Method for producing polyaniline complex composition and polyaniline complex composition

Patent metadata

Field	Value
Publication number	US-2017194068-A1
Application number	US-201515325286-A
Country	US
Kind code	A1
Filing date	Jul 9, 2015
Priority date	Jul 11, 2014
Publication date	Jul 6, 2017
Grant date	—

Abstract

A method for producing a polyaniline complex composition including: removing 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.

First claim

1 . A method for producing a polyaniline complex composition comprising:
removing a solvent from an organic solution that comprises (a) polyaniline doped with a compound represented by the following formula (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:
M(XAR n ) m   (I)

wherein M is a hydrogen atom, an organic free radical or an inorganic free radical, and m is a value of [valence of M/valence of X]; X is an anion group; A is a hydrocarbon group that may comprise a substituent; R is a group represented by —H, —R 1 , —OR 1 , —COR 1 , —COOR 1 , —(C═O)—(COR 1 ) or —(C═O)—(COOR 1 ), and at least one of R is a group represented by —COOR 1 or —(C═O)—(COOR 1 );
wherein R 1 is a hydrocarbon group that may comprise a substituent, a silyl group, an alkylsilyl group, a group represented by —(R 2 O)x-R 3 or a group represented by —(OSiR 3 2 )x-OR 3 (R 2 is independently an alkylene group, R 3 is independently a hydrocarbon group, and x is an integer of 1 or more); and
n is an integer of 1 or more.

2 . A method for producing a polyaniline complex composition comprising:
removing a solvent from an organic solution that comprises (a) polyaniline doped with a compound represented by the following formula (I), (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:
M(XAR n ) m   (I)

wherein M is a hydrogen atom, an organic free radical or an inorganic free radical, and m is a value of [valence of M/valence of X]; X is an anion group; A is a hydrocarbon group that may comprise a substituent; R is a group represented by —H, —R 1 , —OR 1 , —COR 1 , —COOR 1 , —(C═O)—(COR 1 ) or —(C═O)—(COOR 1 ), and at least one of R is a group represented by —COOR 1 or —(C═O)—(COOR 1 );
wherein R 1 is a hydrocarbon group that may comprise a substituent; a silyl group; an alkylsilyl group; a group represented by —(R 2 O)x-R 3 or a group represented by —(OSiR 3 2 )x-OR 3 (R 2 is independently an alkylene group, R 3 is independently a hydrocarbon group, and x is an integer of 1 or more); and
n is an integer of 1 or more.

3 . The method for producing a polyaniline complex composition according to claim 2 , wherein the acidic substance is an organic acid.

4 . The method for producing a polyaniline complex composition according to claim 2 , 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.

5 . The method for producing a polyaniline complex composition according to claim 2 , wherein the acidic substance is a cyclic, chain-like or branched alkyl acid comprising one or more acidic groups.

6 . The method for producing a polyaniline complex composition according to claim 2 , wherein the acidic substance is a substituted or unsubstituted aromatic acid having one or more acidic groups.

7 . The method for producing a polyaniline complex composition according to claim 6 , wherein the aromatic acid is an acid comprising a naphthalene skeleton.

8 . The method for producing a polyaniline complex composition according to claim 1 , wherein aniline doped with the compound represented by the formula (I) is polymerized at a temperature of 0° C. or lower, thereby to obtain the polyaniline.

9 . The method for producing a polyaniline complex composition according to claim 1 , wherein the compound represented by the formula (I) is diisooctylsulfosuccinate.

10 . The method for producing a polyaniline complex composition according to claim 1 , wherein the phenolic compound is alkoxy phenol, alkyl phenol or alkyl naphthol.

11 . The method for producing a polyaniline complex composition according to claim 1 , wherein the phenolic compound is amyl phenol, methoxy phenol or isopropyl phenol.

12 . 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.

13 . 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.

14 . 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), l 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.

15 . 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.

16 . A polyaniline complex composition that is produced by the method according to claim 1 .

17 . A polyaniline complex conductive film comprising the polyaniline complex composition according to claim 16 .

18 . A capacitor that comprises the polyaniline complex conductive film according to claim 17 .

19 . A conductive stacked body comprising:
a substrate; and the polyaniline complex conductive film according to claim 17 that is stacked on the substrate.

20 . A conductive article obtained by forming the conductive stacked body according to claim 19 .

21 . The method for producing a polyaniline complex composition according to claim 2 , wherein aniline doped with the compound represented by the formula (I) is polymerized at a temperature of 0° C. or lower, thereby to obtain the polyaniline.

22 . The method for producing a polyaniline complex composition according to claim 2 , wherein the compound represented by the formula (I) is diisooctylsulfosuccinate.

23 . The method for producing a polyaniline complex composition according to claim 2 , wherein the phenolic compound is alkoxy phenol, alkyl phenol or alkyl naphthol.

24 . The method for producing a polyaniline complex composition according to claim 2 , wherein the phenolic compound is amyl phenol, methoxy phenol or isopropyl phenol.

25 . The method for producing a polyaniline complex composition according to claim 2 , wherein the phenolic compound is p-tert-amylphenol, 4-methoxy phenol or 4-isopropyl phenol.

26 . The method for producing a polyaniline complex composition according to claim 2 , wherein the sulfonic acid or the sulfonate is aromatic sulfonic acid or aromatic sulfonate.

27 . The method for producing a polyaniline complex composition according to claim 2 , wherein the sulfonic acid or the sulfonate is a compound represented by the following formula (4) or

Assignees

• Idemitsu Kosan Co

Inventors

• Onodera Shingo

Classifications

• C08K5/375

  containing six-membered aromatic rings {(C08K5/3725 takes precedence)} · CPC title

• C08J7/14 Primary

  with acids, their salts or anhydrides · CPC title

• C08G73/0266

  Polyanilines or derivatives thereof · CPC title

• C08K5/42

  Sulfonic acids; Derivatives thereof · CPC title

• C08L79/02

  Polyamines · CPC title