# US 10,483,011 B2 · Conductive composition, conductive composition production method, anti-static resin composition and antistatic resin film

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- Number: US 10,483,011 B2
- Document ID: US10483011B2
- Status: Granted
- Kind: B2
- Application number: 14/823,652
- Filed: 2015-08-11
- Published: 2015-12-03
- Granted: 2019-11-19
- Earliest claimed: 2013-02-15
- Assignees: Shin-Etsu Polymer Co., Ltd.
- Applicants: Shin-Etsu Polymer Co., Ltd.; Nissin Chemical Industry Co., Ltd.
- Inventors: Hironao Fujiki; Takanori Suzuki
- Web page: https://patentgrep.com/patent/US10483011B2

## CPC

- H01B 1/127: {comprising five-membered aromatic rings in the main chain, e.g. polypyrroles, polythiophenes}
- 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
- C08L 25/18: Homopolymers or copolymers of aromatic monomers containing elements other than carbon and hydrogen
- C09D 5/022: {Emulsions, e.g. oil in water}
- C09D 5/24: Electrically-conducting paints {(conductive materials H01B1/00)}
- C09D 7/40: Additives
- C09D 7/65: macromolecular (C09D7/41-C09D7/48 take precedence)
- C09D 201/00: Coating compositions based on unspecified macromolecular compounds
- H01B 1/122: {Ionic conductors}
- H01B 1/124: {Intrinsically conductive polymers}
- C08G 73/0266: {Polyanilines or derivatives thereof}
- 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 2261/51: Charge transport
- C08G 2261/794: with polymeric dopants
- C08K 5/15: Heterocyclic compounds having oxygen in the ring
- C08K 5/151: having one oxygen atom in the ring
- 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
- C08L 79/02: Polyamines
- 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
- 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})
- 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)
- 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)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)

## Abstract

A transparent conductive film with fewer problems originating from amine compounds is provided using a conductive composition stably and pseudo-solubly dispersed in a solvent consisting mainly of an organic solvent. This invention relates to: a conductive composition which is pseudo-solubly dispersed in a solvent consisting mainly of an organic solvent and which contains (a) a π-conjugated conductive polymer, (b) polyanions doping the π-conjugated conductive polymer (a), and (c) a reaction product of those anions of the polyanions (b) that were not needed for doping, and an oxirane group- and/or oxetane group-containing organic compound; a production method of said conductive composition; an anti-static resin composition formed by mixing said conductive composition and a resin solution dissolved in an organic solvent; and antistatic resin film formed by curing said antistatic resin composition.

## Claims

### Claim 1

A method for producing a conductive composition comprising:
(a) a π-conjugated conductive polymer,
(b) a polyanion with which the π-conjugated conductive polymer is doped, and
(c) a reaction product of an oxirane group and/or oxetane group-containing organic compound and an anion, the anion being non-doped with the π-conjugated conductive polymer (a) in anions in the polyanion with which the π-conjugated conductive polymer (a) is doped,
wherein the conductive composition is dispersed in a solvent containing a first organic solvent and water,
the method comprising:
adding the oxirane group and/or oxetane group-containing organic compound with a second organic solvent to a water dispersion of the π-conjugated conductive polymer and the polyanion with which the polymer is doped,
reacting the polyanion and the oxirane group and/or oxetane group-containing organic compound with the anion being non-doped with the π-conjugated conductive polymer,
collecting the conductive composition precipitated thereby,
adding the solvent containing the first organic solvent and water to the collected conductive composition,
separating the solvent including the collected conductive composition into an organic phase and an aqueous phase, and
extracting the aqueous phase.

### Claim 2 (depends on 1)

The method of claim 1, further comprising adding a resin that is soluble in the first organic solvent.

### Claim 3 (depends on 1)

The method of claim 1, wherein the π-conjugated conductive polymer has one or more repeating units selected from the group consisting of polypyrroles, polythiophenes, polyacetylenes, polyphenylenes, polyphenylenevinylenes, polyanilines, polyacenes, polythiophenevinylenes, and copolymers of two or more thereof.

### Claim 4 (depends on 3)

The method of claim 3, wherein the π-conjugated conductive polymer is poly(3,4-ethylenedioxythiophene) or polypyrrole.

### Claim 5 (depends on 1)

The method of claim 1, wherein the polyanion comprises one or a mixture of two or more selected from a sulfonic acid group, a phosphoric acid group and a carboxyl group.

### Claim 6 (depends on 1)

The method of claim 1, wherein the polyanion comprises polystyrenesulfonic acid, polyvinylsulfonic acid, polyacryloyloxy-alkylenesulfonic acid, poly(2-acrylamido-2-methyl-1-propanesulfonic acid), or one or more thereof as a copolymerization constituent.

### Claim 7 (depends on 1)

The method of claim 1, wherein the oxirane group and/or oxetane group-containing organic compound is added in the range of 1.0 to 30.0 in a weight ratio relative to the anion group in the polyanion of the π-conjugated conductive polymer with the second organic solvent to the water dispersion.