# US 11,441,051 B2 · 3D hybrid composite coating > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 11,441,051 B2 - Document ID: US11441051B2 - Status: Granted - Kind: B2 - Application number: 16/964,685 - Filed: 2019-01-25 - Published: 2020-11-05 - Granted: 2022-09-13 - Earliest claimed: 2018-01-26 - Assignees: UWM Research Foundation, Inc. - Applicants: UWM Research Foundation, Inc. - Inventors: Junjie Niu; Yongsuk Kim - Web page: https://patentgrep.com/patent/US11441051B2 ## CPC - C09D 163/00: Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins - C09D 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 C09D159/00 - C09D187/00 - C09D 7/62: modified by treatment with other compounds - C09D 127/22: modified by chemical after-treatment - B05D 1/02: performed by spraying - B05D 1/18: performed by dipping - B05D 1/28: performed by transfer from the surfaces of elements carrying the liquid or other fluent material, e.g. brushes, pads, rollers - B05D 2504/00: Epoxy polymers - B05D 2506/10: Fluorinated polymers - C08K 3/36: Silica - C08K 5/101: of monocarboxylic acids - C08K 9/04: Ingredients treated with organic substances {(treated with macromolecular compounds C08K9/08)} - 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) - B05D: PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL (conveying articles or workpieces through baths of liquid B65G, e.g. B65G49/02) - C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09) ## Abstract A coating composition comprises a functionalized epoxy resin and a fluoroalkyl-modified particle, such as activated carbon or silica. The functionalized epoxy resin is a ternary polymer composition comprising one or more epoxy resin moieties linked to a polyethylene backbone through an oxygen atom, fluoroalkyl(poly)propionyl groups being grafted to the polyethylene backbone. The coating compositions have superhydrophobic properties useful for self-cleaning surfaces and bubble release from sensors. ## Claims ### Claim 1 A coating composition comprising: (a) a ternary polymer composition comprising (i) a fluoropolymer comprising a polyethylene backbone optionally containing one or more double bonds, the polyethylene backbone being substituted with a plurality of fluoro groups and optionally a plurality of oxygen atoms; (ii) a plurality of fluoroalkyl(poly)propionyl groups grafted to the polyethylene backbone; and (iii) one or more epoxy resin moieties linked to the polyethylene backbone through an oxygen atom; and (b) a fluoroalkyl-modified particle. ### Claim 2 (depends on 1) The coating composition of claim 1, wherein the fluoropolymer is a dehydrofluorinated polyvinylidene fluoride polymer. ### Claim 3 (depends on 1) The coating composition of claim 1, wherein the ternary polymer comprises a plurality of units selected from the group consisting of wherein R1 is the epoxy resin moiety; each R2 is independently hydrogen or fluoro; and n is ≥0. ### Claim 4 (depends on 1) The coating composition of claim 1, wherein the fluoroalkyl(poly)propionyl group has a formula wherein n is ≥0. ### Claim 5 (depends on 1) The coating composition of claim 1, wherein the one or more epoxy resin moieties have a number average molecular weight of 350 to 1500. ### Claim 6 (depends on 1) The coating composition of claim 1, wherein the one or more epoxy resin moieties comprise bisphenol A. ### Claim 7 (depends on 1) The coating composition of claim 1, wherein at least one of the one or more epoxy resin moieties has formula (II) wherein R3a and R3b, at each occurrence, are independently hydrogen, C1-4alkyl, C1-4haloalkyl, C3-6cycloalkyl, or —C1-3alkylene-C3-6cycloalkyl, or independently R3a and R3b together with the carbon atom to which they attach form a C3-6cycloalkyl, wherein each C3-6cycloalkyl is optionally substituted with 1-4 substituents independently selected from the group consisting of halogen, C1-4alkyl, and C1-4haloalkyl; R4, at each occurrence, is independently halogen, cyano, C1-4alkyl, or C1-4haloalkyl. ### Claim 8 (depends on 7) The coating composition of claim 7, wherein at least one of the one or more epoxy resin moieties has formula (II-a) ### Claim 9 (depends on 7) The coating composition of claim 7, wherein at least one of the one or more epoxy resin moieties has formula (III) ### Claim 10 (depends on 1) The coating composition of claim 1, wherein the fluoroalkyl-modified particle is a fluoroalkyl-modified activated carbon. ### Claim 11 (depends on 1) The coating composition of claim 1, wherein the fluoroalkyl-modified particle is a fluoroalkyl-modified silica. ### Claim 12 (depends on 1) The coating composition of claim 1, wherein the fluoropolymer consists essentially of the polyethylene backbone optionally containing one or more double bonds, the polyethylene backbone being substituted with the plurality of fluoro groups and optionally the plurality of oxygen atoms. ### Claim 13 (depends on 1) The coating composition of claim 1, wherein the fluoropolymer consists of the polyethylene backbone optionally containing one or more double bonds, the polyethylene backbone being substituted with the plurality of fluoro groups and optionally the plurality of oxygen atoms. ### Claim 14 (depends on 1) A method of coating an article comprising contacting the article with the coating composition of claim 1. ### Claim 15 (depends on 14) The method of claim 14, wherein the article is contacted with the coating composition by immersion coating, spray coating, gravure coating, metering rod coating, knife over roll coating, slot orifice coating, or curtain coating. ### Claim 16 (depends on 1) An article coated with the coating composition of claim 1. ### Claim 17 (depends on 16) The article of claim 16, wherein the article is a sensor. ### Claim 18 (depends on 17) The article of claim 17, wherein the sensor is a temperature ultrasonic level and concentration sensor. ### Claim 19 A coating composition prepared by reacting a dehydrofluorinated polyvinylidene fluoride polymer with a fluoroalkylacrylate, a radical initiator, an epoxy resin, and a fluoroalkyl-modified particle. ### Claim 20 A method of preparing a coating composition comprising reacting a dehydrofluorinated polyvinylidene fluoride polymer with a fluoroalkylacrylate, a radical initiator, an epoxy resin, and a fluoroalkyl-modified particle.