# US 2016/0086685 A1 · Impregnation of a non-conductive material with an intrinsically conductive polymer through in-situ polymerization

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- Number: US 2016/0086685 A1
- Document ID: US20160086685A1
- Status: Published application
- Kind: A1
- Application number: 14/891,967
- Filed: 2014-05-19
- Published: 2016-03-24
- Earliest claimed: 2013-05-17
- Assignees: Biotectix, LLC
- Applicants: Biotectix, LLC
- Inventors: Kyle Mallires; Jeffrey L. Hendricks; Sarah Richardson-Burns; Omar Amirana
- Web page: https://patentgrep.com/patent/US20160086685A1

## CPC

- H01B 1/127: {comprising five-membered aromatic rings in the main chain, e.g. polypyrroles, polythiophenes}
- A61L 27/48: with macromolecular fillers
- A61L 27/50: Materials characterised by their function or physical properties {, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials}
- B05D 1/185: {applying monomolecular layers (B05D1/204 takes precedence)}
- B05D 3/108: {Curing}
- C09D 5/24: Electrically-conducting paints {(conductive materials H01B1/00)}
- C09D 175/04: Polyurethanes
- C09D 181/02: Polythioethers; Polythioether-ethers
- C25B 3/00: Electrolytic production of organic compounds
- C25D 9/02: with organic materials
- H01B 1/24: the conductive material comprising carbon-silicon compounds, carbon or silicon
- H01B 13/30: Drying; Impregnating (H01B13/32 takes precedence)
- C08G 2261/1424: containing ether groups, including alkoxy
- C08G 2261/18: conjugated
- C08G 2261/3223: containing one or more sulfur atoms as the only heteroatom, e.g. thiophene
- C08G 2261/43: Chemical oxidative coupling reactions, e.g. with FeCl3
- C08G 2261/44: Electrochemical polymerisation, i.e. oxidative or reductive coupling
- C08G 2261/51: Charge transport
- C08G 2261/792: with low-molecular weight dopants
- C08L 65/00: Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain (C08L7/00 - C08L57/00, C08L61/00 take precedence); Compositions of derivatives of such polymers
- H01B: CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES (selection for magnetic properties H01F1/00; waveguides H01P {; printed circuits H05K})
- 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)
- B05D: PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL (conveying articles or workpieces through baths of liquid B65G, e.g. B65G49/02)
- 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)
- C25B: ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR (anodic or cathodic protection C23F13/00; single-crystal growth C30B)
- C25D: PROCESSES FOR THE ELECTROLYTIC OR ELECTROPHORETIC PRODUCTION OF COATINGS; ELECTROFORMING; APPARATUS THEREFOR
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)

## Abstract

Composite materials are made by impregnating a non-conductive material with a conducting monomer to form a monomer-impregnated non-conductive material, and polymerizing the monomer-impregnated non-conductive material to form the composite material. The composite materials are used in medical devices and implants.

## Claims

### Claim 1

A method of making a composite material, the method comprising: impregnating a non-conductive material with a conducting monomer to form a monomer-impregnated non-conductive material; and polymerizing the monomer-impregnated non-conductive material to form the composite material.

### Claim 2

A method of making a composite material, the method comprising the steps of:
mixing a non-conductive polymer and a conducting monomer to form a non-conductive polymer blend;
enclosing a substrate in the non-conductive polymer blend or coating a surface of the substrate with the non-conductive polymer blend;
drying the non-conductive polymer blend to form a monomer-containing composite; and
polymerizing the monomer-containing composite to form the composite material.

### Claim 3 (depends on 1)

The method of claim 1, wherein the polymerizing step comprises oxidizing the monomer-impregnated non-conductive material or the monomer-containing composite with an oxidizer to form the composite material.

### Claim 4 (depends on 3)

The method of claim 3, wherein the oxidizing step comprises soaking the monomer-impregnated non-conductive material or the monomer-containing composite in an oxidation medium comprising the oxidizer and an optional solvent such that the conducting monomer and the oxidizer react to form the composite material.

### Claim at position 5

5-6. (canceled)

### Claim 7 (depends on 1)

The method of claim 1, wherein the polymerizing step comprises electrochemically polymerizing the monomer within the monomer-impregnated non-conductive material or the monomer-containing composite by placing the monomer-impregnated non-conductive material or the monomer-containing composite in a deposition medium containing counter-ions and a solvent and applying a current.

