WO2001060872A1 - Fluoropolymer resins containing ionic or ionizable groups and products containing the same - Google Patents
Fluoropolymer resins containing ionic or ionizable groups and products containing the same Download PDFInfo
- Publication number
- WO2001060872A1 WO2001060872A1 PCT/US2001/004995 US0104995W WO0160872A1 WO 2001060872 A1 WO2001060872 A1 WO 2001060872A1 US 0104995 W US0104995 W US 0104995W WO 0160872 A1 WO0160872 A1 WO 0160872A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- ionic
- fluoropolymer
- acrylic
- polymer
- membrane
- Prior art date
Links
- 229920002313 fluoropolymer Polymers 0.000 title claims abstract description 63
- 239000004811 fluoropolymer Substances 0.000 title claims abstract description 62
- 229920005989 resin Polymers 0.000 title claims abstract description 24
- 239000011347 resin Substances 0.000 title claims abstract description 24
- 239000012528 membrane Substances 0.000 claims abstract description 68
- 229920000642 polymer Polymers 0.000 claims abstract description 54
- 239000000203 mixture Substances 0.000 claims abstract description 45
- 239000000446 fuel Substances 0.000 claims abstract description 40
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 31
- 229920002959 polymer blend Polymers 0.000 claims abstract description 27
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 27
- 229920000178 Acrylic resin Polymers 0.000 claims abstract description 23
- 239000004925 Acrylic resin Substances 0.000 claims abstract description 23
- 238000000034 method Methods 0.000 claims abstract description 22
- 229920001169 thermoplastic Polymers 0.000 claims abstract description 12
- 239000004416 thermosoftening plastic Substances 0.000 claims abstract description 12
- 239000000178 monomer Substances 0.000 claims description 68
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 51
- -1 poly(vinylidene fluoride) Polymers 0.000 claims description 46
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 36
- 238000002156 mixing Methods 0.000 claims description 24
- 239000002904 solvent Substances 0.000 claims description 21
- 239000006185 dispersion Substances 0.000 claims description 16
- 229920002981 polyvinylidene fluoride Polymers 0.000 claims description 14
- 239000007788 liquid Substances 0.000 claims description 9
- 238000007720 emulsion polymerization reaction Methods 0.000 claims description 8
- 229920001577 copolymer Polymers 0.000 claims description 6
- 238000001125 extrusion Methods 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 229920001484 poly(alkylene) Polymers 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- 125000000524 functional group Chemical group 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- 230000000379 polymerizing effect Effects 0.000 claims description 3
- 239000000945 filler Substances 0.000 claims description 2
- LNGKTPFIOZTXDP-UHFFFAOYSA-N 2-chloro-1,3,3,4,4,5,5,6,6,7,8,8,8-tridecafluoro-7-(trifluoromethyl)oct-1-ene Chemical compound FC(C(C(F)(F)F)(C(C(C(C(C(=CF)Cl)(F)F)(F)F)(F)F)(F)F)F)(F)F LNGKTPFIOZTXDP-UHFFFAOYSA-N 0.000 claims 2
- 238000012662 bulk polymerization Methods 0.000 claims 1
- 239000000839 emulsion Substances 0.000 claims 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract description 5
- 239000004816 latex Substances 0.000 description 27
- 229920000126 latex Polymers 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 238000006116 polymerization reaction Methods 0.000 description 14
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 238000006277 sulfonation reaction Methods 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 239000003999 initiator Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 239000002033 PVDF binder Substances 0.000 description 6
- 239000002245 particle Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- 229920001519 homopolymer Polymers 0.000 description 5
- 239000003014 ion exchange membrane Substances 0.000 description 5
- 150000002500 ions Chemical class 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000002609 medium Substances 0.000 description 5
- 159000000000 sodium salts Chemical class 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 4
