WO2024106476A1 - リチウムイオン二次電池シール材用光硬化型組成物 - Google Patents

リチウムイオン二次電池シール材用光硬化型組成物 Download PDF

Info

Publication number
WO2024106476A1
WO2024106476A1 PCT/JP2023/041122 JP2023041122W WO2024106476A1 WO 2024106476 A1 WO2024106476 A1 WO 2024106476A1 JP 2023041122 W JP2023041122 W JP 2023041122W WO 2024106476 A1 WO2024106476 A1 WO 2024106476A1
Authority
WO
WIPO (PCT)
Prior art keywords
meth
component
acrylate
weight
ion secondary
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2023/041122
Other languages
English (en)
French (fr)
Japanese (ja)
Inventor
佑太 鷹羽
和正 稲田
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Toagosei Co Ltd
Original Assignee
Toagosei Co Ltd
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 Toagosei Co Ltd filed Critical Toagosei Co Ltd
Priority to KR1020257017112A priority Critical patent/KR20250110841A/ko
Priority to CN202380078592.6A priority patent/CN120129988A/zh
Priority to JP2024558926A priority patent/JPWO2024106476A1/ja
Publication of WO2024106476A1 publication Critical patent/WO2024106476A1/ja
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Images

Classifications

    • 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
    • H01M50/10—Primary casings; Jackets or wrappings
    • H01M50/183—Sealing members
    • H01M50/19—Sealing members characterised by the material
    • H01M50/193—Organic material
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/46—Polymerisation initiated by wave energy or particle radiation
    • C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M10/00—Secondary cells; Manufacture thereof
    • H01M10/05—Accumulators with non-aqueous electrolyte
    • H01M10/052—Li-accumulators
    • H01M10/0525—Rocking-chair batteries, i.e. batteries with lithium insertion or intercalation in both electrodes; Lithium-ion batteries
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M10/00—Secondary cells; Manufacture thereof
    • H01M10/05—Accumulators with non-aqueous electrolyte
    • H01M10/058—Construction or manufacture
    • H01M10/0585—Construction or manufacture of accumulators having only flat construction elements, i.e. flat positive electrodes, flat negative electrodes and flat separators
    • 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
    • H01M50/10—Primary casings; Jackets or wrappings
    • H01M50/183—Sealing members
    • H01M50/186—Sealing members characterised by the disposition of the sealing members
    • 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
    • H01M50/10—Primary casings; Jackets or wrappings
    • H01M50/183—Sealing members
    • H01M50/19—Sealing members characterised by the material
    • H01M50/198—Sealing members characterised by the material characterised by physical properties, e.g. adhesiveness or hardness
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2200/00—Chemical nature of materials in mouldable or extrudable form for sealing or packing joints or covers
    • C09K2200/06—Macromolecular organic compounds, e.g. prepolymers
    • C09K2200/0615—Macromolecular organic compounds, e.g. prepolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C09K2200/0625—Polyacrylic esters or derivatives thereof
    • 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 composition for a sealing material for lithium ion secondary batteries, which can be preferably used in the production of lithium ion secondary batteries.
  • acrylate and/or methacrylate will be referred to as (meth)acrylate, acryloyl group and/or methacryloyl group as (meth)acryloyl group, and acrylic acid and/or methacrylic acid as (meth)acrylic acid.
  • lithium-ion secondary batteries which are lightweight and have high energy density, are preferable as high-output power sources for driving vehicles such as electric vehicles (EVs), plug-in hybrid vehicles (PHVs), and hybrid vehicles (HVs), and demand for them is expected to continue to expand in the future.
  • EVs electric vehicles
  • PSVs plug-in hybrid vehicles
  • HVs hybrid vehicles
  • Non-Patent Document 1 a so-called bipolar battery, in which one side of the current collector is a positive electrode and the other side is a negative electrode.
  • Non-Patent Document 1 By stacking bipolar batteries, a compact, high-voltage battery can be manufactured.
  • a single cell of such a bipolar battery has a planar structure, and a sealant is required at the end to seal the electrolyte.
  • Patent Document 1 illustrates the configuration of a bipolar lithium ion secondary battery, and describes that the sealing member is not particularly limited as long as it has adhesion to the positive and negative electrode current collectors and durability against the electrolyte, but that a polymer material, in particular a thermosetting resin, is preferable (Patent Document 1: [0047]).
  • Patent Document 2 illustrates the structure of a bipolar lithium-ion secondary battery, and shows a heat-sealable film as the sealing member. It also shows that wrinkles in the resin collector caused by heat fusion can be eliminated by using a reinforcing member.
  • Patent Document 3 discloses a photocurable composition that can be suitably used as a material for fixing and sealing the sides of an all-solid-state battery equipped with a laminated electrode body.
  • Patent Document 4 discloses an active energy ray-curable coating composition that can also be used as an electrode protectant for lithium-ion batteries.
  • thermosetting resin exemplified as a preferred material in Patent Document 1 requires at least several minutes, and usually several tens of minutes to several hours, to harden, and therefore poses a problem in terms of mass productivity.
  • the heat-sealable film described in Patent Document 2 has the advantage of being able to adhere in a short time, but has the problem of wrinkles occurring when heated to a high temperature. This document solves this problem by using a reinforcing member, but in this case, another problem occurs in that the product configuration and manufacturing process become complicated.
