WO2011087029A1 - 高分子電解質ゲル組成物 - Google Patents
高分子電解質ゲル組成物 Download PDFInfo
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- WO2011087029A1 WO2011087029A1 PCT/JP2011/050383 JP2011050383W WO2011087029A1 WO 2011087029 A1 WO2011087029 A1 WO 2011087029A1 JP 2011050383 W JP2011050383 W JP 2011050383W WO 2011087029 A1 WO2011087029 A1 WO 2011087029A1
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- WIPO (PCT)
- Prior art keywords
- polymer
- group
- functional group
- cationic functional
- vinyl
- Prior art date
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- 239000005518 polymer electrolyte Substances 0.000 title claims abstract description 94
- 239000000203 mixture Substances 0.000 title claims abstract description 74
- 125000002091 cationic group Chemical group 0.000 claims abstract description 119
- 125000000524 functional group Chemical group 0.000 claims abstract description 118
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 108
- 229920006324 polyoxymethylene Polymers 0.000 claims abstract description 90
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 81
- 239000008151 electrolyte solution Substances 0.000 claims abstract description 52
- -1 aliphatic aldehyde Chemical class 0.000 claims description 101
- 150000001875 compounds Chemical class 0.000 claims description 83
- 238000006359 acetalization reaction Methods 0.000 claims description 42
- 150000001299 aldehydes Chemical class 0.000 claims description 35
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 33
- 238000004519 manufacturing process Methods 0.000 claims description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims description 27
- 239000000178 monomer Substances 0.000 claims description 26
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 17
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium group Chemical group [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 claims description 16
- 125000005496 phosphonium group Chemical group 0.000 claims description 15
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 15
- 229920001567 vinyl ester resin Polymers 0.000 claims description 15
- 150000003934 aromatic aldehydes Chemical class 0.000 claims description 12
- 229920001577 copolymer Polymers 0.000 claims description 9
- 238000002156 mixing Methods 0.000 claims description 5
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 2
- 229920000867 polyelectrolyte Polymers 0.000 claims description 2
- 239000003792 electrolyte Substances 0.000 abstract description 24
- 238000004132 cross linking Methods 0.000 abstract description 17
- 230000014759 maintenance of location Effects 0.000 abstract description 17
- 239000000499 gel Substances 0.000 description 84
- 229920000642 polymer Polymers 0.000 description 75
- 238000000034 method Methods 0.000 description 63
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 35
- 150000002500 ions Chemical class 0.000 description 33
- 239000000047 product Substances 0.000 description 31
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
- 150000001241 acetals Chemical class 0.000 description 29
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 23
- 150000001450 anions Chemical class 0.000 description 23
- 229910001416 lithium ion Inorganic materials 0.000 description 23
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 22
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 19
- 239000004593 Epoxy Substances 0.000 description 18
- 239000002253 acid Substances 0.000 description 17
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- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 16
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 14
- 150000004693 imidazolium salts Chemical group 0.000 description 14
- 239000007773 negative electrode material Substances 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
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- 239000000243 solution Substances 0.000 description 11
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- 125000004036 acetal group Chemical group 0.000 description 10
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- 239000003377 acid catalyst Substances 0.000 description 9
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- 150000001768 cations Chemical class 0.000 description 7
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
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- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
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- 229940006460 bromide ion Drugs 0.000 description 4
- 239000003990 capacitor Substances 0.000 description 4
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 4
- 239000011888 foil Substances 0.000 description 4
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 4
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- GHVWODLSARFZKM-UHFFFAOYSA-N trimethyl-[3-methyl-3-(prop-2-enoylamino)butyl]azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CCC(C)(C)NC(=O)C=C GHVWODLSARFZKM-UHFFFAOYSA-N 0.000 description 1
- VLVCPYCLJRZNFA-UHFFFAOYSA-O trimethyl-[4-methyl-4-(prop-2-enoylamino)pentan-2-yl]azanium Chemical compound C[N+](C)(C)C(C)CC(C)(C)NC(=O)C=C VLVCPYCLJRZNFA-UHFFFAOYSA-O 0.000 description 1
- YWWDBCBWQNCYNR-UHFFFAOYSA-O trimethylphosphanium Chemical compound C[PH+](C)C YWWDBCBWQNCYNR-UHFFFAOYSA-O 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F216/00—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 alcohol, ether, aldehydo, ketonic, acetal or ketal radical
- C08F216/02—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 alcohol, ether, aldehydo, ketonic, acetal or ketal radical by an alcohol radical
- C08F216/04—Acyclic compounds
- C08F216/06—Polyvinyl alcohol ; Vinyl alcohol
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F216/00—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 alcohol, ether, aldehydo, ketonic, acetal or ketal radical
- C08F216/38—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 alcohol, ether, aldehydo, ketonic, acetal or ketal radical by an acetal or ketal radical
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/12—Hydrolysis
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/48—Isomerisation; Cyclisation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L29/00—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 an alcohol, ether, aldehydo, ketonic, acetal or ketal radical; Compositions of hydrolysed polymers of esters of unsaturated alcohols with saturated carboxylic acids; Compositions of derivatives of such polymers
- C08L29/14—Homopolymers or copolymers of acetals or ketals obtained by polymerisation of unsaturated acetals or ketals or by after-treatment of polymers of unsaturated alcohols
-
- 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
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M10/00—Secondary cells; Manufacture thereof
- H01M10/05—Accumulators with non-aqueous electrolyte
- H01M10/052—Li-accumulators
- H01M10/0525—Rocking-chair batteries, i.e. batteries with lithium insertion or intercalation in both electrodes; Lithium-ion batteries
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M10/00—Secondary cells; Manufacture thereof
- H01M10/05—Accumulators with non-aqueous electrolyte
- H01M10/056—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes
- H01M10/0564—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes the electrolyte being constituted of organic materials only
- H01M10/0565—Polymeric materials, e.g. gel-type or solid-type
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F218/00—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 acyloxy radical of a saturated carboxylic acid, of carbonic acid or of a haloformic acid
- C08F218/02—Esters of monocarboxylic acids
- C08F218/04—Vinyl esters
- C08F218/08—Vinyl acetate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2800/00—Copolymer characterised by the proportions of the comonomers expressed
- C08F2800/10—Copolymer characterised by the proportions of the comonomers expressed as molar percentages
-
- 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
- H01M2300/0085—Immobilising or gelification of electrolyte
-
- 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
- Y02E60/10—Energy storage using batteries
-
- 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
- Y02E60/13—Energy storage using capacitors
-
- 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
Definitions
- the present invention relates to a polymer electrolyte gel composition, a method for producing the same, and a vinyl acetal polymer used in the polymer electrolyte gel composition.
- a lithium ion secondary battery generally includes a separator interposed between a positive electrode, a negative electrode, and a positive and negative electrode, and the separator is impregnated with an electrolyte solution.
- Lithium ion secondary batteries that use electrolytes have high ionic conductivity, that is, battery performance, because the electrolyte is in a liquid state.
- a strong casing for preventing the battery is indispensable, the shape of the battery is limited, and it is difficult to reduce the thickness and weight.
- a lithium ion secondary battery using an all-solid polymer electrolyte in which an electrolyte salt is dissolved in a polymer compound (hereinafter referred to as “all-solid polymer electrolyte”) is known.
- a lithium ion secondary battery using an all solid polymer electrolyte does not require a special structure for preventing leakage.
- the all solid-type polymer electrolyte can be bonded to the electrode, the separator and the like, the strength and shape retention of the battery can be improved. Therefore, it is very effective in reducing the thickness of the battery and increasing the degree of freedom of battery shape. It is also effective for obtaining a large-area battery.
- the ionic conductivity of the all solid polymer electrolyte has a problem that it is considerably smaller than the ionic conductivity of the electrolytic solution.
- a lithium ion secondary battery using a gel polymer electrolyte (hereinafter referred to as “polymer electrolyte gel”) in which an electrolytic solution is held in a polymer compound is known.
- the lithium ion secondary battery using the polymer electrolyte gel is more active than the lithium ion secondary battery using the all solid polymer electrolyte because the polymer holds the electrolyte in the polymer electrolyte gel. It has excellent contact and ionic conductivity, and has the characteristics that leakage is less likely to occur compared to a lithium ion secondary battery in which a separator is impregnated with an electrolyte without using a polymer electrolyte gel. It attracts attention because it is.
- the larger the proportion of the electrolytic solution in the polymer electrolyte gel that is, the higher the electrolytic solution retention, the better the ionic conductivity.
- polymer compound used in the polymer electrolyte gel examples include ether polymers, methyl methacrylate polymers, acrylonitrile polymers, polyvinylidene fluoride or vinylidene fluoride and hexafluoropropylene.
- ether polymers examples include ether polymers, methyl methacrylate polymers, acrylonitrile polymers, polyvinylidene fluoride or vinylidene fluoride and hexafluoropropylene.
- methyl methacrylate polymers examples include acrylonitrile polymers, polyvinylidene fluoride or vinylidene fluoride and hexafluoropropylene.
- acrylonitrile polymers examples include polyvinylidene fluoride or vinylidene fluoride and hexafluoropropylene.
- Ether-based polymers such as polyethylene oxide, polypropylene oxide or their derivatives and copolymers trap lithium ions due to the high basicity of ether oxygen, and at the same time, they are continuously arranged on the polymer chain. Therefore, efficient hopping movement of trapped lithium ions is induced, and ion conductivity is improved.
- linear polyethylene oxide and polypropylene oxide have a low glass transition point and a low melting point (about 70 ° C. or less)
- durability at high temperatures and shape retention Therefore, it is necessary to take measures such as introducing a cross-linked structure in order to improve the melting point and the solvent resistance.
- vinyl acetal polymers such as polyvinyl formal and polyvinyl butyral are known as polymer compounds used in polymer electrolyte gels. These vinyl acetal polymers are polymers having an oxygen atom in the structure, similar to the ether polymers described above.
- Patent Documents 1 to 3 describe polymer electrolyte gels containing polyvinyl acetal and an electrolytic solution.
- Patent Document 4 it is studied to increase the amount of the electrolytic solution by chemically modifying a hydroxyl group contained in polyvinyl acetal and adjusting the amount thereof.
- Patent Documents 5 and 6 disclose polymer electrolyte gels that are excellent in charge / discharge characteristics, shape retention, etc. by crosslinking an acid-modified product of polyvinyl acetal by energization or by crosslinking polyvinyl acetal using a crosslinking accelerator. A method of manufacturing is described.
