JP6748640B2 - プロトン交換膜用の液体組成物 - Google Patents
プロトン交換膜用の液体組成物 Download PDFInfo
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- JP6748640B2 JP6748640B2 JP2017519898A JP2017519898A JP6748640B2 JP 6748640 B2 JP6748640 B2 JP 6748640B2 JP 2017519898 A JP2017519898 A JP 2017519898A JP 2017519898 A JP2017519898 A JP 2017519898A JP 6748640 B2 JP6748640 B2 JP 6748640B2
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- fluoroalkyl
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- 239000000203 mixture Substances 0.000 title claims description 132
- 239000012528 membrane Substances 0.000 title claims description 65
- 239000007788 liquid Substances 0.000 title claims description 25
- 239000000178 monomer Substances 0.000 claims description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 30
- 229920000642 polymer Polymers 0.000 claims description 23
- -1 fluoroalkyl vinyl ether Chemical compound 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 18
- 238000004519 manufacturing process Methods 0.000 claims description 13
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 claims description 13
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 10
- 229910001413 alkali metal ion Inorganic materials 0.000 claims description 8
- 238000005266 casting Methods 0.000 claims description 8
- 238000002156 mixing Methods 0.000 claims description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 claims description 6
- 125000001033 ether group Chemical group 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000001246 bromo group Chemical group Br* 0.000 claims description 4
- 229920001971 elastomer Polymers 0.000 claims description 4
- 239000000806 elastomer Substances 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 125000002346 iodo group Chemical group I* 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 125000005429 oxyalkyl group Chemical group 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 1
- 125000006663 (C1-C6) perfluoroalkyl group Chemical group 0.000 claims 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 1
- 239000006185 dispersion Substances 0.000 description 19
- 229920000554 ionomer Polymers 0.000 description 18
- 239000007787 solid Substances 0.000 description 18
- 239000002245 particle Substances 0.000 description 16
- 239000000446 fuel Substances 0.000 description 15
- 229920006169 Perfluoroelastomer Polymers 0.000 description 12
- 239000001257 hydrogen Substances 0.000 description 12
- 229910052739 hydrogen Inorganic materials 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 11
- 238000012360 testing method Methods 0.000 description 10
- 229920001973 fluoroelastomer Polymers 0.000 description 8
- 229920000126 latex Polymers 0.000 description 7
- BLTXWCKMNMYXEA-UHFFFAOYSA-N 1,1,2-trifluoro-2-(trifluoromethoxy)ethene Chemical compound FC(F)=C(F)OC(F)(F)F BLTXWCKMNMYXEA-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 230000010287 polarization Effects 0.000 description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- 230000035699 permeability Effects 0.000 description 5