  • Patent Literature 3 discloses a photocurable composition suitable for fixing and sealing the side surfaces of an all-solid-state battery having a laminated electrode body. By using the photocurable composition, it becomes possible to cure in a short time without applying heat, and mass productivity is improved. However, since the all-solid-state battery exemplified here does not contain an electrolyte solution, it is unclear whether the photocurable composition exemplified here can be used as a sealing material for a lithium ion secondary battery that contains an electrolyte solution.
  • Patent Document 4 discloses a photocurable coating composition that has excellent adhesion to aluminum foil (positive electrode foil) and does not deteriorate in appearance or adhesion even after immersion in a solvent used in an electrolyte, but the performance required as a sealant is unclear. That is, there is no mention of the peel adhesion strength with the electrode substrate, the peel adhesion strength with the electrode substrate after immersion in an electrolyte, or the swelling rate of the cured product due to immersion in an electrolyte. Therefore, the present inventors evaluated the composition disclosed in Patent Document 4 and found that the peel adhesion strength to an aluminum foil (positive electrode foil) and/or a copper foil (negative electrode foil) after immersion in a solvent was not necessarily sufficient for use as a sealing material.
  • the inventors conducted extensive research to find a photocurable composition for use as a sealant for lithium-ion secondary batteries that can be applied at room temperature and cured in a short time, has good peel adhesion to the electrode substrate before and after immersion in electrolyte, and has a small swelling rate due to immersion in electrolyte.
  • the present inventors conducted various investigations to solve the above-mentioned problems, and as a result, found that a composition containing a compound having a polybutadiene and/or hydrogenated polybutadiene skeleton, and having two (meth)acryloyl groups with a specific molecular weight, a compound containing two specific types of compounds and having one (meth)acryloyl group in one molecule (hereinafter referred to as a "monofunctional (meth)acrylate”), and a photoradical polymerization initiator in a specific ratio, can be applied at room temperature and cured in a short time, has good peel adhesion strength with an electrode substrate before and after immersion in an electrolyte solution, and has a small swelling rate due to immersion in an electrolyte solution, thereby completing the present invention.
  • the present invention will be described in detail below.
  • composition of the present invention can be applied at room temperature and hardened in a short time, has good peel adhesion to the electrode substrate before and after immersion in electrolyte, and has a small swelling rate due to immersion in electrolyte.
  • FIG. 1 is a cross-sectional view of an example of a bipolar type lithium ion secondary battery.
  • FIG. 2 is a diagram showing an example of a method for producing a lithium ion secondary battery using the composition of the present invention.
  • FIG. 3 is a diagram showing an example of a method for producing a lithium ion secondary battery using the composition of the present invention.
  • Component (A) a compound having a polybutadiene and/or hydrogenated polybutadiene skeleton and two (meth)acryloyl groups in one molecule, the compound having a number average molecular weight of 1000 or more;
  • Component (B) a monofunctional (meth)acrylate containing the following components (B-1) and (B-2) as essential components;
  • Component (B-1) a monofunctional (meth)acrylate having an alkyl or alkenyl group in which the ester residue has 10 to 30 carbon atoms;
  • Component (B-2) a monofunctional (meth)acrylate having an ester residue with 5 to 30 carbon atoms and an alicyclic hydrocarbon group and/or an aromatic hydrocarbon group;
  • Component (C) a monofunctional (meth)acrylate containing a photoradical polymerization initiator,
  • the composition contains 10 to 80% by weight of component (A) and 20 to 90% by weight of component (B) relative to a
  • a method for producing a lithium ion secondary battery comprising applying or injecting the photocurable composition for a lithium ion secondary battery sealant according to any one of [1] to [3] onto a side surface of a constituent material of a lithium ion secondary battery, and then irradiating the applied surface or the injected surface with light.
  • Components (A) to (C) other components, the composition, and methods of use will be described below. The specific compounds given in the description of the components (A) to (C) below may be used alone or in combination of two or more kinds.
  • Component (A) is a compound having a polybutadiene skeleton and/or a hydrogenated polybutadiene skeleton in one molecule, and having an Mn of 1,000 or more and two or more (meth)acryloyl groups.
  • the (meth)acryloyl group in component (A) may be present in a side chain or at a terminal, and is preferably a compound having a (meth)acryloyl group at a terminal, and particularly preferably a compound having (meth)acryloyl groups at both terminals.
  • the Mn (number average molecular weight) of the component (A) is at least 1,000, preferably from 5,000 to 50,000, and more preferably from 10,000 to 30,000. If a compound with an Mn of less than 1,000 is used, the adhesive strength to the aluminum foil decreases.
  • Mn (number average molecular weight) is a value calculated by converting the molecular weight measured by gel permeation chromatography (hereinafter referred to as "GPC") into polystyrene equivalent value.
  • component (A) examples include an oligomer in which a polybutadiene or hydrogenated polybutadiene skeleton and two or more (meth)acryloyl groups are bonded via urethane bonds (hereinafter referred to as "(A1)”), and an oligomer in which a polybutadiene or hydrogenated polybutadiene skeleton and two or more (meth)acryloyl groups are bonded via ester bonds (hereinafter referred to as "(A2)").
  • component (A), (A1) and (A2) are preferred, with (A1) being preferred in that the cured product will have excellent mechanical properties, and a urethane (meth)acrylate oligomer having two (meth)acryloyl groups being more preferred.
