JP4569297B2 - 含フッ素エーテル鎖を含む含フッ素ポリマーからなる固体電解質 - Google Patents
含フッ素エーテル鎖を含む含フッ素ポリマーからなる固体電解質 Download PDFInfo
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- JP4569297B2 JP4569297B2 JP2004544916A JP2004544916A JP4569297B2 JP 4569297 B2 JP4569297 B2 JP 4569297B2 JP 2004544916 A JP2004544916 A JP 2004544916A JP 2004544916 A JP2004544916 A JP 2004544916A JP 4569297 B2 JP4569297 B2 JP 4569297B2
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- fluorine
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- 229910052731 fluorine Inorganic materials 0.000 title claims abstract description 213
- 239000011737 fluorine Substances 0.000 title claims abstract description 177
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title claims abstract description 175
- 229920000642 polymer Polymers 0.000 title claims abstract description 173
- 239000007784 solid electrolyte Substances 0.000 title claims abstract description 63
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- 238000000034 method Methods 0.000 claims abstract description 32
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
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- 239000003990 capacitor Substances 0.000 claims description 16
- 125000000962 organic group Chemical group 0.000 claims description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 claims description 7
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- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 claims description 2
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- 125000001153 fluoro group Chemical group F* 0.000 description 9
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- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 9
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- 238000002360 preparation method Methods 0.000 description 8
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- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical group F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 7
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- 150000007513 acids Chemical class 0.000 description 7
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- 239000005977 Ethylene Substances 0.000 description 6
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 6
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 6
- 229910052783 alkali metal Inorganic materials 0.000 description 6
- 239000000919 ceramic Substances 0.000 description 6