- 229920000728 polyester Polymers 0.000 description 5
- 229960000834 vinyl ether Drugs 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 4
- 238000002356 laser light scattering Methods 0.000 description 4
- 239000002243 precursor Substances 0.000 description 4
- 230000002787 reinforcement Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000013459 approach Methods 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 238000005345 coagulation Methods 0.000 description 3
- 230000015271 coagulation Effects 0.000 description 3
- 230000000875 corresponding effect Effects 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 230000014759 maintenance of location Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 3
- 239000004810 polytetrafluoroethylene Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- RPAJSBKBKSSMLJ-DFWYDOINSA-N (2s)-2-aminopentanedioic acid;hydrochloride Chemical class Cl.OC(=O)[C@@H](N)CCC(O)=O RPAJSBKBKSSMLJ-DFWYDOINSA-N 0.000 description 2
- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 description 2
- ZFPGARUNNKGOBB-UHFFFAOYSA-N 1-Ethyl-2-pyrrolidinone Chemical compound CCN1CCCC1=O ZFPGARUNNKGOBB-UHFFFAOYSA-N 0.000 description 2
- AYCANDRGVPTASA-UHFFFAOYSA-N 1-bromo-1,2,2-trifluoroethene Chemical group FC(F)=C(F)Br AYCANDRGVPTASA-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 239000003792 electrolyte Substances 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 229920002313 fluoropolymer Polymers 0.000 description 2
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000004816 latex Substances 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical class FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 1
- HFNSTEOEZJBXIF-UHFFFAOYSA-N 2,2,4,5-tetrafluoro-1,3-dioxole Chemical compound FC1=C(F)OC(F)(F)O1 HFNSTEOEZJBXIF-UHFFFAOYSA-N 0.000 description 1
- DMWVYCCGCQPJEA-UHFFFAOYSA-N 2,5-bis(tert-butylperoxy)-2,5-dimethylhexane Chemical compound CC(C)(C)OOC(C)(C)CCC(C)(C)OOC(C)(C)C DMWVYCCGCQPJEA-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- QMIWYOZFFSLIAK-UHFFFAOYSA-N 3,3,3-trifluoro-2-(trifluoromethyl)prop-1-ene Chemical group FC(F)(F)C(=C)C(F)(F)F QMIWYOZFFSLIAK-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229920000544 Gore-Tex Polymers 0.000 description 1
- 229920006370 Kynar Polymers 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000003570 air Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- 238000010382 chemical cross-linking Methods 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 229920000295 expanded polytetrafluoroethylene Polymers 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- OFXSXYCSPVKZPF-UHFFFAOYSA-N methoxyperoxymethane Chemical compound COOOC OFXSXYCSPVKZPF-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000001451 organic peroxides Chemical group 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 238000002464 physical blending Methods 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000005518 polymer electrolyte Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