  • the urethane (meth)acrylate oligomer having two (meth)acryloyl groups in (A1) is preferably a urethane (meth)acrylate oligomer having two (meth)acryloyl groups obtained by reacting a polybutadiene diol or a hydrogenated polybutadiene diol (a) [hereinafter referred to as "compound (a)”], a diisocyanate compound (b) [hereinafter referred to as “compound (b)”], and a hydroxyl group-containing (meth)acrylate (c) [hereinafter referred to as "compound (c)”].
  • the Mn of the compound (a) is preferably from 500 to 10,000, and more preferably from 1,000 to 10,000.
  • a polyol other than the compound (a) may be used in combination, if necessary.
  • ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, 1,4-butanediol, 1,6-hexanediol, neopentyl glycol, cyclohexanedimethanol, hydrogenated bisphenol A, and the like can be mentioned.
  • various compounds can be used so long as they have two isocyanate groups in one molecule.
  • Specific examples include tolylene diisocyanate, hydrogenated tolylene diisocyanate, diphenylmethane diisocyanate, hydrogenated diphenylmethane diisocyanate, tolidine diisocyanate, naphthalene diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, xylylene diisocyanate, and hydrogenated xylylene diisocyanate.
  • various compounds can be used so long as they are (meth)acrylates having a hydroxyl group.
  • Specific examples include 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, caprolactone-modified products of 2-hydroxyethyl (meth)acrylate, and glycidol di(meth)acrylate.
  • hydroxyalkyl (meth)acrylates such as 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, and 4-hydroxybutyl (meth)acrylate are preferred.
  • (A2) include an esterification reaction product of polybutadiene or hydrogenated polybutadiene containing two or more hydroxyl groups with (meth)acrylic acid or (meth)acrylic acid halide, and an ester exchange reaction product of polybutadiene or hydrogenated polybutadiene containing two or more hydroxyl groups with (meth)acrylate.
  • Component (A) is commercially available, and specific examples of (A1) include "TEA-1000” (polybutadiene-based urethane acrylate oligomer, Mn: about 3,000) manufactured by Nippon Soda Co., Ltd., "TEAI-1000” (hydrogenated polybutadiene-based urethane acrylate oligomer, Mn: about 3,000) manufactured by Nippon Soda Co., Ltd., "TE-2000” (polybutadiene-based urethane methacrylate oligomer) manufactured by Nippon Soda Co., Ltd., "CN9014” (polybutadiene-based urethane acrylate) manufactured by Sartomer, "CN301” (polybutadiene-based dimethacrylate) manufactured by Sartomer, “CN303” (polybutadiene-based dimethacrylate) manufactured by Sartomer, and “CN307” (polybutadiene diacrylate) manufactured by
  • (A2) examples include "BAC-45” (polybutadiene diacrylate, Mn: 5,000) manufactured by Osaka Organic Chemical Industry Ltd.
  • BAC-45 polybutadiene diacrylate, Mn: 5,000
  • TEAI-1000 TEA-1000
  • CN9014 CN307
  • BAC-45 acryloyl group
  • component (A) a (meth)acrylate oligomer having a polybutadiene hydrogenated skeleton is preferred, and a urethane (meth)acrylate having a polybutadiene hydrogenated skeleton is more preferred.
  • the content of the component (A) should be 10 to 80% by weight, preferably 10 to 60% by weight, and particularly preferably 15 to 50% by weight, of the combined total of the components (A), (B), and (D).
  • components (A) and (B) are referred to as “curable components”, or, when component (D) described below is included, components (A), (B) and (D) are referred to as “curable components”. If the content of component (A) is less than 10% by weight, the swelling rate of the cured product after immersion in the electrolyte increases, and the adhesive strength to the electrode foil after immersion in the electrolyte decreases. On the other hand, if the content exceeds 80% by weight, the adhesive strength of the cured product decreases.
  • Component (B) is a monofunctional (meth)acrylate containing the following components (B-1) and (B-2) as essential components.
  • Component (B-1) a monofunctional (meth)acrylate having an alkyl or alkenyl group in an ester residue having 10 to 30 carbon atoms;
  • Component (B-2) a monofunctional (meth)acrylate having an alicyclic hydrocarbon group and/or aromatic hydrocarbon group in an ester residue having 5 to 30 carbon atoms.
  • ester residue refers to a group represented by R obtained by removing the ester bond from the structural portion represented by -CO-O-R contained in the monofunctional (meth)acrylate.
  • the component (B-1) is a compound having an alkyl group or alkenyl group having 10 to 30 carbon atoms (hereinafter, these groups are collectively referred to as "alkyl group, etc.") and one (meth)acryloyl group.
  • examples of the ester residue having an alkyl group or the like having 10 to 30 carbon atoms include alkyl groups and alkenyl groups, and (poly)alkylene oxide groups having an alkyl group or an alkenyl group.
  • (poly)alkylene oxide group” means a group having one or more alkylene oxide units.
  • compounds having 9 or less carbon atoms, such as alkyl groups have the problem of increasing the swelling rate of the cured product after immersion in an electrolyte solution, while compounds having 31 or more carbon atoms, such as alkyl groups, have the problem of decreasing the adhesive strength to the electrode foil.
  • examples of the compound having an alkyl group include alkyl (meth)acrylates having an alkyl group having 10 to 30 carbon atoms, such as decyl (meth)acrylate, lauryl (meth)acrylate, hexadecyl (meth)acrylate, heptadecyl (meth)acrylate, n-stearyl (meth)acrylate, isostearyl (meth)acrylate, and behenyl (meth)acrylate.
  • Examples of the compound having an alkenyl group include 8-dodecenyl (meth)acrylate and 9-octadecenyl (meth)acrylate.
  • Examples of the (poly)alkylene oxide group having an alkyl group include an alkyl group-containing (poly)alkylene oxide group.
  • Examples of the compound having an alkyl group-containing (poly)alkylene oxide group include alkyl carbitol (meth)acrylates such as octadecyl carbitol (meth)acrylate. In this case, the number of repeating alkylene oxide units is preferably 1 to 8.