- the polymer compound used in the conventional polyelectrolyte gel has a site that interacts with lithium ions, but does not have a site that interacts with anions, that is, the mobility of anions is greater. . If the anion can be strongly attracted in the polymer, the mobility of the anion can be kept small, and in addition, the dissociation degree of the electrolyte salt can be improved. As the degree of dissociation of the electrolyte salt increases, the ion concentration in the polymer electrolyte gel increases and the ionic conductivity increases.
- Patent Document 7 describes an ion conductive polymer having a borosiloxane structure and an ion conductor using the ion conductive polymer.
- this ion conductive polymer is supplemented with anion by Lewis acidic boron in a borosiloxane structure and facilitates single movement of the cation by segment movement of the side chain oligoether bond to facilitate ion conductivity. Is described as improving.
- the ionic conductor of Patent Document 7 is an all-solid-type polymer electrolyte that essentially does not contain an electrolytic solution, it cannot achieve ionic conductivity that can withstand practical use. Further, boron-containing compounds generally have a problem in terms of safety.
- Non-Patent Document 1 an attempt is made to create a polymer having a urea group that can be expected to have a chemical interaction effect with the anion in the electrolyte salt, and to keep the mobility of the anion small.
- the anion cannot be strongly attracted in the polymer, and the mobility of the anion is still higher than that of the lithium ion.
- JP-A-3-43909 Japanese Patent Laid-Open No. 3-43910 JP 2006-253085 A JP 2001-200126 A Japanese Patent Laid-Open No. 2005-50808 JP 2008-159596 A JP 2002-179800 JP
- An object of the present invention is a secondary battery that is excellent in electrolyte retention and ion conductivity, has high mechanical strength and shape retention, does not require an extra step for crosslinking, and has excellent cycle characteristics. It is to provide a polymer electrolyte gel composition capable of providing a polymer, a method for producing the same, and a vinyl acetal polymer used in the polymer electrolyte gel composition.
- the present inventors achieve the above object by forming a polymer electrolyte gel composition using a vinyl acetal polymer containing a cationic functional group.
- the present invention has been completed through further investigation based on the findings.
- the vinyl acetal polymer of the present invention is for a polymer electrolyte gel composition and contains a cationic functional group.
- the vinyl acetal polymer may be obtained by saponifying a copolymer of a vinyl ester monomer and a polymerizable monomer containing a cationic functional group and then acetalizing the copolymer.
- the compounds used for acetalization are aliphatic aldehydes having 1 to 15 carbon atoms, hemiacetalization products of aliphatic aldehydes having 1 to 15 carbon atoms, complete acetalization products of aliphatic aldehydes having 1 to 15 carbon atoms, carbon It is at least one selected from the group consisting of aromatic aldehydes having 7 to 20 carbon atoms, hemiacetalization products of aromatic aldehydes having 7 to 20 carbon atoms, and complete acetalization products of aromatic aldehydes having 7 to 20 carbon atoms. Is preferred.
- the vinyl acetal polymer is obtained by converting a vinyl alcohol polymer from an aldehyde containing a cationic functional group, a hemiacetalized product of an aldehyde containing a cationic functional group, and a complete acetalized product of an aldehyde containing a cationic functional group. It is also preferred to be obtained by acetalization using at least one selected from the group consisting of
- the cationic functional group is preferably at least one selected from the group consisting of a quaternary ammonium group, an imidazolium group, a pyridinium group, a phosphonium group, and a sulfonium group.
- the polymer electrolyte gel composition of the present invention contains the above-mentioned vinyl acetal polymer and an electrolytic solution, and the weight ratio of the vinyl acetal polymer and the electrolytic solution is 0.5: 99.5. ⁇ 9: 91.
- the method for producing the polymer electrolyte gel composition of the present invention includes a step of mixing the vinyl acetal polymer and the electrolytic solution in a ratio of 0.5: 99.5 to 9:91.
- a secondary battery that has excellent electrolyte solution retention and ion conductivity, has high mechanical strength and shape retention, does not require an extra step for crosslinking, and has excellent cycle characteristics.
- the vinyl acetal type polymer useful for manufacture of a polymer electrolyte gel composition can be provided.
- the vinyl acetal polymer of the present invention is for a polymer electrolyte gel composition, and is used for producing a polymer electrolyte gel composition.
- the vinyl acetal polymer contains a cationic functional group.
- Examples of the vinyl acetal polymer of the present invention include those having a structure in which a cationic functional group and a skeleton of the vinyl acetal polymer are bonded only through one or two or more covalent bonds. And a polymer compound containing a structural unit (acetal unit) containing an acetal group represented by formula (I) as a repeating unit.
- Such a polymer compound include a structural unit containing an acetal group represented by formula (I) (acetal unit), a structural unit containing a hydroxyl group represented by formula (II) (vinyl alcohol unit), Preferred examples include polymer compounds containing a repeating unit containing a structural unit containing an ester bond represented by the formula (III) (for example, a structural unit derived from a vinyl ester (vinyl ester unit)).
- This polymer compound may further contain a structural unit containing a chemically modified hydroxyl group represented by formula (IV) as a repeating unit in addition to the above structural unit.
- the polymer compound may further include a structural unit derived from the vinyl compound represented by the formula (V) as a repeating unit.
- Formula (IV) It suffices that at least one of the constituent unit Q d containing the chemically modified hydroxyl group shown and the constituent unit Q e derived from the vinyl compound shown in the formula (V) contains a cationic functional group, for example,
- this polymer compound does not contain a structural unit containing a chemically modified hydroxyl group represented by formula (IV) and a structural unit derived from a vinyl compound represented by formula (V), it is represented by formula (I).
- the structural unit containing an acetal group (acetal unit), the structural unit containing an ester bond shown in Formula (III), or both of them may contain a cationic functional group.
- Q a In the structural unit (acetal unit) containing an acetal group represented by the formula (I) that can be contained in a plurality of the polymer compounds, Q a may be one type or two or more types. . In the structural unit containing an ester bond represented by the formula (III) that can be contained in a plurality of the polymer compounds, each of Q b and Q c may be one type, or two or more types. Also good. In the structural unit containing a chemically modified hydroxyl group represented by the formula (IV) that can be contained in a plurality of the polymer compounds, each of Q d and Q f may be one type, or two or more types. There may be.
- each of Q e and Q g may be one, a kind or two or more May be.
- the arrangement order of each repeating unit is not particularly limited, and may be randomly arranged or may be arranged in a block shape.
- Q a , Q c and Q e are a hydrogen atom, a halogen atom, a substituent having one or more carbon atoms, or a cationic functional group.
- Q b is a single bond or a divalent hydrocarbon chain such as alkylene, alkenylene, alkynylene, phenylene, or naphthylene. These divalent hydrocarbon chains may be substituted with halogen atoms such as fluorine, chlorine and bromine.
- Q d is a substituent having one or more carbon atoms, or a cationic functional group.
- Q f and Q g are a hydrogen atom or a methyl group. The substituent having one or more carbon atoms represented by Q a , Q c , Q d and Q e may contain a cationic functional group.
- Examples of the cationic functional group include a quaternary ammonium group (including piperidinium group, piperazinium group, morpholinium group, etc.), an imidazolium group (including benzimidazolium group, etc.), a pyrazolium group, a pyridinium group, and pyridazinium.
- the vinyl acetal polymer of the present invention may have one kind of cationic functional group or may have two or more kinds of cationic functional groups.
- the availability of raw materials is excellent and the vinyl acetal polymer of the present invention can be easily obtained, so that a quaternary ammonium group, an imidazolium group, a pyridinium group, a phosphonium group, and It is preferably at least one selected from the group consisting of sulfonium groups.
- Examples of the quaternary ammonium group include those represented by the formula (VI).
- Examples of the imidazolium group include those represented by any one of formulas (VII-a) to (VII-e).
- Examples of the pyridinium group include those represented by any one of formulas (VIII-a) to (VIII-d).
- As said phosphonium group what was shown to Formula (IX) is mentioned, for example.
- As said sulfonium group, what was shown to Formula (X) is mentioned, for example.
- R 1 , R 2 and R 3 are each a substituent having one or more carbon atoms
- a 1 , A 2 , A 3 , A 4 and A 5 are each a hydrogen atom.
- the vinyl acetal polymer of the present invention for example, (1) A method of saponifying a copolymer obtained by copolymerizing a vinyl ester monomer represented by vinyl acetate and a polymerizable monomer containing a cationic functional group, (2) The vinyl alcohol polymer is at least selected from the group consisting of an aldehyde containing a cationic functional group, a hemiacetalized product of an aldehyde containing a cationic functional group, and a complete acetalized product of an aldehyde containing a cationic functional group A method of acetalization using one kind, (3) A method in which an alcohol containing a cationic functional group or an epoxy compound containing a cationic functional group is reacted with a vinyl alcohol polymer to introduce a cationic functional group via an ether bond, followed by acetalization, (4) A method in which a carboxylic acid containing a cationic functional group or a derivative
- a method of introducing a cationic functional group through an ether bond by reacting an alcohol containing a cationic functional group or an epoxy compound containing a cationic functional group with a vinyl acetal polymer (6) A method of introducing a cationic functional group via an ester bond by reacting a vinyl acetal polymer with a carboxylic acid containing a cationic functional group or a derivative thereof, Or the method etc. which combined 2 or more types of said method are mentioned.
- the methods (1) and (2) are particularly preferably employed.
- Examples of the polymerizable monomer having a cationic functional group used in the method (1) include a polymerizable monomer having a quaternary ammonium group and a polymerizable monomer having an imidazolium group. And a polymerizable monomer having a pyridinium group, a polymerizable monomer having a phosphonium group, and a polymerizable monomer having a sulfonium group.
- Examples of the polymerizable monomer having a quaternary ammonium group include allyl trimethylammonium, allyltriethylammonium, allylethyldimethylammonium, allyltribenzylammonium, 1-allyl-1-methylpyrrolidinium and the like.
- Examples of the polymerizable monomer having an imidazolium group include 3-methyl-1-vinylimidazolium, 2,3-dimethyl-1-vinylimidazolium, and 2-ethyl-3-methyl-1-vinyl. Examples include imidazolium, 3-methyl-2-phenyl-1-vinylimidazolium, 3-ethyl-1-vinylimidazolium, and the like.