- 229910052744 lithium Inorganic materials 0.000 description 6
- 239000011159 matrix material Substances 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
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- 235000011007 phosphoric acid Nutrition 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical compound FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 6
- GKNWQHIXXANPTN-UHFFFAOYSA-N 1,1,2,2,2-pentafluoroethanesulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)F GKNWQHIXXANPTN-UHFFFAOYSA-N 0.000 description 5
- FRCHKSNAZZFGCA-UHFFFAOYSA-N 1,1-dichloro-1-fluoroethane Chemical compound CC(F)(Cl)Cl FRCHKSNAZZFGCA-UHFFFAOYSA-N 0.000 description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 5
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 5
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- 125000002947 alkylene group Chemical group 0.000 description 5
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- 125000003277 amino group Chemical group 0.000 description 5
- 230000001588 bifunctional effect Effects 0.000 description 5
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- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
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- 229910052757 nitrogen Inorganic materials 0.000 description 5
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 5
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- 238000003756 stirring Methods 0.000 description 5
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- ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 5
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- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 4
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- 150000002825 nitriles Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000002896 organic halogen compounds Chemical class 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 150000002921 oxetanes Chemical class 0.000 description 1
- AVNANMSIFNUHNY-MQQKCMAXSA-N oxiran-2-ylmethyl (2e,4e)-hexa-2,4-dienoate Chemical compound C\C=C\C=C\C(=O)OCC1CO1 AVNANMSIFNUHNY-MQQKCMAXSA-N 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Chemical compound [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- DYFXGORUJGZJCA-UHFFFAOYSA-N phenylmethanediamine Chemical compound NC(N)C1=CC=CC=C1 DYFXGORUJGZJCA-UHFFFAOYSA-N 0.000 description 1
- SNGARVZXPNQWEY-UHFFFAOYSA-N phenylmethanediol Chemical compound OC(O)C1=CC=CC=C1 SNGARVZXPNQWEY-UHFFFAOYSA-N 0.000 description 1
