# US 2016/0177109 A1 · Conductive polymer coatings for three dimensional substrates > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2016/0177109 A1 - Document ID: US20160177109A1 - Status: Published application - Kind: A1 - Application number: 14/944,735 - Filed: 2015-11-18 - Published: 2016-06-23 - Earliest claimed: 2014-11-19 - Assignees: Biotectix, LLC - Applicants: Biotectix, LLC - Inventors: Jeffrey Hendricks; Kyle Mallires; Sarah Richardson-Burns - Web page: https://patentgrep.com/patent/US20160177109A1 ## CPC - C09D 5/24: Electrically-conducting paints {(conductive materials H01B1/00)} - A61L 29/085: {Macromolecular materials} - A61L 29/14: Materials characterised by their function or physical properties {, e.g. lubricating compositions} - A61N 1/04: Electrodes {(electrosurgical electrodes A61B18/14)} - C04B 41/4849: {Sulfur-containing polymers} - C04B 41/83: Macromolecular compounds - C08J 7/042: {with two or more layers, where at least one layer of a composition contains a polymer binder} - C08J 7/0427: {with only one layer of a composition containing a polymer binder (with more layers C08J7/042)} - C08J 7/043: Improving the adhesiveness of the coatings per se, e.g. forming primers (adhesives in the form of films or foils characterised by the primer layers between the polymer carriers and the adhesives C09J7/50) - C08J 7/044: Forming conductive coatings; Forming coatings having anti-static properties - C08J 7/046: Forming abrasion-resistant coatings; Forming surface-hardening coatings - C08J 7/056: Forming hydrophilic coatings - C08L 101/12: characterised by physical features, e.g. anisotropy, viscosity or electrical conductivity (liquid crystal materials or compositions C09K19/00) - C09D 145/00: Coating compositions based on homopolymers or copolymers of compounds having no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic or in a heterocyclic system; Coating compositions based on derivatives of such polymers (based on polymers of cyclic esters of polyfunctional acids C09D131/00; based on polymers of cyclic anhydrides or imides C09D135/00) - C09D 165/00: Coating compositions based on macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain (C09D107/00 - C09D157/00, C09D161/00 take precedence); Coating compositions based on derivatives of such polymers - C09D 201/00: Coating compositions based on unspecified macromolecular compounds - D06M 15/3566: {containing sulfur} - H01M 4/00: Electrodes - H01M 4/366: {as layered products} - H01M 4/608: {containing heterocyclic rings} - A61L 2420/02: Methods for coating medical devices - A61L 2420/06: Coatings containing a mixture of two or more compounds - C08G 2261/1424: containing ether groups, including alkoxy - C08G 2261/3223: containing one or more sulfur atoms as the only heteroatom, e.g. thiophene - C08G 2261/512: Hole transport - C08G 2261/794: with polymeric dopants - C08J 2375/04: Polyurethanes - C08J 2400/12: Polymers characterised by physical features, e.g. anisotropy, viscosity or electrical conductivity - C08J 2465/00: Characterised by the use of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain (C08J2407/00 - C08J2457/00, C08J2461/00 take precedence); Derivatives of such polymers - D06M 2101/40: Fibres of carbon - Y02E 60/10: Energy storage using batteries - 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) - A61L: METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES (preservation of bodies or disinfecting characterised by the agents employed A01N; preserving, e.g. sterilising, food or foodstuffs A23; preparations for medical, dental or toiletry purposes A61K) - A61N: ELECTROTHERAPY; MAGNETOTHERAPY; RADIATION THERAPY; ULTRASOUND THERAPY (measurement of bioelectric currents A61B; surgical instruments, devices or methods for transferring non-mechanical forms of energy to or from the body A61B18/00; anaesthetic apparatus in general A61M; incandescent lamps H01K; infrared radiators for heating H05B) - C04B: LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE {(roofing granules E04D7/005)}; CERAMICS (devitrified glass-ceramics C03C10/00); REFRACTORIES; TREATMENT OF NATURAL STONE - 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) - D06M: TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS - H01M: PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION ## Abstract The present