WO2019131591A1 - Agent adhésif, stratifié, matériau d'enveloppement pour batterie, et batterie - Google Patents

Agent adhésif, stratifié, matériau d'enveloppement pour batterie, et batterie Download PDF

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Publication number
WO2019131591A1
WO2019131591A1 PCT/JP2018/047472 JP2018047472W WO2019131591A1 WO 2019131591 A1 WO2019131591 A1 WO 2019131591A1 JP 2018047472 W JP2018047472 W JP 2018047472W WO 2019131591 A1 WO2019131591 A1 WO 2019131591A1
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WIPO (PCT)
Prior art keywords
anhydride
acid
acid anhydride
adhesive
olefin resin
Prior art date
Application number
PCT/JP2018/047472
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English (en)
Japanese (ja)
Inventor
翔 三木
高年 松尾
神山　達哉
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Dic株式会社
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Application filed by Dic株式会社 filed Critical Dic株式会社
Priority to JP2019542254A priority Critical patent/JP6610985B1/ja
Priority to CN201880079869.6A priority patent/CN111479889B/zh
Publication of WO2019131591A1 publication Critical patent/WO2019131591A1/fr

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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
    • H01M50/102—Primary casings; Jackets or wrappings characterised by their shape or physical structure
    • H01M50/105—Pouches or flexible bags
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B15/00—Layered products comprising a layer of metal
    • B32B15/04—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material
    • B32B15/08—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
    • B32B15/085—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin comprising polyolefins
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/06—Non-macromolecular additives organic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J123/00—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J123/00—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers
    • C09J123/26—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers modified by chemical after-treatment
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
    • Y02E60/10—Energy storage using batteries

Definitions

  • the present invention relates to an adhesive, in particular, a polyolefin-based adhesive suitable for bonding a resin base and a metal base, a laminate obtained using the adhesive, an outer covering material for a secondary battery, and a battery.
  • a secondary battery represented by a lithium ion battery has a configuration in which an electrolytic solution or the like is sealed between a positive electrode, a negative electrode, and between them.
  • a sealing bag for sealing a lead wire for taking out the electricity of the positive electrode and the negative electrode a metal substrate and plastic comprising a heat seal layer made of an olefin resin, a metal foil such as aluminum foil and a metal deposition layer It is known to use the laminated body which bonded together (patent document 1, 2).
  • the olefin resin is nonpolar, adhesion to the metal substrate is difficult.
  • a battery element is sealed by heat-sealing the sealant layers located in the periphery of a battery element, and sealing a battery element.
  • the adhesive for bonding the heat seal layer and the metal substrate needs heat resistance in addition to the adhesiveness between the nonpolar substrate such as an olefin resin and the metal substrate.
  • the present invention has been made in view of such a situation, and it is an object of the present invention to provide an adhesive excellent in adhesion between a nonpolar base such as an olefin resin and a metal base and heat resistance. Do. Furthermore, it is an object of the present invention to provide a laminate obtained using such an adhesive, and a secondary battery package and battery obtained using the laminate.
  • the present invention includes an olefin resin (A), a curing agent (B) containing an epoxy compound, and an acid anhydride (C), and the compounding amount of the acid anhydride (C) is 100 parts by mass of the olefin resin (A)
  • the present invention relates to an adhesive that is 0.05 parts by mass or more and 10 parts by
  • the adhesive of the present invention is excellent in the adhesion between a nonpolar substrate such as an olefin resin and a metal substrate, and heat resistance.
  • the laminate of the present invention is excellent in adhesion and heat resistance.
  • the adhesive of the present invention comprises an olefin resin (A), a curing agent (B) containing an epoxy compound, and an acid anhydride (C).
  • A olefin resin
  • B curing agent
  • C acid anhydride
  • olefin resin (A) used in the adhesive of the present invention homopolymers and copolymers of olefin monomers, copolymers of olefin monomers and other monomers, hydrides and halides of these polymers, acids And polymers having a hydrocarbon backbone as a main component, such as modified products into which functional groups such as hydroxyl groups are introduced, and the like, and one or more types can be used in combination. It is preferable to use a crystalline olefin resin having an acid group or an acid anhydride group and a crystalline olefin resin having a hydroxyl group.
  • An acid-modified olefin resin (A-1) which is a copolymer of an olefin monomer and an ethylenically unsaturated carboxylic acid or an ethylenically unsaturated carboxylic acid anhydride as an olefin resin having an acid group or an acid anhydride group
  • an acid-modified olefin resin (A-2) which is a resin obtained by graft-modifying an ethylenically unsaturated carboxylic acid or an ethylenically unsaturated carboxylic acid anhydride to a polyolefin.
  • the olefin monomer used for the preparation of the acid-modified olefin resin (A-1) is an olefin having 2 to 8 carbon atoms, such as ethylene, propylene, isobutylene, 1-butene, 4-methyl-1-pentene, Hexene, vinyl cyclohexane and the like can be mentioned.
