WO2016031562A1 - 塗工液、塗工膜、及び複合材料 - Google Patents
塗工液、塗工膜、及び複合材料 Download PDFInfo
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- WO2016031562A1 WO2016031562A1 PCT/JP2015/072769 JP2015072769W WO2016031562A1 WO 2016031562 A1 WO2016031562 A1 WO 2016031562A1 JP 2015072769 W JP2015072769 W JP 2015072769W WO 2016031562 A1 WO2016031562 A1 WO 2016031562A1
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- Prior art keywords
- coating film
- coating
- coating liquid
- acid
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Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D127/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Coating compositions based on derivatives of such polymers
- C09D127/02—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Coating compositions based on derivatives of such polymers not modified by chemical after-treatment
- C09D127/12—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Coating compositions based on derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms
- C09D127/16—Homopolymers or copolymers of vinylidene fluoride
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/30—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D101/00—Coating compositions based on cellulose, modified cellulose, or cellulose derivatives
- C09D101/08—Cellulose derivatives
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D103/00—Coating compositions based on starch, amylose or amylopectin or on their derivatives or degradation products
- C09D103/04—Starch derivatives
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D105/00—Coating compositions based on polysaccharides or on their derivatives, not provided for in groups C09D101/00 or C09D103/00
- C09D105/08—Chitin; Chondroitin sulfate; Hyaluronic acid; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D129/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal, or ketal radical; Coating compositions based on hydrolysed polymers of esters of unsaturated alcohols with saturated carboxylic acids; Coating compositions based on derivatives of such polymers
- C09D129/02—Homopolymers or copolymers of unsaturated alcohols
- C09D129/04—Polyvinyl alcohol; Partially hydrolysed homopolymers or copolymers of esters of unsaturated alcohols with saturated carboxylic acids
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/24—Electrically-conducting paints
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/20—Diluents or solvents
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/60—Additives non-macromolecular
- C09D7/61—Additives non-macromolecular inorganic
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/60—Additives non-macromolecular
- C09D7/63—Additives non-macromolecular organic
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/65—Additives macromolecular
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- 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
- H01G11/22—Electrodes
- H01G11/26—Electrodes characterised by their structure, e.g. multi-layered, porosity or surface features
- H01G11/28—Electrodes characterised by their structure, e.g. multi-layered, porosity or surface features arranged or disposed on a current collector; Layers or phases between electrodes and current collectors, e.g. adhesives
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- 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
- H01G11/66—Current collectors
- H01G11/68—Current collectors characterised by their material
-
- 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
- H01G11/66—Current collectors
- H01G11/70—Current collectors characterised by their structure
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M4/00—Electrodes
- H01M4/02—Electrodes composed of, or comprising, active material
- H01M4/64—Carriers or collectors
- H01M4/66—Selection of materials
- H01M4/661—Metal or alloys, e.g. alloy coatings
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M4/00—Electrodes
- H01M4/02—Electrodes composed of, or comprising, active material
- H01M4/64—Carriers or collectors
- H01M4/66—Selection of materials
- H01M4/665—Composites
- H01M4/667—Composites in the form of layers, e.g. coatings
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M4/00—Electrodes
- H01M4/02—Electrodes composed of, or comprising, active material
- H01M4/64—Carriers or collectors
- H01M4/66—Selection of materials
- H01M4/668—Composites of electroconductive material and synthetic resins
-
- 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
Definitions
- the present invention relates to a coating liquid capable of forming a coating film excellent in adhesion and the like on the surface of a base material such as metal, glass, resin, etc., a coating film formed using this coating liquid, and
- the present invention relates to a formation method, a composite material, an electrode plate member, an electrode plate for a power storage device, a manufacturing method thereof, and a power storage device.
- a fluororesin exhibits various properties such as non-adhesiveness, heat resistance, oxidation resistance, weather resistance, chemical resistance, slipperiness, water and oil repellency, and electrical characteristics due to its characteristic structure.
- various functionalities of the coating film formed using a functional coating liquid such as a solution, slurry, paste, etc. (hereinafter collectively referred to as “slurry”) containing a fluororesin
- slurry containing a fluororesin
- PVDF Polyvinylidene fluoride
- One of the characteristics that the coating film should have is excellent adhesion to the substrate. This is because the functionality of the coating film is fully exhibited only when the adhesion to the substrate is excellent.
- PVDF exhibits non-adhesiveness with respect to a general base material, even when a coating liquid simply containing PVDF is used, the adhesion of the formed coating film to the base material is insufficient. . Therefore, various proposals have been made to improve the adhesion of a coating film containing PVDF to a substrate.
- Patent Documents 1 and 2 proposals have been made for further laminating a film or other coating film on a coating film formed by blending PVDF with an acrylic resin.
- Patent Documents 3 and 4 proposals have been proposed to use a modified fluororesin in which a functional group or a modified substance that is expected to improve adhesion is introduced into a basic repeating unit.
- PVDF is widely used as a binder for binding an active material of a lithium ion battery
- a binder solution obtained by dissolving PVDF in an NMP solution is widely used as a dispersion medium.
- the amorphous part of PVDF suitably functions as a polar solvent or electrolyte matrix in the electrolytic solution, and does not completely inhibit the diffusion of lithium ions (Non-patent Document 1).
- the binding force of the active material may be insufficient. For this reason, various measures for improving the binding force of the active material have been studied.
- Patent Document 5 it was obtained by binding the primary particles of the positive electrode active material with a water-soluble polymer binder and binding the secondary particles to each other, or the secondary particles and the current collector with a fluororesin binder or a rubber binder.
- An electrode has been proposed (Patent Document 5).
- Patent Documents 6 and 7 modified PVDF obtained by partially dehydrofluorinating with an alkali and further oxidizing with an oxidizing agent.
- JP 2000-280402 A JP 2005-246923 A JP-A-10-329280 JP 2004-067716 A JP 2007-234277 A JP 2004-071517 A JP 2004-071518 A
- the present invention has been made in view of the above-described problems of the prior art, and the object of the present invention is to contain metal, glass, resin, etc. while containing PVDF exhibiting remarkable non-adhesiveness. With excellent adhesion to the surface of the base material, non-adhesiveness, antifouling properties, chemical resistance, slidability, water repellency, conductivity, antifungal / antibacterial properties, and deodorizing properties An object of the present invention is to provide a coating solution capable of forming a coating film capable of exhibiting various functions.
- the subject of the present invention is a coating film formed using this coating liquid, and a method for forming the same, a composite material, a member for an electrode plate, an electrode plate for a power storage device, a method for manufacturing the same, and a power storage To provide an apparatus.
- the coating liquid shown below is provided.
- the polar solvent is selected from the group consisting of N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, N-ethyl-2-pyrrolidone, and ⁇ -alkoxypropionamides
- the coating liquid according to [1] which is at least one kind.
- the hydrophilic polymer is at least one selected from the group consisting of chitosan derivatives, cellulose derivatives, starch derivatives, unmodified polyvinyl alcohol, and modified polyvinyl alcohol, as described in [1] or [2] above. Coating liquid.
- the chitosan derivative is at least one hydroxyalkyl chitosan selected from the group consisting of hydroxyethyl chitosan, hydroxypropyl chitosan, hydroxybutyl chitosan, and dihydroxypropyl chitosan
- the cellulose derivative includes hydroxyethyl cellulose, hydroxy At least one selected from the group consisting of propylcellulose, methylcellulose, hydroxyethylmethylcellulose, and hydroxypropylmethylcellulose
- the starch derivative is at least selected from hydroxyethyl starch, hydroxypropyl starch, and hydroxybutyl starch 1 type
- the saponification degree of the unmodified polyvinyl alcohol is 98 mol% or less
- the modified polyvinyl alcohol The group consisting of carboxyl group-modified polyvinyl alcohol, carbonyl group-modified polyvinyl alcohol, silanol group-modified polyvinyl alcohol, amino group-modified polyvinyl alcohol
- the coating film shown below and its formation method are provided.
- [7] A coating film formed using the coating liquid according to any one of [1] to [6].
- [8] The coating film according to [7], wherein a contact angle measured according to JIS R3257 is 70 ° or more.
- [9] A method for forming a coating film, comprising a step of heating the coating solution according to any one of [1] to [6] to 80 ° C. or higher.
- the following composite material is provided.
- a composite material comprising: a base material; and the coating film according to [7] or [8], which is integrally disposed on the base material.
- the substrate is at least one selected from the group consisting of metal, glass, natural resin, synthetic resin, ceramics, wood, paper, fiber, nonwoven fabric, woven fabric, and leather.
- a member for an electrode plate comprising: a current collector; and a coating film made of the coating liquid according to [6], disposed on the surface of the current collector.
- the electrode plate for electrical storage apparatuses shown below, its manufacturing method, and an electrical storage apparatus are provided.
- An electrode plate for a power storage device comprising: the electrode plate member according to [12]; and an electrode layer disposed on a surface of the coating film constituting the electrode plate member.
- the electrode plate for a power storage device according to [13] wherein the current collector constituting the electrode member is a copper foil, and the electrode layer contains a negative electrode active material.
- a power storage device comprising: forming a coating film by applying the coating liquid according to [6] to a surface of a current collector, and then forming an electrode layer on the surface of the coating film Manufacturing method of electrode plate.
- a power storage device comprising the electrode plate for a power storage device according to any one of [13] to [16].
- the surface of the base material such as metal, glass, and resin is excellent in adhesion, non-adhesive, antifouling
- a coating solution capable of forming a coating film capable of exhibiting various desired functions such as chemical resistance, slidability, water repellency, conductivity, antifungal / antibacterial properties, and deodorization properties.
- a coating film formed using this coating liquid a method for forming the coating film, a composite material, a member for an electrode plate, an electrode plate for a power storage device, a method for manufacturing the power storage device, and a power storage device. can do.
- the coating liquid of the present invention By using the coating liquid of the present invention, it is possible to produce a coating film provided with various functions such as conductivity and water repellency, and a composite material provided with the coating film provided with such a function. it can.
- the coating liquid of the present invention maintains an appropriate viscosity even when stored for a long period of time, and it is difficult for the filler to settle and separate even when a filler such as a conductive material is contained. For this reason, when the coating liquid of the present invention is used, the contact between the current collector such as aluminum foil and copper foil and the electrode layer is excellent in adhesion and electrolytic solution resistance and in contact with the current collector. It is also possible to form a conductive coating film (thin film) serving as an undercoat layer with improved resistance. Therefore, if the coating liquid of this invention is used, the electrical storage apparatus provided with the electrode plate for electrical storage apparatuses, such as a battery and a capacitor excellent in various characteristics, and this electrical storage apparatus electrode plate can be provided.
- the coating liquid of the present invention is not limited to the power storage device as described above, and examples thereof include paints for electronic materials, inks, toners, rubbers, plastics, ceramics, magnetic materials, adhesives, and liquid crystal color filters. Use in many industrial fields is expected.
