CA2446389A1 - Ion-exchange materials with improved ion conductivity - Google Patents
Ion-exchange materials with improved ion conductivity Download PDFInfo
- Publication number
- CA2446389A1 CA2446389A1 CA002446389A CA2446389A CA2446389A1 CA 2446389 A1 CA2446389 A1 CA 2446389A1 CA 002446389 A CA002446389 A CA 002446389A CA 2446389 A CA2446389 A CA 2446389A CA 2446389 A1 CA2446389 A1 CA 2446389A1
- Authority
- CA
- Canada
- Prior art keywords
- styrenic
- fluorinated
- macromonomers
- repeat units
- proton
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
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- 239000003795 chemical substances by application Substances 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 7
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- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 4
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- 239000001569 carbon dioxide Substances 0.000 claims 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
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- 238000010526 radical polymerization reaction Methods 0.000 description 9
- 229910052731 fluorine Inorganic materials 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- MNCGMVDMOKPCSQ-UHFFFAOYSA-M sodium;2-phenylethenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C=CC1=CC=CC=C1 MNCGMVDMOKPCSQ-UHFFFAOYSA-M 0.000 description 8
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- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
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- 125000000217 alkyl group Chemical group 0.000 description 5
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- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 239000002243 precursor Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical compound OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
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- 238000012360 testing method Methods 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
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- 229910001260 Pt alloy Inorganic materials 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
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- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- DBZUJSZLTDZRCK-UHFFFAOYSA-N (3,5-dichlorobenzoyl) 3,5-dichlorobenzenecarboperoxoate Chemical compound ClC1=CC(Cl)=CC(C(=O)OOC(=O)C=2C=C(Cl)C=C(Cl)C=2)=C1 DBZUJSZLTDZRCK-UHFFFAOYSA-N 0.000 description 1
- SUTQSIHGGHVXFK-UHFFFAOYSA-N 1,2,2-trifluoroethenylbenzene Chemical class FC(F)=C(F)C1=CC=CC=C1 SUTQSIHGGHVXFK-UHFFFAOYSA-N 0.000 description 1
- LGJCFVYMIJLQJO-UHFFFAOYSA-N 1-dodecylperoxydodecane Chemical compound CCCCCCCCCCCCOOCCCCCCCCCCCC LGJCFVYMIJLQJO-UHFFFAOYSA-N 0.000 description 1
- BUCXEFZXWKUCCY-UHFFFAOYSA-N 4-methyl-3-(2-phenylethyl)-1,2,4-oxadiazol-5-one Chemical compound O1C(=O)N(C)C(CCC=2C=CC=CC=2)=N1 BUCXEFZXWKUCCY-UHFFFAOYSA-N 0.000 description 1
- 101100459438 Caenorhabditis elegans nac-1 gene Proteins 0.000 description 1
- GWHJZXXIDMPWGX-UHFFFAOYSA-N Cc1cc(C)c(C)cc1 Chemical compound Cc1cc(C)c(C)cc1 GWHJZXXIDMPWGX-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229920000544 Gore-Tex Polymers 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 239000012901 Milli-Q water Substances 0.000 description 1
- 229910004879 Na2S2O5 Inorganic materials 0.000 description 1
- 239000002033 PVDF binder Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical group [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- QYTDEUPAUMOIOP-UHFFFAOYSA-N TEMPO Chemical group CC1(C)CCCC(C)(C)N1[O] QYTDEUPAUMOIOP-UHFFFAOYSA-N 0.000 description 1
- OHBTULDTCSOWOY-UHFFFAOYSA-N [C].C=C Chemical group [C].C=C OHBTULDTCSOWOY-UHFFFAOYSA-N 0.000 description 1
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- 238000013019 agitation Methods 0.000 description 1
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- 238000000149 argon plasma sintering Methods 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