- PTMHPRAIXMAOOB-UHFFFAOYSA-N phosphoramidic acid Chemical compound NP(O)(O)=O PTMHPRAIXMAOOB-UHFFFAOYSA-N 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920000131 polyvinylidene Polymers 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- HKJYVRJHDIPMQB-UHFFFAOYSA-N propan-1-olate;titanium(4+) Chemical compound CCCO[Ti](OCCC)(OCCC)OCCC HKJYVRJHDIPMQB-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 238000005549 size reduction Methods 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- 125000005208 trialkylammonium group Chemical group 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- LFBULLRGNLZJAF-UHFFFAOYSA-N trimethoxy(oxiran-2-ylmethoxymethyl)silane Chemical compound CO[Si](OC)(OC)COCC1CO1 LFBULLRGNLZJAF-UHFFFAOYSA-N 0.000 description 1
- ZNXDCSVNCSSUNB-UHFFFAOYSA-N trimethoxy-[2-(oxiran-2-ylmethoxy)ethyl]silane Chemical compound CO[Si](OC)(OC)CCOCC1CO1 ZNXDCSVNCSSUNB-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
Classifications
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/15—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on an electrochromic effect
- G02F1/1506—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on an electrochromic effect caused by electrodeposition, e.g. electrolytic deposition of an inorganic material on or close to an electrode
- G02F1/1508—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on an electrochromic effect caused by electrodeposition, e.g. electrolytic deposition of an inorganic material on or close to an electrode using a solid electrolyte
-
- 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
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G11/00—Hybrid capacitors, i.e. capacitors having different positive and negative electrodes; Electric double-layer [EDL] capacitors; Processes for the manufacture thereof or of parts thereof
- H01G11/54—Electrolytes
- H01G11/56—Solid electrolytes, e.g. gels; Additives therein
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
- H01G9/004—Details
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- 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
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- 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
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- 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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- 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
- H01M8/1046—Mixtures of at least one polymer and at least one additive