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- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
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- 238000013112 stability test Methods 0.000 description 1
- 238000012430 stability testing Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical compound FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
Classifications
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- 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
- H01M8/1041—Polymer electrolyte composites, mixtures or blends
- H01M8/1044—Mixtures of polymers, of which at least one is ionically conductive
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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
- C08J5/2206—Films, membranes or diaphragms based on organic and/or inorganic macromolecular compounds
- C08J5/2218—Synthetic macromolecular compounds
- C08J5/2231—Synthetic macromolecular compounds based on macromolecular compounds obtained by reactions involving unsaturated carbon-to-carbon bonds
- 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
-
- 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
- C08J5/2206—Films, membranes or diaphragms based on organic and/or inorganic macromolecular compounds
- C08J5/2275—Heterogeneous membranes
- C08J5/2281—Heterogeneous membranes fluorine containing heterogeneous membranes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L27/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers
- C08L27/02—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L27/12—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L27/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers
- C08L27/02—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L27/12—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms
- C08L27/18—Homopolymers or copolymers or tetrafluoroethene
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D127/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Coating compositions based on derivatives of such polymers
- C09D127/02—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Coating compositions based on derivatives of such polymers not modified by chemical after-treatment
- C09D127/12—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Coating compositions based on derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D127/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Coating compositions based on derivatives of such polymers
- C09D127/02—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Coating compositions based on derivatives of such polymers not modified by chemical after-treatment
- C09D127/12—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Coating compositions based on derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms
