WO2015080155A1 - Encre photodurcissable pour jet d'encre - Google Patents

Encre photodurcissable pour jet d'encre Download PDF

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Publication number
WO2015080155A1
WO2015080155A1 PCT/JP2014/081252 JP2014081252W WO2015080155A1 WO 2015080155 A1 WO2015080155 A1 WO 2015080155A1 JP 2014081252 W JP2014081252 W JP 2014081252W WO 2015080155 A1 WO2015080155 A1 WO 2015080155A1
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WIPO (PCT)
Prior art keywords
ink composition
cured film
compound
meth
weight
Prior art date
Application number
PCT/JP2014/081252
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English (en)
Japanese (ja)
Inventor
裕矢 堀川
Original Assignee
Jnc株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Jnc株式会社 filed Critical Jnc株式会社
Priority to KR1020167017082A priority Critical patent/KR102232050B1/ko
Priority to JP2015550963A priority patent/JP6520717B2/ja
Priority to CN201480064635.6A priority patent/CN105765010B/zh
Publication of WO2015080155A1 publication Critical patent/WO2015080155A1/fr

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Classifications

    • 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
    • C09D11/00—Inks
    • C09D11/30—Inkjet printing inks
    • C09D11/38—Inkjet printing inks characterised by non-macromolecular additives other than solvents, pigments or dyes
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M50/00—Constructional details or processes of manufacture of the non-active parts of electrochemical cells other than fuel cells, e.g. hybrid cells
    • H01M50/40—Separators; Membranes; Diaphragms; Spacing elements inside cells
    • H01M50/409—Separators, membranes or diaphragms characterised by the material
    • H01M50/411—Organic material
    • H01M50/414—Synthetic resins, e.g. thermoplastics or thermosetting resins
    • H01M50/42—Acrylic resins
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41J—TYPEWRITERS; SELECTIVE PRINTING MECHANISMS, i.e. MECHANISMS PRINTING OTHERWISE THAN FROM A FORME; CORRECTION OF TYPOGRAPHICAL ERRORS
    • B41J2/00—Typewriters or selective printing mechanisms characterised by the printing or marking process for which they are designed
    • B41J2/005—Typewriters or selective printing mechanisms characterised by the printing or marking process for which they are designed characterised by bringing liquid or particles selectively into contact with a printing material
    • B41J2/01—Ink jet
    • 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
    • C09D11/00—Inks
    • C09D11/02—Printing inks
    • C09D11/10—Printing inks based on artificial resins
    • C09D11/101—Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing
    • 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
    • C09D11/00—Inks
    • C09D11/30—Inkjet printing inks
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
    • H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
    • H01B3/30—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes
    • H01B3/44—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes vinyl resins; acrylic resins
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
    • H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
    • H01B3/30—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes
    • H01B3/44—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes vinyl resins; acrylic resins
    • H01B3/447—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes vinyl resins; acrylic resins from acrylic compounds
    • 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
    • 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

