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
Links
- -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
- 238000009825 accumulation Methods 0.000 description 1
- 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
- 230000009467 reduction Effects 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
- 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 |
|---|---|---|---|
| CA2293845 | 1999-12-29 | ||
| 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 |
| 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 (enExample) |
| EP (1) | EP1242486B1 (enExample) |
| JP (1) | JP5007009B2 (enExample) |
| AT (1) | ATE282649T1 (enExample) |
| AU (1) | AU2338301A (enExample) |
| DE (1) | DE60016030T2 (enExample) |
| WO (1) | WO2001049760A1 (enExample) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE60016030T2 (de) * | 1999-12-29 | 2005-12-01 | Hydro-Québec, Montréal | Fluorelastomer mit niedriger glasübergangstemperatur auf basis von hexafluoropropen und frei von tetrafluoroethylen und siloxangruppen |
| WO2001049757A1 (fr) * | 1999-12-29 | 2001-07-12 | HYDRO-QUéBEC | Elastomeres fluorosulfones a faible tg a base de fluorure de vinylidene |
| 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 |
| US6861489B2 (en) * | 2001-12-06 | 2005-03-01 | Gore Enterprise Holdings, Inc. | Low equivalent weight ionomer |
| US7094851B2 (en) * | 2001-12-06 | 2006-08-22 | Gore Enterprise Holdings, Inc. | Low equivalent weight ionomer |
| AU2003303313A1 (en) | 2002-12-20 | 2004-08-23 | Exxonmobil Chemical Patents Inc. | Polymerization processes |
| WO2004058828A1 (en) | 2002-12-20 | 2004-07-15 | Exxonmobil Chemical Patents Inc. | Polymerization processes |
| US7425601B2 (en) | 2002-12-20 | 2008-09-16 | Exxonmobil Chemical Patents Inc. | Polymers with new sequence distributions |
| US7414100B2 (en) | 2004-06-21 | 2008-08-19 | 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 |
| JP5512541B2 (ja) * | 2007-12-28 | 2014-06-04 | ソルヴェイ・スペシャルティ・ポリマーズ・イタリー・エッセ・ピ・ア | フルオロアリルフルオロサルフェートへの付加反応 |
| 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 |
| JP6640863B2 (ja) | 2015-02-12 | 2020-02-05 | スリーエム イノベイティブ プロパティズ カンパニー | ペンダントスルホニル基を有するテトラフルオロエチレン／ヘキサフルオロプロピレンコポリマー |
| US10730980B2 (en) | 2015-02-12 | 2020-08-04 | 3M Innovative Properties Company | Tetrafluoroethylene/hexafluoropropylene copolymers including perfluoroalkoxyalkyl pendant groups |
| CN107223139B (zh) | 2015-02-12 | 2020-06-30 | 3M创新有限公司 | 包含全氟烷氧基烷基侧基的四氟乙烯/六氟丙烯共聚物及其制备和使用方法 |
| 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 |
| WO2023017701A1 (ja) * | 2021-08-10 | 2023-02-16 | 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 |
| JP4657390B2 (ja) * | 1997-07-25 | 2011-03-23 | アセップ・インク | ペルフルオロビニルイオン化合物および重合体型のイオン電導体の成分、選択膜の成分または触媒の成分としてのそれらの使用 |
| US6025092A (en) * | 1998-02-13 | 2000-02-15 | E. I. Du Pont De Nemours And Company | Fluorinated ionomers and their uses |
| CA2321695A1 (en) * | 1998-03-03 | 1999-09-10 | Mark Gerrit Roelofs | Substantially fluorinated ionomers |
| CN1142976C (zh) * | 1998-05-29 | 2004-03-24 | 纳幕尔杜邦公司 | 纤维及其制法 |
| WO2001049757A1 (fr) * | 1999-12-29 | 2001-07-12 | HYDRO-QUéBEC | Elastomeres fluorosulfones a faible tg a base de fluorure de vinylidene |
| DE60016030T2 (de) * | 1999-12-29 | 2005-12-01 | Hydro-Québec, Montréal | Fluorelastomer mit niedriger glasübergangstemperatur auf basis von hexafluoropropen und frei von tetrafluoroethylen und siloxangruppen |
-
2000