- Examples of the polymerizable monomer having a pyridinium group include 1-methyl-2-vinylpyridinium, 1-methyl-3-vinylpyridinium, 1-methyl-4-vinylpyridinium, and 1-ethyl-2-vinyl. Examples thereof include pyridinium, 1-ethyl-3-vinylpyridinium, 1-ethyl-4-vinylpyridinium and the like.
- Examples of the polymerizable monomer having a phosphonium group include (3-acrylamidopropyl) trimethylphosphonium, (3-methacrylamideamidopropyl) trimethylphosphonium, (3-acrylamido-3,3-dimethylpropyl) trimethylphosphonium, Trimethyl (2-vinylbenzyl) phosphonium, trimethyl (3-vinylbenzyl) phosphonium, trimethyl (4-vinylbenzyl) phosphonium, tributyl (2-vinylbenzyl) phosphonium, tributyl (3-vinylbenzyl) phosphonium, tributyl (4-vinyl) (Benzyl) phosphonium and the like.
- Examples of the polymerizable monomer having a sulfonium group include dimethyl (2-vinylphenyl) sulfonium, dimethyl (3-vinylphenyl) sulfonium, dimethyl (4-vinylphenyl) sulfonium, and the like.
- anion corresponding to the cation of the polymerizable monomer containing the cationic functional group examples include chloride ion, bromide ion, iodide ion, nitrate ion, hexafluorophosphate ion, and tetrafluoroboric acid.
- the above polymerizable monomer containing a cationic functional group may be used alone or in combination of two or more.
- diallyldimethylammonium chloride, (3-methacrylamidopropyl) trimethylammonium chloride, and (3-acrylamido-3,3-dimethylpropyl) trimethylammonium chloride are particularly preferable.
- the conditions for copolymerizing the vinyl ester monomer and the polymerizable monomer containing a cationic functional group are not particularly limited, and in the case of producing an ordinary vinyl ester polymer. Conditions can be adopted. Moreover, the conditions at the time of saponifying the obtained copolymer are not particularly limited, and for example, the conditions for saponifying a normal vinyl ester polymer with alkali, acid, aqueous ammonia, etc. can be adopted.
- the compounds used for acetalization include aliphatic aldehydes having 1 to 15 carbon atoms, hemiacetalized products of aliphatic aldehydes having 1 to 15 carbon atoms, and aliphatic aldehydes having 1 to 15 carbon atoms. Selected from the group consisting of a complete acetalized product of C7-20 aromatic aldehyde, a hemiacetalized product of C7-20 aromatic aldehyde, and a complete acetalized product of C7-20 aromatic aldehyde. It is preferable that there is at least one.
- examples of aliphatic aldehydes having 1 to 15 carbon atoms, hemiacetalization products of aliphatic aldehydes having 1 to 15 carbon atoms, and complete acetalization products of aliphatic aldehydes having 1 to 15 carbon atoms include formaldehyde and acetaldehyde.
- aromatic aldehydes having 7 to 20 carbon atoms examples include benzaldehyde, 2- Examples thereof include methylbenzaldehyde, 3-methylbenzaldehyde, 4-methylbenzaldehyde, p-hydroxybenzaldehyde, m-hydroxybenzaldehyde and the like.
- acetalization Only one type of compound used for the acetalization may be used, or two or more types may be used in combination. Among these, formaldehyde, acetaldehyde, n-butyraldehyde, and benzaldehyde are preferable, and n-butyraldehyde is particularly preferable.
- the conditions for acetalization include, for example, an aqueous solution of a polymer to be acetalized (typically a vinyl alcohol polymer containing a cationic functional group) and the compound used for the acetalization (such as an aldehyde).
- Examples thereof include a solvent method in which an acetalization reaction is performed with a compound (aldehyde or the like) to be used, and a polymer is precipitated from the reaction solution with a poor solvent (water or the like) for the obtained acetalization product.
- the aqueous medium method is preferable.
- the acid catalyst inorganic acids such as hydrochloric acid, nitric acid, sulfuric acid and carbonic acid, and organic acids such as acetic acid and propionic acid can be used. Of these, hydrochloric acid and nitric acid are particularly preferred.
- Examples of the vinyl alcohol polymer used in the methods (2), (3) and (4) include a saponification of a vinyl ester polymer obtained by polymerizing a vinyl ester monomer such as vinyl acetate. What is obtained by doing this can be used, and polyvinyl alcohol obtained by saponifying a homopolymer of vinyl acetate can be preferably used.
- Examples of the aldehyde containing a cationic functional group, the hemiacetalized product of an aldehyde containing a cationic functional group, and the complete acetalized product of an aldehyde containing a cationic functional group used in the method (2) are as follows. Examples thereof include a compound having a quaternary ammonium group, a compound having an imidazolium group, a compound having a pyridinium group, a compound having a phosphonium group, and a compound having a sulfonium group.
- Examples of the compound having a quaternary ammonium group include (formylmethyl) trimethylammonium, (1-formylethyl) trimethylammonium, (2-formylethyl) trimethylammonium, (1-formylpropyl) trimethylammonium, 2-formylpropyl) trimethylammonium, (3-formylpropyl) trimethylammonium, (2-formylphenyl) trimethylammonium, (3-formylphenyl) trimethylammonium, (4-formylphenyl) trimethylammonium, (4-formylbenzyl) Trimethylammonium, triethyl (formylmethyl) ammonium, triethyl (1-formylethyl) ammonium, triethyl (2-formylethyl) ammonium, Ethyl (1-formylpropyl) ammonium, triethyl (2-formylpropyl) ammonium, triethyl (3
- Examples of the compound having an imidazolium group include 3- (formylmethyl) -1-methyl-1H-imidazol-3-ium and 3- (1-formylethyl) -1-methyl-1H-imidazole-3. -Ium, 3- (2-formylethyl) -1-methyl-1H-imidazol-3-ium, 3- (1-formylpropyl) -1-methyl-1H-imidazol-3-ium, 3- (2- Formylpropyl) -1-methyl-1H-imidazol-3-ium, 3- (3-formylpropyl) -1-methyl-1H-imidazol-3-ium, 1-ethyl-3- (formylmethyl) -1H- Imidazole-3-ium, 1-ethyl-3- (1-formylethyl) -1H-imidazol-3-ium, 1-ethyl-3- (2-formylethyl) -1H-imidazol-3-ium, 1-ethyl-3- (1-form
- Examples of the compound having a pyridinium group include 1-methylpyridinium-2-carbaldehyde, 1-methylpyridinium-3-carbaldehyde, 1-methylpyridinium-4-carbaldehyde and the like.
- Examples of the compound having a phosphonium group include (formylmethyl) trimethylphosphonium, triethyl (formylmethyl) phosphonium, triethyl (2-formylethyl) phosphonium, (2-formylethyl) triisopropylphosphonium, tributyl (2-formyl).
- Ethyl) phosphonium triethyl (3-formylpropyl) phosphonium, (3-formylpropyl) triisopropylphosphonium, tributyl (3-formylpropyl) phosphonium, (formylmethyl) triphenylphosphonium, (2-formylethyl) triphenylphosphonium, (3-formylpropyl) triphenylphosphonium, 2-hydroxy-4-tributylphosphoniotetrahydropyran, tributyl (1,3-dioxolane) 2-yl) phosphonium, tributyl (1,3-dioxolan-2-ylmethyl) phosphonium, (1,3-dioxan-2-ylmethyl) triphenylphosphonium, (1,3-dioxolan-2-ylmethyl) triphenylphosphonium, etc. Is mentioned.
- Examples of the compound having a sulfonium group include 4-formylphenyldimethylsulfonium, 4-formylphenyldiphenylsulfonium, 2-hydroxy-4-dimethylsulfoniotetrahydropyran, 2,2-dimethoxyethyldimethylsulfonium, 2,2 -Dimethoxyethyldiphenylsulfonium, 2,2-diethoxyethyldimethylsulfonium, 2,2-diethoxyethyldiphenylsulfonium and the like.
- Examples of the anion corresponding to the cation of the aldehyde containing the cationic functional group, the hemiacetalized product of the aldehyde containing the cationic functional group, and the complete acetalized product of the aldehyde containing the cationic functional group include chloride ions, Bromide ion, iodide ion, nitrate ion, hexafluorophosphate ion, tetrafluoroborate ion, hexafluoroarsenate ion, perchlorate ion, methanesulfonate ion, trifluoromethanesulfonate ion, bis (trifluoro) Lomethanesulfonyl) imido ion, bis (perfluoroethanesulfonyl) imido ion, tris (trifluoromethanesulfonyl) methyl acid ion, tris (per
- the aldehyde containing the cationic functional group, the hemiacetalized product of the aldehyde containing the cationic functional group, and the complete acetalized product of the aldehyde containing the cationic functional group may be used alone or in combination of two or more. May be used in combination.
- hexafluorophosphate (formylmethyl) trimethylammonium and hexafluorophosphate 3- (2,2-dimethoxyethyl) -1-methyl-1H-imidazol-3-ium are particularly preferable.
- the conditions for acetalizing the vinyl alcohol polymer may be employed when, for example, polyvinyl butyral is produced by reacting polyvinyl alcohol with n-butyraldehyde in the presence of an acid catalyst.
- Various known conditions can be adopted.
- Examples of the alcohol containing a cationic functional group and the epoxy compound containing a cationic functional group used in the method (3) include alcohols having a quaternary ammonium group and alcohols having an imidazolium group. , Alcohols having pyridinium groups, alcohols having phosphonium groups, alcohols having sulfonium groups, epoxy compounds having quaternary ammonium groups, epoxy compounds having imidazolium groups, epoxy compounds having pyridinium groups, phosphonium groups And an epoxy compound having a sulfonium group.
- Examples of the alcohols having a quaternary ammonium group include (2-hydroxyethyl) trimethylammonium, triethyl (2-hydroxyethyl) ammonium, (3-hydroxypropyl) trimethylammonium, triethyl (3-hydroxypropyl). Ammonium, (4-hydroxybutyl) trimethylammonium, triethyl (4-hydroxybutyl) ammonium and the like can be mentioned.
