WO2017195266A1 - ラミネート用接着剤、それを用いた積層体、及び二次電池 - Google Patents
ラミネート用接着剤、それを用いた積層体、及び二次電池 Download PDFInfo
- Publication number
- WO2017195266A1 WO2017195266A1 PCT/JP2016/063838 JP2016063838W WO2017195266A1 WO 2017195266 A1 WO2017195266 A1 WO 2017195266A1 JP 2016063838 W JP2016063838 W JP 2016063838W WO 2017195266 A1 WO2017195266 A1 WO 2017195266A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- polyolefin resin
- adhesive
- laminate
- laminating
- epoxy compound
- Prior art date
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- 230000001070 adhesive effect Effects 0.000 title claims abstract description 37
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- 230000008025 crystallization Effects 0.000 claims abstract description 31
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- 239000008151 electrolyte solution Substances 0.000 claims abstract description 19
- 229910052751 metal Inorganic materials 0.000 claims abstract description 18
- 239000002184 metal Substances 0.000 claims abstract description 18
- 150000001875 compounds Chemical class 0.000 claims abstract description 15
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims abstract description 14
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims abstract description 14
- 238000004519 manufacturing process Methods 0.000 claims abstract description 12
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
- 238000007789 sealing Methods 0.000 claims description 14
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- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 10
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- 229910013870 LiPF 6 Inorganic materials 0.000 description 2
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- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
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- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000009820 dry lamination Methods 0.000 description 1
- BXKDSDJJOVIHMX-UHFFFAOYSA-N edrophonium chloride Chemical compound [Cl-].CC[N+](C)(C)C1=CC=CC(O)=C1 BXKDSDJJOVIHMX-UHFFFAOYSA-N 0.000 description 1
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- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
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- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical group O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 1
- 229940091173 hydantoin Drugs 0.000 description 1
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- 230000001771 impaired effect Effects 0.000 description 1
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- 239000005453 ketone based solvent Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
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- 229920000092 linear low density polyethylene Polymers 0.000 description 1
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- 229920002223 polystyrene Polymers 0.000 description 1
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- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
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- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
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- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
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Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- 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
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- 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
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- 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
- B32B15/092—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 epoxy resins
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B32B7/00—Layered products characterised by the relation between layers; Layered products characterised by the relative orientation of features between layers, or by the relative values of a measurable parameter between layers, i.e. products comprising layers having different physical, chemical or physicochemical properties; Layered products characterised by the interconnection of layers
- B32B7/04—Interconnection of layers
- B32B7/12—Interconnection of layers using interposed adhesives or interposed materials with bonding properties
-
- 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
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- C09J11/06—Non-macromolecular additives organic
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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
- 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
- C09J123/02—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 not modified by chemical after-treatment
- C09J123/10—Homopolymers or copolymers of propene
-
- 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
- C09J123/02—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 not modified by chemical after-treatment
- C09J123/18—Homopolymers or copolymers of hydrocarbons having four or more carbon atoms
- C09J123/20—Homopolymers or copolymers of hydrocarbons having four or more carbon atoms having four to nine carbon atoms
-
- 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
- C09J123/28—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 by reaction with halogens or compounds containing halogen
-
- 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
- C09J151/00—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers
- C09J151/06—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers grafted on to homopolymers or copolymers of aliphatic hydrocarbons containing only one carbon-to-carbon double bond
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- H01M4/02—Electrodes composed of, or comprising, active material
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- H01M50/102—Primary casings; Jackets or wrappings characterised by their shape or physical structure
- H01M50/105—Pouches or flexible bags
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- H01M50/00—Constructional details or processes of manufacture of the non-active parts of electrochemical cells other than fuel cells, e.g. hybrid cells
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- H01M50/116—Primary casings; Jackets or wrappings characterised by the material
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- H01M50/10—Primary casings; Jackets or wrappings
- H01M50/116—Primary casings; Jackets or wrappings characterised by the material
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- H01M50/00—Constructional details or processes of manufacture of the non-active parts of electrochemical cells other than fuel cells, e.g. hybrid cells
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- H01M50/116—Primary casings; Jackets or wrappings characterised by the material
- H01M50/124—Primary casings; Jackets or wrappings characterised by the material having a layered structure
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- H01M50/00—Constructional details or processes of manufacture of the non-active parts of electrochemical cells other than fuel cells, e.g. hybrid cells
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- H01M50/116—Primary casings; Jackets or wrappings characterised by the material
- H01M50/124—Primary casings; Jackets or wrappings characterised by the material having a layered structure
- H01M50/126—Primary casings; Jackets or wrappings characterised by the material having a layered structure comprising three or more layers
- H01M50/129—Primary casings; Jackets or wrappings characterised by the material having a layered structure comprising three or more layers with two or more layers of only organic material
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2457/00—Electrical equipment
- B32B2457/18—Fuel cells
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- 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
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- 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
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- Y02P20/141—Feedstock
Definitions
- the present invention relates to a laminating adhesive for sealing an electrolyte used for a secondary battery, a laminate using the same, and a secondary battery.
- Secondary batteries typified by lithium ion batteries have a configuration in which a positive electrode, a negative electrode, and an electrolyte solution are enclosed between them. Moreover, as an encapsulating bag for enclosing a lead wire for taking out electricity of the positive electrode and the negative electrode to the outside, a laminated body in which a metal foil such as an aluminum foil or a metal vapor deposition layer and a plastic are bonded together is used.
