# US 10,501,590 B2 · Solid composites containing polymeric matrix with carbon fibers embedded therein > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,501,590 B2 - Document ID: US10501590B2 - Status: Granted - Kind: B2 - Application number: 15/158,012 - Filed: 2016-05-18 - Published: 2016-10-27 - Granted: 2019-12-10 - Earliest claimed: 2012-02-28 - Assignees: UT-Battelle, LLC - Applicants: Ut-Battelle, LLC - Inventors: Frederic Vautard; Soydan Ozcan; Felix Leonard Paulauskas - Web page: https://patentgrep.com/patent/US10501590B2 ## CPC - C08J 5/06: using pretreated fibrous materials - C08L 63/10: Epoxy resins modified by unsaturated compounds - C08J 2333/04: esters - 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 - Y10T 428/249948: Fiber is precoated - Y10T 428/2918: including free carbon or carbide or therewith [not as steel] - 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) - Y10T: TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION ## Abstract A functionalized carbon fiber having covalently bound on its surface a partially cured epoxy or amine-containing sizing agent, wherein at least a portion of epoxide or amine groups in the sizing agent are available as uncrosslinked epoxide or amine groups, which corresponds to a curing degree of epoxide or amine groups of no more than about 0.6. Composites comprised of these functionalized carbon fibers embedded in a polymeric matrix are also described. Methods for producing the functionalized carbon fibers and composites thereof are also described. ## Claims ### Claim 1 A solid composite in which carbon fibers are embedded in a polymeric matrix derived from an unsaturated precursor resin containing carbon-carbon double bonds, wherein said carbon fibers have covalently bonded on their surfaces a partially cured sizing agent comprised of an epoxy resin, wherein said epoxy resin is covalently attached to a linking group that contains an accessible unsaturated group capable of reacting with said carbon-carbon double bonds via a vinyl addition reaction, and at least a portion of epoxide groups in the sizing agent are available as uncrosslinked epoxide groups, which corresponds to a curing degree of epoxide groups of no more than about 0.6. ### Claim 2 (depends on 1) The solid composite of claim 1, wherein said polymeric matrix is a thermoset. ### Claim 3 (depends on 2) The solid composite of claim 2, wherein said thermoset is derived from vinyl-addition polymerization of an unsaturated resin containing carbon-carbon double bonds. ### Claim 4 (depends on 3) The solid composite of claim 3, wherein said unsaturated resin is a vinyl ester resin. ### Claim 5 (depends on 3) The solid composite of claim 3, wherein said unsaturated resin is an unsaturated polyester resin. ### Claim 6 (depends on 3) The solid composite of claim 3, wherein said unsaturated resin is in admixture with at least one unsaturated reactive diluent that is cured with the unsaturated resin. ### Claim 7 (depends on 6) The solid composite of claim 6, wherein said unsaturated reactive diluent is selected from the group consisting of styrene, divinyl benzenes, methacrylates, acrylates, and vinyl esters. ### Claim 8 (depends on 1) The solid composite of claim 1, wherein said polymeric matrix is derived from an acrylate or methacrylate resin. ### Claim 9 (depends on 1) The solid composite of claim 1, wherein said polymeric matrix is a thermoplastic. ### Claim 10 (depends on 1) The solid composite of claim 1, wherein said epoxy resin possesses a curing degree of surface epoxide groups of no more than about 0.5. ### Claim 11 (depends on 1) The solid composite of claim 1, wherein said epoxy resin possesses a curing degree of surface epoxide groups of no more than about 0.4. ### Claim 12 (depends on 1) The solid composite of claim 1, wherein said epoxy resin is comprised of a difunctional epoxy resin. ### Claim 13 (depends on 12) The solid composite of claim 12, wherein said difunctional epoxy resin is selected from one or both of bisphenol A diglycidyl ether and ethylene glycol diglycidyl ether. ### Claim 14 (depends on 1) The solid composite of claim 1, wherein said epoxy resin is trifunctional or a higher functional epoxy resin. ### Claim 15 (depends on 1) The solid composite of claim 1, wherein said partially cured sizing agent is a flexible gel. ### Claim 16 A solid composite in which carbon fibers are embedded in a polymeric matrix derived from an unsaturated precursor resin containing carbon-carbon double bonds, wherein said carbon fibers have covalently bonded on their surfaces a partially cured amine-containing sizing agent, wherein said amine-containing sizing agent is covalently attached to a linking group that contains an accessible unsaturated group capable of reacting with said carbon-carbon double bonds via a vinyl addition reaction, and at least a portion of amine groups in the sizing agent are available as uncrosslinked amine groups, which corresponds to a curing degree of amine groups of no more than about 0.6. ### Claim 17 (depends on 16) The solid composite of claim 16, wherein said polymeric matrix is a thermoset. ### Claim 18 (depends on 17) The solid composite of claim 17, wherein said thermoset is an acrylate resin, vinyl ester resin, or polyester resin that covalently bonds with amine groups of the amine-containing sizing agent. ### Claim 19 (depends on 18) The solid composite of claim 18, wherein said resin is an acrylate, a vinyl sulfone, a vinyl ester, a polyester, or an unsaturated resin containing an acrylate monomer or a vinyl ester monomer in admixture with at least one unsaturated reactive diluent. ### Claim 20 (depends on 19) The solid composite of claim 19, wherein said unsaturated reactive diluent is selected from the group consisting of styrene, divinyl benzenes, methacrylates, and vinyl esters. ### Claim 21 (depends on 16) The solid composite of claim 16, wherein said polymeric matrix is a thermoplastic derived from a monomer containing a functionality that covalently bonds with the uncrosslinked amine groups of the sizing agent. ### Claim 22 (depends on 21) The solid composite of claim 21, wherein said functionality is selected from an ester, a carboxylic acid, a urethane, an aldehyde, and a ketone.