- Examples of the alcohol having an imidazolium group include 3- (hydroxymethyl) -1-methyl-1H-imidazol-3-ium, 1,2-diethyl-3- (hydroxymethyl) -1H-imidazole- 3-ium, 3- (2-hydroxyethyl) -1-methyl-1H-imidazol-3-ium, 3- (3-hydroxypropyl) -1-methyl-1H-imidazol-3-ium, 3- (4 -Hydroxybutyl) -1-methyl-1H-imidazol-3-ium, 2- (hydroxymethyl) -1,3-dimethyl-1H-imidazol-3-ium, 2- (2-hydroxyethyl) -1,3 -Dimethyl-1H-imidazole-3-ium, 2- (3-hydroxypropyl) -1,3-dimethyl-1H-imidazole-3-iu 2- (4-hydroxybutyl) -1,3-dimethyl-1H-imidazol-3-ium, 2- (hydroxymethyl) -1,3,4-trimethyl-1H
- Examples of the alcohols having a pyridinium group include 2- (hydroxymethyl) -1-methylpyridinium, 2- (2-hydroxyethyl) -1-methylpyridinium, 2- (3-hydroxypropyl) -1- Methylpyridinium, 2- (4-hydroxybutyl) -1-methylpyridinium, 3- (hydroxymethyl) -1-methylpyridinium, 4- (hydroxymethyl) -1-methylpyridinium, 1-ethyl-3- (hydroxymethyl) ) Pyridinium and the like.
- Examples of the alcohols having a phosphonium group include (hydroxymethyl) trimethylphosphonium, (2-hydroxyethyl) trimethylphosphonium, (3-hydroxypropyl) trimethylphosphonium, (4-hydroxybutyl) trimethylphosphonium, triethyl (hydroxy And methyl) phosphonium, (hydroxymethyl) tripropylphosphonium, triisopropyl (hydroxymethyl) phosphonium, tributyl (hydroxymethyl) phosphonium, (hydroxymethyl) triphenylphosphonium, and the like.
- Examples of the alcohol having a sulfonium group include (hydroxymethyl) dimethylsulfonium, (2-hydroxyethyl) dimethylsulfonium, (3-hydroxypropyl) dimethylsulfonium, (4-hydroxybutyl) dimethylsulfonium, dibutyl (hydroxyl). And methyl) sulfonium and (hydroxymethyl) diphenylsulfonium.
- Examples of the epoxy compound having a quaternary ammonium group include glycidyl trimethyl ammonium, triethyl glycidyl ammonium, glycidyl tripropyl ammonium, glycidyl triisopropyl ammonium, and tributyl glycidyl ammonium.
- Examples of the epoxy compound having an imidazolium group include 3-glycidyl-1-methyl-1H-imidazol-3-ium, 1,2-diethyl-3-glycidyl-1H-imidazol-3-ium, 2- Glycidyl-1,3-dimethyl-1H-imidazol-3-ium, 2-glycidyl-1,3,4-trimethyl-1H-imidazol-3-ium, 2-glycidyl-1,3,4,5-tetramethyl -1H-imidazole-3-ium, 4-glycidyl-1,3-dimethyl-1H-imidazole-3-ium, 4-glycidyl-1,2,3-trimethyl-1H-imidazole-3-ium, 4-glycidyl -1,2,3,5-tetramethyl-1H-imidazol-3-ium and the like.
- Examples of the epoxy compound having a pyridinium group include 2-glycidyl-1-methylpyridinium, 3-glycidyl-1-methylpyridinium, 4-glycidyl-1-methylpyridinium, and 1-ethyl-3-glycidylpyridinium. Can be mentioned.
- Examples of the epoxy compound having a phosphonium group include glycidyltrimethylphosphonium, triethylglycidylphosphonium, glycidyltripropylphosphonium, glycidyltriisopropylphosphonium, tributylglycidylphosphonium, glycidyltriphenylphosphonium, and the like.
- Examples of the epoxy compound having a sulfonium group include glycidyldimethylsulfonium, dibutylglycidylsulfonium, glycidyldiphenylsulfonium, and the like.
- Examples of the anion corresponding to the cation of the alcohol containing the cationic functional group and the epoxy compound containing the cationic functional group include chloride ion, bromide ion, iodide ion, nitrate ion, and hexafluorophosphate.
- Examples include acid ions, tris (trifluoromethanesulfonyl) methyl acid ions, tris (perfluoroethanesulfonyl) methyl acid ions, tetrachloroaluminate ions, hexafluorosilicate ions, and the like, but are not particularly limited.
- Only one kind of the above-mentioned alcohol containing a cationic functional group and an epoxy compound containing a cationic functional group may be used, or two or more kinds may be used in combination.
- glycidyltrimethylammonium hexafluorophosphate and 3-glycidyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate are particularly preferable.
- the alcohol is usually reacted with sulfuric acid to obtain ether.
- the conditions for obtaining the epoxide and for reacting the epoxide with alcohol in the presence of an acid catalyst can be employed.
- examples of the compound used for acetalization of the obtained vinyl alcohol polymer containing a cationic functional group include the compounds described above as examples of the compound used for acetalization in the method (1). It is done.
- part or all of the compound used for the acetalization includes an aldehyde containing a cationic functional group, a hemiacetalized product of an aldehyde containing a cationic functional group, and a cationic functional group.
- the compound mentioned above may be sufficient as the example of the complete acetalization thing of an aldehyde.
- the conditions for acetalization for example, known conditions such as those employed when producing polyvinyl butyral by reacting polyvinyl alcohol with n-butyraldehyde in the presence of an acid catalyst can be employed.
- Examples of the carboxylic acid containing a cationic functional group and a derivative of the carboxylic acid containing the cationic functional group used in the method (4) include a compound having a quaternary ammonium group, an imidazolium group , A compound having a pyridinium group, a compound having a phosphonium group, a compound having a sulfonium group, and the like.
- Examples of the compound having a quaternary ammonium group include betaine (glycine betaine), alanine betaine, phenylalanine betaine, leucine betaine, (2-carboxyphenyl) trimethylammonium, (3-carboxyphenyl) trimethylammonium, (4 -Carboxyphenyl) trimethylammonium, (2-carboxyphenyl) triethylammonium, (3-carboxyphenyl) triethylammonium, (4-carboxyphenyl) triethylammonium and the like.
- Examples of the compound having an imidazolium group include 3- (carboxymethyl) -1-methyl-1H-imidazol-3-ium and 3- (carboxymethyl) -1,2-diethyl-1H-imidazole-3. -Ium, 3- (1-carboxyethyl) -1-methyl-1H-imidazol-3-ium, 3- (2-carboxyethyl) -1-methyl-1H-imidazol-3-ium and the like.
- Examples of the compound having a pyridinium group include 2-carboxy-1-methylpyridinium, 3-carboxy-1-methylpyridinium, 4-carboxy-1-methylpyridinium, 3-carboxy-1-ethylpyridinium, and the like. It is done.
- Examples of the compound having a phosphonium group include trimethylphosphonioacetic acid, tributylphosphonioacetic acid, triphenylphosphonioacetic acid, 2-tributylphosphoniobenzoic acid, 3-tributylphosphoniobenzoic acid, and 4-tributylphosphoniobenzoic acid. An acid etc. are mentioned.
- Examples of the compound having a sulfonium group include dimethylsulfonioacetic acid, dibutylsulfonioacetic acid, diphenylsulfonioacetic acid, 2-dibutylsulfoniobenzoic acid, 3-dibutylsulfoniobenzoic acid, and 4-dibutylsulfoniobenzoic acid.
- anion corresponding to the cation of the carboxylic acid containing the cationic functional group and the derivative of the carboxylic acid containing the cationic functional group include chloride ion, bromide ion, iodide ion, nitrate ion, hexa Fluorophosphate ion, tetrafluoroborate ion, hexafluoroarsenate ion, perchlorate ion, methanesulfonate ion, trifluoromethanesulfonate ion, bis (trifluoromethanesulfonyl) imido ion, bis (perfluoro Examples thereof include, but are not limited to, ethanesulfonyl) imido ion, tris (trifluoromethanesulfonyl) methyl acid ion, tris (perfluoroethanesulfonyl) methyl acid ion, tet
- the carboxylic acid containing the cationic functional group and the derivative of the carboxylic acid containing the cationic functional group may be used alone or in combination of two or more.
- betaine hexafluorophosphate and (4-carboxyphenyl) trimethylammonium hexafluorophosphate are particularly preferable.
- the alcohol and carboxylic acid are usually reacted under an acid or base catalyst.
- the conditions for obtaining the ester can be employed.
- examples of the compound used for acetalization of the obtained vinyl alcohol polymer containing a cationic functional group include the compounds described above as examples of the compound used for acetalization in the method (1). It is done.
- part or all of the compound used for the acetalization includes an aldehyde containing a cationic functional group, a hemiacetalized product of an aldehyde containing a cationic functional group, and a cationic functional group.
- the compound mentioned above may be sufficient as the example of the complete acetalization thing of an aldehyde.
- the conditions for acetalization for example, known conditions such as those employed when producing polyvinyl butyral by reacting polyvinyl alcohol with n-butyraldehyde in the presence of an acid catalyst can be employed.
- the vinyl acetal polymer used in the methods (5) and (6) is obtained by acetalizing the vinyl alcohol polymer used in the methods (2), (3) and (4) described above.
- the compound used for acetalization of the vinyl alcohol polymer include the compounds described above as examples of the compound used for acetalization in Method (1).
- part or all of the compound used for the acetalization includes an aldehyde containing a cationic functional group, a hemiacetalized product of an aldehyde containing a cationic functional group, and a cationic functional group.
- the compound mentioned above may be sufficient as the example of the complete acetalization thing of an aldehyde.
- the conditions for acetalization for example, known conditions such as those employed when producing polyvinyl butyral by reacting polyvinyl alcohol with n-butyraldehyde in the presence of an acid catalyst can be employed.
- Examples of the alcohol containing a cationic functional group and the epoxy compound containing a cationic functional group used in the method (5) include an alcohol containing a cationic functional group used in the method (3), And the above-mentioned compound is mentioned as an example of the epoxy compound containing a cationic functional group.
- an alcohol is usually obtained by reacting alcohol with sulfuric acid. The conditions for reacting epoxide with alcohol in the presence of an acid catalyst can be employed.
- Examples of the carboxylic acid containing the cationic functional group and the derivative of the carboxylic acid containing the cationic functional group used in the method (6) include the cationic functional group used in the method (4).
- Examples of the carboxylic acid containing, and derivatives of the carboxylic acid containing the cationic functional group include the compounds described above.
- an ester is usually obtained by reacting an alcohol and a carboxylic acid under an acid or base catalyst. Case conditions can be adopted.
- the degree of polymerization of the vinyl alcohol polymer used as a raw material for the vinyl acetal polymer used in (5) and (6) is an average polymerization measured according to the polyvinyl alcohol test method specified in JIS K 6726-1994. The degree is preferably in the range of 100 to 5000, more preferably in the range of 150 to 3500, and still more preferably in the range of 200 to 2500.