- Patent Document 1 discloses an encapsulating bag that uses maleic acid-modified polyolefin resin for the innermost layer of the laminate and has a heat seal portion made of the same maleic acid-modified polyolefin resin, thereby improving the sealing reliability. Proposed.
- a maleic acid-modified polyolefin resin is generally used as an adhesive resin because it is excellent in adhesion to metal and heat sealability.
- it when used as a sealing film for a battery as described above, it exhibits excellent adhesion immediately after lamination at a high temperature, but has a low electrolytic solution resistance, causes delamination over time, and is used as a sealing film. I can't.
- Patent Document 2 discloses a battery including a metal layer, a surface treatment layer formed on the surface of the metal layer, and an adhesive resin layer made of polyolefin in which a carboxylic acid group formed on the surface treatment layer or a derivative thereof is modified. It describes about the laminated body for electrolyte solution sealing films, or the laminated body for battery electrode part protective films.
- Patent Document 3 includes (A) a polyolefin resin having at least one functional group selected from the group consisting of an acid anhydride group, a carboxyl group, and a carboxylic acid metal salt, and (B) two or more epoxy groups. And an adhesive resin composition comprising an epoxidized vegetable oil having a molecular weight of 3000 or less and a blending amount of the component (B) of 0.01 to 5 parts by mass with respect to 100 parts by mass of the component (A). .
- Patent Document 4 contains an acid-modified polyolefin resin (A) and a polyurethane resin (B), and is characterized in that (B) is 0.5 to 100 parts by mass with respect to 100 parts by mass of (A).
- the resin composition for the binder for secondary battery electrodes is described.
- JP 09-283101 A WO2007017043 Publication Japanese Patent Laid-Open No. 08-193148 JP 2010-277959 A
- An object of the present invention is to provide an unprecedented laminate adhesive, which is excellent in adhesion between the metal layer and the plastic layer of the laminate, and also has an electrolyte solution resistance even at low temperature curing, and its retention rate is high, It is an object to provide an adhesive composition for a laminate laminate that does not cause delamination, a manufacturing method thereof, a laminate using the adhesive, and a secondary battery.
- the polyolefin resin (A) contains propylene and 1-butene as monomers.
- the above problems have been solved by a laminating adhesive which is a polymer having a main component and a crystallization peak temperature in the range of 28 ° C to 38 ° C.
- the method for producing an adhesive according to the present invention can provide a laminate that solves the problems of the present invention by having an aging step in the range of 25 to 80 ° C.
- an adhesive composition, a production method thereof, a laminate using the adhesive, and a secondary battery can be provided.
- a laminate that solves the problems of the present invention can be provided by having an aging step in the range of 25 to 80 ° C. Since the said temperature is lower than the process temperature until now, it becomes possible to contribute to the cost reduction by energy saving at the time of manufacture.
- 13 is a 13 C-NMR chart of polypropylene as a standard product. It is a 13 C-NMR chart of polybutene-1 as a sample. 13 is a 13 C-NMR chart of polypropylene (a copolymer with ethylene) as a sample. 3 is a 13 C-NMR chart of hardlen NS-2002 used in Examples 1 to 4 as the polyolefin resin (A). 6 is a 13 C-NMR chart of GMP5070E used in Example 5 as a polyolefin resin (A). 3 is a 13 C-NMR chart of GMP3020E used in Comparative Example 1 as a polyolefin resin (A).
- 6 is a 13 C-NMR chart of Aurolen 350S used in Comparative Example 4 as a polyolefin resin (A).
- 10 is a 13 C-NMR chart of Aurolen 550S used in Comparative Example 5 as a polyolefin resin (A).
- the present invention includes the following items. 1.
- the polyolefin resin (A) is a polymer mainly composed of propylene and 1-butene as monomers, and is crystallized.
- the polyolefin resin (A) contains a modified polyolefin resin having an acid value of 1 to 200 mgKOH / g and / or a modified polyolefin resin having a hydroxyl value of 1 to 200 mgKOH / g.
- the epoxy compound (B) contains an epoxy compound having two or more epoxy groups in one molecule and one or more hydroxyl groups in one molecule and having a weight average molecular weight of 3000 or less as an essential component. Or 2. Adhesive for laminating according to 4). An epoxy compound (B) is blended at a ratio of 0.01 to 30 parts by mass with respect to 100 parts by mass of the polyolefin resin (A). ⁇ 3. An adhesive for laminating according to any one of 5. Further, it contains a thermoplastic elastomer, a tackifier, a catalyst, a phosphoric acid compound, a melamine resin, a silane coupling agent, or a reactive elastomer. ⁇ 4.
- a method for producing a laminate having a step of aging in the range of 25 to 80 ° C., 8.6. 6.
- the polyolefin resin (A) of the present invention is a polymer mainly composed of propylene and 1-butene as monomers, and is characterized by a crystallization peak temperature in the range of 28 ° C to 38 ° C.
- the polyolefin resin (A) is mainly composed of propylene and 1-butene as monomers.
- the total number of moles of propylene and 1-butene used as monomers is the total number of moles of monomers. It is said that it is a polymer of 50% or more.
- the total number of moles of propylene and 1-butene is preferably 80% or more of the total number of moles of monomers.
- the polyolefin resin (A) of the present invention may contain other monomers such as ethylene as long as it contains propylene as a monomer and 1-butene as a main component.
- 1-butene are each preferably less than the number of moles, more preferably not contained.
- the contrast of the number of moles of propylene, 1-butene, ethylene and the like as the monomer constituting the polyolefin resin (A) is determined by the peak height of 13 C-NMR.
