WO2016021279A1 - 金属箔と樹脂フィルムのラミネート用接着剤、該組成物を用いた積層体、電池外装用包装材および電池ケース - Google Patents
金属箔と樹脂フィルムのラミネート用接着剤、該組成物を用いた積層体、電池外装用包装材および電池ケース Download PDFInfo
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- WO2016021279A1 WO2016021279A1 PCT/JP2015/064963 JP2015064963W WO2016021279A1 WO 2016021279 A1 WO2016021279 A1 WO 2016021279A1 JP 2015064963 W JP2015064963 W JP 2015064963W WO 2016021279 A1 WO2016021279 A1 WO 2016021279A1
- Authority
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- WIPO (PCT)
- Prior art keywords
- adhesive
- resin film
- metal foil
- laminating
- polyol
- Prior art date
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- 229910052751 metal Inorganic materials 0.000 title claims abstract description 76
- 239000002184 metal Substances 0.000 title claims abstract description 76
- 238000010030 laminating Methods 0.000 title claims abstract description 52
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- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 33
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- 239000012790 adhesive layer Substances 0.000 claims description 31
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- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 7
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- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 7
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- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 3
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
- C09J2203/33—Applications of adhesives in processes or use of adhesives in the form of films or foils for batteries or fuel cells
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J2475/00—Presence of polyurethane
-
- 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 is produced using a metal foil and resin film laminating adhesive suitable for an adhesive for a secondary battery exterior material such as a lithium ion battery, and the metal foil and resin film laminating adhesive.
- the present invention relates to a laminate, a battery exterior packaging material using the laminate, and a battery case obtained by molding the battery exterior packaging material.
- a lithium-containing compound is used as a positive electrode material, and a carbon material such as graphite or coke is used as a negative electrode material. Furthermore, between the positive electrode and the negative electrode, an electrolytic solution in which a lithium salt such as LiPF 6 or LiBF 4 is dissolved in an aprotic solvent having osmotic power such as propylene carbonate or ethylene carbonate, or an electrolytic solution thereof is used. An electrolyte layer made of impregnated polymer gel is provided.
- a packaging material for battery cases a laminate in which a heat-resistant resin stretched film layer as an outer layer, an aluminum foil layer, and an unstretched thermoplastic resin film layer as an inner layer are sequentially laminated is known. Yes.
- a solvent having a penetrating power such as an electrolyte solution passes through a film layer serving as a sealant in a laminate used for the exterior of the battery. Then, the laminate strength between the aluminum foil layer and the resin film layer is lowered, which may cause the electrolyte to leak out.
- an adhesive layer containing a resin containing a functional group reactive with an isocyanate such as an acid anhydride group, a carboxyl group or a hydroxyl group, and a polyfunctional isocyanate compound is provided between the aluminum foil layer and the inner layer.
- Patent Document 1 a modified polyolefin resin obtained by graft polymerization of an ethylenically unsaturated carboxylic acid or an anhydride thereof to a propylene homopolymer or a copolymer of propylene and ethylene and a polyfunctional isocyanate compound are used as an organic solvent. Describes a method of forming an adhesive layer by using a solvent-type adhesive dissolved or dispersed in the above.
- Patent Document 2 an adhesive composition containing a polyolefin polyol and a polyfunctional isocyanate curing agent as essential components and further added with a thermoplastic elastomer and / or a tackifier is disclosed in Patent Document 3,
- Adhesive compositions containing one or more polyisocyanate compounds selected from the group consisting of diisocyanates are described.
- JP 2010-92703 A Japanese Patent Laying-Open No. 2005-63685 JP2011-187385A
- the modified polyolefin resin of Patent Document 1 has a change over time during long-term storage or after dissolution of the solvent, and often the operability during application may become unstable, and the adhesive strength of the formed adhesive layer There was a risk of variations. Moreover, there also existed a possibility that it might be inferior to the adhesive force in high temperature supposing the vehicle-mounted use etc.
- the present invention has been completed under such background art, and its purpose is to have excellent adhesive strength and a metal foil for lamination and a resin film suitable for joining an aluminum foil and a heat-fusible resin film. It is to provide an adhesive for laminating. Another object of the present invention is to provide a laminate of a metal foil and a resin film that is excellent in heat resistance and electrolytic solution resistance and is suitable for a battery exterior packaging material. Furthermore, the other object of this invention is to provide the battery case excellent in the heat resistance and electrolyte solution resistance formed using the packaging material for battery exterior which consists of this laminated body.
- a polyol used for a polyurethane-based adhesive Polyester polyol (a2) having a linear polyolefin polyol (a1) and / or a hydrogenated dimer acid-derived structural unit and a hydrogenated dimer diol-derived structural unit, a saturated or unsaturated cyclic hydrocarbon structure and two or more
- Polyester polyol (a2) having a linear polyolefin polyol (a1) and / or a hydrogenated dimer acid-derived structural unit and a hydrogenated dimer diol-derived structural unit, a saturated or unsaturated cyclic hydrocarbon structure, Polyurethane polyol (A) obtained by polyaddition of a component containing a hydroxyl group-containing hydrocarbon compound (b) having two or more hydroxyl groups and a polyisocyanate (c), and a saturated aliphatic and / or saturated alicyclic ring An adhesive for laminating a metal foil and a resin film, having the formula polyisocyanate (B).
- the adhesive for laminating a metal foil and a resin film of the present invention has excellent adhesive strength, and the laminate of the metal foil and the resin film formed using the adhesive for laminating the metal foil and the resin film is heat resistant. Since it is excellent in resistance to electrolytic solution, it is suitable as a material for packaging materials for battery exteriors used in the production of secondary batteries such as lithium ion batteries. Moreover, the battery case molded using the packaging material for battery exterior of the present invention is excellent in heat resistance and electrolytic solution resistance, and by using it, it is possible to provide a safe secondary battery having a long life. it can.
- the adhesive for laminating a metal foil and a resin film of the present invention includes a chain polyol polyol (a1) and / or a polyester polyol (a2) having a structural unit derived from a hydrogenated dimer acid and a structural unit derived from a hydrogenated dimer diol.
- Polyurethane polyol (A) obtained by polyaddition of a component containing a hydroxyl group-containing hydrocarbon compound (b) having both a saturated or unsaturated cyclic hydrocarbon structure and two or more hydroxyl groups, and a polyisocyanate (c) ) And saturated aliphatic and / or saturated alicyclic polyisocyanate (B).
- the polyurethane polyol (A) corresponds to a main agent
- the saturated aliphatic and / or saturated alicyclic polyisocyanate (B) corresponds to a curing agent.
- the adhesive for laminating a metal foil and a resin film of the present invention can be suitably used for adhering a metal foil and a resin film, and is particularly useful as an adhesive for laminating a metal foil and a resin film.
- “to” in this specification means a value not less than the value before the description of “to” and not more than the value after the description of “to”.
- the polyurethane polyol (A) used in the present invention is obtained by polyaddition of components containing the components (a1) and / or (a2), the component (b), and the component (c) as described above. .
- the “chain polyolefin polyol (a1)” in the present invention means a polyolefin polyol (a1) that does not contain an alicyclic structure.
- the linear polyolefin polyol (a1) (hereinafter, also referred to as “polyolefin polyol (a1)”) used in the present invention is a polyolefin skeleton formed by polymerizing or copolymerizing one or two or more olefins, and two or more. If it contains the hydroxyl group of this and does not have an alicyclic structure, it will not restrict
- polydiene polyols such as polybutadiene polyol and polyisoprene polyol, graft polymers of polydiene polyol and polyolefin, and hydrogenated products of these polydiene polyols and graft polymers.
- polydiene polyols such as polybutadiene polyol and polyisoprene polyol
- graft polymers of polydiene polyol and polyolefin graft polymers of polydiene polyol and polyolefin
- hydrogenated products of these polydiene polyols and graft polymers are preferable.
- a chain polyolefin polyol that does not substantially contain an unsaturated hydrocarbon structure in the structure is preferable.
- examples thereof include various polydiene polyols mentioned above and hydrogenated products of graft polymers. Examples of these commercially available products include GI-1000, GI-2000, GI-3000 (all manufactured by Nippon Soda Co., Ltd.)
