DE60016030T2 - Fluorelastomer mit niedriger glasübergangstemperatur auf basis von hexafluoropropen und frei von tetrafluoroethylen und siloxangruppen - Google Patents
Fluorelastomer mit niedriger glasübergangstemperatur auf basis von hexafluoropropen und frei von tetrafluoroethylen und siloxangruppen Download PDFInfo
- Publication number
- DE60016030T2 DE60016030T2 DE60016030T DE60016030T DE60016030T2 DE 60016030 T2 DE60016030 T2 DE 60016030T2 DE 60016030 T DE60016030 T DE 60016030T DE 60016030 T DE60016030 T DE 60016030T DE 60016030 T2 DE60016030 T2 DE 60016030T2
- Authority
- DE
- Germany
- Prior art keywords
- perfluoro
- hfp
- copolymerization
- vinyl ether
- pfso
- 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
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- -1 SILOXANE GROUPS Chemical group 0.000 title claims abstract description 37
- 230000009477 glass transition Effects 0.000 title claims abstract description 9
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical compound FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 title claims description 33
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical compound FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 claims abstract description 67
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 claims abstract description 50
- 229920001971 elastomer Polymers 0.000 claims abstract description 29
- 239000000806 elastomer Substances 0.000 claims abstract description 26
- 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 12
- 239000003999 initiator Substances 0.000 claims abstract description 10
- 238000000034 method Methods 0.000 claims description 41
- 229920001577 copolymer Polymers 0.000 claims description 30
- 239000000178 monomer Substances 0.000 claims description 30
- 229920001973 fluoroelastomer Polymers 0.000 claims description 23
- 238000007334 copolymerization reaction Methods 0.000 claims description 21
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 19
- 230000008569 process Effects 0.000 claims description 17
- 239000002904 solvent Substances 0.000 claims description 15
- 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 14
- 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 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 239000000446 fuel Substances 0.000 claims description 8
- 239000000839 emulsion Substances 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical compound FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 claims description 7
- MUMBMUMIEGCCII-UHFFFAOYSA-N 1-ethenoxy-3-ethoxypropane Chemical compound CCOCCCOC=C MUMBMUMIEGCCII-UHFFFAOYSA-N 0.000 claims description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 239000003208 petroleum Substances 0.000 claims description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 5
- 238000005516 engineering process Methods 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 4
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 4
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 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
- 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
- 150000001875 compounds Chemical class 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 claims description 3
- 238000010528 free radical solution polymerization reaction 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
- 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
- XRYWSOJOSFWGLH-UHFFFAOYSA-N 2-(3-ethenoxy-1,1,2,2,3,3-hexafluoropropoxy)-1,1,1,2,3,3,3-heptafluoropropane Chemical group 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 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
- 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 2
- FDMFUZHCIRHGRG-UHFFFAOYSA-N 3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C=C FDMFUZHCIRHGRG-UHFFFAOYSA-N 0.000 claims description 2
- 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 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
- 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
- 229910052731 fluorine Inorganic materials 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
- 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 1
- 150000003863 ammonium salts Chemical class 0.000 claims 1
- QDGONURINHVBEW-UHFFFAOYSA-N dichlorodifluoroethylene Chemical group FC(F)=C(Cl)Cl QDGONURINHVBEW-UHFFFAOYSA-N 0.000 claims 1
- CWINGZLCRSDKCL-UHFFFAOYSA-N ethoxycarbonyloxy ethyl carbonate Chemical compound CCOC(=O)OOC(=O)OCC CWINGZLCRSDKCL-UHFFFAOYSA-N 0.000 claims 1
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical class OS(F)(=O)=O UQSQSQZYBQSBJZ-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
- 239000005518 polymer electrolyte Substances 0.000 claims 1
- VHGUWVJGVBMLLC-UHFFFAOYSA-N tert-butyl cyclohexyloxycarbonyloxy carbonate Chemical compound CC(C)(C)OC(=O)OOC(=O)OC1CCCCC1 VHGUWVJGVBMLLC-UHFFFAOYSA-N 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 abstract description 11
- 230000015572 biosynthetic process Effects 0.000 abstract description 10
- 150000002978 peroxides Chemical class 0.000 abstract description 5
- 150000001336 alkenes Chemical class 0.000 abstract description 4
- 150000008049 diazo compounds Chemical class 0.000 abstract description 2
- 239000003502 gasoline Substances 0.000 abstract description 2
- 150000002976 peresters Chemical class 0.000 abstract description 2