- H01M8/1048—Ion-conducting additives, e.g. ion-conducting particles, heteropolyacids, metal phosphate or polybenzimidazole with phosphoric acid
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- H01M8/00—Fuel cells; Manufacture thereof
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- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
- H01G9/004—Details
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- H01G9/025—Solid electrolytes
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Description
(A)含フッ素エーテル由来の式(D):
−(d1)n1−(d2)n2−(d3)n3−(d4)n4−
(式中、
(d1)は−(OCF2CF2CF2)−、
(d2)は−(OCFX1CF2)−または−(OCF2CFX1)−
(d3)は−(OCFX2)−、
(d4)は−(OCH2CF2CF2)−または−(OCF2CF2CH2)−
;n1、n2、n3、n4は同じかまたは異なり0または1以上の整数で、かつn1+n2+n3+n4が5〜200の整数;X1、X2は同じかまたは異なりFまたはCF3)で示される構造単位を有する非晶性の含フッ素ポリマーであって、式(4):
−(K)−(L)− (4)
(式中、構造単位Kは、式(D1):
−(d1) n1 −(d2) n2 −(d3) n3 −(d4) n4 −
(式中、
(d1)は−(OCF 2 CF 2 CF 2 )−、
(d2)は−(OCFX 1 CF 2 )−または−(OCF 2 CFX 1 )−
(d3)は−(OCFX 2 )−、
(d4)は−(OCH 2 CF 2 CF 2 )−または−(OCF 2 CF 2 CH 2 )−
;n1、n2、n3、n4は同じかまたは異なり0または1以上の整数で、かつn1+n2+n3+n4が5〜100の整数;X 1 、X 2 は同じかまたは異なりFまたはCF 3 )で示される構造単位D1を側鎖に含む含フッ素エチレン性単量体由来の構造単位;構造単位Lは、構造単位Kを与える単量体と共重合可能な単量体に由来する構造単位)で示され、構造単位Kを0.01〜100モル%および構造単位Lを0〜99.99モル%含む非晶性の含フッ素ポリマー、および
(B)電解質化合物
を含み、交流複素インピーダンス法で測定したイオン伝導性が25℃で10-10〜101S/cmである含フッ素高分子固体電解質に関する。
(A)前記非晶性の含フッ素ポリマー、
(B)電解質化合物、および
(C)有機溶媒および/または水
を含み、交流複素インピーダンス法で測定したイオン伝導性が25℃で10-10〜101S/cmである含フッ素高分子固体電解質に関する。
(d1):−(OCF2CF2CF2)n1−、
(d2):−(OCFX1CF2)n2−または−(OCF2CFX1)n2−
(d3):−(OCFX2)n3−、
(d4):−(OCH2CF2CF2)n4−または−(OCF2CF2CH2)n4−
(X1、X2、n1、n2、n3およびn4は前記と同じ)
で示される含フッ素エーテル単位を少なくとも5連鎖、特に5〜200個、さらに好ましくは5〜100個連鎖で有する構造単位Dのうち、前記含フッ素エーテル単位を5〜100個連鎖で有する構造単位D1を含む点にある。連鎖が5未満のときは構造単位Dを導入することにより得られる優れたイオン伝導性や熱的・電気的安定性などが不充分となる。200を超えると本発明の固体電解質の作製時に作業性が悪化するほか、電解質化合物や溶媒との混合性が悪くなるため好ましくない。
(M1)−(M)−(M2) (1)
(式中、構造単位Mは、
(M3)−(M)−(M4) (2)
(式中、構造単位Mは、
(M5)−(M)−(M6) (3)
(式中、構造単位Mは、
−O−R−O−、
−HN−R−NH−
(Rは炭素数1〜50のエーテル結合を含んでもよい2価の炭化水素基)といった、2官能アルコール、2官能アミン由来の構造単位があげられる。
−(OCH2CH2)−、
−(OCH(CH3)CH2)−
というエーテル鎖の繰り返し単位をもつものは、イオン伝導性が高い点で望ましく、Rが単環、芳香環、複素環などかさ高い基を持つ場合は強度が向上する点で望ましい。
(Y1はCF3、CH3またはHCF2、R20は炭素数1〜49のエーテル結合を含んでもよい2価の炭化水素基、Y2は
−CH2−、
−CF2−、
−O−、
−CO−
で示される基のいずれかである。また、n7、n8は同じかまたは異なり、0または1)
R20のうち、好ましくは炭素数1〜20の含フッ素アルキル基である。
CH3−、
CF3−CF2−、
CF3−CF2−CF2−、
CF3−CH2−、
CF3−CF2−CH2−、
HCF2−CF2CF2−CH2−、
HCF2−(CF2CF2)2−CH2−、
CF3−CO−、
CF3−CF2−CO−、
HCF2−CF2CF2−CO−、
HCF2−(CF2CF2)2−CO−、
CF3−O−、
CH3−O−、
CF3−CF2−O−、
CF3−CF2−CF2−O−、
CF3−CH2−O−、
CF3−CF2−CH2−O−、
HCF2−CF2CF2−CH2−O−、