- C09D127/18—Homopolymers or copolymers of tetrafluoroethene
-
- 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
- H01M8/1081—Polymeric electrolyte materials characterised by the manufacturing processes starting from solutions, dispersions or slurries exclusively of polymers
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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
- C08J2327/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers
- C08J2327/02—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers not modified by chemical after-treatment
- C08J2327/12—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms
- C08J2327/18—Homopolymers or copolymers of tetrafluoroethylene
-
- 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
- C08J2327/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers
- C08J2327/22—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers modified by chemical after-treatment
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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Description
本出願は、2014年10月20日出願の欧州特許出願第14189535.9号に対する優先権を主張するものであり、この出願の全内容は、あらゆる目的のために参照により本明細書に援用される。
− 液体媒体[媒体(L)]と;
− 少なくとも1個の−SO3Z基(式中、Zは、H,アルカリ金属イオンまたはNH4 +である)を含有する少なくとも1種のエチレン性不飽和フッ素化モノマー[モノマー(A)]に由来する繰り返し単位と、少なくとも1種のエチレン性不飽和フッ素化モノマー[モノマー(B)]に由来する繰り返し単位とを含む少なくとも1種のポリマー[成分(I)]と;
− 少なくとも1種のパーフルオロエラストマー[成分(II)]と
を含む組成物[組成物(C)]であって、
前記成分(I)と前記成分(II)との間の重量比が95/5〜70/30である組成物に関する。
(i)第1液体媒体[媒体(I)]中に成分(I)を含む組成物[組成物(C1)]を提供する工程と;
(ii)組成物(dC1)の総重量に対して10重量%未満の量で前記成分(I)を含む、希釈された液体媒体[媒体(dI)]中の希釈された前記組成物[組成物(dC1)]を得るために、前記組成物(C1)を液体媒体[媒体(d)]で希釈する工程と;
(iii)95/5〜70/30の前記成分(I)対前記成分(II)の重量比からなる、第3液体媒体[媒体(III)]中の希釈された混合組成物(dC3)を提供するために、前記組成物(dC1)を、第2液体媒体[媒体(II)]中に成分(II)を含む組成物[組成物(C2)]と混合する工程と、
(iv)媒体(L)、成分(I)および成分(II)を含む組成物(C)であって、前記成分(I)および前記成分(II)が、前記組成物の総重量を基準として少なくとも15重量%の量で存在する組成物(C)を提供するために、前記媒体(III)を前記組成物(dC3)から部分的に除去する工程と
を含む方法に関する。
− CF2=CF(CF2)pSO3Z(式中、pは、0〜10、好ましくは1〜6の整数であり、より好ましくはpは2または3に等しく、好ましくはZは上に定義された通りである);
− CF2=CF−O−(CF2)mSO3Z(式中、mは、1〜10、好ましくは1〜6、より好ましくは2〜4の整数であり、さらにより好ましくはmは2に等しく、好ましくはZは上に定義された通りである);
− CF2=CF−(OCF2CF(RF1))w−O−CF2(CF(RF2))ySO3Z(式中、wは、0〜2の整数であり、互いに等しいかもしくは異なる、RF1およびRF2は独立して、F、Clまたは、1個もしくは複数個のエーテル酸素原子で場合により置換された、C1〜C10フルオロアルキル基であり、yは、0〜6の整数であり;好ましくはwは1であり、RF1は−CF3であり、yは1であり、RF2はFであり、好ましくはZは上に定義された通りである);
− CF2=CF−Ar−SO3Z(式中、Arは、C5〜C15の芳香族またはヘテロ芳香族置換基であり、好ましくはZは上に定義された通りである)
からなる群から選択される。
− テトラフルオロエチレン、ペンタフルオロプロピレン、ヘキサフルオロプロピレン、およびヘキサフルオロイソブチレンなどの、C2〜C8フルオロオレフィン;
− フッ化ビニリデン;
− クロロトリフルオロエチレンおよびブロモトリフルオロエチレンなどの、C2〜C8クロロ−および/またはブロモ−および/またはヨード−フルオロオレフィン;
− 式CF2=CFORf1(式中、Rf1は、C1〜C6フルオロアルキル、例えば−CF3、−C2F5、−C3F7である)のフルオロアルキルビニルエーテル;
− 式CF2=CFORO1(式中、RO1は、1つもしくは複数のエーテル基を有するC1〜C12フルオロ−オキシアルキル、例えばパーフルオロ−2−プロポキシ−プロピルである)のフルオロ−オキシアルキルビニルエーテル;
− 式CF2=CFOCF2ORf2(式中、Rf2は、C1〜C6フルオロアルキル、例えば−CF3、−C2F5、−C3F7であるかまたは、−C2F5−O−CF3のような、1つもしくは複数のエーテル基を有するC1〜C6フルオロオキシアルキル基である)のフルオロアルキル−メトキシ−ビニルエーテル;
− 式:
(式中、互いに等しいかもしくは異なる、Rf3、Rf4、Rf5およびRf6のそれぞれは独立して、フッ素原子;1個もしくは複数個の酸素原子を場合により含む、C1〜C6フルオロ(ハロ)フルオロアルキル基、例えば−CF3、−C2F5、−C3F7、−OCF3、−OCF2CF2OCF3である)