- the saponification degree of the vinyl alcohol polymer used as the raw material for the vinyl acetal polymer used in the methods (5) and (6) is preferably 80 mol% or more.
- the degree of acetalization of the vinyl acetal polymer of the present invention is preferably in the range of 0.1 to 85 mol%, more preferably in the range of 1 to 83 mol%, and still more preferably in the range of 10 to 80 mol%. It is a range.
- the “degree of acetalization” means the ratio of the number of moles of the constituent unit constituting the acetal unit to the total number of moles of the constituent unit constituting the acetal unit, the vinyl alcohol unit and the vinyl ester unit.
- the number of moles of the structural unit constituting the acetal unit is usually twice the number of moles of the acetal unit.
- the vinyl acetal polymer is a structural unit containing an acetal group represented by the above formula (I) (acetal unit): n I mol, a structural unit containing a hydroxyl group represented by the above formula (II).
- acetal unit n I mol
- a structural unit containing a hydroxyl group represented by the above formula (II) a structural unit containing a hydroxyl group represented by the above formula (II).
- degrees of acetalization those based on the acetal unit corresponding to the acetal of formaldehyde are “formalization degree”, those based on the acetal unit corresponding to the acetal acetal are “acetoacetalization degree”, Those based on acetal units corresponding to the acetal of butyraldehyde will be specifically referred to as “degree of butyralization”.
- the vinyl acetal polymer is a structural unit containing an acetal group represented by the above formula (I) and Q a is a propyl group (acetal unit corresponding to an acetal of butyraldehyde): n I (Bu) mol, a structural unit containing an acetal group represented by the above formula (I), wherein Q a is a methyl group (acetal unit corresponding to an acetaldehyde acetaldehyde): n I (Ac) mole,
- Q a is a methyl group (acetal unit corresponding to an acetaldehyde acetaldehyde): n I (Ac) mole
- Butyralization degree (mol%) 100 ⁇ [n I (Bu) ⁇ 2] / [n I (Bu) ⁇ 2 + n I (Ac) ⁇ 2 + n II + n III ]
- Degree of acetoacetalization (mol%) 100 ⁇ [n I (Ac) ⁇ 2] / [n I (Bu) ⁇ 2 + n I (Ac) ⁇ 2 + n II + n III ]
- the vinyl ester monomer unit content of the vinyl acetal polymer of the present invention is preferably in the range of 0.01 to 20 mol%, more preferably in the range of 0.05 to 15 mol%, The range is preferably from 0.1 to 10 mol%.
- the content of the vinyl ester monomer unit is the total constitutional unit constituting the vinyl acetal polymer (however, one acetal unit composed of two constitutional units is composed of two constitutional units and The number of moles of vinyl ester monomer units in the number of moles). Further, among the contents of vinyl ester monomer units, those based on vinyl acetate units will be specifically referred to as “vinyl acetate unit contents”.
- the content of vinyl alcohol units in the vinyl acetal polymer of the present invention is preferably in the range of 0.1 to 50 mol%, more preferably in the range of 1 to 40 mol%, still more preferably 10 to 30 mol%. % Range.
- the content of vinyl alcohol units is the total constituent units constituting the vinyl acetal polymer (however, one acetal unit composed of two constituent units is considered to be two constituent units. ) Means the ratio of the number of moles of vinyl alcohol units to the number of moles.
- the cationic functional group content of the vinyl acetal polymer of the present invention varies depending on the method for producing the vinyl acetal polymer.
- it is preferably in the range of 0.01 to 30 mol%, more preferably in the range of 0.05 to 20 mol%. More preferably, it is in the range of 0.1 to 10 mol%.
- the method (2) is employed, it is preferably in the range of 0.1 to 85 mol%, more preferably in the range of 1 to 83 mol%, and still more preferably in the range of 10 to 80 mol%.
- the content of the cationic functional group refers to all structural units constituting the vinyl acetal polymer (however, one acetal unit composed of two structural units is considered as two structural units. ) Means the ratio of the number of moles of the cationic functional group to the number of moles.
- the vinyl acetal polymer of the present invention is easy to prepare a gel, it preferably contains two or more acetal units not containing a cationic functional group, and contains an acetal group represented by the above formula (I). More preferably, Qa contains two or more structural units that do not contain a cationic functional group.
- Specific examples of such a vinyl acetal polymer include a constitutional unit containing an acetal group represented by the above formula (I), wherein Q a is a propyl group, and Q a is a methyl group.
- the vinyl acetal polymer of the present invention is not particularly limited in its use as long as it is used for producing a polymer electrolyte gel composition, but has excellent electrolytic solution retention and ionic conductivity, and high mechanical strength.
- the vinyl acetal of the present invention is a polymer electrolyte gel composition that has a shape-retaining property and does not require an extra step for crosslinking and can provide a secondary battery with excellent cycle characteristics.
- the present invention contains the vinyl acetal polymer of the present invention and an electrolytic solution, and the weight ratio of the vinyl acetal polymer of the present invention to the electrolytic solution is 0.5: 99.5 to 9 : 91 is included.
- the polymer electrolyte gel composition of the present invention is usually a so-called gel.
- the electrolytic solution used in the polymer electrolyte gel composition of the present invention one containing an electrolyte can be used, and preferably one containing an electrolyte and a non-aqueous solvent, for example, an electrolyte as a non-aqueous solvent. A dissolved one can be used.
- the electrolytic solution may further contain various additives as necessary.
- the electrolyte described above is dissolved in a non-aqueous solvent can be used which can produce ions, for example, lithium hexafluorophosphate (LiPF 6), lithium tetrafluoroborate (LiBF 4) , Lithium hexafluoroarsenate (LiAsF 6 ), lithium perchlorate (LiClO 4 ), lithium trifluoromethanesulfonate (CF 3 SO 3 Li), lithium bis (trifluoromethanesulfonyl) imide (LiN (SO 2 CF 3 ) 2 ), bis (perfluoroethanesulfonyl) imidolithium (LiN (SO 2 C 2 F 5 ) 2 ), tris (trifluoromethanesulfonyl) methyllithium (LiC (SO 2 CF 3 ) 3 ), tris (perfluoroethanesulfonyl) ) methyl lithium (LiC (SO 2 C
- lithium salts sodium salts, magnesium salts, calcium salts, and the like can be given. These electrolytes may be used alone or in combination of two or more. Among these, lithium salts are preferable, and lithium hexafluorophosphate and lithium bis (trifluoromethanesulfonyl) imide are particularly preferable.
- non-aqueous solvent examples include lactones such as ⁇ -butyrolactone, ⁇ -valerolactone, ⁇ -valerolactone, and ⁇ -caprolactone; ethylene carbonate, propylene carbonate, butylene carbonate, vinylene carbonate, dimethyl carbonate, ethyl methyl carbonate, Carbonates such as diethyl carbonate; ethers such as 1,2-dimethoxyethane, 1-ethoxy-2-methoxyethane, 1,2-diethoxyethane, tetrahydrofuran, 2-methyltetrahydrofuran; nitriles such as acetonitrile; sulfolane compounds; And phosphoric acid esters; pyrrolidones and the like.
- lactones such as ⁇ -butyrolactone, ⁇ -valerolactone, ⁇ -valerolactone, and ⁇ -caprolactone
- ethylene carbonate propylene carbonate
- non-aqueous solvents may be used alone or in combination of two or more.
- lactones and carbonates are preferable, and ⁇ -butyrolactone, ethylene carbonate, propylene carbonate, dimethyl carbonate, ethyl methyl carbonate, and diethyl carbonate are more preferable.
- carbonate ester it is preferable to use together cyclic carbonate ester and chain carbonate ester from a viewpoint of coexistence of acceleration
- the concentration of the electrolyte is preferably within a range of 0.01 to 20 mol / L, more preferably 0.05 to 20 mol / L as the electrolytic solution at 25 ° C.
- the range is 10 mol / L, and more preferably in the range of 0.1 to 5 mol / L.
- electrolytic solution 0.5: 99.5-9: 91.
- the weight of the vinyl acetal polymer in the above weight ratio does not include the weight of the counter anion of the cationic functional group contained in the vinyl acetal polymer.
- the polymer electrolyte gel composition of the present invention has high mechanical strength and shape retention and does not require an extra step for crosslinking, it is preferably produced without undergoing a crosslinking step. Depending on the use of the polymer electrolyte gel composition of the present invention, it may be produced through a crosslinking step with a crosslinking accelerator.
- the polymer electrolyte gel composition of the present invention may be composed only of the vinyl acetal polymer of the present invention and an electrolytic solution, but may further contain other components. Examples of such other components include fillers, the above-described crosslinking accelerators, and reaction products thereof.
- the total proportion of the vinyl acetal polymer of the present invention and the electrolytic solution in the polymer electrolyte gel composition of the present invention is preferably 50% by weight or more, more preferably 80% by weight or more, More preferably, it is 95% by weight or more.
- the polymer electrolyte gel composition of the present invention is obtained by mixing the vinyl acetal polymer of the present invention and an electrolytic solution in a weight ratio of 0.5: 99.5 to 9:91 before mixing,
- the method of mixing the vinyl acetal polymer of the present invention and the electrolytic solution is preferable because a more uniform polymer electrolyte gel composition can be obtained.
- Specific examples of the method for producing the polymer electrolyte gel composition of the present invention or a molded article comprising the composition include the following first to third methods.
- the above-mentioned electrolytic solution is added to a solution obtained by dissolving the vinyl acetal polymer of the present invention in an organic solvent, and the electrolytic solution obtained by dissolving the vinyl acetal polymer of the present invention in an organic solvent. And the organic solvent is removed by evaporation before or after the molding process.
- the organic solvent is not particularly limited as long as it can dissolve the vinyl acetal polymer of the present invention.
- Examples thereof include alcohols such as methanol, ethanol and propanol; ketones such as acetone, methyl ethyl ketone and cyclohexanone; N, Amides such as N-dimethylacetamide and N, N-dimethylformamide; ethers such as dioxane and tetrahydrofuran; chlorinated hydrocarbons such as methylene chloride and chloroform; aromatic hydrocarbons such as toluene, xylene, styrene and pyridine; dimethyl sulfoxide and the like And carboxylic acids such as acetic acid.