HCF2−(CF2CF2)2−CH2−O−、
CH3−CH2−、
CH3−CH2CH2−CH2−、
CH3−CO−、
CH3−CH2−CO−、
CH3−O−、
CH3−CH2CH2−O−、
CH3−(OCH2CH2)5−O−、
CH3−(OCH(CH3)CH2)5−O−
(R21は、炭素数1〜50のエーテル結合を含んでもよい1価の炭化水素基であり、かつ末端に非イオン性官能基を含むものか、または、−OH基、−NH2基、−NO2基、−SO3H基;Y4は、
−CH2−、
−CF2−、
−O−、
−CO−
で示される基のいずれかである。)
CH3OCO−CH2−、
CH3OCO−CF2CF2CF2−CH2−、
CH3OCO−(CF2CF2)2−CH2−、
CH3COO−CH2CH2(OCH2CH2)5−O−、
CH3COO−CH(CH3)CH2(OCH(CH3)CH2)5−O−、
CH3OCOO−CF2−、
CH3OCOO−CH2−、
CH3OCOO−CF2CF2−CH2−、
CH3OCOO−(CF2CF2)2−CH2−、
H2N−CF2CF2−CO−、
NC−CF2CF2−CO−、
NC−(CF2CF2)2−CO−、
H2NSO2−CF2CF2−O−、
H2NSO2−CF2CF2OCF2CF2−O−、
H2NCO−CH2CH2−O−、
H2NCO−CF2−CF2−CH2−O−
(R22は炭素数1〜50のエーテル結合を含んでもよい1価の炭化水素基であり、架橋可能な官能基を含むものか、または、−OH基、−NH2基、−NO2基、−SO3H基;Y5は、
−CH2−、
−CF2−、
−O−、
−CO−
で示される基のいずれかである)。
H2N−R3−NH2 、 HO−R3−OH
(R3は炭素数1〜30のエーテル結合を含んでもよい2価のアルキレン基、アルケニレン基、シクロアルキレン基、アリール基、アラルキレン基、テトラヒドロピラニレン基、またはそれらの誘導体であり、フッ素原子を含んでいてもよい)で示されるジアミン誘導体またはジオール誘導体。
−(K)−(L)− (4)
(式中、構造単位Kは、式(D1):
−(d1)n1−(d2)n2−(d3)n3−(d4)n4−
(式中、
(d1)は−(OCF2CF2CF2)−、
(d2)は−(OCFX1CF2)−または−(OCF2CFX1)−
(d3)は−(OCFX2)−、
(d4)は−(OCH2CF2CF2)−または−(OCF2CF2CH2)−
;n1、n2、n3、n4は同じかまたは異なり0または1以上の整数で、かつn1+n2+n3+n4が5〜100の整数;X1、X2は同じかまたは異なりFまたはCF3)で示される構造単位D1を側鎖に含む含フッ素エチレン性単量体由来の構造単位;構造単位Lは、構造単位Kを与える単量体と共重合可能な単量体に由来する構造単位)で示され、構造単位Kを0.01〜100モル%および構造単位Lを0〜99.99モル%含む非晶性含フッ素ポリマー。
−(K1)−(L1)− (5)
(式中、構造単位K1は式(K1):
−(K2)−(L2)− (6)
(式中、構造単位K2は式(K2):
−(K3)−(L3)− (7)
(式中、構造単位K3は式(K3):
CH2=CHCH2O−Rf、
CF2=CFO−Rf、
CF2=CFCF2O−Rf、
CH2=CFO−Rf、
CH2=CFCF2O−Rf、
CF2=CHO−Rf、
CF2=CHCF2O−Rf
CH2=CHO−Rf、
CH2=CFCF2O−Rf、
CF2=CHO−Rf
といった単量体は単独重合が可能であり、特に望ましい。
CH2=CHCOO−Rf、
CH2=C(CH3)COO−Rf、
CH2=CFCOO−Rf
が重合性が良好で、得られるポリマーの強度が高く、分極性のカルボニル基を含むため、電解質化合物のイオン解離性を高めるため特に望ましい。
(Y7は炭素数1〜30のエーテル結合を含んでもよい1価の炭化水素基、Y8は末端が、
−CH2−、
−CF2−、
−CO−
で示される、炭素数1〜30のエーテル結合を含んでもよい2価の炭化水素基。また、n9は0または1)。
CH2=CFCOO−CH2CF(CF3)−(OCF2CF(CF3))20−OCF2CF2CF3、
CH2=CFCOO−CH2CF2CF2−(OCH2CF2CF2 ) 5 −OCH2CF2CF3、
CH2=CFCOO−CH2CF2CF2−(OCH2CF2CF2 ) 20 −OCH2CF2CF3、
CH2=CFCOO−CH2CF2CF2−(OCF2CF2CF2 ) 5 −OCF2CF2CF3、
CH2=CFCOO−CH2CF2CF2−(OCF2CF2CF2 ) 20 −OCF2CF2CF3、
CH2=CFCOO−CH2CH2CH2CF2CF2−(OCH2CF2CF2 ) 5 −OCH2CF2COOH、
CH2=CFCOO−CH2CH2CH2−(OCH2CF2CF2 ) 20 −OCH2CF2COOH、
CH2=CFCOO−CH2CH2CH2CF2CF2−(OCH2CF2CF2 ) 5 −OCH2CF2COOCH3、
CH2=CFCOO−CH2CH2CH2−(OCH2CF2CF2 ) 20 −OCH2CF2COOCH3
CX10X11=CX12X13 (15)
(式中、X10、X11、X12、X13は同じかまたは異なり、H、F、Cl、CH3またはCF3)で示されるフッ素原子を含むかまたは含まないオレフィン類。
CZ1Z2=CZ3Z4
(式中、Z1、Z2、Z3、Z4は同じかまたは異なり水素原子、ハロゲン原子、CH3またはCF3)で表される単量体を用いて得られる数平均分子量10,000〜1,000,000のポリマーが好ましい。