- the present invention is not limited to the following embodiments.
- the present inventors have included a hydrophilic polymer and polyvinylidene fluoride (PVDF) in a polar solvent, so that the functionality derived from the fluororesin such as non-adhesiveness and water repellency, and the substrate
- PVDF polyvinylidene fluoride
- the coating liquid of the present invention contains a polar solvent, a hydrophilic polymer having hydrophilicity as well as binding properties and dispersibility to a filler such as a conductive material, and PVDF.
- a concentration gradient of each component occurs. Specifically, in the lower layer in the coating film (layer in contact with the base material), the ratio of the hydrophilic polymer is relatively increased, and the adhesion to the base material is exhibited. In addition, in the upper layer (surface layer (layer opposite to the base material)) in the coating layer, the PVDF content is relatively increased, and non-adhesiveness, water repellency, chemical resistance, and the like are exhibited. Moreover, since the concentration gradients of the two components of the hydrophilic polymer and PVDF are both continuous, no interface is formed between the two components, and the possibility of interfacial peeling is extremely low.
- the coating liquid of the present invention contains a hydrophilic polymer.
- the hydrophilic polymer is a polymer (polymer) having a hydrophilic functional group such as a hydroxyl group or a carboxyl group in its molecular structure.
- Specific examples of the hydrophilic polymer include chitosan derivatives, cellulose derivatives, starch derivatives, unmodified polyvinyl alcohol, and modified polyvinyl alcohol.
- Chitosan derivatives are preferred because of their good solubility in organic solvents.
- the chitosan derivative one obtained from the market can be used as it is.
- Specific examples of chitosan derivatives include hydroxyalkyl chitosan, carboxyalkyl chitosan, carboxyacyl chitosan, succinyl chitosan, and cationized chitosan. Of these, hydroxyalkyl chitosan, carboxyalkyl chitosan, and carboxyacyl chitosan are preferable.
- Hydroxyalkyl chitosan is a natural polymer derived from living organisms and has a low environmental impact.
- hydroxyalkyl chitosan hydroxyethyl chitosan, hydroxypropyl chitosan, hydroxybutyl chitosan, hydroxybutyl hydroxypropyl chitosan, and dihydroxypropyl chitosan are preferable.
- Hydroxyalkyl chitosan can be produced, for example, by reacting an amino group of chitosan with alkylene oxide or oxirane methanol. However, hydroxyalkyl chitosan produced by other methods can also be used. Moreover, what mixed and reacted the alkylene oxide and oxirane methanol may be used.
- hydroxybutylchitosan can be obtained.
- dihydroxypropyl chitosan can be obtained by stirring and dispersing chitosan in a medium such as hydrous isopropyl alcohol, adding oxirane methanol, and then heating and stirring.
- the hydroxyalkyl chitosan has a hydroxyalkylation degree of preferably 0.5 to 4.
- the dispersibility of the conductive material can be improved.
- the hydroxyalkylation degree of hydroxyalkylchitosan is less than 0.5, the dispersibility of the filler and the stability of the slurry (coating liquid) may be insufficient.
- the filler dispersibility does not change even when the hydroxyalkylation degree of the hydroxyalkylchitosan exceeds 4, so that it tends to be uneconomical.
- “Hydroxyalkylation degree (no unit)” means the rate of addition of alkylene oxide or oxirane methanol to chitosan. That is, “hydroxyalkylation degree of 0.5 to 4” means that 0.5 to 4 mol of alkylene oxide or oxirane methanol is added per one (1 mol) of pyranose ring constituting chitosan. means. In order to obtain a hydroxyalkylchitosan having a hydroxyalkylation degree within the above range, 0.6 to 10 moles of alkylene oxide or oxiranemethanol per chitosan per pyranose ring (1 mole) constituting chitosan. Can be reacted.
- the weight average molecular weight of the hydroxyalkyl chitosan is preferably 2,000 to 350,000, and more preferably 5,000 to 250,000.
- the weight average molecular weight of the hydroxyalkyl chitosan is less than 2,000, the strength of the coating film may be insufficient.
- the weight average molecular weight of the hydroxyalkyl chitosan exceeds 350,000, the viscosity of the coating liquid tends to increase, and it tends to be difficult to increase the solid content concentration of a filler such as a conductive material.
- the content of the chitosan derivative in the coating liquid is preferably 0.1 to 40 parts by weight, and preferably 0.5 to 20 parts by weight, when the total amount of the coating liquid is 100 parts by weight. Further preferred.
- Cellulose derivatives are preferred because they are hydrophilic polymers with excellent safety.
- the cellulose derivative one obtained from the market can be used as it is, and it may be used alone or as a mixture.
- Specific examples of cellulose derivatives include methylcellulose, ethylcellulose, butylcellulose, carboxymethylcellulose, hydroxymethylcellulose, hydroxyethylcellulose, hydroxypropylcellulose, hydroxyethylmethylcellulose, hydroxypropylmethylcellulose, cellulose acetate, alkali cellulose, viscose, cellulose sulfate, and fatty acid cellulose. And cationized cellulose. Of these, hydroxyethyl cellulose, hydroxypropyl cellulose, methyl cellulose, hydroxyethyl methyl cellulose, and hydroxypropyl methyl cellulose are preferable.
- the content of the cellulose derivative in the coating liquid is preferably 0.1 to 40 parts by mass, and preferably 0.5 to 20 parts by mass when the total amount of the coating liquid is 100 parts by mass. Further preferred.
- Starch derivatives are preferred because they are hydrophilic polymers with excellent safety. As the starch derivatives, those obtained from the market can be used as they are, and they may be used alone or as a mixture. Specific examples of starch derivatives include hydroxyethyl starch, hydroxypropyl starch, hydroxybutyl starch, carboxymethyl starch, and cationized starch. Of these, hydroxyethyl starch, hydroxypropyl starch, and hydroxybutyl starch are preferred.
- the content of the starch derivative in the coating liquid is preferably 0.1 to 40 parts by mass, and preferably 0.5 to 20 parts by mass, when the total amount of the coating liquid is 100 parts by mass. Further preferred.
- Polyvinyl alcohol may be unmodified PVA or modified PVA.
- PVA can be used individually by 1 type or in combination of 2 or more types.
- PVA is preferable because it is a hydrophilic polymer with a low environmental load.
- Unmodified PVA is a known resin obtained by saponifying polyvinyl acetate.
- the degree of saponification of the unmodified PVA is preferably 98% or less, more preferably 70 to 98%. It should be noted that unmodified PVA having a saponification degree exceeding 98% and not more than 100% tends to be difficult to uniformly dissolve in a polar solvent.
- the unmodified PVA preferably has a polymerization degree of 300 to 5,000 and a saponification degree of 70 to 98%.
- an unmodified PVA for example, a trade name “Kuraray Poval” (manufactured by Kuraray Co., Ltd.), a trade name “Gohsenol” (manufactured by Nippon Gosei Kagaku Kogyo Co., Ltd.), and a trade name “Denka Poval” (manufactured by Denki Kagaku Kogyo Co., Ltd.)
- Commercial products such as trade name “J-Poval” (manufactured by Nippon Vinegar Poval) can be obtained from the market and used.
- Modified PVA is a hydrophilic polymer in which a functional group other than a hydroxyl group and an acetate group is introduced into the unmodified PVA.
- Specific examples of the modified PVA include carboxyl group-modified PVA, carbonyl group-modified PVA, silanol group-modified PVA, amino group-modified PVA, cation-modified PVA, sulfonic acid group-modified PVA, and acetoacetyl group-modified PVA.
- the trade name “Goselan” (sulfonic acid group-modified PVA), the trade name “Gosefimer K” (cation modified PVA), the trade name “Gosefimer Z” (acetoacetyl group-modified PVA), Product name “GOHSENAL” (carboxyl group-modified PVA) (manufactured by Nippon Synthetic Chemical Industry Co., Ltd.); product name “D polymer” (carbonyl group-modified PVA), product name “A series” (carboxyl group-modified PVA) (above, Commercially available products such as “Kuraray C polymer” (cation modified PVA) and product name “Kuraray R polymer” (silanol modified PVA) (above, manufactured by Kuraray Co., Ltd.) from the market. Can be used.
- the content of PVA in the coating liquid is preferably 1 to 40 parts by mass, and more preferably 1 to 20 parts by mass, when the total amount of the coating liquid is 100 parts by mass.
- the coating liquid of the present invention is excellent in adhesion to the substrate by selecting and containing a hydrophilic polymer having an appropriate function according to the field of use, and is non-adhesive, chemical resistant, heat resistant,
- coating liquids that can form a coating film that exhibits functionality specific to fluororesin such as weather resistance include paints, inks, magnetic materials, ceramics, power storage devices, adhesives, electronic materials, and liquid crystal color filters. It is expected to be used in various fields such as pharmaceuticals, cosmetics, fragrances, and building materials.
- a conductive material such as carbon black
- it is used as a conductive coating solution that can form an undercoat layer or an electrode layer of a current collector constituting a power storage device such as a lithium ion secondary battery or a capacitor. be able to.
- PVDF Polyvinylidene fluoride
- the coating liquid of the present invention contains polyvinylidene fluoride (PVDF).
- PVDF is a fluororesin obtained by emulsion polymerization or suspension polymerization of vinylidene fluoride.
- products of various grades such as trade name “KF polymer” (manufactured by Kureha Co., Ltd.) and trade name “kynar” (manufactured by Arkema) can be obtained from the market and used.
- the content of PVDF in the coating liquid is preferably 0.02 to 40 parts by mass, more preferably 0.02 to 20 parts by mass, when the total amount of the coating liquid is 100 parts by mass. preferable.
- the coating liquid of the present invention contains a polar solvent.
- polar solvents include formamide, N-methylformamide, N-ethylformamide, N, N-dimethylformamide, N, N-diethylformamide, vinylformamide, vinylacetamide, acetamide, N-methylacetamide, N-ethyl Acetamide, N, N-dimethylacetamide, N, N-diethylacetamide, N-methyl-2-pyrrolidone, N-ethyl-2-pyrrolidone, vinylpyrrolidone, piperidone, N-methylpiperidone, N-ethylpiperidone, hexamethylphosphoric tri Amides such as amides, 1,3-dimethyl-2-imidazolidinone, methyloxazolidinone, ethyloxazolidinone, ⁇ -alkoxypropionamides; methyl alcohol, ethyl alcohol, isopropyl alcohol Alcohols such as
- aprotic polarities such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, N-ethyl-2-pyrrolidone, ⁇ -alkoxypropionamides, etc.
- a solvent is preferred.
- These polar solvents can be used singly or in combination of two or more.
- a commercial item may be used as it is, and what was refine
- the coating liquid of the present invention further contains a polybasic acid.
- a polybasic acid in addition to the polybasic acid itself, acid anhydrides, salts of some or all of the carboxyl groups, alkyl esters, amides, imides, amideimides, and the like can be used.