- 229920003303 ion-exchange polymer Polymers 0.000 description 4
- 229920000058 polyacrylate Polymers 0.000 description 4
- 229920000867 polyelectrolyte Polymers 0.000 description 4
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 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 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 description 3
- KFNGWPXYNSJXOP-UHFFFAOYSA-N 3-(2-methylprop-2-enoyloxy)propane-1-sulfonic acid Chemical compound CC(=C)C(=O)OCCCS(O)(=O)=O KFNGWPXYNSJXOP-UHFFFAOYSA-N 0.000 description 3
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 239000003456 ion exchange resin Substances 0.000 description 3
- 125000003010 ionic group Chemical group 0.000 description 3
- 239000004810 polytetrafluoroethylene Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 3
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- XFCMNSHQOZQILR-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOC(=O)C(C)=C XFCMNSHQOZQILR-UHFFFAOYSA-N 0.000 description 2
- RCEJCSULJQNRQQ-UHFFFAOYSA-N 2-methylbutanenitrile Chemical compound CCC(C)C#N RCEJCSULJQNRQQ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 229920000557 Nafion® Polymers 0.000 description 2
- 229920002274 Nalgene Polymers 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229920004896 Triton X-405 Polymers 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001253 acrylic acids Chemical class 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
- 239000002280 amphoteric surfactant Substances 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 239000012986 chain transfer agent Substances 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 2
- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 239000005518 polymer electrolyte Substances 0.000 description 2
- 239000002952 polymeric resin Substances 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical class OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 235000011044 succinic acid Nutrition 0.000 description 2
- 229920003002 synthetic resin Polymers 0.000 description 2
- 229920001897 terpolymer Polymers 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 2
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- AVTLBBWTUPQRAY-UHFFFAOYSA-N 2-(2-cyanobutan-2-yldiazenyl)-2-methylbutanenitrile Chemical compound CCC(C)(C#N)N=NC(C)(CC)C#N AVTLBBWTUPQRAY-UHFFFAOYSA-N 0.000 description 1
- FTALTLPZDVFJSS-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl prop-2-enoate Chemical compound CCOCCOCCOC(=O)C=C FTALTLPZDVFJSS-UHFFFAOYSA-N 0.000 description 1
- OLQFXOWPTQTLDP-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCO OLQFXOWPTQTLDP-UHFFFAOYSA-N 0.000 description 1
- PRAMZQXXPOLCIY-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)ethanesulfonic acid Chemical compound CC(=C)C(=O)OCCS(O)(=O)=O PRAMZQXXPOLCIY-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- FRFUQJFVJRYYDZ-UHFFFAOYSA-N 2-methyl-n-(2-methylpropyl)prop-2-enamide Chemical compound CC(C)CNC(=O)C(C)=C FRFUQJFVJRYYDZ-UHFFFAOYSA-N 0.000 description 1
- CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 description 1
- AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical compound OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-UHFFFAOYSA-N 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
- GETJHIYPEXUGHO-UHFFFAOYSA-N 3-(prop-2-enoylamino)propane-1-sulfonic acid Chemical compound OS(=O)(=O)CCCNC(=O)C=C GETJHIYPEXUGHO-UHFFFAOYSA-N 0.000 description 1
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 1
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 description 1
- KFDVPJUYSDEJTH-UHFFFAOYSA-N 4-ethenylpyridine Chemical compound C=CC1=CC=NC=C1 KFDVPJUYSDEJTH-UHFFFAOYSA-N 0.000 description 1
- ORDRGXFSRBRQQG-UHFFFAOYSA-N 6-methylheptyl 2-sulfanylpropanoate Chemical compound CC(C)CCCCCOC(=O)C(C)S ORDRGXFSRBRQQG-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- FVCPXLWAKNJIKK-UHFFFAOYSA-N Dimexano Chemical compound COC(=S)SSC(=S)OC FVCPXLWAKNJIKK-UHFFFAOYSA-N 0.000 description 1
- 241001547070 Eriodes Species 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical group [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 102100035115 Testin Human genes 0.000 description 1