テトラフルオロホウ酸、ヘキサフルオロ燐酸、過塩素酸、ヘキサフルオロ砒素酸、硝酸、硫酸、燐酸、フッ酸、塩酸、臭化水素酸、ヨウ化水素酸、チオシアン酸などの無機酸;トリフルオロメタンスルホン酸、ペンタフルオロエタンスルホン酸、ヘプタフルオロプロピルスルホン酸、ビス(トリフルオロメタンスルホニル)イミド酸、酢酸、トリフルオロ酢酸、プロピオン酸、ベンゼンスルホン酸、トルエンスルホン酸、n−ヘキサンスルホン酸、n−オクチルスルホン酸、セチルスルホン酸、p−クロロベンゼンスルホン酸、フェノールスルホン酸、4−ニトロトルエン−2−スルホン酸、2−スルホ安息香酸、ニトロベンゼンスルホン酸、スルホコハク酸、スルホセバシン酸などの有機酸があげられ、特に好ましくは硝酸、硫酸、塩酸、含フッ素アルキルスルホン酸などの強酸があげられる。
金属陽イオン、アンモニウムイオン、アミジニウムイオンおよびグアジニウムイオンよりなる群から選ばれる少なくとも1種の陽イオンと、塩素イオン、臭素イオン、ヨウ素イオン、過塩素酸イオン、チオシアン酸イオン、テトラフルオロホウ素イオン、硝酸イオン、炭酸イオン、硫酸イオン、次亜塩素酸イオン、AsF6 -、PF6 -、ステアリルスルホン酸イオン、オクチルスルホン酸イオン、ドデシルベンゼンスルホン酸イオン、ナフタレンスルホン酸イオン、ドデシルナフタレンスルホン酸イオン、R4SO3 -、(R4SO2)(R5SO2)N-、(R4SO2)(R5SO2)(R6SO2)C-および(R4SO2)(R5SO2)TC-[ただし、R4、R5、R6はハロゲンで置換されたアルキル基またはアリール基であり、Tは電子吸引性基を示す]よりなる群から選ばれる陰イオンとからなる化合物が好ましくあげられる。
また、水素イオン、金属陽イオン、アンモニウムイオン、アミジニウムイオンおよびグアジニウムイオンよりなる群から選ばれる陽イオンと高分子アニオンとからなるものも使用できる。
液状イオン性化合物は、流状でも、また、ポリマーと複合することによって固体状になったものでも利用でき、種々の公知のイオン性液体を利用することができる(Nature,362,137,(1993)、Journal of Chemical Society Chemical Communication、929、(1993))。具体的には、環状アミジンまたはピリジンのオニウム塩であることが望ましい。
1H−NMR測定条件:300MHz(テトラメチルシラン=0ppm)
19F−NMR測定条件:300MHz(トリクロロフルオロメタン=0ppm)
ドライアイスコンデンサをつけた1L四つ口フラスコにCsF(4.2g)、トリグライム(220ml)を入れ撹拌しながら−10〜10℃でヘキサフルオロプロピレンオキシド(HFPO)を189gを吹き込んだ。20時間後、メタノールを46.5g入れ、反応を停止した。反応後、HCFC−141b/水で分液、濃縮し粘液を得た。このものはGPC、1H−NMR、19F−NMRでの分析の結果、末端がメチルエステルであるHFPO開環重合体であることがわかった。数平均分子量は3900であった。
乾燥した耐圧密閉容器中にCsF(4.2g)、トリグライム(220ml)を入れ撹拌しながら−10〜10℃でヘキサフルオロプロピレンオキシド(HFPO)189gを吹き込んだ。20時間後、プロピレンオキシド66gを導入した。導入後、徐々に温度を上げ、40〜60℃で24時間攪拌を行なったのち、酢酸クロライド5gを導入し反応を終了した。反応後、HCFC−141b/水で分液し、濃縮後、136gのゴム状の固体を得た。このもののGPC、1H−NMR、19F−NMRでの分析の結果、末端が酢酸エステルであるHFPO/プロピレンオキシドの開環重合体であることがわかった。組成はモル比で46/54、数平均分子量は5500であった。
乾燥した耐圧密閉容器中にCsF(4.2g)、トリグライム(220ml)を入れ撹拌しながら−10〜10℃でヘキサフルオロプロピレンオキシド(HFPO)189gを吹き込んだ。20時間後、プロピレンオキシド66gを導入した。導入後、徐々に温度を上げ、40〜60℃で24時間攪拌を行なったのち、酢酸クロライド8gを導入し反応を終了した。反応後、HCFC−141b/水で分液し、濃縮後、131gのゴム状の固体を得た。このもののGPC、1H−NMR、19F−NMRでの分析の結果、末端が酢酸エステルであるHFPO/プロピレンオキシドの開環重合体であることがわかった。組成はモル比で46/54、数平均分子量は5600であった。
乾燥した耐圧密閉容器中にCsF(4.2g)、トリグライム(220ml)を入れ撹拌しながら−10〜10℃でヘキサフルオロプロピレンオキシド(HFPO)189gを吹き込んだ。20時間後、プロピレンオキシド66gおよびグリシジルアクリレート16gを導入した。導入後、徐々に温度を上げ、40〜60℃で24時間攪拌を行なったのち、酢酸クロライド5gを導入し反応を終了した。反応後、HCFC−141b/水で分液し、濃縮後、139gのゴム状の固体を得た。このもののGPC、1H−NMR、19F−NMRでの分析の結果、末端が酢酸エステルであるHFPO/プロピレンオキシド/グリシジルアクリレートの開環重合体であることがわかった。組成はモル比で47/46/7、数平均分子量は5300であった。
乾燥した耐圧密閉容器中にCsF(4.2g)、トリグライム(220ml)を入れ撹拌しながら−10〜10℃でヘキサフルオロプロピレンオキシド(HFPO)189gを吹き込んだ。20時間後、プロピレンオキシド66gおよびグリシジルエトキシシラン62gを導入した。導入後、徐々に温度を上げ、40〜60℃で24時間攪拌を行なったのち、酢酸クロライド5gを導入し反応を終了した。反応後、HCFC−141b/水で分液し、濃縮後、139gのゴム状の固体を得た。このもののGPC、1H−NMR、19F−NMRでの分析の結果、末端が酢酸エステルであるHFPO/プロピレンオキシド/グリシジルアクリレートの開環重合体であることがわかった。組成はモル比で45/46/9、数平均分子量は6200であった。