### Claim at position 7

8-12. (canceled)

### Claim 13 (depends on 1)

The method of claim 1, wherein the impregnating step comprises delivering a gas containing the conducting monomer or a liquid containing the conducting monomer into a sealed chamber containing the non-conductive material to form the monomer-impregnated non-conductive material.

### Claim 14 (depends on 13)

The method of claim 13, wherein the chamber is at a pressure below atmospheric pressure to increase the porosity of the non-conductive material.

### Claim at position 10

15-16. (canceled)

### Claim 17 (depends on 1)

The method of claim 1, wherein the polymerizing step comprises delivering a gas containing the oxidizer or a liquid containing the oxidizer into a sealed chamber containing the monomer-impregnated non-conductive material or the monomer-containing composite to form the composite material.

### Claim 18 (depends on 17)

The method of claim 17, wherein the chamber is at a pressure below atmospheric pressure to increase the porosity of the monomer-impregnated non-conductive material.

### Claim at position 13

19-21. (canceled)

### Claim 22 (depends on 1)

The method of claim 1, wherein the non-conductive material is dissolved or melted before the impregnating step, and the method further comprises the step of coating the non-conductive material onto a scaffold or substrate or molding the non-conductive material around the scaffold or substrate to enclose the scaffold or substrate within the non-conductive material.

### Claim at position 15

23-24. (canceled)

### Claim 25 (depends on 1)

The method of claim 1, wherein the non-conductive material is impregnated and the monomer-impregnated non-conductive material is polymerized in a single step reaction.

### Claim 26 (depends on 25)

The method of claim 25 wherein an oxidation medium contains the conducting monomer, a solvent, and an oxidizer such that the conducting monomer and the oxidizer react and the conducting monomer is polymerized to form the composite material.

### Claim at position 18

27-34. (canceled)

### Claim 35 (depends on 1)

The method of claim 1, wherein the non-conductive material or substrate comprises a tube, scaffold, rod, fiber, mesh, ring, patch, sheet, sponge, gel, foam, bag, balloon, particle, powder, pellet, hook and loop fastener, film, needle, braid, weaved material, knitted material, extruded material, or injection-molded material.

### Claim 36

(canceled)

### Claim 37 (depends on 1)

The method of claim 1, wherein the method further comprises electrochemically depositing a conductive polymer on a surface of the composite material.

### Claim at position 22

38-41. (canceled)

### Claim 42 (depends on 1)

The method of claim 1, wherein the conducting monomer comprises acetylene, fluorene, para-phenylene, pyrene, pyrrole, carbazole, indole, phenyl azide, aniline, thiophene, pyridine, or a mixture or functionalized derivative thereof; the conducting monomer comprises 3,4-ethylenedioxythiophene (EDOT) or a functionalized derivative thereof; the conducting monomer comprises 3,4-ethylenedioxythiophene, hydroxymethyl-EDOT, EDOT-vinyl, EDOT-ether allyl, EDOT-COOH, EDOT-MeOH, EDOT-silane, EDOT-vinyl, EDOT-acrylate, EDOT-silane, EDOT-sulfonate, EDOT-amine, EDOT-amide, EDOT-thiol, ProDOT (3,4-Propylenedioxythiophene), 3,4-(2,2-Dimethylpropylenedioxy)thiophene, 3,4-(2′,2′-Diethylpropylene)dioxythiophene, or a dimerized or trimerized derivative of EDOT; or the conducting monomer comprises hydroxymethyl-EDOT, EDOT-vinyl, EDOT-ether allyl, or EDOT-acrylate.

### Claim at position 24

43-45. (canceled)

### Claim 46 (depends on 1)

The method of claim 1, wherein the non-conductive material or the non-conductive polymer blend comprises a plastic; a synthetic material comprising polyethylene terephthalate (PET), high-density polyethylene (HDPE), low-density polyethylene (LDPE), ultra-high-molecular-weight polyethylene (UHMWPE), polycarbonate, polystyrene, poly(methyl methacrylate) (PMMA), poly(2-hydroxyethyl methacrylate) (PHEMA), polyacrylamide, polyacrylic acid, thermoset, polyurethane, thermoplastic polyurethane, polyurethane foam, polytetrafluoroethylene (PTFE), ePTFE (GORE-TEX), polydimethylsiloxane (PDMS), poly(lactic-co-glycolic acid) (PLGA), poly-L-lactide (PLLA), polyglycolic acid (PGA), polyether ether ketone (PEEK), isoprene, polyvinyl chloride (PVC), polyether block amide (PEBAX), silicone, polyaldehyde, polypropylene, polybutadiene, styrene-isoprene-butadiene-styrene (SIBS), block copolymers, sulfonated block copolymers, sulfonated perfluoronated polymers, polymer electrolyte membranes (PEM), nitrile butadiene rubber (NBR), synthetic rubber, nylon, polyester, polyamide, polyimide, polyurea, or a functionalized derivative thereof; a natural material comprising fibrin, collagen, cellulose, chitin/chitosan, alginate, carrageenan, silk, wool, lignin, gelatin, cotton, keratin, natural rubber, or a poly(amino acid); or a degradable material comprising polycaprolactone, polyglycolic acid, poly(lactic-co-glycolic acid) (PLGA), polyactic acid, a polyanhydride, poly(β-hydroxybutyrate), a poly(ortho-ester), or a polyiminocarbonate.