のフルオロジオキソール
からなる群から選択される。
− C3〜C8フルオロオレフィン、好ましくはテトラフルオロエチレンおよび/またはヘキサフルオロプロピレン;
− クロロトリフルオロエチレンおよび/またはブロモトリフルオロエチレンのような、クロロ−および/またはブロモ−および/またはヨード−C2〜C6フルオロオレフィン;
− 式CF2=CFORf1(式中、Rf1は、C1〜C6フルオロアルキル、例えば−CF3、−C2F5、−C3F7である)のフルオロアルキルビニルエーテル;
− 式CF2=CFORO1(式中、RO1は、パーフルオロ−2−プロポキシ−プロピルのような、1つもしくは複数のエーテル基を有するC1〜C12フルオロオキシアルキルである)のフロオロ−オキシアルキルビニルエーテル
からなる群から選択される。
− R1R2C=CH−(CF2)j−CH=CR3R4(式中、jは、2〜10、好ましくは4〜8の整数であり、互いに等しいかもしくは異なる、R1、R2、R3、R4は、−H、−FまたはC1〜C5アルキルもしくは(パー)フルオロアルキル基である);
− A2C=CB−O−E−O−CB=CA2[式中、互いに等しいかもしくは異なる、Aのそれぞれは独立して、−F、−Cl、および−Hから選択され;互いに等しいかもしくは異なる、Bのそれぞれは独立して、−F、−Cl、−Hおよび−ORB(ここで、RBは、部分的に、実質的にまたは完全にフッ素化または塩素化されていることができる分岐鎖もしくは直鎖アルキルラジカルである)から選択され;Eは、エーテル結合が挿入されていてもよい、場合によりフッ素化された、2〜10個の炭素原子を有する二価基であり;好ましくはEは、zが3〜5の整数である、−(CF2)z−基である];ならびに
− R6R7C=CR5−E−O−CB=CA2(式中、E、AおよびBは、上に定義されたものと同じ意味を有し;互いに等しいかもしくは異なる、R5、R6、R7は、−H、−FまたはC1〜C5アルキルもしくはフルオロアルキル基である)
のものから選択される。
− テトラフルオロエチレン(TFE)およびヘキサフルオロプロペン(HFP)などの、C3〜C8パーフルオロオレフィン;
− CF2=CFORf(パー)フルオロアルキルビニルエーテル(PAVE)(式中、Rfは、C1〜C6パーフルオロアルキル基、例えばCF3、C2F5、C3F7である);
− クロロトリフルオロエチレン(CTFE)などの、クロロ−および/またはブロモ−および/またはヨード−C2〜C6フルオロオレフィン;ならびに
− パーフルオロジオキソール
からなる群から選択される。
(A)フィルムを得るために上に詳述されたような組成物をキャストする工程、または含浸支持体を得るために前記組成物を多孔質支持体上へ含浸させる工程と;
(B)乾燥フィルムを得るために前記フィルムから、または乾燥含浸支持体を得るために前記含浸支持体から媒体(L)を除去する工程と;
(C)前記乾燥フィルムまたは前記乾燥含浸支持体を140℃〜230℃の温度で加熱する工程と
を含む方法に関する。
組成物(C1)
75重量%の水と、−SO3H官能基を含有し、EW=700g/eqを有する25重量%のポリマーとを含むフッ素化アイオノマー分散系−SOLVAY SPECIALTY POLYMERS ITALY S.p.A.によって得られる。
75重量%の水と、−SO3H官能基を含有し、EW=790g/eqを有する25重量%のポリマーとを含むフッ素化アイオノマー分散系−SOLVAY SPECIALTY POLYMERS ITALY S.p.A.によって得られる。
75重量%の水と、−SO3H官能基を含有し、EW=950g/eqを有する25重量%のポリマーとを含むフッ素化アイオノマー分散系−SOLVAY SPECIALTY POLYMERS ITALY S.p.A.によって得られる。
水性分散系の形態下での15重量%のテトラフルオロエチレン(TFE) パーフルオロメチル−ビニル−エーテル(MVE)コポリマーを含むパーフルオロエラストマー−SOLVAY SPECIALTY POLYMERS ITALY S.p.A.によって得られる。
3つの水性フッ素化アイオノマー分散系のそれぞれを、8重量%未満の前記成分(I)の含有量が達せられるまで水で希釈した。
上の実施例1によって開示されたように製造された分散系を次に使用してキャスト膜および強化膜を製造した。
上の実施例2に開示されたように製造された膜A、A(*)、DおよびD(*)を、それらの電気化学性能について試験した。
上の実施例2に開示されたように製造された膜BおよびB(*)を、沸騰水中での処理後に、吸水について試験した。
上の実施例2に開示されたように製造された膜CおよびC(*)を、DILLARD D.A.ら.On the use of pressure−loaded blister test to characterize the strenght and durability of proton exchange membranes.J. Fuel Cell Sci.Technol.2009,vol.6,no.3.によって記載されているものに類似の社内製造装置で試験した。
上の実施例2に開示されたように製造された膜A、A(*)、DおよびD(*)を、水素に対する透過性について試験した。
膜Eおよび(E*)を、適用されるいかなるエッジ保護(すなわち、サブガスケット)もなしに、HT400市販電極(Solvicore製の)と一体となった燃料電池装置(25cm2Fuel Cell Technologiesセル)での開回路電圧(OCV)保持試験で試験した。
膜A、A(*)、D、D(*)、F(*)およびG(*)についての分極曲線は、次の通りに得られた。
− セル温度 90℃
− 露点反応剤 65℃
− 圧力 1.5バール絶対
得られる分極曲線を図6aに示す。
− セル温度 65℃
− 露点反応剤 70℃
− 圧力 1.5バール絶対
得られる分極曲線を図6bに示す。
Claims (15)
- − 水を含む液体媒体[媒体(L)]と;
− 少なくとも1個の−SO3Z基(式中、Zは、H,アルカリ金属イオンまたはNH4 +である)を含有する少なくとも1種のエチレン性不飽和フッ素化モノマー[モノマー(A)]に由来する繰り返し単位と、少なくとも1種のエチレン性不飽和フッ素化モノマー[モノマー(B)]に由来する繰り返し単位とを含む少なくとも1種のポリマー[成分(I)]と;
− 少なくとも1種のパーフルオロエラストマー[成分(II)]と
を含み、成分(II)がC 3 〜C 8 パーフルオロオレフィンおよびCF 2 =CFOR f (パー)フルオロアルキルビニルエーテル(式中、R f は、C 1 〜C 6 パーフルオロアルキル基である)に由来する繰り返し単位を含む、組成物[組成物(C)]であって、
