JP6425289B2 - 新たな化合物およびこれを用いた高分子電解質膜 - Google Patents
新たな化合物およびこれを用いた高分子電解質膜 Download PDFInfo
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- JP6425289B2 JP6425289B2 JP2017518345A JP2017518345A JP6425289B2 JP 6425289 B2 JP6425289 B2 JP 6425289B2 JP 2017518345 A JP2017518345 A JP 2017518345A JP 2017518345 A JP2017518345 A JP 2017518345A JP 6425289 B2 JP6425289 B2 JP 6425289B2
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- 239000012528 membrane Substances 0.000 title claims description 72
- 150000001875 compounds Chemical class 0.000 title claims description 45
- 239000005518 polymer electrolyte Substances 0.000 title claims description 40
- 239000000446 fuel Substances 0.000 claims description 45
- 229920000642 polymer Polymers 0.000 claims description 43
- 239000003792 electrolyte Substances 0.000 claims description 39
- 229910052739 hydrogen Inorganic materials 0.000 claims description 31
- 125000005843 halogen group Chemical group 0.000 claims description 29
- 239000001257 hydrogen Substances 0.000 claims description 28
- 239000000178 monomer Substances 0.000 claims description 27
- 239000000126 substance Substances 0.000 claims description 26
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 239000007800 oxidant agent Substances 0.000 claims description 16
- 230000001590 oxidative effect Effects 0.000 claims description 15
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 12
- 239000011737 fluorine Substances 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 9
- 230000000712 assembly Effects 0.000 claims description 4
- 238000000429 assembly Methods 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 230000000379 polymerizing effect Effects 0.000 claims 1
- 239000010410 layer Substances 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 21
- 150000002500 ions Chemical class 0.000 description 21
- 239000003054 catalyst Substances 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 12
- 239000002904 solvent Substances 0.000 description 10
- 238000009792 diffusion process Methods 0.000 description 9
- 125000000524 functional group Chemical group 0.000 description 9
- 239000007789 gas Substances 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- -1 polyethylene naphthalate Polymers 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 230000008901 benefit Effects 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 150000001555 benzenes Chemical group 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 238000005342 ion exchange Methods 0.000 description 6
- 230000009257 reactivity Effects 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 5
- 239000003014 ion exchange membrane Substances 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- 125000000542 sulfonic acid group Chemical group 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 150000001768 cations Chemical class 0.000 description 4
- 238000007599 discharging Methods 0.000 description 4
- 230000005611 electricity Effects 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
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- 125000005647 linker group Chemical group 0.000 description 4
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- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000008151 electrolyte solution Substances 0.000 description 3