### Claim at position 26

47-51. (canceled)

### Claim 52 (depends on 3)

The method of claim 3, wherein the oxidizer comprises benzoyl peroxide, hydrogen peroxide, iron(III) para-toluenesulfonate, iron(III) chloride, gold (III) chloride, iodine or bromine; the solvent comprises dichloromethane, acetonitrile, dimethylsulfoxide, N,N-dimethylformamide, chloroform, tetrahydrofuran, isopropanol, methanol, ethanol, n-butanol, acetone, methyl ethyl ketone, benzonitrile, toluene, propylene carbonate, or water.

### Claim at position 28

53-54. (canceled)

### Claim 55 (depends on 3)

The method claim 3, wherein the solvent further comprises a counterfoil comprising a negatively charge 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 56

(canceled)

### Claim 57 (depends on 55)

The method of claim 55, wherein the 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, a polyacrylate, a polyamino acid, polydopamine, sulfonated poly ether ether ketone (S-PEEK), a sulfonated polyurethane, vinyl sulfonate, styrene sulfonate, allyl sulfonate, ethyl acrylate sulfonate, butyl acrylate sulfonate, acryl sulfonate, methacryl sulfonate, 2-acrylamide-2-methylpropane sulfonate, isoprene sulfonate, vinyl carboxylate, styrene carboxylate, allyl carboxylate, acryl carboxylate, methacryl carboxylate, 2-acrylamide-2-methylpropane carboxylate, isoprene carboxylate, an acrylate, an amino acid, dopamine, sulfonated ether ether ketone (S-PEEK), a sulfonated urethane, or a mixture thereof; or the counterion comprises sulfonic acid, fluorosulfonate, toluene sulfonate, taurine, anthraquinone sulfonate, vinyl sulfonate, 2-acrylamido-2-methyl-1-propanesulfonic acid, polystyrene sulfonate, polyvinyl sulfonate, sulfonated polytetrafluoroethylene, polyanetholesuflonic acid, a salt or functionalized derivitive thereof, or a mixture thereof; the counterion comprises para-toluenesulfonate (tosylate), trifluoromethanesulfonate (triflate), naphthalene sulfonate, camphor sulfonate, benzene sulfonate, perchlorate, tetrafluoroborate, hexafluorophosphate, dodecylbenzene sulfonic acid, fluoride, chloride, bromide, or iodide or a salt or mixture thereof; or the counterion is a salt comprising a lithium (Li+), sodium (NA+), potassium (K+), hydrogen (H+), hydronium, ammonium, tetraethylammonium, tetrapropylammonium, or tetrabutylammonium cation.

### Claim at position 32

58-60. (canceled)

### Claim 61 (depends on 1)

The method of claim 1, wherein the non-conductive material is impregnated with the conducting monomer and a crosslinking agent to form the monomer-impregnated non-conductive material; or the monomer-impregnated non-conductive material or the monomer-containing composite is in the presence of a crosslinking agent during polymerization.

### Claim 62

(canceled)

### Claim 63 (depends on 61)

The method of claim 61, wherein the crosslinking agent comprises a monomer functionalized with a silane, an acrylate, a methacrylate, epoxide, glycidyl ether, vinyl, allyl, azide, a derivative thereof, or a combination thereof.

### Claim 64 (depends on 3)

The method of claim 3, wherein the infusion medium, the oxidation medium or the polymerization medium further comprises a surfactant.

### Claim at position 37

65-70. (canceled)

### Claim 71 (depends on 1)

A composite material comprising a non-conductive material impregnated with a conducting polymer, the composite material being prepared by the method of claim 1.

### Claim at position 39

72-99. (canceled)