JP2005526875A - ビニル含有スルホン酸を含む混合物、ポリビニルスルホン酸を含む高分子電解質膜、および燃料電池におけるその使用 - Google Patents
ビニル含有スルホン酸を含む混合物、ポリビニルスルホン酸を含む高分子電解質膜、および燃料電池におけるその使用 Download PDFInfo
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- JP2005526875A JP2005526875A JP2003573057A JP2003573057A JP2005526875A JP 2005526875 A JP2005526875 A JP 2005526875A JP 2003573057 A JP2003573057 A JP 2003573057A JP 2003573057 A JP2003573057 A JP 2003573057A JP 2005526875 A JP2005526875 A JP 2005526875A
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- membrane
- vinyl
- polymer
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- 239000012528 membrane Substances 0.000 title claims abstract description 150
- 229920002554 vinyl polymer Polymers 0.000 title claims abstract description 69
- 239000000446 fuel Substances 0.000 title claims abstract description 59
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 title claims abstract description 59
- 239000000203 mixture Substances 0.000 title claims abstract description 42
- 239000005518 polymer electrolyte Substances 0.000 title abstract description 17
- 150000003460 sulfonic acids Chemical class 0.000 title description 8
- 229920000642 polymer Polymers 0.000 claims abstract description 69
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims abstract description 31
- 229920001940 conductive polymer Polymers 0.000 claims abstract description 7
- 239000000126 substance Substances 0.000 claims abstract description 6
- 238000002156 mixing Methods 0.000 claims abstract description 4
- 230000000379 polymerizing effect Effects 0.000 claims abstract description 3
- -1 ethyleneoxy group Chemical group 0.000 claims description 84
- 125000001072 heteroaryl group Chemical group 0.000 claims description 45
- 238000000034 method Methods 0.000 claims description 37
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 30
- 239000002253 acid Substances 0.000 claims description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 125000006732 (C1-C15) alkyl group Chemical group 0.000 claims description 26
- 229910052736 halogen Inorganic materials 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 26
- 238000006116 polymerization reaction Methods 0.000 claims description 25
- 150000002431 hydrogen Chemical class 0.000 claims description 20
- 125000005843 halogen group Chemical group 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 13
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- 229920002492 poly(sulfone) Polymers 0.000 claims description 13
- 238000004132 cross linking Methods 0.000 claims description 12
- 239000001301 oxygen Chemical group 0.000 claims description 12
- 239000000178 monomer Substances 0.000 claims description 8
- 239000003999 initiator Substances 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical group O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 5
- 238000010894 electron beam technology Methods 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 239000002322 conducting polymer Substances 0.000 claims description 4
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 74
- 239000003054 catalyst Substances 0.000 description 59
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 30
- 125000003118 aryl group Chemical group 0.000 description 23
- 229920005597 polymer membrane Polymers 0.000 description 21
- 239000000243 solution Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 239000000654 additive Substances 0.000 description 16
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 15
- 239000000463 material Substances 0.000 description 15
- 239000002245 particle Substances 0.000 description 14
- 239000000725 suspension Substances 0.000 description 14
- 239000003792 electrolyte Substances 0.000 description 13
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 13
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 12
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 12