Definitions

  • the present invention relates to a photocurable inkjet ink (also simply referred to as “ink composition” in the present invention) that is suitably used for an insulating part of a secondary battery such as a lithium ion storage battery or an insulating part of an electronic component. More specifically, the present invention relates to the production of a secondary battery having a current collector coated with a positive electrode active material, a current collector coated with a negative electrode active material, and a separator, and an electromagnetic shielding case and an electromagnetic shielding material. It relates to a suitable ink composition.
  • some secondary batteries have a structure in which a spiral wound electrode group is housed in a rectangular or cylindrical battery case, but there is a limit to reducing the thickness. Therefore, batteries using a folded structure or a laminated structure instead of a wound body are also manufactured.
  • a battery having a structure in which a laminated electrode group is sealed with an aluminum laminate is very effective in terms of weight reduction.
  • a gap or wrinkle occurs in the laminated body electrode group due to the pressure during lamination, there is a possibility of causing a short circuit or a function deterioration.
  • Even for an exterior other than an aluminum laminate it is necessary to prevent the laminate electrode group from being displaced or uneven in thickness due to long-term use.
  • an insulating resin film can be efficiently produced by applying and curing an ink composition on a metal substrate such as a metal current collector.
  • a metal substrate such as a metal current collector.
  • the conventional photo-curable composition that can be applied by the ink-jet printing method cannot achieve both electrolytic solution resistance and adhesion to a metal current collector.
  • an object of the present invention is to provide an insulating resin film having resistance to an electrolytic solution and adhesion to a metal current collector by inkjet printing on a metal current collector of a secondary battery and photocuring.
  • An ink composition that can form an ink, and ink-jet printing on a metal substrate of an electromagnetic shielding material and photocuring to form an insulating resin film having resistance to a cleaning agent and adhesion to a metal substrate.
  • An object of the present invention is to provide an ink composition that can be used.
  • the present inventors have (meth) acrylate monomer (A) having a phosphate ester and having 1 to 3 acryloyl groups in one molecule and — (CH 2 —CH 2 —O) n — (n> 3)
  • An ink composition comprising a reactive compound (B) other than (A) having no structure, and at least one selected from a benzyl ketal compound and an ⁇ -hydroxyacetophenone compound as a photopolymerization initiator (C).
  • a photocurable composition in which the addition amount of the (meth) acrylate monomer (A) having a phosphate ester group is 0.01 to 5.5 parts by weight with respect to 100 parts by weight of the total amount of the reactive compound (B).
  • the material is highly resistant to the electrolyte used in the secondary battery, has high adhesion to a metal current collector such as aluminum, and is useful as an insulating resin for use in the secondary battery. It has high resistance to cleaning agents used when washing lubricants used in press molding and high adhesion to metal substrates, and is useful as an insulating resin that can be formed by printing on a metal base material for electromagnetic shielding materials. Based on this finding, the present invention has been completed. That is, the present invention includes the following items.
  • (meth) acrylate monomer (A) which is at least one selected from compounds having a phosphate ester represented by general formulas (1-1) and (1-2), and 1 to 3 per molecule
  • C) An (meth) acrylate monomer having a phosphate ester with respect to 100 parts by weight of the total amount of the reactive compound (B), the ink composition comprising at least one selected from benzyl ketal compounds and ⁇ -hydroxyacetophenone compounds
  • each R 1 is independently hydrogen or methyl).
  • the trifunctional (meth) acrylate compound is 0 to 80% by weight
  • the bifunctional (meth) acrylate compound is 10 to 100
  • the photocurable ink-jet ink according to [1] containing 1% by weight and 0 to 60% by weight of a monofunctional (meth) acrylate compound.
  • the reactive compound (B) is trimethylolpropane triacrylate, pentaerythritol triacrylate, 2-hydroxy-3-acryloyloxypropyl methacrylate, neopentyl glycol diacrylate, tricyclodecane dimethanol diacrylate, Dipropylene glycol diacrylate, tripropylene glycol diacrylate, propoxylated (2) neopentyl glycol diacrylate, bisphenol F EO-modified diacrylate, neopentyl glycol hydroxypivalate ester diacrylate, dioxane glycol diacrylate, 1,3- Butylene glycol diacrylate, isobornyl (meth) acrylate, dicyclopentanyl (meth) acrylate and benzyl meta It is at least one selected from the relations, the light-curable inkjet ink according to [1] or [2].
  • the photopolymerization initiator (C) contains 2,2-dimethoxy-2-phenylacetophenone, 2,2-diethoxy-2-phenylacetophenone, 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methyl- At least one selected from 1-phenyl-1-propanone and 2-hydroxy-1- ⁇ 4- [4- (2-hydroxy-2-methyl-propionyl) -benzyl] phenyl ⁇ -2-methyl-1-propanone
  • the photocurable inkjet ink according to any one of [1] to [3].
  • an insulating film having high adhesion to metal can be formed by a printing method, and particularly when a secondary battery is manufactured, an electrolyte-resistant material is formed on a metal current collector.
  • a high insulating film can be formed.
  • an insulating film having high resistance to the cleaning agent can be formed on the metal substrate of the electromagnetic wave shielding material.
  • the photocurable inkjet ink of the present invention is a (meth) acrylate monomer (A) that is at least one selected from compounds having a phosphate ester represented by general formulas (1-1) and (1-2).
  • the ink composition has an addition amount of the (meth) acrylate monomer (A) having a phosphate ester of 0.01 to 5.5 parts by weight with respect to 100 parts by weight of the total amount of B).
  • each R 1 is independently hydrogen or methyl.
  • the ink composition of the present invention may be colorless or colored.
  • (meth) acrylate is used to indicate both or one of acrylate and methacrylate.
  • the “(meth) acryloyl group” is used to indicate both or one of an acryloyl group and a methacryloyl group.
  • the ink composition of the present invention may contain a polymerization inhibitor, a photopolymerizable compound other than the (meth) acrylate monomer (A) having a phosphate ester, a thermosetting compound, and the like.
  • the (meth) acrylate monomer (A) having a phosphate ester of the present invention is at least one selected from compounds having a phosphate ester represented by formula (1-1) or (1-2).
  • a compound having a phosphate ester represented by the general formulas (1-1) and (1-2) may be used in combination.
  • each R 1 is independently hydrogen or methyl.
  • the (meth) acrylate monomer (A) having a phosphate ester may be a synthetic product or a commercially available product.
  • Examples of commercially available products include light ester P-1M, light ester P-2M, and light acrylate P-1A (all trade names: Kyoeisha) Chemical Co., Ltd.) and EBECRYL168 (trade name; Daicel Ornex Co., Ltd.).
  • the content of the (meth) acrylate monomer (A) having a phosphate ester in the ink composition of the present invention is 0.01 to 5.5 parts by weight with respect to 100 parts by weight of the total amount of the reactive compound (B).
  • the cured film formed from the ink composition of the present invention is preferable because it has high electrolytic solution resistance and high adhesion to a metal current collector, and high cleaning agent resistance and high adhesion to a metal substrate.
  • the amount is from 01 to 3.5 parts by weight, more preferably from 0.01 to 2.5 parts by weight.
  • the reactive compound (B) other than the (meth) acrylate monomer (A) having a phosphate ester according to the present invention includes a metal current collector and the like when the number of acryloyl groups in one molecule is 1 to 3 High adhesion to metal substrates, and resistance to battery electrolytes such as alkylene carbonates and cleaning agents such as hydrochlorofluorocarbons without the — (CH 2 —CH 2 —O) n — (n> 3) structure It is preferable because it is high.
  • the reactive compound (B) of the present invention comprises a trifunctional (meth) acrylate compound 0 to 80% by weight, a bifunctional (meth) acrylate compound 10 to 100% by weight, a monofunctional (B)
  • the meth) acrylate compound is contained in an amount of 0 to 60% by weight, it is preferable as an insulating film for an electromagnetic wave shielding material because the cured film has high cleaning agent resistance and high adhesion to a metal substrate.
  • the cured film is preferable as an insulating film for a battery because it has high resistance to electrolyte and high adhesion to a metal current collector.
  • reactive compound (B) of the present invention examples include trimethylolpropane triacrylate, pentaerythritol triacrylate, 2-hydroxy-3-acryloyloxypropyl methacrylate, neopentyl glycol diacrylate, tricyclodecane dimethanol.
  • the ink composition of the present invention contains a photopolymerization initiator (C).
  • the photopolymerization initiator (C) is preferably a compound capable of generating radicals upon irradiation with ultraviolet rays or visible rays. Further, a benzyl ketal compound or an ⁇ -hydroxyacetophenone compound is photocured and cured. It is preferable from the viewpoint that the adhesion of the film to the metal substrate including the metal current collector, the electrolyte solution resistance, and the detergent resistance can be compatible.
  • benzyl ketal compound examples include 2,2-dimethoxy-2-phenylacetophenone and 2,2-diethoxy-2-phenylacetophenone.