  • olefins having 3 to 8 carbon atoms are preferable, in particular, propylene and 1-butene are more preferable, and using propylene and 1-butene in combination is particularly preferable for the solvent because the adhesive strength is good. It is preferable from the point which is excellent in tolerance and excellent in adhesive strength.
  • Examples of the ethylenically unsaturated carboxylic acid or ethylenically unsaturated carboxylic acid anhydride used for copolymerization with an olefin-based monomer include, for example, acrylic acid, methacrylic acid, maleic acid, itaconic acid, citraconic acid, mesaconic acid, and maleic anhydride Acid, 4-methylcyclohex-4-ene-1,2-dicarboxylic acid anhydride, bicyclo [2.2.2] oct-5-ene-2,3-dicarboxylic acid anhydride, 1,2,3,3, 4,5,8,9,10-Octahydronaphthalene-2,3-dicarboxylic acid anhydride, 2-octa-1,3-diketospiro [4.4] non-7-ene, bicyclo [2.2.1 ] Hept-5-ene-2,3-dicarboxylic anhydride, maleopimaric acid, tetrahydrophthalic anhydride,
  • the reactivity with an olefin monomer, the reactivity with acid anhydride after copolymerization are excellent, and the molecular weight of the compound itself is small, and the functional group concentration in the case of making a copolymer becomes high.
  • maleic anhydride is preferred. These can be used alone or in combination of two or more.
  • a compound having an ethylenically unsaturated group in addition to an olefin monomer, a tyrene unsaturated carboxylic acid or an ethylenically unsaturated carboxylic acid anhydride, such as styrene, Butadiene, isoprene and the like may be used in combination.
  • the polyolefin used to prepare the acid-modified olefin resin (A-2) includes homopolymers and copolymers of olefins having 2 to 8 carbon atoms, and co-polymers of olefins having 2 to 8 carbon atoms and other monomers. Polymers, etc. may be mentioned.
  • polyethylene such as high density polyethylene (HDPE), low density polyethylene (LDPE), linear low density polyethylene resin, polypropylene, polyisobutylene, poly (1-butene), Poly (4-methyl-1-pentene), polyvinylcyclohexane, ethylene / propylene block copolymer, ethylene / propylene random copolymer, ethylene / 1-butene copolymer, ethylene / 4-methyl-1-pentene copolymer Combination, ⁇ -olefin copolymer such as ethylene / hexene copolymer, ethylene / vinyl acetate copolymer Coalesced, ethylene methyl methacrylate copolymer, ethylene-vinyl acetate-methyl methacrylate copolymer, and the like propylene-1-butene copolymer.
  • HDPE high density polyethylene
  • LDPE low density polyethylene
  • LDPE low density polyethylene
  • linear low density polyethylene resin polypropy
  • homopolymers of olefins having 3 to 8 carbon atoms and copolymers of two or more of olefins having 3 to 8 carbon atoms are preferable, from the viewpoint of achieving good adhesion strength, and propylene alone
  • a polymer or a propylene / 1-butene copolymer is more preferable, and a propylene / 1-butene copolymer is particularly preferable in that it is excellent in resistance to a solvent and excellent in adhesive strength.
  • the ethylenically unsaturated carboxylic acid or ethylenically unsaturated carboxylic acid anhydride used for graft modification with a polyolefin is used for copolymerization with an olefin monomer in the preparation of the acid-modified olefin resin (A-1) described above
  • A-1 acid-modified olefin resin
  • maleic anhydride is preferred. These can be used alone or in combination of two or more.
  • the polyolefin in order to cause the polyolefin to react with the ethylenically unsaturated carboxylic acid or the ethylenically unsaturated carboxylic acid anhydride by graft modification, specifically, the polyolefin is melted, and the ethylenically unsaturated carboxylic acid or the ethylenically unsaturated carboxylic acid is melted therein.
  • a method of adding an acid anhydride (grafting monomer) for grafting reaction dissolving a polyolefin in a solvent to form a solution, and adding an ethylenically unsaturated carboxylic acid or an ethylenically unsaturated carboxylic acid anhydride thereto to cause a grafting reaction Method, mixing polyolefin dissolved in organic solvent and ethylenic unsaturated carboxylic acid or ethylenic unsaturated carboxylic acid anhydride, heating at temperature above softening temperature or melting point of polyolefin, radical polymerization and hydrogen in molten state The method etc. which perform a withdrawal reaction simultaneously are mentioned.
  • the grafting reaction in order to graft-copolymerize the graft monomer efficiently, it is preferable to carry out the grafting reaction in the presence of a radical initiator.
  • the grafting reaction is usually carried out at 60 to 350.degree.
  • the proportion of the radical initiator used is usually in the range of 0.001 to 1 part by weight with respect to 100 parts by weight of the polyolefin before modification.