- the carboxyl group salt include ammonium salts and amine salts.
- a derivative obtained by modifying a part or all of the carboxyl groups of the polybasic acid with N-hydroxysuccinimide, N-hydroxysulfosuccinimide, or a derivative thereof can be used as the polybasic acid.
- the derivative of the polybasic acid is preferably a compound that generates a polybasic acid upon heating when forming a coating film.
- polybasic acid examples include the following dibasic acid, tribasic acid, tetrabasic acid, and hexabasic acid.
- polybasic acid derivative shown below especially an acid anhydride.
- [Dibasic acids] Oxalic acid, malonic acid, succinic acid, methyl succinic acid, glutaric acid, methyl glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, maleic acid, methyl maleic acid, fumaric acid, methyl fumaric acid Acid, itaconic acid, muconic acid, citraconic acid, glutaconic acid, acetylenedicarboxylic acid, tartaric acid, malic acid, spicrispolic acid, glutamic acid, glutathione, aspartic acid, cystine, acetylcystine, diglycolic acid, iminodiacetic acid, hydroxyethyliminodioxy Acetic acid, thiodiglycolic acid, thionyl diglycolic acid, sulfonyldiglycolic acid, polyethylene oxide diglycolic acid (PEG acid), pyridinedicarboxylic acid,
- Citric acid 1,2,3-propanetricarboxylic acid, 1,2,4-butanetricarboxylic acid, 2-phosphono-1,2,4-butanetricarboxylic acid, trimellitic acid, 1,2, 4-cyclohexanetricarboxylic acid.
- other polybasic acid as shown below together with said polybasic acid. That is, specific examples of “other polybasic acids” include tribasic acids such as isocitric acid, aconitic acid, nitrilotriacetic acid, hydroxyethylethylenediaminetriacetic acid, carboxyethylthiosuccinic acid and trimesic acid; ethylenediamine N, N ′ 1,4,5,8-naphthalenetetracarboxylic acid; pentenetetracarboxylic acid; hexenetetracarboxylic acid; glutamic acid diacetic acid; maleated methylcyclohexenetetracarboxylic acid, furantetracarboxylic acid, benzophenonetetracarboxylic acid, phthalocyanine Monocyclic tetracarboxylic acids such as tetracarboxylic acid, 1,2,3,4-cyclobutanetetracarboxylic acid, cyclopenta
- the polybasic acid is a hydrophilic polymer, PVDF, and other resin component cross-linking agents optionally added during heat-drying Acts as For this reason, the coating film which has the adhesiveness and solvent resistance which were very excellent with respect to the collector which comprises the metal material surface and an electrical storage apparatus can be formed.
- the content of the polybasic acid in the coating liquid is preferably 0.01 to 40 parts by weight, and preferably 0.01 to 20 parts by weight, when the total amount of the coating liquid is 100 parts by weight. Is more preferable.
- the coating liquid of the present invention preferably further contains a conductive material.
- a conductive material include acetylene black, ketjen black, graphite, furnace black, single-walled carbon nanofiber, multi-walled carbon nanofiber, single-walled carbon nanotube, multi-walled carbon nanotube, and graphene. Inclusion of these conductive materials further improves the electrical contact of the coating film (undercoat layer) formed on the surface of the current collectors that make up power storage devices such as lithium secondary batteries and capacitors. To do. That is, since the conductivity of the coating film is ensured, the internal resistance of the electrode layer is reduced and the capacity density is increased.
- the content of the conductive material in the coating liquid is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, when the total amount of the coating liquid is 100 parts by mass. preferable.
- the amount of each component contained in the coating liquid of the present invention is preferably in the following ranges when the total amount of the coating liquid is 100 parts by mass. That is, the content of the hydrophilic polymer is preferably 0.1 to 40 parts by mass, and more preferably 0.5 to 20 parts by mass.
- the PVDF content is preferably 0.02 to 40 parts by mass, and more preferably 0.02 to 20 parts by mass.
- the content of the polybasic acid is preferably 0.01 to 40 parts by mass, and more preferably 0.01 to 20 parts by mass.
- the content of the conductive material is preferably 0.1 to 30 parts by mass, and more preferably 1 to 20 parts by mass.
- the solid content in the coating solution is preferably 1 to 35% by mass.
- the content of the hydrophilic polymer is less than 0.1 part by mass, the strength and adhesion of the formed coating film are insufficient, and the components in the coating film are easily dropped from the coating film.
- the content of the hydrophilic polymer exceeds 40 parts by mass, a uniform solution cannot be obtained.
- the content of PVDF is less than 0.02 parts by mass, various functions such as non-adhesiveness and chemical resistance on the surface of the formed coating film are insufficient.
- the content of PVDF exceeds 40 parts by mass, a uniform solution cannot be obtained.
- the polybasic acid content is less than 0.01 parts by mass, the degree of crosslinking tends to be insufficient, and the crosslinking density of the formed coating film may be lowered. For this reason, while the adhesiveness with respect to a base material falls, the insolubility with respect to a solvent falls and it exists in the tendency for non-swelling property to also fall.
- the content of the polybasic acid exceeds 40 parts by mass, the flexibility of the formed coating film tends to be lowered, and it may be disadvantageous in terms of economy.
- the content of the conductive material is less than 0.1 parts by mass, the conductivity of the formed coating film may be insufficient.
- the content of the conductive material exceeds 30 parts by mass, other components may be relatively insufficient, and the performance of the formed coating film may be deteriorated.
- the hydrophilic polymer content is 1 to 100 parts by mass with respect to 100 parts by mass of the total coating liquid. It is preferable that the content is 15 parts by mass, the PVDF content is 0.1 to 10 parts by mass, the polybasic acid content is 1 to 10 parts by mass, and the conductive material content is 1 to 20 parts by mass.
- the coating liquid of the present invention is used as a coating liquid for forming a water-repellent coating film for antifouling provided on the surface of a ceramic or metal material, the coating liquid is hydrophilic relative to 100 parts by mass of the total amount of the coating liquid.
- the content of the functional polymer is preferably 0.1 to 15 parts by mass, the content of PVDF is 0.1 to 20 parts by mass, and the content of the polybasic acid is preferably 0.1 to 10 parts by mass.
- the coating solution may be made of a resin other than a hydrophilic polymer (other resins).
- Component is preferably added as a binder.
- the other resin component include conventionally known resins such as polyvinyl acetal, fluorine-containing polymer (excluding PVDF), styrene polymer, polyamide, polyimide, and polyamideimide.
- these resin components those obtained from the market may be used as they are, and it is also preferable to use those obtained by taking into consideration the solubility in a solvent and the dispersibility in a dispersion medium.
- the content of the other resin component in the coating liquid is preferably 10 to 2,000 parts by mass, more preferably 10 to 1,000 parts by mass with respect to 100 parts by mass of the hydrophilic polymer. .
- the content of other resin components in the coating liquid is preferably 1 to 40 parts by mass, preferably 5 to 20 parts by mass, when the total amount of the coating liquid is 100 parts by mass. Further preferred.
- the content of other resin components is less than 1 part by mass when the total amount of the coating liquid is 100 parts by mass, the strength of the coating film to be formed and the adhesion to the substrate are likely to be insufficient. Each component may easily fall off from the film.
- the content of other resin components exceeds 40 parts by mass when the total amount of the coating liquid is 100 parts by mass, it may be difficult to obtain a uniform solution. Further, when the content of other resin components exceeds 40 parts by mass when the total amount of the coating liquid is 100 parts by mass, the fluidity of the coating liquid is reduced when the conductive material is contained. At the same time, the conductive material is obscured by other resin components, and the conductivity of the conductive material tends to be insufficient.
- the polybasic acid acts as a crosslinking agent for the hydrophilic polymer, PVDF, and other resin components during heat drying. For this reason, the coating film which has the outstanding adhesiveness with respect to the surface of base materials, such as a metal material, solvent resistance, and water resistance, can be formed.
- the content of the polybasic acid in the coating liquid is preferably 1 to 150 parts by mass per 100 parts by mass of the other resin components, and preferably 2 to 100 parts by mass. More preferably it is.
- the content of the polybasic acid is less than 1 part by mass per 100 parts by mass of the other resin components, the crosslinking density of the formed crosslinked polymer is lowered, and the adhesion of the coating film to the substrate tends to be insufficient. .
- the content of the polybasic acid when used in a battery, if the content of the polybasic acid is less than 1 part by mass per 100 parts by mass of the other resin components, the formed crosslinked polymer is insoluble, non-swellable, and electrochemical In some cases, the stability of the product becomes insufficient. On the other hand, if the content of the polybasic acid exceeds 150 parts by mass per 100 parts by mass of the other resin components, the flexibility of the formed coating film may be lowered and disadvantageous in terms of economy. There is a tendency.
- the coating liquid of the present invention may contain a crosslinking agent (excluding polybasic acid).
- a crosslinking agent include epoxy compounds such as ethylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether, and glycerol polyglycidyl ether; toluylene diisocyanate, xylylene diisocyanate, hexamethylene diisocyanate, phenyl diisocyanate, and the like.
- Isocyanate compounds phenol compounds, alcohols, active methylenes, mercaptans, acid amides, imides, amines, imidazoles, ureas, carbamic acids, imines, oximes, sulfites
- Block isocyanate compounds blocked with blocking agents such as: Aldehyde compounds such as glyoxal, glutaraldehyde, dialdehyde starch; polyethylene glycol diacrylate, (Meth) acrylate compounds such as reethylene glycol dimethacrylate and hexanediol diacrylate; methylol compounds such as methylolmelamine and dimethylolurea; organic acid metal salts such as zirconyl acetate, zirconyl carbonate and titanium lactate; aluminum trimethoxide, aluminum trimethoxide Metal alkoxide compounds such as butoxide, titanium tetraethoxide, titanium tetrabutoxide, zirconium tetrabut
- the content of the crosslinking agent in the coating solution is preferably 0.01 to 200% by mass with respect to the total of the hydrophilic polymer, PVDF, and other resin components.
- the present invention can be achieved by adding a hydrophilic polymer, PVDF, and a polybasic acid to be added as necessary to a polar solvent and dissolving it.
- the coating liquid can be prepared.
- the order of adding each component to the polar solvent may be any. Moreover, although it is sufficient if it stirs on room temperature conditions, you may stir on heating conditions as needed.
- the coating liquid of the present invention is a dispersion coating liquid containing a conductive material, a polar polymer (dispersion medium) containing a hydrophilic polymer, PVDF, a conductive material, and a polybasic acid added as necessary
- the coating liquid of the present invention can be prepared by mixing and dispersing using a mixer.
- a mixer a ball mill, sand mill, pigment disperser, crusher, ultrasonic disperser, homogenizer, planetary mixer, Hobart mixer, or the like can be used.