- polystyrene resin (A) of the present invention examples include copolymers of olefins having 2 to 8 carbon atoms and copolymers of olefins having 2 to 8 carbon atoms and other monomers.
- polyethylene such as high density polyethylene (HDPE), low density polyethylene (LDPE), linear low density polyethylene resin, polypropylene, polyisobutylene, poly (1-butene), poly-4-methylpentene, polyvinyl Cyclohexane, polystyrene, poly (p-methylstyrene), poly ( ⁇ -methylstyrene), ethylene / propylene block copolymer, ethylene / propylene random copolymer, ethylene / butene-1 copolymer, ethylene / 4-methyl -1-pentene copolymer, ⁇ -olefin copolymer such as ethylene / hexene copolymer, ethylene / vinyl acetate copoly
- the polyolefin resin (A) of the present invention is characterized in that its crystallization peak temperature is in the range of 28 ° C to 38 ° C.
- the crystallization peak temperature in the present invention is the top temperature of the crystallization peak when the temperature is increased and melted to form a cooling resin and the temperature is increased again.
- the top temperature of the crystallization peak in the present invention was measured by a differential scanning calorimetry (DSC method).
- the polyolefin resin having different crystallization peak temperatures may be used alone or in combination, as long as the crystallization peak temperature is in the range of 28 ° C to 38 ° C.
- the crystallization peak calorific value described in the Examples and the like is a value measured from the area of the crystallization peak when the temperature is increased and melted to form a cooling resin and the temperature is increased again.
- the polyolefin resin (A) of the present invention may contain a modified polyolefin resin having an acid value of 1 to 200 mgKOH / g and / or a modified polyolefin resin having a hydroxyl value of 1 to 200 mgKOH / g.
- the polyolefin resin (A) used in the present invention can be variously used as described above, and in particular, a modified polyolefin resin in which various functional groups (for example, carboxyl group, hydroxyl group, etc.) are introduced into the polyolefin resin is more preferable. .
- a modified polyolefin resin having an acid value of 1 to 200 mgKOH / g (hereinafter referred to as acid-modified polyolefin resin) And / or a modified polyolefin resin having a hydroxyl value of 1 to 200 mgKOH / g (hereinafter referred to as a hydroxyl group-modified polyolefin resin) is more preferred.
- the acid-modified polyolefin resin is a polyolefin resin having a carboxyl group or a carboxylic anhydride group in the molecule, and is synthesized by modifying the polyolefin with an unsaturated carboxylic acid or a derivative thereof.
- this modification method graft modification or copolymerization can be used.
- the acid-modified polyolefin resin is a graft-modified polyolefin obtained by graft-modifying or copolymerizing at least one polymerizable ethylenically unsaturated carboxylic acid or a derivative thereof on a polyolefin resin before modification.
- the polyolefin resin before modification include the above-described polyolefin resins, and among them, a homopolymer of propylene, a copolymer of propylene and ⁇ -olefin, and the like are preferable. These can also be used individually by 1 type and can also be used in combination of 2 or more type.
- Examples of the ethylenically unsaturated carboxylic acid or its derivative to be graft-modified or copolymerized with the polyolefin resin before modification include acrylic acid, methacrylic acid, maleic acid, itaconic acid, citraconic acid, mesaconic acid, maleic anhydride, 4- Methylcyclohex-4-ene-1,2-dicarboxylic anhydride, bicyclo [2.2.2] oct-5-ene-2,3-dicarboxylic anhydride, 1,2,3,4,5, 8,9,10-octahydronaphthalene-2,3-dicarboxylic 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, methyl-bicyclo [2.2.1] hept-5-en
- a graft monomer selected from an ethylenically unsaturated carboxylic acid or a derivative thereof onto a polyolefin resin before modification various methods can be employed. For example, a method in which a polyolefin resin is melted and a graft monomer is added thereto to cause a graft reaction, a method in which a polyolefin resin is dissolved in a solvent to form a solution and a graft monomer is added thereto to cause a graft reaction, and a solution is dissolved in an organic solvent.
- Examples thereof include a method in which a polyolefin resin is mixed with the unsaturated carboxylic acid and the like, heated at a temperature equal to or higher than the softening temperature or melting point of the polyolefin resin, and simultaneously subjected to radical polymerization and hydrogen abstraction reaction in a molten state.
- a polyolefin resin is mixed with the unsaturated carboxylic acid and the like, heated at a temperature equal to or higher than the softening temperature or melting point of the polyolefin resin, and simultaneously subjected to radical polymerization and hydrogen abstraction reaction in a molten state.
- a radical initiator in order to efficiently graft copolymerize the graft monomer, it is preferable to carry out the grafting reaction in the presence of a radical initiator.
- the grafting reaction is usually performed under conditions of 60 to 350 ° C.
- the ratio of the radical initiator used is usually in the range of 0.001 to 1 part by mass with respect to 100 parts by mass of
- radical initiator can be used for the adhesive agent of this invention, although an imidazole type radical initiator can be mentioned as a preferable initiator, It is not restricted to these.
- imidazole type radical initiator can be mentioned as a preferable initiator, It is not restricted to these.
- triphenylphosphine, 1,8-diazabicyclo (5.4.0) undecene-7 (DBU) -phenol salt, DBU-octylate and the like can be mentioned.
- acid-modified polyolefin resins examples include maleic anhydride-modified polypropylene, ethylene- (meth) acrylic acid copolymer, ethylene-acrylic acid ester-maleic anhydride terpolymer, or ethylene-methacrylic acid ester- A maleic anhydride terpolymer may be mentioned.