  • organic peroxides are preferred, such as benzoyl peroxide, dichloro benzoyl peroxide, dicumyl peroxide, di-tert-butyl peroxide, 2,5-dimethyl-2,5-di (peroxide benzoate) hexyne-3, 1,4-bis (tert-butylperoxyisopropyl) benzene, lauroyl peroxide, tert-butyl peracetate, 2,5-dimethyl-2,5-di (tert-butylperoxy) hexyne-3,2,5-dimethyl- 2.5-di (tert-butylperoxy) hexane, tert-butyl perbenzoate, tert-butyl perphenyl acetate, tert-butyl perisobutyrate, tert-butyl per-sec-octoate, tert- Chill perpivalate and cumyl peroxide, ter
  • the radical initiator may be selected optimally depending on the process of the grafting reaction, and generally, dicumyl peroxide, di-tert-butyl peroxide, 2,5-dimethyl-2,5-di (tert-butylperoxy) hexine Dialkyl peroxides such as -3,2,5-dimethyl-2,5-di (tert-butylperoxy) hexane and 1,4-bis (tert-butylperoxyisopropyl) benzene are preferably used.
  • the adhesion of the metal layer is further improved, and the electrolyte resistance is excellent. It is preferable to use one having an acid value of ⁇ 200 mg KOH / g.
  • the olefin resin (A-3) having a hydroxyl group a copolymer of a polyolefin and a hydroxyl group-containing (meth) acrylic acid ester or a hydroxyl group-containing vinyl ether, or a polyolefin grafted with a hydroxyl group-containing (meth) acrylic acid ester or a hydroxyl group-containing vinyl ether
  • the modified resin is mentioned.
  • the polyolefin those similar to those used for the preparation of the olefin resin (A-2) can be used.
  • the modification method the same method as the method for preparing the acid-modified olefin resin (A-1) or (A-2) can be used.
  • hydroxyl group-containing (meth) acrylates used for modification include hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate, glycerol (meth) acrylate, lactone modified hydroxyethyl (meth) acrylate, polyethylene glycol mono (meth) acrylate And polypropylene glycol mono (meth) acrylate.
  • hydroxyl group-containing vinyl ether include 2-hydroxyethyl vinyl ether, diethylene glycol monovinyl ether, 4-hydroxybutyl vinyl ether and the like.
  • olefin resin (A-3) having a hydroxyl group is used as the olefin resin (A)
  • the adhesion of the metal layer is further improved and the electrolyte resistance is excellent, so a hydroxyl value of 1 to 200 mg KOH / g It is preferable to use the one which it has.
  • the polyolefin used for the preparation of the acid-modified olefin resin (A-2) or the olefin resin (A-3) having a hydroxyl group may be used as it is without modification.
  • the weight average molecular weight of the olefin resin (A) is preferably 40,000 or more. In addition, in order to ensure appropriate fluidity, the weight average molecular weight of the olefin resin (A) is preferably 150,000 or less.
  • the weight average molecular weight (Mw) and the number average molecular weight (Mn) are values measured by gel permeation chromatography (GPC) under the following conditions.
  • the melting point of the olefin resin (A) is preferably 50 ° C. or more, more preferably 60 ° C. or more, and more preferably 65 ° C. or more.
  • the melting point of the olefin resin (A) is preferably 120 ° C. or less, more preferably 90 ° C. or less, and still more preferably 85 ° C. or less.
  • the melting point of the olefin resin is measured by DSC (differential scanning calorimetry). Specifically, the temperature is increased from 10 ° C./min to 10 ° C./min, and then cooled to 10 ° C./min to remove the heat history, and then the temperature is reached again at 10 ° C./min. Heat up to the point. The peak temperature at the second temperature rise is taken as the melting point. In addition, the temperature-fall achieving temperature is set to a temperature lower by 50 ° C. or more than the crystallization temperature, and the temperature-rise achieving temperature is set to a temperature higher by about 30 ° C. or more than the melting point temperature. The final temperature for temperature drop and the final temperature for temperature rise are determined by trial measurement.
  • An epoxy compound is used as the curing agent (B). It is not particularly limited as long as it is a compound having an epoxy group in the molecule, and, for example, ethylene glycol, propylene glycol, hexanediol, neopentyl glycol, trimethylolethane, trimethylolpropane, pentaerythritol, glycerin, diglycerin, sorbitol, spiro Polyglycidyl ether type epoxy resin of aliphatic polyol such as glycol or hydrogenated bisphenol A; Bisphenol type epoxy resins such as bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, bisphenol AD type epoxy resin; Aromatic epoxy resins such as phenol novolac resins and novolac type epoxy resins which are glycidyl ales of cresol novolac resins; Polyglycidyl ethers of polyols which are ethylene oxide or propylene oxide adducts of aromatic
  • the epoxy compound used in the present invention is preferably an epoxy compound having two or more epoxy groups and one or more hydroxyl groups in one molecule, and having a weight average molecular weight of 3,000 or less.
  • a compound other than the epoxy resin may be used in combination.
  • Other curing agents that can be used in combination with the epoxy resin include polyfunctional isocyanate compounds, aziridine group-containing compounds, carbodiimides, oxazolines, amino resins and the like.