- 101710070533 Testin Proteins 0.000 description 1
- KYIKRXIYLAGAKQ-UHFFFAOYSA-N abcn Chemical compound C1CCCCC1(C#N)N=NC1(C#N)CCCCC1 KYIKRXIYLAGAKQ-UHFFFAOYSA-N 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 150000008360 acrylonitriles Chemical class 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000005210 alkyl ammonium group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical class 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- BTBJBAZGXNKLQC-UHFFFAOYSA-N ammonium lauryl sulfate Chemical compound [NH4+].CCCCCCCCCCCCOS([O-])(=O)=O BTBJBAZGXNKLQC-UHFFFAOYSA-N 0.000 description 1
- 229940063953 ammonium lauryl sulfate Drugs 0.000 description 1
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 238000000429 assembly Methods 0.000 description 1
- 230000000712 assembly Effects 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- YQHLDYVWEZKEOX-UHFFFAOYSA-N cumene hydroperoxide Chemical compound OOC(C)(C)C1=CC=CC=C1 YQHLDYVWEZKEOX-UHFFFAOYSA-N 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
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- TXEYQDLBPFQVAA-UHFFFAOYSA-N tetrafluoromethane Chemical compound FC(F)(F)F TXEYQDLBPFQVAA-UHFFFAOYSA-N 0.000 description 1
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- C08J5/2243—Synthetic macromolecular compounds based on macromolecular compounds obtained by reactions involving unsaturated carbon-to-carbon bonds obtained by introduction of active groups capable of ion-exchange into compounds of the type C08J5/2231
- C08J5/225—Synthetic macromolecular compounds based on macromolecular compounds obtained by reactions involving unsaturated carbon-to-carbon bonds obtained by introduction of active groups capable of ion-exchange into compounds of the type C08J5/2231 containing fluorine
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F259/00—Macromolecular compounds obtained by polymerising monomers on to polymers of halogen containing monomers as defined in group C08F14/00
- C08F259/08—Macromolecular compounds obtained by polymerising monomers on to polymers of halogen containing monomers as defined in group C08F14/00 on to polymers containing fluorine
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- C08F8/44—Preparation of metal salts or ammonium salts
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- C08L27/16—Homopolymers or copolymers or vinylidene fluoride
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- H01M8/1016—Fuel cells with solid electrolytes characterised by the electrolyte material
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- H01M8/10—Fuel cells with solid electrolytes
- H01M8/1016—Fuel cells with solid electrolytes characterised by the electrolyte material
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- H01M8/1069—Polymeric electrolyte materials characterised by the manufacturing processes
- H01M8/1081—Polymeric electrolyte materials characterised by the manufacturing processes starting from solutions, dispersions or slurries exclusively of polymers
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
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- C08J2327/16—Homopolymers or copolymers of vinylidene fluoride
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- 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
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- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
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- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Sustainable Development (AREA)
- Sustainable Energy (AREA)
- Dispersion Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Materials Engineering (AREA)
- Composite Materials (AREA)
- Fuel Cell (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Cell Separators (AREA)
- Conductive Materials (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
Abstract
Description
Claims
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2001560254A JP4837216B2 (en) | 2000-02-15 | 2001-02-15 | Fluoropolymer resin containing ionic or ionizable groups and product containing the same |
CA2369696A CA2369696C (en) | 2000-02-15 | 2001-02-15 | Fluoropolymer resins containing ionic or ionizable groups and products containing the same |