- 239000002828 fuel tank Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- NCYNKWQXFADUOZ-UHFFFAOYSA-N 1,1-dioxo-2,1$l^{6}-benzoxathiol-3-one Chemical compound C1=CC=C2C(=O)OS(=O)(=O)C2=C1 NCYNKWQXFADUOZ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- SJOWFKIGZWAXRA-UHFFFAOYSA-N FC1=C(C=CC(=C1)F)SC1=CC=C(C=C1)S(=O)(=O)O.FC1=C(C=CC(=C1)F)SC1=CC=C(C=C1)S(=O)(=O)O Chemical compound FC1=C(C=CC(=C1)F)SC1=CC=C(C=C1)S(=O)(=O)O.FC1=C(C=CC(=C1)F)SC1=CC=C(C=C1)S(=O)(=O)O SJOWFKIGZWAXRA-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 102000004310 Ion Channels Human genes 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000006479 redox reaction Methods 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- OKMMJDMJHRQHEZ-UHFFFAOYSA-N 4-[(2,4-difluorophenyl)sulfanylmethyl]benzenesulfonic acid Chemical compound FC1=C(C=CC(=C1)F)SCC1=CC=C(C=C1)S(=O)(=O)O OKMMJDMJHRQHEZ-UHFFFAOYSA-N 0.000 description 1
- NWYHLYHCONETMH-UHFFFAOYSA-N 4-bromobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(Br)C=C1.OS(=O)(=O)C1=CC=C(Br)C=C1 NWYHLYHCONETMH-UHFFFAOYSA-N 0.000 description 1
- LRQAPWAUROCOCZ-UHFFFAOYSA-N FC1=C(C=CC(=C1)F)S.FC1=C(C=CC(=C1)F)S Chemical compound FC1=C(C=CC(=C1)F)S.FC1=C(C=CC(=C1)F)S LRQAPWAUROCOCZ-UHFFFAOYSA-N 0.000 description 1
- 229910000820 Os alloy Inorganic materials 0.000 description 1
- 239000002033 PVDF binder Substances 0.000 description 1
- 229910001252 Pd alloy Inorganic materials 0.000 description 1
- 239000004693 Polybenzimidazole Substances 0.000 description 1
- 239000004695 Polyether sulfone Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 239000004734 Polyphenylene sulfide Substances 0.000 description 1
- 229910000929 Ru alloy Inorganic materials 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003570 air Substances 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 238000007607 die coating method Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000002001 electrolyte material Substances 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000002737 fuel gas Substances 0.000 description 1
- 229920000554 ionomer Polymers 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 239000003345 natural gas Substances 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 238000007344 nucleophilic reaction Methods 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- IYZXTLXQZSXOOV-UHFFFAOYSA-N osmium platinum Chemical compound [Os].[Pt] IYZXTLXQZSXOOV-UHFFFAOYSA-N 0.000 description 1
- 230000033116 oxidation-reduction process Effects 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- CFQCIHVMOFOCGH-UHFFFAOYSA-N platinum ruthenium Chemical compound [Ru].[Pt] CFQCIHVMOFOCGH-UHFFFAOYSA-N 0.000 description 1
- 229920001643 poly(ether ketone) Polymers 0.000 description 1
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 description 1
- 229920002627 poly(phosphazenes) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002480 polybenzimidazole Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920005597 polymer membrane Polymers 0.000 description 1
- 229920006380 polyphenylene oxide Polymers 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000010248 power generation Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000012495 reaction gas Substances 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000000807 solvent casting Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
Classifications
-
- 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
- H01M8/1039—Polymeric electrolyte materials halogenated, e.g. sulfonated polyvinylidene fluorides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/44—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing doubly-bound oxygen atoms bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/14—Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
-
- 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
-
- 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
- H01M8/1004—Fuel cells with solid electrolytes characterised by membrane-electrode assemblies [MEA]
-
- 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