  • polyfunctional isocyanate compounds 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, xylylene diisocyanate, diphenylmethane diisocyanate, isophorone diisocyanate, 1,5-naphthalene diisocyanate, hexamethylene diisocyanate, bis (4-isocyanatocyclohexyl) ) Methane or diisocyanates such as hydrogenated diphenylmethane diisocyanate and compounds derived therefrom, ie, isocyanurate, adduct, biuret type, uretdione, allophanate, prepolymer having isocyanate residue (diisocyanate) of the above diisocyanate And low polymers obtained from polyols, or complexes of these.
  • a compound obtained by reacting a part of the isocyanate group of the polyfunctional isocyanate compound as described above with a compound having reactivity with the isocyanate group may be used as a curing agent.
  • Compounds having reactivity with an isocyanate group include compounds containing an amino group such as butylamine, hexylamine, octylamine, 2-ethylhexylamine, dibutylamine, ethylenediamine, benzylamine and aniline: methanol, ethanol, propanol, isopropanol , Hydroxyl-containing compounds such as butanol, hexanol, octanol, 2-ethylhexyl alcohol, dodecyl alcohol, ethylene glycol, propylene glycol, benzyl alcohol, phenol and the like: allyl glycidyl ether, 2-ethylhexyl glycidyl ether, phenyl
  • aziridine group-containing compound for example, N, N′-hexamethylene-1,6-bis (1-aziridinecarboxamide), N, N′-diphenylmethane-4,4′-bis (1-aziridinecarboxamide) Trimethylolpropane-tri- ⁇ -aziridinyl propionate), N, N′-toluene-2,4-bis (1-aziridinecarboxamide), triethylenemelamine, trimethylolpropane-tri- ⁇ (2 -Methylaziridine) propionate, bisisophthaloyl-1-2-methylaziridine, tri-1-aziridinyl phosphine oxide, tris-1-2-methylaziridine phosphine oxide, etc. may be mentioned.
  • carbodiimides include N, N'-di-o-toluylcarbodiimide, N, N'-diphenylcarbodiimide, N, N'-di-2,6-dimethylphenylcarbodiimide, N, N'-bis (2,6- Diisopropylphenyl) carbodiimide, N, N′-dioctyldecylcarbodiimide, N-triyl-N′-cyclohexylcarbodiimide, N, N′-di-2,2-tert.
  • Monooxazoline compounds such as 2-oxazoline, 2-methyl-2-oxazoline, 2-phenyl-2-oxazoline, 2,5-dimethyl-2-oxazoline, 2,4-diphenyl-2-oxazoline and the like as oxazoline 2,2 '-(1,3-phenylene) -bis (2-oxazoline), 2,2'-(1,2-ethylene) -bis (2-oxazoline), 2,2 '-(1,4 butylene) And -bis (2-oxazoline), 2,2 '-(1,4-phenylene) -bis (2-oxazoline) and the like.
  • amino resin examples include melamine resin, benzoguanamine resin, urea resin and the like.
  • the compounding amount of the curing agent (B) is preferably 0.01 parts by mass or more, more preferably 0.1 parts by mass or more, and more preferably 0.5 parts by mass with respect to 100 parts by mass of the olefin resin (A). More preferably it is part or more. Further, the compounding amount of the curing agent (B) is preferably 10 parts by mass or less, more preferably 8 parts by mass or less, and 5 parts by mass or less with respect to 100 parts by mass of the olefin resin (A). Is more preferred. This makes it possible to develop excellent adhesion and chemical resistance.
  • an acid anhydride (C) a cyclic aliphatic acid anhydride, an aromatic acid anhydride, unsaturated carboxylic acid anhydride etc. are mentioned, It can be used 1 type or in combination of 2 or more types. More specifically, for example, phthalic anhydride, trimellitic anhydride, pyromellitic anhydride, benzophenone tetracarboxylic acid anhydride, dodecenyl succinic anhydride, polyadipic anhydride, polyazelaic anhydride, polysebacic acid Anhydride, poly (ethyloctadecanedioic acid) anhydride, poly (phenylhexadecanedioic acid) anhydride, tetrahydrophthalic anhydride, methyltetrahydrophthalic anhydride, methylhexahydrophthalic anhydride, hexahydrophthalic anhydride , Methylhymic acid anhydride, trialkyl
  • glycols that can be used for modification include alkylene glycols such as ethylene glycol, propylene glycol and neopentyl glycol; and polyether glycols such as polyethylene glycol, polypropylene glycol and potty tetramethylene ether glycol. Furthermore, copolymerized polyether glycols of two or more of these glycols and / or polyether glycols can also be used.
  • alkylene glycols such as ethylene glycol, propylene glycol and neopentyl glycol
  • polyether glycols such as polyethylene glycol, polypropylene glycol and potty tetramethylene ether glycol.
  • copolymerized polyether glycols of two or more of these glycols and / or polyether glycols can also be used.