- the conductive material is mixed in advance using a mixer such as a crusher, a planetary mixer, a Henschel mixer, an omni mixer, etc., and then a hydrophilic polymer, PVDF, and other optional components are added to make it uniform. It is also preferable to mix them. By these methods, a uniform coating solution can be easily prepared.
- the coating film of this invention is formed using the above-mentioned coating liquid.
- a coating film can be formed by drying a coating film formed by applying a coating solution on the surface of a substrate.
- the coating amount when the coating solution is applied to the surface of the substrate is not particularly limited, but is usually an amount such that the thickness of the coating film to be formed is 0.05 to 100 ⁇ m, preferably 0.1 to 50 ⁇ m. If it is.
- the substrate include metals such as aluminum, copper, nickel, and stainless steel, glass, natural resin, synthetic resin, ceramics, wood, paper, fiber, nonwoven fabric, woven fabric, and leather.
- collectors such as aluminum foil, copper foil, and stainless steel foil, as a base material.
- Coating liquids are, for example, gravure coat, gravure reverse coat, roll coat, Mayer bar coat, blade coat, knife coat, air knife coat, comma coat, slot die coat, slide die coat, dip coat, extrusion coat, spray coat, It can apply
- a coating film may be formed by applying a coating solution so that the dry thickness is preferably 0.1 to 100 ⁇ m, more preferably 0.1 to 50 ⁇ m, and particularly preferably 0.1 to 20 ⁇ m, followed by drying by heating. Can be formed. In many cases, it is difficult to apply uniformly so that the film thickness after drying is less than 0.1 ⁇ m. On the other hand, when the film thickness after drying exceeds 100 ⁇ m, the flexibility of the coating film may decrease.
- a coating film can be formed.
- the heat drying is preferably performed at 80 ° C. or higher for 1 second or longer, more preferably 80 to 250 ° C. for 1 second to 60 minutes.
- hydrophilic polymers and PVDF polymers in the coating liquid can be sufficiently crosslinked, and the adhesion of the formed coating film to the substrate and coating
- the electrochemical stability of the film can be improved.
- the adhesiveness with respect to the base material of a coating film and the electrochemical stability of a coating film may become inadequate.
- the coating liquid of the present invention containing a conductive material is useful as a material for forming a conductive coating film for an electrode plate constituting a power storage device such as a secondary battery or a capacitor.
- the coating liquid of the present invention containing a conductive material is applied to the surface of the current collector to form a coating film.
- the thickness of the coating film is preferably 0.1 to 10 ⁇ m, more preferably 0.1 to 5 ⁇ m, and particularly preferably 0.1 to 2 ⁇ m.
- an electrode layer such as a positive electrode layer for a battery, a negative electrode layer for a battery, or a polarizable electrode for a capacitor is formed on the surface of the formed coating film, the electrical resistance between the electrode layer and the current collector
- the electrode plate for a power storage device can be manufactured with a small environmental load.
- the coating liquid of the present invention is applied to the surface of an article or the like, a coating film can be formed on the surface of the article or the like.
- the coating liquid of this invention is useful as a material for forming the water-repellent coating film arrange
- the coating film is applied to the surface of an article or the like and dried by heating so that the dry film thickness is, for example, 0.1 to 200 ⁇ m, preferably 0.5 to 100 ⁇ m, more preferably 1 to 50 ⁇ m, the water resistance is improved.
- An excellent water-repellent coating film can be formed. When heat-dried at a temperature of 80 ° C. or higher, a water-repellent coating film that is firmly adhered to the surface of an article or the like can be formed.
- Controlling the wettability of the article surface is a very important technology. Specifically, by imparting water repellency to the article surface, many functions such as anti-fogging property, water drainage, frosting / defrosting property and the like are exhibited. For example, if the water repellency on the surface of the structure is increased, adhesion of rainwater and the like can be suppressed, so that antifouling properties can be exhibited.
- a contact angle with water is used.
- the larger the contact angle the smaller the surface free energy and the higher the water repellency.
- the water repellency increases as the contact angle of the surface of the building outer wall with water increases, rainwater or the like hardly adheres. For this reason, it becomes easy to maintain the beauty of the building and reduce the frequency of cleaning.
- the contact angle of the coating film of the present invention measured according to JIS R3257 is preferably 70 ° or more, and exhibits high water repellency.
- the coating film of the present invention having high water repellency is previously formed as a primer layer on the surface of a hydrophilic substrate such as glass or metal, the hydrophobicity can be increased when a hydrophobic polymer such as a fluororesin is applied. The adhesion of the polymer can be improved.
- the contact angle of the coating film can be measured according to the following method. First, a coating solution is applied on an aluminum plate and then dried at 200 ° C. for 10 seconds to form a coating film (dry film thickness 0.7 ⁇ m). And the contact angle with respect to the water of the formed coating film surface is measured and computed according to the sessile drop method based on JISR3257.
- a contact angle meter (trade name “Drop Master 100”) manufactured by Kyowa Interface Science Co., Ltd. was used, and the contact angle was measured under conditions of 25 ° C. and a relative humidity of 60%.
- the composite material of the present invention includes a base material and the above-described coating film integrally disposed on the base material.
- the substrate metal, glass, natural resin, synthetic resin, ceramics, wood, paper, fiber, non-woven fabric, woven fabric, and leather can be used. That is, when the coating liquid of the present invention is used, the above-mentioned base material and the coating film to be formed are integrated, and water repellency, non-adhesiveness, chemical resistance, slidability, conductivity, antibacterial / deodorant
- a composite material having excellent properties, texture, anti-fogging properties, paper strength, dyeability, water resistance, and antifouling properties is provided.
- a composite material in which a coating film is formed on a metal substrate such as aluminum, copper, nickel, and stainless steel is useful as a member for an electrode plate that constitutes a power storage device.
- An electrode plate for a power storage device includes the above-described electrode plate member and an electrode layer disposed on the surface of a coating film constituting the electrode plate member.
- Specific examples of the electrode plate for a power storage device include a positive electrode plate in which the electrode layer contains a positive electrode active material, a negative electrode plate in which the electrode layer contains a negative electrode active material, and an electrode plate for a capacitor in which the electrode layer is a polarizable electrode. Can be mentioned.
- examples of the positive electrode current collector include metal foils such as aluminum, tantalum, niobium, titanium, hafnium, zirconium, stainless steel, zinc, tungsten, bismuth, and antimony.
- the positive electrode current collector is preferably an aluminum foil that has excellent corrosion resistance with respect to the electrolytic solution and is lightweight and easy to machine.
- examples of the negative electrode current collector include metal foils such as copper, stainless steel, and aluminum.
- the thickness of the current collector such as a metal foil is preferably 5 to 30 ⁇ m, and more preferably 8 to 25 ⁇ m.
- the surface of the current collector may be previously treated with a coupling agent such as silane, titanate, or aluminum.
- a coating liquid is applied to the surface of the current collector, and then a coating film is formed by heating and drying.
- the film thickness (dry thickness) of the coating film is preferably 0.1 to 10 ⁇ m, more preferably 0.1 to 5 ⁇ m, and particularly preferably 0.1 to 2 ⁇ m.
- the thickness of the coating film is less than 0.1 ⁇ m, it may be difficult to apply uniformly.
- the film thickness of the coating film exceeds 10 ⁇ m, the flexibility of the coating film may be lowered.
- gravure coat, gravure reverse coat, roll coat, Meyer bar coat, blade coat, knife coat, air knife coat, comma coat, slot die coat, slide die coat, dip coat Etc. can be used.
- the drying conditions are preferably 100 to 250 ° C. and 1 second to 60 minutes.
- the hydrophilic polymer as a binder and PVDF are sufficiently cross-linked to improve the adhesion of the formed coating film to the current collector and the electrochemical stability to the electrolytic solution. it can.
- the heat drying condition is less than 100 ° C. or less than 1 second, the adhesion of the coating film to the current collector and the electrochemical stability to the electrolytic solution may be insufficient.
- an electrode plate for a power storage device can be obtained.
- the conditions for the press treatment are preferably 500 to 7,500 kgf / cm 2 . If it is less than 500 kgf / cm 2 , the uniformity of the electrode layer may be difficult to improve. On the other hand, if it exceeds 7,500 kgf / cm 2 , the electrode plate itself including the current collector tends to be damaged.
- the power storage device of the present invention includes the above-described electrode plate for a power storage device, and is useful as a secondary battery or a capacitor.
- the secondary battery is a non-aqueous electrolyte secondary battery manufactured using the above-described electrode plates for a power storage device (a positive electrode plate and a negative electrode plate).
- a non-aqueous electrolyte obtained by dissolving a solute lithium salt in an organic solvent or an ionic liquid is used.
- lithium salt contained in the non-aqueous electrolyte include inorganic lithium salts such as LiClO 4 , LiBF 4 , LiPF 6 , LiAsF 6 , LiCl, LiBr; LiB (C 6 H 5 ) 4 , LiN (SO 2 CF 3 ) 2 , LiC (SO 2 CF 3 ) 3 , LiOSO 2 CF 3 , LiOSO 2 C 2 F 5 , LiOSO 2 C 3 F 7 , LiOSO 2 C 4 F 9 , LiOSO 2 C 5 F 11 , LiOSO 2 C Organic lithium salts such as 6 F 13 and LiOSO 2 C 7 F 15 can be mentioned.
- inorganic lithium salts such as LiClO 4 , LiBF 4 , LiPF 6 , LiAsF 6 , LiCl, LiBr; LiB (C 6 H 5 ) 4 , LiN (SO 2 CF 3 ) 2 , LiC (SO 2 CF 3 ) 3 , LiOSO 2
- organic solvent examples include cyclic esters, chain esters, cyclic ethers, chain ethers and the like.
- cyclic esters include ethylene carbonate, propylene carbonate, butylene carbonate, ⁇ -butyrolactone, vinylene carbonate, 2-methyl- ⁇ -butyrolactone, acetyl- ⁇ -butyrolactone, and ⁇ -valerolactone.
- chain esters include dimethyl carbonate, diethyl carbonate, dibutyl carbonate, dipropyl carbonate, methyl ethyl carbonate, methyl butyl carbonate, methyl propyl carbonate, ethyl butyl carbonate, ethyl propyl carbonate, butyl propyl carbonate, alkyl propionate
- esters, dialkyl esters of malonic acid, and alkyl esters of acetic acid examples include esters, dialkyl esters of malonic acid, and alkyl esters of acetic acid.
- cyclic ethers include tetrahydrofuran, alkyltetrahydrofuran, dialkylalkyltetrahydrofuran, alkoxytetrahydrofuran, dialkoxytetrahydrofuran, 1,3-dioxolane, alkyl-1,3-dioxolane, 1,4-dioxolane and the like.
- chain ethers include 1,2-dimethoxyethane, 1,2-diethoxyethane, diethyl ether, ethylene glycol dialkyl ether, diethylene glycol dialkyl ether, triethylene glycol dialkyl ether, tetraethylene glycol dialkyl ether, and the like. Can be mentioned.