  • alkyl (meth)acrylates having a branched structure and 17 to 30 carbon atoms such as isostearyl (meth)acrylate, are preferred.
  • the component (B-2) is a compound having an ester residue with 5 to 30 carbon atoms, an alicyclic hydrocarbon group and/or an aromatic hydrocarbon group, and one (meth)acryloyl group.
  • examples of the alicyclic hydrocarbon group having 5 to 30 carbon atoms include cyclic alkyl groups and cyclic alkenyl groups.
  • examples of the alicyclic hydrocarbon group and aromatic hydrocarbon group include a (poly)alkylene oxide group having an alicyclic hydrocarbon group, and a (poly)alkylene oxide group having an aromatic hydrocarbon group.
  • the alicyclic hydrocarbon group and aromatic hydrocarbon group may be a functional group further having an alkyl group in a part of the cyclic skeleton.
  • examples of the compound having a cyclic alkyl group include (meth)acrylates having a cyclic alkyl group having 5 to 30 carbon atoms, such as cyclohexyl (meth)acrylate, isobornyl (meth)acrylate, dicyclopentanyl (meth)acrylate, and t-butylcyclohexyl (meth)acrylate.
  • examples of the compound having a cyclic alkenyl group include cyclohexenyl (meth)acrylate and dicyclopentenyl (meth)acrylate.
  • An example of the compound having a cyclic alkyl group-containing (poly)alkylene oxide group is dicyclopentenyloxyethyl (meth)acrylate.
  • Examples of the monofunctional (meth)acrylate having an aromatic hydrocarbon group of the component (B-2) include aromatic monofunctional (meth)acrylates such as benzyl (meth)acrylate, phenoxyethyl (meth)acrylate, o-phenylphenoxy (meth)acrylate, and p-cumylphenol ethylene (meth)acrylate.
  • aromatic monofunctional (meth)acrylates such as benzyl (meth)acrylate, phenoxyethyl (meth)acrylate, o-phenylphenoxy (meth)acrylate, and p-cumylphenol ethylene (meth)acrylate.
  • Examples of the compound having a (poly)alkylene oxide group having an alkyl group-containing aromatic group include (meth)acrylates of alkylphenol alkylene oxide adducts having an alkyl group having 4 to 20 carbon atoms, such as (meth)acrylates of nonylphenol ethylene oxide adducts and (meth)acrylates of nonylphenol propylene oxide adducts.
  • the number of repeating alkylene oxide units is preferably 1 to 8.
  • the component (B) may contain a monofunctional (meth)acrylate other than the components (B-1) and (B-2) [hereinafter referred to as “component (B-3)”], but it is preferable that it does not contain such a monofunctional (meth)acrylate.
  • Examples of the component (B-3) include monofunctional (meth)acrylates having an alkyl group with 9 or less carbon atoms in the ester residue, such as n-butyl (meth)acrylate, isobutyl (meth)acrylate, t-butyl (meth)acrylate, pentyl (meth)acrylate, and n-octyl (meth)acrylate; monofunctional (meth)acrylates having an alkenyl group with 9 or less carbon atoms in the ester residue, such as pentenyl (meth)acrylate, butenyl (meth)acrylate, and hexenyl (meth)acrylate; monofunctional (meth)acrylates having a heterocycle, such as tetrahydrofurfuryl (meth)acrylate; 2-hydroxyethyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, and the like.
  • Examples of such monofunctional (meth)acrylates include monofunctional (meth)acrylates having a hydroxyl group, such as 4-hydroxybutyl (meth)acrylate, and glycidyl (meth)acrylate; monofunctional (meth)acrylates having an epoxy group, such as glycidyl (meth)acrylate; monofunctional (meth)acrylates having a maleimide group, such as (meth)acrylolyloxyethylhexahydrophthalimide; and monofunctional (meth)acrylates containing an alkoxyl group, such as 3-(meth)acryloxypropylmethyldimethoxysilane, 3-(meth)acryloxypropyltrimethoxysilane, 3-(meth)acryloxypropylmethyldiethoxysilane, and 3-(meth)acryloxypropyltriethoxysilane.
  • monofunctional (meth)acrylates having a hydroxyl group such as 4-hydroxybutyl (meth)acrylate, and glycid
  • the content of component (B) must be 20 to 90% by weight, preferably 40 to 90% by weight, and more preferably 50 to 85% by weight, based on 100% by weight of the total amount of the curable components. Furthermore, the content of (B-1) is 15 to 70% by weight, preferably 30 to 70% by weight, based on 100% by weight of the total amount of the curable components. If the content of the (B-1) component is less than 15% by weight, the swelling ratio of the cured product after immersion in the electrolyte increases, and the adhesive strength to the electrode foil after immersion in the electrolyte decreases. On the other hand, if the content exceeds 70% by weight, the adhesive strength of the cured product decreases.
  • the content of (B-2) is 5 to 50% by weight, preferably 10 to 40% by weight, based on 100% by weight of the total amount of the curable components. If the content of the (B-2) component is less than 5% by weight, the swelling ratio of the cured product after immersion in the electrolyte increases, and the adhesive strength to the electrode foil after immersion in the electrolyte decreases. On the other hand, if the content exceeds 70% by weight, the adhesive strength of the cured product decreases. It is preferable that the (B-3) component is not contained, and when it is contained, its content is preferably 8% by weight or less based on 100% by weight of the total amount of the curable components. By making the content ratio 8% by weight or less, the swelling rate of the cured product after immersion in an electrolyte solution can be reduced.
  • Component (C) is a photoradical polymerization initiator.
  • the component (C) is a compound that generates radicals when irradiated with active energy rays and initiates polymerization of a compound having an ethylenically unsaturated group.
  • component (C) examples include benzil dimethyl ketal, benzil, benzoin, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1-[4-(2-hydroxyethoxy)phenyl]-2-hydroxy-2-methyl-1-propan-1-one, oligo[2-hydroxy-2-methyl-1-[4-1-(methylvinyl)phenyl]propanone, 2-hydroxy-1-[4-[4-(2-hydroxy-2-methyl-propionyl)benzyl]phenyl]-2-methylpropanone, propan-1-one, 2-methyl-1-[4-(methylthio)]phenyl]-2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)butan-1-one, 2-dimethylamino