- 229920002554 vinyl polymer Polymers 0.000 abstract 1
- 229920001897 terpolymer Polymers 0.000 description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 238000005481 NMR spectroscopy Methods 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 239000012528 membrane Substances 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 239000000047 product 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
- 230000008901 benefit Effects 0.000 description 4
- 238000007720 emulsion polymerization reaction Methods 0.000 description 4
- 238000002411 thermogravimetry Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 125000001246 bromo group Chemical group Br* 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 238000012512 characterization method Methods 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 238000012552 review Methods 0.000 description 3
- 238000010557 suspension polymerization reaction Methods 0.000 description 3
- 229920006029 tetra-polymer Polymers 0.000 description 3
- 229920003934 Aciplex® Polymers 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-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
- 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
- 150000001298 alcohols Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 125000001153 fluoro group Chemical group F* 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
- 229910052740 iodine Chemical group 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 150000008442 polyphenolic compounds Chemical class 0.000 description 2
- 235000013824 polyphenols Nutrition 0.000 description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 229920003249 vinylidene fluoride hexafluoropropylene elastomer Polymers 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 description 1
- 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
- GFLUWOXITVIXTN-UHFFFAOYSA-N 1,1,1,2,3,3-hexafluoro-2-(1,1,2,2,2-pentafluoroethoxy)-3-(1,2,2-trifluoroethenoxy)propane sulfuryl difluoride Chemical compound FS(F)(=O)=O.FC(F)=C(F)OC(F)(F)C(F)(C(F)(F)F)OC(F)(F)C(F)(F)F GFLUWOXITVIXTN-UHFFFAOYSA-N 0.000 description 1
- JILAKKYYZPDQBE-UHFFFAOYSA-N 1,1,2,2,3,3,4,4-octafluoro-1,4-diiodobutane Chemical compound FC(F)(I)C(F)(F)C(F)(F)C(F)(F)I JILAKKYYZPDQBE-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
- 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 description 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- 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 1
- NGOCAPPEAVAHQM-UHFFFAOYSA-N 2-fluoroprop-1-ene Chemical compound CC(F)=C NGOCAPPEAVAHQM-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-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
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 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
- 235000019502 Orange oil Nutrition 0.000 description 1
- 239000002033 PVDF binder Substances 0.000 description 1
- TWLNVQNCJFIEEU-UHFFFAOYSA-N [N].CC(C)=O Chemical compound [N].CC(C)=O TWLNVQNCJFIEEU-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
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- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 239000003945 anionic surfactant Substances 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
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000007942 carboxylates Chemical group 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 239000012986 chain transfer agent Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical compound FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 238000007872 degassing 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
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 150000001993 dienes Chemical class 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
- 238000012674 dispersion polymerization Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000000806 fluorine-19 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229920002313 fluoropolymer Polymers 0.000 description 1
- 239000004811 fluoropolymer Substances 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
- 230000010354 integration Effects 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 229920002521 macromolecule Polymers 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
- 238000000465 moulding Methods 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
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- 125000001424 substituent group Chemical group 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
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 238000004073 vulcanization 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
- C08F214/28—Hexyfluoropropene
-
- 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
- C08F216/1466—Monomers containing sulfur
- C08F216/1475—Monomers containing sulfur and oxygen
-
- 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
-
- 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]
- Y10T428/1397—Single layer [continuous layer]
-
- 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
- Y10T428/21—Circular sheet or circular blank
- Y10T428/215—Seal, gasket, or packing
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)
- Laminated Bodies (AREA)