  • ⁇ -hydroxyacetophenone compound examples include 1 -Hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methyl-1-phenyl-1-propanone, 2-hydroxy-1- ⁇ 4- [4- (2-hydroxy-2-methyl-propionyl) -benzyl] phenyl ⁇ -2-Methyl-1-propanone.
  • the photopolymerization initiator (C) may be one type or a mixture of two or more types.
  • the content of the photopolymerization initiator (C) is 3 to 20% by weight with respect to the total weight of the ink composition, the photocuring property against ultraviolet rays is excellent, and the metal foil of the resulting cured film is used. It is preferable because of its high adhesion to the metal substrate, more preferably 5 to 15% by weight, still more preferably 7 to 15% by weight.
  • the ink composition of the present invention may contain a polymerization inhibitor in order to improve storage stability.
  • a polymerization inhibitor include 4-methoxyphenol, hydroquinone, hindered amine, and phenothiazine.
  • the polymerization inhibitor used in the ink composition of the present invention may be one type or a mixture of two or more types.
  • the content of the polymerization inhibitor is 0.01 to 1% by weight based on the total weight of the ink composition because the increase in viscosity is small even during long-term storage, taking into account the balance with photocurability. Then, it is more preferably 0.01 to 0.5% by weight, and still more preferably 0.01 to 0.2% by weight.
  • the ink composition of the present invention may contain a thermosetting compound.
  • the thermosetting compound is not particularly limited as long as it is a compound having a functional group capable of thermosetting, and bismaleimide, a phenol resin, a resin containing a phenolic hydroxyl group, a melamine resin, an epoxy compound. Etc.
  • the thermosetting compound used in the ink composition of the present invention may be one type or a mixture of two or more types.
  • thermosetting compound Curing obtained when the content of the thermosetting compound is 2 to 50 parts by weight with respect to 100 parts by weight of the total amount of the reactive compound (B) other than the (meth) acrylate monomer (A) having a phosphate ester It is preferable because the heat resistance of the film is improved, more preferably 5 to 30 parts by weight, still more preferably 10 to 20 parts by weight.
  • bismaleimide examples include compounds represented by the following general formula (1).
  • the bismaleimide represented by the following general formula (1) is a compound obtained by reacting, for example, a diamine and maleic anhydride.
  • R 10 and R 12 are each independently hydrogen or methyl, and R 11 is a divalent group represented by the following general formula (2).
  • R 13 and R 14 each independently represents an alkylene having 1 to 18 carbon atoms in which arbitrary non-continuous methylene may be replaced by oxygen, or an aromatic ring that may have a substituent. It is a cycloalkylene which may have a valent group or a substituent. Examples of the substituent in the aromatic ring and cycloalkylene include carboxyl, hydroxyl, alkyl having 1 to 5 carbons, and alkoxy having 1 to 5 carbons. Because it has a high heat resistance resulting cured film, it is preferable R 13 and R 14 is a divalent group represented by independently following either equation.
  • X is a divalent group represented by any of the following formulas.
  • the bismaleimide may be one kind or a mixture of two or more kinds. [1.5.2 Phenol resin or resin containing a phenolic hydroxyl group]
  • phenol resin a novolak resin obtained by a condensation reaction between an aromatic compound having a phenolic hydroxyl group and an aldehyde is preferably used.
  • resin containing a phenolic hydroxyl group a vinylphenol homopolymer (hydrogenated product) is used.
  • vinylphenol copolymers (including hydrogenated products) of vinylphenol and a compound copolymerizable therewith are preferably used.
  • aromatic compounds having a phenolic hydroxyl group include phenol, o-cresol, m-cresol, p-cresol, o-ethylphenol, m-ethylphenol, p-ethylphenol, o-butylphenol, m-butylphenol.
  • P-butylphenol o-xylenol, 2,3-xylenol, 2,4-xylenol, 2,5-xylenol, 3,4-xylenol, 3,5-xylenol, 2,3,5-trimethylphenol, 3, 4,5-trimethylphenol, p-phenylphenol, resorcinol, hydroquinone, hydroquinone monomethyl ether, pyrogallol, bisphenol A, bisphenol F, diphenol containing terpene skeleton, gallic acid, gallic ester, ⁇ -naphthol and ⁇ -naphth Thor.
  • aldehydes include formaldehyde, paraformaldehyde, furfural, benzaldehyde, nitrobenzaldehyde and acetaldehyde.
  • the compound copolymerizable with vinylphenol include (meth) acrylic acid or a derivative thereof, styrene or a derivative thereof, maleic anhydride, vinyl acetate, and acrylonitrile.
  • phenolic resins include Resitop PSM-6200 (trade name; Gunei Chemical Co., Ltd.), Shonor BRG-555 (trade name; Showa Denko Co., Ltd.), and resins containing phenolic hydroxyl groups.
  • Resitop PSM-6200 trade name; Gunei Chemical Co., Ltd.
  • Shonor BRG-555 trade name; Showa Denko Co., Ltd.
  • resins containing phenolic hydroxyl groups resins containing phenolic hydroxyl groups.
  • Specific examples include Marca Linker M S-2G, Marca Linker CST70, and Marca Linker PHM-C (all trade names: Maruzen Petrochemical Co., Ltd.). *
  • the phenol resin used in the ink composition of the present invention or the resin containing a phenolic hydroxyl group may be a single compound or a mixture of two or more compounds.
  • the melamine resin is not particularly limited as long as it is a resin produced by polycondensation of melamine and formaldehyde, and examples thereof include methylol melamine, etherified methylol melamine, benzoguanamine, methylol benzoguanamine, etherified methylol benzoguanamine, and condensates thereof. It is done. Among these, etherified methylol melamine is preferable in that the resulting cured film has good chemical resistance.
  • melamine resin examples include Nicalac MW-30, MW-30HM, MW-390, MW-100LM, and MX-750LM (all trade names: Sanwa Chemical Co., Ltd.).
  • the melamine resin may be one type or a mixture of two or more types.
  • the ink composition of the present invention may contain an epoxy compound in order to improve the strength of the obtained cured film or the like.
  • the epoxy compound is not particularly limited as long as it has at least one structure represented by the following formula (3-1) or formula (3-2) in one molecule.
  • the epoxy compound examples include novolak type (phenol novolak type and cresol novolak type), bisphenol A type, bisphenol F type, trisphenol methane type, hydrogenated bisphenol A type, hydrogenated bisphenol F type, bisphenol S type, and tetrapheny.
  • an epoxy resin produced by a known method may be used, or a commercially available product may be used.
  • Examples of commercially available products are jER828, 834, 1001, and 1004 (all trade names: manufactured by Mitsubishi Chemical Corporation), Epicron 840, 850, 1050, 1050, and 2055 (all trade names: DIC). Epototo YD-011, YD-013, YD-127, YD-128 (all trade names: Nippon Steel Chemical Co., Ltd.), D.E.R.
  • the epoxy resin that can be used in the ink composition of the present invention may be a single compound or a mixture of two or more compounds.
  • Viscosity of ink composition of the present invention When the ink composition of the present invention has a viscosity at 25 ° C. of 1 to 50 mPa ⁇ s measured with an E-type viscometer, the ink composition of the present invention has good ejection properties when applied by an ink jet method. .
  • the viscosity of the ink of the present invention at 25 ° C. is more preferably 2 to 40 mPa ⁇ s, and further preferably 4 to 30 mPa ⁇ s.
  • the ink composition of the present invention can be prepared by mixing each component as a raw material by a known method.
  • the ink composition of the present invention includes the components (A) to (C) and, if necessary, a surfactant, an ultraviolet absorber, an antioxidant, a polymerization inhibitor, a thermally reactive compound, a thermal polymerization initiator, and the like. It is preferable to prepare by mixing and degassing the obtained solution using a membrane filter made of, for example, ultra high molecular weight polyethylene (UPE).
  • UPE ultra high molecular weight polyethylene
  • the ink composition of the present invention can be applied using a known ink jet method.
  • the ink jet method include a piezo method in which mechanical energy is applied to ink to eject the ink from the ink jet head, and a thermal method in which thermal energy is applied to the ink to eject ink.
  • a coating device used when coating with the ink composition of the present invention for example, energy corresponding to a coating signal is applied to an ink composition in an ink jet head having an ink storage portion in which the ink composition is stored. And an apparatus that performs coating (drawing) corresponding to the coating signal while generating ink droplets by the energy.
  • the ink jet coating apparatus is not limited to one in which the ink jet head and the ink container are separated, and may be one in which they are inseparably integrated.
  • the ink storage unit may be integrated with the ink jet head so as to be separable or non-separable and mounted on the carriage, or may be provided at a fixed portion of the apparatus.
  • the ink composition may be supplied to the inkjet head via an ink supply member, for example, a tube.
  • the ink jet head may be heated, and the heating temperature is preferably 80 ° C. or less, and more preferably 50 ° C. or less.
  • the viscosity of the ink composition of the present invention at the heating temperature is preferably 1.0 to 30 mPa ⁇ s.
  • the film obtained from the ink composition of the present invention (also simply referred to as “cured film” in the present invention) is obtained by applying the above-described ink composition of the present invention to the substrate surface by an inkjet method, and then applying ultraviolet rays, visible light, etc. It is obtained by irradiating and curing the light.