  • the content of component (C) is 0.1 to 20 parts by weight, preferably 0.2 to 10 parts by weight, and more preferably 0.5 to 5 parts by weight, per 100 parts by weight of the total curable components. If the content of component (C) is less than 0.1 part by weight, the photocurability of the composition will decrease, and if it exceeds 20 parts by weight, the solvent resistance of the cured product after immersion in the electrolyte will decrease.
  • composition of the present invention contains the above-mentioned components (A), (B), and (C) as essential components, but can also contain various components that are commonly used as sealing materials.
  • the compound include a compound having an ethylenically unsaturated group other than the components (A) and (B) (hereinafter referred to as “component (D)”), a filler (hereinafter referred to as “component (E)”), a photoacid generator, a silane coupling agent, an antioxidant, an ultraviolet absorber, a light stabilizer, a tackifier, a thiol compound, a plasticizer, a fluorescent agent, a colorant, a pigment, a dispersant and/or an antistatic agent.
  • Component (D) is a compound having an ethylenically unsaturated group and is a compound other than components (A) and (B).
  • the ethylenically unsaturated group in component (D) include a (meth)acryloyl group, a (meth)acrylamide group, a vinyl group, and an allyl group. Of these, a (meth)acryloyl group is preferred because of its excellent copolymerizability with other components.
  • component (D) Various compounds having an ethylenically unsaturated group can be used as component (D), such as compounds having two (meth)acryloyl groups in one molecule (hereafter referred to as “bifunctional (meth)acrylates”) and compounds having three or more (meth)acryloyl groups (hereafter referred to as “tri- or higher functional (meth)acrylates”).
  • bifunctional (meth)acrylates compounds having two (meth)acryloyl groups in one molecule
  • tri- or higher functional (meth)acrylates compounds having three or more (meth)acryloyl groups
  • bifunctional (meth)acrylate examples include di(meth)acrylates having a divalent alkyl group, such as ethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, tetramethylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, and nonanediol di(meth)acrylate; polyalkylene glycol di(meth)acrylates, such as polyethylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, and polytetramethylene glycol di(meth)acrylate; di(meth)acrylates having an alicyclic group, such as tricyclodecane dimethylol di(meth)acrylate; di(meth)acrylates of alkylene oxide adducts of bisphenol A; and urethane di(meth)acrylate.
  • trifunctional or higher (meth)acrylates include trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, and tris(2-(meth)acryloyloxyethyl)isocyanurate.
  • component (D) is preferably 8% by weight or less, and more preferably 0 to 5% by weight, based on 100% by weight of the curable component.
  • Component (E) is a filler.
  • the component (E) include metal oxides such as silica and alumina, and polymer fine particles such as polyethylene fine particles, polypropylene fine particles, crosslinked acrylic fine particles, and crosslinked polystyrene fine particles.
  • the particle size of the fine particles is preferably 0.1 to 200 ⁇ m, and more preferably 1 to 100 ⁇ m.
  • component (E) when applying by inkjet or spray, it is preferable to not include the (E) component or to keep it to a very small amount.
  • the content of component (E) is preferably 0 to 60% by weight based on 100% by weight of the composition.
  • the present invention relates to a photocurable composition for lithium-ion secondary battery sealing material, which contains the above-mentioned components (A) to (C) in the above-mentioned ratios.
  • the proportion of the curable component in the composition is preferably 40 to 99.9% by weight, and more preferably 50 to 99.5% by weight, based on 100% by weight of the composition.
  • the total content of the curable component and the component (E) in 100 weight% of the composition is preferably 80 to 99.9 weight%, more preferably 90 to 99.9 weight%, and even more preferably 95 to 99.9 weight%.
  • the composition can be produced by stirring and mixing the above-mentioned components (A) to (C) and, if necessary, other components, in a conventional manner. In this case, heating may be performed as necessary.
  • the heating temperature may be appropriately set depending on the components, base material, purpose, etc. used, but is preferably 30 to 80°C.
  • the viscosity of the composition may be adjusted depending on the coating method, but is preferably 10 to 100,000 mPa ⁇ s at 25° C., and more preferably 100 to 10,000 mPa ⁇ s.
  • the method of using the composition of the present invention may be a conventional method, and includes, for example, a method including a step of applying or injecting the composition of the present invention to a material constituting a lithium ion secondary battery, and a step of irradiating the applied or injected composition with light to cure it.
  • Materials that make up a lithium-ion secondary battery include a current collector foil, a positive electrode active material, a negative electrode active material, a separator, and an electrolyte.
  • collector foil examples include aluminum and copper.
  • the active material may be appropriately selected depending on the type of battery.
  • the positive electrode active material may be a lithium-transition metal composite oxide, a lithium-transition metal phosphate compound, or a lithium-transition metal sulfate compound.
  • the negative electrode active material include metals such as Si and Sn; metal oxides such as TiO, Ti2O3 , TiO2 , SiO2 , SiO, and SnO2 ; composite oxides of lithium and transition metals; Li-Pb alloys, Li-Al alloys; and carbon materials such as graphite, carbon black, activated carbon, carbon fiber, coke, soft carbon, and hard carbon.
  • Separators include microporous membrane films made of polyolefins such as polyethylene and polypropylene, multilayer films of porous polyethylene film and polypropylene, nonwoven fabrics made of polyester fibers, aramid fibers, glass fibers, etc., and those with ceramic particles such as silica, alumina, and titania attached to their surfaces.