- An ionic liquid is a liquid consisting only of ions, which is a combination of an organic cation and an anion.
- organic cation include dialkylimidazolium cations such as 1-ethyl-3-methylimidazolium ion, trialkylimidazolium cations such as 1,2-dimethyl-3-propylimidazolium ion, and dimethylethylmethoxyammonium ion.
- tetraalkylammonium ions such as 1-butylpyridinium ion, dialkylpyrrolidinium ions such as methylpropylpyrrolidinium ion, and methylpropylpiperidinium ion.
- anion which is a counter ion of the organic cation examples include AlCl 4 ⁇ , PF 6 ⁇ , PF 3 (C 2 F 5 ) 3 ⁇ , PF 3 (CF 3 ) 3 ⁇ , BF 4 ⁇ and BF 2 (CF 3 ) 2 ⁇ , BF 3 (CF 3 ) ⁇ , CF 3 SO 3 ⁇ (TfO; triflate anion), (CF 3 SO 2 ) 2 N ⁇ (TFSI; trifluoromethanesulfonyl), (FSO 2 ) 2 N ⁇ (FSI; fluorosulfonyl), (CF 3 SO 2 ) 3 C ⁇ (TFSM) and the like can be mentioned.
- Capacitor Specific examples of the capacitor in the power storage device of the present invention include an electric double layer capacitor and a lithium ion capacitor.
- the content of the hydrophilic polymer in the coating liquid used for forming the coating film constituting the electrode plate for the capacitor is preferably 1 to 40 parts by mass with respect to 100 parts by mass of the total amount of the coating liquid.
- the amount is more preferably 1 to 20 parts by mass, and particularly preferably 2 to 10 parts by mass. If the amount of the hydrophilic polymer is too small, the coating film component may easily fall off from the coating film. On the other hand, when the amount of the hydrophilic polymer is too large, the conductive material is covered with the hydrophilic polymer, and the internal resistance of the electrode plate tends to increase.
- the content of PVDF in the coating liquid is preferably 0.02 to 20 parts by mass, more preferably 0.05 to 15 parts by mass with respect to 100 parts by mass of the total amount of the coating liquid.
- the amount is preferably 0.1 to 10 parts by mass.
- the polybasic acid is preferably the above-described trivalent or higher polybasic acid and acid anhydride thereof from the viewpoint of the crosslinkability of the hydrophilic polymer used as the binder.
- the content of the polybasic acid in the coating liquid is preferably 1 to 300 parts by mass, and more preferably 10 to 200 parts by mass with respect to 100 parts by mass in total of the hydrophilic polymer and PVDF.
- the content of the polybasic acid is less than 1 part by mass with respect to 100 parts by mass in total of the hydrophilic polymer and PVDF, the crosslinking density of the formed crosslinked polymer is lowered.
- the adhesiveness with respect to the electrical power collector of the coating film formed, the insolubility with respect to electrolyte solution, non-swelling property, and electrochemical stability may become inadequate.
- the content of the polybasic acid exceeds 300 parts by mass with respect to 100 parts by mass of the total of the hydrophilic polymer and PVDF, the flexibility of the formed coating film layer is lowered, and the economical aspect May be disadvantageous.
- conductive carbon such as acetylene black, ketjen black, carbon black, carbon nanofiber, carbon nanotube, and graphene.
- conductive carbon By using conductive carbon as the conductive material, the electrical contact of the coating film is further improved. For this reason, the internal resistance of the obtained capacitor can be lowered and the capacitance density can be increased.
- the content of the conductive material in the coating liquid is usually 0.1 to 20 parts by mass, preferably 2 to 15 parts by mass with respect to 100 parts by mass of the total amount of the coating liquid.
- the coating liquid is preferably processed by physical processing means before coating as required.
- the physical processing means include processing means using a bead mill, ball mill, sand mill, pigment disperser, crusher, ultrasonic disperser, homogenizer, planetary mixer, Hobart mixer and the like.
- the conductive material is mixed in advance using a mixer such as a crusher, a planetary mixer, a Henschel mixer, an omni mixer, etc., and then a hydrophilic polymer solution as a binder is added and mixed uniformly. It is also preferable. Thereby, while being able to prepare a uniform coating liquid easily, the more favorable electrode plate for capacitors can be manufactured.
- the current collector constituting the electrode plate for the capacitor is made of a material having conductivity and electrochemical durability. From the viewpoint of heat resistance, metal materials such as aluminum, titanium, tantalum, stainless steel, gold, and platinum are preferable, and aluminum and platinum are more preferable.
- the shape of the current collector is not particularly limited, but a sheet-like material having a thickness of about 0.001 to 0.5 mm is usually used.
- the method for forming the coating film is not particularly limited, but the coating film can be formed by applying the coating liquid to the current collector and then drying.
- Examples of the application method of the coating liquid include a doctor blade method, a dip method, a reverse roll method, a direct roll method, a gravure method, an extrusion method, a brush coating method, and a spray coating method.
- the viscosity of the coating liquid varies depending on the type of coating machine used and the shape of the coating line, but is usually 10 to 100,000 mPa ⁇ s, preferably 50 to 50,000 mPa ⁇ s, more preferably 100 to It is 20,000 mPa ⁇ s.
- the amount of coating liquid to be applied is such that the thickness of the coating film to be formed is usually 0.05 to 100 ⁇ m, preferably 0.1 to 10 ⁇ m.
- the capacitor of the present invention having the above electrode plate can produce an electric double layer capacitor or a lithium ion capacitor according to a conventional method using components such as the above electrode plate, electrolytic solution, and separator. Specifically, for example, it can be manufactured by stacking electrode plates via a separator, winding the plate according to the shape of the capacitor, folding the plate into a container, injecting the electrolyte into the container, and sealing.
- the electrolytic solution it is preferable to use a nonaqueous electrolytic solution obtained by dissolving an electrolyte in an organic solvent.
- the electrolyte for the electric double layer capacitor include tetraethylammonium tetrafluoroborate, triethylmonomethylammonium tetrafluoroborate, tetraethylammonium hexafluorophosphate, and the like.
- the electrolyte for the lithium ion capacitor include lithium salts such as LiI, LiClO 4 , LiAsF 6 , LiBF 4 , and LiPF 6 .
- Examples of the organic solvent for dissolving the electrolyte include carbonates such as propylene carbonate, ethylene carbonate and butylene carbonate; lactones such as ⁇ -butyrolactone; sulfolanes; nitriles such as acetonitrile. Of these, carbonates having a high withstand voltage are preferable.
- the concentration of the electrolyte in the nonaqueous electrolytic solution is usually 0.5 mol / L or more, preferably 0.8 mol / L or more.
- separator a microporous film or non-woven fabric made of polyolefin such as polyethylene or polypropylene; a porous film mainly made of pulp called electrolytic capacitor paper; and the like can be used.
- a separator in which inorganic ceramic powder and a resin binder are dispersed in a solvent may be applied and dried on the electrode layer.
- a solid electrolyte or a gel electrolyte may be used instead of the separator.
- Example I-1 ⁇ Preparation of coating solution> (Example I-1)
- 5 parts of hydroxypropyl chitosan and 5 parts of PVDF (trade name “kynar 741”, manufactured by Arkema) were dispersed to obtain a dispersion.
- the mixture was stirred at 50 ° C. for 2 hours to prepare a coating solution.
- Table I-1 shows the type and amount of hydrophilic polymer (saponification degree for unmodified polyvinyl alcohol and modified polyvinyl alcohol), the amount of PVDF, the type and amount of polybasic acid, and the type and amount of polar solvent.
- a coating solution was prepared in the same manner as in Example I-1 except that described above. The meanings of the abbreviations in Table I-1 are shown below.
- NMP N-methyl-2-pyrrolidone
- NEP N-ethyl-2-pyrrolidone
- DMF N, N-dimethylformamide
- DMAc N, N-dimethylacetamide
- DMMPA N, N-dimethyl- ⁇ -methoxypropionamide
- DMBPA N , N-Dimethyl- ⁇ -butoxypropionamide
- Example 1 ⁇ Preparation and Evaluation of Conductive Coating Liquid and Conductive Coating Film> (Example 1)
- Conductive coating liquid 6 parts of acetylene black and 94 parts of the coating liquid of Example I-1 were mixed and stirred using a planetary mixer for 120 minutes at a rotational speed of 60 rpm for conductive coating liquid.
- a planetary mixer for 120 minutes at a rotational speed of 60 rpm for conductive coating liquid.
- Examples 2 to 20, Comparative Examples 1 and 2 A conductive coating solution is prepared in the same manner as in Example 1 except that the type and amount of the coating solution and the type and amount of the filler (conductive material) are as shown in Table I-2. At the same time, a conductive coating film was formed. In addition, adhesion evaluation and surface resistivity measurement were performed in the same manner as in Example 1 described above. The results are shown in Table I-2. The meanings of the abbreviations in Table I-2 are shown below.
- AB Acetylene black (trade name “Denka Black HS-100”, manufactured by Denki Kagaku Kogyo Co., Ltd.) KB: Ketjen Black (trade name “ECP600JD”, manufactured by Lion Corporation) FB: Furnace Black (trade name “Toka Black # 4500”, manufactured by Tokai Carbon Co., Ltd.) CNT: carbon nanotube (manufactured by Tokyo Chemical Industry Co., Ltd., multilayer type, diameter 40-60 nm, length 1-2 ⁇ m)
- Example 21 ⁇ Application to batteries> (Example 21)
- the conductive coating solution of Example 1 was applied to one side of an aluminum foil (current collector) having a thickness of 20 ⁇ m. After heat drying for 2 minutes in an oven at 110 ° C., heat drying was performed for 2 minutes in an oven at 180 ° C. to form a 1 ⁇ m thick conductive coating film on one side of the current collector.
- an electrode layer (positive electrode active material layer) having a dry film thickness of 100 ⁇ m was formed on the conductive coating film.
- the film was aged in a vacuum oven at 80 ° C. for 48 hours to sufficiently remove volatile components (water, solvent, etc.), and the positive electrode plate Obtained.
- an electrode layer (negative electrode active material layer) having a dry film thickness of 100 ⁇ m was formed on the conductive coating film.
- the film was aged in a vacuum oven at 80 ° C. for 48 hours to sufficiently remove volatile components (water, solvent, etc.), and the negative electrode plate Obtained.
- the obtained positive electrode plate and negative electrode plate are made of polyolefin (polypropylene, polyethylene, or a copolymer thereof) having a three-dimensional pore structure (sponge-like) and wider than the positive electrode plate.
- the electrode body was produced by spirally winding through a separator made of a conductive film. The produced electrode body was inserted into a bottomed cylindrical stainless steel container also serving as a negative electrode terminal.