  • it is 0.05 mass part or more with respect to 100 mass parts of olefin resin (A), and, as for the compounding quantity of an acid anhydride (C), it is more preferable that it is 0.8 mass part or more. Moreover, it is preferable that it is 10 mass parts or less with respect to 100 mass parts of olefin resin (A), and, as for the compounding quantity of an acid anhydride (C), it is more preferable that it is 8 mass parts or less. Thereby, the adhesion between the adhesive and the metal is improved, and an adhesive having excellent initial adhesive strength and adhesive strength after heat sealing can be obtained.
  • the acid anhydride (C) used by this invention is equipped with a polar group, and is excellent in the affinity to a metal base material.
  • the molecular weight is relatively small, movement is relatively easy. It is thought that the coated adhesive moves to the metal substrate side until it completely cures, and plays a role like a so-called anchor agent, thereby contributing to the improvement of adhesion and heat resistance.
  • the acid anhydride (C) contained in the adhesive is too large, the acid anhydride (C) forms a pseudo low layer between the metal substrate and the adhesive, It is considered that the adhesion is reduced due to this.
  • the adhesive of the present invention can ensure fluidity by expressing an organic solvent (D) in addition to the above-mentioned components, and can exhibit appropriate coatability.
  • organic solvent is not particularly limited as long as it can be removed by volatilization by heating in the drying step during adhesive coating, for example, aromatic organic solvents such as toluene and xylene; n-hexane, Aliphatic organic solvents such as n-heptane; alicyclic organic solvents such as cyclohexane and methylcyclohexane; halogen organic solvents such as trichloroethylene, dichloroethylene, chlorobenzene and chloroform; ketone solvents such as methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone Ester solvents such as ethyl acetate and butyl acetate; alcohol solvents such as ethanol, methanol, n-propanol, 2-propanol (iso
  • the solubility is excellent, and therefore it is an alicyclic
  • a mixed solvent of a system organic solvent, an ester solvent and an alcohol solvent it is preferable to use a mixed solvent of methylcyclohexane, ethyl acetate and isopropyl alcohol because of its excellent solubility.
  • the amount of the organic solvent used is preferably such that the proportion of the olefin resin (A) is 10 to 30% by mass with respect to the total mass of the olefin resin (A) and the organic solvent (D). Thereby, it can be set as the adhesive agent excellent in coating nature and the wettability to a metal film.
  • additives such as tackifiers, plasticizers, thermoplastic elastomers, reactive elastomers, phosphoric acid compounds, silane coupling agents and adhesion promoters can be used as needed.
  • the content of these additives may be appropriately adjusted within the range that does not impair the function of the adhesive of the present invention.
  • tackifiers examples include rosin-based or rosin ester-based tackifiers, terpene-based or terpene-phenol-based tackifiers, saturated hydrocarbon resins, coumarone-based tackifiers, coumarone-indene-based tackifiers. Agents, styrene resin-based tackifiers, xylene resin-based tackifiers, phenol resin-based tackifiers, petroleum resin-based tackifiers, and the like. These may be used alone or in combination of two or more.
  • plasticizer examples include polyisoprene, polybutene, and process oil.
  • thermoplastic elastomer examples include styrene-butadiene copolymer (SBS), hydrogenated product of styrene-butadiene copolymer (SEBS), SBBS, styrene-isoprene.
  • SEPS styrene-butadiene copolymer
  • SEBS hydrogenated product of styrene-butadiene copolymer
  • SBBS styrene-isoprene.
  • Copolymerized hydrogenated substances SEPS
  • TPS styrene block copolymers
  • TPO olefin-based elastomers
  • reactive elastomers obtained by acid-modifying these elastomers can be mentioned.
  • phosphoric acid compounds include phosphoric acids such as hypophosphorous acid, phosphorous acid, orthophosphoric acid, and hypophosphoric acid, for example, condensed phosphoric acids such as metaphosphoric acid, pyrophosphoric acid, tripolyphosphoric acid, polyphosphoric acid, ultraphosphoric acid, etc.
  • silane coupling agent for example, ⁇ -aminopropyltriethoxysilane, ⁇ -aminopropyltrimethoxysilane, N- ⁇ (aminoethyl) - ⁇ -aminopropyltrimethoxysilane, N- ⁇ (aminoethyl) - ⁇ - Aminosilanes such as aminopropyltrimethyldimethoxysilane, N-phenyl- ⁇ -aminopropyltrimethoxysilane, etc .; ⁇ - (3,4-epoxycyclohexyl) ethyltrimethoxysilane, ⁇ -glycidoxypropyltrimethoxysilane, ⁇ -glycid Epoxysilanes such as xylpropyltriethoxysilane; vinylsilanes such as vinyltris ( ⁇ -methoxyethoxy) silane, vinyltriethoxysilane, vinyltrimethoxysilane,
  • the adhesive of the present invention can be prepared by mixing the above-described components. Under the present circumstances, although each component may be mixed simultaneously and it is good also as an adhesive agent, components other than a hardening agent (B) are previously mixed, the premixer is adjusted, and the hardening agent (B) is mixed at the time of use of an adhesive agent. It is preferable to use a two-component type adhesive because it is excellent in the stability and the workability of the adhesive.