RU2001130757/04A RU2264420C2 (en) | 2000-02-15 | 2001-02-15 | Fluoropolymers containing ionic or ionizable groups and product containing indicated fluoropolymers |
KR1020017013043A KR100743845B1 (en) | 2000-02-15 | 2001-02-15 | Fluoropolymer resins containing ionic or ionizable groups and products containing the same |
EP01916103A EP1177221A4 (en) | 2000-02-15 | 2001-02-15 | Fluoropolymer resins containing ionic or ionizable groups and products containing the same |
MXPA01010408A MXPA01010408A (en) | 2000-02-15 | 2001-02-15 | Fluoropolymer resins containing ionic or ionizable groups and products containing the same. |
IL145673A IL145673A (en) | 2000-02-15 | 2001-09-25 | Fluoropolymer resins containing ionic or ionizable groups and products containing the same |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US18273200P | 2000-02-15 | 2000-02-15 | |
US60/182,732 | 2000-02-15 | ||
US09/774,266 US6780935B2 (en) | 2000-02-15 | 2001-01-30 | Fluoropolymer resins containing ionic or ionizable groups and products containing the same |
US09/774,266 | 2001-01-30 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2001060872A1 true WO2001060872A1 (en) | 2001-08-23 |
Family
ID=26878363
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2001/004995 WO2001060872A1 (en) | 2000-02-15 | 2001-02-15 | Fluoropolymer resins containing ionic or ionizable groups and products containing the same |
Country Status (11)
Country | Link |
---|---|
US (2) | US6780935B2 (en) |
EP (1) | EP1177221A4 (en) |
JP (1) | JP4837216B2 (en) |
KR (1) | KR100743845B1 (en) |
CN (1) | CN1142193C (en) |
CA (1) | CA2369696C (en) |
IL (1) | IL145673A (en) |
MX (1) | MXPA01010408A (en) |
RU (1) | RU2264420C2 (en) |
TW (1) | TWI302540B (en) |
WO (1) | WO2001060872A1 (en) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1455407A2 (en) * | 2003-03-06 | 2004-09-08 | Atofina Chemicals, Inc. | Non-perfluoropolymer resins containing ionic or ionizable groups and products containing the same |
EP1505120A1 (en) * | 2003-07-30 | 2005-02-09 | Atofina Chemicals, Inc. | Resin compositions containing ionic or ionizable groups with small domain sizes and improved conductivity |
WO2006019508A2 (en) | 2004-07-14 | 2006-02-23 | Arkema Inc. | Multi-layer polyelectrolyte membrane |
WO2008002747A1 (en) * | 2006-06-29 | 2008-01-03 | Avery Dennison Corporation | Polyvinylidene fluoride films and laminates thereof |
US8153329B2 (en) | 2004-06-24 | 2012-04-10 | Konica Minolta Holdings, Inc. | Proton conducting electrolyte membrane and production method thereof and solid polymer fuel cell using the same |
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Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5272186A (en) * | 1992-05-01 | 1993-12-21 | E. I. Du Pont De Nemours And Company | Concentration of fluoropolymer dispersions using acrylic polymers of high acid content |
US5880204A (en) * | 1995-09-27 | 1999-03-09 | Alliedsignal Inc. | Room temperature coalescable aqueous fluoropolymer dispersions and method for their manufacture |
US5962140A (en) * | 1996-06-25 | 1999-10-05 | Acushnet Company | Golf ball comprising fluoropolymer |
Family Cites Families (44)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US1810528A (en) | 1929-06-12 | 1931-06-16 | Hotchkiss Co E H | Stapling machine |
US1996222A (en) | 1933-09-01 | 1935-04-02 | Vogel Max | Stapling machine |
DE1078329B (en) | 1955-04-27 | 1960-03-24 | Du Pont | Process for the production of an elastic copolymer from vinylidene fluoride and another fluoroolefin |
US2987729A (en) | 1959-02-10 | 1961-06-13 | Melpar Inc | Stapling device |
GB975031A (en) * | 1960-02-01 | 1964-11-11 | American Mach & Foundry | Ion permeable membranes |
US3178399A (en) | 1961-08-10 | 1965-04-13 | Minnesota Mining & Mfg | Fluorine-containing polymers and preparation thereof |
US3475396A (en) | 1966-07-06 | 1969-10-28 | Diamond Shamrock Corp | Process for polymerizing vinylidene fluoride |
US3504837A (en) | 1968-04-24 | 1970-04-07 | Werner Schafroth | Stapling machine and method of forming staples |
DE1959147C3 (en) * | 1968-11-26 | 1979-12-06 | E.I. Du Pont De Nemours And Co., Wilmington, Del. (V.St.A.) | Fluorocarbon polymer surfactant article |