- alcohols such as methanol, ethanol and propanol
- ketones such as acetone, methyl ethyl ketone and cyclohexanone
- N Amides such as N-dimethylacetamide and N, N-dimethylformamide
- ethers such as dioxane and tetrahydrofuran
- the second method is a method in which the mixture of the vinyl acetal polymer of the present invention and the electrolytic solution is molded into a predetermined shape, for example, a method that does not use an organic solvent as described in the first method. Is mentioned.
- the third method is a method in which the vinyl acetal polymer of the present invention is formed by cast film formation, melt extrusion film formation, or the like to produce a film, and this film is impregnated in the electrolytic solution.
- the polymer electrolyte gel composition of the present invention uses the vinyl acetal polymer containing the cationic functional group of the present invention described above, the electrolyte solution retention is excellent even without an extra step for crosslinking. At the same time, it is presumed that the cationic functional group in the molecular chain can promote ionization of the electrolyte, and the ionic conductivity is improved. In addition, since the cationic functional group in the molecular chain can efficiently trap the anion contained in the electrolyte and improve the transport number of the cation, the secondary battery using the polymer electrolyte gel composition of the present invention can be used. It is presumed that the cycle characteristics are improved when the is manufactured.
- the use of the polymer electrolyte gel composition of the present invention is not particularly limited, but it makes use of the excellent electrolyte solution retention, ion conductivity, mechanical strength, shape retention, etc. of the polymer electrolyte gel composition of the present invention. Therefore, it is preferably used as a constituent member of a battery or a capacitor, more preferably used as a constituent member of a secondary battery or a capacitor because it has excellent cycle characteristics, and a lithium ion secondary battery or lithium It is more preferable to use as a constituent member of an ion capacitor, and it is particularly preferable to use as a constituent member of a lithium ion secondary battery.
- a secondary battery using a polymer electrolyte gel usually has a pair of electrodes, a separator, and a polymer electrolyte gel disposed between each electrode and the separator.
- the polymer electrolyte gel composition of this invention can be used as a polymer electrolyte gel of the said secondary battery.
- the shape of the polymer electrolyte gel composition of the present invention in the secondary battery depends on the shape of the target secondary battery, the production method thereof, and the like, for example, a thin film having a thickness of 1 to 500 ⁇ m, or a pair And a gap formed in the separator disposed between them, and a shape formed by solidification after a molten polymer electrolyte gel continuously enters around these gaps.
- the positive electrode constituting one of the pair of electrodes a positive electrode current collector having a structure in which a positive electrode active material layer is formed can be used.
- the negative electrode constituting the other the negative electrode current collector is used. What has the structure in which the negative electrode active material layer was formed can be used.
- the secondary battery using a polymer electrolyte gel has an exterior member. The secondary battery can be protected by wrapping the electrode, the separator, and the polymer electrolyte gel as a whole with an exterior member.
- the positive electrode current collector for example, a plate or foil made of aluminum, nickel, stainless steel or the like can be used, and aluminum foil is preferable.
- the positive electrode active material layer includes, for example, a positive electrode active material and a binder, and may further include a conductive aid as necessary.
- a material capable of inserting and extracting lithium can be used, and examples thereof include a lithium-containing transition metal oxide and a lithium-containing transition metal phosphate compound.
- a lithium-containing transition metal oxide LiCoO 2 , LiNiO 2 , LiMn 2 O 4 , LiNi 0.5 Co 0.5 O 2 , LiNi 0.5 Co 0.3 Mn 0.2 O 2 , LiFePO 4 , LiFe 0. 5 Mn 0.5 PO 4 or the like.
- binder contained in the positive electrode active material layer examples include polyvinylidene fluoride (PVdF).
- Examples of the conductive assistant contained in the positive electrode active material layer include ketjen black, acetylene black, carbon black, and carbon nanotube.
- the positive electrode is dispersed and kneaded in a solvent such as N-methyl-2-pyrrolidone together with a binder and, if necessary, a conductive auxiliary agent, if necessary, and then applied onto the positive electrode current collector, It can be produced by removing the solvent by drying.
- the positive electrode active material layer may be formed only on one side of the positive electrode current collector or on both sides.
- the negative electrode current collector for example, a plate or foil made of copper, nickel, stainless steel or the like can be used, and copper foil is preferable.
- the negative electrode active material layer includes, for example, a negative electrode active material and a binder, and may further include a conductive aid as necessary.
- a material capable of inserting and extracting lithium can be used.
- lithium metal natural graphite, artificial graphite, mesocarbon microbeads (MCMB), hard Carbon materials such as carbon; metal oxides such as iron oxide, ruthenium oxide, molybdenum oxide, and tungsten oxide; polymer materials such as polyacetylene and polypyrrole; simple elements or alloys of metal elements or metalloid elements capable of forming an alloy with lithium Compound etc. are mentioned.
- Examples of simple metal elements or metalloid elements that can form an alloy with lithium include magnesium, boron, arsenic, aluminum, gallium, indium, silicon, germanium, tin, lead, antimony, bismuth, cadmium, silver, Zinc, hafnium, zirconium, yttrium, palladium, platinum and the like can be mentioned.
- alloys or compounds of metal elements or metalloid elements capable of forming an alloy with lithium include, for example, LiAl, AlSb, CuMgSb, SiB 4 , SiB 6 , Mg 2 Si, Mg 2 Sn, Ni 2 Si, TiSi 2, MoSi 2, CoSi 2 , NiSi 2, CaSi 2, CrSi 2, Cu 5 Si, FeSi 2, MnSi 2, NbSi 2, TaSi 2, VSi 2, WSi 2, ZnSi 2, SiC, Si 3 N 4, Examples thereof include Si 2 N 2 O, SiO, SiO 2 , SnO, SnO 2 , SnSiO 3 , LiSiO, and LiSnO.
- the negative electrode active material may be used in the form of a powder, may be used in the form of a film or sheet, and may be used by forming a thin film on the negative electrode current collector. Is preferred.
- binder contained in the negative electrode active material layer examples include polyvinylidene fluoride (PVdF), styrene-butadiene rubber (SBR), and derivatives thereof.
- PVdF polyvinylidene fluoride
- SBR styrene-butadiene rubber
- Examples of the conductive additive contained in the negative electrode active material layer include ketjen black, acetylene black, carbon black, and carbon nanotube.
- the negative electrode is produced, for example, by dispersing and kneading the negative electrode active material in a solvent together with a binder and, if necessary, a conductive auxiliary agent, and then applying the negative electrode active material on the negative electrode current collector and drying and removing the solvent. be able to.
- the negative electrode active material layer may be formed only on one side of the negative electrode current collector or on both sides.
- the separator examples include polyolefins such as polyethylene and polypropylene; fluorine resins such as polytetrafluoroethylene (PTFE); microporous membranes and nonwoven fabrics formed from synthetic resins such as porous vinylon; ceramic nonwoven fabrics, and the like
- PTFE polytetrafluoroethylene
- a porous body made of a material can be used.
- the separator may have a single layer structure or may have a laminated structure in which two or more porous bodies are laminated.
- a cylindrical or square metal can made of nickel or stainless steel, an aluminum laminate film, or the like can be used.
- an aluminum laminate film is used as an exterior member
- the shape of the secondary battery can be freely designed, and the secondary battery can be made lighter than when a metal can is used as the exterior member.
- the polymer electrolyte gel composition of the present invention is used, liquid leakage, which is a problem when producing a secondary battery using only an electrolytic solution containing no polymer using an aluminum laminate film as an exterior member, is suppressed. A safer secondary battery can be manufactured.
- a pair of electrodes and a separator disposed between the pair of electrodes are disposed inside a bag-shaped exterior member, and then in a molten state inside the exterior member.
- Examples thereof include a method for producing the polymer electrolyte gel composition of the present invention by pouring, cooling and solidifying.
- a gas introduction tube and a vacuum distillation apparatus were attached to the flask, and unreacted vinyl acetate monomer was driven out while blowing methanol vapor into the polymerization reaction solution under reduced pressure to obtain a 44.3% by weight methanol solution of the copolymer. Obtained.
- polymer P contained 4 mol% of structural units derived from (3-methacrylamideamidopropyl) trimethylammonium chloride, 1 mol% of vinyl acetate units, and 95 mol% of vinyl alcohol units.
- the Brookfield viscosity of the 4% aqueous solution at 20 ° C. was 34.1 centipoise.
- polymer A had a butyralization degree of 78 mol%, a vinyl acetate unit content of 1 mol%, a vinyl alcohol unit content of 17 mol%, and a cation-modified unit content of 4 mol% (cationic The functional group content was 4 mol%).
- the resulting polymer B had a butyralization degree of 39 mol%, an acetoacetalization degree of 39 mol%, a vinyl acetate unit content of 1 mol%, a vinyl alcohol unit content of 17 mol%, and a cation-modified unit.
- the content was 4 mol% (cationic functional group content was 4 mol%).
- the resulting polymer C had a butyralization degree of 39 mol%, a vinyl acetate unit content of 1 mol%, a vinyl alcohol unit content of 21 mol%, and a cation-modified unit content of 39 mol% (cationic The functional group content was 19.5 mol%).
- the resulting polymer D had a butyralization degree of 26 mol%, an acetoacetalization degree of 26 mol%, a vinyl acetate unit content of 1 mol%, a vinyl alcohol unit content of 21 mol%, and a cation-modified unit content.
- the content was 26 mol% (cationic functional group content was 13 mol%).
- Example 1 5 parts by weight of Polymer A (however, not including the weight of counter anion) and 95 parts by weight of ethanol were mixed and stirred for 1 hour to prepare a polymer solution.
- An electrolytic solution dissolved in was prepared. 95 parts by weight of the prepared electrolytic solution was mixed with the above polymer solution and stirred sufficiently until uniform to obtain a mixed solution.
- the entire amount of the mixed solution is poured into a previously prepared “Teflon” tray-like container, dried at 50 ° C. for 5 hours, and then dried under reduced pressure at 70 ° C. for 3 hours in a vacuum dryer. Ethanol was removed, and a thin film polymer electrolyte gel composition having a thickness of about 200 ⁇ m in a state of being in close contact with a “Teflon” container was prepared.
- Example 2 In Example 1, a polymer electrolyte gel composition was prepared in the same manner as in Example 1 except that the polymer B was used instead of the polymer A.
- Example 3 In Example 1, a polymer electrolyte gel composition was prepared in the same manner as in Example 1 except that the polymer C was used instead of the polymer A.
- Example 4 In Example 1, a polymer electrolyte gel composition was produced in the same manner as in Example 1 except that the polymer D was used instead of the polymer A.
