Polyanilines and methods thereof

Patent metadata

Field	Value
Publication number	US-11248089-B2
Application number	US-202016818517-A
Country	US
Kind code	B2
Filing date	Mar 13, 2020
Priority date	Apr 10, 2019
Publication date	Feb 15, 2022
Grant date	Feb 15, 2022

Abstract

The present disclosure provides polyanilines, articles thereof, and methods of forming polyanilines. In at least one aspect, a polyaniline has a thermal stability of about 100° C. or greater, a weight average molecular weight (Mw) of from about 50,000 g/mol to about 150,000 g/mol and a molecular weight distribution (Mw/Mn) of from about 1 to about 5. In at least one aspect, a film includes a polyaniline, the film having a hydrocarbon content of about 1 wt % or less, based on the total weight of the film. In at least one aspect, a method includes introducing an emulsion of an aqueous solution of an aniline and an alkyl-substituted aryl sulfonic acid having 1 wt % or less of hydrocarbon content into a flow reactor, the flow reactor having a length of tubing having an inner diameter. The method includes polymerizing the monomer within the tube to form a polyaniline.

First claim

What is claimed is:

1. A polyaniline having:
a thermal stability of about 100° C. or greater,
a weight average molecular weight (Mw) of from about 50,000 g/mol to about 150,000 g/mol, as determined by gel permeation chromatography,
a number average molecular weight (Mn) of from about 50,000 g/mol to about 100,000 g/mol, as determined by gel permeation chromatography,
a z-average molecular weight (Mz) of from about 100,000 g/mol to about 250,000 g/mol, as determined by gel permeation chromatography,
a peak average molecular weight (Mp) of from about 50,000 g/mol to about 150,000 g/mol, and
a molecular weight distribution (Mw/Mn) of from about 1 to about 5, as determined by gel permeation chromatography.

2. The polyaniline of claim 1 , wherein the polyaniline is an acidified polyaniline having a plurality of conjugate base counterions.

3. The polyaniline of claim 1 , wherein the polyaniline has an Mw of from about 75,000 g/mol to about 100,000 g/mol, as determined by gel permeation chromatography.

4. The polyaniline of claim 1 , wherein the polyaniline has an Mw of from about 110,000 g/mol to about 140,000 g/mol, as determined by gel permeation chromatography.

5. The polyaniline of claim 1 , wherein the polyaniline has an Mn of from about 72,000 g/mol to about 74,000 g/mol.

6. The polyaniline of claim 1 , wherein the polyaniline has a molecular weight distribution (Mw/Mn) of from about 1 to about 3, as determined by gel permeation chromatography.

7. The polyaniline of claim 6 , wherein the polyaniline has an Mw/Mn of from about 1.5 to about 1.9, as determined by gel permeation chromatography.

8. The polyaniline of claim 1 , wherein the polyaniline has an Mz of from about 152,000 g/mol to about 204,000 g/mol.

9. The polyaniline of claim 1 , wherein the polyaniline has an Mp of from about 113,000 g/mol to about 136,000 g/mol.

10. The polyaniline of claim 1 , wherein the polyaniline has a thermal stability of from about 150° C. to about 160° C.

11. The polyaniline of claim 1 , wherein the polyaniline is represented by Formula (I):

wherein:
each instance of R 1 , R 2 , R 3 , and R 4 is independently selected from hydrogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 aryl, substituted or unsubstituted C1-C20 alkaryl, substituted or unsubstituted C1-C20 arlyalkyl, substituted or unsubstituted C1-C20 alkoxyl, and halogen, wherein one or more instances of R 1 , R 2 , R 3 , and R 4 are optionally substituted with a group independently selected from C1-C20 alkxoyl and halogen;
each instance of A − is an anionic ligand; and
n is an integer such that the polyaniline has a weight average molecular weight (Mw) of from about 55,000 g/mol to about 80,000 g/mol.

12. The polyaniline of claim 11 , wherein each instance of A− is dinonylnaphthalene sulfonate.

13. A film comprising the polyaniline of claim 1 , wherein the film has a hydrocarbon content of about 1 wt % or less, based on the total weight of the film.

14. The film of claim 13 , wherein the film has a hydrocarbon content of about 0.5 wt % or less, based on the total weight of the film.

15. The film of claim 14 , wherein the film comprises about 0.5 wt % or less of naphthalene, based on the total weight of the film.

16. The film of claim 15 , wherein the film has an outgassing % of about 0.5% or less.

17. A polyaniline having:
a thermal stability of about 100° C. or greater,
an Mw of from about 110,000 g/mol to about 140,000 g/mol, as determined by gel permeation chromatography,
an Mn of from about 72,000 g/mol to about 74,000 g/mol, as determined by gel permeation chromatography,
an Mz of from about 152,000 g/mol to about 204,000 g/mol, as determined by gel permeation chromatography,
a peak average molecular weight (Mp) of from about 113,000 g/mol to about 136,000 g/mol, and
a molecular weight distribution (Mw/Mn) of from about 1.5 to about 1.9, as determined by gel permeation chromatography.

18. The polyaniline of claim 17 , wherein the polyaniline has a thermal stability of from about 150° C. to about 160° C.

19. A film comprising the polyaniline of claim 18 , wherein the film comprises about 0.5 wt % or less of naphthalene, based on the total weight of the film.

20. The film of claim 19 , wherein the film has an outgassing % of about 0.5% or less.

Assignees

• Boeing Co

Inventors

• Kinlen Patrick J
• Flack Matthew A
• Bruton Eric A

Classifications

• C08J5/18

  Manufacture of films or sheets · CPC title

• C08L79/02

  Polyamines · CPC title

• C08J2379/02

  Polyamines · CPC title

• C08G73/0266 Primary

  Polyanilines or derivatives thereof · CPC title

• C09D179/02

  Polyamines · CPC title