# US 10,501,618 B2 · Epoxy resin composition, and film, prepreg, and fiber-reinforced plastic using same > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,501,618 B2 - Document ID: US10501618B2 - Status: Granted - Kind: B2 - Application number: 15/100,556 - Filed: 2014-12-02 - Published: 2016-10-13 - Granted: 2019-12-10 - Earliest claimed: 2013-12-02 - Assignees: Mitsubishi Chemical Corporation - Applicants: Mitsubishi Chemical Corporation - Inventors: Tomoko Ishimoto; Manabu Kaneko; Tetsuya Atsumi; Kenichi Watanabe - Web page: https://patentgrep.com/patent/US10501618B2 ## CPC - C08L 63/00: Compositions of epoxy resins; Compositions of derivatives of epoxy resins - B32B 1/08: Tubular products - B32B 27/04: as impregnant, bonding, or embedding substance {(not used)} - B32B 27/38: comprising epoxy resins - C08G 59/20: characterised by the epoxy compounds used - C08G 59/223: {together with monoepoxy compounds} - C08G 59/226: {Mixtures of di-epoxy compounds} - C08G 59/24: carbocyclic - C08G 59/245: {aromatic} - C08G 59/26: heterocyclic - C08G 59/3227: {Compounds containing acyclic nitrogen atoms} - C08G 59/4021: {Ureas; Thioureas; Guanidines; Dicyandiamides} - C08G 59/44: Amides - C08J 5/04: Reinforcing macromolecular compounds with loose or coherent fibrous material - C08J 5/18: Manufacture of films or sheets - C08J 5/243: {using carbon fibres} - C08K 7/06: Elements - C08J 2363/00: Characterised by the use of epoxy resins; Derivatives of epoxy resins - C08J 2463/00: Characterised by the use of epoxy resins; Derivatives of epoxy resins - C08J 2463/02: Polyglycidyl ethers of bis-phenols - C08J 2471/00: Characterised by the use of polyethers obtained by reactions forming an ether link in the main chain; Derivatives of such polymers - C08L 2205/02: containing two or more polymers of the same C08L -group - C08L 2205/03: containing three or more polymers in a blend - C08L 2205/16: Fibres; Fibrils - C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06) - B32B: LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - 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) - C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09) ## Abstract Provided are an epoxy resin composition which contains an epoxy resin and a curing agent, and satisfies the following (1), (2), and (3): (1) the bending elastic modulus of a cured product of the epoxy resin composition is 3.3 GPa or higher; (2) the bending strain at break of the cured product of the epoxy resin composition is 9% or higher; and (3) the fiber-reinforced plastic α formed of the cured product of the epoxy resin composition and a reinforcing fiber substrate in which carbon fibers, which are continuous fibers, are evenly aligned in one direction has 90° bending strength of 95 MPa or higher, and a film, a prepreg, and fiber-reinforced plastic that are produced by using the epoxy resin composition. ## Claims ### Claim 1 An epoxy resin composition, comprising an epoxy resin and a curing agent, and satisfying the following (1), (2), and (3): (1) a bending elastic modulus of a cured product of the epoxy resin composition is 3.3 GPa or higher; (2) a bending strain at break of the cured product of the epoxy resin composition is 9% or higher; and (3) a fiber-reinforced plastic a formed of the cured product of the epoxy resin composition and a reinforcing fiber substrate in which carbon fibers, which are continuous fibers, are evenly aligned in one direction has 90° bending strength of 95 MPa or higher, wherein the epoxy resin comprises: (A) an oxazolidone ring-containing epoxy resin, which is not a glycidylamine epoxy resin, in an amount of 30 parts by mass to 70 parts by mass; (B-1) a glycidylamine epoxy resin not having an oxazolidone ring in an amount of 1 part by mass to 30 parts by mass; (C) a bisphenol bifunctional epoxy resin having the number average molecular weight of 600 or more, which does not have oxazolidone ring and is not a glycidylamine epoxy resin, in an amount of 5 parts by mass to 30 parts by mass; (D) a phenoxy resin in an amount of 1 part by mass to 15 parts by mass; and (E) a curing agent in an amount of 1 part by mass to 25 parts by mass, each of the amounts of (A), (B-1) , (C), (D), and (E) being relative to 100 parts by mass of a total amount of all epoxy resins contained in the epoxy resin composition. ### Claim 2 (depends on 1) The epoxy resin composition according to claim 1, wherein the 90° bending strain at break of the fiber-reinforced plastic α is 1.3% or higher. ### Claim 3 (depends on 1) A film, comprising the epoxy resin composition according to claim 1. ### Claim 4 (depends on 1) The epoxy resin composition according to claim 1, further comprising: (G) a low viscosity epoxy resin, which does not contain an oxazolidone ring and is neither a diglycidylamine epoxy resin nor glycidylphthalimide, wherein a total amount of the components (A), (B-1) , (C), and (G) is 75 parts by mass or more relative to 100 parts by mass of the total amount of the epoxy resin contained in the epoxy resin composition. ### Claim 5 (depends on 1) The epoxy resin composition according to claim 1, wherein the epoxy resin composition further satisfies the following (4): (4) a tensile lap-shear strength is 9.5 MPa or higher when measurement is made based on JIS K 6850 by using A5052 aluminum as a subject for adhesion. ### Claim 6 (depends on 1) The epoxy resin composition according to claim 1, wherein the component (B-1) is glycidylaniline. ### Claim 7 (depends on 1) The epoxy resin composition according to claim 1, wherein the component (B-1) is N,N-diglycidyl-o-toluidine. ### Claim 8 (depends on 1) The epoxy resin composition according to claim 1, wherein a number average molecular weight of the component (B-1) is 300 or less. ### Claim 9 (depends on 1) A prepreg comprising a reinforcing fiber substrate and the epoxy resin composition according to claim 1 impregnated in the reinforcing fiber substrate. ### Claim 10 (depends on 1) A fiber-reinforced plastic, comprising a cured product of the epoxy resin composition according to claim 1 and a reinforcing fiber. ### Claim 11 (depends on 10) The fiber-reinforced plastic according to claim 10 having a tubular shape. ### Claim 12 An epoxy resin composition, comprising an epoxy resin and a curing agent, and satisfying the following (1), (2), and (3): (1) the bending elastic modulus of a cured product of the epoxy resin composition is 3.3 GPa or higher; (2) the bending strain at break of the cured product of the epoxy resin composition is 9% or higher; and (3) the fiber-reinforced plastic a formed of the cured product of the epoxy resin composition and a reinforcing fiber substrate in which carbon fibers, which are continuous fibers, are evenly aligned in one direction has 90° bending strength of 95 MPa or higher, wherein the epoxy resin comprises: (A) an oxazolidone ring-containing epoxy resin, which is not a glycidylamine epoxy resin, in an amount of 30 parts by mass to 70 parts by mass; (B-2) glycidylphthalimide in an amount of 1 part by mass to 15 parts by mass; (C) a bisphenol bifunctional epoxy resin having the number average molecular weight of 600 or more, which does not have an oxazolidone ring and is not a glycidylamine epoxy resin, in an amount of 5 parts by mass to 30 parts by mass; (D) a phenoxy resin in an amount of 1 part by mass to 15 parts by mass; and (E) a curing agent in an amount of 1 part by mass to 25 parts by mass, each of the amounts of (A), (B-2), (C), (D), and (E) being relative to 100 parts by mass of a total amount of all epoxy resins contained in the epoxy resin composition. ### Claim 13 (depends on 12) The epoxy resin composition according to claim 12, wherein the 90° bending strain at break of the fiber-reinforced plastic a is 1.3% or higher. ### Claim 14 (depends on 12) A film, comprising the epoxy resin composition according to claim 12. ### Claim 15 (depends on 12) The epoxy resin composition according to claim 12, further comprising: (G) a low viscosity epoxy resin, which does not contain an oxazolidone ring and is neither a diglycidylamine epoxy resin nor glycidylphthalimide, wherein a total amount of the components (A), (B-2), (C), and (G) is 75 parts by mass or more relative to 100 parts by mass of the total amount of the epoxy resin contained in the epoxy resin composition. ### Claim 16 (depends on 12) A prepreg comprising a reinforcing fiber substrate and the epoxy resin composition according to claim 12 impregnated in the reinforcing fiber substrate. ### Claim 17 (depends on 12) A fiber-reinforced plastic, comprising a cured product of the epoxy resin composition according to claim 12 and a reinforcing fiber. ### Claim 18 (depends on 17) The fiber-reinforced plastic according to claim 17 having a tubular shape.