- Example 1 a polymer electrolyte gel composition was prepared in the same manner as in Example 1 except that the polymer Y was used instead of the polymer A, and tetrahydrofuran was used instead of ethanol.
- Example 2 A polymer electrolyte gel was prepared in the same manner as in Example 1, except that polyvinyl butyral (Kuraray Europ Gesellshaft Mitsche Bechlenktel “Movital” B60H) (polymer W) (polymer W) was used instead of polymer A. A composition was prepared.
- Example 3 a polymer electrolyte gel composition was produced in the same manner as in Example 1 except that the polymer Z was used instead of the polymer A.
- Example 4 In Example 3, the usage amount of the polymer C was changed from 5 parts by weight to 10 parts by weight, and the usage amount of the prepared electrolyte was changed from 95 parts by weight to 90 parts by weight.
- a polymer electrolyte gel composition was prepared by the method.
- Example 5 In Example 3, the amount of the polymer C used was changed from 5 parts by weight to 0.4 parts by weight, and the amount of the prepared electrolyte used was changed from 95 parts by weight to 99.6 parts by weight. 3 was used to prepare a polymer electrolyte gel composition.
- the container made of “Teflon” containing the ionic conductivity polymer electrolyte gel composition was transferred into a glove box filled with argon gas, and after peeling the polymer electrolyte gel composition from the container made of “Teflon”, A sample piece for measurement was obtained by cutting into a circle having a diameter of 1 cm.
- the measurement sample piece was sandwiched between stainless steel electrodes to prepare a cell. This cell was connected to an impedance analyzer with a lead wire, and the resistance value of the sample was measured at 20 ° C. by the AC impedance method.
- the measurement was performed in an argon atmosphere, and the ion conductivity ⁇ was calculated from the resistance value, thickness (about 200 ⁇ m) of the measurement sample piece, and the area of the stainless steel electrode.
- Cycle characteristics Aluminum foil having a thickness of 20 ⁇ m for the positive electrode current collector, lithium cobaltate (LiCoO 2 ) for the positive electrode active material, a microporous polyethylene film having a thickness of 25 ⁇ m for the separator, graphite powder for the negative electrode active material, and 15 ⁇ m for the negative electrode current collector
- the polymer electrolyte gel composition having the same composition as the polymer electrolyte gel composition in each of the above Examples or Comparative Examples is used as the polymer electrolyte gel.
- a lithium ion secondary battery was manufactured. Charging / discharging was performed using the above lithium ion secondary battery, and the cycle characteristics were examined. The cycle characteristics are as follows: charge / discharge is repeated 100 cycles at 23 ° C.
- the weight ratio of the vinyl acetal polymer and the electrolyte solution in the polymer electrolyte gel composition is the same, but the vinyl acetal polymer does not contain a cationic functional group (Comparative Examples 1 to 3).
- the ion conductivity was low, and the cycle characteristics in the secondary battery were also inferior.
- the polymer electrolyte gel composition may not have sufficient strength, and may cause liquid leakage. It has been found that it is difficult to ensure sufficient safety when used as a polymer electrolyte gel.
- the polymer electrolyte gel composition of the present invention can be suitably used for polymer electrolyte gels of batteries and capacitors.
- the batteries when used as a polymer electrolyte gel for a secondary battery, particularly a lithium ion secondary battery, it exhibits high electrical load characteristics due to excellent ionic conductivity, and also effectively traps anions to reduce the internal resistance of the battery. It shows excellent repeated charge / discharge characteristics (cycle characteristics) because it can suppress the increase.
- the polymer electrolyte gel composition of the present invention can also be used for secondary batteries using sodium ions, magnesium ions, and calcium ions as charge transfer bodies.
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Abstract
Description
上記の高分子化合物において各繰り返し単位の配列順序は特に限定されず、ランダムに配列されていてもよいし、ブロック状に配列されていてもよい。
(1)酢酸ビニルに代表されるビニルエステル系単量体とカチオン性官能基を含む重合性単量体とを共重合して得られる共重合体をケン化した後、アセタール化する方法、
(2)ビニルアルコール系重合体を、カチオン性官能基を含むアルデヒド、カチオン性官能基を含むアルデヒドのヘミアセタール化物、および、カチオン性官能基を含むアルデヒドの完全アセタール化物からなる群より選ばれる少なくとも1種を用いてアセタール化する方法、
(3)ビニルアルコール系重合体にカチオン性官能基を含むアルコールまたはカチオン性官能基を含むエポキシ化合物を反応させて、エーテル結合を介してカチオン性官能基を導入した後、アセタール化する方法、
(4)ビニルアルコール系重合体にカチオン性官能基を含むカルボン酸またはその誘導体を反応させて、エステル結合を介してカチオン性官能基を導入した後、アセタール化する方法、
(5)ビニルアセタール系重合体にカチオン性官能基を含むアルコールまたはカチオン性官能基を含むエポキシ化合物を反応させて、エーテル結合を介してカチオン性官能基を導入する方法、
(6)ビニルアセタール系重合体にカチオン性官能基を含むカルボン酸またはその誘導体を反応させて、エステル結合を介してカチオン性官能基を導入する方法、
あるいは、上記の方法の2種以上を組み合わせた方法などが挙げられる。これらの中でも、特に方法(1)および(2)が好適に採用される。
アセタール化する際の条件としては、例えば、ポリビニルアルコールにn-ブチルアルデヒドを酸触媒の存在下反応させてポリビニルブチラールを製造する際に採用されるような公知の条件を採用できる。
アセタール化する際の条件としては、例えば、ポリビニルアルコールにn-ブチルアルデヒドを酸触媒の存在下反応させてポリビニルブチラールを製造する際に採用されるような公知の条件を採用できる。
ビニルアルコール系重合体のアセタール化に用いられる化合物としては、方法(1)において、アセタール化に用いられる化合物の例として上記した化合物が挙げられる。また、当該アセタール化に用いられる化合物の一部または全部は、方法(2)において、カチオン性官能基を含むアルデヒド、カチオン性官能基を含むアルデヒドのヘミアセタール化物、および、カチオン性官能基を含むアルデヒドの完全アセタール化物の例として上記した化合物であってもよい。
アセタール化する際の条件としては、例えば、ポリビニルアルコールにn-ブチルアルデヒドを酸触媒の存在下反応させてポリビニルブチラールを製造する際に採用されるような公知の条件を採用できる。
アセタール化度(モル%)=100×[nI×2]/[nI×2 + nII + nIII]
ブチラール化度(モル%)=100×[nI(Bu)×2]/[nI(Bu)×2 + nI(Ac)×2 + nII + nIII]
アセトアセタール化度(モル%)=100×[nI(Ac)×2]/[nI(Bu)×2 + nI(Ac)×2 + nII + nIII]
上記のリチウムと合金を形成可能な金属元素もしくは半金属元素の単体としては、例えば、マグネシウム、ホウ素、ヒ素、アルミニウム、ガリウム、インジウム、ケイ素、ゲルマニウム、スズ、鉛、アンチモン、ビスマス、カドミウム、銀、亜鉛、ハフニウム、ジルコニウム、イットリウム、パラジウム、白金等が挙げられる。また、上記のリチウムと合金を形成可能な金属元素もしくは半金属元素の合金または化合物としては、例えば、LiAl、AlSb、CuMgSb、SiB4、SiB6、Mg2Si、Mg2Sn、Ni2Si、TiSi2、MoSi2、CoSi2、NiSi2、CaSi2、CrSi2、Cu5Si、FeSi2、MnSi2、NbSi2、TaSi2、VSi2、WSi2、ZnSi2、SiC、Si3N4、Si2N2O、SiO、SiO2、SnO、SnO2、SnSiO3、LiSiO、LiSnO等が挙げられる。