  • the amount of light to be irradiated (exposure amount) when irradiating ultraviolet rays, visible rays, or the like depends on the ink composition, but the integrated light meter UIT-201 equipped with a photoreceiver UVD-365PD manufactured by USHIO INC. 100 to 5,000 mJ / cm 2 is preferable, 300 to 4,000 mJ / cm 2 is more preferable, and 500 to 3,000 mJ / cm 2 is more preferable. Further, the wavelength of ultraviolet rays or visible rays to be irradiated is preferably 200 to 500 nm, and more preferably 250 to 450 nm.
  • the exposure amount described below is a value measured by an integrated light meter UIT-201 equipped with a photoreceiver UVD-365PD manufactured by USHIO INC.
  • the exposure apparatus is not particularly limited as long as it is equipped with an electrodeless lamp, a high-pressure mercury lamp, an ultra-high pressure mercury lamp, a metal halide lamp, a halogen lamp, etc., and irradiates ultraviolet rays, visible rays, etc. in the range of 200 to 500 nm. . *
  • the metal substrate including the metal current collector to which the ink composition of the present invention is applied is not particularly limited as long as it can be an object to which the ink composition is applied, and the shape is not limited to a flat plate shape. It may be curved.
  • the material of the metal substrate including the metal current collector is not particularly limited, and examples thereof include aluminum, copper, nickel, and stainless steel. *
  • the thickness of the metal substrate including the metal current collector is not particularly limited, but if it is 50 ⁇ m or less, printing can be performed while winding it with a roll, which is preferable because it is efficient. *
  • the roll after winding is used for the purpose of completely winding the unreacted ink composition by winding it through an exposure process after printing. You may heat. *
  • an insulating film can be produced on the current collector and electromagnetic wave shielding material used in the secondary battery using the cured film of the present invention.
  • reaction raw materials used in Examples and Comparative Examples are indicated by abbreviations. This abbreviation is used in the following description.
  • EB168 (EBECRYL168, trade name: manufactured by Daicel Ornex Co., Ltd.): Mixture of 2-methacryloxyethyl acid phosphate
  • DPGDA Dipropylene glycol diacrylate
  • NPDA Neopentyl glycol diacrylate
  • HPNDA Neopentyl glycol hydroxypivalate ester
  • Diacrylate SR9003 (trade name: manufactured by Sartomer): propoxylation (2) neopentyl glycol diacrylate
  • TPGDA tripropylene glycol diacrylate 701A (NK ester 701A, trade name: manufactured by Shin-Nakamura Chemical Co., Ltd.): 2- Hydroxy-3-acryloyloxypropyl methacrylate 1,3-BGDA: 1,3-butylene glycol diacrylate FA-513AS (funcryl FA-51 AS, trade name: manufactured by Hitachi Chemical Co., Ltd.): dicyclopentanyl acrylate IBXA: isobornyl acryl
  • Example 1 As the acrylate monomer (A), EB168, DPGDA as the compound (B), Irg1173 as the photopolymerization initiator (C), PF656 as the surfactant (D) are mixed in the following composition ratio, and manufactured by UPE The membrane filter (0.2 ⁇ m) was used to obtain a filtrate (ink composition 1).
  • A EB168 0.25g
  • B 4.75 g of DPGDA
  • C Irg1173
  • D PF656 0.001g
  • an aluminum current collector (20 ⁇ m thick aluminum foil manufactured by Hosen Co., Ltd.) cut into a 6 cm square was prepared.
  • Ink composition 1 is injected into an ink jet apparatus (ULVAC ID-225) equipped with KM512MH (14 pL) manufactured by Konica Minolta IJ Co., Ltd. as an ink jet head, and discharge voltage is 13 V, head temperature is 30 ° C., drive frequency is 5 kHz, and coating Under a discharge condition of once, the printing resolution was set to 841 dpi, and coating was performed in the range of 5 cm square on the prepared substrate.
  • the ink composition is obtained.
  • An aluminum foil on which a cured film of product 1 was formed was obtained. The following measurements and evaluations were performed using the aluminum foil on which the cured film was formed.
  • Measurement of film thickness Measurement was performed using a Digimatic Micrometer (manufactured by Mitutoyo Corporation). It was 13 micrometers when the thickness of the aluminum foil in which the cured film similarly measured was not formed from the thickness of the aluminum foil in which the cured film of the ink composition 1 was formed was subtracted. The average value of three measurements was used as the film thickness value.
  • Example 2 As shown below, an ink composition 2 was prepared in the same manner as in Example 1 except that the ratio of each compound was changed. The viscosity measured in the same manner as in Example 1 is shown below.
  • the viscosity of the ink composition 2 was 10.0 mPa ⁇ s.
  • a cured film was formed using the ink composition 2 under the same conditions as in Example 1, a cured film having a thickness of 12 ⁇ m was obtained. The cured film was evaluated for substrate adhesion and electrolyte resistance under the same conditions as in Example 1. The results are shown in Table 1.
  • Example 3 As shown below, an ink composition 3 was prepared in the same manner as in Example 1 except that the ratio of each compound was changed. The viscosity measured in the same manner as in Example 1 is shown below.
  • the viscosity of the ink composition 3 was 9.7 mPa ⁇ s.
  • a cured film was formed using this ink composition 3 under the same conditions as in Example 1, a cured film having a thickness of 12 ⁇ m was obtained.
  • the cured film was evaluated for substrate adhesion and electrolyte resistance under the same conditions as in Example 1. The results are shown in Table 1.
  • Example 4 As shown below, an ink composition 4 was prepared in the same manner as in Example 1, except that the ratio of each compound was changed. The viscosity measured in the same manner as in Example 1 is shown below.
  • the viscosity of the ink composition 4 was 9.4 mPa ⁇ s.
  • a cured film was formed using this ink composition 4 under the same conditions as in Example 1, a cured film having a thickness of 12 ⁇ m was obtained. The cured film was evaluated for substrate adhesion and electrolyte resistance under the same conditions as in Example 1. The results are shown in Table 1.
  • Example 5 As shown below, an ink composition 5 was prepared in the same manner as in Example 1 except that the ratio of each compound was changed. The viscosity measured in the same manner as in Example 1 is shown below.
  • the viscosity of the ink composition 5 was 12.2 mPa ⁇ s.
  • a cured film was formed using this ink composition 5 under the same conditions as in Example 1, a cured film having a thickness of 12 ⁇ m was obtained. The cured film was evaluated for substrate adhesion and electrolyte resistance under the same conditions as in Example 1. The results are shown in Table 1.
  • Example 6 As shown below, an ink composition 6 was prepared in the same manner as in Example 1 except that the ratio of each compound was changed. The viscosity measured in the same manner as in Example 1 is shown below.
  • the viscosity of the ink composition 6 was 15.5 mPa ⁇ s.
  • a cured film was formed using this ink composition 6 under the same conditions as in Example 1 except that the head temperature was set to 35 ° C., a cured film having a thickness of 13 ⁇ m was obtained.
  • the cured film was evaluated for substrate adhesion and electrolyte resistance under the same conditions as in Example 1. The results are shown in Table 1.
  • Example 7 As shown below, an ink composition 7 was prepared in the same manner as in Example 1 except that the ratio of each compound was changed. The viscosity measured in the same manner as in Example 1 is shown below.
  • the viscosity of the ink composition 7 was 12.0 mPa ⁇ s.
  • a cured film was formed using this ink composition 7 under the same conditions as in Example 1, a cured film having a thickness of 12 ⁇ m was obtained.
  • the cured film was evaluated for substrate adhesion and electrolyte resistance under the same conditions as in Example 1. The results are shown in Table 1.
  • Example 8 As shown below, an ink composition 8 was prepared in the same manner as in Example 1 except that the ratio of each compound was changed. The viscosity measured in the same manner as in Example 1 is shown below.
  • the viscosity of the ink composition 8 was 6.7 mPa ⁇ s.
  • a cured film was formed under the same conditions as in Example 1 except that the discharge voltage was set to 11 V. As a result, a cured film having a thickness of 12 ⁇ m was obtained. The cured film was evaluated for substrate adhesion and electrolyte resistance under the same conditions as in Example 1. The results are shown in Table 1.
  • Example 9 As shown below, an ink composition 9 was prepared in the same manner as in Example 1 except that the ratio of each compound was changed. The viscosity measured in the same manner as in Example 1 is shown below.
  • the viscosity of the ink composition 9 was 21.6 mPa ⁇ s.
  • a cured film was formed using this ink composition 9 under the same conditions as in Example 1 except that the head temperature was set to 40 ° C., a cured film having a thickness of 15 ⁇ m was obtained.
  • the cured film was evaluated for substrate adhesion and electrolyte resistance under the same conditions as in Example 1. The results are shown in Table 1.
  • Example 10 As shown below, an ink composition 10 was prepared in the same manner as in Example 1 except that the ratio of each compound was changed. The viscosity measured in the same manner as in Example 1 is shown below.
  • the viscosity of the ink composition 10 was 16.6 mPa ⁇ s.
  • a cured film was formed using this ink composition 10 under the same conditions as in Example 1 except that the head temperature was set to 35 ° C., a cured film having a thickness of 14 ⁇ m was obtained.
  • the cured film was evaluated for substrate adhesion and electrolyte resistance under the same conditions as in Example 1. The results are shown in Table 1.
  • Example 11 As shown below, an ink composition 11 was prepared in the same manner as in Example 1 except that the ratio of each compound was changed. The viscosity measured in the same manner as in Example 1 is shown below.