  • the adhesive of the present invention is excellent in the adhesion between a nonpolar substrate such as an olefin resin and a metal substrate, and heat resistance.
  • the laminate of the present invention is disposed between the first substrate, the second substrate, the first substrate and the second substrate, and the first substrate and the second substrate And an adhesive layer to be pasted together.
  • the adhesive layer is a cured coating of the above-mentioned adhesive.
  • other substrates may be included.
  • the adhesive layer for bonding the first substrate to another substrate, and the second substrate to another substrate may or may not be a cured coating of the adhesive of the present invention. Good.
  • first substrate, the second substrate, and other substrates examples include paper, olefin resins, acrylonitrile-butadiene-styrene copolymer (ABS resin), polyvinyl chloride resins, and fluorine resins.
  • Synthetic resin film obtained from poly (meth) acrylic resin, carbonate resin, polyamide resin, polyimide resin, polyphenylene ether resin, polyphenylene sulfide resin or polyester resin, metal such as copper foil, aluminum foil Foil etc. can be used.
  • the adhesive of the present invention is excellent in the adhesion between a nonpolar substrate such as an olefin resin and a metal substrate, so that one of the first substrate and the second substrate is nonpolar. It is preferable that the other is a metal base, but it is not limited thereto.
  • the laminate of the present invention is obtained by applying the adhesive of the present invention to one of the first substrate and the second substrate, then laminating the other, and curing the adhesive. After applying the adhesive, it is preferable to provide a drying process before laminating the first substrate and the second substrate.
  • a coating method of the adhesive a gravure coater method, a microgravure coater method, a reverse coater method, a bar coater method, a roll coater method, a die coater method or the like can be used.
  • the coating amount of the adhesive is preferably adjusted so that the coating weight after drying is 0.5 to 20.0 g / m 2 .
  • the temperature of the laminating roll at the time of laminating the first substrate and the second substrate is preferably 25 to 120 ° C., and the pressure is preferably 3 to 300 kg / cm 2 . It is preferable to provide an aging process after laminating the first base and the second base.
  • the aging conditions are preferably 25 to 100 ° C. for 12 to 240 hours.
  • the battery packaging material of the present invention comprises, as an example, a first substrate, a second substrate, a third substrate, and a first substrate and a second substrate bonded to each other. And an adhesive layer, and a second adhesive layer for bonding the second base and the third base.
  • the first substrate is a polyolefin film and the second substrate is a metal foil.
  • the third substrate is a resin film of nylon, polyester or the like.
  • the first adhesive layer is a cured coating of the adhesive of the present invention.
  • the second adhesive layer may or may not be a cured coating of the adhesive of the present invention.
  • the other substrate may be disposed on the side of the third substrate opposite to the side on which the second adhesive layer is provided, with or without the adhesive layer, or the coating layer may be provided. Good. It is not necessary to provide another base material or a coating layer.
  • the polyolefin film may be appropriately selected from conventionally known olefin resins.
  • polyethylene, polypropylene, an ethylene-propylene copolymer, etc. can be used. It is preferably a non-oriented film.
  • the thickness of the polyolefin film is not particularly limited, but is preferably 10 ⁇ m or more, more preferably 20 ⁇ m or more, and still more preferably 25 ⁇ m or more. The thickness is preferably 100 ⁇ m or less, more preferably 95 ⁇ m or less, and still more preferably 90 ⁇ m or less.
  • the first base material functions as a sealant layer when the battery packaging materials of the present invention are heat-sealed and bonded to each other when manufacturing a battery to be described later.
  • metal foil aluminum, copper, nickel etc. are mentioned. These metal foils are sandblasted, polished, degreased, etched, surface-treated by immersion in rust inhibitor or spray, trivalent chromium conversion treatment, phosphate conversion treatment, sulfide conversion treatment, anodic oxide film formation, It may be subjected to surface treatment such as fluorine resin coating. Among these, those subjected to trivalent chromium chemical conversion treatment are preferable from the viewpoint of excellent adhesion retention performance (environmental deterioration resistance) and corrosion resistance.
  • the thickness of the metal film is preferably in the range of 10 to 100 ⁇ m from the viewpoint of preventing corrosion.
  • resin films that can be used as the third substrate include resins such as polyester resin, polyamide resin, epoxy resin, acrylic resin, fluorine resin, polyurethane resin, silicone resin, phenol resin, and mixtures and copolymers of these.
  • a film is mentioned.
  • a polyester resin and a polyamide resin are preferably mentioned, and a biaxially stretched polyester resin and a biaxially stretched polyamide resin are more preferably mentioned.
  • the polyester resin include polyethylene terephthalate, polybutylene terephthalate, polyethylene naphthalate, polybutylene naphthalate, copolymer polyester, polycarbonate and the like.
  • Specific examples of the polyamide resin include nylon 6, nylon 6, 6, copolymer of nylon 6 and nylon 6, 6, nylon 6, 10, polymethaxylylene adipamide (MXD6), etc.
  • the coating layer can be formed of, for example, polyvinylidene chloride, polyester resin, urethane resin, acrylic resin, epoxy resin or the like. It is preferable to form by 2 liquid hardening type resin.
