Organically soluble conductive polymers

Patent metadata

Field	Value
Publication number	US-11352509-B2
Application number	US-201916703415-A
Country	US
Kind code	B2
Filing date	Dec 4, 2019
Priority date	Dec 4, 2019
Publication date	Jun 7, 2022
Grant date	Jun 7, 2022

Abstract

Polymerize ethylenedioxythiophene (EDOT) in a polymerization process using dinonylnaphthalenesulfonic acid (DNNSA) as the dopant and Fe(III) p-toluenesulfonate (Fe (III) p-TSA) as the oxidizing agent to produce an organically soluble polyethylenedioxythiophene (PEDOT).

First claim

What is claimed is:

1. A method of producing an electrically conductive polymer that is soluble in an organic solvent, comprising:
forming a first solution comprising ethylenedioxythiophene (EDOT) monomers and dinonylnapthalenesulfonic acid (DNNSA);
introducing a transition-metal p-toluenesulfonic acid (p-TSA) with the first solution, wherein a molar ratio of transition-metal p-TSA to EDOT monomers is about 1 or greater, to form a product mixture comprising polyethylenedioxythiophene (PEDOT) doped with a plurality of anions of the DNNSA and p-TSA, wherein a molar ratio of DNNSA anions to p-TSA anions is about 1 or greater;
washing the product mixture with an aqueous solution;
retaining an organic phase of the product mixture, the organic phase comprising the PEDOT doped with anions of the DNNSA and the p-TSA; and
isolating the PEDOT doped with anions of the DNNSA and the p-TSA from the organic phase.

2. The method of claim 1 , wherein the EDOT monomers are unfunctionalized monomers.

3. The method of claim 1 , wherein the transition-metal p-TSA is Fe (III) p-TSA.

4. The method of claim 1 , wherein the DNNSA and the EDOT monomers are provided in a molar ratio of the DNNSA to the EDOT monomers of about 1 or greater.

5. The method of claim 1 , wherein the aqueous solution is a non-alkaline aqueous solution.

6. The method of claim 1 , wherein the EDOT monomers, the transition-metal p-toluenesulfonic acid (p-TSA), and the DNNSA are reacted at room temperature.

7. The method of claim 1 , further comprising drying the PEDOT doped with anions at a temperature, wherein the temperature is not greater than 100° C.

8. The method of claim 1 , further comprising introducing a resin to the PEDOT doped with the anions of the DNNSA and the p-TSA to form a mixture.

9. The method of claim 8 , wherein the resin is selected from the group consisting of polyvinylbutyral, ethylene-vinyl acetate, polyimide, polyolefin, polyurethane, silicone, polyvinylchloride, nitrile rubber, and combinations thereof.

10. The method of claim 9 , wherein the resin is polyvinylbutyral.

11. The method of claim 8 , further comprising depositing the mixture onto a carbon allotrope material.

12. The method of claim 11 , wherein the carbon allotrope material is selected from the group consisting of single-walled carbon nanotubes, carbon fibers, and combinations thereof.

13. The method of claim 1 , wherein:
the EDOT monomers are unfunctionalized monomers, and
the transition-metal p-TSA is Fe (III) p-TSA.

14. The method of claim 1 , wherein:
the transition-metal p-TSA is Fe (III) p-TSA, and
the DNNSA and the EDOT monomers are provided in a molar ratio of the DNNSA to the EDOT monomers of about 1 or greater.

15. The method of claim 1 , wherein:
the transition-metal p-TSA is Fe (III) p-TSA, and
the EDOT monomers, the Fe (III) p-TSA, and the DNNSA are reacted at room temperature.

16. The method of claim 1 , wherein:
the transition-metal p-TSA is Fe (III) p-TSA, and
the aqueous solution is a non-alkaline aqueous solution.

17. The method of claim 4 , wherein the molar ratio of transition-metal p-TSA to EDOT monomers is about 1.1.

18. The method of claim 17 , wherein the molar ratio of DNNSA to EDOT monomers is about 1.7.

19. The method of claim 1 , further comprising:
drying the PEDOT doped with anions at a temperature, wherein the temperature is not greater than 100° C., and
introducing a polyvinylbutyral resin to the PEDOT doped with the anions of the DNNSA and the p-TSA to form a mixture.

20. The method of claim 1 , wherein:
the transition-metal p-TSA is Fe (III) p-TSA,
the DNNSA and the EDOT monomers are provided in a molar ratio of the DNNSA to the EDOT monomers of about 1 or greater,
the EDOT monomers, the Fe (III) p-TSA, and the DNNSA are reacted at room temperature, and
the aqueous solution is a non-alkaline aqueous solution.

Assignees

• Boeing Co

Inventors

• Kinlen Patrick John

Classifications

• C09D165/00

  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 · CPC title

• C08G2261/792

  with low-molecular weight dopants · CPC title

• C08G2261/334

  containing heteroatoms · CPC title

• C08G2261/41

  Organometallic coupling reactions · CPC title

• C08G61/126 Primary

  with a five-membered ring containing one sulfur atom in the ring · CPC title