- EC ethylene carbonate
- PC propylene carbonate
- DME diimethoxyethane
- Example 22 to 26, Comparative Examples 3 to 4 A positive electrode plate, a negative electrode plate and a battery were produced in the same manner as in Example 21 except that the conductive coating solution shown in Table I-3 was used. Further, the charge / discharge capacity retention ratio was measured and calculated in the same manner as in Example 21 described above. The results are shown in Table I-3.
- Example 27 Using a comma roll coater, the conductive coating solution of Example 1 was applied to one side of an aluminum foil (current collector) having a thickness of 20 ⁇ m. After heat drying for 2 minutes in an oven at 110 ° C., heat drying was performed for 2 minutes in an oven at 180 ° C. to form a conductive coating film having a thickness of 0.5 ⁇ m on one side of the current collector.
- Two of the obtained polarizable electrode plates cut into a circle having a diameter of 15 mm were prepared and dried at 200 ° C. for 20 hours.
- a stainless steel coin-type outer container (diameter 20 mm, high diameter) in which a circular cellulose separator with a diameter of 18 mm and a thickness of 40 ⁇ m is sandwiched between two polarizable electrode plates facing each other and a polypropylene packing is installed. And a stainless steel thickness of 0.25 mm).
- the outer container After injecting the electrolyte so that no air remains in the coin-type outer container, the outer container is covered with a 0.2 mm thick stainless steel cap through a packing, and the container is sealed, and the diameter is A capacitor having a thickness of 20 mm and a thickness of about 2 mm was produced.
- As the electrolytic solution a solution obtained by dissolving tetraethylammonium tetrafluoroborate in propylene carbonate at a concentration of 1 mol / liter was used.
- the capacitance and internal resistance of the produced capacitor were measured at a current density of 20 mA / cm 2 and evaluated according to the following evaluation criteria. The results are shown in Table I-4.
- Capacitance evaluation criteria A: The capacitance is 20% or more larger than that of Comparative Example 5. B: Capacitance larger by 10% or more and less than 20% than Comparative Example 5. C: The capacitance is equal to or less than that of Comparative Example 5.
- Example 28 to 32 A capacitor was fabricated in the same manner as in Example 27 except that the conductive coating solution shown in Table I-4 was used. In addition, the capacitance and internal resistance were measured and evaluated in the same manner as in Example 27 described above. The results are shown in Table I-4.
- Example 5 A capacitor was fabricated in the same manner as in Example 27 except that the conductive coating solution shown in Table I-4 was used. Further, the capacitance and internal resistance were measured in the same manner as in Example 27 described above, and used as a reference for evaluating the capacitance and internal resistance of the capacitors of Examples 27 to 32.
- Example 33 Formation of coating film Using a bar coater (No. 12), the coating liquid of Example I-1 was 4 g / m 2 on the surface of a 1 mm thick glass plate (100 mm ⁇ 100 mm). It applied so that it might become. The glass plate coated with the coating solution under the drying conditions shown in Table II-1 was heated and dried to obtain a test material having a coating film formed on the glass plate.
- Example 34 to 52 Comparative Examples 6 to 7, Reference Example 1
- a coating film was formed in the same manner as in Example 33 except that the coating solution shown in Table II-1 was used.
- adhesion evaluation and contact angle measurement were performed in the same manner as in Example 33 described above. The results are shown in Table II-1.
- the coating films of Examples 33 to 52 had good adhesion to the glass plate as the hydrophilic substrate and had sufficiently high hydrophobicity on the surface. It was.
- the coating film of Comparative Example 6 had good adhesion to the glass plate, but its surface hydrophobicity was insufficient.
- the coating film of Comparative Example 7 had a sufficiently high hydrophobicity on the surface, but the adhesion to the glass plate was insufficient.
- the coating film of Reference Example 1 had insufficient adhesion to the glass plate.
- the coating liquid of the present invention includes a coating film provided with various functions such as conductivity and water repellency, a composite material including the coating film provided with such a function, a battery excellent in various characteristics, It is useful as a material for manufacturing a power storage device electrode plate such as a capacitor and a power storage device including the power storage device electrode plate.
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Abstract
Description
[1]極性溶媒と、親水性ポリマーと、ポリフッ化ビニリデンと、を含有する塗工液。
[2]前記極性溶媒が、N,N-ジメチルホルムアミド、N,N-ジメチルアセトアミド、N-メチル-2-ピロリドン、N-エチル-2-ピロリドン、及びβ-アルコキシプロピオンアミド類からなる群より選択される少なくとも1種である前記[1]に記載の塗工液。
[3]前記親水性ポリマーが、キトサン誘導体、セルロース誘導体、デンプン誘導体、未変性ポリビニルアルコール、及び変性ポリビニルアルコールからなる群より選択される少なくとも1種である前記[1]又は[2]に記載の塗工液。
[4]前記キトサン誘導体が、ヒドロキシエチルキトサン、ヒドロキシプロピルキトサン、ヒドロキシブチルキトサン、及びジヒドロキシプロピルキトサンからなる群より選択される少なくとも1種のヒドロキシアルキルキトサンであり、前記セルロース誘導体が、ヒドロキシエチルセルロース、ヒドロキシプロピルセルロース、メチルセルロース、ヒドロキシエチルメチルセルロース、及びヒドロキシプロピルメチルセルロースからなる群より選択される少なくとも1種であり、前記デンプン誘導体が、ヒドロキシエチルデンプン、ヒドロキシプロピルデンプン、及びヒドロキシブチルデンプンからなるより選択される少なくとも1種であり、前記未変性ポリビニルアルコールの鹸化度が、98モル%以下であり、前記変性ポリビニルアルコールが、カルボキシル基変性ポリビニルアルコール、カルボニル基変性ポリビニルアルコール、シラノール基変性ポリビニルアルコール、アミノ基変性ポリビニルアルコール、カチオン変性ポリビニルアルコール、スルホン酸基変成ポリビニルアルコール、及びアセトアセチル基変性ポリビニルアルコールからなる群より選択される少なくとも1種である前記[3]に記載の塗工液。
[5]さらに多塩基酸を含有する前記[1]~[4]のいずれかに記載の塗工液。