  • the two-component curable resin that forms the coating layer include a two-component curable urethane resin, a two-component curable polyester resin, and a two-component curable epoxy resin.
  • a matting agent may be blended in the coating layer.
  • Examples of the matting agent include fine particles having a particle size of about 0.5 nm to 5 ⁇ m.
  • the material of the matting agent is not particularly limited, and examples thereof include metals, metal oxides, inorganic substances, and organic substances.
  • the shape of the matting agent is also not particularly limited, and examples thereof include spheres, fibers, plates, indeterminate shapes, and balloons.
  • talc silica, graphite, kaolin, montmorrroid, montmorillonite, synthetic mica, hydrotalcite, silica gel, zeolite, aluminum hydroxide, magnesium hydroxide, zinc oxide, magnesium oxide, aluminum oxide , Neodymium oxide, antimony oxide, titanium oxide, cerium oxide, calcium sulfate, barium sulfate, calcium carbonate, calcium silicate, lithium carbonate, calcium benzoate, calcium oxalate, magnesium stearate, carbon black, carbon nanotubes, high melting point Nylon, crosslinked acrylic, crosslinked styrene, crosslinked polyethylene, benzoguanamine, gold, aluminum, copper, nickel and the like can be mentioned.
  • matting agents may be used alone or in combination of two or more.
  • the surface of the matting agent may be subjected to various surface treatments such as insulation treatment and high dispersion treatment.
  • Heat and pressure air forming method A concave portion is formed by sandwiching the battery packaging material between a lower mold having a hole to which high-temperature, high-pressure air is supplied and an upper mold having a pocket-shaped recess and supplying air while heating and softening. how to.
  • Pre-heater flat plate pneumatic molding method After heating and softening the battery packaging material, the air is supplied by holding it between the lower mold having a hole to which high-pressure air is supplied and the upper mold having a pocket-shaped recess. How to form a recess.
  • Drum-type vacuum forming method A method of forming a recess by vacuuming the recess of a drum having a pocket-shaped recess after partially heating and softening the battery packaging material with a heating drum.
  • -Pin molding method A method in which the bottom sheet is heated and softened and then crimped with a pocket-shaped uneven mold.
  • Pre-heater plug-assisted pressure forming method After heating and softening the battery packaging material, the air is supplied by holding it between the lower mold having a hole to which high-pressure air is supplied and the upper mold having a pocket-shaped recess.
  • the battery packaging material of the present invention can be suitably used as a battery container in which battery elements such as a positive electrode, a negative electrode, and an electrolyte are sealed and housed.
  • the battery of the present invention is a battery packaging material having a positive electrode, a negative electrode, and an electrolyte, in the battery packaging material of the present invention, in which the metal terminal connected to each of the positive electrode and the negative electrode protrudes outward. It is obtained by coating so that flanges (areas where sealant layers are in contact) can be formed on the periphery of the element, and the sealant layers of the flanges are heat sealed and sealed.
  • the battery obtained using the battery packaging material of the present invention may be either a primary battery or a secondary battery, but is preferably a secondary battery.
  • the secondary battery is not particularly limited, and examples thereof include lithium ion batteries, lithium ion polymer batteries, lead storage batteries, nickel hydrogen storage batteries, nickel cadmium storage batteries, nickel iron storage batteries, nickel zinc storage batteries, silver oxide zinc storage batteries, Metal air batteries, polyvalent cation batteries, capacitors, capacitors and the like can be mentioned.
  • lithium ion batteries and lithium ion polymer batteries can be mentioned as preferable applications of the battery packaging material of the present invention.
  • the prepared adhesive was applied to a glossy surface of an aluminum foil (aluminum foil "1N30H” manufactured by Toyo Aluminum Co., Ltd .: film thickness 30 ⁇ m) with a bar coater at a coating amount of 2 g / m 2 (dry) and dried at 80 ° C for 1 minute Thereafter, it was laminated at 100 ° C. with an unstretched polyolefin film (“ET-20” film thickness: 40 ⁇ m manufactured by Okamoto Co., Ltd.).
  • a bar coater at a coating amount of 4 g / m 2 (dry)
  • a 25 ⁇ m-thick stretched polyamide film was laminated.
  • curing (aging) at 80 ° C. for 2 days was performed to obtain a laminate.
  • Example 2 An adhesive was prepared in the same manner as in Example 1 except that the composition of the adhesive used for laminating the aluminum foil and the unstretched polyolefin film was changed to the composition described in Tables 1 and 2, to obtain a laminate.
  • Toyo Tack PMA-L maleic anhydride modified olefin resin, acid value: 35 mg KOH / g, melting point: 70 ° C.
  • Toyo tack PMA-KE manufactured by Toyobo Co., Ltd . maleic anhydride modified olefin resin, acid number: 44 mg KOH / g, melting point: 80 ° C.