invention generally relates to compositions and methods for the preparation of conductive polymer coatings, and methods for application of the coatings to three-dimensional substrates. ## Claims ### Claim at position 1 1-111: (canceled) ### Claim 112 An electrically conductive polymeric coating derived from a coating precursor composition comprising: a conductive polymer component comprising poly(3,4-ethylenedioxythiophene) and a primary counterion comprising one or more repeat units having a negatively charged functional group; a secondary doping agent; a crosslinking agent; a surfactant component; and a flexibility enhancer comprising polyacrylic acid, poly(acrylamide-co-acrylic acid), polyvinylpyrrolidone, polyvinyl alcohol, poloxypropylene-polyoxyethylene polaxamer, poly(2-acrylamido-2-methyl-1-propanesulfonic acid), sulfonated polytetrafluoroethylene, polystyrene sulfonic acid, polystyrene sulfonate, poly(acrylic acid-co-maleic acid), poly(2-hydroxyethyl methacrylate), polyanetholesulfonic acid sodium salt, polyvinyl sulfonic acid sodium salt, poly(1-vinylpyrrolidone-co-vinyl acetate), polystyrene-block-poly(ethylene-r-butylene)-block-polystyrene sulfonate, polyethylene glycol, polyethylene oxide, or a combination thereof. ### Claim 113 An electrically conductive polymeric coating derived from a coating precursor composition comprising: a conductive polymer component comprising poly(3,4-ethylenedioxythiophene) and a primary counterion comprising one or more repeat units having a negatively charged functional group; a secondary doping agent; a crosslinking agent; a surfactant component; and a flexibility enhancer comprising a hydrophilic polymer, wherein the electrical resistance of the coating increases by no greater than 50% after 600 flexing cycles when the coating is applied to a substrate having an outer diameter of 0.25 inches and each cycle comprises flexing the coated substrate about a bend radius of 1.25 inches. ### Claim 114 An electrically conductive polymeric coating derived from a coating precursor composition comprising: a conductive polymer component comprising poly(3,4-ethylenedioxythiophene) and a primary counterion comprising one or more repeat units having a negatively charged functional group; a secondary doping agent; a crosslinking agent; a surfactant component; and a conductive filler comprising metal particles, carbon black, carbon fiber, graphite, graphene, carbon nanotubes, carbon fiber silicon, silicon particles, or a combination thereof, wherein the conductive filler is present in the electrically conductive polymeric coating in an amount sufficient to reduce the contact resistance of the polymeric coating, and wherein the conductive filler is present in the coating precursor composition in a concentration of no more than about 25% of the composition on a weight per volume basis. ### Claim 115 (depends on 112) The coating of claim 112 wherein the primary counterion comprises a negatively charged functional group comprising a phosphate group, a phosphonate group, a sulfamate group, a carboxylate group, a sulfate group, a sulfonate group, or a combination thereof. ### Claim 116 (depends on 112) The coating of claim 112 wherein the primary counterion comprises polyvinyl sulfonate, polystyrene sulfonate, polyallyl sulfonate, polyethyl acrylate sulfonate, polybutyl acrylate sulfonate, polyacryl sulfonate, polymethacryl sulfonate, poly-2-acrylamide-2-methylpropane sulfonate, polyisoprene sulfonate, polyvinyl carboxylate, polystyrene carboxylate, polyallyl carboxylate, polyacryl carboxylate, polymethacryl carboxylate, poly-2-acrylamide-2-methylpropane carboxylate, polyisoprene carboxylate, polyacrylates, polyglutamates, polydopamines, sulfonated poly ether ether ketones (S-PEEK), sulfonated polyurethanes, or a combination thereof. ### Claim 117 (depends on 116) The coating of claim 116 wherein the primary counterion comprises polystyrene sulfonate. ### Claim 118 (depends on 112) The coating of claim 112 wherein the coating precursor composition comprises PEDOT:PSS in the form of aqueous dispersion. ### Claim 119 (depends on 112) The coating of claim 112 wherein the coating precursor composition comprises an organic solvent. ### Claim 120 (depends on 112) The coating of claim 112 wherein the secondary doping agent comprises a low volatility polar solvent