# US 11,898,067 B2 · Reactive 2-component adhesive system in film form having improved heat-and-humidity resistance > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 11,898,067 B2 - Document ID: US11898067B2 - Status: Granted - Kind: B2 - Application number: 16/466,148 - Filed: 2017-11-22 - Published: 2020-02-27 - Granted: 2024-02-13 - Earliest claimed: 2016-12-05 - Assignees: Tesa SE - Applicants: Tesa SE - Inventors: Uwe Schümann; Clementine Pradier - Web page: https://patentgrep.com/patent/US11898067B2 ## CPC - C09J 4/06: {Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond} in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00 - C09J 7/10: without carriers - C09J 5/04: involving separate application of adhesive ingredients to the different surfaces to be joined - C09J 7/385: {Acrylic polymers} - C08K 3/20: Oxides; Hydroxides {(graphene oxides C08K3/042)} - C08K 5/14: Peroxides - C08K 5/17: Amines; Quaternary ammonium compounds - C08K 5/56: Organo-metallic compounds, i.e. organic compounds containing a metal-to-carbon bond - C08L 39/06: Homopolymers or copolymers of N-vinyl-pyrrolidones - C08L 75/04: Polyurethanes - C09J 2203/00: Applications of adhesives in processes or use of adhesives in the form of films or foils - C09J 2301/408: additives as essential feature of the adhesive layer - C09J 2433/00: Presence of (meth)acrylic polymer - C09J 2475/00: Presence of polyurethane - 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) - C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09) - C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06) ## Abstract The present invention relates to a reactive adhesive film comprising (a) a polymeric film-forming matrix, (b) at least one reactive monomer or reactive resin, and (c) a reagent selected from an initiator, in particular a radical initiator, or an activator, featuring enhanced heat-and-humidity resistance, and to a reactive 2-component adhesive system in film form for bonding diverse materials, such as, for example, metal, wood, glass and/or plastic material. ## Claims ### Claim 1 A reactive adhesive film, comprising: (a) a polymeric film-forming matrix; (b) at least one reactive monomer or reactive resin; and (c) a reagent, wherein the reagent is at least an activator, the reagent optionally including one of an initiator or a radical initiator, wherein the at least one reactive monomer or reactive resin comprises at least a cyclic, non-aromatic, nitrogen-containing vinyl compound ; further wherein the only reactive component of the reactive adhesive film is (i) the at least one reactive monomer or reactive resin and (ii) the reagent. ### Claim 2 (depends on 1) The reactive adhesive film as claimed in claim 1, wherein the cyclic, non-aromatic nitrogen-containing vinyl compound comprises a cyclic amide. ### Claim 3 (depends on 1) The reactive adhesive film as claimed in claim 1, further comprising at least one compound selected from the group consisting of an acrylic acid, an acrylic acid ester, a methacrylic acid, and a methacrylic acid ester. ### Claim 4 (depends on 1) The reactive adhesive film as claimed in claim 1, wherein the polymeric film-forming matrix comprises a thermoplastic polymer, a thermoplastic polyurethane, an elastomer, or a thermoplastic elastomer. ### Claim 5 (depends on 1) The reactive adhesive film as claimed in claim 1, wherein the initiator comprises a peroxide, a hydroperoxide, or dimethylbenzyl hydroperoxide. ### Claim 6 (depends on 1) The reactive adhesive film as claimed in claim 1, wherein the activator comprises an amine, a dihydropyridine derivative, a transition metal salt, a transition metal complex, or iron(II) phthalocyanine. ### Claim 7 (depends on 1) The reactive adhesive film as claimed in claim 1, wherein the reactive adhesive film has pressure-sensitive adhesive properties. ### Claim 8 (depends on 1) The reactive adhesive film as claimed in claim 1, comprising the activator, the radical initiator, and further comprising: (I) from 10 to 90% by weight of the polymeric film-forming matrix, from 10 to 90% by weight of the at least one reactive monomer or reactive resin, and from 1 to 20% by weight of the radical initiator; or (II) from 10 to 90% by weight of the polymeric film-forming matrix, from 10 to 90% by weight of the at least one reactive monomer or reactive resin, and from greater than 0 to 10% by weight of the activator. ### Claim 9 (depends on 2) The reactive adhesive film as claimed in claim 2, wherein the cyclic, non-aromatic, nitrogen-containing vinyl compound is N-vinylcaprolactam or N-vinylpyrrolidone. ### Claim 10 (depends on 3) The