- 125000002950 monocyclic group Chemical group 0.000 description 12
- 125000003367 polycyclic group Chemical group 0.000 description 12
- 238000005341 cation exchange Methods 0.000 description 11
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- 150000003009 phosphonic acids Chemical class 0.000 description 7
- 229920000137 polyphosphoric acid Polymers 0.000 description 7
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- 239000004693 Polybenzimidazole Substances 0.000 description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 229920002313 fluoropolymer Polymers 0.000 description 6
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
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- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 5
- 238000005507 spraying Methods 0.000 description 5
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 239000004734 Polyphenylene sulfide Substances 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 239000003431 cross linking reagent Substances 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
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- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 4
- 229920001643 poly(ether ketone) Polymers 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 229920000139 polyethylene terephthalate Polymers 0.000 description 4
- 239000005020 polyethylene terephthalate Substances 0.000 description 4
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- 238000002360 preparation method Methods 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 238000002407 reforming Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000006277 sulfonation reaction Methods 0.000 description 4
- ZTWTYVWXUKTLCP-UHFFFAOYSA-N vinylphosphonic acid Chemical class OP(O)(=O)C=C ZTWTYVWXUKTLCP-UHFFFAOYSA-N 0.000 description 4
- VMLKTERJLVWEJJ-UHFFFAOYSA-N 1,5-naphthyridine Chemical compound C1=CC=NC2=CC=CN=C21 VMLKTERJLVWEJJ-UHFFFAOYSA-N 0.000 description 3
- 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
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 3
- 239000002028 Biomass Substances 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
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- 229910019142 PO4 Inorganic materials 0.000 description 3
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- 238000007606 doctor blade method Methods 0.000 description 3
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- 238000010438 heat treatment Methods 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
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- NOBYOEQUFMGXBP-UHFFFAOYSA-N (4-tert-butylcyclohexyl) (4-tert-butylcyclohexyl)oxycarbonyloxy carbonate Chemical compound C1CC(C(C)(C)C)CCC1OC(=O)OOC(=O)OC1CCC(C(C)(C)C)CC1 NOBYOEQUFMGXBP-UHFFFAOYSA-N 0.000 description 2
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- UQSNKBSJGIHNFF-UHFFFAOYSA-M potassium 1-fluorohexane-1-sulfonate Chemical compound FC(CCCCC)S(=O)(=O)[O-].[K+] UQSNKBSJGIHNFF-UHFFFAOYSA-M 0.000 description 1
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- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
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- LVTHXRLARFLXNR-UHFFFAOYSA-M potassium;1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate Chemical compound [K+].[O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F LVTHXRLARFLXNR-UHFFFAOYSA-M 0.000 description 1
- GLGXXYFYZWQGEL-UHFFFAOYSA-M potassium;trifluoromethanesulfonate Chemical compound [K+].[O-]S(=O)(=O)C(F)(F)F GLGXXYFYZWQGEL-UHFFFAOYSA-M 0.000 description 1
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- RAJUSMULYYBNSJ-UHFFFAOYSA-N prop-1-ene-1-sulfonic acid Chemical compound CC=CS(O)(=O)=O RAJUSMULYYBNSJ-UHFFFAOYSA-N 0.000 description 1
- XWCIXXXLOAAWPU-UHFFFAOYSA-N prop-1-enylphosphonic acid Chemical compound CC=CP(O)(O)=O XWCIXXXLOAAWPU-UHFFFAOYSA-N 0.000 description 1
- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
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- 239000010948 rhodium Substances 0.000 description 1
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- QBJDFZSOZNDVDE-UHFFFAOYSA-M sodium;1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F QBJDFZSOZNDVDE-UHFFFAOYSA-M 0.000 description 1
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- XGPOMXSYOKFBHS-UHFFFAOYSA-M sodium;trifluoromethanesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C(F)(F)F XGPOMXSYOKFBHS-UHFFFAOYSA-M 0.000 description 1
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- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
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- WYKYCHHWIJXDAO-UHFFFAOYSA-N tert-butyl 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOC(C)(C)C WYKYCHHWIJXDAO-UHFFFAOYSA-N 0.000 description 1
- PFBLRDXPNUJYJM-UHFFFAOYSA-N tert-butyl 2-methylpropaneperoxoate Chemical compound CC(C)C(=O)OOC(C)(C)C PFBLRDXPNUJYJM-UHFFFAOYSA-N 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 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
- TXEYQDLBPFQVAA-UHFFFAOYSA-N tetrafluoromethane Chemical group FC(F)(F)F TXEYQDLBPFQVAA-UHFFFAOYSA-N 0.000 description 1
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- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
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- PGOMVYSURVZIIW-UHFFFAOYSA-N trifluoro(nitroso)methane Chemical compound FC(F)(F)N=O PGOMVYSURVZIIW-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- B01D71/06—Organic material
- B01D71/38—Polyalkenylalcohols; Polyalkenylesters; Polyalkenylethers; Polyalkenylaldehydes; Polyalkenylketones; Polyalkenylacetals; Polyalkenylketals
- B01D71/381—Polyvinylalcohol
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- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M8/00—Fuel cells; Manufacture thereof
- H01M8/10—Fuel cells with solid electrolytes
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01D71/00—Semi-permeable membranes for separation processes or apparatus characterised by the material; Manufacturing processes specially adapted therefor
- B01D71/06—Organic material
- B01D71/58—Other polymers having nitrogen in the main chain, with or without oxygen or carbon only
- B01D71/62—Polycondensates having nitrogen-containing heterocyclic rings in the main chain
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- C—CHEMISTRY; METALLURGY
- 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
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/20—Manufacture of shaped structures of ion-exchange resins
- C08J5/22—Films, membranes or diaphragms
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- C—CHEMISTRY; METALLURGY
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- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/20—Manufacture of shaped structures of ion-exchange resins
- C08J5/22—Films, membranes or diaphragms
- C08J5/2206—Films, membranes or diaphragms based on organic and/or inorganic macromolecular compounds
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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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- H01M8/1016—Fuel cells with solid electrolytes characterised by the electrolyte material
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- H01M8/1027—Polymeric electrolyte materials characterised by the chemical structure of the main chain of the ion-conducting polymer having carbon, oxygen and other atoms, e.g. sulfonated polyethersulfones [S-PES]
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- H01M8/1016—Fuel cells with solid electrolytes characterised by the electrolyte material
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- H01M8/102—Polymeric electrolyte materials characterised by the chemical structure of the main chain of the ion-conducting polymer