  • electrolyte examples include ethylene carbonate, propylene carbonate, dimethyl carbonate, methyl ethyl carbonate, and diethyl carbonate, and a mixture of these may also be used.
  • Application and injection methods may be any known method, including the use of a dispenser, jet dispenser, screen printing, natural coater, knife belt coater, floating knife, knife over roll, knife on blanket, spray, dip, kiss roll, squeeze roll, reverse roll, air blade, curtain flow coater, comma coater, gravure coater, microgravure coater, die coater, and curtain coater.
  • Examples of light include visible light and ultraviolet light, with ultraviolet light being preferred since inexpensive equipment can be used.
  • various light sources can be used, such as pressurized or high-pressure mercury lamps, metal halide lamps, xenon lamps, electrodeless discharge lamps, carbon arc lamps, and LEDs.
  • high-pressure mercury lamps, metal halide lamps, and LEDs are preferred.
  • the amount of ultraviolet light irradiation is preferably 50 to 5,000 mJ/cm 2 in the UV-A region (near 365 nm), and more preferably 100 to 3,000 mJ/cm 2.
  • the illuminance of ultraviolet light is preferably 10 to 5,000 mW/cm 2 in the UV-A region (near 365 nm), and more preferably 100 to 2,000 mW/cm 2 .
  • FIG. 1 is a cross-sectional view of an example of a bipolar type lithium ion secondary battery.
  • a positive electrode active material 12, a separator 13, and a negative electrode active material 14 are disposed in a space sandwiched between current collector foils 11.
  • An electrolyte solution is present in the space between the positive electrode active material 12, the separator 13, and the negative electrode active material 14.
  • the outer periphery is sealed by a sealing member 15 which is a cured product of a composition to prevent leakage of the electrolyte solution.
  • the composition of the present invention is particularly suitable as a sealing material for lithium ion secondary batteries having such a structure.
  • Fig. 1 shows an example of two layers for ease of understanding, in reality, a structure having several tens of layers may be used.
  • FIG. 2 shows an example in which the battery constituent materials are laminated, the composition of the present invention is applied from the side so as to fill the laminate, and light is irradiated from the side.
  • FIG. 2(1) shows an example of a process in which battery constituent materials are laminated (21 in FIG. 2) and then the composition of the present invention is applied from the side so as to fill the laminate.
  • Specific examples of the application method include a dispenser, a jet dispenser, an inkjet, a spray, etc.
  • Figure 2 (1) shows an example in which a 22 dispenser is used.
  • the electrolyte can be injected into the inside with a syringe or the like after the composition has been cured.
  • the composition of the present invention can be injected again from above the hole with a dispenser or the like, and then photocured. This allows the hole of the injection port to be sealed.
  • the composition may be applied to three of the four side surfaces and cured, and the electrolyte may be poured from the open side surface while leaving the remaining side open. After pouring a predetermined amount of electrolyte, the composition may be applied to the last side surface and cured, thereby sealing all four sides.
  • FIG. 3 shows an example of a method for producing a lithium ion secondary battery by applying and curing a composition in the process of laminating battery constituent materials.
  • a current collector foil is prepared having active material (12 positive electrode active material or 14 negative electrode active material) applied to the center portion of both sides.
  • the composition (15') of the present invention is applied to the outer periphery as shown in 32.
  • the application method is preferably screen printing or a dispenser.
  • the separator 13 is placed over the substrate as shown at 33, and ultraviolet (UV) rays are irradiated from above by the ultraviolet irradiator 23 as shown at 34.
  • a polyolefin-based material is used for the separator 13, which is preferable because it transmits ultraviolet rays.
  • the composition (15') of the present invention is applied to the outer peripheral portion, and as shown in 36, ultraviolet rays are irradiated from above by the ultraviolet irradiation device 23 to cause curing.
  • a current collector foil having active material (12 positive electrode active material or 14 negative electrode active material) applied to the center portion of both sides is laminated.
  • the composition can be bonded by applying pressure at room temperature. If the composition does not have adhesive properties, it can be bonded by applying pressure with a press at about 60 to 100° C. The temperature at this time is lower than that of a heat-sealing sealant, so wrinkles and warping due to thermal expansion can be suppressed.
  • the electrolyte can be injected in the same manner as described in Fig. 2. Alternatively, ultraviolet light may be irradiated between 32 and 33, and the electrolyte may be injected before laminating the separator 13 and before laminating the electrode foil 37.
  • Production Example 1 [Production of bifunctional urethane acrylate having a hydrogenated polybutadiene skeleton] A 3 L four-neck separable flask was charged with 962 g (0.48 moles of hydroxyl groups) of GI-3000 (hydroxyl value 28.0 mg KOH/g, Mn approximately 4,000) manufactured by Nippon Soda Co., Ltd.
  • IBXA isobornyl acrylate
  • HBA 4-hydroxybutyl acrylate
  • the resulting product was a mixture containing 70% of a urethane acrylate having a hydrogenated polybutadiene skeleton (hereinafter referred to as "PUA-1") and 30% of IBXA as a diluent monomer.
  • the product was analyzed by GPC, and the peak of the PUA-1 component was confirmed to be distinct from that of the monomer component.
  • the polystyrene-equivalent molecular weight of the PUA-1 component was Mn 19,000 and Mw 34,500.