reactive adhesive film as claimed in claim 3, wherein the at least one compound is selected from the group consisting of methyl methacrylate, methacrylic acid, cyclohexyl methacrylate, tetrahydrofurfuryl methacrylate, 2-phenoxyethyl methacrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl methacrylate, 4-hydroxybutyl methacrylate, a hydroxybutyl-methacrylate isomer mixture, di(ethylene glycol)methyl ether methacrylate, and ethylene glycol dimethacrylate. ### Claim 11 (depends on 1) The reactive adhesive film as claimed in claim 1, comprising from 20 to 50% by weight of the polymeric film-forming matrix, from 40 to 70% by weight of the at least one reactive monomer or reactive resin, and from 0.1 to 5% by weight of the activator. ### Claim 12 (depends on 1) A reactive adhesive film system comprising a first reactive adhesive film and a second reactive adhesive film as claimed in claim 1, the first reactive adhesive film comprising: a polymeric film forming matrix; at least one reactive monomer or reactive resin; and a reagent, wherein the reagent is one of an initiator or a radical initiator, wherein the at least one reactive monomer or reactive resin comprises a nitrogen containing vinyl compound, a nitrogen containing oligomeric compound having carbon carbon double bond(s). ### Claim 13 (depends on 1) A reactive adhesive film system comprising two or more reactive adhesive films, wherein: a first of the two or more reactive adhesive films comprises a reactive adhesive film comprising: a polymeric film forming matrix; at least one reactive monomer or reactive resin; and a reagent, wherein the reagent is one of an initiator or a radical initiator, wherein the at least one reactive monomer or reactive resin comprises a nitrogen containing vinyl compound, a nitrogen containing oligomeric compound having carbon carbon double bond(s); a second of the two or more reactive adhesive films comprises a he reactive adhesive film as claimed in claim 1; and the first of the two or more reactive adhesive films and the second of the two or more reactive films are each present alternately. ### Claim 14 (depends on 12) The reactive adhesive film system as claimed in claim 12, further comprising films, layers, adhesives, backings, release papers, or release liners. ### Claim 15 (depends on 1, 12) A method of bonding materials of metal, wood, glass, or plastic, comprising bonding metal, wood, glass, or plastic materials with the reactive adhesive film as claimed in claim 1 or the reactive adhesive film system as claimed in claim 12. ### Claim 16 (depends on 1) A method for producing a reactive adhesive film as claimed in claim 1, wherein the method comprising: 1. dissolving and/or finely distributing ingredients in one or more solvent(s) and/or water; 2. mixing the dissolved and/or finely distributed ingredients; 3. coating a release liner, a release paper, a backing material, or a pressure-sensitive adhesive with the mixture of the dissolved and/or finely distributed ingredients to form a reactive adhesive film; 4. evaporating the one or more solvent(s) and/or water from the reactive adhesive film to form a dried reactive adhesive film; and 5. optionally winding the dried reactive adhesive film into a roll, wherein the ingredients comprise: (a) the polymeric film-forming matrix; (b) the at least one reactive monomer or reactive resin; and (c) the reagent with at least the activator and either an initiator or a radical initiator. ### Claim 17 (depends on 1) A kit for providing a two-component adhesive film system, comprising: at least one first reactive adhesive film, the first reactive adhesive film comprising: a polymeric film forming matrix; at least one reactive monomer or reactive resin; and a reagent, wherein the reagent is one of an initiator or a radical initiator, wherein the at least one reactive monomer or reactive resin comprises a nitrogen containing vinyl compound, a nitrogen containing oligomeric compound having carbon carbon double bond(s) ; and (ii) at least one second reactive adhesive film as claimed in claim 1. ### Claim 18 (depends on 12) A composite bonded by the reactive adhesive film system as claimed in claim 12. ### Claim 19 (depends on 12) The reactive adhesive film as claimed in claim 12, further comprising the activator, the radical initiator, and further comprising from 20 to 50% by weight of the polymeric film-forming matrix, from 40 to 70% by weight of the at least one reactive monomer or reactive resin, and from 5 to 15% by weight of the radical initiator. ### Claim 20 (depends on 17) A composite bonded by the kit as claimed in claim 17.