Conductive aniline polymer, method for producing same, and method for producing conductive film

Inactive Publication Date: 2013-08-15
MITSUBISHI RAYON CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Benefits of technology

The present invention is about a new type of conductive material called aniline polymer. This polymer has very high conductivity, meaning it can conduct electricity very well. The invention also provides a method for mass-producing this polymer. This allows for the creation of high-conductivity conductive films.

Problems solved by technology

However, a copolymer obtained by the method described in Patent Literature 1 has a low rate of sulfonation and a low solubility in water alone, and therefore causes a problem of poor workability.
In addition, the copolymer has a problem of low conductivity due to difficulty in purification and the presence of impurities.
As a result, a side reaction such as conversion of acidic group-substituted aniline as a starting material monomer to an azo compound is not sufficiently suppressed.
Therefore, a byproduct contained in the polymer prevents the improvement of conductivity.
However, impurities cannot be removed sufficiently during separation of polymer from a polymerization reaction solution by filtration.
Therefore, the resultant polymer cannot necessarily satisfy conductive performance as compared with the other conductive polymers.

Method used

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  • Conductive aniline polymer, method for producing same, and method for producing conductive film
  • Conductive aniline polymer, method for producing same, and method for producing conductive film
  • Conductive aniline polymer, method for producing same, and method for producing conductive film

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first embodiment

[0090]In this embodiment, a polymerization step (Z1) shown below is used as the polymerization step (Z).

[0091]The method for producing a conductive aniline polymer of the embodiment includes a polymerization step (Z1) of polymerizing an aniline derivative (A) in a solution containing a basic compound (B), a solvent (C), and an oxidizing agent (D) at a liquid temperature lower than 25° C.

[0092]Hereinafter, each component used in the polymerization step (Z1) will be specifically described.

Aniline Derivative (A)

[0093]An aniline derivative (A) used in the polymerization step (Z1) of the embodiment is a compound represented by the following formula (2). Specifically, the aniline derivative (A) is preferably a compound selected from the group consisting of an acidic group-substituted aniline, an alkali metal salt, an alkaline earth metal salt, an ammonium salt, and a substituted ammonium salt thereof.

[0094]In the formula (2), R5 to R9 are each independently —H, a linear or branched alkyl ...

second embodiment

[0221]In the embodiment, a polymerization step (Z2) shown below is used as the polymerization step (Z).

[0222]A method for producing a conductive aniline polymer (P) of the embodiment includes a polymerization step (Z2) of adding an aniline derivative (A) represented by the formula (2) and an oxidizing agent (D) to a solution in which a conductive aniline polymer (P-1) having a repeating unit represented by the formula (1) is dissolved in a solvent (C) or a dispersion in which the conductive aniline polymer (P-1) is dispersed in a solvent (C) to polymerize the aniline derivative.

[0223]In the polymerization step (Z2), a basic compound (B) may be further added to a solution or a dispersion of the conductive aniline polymer (P-1) to polymerize the aniline derivative, if necessary.

Conductive Aniline Polymer (P-1)

[0224]A conductive aniline polymer (P-1) used in the polymerization step (Z2) of the embodiment has a repeating unit represented by the formula (1).

[0225]The conductive aniline p...

example 1-1

[0307]First, 200 mmol of ammonium peroxodisulfate and 1.0 g of sulfuric acid were dissolved in 150 mL of a mixed solvent of water and acetonitrile (volume ratio: 1:1) cooled to 0° C. in an ethylene glycol bath at a stirring power of 0.7 kw / m3 to give a solution (polymerization initiation temperature: reaction solution temperature, 1.5° C.). Next, to the solution, a solution of 200 mmol of 2-aminoanisole-4-sulfonic acid and 200 mmol of triethylamine in 150 mL of a mixed solvent of water and acetonitrile (volume ratio: 1:1) was added dropwise at 200 mmol / hr. After completion of the dropwise addition, the reaction solution was kept for 2 hours under stirring at a stirring rotation speed of 200 rpm while the temperature of the refrigerant was adjusted so that the temperature (retention temperature) of the reaction solution was 0° C. (polymerization step (Z1)). The maximum temperature of the reaction solution in the polymerization step (Z1) was 8° C. when the amount of the added monomer ...

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Abstract

When measuring the molecular mass distribution of conductive aniline polymer of formula (1) by GPC and converting its retention time into molecular mass (M) in terms of sodium polystyrene sulfonate, for the molecular mass (M), the area ratio (X / Y) of the area (X) of a region of 15,000 Da or more to the area (Y) of a region of less than 15,000 Da is 1.20 or more. A method for producing such a polymer includes: polymerization step (Z1) where specific aniline derivative (A) is polymerized in a solution containing basic compound (B), solvent (C), and oxidizing agent (D) at a liquid temperature lower than 25° C.; or polymerization step (Z2) where specific aniline derivative (A) and oxidizing agent (D) are added to and polymerized in a solution of a conductive aniline polymer (P-1) with a unit of formula (1) dissolved or dispersed in a solvent (C).

Description

TECHNICAL FIELD[0001]The present invention relates to a conductive aniline polymer, a method for producing the same, and a method for producing a conductive film.[0002]This application claims the priority based upon Japanese Patent Application No. 2010-240039 filed on Oct. 26, 2010, Japanese Patent Application No. 2011-006849 filed on Jan. 17, 2011, Japanese Patent Application No. 2011-032053 filed on Feb. 17, 2011, Japanese Patent Application No. 2011-071517 filed on Mar. 29, 2011, and Japanese Patent Application No. 2011-083579 filed on Apr. 5, 2011, the contents of which are incorporated herein by reference.BACKGROUND ART[0003]As a conductive polymer for various applications, a conductive sulfonated polyaniline polymer has been known.[0004]As a method for producing a sulfonated polyaniline, for example, Patent Literature 1 discloses a method for producing an aniline copolymer, the method including copolymerizing alkoxy group-substituted aminobenzenesulfonic acid with at least one...

Claims

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Application Information

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IPC IPC(8): C09D5/24
CPCC09D5/24C08L79/02C08G73/0266C09D179/02H01B1/128H01B13/30C08G73/00C08J5/18B05D5/12
Inventor YAMADA, KOHEIHORIUCHI, YASUSHIHACHIYA, YUKIKOUZAWA, MASASHISAKAI, TAKAHIROTAKAGI, TAMAE
Owner MITSUBISHI RAYON CO LTD
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