  • the viscosity of the ink composition 11 was 14.8 mPa ⁇ s.
  • a cured film was formed using this ink composition 11 under the same conditions as in Example 1 except that the head temperature was set to 35 ° C., a cured film having a thickness of 13 ⁇ m was obtained.
  • the cured film was evaluated for substrate adhesion and electrolyte resistance under the same conditions as in Example 1. The results are shown in Table 1.
  • Example 12 As shown below, an ink composition 12 was prepared in the same manner as in Example 1 except that the ratio of each compound was changed. The viscosity measured in the same manner as in Example 1 is shown below.
  • the viscosity of the ink composition 12 was 42.1 mPa ⁇ s.
  • a cured film was formed under the same conditions as in Example 1 except that the head temperature was set to 50 ° C., and a cured film having a thickness of 15 ⁇ m was obtained. The cured film was evaluated for substrate adhesion and electrolyte resistance under the same conditions as in Example 1. The results are shown in Table 1.
  • Example 13 As shown below, an ink composition 13 was prepared in the same manner as in Example 1 except that the ratio of each compound was changed. The viscosity measured in the same manner as in Example 1 is shown below.
  • the viscosity of the ink composition 13 was 6.7 mPa ⁇ s.
  • a cured film was formed under the same conditions as in Example 1 except that the discharge voltage was set to 11 V. As a result, a cured film having a thickness of 13 ⁇ m was obtained.
  • the cured film was evaluated for substrate adhesion and electrolyte resistance under the same conditions as in Example 1. The results are shown in Table 1.
  • Example 14 As shown below, an ink composition 14 was prepared in the same manner as in Example 1 except that the ratio of each compound was changed. The viscosity measured in the same manner as in Example 1 is shown below.
  • the viscosity of the ink composition 14 was 9.8 mPa ⁇ s.
  • a cured film was formed using this ink composition 14 under the same conditions as in Example 1, a cured film having a thickness of 13 ⁇ m was obtained.
  • the cured film was evaluated for substrate adhesion and electrolyte resistance under the same conditions as in Example 1. The results are shown in Table 1.
  • Example 15 As shown below, an ink composition 15 was prepared in the same manner as in Example 1 except that the ratio of each compound was changed. The viscosity measured in the same manner as in Example 1 is shown below.
  • the viscosity of the ink composition 15 was 9.0 mPa ⁇ s.
  • a cured film was formed using this ink composition 15 under the same conditions as in Example 1, a cured film having a thickness of 13 ⁇ m was obtained.
  • the cured film was evaluated for substrate adhesion and electrolyte resistance under the same conditions as in Example 1. The results are shown in Table 1.
  • Example 16 As shown below, an ink composition 16 was prepared in the same manner as in Example 1 except that the ratio of each compound was changed. The viscosity measured in the same manner as in Example 1 is shown below.
  • the viscosity of the ink composition 16 was 6.8 mPa ⁇ s.
  • a cured film was formed using this ink composition 16 under the same conditions as in Example 1 except that the discharge voltage was set to 11 V, a cured film having a thickness of 14 ⁇ m was obtained.
  • the cured film was evaluated for substrate adhesion and electrolyte resistance under the same conditions as in Example 1. The results are shown in Table 1.
  • Example 17 As shown below, an ink composition 17 was prepared in the same manner as in Example 1 except that the ratio of each compound was changed. The viscosity measured in the same manner as in Example 1 is shown below.
  • the viscosity of the ink composition 17 was 21.9 mPa ⁇ s.
  • a cured film was formed under the same conditions as in Example 1 except that the head temperature was set to 40 ° C., and a cured film having a thickness of 15 ⁇ m was obtained.
  • the cured film was evaluated for substrate adhesion and electrolyte resistance under the same conditions as in Example 1. The results are shown in Table 1.
  • Example 18 As shown below, an ink composition 18 was prepared in the same manner as in Example 1, except that the ratio of each compound was changed. The viscosity measured in the same manner as in Example 1 is shown below.
  • the viscosity of the ink composition 18 was 15.8 mPa ⁇ s.
  • a cured film was formed using this ink composition 18 under the same conditions as in Example 1 except that the head temperature was set to 35 ° C., a cured film having a thickness of 14 ⁇ m was obtained.
  • the cured film was evaluated for substrate adhesion and electrolyte resistance under the same conditions as in Example 1. The results are shown in Table 1.
  • Example 19 As shown below, an ink composition 19 was prepared in the same manner as in Example 1, except that the ratio of each compound was changed. The viscosity measured in the same manner as in Example 1 is shown below.
  • the viscosity of the ink composition 19 was 16.4 mPa ⁇ s.
  • a cured film was formed using this ink composition 19 under the same conditions as in Example 1 except that the head temperature was set to 35 ° C., a cured film having a thickness of 14 ⁇ m was obtained.
  • the cured film was evaluated for substrate adhesion and electrolyte resistance under the same conditions as in Example 1. The results are shown in Table 1.
  • Example 20 As shown below, an ink composition 20 was prepared in the same manner as in Example 1 except that the ratio of each compound was changed. The viscosity measured in the same manner as in Example 1 is shown below.
  • the viscosity of the ink composition 20 was 14.7 mPa ⁇ s.
  • a cured film was formed using this ink composition 20 under the same conditions as in Example 1 except that the head temperature was set to 35 ° C., a cured film having a thickness of 14 ⁇ m was obtained.
  • the cured film was evaluated for substrate adhesion and electrolyte resistance under the same conditions as in Example 1. The results are shown in Table 1.
  • Example 21 As shown below, an ink composition 21 was prepared in the same manner as in Example 1 except that the ratio of each compound was changed. The viscosity measured in the same manner as in Example 1 is shown below.
  • the viscosity of the ink composition 21 was 34.8 mPa ⁇ s.
  • a cured film was formed using this ink composition 21 under the same conditions as in Example 1 except that the head temperature was set to 50 ° C., a cured film having a thickness of 15 ⁇ m was obtained.
  • the cured film was evaluated for substrate adhesion and electrolyte resistance under the same conditions as in Example 1. The results are shown in Table 1.
  • Example 22 As shown below, an ink composition 22 was prepared in the same manner as in Example 1 except that the ratio of each compound was changed. The viscosity measured in the same manner as in Example 1 is shown below.
  • the viscosity of the ink composition 22 was 19.7 mPa ⁇ s.
  • a cured film was formed under the same conditions as in Example 1 except that the head temperature was set to 40 ° C. As a result, a cured film having a thickness of 16 ⁇ m was obtained.
  • the cured film was evaluated for substrate adhesion and electrolyte resistance under the same conditions as in Example 1. The results are shown in Table 1.
  • Example 23 As shown below, an ink composition 23 was prepared in the same manner as in Example 1 except that the ratio of each compound was changed. The viscosity measured in the same manner as in Example 1 is shown below.
  • the viscosity of the ink composition 23 was 9.9 mPa ⁇ s.
  • a cured film was formed using this ink composition 23 under the same conditions as in Example 1, a cured film having a thickness of 14 ⁇ m was obtained.
  • the cured film was evaluated for substrate adhesion and electrolyte resistance under the same conditions as in Example 1. The results are shown in Table 1.
  • Example 24 As shown below, an ink composition 24 was prepared in the same manner as in Example 1 except that the ratio of each compound was changed. The viscosity measured in the same manner as in Example 1 is shown below.
  • the viscosity of the ink composition 24 was 8.5 mPa ⁇ s.
  • a cured film was formed using this ink composition 24 under the same conditions as in Example 1, a cured film having a thickness of 13 ⁇ m was obtained.
  • the cured film was evaluated for substrate adhesion and electrolyte resistance under the same conditions as in Example 1. The results are shown in Table 1.
  • Example 25 As shown below, an ink composition 25 was prepared in the same manner as in Example 1, except that the ratio of each compound was changed. The viscosity measured in the same manner as in Example 1 is shown below.
  • the viscosity of the ink composition 25 was 37.2 mPa ⁇ s.
  • the SUS substrate coated with the ink composition 25 is irradiated with ultraviolet rays at a UV exposure amount of 2,000 mJ / cm 2 using a UV irradiation device (J-CURE 1500 manufactured by JATEC Co., Ltd.).
  • substrate with which the cured film of the thing 25 was formed was obtained. The following measurement and evaluation were performed using the SUS substrate on which the cured film was formed.
  • Measurement of film thickness Measurement was performed using a Digimatic Micrometer (manufactured by Mitutoyo Corporation). It was 15 micrometers when the thickness of the SUS board
  • Example 26 As shown below, an ink composition 26 was prepared in the same manner as in Example 1 except that the ratio of each compound was changed. The viscosity measured in the same manner as in Example 1 is shown below.
  • the viscosity of the ink composition 26 was 28.1 mPa ⁇ s.
  • a cured film was formed under the same conditions as in Example 25 except that the head temperature was set to 45 ° C., and a cured film having a thickness of 15 ⁇ m was obtained. The cured film was evaluated for substrate adhesion and detergent resistance under the same conditions as in Example 25. The results are shown in Table 2.