- the number average molecular weight of the polyolefin polyol (a1) is preferably 1000 to 10,000. If the number average molecular weight is 1000 or more, the adhesive force of the adhesive layer obtained from the adhesive for laminating the metal foil and the resin film of the present invention is not easily lowered even when in contact with the electrolytic solution, and the number average molecular weight is 10 If it is 1,000 or less, the solubility of the polyurethane polyol (G) described later in a solvent and the operability at the time of applying the adhesive for laminating the metal foil and resin film of the present invention will be good.
- the number average molecular weight in the present invention is measured at normal temperature using gel permeation chromatography (Showa Denko Co., Ltd., Shodex GPC System-11, “Shodex” (registered trademark)) under the following conditions. This is a value obtained using a polystyrene calibration curve.
- Eluent Tetrahydrofuran Detector: Differential refractometer (RI)
- polyester polyol (a2) having a structural unit derived from hydrogenated dimer acid and a structural unit derived from hydrogenated dimer diol The polyester polyol (a2) (hereinafter also referred to as “polyester polyol (a2)”) having a structural unit derived from a hydrogenated dimer acid and a structural unit derived from a hydrogenated dimer diol used in the present invention is the From the viewpoint of the electrolytic solution resistance of the adhesive layer obtained from the adhesive for laminating the metal foil and the resin film, it has a structural unit derived from hydrogenated dimer acid and a structural unit derived from hydrogenated dimer diol.
- dimer acid refers to a dimer obtained by reacting a fatty acid having 14 to 22 carbon atoms having an ethylenic double bond (hereinafter also referred to as “unsaturated fatty acid A”) at the double bond portion.
- This refers to body acid.
- unsaturated fatty acid A having 2 to 4 ethylenic double bonds and unsaturated fatty acid A having 1 to 4 ethylenic double bonds more preferably unsaturated fatty acid A having 2 ethylenic double bonds
- Examples of the unsaturated fatty acid A include tetradecenoic acid (tuzuic acid, mascoic acid, myristoleic acid), hexadecenoic acid (such as palmitoleic acid), octadecenoic acid (such as oleic acid, elaidic acid, and vaccenic acid), eicosenoic acid (gadrene).
- tetradecenoic acid tuzuic acid, mascoic acid, myristoleic acid
- hexadecenoic acid such as palmitoleic acid
- octadecenoic acid such as oleic acid, elaidic acid, and vaccenic acid
- eicosenoic acid eicosenoic acid
- the obtained dimer acid is usually a dimer acid mixture having a different structure depending on the bonding site or isomerization of a double bond, and may be used separately, but can be used as it is. Further, the obtained dimer acid contains a small amount of monomeric acid (for example, 6% by weight or less, particularly 4% by weight or less), a polymer acid or more such as trimer acid (for example, 6% by weight or less, particularly 4% by weight or less). May be.
- hydrogenated dimer acid refers to a saturated dicarboxylic acid obtained by hydrogenating the carbon-carbon double bond of the dimer acid.
- examples of commercially available hydrogenated dimer acids include EMPOL1008 and EMPOL1062 (both manufactured by BASF), PRIPOL1009 and the like (manufactured by Croda).
- the “hydrogenated dimer diol” refers to reducing at least one of the dimer acid, the hydrogenated dimer acid and a lower alcohol ester thereof in the presence of a catalyst, and converting the carboxylic acid or carboxylate part of the dimer acid to an alcohol.
- the main component is a diol obtained by hydrogenating the double bond. Examples of commercially available hydrogenated dimer diols include Sovermol 908 (BASF) and PRIPOL 2033 (Croda).
- the polyester polyol (a2) used in the present invention comprises a condensation reaction between an acid component having the hydrogenated dimer acid as an essential component and an alcohol component having the hydrogenated dimer diol as an essential component in the presence of an esterification catalyst.
- an ester exchange reaction between an ester component having the lower alkyl ester of the hydrogenated dimer acid as an essential component and an alcohol component having the hydrogenated dimer diol as an essential component in the presence of a transesterification catalyst. Can be manufactured.
- hydroxyl group-containing hydrocarbon compound (b) having both a saturated or unsaturated cyclic hydrocarbon structure and two or more hydroxyl groups is: From the viewpoint of the electrolytic solution resistance of the adhesive layer obtained from the adhesive for laminating the metal foil and the resin film of the present invention, it has an unsaturated or saturated alicyclic hydrocarbon structure and two or more hydroxyl groups. There is no particular limitation as long as the structure of the portion is a compound comprising a hydrocarbon.
- saturated cyclic hydrocarbon structures include cycloalkane skeletons such as cyclopentane skeleton, cyclohexane skeleton and cycloheptane skeleton, saturated alicyclic structures having a crosslinked structure such as norbornane skeleton, adamantane skeleton, and tricyclodecane skeleton.
- saturated cyclic hydrocarbon (b) having such a structure include cyclopentanediol, cyclohexanediol, cyclohexanedimethanol, norbornanediol, adamantanediol, and tricyclodecane dimethanol.
- adamantanetriol manufactured by Idemitsu Kosan Co., Ltd., Mitsubishi Gas Chemical Co., Ltd.
- TCD alcohol DM manufactured by Oxair
- the unsaturated cyclic hydrocarbon structure includes cyclopentene skeleton, cyclohexene skeleton, cycloheptene skeleton, cycloalkene skeleton such as [4n] annulene skeleton, benzene skeleton, naphthalene skeleton, anthracene skeleton, azulene skeleton, and conjugated such as [4n + 2] annulene skeleton.
- Examples thereof include unsaturated alicyclic structures having a crosslinked structure such as a ring structure and a dicyclopentadiene skeleton.
- Examples of the polyol (b) having such a structure include cyclohexenediol, biphenol, bisphenol, naphthalenediol, dicyclopentadiene. Examples include enildimethanol. These can be used individually or in mixture of 2 or more types. Bisphenol is preferable, and bisphenol A, bisphenol B, bisphenol C, bisphenol E, bisphenol F, bisphenol G, bisphenol Z, and the like are mentioned, and bisphenol A is more preferable.
- the polyisocyanate (c) used in the present invention is not particularly limited as long as it is a compound containing two or more isocyanato groups or a multimer thereof.
- saturated fats such as 1,4-cyclohexane diisocyanate, isophorone diisocyanate, methylene bis (4-cyclohexyl isocyanate), 1,3-bis (isocyanatomethyl) cyclohexane, 1,4-bis (isocyanatomethyl) cyclohexane, norbornane diisocyanate
- Aromatic diisocyanates such as cyclic diisocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, diphenylmethane-4,4'-diisocyanate, 1,3-xylylene diisocyanate, 1,4-xylylene diisocyanate, Aliphatic diisocyanates such as hexam
- Saturated alicyclic diisocyanates are preferred, 1,4-cyclohexane diisocyanate, isophorone diisocyanate, methylene bis (4-cyclohexyl isocyanate), 1,3-bis (isocyanatomethyl) cyclohexane, 1,4-bis (isocyanatomethyl) And cyclohexane, norbornane diisocyanate, and the like.
- isophorone diisocyanate (3-isocyanatomethyl-3,5,5-trimethylcyclohexylisocyanate), methylenebis (4-cyclohexylisocyanate) (also known as dicyclohexylmethane-4,4). '-Diisocyanate).
- Examples of these commercially available products include Death Module I, Death Module W (each manufactured by Bayer), IPDI, and H12MDI (each manufactured by Degussa).
- the polyurethane polyol (A) used in the present invention may be produced in the presence or absence of a known urethanization catalyst such as dibutyltin dilaurate, dioctyltin dilaurate, bismuth tris 2-ethylhexanoate, zirconium tetraacetylacetonate.
- a known urethanization catalyst such as dibutyltin dilaurate, dioctyltin dilaurate, bismuth tris 2-ethylhexanoate, zirconium tetraacetylacetonate.
- a known urethanization catalyst such as dibutyltin dilaurate, dioctyltin dilaurate, bismuth tris 2-ethylhexanoate, zirconium tetraacetylacetonate.
- the reaction in the presence of a catalyst is preferable in terms of shortening the reaction time.
- This catalyst is preferably present because it also acts as a curing accelerator when the polyurethane polyol (A) reacts with the saturated aliphatic and / or saturated alicyclic polyisocyanate (B) to cure.
- the amount used is (a1), (a2), (b) and
- the amount of component (c) is preferably 0.001 to 1 part by weight, more preferably 0.005 to 0.5 part by weight, and still more preferably 0.01 to 0.3 part by weight based on 100 parts by weight of the total component.