- the hydroxyl group-modified polyolefin resin is a polyolefin resin having a hydroxyl group in the molecule, and is synthesized by graft modification or copolymerization of a polyolefin with a hydroxyl group-containing (meth) acrylic acid ester or a hydroxyl group-containing vinyl ether described later.
- the polyolefin resin before modification and the modification method are the same as in the case of acid-modified polyolefin resin.
- Examples of the hydroxyl group-containing (meth) acrylic acid ester include hydroxyethyl (meth) acrylate; hydroxypropyl (meth) acrylate, glycerol (meth) acrylate; lactone modified hydroxyethyl (meth) acrylate, (meth) acrylic acid.
- Examples include polyethylene glycol and polypropylene glycol (meth) acrylate.
- Examples of the hydroxyl group-containing vinyl ether include 2-hydroxyethyl vinyl ether, diethylene glycol monovinyl ether, 4-hydroxybutyl vinyl ether and the like.
- epoxy compound (B) examples include ethylene glycol, propylene glycol, hexanediol, neopentyl glycol, trimethylolethane, trimethylolpropane, pentaerythritol, glycerin, diglycerin, sorbitol, spiroglycol, or hydrogenated bisphenol. Examples thereof include polyol diglycidyl ether type epoxy resins such as A.
- aromatic epoxy resins such as diglycidyl ether type epoxy resins such as bisphenol A, bisphenol F, bisphenol S and bisphenol AD, and novolac type epoxy resins which are glycidyl ales of phenol novolac resins and cresol novolac resins;
- diglycidyl ether type epoxy resins of polyols such as ethylene oxide or propylene oxide adducts of compounds.
- polyglycidyl ether type epoxy resin of polyether polyol such as polyethylene glycol, polypropylene glycol or polytetramethylene glycol; bis (3,4-epoxycyclohexylmethyl) adipate, 3,4-epoxycyclohexylmethyl-3 ′, 4 ′ -Cycloaliphatic polyepoxy resins such as epoxy cyclohexyl carboxylate.
- polyglycidyl ester type epoxy resin of polycarboxylic acid such as propanetricarboxylic acid, butanetetracarboxylic acid, adipic acid, phthalic acid, terephthalic acid or trimellitic acid; butadiene, hexadiene, octadiene, dodecadiene, cyclooctadiene, ⁇ - Examples thereof include bisepoxy resins of hydrocarbon diene such as pinene or vinylcyclohexene.
- an epoxy resin of a diene polymer such as polybutadiene or polyisoprene; or a glycidylamine type epoxy resin such as tetraglycidyldiaminodiphenylmethane, tetraglycidylbisaminomethylcyclohexane, diglycidylaniline or tetraglycidylmetaxylylenediamine, or a triazine or Examples thereof include epoxy resins containing various heterocyclic rings such as hydantoin.
- an aromatic epoxy resin such as a bisphenol A type epoxy resin because of good adhesion and corrosion resistance.
- the bisphenol A type epoxy resin include “EPICLON 850, 860, 1050, 1055, 2055” manufactured by DIC Corporation, “jER828, 834, 1001, 1002, 1004, 1007” manufactured by Mitsubishi Chemical Corporation, and the like. Is mentioned.
- the epoxy resin which has 2 or more of epoxy groups in 1 molecule, 1 or more of hydroxyl groups in 1 molecule, and an epoxy compound whose weight average molecular weight is 3000 or less is an essential component may be sufficient. .
- the epoxy compound (B) is preferably blended at a ratio of 0.01 to 30 parts by mass with respect to 100 parts by mass of the polyolefin resin (A).
- the amount is less than 0.01 parts by mass, the adhesive force to the substrate is lowered, which is not preferable.
- the cohesive force of a coating film becomes low and is unpreferable.
- thermoplastic elastomers in the present invention, known and commonly used thermoplastic elastomers, tackifiers, catalysts, phosphoric acid compounds, melamine resins, silane coupling agents, or reactive elastomers can be used as other additives.
- the content of these additives can be appropriately adjusted and used as long as the function of the adhesive of the present invention is not impaired.
- the laminate of the present invention comprises the laminate adhesive composition of the present invention comprising a metal layer such as an aluminum foil and one or several plastic layers such as a polyolefin sheet such as polyethylene and polypropylene, and a polyester such as polyethylene terephthalate. It is obtained by pasting together.
- the adhesive composition for laminates of the present invention can be applied to any suitable solvent or dispersant such as, for example, ester solvents, ketone solvents, aromatic hydrocarbons, aliphatic hydrocarbons, alicyclic hydrocarbons, etc.
- the adhesive layer can be formed by dissolving / dispersing in a ratio and applying and drying on a metal foil using a known coating method such as a roll coating method, a gravure coating method, or a bar coating method.
- the dry coating weight of the laminating adhesive composition of the present invention is preferably in the range of 0.5 to 20.0 g / m 2 . If it is less than 0.5 g / m 2 , there will be a difficulty in continuous uniform application, while if it exceeds 20.0 g / m 2 , the solvent detachability after application will be reduced, workability will be significantly reduced, and the residual solvent Problems arise.
- the laminated body of the present invention is obtained by stacking the plastic layers and bonding them by dry lamination (dry laminating method).
- the temperature of the laminate roll is preferably about room temperature to 120 ° C.
- the pressure is preferably about 3 to 300 kg / cm 2 .
- the laminated body of this invention performs aging after preparation.
- the aging conditions are preferably a temperature of 25 to 80 ° C. and a time of 12 to 240 hours, during which the adhesive strength is generated.