  • Example 27 As shown below, an ink composition 27 was prepared in the same manner as in Example 1 except that the ratio of each compound was changed. The viscosity measured in the same manner as in Example 1 is shown below.
  • the viscosity of the ink composition 27 was 19.9 mPa ⁇ s.
  • a cured film was formed under the same conditions as in Example 25 except that the head temperature was set to 40 ° C. As a result, a cured film having a thickness of 16 ⁇ m was obtained. The cured film was evaluated for substrate adhesion and detergent resistance under the same conditions as in Example 25. The results are shown in Table 2.
  • Example 1 Comparative Example 1 As shown below, an ink composition 28 was prepared in the same manner as in Example 1, except that the ratio of each compound was changed. The viscosity measured in the same manner as in Example 1 is shown below. (B) DPGDA 5g (C) Irg1173 0.7g (D) PF656 0.001g The viscosity of the ink composition 28 was 9.4 mPa ⁇ s. When a cured film was formed using this ink composition 28 under the same conditions as in Example 1, a cured film having a thickness of 13 ⁇ m was obtained. The cured film was evaluated for substrate adhesion and electrolyte resistance under the same conditions as in Example 1. The results are shown in Table 1.
  • Example 2 As shown below, an ink composition 29 was prepared in the same manner as in Example 1 except that the ratio of each compound was changed. The viscosity measured in the same manner as in Example 1 is shown below.
  • A EB168 0.5g
  • B DPGDA 4.5g
  • C Irg1173 0.7g
  • D PF656 0.001g
  • the viscosity of the ink composition 29 was 13.2 mPa ⁇ s.
  • a cured film was formed under the same conditions as in Example 1 except that the head temperature was set to 35 ° C. A cured film having a thickness of 13 ⁇ m was obtained. The cured film was evaluated for substrate adhesion and electrolyte resistance under the same conditions as in Example 1. The results are shown in Table 1.
  • Example 3 Comparative Example 3
  • an ink composition 30 was prepared in the same manner as in Example 1 except that the ratio of each compound was changed.
  • the viscosity measured in the same manner as in Example 1 is shown below.
  • the viscosity of the ink composition 30 was 18.0 mPa ⁇ s.
  • a cured film was formed under the same conditions as in Example 1 except that the head temperature was set to 40 ° C.
  • a cured film having a thickness of 14 ⁇ m was obtained.
  • the cured film was evaluated for substrate adhesion and electrolyte resistance under the same conditions as in Example 1. The results are shown in Table 1.
  • Example 4 As shown below, an ink composition 31 was prepared in the same manner as in Example 1, except that the ratio of each compound was changed. The viscosity measured in the same manner as in Example 1 is shown below.
  • the viscosity of the ink composition 31 was 8.7 mPa ⁇ s.
  • a cured film was formed using this ink composition 31 under the same conditions as in Example 1, a cured film having a thickness of 13 ⁇ m was obtained. The cured film was evaluated for substrate adhesion and electrolyte resistance under the same conditions as in Example 1. The results are shown in Table 1.
  • Example 5 Comparative Example 5
  • an ink composition 32 was prepared in the same manner as in Example 1 except that the ratio of each compound was changed.
  • the viscosity measured in the same manner as in Example 1 is shown below.
  • the viscosity of the ink composition 32 was 12.4 mPa ⁇ s.
  • a cured film was formed under the same conditions as in Example 1 using this ink composition 32, a cured film having a thickness of 13 ⁇ m was obtained.
  • the cured film was evaluated for substrate adhesion and electrolyte resistance under the same conditions as in Example 1. The results are shown in Table 1.
  • Example 6 Comparative Example 6
  • an ink composition 33 was prepared in the same manner as in Example 1, except that the ratio of each compound was changed.
  • the viscosity measured in the same manner as in Example 1 is shown below.
  • the viscosity of the ink composition 33 was 14.3 mPa ⁇ s.
  • a cured film was formed under the same conditions as in Example 1 except that the head temperature was set to 35 ° C.
  • a cured film having a thickness of 13 ⁇ m was obtained.
  • the cured film was evaluated for substrate adhesion and electrolyte resistance under the same conditions as in Example 1. The results are shown in Table 1.
  • Example 7 an ink composition 34 was prepared in the same manner as in Example 1, except that the ratio of each compound was changed. The viscosity measured in the same manner as in Example 1 is shown below.
  • the viscosity of the ink composition 34 was 9.9 mPa ⁇ s.
  • a cured film was formed using this ink composition 34 under the same conditions as in Example 1, a cured film having a thickness of 13 ⁇ m was obtained. The cured film was evaluated for substrate adhesion and electrolyte resistance under the same conditions as in Example 1. The results are shown in Table 1.
  • Example 8 As shown below, an ink composition 35 was prepared in the same manner as in Example 1, except that the ratio of each compound was changed. The viscosity measured in the same manner as in Example 1 is shown below.
  • the viscosity of the ink composition 35 was 11.5 mPa ⁇ s.
  • a cured film was formed using this ink composition 35 under the same conditions as in Example 1, a cured film having a thickness of 12 ⁇ m was obtained. The cured film was evaluated for substrate adhesion and electrolyte resistance under the same conditions as in Example 1. The results are shown in Table 1.
  • Example 9 an ink composition 36 was prepared in the same manner as in Example 1, except that the ratio of each compound was changed. The viscosity measured in the same manner as in Example 1 is shown below.
  • the viscosity of the ink composition 36 was 25.8 mPa ⁇ s.
  • a cured film was formed under the same conditions as in Example 1 except that the head temperature was set to 40 ° C. As a result, a cured film having a thickness of 15 ⁇ m was obtained. The cured film was evaluated for substrate adhesion and electrolyte resistance under the same conditions as in Example 1. The results are shown in Table 1.
  • Example 10 Comparative Example 10
  • an ink composition 37 was prepared in the same manner as in Example 1 except that the ratio of each compound was changed.
  • the viscosity measured in the same manner as in Example 1 is shown below.
  • the viscosity of the ink composition 37 was 17.7 mPa ⁇ s.
  • a cured film was formed under the same conditions as in Example 1 except that the head temperature was set to 35 ° C., and a cured film having a thickness of 14 ⁇ m was obtained.
  • the cured film was evaluated for substrate adhesion and electrolyte resistance under the same conditions as in Example 1. The results are shown in Table 1.
  • Example 11 an ink composition 38 was prepared in the same manner as in Example 1 except that the ratio of each compound was changed. The viscosity measured in the same manner as in Example 1 is shown below.
  • the viscosity of the ink composition 38 was 24.7 mPa ⁇ s.
  • a cured film was formed under the same conditions as in Example 1 except that the head temperature was set to 40 ° C. As a result, a cured film having a thickness of 15 ⁇ m was obtained. The cured film was evaluated for substrate adhesion and electrolyte resistance under the same conditions as in Example 1. The results are shown in Table 1.
  • Example 12 Comparative Example 12
  • an ink composition 39 was prepared in the same manner as in Example 1 except that the ratio of each compound was changed.
  • the viscosity measured in the same manner as in Example 1 is shown below.
  • the viscosity of the ink composition 39 was 24.8 mPa ⁇ s.
  • a cured film was formed under the same conditions as in Example 1 except that the head temperature was set to 40 ° C.
  • a cured film having a thickness of 15 ⁇ m was obtained.
  • the cured film was evaluated for substrate adhesion and electrolyte resistance under the same conditions as in Example 1. The results are shown in Table 1.
  • Example 13 an ink composition 40 was prepared in the same manner as in Example 1 except that the ratio of each compound was changed. The viscosity measured in the same manner as in Example 1 is shown below.
  • the viscosity of the ink composition 40 was 20.2 mPa ⁇ s.
  • a cured film was formed under the same conditions as in Example 1 except that the head temperature was set to 40 ° C. As a result, a cured film having a thickness of 16 ⁇ m was obtained. The cured film was evaluated for substrate adhesion and electrolyte resistance under the same conditions as in Example 1. The results are shown in Table 1.
  • Example 14 an ink composition 41 was prepared in the same manner as in Example 1 except that the ratio of each compound was changed. The viscosity measured in the same manner as in Example 1 is shown below.
  • B IB-XA 2.95 g
  • B M-208 2.00g
  • C Irg1173 0.7g
  • D PF656 0.001g
  • the viscosity of the ink composition 41 was 28.0 mPa ⁇ s.
  • a cured film was formed under the same conditions as in Example 25 except that the head temperature was set at 45 ° C., and a cured film having a thickness of 15 ⁇ m was obtained. The cured film was evaluated for substrate adhesion and detergent resistance under the same conditions as in Example 25. The results are shown in Table 2.
  • Example 15 an ink composition 42 was prepared in the same manner as in Example 1, except that the ratio of each compound was changed. The viscosity measured in the same manner as in Example 1 is shown below.
  • the viscosity of the ink composition 42 was 9.6 mPa ⁇ s.
  • a cured film was formed using this ink composition 42 under the same conditions as in Example 25 except that the head temperature was set to 30 ° C., a cured film having a thickness of 13 ⁇ m was obtained. The cured film was evaluated for substrate adhesion and detergent resistance under the same conditions as in Example 25. The results are shown in Table 2.
  • the photocurable inkjet ink of the present invention is useful for producing an insulating cured film inside the secondary battery and on the electromagnetic shielding material.