[6]アセチレンブラック、ケッチェンブラック、黒鉛、ファーネスブラック、単層カーボンナノファイバー、多層カーボンナノファイバー、単層カーボンナノチューブ、多層カーボンナノチューブ、及びグラフェンからなる群より選択される少なくとも一種の導電性材料をさらに含有する前記[1]~[5]のいずれかに記載の塗工液。
[7]前記[1]~[6]のいずれかに記載の塗工液を用いて形成される塗工膜。
[8]JIS R3257に準拠して測定される接触角が70°以上である前記[7]に記載の塗工膜。
[9]前記[1]~[6]のいずれかに記載の塗工液を80℃以上に加熱する工程を含む塗工膜の形成方法。
[10]基材と、前記基材上に一体的に配設された前記[7]又は[8]に記載の塗工膜と、を備える複合材料。
[11]前記基材が、金属、ガラス、天然樹脂、合成樹脂、セラミックス、木材、紙、繊維、不織布、織布、及び皮革からなる群より選択される少なくとも一種である前記[10]に記載の複合材料。
[12]集電体と、前記集電体の表面上に配設された、前記[6]に記載の塗工液からなる塗工膜と、を備える電極板用部材。
[13]前記[12]に記載の電極板用部材と、前記電極板用部材を構成する前記塗工膜の表面上に配設された電極層と、を備える蓄電装置用電極板。
[14]前記電極用部材を構成する前記集電体がアルミニウム箔であり、前記電極層が正極活物質を含有する前記[13]に記載の蓄電装置用電極板。
[15]前記電極用部材を構成する前記集電体が銅箔であり、前記電極層が負極活物質を含有する前記[13]に記載の蓄電装置用電極板。
[16]前記電極用部材を構成する前記集電体がアルミニウム箔であり、前記電極層が分極性電極である前記[13]に記載の蓄電装置用電極板。
[17]前記[6]に記載の塗工液を集電体の表面に塗布して塗工膜を形成した後、前記塗工膜の表面上に電極層を形成する工程を有する蓄電装置用電極板の製造方法。
[18]前記[13]~[16]のいずれかに記載の蓄電装置用電極板を備える蓄電装置。
[19]二次電池又はキャパシタである前記[18]に記載の蓄電装置。
以下、本発明の実施の形態について説明するが、本発明は以下の実施の形態に限定されるものではない。本発明者らは、鋭意検討した結果、極性溶媒中に親水性ポリマーとポリフッ化ビニリデン(PVDF)を含有させることで、非粘着性及び撥水性などのフッ素樹脂に由来する機能性と、基材への密着性とを確保できることを見出し、本発明を完成するに至った。すなわち、本発明の塗工液は、極性溶媒と、導電性材料などのフィラーに対する結着性及び分散性とともに親水性を有する親水性ポリマーと、PVDFとを含有するものである。
本発明の塗工液は親水性ポリマーを含有する。親水性ポリマーは、水酸基やカルボキシル基などの親水性の官能基をその分子構造中に有するポリマー(高分子)である。親水性ポリマーの具体例としては、キトサン誘導体、セルロース誘導体、デンプン誘導体、未変性ポリビニルアルコール、及び変性ポリビニルアルコールを挙げることができる。
本発明の塗工液はポリフッ化ビニリデン(PVDF)を含有する。PVDFは、フッ化ビニリデンの乳化重合や懸濁重合によって得られるフッ素系樹脂である。PVDFとしては、商品名「KFポリマー」(クレハ社製)、商品名「kynar」(アルケマ社製)などの種々のグレードのものを市場から入手して使用することができる。
本発明の塗工液は極性溶媒を含有する。極性溶媒の具体例としては、ホルムアミド、N-メチルホルムアミド、N-エチルホルムアミド、N,N-ジメチルホルムアミド、N,N-ジエチルホルムアミド、ビニルホルムアミド、ビニルアセトアミド、アセトアミド、N-メチルアセトアミド、N-エチルアセトアミド、N,N-ジメチルアセトアミド、N,N-ジエチルアセトアミド、N-メチル-2-ピロリドン、N-エチル-2-ピロリドン、ビニルピロリドン、ピペリドン、N-メチルピペリドン、N-エチルピペリドン、ヘキサメチルホスホリックトリアミド、1,3-ジメチル-2-イミダゾリジノン、メチルオキサゾリジノン、エチルオキサゾリジノン、β-アルコキシプロピオンアミド類などのアミド類;メチルアルコール、エチルアルコール、イソプロピルアルコール、プロピルアルコール、ブチルアルコールなどのアルコール類;エチレンカーボネート、エチルメチルカーボネート、ジエチルカーボネート、ジメチルカーボネート、プロピレンカーボネート、ブチレンカーボネートなどのカーボネート類;ジメチルスルホキシドなどスルホキシド類;テトラメチレンスルホンなどのスルホン類を挙げることができる。
本発明の塗工液は、さらに多塩基酸を含有することが好ましい。多塩基酸としては、多塩基酸そのもののほか、酸無水物、一部又は全部のカルボキシル基の塩、アルキルエステル、アミド、イミド、アミドイミドなどを用いることができる。カルボキシル基の塩としては、アンモニウム塩やアミン塩などがある。また、多塩基酸の一部又は全部のカルボキシル基をN-ヒドロキシスクシンイミド、N-ヒドロキシスルホスクシンイミド、又はこれらの誘導体によって修飾した誘導体などを多塩基酸として用いることもできる。なお、多塩基酸の誘導体としては、塗工膜を形成する際の加熱時に多塩基酸を生成する化合物であることが好ましい。
本発明の塗工液は、さらに導電性材料を含有することが好ましい。導電性材料の具体例としては、アセチレンブラック、ケッチェンブラック、黒鉛、ファーネスブラック、単層カーボンナノファイバー、多層カーボンナノファイバー、単層カーボンナノチューブ、多層カーボンナノチューブ、及びグラフェンなどを挙げることができる。これらの導電性材料を含有させることで、リチウム二次電池やキャパシタなどの蓄電装置を構成する集電体の表面に形成される塗工膜(アンダーコート層)の電気的な接触性が一段と向上する。すなわち、塗工膜の導電性が確保されるため、電極層の内部抵抗が小さくなるとともに、容量密度が高まる。
本発明の塗工液に含まれる各成分の量は、塗工液の全量を100質量部とした場合に、それぞれ以下に示す範囲であることが好ましい。すなわち、親水性ポリマーの含有量は、0.1~40質量部であることが好ましく、0.5~20質量部であることがさらに好ましい。PVDFの含有量は、0.02~40質量部であることが好ましく、0.02~20質量部であることがさらに好ましい。多塩基酸の含有量は、0.01~40質量部であることが好ましく、0.01~20質量部であることがさらに好ましい。導電性材料の含有量は、0.1~30質量部であることが好ましく、1~20質量部であることがさらに好ましい。なお、塗工液中の固形分の含有量は、1~35質量%であることが好ましい。
物理的強度、耐久性、耐摩耗性、及び基材に対する接着性などの特性を形成される塗工膜にさらに付与したい場合には、塗工液に、親水性ポリマー以外の樹脂(その他の樹脂成分)をバインダーとして添加することが好ましい。その他の樹脂成分の具体例としては、ポリビニルアセタール、含フッ素高分子(PVDFを除く)、スチレン系重合体、ポリアミド、ポリイミド、及びポリアミドイミドなどの従来公知の樹脂を挙げることができる。これらの樹脂成分は、市場から入手したものをそのまま使用してもよく、溶媒への溶解性や分散媒への分散性等を考慮して誘導体としたものを用いることも好ましい。
本発明の塗工液には、架橋剤(多塩基酸を除く)を含有させることができる。架橋剤の具体例としては、エチレングリコールジグリシジルエーテル、ポリエチレングリコールジグリシジルエーテル、グリセロールポリグリシジルエーテルなどのエポキシ化合物;トルイレンジイソシアナート、キシリレンジイソシアナート、ヘキサメチレンジイソシアナート、フェニルジイソシアナートなどのイソシアナート化合物;前記イソシアナート化合物をフェノール類、アルコール類、活性メチレン類、メルカプタン類、酸アミド類、イミド類、アミン類、イミダゾール類、尿素類、カルバミン酸類、イミン類、オキシム類、亜硫酸類などのブロック剤でブロックしたブロックイソシアナート化合物;グリオキサール、グルタルアルデヒド、ジアルデヒド澱粉などのアルデヒド化合物;ポリエチレングリコールジアクリレート、ポリエチレングリコールジメタクリレート、ヘキサンジオールジアクリレートなどの(メタ)アクリレート化合物;メチロールメラミン、ジメチロール尿素のなどのメチロール化合物;酢酸ジルコニル、炭酸ジルコニル、乳酸チタンなどの有機酸金属塩;アルミニウムトリメトキシド、アルミニウムトリブトキシド、チタニウムテトラエトキシド、チタニウムテトラブトキシド、ジルコニウムテトラブトキシド、アルミニウムジプロポキシドアセチルアセトネート、チタニウムジメトキシドビス(アセチルアセトネート)、チタニウムジブトキシドビス(エチルアセトアセテート)などの金属アルコキシド化合物;ビニルメトキシシラン、ビニルエトキシシラン、3-グリシドキシプロピルトリメトキシシラン、3-グリシドキシプロピルトリエトキシシラン、3-メタクリロキシプロピルトリメトキシシラン、3-アミノプロピルトリメトキシシラン、3-アミノプロピルトリエトキシシラン、3-イソシアネートプロピルトリエトキシシラン、イミダゾールシランなどのシランカップリング剤;メチルトリメトキシシラン、テトラエトキシシラン、メチルトリエトキシシランなどのシラン化合物;カルボジイミド化合物を挙げることができる。
本発明の塗工液が導電性材料を含有しない溶液である場合は、親水性ポリマー、PVDF、及び必要に応じて添加する多塩基酸などを極性溶媒に添加して溶解させれば、本発明の塗工液を調製することができる。各成分を極性溶媒に溶解させる際には、各成分を極性溶媒に添加する順番はどのようにしてもよい。また、室温条件下で撹拌すれば十分であるが、必要に応じて加熱条件下で撹拌してもよい。
本発明の塗工膜は、前述の塗工液を用いて形成される。例えば、基材の表面に塗工液を塗布して形成した塗膜を乾燥することによって、塗工膜を形成することができる。塗工液を基材の表面に塗布する際の塗布量は特に限定されないが、形成される塗工膜の厚さが、通常、0.05~100μm、好ましくは0.1~50μmとなる量であればよい。基材としては、アルミニウム、銅、ニッケル、ステンレスなどの金属、ガラス、天然樹脂、合成樹脂、セラミックス、木材、紙、繊維、不織布、織布、皮革などを挙げることができる。蓄電装置を構成する電極板用部材を製造する場合には、アルミニウム箔、銅箔、及びステンレス箔などの集電体を基材として用いることが好ましい。
本発明の複合材料は、基材と、基材上に一体的に配設された上述の塗工膜とを備える。基材としては、金属、ガラス、天然樹脂、合成樹脂、セラミックス、木材、紙、繊維、不織布、織布、及び皮革を用いることができる。すなわち、本発明の塗工液を用いれば、上記の基材と形成される塗工膜とが一体化され、撥水性、非粘着性、耐薬品性、摺動性、導電性、抗菌・防臭性、風合い、防曇性、紙力、染色性、耐水性、及び防汚染性などに優れた複合材料が提供される。特に、アルミニウム、銅、ニッケル、及びステンレスなどの金属製の基材上に塗工膜を形成した複合材料は、蓄電装置を構成する電極板用部材として有用である。
本発明の蓄電装置用電極板は、前述の電極板用部材と、この電極板用部材を構成する塗工膜の表面上に配設された電極層とを備える。蓄電装置用電極板の具体例としては、電極層が正極活物質を含有する正極板、電極層が負極活物質を含有する負極板、及び電極層が分極性電極であるキャパシタ用の電極板などを挙げることができる。
本発明の蓄電装置は、前述の蓄電装置用電極板を備えるものであり、二次電池やキャパシタとして有用である。
本発明の蓄電装置のうち、二次電池は、前述の蓄電装置用電極板(正極板及び負極板)を用いて作製される非水電解液二次電池である。リチウム系の非水リチウムイオン電池を作製する場合には、溶質のリチウム塩を有機溶剤やイオン液体に溶解して得られる非水電解液が用いられる。非水電解液に含有されるリチウム塩の具体例としては、LiClO4、LiBF4、LiPF6、LiAsF6、LiCl、LiBrなどの無機リチウム塩;LiB(C6H5)4、LiN(SO2CF3)2、LiC(SO2CF3)3、LiOSO2CF3、LiOSO2C2F5、LiOSO2C3F7、LiOSO2C4F9、LiOSO2C5F11、LiOSO2C6F13、LiOSO2C7F15などの有機リチウム塩を挙げることができる。
本発明の蓄電装置のうちのキャパシタの具体例としては、電気二重層キャパシタ、リチウムイオンキャパシタなどを挙げることができる。キャパシタ用の電極板を構成する塗工膜の形成に用いる塗工液中の親水性ポリマーの含有量は、塗工液の全量100質量部に対して、1~40質量部であることが好ましく、1~20質量部であることがさらに好ましく、2~10質量部であることが特に好ましい。親水性ポリマーの量が少なすぎると、塗工膜から塗工膜成分が脱落しやすくなる場合がある。一方、親水性ポリマーの量が多すぎると、導電性材料が親水性ポリマーに覆い隠されてしまい、電極板の内部抵抗が増大する傾向にある。
(例I-1)