- H01M8/103—Polymeric electrolyte materials characterised by the chemical structure of the main chain of the ion-conducting polymer having nitrogen, e.g. sulfonated polybenzimidazoles [S-PBI], polybenzimidazoles with phosphoric acid, sulfonated polyamides [S-PA] or sulfonated polyphosphazenes [S-PPh]
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- H01M8/1016—Fuel cells with solid electrolytes characterised by the electrolyte material
- H01M8/1018—Polymeric electrolyte materials
- H01M8/102—Polymeric electrolyte materials characterised by the chemical structure of the main chain of the ion-conducting polymer
- H01M8/1032—Polymeric electrolyte materials characterised by the chemical structure of the main chain of the ion-conducting polymer having sulfur, e.g. sulfonated-polyethersulfones [S-PES]
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M8/00—Fuel cells; Manufacture thereof
- H01M8/10—Fuel cells with solid electrolytes
- H01M8/1016—Fuel cells with solid electrolytes characterised by the electrolyte material
- H01M8/1018—Polymeric electrolyte materials
- H01M8/1069—Polymeric electrolyte materials characterised by the manufacturing processes
- H01M8/1072—Polymeric electrolyte materials characterised by the manufacturing processes by chemical reactions, e.g. insitu polymerisation or insitu crosslinking
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2323/00—Details relating to membrane preparation
- B01D2323/34—Use of radiation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2325/00—Details relating to properties of membranes
- B01D2325/24—Mechanical properties, e.g. strength
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2325/00—Details relating to properties of membranes
- B01D2325/26—Electrical properties
-
- C—CHEMISTRY; METALLURGY
- 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
- C08J2379/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen, or carbon only, not provided for in groups C08J2361/00 - C08J2377/00
- C08J2379/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08J2379/06—Polyhydrazides; Polytriazoles; Polyamino-triazoles; Polyoxadiazoles
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M4/00—Electrodes
- H01M4/86—Inert electrodes with catalytic activity, e.g. for fuel cells
- H01M4/8605—Porous electrodes
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M4/00—Electrodes
- H01M4/86—Inert electrodes with catalytic activity, e.g. for fuel cells
- H01M4/90—Selection of catalytic material
- H01M4/92—Metals of platinum group
- H01M4/921—Alloys or mixtures with metallic elements
-
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/30—Hydrogen technology
- Y02E60/50—Fuel cells
-
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P70/00—Climate change mitigation technologies in the production process for final industrial or consumer products
- Y02P70/50—Manufacturing or production processes characterised by the final manufactured product
Abstract
Description
A)ポリマーを、ビニル含有スルホン酸と混合するステップと、
B)ステップA)からの混合物を使用して支持体上に平面構造体を形成するステップと、
C)ステップB)からの平面構造体中に存在する、ビニル含有スルホン酸を重合するステップと
を含む方法により得ることが可能である膜を提供する。
パースルホン化された添加剤の特に限定されるものではない具体例としては、トリフルオロメタンスルホン酸、トリフルオロメタンスルホン酸カリウム、トリフルオロメタンスルホン酸ナトリウム、トリフルオロメタンスルホン酸リチウム、トリフルオロメタンスルホン酸アンモニウム、パーフルオロヘキサンスルホン酸カリウム、パーフルオロヘキサンスルホン酸ナトリウム、パーフルオロヘキサンスルホン酸リチウム、パーフルオロヘキサンスルホン酸アンモニウム、パーフルオロヘキサンスルホン酸、ノナフルオロブタンスルホン酸カリウム、ノナフルオロブタンスルホン酸ナトリウム、ノナフルオロブタンスルホン酸リチウム、ノナフルオロブタンスルホン酸アンモニウム、ノナフルオロブタンスルホン酸セシウム、パーフルオロヘキサンスルホン酸トリエチルアンモニウム、およびパーフルオロスルホンイミドが挙げられる。
および/または式
および/または式
および/または下式
および/または下式
あることが好ましい。
下式
下式
(式中、Rは、C1〜C15−アルキル基、C5〜C20−アリールもしくはヘテロアリール基、NR’、−SO2、PR’,Si(R’)2であり、ただし上記の基は、置換されていてもよく、基R’はそれぞれ、互いに独立して、水素、C1〜C15−アルキル基、C1〜C15−アルコキシ基、C5〜C20−アリールもしくはヘテロアリール基であり、またnは少なくとも2である。)が特に好ましい。
ビニルスルホン酸の調製
直径5.5cmを有するカラムに、高さ20cmまでアルドリッチ社製のドウェックス50W−X4型の架橋したスルホン化ポリスチレンからなるイオン交換樹脂を装入する。その後、そのカラムを通してビニルスルホン酸ナトリウム25%力価水溶液100ml(0.19モル)を通過させ、80〜90ml(0.16モル)のビニルスルホン酸を回収する。その後、回転蒸発器上で溶液体積を減少させ、それによりビニルスルホン酸の濃度を30重量%とする。