US3642187A (en) | 1970-05-14 | 1972-02-15 | Flynn & Emrich Co | Stitching head |
US3857827A (en) | 1974-01-25 | 1974-12-31 | Pennwalt Corp | Method of preparing high-quality vinylidene fluoride polymer in aqueous emulsion |
JPS551351B2 (en) * | 1974-03-07 | 1980-01-12 | ||
FR2268094B1 (en) | 1974-04-16 | 1976-10-08 | Rhone Poulenc Textile | |
US4191811A (en) * | 1977-03-01 | 1980-03-04 | Ionics, Incorported | Ion exchange membranes based upon polyphenylene sulfide and fluorocarbon polymeric binder |
JPS6053059B2 (en) * | 1978-07-11 | 1985-11-22 | 旭化成株式会社 | Improved cation exchange membrane manufacturing method |
IT1166581B (en) | 1979-01-17 | 1987-05-05 | Oronzio De Nora Impianti | CATIONIC MEMBRANES BASED ON STYRENE DIVINYLBENZENE AND 2- OR 4-VINYLPYRIDINE OR ACRYLIC ACID SULPHONATED COPOLYMERS, PROCEDURE FOR THEIR PREPARATION AND USE IN ELECTROLYSIS CELLS |
JPS6024812B2 (en) | 1979-11-09 | 1985-06-14 | 呉羽化学工業株式会社 | Vinylidene chloride resin casing |
US4318555A (en) | 1980-01-15 | 1982-03-09 | Eastman Kodak Company | Stapler |
US4421264A (en) | 1981-06-26 | 1983-12-20 | International Business Machines Corporation | Variable thickness set compensation for stapler |
US4583276A (en) | 1983-06-23 | 1986-04-22 | Swingline, Inc. | Method of forming and driving staples |
US4569978A (en) | 1984-07-25 | 1986-02-11 | Pennwalt Corporation | Emulsion polymerization of vinylidene fluoride polymers in the presence of trichlorofluoromethane as chain transfer agent |
DE3533840A1 (en) | 1985-09-23 | 1987-04-02 | Bosch Gmbh Robert | POWERFUL WRAPPING DEVICE, IN PARTICULAR FOR STAPLES |
FR2600265B1 (en) * | 1986-06-20 | 1991-09-06 | Rhone Poulenc Rech | DRY AND HYDROPHILIC SEMI-PERMEABLE MEMBRANES BASED ON VINYLIDENE POLYFLUORIDE |
US5007483A (en) | 1988-02-03 | 1991-04-16 | Mcguire Douglas K | Hoof-buffing tool kit for farriers |
US5093427A (en) | 1990-05-10 | 1992-03-03 | Atochem North America, Inc. | Copolymers of vinylidene fluoride and hexafluoropropylene and process for preparing the same |
JP3128938B2 (en) * | 1992-03-27 | 2001-01-29 | ジェイエスアール株式会社 | Method for producing aqueous fluoropolymer dispersion |
SE500140C2 (en) | 1992-06-30 | 1994-04-25 | Isaberg Ab | Stapler with flattening mechanism |
DE4243995C2 (en) * | 1992-12-23 | 1996-07-25 | Gore W L & Ass Gmbh | Permanent hydrophilic modification for fluoropolymers and methods for generating the modification |
DE4326130A1 (en) | 1993-08-04 | 1995-02-09 | Huels Chemische Werke Ag | Thermoplastic multilayer composites |
JP3345788B2 (en) * | 1993-12-26 | 2002-11-18 | ジャパンゴアテックス株式会社 | Separator for electrochemical reactor |
JPH07187487A (en) | 1993-12-28 | 1995-07-25 | Toshiba Corp | Stapler and image forming device having stapler |
DE4410148A1 (en) * | 1994-03-24 | 1995-09-28 | Huels Chemische Werke Ag | Multi-layer plastic tube |
US5468574A (en) | 1994-05-23 | 1995-11-21 | Dais Corporation | Fuel cell incorporating novel ion-conducting membrane |
US5795668A (en) | 1994-11-10 | 1998-08-18 | E. I. Du Pont De Nemours And Company | Fuel cell incorporating a reinforced membrane |
US5599614A (en) * | 1995-03-15 | 1997-02-04 | W. L. Gore & Associates, Inc. | Integral composite membrane |
AU2928397A (en) | 1996-04-30 | 1997-11-19 | W.L. Gore & Associates, Inc. | Integral multi-layered ion-exchange composite membranes |
JPH108009A (en) * | 1996-06-26 | 1998-01-13 | Elf Atochem Japan Kk | Adhesion of poly(vinylidene fluoride) resin to metal and composite material of poly(vinylidene fluoride) adhesive to metal |
EP0938755B1 (en) | 1996-11-01 | 2004-03-10 | E.I. Du Pont De Nemours And Company | Highly conductive ion exchange polymer and process |
US6444343B1 (en) * | 1996-11-18 | 2002-09-03 | University Of Southern California | Polymer electrolyte membranes for use in fuel cells |
US6025092A (en) * | 1998-02-13 | 2000-02-15 | E. I. Du Pont De Nemours And Company | Fluorinated ionomers and their uses |
JP4150867B2 (en) * | 1998-05-13 | 2008-09-17 | ダイキン工業株式会社 | Materials for solid polymer electrolytes suitable for use in fuel cells |
US6076720A (en) | 1998-07-22 | 2000-06-20 | Deng; Jinn-Yi | Stapler with staples of different sizes |