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- 239000013043 chemical agent Substances 0.000 description 1
- 239000000460 chlorine Chemical group 0.000 description 1
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- 125000002541 furyl group Chemical group 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
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- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
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- 230000000977 initiatory effect Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
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- 125000003010 ionic group Chemical group 0.000 description 1
- 229920000554 ionomer Polymers 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000004807 localization Effects 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- QLOAVXSYZAJECW-UHFFFAOYSA-N methane;molecular fluorine Chemical compound C.FF QLOAVXSYZAJECW-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000002103 osmometry Methods 0.000 description 1
- 150000002976 peresters Chemical class 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 238000005502 peroxidation Methods 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 238000002229 photoelectron microspectroscopy Methods 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
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- 239000011148 porous material Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000005588 protonation Effects 0.000 description 1
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- 239000012048 reactive intermediate Substances 0.000 description 1
- 238000012552 review Methods 0.000 description 1
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- 238000001998 small-angle neutron scattering Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Inorganic materials [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical compound FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 description 1
- 239000003930 superacid Substances 0.000 description 1
- 239000004032 superbase Substances 0.000 description 1
- 150000007525 superbases Chemical class 0.000 description 1
- 239000002352 surface water Substances 0.000 description 1
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- 239000005061 synthetic rubber Substances 0.000 description 1
- 238000004627 transmission electron microscopy Methods 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
- H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
- H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
- H01B1/122—Ionic conductors
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J39/00—Cation exchange; Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
- B01J39/08—Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
- B01J39/16—Organic material
- B01J39/17—Organic material containing also inorganic materials, e.g. inert material coated with an ion-exchange resin
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J39/00—Cation exchange; Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
- B01J39/08—Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
- B01J39/16—Organic material
- B01J39/18—Macromolecular compounds
- B01J39/20—Macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J47/00—Ion-exchange processes in general; Apparatus therefor
- B01J47/12—Ion-exchange processes in general; Apparatus therefor characterised by the use of ion-exchange material in the form of ribbons, filaments, fibres or sheets, e.g. membranes
-
- 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
- C08J5/2237—Synthetic macromolecular compounds based on macromolecular compounds obtained by reactions involving unsaturated carbon-to-carbon bonds 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
- C08J5/2218—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
-
- 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
- H01M8/02—Details
- H01M8/0289—Means for holding the electrolyte
-
- 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