- the polyaddition reaction may be performed by reacting the polyolefin polyol (a1) and / or the polyester polyol (a2), the hydroxyl group-containing cyclic hydrocarbon compound (b), and the polyisocyanate (c) all at once.
- the polyolefin polyol (a1) and / or the polyester polyol (a2) and the hydroxyl group-containing cyclic hydrocarbon compound (b) are reacted with the polyisocyanate (c) separately or in appropriate combination, The components may be mixed and further reacted.
- a polyurethane polyisocyanate is obtained by reacting a hydroxyl group-containing cyclic hydrocarbon compound (b) with a polyisocyanate (c), and then a polyolefin polyol (a1) and / or a polyester polyol (a2) is reacted. To obtain a polyurethane polyol (A).
- the polyaddition reaction may be performed in a solvent.
- a solvent there is no restriction
- the ratio of the number of isocyanate groups contained in the polyisocyanate (c) to the number of hydroxyl groups contained in the components (a1), (a2) and (b) when the polyurethane polyol (A) is produced (hereinafter referred to as “NCO / OH ratio”) Is also preferably 0.5 to 1.3, more preferably 0.7 to 1.2, and still more preferably 0.8 to 1.1. If it is 0.5 or more, the adhesive force of the adhesive layer obtained from the adhesive for laminating the metal foil and the resin film of the present invention is less likely to be lowered even in contact with the electrolytic solution.
- the number of hydroxyl groups contained in each polyol component can be determined by a known method such as a titration method such as JIS K 1557-1 or a spectroscopic method such as JIS K 1557-6. In Examples described later, JIS K1557-1 (titration method) was used.
- the number of isocyanate groups contained in each isocyanate component can be determined by a known method such as a titration method such as JIS K 6806.
- the ratio of the hydroxyl group-containing cyclic hydrocarbon compound (b) to the total amount of the components (a1) and (a2) being 100 parts by mass is preferably 5 to 100 parts by mass.
- the amount is more preferably 10 to 50 parts by mass, and further preferably 10 to 45 parts by mass. If it is 5 parts by mass or more, the adhesive strength of the adhesive layer obtained from the adhesive for laminating the metal foil and the resin film of the present invention will not easily decrease even when it comes into contact with the electrolyte, and if it is 100 parts by mass or less.
- the solubility of the polyurethane polyol (A) in a solvent and the operability during application of the adhesive for laminating the metal foil and the resin film of the present invention are improved.
- the saturated aliphatic and / or saturated alicyclic polyisocyanate (B) in the present invention (hereinafter also referred to as “polyisocyanate (B)”) is blended as a curing agent in the adhesive for laminating a metal foil and a resin film of the present invention. It is described separately from the polyisocyanate (c) described as a raw material in the production of the aforementioned polyurethane polyol (A).
- the saturated aliphatic and / or saturated alicyclic polyisocyanate (B) used in the present invention is not particularly limited as long as it is a compound comprising two or more isocyanate groups or a multimer thereof.
- aliphatic diisocyanates such as hexamethylene diisocyanate, 2,4,4-trimethylhexamethylene diisocyanate, 2,2,4-trimethylhexanemethylene diisocyanate, 1,4-cyclohexane diisocyanate, isophorone diisocyanate, methylene bis (4-cyclohexyl isocyanate) 1,3-bis (isocyanatomethyl) cyclohexane, 1,4-bis (isocyanatomethyl) cyclohexane, saturated alicyclic diisocyanates such as norbornane diisocyanate, and allophanated multimers, isocyanurates, and biuret-modified products Etc.
- the NCO / OH ratio of the polyisocyanate (B) to the polyurethane polyol (A) is preferably 1 to 20, more preferably 1 to 15, and still more preferably 1 to 13. If the NCO / OH ratio is 1 or more, the adhesive strength of the adhesive layer obtained from the adhesive for laminating the metal foil and the resin film of the present invention is particularly good, and the NCO / OH ratio is 20 or less. If it is, the adhesive force of the adhesive layer obtained from the adhesive for laminating the metal foil and the resin film of the present invention will not easily decrease even if it comes into contact with the electrolytic solution.
- the adhesive for laminating a metal foil and a resin film of the present invention may contain a solvent (C).
- the solvent (C) is not particularly limited as long as it can dissolve or disperse the polyurethane polyol (A) and the polyisocyanate (B).
- aromatic organic solvents such as toluene and xylene
- alicyclic organic solvents such as cyclohexane, methylcyclohexane and ethylcyclohexane
- aliphatic organic solvents such as n-hexane and n-heptane
- ethyl acetate propyl acetate
- ester organic solvents such as butyl acetate
- ketone organic solvents such as acetone, methyl ethyl ketone, and methyl butyl ketone.
- the content of the solvent (C) is preferably 40 to 95 parts by weight, preferably 50 to 95 parts per 100 parts by weight of the adhesive for laminating the metal foil and resin film comprising the components (A), (B) and (C).
- the amount is more preferably part by mass, and further preferably 80 to 90 parts by mass.
- the operability at the time of applying the adhesive for laminating the metal foil and resin film of the present invention will be good, and if it is 95 parts by mass or less, for laminating the metal foil and resin film of the present invention.
- the thickness controllability of the laminate obtained by applying and curing the adhesive is improved.
- the adhesive for laminating a metal foil and a resin film of the present invention may contain additives such as a reaction accelerator, a tackifier, and a plasticizer as necessary.
- the reaction accelerator is for accelerating the reaction of the polyurethane polyol (A) and the polyisocyanate (B), and is, for example, dioctyltin dilaurate, dioctyltin diacetate or a tertiary amine which is an organic tin compound. 2,4,6-tris (dimethylaminomethyl) phenol, dimethylaniline, dimethylparatoluidine, N, N-di ( ⁇ -hydroxyethyl) -p-toluidine and the like. These reaction accelerators can be used alone or in combination of two or more.
- the tackifier is not particularly limited.
- polyterpene resin, rosin resin and the like can be mentioned.
- petroleum system aliphatic (C5) resin, aromatic (C9) resin, copolymer (obtained from naphtha cracked oil fraction) C5 / C9) resin, alicyclic resin and the like.
- the hydrogenated resin which hydrogenated the double bond part of these resin is mentioned.
- This tackifier may be used alone or in combination of two or more.
- the plasticizer is not particularly limited, and examples thereof include liquid rubber such as polyisoprene and polybutene, and process oil.
- thermoplastic resin such as an acid-modified polyolefin resin or a thermoplastic elastomer may be included as long as the effect of the present invention is not impaired.
- thermoplastic resin and thermoplastic elastomer that can be blended include ethylene-vinyl acetate copolymer resin, ethylene-ethyl acrylate copolymer resin, SEBS (styrene-ethylene-butylene-styrene), and SEPS (styrene-ethylene-propylene-styrene). ) And the like.
- the metal foil and the resin film are obtained from the adhesive for laminating the metal foil and the resin film of the present invention (hereinafter sometimes simply referred to as “laminating adhesive of the present invention”). It is joined through layers. Moreover, if the layer which joined the metal foil and the resin film via the adhesive bond layer obtained from the adhesive agent for lamination of the present invention is contained in the laminate of the present invention, the metal foils and / or the resin films may be combined. May include a layer bonded through an adhesive layer obtained from the adhesive for lamination of the present invention. As this bonding method, a known method such as a heat lamination method or a dry lamination method can be used.
- the heat lamination method is a laminate by heating and extruding the laminating adhesive of the present invention containing no solvent (C) on the surface of the layer in contact with the adhesive layer, or with the layer in contact with the adhesive layer. In this method, an adhesive layer is formed between the layers.
- the dry lamination method is a laminate in which the adhesive for laminating of the present invention containing the solvent (C) is applied to the surface of the layer in contact with the adhesive layer, dried, and then overlapped with the other layer and pressure-bonded. In this method, an adhesive layer is formed between the layers.
- the use of the laminate of the present invention is not particularly limited, but a useful application is packaging.
- the contents to be packaged in this laminate include liquid materials containing acids, alkalis, organic solvents, etc., such as putty (thickening putty, thinning putty etc.), paint (oil-based paint etc.), lacquer ( Clear lacquers, etc.) and solvent-based ones such as automotive compounds.
- this laminated body is suitable also for packaging the electrolyte solution of a lithium ion battery, it can be used as a packaging material for battery exteriors, and is preferable.