- the laminate of the present invention can be used as an electrolytic solution sealing film or an electrode part protective film for a primary or secondary battery.
- the laminate is used by contacting the plastic layer side with a polar organic solvent and / or salts.
- Particularly suitable for use as a secondary battery electrolyte sealing film or secondary battery electrode part protective film for non-aqueous electrolyte batteries, solid batteries, etc. by using it in contact with a non-aqueous electrolyte containing a polar organic solvent and salt.
- it can be used as a battery sealing bag by folding and heat-sealing so that the plastic layers face each other. Since the adhesive used in the present invention is excellent in heat sealability, it prevents leakage of the non-aqueous electrolyte and enables long-term use as a battery.
- polar organic solvent examples include aprotic polar solvents such as alkyl carbonates, esters, and ketones. Specifically, ethylene carbonate, propylene carbonate, butylene carbonate, dimethyl carbonate, ethyl methyl carbonate, diethyl carbonate, ⁇ -butyrolactone, 1,2-dimethoxyethane, tetrahydrofuran, 2-methyltetrahydrofuran, 1,3- Examples include dioxolane, 4-methyl-1,3-dioxolane, methyl formate, 4-methyl-1,3-dioxomethyl formate, methyl acetate, and methyl propionate.
- the salt include alkali metal salts such as lithium salt, sodium salt and potassium salt. For batteries, lithium salts such as LiPF 6 , LiBF 4 , and Li-imide are generally used.
- the non-aqueous electrolyte is obtained by dissolving 0.5 to 3 mmol of the alkali metal salt in an aprotic polar organic solvent such as a cyclic carbonate, a chain carbonate, or a mixture thereof. Even if the laminate of the present invention is used in contact with the polar solvent and / or salts, particularly a non-aqueous electrolyte that is a mixture thereof, it does not cause delamination of the metal layer, adhesive layer, and plastic layer over a long period of time. Can be used.
- the battery of the present invention is a battery having a battery electrolyte sealing film or a battery electrode part protective film comprising the laminate.
- the battery of the present invention can be used stably as a battery for a long time since the film does not cause delamination and can prevent leakage of the nonaqueous electrolyte.
- the laminate of the present invention has excellent adhesion between the metal layer and the plastic layer and excellent durability against polar organic solvents or salts, and does not cause delamination even when contacted with a nonaqueous electrolyte or the like. . Therefore, a battery using such a laminate as a battery electrolyte sealing film or a battery electrode protective film, and a secondary battery using a secondary battery electrolyte sealing film or a secondary battery electrode protective film are: Can be used stably for a long time.
- each polyolefin resin (A) was analyzed by 13 C-NMR, and the structure of the contained monomer was identified from the spectrum.
- Measuring solvent: CDC1 3 Measurement temperature: 25 ° C Accumulation count: 1000 times
- the charts of FIGS. 1 to 3 were quoted from “Infrared Absorption and 13 CNMR Spectra of Major Polymers” (Japan Analytical Chemical Society / Polymer Analysis Research Meeting).
- Example 1 Add 100 parts of Hardren NS-2002, 0.01 part of Curazole 2E4MZ, 0.5 part of Denacol EX-321, stir well, apply 5 g / m 2 (dry) to aluminum foil with a bar coater, 80 ° C- After drying for 1 minute, it was bonded to a CPP film at 100 ° C. to prepare a coated product. Thereafter, the initial adhesive strength was measured after aging at 60 ° C. for 5 days.
- Example 2 Example 2 to (Example 5) Other components were blended as shown in Table 1, and an adhesive was prepared in the same manner as in Example 1. Furthermore, each laminated body was produced by the same production method as the laminated body 1. The laminates obtained in each example were evaluated for adhesion performance and electrolytic solution resistance (retention rate), and Table 1 shows the results. The conditions for each test are as follows.
- the crystallization peak temperature and the crystallization peak calorie were measured under the following conditions.
- Equipment Hitachi High-Tech Science / X-DSC7000 Container: Hitachi High-Tech Science / Open type aluminum container Conditions: Sample 5 mg, Reference: Empty container, Atmosphere: Nitrogen flow 20 mL / min Measurement temperature: 30 ° C. (0 min) ⁇ ⁇ 10 ° C./min ⁇ 80° C. (0 min) ⁇ 10 ° C./min ⁇ 200° C./min
- the hardlen NS-2002 and GMP5070E which are the polyolefin resins (A) used in the examples, are mainly composed of propylene and 1-butene as monomers as compared with the NMR measurement samples, and further crystallized.
- the peak temperature is in the range of 28 ° C to 38 ° C.
- GMP3020E, GMP7550E, Aurolen 350S, and Aurolen 550S which are polyolefin resins (A) used in Comparative Examples, are mainly composed of propylene and 1-butene as monomers by comparison with NMR measurement standards. Although it is a component, the crystallization peak temperature is outside the range of 28 ° C to 38 ° C.
- the polyolefin resin (A) is mainly composed of propylene and 1-butene as monomers, those having a crystallization peak temperature in the range of 28 ° C. to 38 ° C. are resistant to electrolyte solution (retention rate). Although it is excellent in that the problem of the present invention can be solved, it is clear that a substance outside the temperature range does not lead to the solution of the problem. From the above results, it was revealed that the laminate obtained using the present adhesive was excellent in initial adhesive strength and electrolytic solution resistance (retention rate).
- the laminate adhesive of the present invention is excellent in the adhesion between the metal layer and the plastic layer, has an electrolyte solution resistance even at low temperature curing, and has a high retention rate, the laminate obtained using the present adhesive is It can be suitably used as a laminate for a secondary battery because it has resistance to electrolytic solution even at low temperature curing and does not cause delamination over time.