- H01M8/102—Polymeric electrolyte materials characterised by the chemical structure of the main chain of the ion-conducting polymer
- H01M8/1025—Polymeric electrolyte materials characterised by the chemical structure of the main chain of the ion-conducting polymer having only carbon and oxygen, e.g. polyethers, sulfonated polyetheretherketones [S-PEEK], sulfonated polysaccharides, sulfonated celluloses or sulfonated polyesters
-
- 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
- H01M8/102—Polymeric electrolyte materials characterised by the chemical structure of the main chain of the ion-conducting polymer
- 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]
-
- 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
- H01M8/102—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
- H01M8/18—Regenerative fuel cells, e.g. redox flow batteries or secondary fuel cells
-
- 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
- H01M8/18—Regenerative fuel cells, e.g. redox flow batteries or secondary fuel cells
- H01M8/184—Regeneration by electrochemical means
-
- 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
- H01M8/18—Regenerative fuel cells, e.g. redox flow batteries or secondary fuel cells
- H01M8/184—Regeneration by electrochemical means
- H01M8/188—Regeneration by electrochemical means by recharging of redox couples containing fluids; Redox flow type batteries
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M2300/00—Electrolytes
- H01M2300/0017—Non-aqueous electrolytes
- H01M2300/0065—Solid electrolytes
- H01M2300/0082—Organic polymers
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Manufacturing & Machinery (AREA)
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Description
[化学式1]
Aはスルホニル基(−SO2−)またはカルボニル基(−CO−)であり、
R1、R3およびR5は互いに同一または異なり、それぞれ独立に、水素またはハロゲン基であり、
R2およびR4は互いに同一または異なり、それぞれ独立に、水素、ヒドロキシ基、またはハロゲン基であり、
R6およびR7は互いに同一または異なり、それぞれ独立に、水素またはハロゲン基であり、
R8〜R10は互いに同一または異なり、それぞれ独立に、水素、−SO3H、−SO3 −M+、−COOH、−COO−M+、−PO3H2、−PO3H−M+、および−PO3 2−2M+からなる群より選択され、
R8〜R10のうちの少なくとも1つは−SO3H、−SO3 −M+、−COOH、−COO−M+、−PO3H2、−PO3H−M+、および−PO3 2−2M+からなる群より選択され、
Mは1族元素であり、
aは0〜3の整数であり、
aが2以上の整数の場合、複数のR6およびR7はそれぞれ独立に、互いに同一または異なる。
前記膜−電極接合体の間に備えられるバイポーラプレートを含むスタックと、
前記スタックに燃料を供給する燃料供給部と、
前記スタックに酸化剤を供給する酸化剤供給部とを含む高分子電解質型燃料電池を提供する。
正極および正極電解液を含む正極セルと、
負極および負極電解液を含む負極セルと、
前記正極セルと前記負極セルとの間に備えられる、前述した高分子電解質膜とを含むレドックスフロー電池を提供する。
前記化学式1のAがカルボニル基(−CO−)で、aが0の場合の、化学式1で表される化合物は、下記反応式1のような方式で製造される。
[反応式1]
1H NMR(500MHz,DMSO−D6)δ8.5(1H,brs),8.09(1H,m),7.90(3H,m),7.70(1H,m),7.16(1H,m),6.78(2H,m)
[M+H]+=298
前記化学式1のAがスルホニル基(−SO2−)で、aが0の場合の、化学式1で表される化合物は、下記反応式2のような方式で製造される。
[反応式2]
1H NMR(500MHz,DMSO−D6)δ8.52(1H,brs),8.11(2H,d),7.97(2H,d),7.72(1H,m),7.09(1H,m),6.85(1H,m)
[M+H]+=334
前記化学式1のAがスルホニル基(−SO2−)で、aが0の場合の、化学式1で表される化合物は、下記反応式3のような方式で製造される。
[反応式3]
1H NMR(500MHz,DMSO−D6)δ8.45(1H,brs),7.75(3H,m),7.51(2H,m),7.27(1H,m),7.03(1H,m),5.17(1H,s)
[M+H]+=348
前記重合体の合成例1で得られた重合体を用いて分離膜を製造し、GPCにより分子量を測定し、純粋膜の陽イオン伝導度およびイオン交換容量(IEC)を測定した結果を記載した。
実施例1と同様の方法でスルホン酸の位置がスルホニルリンカーを基準としてメタ位にあるモノマーを用いて重合体を製造した。重合体を用いて分離膜を製造し、純粋膜の陽イオン伝導度およびイオン交換容量(IEC)を測定した結果を下記表2に示した。
200a:アノード
200b:カソード
10、20:タンク
11、21:ポンプ
31:電解質膜
32:正極セル
33:負極セル
41:正極電解液
42:負極電解液
60:スタック
70:酸化剤供給部
80:燃料供給部
81:燃料タンク
82:ポンプ
Claims (15)
- 下記化学式1で表される化合物:
[化学式1]
Aはスルホニル基(−SO2−)であり、
R1、R3およびR5は互いに同一または異なり、それぞれ独立に、水素またはハロゲン基であり、R1、R3及びR5の少なくとも2つがハロゲン基であり、
R2およびR4は互いに同一または異なり、それぞれ独立に、水素、ヒドロキシ基、またはハロゲン基であり、
R6およびR7は互いに同一または異なり、それぞれ独立に、水素またはハロゲン基であり、
R8〜R10は互いに同一または異なり、それぞれ独立に、水素、−SO3H、−SO3 −M+、−COOH、−COO−M+、−PO3H2、−PO3H−M+、および−PO3 2−2M+からなる群より選択され、
R8〜R10のうちの少なくとも1つは−SO3H、および−SO3 −M+ からなる群より選択され、
Mは1族元素であり、
aは0〜3の整数であり、
aが2以上の整数の場合、複数のR6およびR7はそれぞれ独立に、互いに同一または異なる。 - R1、R3およびR5の少なくとも2つがフッ素である、