- the metal foil is an aluminum foil
- the resin film includes a heat-fusible resin film
- an outer layer made of a heat-resistant resin film is provided outside the aluminum foil. .
- the packaging material for battery exteriors of this invention provides the outer layer which consists of a heat resistant resin film in the outer side of metal foil of the laminated body of this invention. Moreover, in order to improve characteristics, such as mechanical strength and electrolyte solution resistance, it can be set as the structure which added the 1st intermediate resin layer or / and the 2nd intermediate resin layer, etc. as needed. As a preferable form, it can be specifically configured as follows.
- the adhesive layer means “an adhesive layer obtained from the laminating adhesive of the present invention”, and the metal foil layer is exemplified as an aluminum foil layer.
- outer layer / aluminum foil layer / adhesive layer / resin film layer (2) outer layer / first intermediate resin layer / aluminum foil layer / adhesive layer / resin film layer (3) outer layer / aluminum foil layer / second intermediate Resin layer / adhesive layer / resin film layer (4) outer layer / first intermediate resin layer / aluminum foil layer / second intermediate resin layer / adhesive layer / resin film layer (5) coat layer / outer layer / aluminum foil layer / Adhesive layer / resin film layer (6) coat layer / outer layer / first intermediate resin layer / aluminum foil layer / adhesive layer / resin film layer (7) coat layer / outer layer / aluminum foil layer / second intermediate resin layer / Adhesive layer / resin film layer (8) coat layer / outer layer / first intermediate resin layer / aluminum foil layer / second intermediate resin layer / adhesive layer / resin film layer
- the first intermediate resin layer polyamide resin, polyester resin, polyethylene resin or the like is used for the purpose of improving the mechanical strength of the battery exterior packaging material.
- a polyamide resin, a polyester resin, or a heat-adhesive extruded resin such as polyethylene resin or polypropylene is used mainly for the purpose of improving the resistance to electrolyte.
- the resin film layer a single-layer resin film or a multilayer resin film (produced by two-layer coextrusion or three-layer coextrusion) can be used.
- the second intermediate resin layer can also be a single-layer resin film or a multilayer co-extruded resin film.
- the thicknesses of the first intermediate resin layer and the second intermediate resin layer are not particularly limited, but when they are provided, they are usually about 0.1 to 30 ⁇ m.
- the resin film used for the outer layer is excellent in heat resistance, moldability, insulation, etc., and a stretched film of polyamide (nylon) resin or polyester resin is generally used.
- the thickness of the outer layer film is about 9 to 50 ⁇ m. If the thickness is less than 9 ⁇ m, the stretched film is insufficiently stretched when the packaging material is formed, necking occurs in the aluminum foil, and molding defects tend to occur. On the other hand, in the case of a thickness exceeding 50 ⁇ m, the effect of formability is not particularly improved, but conversely, the volume energy density is lowered and only the cost is increased.
- the thickness of the outer layer film is more preferably about 10 to 40 ⁇ m, and further preferably 20 to 30 ⁇ m.
- the film used for this outer layer is cut into a predetermined size so that each of the three directions of 0 °, 45 °, and 90 ° is the tensile direction when the stretched direction of the stretched film is 0 °.
- the tensile strength is 150 N / mm 2 or more, preferably 200 N / mm 2 or more, more preferably 250 N / mm 2 or more, and the elongation by pulling in three directions is 80% or more, It is preferable to use a material that is preferably 100% or more, more preferably 120% or more, from the viewpoint of obtaining a sharper shape.
- the tensile strength is 150 N / mm 2 or more, or the elongation by tension is 80% or more, the above effect is sufficiently exhibited.
- the tensile strength and the elongation value due to tension are values until breakage in a film tensile test (test piece length 150 mm ⁇ width 15 mm ⁇ thickness 9 to 50 ⁇ m, pulling speed 100 mm / min). Test specimens are cut out in three directions.
- the metal foil plays a role of barrier properties against water vapor and the like, and as a material, an O material (soft material) of a pure aluminum system or an aluminum-iron system alloy is generally used and preferable.
- the thickness of the aluminum foil is preferably about 10 to 100 ⁇ m in order to ensure processability and barrier properties to prevent oxygen and moisture from entering the package. If the thickness of the aluminum foil is less than 10 ⁇ m, the aluminum foil may break during molding or a pinhole may occur, which may lead to the ingress of oxygen or moisture.
- the aluminum foil generally has a thickness of about 30 to 50 ⁇ m, and preferably has a thickness of 40 to 50 ⁇ m.
- the aluminum foil is preferably subjected to a chemical conversion treatment such as an undercoat treatment such as a silane coupling agent or a titanium coupling agent, or a chromate treatment in order to improve the adhesion to the resin film and the corrosion resistance.
- the resin film is preferably a heat-fusible resin film such as polypropylene, polyethylene, maleic acid-modified polypropylene, ethylene-acrylate copolymer, or ionomer resin. These resins have a heat-sealing property and play a role of improving chemical resistance against an electrolytic solution or the like of a lithium secondary battery having strong corrosivity.
- the film thickness is preferably 9 to 100 ⁇ m, more preferably 20 to 80 ⁇ m, and most preferably 40 to 80 ⁇ m. When the thickness of the resin film is 9 ⁇ m or more, sufficient heat seal strength is obtained, and the corrosion resistance against the electrolytic solution and the like is good. If the thickness of the resin film is 100 ⁇ m or less, the strength of the packaging material for battery exterior is sufficient and the moldability is good.
- a coat layer may be provided on the outer layer.
- a method for forming the coating layer there are a method of coating a gas barrier polymer, a method of depositing an inorganic oxide such as aluminum metal or silicon oxide / aluminum oxide, and coating a thin film of a metal and an inorganic material.
- the battery case of this invention is obtained by shape
- the packaging material for battery exterior of the present invention is excellent in electrolytic solution resistance, heat resistance, water vapor and other gas barrier properties, and is suitably used as a battery case for secondary batteries, particularly lithium ion batteries.
- the packaging material for battery exterior of the present invention has very good moldability, the battery case of the present invention can be easily obtained by molding according to a known method.
- the forming method is not particularly limited, but when it is formed by deep drawing or stretch forming, a battery case having a complicated shape and high dimensional accuracy can be produced.
- polyurethane polyisocyanate (3) A methyl ethyl ketone solution of polyurethane polyisocyanate (hereinafter referred to as polyurethane polyisocyanate (3)) was obtained in the same manner as in Synthesis Example 2 except that 20 g of bisphenol F (manufactured by Honshu Chemical Industry) was used instead of bisphenol A. .
- Synthesis Examples 5 to 10, Comparative Synthesis Examples 11 to 13 Synthesis was carried out in the same manner as in Synthesis Example 3 with the components and amounts shown in Table 2, and a polyurethane solution of polyurethane polyols (4) to (13) or a mixed solvent solution of toluene and methyl ethyl ketone (solid content concentration 18% by mass) )
- GI-1000 and GI-2000 are hydrogenated polybutadiene polyols manufactured by Nippon Soda
- G-1000 is polybutadiene polyol manufactured by Nippon Soda
- 14BG is 1,4-butanediol manufactured by Mitsubishi Chemical.
- Synthesis Examples 1 to 10 and Comparative Synthesis Examples 11 to 13 are shown in Tables 1 and 2.
- Example 1 "Duranate TKA-100" (produced by Asahi Kasei Chemicals Corporation, hexamethylene diisocyanate isocyanurate) was added to 33.33 g (solid content 6.00 g, toluene 27.33 g) of the polyurethane polyol (4) obtained in Synthesis Example 4. 0.34 g and toluene 15.08 g were added to prepare an adhesive 1 for laminating a metal foil and a resin film. Next, using this laminating adhesive 1, a battery exterior packaging material having a structure of outer layer / outer layer adhesive / aluminum foil layer / laminating adhesive 1 / resin film is formed by the dry lamination method as follows. Manufactured.
- Outer layer stretched polyamide film (thickness 25 ⁇ m)
- Adhesive for outer layer Adhesive for urethane-based dry lamination (Toyo Morton Co., Ltd .: AD502 / CAT10, application amount 3 g / m 2 (at the time of application))
- Aluminum foil layer Aluminum-iron alloy aluminum foil (AA standard 8079-O material, thickness 40 ⁇ m)
- Laminating adhesive 1 Laminating adhesive 1 for the above metal foil and resin film (coating amount: 2 ⁇ m thickness after drying)
- Resin film Unstretched polypropylene film (thickness 30 ⁇ m)
- Examples 2 to 7, Comparative Examples 1 to 5 In the same manner as in Example 1, the adhesives 2 to 12 for laminating the metal foil and the resin film were prepared with the components and amounts shown in Table 3, and the adhesives for laminating the respective metal foil and the resin film were prepared. Using this, a packaging material for battery exterior was produced.