- a Peak indicating the methyl group of polybutene-1 (corresponding to A in FIG. 2)
- b Peak indicating the methyl group of polypropylene (corresponding to A in FIG. 1)
- c Peak indicating methylene group of polypropylene (corresponding to B in FIG. 1)
- d Methyl group of copolymer with polyethylene (corresponding to A in FIG. 3)
- e Peak indicating the methyl group of polypropylene (corresponding to A in FIG. 1)
- f Peak indicating methylene group of polypropylene (corresponding to B in FIG. 1)
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Abstract
Description
また、本発明に係る接着剤の製造方法においては、25~80℃の範囲でエージングする工程を有することにより、本願発明の課題を解決する積層体を提供することができる。
また、接着剤の製造方法においては、25~80℃の範囲でエージングする工程を有することにより、本願発明の課題を解決する積層体を提供することができる。当該温度は、これまでの処理温度より低温であるため、製造時における省エネルギーによるコスト低減に資することが可能となる。
1.ポリオレフィン樹脂(A)と、エポキシ化合物(B)とを含有するラミネート用接着剤において、ポリオレフィン樹脂(A)が、単量体としてプロピレン及び1-ブテンを主成分とする重合体であり、結晶化ピーク温度が28℃~38℃の範囲であるラミネート用接着剤、
2.ポリオレフィン樹脂(A)が、酸価が1~200mgKOH/gである変性ポリオレフィン樹脂、及び/又は水酸基価が1~200mgKOH/gである変性ポリオレフィン樹脂を含有する1.に記載のラミネート用接着剤、
3.エポキシ化合物(B)が、エポキシ基を1分子中に2つ以上、且つ水酸基を1分子中に1つ以上有し、重量平均分子量が3000以下であるエポキシ化合物を必須の成分とする、1.又は2.に記載のラミネート用接着剤、
4.前記ポリオレフィン樹脂(A)100質量部に対して、エポキシ化合物(B)が0.01~30質量部の割合で配合された1.~3.の何れかに記載のラミネート用接着剤、
5.更に、熱可塑性エラストマー、粘着付与剤、触媒、燐酸化合物、メラミン樹脂、シランカップリング剤、又は反応性エラストマーを含有する1.~4.の何れかに記載のラミネート用接着剤、
6.1.~5.の何れかに記載のラミネート用接着剤を、金属層とポリオレフィン樹脂層間で使用してなる積層体、
7.6.に記載の積層体の製造方法において、25~80℃の範囲でエージングする工程を有する積層体の製造方法、
8.6.に記載の積層体、或いは7.に記載の製造方法により得られる積層体を電解液封止フィルム又は電極部保護フィルムとして用いた二次電池。
本発明のポリオレフィン樹脂(A)は、単量体としてプロピレン及び1-ブテンを主成分とする重合体であり、結晶化ピーク温度が28℃~38℃の範囲であることに特徴を有する。
特に、プロピレン、及び1-ブテンの合計モル数は、単量体全体のモル数の80%以上であることが好ましい。
また、本発明のポリオレフィン樹脂(A)は、単量体としてプロピレン、及び1-ブテンを主成分としている限り、その他の単量体、例えばエチレン等を含んでもよく、その場合には、プロピレン、及び1-ブテンの各々のモル数より少ない重合体であることが好ましく、更には含まれないことがより好ましい。
ここで、ポリオレフィン樹脂(A)を構成する単量体としてのプロピレン、1-ブテン、及びエチレン等のモル数の対比は、13C-NMRのピーク高さによって判断される。
具体的には、例えば、高密度ポリエチレン(HDPE)、低密度ポリエチレン(LDPE)、線状低密度ポリエチレン樹脂などのポリエチレン、ポリプロピレン、ポリイソブチレン、ポリ(1-ブテン)、ポリ4-メチルペンテン、ポリビニルシクロヘキサン、ポリスチレン、ポリ(p-メチルスチレン)、ポリ(α-メチルスチレン)、エチレン・プロピレンブロック共重合体、エチレン・プロピレンランダム共重合体、エチレン・ブテン-1共重合体、エチレン・4-メチル-1-ペンテン共重合体、エチレン・へキセン共重合体などのα-オレフィン共重合体、エチレン・酢酸ビニル共重合体、エチレン・アクリル酸共重合体、エチレン・メチルメタクリレート共重合体、エチレン・酢酸ビニル・メチルメタクリレート共重合体、アイオノマー樹脂などを挙げることができる。更に、これらポリオレフィンを塩素化した塩素化ポリオレフィンも使用することができる。
本発明においては、異なる結晶化ピーク温度を有するポリオレフィン樹脂を単独で用いても、或いは併用しても、その結晶化ピーク温度が28℃~38℃の範囲内にある限りにおいて限定されない。
また、実施例等に記載される結晶化ピーク熱量は、昇温融解後冷却樹脂化し、再度昇温した際の結晶化ピークの面積から測定した値である。
