# US 10,872,709 B2 · Method for producing polyaniline complex composition and polyaniline complex composition > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,872,709 B2 - Document ID: US10872709B2 - Status: Granted - Kind: B2 - Application number: 15/325,286 - Filed: 2015-07-09 - Published: 2017-07-06 - Granted: 2020-12-22 - Earliest claimed: 2014-07-11 - Assignees: Idemitsu Kosan Co., Ltd. - Applicants: Idemitsu Kosan Co., Ltd. - Inventors: Shingo Onodera - Web page: https://patentgrep.com/patent/US10872709B2 ## CPC - H01B 1/12: organic substances {(organic macromolecular compounds or compositions C08)} - B32B 27/281: {comprising polyimides} - C08G 73/0266: {Polyanilines or derivatives thereof} - C08J 7/14: with acids, their salts or anhydrides - C08K 5/13: Phenols; Phenolates - C08K 5/375: containing six-membered aromatic rings {(C08K5/3725 takes precedence)} - C08K 5/42: Sulfonic acids; Derivatives thereof - C08L 79/02: Polyamines - H01B 1/124: {Intrinsically conductive polymers} - H01B 1/128: {comprising six-membered aromatic rings in the main chain, e.g. polyanilines, polyphenylenes} - B32B 2307/202: Conductive - 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}) - B32B: LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - 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) - C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09) - C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06) ## Abstract A method for producing a polyaniline complex composition including: removing a solvent from an organic solution that includes (a) polyaniline doped with a compound represented by M(XARn)m (I) and (b) a phenolic compound, thereby to obtain a composition; and immersing the composition in (c) a solution that comprises at least one of sulfonic acid and sulfonate, followed by drying. ## Claims ### Claim 1 A method for producing a polyaniline complex composition comprising: removing a solvent from an organic solution that comprises (a) polyaniline doped with sodium diisooctylsulfosuccinate and (b) a phenolic compound, thereby to obtain a composition; and immersing the composition in (c) a solution that comprises at least one of sulfonic acid and sulfonate, followed by drying. ### Claim 2 (depends on 1) The method for producing a polyaniline complex composition according to claim 1, wherein aniline doped with sodium diisooctylsulfosuccinate is polymerized at a temperature of 0° C. or lower, thereby to obtain the polyaniline. ### Claim 3 (depends on 1) The method for producing a polyaniline complex composition according to claim 1, wherein the phenolic compound is alkoxy phenol, alkyl phenol or alkyl naphthol. ### Claim 4 (depends on 1) The method for producing a polyaniline complex composition according to claim 1, wherein the phenolic compound is amyl phenol, methoxy phenol or isopropyl phenol. ### Claim 5 (depends on 1) The method for producing a polyaniline complex composition according to claim 1, wherein the phenolic compound is p-tert-amylphenol, 4-methoxy phenol or 4-isopropyl phenol. ### Claim 6 (depends on 1) The method for producing a polyaniline complex composition according to claim 1, wherein the sulfonic acid or the sulfonate is aromatic sulfonic acid or aromatic sulfonate. ### Claim 7 (depends on 1) The method for producing a polyaniline complex composition according to claim 1, wherein the sulfonic acid or the sulfonate is a compound represented by the following formula (4) or (5), or salt thereof; wherein in the formula (4), 1 is 1 or more, m is 0 or more and n is 0 or more, and if one of m and n is 0, the other is 1 or more; and wherein in the formula (5), q is 1 or more, p is 0 or more, R is independently an alkyl group including 1 to 20 carbon atoms, a carboxy group, a hydroxyl group, a nitro group, a cyano group or an amino group. ### Claim 8 (depends on 1) The method for producing a polyaniline complex composition according to claim 1, wherein the sulfonic acid or the sulfonate is naphthalene sulfonic acid, phenol sulfonic acid, sulfophthalic acid, sulfoisophthalic acid, sulfosalcylic acid or salt thereof. ### Claim 9 (depends on 1) A polyaniline complex composition that is produced by the method according to claim 1. ### Claim 10 (depends on 9) A polyaniline complex conductive film comprising the polyaniline complex composition according to claim 9. ### Claim 11 (depends on 10) A capacitor that comprises the polyaniline complex conductive