Continuous flow process for preparing conducting polymers

Patent metadata

Field	Value
Publication number	US-11738320-B2
Application number	US-202117380088-A
Country	US
Kind code	B2
Filing date	Jul 20, 2021
Priority date	Dec 12, 2017
Publication date	Aug 29, 2023
Grant date	Aug 29, 2023

Abstract

The present disclosure relates to a continuous flow process for preparing conducting polymers, for example polyaniline. The continuous flow process can provide a controlled synthesis of a conducting polymer from an emulsion comprising a polymerizable organic monomer and a free radical initiator in flow within a temperature controlled continuous flow reactor comprising at least one mixing element. The present disclosure also relates to the conducting polymers prepared by the continuous flow process.

First claim

The invention claimed is:

1. A process, comprising:
introducing a polymerizable organic monomer into a first continuous flow mixer as a neat liquid or with an organic solvent;
introducing, separately from the polymerizable organic monomer, a protonic acid into the first continous flow mixer to form an organic soluble monomer salt;
forming a reactant mixture by introducing the organic soluble monomer salt and an aqueous stream comprising a free radical initiator into a second continuous flow mixer that is in series with the first continous flow mixer; and
introducing the reactant mixture into a tubular reactor to form a conducting polymer or salt thereof.

2. The process of claim 1 , wherein the first continuous flow mixer is a continuous flow reactor comprising a mixing element disposed therein.

3. The process of claim 2 , wherein the mixing element is a static mixing element.

4. The process of claim 1 , wherein the second continuous flow mixer is a continuous flow reactor comprising a mixing element disposed therein.

5. The process of claim 4 , wherein the mixing element is a static mixing element.

6. The process of claim 1 , wherein the tubular reactor comprises a static mixing element disposed therein.

7. The process of claim 1 , wherein the reactant mixture is an emulsion.

8. The process of claim 1 , wherein the tubular reactor is a continous flow tubular reactor comprising one or more static mixing elements disposed therein.

9. The process of claim 8 , wherein the tubular reactor comprises five or more static mixing elements disposed therein.

10. The process of claim 1 , wherein the conducting polymer is selected from the group consisting of a polyarylamine, a polyarylthiol, a polypyrrole, a polycarbazole, a polyindole, a polyazepine, a polythiophene, a poly(3,4-ethylenedioxythiophene), a poly(3,4-propylenedioxythiophene), and combination(s) thereof.

11. The process of claim 1 , wherein the polymerizable organic monomer is selected from the group consisting of an arylamine, an arylthiol, a pyrrole, a carbazole, an indole, an azepine, a thiophene, a 3,4-ethylenedioxythiophene, a 3,4-propylenedioxythiophene monomer, and combination(s) thereof.

12. The process of claim 1 , wherein the conducting polymer is a polyaniline and the polymerizable organic monomer is an aniline.

13. The process of claim 1 , wherein the conducting polymer is a poly(3,4-ethylenedioxythiophene) and the polymerizable organic monomer is a 3,4-ethylenedioxythiophene.

14. The process of claim 1 , wherein the conducting polymer is a poly(3,4-propylenedioxythiophene) and the polymerizable organic monomer is a 3,4-propylenedioxythiophene monomer.

15. The process of claim 1 , wherein introducing the reactant mixture into the tubular reactor comprises controlling the temperature at about −5° C. to about 5° C. with a variation of about 2° C. or less.

16. The process of claim 1 , wherein the tubular reactor has an internal diameter of about 2 mm to about 20 mm.

17. The process of claim 16 , wherein the tubular reactor has an internal diameter of about 5 mm to about 10 mm.

18. The process of claim 1 , wherein the protonic acid is dinonylnaphthalenesulfonic acid (DNNSA).

19. The process of claim 1 , wherein the free radical initiator is ammonium persulfate.

20. The process of claim 1 , wherein the conducting polymer comprises a number average molecular weight of about 10,000 g/mol to about 120,000 g/mol.

Assignees

• Boeing Co
• Commw Scient Ind Res Org

Inventors

• Kohl Thomas
• Tsanaktsidis John
• Hornung Christian
• Kinlen Patrick
• Bruton Eric
• Flack Matthew
• Zweig Andrew

Classifications

• B01J19/0013 Primary

  Controlling the temperature of the process · CPC title

• B01J19/1812

  Tubular reactors · CPC title

• C08G61/126

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

• C08G73/0266 Primary

  Polyanilines or derivatives thereof · CPC title

• C08K5/01

  Hydrocarbons {(C08K5/0091 takes precedence)} · CPC title