例えば、トリフェニルフォスフィン、1,8-ジアザビシクロ(5.4.0)ウンデセン-7(DBU)-フェノール塩、DBU-オクチル酸塩等を挙げることができる。
前記水酸基含有(メタ)アクリル酸エステルとしては、(メタ)アクリル酸ヒドロキエチル;(メタ)アクリル酸ヒドロキシプロピル、(メタ)アクリル酸グリセロール;ラクトン変性(メタ)アクリル酸ヒドロキシエチル、(メタ)アクリル酸ポリエチレングリコール、(メタ)アクリル酸ポリプロピレングリコール等が挙げられ、前記水酸基含有ビニルエーテルとしては、2-ヒドロキシエチルビニルエーテル、ジエチレングリコールモノビニルエーテル、4-ヒドロキシブチルビニルエーテル等が挙げられる。
本発明のエポキシ化合物(B)としては、例えば、エチレングリコール、プロピレングリコール、ヘキサンジオール、ネオペンチルグリコール、トリメチロールエタン、トリメチロールプロパン、ペンタエリトリトール、グリセリン、ジグリセリン、ソルビトール、スピログリコールもしくは水添ビスフェノールA等のポリオールジグリシジルエーテル型エポキシ樹脂が挙げられる。
更に、ポリエチレングリコール、ポリプロピレングリコールもしくはポリテトラメチレングリコール等のポリエーテルポリオールのポリグリシジルエーテル型エポキシ樹脂;ビス(3,4-エポキシシクロヘキシルメチル)アジペート、3,4-エポキシシクロヘキシルメチル-3’,4’-エポキシシクロヘキシルカルボキシレート等の環状脂肪族型ポリエポキシ樹脂が挙げられる。
具体例として、ビスフェノールA型エポキシ樹脂としては、DIC(株)製「EPICLON 850、860、1050、1055、2055」、三菱化学(株)製「jER828、834、1001、1002、1004、1007」等が挙げられる。
また、エポキシ基を1分子中に2つ以上、且つ水酸基を1分子中に1つ以上有し、重量平均分子量が3000以下であるエポキシ化合物を必須の成分とする、エポキシ樹脂であってもよい。
0.01質量部より少ないと、基材への接着力が低くなって好ましくない。
また、30質量部より多いと、塗膜の凝集力が低くなって好ましくない。
本発明では、その他の添加剤として、公知慣用の熱可塑性エラストマー、粘着付与剤、触媒、燐酸化合物,メラミン樹脂、シランカップリング剤、又は反応性エラストマーを用いることができる。これらの添加剤の含有量は、本発明の接着剤の機能を損なわない範囲内で適宜調整して用いることができる。
本発明の積層体は、本発明のラミネート用接着剤組成物を、アルミニウム箔等の金属層とポリエチレン、ポリプロピレン等のポリオレフィンシート、ポリエチレンテレフタレート等のポリエステルなどの1種または数種のプラスチック層とを張り合わせて得られるものである。
また、本発明の積層体は、作製後エージングを行うことが好ましい。エージング条件は、好ましい温度は25~80℃、時間は12~240時間であり、この間に接着強度が生じる。
本発明の積層体は、一次または二次電池の電解液封止フィルムまたは電極部保護フィルムとして使用できるが、この場合プラスチック層側に極性有機溶媒及び/または塩類等と接触させて使用する。特に極性有機溶媒及び塩を含む非水電解質と接触させる状態で使用することにより、特に非水電解質電池、固体電池等の二次電池電解液封止フィルムまたは二次電池電極部保護フィルムとして好適に使用することができる。この場合、プラスチック層が対向するように折り重ねてヒートシールすることにより、電池用封止袋として使用することができる。本発明で用いている接着剤はヒートシール性に優れるため、非水電解質の漏洩を防止し、電池として長期使用が可能になる。
塩としては、リチウム塩、ナトリウム塩、カリウム塩等のアルカリ金属塩があげられる。電池用としてはLiPF6、LiBF4、Li-イミド等のリチウム塩が一般的に使用される。
本発明の積層体は前記極性溶媒及び/または塩類、特にそれらの混合物である非水電解質と接触する状態で使用しても金属層、接着層、プラスチック層の層間剥離を生じることなく、長期にわたって使用することができる。
各種ポリオレフィン樹脂(A)の構造については、13C-NMRにて分析し、そのスペクトルから、含まれる単量体の構造を特定した。
装置名:ECX-400P(JEOL社製)
測定溶剤:CDC13
測定温度:25℃
積算回数:1000回
また、図1~3のチャートは、『主要ポリマーの赤外吸収および13CNMRスペクトル集』(日本分析化学会/高分子分析研究懇談会)より引用した。
ハードレンNS-2002を100部、キュアゾール2E4MZを0.01部、デナコールEX-321を0.5部入れて良く攪拌し、アルミフォイルにバーコーターで5g/m2(dry)塗布し、80℃-1分乾燥させた後、CPPフィルムと100℃で貼り合せて塗工物を作製した。その後、60℃-5日エージングさせた後に初期接着強度を測定した。
その他の成分を表1のとおりに配合し、実施例1と同様に接着剤を作製した。更に積層体1と同様の作製方法により各積層体を作製した。
各例で得られた積層体において、接着性能、耐電解液性(保持率)を評価し、表1にその結果を示す。
なお、各試験の条件は以下のとおりである。
(株)エー・アンド・ディー製テンシロン試験において、試料を15mm幅にカットし、180℃剥離強度(180℃N/15mm)を測定した。
本発明において、結晶化ピーク温度及び結晶化ピーク熱量の測定は以下の条件で行った。
装置:日立ハイテクサイエンス/X-DSC7000
容器:日立ハイテクサイエンス/オープン型アルミ容器