- H01M8/1023—Polymeric electrolyte materials characterised by the chemical structure of the main chain of the ion-conducting polymer having only carbon, e.g. polyarylenes, polystyrenes or polybutadiene-styrenes
-
- 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
-
- 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. in situ polymerisation or in situ crosslinking
-
- 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
- C08J2325/00—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 an aromatic carbocyclic ring; Derivatives of such polymers
- C08J2325/02—Homopolymers or copolymers of hydrocarbons
- C08J2325/04—Homopolymers or copolymers of styrene
- C08J2325/08—Copolymers of styrene
-
- 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
-
- 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
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Sustainable Development (AREA)
- Sustainable Energy (AREA)
- Electrochemistry (AREA)
- Inorganic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Fuel Cell (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Conductive Materials (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Treatments Of Macromolecular Shaped Articles (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US29120501P | 2001-05-15 | 2001-05-15 | |
| US60/291,205 | 2001-05-15 | ||
| PCT/CA2002/000703 WO2002093676A2 (en) | 2001-05-15 | 2002-05-13 | Ion-exchange materials with improved ion conductivity |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2446389A1 true CA2446389A1 (en) | 2002-11-21 |
Family
ID=23119329
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002446389A Abandoned CA2446389A1 (en) | 2001-05-15 | 2002-05-13 | Ion-exchange materials with improved ion conductivity |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US6765027B2 (enExample) |
| EP (1) | EP1393398A2 (enExample) |
| JP (1) | JP2004529472A (enExample) |
| AU (1) | AU2002257443A1 (enExample) |
| CA (1) | CA2446389A1 (enExample) |
| WO (1) | WO2002093676A2 (enExample) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2003210939A1 (en) * | 2002-02-06 | 2003-09-02 | Battelle Memorial Institute | Polymer electrolyte membrane fuel cell system |
| US7572535B2 (en) * | 2002-05-13 | 2009-08-11 | Polyfuel, Inc. | Ion conductive copolymers containing one or more hydrophobic oligomers |
| CA2485971A1 (en) * | 2002-05-13 | 2004-05-21 | Polyfuel, Inc. | Ion conductive block copolymers |
| US20040197613A1 (en) * | 2003-04-04 | 2004-10-07 | Patrick Curlier | Microfuel cells for use particularly in portable electronic devices and telecommunications devices |
| WO2005049696A1 (en) | 2003-11-13 | 2005-06-02 | Polyfuel Inc. | Ion conductive copolymers containing one or more hydrophobic oligomers |
| WO2005090439A2 (en) * | 2004-03-12 | 2005-09-29 | Polyfuel, Inc. | Ion-conductive copolymers containing one or more ion-conducting oligomers |
| JP2005334263A (ja) * | 2004-05-26 | 2005-12-08 | Tokuyama Corp | イオントフォレーシス装置及びイオン交換膜 |
| US7799485B2 (en) * | 2004-07-09 | 2010-09-21 | Nissan Motor Co., Ltd. | Fuel cell system and composition for electrode |
| WO2006006502A1 (ja) * | 2004-07-09 | 2006-01-19 | Nissan Motor Co., Ltd. | 燃料電池システム及び固体高分子電解質膜 |
| KR100598159B1 (ko) * | 2004-08-05 | 2006-07-07 | 한양대학교 산학협력단 | 폴리스티렌 술폰산이 그라프트된 폴리술폰 공중합물및 그제조방법, 이를 이용한 연료전지용 고분자 전해질막 |
| WO2006013995A1 (en) * | 2004-08-05 | 2006-02-09 | Toyota Jidosha Kabushiki Kaisha | Highly hydrophilic support, catalyst-supporting support, electrode for fuel cell, method for producing the same, and polymer electrolyte fuel cell including the same |
| KR20080018181A (ko) * | 2005-05-24 | 2008-02-27 | 폴리퓨얼, 인코포레이티드 | 이온-전도성 올리고머를 함유하는 이온 전도성 코폴리머 |
| JP2008542505A (ja) * | 2005-06-01 | 2008-11-27 | ポリフューエル・インコーポレイテッド | イオン伝導性架橋コポリマー |
| CA2607966A1 (en) * | 2005-06-01 | 2006-12-07 | Polyfuel Inc. | Ion-conducting polymers containing pendant ion conducting groups |
| WO2007068453A2 (en) * | 2005-12-14 | 2007-06-21 | Novartis Ag | Method for preparing silicone hydrogels |
| JP5205694B2 (ja) * | 2005-12-15 | 2013-06-05 | 日産自動車株式会社 | 燃料、燃料電池システム及び燃料電池車輌 |