N-メチル-2-ピロリドン88部に、ヒドロキシプロピルキトサン5部及びPVDF(商品名「kynar741」、アルケマ社製)5部を分散させて分散液を得た。得られた分散液にピロメリット酸2部を加えた後、50℃で2時間撹拌して塗工液を調製した。
親水性ポリマーの種類及び量(未変性ポリビニルアルコール及び変性ポリビニルアルコールについては鹸化度)、PVDFの量、多塩基酸の種類及び量、並びに極性溶媒の種類及び量を表I-1に示すようにしたこと以外は、前述の例I-1と同様にして塗工液を調製した。なお、表I-1中の略号の意味を以下に示す。
NMP:N-メチル-2-ピロリドン
NEP:N-エチル-2-ピロリドン
DMF:N,N-ジメチルホルムアミド
DMAc:N,N-ジメチルアセトアミド
DMMPA:N,N-ジメチル-β-メトキシプロピオンアミド
DMBPA:N,N-ジメチル-β-ブトキシプロピオンアミド
(実施例1)
(1)導電性塗工液
アセチレンブラック6部及び例I-1の塗工液94部を配合し、プラネタリーミキサーを使用して、回転数60rpmで120分間撹拌混合して導電性塗工液を調製した。
コンマロールコーターを使用し、調製した導電性塗工液を厚さ20μmのアルミニウム箔(集電体)の片面に塗布した。110℃のオーブンで2分間加熱乾燥した後、180℃のオーブンで2分間加熱乾燥して、膜厚1μmの導電性塗工膜を集電体の片面上に形成した。
形成した導電性塗工膜にカッターを用いて直交する縦横11本ずつの平行線を1mmの間隔で引き、1cm2の範囲内に100個の升目を形成した。升目を形成した導電性塗工膜の表面にメンディングテープを貼り付けた。メンディングテープを剥離し、剥離しなかった升目の個数(10回の平均値)を求め、集電体に対する導電性塗工膜の密着性の指標とした。結果を表I-2に示す。
コンマロールコーターを使用し、調製した導電性塗工液をPETフィルム上に塗布した後、180℃のオーブンで5分間乾燥して、導電性塗工膜(乾燥膜厚4μm)をPETフィルム上に形成した。形成した導電性塗工膜の表面抵抗率を、JIS K 7194に準拠した四探針法により測定した。結果を表I-2に示す。なお、四探針法による表面抵抗率の測定には、商品名「ロレスターGP、MCP-T610」(三菱化学アナリテック社製)を使用し、25℃、相対湿度60%の条件下で測定した。
塗工液の種類及び量、並びにフィラー(導電性材料)の種類及び量を表I-2に示すようにしたこと以外は、前述の実施例1と同様にして導電性塗工液を調製するとともに、導電性塗工膜を形成した。また、前述の実施例1と同様にして密着性の評価及び表面抵抗率の測定を行った。結果を表I-2に示す。なお、表I-2中の略号の意味を以下に示す。
AB:アセチレンブラック(商品名「デンカブラックHS-100」、電気化学工業社製)
KB:ケッチェンブラック(商品名「ECP600JD」、ライオン社製)
FB:ファーネスブラック(商品名「トーカブラック#4500」、東海カーボン社製)
CNT:カーボンナノチューブ(東京化成工業社製、多層型、直径40~60nm、長さ1~2μm)
(実施例21)
(1)正極電極板
コンマロールコーターを使用し、実施例1の導電性塗工液を厚さ20μmのアルミニウム箔(集電体)の片面に塗布した。110℃のオーブンで2分間加熱乾燥した後、180℃のオーブンで2分間加熱乾燥して、膜厚1μmの導電性塗工膜を集電体の片面上に形成した。
コンマロールコーターを使用し、実施例1の導電性塗工液を銅箔(集電体)の片面に塗布した。110℃のオーブンで2分間加熱乾燥した後、180℃のオーブンで2分間加熱乾燥して、膜厚が1μmの導電性塗工膜を集電体の片面上に形成した。
得られた正極電極板及び負極電極板を、三次元空孔構造(海綿状)を有する、正極電極板より幅広のポリオレフィン系(ポリプロピレン、ポリエチレン、又はこれらの共重合体)の多孔性フィルムからなるセパレータを介して渦巻き状に捲回して電極体を作製した。作製した電極体を、負極端子を兼ねた有底円筒状のステンレス容器内に挿入した。EC(エチレンカーボネート):PC(プロピレンカーボネート):DME(ジメトキシエタン)=1:1:2(体積比)で全量1リットルになるように調製した混合溶媒に、支持塩として1モルのLiPF6を溶解して得た電解液を注液して、AAサイズで定格容量500mAhの電池を作製した。
充放電測定装置を使用して、25℃の温度条件で作製した電池の充放電容量維持率を測定及び算出した。20セルずつ、充電電流0.2CAの電流値で、充電方向から電池電圧4.1Vになるまで充電した。10分間休止した後、同一電流で2.75Vになるまで放電した。10分間休止した後、以下同一条件で100サイクルの充放電を繰り返して充放電特性を評価した。1サイクル目の充放電容量値を100%とした場合における、100回目の充放電容量値(充放電容量維持率)は98%であった。
表I-3に示す導電性塗工液を用いたこと以外は、前述の実施例21と同様にして正極電極板及び負極電極板と電池を作製した。また、前述の実施例21と同様にして充放電容量維持率を測定及び算出した。結果を表I-3に示す。
(実施例27)
コンマロールコーターを使用し、実施例1の導電性塗工液を厚さ20μmのアルミニウム箔(集電体)の片面に塗布した。110℃のオーブンで2分加熱乾燥した後、180℃のオーブンで2分間加熱乾燥して、膜厚0.5μmの導電性塗工膜を集電体の片面上に形成した。
A:比較例5よりも静電容量が20%以上大きい。
B:比較例5よりも静電容量が10%以上20%未満大きい。
C:比較例5と静電容量が同等以下である。
A:比較例5よりも内部抵抗が20%以上小さい。
B:比較例5よりも内部抵抗が10%以上20%未満小さい。
C:比較例5と内部抵抗が同等以下である。
表I-4に示す導電性塗工液を用いたこと以外は、前述の実施例27と同様にしてキャパシタを作製した。また、前述の実施例27と同様にして静電容量及び内部抵抗を測定し及び評価した。結果を表I-4に示す。
表I-4に示す導電性塗工液を用いたこと以外は、前述の実施例27と同様にしてキャパシタを作製した。また、前述の実施例27と同様にして静電容量及び内部抵抗を測定し、実施例27~32のキャパシタの静電容量及び内部抵抗を評価する基準とした。
(実施例33)
(1)塗工膜の形成
バーコーター(No.12)を用いて、板厚1mmのガラス板(100mm×100mm)の表面に例I-1の塗工液を4g/m2の乾燥膜量となるように塗布した。表II-1に示す乾燥条件で塗工液を塗布したガラス板を加熱乾燥し、ガラス板上に塗工膜が形成された供試材を得た。
形成した塗工膜にカッターを用いて直交する縦横11本ずつの平行線を1mmの間隔で引き、1cm2の範囲内に100個の升目を形成した。升目を形成した塗工膜の表面にメンディングテープを貼り付けた。メンディングテープを剥離し、剥離しなかった升目の個数(10回の平均値)を求め、親水性基材に対する塗工膜の密着性の指標とした。結果を表II-1に示す。
水平状態にした供試材の塗工膜の表面に純水2μLを滴下した。接触角計(商品名「DropMaster100」、協和界面科学社製)を使用し、JIS R3257に準拠して水滴の接触角を測定した。結果を表II-1に示す。
表II-1に示す塗工液を用いたこと以外は、前述の実施例33と同様にして塗工膜を形成した。また、前述の実施例33と同様にして密着性の評価及び接触角の測定を行った。結果を表II-1に示す。
Claims (19)
- 極性溶媒と、親水性ポリマーと、ポリフッ化ビニリデンと、を含有する塗工液。
- 前記極性溶媒が、N,N-ジメチルホルムアミド、N,N-ジメチルアセトアミド、N-メチル-2-ピロリドン、N-エチル-2-ピロリドン、及びβ-アルコキシプロピオンアミド類からなる群より選択される少なくとも1種である請求項1に記載の塗工液。
- 前記親水性ポリマーが、キトサン誘導体、セルロース誘導体、デンプン誘導体、未変性ポリビニルアルコール、及び変性ポリビニルアルコールからなる群より選択される少なくとも1種である請求項1又は2に記載の塗工液。
- 前記キトサン誘導体が、ヒドロキシエチルキトサン、ヒドロキシプロピルキトサン、ヒドロキシブチルキトサン、及びジヒドロキシプロピルキトサンからなる群より選択される少なくとも1種のヒドロキシアルキルキトサンであり、
前記セルロース誘導体が、ヒドロキシエチルセルロース、ヒドロキシプロピルセルロース、メチルセルロース、ヒドロキシエチルメチルセルロース、及びヒドロキシプロピルメチルセルロースからなる群より選択される少なくとも1種であり、
前記デンプン誘導体が、ヒドロキシエチルデンプン、ヒドロキシプロピルデンプン、及びヒドロキシブチルデンプンからなるより選択される少なくとも1種であり、
前記未変性ポリビニルアルコールの鹸化度が、98モル%以下であり、
前記変性ポリビニルアルコールが、カルボキシル基変性ポリビニルアルコール、カルボニル基変性ポリビニルアルコール、シラノール基変性ポリビニルアルコール、アミノ基変性ポリビニルアルコール、カチオン変性ポリビニルアルコール、スルホン酸基変成ポリビニルアルコール、及びアセトアセチル基変性ポリビニルアルコールからなる群より選択される少なくとも1種である請求項3に記載の塗工液。 - さらに多塩基酸を含有する請求項1~4のいずれか一項に記載の塗工液。
- アセチレンブラック、ケッチェンブラック、黒鉛、ファーネスブラック、単層カーボンナノファイバー、多層カーボンナノファイバー、単層カーボンナノチューブ、多層カーボンナノチューブ、及びグラフェンからなる群より選択される少なくとも一種の導電性材料をさらに含有する請求項1~5のいずれか一項に記載の塗工液。
- 請求項1~6のいずれか一項に記載の塗工液を用いて形成される塗工膜。
- JIS R3257に準拠して測定される接触角が70°以上である請求項7に記載の塗工膜。
- 請求項1~6のいずれか一項に記載の塗工液を80℃以上に加熱する工程を含む塗工膜の形成方法。
- 基材と、前記基材上に一体的に配設された請求項7又は8に記載の塗工膜と、を備える複合材料。
- 前記基材が、金属、ガラス、天然樹脂、合成樹脂、セラミックス、木材、紙、繊維、不織布、織布、及び皮革からなる群より選択される少なくとも一種である請求項10に記載の複合材料。
- 集電体と、前記集電体の表面上に配設された、請求項6に記載の塗工液からなる塗工膜と、を備える電極板用部材。
- 請求項12に記載の電極板用部材と、
前記電極板用部材を構成する前記塗工膜の表面上に配設された電極層と、を備える蓄電装置用電極板。 - 前記電極用部材を構成する前記集電体がアルミニウム箔であり、
前記電極層が正極活物質を含有する請求項13に記載の蓄電装置用電極板。 - 前記電極用部材を構成する前記集電体が銅箔であり、
前記電極層が負極活物質を含有する請求項13に記載の蓄電装置用電極板。 - 前記電極用部材を構成する前記集電体がアルミニウム箔であり、
前記電極層が分極性電極である請求項13に記載の蓄電装置用電極板。 - 請求項6に記載の塗工液を集電体の表面に塗布して塗工膜を形成した後、前記塗工膜の表面上に電極層を形成する工程を有する蓄電装置用電極板の製造方法。
- 請求項13~16のいずれか一項に記載の蓄電装置用電極板を備える蓄電装置。
- 二次電池又はキャパシタである請求項18に記載の蓄電装置。
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CN113117154A (zh) * | 2019-12-31 | 2021-07-16 | 东莞市先健医疗有限公司 | 亲水涂层溶液、其制备方法及涂覆该涂层溶液的医疗器械 |
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CN115260905A (zh) * | 2022-08-31 | 2022-11-01 | 华南理工大学 | 一种淀粉基降解型防水防油涂料及其制备方法和应用 |
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JP6166235B2 (ja) | 2017-07-19 |
TWI667299B (zh) | 2019-08-01 |
EP3187553B1 (en) | 2019-12-25 |
CN106795388A (zh) | 2017-05-31 |
US10619070B2 (en) | 2020-04-14 |
EP3187553A4 (en) | 2018-03-07 |
CN106795388B (zh) | 2020-04-10 |
KR102071237B1 (ko) | 2020-01-30 |
TW201612261A (en) | 2016-04-01 |
EP3187553A1 (en) | 2017-07-05 |
JP2016044275A (ja) | 2016-04-04 |
KR20170044185A (ko) | 2017-04-24 |
US20170226365A1 (en) | 2017-08-10 |
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