条件:試料5mg、リファレンス:空容器、雰囲気:窒素フロー20mL/min
測定温度:30℃(0min)→ -10℃/min → -80℃(0min)→ 10℃/min → 200℃/min
積層体を電解液「エチレンカーボネート:エチルメチルカーボネート:ジメチルカーボネート=1:1:1(wt%)+LiPF6:1mol+ビニレンカーボネート:1wt%」に85℃-7日間浸漬させ、浸漬前後の接着強度の保持率から以下のとおりに評価を実施した。
○:60%以上、△:60~50%、×:50%以下
(NMRチャート図4参照)
・GMP5070E(ロッテケミカル社製)変性ポリオレフィン樹脂 不揮発分100% 結晶化ピーク温度28.8℃ 結晶化ピーク熱量31.0mj/mg
(NMRチャート図5参照)
・キュアゾール 2E4MZ(四国化成工業株式会社製)イミダゾール 不揮発分100%
・U-CAT SA 1(サンアプロ株式会社製)DBU-フェノール塩 不揮発分100%
・U-CAT SA 102(サンアプロ株式会社製)DBU-オクチル酸塩 不揮発分100%
・FTR-8120(三井化学社製)粘着付与剤 不揮発分100%
・デナコール EX-321(ナガセケムテックス株式会社製)エポキシ樹脂 エポキシ当量140 不揮発分100%
・エピクロン 860(DIC株式会社製)ビスフェノールA型エポキシ樹脂 エポキシ当量240 不揮発分100%
比較例として、表2のとおりに配合し、実施例と同様にして積層体を作製した。さらに、その積層体を用い、初期接着強度、耐電解液性(保持率)を評価した。結果を表2に示す。
(NMRチャート図6参照)
・GMP7550E(ロッテケミカル社製)変性ポリオレフィン樹脂 不揮発分100% 結晶化ピーク温度24.6℃ 結晶化ピーク熱量19.1mj/mg
・アウローレン 350S(日本製紙社製)変性ポリオレフィン樹脂 不揮発分100% 結晶化ピーク温度8.6℃ 結晶化ピーク熱量3.9mj/mg
(NMRチャート図7参照)
・アウローレン 550S(日本製紙社製)変性ポリオレフィン樹脂 不揮発分100% 結晶化ピーク温度38.9℃ 結晶化ピーク熱量37.0mj/mg
(NMRチャート図8参照)
・キュアゾール 2E4MZ(四国化成工業株式会社製)イミダゾール 不揮発分100%
・U-CAT SA 1(サンアプロ株式会社製)DBU-フェノール塩 不揮発分100%
・デナコール EX-321(ナガセケムテックス株式会社製)エポキシ樹脂 エポキシ当量140 不揮発分100%
・エピクロン 860(DIC株式会社製)ビスフェノールA型エポキシ樹脂 エポキシ当量240 不揮発分100%
一方、比較例に用いられたポリオレフィン樹脂(A)である、GMP3020E、GMP7550E、アウローレン 350S、アウローレン 550Sは、NMR測定の標品との対比により、単量体としてプロピレン及び1-ブテンを主成分としているが、結晶化ピーク温度が28℃~38℃の範囲外にあるものである。
従って、ポリオレフィン樹脂(A)が単量体としてプロピレン及び1-ブテンを主成分としていても、結晶化ピーク温度が28℃~38℃の範囲内にあるものは、耐電解液性(保持率)に優れ、本発明の課題の解決が可能であるが、当該温度の範囲外にあるものは課題解決に至らないがことが明らかである。
以上の結果から、本接着剤を用いて得られる積層体は、初期接着強度、耐電解液性(保持率)に優れることが明らかとなった。
b:ポリプロピレンのメチル基を示すピーク(図1のAに相当)
c:ポリプロピレンのメチレン基を示すピーク(図1のBに相当)
d:ポリエチレンとの共重合体のメチル基(図3のAに相当)
e:ポリプロピレンのメチル基を示すピーク(図1のAに相当)
f:ポリプロピレンのメチレン基を示すピーク(図1のBに相当)
Claims (8)
- ポリオレフィン樹脂(A)と、エポキシ化合物(B)とを含有するラミネート用接着剤において、
ポリオレフィン樹脂(A)が、単量体としてプロピレン及び1-ブテンを主成分とする重合体であり、結晶化ピーク温度が28℃~38℃の範囲であるラミネート用接着剤。 - ポリオレフィン樹脂(A)が、酸価が1~200mgKOH/gである変性ポリオレフィン樹脂、及び/又は水酸基価が1~200mgKOH/gである変性ポリオレフィン樹脂を含有する請求項1に記載のラミネート用接着剤。
- エポキシ化合物(B)が、エポキシ基を1分子中に2つ以上、且つ水酸基を1分子中に1つ以上有し、重量平均分子量が3000以下であるエポキシ化合物を必須の成分とする、請求項1又は2に記載のラミネート用接着剤。
- 前記ポリオレフィン樹脂(A)100質量部に対して、エポキシ化合物(B)が0.01~30質量部の割合で配合された請求項1~3の何れかに記載のラミネート用接着剤。
- 更に、熱可塑性エラストマー、粘着付与剤、触媒、燐酸化合物、メラミン樹脂、シランカップリング剤、又は反応性エラストマーを含有する請求項1~4の何れかに記載のラミネート用接着剤。
- 請求項1~5の何れかに記載のラミネート用接着剤を、金属層とポリオレフィン樹脂層間で使用してなる積層体。
- 請求項6に記載の積層体の製造方法において、25~80℃の範囲でエージングする工程を有する積層体の製造方法。
- 請求項6に記載の積層体、或いは請求項7に記載の製造方法により得られる積層体を電解液封止フィルム又は電極部保護フィルムとして用いた二次電池。
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