  • the acid value of the olefin resin is a coefficient (f) obtained from a calibration curve prepared by using a solution of maleic anhydride in chloroform using FT-IR (FT-IR 4200, manufactured by JASCO Corporation), a maleic anhydride-modified polyolefin solution Calculated using the following formula using the absorbance (I) of the stretching peak (1780 cm -1 ) of the anhydride ring of maleic anhydride and the absorbance (II) of the stretching peak (1720 cm -1 ) of the carbonyl group of maleic acid in .
  • the molecular weight of maleic anhydride is 98.06
  • the molecular weight of potassium hydroxide is 56.11.
  • Bonding strength of the interface between aluminum foil and unstretched polyolefin film of the laminate is 50 mm / min, peeling width 15 mm, peeling form T type using "Autograph AGS-J" manufactured by Shimadzu Corporation. evaluated.
  • the unstretched polyolefin film side of the laminate was valley-folded, and the heat-seal bar was applied to the unstretched polyolefin film sides under the condition of 190 ° C. for 3 seconds. Then, using “Autograph AGS-J” manufactured by Shimadzu Corporation, the interface was evaluated when peeled at 1 cm under the conditions of peeling speed 500 mm / min, peeling width 15 mm, peeling form T type.
  • ⁇ Peeling between unstretched polyolefin film / unstretched polyolefin film is 90% or more (especially excellent in practical use)
  • ⁇ Peeling between unstretched polyolefin film / unstretched polyolefin film is 60% or more and less than 90% (practically excellent)
  • ⁇ Peeling between unstretched polyolefin film / unstretched polyolefin film is 50% or more and less than 60% (practical range)
  • X Peeling between unstretched polyolefin film / unstretched polyolefin film is less than 50%
  • the adhesive of the present invention is more excellent in heat resistance than the adhesive of the comparative example.
  • the adhesive of the present invention is excellent in the adhesion between a nonpolar base such as an olefin resin and a metal base, heat resistance, and the laminate obtained by using the adhesive of the present invention is, for example, a battery packaging material. It can be used suitably.
  • the application of the adhesive of the present invention is not limited to battery packaging materials and laminates therefor, and adhesion between non-polar substrates such as household electric appliance skins, furniture materials, building interior members and metal substrates Are widely available in areas where they are required.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Electrochemistry (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Sealing Battery Cases Or Jackets (AREA)
  • Laminated Bodies (AREA)

Abstract

L'invention fournit un agent adhésif excellent en termes de résistance à la chaleur et d'adhérence entre un substrat non polaire tel qu'une résine oléfine et un substrat métallique, un stratifié d'une excellente résistance à la chaleur obtenu à l'aide de cet agent adhésif, et un matériau d'enveloppement pour batterie. Plus précisément, l'invention concerne un agent adhésif qu contient une résine oléfine (A), un agent de durcissement (B) contenant un composé époxy, et un acide anhydride (C), la quantité dans laquelle est mélangée l'acide anhydride (C) étant supérieure ou égale à 0,05 partie en masse et inférieure ou égale à 10 parties en masse pour 100 parties de résine oléfine (A). L'invention concerne également un pré-mélange destiné à cet agent adhésif, un stratifié mettant en œuvre cet agent adhésif, un matériau d'enveloppement pour batterie, et une batterie.
PCT/JP2018/047472 2017-12-26 2018-12-25 Agent adhésif, stratifié, matériau d'enveloppement pour batterie, et batterie WO2019131591A1 (fr)

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JP2019542254A JP6610985B1 (ja) 2017-12-26 2018-12-25 接着剤、積層体、電池用包装材及び電池
CN201880079869.6A CN111479889B (zh) 2017-12-26 2018-12-25 粘接剂、层叠体、电池用包装材料以及电池

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JP6777255B1 (ja) * 2019-12-27 2020-10-28 東洋インキＳｃホールディングス株式会社 太陽電池モジュール形成用シート用プライマー、および太陽電池モジュール形成用シート、並びに太陽電池モジュール
WO2021106849A1 (fr) * 2019-11-27 2021-06-03 東洋紡株式会社 Composition adhésive à base de polyoléfine
CN117050235A (zh) * 2023-08-16 2023-11-14 达高工业技术研究院(广州)有限公司 胶黏树脂及其制备方法和复合胶黏剂及其应用
WO2024053576A1 (fr) * 2022-09-08 2024-03-14 三井化学株式会社 Composition adhésive, stratifié, matériau de conditionnement et matériau de conditionnement pour boîtiers de batterie

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CN114262579B (zh) * 2021-12-30 2023-11-24 江苏睿捷新材料科技有限公司 金属复合膜及其应用
CN115074056B (zh) * 2022-06-29 2023-03-21 惠州市广麟材耀科技有限公司 锂电池封装用铝塑膜内层胶黏剂及其制备方法

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JP2020029561A (ja) 2020-02-27
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CN111479889A (zh) 2020-07-31
CN111479889B (zh) 2022-06-07
JPWO2019131591A1 (ja) 2019-12-26
JP6825677B2 (ja) 2021-02-03
TW201937780A (zh) 2019-09-16

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