- 2000-12-29 DE DE60016030T patent/DE60016030T2/de not_active Expired - Lifetime
- 2000-12-29 EP EP00986958A patent/EP1242486B1/fr not_active Expired - Lifetime
- 2000-12-29 JP JP2001550300A patent/JP5007009B2/ja not_active Expired - Fee Related
- 2000-12-29 WO PCT/CA2000/001589 patent/WO2001049760A1/fr not_active Ceased
- 2000-12-29 AT AT00986958T patent/ATE282649T1/de not_active IP Right Cessation
- 2000-12-29 AU AU23383/01A patent/AU2338301A/en not_active Abandoned
- 2000-12-29 US US10/168,525 patent/US20030153699A1/en not_active Abandoned
-
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 |
|---|---|
| US20030153699A1 (en) | 2003-08-14 |
| EP1242486A1 (fr) | 2002-09-25 |
| JP2003519261A (ja) | 2003-06-17 |
| US20120231369A1 (en) | 2012-09-13 |
| JP5007009B2 (ja) | 2012-08-22 |
| WO2001049760A1 (fr) | 2001-07-12 |
| ATE282649T1 (de) | 2004-12-15 |
| DE60016030D1 (de) | 2004-12-23 |
| EP1242486B1 (fr) | 2004-11-17 |
| US20100330317A1 (en) | 2010-12-30 |
| US20070293643A1 (en) | 2007-12-20 |
| AU2338301A (en) | 2001-07-16 |
| US20050282986A1 (en) | 2005-12-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE60016030T2 (de) | Fluorelastomer mit niedriger glasübergangstemperatur auf basis von hexafluoropropen und frei von tetrafluoroethylen und siloxangruppen | |
| DE60018476T2 (de) | Fluorosulfoneelastomere mit niedrigem tg basierend auf vinylidenfluorit | |
| EP0774472B1 (de) | Peroxidisch vernetzbare Fluorkautschuke, ein Verfahren zu deren Herstellung und deren Verwendung | |
| KR940000016B1 (ko) | 경화성 플루오로엘라스토머의 제조방법 및 제품 | |
| DE69830353T2 (de) | Thermisch verarbeitbare fluorierte Polymere | |
| DE69405618T2 (de) | (Co)polymerisation aus fluorierten olefinischen Monomeren in wässriger Emulsion | |
| DE69617042T2 (de) | Fluorhaltige, elastische copolymere, härtbare zusammensetzung und daraus hergestellte dichtungsmasse | |
| DE69212168T2 (de) | Vernetzte fluoroelastomere zusammensetzungen | |
| EP1068246B1 (de) | Verfahren zur herstellung von teilfluorierten fluorpolymeren | |
| DE60319844T2 (de) | Fluorelastomere mit niedertemperatureigenschaften und lösungsmittelbeständigkeit | |
| EP1591461B1 (en) | Method of producing thermoplastic fluoropolymers using alkyl sulfonate surfactants | |
| JP2004502786A (ja) | 低いＴｇを示すフッ化ビニリデンを主成分とする、架橋性ブロモスルホン化フルオロエラストマー | |
| DE69403692T2 (de) | Radikalisches (co)Polymerisationsverfahren von fluorhaltigen olefinischen Monomeren | |
| DE60317530T2 (de) | Fluorpolymere mit verbessertem druckverformungsrest | |
| DE68925009T2 (de) | Fluorenthaltendes nichtkristallines Copolymer. | |
| US20030153702A1 (en) | Fluorinated elastomers with low glass transition temperatures based on vinylidene fluoride and free of tetrafluoroethylene or siloxane group | |
| EP1833860B1 (en) | Fluoroelastomers having low glass transition temperature | |
| EP1189954A1 (de) | Schnell vernetzendes fluorpolymer | |
| DE69210901T2 (de) | Ionisch vulkanisierbare, fluorelastomere Copolymere | |
| DE19939043B4 (de) | Verfahren zur Herstellung fluorierten Copolymers, fluoriertes Copolymer, vernetzbare Zusammensetzung, welche dasselbe und Dichtungsmaterial enthält | |
| WO2000018811A1 (de) | Verfahren zur herstellung eines schnellvernetzbaren fluorkautschukes | |
| DE69610815T2 (de) | Elastisches fluorkohlenwasserstoff-enthaltendes Harz und Verfahren zu seiner Herstellung | |
| WO2026006652A1 (en) | Process of producing fluoropolymers using alkylsulfosuccinate |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition |