Polyol-based compositions comprising cationic group-functionalized polyphenylene polymers

Patent metadata

Field	Value
Publication number	US-10312541-B2
Application number	US-201615204523-A
Country	US
Kind code	B2
Filing date	Jul 7, 2016
Priority date	Jul 30, 2015
Publication date	Jun 4, 2019
Grant date	Jun 4, 2019

Abstract

Disclosed herein are embodiments of compositions comprising polyols and cationic group-functionalized polyphenylene polymers suitable for use in electrochemical systems. The disclosed composition exhibit improved dispersion properties and further provide anion exchange polymer membranes exhibited improved chemical and mechanical properties. Also disclosed herein are methods of making and using the disclosed compositions.

First claim

I claim:

1. A composition for use in an electrochemical system, comprising:
a cationic group-functionalized polyphenylene polymer having a structure satisfying a formula

wherein each of R 1 , R 2 , R 3 , R 4 , and R 6 independently is selected from hydrogen, fluoro, an aliphatic group, an aryl group, or a combination thereof; R 7 is selected from aliphatic, aryl, carbonyl, sulfonyl, or a combination thereof; each X independently is selected from a cationic functional group; n ranges from 2 to 1000, m ranges from 1 to 4; and p ranges from 0 to 3; and
a dispersion medium comprising a polyol having a methyl to hydroxyl ratio that provides a value ranging from 1 to 2.

2. The composition of claim 1 , wherein each X independently is selected from ammonium, sulfonium, phosphonium, guanidinium, imidazolium, phosphazinium, or combinations thereof.

3. The composition of claim 1 , wherein R 7 is carbonyl, sulfonyl, alkyl, phenyl, or phenyl alkyl.

4. The composition of claim 1 , wherein the cationic group-functionalized polyphenylene polymer is selected from

5. The composition of claim 1 , wherein the polyol is a diol comprising a hydroxyl group located at C1 of the diol and a hydroxyl group at C2 of the diol.

6. The composition of claim 1 , wherein the dispersion medium comprises 1,2-propanediol, 1,2-propanediol, 1,3-propanediol, ethylene glycol, 1,2-butanediol, 1,3-butanediol, 2,3-butanediol, 1,4-butanediol, and combinations thereof.

7. The composition of claim 1 , wherein the composition further comprises one or more electrocatalysts.

8. The composition of claim 7 , wherein the electrocatalyst comprises a metal selected from platinum, gold, iridium, palladium, or a combination thereof; a transition metal selected from ruthenium, iron, chromium, cobalt, molybdenum, manganese, magnesium, nickel, osmium, rhodium, tungsten, rhenium, yttrium, titanium, or combinations thereof; a metal alloy selected from a platinum/chromium alloy, a platinum/cobalt alloy, a platinum/iron alloy, or a combination thereof; a transition metal alloy; a carbon-based catalyst selected from porous carbon particulate, fiber, graphene, or combinations thereof; or a combination thereof.

9. The composition of claim 1 , wherein the composition further comprises a dilution solvent having a boiling temperature below a boiling temperature of the dispersion medium.

10. An anion exchange polymer membrane for use in an electrochemical system, comprising a cationic group-functionalized polyphenylene polymer having a structure satisfying a formula

wherein each of R 1 , R 2 , R 3 , R 4 , and R 6 independently is selected from hydrogen, fluoro, an aliphatic group, an aryl group, or a combination thereof; R 7 is selected from carbonyl, sulfonyl, aliphatic, aryl, or a combination thereof; each X independently is selected from a cationic functional group; n ranges from 2 to 1000, m ranges from 1 to 4; and p ranges from 0 to 3; and wherein the anion exchange polymer membrane exhibits a tensile strength ranging from 12 MPa to 35 MPa, a elongation percentage ranging from 2% to 44%, a tensile toughness of 1 MPa to 20MPa, or a combination thereof.

11. The anion exchange polymer membrane of claim 10 , further comprising one or more electrocatalysts.

12. The anion exchange polymer membrane of claim 11 , wherein the one or more electrocatalyst is uniformly distributed in the anion exchange polymer membrane.

13. The anion exchange polymer membrane of claim 11 wherein the electrocatalyst comprises a metal, a transition metal, a metal alloy, a transition metal alloy, a carbon-based catalyst, or a combination thereof.

14. The anion exchange polymer membrane of claim 10 , wherein the electrochemical system is an alkaline electrochemical system.

15. The anion exchange polymer membrane of claim 10 , wherein the electrochemical system is an acidic electrochemical system.

16. An electrochemical device, comprising:
a composition comprising a cationic group-functionalized polyphenylene polymer having a structure satisfying a formula

wherein each of R 1 , R 2 , R 3 , R 4 , and R 6 independently is selected from hydrogen, fluoro, an aliphatic group, an aryl group, or a combination thereof; R 7 is selected from carbonyl, sulfonyl, aliphatic, aryl, or a combination thereof; each X independently is selected from a cationic functional group; n ranges from 2 to 1000, m ranges from 1 to 4; and p ranges from 0 to 3; and
a dispersion medium comprising a polyol having a methyl to hydroxyl ratio that provides a value ranging from 1 to 2.

17. An electrochemical device, comprising an anion exchange membrane comprising a cationic group-functionalized polyphenylene polymer having a structure satisfying a formula

wherein each of R 1 , R 2 , R 3 , R 4 , and R 6 independently is selected from hydrogen, fluoro, an aliphatic group, an aryl group, or a combination thereof; R 7 is selected from carbonyl, sulfonyl, aliphatic, aryl, or a combination thereof; each X independently is selected from a cationic functional group; n ranges from 2 to 1000, m ranges from 1 to 4; and p ranges from 0 to 3; and wherein the anion exchange polymer membrane exhibits a tensile strength ranging from 12 MPa to 35 MPa, a elongation percentage ranging from 2% to 44%, a tensile toughness of 1 MPa to 20MPa, or a combination thereof.

Assignees

• Los Alamos Nat Security Llc
• Triad Nat Security Llc

Inventors

• Kim Yu Seung

Classifications

• C08G2261/143

  Side-chains containing nitrogen · CPC title

• Y02P70/56

  Cross-Sectional Technologies · mapped topic

• C08G2261/148

  Side-chains having aromatic units · CPC title

• H01M4/881

  Electrolytic membranes · CPC title

• H01M8/1081

  starting from solutions, dispersions or slurries exclusively of polymers · CPC title