高分子電解質ゲル組成物を用いた二次電池の場合、容量の大きなリチウム金属を負極に利用できる利点がある。負極活物質としてリチウム金属を使用すると、黒鉛粉末などの炭素材料を使用した場合に比べて二次電池の電池容量を飛躍的に向上させることができる。
負極活物質は粉末の状態で用いてもよいし、フィルムやシートの状態で用いてもよいし、負極集電体上に薄膜を形成して用いてもよいが、粉末の状態で用いられるのが好ましい。
撹拌機、温度計、滴下ロートおよび還流冷却器を付したフラスコ中に、酢酸ビニル2500g(29モル)、メタノール697gおよび(3-メタクリルアミドプロピル)トリメチルアンモニウムクロリド4.5g(0.020モル)を仕込んだ。次いで当該フラスコを恒温槽内に据えて撹拌しながら系内を窒素置換し、内温を60℃まで昇温した。その後、2,2’-アゾビスイソブチロニトリル3.5g(0.021モル)をメタノール50gと共に添加して重合を開始した。重合時間3時間の間に(3-メタクリルアミドプロピル)トリメチルアンモニウムクロリドの50重量%メタノール溶液340g((3-メタクリルアミドプロピル)トリメチルアンモニウムクロリドを0.77モル含む)を一定速度で滴下した。重合停止時の系内の固形分濃度は49.8重量%であった。
上記のフラスコにガス導入管および減圧蒸留装置を取り付け、減圧下に重合反応液中にメタノール蒸気を吹きこみながら未反応の酢酸ビニルモノマーを追い出して、共重合体の44.3重量%メタノール溶液を得た。
得られた重合体Pは、(3-メタクリルアミドプロピル)トリメチルアンモニウムクロリドに由来する構成単位を4モル%、酢酸ビニル単位を1モル%、ビニルアルコール単位を95モル%含有していた。また、4%水溶液の20℃におけるブルックフィールド粘度は、34.1センチポアズであった。
得られた重合体Aのブチラール化度は78モル%、酢酸ビニル単位の含有量は1モル%、ビニルアルコール単位の含有量は17モル%、カチオン変性単位の含有量は4モル%(カチオン性官能基含有量は4モル%)であった。
製造例1において、使用するn-ブチルアルデヒド75g(1.0モル)の代わりに、n-ブチルアルデヒド37g(0.51モル)およびアセトアルデヒド23g(0.52モル)の混合物を用いて、製造例1と同様の方法により、カチオン変性ポリビニルアセタール(重合体B)を得た。
得られた重合体Bのブチラール化度は39モル%、アセトアセタール化度は39モル%、酢酸ビニル単位の含有量は1モル%、ビニルアルコール単位の含有量は17モル%、カチオン変性単位の含有量は4モル%(カチオン性官能基含有量は4モル%)であった。
製造例1において、使用する重合体P110gの代わりに、ポリビニルアルコール(株式会社クラレ製「ポバール」PVA-117)110gを用い、また、使用するn-ブチルアルデヒド75g(1.0モル)の代わりに、n-ブチルアルデヒド37g(0.51モル)および六フッ化リン酸3-(2,2-ジメトキシエチル)-1-メチル-1H-イミダゾール-3-イウム163g(0.52モル)の混合物を用いて、製造例1と同様の方法により、カチオン変性ポリビニルアセタール(重合体C)を得た。
得られた重合体Cのブチラール化度は39モル%、酢酸ビニル単位の含有量は1モル%、ビニルアルコール単位の含有量は21モル%、カチオン変性単位の含有量は39モル%(カチオン性官能基含有量は19.5モル%)であった。
製造例3において、使用するn-ブチルアルデヒド37g(0.51モル)および六フッ化リン酸3-(2,2-ジメトキシエチル)-1-メチル-1H-イミダゾール-3-イウム163g(0.52モル)の混合物の代わりに、n-ブチルアルデヒド25g(0.35モル)、アセトアルデヒド15g(0.34モル)および六フッ化リン酸3-(2,2-ジメトキシエチル)-1-メチル-1H-イミダゾール-3-イウム109g(0.34モル)の混合物を用いて、製造例3と同様の方法により、カチオン変性ポリビニルアセタール(重合体D)を得た。
得られた重合体Dのブチラール化度は26モル%、アセトアセタール化度は26モル%、酢酸ビニル単位の含有量は1モル%、ビニルアルコール単位の含有量は21モル%、カチオン変性単位の含有量は26モル%(カチオン性官能基含有量は13モル%)であった。
還流冷却器、温度計、イカリ型攪拌翼を備えた2リットルガラス製容器に、イオン交換水1350g、ポリビニルアルコール(株式会社クラレ製「ポバール」PVA-117)110gを仕込み、120rpmで攪拌しながら、95℃で、60分かけてポリビニルアルコールを完全に溶解した(ポリビニルアルコールの濃度7.5重量%)。この水溶液を120rpmで攪拌下、10℃まで約30分かけて徐々に冷却した後、ホルマリン(37重量%ホルムアルデヒド水溶液)84g(ホルムアルデヒドを1.0モル含む)と20重量%の塩酸131mLを添加し、アセタール化反応を25分間行った。その後、150分かけて45℃まで昇温し、240分間保持後、室温まで冷却した。析出した樹脂をイオン交換水で洗浄後、水酸化ナトリウム水溶液を添加して中和を行い、イオン交換水で再度洗浄し、乾燥して、無変性ポリビニルホルマール(重合体Y)を得た。
得られた重合体Yのホルマール化度は78モル%、酢酸ビニル単位の含有量は1モル%、ビニルアルコール単位の含有量は21モル%であった。
製造例5において、使用するホルマリン(37重量%ホルムアルデヒド水溶液)84g(ホルムアルデヒドを1.0モル含む)の代わりに、n-ブチルアルデヒド37g(0.51モル)およびアセトアルデヒド23g(0.52モル)の混合物を用いて、製造例5と同様の方法により、無変性ポリビニルアセタール(重合体Z)を得た。
得られた重合体Zのブチラール化度は39モル%、アセトアセタール化度は39モル%、酢酸ビニル単位の含有量は1モル%、ビニルアルコール単位の含有量は21モル%であった。
重合体A 5重量部(但し、カウンターアニオンの重量を含まない)とエタノール95重量部とを混合し、1時間攪拌して重合体溶液を調製した。また、別途、炭酸エチレンと炭酸エチルメチルとを炭酸エチレン:炭酸エチルメチル=3:7の重量比で混合した非水系溶媒に、電解質として六フッ化リン酸リチウムを1.0モル/Lの濃度で溶解した電解液を調製した。調製した電解液95重量部を上記の重合体溶液と混合し、均一になるまで充分攪拌して混合液とした。次に、あらかじめ準備した「テフロン」製のトレー状の容器中にこの混合液の全量を注ぎ込み、50℃で5時間加熱乾燥し、その後、真空乾燥機中で70℃で3時間減圧乾燥してエタノールを取り除き、「テフロン」製の容器に密着した状態の厚さ約200μmの薄膜状の高分子電解質ゲル組成物を作製した。
実施例1において、重合体Aの代わりに重合体Bを使用したこと以外は実施例1と同様の方法により、高分子電解質ゲル組成物を作製した。
実施例1において、重合体Aの代わりに重合体Cを使用したこと以外は実施例1と同様の方法により、高分子電解質ゲル組成物を作製した。
実施例1において、重合体Aの代わりに重合体Dを使用したこと以外は実施例1と同様の方法により、高分子電解質ゲル組成物を作製した。
実施例1において、重合体Aの代わりに重合体Yを使用し、エタノールの代わりにテトラヒドロフランを使用したこと以外は実施例1と同様の方法により、高分子電解質ゲル組成物を作製した。
実施例1において、重合体Aの代わりにポリビニルブチラール(クラレイ ユーロップ ゲゼルシャフト ミット ベシュレンクテル ハフツング製「モビタール」B60H)(重合体W)を使用したこと以外は実施例1と同様の方法により、高分子電解質ゲル組成物を作製した。
実施例1において、重合体Aの代わりに重合体Zを使用したこと以外は実施例1と同様の方法により、高分子電解質ゲル組成物を作製した。
実施例3において、重合体Cの使用量を5重量部から10重量部に変更し、調製した電解液の使用量を95重量部から90重量部に変更したこと以外は実施例3と同様の方法により、高分子電解質ゲル組成物を作製した。
実施例3において、重合体Cの使用量を5重量部から0.4重量部に変更し、調製した電解液の使用量を95重量部から99.6重量部に変更したこと以外は実施例3と同様の方法により、高分子電解質ゲル組成物を作製した。
前述の真空乾燥機中における減圧乾燥の後、高分子電解質ゲル組成物の表面が湿潤していなかったものを液漏れ「なし」、湿潤していたものを液漏れ「あり」と評価した。
高分子電解質ゲル組成物を「テフロン」製の容器から剥離するときに、破断しなかったものを機械的強度「充分」、破断したものを機械的強度「不充分」と評価した。
高分子電解質ゲル組成物の入った「テフロン」製の容器をアルゴンガスで充満させたグローブボックス内に移し入れ、高分子電解質ゲル組成物を「テフロン」製の容器から剥離した後、直径1cmの円状に切断し、測定用試料片を得た。この測定用試料片をステンレス電極に挟みこみセルを作製した。このセルをリード線でインピーダンスアナライザーにつなぎ、交流インピーダンス法により20℃にて試料の抵抗値を測定した。測定は、アルゴン雰囲気中で行い、測定用試料片の抵抗値、厚み(約200μm)および、ステンレス電極の面積からイオン伝導度σを算出した。
正極集電体に厚み20μmのアルミニウム箔、正極活物質にコバルト酸リチウム(LiCoO2)、セパレータに厚み25μmの微孔性ポリエチレンフィルム、負極活物質に黒鉛粉末、負極集電体に厚み15μmの銅箔を用い、外装部材にアルミラミネートフィルムを用い、さらに高分子電解質ゲルとして上記の各実施例または比較例における高分子電解質ゲル組成物と同様の組成を有する高分子電解質ゲル組成物を用いたリチウムイオン二次電池を作製した。
上記のリチウムイオン二次電池を用いて充放電を行い、サイクル特性を調べた。サイクル特性は、23℃で500mAの定電流定電圧充電を上限4.2Vまで2時間行った後、500mAの定電流放電を終止電圧3.0Vまで行うという充放電を100サイクル繰返し、1サイクル目の放電容量を100%としたときの100サイクル目の放電容量維持率、すなわち、〔500mA放電における100サイクル目の放電容量〕/〔500mA放電における1サイクル目の放電容量〕×100(%)により求められる値から評価した。
Claims (7)
- 高分子電解質ゲル組成物用のビニルアセタール系重合体であって、カチオン性官能基を含むビニルアセタール系重合体。
- ビニルエステル系単量体とカチオン性官能基を含む重合性単量体との共重合体をケン化した後、アセタール化することによって得られる、請求項1に記載のビニルアセタール系重合体。
- 前記アセタール化に用いられる化合物が、炭素数1~15の脂肪族アルデヒド、炭素数1~15の脂肪族アルデヒドのヘミアセタール化物、炭素数1~15の脂肪族アルデヒドの完全アセタール化物、炭素数7~20の芳香族アルデヒド、炭素数7~20の芳香族アルデヒドのヘミアセタール化物、および、炭素数7~20の芳香族アルデヒドの完全アセタール化物からなる群より選ばれる少なくとも1種である、請求項2に記載のビニルアセタール系重合体。
- ビニルアルコール系重合体を、カチオン性官能基を含むアルデヒド、カチオン性官能基を含むアルデヒドのヘミアセタール化物、および、カチオン性官能基を含むアルデヒドの完全アセタール化物からなる群より選ばれる少なくとも1種を用いてアセタール化することによって得られる、請求項1に記載のビニルアセタール系重合体。
- 前記カチオン性官能基が、第四級アンモニウム基、イミダゾリウム基、ピリジニウム基、ホスホニウム基およびスルホニウム基からなる群より選ばれる少なくとも1種である、請求項1~4のいずれか1項に記載のビニルアセタール系重合体。
- 請求項1~5のいずれか1項に記載のビニルアセタール系重合体と電解液とを含有し、当該ビニルアセタール系重合体と当該電解液との重量比が0.5:99.5~9:91である高分子電解質ゲル組成物。
- 請求項1~5のいずれか1項に記載のビニルアセタール系重合体と電解液とを0.5:99.5~9:91の割合で混合する工程を含む、高分子電解質ゲル組成物の製造方法。
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JP5718227B2 (ja) | 2015-05-13 |
KR101757178B1 (ko) | 2017-07-12 |
US9356318B2 (en) | 2016-05-31 |
EP2524932A4 (en) | 2014-06-04 |
TWI498376B (zh) | 2015-09-01 |
EP2524932A1 (en) | 2012-11-21 |
US20120321963A1 (en) | 2012-12-20 |
TW201137018A (en) | 2011-11-01 |
EP2524932B1 (en) | 2015-11-25 |
KR20120125498A (ko) | 2012-11-15 |
CN102791747A (zh) | 2012-11-21 |
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