- the acid-modified polypropylene is acid-modified polypropylene (acid value 20 mg / KOH) modified with maleic anhydride and octyl acrylate
- Millionate MR-200 is polymer diphenylmethane diisocyanate manufactured by Nippon Polyurethane.
- the 180 ° peel strength between the aluminum foil layer and the unstretched polypropylene film layer is measured using the test piece in the same manner as in the above (1).
- the adhesives for laminating the metal foil and the resin film of the present invention show the normal T-shaped peel strength, the T-shaped peel strength after immersion in the electrolyte solution, and the atmosphere at 85 ° C. It turns out that it is excellent in any of T character peeling strength.
- the metal foil and resin film laminating adhesive of the present invention has an excellent adhesive force even after immersion in an electrolyte or at a high temperature, particularly an aluminum foil and a heat-fusible resin film. It is suitable for joining.
- the laminate of the present invention is excellent in heat resistance and electrolytic solution resistance, it is suitably used for a packaging material for battery exteriors used in the production of secondary batteries such as lithium ion batteries, and this laminate is molded. Thus, a battery case excellent in heat resistance and electrolytic solution resistance can be produced. By using the battery case, a safe secondary battery with a long life can be manufactured.
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Abstract
Description
〔1〕 ポリウレタン系接着剤に用いるポリオールであって、
鎖状ポリオレフィンポリオール(a1)及び/又は水添ダイマー酸由来の構成単位と水添ダイマージオール由来の構成単位とを有するポリエステルポリオール(a2)、飽和又は不飽和の環式炭化水素構造と2つ以上の水酸基とを併せ持つ水酸基含有炭化水素化合物(b)、及びポリイソシアネート(c)を含有する成分を重付加して得られる、ポリウレタンポリオール。
〔2〕 鎖状ポリオレフィンポリオール(a1)及び/又は水添ダイマー酸由来の構成単位と水添ダイマージオール由来の構成単位とを有するポリエステルポリオール(a2)、飽和又は不飽和の環式炭化水素構造と2つ以上の水酸基とを併せ持つ水酸基含有炭化水素化合物(b)、及びポリイソシアネート(c)を含有する成分を重付加して得られるポリウレタンポリオール(A)と、飽和脂肪族及び/又は飽和脂環式ポリイソシアネート(B)と、を有する、金属箔と樹脂フィルムのラミネート用接着剤。
〔3〕 前記水酸基含有炭化水素化合物(b)が、架橋構造を有する飽和脂環構造を含むポリオールである、〔2〕に記載の金属箔と樹脂フィルムのラミネート用接着剤。
〔4〕 前記水酸基含有炭化水素化合物(b)が、ビスフェノール化合物である、〔2〕又は〔3〕に記載の金属箔と樹脂フィルムのラミネート用接着剤。
〔5〕 前記ポリイソシアネート(c)が、飽和脂環式ジイソシアネートである、〔2〕~〔4〕のいずれかに記載の金属箔と樹脂フィルムのラミネート用接着剤。
〔6〕 前記鎖状ポリオレフィンポリオール(a1)が、実質的に不飽和炭化水素構造を含まないポリオレフィンポリオールである、〔2〕~〔5〕のいずれかに記載の金属箔と樹脂フィルムのラミネート用接着剤。
〔7〕 (b)成分が、(a1)及び(a2)成分の総量100質量部に対して5~100質量部であり、(c)成分に含まれるイソシアナト基数の比率が、(a1)、(a2)及び(b)成分に含まれる水酸基数に対して、0.5~1.3である、〔2〕~〔6〕のいずれかに記載の金属箔と樹脂フィルムのラミネート用接着剤。
〔8〕 前記ポリウレタンポリオール(A)に含まれる水酸基数に対する、ポリイソシアネート(B)に含まれるイソシアナト基数の比率が、1~15である、〔2〕~〔7〕のいずれかに記載の金属箔と樹脂フィルムのラミネート用接着剤。
〔9〕 溶剤(C)をさらに含む、〔2〕~〔8〕のいずれかに記載の金属箔と樹脂フィルムのラミネート用接着剤。
〔10〕 金属箔と樹脂フィルムが、〔2〕~〔9〕のいずれかに記載の金属箔と樹脂フィルムのラミネート用接着剤から得られる接着剤層を介して積層された、積層体。
〔11〕 前記金属箔がアルミニウム箔であり、前記樹脂フィルムが熱融着性樹脂フィルムを含有する、〔10〕に記載の積層体。
〔12〕 前記金属箔の厚さが10~100μmであり、前記樹脂フィルムの厚さが9~100μmである、〔10〕又は〔11〕に記載の積層体。
〔13〕 〔10〕~〔12〕のいずれかに記載の積層体を用いて得られる、電池外装用包装材。
〔14〕 〔13〕に記載の電池外装用包装材を用いて得られる、電池ケース。
〔15〕 〔13〕に記載の電池外装用包装材を深絞り成形又は張り出し成形する、電池ケースの製造方法。
本発明の金属箔と樹脂フィルムのラミネート用接着剤において、前記ポリウレタンポリオール(A)は主剤に当たり、前記飽和脂肪族及び/又は飽和脂環式ポリイソシアネート(B)は硬化剤に当たる。
ここで、本明細書における「~」は、「~」という記載の前の値以上、「~」という記載の後の値以下を意味する。
本発明に用いられるポリウレタンポリオール(A)は、上述したように(a1)及び/又は(a2)成分と、(b)成分と、(c)成分とを含有する成分を重付加して得られる。
本発明の「鎖状ポリオレフィンポリオール(a1)」は、脂環構造を含まないポリオレフィンポリオール(a1)を意味する。
本発明に用いられる鎖状ポリオレフィンポリオール(a1)(以下、「ポリオレフィンポリオール(a1)」ともいう)は、1種又は2種以上のオレフィンを重合又は共重合させてなるポリオレフィン骨格と、2つ以上の水酸基とを含有し、かつ脂環構造を有さないものであれば特に制限されない。具体例としては、ポリブタジエンポリオール、ポリイソプレンポリオールなどのポリジエンポリオール、ポリジエンポリオールとポリオレフィンのグラフト重合物およびこれらのポリジエンポリオールやグラフト重合物の水素添加物等が挙げられる。これらは、単独又は2種以上混合して使用することができる。本発明の金属箔と樹脂フィルムのラミネート用接着剤から得られる接着剤層の耐電解液性の観点からは、構造中に実質的に不飽和炭化水素構造を含まない、鎖状ポリオレフィンポリオールが好ましく、例えば、上記に挙げた各種ポリジエンポリオールやグラフト重合物の水素添加物が挙げられる。これらの市販品としては、例えば、GI-1000、GI-2000、GI-3000(いずれも日本曹達株式会社製)、エポール(出光興産株式会社製)等が挙げられる。
カラム:昭和電工株式会社製、KF-806L