撹拌装置および温度計を備えた100mlのガラス製四ツ口フラスコに、含フッ素エーテルを側鎖に含有するαフルオロアクリレート:
CH2=CFCOOCH2CF2CF2(OCF2CF2CF2)7OCF2CF2CF3
5gを20mlのMIBK溶液に溶解し、AIBN0.02gを加え充分に窒素置換を行なったのち、窒素気流下70℃で8時間撹拌を行なった。得られた溶液をヘキサンを貧溶媒として再沈、固体を分離、真空乾燥させ、半透明なゴム状固体4.1gを得た。
撹拌装置および温度計を備えた100mlのガラス製四ツ口フラスコに、含フッ素エーテルを側鎖に含有するαフルオロアクリレート:
CH2=CFCOOCH2CF2CF2(OCF2CF2CF2)7OCF2CF2CF3
5g、メチルメタクリレート0.6g、グリシジルメタクリレート0.9gを20mlのMIBK溶液に溶解し、AIBN0.07gを加え充分に窒素置換を行なったのち、窒素気流下70℃で8時間撹拌を行なった。得られた溶液をヘキサンを貧溶媒として再沈、固体を分離、真空乾燥させ、無色透明なゴム状重合体4.5gを得た。
末端がメトキシシリル基であるオプツールDSX(ダイキン工業(株)の商品名)20gをパーフルオロヘキサン100mlに溶かし、トリフルオロ酢酸0.5gを入れ、キャスト後、室温で静置した。2日後、溶媒(パーフルオロヘキサン)に不溶ゴム状の固体からなるポリマー膜が得られた。IR分析の結果、メトキシ基がほとんど消失しており、架橋体であることが確認できた。
参考例4で得られたポリマー10gと2gのエチレンジオールジアクリレート、0.1gの光ラジカル発生剤(IRGACURE907、チバスペシャルテイ・ケミカルズ社製)をMIBK20mlに溶解させ、キャストフィルムを作った。溶媒蒸発後、UVランプにより紫外線を1500mJ照射した。照射後、得られた固体ポリマーは溶媒(アセトン、MIBK、DMF、NMPといった極性有機溶媒)に不溶となり、IR分析の結果、アクリル由来の炭素炭素二重結合が消失しており、架橋体であることが確認できた。
参考例2で得られたポリマー10gと2gのジエチレングリコール−2,3−エポキシプロピル−2,3−エポキシ−2−メチルプロピルエーテルおよび0.1gの光カチオン発生剤であるジフェニルヨードニウムトリフルオロメタンスルホネートをMIBK20mlに溶解させ、キャストフィルムを作った。溶媒蒸発後、UVランプで紫外線を1500mJ照射した。照射後、さらに80℃で1時間加熱した。得られた固体ポリマーは溶剤(参考例7と同じ)に不溶となり、架橋体であることが確認できた。
実施例2で得られたポリマー10gと光カチオン発生剤であるジフェニルヨードニウムトリフルオロメタンスルホネート0.5gをMIBK20mlに溶解させ、キャストフィルムを作った。溶媒蒸発後、UVランプで紫外線を1500mJ照射した。照射後、さらに80℃で1時間加熱した。得られた固体ポリマーは溶剤(参考例7と同じ)に不溶となり、架橋体であることが確認できた。
過塩素酸リチウムを1モル/リットルの濃度で溶解させたアセトン溶液90重量部に、参考例1で得られた含フッ素ポリマーを30重量部加え、のちにアセトンを蒸発させ、ゴム状の含フッ素高分子固体電解質を得た。
参考例9と同様の手法で、重量平均分子量20,000のPEOを用い高分子固体電解質を調製し、イオン伝導性を調べた結果、イオン伝導度は、8×10-8S/cmであった。
過塩素酸リチウムを1モル/リットルの濃度で溶解させたプロピレンカーボネート溶液30重量部に、参考例1で得られた含フッ素ポリマーを30重量部加えて、含フッ素高分子固体電解質を得た。
過塩素酸リチウムを1モル/リットルの濃度で溶解させたプロピレンカーボネート溶液30重量部に、重量平均分子量約30万のポリフッ化ビニリデン7重量部を約100℃の温度で充分溶解させた。得られた溶液の温度を50℃まで下げ、その中に参考例1で得られた含フッ素ポリマーを30重量部加えて含フッ素高分子固体電解質を得た。
3.5gのテトラエチルアンモニウムテトラフルオロボレート(Et4NBF4)を16gのプロピレンカーボネートに溶解させた。つぎに、参考例7で得られたフィルム2gをこの溶液に浸漬させ、80℃で1時間静置した。フィルムを取り出し、100℃で2時間真空乾燥し、固体高分子電解質フィルムを得た。
3.5gのテトラエチルアンモニウムテトラフルオロボレート(Et4NBF4)を16gのアセトンに溶解させた。ついで参考例7で得られたフィルム2gをこの溶液に浸漬させ、30℃で1時間静置した。フィルムを取り出し、アセトンを蒸発させ、固体高分子電解質フィルムを得た。このフィルム状試料の両サイドをニッケルのブロッキング電極ではさみ、交流複素インピーダンス法で、25℃におけるイオン伝導度を測定した。イオン伝導度は4×10-7S/cmであった。
参考例8で得られた含フッ素ポリエーテル架橋体のフィルム1gを5gのペンタフルオロエタンカルボン酸に25℃で1時間浸漬した。100℃で1時間乾燥させたのち、固体状フィルムを取り出し、固体高分子電解質フィルムを得た。
参考例6で得られた含フッ素ポリエーテルフィルム1gを、1gのヘプタフルオロプロピルスルホン酸を溶解したアセトン20g中に浸漬した。アセトンを蒸発させ、ゴム状固体高分子電解質を得た。これを白金電極ではさみ、プロトン伝導度を交流複素インピーダンス法を用いて測定したところ、25℃で3×10-1S/cmであった。
Claims (16)
- (A)式(4):
−(K)−(L)− (4)
(式中、構造単位Kは、式(D1):
−(d1) n1 −(d2) n2 −(d3) n3 −(d4) n4 −