前記成分(I)と前記成分(II)との間の重量比が95/5〜70/30である組成物。 - 非過フッ素化モノマーに由来する繰り返し単位が、成分(II)の総重量に関して重量で2%よりも下である、請求項1に記載の組成物。
- 前記成分(I)と前記成分(II)との間の前記重量比が90/10〜80/20である、請求項1又は2に記載の組成物。
- 前記組成物(C)が、前記組成物の総重量を基準として1重量%〜40重量%の量で前記成分(I)を含む、請求項1〜3のいずれか一項に記載の組成物。
- 前記組成物(C)が、前記組成物の総重量を基準として0.05重量%〜18重量%の量で前記成分(II)を含む、請求項1〜4のいずれか一項に記載の組成物。
- 前記組成物(C)が、前記組成物の総重量を基準として5重量%〜45重量%の総量で前記成分(I)および前記成分(II)を含む、請求項1〜5のいずれか一項に記載の組成物。
- 前記モノマー(A)が、
CF2=CF(CF2)pSO3Z(式中、pは、0〜10の整数であり、Zは、H、アルカリ金属イオンまたはNH4 +である);
CF2=CF−O−(CF2)mSO3Z(式中、mは、1〜10の整数であり、Zは、H、アルカリ金属イオンまたはNH4 +である);
CF2=CF−(OCF2CF(RF1))w−O−CF2(CF(RF2))ySO3Z(式中、wは、0〜2の整数であり、互いに等しいかもしくは異なる、RF1およびRF2は独立して、F、Clまたは、1個もしくは複数個のエーテル酸素で場合により置換された、C1〜C10フルオロアルキル基であり、yは、0〜6の整数であり、Zは、H、アルカリ金属イオンまたはNH4 +である);ならびに
CF2=CF−Ar−SO3Z(式中、Arは、C5〜C15の芳香族またはヘテロ芳香族置換基であり、Zは、H、アルカリ金属イオンまたはNH4 +である)
からなる群から選択される、請求項1〜6のいずれか一項に記載の組成物。 - 前記モノマー(B)が、
− C2〜C8フルオロオレフィン;
− フッ化ビニリデン;
− C2〜C8のクロロ−および/またはブロモ−および/またはヨードフルオロオレフィン;
− 式CF2=CFORf1(式中、Rf1は、C1〜C6フルオロアルキルである)のフルオロアルキルビニルエーテル;
− CF2=CFORO1(式中、RO1は、1つもしくは複数のエーテル基を有するC1〜C12フルオロ−オキシアルキルである);
− CF2=CFOCF2ORf2(式中、Rf2は、C1〜C6フルオロアルキルまたは1つもしくは複数のエーテル基を有するC1〜C6フルオロオキシアルキルである)
− 式:
(式中、互いに等しいかもしくは異なる、Rf3、Rf4、Rf5、Rf6のそれぞれは独立して、フッ素原子;1個もしくは複数個の酸素原子を場合により含む、C1〜C6フルオロ(ハロ)フルオロアルキルである)
のフルオロジオキソール
からなる群から選択される、請求項1〜7のいずれか一項に記載の組成物。 - 成分(I)が、ビス−オレフィンに由来する繰り返し単位をさらに含む、請求項1〜8のいずれか一項に記載の組成物。
- 前記ビス−オレフィンが、
− R1R2C=CH−(CF2)j−CH=CR3R4(式中、jは、2〜10、好ましくは4〜8の整数であり、互いに等しいかもしくは異なる、R1、R2、R3、R4は、−H、−FまたはC1〜C5アルキルもしくは(パー)フルオロアルキル基である);
− A2C=CB−O−E−O−CB=CA2[式中、互いに等しいかもしくは異なる、Aのそれぞれは独立して、−F、−Cl、および−Hから選択され;互いに等しいかもしくは異なる、Bのそれぞれは独立して、−F、−Cl、−Hおよび−ORB(ここで、RBは、部分的に、実質的にまたは完全にフッ素化または塩素化され得る分岐鎖もしくは直鎖アルキルラジカルである)から選択され;Eは、エーテル結合が挿入されていてもよい、場合によりフッ素化された、2〜10個の炭素原子を有する二価基であり;好ましくはEは、zが3〜5の整数である、−(CF2)z−基である];
− R6R7C=CR5−E−O−CB=CA2(式中、E、AおよびBは、上に定義されたものと同じ意味を有し;互いに等しいかもしくは異なる、R5、R6、R7は、−H、−FまたはC1〜C5アルキルもしくはフルオロアルキル基である)
からなる群から選択される、請求項9に記載の組成物。 - 成分(II)が、テトラフルオロエチレン(TFE)およびパーフルオロメチル−ビニル−エーテル(MVE)に由来する繰り返し単位を含む、請求項1〜10のいずれか一項に記載の組成物。
- 請求項1〜11のいずれか一項に記載の組成物(C)の製造方法であって、
(i)第1液体媒体[媒体(I)]中に成分(I)を含む組成物[組成物(C1)]を提供する工程と;
(ii)組成物(dC1)の総重量に対して10重量%未満の量で前記成分(I)を含む、希釈された液体媒体[媒体(dI)]中の希釈された前記組成物[組成物(dC1)]を得るために、前記組成物(C1)を液体媒体[媒体(d)]で希釈する工程と;
(iii)95/5〜70/30の前記成分(I)と前記成分(II)との間の重量比からなる、第3液体媒体[媒体(III)]中の希釈された混合組成物(dC3)を提供するために、前記組成物(dC1)を、第2液体媒体[媒体(II)]中に成分(II)を含む組成物[組成物(C2)]と混合する工程と、
(iv)媒体(L)、成分(I)および成分(II)を含む組成物(C)であって、前記成分(I)および前記成分(II)が、前記組成物の総重量を基準として少なくとも15重量%の量で存在する組成物(C)を提供するために、前記媒体(III)を前記組成物(dC3)から部分的に除去する工程と
を含み、
前記媒体(I)、媒体(d)および媒体(II)は、それぞれ独立して、媒体(L)に関連して上に詳述された群から選択される、方法。 - 前記成分(I)と前記成分(II)との間の前記重量比が90/10〜80/20である、請求項12に記載の方法。
- 請求項1に記載の組成物(C)を含む物品であって、好ましくは前記物品がプロトン交換膜である物品。
- プロトン交換膜の製造方法であって、前記方法が、次の工程:
(A)フィルムを得るために請求項1に記載の組成物(C)をキャストする工程、または含浸支持体を得るために前記組成物(C)を多孔質支持体上へ含浸させる工程と;
(B)乾燥フィルムを得るために前記フィルムから、または乾燥含浸支持体を得るために前記含浸支持体から媒体(L)を除去する工程と;
(C)前記乾燥フィルムまたは前記乾燥含浸支持体を140℃〜230℃の温度で加熱してプロトン交換膜を得る工程と
を含む方法。
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