カラム温度:40℃
試料:試料ポリマーの0.2質量%テトラヒドロフラン溶液
流量:2ml/分
溶離液:テトラヒドロフラン
検出器:示差屈折率計(RI)
本発明に用いられる、水添ダイマー酸由来の構成単位と、水添ダイマージオール由来の構成単位とを有するポリエステルポリオール(a2)(以下、「ポリエステルポリオール(a2)」ともいう)は、本発明の金属箔と樹脂フィルムのラミネート用接着剤から得られる接着剤層の耐電解液性の観点から、水添ダイマー酸由来の構成単位と、水添ダイマージオール由来の構成単位とを有する。
本発明に用いられる飽和又は不飽和の環式炭化水素構造と2つ以上の水酸基とを併せ持つ水酸基含有炭化水素化合物(b)(以下、「水酸基含有環式炭化水素(b)」ともいう)は、本発明の金属箔と樹脂フィルムのラミネート用接着剤から得られる接着剤層の耐電解液性の観点から、不飽和又は飽和脂環式炭化水素構造と2つ以上の水酸基を有し、その他の部分の構造が炭化水素から成る化合物であれば特に制限はない。
飽和環式炭化水素構造としては、シクロペンタン骨格、シクロヘキサン骨格、シクロヘプタン骨格等のシクロアルカン骨格、ノルボルナン骨格、アダマンタン骨格、トリシクロデカン骨格等の架橋構造を有する飽和脂環構造等が挙げられ、そのような構造を持つ水酸基含有環式炭化水素(b)としては、シクロペンタンジオール、シクロヘキサンジオール、シクロヘキサンジメタノール、ノルボルナンジオール、アダマンタンジオール、トリシクロデカンジメタノール等が挙げられる。これらは、単独又は2種以上混合して使用することができる。好ましくは架橋構造を有する飽和脂環構造を含むものであり、ノルボルナンジオール、アダマンタンジオール、トリシクロデカンジメタノール等が好ましい例として挙げられる。それらの市販品としては、アダマンタントリオール(出光興産株式会社製、三菱ガス化学株式会社製)、TCDアルコールDM(オクセア社製)等が挙げられる。
本発明に用いるポリイソシアネート(c)としては、イソシアナト基を2つ以上含有する化合物、もしくはその多量体であれば特に制限は無い。例えば、1,4-シクロヘキサンジイソシアネート、イソホロンジイソシアネート、メチレンビス(4-シクロヘキシルイソシアネート)、1,3-ビス(イソシアナトメチル)シクロヘキサン、1,4-ビス(イソシアナトメチル)シクロヘキサン、ノルボルナンジイソシアネート等の飽和脂環式ジイソシアネート、2,4-トリレンジイソシアネート、2,6-トリレンジイソシアネート、ジフェニルメタン-4,4′-ジイソシアネート、1,3-キシリレンジイソシアネート、1,4-キシリレンジイソシアネート等の芳香族ジイソシアネート、ヘキサメチレンジイソシアネート、2,4,4-トリメチルヘキサメチレンジイソシアネート、2,2,4-トリメチルヘキサンメチレンジイソシアネート等の脂肪族ジイソシアネート、またこれらのアロファネート化多量体、イソシアヌレート化物、ビウレット変性物等が挙げられる。これらは、単独又は2種以上混合して使用することができる。好ましくは飽和脂環式ジイソシアネートであり、1,4-シクロヘキサンジイソシアネート、イソホロンジイソシアネート、メチレンビス(4-シクロヘキシルイソシアネート)、1,3-ビス(イソシアナトメチル)シクロヘキサン、1,4-ビス(イソシアナトメチル)シクロヘキサン、ノルボルナンジイソシアネート等が挙げられ、特に好ましくはイソホロンジイソシアネート(3-イソシアナートメチル-3,5,5-トリメチルシクロへキシルイソシアネート)、メチレンビス(4-シクロヘキシルイソシアネート)(別名:ジシクロへキシルメタンー4,4’-ジイソシアネート)である。これらの市販品としては、デスモジュールI、デスモジュールW(それぞれバイエル社製)、IPDI、H12MDI(それぞれデグッサ社製)等が挙げられる。
本発明に用いるポリウレタンポリオール(A)の製造方法としては、ジブチルスズジラウレート、ジオクチルスズジラウレート、ビスマストリス2-エチルヘキサノエート、ジルコニウムテトラアセチルアセトネートのような公知のウレタン化触媒の存在下又は非存在下で、ポリオレフィンポリオール(a1)及び/又はポリエステルポリオール(a2)と、水酸基含有環式炭化水素化合物(b)と、ポリイソシアネート(c)とを重付加反応させることにより行える。触媒の存在下で反応させた方が、反応時間を短縮する意味では好ましい。またこの触媒は、ポリウレタンポリオール(A)と飽和脂肪族及び/又は飽和脂環式ポリイソシアネート(B)が反応して硬化する際の、硬化促進剤としても作用する為、存在することが好ましい。ただし、多く使用しすぎると、最終的に金属箔と樹脂フィルムのラミネート用接着剤としての物性に悪影響を及ぼす可能性があるので、使用量は、(a1)、(a2)、(b)および(c)成分の総量100質量部に対して0.001~1質量部であることが好ましく、0.005~0.5質量部がより好ましく、0.01~0.3質量部が更に好ましい。また重付加の反応は、ポリオレフィンポリオール(a1)及び/又はポリエステルポリオール(a2)と、水酸基含有環式炭化水素化合物(b)と、ポリイソシアネート(c)とを全て一度に反応させても良いし、ポリオレフィンポリオール(a1)及び/又はポリエステルポリオール(a2)と、水酸基含有環式炭化水素化合物(b)とをそれぞれ別々に、もしくは適当に組み合わせてポリイソシアネート(c)と反応させた後、全ての成分を混合してさらに反応させても良い。後者の方法は例えば、水酸基含有環式炭化水素化合物(b)とポリイソシアネート(c)を反応させてポリウレタンポリイソシアネートを得た後、ポリオレフィンポリオール(a1)及び/又はポリエステルポリオール(a2)を反応させてポリウレタンポリオール(A)を得る、といった方法が挙げられる。
本発明における飽和脂肪族及び/又は飽和脂環式ポリイソシアネート(B)(以下、「ポリイソシアネート(B)」ともいう)は本発明の金属箔と樹脂フィルムのラミネート用接着剤に硬化剤として配合するものであり、前述のポリウレタンポリオール(A)製造の際の原料として記載したポリイソシアネート(c)とは区別して記載する。
本発明の金属箔と樹脂フィルムのラミネート用接着剤は、溶剤(C)を含んでも良い。溶剤(C)は、ポリウレタンポリオール(A)およびポリイソシアネート(B)を溶解又は分散可能なものであれば特に制限されない。例えば、トルエン、キシレン等の芳香族系有機溶剤、シクロヘキサン、メチルシクロヘキサン、エチルシクロヘキサン等の脂環式系有機溶剤、n-ヘキサン、n-ヘプタン等の脂肪族系有機溶剤、酢酸エチル、酢酸プロピル、酢酸ブチル等のエステル系有機溶剤、アセトン、メチルエチルケトン、メチルブチルケトン等のケトン系有機溶剤などが挙げられる。これらは、単独又は2種以上混合して使用することができる。
これらの中では、特にポリウレタンポリオール(A)の溶解性の見地から、酢酸エチル、酢酸プロピル、酢酸ブチル、トルエン、メチルシクロヘキサン、メチルエチルケトンが好ましく、トルエン、メチルエチルケトンがより好ましい。
溶剤(C)の含有量は、(A)、(B)及び(C)成分からなる金属箔と樹脂フィルムのラミネート用接着剤100質量部に対し、40~95質量部が好ましく、50~95質量部であることがより好ましく、80~90質量部であることが更に好ましい。40質量部以上であれば、本発明の金属箔と樹脂フィルムのラミネート用接着剤の塗布時の操作性が良好となり、95質量部以下であれば、本発明の金属箔と樹脂フィルムのラミネート用接着剤を塗布・硬化して得られる積層体の厚み制御性が良好となる。
本発明の金属箔と樹脂フィルムのラミネート用接着剤は、必要に応じて、反応促進剤、粘着付与剤、可塑剤等の添加剤を含有していてもよい。反応促進剤は、ポリウレタンポリオール(A)およびポリイソシアネート(B)の反応を促進するためのものであり、たとえば、有機スズ化合物であるジオクチルスズジラウレート、ジオクチルスズジアセテートや、第3級アミンである2、4、6-トリス(ジメチルアミノメチル)フェノール、ジメチルアニリン、ジメチルパラトルイジン、N、N-ジ(β-ヒドロキシエチル)-p-トルイジン等が挙げられる。これらの反応促進剤は、単独又は2種以上を併用することができる。