  • Production Example 2 [Production of bifunctional urethane acrylate having hydrogenated polybutadiene skeleton] The same procedure as in Production Example 1 was repeated except that IBXA in Production Example 1 was changed to isostearyl acrylate (hereinafter, referred to as "ISTA"), and a mixture containing 70% PUA-1 and 30% ISTA was obtained.
  • IBXA isostearyl acrylate
  • the flask was equipped with a thermometer, a gas inlet tube, a dropping funnel, and a reflux condenser, and the contents were stirred while blowing in a mixed gas of oxygen and nitrogen (5% oxygen), and further refluxed in an oil bath at 120° C. for 2 hours.
  • This solution was transferred to a separating funnel and washed with pure water three times.
  • 0.012 g of 4-methoxyphenol was added as a polymerization inhibitor, and the mixture was stirred at 80°C while blowing in dry air, and gradually distilled off under reduced pressure.
  • GI-AA bifunctional acrylate
  • the molecular weight of GI-AA was Mn of 3,000 and Mw of 4,200.
  • Examples 1 to 7 and Comparative Examples 1 to 10 1) Production of photocurable composition for lithium ion secondary battery sealing material Each component shown in Tables 1 and 2 below was blended in the ratio shown in Tables 1 and 2, and stirred and mixed in a conventional manner to obtain a photocurable composition for lithium ion secondary battery sealing material. In preparing the composition, heating to about 80° C. was performed as necessary.
  • the number of parts of PUA-1 in the table indicates the number of parts of only the urethane acrylate component contained in the product of Production Example 1 or Production Example 2. Furthermore, the number of parts of component (B) includes the component (B) contained in the product of Production Example 1, and the number of parts of component (B) indicates the total number of parts of component (B) contained in the product of Production Example 1 and component (B) added later.
  • ⁇ (C) Component ONE ⁇ -hydroxyalkylphenone photopolymerization initiator (ESACURE ONE manufactured by IGM Resins)
  • O-184 1-hydroxy-cyclohexyl-phenyl-ketone (Omnirad 184, manufactured by IGM Resins)
  • O-651 2,2-dimethoxy-1,2-diphenylethan-1-one (Omnirad 651, manufactured by IGM Resins)
  • compositions obtained above were used to evaluate initial peel strength, peel strength after immersion in an electrolyte solvent, and swelling after immersion in an electrolyte solvent according to the following methods. The results are shown in Tables 1 and 2.
  • the curing conditions were as follows: a 365 nm LED (surface-type LED irradiator manufactured by CCS Corporation) was used, and irradiation was performed from the PET film side for 5 seconds with an illuminance of 1000 mW/ cm2 (measured with a C12684 illuminometer manufactured by Hamamatsu Photonics K.K.). The cured sample was cut into a 10 mm wide strip, the PET film side was attached to a metal plate with double-sided tape, the metal foil was bent 180° and slightly peeled off, and the 180° peel strength was measured using an Instron 5564 (manufactured by Instron Japan Co., Ltd.). The tensile speed was 60 mm/s. Measurement results of 1 N/cm or less were marked x, 1 N/cm to 5 N/cm were marked ⁇ , and 5 N/cm or more were marked ⁇ .
  • composition obtained above was poured into a silicone mold cut to an arbitrary size and 1 mm thick, and then laminated with a 75 ⁇ m thick silicone-treated release PET film (HTA manufactured by Fujimori Kogyo Co., Ltd.) to eliminate polymerization inhibition due to oxygen, and photocured.
  • the curing conditions were 365 nm LED (surface type LED irradiator manufactured by CCS Co., Ltd.) and irradiated from both sides for 5 seconds at an illuminance of 1000 mW/cm 2 (measured with a C12684 illuminometer manufactured by Hamamatsu Photonics Co., Ltd.).
  • the PET film was then peeled off to obtain a cured product.
  • the compositions of the present invention were excellent in the initial peel strength and the peel strength after immersion in the electrolyte solvent against aluminum and copper, and further, had a small swelling ratio after immersion in the electrolyte solvent.
  • the comparative compositions not containing the component (B-1) were as follows.
  • the composition of Comparative Example 1 had a significant decrease in initial peel strength against aluminum and peel strength after immersion in an electrolyte solvent.
  • the composition of Comparative Example 5 had a significant decrease in initial peel strength against aluminum and copper and peel strength after immersion in an electrolyte solvent.
  • the composition of Comparative Example 6 had no problem with the initial peel strength against aluminum and copper, but the peel strength after immersion in an electrolyte solvent was significantly decreased and the swelling ratio after immersion in an electrolyte solvent was large.
  • the compositions of Comparative Examples 2 to 4 not containing the component (B-2) showed a significant decrease in the initial peel strength to aluminum and copper and in the peel strength after immersion in the electrolyte solvent.
  • the comparative compositions not containing the component (A) were as follows.
  • the compositions of Comparative Examples 7 and 8 showed a slight decrease in initial peel strength against aluminum and copper, a large decrease in peel strength after immersion in an electrolyte solvent, and a large swelling ratio after immersion in an electrolyte solvent.
  • Comparative Example 9 showed a large decrease in initial peel strength against aluminum and copper and peel strength after immersion in an electrolyte solvent.
  • the composition of Comparative Example 10 showed no problem in initial peel strength against aluminum and copper, but a large decrease in peel strength after immersion in an electrolyte solvent.
  • the present invention relates to a photocurable composition for use as a sealing material for lithium ion secondary batteries, which can be preferably used in the manufacture of lithium ion secondary batteries.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Electrochemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Materials Engineering (AREA)
  • Manufacturing & Machinery (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
PCT/JP2023/041122 2022-11-17 2023-11-15 リチウムイオン二次電池シール材用光硬化型組成物 Ceased WO2024106476A1 (ja)

