# US 10,767,040 B2 · Thermosetting epoxy resin compositions useful as structural reinforcement or structural foam > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,767,040 B2 - Document ID: US10767040B2 - Status: Granted - Kind: B2 - Application number: 16/308,625 - Filed: 2017-06-20 - Published: 2019-09-05 - Granted: 2020-09-08 - Earliest claimed: 2016-06-20 - Assignees: Sika Technology AG - Applicants: Sika Technology AG - Inventors: John Hanley - Web page: https://patentgrep.com/patent/US10767040B2 ## CPC - C08J 9/0061: {characterized by the use of several polymeric components} - C08G 18/10: Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step - C08G 18/4854: {Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group} - C08G 18/73: acyclic - C08G 59/4021: {Ureas; Thioureas; Guanidines; Dicyandiamides} - C08G 59/4246: {polymers with carboxylic terminal groups} - C08G 59/4253: {Rubbers} - C08J 9/0066: {Use of inorganic compounding ingredients} - C08J 9/08: developing carbon dioxide - C08J 9/103: {Azodicarbonamide} - C08J 9/105: {containing sulfur} - C08J 9/32: from compositions containing microballoons, e.g. syntactic foams - C08L 63/00: Compositions of epoxy resins; Compositions of derivatives of epoxy resins - C09D 5/00: Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced {(electrically insulating plastics, resins or waxes H01B3/30)}; Filling pastes - C09D 163/00: Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins - C09J 163/00: Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins - C08G 59/22: Di-epoxy compounds - C08G 59/226: {Mixtures of di-epoxy compounds} - C08J 2203/02: CO2-releasing, e.g. NaHCO3 and citric acid - C08J 2203/04: N2 releasing, ex azodicarbonamide or nitroso compound - C08J 2203/22: Expandable microspheres, e.g. Expancel® - C08J 2205/10: Rigid foams - C08J 2363/00: Characterised by the use of epoxy resins; Derivatives of epoxy resins - C08J 2363/02: Polyglycidyl ethers of bis-phenols - C08J 2409/00: Characterised by the use of homopolymers or copolymers of conjugated diene hydrocarbons - C08J 2409/02: Copolymers with acrylonitrile - C08J 2463/00: Characterised by the use of epoxy resins; Derivatives of epoxy resins - C08J 2475/04: Polyurethanes - C08J 2475/08: from polyethers - C08L 2203/14: used for foams - C08L 2205/025: containing two or more polymers of the same hierarchy C08L, and differing only in parameters such as density, comonomer content, molecular weight, structure - C08L 2205/035: containing four or more polymers in a blend - C08J: WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H (working, e.g. shaping, of plastics B29) - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06) - C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D) - 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) ## Abstract Thermosetting epoxy resin compositions on the one hand at room temperature in the incompletely cured state exhibit extremely slight alteration in shape and on the other hand develop a high surface tack, and, moreover, in the fully cured state are of high impact strength and at the same time exhibits high adhesion, particularly to metallic substrates. These compositions are ideally suited to the production of self-adhesive reinforcing elements. ## Claims ### Claim 1 A thermosetting epoxy resin composition comprising from 17.5 to 30 weight % of at least one liquid epoxy resin A having on average more than one epoxide group per molecule; from 1 to 5 weight % of at least one hardener B for epoxy resins which is activated by elevated temperature; from 0 to 2 weight % of at least one accelerator C; from 5 to 12 weight %, of at least one polymeric impact modifier D, which is a terminally blocked polyurethane prepolymer; from 1 to 5 weight % of at least one polyisoprene E; from 5 to 10 weight % of at least one carboxyl- or epoxide- terminated acrylonitrile/butadiene copolymer F which is liquid at room temperature; from 15 to 20 weight % of at least one carboxyl- or epoxide- terminated acrylonitrile/butadiene copolymer G which is solid at room temperature; based on a total weight of the epoxy resin composition. ### Claim 2 (depends on 1) The thermosetting epoxy resin composition according to claim 1, further comprising at least one physical or chemical blowing agent H in an amount of from 0.1 to 3 weight %, based on the total weight of the epoxy resin composition. ### Claim 3 (depends on 2) A structural foam obtained by heating the thermosetting epoxy resin composition according to claim 2. ### Claim 4 (depends on 1) The thermosetting epoxy resin composition according to claim 1, wherein the thermosetting epoxy resin composition is tacky at room temperature. ### Claim 5 (depends on 1) The thermosetting epoxy resin composition according to claim 1, wherein the thermosetting epoxy resin composition has a viscosity at 80° C. in a range of from 900 to 5 000 Pa·s, the viscosity being determined oscillographically by a rheometer with heatable plate (MCR 201, Anton Paar) (1000 μm gap, measurement plate diameter: 25 mm (plate/plate), deformation 0.01 at 5 Hz, temperature: 80° C.). ### Claim 6 (depends on 1) The thermosetting epoxy resin composition according to claim 1, wherein the thermosetting epoxy resin composition has a viscosity at 30° C. in a range of from 5 000 to 50 000 Pa·s, the viscosity being determined oscillographically by a rheometer with heatable plate (MCR 201, Anton Paar) (1000 μm gap, measurement plate diameter: 25 mm (plate/plate), deformation 0.01 at 5 Hz, temperature: 30° C.). ### Claim 7 (depends on 1) The thermosetting epoxy resin composition according to claim 1, wherein the at least one accelerator C comprises at least one substituted urea selected from the group consisting of 3-(3-chloro-4-methylphenyl)-1,1-dimethylurea (chlortoluron), p-chlorophenyl-N,N-dimethylurea (monuron), 3-phenyl-1,1-dimethylurea (fenuron), 3,4-dichlorophenyl-N,N-dimethylurea (diuron), N,N-dimethylurea, N-isobutyl-N′,N′-dimethylurea, and 1,1′-(hexane-1,6-diyl)bis(3,3′ -dimethylurea). ### Claim 8 (depends on 1) The thermosetting epoxy resin composition according to claim 1, comprising from 0.3 to 0.5 weight % of the at least one accelerator C. ### Claim 9 (depends on 1) The thermosetting epoxy resin composition according to claim 1, wherein the at least one impact modifier D is a terminally blocked polyurethane prepolymer represented by formula (I); where R1 is a p-valent residue of a linear or branched polyurethane prepolymer PU1, terminated with isocyanate groups, following the removal of the terminal isocyanate groups; p is from 2 to 8; and R independently at each occurrence is a substituent selected from the group consisting of where R5, R6, R7 and R8 each independently of one another are an alkyl or cycloalkyl or aralkyl or arylalkyl group, or R5 together with R6, or R7 together with R8, form part of a 4- to 7-membered ring which is optionally substituted; R9, R9′ and R10° each independently of one another are an alkyl or aralkyl or arylalkyl group or are an alkyloxy or aryloxy or aralkyloxy group; R11 is an alkyl group, R12, R13 and R14 each independently of one another are an alkylene group having 2 to 5 C atoms which optionally has double bonds or is optionally substituted, or are a phenylene group or are a hydrogenated phenylene group; R15, R16 and R17 each independently of one another are H or are an alkyl group or are an aryl group or an aralkyl group; and R18 is an aralkyl group or is a mono- or polycyclic, substituted or unsubstituted aromatic group which optionally has aromatic hydroxyl groups; R4 is a residue of an aliphatic, cycloaliphatic, aromatic or araliphatic epoxide containing a primary or secondary hydroxyl group, after the removal of the hydroxyl and epoxide groups; and m is 1, 2, or 3. ### Claim 10 (depends on 1) The thermosetting epoxy resin composition according to claim 1, wherein the at least one polyisoprene E is a polyisoprene which is liquid at room temperature. ### Claim 11 (depends on 1) The thermosetting epoxy resin composition according to claim 1, comprising from 1 to 3 weight % of the at least one polyisoprene E. ### Claim 12 (depends on 1) The thermosetting epoxy resin composition according to claim 1, wherein the at least one carboxyl- or epoxide-terminated acrylonitrile/butadiene copolymer F which is liquid at room temperature is an epoxide-terminated acrylonitrile/butadiene copolymer having an elastomer fraction of from 35 to 45 weight %. ### Claim 13 (depends on 1) The thermosetting epoxy resin composition according to claim 1, wherein the at least one carboxyl- or epoxide-terminated acrylonitrile/butadiene copolymer G which is solid at room temperature is an epoxide-terminated acrylonitrile/butadiene copolymer having an elastomer fraction of from 25 to 35 weight %. ### Claim 14 (depends on 1) The thermosetting epoxy resin composition according to claim 1, comprising from 16 to 20 weight % of the at least one carboxyl- or epoxide-terminated acrylonitrile/butadiene copolymer G. ### Claim 15 (depends on 1) The thermosetting epoxy resin composition according to claim 1, wherein the at least one carboxyl- or epoxide-terminated acrylonitrile/butadiene copolymer G is an epoxide-terminated acrylonitrile/butadiene copolymer that is a reaction product of at least one acrylonitrile/butadiene copolymer and a solid epoxy resin that is bisphenol A-based solid resin, bisphenol F-based solid resin, or both. ### Claim 16 (depends on 1) An article having a three-dimensional extent comprising the thermosetting epoxy resin composition according to claim 1. ### Claim 17 (depends on 1) A method for reinforcing outer surfaces or hollow cavities of structural components, comprising the steps of i) placing the thermosetting epoxy resin composition according to claim 1 onto outer surfaces or into cavities of structural components; ii) heating the thermosetting epoxy resin composition to a temperature of 100-220° C. ### Claim 18 (depends on 17) A reinforced article obtained from the method according to claim 17. ### Claim 19 (depends on 1) A method for reinforcing heat-stable materials, comprising the steps of i) placing the thermosetting epoxy resin composition according to claim 1 onto heat-stable materials; ii) heating the thermosetting epoxy resin composition to a temperature of 100-220° C. ### Claim 20 (depends on 1) A fully cured epoxy resin composition obtained by heating a thermosetting epoxy resin composition according to claim 1 to a temperature of 100-220° C.