CA2356293A1 (en) * | 1998-12-22 | 2000-06-29 | David Systems Technology S.L. | Membrane-electrode assembly and method of its production |
US6423784B1 (en) * | 1999-12-15 | 2002-07-23 | 3M Innovative Properties Company | Acid functional fluoropolymer membranes and method of manufacture |
-
2001
- 2001-01-30 US US09/774,266 patent/US6780935B2/en not_active Expired - Lifetime
- 2001-02-15 RU RU2001130757/04A patent/RU2264420C2/en active
- 2001-02-15 WO PCT/US2001/004995 patent/WO2001060872A1/en active Application Filing
- 2001-02-15 JP JP2001560254A patent/JP4837216B2/en not_active Expired - Lifetime
- 2001-02-15 CN CNB018002137A patent/CN1142193C/en not_active Expired - Lifetime
- 2001-02-15 KR KR1020017013043A patent/KR100743845B1/en active IP Right Grant
- 2001-02-15 MX MXPA01010408A patent/MXPA01010408A/en active IP Right Grant
- 2001-02-15 CA CA2369696A patent/CA2369696C/en not_active Expired - Lifetime
- 2001-02-15 EP EP01916103A patent/EP1177221A4/en not_active Withdrawn
- 2001-03-08 TW TW090103434A patent/TWI302540B/en not_active IP Right Cessation
- 2001-09-25 IL IL145673A patent/IL145673A/en active IP Right Grant
-
2003
- 2003-09-24 US US10/670,095 patent/US6872781B2/en not_active Expired - Lifetime
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5272186A (en) * | 1992-05-01 | 1993-12-21 | E. I. Du Pont De Nemours And Company | Concentration of fluoropolymer dispersions using acrylic polymers of high acid content |
US5880204A (en) * | 1995-09-27 | 1999-03-09 | Alliedsignal Inc. | Room temperature coalescable aqueous fluoropolymer dispersions and method for their manufacture |
US5962140A (en) * | 1996-06-25 | 1999-10-05 | Acushnet Company | Golf ball comprising fluoropolymer |
Non-Patent Citations (1)
Title |
---|
See also references of EP1177221A4 * |
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US9447217B2 (en) | 2001-09-07 | 2016-09-20 | Itm Power (Research) Limited | Method for producing a membrane electrode including forming the membrane in situ |
EP1455407A2 (en) * | 2003-03-06 | 2004-09-08 | Atofina Chemicals, Inc. | Non-perfluoropolymer resins containing ionic or ionizable groups and products containing the same |
JP2004269875A (en) * | 2003-03-06 | 2004-09-30 | Atofina Chemicals Inc | Ionic or ionizable functional group-containing non-perfluorinated polymer resin and product containing the resin |
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EP1505120A1 (en) * | 2003-07-30 | 2005-02-09 | Atofina Chemicals, Inc. | Resin compositions containing ionic or ionizable groups with small domain sizes and improved conductivity |
JP2005050816A (en) * | 2003-07-30 | 2005-02-24 | Arkema Inc | Ion having small particle boundary size and improved conductivity or resin including ionized group |
US8153329B2 (en) | 2004-06-24 | 2012-04-10 | Konica Minolta Holdings, Inc. | Proton conducting electrolyte membrane and production method thereof and solid polymer fuel cell using the same |
WO2006019508A2 (en) | 2004-07-14 | 2006-02-23 | Arkema Inc. | Multi-layer polyelectrolyte membrane |
EP1794823A2 (en) * | 2004-07-14 | 2007-06-13 | Arkema Inc. | Multi-layer polyelectrolyte membrane |
EP1794823A4 (en) * | 2004-07-14 | 2009-12-16 | Arkema Inc | Multi-layer polyelectrolyte membrane |
US8846267B2 (en) | 2005-06-27 | 2014-09-30 | Itm Power (Research) Ltd. | Membrane electrode assemblies |
WO2008002747A1 (en) * | 2006-06-29 | 2008-01-03 | Avery Dennison Corporation | Polyvinylidene fluoride films and laminates thereof |
Also Published As
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JP2003523419A (en) | 2003-08-05 |
CA2369696A1 (en) | 2001-08-23 |
US6780935B2 (en) | 2004-08-24 |
CN1362971A (en) | 2002-08-07 |
US20040092661A1 (en) | 2004-05-13 |
IL145673A0 (en) | 2002-06-30 |
EP1177221A1 (en) | 2002-02-06 |
TWI302540B (en) | 2008-11-01 |
CN1142193C (en) | 2004-03-17 |
US6872781B2 (en) | 2005-03-29 |
KR100743845B1 (en) | 2007-08-02 |
RU2264420C2 (en) | 2005-11-20 |
IL145673A (en) | 2009-09-22 |
EP1177221A4 (en) | 2006-11-08 |
MXPA01010408A (en) | 2002-05-06 |
US20030064267A1 (en) | 2003-04-03 |
JP4837216B2 (en) | 2011-12-14 |
KR20020000798A (en) | 2002-01-05 |
CA2369696C (en) | 2011-12-13 |
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