film according to claim 10. ### Claim 12 (depends on 10) A conductive stacked body comprising: a substrate; and the polyaniline complex conductive film according to claim 10 that is stacked on the substrate. ### Claim 13 (depends on 12) A conductive article obtained by forming the conductive stacked body according to claim 12. ### Claim 14 A method for producing a polyaniline complex composition comprising: removing a solvent from an organic solution that comprises (a) polyaniline doped with sodium diisooctylsulfosuccinate (b) a phenolic compound, and an acidic substance or a salt of the acidic substance, thereby to obtain a composition; and immersing the composition in (c) a solution that comprises at least one of sulfonic acid and sulfonate, followed by drying. ### Claim 15 (depends on 14) The method for producing a polyaniline complex composition according to claim 14, wherein the acidic substance is an organic acid. ### Claim 16 (depends on 14) The method for producing a polyaniline complex composition according to claim 14, wherein the acidic substance is one or more acidic substances comprising one or more acidic groups selected from a sulfonic acid group, a phosphoric acid group, a phosphonic acid group and a carboxy group. ### Claim 17 (depends on 14) The method for producing a polyaniline complex composition according to claim 14, wherein the acidic substance is a cyclic, chain-like or branched alkyl acid comprising one or more acidic groups. ### Claim 18 (depends on 14) The method for producing a polyaniline complex composition according to claim 14, wherein the acidic substance is a substituted or unsubstituted aromatic acid having one or more acidic groups. ### Claim 19 (depends on 18) The method for producing a polyaniline complex composition according to claim 18, wherein the aromatic acid is an acid comprising a naphthalene skeleton. ### Claim 20 (depends on 14) The method for producing a polyaniline complex composition according to claim 14, wherein aniline doped with sodium diisooctylsulfosuccinate is polymerized at a temperature of 0° C. or lower, thereby to obtain the polyaniline. ### Claim 21 (depends on 14) The method for producing a polyaniline complex composition according to claim 14, wherein the phenolic compound is alkoxy phenol, alkyl phenol or alkyl naphthol. ### Claim 22 (depends on 14) The method for producing a polyaniline complex composition according to claim 14, wherein the phenolic compound is amyl phenol, methoxy phenol or isopropyl phenol. ### Claim 23 (depends on 14) The method for producing a polyaniline complex composition according to claim 14, wherein the phenolic compound is p-tert-amylphenol, 4-methoxy phenol or 4-isopropyl phenol. ### Claim 24 (depends on 14) The method for producing a polyaniline complex composition according to claim 14, wherein the sulfonic acid or the sulfonate is aromatic sulfonic acid or aromatic sulfonate. ### Claim 25 (depends on 14) The method for producing a polyaniline complex composition according to claim 14, wherein the sulfonic acid or the sulfonate is a compound represented by the following formula (4) or (5), or salt thereof; wherein in the formula (4), 1 is 1 or more, m is 0 or more and n is 0 or more, and if one of m and n is 0, the other is 1 or more; and wherein in the formula (5), q is 1 or more, p is 0 or more, R is independently an alkyl group including 1 to 20 carbon atoms, a carboxy group, a hydroxyl group, a nitro group, a cyano group or an amino group. ### Claim 26 (depends on 14) The method for producing a polyaniline complex composition according to claim 14, wherein the sulfonic acid or the sulfonate is naphthalene sulfonic acid, phenol sulfonic acid, sulfophthalic acid, sulfoisophthalic acid, sulfosalcylic acid or salt thereof. ### Claim 27 (depends on 14) A polyaniline complex composition that is produced by the method according to claim 14. ### Claim 28 (depends on 27) A polyaniline complex conductive film comprising the polyaniline complex composition according to claim 27. ### Claim 29 (depends on 28) A capacitor that comprises the polyaniline complex conductive film according to claim 28. ### Claim 30 (depends on 28) A conductive stacked body comprising: a substrate; and the polyaniline complex conductive film according to claim 28 that is stacked on the substrate. ### Claim 31 (depends on 30) A conductive article obtained by forming the conductive stacked body according to claim 30.