selected from the group consisting of ethylene glycol, sorbitol, glycerol, dimethylsulfoxide, N,N-dimethylformamide, erythritol, 2-nitroethanol, methoxyphenol, N,N-dimethylacetamide, N-methylpyrrolidone, succinimide, propylene glycol, and combinations thereof. ### Claim 121 (depends on 112) The coating of claim 112 wherein the surfactant component comprises one or more anionic surfactants selected from the group consisting of alkylbenzenesulfonic acids and salts thereof, organosulfates, carboxylates, and natural fatty acids and salts thereof. ### Claim 122 (depends on 121) The coating of claim 121 wherein the surfactant component comprises dodecylbenzenesulfonic acid or sodium dodecyl sulfate. ### Claim 123 (depends on 112) The coating of claim 112 wherein the coating precursor composition comprises a crosslinking agent comprised of 3-glycidyloxypropyl trimethoxysilane, 3-(trimethoxysilyl)propyl methacrylate, 3-(trimethoxysilyl)propyl acrylate, vinyltrimethoxysilane, allyltrimethoxysilane, tetrakis(trimethylsilyloxy)silane, poly(ethylene glycol) diglycidyl ether, poly(ethylene glycol) diacrylate, poly(ethylene glycol) dimethacrylate, poly(ethylene glycol) divinyl ether, branched trialkyloxy silanes, branched epoxides, or branched acrylates or methacrylates. ### Claim 124 (depends on 112) The coating of claim 112 wherein the coating precursor composition comprises a conductive filler comprised of metal particles, carbon black, carbon fiber, graphite, graphene, carbon nanotubes, carbon fiber silicon, silicon particles, or a combination thereof, wherein the conductive filler is present in the electrically conductive polymeric coating in an amount sufficient to reduce the contact resistance of the polymeric coating, and wherein the conductive filler is present in the coating precursor composition in a concentration of no more than about 25% of the composition on a weight per volume basis. ### Claim 125 (depends on 124) The coating of claim 124 wherein the conductive filler comprises carbon fiber, carbon nanotubes, stainless steel flakes, nickel flakes, stainless steel nanopowder, graphite, graphene, noble metal spheres, or a combination thereof. ### Claim 126 (depends on 112) The coating of claim 112 wherein the coating precursor composition comprises a monomer additive comprising one or more methacrylate, acrylate, acrylamide, or vinyl based monomers. ### Claim 127 (depends on 112) The coating of claim 112 wherein the coating precursor composition comprises a stabilizer selected from the group consisting of 2,2,6,6-tetramethyl piperidine and its derivatives, benzophenones, benzofuranones, oxanilides, p-phenylenediamines, N-(1,3-dimethylbutyl)-N′-phenyl-p-phenylenediamine, N-isopropyl-N′-phenyl-p-phenylenediamine, 6-ethoxy-2,2,4-trimethyl-1,2-dihydroquinoline, ethylene diurea, hindered phenols, aromatic amines, benzotriazoles, hydroxyphenyltriazines, and combinations thereof. ### Claim 128 (depends on 112) The coating of claim 112 wherein the coating precursor composition comprises a swelling agent, and wherein the swelling agent comprises a polar solvent. ### Claim 129 (depends on 112) A method of coating a substrate with an electrically conductive coating, the method comprising: preparing a coating precursor composition as set forth in claim 112; applying the coating precursor composition to a three-dimensional substrate using a dip coating process; and thermally curing the applied coating composition to form a coated substrate. ### Claim 130 (depends on 112) A cylindrical tube electrode comprising: a cylindrical tube comprising an inner lumen and an outer surface, and an electrically conductive polymeric coating adhered to the outer surface, wherein the electrically conductive polymeric coating comprises one or more conductive layers, and wherein one or more of said conductive layers comprises the electrically conductive polymeric coating of claim 112. ### Claim 131 (depends on 112) An electrically conductive foam composition comprising: a substrate comprising polyurethane foam, and an electrically conductive polymeric coating adhered to the surface of the substrate, wherein the electrically conductive polymeric coating comprises one or more conductive layers, and wherein one or more of said conductive layers comprises the electrically conductive polymeric coating of claim 112.