- Paints Or Removers (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA002293845A CA2293845A1 (fr) | 1999-12-29 | 1999-12-29 | Elastomeres fluorosulfones a faible tg a base d'hexafluoropropene et ne contenant ni du tetrafluoroethylene, ni de groupement siloxane |
| CA2293845 | 1999-12-29 | ||
| CA002299621A CA2299621A1 (fr) | 2000-02-24 | 2000-02-24 | Elastomeres fluorosulfones a faible tg a base d'hexafluoropropene et ne contenant ni du tetrafluoroethylene, ni de groupement siloxane |
| CA2299621 | 2000-02-24 | ||
| PCT/CA2000/001589 WO2001049760A1 (fr) | 1999-12-29 | 2000-12-29 | ELASTOMERES FLUOROSULFONES A FAIBLE Tg A BASE D'HEXAFLUOROPROPENE ET NE CONTENANT NI DU TETRAFLUOROETHYLENE, NI DE GROUPEMENT SILOXANE |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60016030D1 DE60016030D1 (de) | 2004-12-23 |
| DE60016030T2 true DE60016030T2 (de) | 2005-12-01 |
Family
ID=25681439
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60016030T Expired - Lifetime DE60016030T2 (de) | 1999-12-29 | 2000-12-29 | Fluorelastomer mit niedriger glasübergangstemperatur auf basis von hexafluoropropen und frei von tetrafluoroethylen und siloxangruppen |
Country Status (7)
| Country | Link |
|---|---|
| US (5) | US20030153699A1 (https=) |
| EP (1) | EP1242486B1 (https=) |
| JP (1) | JP5007009B2 (https=) |
| AT (1) | ATE282649T1 (https=) |
| AU (1) | AU2338301A (https=) |
| DE (1) | DE60016030T2 (https=) |
| WO (1) | WO2001049760A1 (https=) |
Families Citing this family (22)
| 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 |
| 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 |
| US7094851B2 (en) * | 2001-12-06 | 2006-08-22 | Gore Enterprise Holdings, Inc. | Low equivalent weight ionomer |
| US6861489B2 (en) * | 2001-12-06 | 2005-03-01 | 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 |
| US20100093878A1 (en) * | 2007-12-27 | 2010-04-15 | E.I. Du Pont De Nemours And Company | Crosslinkable fluoropolymer, crosslinked fluoropolymers and crosslinked fluoropolymer membranes |
| WO2009083451A1 (en) * | 2007-12-28 | 2009-07-09 | Solvay Solexis S.P.A. | Addition reaction to fluoroallylfluorosulfate |
| US8765217B2 (en) * | 2008-11-04 | 2014-07-01 | Entrotech, Inc. | Method for continuous production of (meth)acrylate syrup and adhesives therefrom |
| US8329079B2 (en) | 2009-04-20 | 2012-12-11 | Entrochem, Inc. | Method and apparatus for continuous production of partially polymerized compositions and polymers therefrom |
| US20130090439A1 (en) * | 2011-10-05 | 2013-04-11 | Honeywell International Inc. | Polymerization Of 2,3,3,3-Tetrafluoropropene And Polymers Formed From 2,3,3,3-Tetrafluoropropene |
| US9234062B2 (en) | 2011-12-14 | 2016-01-12 | Honeywell International Inc. | Process, properties, and applications of graft copolymers |
| DK3256501T3 (en) | 2015-02-12 | 2019-03-18 | 3M Innovative Properties Co | TETRAFLUORETHYLEN / HEXAFLUORPROPYLEN COPOLYMERS INCLUDING PERFLUORAL COXYALKYL GROUPS AS PREPARATIONS AND METHODS OF PRODUCTION AND USE PROCEDURES |
| US10730980B2 (en) | 2015-02-12 | 2020-08-04 | 3M Innovative Properties Company | Tetrafluoroethylene/hexafluoropropylene copolymers including perfluoroalkoxyalkyl pendant groups |
| US10844152B2 (en) * | 2015-02-12 | 2020-11-24 | 3M Innovative Properties Company | Tetrafluoroethylene and perfluorinated allyl ether copolymers |
| CN108503738B (zh) * | 2018-04-16 | 2020-06-26 | 中国海洋石油集团有限公司 | 一种聚偏氟乙烯树脂及其制备方法与应用 |
| CN112174855B (zh) * | 2020-11-16 | 2021-09-24 | 福州大学 | 一种磺酰氟类产物的制备方法 |
| JP7206535B1 (ja) | 2021-08-10 | 2023-01-18 | ダイキン工業株式会社 | 低粘度含フッ素エラストマーの製造方法 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 |
| US5478905A (en) * | 1995-02-06 | 1995-12-26 | E. I. Du Pont De Nemours And Company | Amorphous tetrafluoroethylene/hexafluoropropylene copolymers |
| US5674957A (en) * | 1995-03-10 | 1997-10-07 | The University Of North Carolina At Chapel Hill | Nonaqueous polymerization of fluoromonomers |
| 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 |
| 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 |
-
2000
- 2000-12-29 WO PCT/CA2000/001589 patent/WO2001049760A1/fr not_active Ceased
- 2000-12-29 US US10/168,525 patent/US20030153699A1/en not_active Abandoned
- 2000-12-29 AU AU23383/01A patent/AU2338301A/en not_active Abandoned
- 2000-12-29 AT AT00986958T patent/ATE282649T1/de not_active IP Right Cessation
- 2000-12-29 JP JP2001550300A patent/JP5007009B2/ja not_active Expired - Fee Related
- 2000-12-29 EP EP00986958A patent/EP1242486B1/fr not_active Expired - Lifetime
- 2000-12-29 DE DE60016030T patent/DE60016030T2/de not_active Expired - Lifetime
-
2005
- 2005-07-18 US US11/182,858 patent/US20050282986A1/en not_active Abandoned
-
2007
- 2007-07-18 US US11/779,551 patent/US20070293643A1/en not_active Abandoned
-
2010
- 2010-09-09 US US12/878,444 patent/US20100330317A1/en not_active Abandoned
-
2012
- 2012-04-18 US US13/450,074 patent/US20120231369A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| AU2338301A (en) | 2001-07-16 |
| WO2001049760A1 (fr) | 2001-07-12 |
| US20070293643A1 (en) | 2007-12-20 |
| US20050282986A1 (en) | 2005-12-22 |
| ATE282649T1 (de) | 2004-12-15 |
| US20120231369A1 (en) | 2012-09-13 |
| US20030153699A1 (en) | 2003-08-14 |
| JP5007009B2 (ja) | 2012-08-22 |
| US20100330317A1 (en) | 2010-12-30 |
| DE60016030D1 (de) | 2004-12-23 |
| EP1242486B1 (fr) | 2004-11-17 |
| JP2003519261A (ja) | 2003-06-17 |
| EP1242486A1 (fr) | 2002-09-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition |