# US 9,751,973 B2 · Epoxy systems for composites > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 9,751,973 B2 - Document ID: US9751973B2 - Status: Granted - Kind: B2 - Application number: 15/060,411 - Filed: 2016-03-03 - Published: 2016-08-25 - Granted: 2017-09-05 - Earliest claimed: 2010-06-24 - Assignees: Hexion Inc. - Applicants: Larry Steven Corley; Robert D. Farris; Carlton E. Ash - Inventors: Larry Steven Corley; Robert D. Farris; Carlton E. Ash - Web page: https://patentgrep.com/patent/US9751973B2 ## CPC - C08G 59/5013: {containing more than seven carbon atoms, e.g. fatty amines} - C08G 59/5006: {aliphatic} - C08G 59/5033: {aromatic} - C08G 59/504: {containing an atom other than nitrogen belonging to the amine group, carbon and hydrogen} - C08G 59/56: together with other curing agents - C08J 5/043: {with glass fibres} - C08L 63/00: Compositions of epoxy resins; Compositions of derivatives of epoxy resins - F03D 1/0675: {of the blades} - C08J 2363/00: Characterised by the use of epoxy resins; Derivatives of epoxy resins - Y02E 10/72: Wind turbines with rotation axis in wind direction - Y02P 70/50: Manufacturing or production processes characterised by the final manufactured product - 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) - C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06) - F03D: WIND MOTORS - Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION - Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS ## Abstract Compositions and methods for forming epoxy resin systems are provided. In one embodiment, a composition is provided for an epoxy resin system including a reaction product of an epoxy resin component and a curing agent component comprising a first amine compound having the formula R1R2R3N, wherein R1 and R2 are independently an aliphatic or alicyclic organic functional group and R3 is an alkyl group, having a backbone of 2-18 carbon atoms, and a second amine compound having one or more primary or secondary amine groups, with the stoichiometic ratio of —NH bonds of the second amine compound to the epoxy groups of the epoxy resin component being from 1:20 to about 21:20. The composition may be used to form composites, such as used in commercial wind turbine blade manufacturing. ## Claims ### Claim 1 A method for preparing an epoxy resin product, comprising: providing an epoxy resin component to a mixing device; providing a curing agent component to the mixing device, and the curing agent component comprising: a first amine compound represented by the formula: wherein R1 and R2 each comprise an organic functional group having from 1-6 carbon atoms, and R3 comprises an aralkyl group; and a second amine compound having one or more primary amine groups, one or more secondary amine groups, or combinations thereof, wherein the stoichiometric ratio of the —NH bonds of the second amine compound to the epoxy groups of the epoxy resin component is from 3:10 to 19:20 and the molar ratio of the second amine compound to the first amine compound is from about 0.01:1 to about 100:1; and reacting the epoxy resin component and curing agent. ### Claim 2 (depends on 1) The method of claim 1, wherein the reaction of the epoxy resin component and the curing agent exhibits a maximum exothermic temperature of 230° C. or lower for a 100 gram mass in a water bath at 70° C. ### Claim 3 (depends on 1) The method of claim 1, wherein the second amine compound comprises one or more amine compounds selected from the group consisting of a polyether diamine, a saturated aliphatic ring diamine, and combinations thereof. ### Claim 4 (depends on 1) The method of claim 1, wherein the R3 further comprises a functional group selected from the group consisting of a primary amine group, a secondary amine group, a tertiary amine group, and combinations thereof. ### Claim 5 (depends on 1) The method of claim 1, wherein R1 and R2 each comprise a functional group selected from the group consisting of a methyl group, an ethyl group, a propyl group, a C5-C6 carbocyclic aliphatic ring, a C5-C6 heterocyclic aliphatic ring, a C5-C6 saturated aliphatic ring, a C5-C6 unsaturated aliphatic ring, and combinations thereof. ### Claim 6 (depends on 1) The method of claim 1, wherein the R3 group comprises a benzyl group. ### Claim 7 (depends on 1) The method of claim 1, wherein the polyether diamine has the formula: H2NCH(CH3)CH2[OCH2CH(CH3)]XNH2, and x is from 2 to 70. ### Claim 8 (depends on 1) The method of claim 1, wherein the epoxy resin component further comprises: a polyglycidyl ether of a compound selected from the group consisting of an aliphatic glycol, a cycloaliphatic glycol, a triol, a polyol, a polyglycol, and combinations thereof, a polyacrylate or polymethacrylate ester of a polyol, or a combination thereof. ### Claim 9 (depends on 1) The method of claim 1, wherein the composition of the epoxy resin component and the curing agent exhibits a Tg of 75° C. at a cure time of less than 3 hours as measured by Differential Scanning Calorimetry. ### Claim 10 (depends on 1) The method of claim 1, further comprising providing a reinforcing fiber substrate; and contacting the reinforcing fiber substrate with the epoxy resin system. ### Claim 11 (depends on 10) The method of claim 10, wherein the reinforced fiber substrate comprises one or more layers of fiberglass material. ### Claim 12 (depends on 10) The method of claim 10, wherein the contacting the reinforcing fiber substrate with the epoxy resin system comprises an application process selected from the group consisting of an infusion process, a molding process, a layering process, and combinations thereof. ### Claim 13 A composition comprising an epoxy resin system, the epoxy resin system comprising a reaction product of: an epoxy resin component; and a curing agent component comprising: a first amine compound represented by the formula: wherein R1 and R2 each comprise an organic functional group having from 1-6 carbon atoms, and R3 comprises an aralkyl group; a second amine compound having one or more primary amine groups, one or more secondary amine groups, or combinations thereof, wherein the stoichiometric ratio of the —NH bonds of the second amine compound to the epoxy groups of the epoxy resin component is from about 1:20 to about 19:20 and the molar ratio of the second amine compound to the first amine compound is from about 0.01:1 to about 100:1. ### Claim 14 (depends on 13) The composition of claim 13, wherein the second amine compound comprises one or more amine compounds selected from the group consisting of a polyether diamine, a saturated aliphatic ring diamine, a linear aliphatic amine, and combinations thereof. ### Claim 15 (depends on 13) The composition of claim 13, wherein the R3 group further comprises a functional group selected from the group consisting of a primary amine group, a secondary amine group, a tertiary amine group, and combinations thereof. ### Claim 16 (depends on 13) The composition of claim 13, wherein R1 and R2 each comprise a functional group selected from the group consisting of a methyl group, an ethyl group, a propyl group, a C5-C6 carbocyclic aliphatic ring, a C5-C6 heterocyclic aliphatic ring, a C5-C6 saturated aliphatic ring, a C5-C6 unsaturated aliphatic ring, and combinations thereof. ### Claim 17 (depends on 13) The composition of claim 13, wherein the R3 group comprises a benzyl group. ### Claim 18 (depends on 14) The composition of claim 14, wherein the polyether diamine has the formula: H2NCH(CH3)CH2[OCH2CH(CH3)]XNH2, and x is from 2 to 70. ### Claim 19 (depends on 13) The composition of claim 13, wherein the epoxy resin component further comprises: a polyglycidyl ether of a compound selected from the group consisting of an aliphatic glycol, a cycloaliphatic glycol, a triol, a polyol, a polyglycol, and combinations thereof, a polyacrylate or polymethacrylate ester of a polyol, or a combination thereof. ### Claim 20 (depends on 13) The composition of claim 13, wherein, when cured, the reaction product of the epoxy resin component and the curing agent exhibits a Tg of 75° C. or higher at a cure time of three hours or less as measured by Differential Scanning Calorimetry. ### Claim 21 (depends on 13) The composition of claim 13, wherein, when curing, the reaction product of the epoxy resin component and the curing agent exhibits a maximum exothermic temperature of 230° C. or lower for a 100 gram mass in a water bath at 70° C. ### Claim 22 (depends on 13) The composition of claim 13, wherein the curing agent further comprises a modified amine compound selected from the group consisting of a secondary amine, a Mannich base, an amine-epoxy adduct, and combinations thereof. ### Claim 23 (depends on 13) The composition of claim 13, wherein R1 and R2 are both methyl functional groups. ### Claim 24 (depends on 13) The composition of claim 13, wherein the composition further comprises a mineral material selected from the group consisting of clay, boehmite, calcium carbonates, aluminosilicates, silica, and combinations thereof.