Priority Applications (3)

Application Number Priority Date Filing Date Title
KR1020257017112A KR20250110841A (ko) 2022-11-17 2023-11-15 리튬 이온 2차 전지 밀봉재용 광경화형 조성물
CN202380078592.6A CN120129988A (zh) 2022-11-17 2023-11-15 锂离子二次电池密封材料用光固化型组合物
JP2024558926A JPWO2024106476A1 (https=) 2022-11-17 2023-11-15

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2022183810 2022-11-17
JP2022-183810 2022-11-17

Publications (1)

Publication Number Publication Date
WO2024106476A1 true WO2024106476A1 (ja) 2024-05-23

Family

ID=91084523

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2023/041122 Ceased WO2024106476A1 (ja) 2022-11-17 2023-11-15 リチウムイオン二次電池シール材用光硬化型組成物

Country Status (4)

Country Link
JP (1) JPWO2024106476A1 (https=)
KR (1) KR20250110841A (https=)
CN (1) CN120129988A (https=)
WO (1) WO2024106476A1 (https=)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN118800946A (zh) * 2024-06-28 2024-10-18 深圳市贝特瑞新能源技术研究院有限公司 双极性电池及其制备方法

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0733837A (ja) * 1993-07-20 1995-02-03 Three Bond Co Ltd 光硬化性樹脂組成物
KR20110101331A (ko) * 2010-03-08 2011-09-16 주식회사 엘지화학 신규한 구조의 전지팩 제조방법
JP2019175778A (ja) * 2018-03-29 2019-10-10 凸版印刷株式会社 バイポーラ電池ユニット及びバイポーラ電池
CN114316809A (zh) * 2022-01-10 2022-04-12 南亚新材料科技股份有限公司 锂电池用密封胶及其制备方法

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5455098B2 (ja) 2013-04-05 2014-03-26 住友電気工業株式会社 リアクトル
JP6659254B2 (ja) 2015-06-30 2020-03-04 日産自動車株式会社 二次電池およびその製造方法
JP6861016B2 (ja) 2015-11-19 2021-04-21 三洋化成工業株式会社 リチウムイオン電池
JP7235415B2 (ja) 2020-07-09 2023-03-08 トヨタ自動車株式会社 全固体電池および該全固体電池に用いる樹脂層形成用材料

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0733837A (ja) * 1993-07-20 1995-02-03 Three Bond Co Ltd 光硬化性樹脂組成物
KR20110101331A (ko) * 2010-03-08 2011-09-16 주식회사 엘지화학 신규한 구조의 전지팩 제조방법
JP2019175778A (ja) * 2018-03-29 2019-10-10 凸版印刷株式会社 バイポーラ電池ユニット及びバイポーラ電池
CN114316809A (zh) * 2022-01-10 2022-04-12 南亚新材料科技股份有限公司 锂电池用密封胶及其制备方法

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN118800946A (zh) * 2024-06-28 2024-10-18 深圳市贝特瑞新能源技术研究院有限公司 双极性电池及其制备方法

Also Published As

Publication number Publication date
KR20250110841A (ko) 2025-07-21
CN120129988A (zh) 2025-06-10
JPWO2024106476A1 (https=) 2024-05-23

Similar Documents

Publication Publication Date Title
JP5928578B2 (ja) 硬化膜を有する金属基材の製造方法
JP7235037B2 (ja) 高分子電解質接着用、又は高分子電解質シール用硬化型組成物
JP6106355B2 (ja) プラスチック製フィルム又はシート用活性エネルギー線硬化型接着剤組成物
JP5935668B2 (ja) 活性エネルギー線硬化型コーティング剤組成物
JP6107640B2 (ja) 活性エネルギー線硬化型コーティング剤組成物
JP5853859B2 (ja) プラスチック製フィルム又はシート用活性エネルギー線硬化型接着剤組成物
WO2016194937A1 (ja) （メタ）アクリル系共重合体、それを含む粘着組成物および粘着シート、並びにそれを用いた被覆材及び塗装物
WO2024106476A1 (ja) リチウムイオン二次電池シール材用光硬化型組成物
JP6137172B2 (ja) 活性エネルギー線硬化型組成物、並びに、硬化膜を有する金属基材及びその製造方法
KR102670018B1 (ko) 전고체 전지 및 당해 전고체 전지에 이용하는 광경화형 조성물
JP7318366B2 (ja) 触媒層用活性エネルギー線硬化型組成物及び積層体
JP2014009339A (ja) プラスチック製フィルム又はシート用活性エネルギー線硬化型接着剤組成物
CN116323727B (zh) 燃料电池用光固化型片状密封剂、固化物、燃料电池及密封方法
JP2014051654A (ja) 活性エネルギー線硬化型コーティング剤組成物
CN116249726A (zh) 燃料电池用构件及其制造方法
WO2014024826A1 (ja) 活性エネルギー線硬化型コーティング剤組成物
JP2018104635A (ja) 活性エネルギー線硬化性接着剤組成物、偏光板用接着剤組成物、偏光板用接着剤およびそれを用いた偏光板
JP6183036B2 (ja) 絶縁性硬化膜を有する金属基材の製造方法
JP5835055B2 (ja) プラスチック製フィルム又はシート用活性エネルギー線硬化型接着剤組成物
CN120209632A (zh) 一种uv喷墨胶水及其制备方法和应用
CN121718215A (zh) 一种边缘绝缘防护光固化喷印油墨及其制备方法和应用
CN121642483A (zh) 绝缘层、绝缘膜、固化粘接方法、电池包和用电设备
JP2007002193A (ja) （メタ）アクリル基含有ケイ素化合物、それを用いる感光性樹脂組成物及びその硬化物
WO2026079347A1 (ja) 光硬化性組成物
JP2015117349A (ja) 活性エネルギー線硬化型コーティング組成物

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 23891623

Country of ref document: EP

Kind code of ref document: A1

WWE Wipo information: entry into national phase

Ref document number: 2024558926

Country of ref document: JP

WWE Wipo information: entry into national phase

Ref document number: CN2023800785926

Country of ref document: CN

Ref document number: 202380078592.6

Country of ref document: CN

WWP Wipo information: published in national office

Ref document number: 202380078592.6

Country of ref document: CN

NENP Non-entry into the national phase

Ref country code: DE

WWP Wipo information: published in national office

Ref document number: 1020257017112

Country of ref document: KR

122 Ep: pct application non-entry in european phase

Ref document number: 23891623

Country of ref document: EP

Kind code of ref document: A1