Polymer compound for a conductive polymer and method for producing same

Patent metadata

Field	Value
Publication number	US-9527937-B2
Application number	US-201514731080-A
Country	US
Kind code	B2
Filing date	Jun 4, 2015
Priority date	Jul 18, 2014
Publication date	Dec 27, 2016
Grant date	Dec 27, 2016

Abstract

The present invention provides a polymer compound for a conductive polymer, containing one or more repeating units (a) represented by the following general formula (1), the polymer compound for a conductive polymer being synthesized by ion-exchange of a lithium salt, a sodium salt, a potassium salt, or a nitrogen compound salt of a sulfonic acid residue, and having a weight average molecular weight in the range of 1,000 to 500,000.

There can be provided a polymer compound for a conductive polymer having a specific superacidic sulfo group which is soluble in an organic solvent, and suitably used for a fuel cell or a dopant for a conductive material.

First claim

What is claimed is:

1. A polymer compound for a conductive polymer, comprising one or more repeating units (a) represented by the following general formula (1),
the polymer compound for a conductive polymer being synthesized by ion-exchange of a lithium salt, a sodium salt, a potassium salt, or a nitrogen compound salt of a sulfonic acid residue, and having a weight average molecular weight in the range of 1,000 to 500,000,

wherein R 1 represents a hydrogen atom or a methyl group; R 2 represents a single bond, an ester group, or a linear, branched, or cyclic hydrocarbon group having 1 to 12 carbon atoms that optionally includes either or both of an ether group and an ester group; Z represents a single bond, a phenylene group, a naphthylene group, an ether group, or an ester group; and “a” is a number satisfying 0<a≦1.0.

2. The polymer compound for a conductive polymer according to claim 1 , further comprising a repeating unit (b) represented by the following general formula (2),

wherein “b” is a number satisfying 0<b<1.0.

3. The polymer compound for a conductive polymer according to claim 1 , wherein the repeating unit (a) represented by the general formula (1) includes one or more kinds selected from repeating units (a1) to (a3) respectively represented by the following general formulae (3-1) to (3-3),

wherein R 1 and R 2 have the same meanings as defined above; a1, a2, and a3 are each a number satisfying 0≦a1≦1.0, 0≦a2≦1.0, 0≦a3≦1.0, and 0<a1+a2+a3≦1.0; and m is 0 or 1.

4. The polymer compound for a conductive polymer according to claim 2 , wherein the repeating unit (a) represented by the general formula (1) includes one or more kinds selected from repeating units (a1) to (a3) respectively represented by the following general formulae (3-1) to (3-3),

wherein R 1 and R 2 have the same meanings as defined above; a1, a2, and a3 are each a number satisfying 0≦a1≦1.0, 0≦a2≦1.0, 0≦a3≦1.0, and 0<a1+a2+a3≦1.0; and m is 0 or 1.

5. The polymer compound for a conductive polymer according to claim 1 , wherein the lithium salt, the sodium salt, the potassium salt, or the nitrogen compound salt of the sulfonic acid residue is composed of a repeating unit represented by the following general formula (4),

wherein R 1 , R 2 , Z, and “a” have the same meanings as defined above; and X represents lithium, sodium, potassium, or a nitrogen compound represented by the following general formula (5),

wherein R 101d , R 101e , R 101f , and R 101g each represent a hydrogen atom, a linear, branched, or cyclic alkyl group, alkenyl group, oxoalkyl group, or oxoalkenyl group each having 1 to 12 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an aralkyl group or an aryloxoalkyl group each having 7 to 12 carbon atoms where a part or all of hydrogen atoms in these groups are optionally substituted by an alkoxy group(s); R 101d and R 101e , or R 101d , R 101e , and R 101f optionally form a ring, and when the ring is formed, R 101d and R 101e , or R 101d , R 101e , and R 101f each represent an alkylene group having 3 to 10 carbon atoms or a heteroaromatic ring having therein the nitrogen atom in the formula.

6. The polymer compound for a conductive polymer according to claim 2 , wherein the lithium salt, the sodium salt, the potassium salt, or the nitrogen compound salt of the sulfonic acid residue is composed of a repeating unit represented by the following general formula (4),

wherein R 1 , R 2 , Z, and “a” have the same meanings as defined above; and X represents lithium, sodium, potassium, or a nitrogen compound represented by the following general formula (5),

wherein R 101d , R 101e , R 101f , and R 101g each represent a hydrogen atom, a linear, branched, or cyclic alkyl group, alkenyl group, oxoalkyl group, or oxoalkenyl group each having 1 to 12 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an aralkyl group or an aryloxoalkyl group each having 7 to 12 carbon atoms where a part or all of hydrogen atoms in these groups are optionally substituted by an alkoxy group(s); R 101d and R 101e , or R 101d , R 101e , and R 101f optionally form a ring, and when the ring is formed, R 101d and R 101e , or R 101d , R 101e , and R 101f each represent an alkylene group having 3 to 10 carbon atoms or a heteroaromatic ring having therein the nitrogen atom in the formula.

7. The polymer compound for a conductive polymer according to claim 3 , wherein the lithium salt, the sodium salt, the potassium salt, or the nitrogen compound salt of the sulfonic acid residue is composed of a repeating unit represented by the following general formula (4),

wherein R 1 , R 2 , Z, and “a” have the same meanings as defined above; and X represents lithium, sodium, potassium, or a nitrogen compound represented by the following general formula (5),

wherein R 101d , R 101e , R 101f , and R 101g each represent a hydrogen atom, a linear, branched, or cyclic alkyl group, alkenyl group, oxoalkyl group, or oxoalkenyl group each having 1 to 12 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an aralkyl group or an aryloxoalkyl group each having 7 to 12 carbon atoms where a part or all of hydrogen atoms in these groups are optionally substituted by an alkoxy group(s); R 101d and R 101e , or R 101d , R 101e , and R 101f optionally form a ring, and when the ring is formed, R 101d and R 101e , or R 101d , R 101e , and R 101f each represent an alkylene group having 3 to 10 carbon atoms or a heteroaromatic ring having therein the nitrogen atom in the formula.

8. The polymer compound for a conductive polymer according to claim 4 , wherein the lithium salt, the sodium salt, the potassium salt, or the nitrogen compound salt of the sulfonic acid residue is composed of a repeating unit represented by the following general formula (4),

wherein R 1 , R 2 , Z, and “a” have the same meanings as defined above; and X represents lithium, sodium, potassium, or a nitrogen compound represented by the following general formula (5),

wherein R 101d , R 101e , R 101f , and R 101g each represent a hydrogen atom, a linear, branched, or cyclic alkyl group, alkenyl group, oxoalkyl group, or oxoalkenyl group each having 1 to 12 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an aralkyl group or an aryloxoalkyl group each having 7 to 12 carbon atoms where a part or all of hydrogen atoms in these groups are optionally substituted by an alkoxy group(s); R 101d and R 101e , or R 101d , R 101e , and R 10

Assignees

• Shinetsu Chemical Co

Inventors

• Hatakeyama Jun
• Hasegawa Koji
• Nagasawa Takayuki
• Sagehashi Masayoshi
• Ohashi Masaki

Classifications

• C08F212/30

  Sulfur · CPC title

• C08F212/20

  Fluorine · CPC title

• C09D125/18

  Homopolymers or copolymers of aromatic monomers containing elements other than carbon and hydrogen · CPC title

• C08F22/26 Primary

  of unsaturated alcohols {(C08F22/1006 takes precedence)} · CPC title

• C08F22/10

  Esters · CPC title