固有粘度1.0dl/gを有するポリベンズイミダゾールポリマー100gを、89%力価リン酸250ml中で160℃において4時間処理する。その後、吸引フィルタを通す濾過により過剰の酸を除去し、固形物を水で3回洗浄する。その後、こうして得られたポリマーを100mlの10%力価水酸化アンモニウム(NH4OH)で2回中和し、その後蒸留水で2回処理する。その後、このポリマーを160℃で1時間処理し、それにより残渣の水分含量を8%とする。
Claims (20)
- ポリビニルスルホン酸を主成分とし、かつ
A)あるポリマーをビニル含有スルホン酸と混合するステップと、
B)ステップA)からの混合物を使用して、支持体上に平面構造体を形成するステップと、
C)ステップB)からの平面構造体中に存在する、ビニル含有スルホン酸を重合するステップと
を含む方法によって得ることができる、プロトン伝導性高分子膜。 - ステップA)において使用される前記ポリマーが、1つの反復単位内または異なる反復単位内に少なくとも1個の窒素、酸素および/または硫黄原子を含有する高温安定性ポリマーであることを特徴とする、請求項1に記載の膜。
- ステップA)において1種以上のポリアゾールおよび/またはポリスルホンが使用されることを特徴とする、請求項1に記載の膜。
- ステップA)において調製される前記混合物が、下式
および/または式
および/または式
- ステップA)において調製される前記混合物が、ビニル含有ホスホン酸を含むことを特徴とする、請求項1に記載の膜。
- ステップA)において調製される前記混合物が、下式
および/または式
および/または式
- ビニル含有ホスホン酸のビニル含有スルホン酸に対する重量比が、1:100〜99:1の範囲にあることを特徴とする、請求項5または6に記載の膜。
- ステップA)において調製される前記混合物が、架橋することが可能なモノマーを含有することを特徴とする、請求項1に記載の膜。
- ステップC)における重合が、フリーラジカルを形成することが可能な物質によって行われることを特徴とする、請求項1に記載の膜。
- ステップC)における重合が、IRもしくはNIR光、UV光、β線、γ線、および/または電子ビームによる照射によって行われることを特徴とする、請求項1に記載の膜。
- 前記膜が、少なくとも0.001S/cmの固有伝導度を有することを特徴とする、請求項1に記載の膜。
- 前記膜が、1〜90重量%の前記ポリマーと、99〜0.5重量%のポリビニルホスホン酸とを含むことを特徴とする、請求項1に記載の膜。
- 前記膜が、触媒的に活性な成分を含む層を有することを特徴とする、請求項1に記載の膜。
- 請求項4に規定するビニル含有スルホン酸と、前記ビニル含有スルホン酸中への少なくとも1重量%の溶解度を有する少なくとも1種のポリマーとを含む混合物。
- 使用する前記ポリマーが、1つの反復単位内または異なった反復単位内に少なくとも1個の窒素、酸素および/または硫黄原子を含有するポリマーであることを特徴とする、請求項11に記載の混合物。
- 架橋することが可能な少なくとも1種のモノマーを含有することを特徴とする、請求項11に記載の混合物。
- フリーラジカルを形成することが可能である少なくとも1種の開始剤を含有することを特徴とする、請求項11に記載の混合物。
- 前記混合物が、少なくとも1種のビニル含有ホスホン酸を含むことを特徴とする、請求項11に記載の混合物。
- 請求項1から13までのいずれか一項に記載の少なくとも1つの膜を含んだ膜電極単位。
- 請求項19に記載の膜電極単位の1種以上、および/または請求項1から13のいずれかに記載の膜の1種以上を含んだ燃料電池。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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DE10209684A DE10209684A1 (de) | 2002-03-06 | 2002-03-06 | Lösung aus Vinylsulfonsäure, Verfahren zur Herstellung einer Polymerelektrolytmembran aus Polyvinylsulfonsäure und deren Anwendung in Brennstoffzellen |
DE10210500A DE10210500A1 (de) | 2002-03-11 | 2002-03-11 | Lösung aus Vinylphosphonsäure und Vinylsulfonsäure, Verfahren zur Herstellung einer Polymerelektrolytmembran aus Polyvinylphosphonsäure und Polyvinylsulfonsäure und deren Anwendung in Brennstoffzellen |
PCT/EP2003/002395 WO2003074595A1 (de) | 2002-03-06 | 2003-03-04 | Mischungen umfassend vinylhaltige sulfonsäure, polymerelektrolytmembranen umfassend polyvinylsulfonsäure und deren anwendung in brennstoffzellen |
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EP (1) | EP1485427B1 (ja) |
JP (1) | JP2005526875A (ja) |
KR (1) | KR20040107473A (ja) |
CN (1) | CN1318484C (ja) |
AT (1) | ATE316111T1 (ja) |
CA (1) | CA2477863A1 (ja) |
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WO (1) | WO2003074595A1 (ja) |
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JP2007504333A (ja) * | 2003-09-04 | 2007-03-01 | ペミアス ゲーエムベーハー | 高分子膜がホスホン酸ポリマーを含む、触媒層でコーティングされたプロトン伝導性高分子膜、膜/電極ユニットおよび燃料電池におけるその使用 |
JP2007087670A (ja) * | 2005-09-20 | 2007-04-05 | Ricoh Co Ltd | 固体電解質、固体電解質の製造方法、燃料電池、及び電子機器 |
WO2007123268A1 (ja) | 2006-04-19 | 2007-11-01 | Toyota Jidosha Kabushiki Kaisha | スルホン基含有モノマーのビニル重合体、その製造方法、高分子電解質、高分子電解質膜、及び燃料電池 |
WO2007142031A1 (ja) * | 2006-06-09 | 2007-12-13 | Shin-Etsu Chemical Co., Ltd. | ダイレクトメタノール型燃料電池用電解質膜・電極接合体 |
JP2010508619A (ja) * | 2005-10-29 | 2010-03-18 | ビーエーエスエフ、フューエル、セル、ゲゼルシャフト、ミット、ベシュレンクテル、ハフツング | ホスホン酸及び/又はスルホン酸基を含むポリマーを含む燃料電池用の膜、膜電極アッセンブリ及びその燃料電池での使用法 |
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Also Published As
Publication number | Publication date |
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EP1485427B1 (de) | 2006-01-18 |
ATE316111T1 (de) | 2006-02-15 |
CN1318484C (zh) | 2007-05-30 |
EP1485427A1 (de) | 2004-12-15 |
WO2003074595A1 (de) | 2003-09-12 |
CN1649945A (zh) | 2005-08-03 |
DE50302234D1 (de) | 2006-04-06 |
CA2477863A1 (en) | 2003-09-12 |
KR20040107473A (ko) | 2004-12-20 |
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