation avec des alcenes fluores |
| US7422795B2 (en) * | 2004-06-21 | 2008-09-09 | E.I. Du Pont De Nemours And Company | Polytrimethylene ether ester elastomer flexible films |
-
2000
- 2000-12-29 US US10/168,524 patent/US20030148158A1/en not_active Abandoned
- 2000-12-29 WO PCT/CA2000/001585 patent/WO2001049757A1/fr not_active Ceased
- 2000-12-29 DE DE60018476T patent/DE60018476T2/de not_active Expired - Lifetime
- 2000-12-29 JP JP2001550297A patent/JP2003519259A/ja active Pending
- 2000-12-29 EP EP00988537A patent/EP1252205B1/fr not_active Expired - Lifetime
- 2000-12-29 AU AU24961/01A patent/AU2496101A/en not_active Abandoned
- 2000-12-29 AT AT00988537T patent/ATE290026T1/de not_active IP Right Cessation
-
2005
- 2005-07-12 US US11/178,786 patent/US20060014889A1/en not_active Abandoned
-
2007
- 2007-02-02 US US11/670,826 patent/US20070185293A1/en not_active Abandoned
-
2011
- 2011-01-24 US US13/012,636 patent/US20110117306A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| AU2496101A (en) | 2001-07-16 |
| DE60018476D1 (de) | 2005-04-07 |
| ATE290026T1 (de) | 2005-03-15 |
| US20060014889A1 (en) | 2006-01-19 |
| EP1252205B1 (fr) | 2005-03-02 |
| EP1252205A1 (fr) | 2002-10-30 |
| JP2003519259A (ja) | 2003-06-17 |
| WO2001049757A1 (fr) | 2001-07-12 |
| US20070185293A1 (en) | 2007-08-09 |
| US20110117306A1 (en) | 2011-05-19 |
| US20030148158A1 (en) | 2003-08-07 |
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| 8364 | No opposition during term of opposition |