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Abstract

Problème : fournir une composition d'encre telle qu'un film de résine isolant puisse être formé, ayant une résistance à un électrolyte liquide et une adhérence à un collecteur métallique, par impression au jet d'encre et photodurcissement du collecteur métallique d'une cellule secondaire, et fournir une composition d'encre telle qu'un film de résine isolant puisse être formé, ayant une résistance aux détergents et une adhérence à un substrat métallique, par impression au jet d'encre et photodurcissement du substrat métallique d'un matériau de blindage électromagnétique. Solution : composition d'encre comprenant un (méth)acrylate monomère (A) ayant un ester d'acide phosphorique représenté par les formules générales (1-1) et (1-2), un composé réactif (B) autre que (A), ayant 1 à 3 groupes acryloyle dans chacune de ses molécules, et n'ayant pas la structure -(CH2-CH2-O)n-(n > 3), et un composé à base de benzyl-cétal et/ou un composé à base de α-hydroxyacétophénone en tant qu'amorceur de photopolymérisation (C), la quantité ajoutée du (méth)acrylate monomère (A) ayant un ester d'acide phosphorique dans l'encre photodurcissable pour jet d'encre étant 0,01 à 5,5 parties en poids par rapport à un total de 100 parties en poids du composé réactif (B). (Dans les formules générales (1-1) et (1-2), chaque R1 représente d'une manière indépendante un hydrogène ou un groupe méthyle).
PCT/JP2014/081252 2013-11-27 2014-11-26 Encre photodurcissable pour jet d'encre WO2015080155A1 (fr)

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KR1020167017082A KR102232050B1 (ko) 2013-11-27 2014-11-26 광경화성 잉크젯 잉크
JP2015550963A JP6520717B2 (ja) 2013-11-27 2014-11-26 光硬化性インクジェットインク
CN201480064635.6A CN105765010B (zh) 2013-11-27 2014-11-26 光硬化性喷墨墨水、硬化膜、绝缘膜、电磁波屏蔽材、构件及二次电池

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WO2018070488A1 (fr) * 2016-10-14 2018-04-19 デンカ株式会社 Composition
CN107987605A (zh) * 2017-11-09 2018-05-04 苏州同里印刷科技股份有限公司 一种包装盒绿色印刷工艺
WO2019013047A1 (fr) * 2017-07-14 2019-01-17 サカタインクス株式会社 Composition d'encre pour impression à jet d'encre de type photodurcissable
JP2019044174A (ja) * 2017-08-31 2019-03-22 株式会社デュプロ 活性エネルギー線硬化性インクジェットインク、印刷物、インクジェット記録装置、インクジェット記録方法
WO2019189157A1 (fr) * 2018-03-30 2019-10-03 太陽インキ製造株式会社 Composition durcissable pour l'impression à jet d'encre, produit durci correspondant et composant électronique comportant ledit produit durci
JP2019178288A (ja) * 2018-03-30 2019-10-17 太陽インキ製造株式会社 インクジェット印刷用の硬化性組成物、その硬化物及びその硬化物を有する電子部品
JP2019178287A (ja) * 2018-03-30 2019-10-17 太陽インキ製造株式会社 インクジェット印刷用の硬化性組成物、その硬化物及びその硬化物を有する電子部品
WO2021182464A1 (fr) * 2020-03-10 2021-09-16 Jnc株式会社 Composition photodurcissable
JP7340306B1 (ja) * 2023-03-28 2023-09-07 サカタインクス株式会社 光硬化型インクジェット印刷用インク組成物

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112898824B (zh) * 2019-12-04 2022-08-02 中山大学 一种用于玻璃基材的uv-led光固化喷墨墨水及其制备方法

Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH09172287A (ja) * 1995-12-18 1997-06-30 Fujitsu Ltd 電子機器筐体及びそれを有する電子機器
JP2003347692A (ja) * 2002-05-23 2003-12-05 Nec Corp プリント配線板、及び該プリント配線板で用いられる電磁波シールド方法
JP2005126540A (ja) * 2003-10-23 2005-05-19 Union Chemicar Co Ltd 紫外線硬化型インクジェットインク組成物
JP2007169462A (ja) * 2005-12-22 2007-07-05 Toyo Ink Mfg Co Ltd 導電性インキ、導電回路および非接触型メディア
JP2009235272A (ja) * 2008-03-27 2009-10-15 Nisshin Steel Co Ltd エッチングレジスト用インクジェットインキ組成物
JP2010229378A (ja) * 2008-04-09 2010-10-14 Chisso Corp インクジェット用インクおよびインクから得られた硬化膜
JP2011198743A (ja) * 2010-02-25 2011-10-06 Kobe Steel Ltd リチウムイオン二次電池用正極およびリチウムイオン二次電池用正極集電体の製造方法
JP2011200763A (ja) * 2010-03-24 2011-10-13 Nisshin Steel Co Ltd 活性エネルギー線硬化型インクジェットインキによって、樹脂皮膜でマスクされた金属板を製造する方法
JP2012162615A (ja) * 2011-02-04 2012-08-30 Nisshin Steel Co Ltd 活性エネルギー線硬化型インクジェットインキ組成物および樹脂被覆金属板
JP2012162616A (ja) * 2011-02-04 2012-08-30 Nisshin Steel Co Ltd 表面加工用樹脂被覆金属板およびその製造方法、ならびに金属化粧板の製造方法
JP2013105646A (ja) * 2011-11-15 2013-05-30 Seiko Epson Corp 固体電解質層形成用組成物、固体電解質層の形成方法、固体電解質層およびリチウムイオン二次電池

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100337707B1 (ko) 2000-09-25 2002-05-22 정근창 포케팅 전극체 및 그 제조방법과 이를 이용한 리튬이온이차전지
JP2006028377A (ja) * 2004-07-16 2006-02-02 Fuji Photo Film Co Ltd インク組成物及び画像形成方法
JP5224694B2 (ja) 2007-02-06 2013-07-03 富士フイルム株式会社 インクジェット記録用インク組成物、及び、インクジェット記録方法
WO2009118976A1 (fr) * 2008-03-27 2009-10-01 日新製鋼株式会社 Composition d'encre pour jet d'encre pour la gravure d'un résist
JP5272494B2 (ja) 2008-04-23 2013-08-28 日産自動車株式会社 双極型二次電池
JP2014112576A (ja) 2012-11-28 2014-06-19 Tatsuta Electric Wire & Cable Co Ltd シールドフィルム
JP2014156100A (ja) 2013-02-18 2014-08-28 Shinsei:Kk 金属と樹脂の一体成形品

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH09172287A (ja) * 1995-12-18 1997-06-30 Fujitsu Ltd 電子機器筐体及びそれを有する電子機器
JP2003347692A (ja) * 2002-05-23 2003-12-05 Nec Corp プリント配線板、及び該プリント配線板で用いられる電磁波シールド方法
JP2005126540A (ja) * 2003-10-23 2005-05-19 Union Chemicar Co Ltd 紫外線硬化型インクジェットインク組成物
JP2007169462A (ja) * 2005-12-22 2007-07-05 Toyo Ink Mfg Co Ltd 導電性インキ、導電回路および非接触型メディア
JP2009235272A (ja) * 2008-03-27 2009-10-15 Nisshin Steel Co Ltd エッチングレジスト用インクジェットインキ組成物
JP2010229378A (ja) * 2008-04-09 2010-10-14 Chisso Corp インクジェット用インクおよびインクから得られた硬化膜
JP2011198743A (ja) * 2010-02-25 2011-10-06 Kobe Steel Ltd リチウムイオン二次電池用正極およびリチウムイオン二次電池用正極集電体の製造方法
JP2011200763A (ja) * 2010-03-24 2011-10-13 Nisshin Steel Co Ltd 活性エネルギー線硬化型インクジェットインキによって、樹脂皮膜でマスクされた金属板を製造する方法
JP2012162615A (ja) * 2011-02-04 2012-08-30 Nisshin Steel Co Ltd 活性エネルギー線硬化型インクジェットインキ組成物および樹脂被覆金属板
JP2012162616A (ja) * 2011-02-04 2012-08-30 Nisshin Steel Co Ltd 表面加工用樹脂被覆金属板およびその製造方法、ならびに金属化粧板の製造方法
JP2013105646A (ja) * 2011-11-15 2013-05-30 Seiko Epson Corp 固体電解質層形成用組成物、固体電解質層の形成方法、固体電解質層およびリチウムイオン二次電池

Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2021008621A (ja) * 2016-10-14 2021-01-28 デンカ株式会社 組成物
WO2018070488A1 (fr) * 2016-10-14 2018-04-19 デンカ株式会社 Composition
CN109689700A (zh) * 2016-10-14 2019-04-26 电化株式会社 组合物
JPWO2018070488A1 (ja) * 2016-10-14 2019-07-25 デンカ株式会社 組成物
JP7057403B2 (ja) 2016-10-14 2022-04-19 デンカ株式会社 組成物
CN109689700B (zh) * 2016-10-14 2022-04-05 电化株式会社 组合物
WO2019013047A1 (fr) * 2017-07-14 2019-01-17 サカタインクス株式会社 Composition d'encre pour impression à jet d'encre de type photodurcissable
AU2018300886B2 (en) * 2017-07-14 2023-07-06 Sakata Inx Corporation Ink composition for photocurable inkjet printing
US11053399B2 (en) 2017-07-14 2021-07-06 Sakata Inx Corporation Photocurable inkjet printing ink composition
JP2019019208A (ja) * 2017-07-14 2019-02-07 サカタインクス株式会社 光硬化型インクジェット印刷用インク組成物
JP2019044174A (ja) * 2017-08-31 2019-03-22 株式会社デュプロ 活性エネルギー線硬化性インクジェットインク、印刷物、インクジェット記録装置、インクジェット記録方法
JP7267526B2 (ja) 2017-08-31 2023-05-02 株式会社デュプロ 活性エネルギー線硬化性インクジェットインク、印刷物、インクジェット記録装置、インクジェット記録方法
CN107987605A (zh) * 2017-11-09 2018-05-04 苏州同里印刷科技股份有限公司 一种包装盒绿色印刷工艺
JP2019178287A (ja) * 2018-03-30 2019-10-17 太陽インキ製造株式会社 インクジェット印刷用の硬化性組成物、その硬化物及びその硬化物を有する電子部品
JP2019178288A (ja) * 2018-03-30 2019-10-17 太陽インキ製造株式会社 インクジェット印刷用の硬化性組成物、その硬化物及びその硬化物を有する電子部品
WO2019189157A1 (fr) * 2018-03-30 2019-10-03 太陽インキ製造株式会社 Composition durcissable pour l'impression à jet d'encre, produit durci correspondant et composant électronique comportant ledit produit durci
EP3778793A4 (fr) * 2018-03-30 2022-04-27 Taiyo Ink Mfg. Co., Ltd. Composition durcissable pour l'impression à jet d'encre, produit durci correspondant et composant électronique comportant ledit produit durci
JP7112170B2 (ja) 2018-03-30 2022-08-03 太陽インキ製造株式会社 インクジェット印刷用の硬化性組成物、その硬化物及びその硬化物を有する電子部品
US11535766B2 (en) 2018-03-30 2022-12-27 Taiyo Ink Mfg. Co., Ltd. Curable composition for inkjet printing, cured product of same, and electronic component having the cured product
WO2021182464A1 (fr) * 2020-03-10 2021-09-16 Jnc株式会社 Composition photodurcissable
JP7340306B1 (ja) * 2023-03-28 2023-09-07 サカタインクス株式会社 光硬化型インクジェット印刷用インク組成物

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