本発明の積層体は、金属箔と樹脂フィルムを本発明の金属箔と樹脂フィルムのラミネート用接着剤(以下、単に「本発明のラミネート用接着剤」ということがある。)から得られる接着剤層を介して接合したものである。また本発明の積層体中に、金属箔と樹脂フィルムを本発明のラミネート用接着剤から得られる接着剤層を介して接合した層が含まれれば、他に金属箔同士及び/又は樹脂フィルム同士が本発明のラミネート用接着剤から得られる接着剤層を介して接合した層を含んでも良い。この接合方法は、ヒートラミネーション方式やドライラミネーション方式等の公知の方法を用いることができる。ヒートラミネーション方式とは、溶剤(C)を含まない本発明のラミネート用接着剤を、接着剤層に接する層表面にて加熱溶融、又は接着剤層に接する層と共に加熱押し出しすることにより、積層体の層間に介在させ、接着剤層を形成する方式である。また、ドライラミネーション方式とは、溶剤(C)を含む本発明のラミネート用接着剤を接着剤層に接する層表面に塗布、乾燥せしめた後に他方の層と重ね合せて圧着することにより、積層体の層間に介在させ、接着剤層を形成する方式である。
本発明の電池外装用包装材は、本発明の積層体の、金属箔の外側に耐熱性樹脂フィルムからなる外層を設けたものである。また、必要に応じて、機械的強度や耐電解液性などの特性を高めるために、第1中間樹脂層又は/及び第2中間樹脂層等を付加した構成にすることができる。好ましい形態としては、具体的に次のような構成にすることができる。なお、接着剤層は「本発明のラミネート用接着剤から得られる接着剤層」を意味し、金属箔層をアルミニウム箔層として例示している。
(1)外層/アルミニウム箔層/接着剤層/樹脂フィルム層
(2)外層/第1中間樹脂層/アルミニウム箔層/接着剤層/樹脂フィルム層
(3)外層/アルミニウム箔層/第2中間樹脂層/接着剤層/樹脂フィルム層
(4)外層/第1中間樹脂層/アルミニウム箔層/第2中間樹脂層/接着剤層/樹脂フィルム層
(5)コート層/外層/アルミニウム箔層/接着剤層/樹脂フィルム層
(6)コート層/外層/第1中間樹脂層/アルミニウム箔層/接着剤層/樹脂フィルム層
(7)コート層/外層/アルミニウム箔層/第2中間樹脂層/接着剤層/樹脂フィルム層
(8)コート層/外層/第1中間樹脂層/アルミニウム箔層/第2中間樹脂層/接着剤層/樹脂フィルム層
外層に使用する樹脂フィルムは、耐熱性、成形性、絶縁性等に優れたものであり、ポリアミド(ナイロン)樹脂又はポリエステル樹脂の延伸フィルムが一般的に使用される。この外層フィルムの厚さは、9~50μm程度であり、9μm未満では包装材の成形を行うときに延伸フィルムの伸びが不足し、アルミニウム箔にネッキングが生じ、成形不良が起こり易い。一方、50μmを超える厚さの場合は、特段、成形性の効果が向上する訳でもなく、逆に体積エネルギー密度を低下させるとともにコストアップにつながるだけである。外層フィルムの厚さは10~40μm程度であることがより好ましく、20~30μmであることがさらに好ましい。
金属箔は、水蒸気等に対するバリア性の役割を担うもので、材質としては純アルミニウム系又はアルミニウム-鉄系合金のO材(軟質材)が一般的に使用され、かつ好ましい。アルミニウム箔の厚さとしては、加工性の確保及び酸素や水分の包装内への浸入を防止するバリア性確保のために、10~100μm程度が好ましい。アルミニウム箔の厚さが10μm未満の場合は、成形時においてアルミニウム箔の破断が生じたり、ピンホールが発生したりして酸素や水分の浸入のおそれがある。一方、アルミニウム箔の厚さが100μmを超えた場合は、成形時の破断の改善効果やピンホール発生防止効果が特段向上するわけでなく、単に包装材の総厚さが厚く、質量が増加し、体積エネルギー密度が低下する。アルミニウム箔は、一般的に30~50μm程度の厚さのものが使用され、40~50μmの厚さのものを使用することが好ましい。なお、アルミニウム箔には、樹脂フィルムとの接着性向上や耐食性向上のため、シランカップリング剤やチタンカップリング剤等のアンダーコート処理、クロメート処理等の化成処理をしておくことが好ましい。
樹脂フィルムとしては、ポリプロピレン、ポリエチレン、マレイン酸変性ポリプロピレン、エチレン-アクリレート共重合体又はアイオノマー樹脂などの熱融着性樹脂フィルムが好ましい。これらの樹脂は、ヒートシール性を有し、腐食性の強いリチウム二次電池の電解液等に対する耐薬品性を向上させる役割を担うものである。これらのフィルム厚さは、9~100μmが好ましく、より好ましくは20~80μmであり、40~80μmであるのが最も好ましい。樹脂フィルムの厚さが9μm以上であれば、十分なヒートシール強度が得られ、電解液等に対する耐食性が良好となる。樹脂フィルムの厚さが100μm以下であれば、電池外装用包装材の強度が十分でありかつ、成形性が良好となる。
本発明の電池外装用包装材は、外層の上にコート層を設けてもよい。コート層の形成法としては、ガスバリア性のポリマーをコートする方法、アルミニウム金属や酸化ケイ素・酸化アルミニウム等の無機酸化物を蒸着し、金属及び無機物の薄膜をコートする方法などがある。コート層を設けることにより、水蒸気及びその他のガスバリア性がより優れた積層体が得られる。
本発明の電池ケースは本発明の電池外装用包装材を成形することによって得られる。本発明の電池外装用包装材は耐電解液性や耐熱性、水蒸気及びその他のガスバリア性に優れており、二次電池、特にリチウムイオン電池用の電池ケースとして好適に用いられる。また、本発明の電池外装用包装材は成形性が非常に良好である為、公知の方法に従って成形することにより、本発明の電池ケースを簡便に得ることができる。成形の方法は特に限定されないが、深絞り成形又は張り出し成形によって成形すると、複雑な形状や寸法精度が高い電池ケースを作製することができる。
攪拌機、水分離器付き反応容器中に、水添ダイマージオールとして「Sovermol908」(BASF社製)を220.00g、水添ダイマー酸として「EMPOL1008」(BASF社製)を230.00g、触媒のブチルスズジラウレートとして「KS-1260」(堺化学工業製)を0.10g仕込み、約240℃、常圧下から始めて縮合水を流出させながら減圧しつつ脱水エステル化反応を行い、ポリエステルポリオール(以下、ポリエステルポリオール(1)と記す。)を得た。
攪拌装置、温度計およびコンデンサーを備えた反応容器中に、ビスフェノールA(新日鐵化学製、化合物名2,2-ビス(4-ヒドロキシフェニル)プロパン)を23.29g、「KS-1260」(堺化学工業製、ジブチルスズジラウレート)を0.01gおよび、「デスモジュールI」(バイエル社製イソホロンジイソシアネート)を34.02g、メチルエチルケトンを113.13g投入し、撹拌しながら、オイルバスを用いて85~90℃に昇温した。その後、2.5時間撹拌しながら反応を継続して、ポリウレタンポリイソシアネート(以下、ポリウレタンポリイソシアネート(2)と記す。)のメチルエチルケトン溶液を得た。
ビスフェノールAの代わりにビスフェノールF(本州化学工業製)20gを用いた以外は、合成例2と同様にして、ポリウレタンポリイソシアネート(以下、ポリウレタンポリイソシアネート(3)と記す。)のメチルエチルケトン溶液を得た。
攪拌装置、温度計およびコンデンサーを備えた反応容器中に、ポリエステルポリオール(1)を112.50g、「TCDアルコールDM」(オクセア社製、トリシクロデカンジメタノール)12.50g、ヒドロキノンモノメチルエーテル(和光純薬工業製)を0.04g、「KS-1260」(堺化学工業製、ジブチルスズジラウレート)を0.03gおよび、「デスモジュールW」(バイエル社製、メチレンビス(4-シクロヘキシルイソシアネート))を28.97g、トルエンを70g投入し、撹拌しながら、オイルバスを用いて85~90℃に昇温した。その後、2.5時間撹拌しながら反応を継続した。その後、赤外吸収スペクトルを測定し、イソシアナト基の吸収が消失していることを確認して反応を終了し、さらにトルエンを636.5g投入して撹拌溶解し、ポリウレタンポリオール(以下、ポリウレタンポリオール(4)と記す。)のトルエン溶液(固形分濃度18質量%)を得た。
合成例3と同様の方法で、表2に示すとおりの成分、量で合成を行い、ポリウレタンポリオール(4)~(13)のトルエン溶液もしくはトルエンとメチルエチルケトンの混合溶媒溶液(固形分濃度18質量%)を得た。
表2中、GI-1000、GI-2000は日本曹達製水添ポリブタジエンポリオール、G-1000は日本曹達製ポリブタジエンポリオール、14BGは三菱化学製1,4-ブタンジオールである。
合成例1~10および比較合成例11~13について、表1、2に示す。