| US20070170401A1 (en) * | 2005-12-28 | 2007-07-26 | Che-Hsiung Hsu | Cationic compositions of electrically conducting polymers doped with fully-fluorinated acid polymers |
| US8232225B2 (en) | 2006-01-13 | 2012-07-31 | American Peat Technology, Llc | Production of multifunctional granular medium by partial activation of partially decomposed organic matter |
| JP4923598B2 (ja) * | 2006-02-02 | 2012-04-25 | トヨタ自動車株式会社 | 高親水化担体、触媒担持担体、燃料電池用電極、その製造方法、及びこれを備えた固体高分子型燃料電池 |
| GB0611600D0 (en) * | 2006-06-13 | 2006-07-19 | Itm Fuel Cells Ltd | Improvements to membranes |
| WO2008073901A2 (en) * | 2006-12-08 | 2008-06-19 | Uti Limited Partnership | Metal-organic solids for use in proton exchange membranes |
| US20100279198A1 (en) * | 2007-02-16 | 2010-11-04 | Polyfuel, Inc. | Composite polymer electrolyte membranes |
| TWI327195B (en) * | 2007-04-30 | 2010-07-11 | Asustek Comp Inc | Rotating mechanism and electronic device using the same |
| US20140142252A1 (en) * | 2012-11-19 | 2014-05-22 | Sangho Cho | Self-assembled structures, method of manufacture thereof and articles comprising the same |
| US10078261B2 (en) | 2013-09-06 | 2018-09-18 | Rohm And Haas Electronic Materials Llc | Self-assembled structures, method of manufacture thereof and articles comprising the same |
| JP6781434B2 (ja) * | 2015-07-13 | 2020-11-04 | ダイキン工業株式会社 | 含フッ素重合体 |
| CN105111348B (zh) * | 2015-09-06 | 2017-07-18 | 上海应用技术学院 | 一种强酸性阳离子交换树脂粉末及其制备方法 |
| JP6536477B2 (ja) * | 2016-05-13 | 2019-07-03 | トヨタ自動車株式会社 | 燃料電池 |
| RU2738721C1 (ru) * | 2020-02-03 | 2020-12-15 | Федеральное государственное бюджетное учреждение науки Ордена Трудового Красного Знамени Институт химии силикатов им. И.В. Гребенщикова Российской академии наук (ИХС РАН) | Способ получения гибридной электролитической мембраны на основе сшитого поливинилового спирта |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US4012303A (en) * | 1974-12-23 | 1977-03-15 | Hooker Chemicals & Plastics Corporation | Trifluorostyrene sulfonic acid membranes |
| NO843527L (no) * | 1983-09-06 | 1985-03-07 | Chlorine Eng Corp Ltd | Fremgangsmaate for fremstilling av en membran av podepolymer |
| US5328956A (en) | 1990-11-13 | 1994-07-12 | Kao Corporation | Propylene (co)polymer and process for the preparation of the same |
| US5322912A (en) | 1992-11-16 | 1994-06-21 | Xerox Corporation | Polymerization processes and toner compositions therefrom |
| US5449724A (en) | 1994-12-14 | 1995-09-12 | Xerox Corporation | Stable free radical polymerization process and thermoplastic materials produced therefrom |
| US5530079A (en) * | 1995-01-03 | 1996-06-25 | Xerox Corporation | Polymerization processes |
| TW513446B (en) | 1997-02-21 | 2002-12-11 | Idemitsu Petrochemical Co | Graft copolymer and styrene-based resin composition |
| US6156858A (en) * | 1997-06-25 | 2000-12-05 | Xerox Corporation | Stable free radical polymerization processes |
| US6121397A (en) * | 1997-07-14 | 2000-09-19 | Xerox Corporation | Polymerization processes using oligomeric compound, monomer and surfactant |
| US6248469B1 (en) * | 1997-08-29 | 2001-06-19 | Foster-Miller, Inc. | Composite solid polymer electrolyte membranes |
-
2002
- 2002-05-13 JP JP2002590443A patent/JP2004529472A/ja not_active Ceased
- 2002-05-13 EP EP02727111A patent/EP1393398A2/en not_active Withdrawn
- 2002-05-13 AU AU2002257443A patent/AU2002257443A1/en not_active Abandoned
- 2002-05-13 WO PCT/CA2002/000703 patent/WO2002093676A2/en not_active Ceased
- 2002-05-13 US US10/144,663 patent/US6765027B2/en not_active Expired - Fee Related
- 2002-05-13 CA CA002446389A patent/CA2446389A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| AU2002257443A1 (en) | 2002-11-25 |
| WO2002093676A2 (en) | 2002-11-21 |
| US20030078308A1 (en) | 2003-04-24 |
| EP1393398A2 (en) | 2004-03-03 |
| WO2002093676A3 (en) | 2003-06-19 |
| US6765027B2 (en) | 2004-07-20 |
| JP2004529472A (ja) | 2004-09-24 |
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| Date | Code | Title | Description |
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| EEER | Examination request | ||
| FZDE | Discontinued |