# US 10,766,229 B2 · Adhesive, laminate, packaging material for battery casing, battery case, and method of producing battery case > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,766,229 B2 - Document ID: US10766229B2 - Status: Granted - Kind: B2 - Application number: 16/608,973 - Filed: 2018-10-04 - Published: 2020-06-18 - Granted: 2020-09-08 - Earliest claimed: 2017-11-16 - Assignees: Showa Denko K.K. - Applicants: Showa Denko K.K. - Inventors: Kentarou Takahashi; Hiroto Kouka; Yasuhiro Nakagawa - Web page: https://patentgrep.com/patent/US10766229B2 ## CPC - B32B 15/095: comprising polyurethanes - C09J 175/14: Polyurethanes having carbon-to-carbon unsaturated bonds - B32B 7/12: using interposed adhesives or interposed materials with bonding properties - B32B 15/20: comprising aluminium or copper {(B32B15/016 and B32B15/017 take precedence)} - B32B 27/40: comprising polyurethanes - C08G 18/12: using two or more compounds having active hydrogen in the first polymerisation step - C08G 18/244: {tin salts of carboxylic acids} - C08G 18/6588: {with compounds of group C08G18/3203} - C08G 18/6715: {Unsaturated monofunctional alcohols or amines} - C08G 18/757: {containing at least two isocyanate or isothiocyanate groups linked to the cycloaliphatic ring by means of an aliphatic group} - C08G 18/792: {formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates} - C09J 4/00: Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond {; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16} - C09J 11/06: organic - C09J 175/04: Polyurethanes - C09J 175/16: having terminal carbon-to-carbon unsaturated bonds - H01M 50/124: having a layered structure - C09J 2203/33: for batteries or fuel cells - H01M 50/10: Primary casings; Jackets or wrappings - Y02E 60/10: Energy storage using batteries - B32B: LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM - C09J: ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES (preparation of glue or gelatine C09H) - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - H01M: PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY - Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION ## Abstract The present invention provides an adhesive for laminating a metal foil and a resin film, including: (A) 1% to 20% by mass of polyurethane which has at least one functional group selected from the group consisting of a hydroxy group, an acryloyl group, and a carboxy group; (B) 30% to 90% by mass of a monomer which does not has an active hydrogen and has two or more ethylenically unsaturated bonds; (C) 1% to 55% by mass of an aliphatic monomer which has one ethylenically unsaturated bond; (D) 1% to 15% by mass of a polyisocyanate compound; and (E) 0.5% to 5% by mass of a photoinitiator. The (B) has a cyclic structure, and the (C) has a linear hydrocarbon group, a branched hydrocarbon group, or a cycloalkyl group. ## Claims ### Claim 1 An adhesive for laminating a metal foil and a resin film, comprising: (A) 1% to 20% by mass of polyurethane which has at least one functional group selected from the group consisting of a hydroxy group, an acryloyl group, and a carboxy group; (B) 30% to 90% by mass of a monomer which does not has an active hydrogen group and has two or more ethylenically unsaturated bonds; (C) 1% to 55% by mass of an aliphatic monomer which has one ethylenically unsaturated bond; (D) 1% to 15% by mass of a polyisocyanate compound; and (E) 0.5% to 5% by mass of a photoinitiator, wherein the (B) has at least one cyclic structure selected from the group consisting of an alicyclic structure, an aromatic ring structure, and a heterocyclic structure, and the (C) has at least one group selected from the group consisting of an open chain hydrocarbon group having 1 to 12 carbon atoms and an alicyclic group having 5 to 10 carbon atoms. ### Claim 2 (depends on 1) The adhesive according to claim 1, wherein the (A) has at least one selected from the group consisting of polyurethane polyol (a1), polyurethane acrylate (a2), and carboxy group-containing polyurethane (a3). ### Claim 3 (depends on 2) The adhesive according to claim 2, wherein the polyurethane polyol (a1) is polyurethane polyol obtained by copolymerizing (1) polyol, (2) hydrocarbon having a saturated or unsaturated cyclic hydrocarbon structure and two or more hydroxy groups, and (3) polyisocyanate compound. ### Claim 4 (depends on 3) The adhesive according to claim 3, wherein the polyol is at least one selected from the group consisting of (1a) polyolefin polyol which does not have an alicyclic structure and (1b) polyester polyol which has a constitutional unit derived from a hydrogenated dimer acid and a constitutional unit derived from a hydrogenated dimer diol. ### Claim 5 (depends on 2) The adhesive according to claim 2, wherein the polyurethane acrylate (a2) is polyurethane acrylate obtained by copolymerizing (1) polyol, (2) hydrocarbon having a saturated or unsaturated cyclic hydrocarbon structure and two or more hydroxy groups, (3) polyisocyanate compound, and (4) (meth)acrylate having one or more hydroxy groups. ### Claim 6 (depends on 2) The adhesive according to claim 2, wherein the carboxy group-containing polyurethane (a3) is carboxy group-containing polyurethane obtained by copolymerizing (1) polyol, (2) hydrocarbon having a saturated or unsaturated cyclic hydrocarbon structure and two or more hydroxy groups, (3) polyisocyanate compound, and (5) compound having one or more hydroxy groups and one or more carboxy groups. ### Claim 7 (depends on 1) The adhesive according to claim 1, wherein the (C) contains an aliphatic monomer (c1) containing an active hydrogen group and having one ethylenically unsaturated bond. ### Claim 8 (depends on 1) The adhesive according to claim 1, wherein the (C) contains an aliphatic monomer (c2) containing phosphorus and having one ethylenically unsaturated bond. ### Claim 9 (depends on 7) The adhesive according to claim 7, wherein a ratio (NCO/active hydrogen) of the number of isocyanate groups contained in the (D) to the total number of active hydrogens contained in the (A) and the (c1) is 1.5 or greater. ### Claim 10 (depends on 1) A laminate, wherein a metal foil and a resin film are laminated by interposing an adhesive layer formed by curing the adhesive according to claim 1 therebetween. ### Claim 11 (depends on 10) The laminate according to claim 10, wherein the metal foil is an aluminum foil, and the resin film includes a thermally fusible resin film. ### Claim 12 (depends on 10) The laminate according to claim 10, wherein a thickness of the metal foil is in a range of 10 to 100 μm, and a thickness of the resin film is in a range of 9 to 100 μm. ### Claim 13 (depends on 10) A packaging material for a battery casing, comprising: the laminate according to claim 10. ### Claim 14 (depends on 13) A battery case comprising: the packaging material for a battery casing according to claim 13. ### Claim 15 (depends on 13) A method of producing a battery case, comprising: performing deep drawing molding or stretch molding on the packaging material for a battery casing according to claim 13.