合成例4で得たポリウレタンポリオール(4)のトルエン溶液33.33g(固形分6.00g、トルエン27.33g)に「デュラネートTKA-100」(旭化成ケミカルズ株式会社製、ヘキサメチレンジイソシアネートイソシアヌレート化物)0.34g、トルエン15.08gを加えて金属箔と樹脂フィルムのラミネート用接着剤1を調製した。 次いで、このラミネート用接着剤1を用いて、以下のようにして外層/外層用接着剤/アルミニウム箔層/ラミネート用接着剤1/樹脂フィルムの構造を有する電池外装用包装材をドライラミネーション方式で製造した。
外層:延伸ポリアミドフィルム(厚さ25μm)
外層用接着剤:ウレタン系ドライラミネート用接着剤(東洋モートン株式会社製:AD502/CAT10、塗布量3g/m2(塗布時))
アルミニウム箔層:アルミニウム-鉄系合金のアルミニウム箔(AA規格8079-O材、厚さ40μm)
ラミネート用接着剤1:上記金属箔と樹脂フィルムのラミネート用接着剤1(塗布量:乾燥後の厚さが2μm)
樹脂フィルム:未延伸ポリプロピレンフィルム(厚さ30μm)
実施例1と同様の方法で、表3に示すとおりの成分、量で金属箔と樹脂フィルムのラミネート用接着剤2~12の調製を行い、それぞれの金属箔と樹脂フィルムのラミネート用接着剤を用いて電池外装用包装材を製造した。
表3中、酸変性ポリプロピレンは、無水マレイン酸およびアクリル酸オクチルで変性した酸変性ポリプロピレン(酸価20mg/KOH)であり、ミリオネートMR-200は、日本ポリウレタン製ポリメリックジフェニルメタンジイソシアネートである。
得られた電池ケース用包装材料について、常態T字剥離強度、電解液溶媒浸漬後のT字剥離強度および85℃雰囲気下でのT字剥離強度を測定した。測定の条件、方法は下記の(1)~(3)の通りである。各試験は、n=2で行い、その平均値をとった。また、結果を表4に示す(単位は全てN/15mm)。
(1)常態T字剥離強度
長さ150mm×幅15mmの試験片およびオートグラフAG-X(株式会社島津製作所製)を用いて、23℃×50%RH雰囲気下に剥離速度100mm/minで剥離させ、アルミニウム箔層と未延伸ポリプロピレンフィルム層間の180°剥離強度を測定した。
(2)電解液溶媒浸漬後のT字剥離強度
長さ150mm×幅15mmの試験片を電解液溶媒(エチレンカーボネート/ジエチルカーボネート、質量比50/50)に浸漬し、85℃雰囲気下に1日放置した後に取り出し、その試験片を用いて上記(1)と同様にしてアルミニウム箔層と未延伸ポリプロピレンフィルム層間の180°剥離強度を測定する。
(3)85℃雰囲気下でのT字剥離強度
長さ150mm×幅15mmの試験片およびオートグラフAG-X(株式会社島津製作所製)を用いて、85℃雰囲気下に放置し、試験片の温度が85℃になった後に剥離速度100mm/minで剥離させ、アルミニウム箔層と未延伸ポリプロピレンフィルム層間の180°剥離強度を測定する。
Claims (15)
- ポリウレタン系接着剤に用いるポリオールであって、
鎖状ポリオレフィンポリオール(a1)及び/又は水添ダイマー酸由来の構成単位と水添ダイマージオール由来の構成単位とを有するポリエステルポリオール(a2)、飽和又は不飽和の環式炭化水素構造と2つ以上の水酸基とを併せ持つ水酸基含有炭化水素化合物(b)、及びポリイソシアネート(c)を含有する成分を重付加して得られる、ポリウレタンポリオール。 - 鎖状ポリオレフィンポリオール(a1)及び/又は水添ダイマー酸由来の構成単位と水添ダイマージオール由来の構成単位とを有するポリエステルポリオール(a2)、飽和又は不飽和の環式炭化水素構造と2つ以上の水酸基とを併せ持つ水酸基含有炭化水素化合物(b)、及びポリイソシアネート(c)を含有する成分を重付加して得られるポリウレタンポリオール(A)と、
飽和脂肪族及び/又は飽和脂環式ポリイソシアネート(B)と
を有する、金属箔と樹脂フィルムのラミネート用接着剤。 - 前記水酸基含有炭化水素化合物(b)が、架橋構造を有する飽和脂環構造を含むポリオールである、請求項2に記載の金属箔と樹脂フィルムのラミネート用接着剤。
- 前記水酸基含有炭化水素化合物(b)が、ビスフェノール化合物である、請求項2又は3に記載の金属箔と樹脂フィルムのラミネート用接着剤。
- 前記ポリイソシアネート(c)が、飽和脂環式ジイソシアネートである、請求項2~4のいずれか1項に記載の金属箔と樹脂フィルムのラミネート用接着剤。
- 前記鎖状ポリオレフィンポリオール(a1)が、実質的に不飽和炭化水素構造を含まないポリオレフィンポリオールである、請求項2~5のいずれか1項に記載の金属箔と樹脂フィルムのラミネート用接着剤。
- (b)成分が、(a1)及び(a2)成分の総量100質量部に対して5~100質量部であり、(c)成分に含まれるイソシアナト基数の比率が、(a1)、(a2)及び(b)成分に含まれる水酸基数に対して、0.5~1.3である、請求項2~6のいずれか1項に記載の金属箔と樹脂フィルムのラミネート用接着剤。
- 前記ポリウレタンポリオール(A)に含まれる水酸基数に対する、ポリイソシアネート(B)に含まれるイソシアナト基数の比率が、1~15である、請求項2~7のいずれか1項に記載の金属箔と樹脂フィルムのラミネート用接着剤。
- 溶剤(C)をさらに含む、請求項2~8のいずれか1項に記載の金属箔と樹脂フィルムのラミネート用接着剤。
- 金属箔と樹脂フィルムが、請求項2~9のいずれか1項に記載の金属箔と樹脂フィルムのラミネート用接着剤から得られる接着剤層を介して積層された、積層体。
- 前記金属箔がアルミニウム箔であり、前記樹脂フィルムが熱融着性樹脂フィルムを含有する、請求項10に記載の積層体。
- 前記金属箔の厚さが10~100μmであり、前記樹脂フィルムの厚さが9~100μmである、請求項10又は11に記載の積層体。
- 請求項10~12のいずれか1項に記載の積層体を用いて得られる、電池外装用包装材。
- 請求項13に記載の電池外装用包装材を用いて得られる、電池ケース。
- 請求項13に記載の電池外装用包装材を深絞り成形又は張り出し成形する、電池ケースの製造方法。
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KR1020167036344A KR102005305B1 (ko) | 2014-08-05 | 2015-05-25 | 금속박과 수지 필름의 라미네이트용 접착제, 그 조성물을 사용한 적층체, 전지 외장용 포장재 및 전지 케이스 |
CN201580035853.1A CN106661413B (zh) | 2014-08-05 | 2015-05-25 | 金属箔与树脂膜的层压用粘接剂、使用该组合物的叠层体、电池外包装用包装材和电池外壳 |
JP2016539880A JP6374969B2 (ja) | 2014-08-05 | 2015-05-25 | 金属箔と樹脂フィルムのラミネート用接着剤、該組成物を用いた積層体、電池外装用包装材および電池ケース |
US15/326,137 US20170207427A1 (en) | 2014-08-05 | 2015-05-25 | Adhesive for laminating metal foil to resin film, laminate obtained using said composition, packaging material for battery casing, and battery case |
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WO2018116555A1 (ja) * | 2016-12-22 | 2018-06-28 | 昭和電工株式会社 | 接着剤、これを用いた積層体、電池外装材、並びに電池ケース及びその製造方法 |
WO2019097887A1 (ja) | 2017-11-16 | 2019-05-23 | 昭和電工株式会社 | 接着剤、積層体、電池外装用包装材、電池ケース、及び電池ケースの製造方法 |
JP2020105294A (ja) * | 2018-12-26 | 2020-07-09 | 昭和電工株式会社 | ポリウレタンポリオール及び接着剤組成物 |
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JPWO2016021279A1 (ja) | 2017-04-27 |
US20170207427A1 (en) | 2017-07-20 |
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