請求項1に記載の化合物。 - 前記R1およびR3がフッ素であり、前記R2、R4およびR5が水素である請求項1に記載の化合物。
- 前記aが0である請求項1に記載の化合物。
- 前記aが1〜3の整数である請求項1に記載の化合物。
- 前記化学式1で表される化合物は下記の構造の中から選択されるいずれか1つである請求項1に記載の化合物:
- 請求項1から6のいずれか1項に記載の化合物を単量体として重合させた重合体。
- 前記重合体は前記単量体を0.1モル%〜100モル%を含む請求項7に記載の重合体。
- 請求項7又は8に記載の重合体を含む高分子電解質膜。
- 前記重合体の重量平均分子量が500g/mol以上5,000,000g/mol以下である請求項9に記載の高分子電解質膜。
- 前記高分子電解質膜の厚さが1μm以上500μm以下である請求項9又は10に記載の高分子電解質膜。
- 前記高分子電解質膜のイオン伝導度が0.01S/cm以上0.5S/cm以下である請求項9から11のいずれか1項に記載の高分子電解質膜。
- アノードと、カソードと、前記アノードと前記カソードとの間に備えられた、請求項9から12のいずれか1項に記載の高分子電解質膜とを含む膜−電極接合体。
- 2以上の、請求項13に記載の膜−電極接合体と、
前記膜−電極接合体の間に備えられるバイポーラプレートを含むスタックと、
前記スタックに燃料を供給する燃料供給部と、
前記スタックに酸化剤を供給する酸化剤供給部とを含む高分子電解質型燃料電池。 - 正極および正極電解液を含む正極セルと、
負極および負極電解液を含む負極セルと、
前記正極セルと前記負極セルとの間に備えられる、請求項9から12のいずれか1項に記載の高分子電解質膜とを含むレドックスフロー電池。
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Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3022320A (en) * | 1959-01-13 | 1962-02-20 | Du Pont | Polycarboxydiphenyl sulfones and anhydrides thereof |
US3055930A (en) * | 1959-02-26 | 1962-09-25 | Geigy Chem Corp | New benzophenone sulphonic acid amides |
JPS62216176A (ja) * | 1986-03-15 | 1987-09-22 | Agency Of Ind Science & Technol | レドツクス電池用電解液 |
TW245719B (ja) | 1990-09-10 | 1995-04-21 | Sterling Winthrop Inc | |
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KR100446662B1 (ko) | 2002-03-22 | 2004-09-04 | 주식회사 엘지화학 | 연료 전지용 복합 폴리머 전해질 막 및 그의 제조방법 |
JP3975908B2 (ja) * | 2002-08-22 | 2007-09-12 | Jsr株式会社 | 新規な芳香族スルホン酸エステル誘導体、ポリアリーレン、スルホン酸基を有するポリアリーレンおよびその製造方法、ならびにプロトン伝導膜およびその製造方法 |
WO2004050654A1 (ja) * | 2002-11-29 | 2004-06-17 | Shionogi & Co., Ltd. | ピロリジン化合物の合成とその塩 |
JP2005197236A (ja) | 2003-12-09 | 2005-07-21 | Honda Motor Co Ltd | 固体高分子型燃料電池およびそれに用いる膜・電極構造体 |
DE602004016469D1 (de) | 2003-12-09 | 2008-10-23 | Honda Motor Co Ltd | Membran-Elektroden-Einheit und Polymer-Elektrolytbrennstoffzelle enthaltend diesselbe |
JP2006152009A (ja) | 2004-11-08 | 2006-06-15 | Yamaguchi Univ | スルホン化芳香族ポリイミド及び該ポリイミドよりなる電解質膜 |
JP2006299080A (ja) | 2005-04-20 | 2006-11-02 | Yamaguchi Univ | 多スルホン化芳香族化合物、スルホン化ポリマー、固体高分子電解質およびプロトン伝導膜 |
JP5044131B2 (ja) * | 2005-07-07 | 2012-10-10 | 富士フイルム株式会社 | 固体電解質複層フィルムの製造方法及び製造設備 |
JP4657055B2 (ja) | 2005-08-03 | 2011-03-23 | 旭化成株式会社 | 電解質膜の製造方法 |
US8222367B2 (en) | 2005-09-30 | 2012-07-17 | Battelle Memorial Institute | Polymers for use in fuel cell components |
JP2007213937A (ja) | 2006-02-08 | 2007-08-23 | Honda Motor Co Ltd | 固体高分子型燃料電池用膜−電極構造体及びその製造方法 |
JP2008097907A (ja) * | 2006-10-10 | 2008-04-24 | Toyobo Co Ltd | 高分子電解質膜、膜/電極接合体及びそれを用いた燃料電池 |
US20100068592A1 (en) | 2007-08-09 | 2010-03-18 | Matsushita Electric Industrial Co., Ltd. | Electrodes for use in hydrocarbon-based membrane electrode assemblies of direct oxidation fuel cells |
WO2009035131A1 (ja) * | 2007-09-11 | 2009-03-19 | Sumitomo Chemical Company, Limited | 高分子電解質膜の製造方法、高分子電解質膜、膜-電極接合体及び燃料電池 |
US7888433B2 (en) * | 2008-05-09 | 2011-02-15 | Gm Global Technology Operations, Inc. | Sulfonated-polyperfluoro-cyclobutane-polyphenylene polymers for PEM fuel cell applications |
JP2012046741A (ja) | 2010-07-28 | 2012-03-08 | Sumitomo Chemical Co Ltd | 高分子電解質組成物、高分子電解質および含硫黄複素環芳香族化合物 |
WO2013153696A1 (ja) * | 2012-04-13 | 2013-10-17 | 株式会社カネカ | 高分子電解質およびその利用 |
KR20130015228A (ko) | 2011-08-02 | 2013-02-13 | 삼성에스디아이 주식회사 | 레독스 플로우 전지용 격리막 및 이를 포함하는 레독스 플로우 전지 |
JP6171342B2 (ja) | 2011-12-20 | 2017-08-02 | 東レ株式会社 | 高分子電解質組成物、およびそれを用いた高分子電解質膜、膜電極複合体および固体高分子型燃料電池 |
WO2014034415A1 (ja) | 2012-08-31 | 2014-03-06 | 東洋紡株式会社 | バナジウム系レドックス電池用イオン交換膜、複合体、及びバナジウム系レドックス電池 |
KR101546816B1 (ko) * | 2012-11-09 | 2015-08-25 | 한국화학연구원 | 부분 가지형 블록 공중합체를 포함하는 이온전도성 고분자 및 이의 용도 |
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