(式中、
(d1)は−(OCF 2 CF 2 CF 2 )−、
(d2)は−(OCFX 1 CF 2 )−または−(OCF 2 CFX 1 )−
(d3)は−(OCFX 2 )−、
(d4)は−(OCH 2 CF 2 CF 2 )−または−(OCF 2 CF 2 CH 2 )−
;n1、n2、n3、n4は同じかまたは異なり0または1以上の整数で、かつn1+n2+n3+n4が5〜100の整数;X 1 、X 2 は同じかまたは異なりFまたはCF 3 )で示される構造単位D1を側鎖に含む含フッ素エチレン性単量体由来の構造単位;構造単位Lは、構造単位Kを与える単量体と共重合可能な単量体に由来する構造単位)で示され、構造単位Kを0.01〜100モル%および構造単位Lを0〜99.99モル%含む非晶性の含フッ素ポリマー、および
(B)電解質化合物
を含み、交流複素インピーダンス法で測定したイオン伝導性が25℃で10-10〜101S/cmである含フッ素高分子固体電解質。 - (A)式(4):
−(K)−(L)− (4)
(式中、構造単位Kは、式(D1):
−(d1) n1 −(d2) n2 −(d3) n3 −(d4) n4 −
(式中、
(d1)は−(OCF 2 CF 2 CF 2 )−、
(d2)は−(OCFX 1 CF 2 )−または−(OCF 2 CFX 1 )−
(d3)は−(OCFX 2 )−、
(d4)は−(OCH 2 CF 2 CF 2 )−または−(OCF 2 CF 2 CH 2 )−
;n1、n2、n3、n4は同じかまたは異なり0または1以上の整数で、かつn1+n2+n3+n4が5〜100の整数;X 1 、X 2 は同じかまたは異なりFまたはCF 3 )で示される構造単位D1を側鎖に含む含フッ素エチレン性単量体由来の構造単位;構造単位Lは、構造単位Kを与える単量体と共重合可能な単量体に由来する構造単位)で示され、構造単位Kを0.01〜100モル%および構造単位Lを0〜99.99モル%含む非晶性の含フッ素ポリマー、
(B)電解質化合物、および
(C)有機溶媒および/または水
を含み、交流複素インピーダンス法で測定したイオン伝導性が25℃で10-10〜101S/cmである含フッ素高分子固体電解質。 - 非晶性含フッ素ポリマー(A)が、式(5):
−(K1)−(L1)− (5)
(式中、構造単位K1は式(K1):
- 非晶性含フッ素ポリマー(A)が、式(7):
−(K3)−(L3)− (7)
(式中、構造単位K3は式(K3):
- 非晶性含フッ素ポリマー(A)が、式(5):
−(K1)−(L1)− (5)
(式中、構造単位K1は式(K1):
- 非晶性含フッ素ポリマー(A)が、式(7):
−(K3)−(L3)− (7)
(式中、構造単位K3は式(K3):
- 成分(C)の有機溶媒が非プロトン性有機溶媒であり、かつカーボネート類、エーテル類またはエステル類である請求項2または6〜8のいずれかに記載の含フッ素高分子固体電解質。
- 非プロトン性有機溶媒が、プロピレンカーボネート、エチレンカーボネート、ジメチルカーボネート、ジエチルカーボネート、メチルエチルカーボネート、ブチレンカーボネート、γ−ブチロラクトン、3−メチル−2オキサゾリン、テトラヒドロフランおよびトリエチレングリコールジメチルエーテルよりなる群から選ばれる少なくとも1種である請求項9記載の含フッ素高分子固体電解質。
- 成分(C)が、水またはアルコール類である請求項2または6〜8のいずれかに記載の含フッ素高分子固体電解質。
- 請求項1〜11のいずれかに記載の含フッ素高分子固体電解質を用いてなる電気化学デバイス。
- 請求項1〜11のいずれかに記載の含フッ素高分子固体電解質を用いてなる電池。
- 請求項1〜11のいずれかに記載の含フッ素高分子固体電解質を用いてなるキャパシタ。
- 請求項1〜11のいずれかに記載の含フッ素高分子固体電解質を用いてなる固体表示素子。
- 請求項1〜11のいずれかに記載の含フッ素高分子固体電解質を用いてなるセンサー。
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PCT/JP2003/012631 WO2004036599A1 (ja) | 2002-10-03 | 2003-10-02 | 含フッ素エーテル鎖を含む含フッ素ポリマーからなる固体電解質 |
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US (1) | US7682753B2 (ja) |
EP (1) | EP1551036A1 (ja) |
JP (1) | JP4569297B2 (ja) |
CN (1) | CN100367415C (ja) |
AU (1) | AU2003268729A1 (ja) |
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EP1551036A1 (en) | 2005-07-06 |
US20050170255A1 (en) | 2005-08-04 |
CN1703761A (zh) | 2005-11-30 |
CN100367415C (zh) | 2008-02-06 |
JPWO2004036599A1 (ja) | 2006-02-16 |
US7682753B2 (en) | 2010-03-23 |
AU2003268729A1 (en) | 2004-05-04 |
CA2500172A1 (en) | 2004-04-29 |
WO2004036599A1 (ja) | 2004-04-29 |
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