# US 10,312,541 B2 · Polyol-based compositions comprising cationic group-functionalized polyphenylene polymers

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- Number: US 10,312,541 B2
- Document ID: US10312541B2
- Status: Granted
- Kind: B2
- Application number: 15/204,523
- Filed: 2016-07-07
- Published: 2017-02-02
- Granted: 2019-06-04
- Earliest claimed: 2015-07-30
- Assignees: Triad National Security, LLC
- Applicants: Los Alamos National Security, LLC
- Inventors: Yu Seung Kim
- Web page: https://patentgrep.com/patent/US10312541B2

## CPC

- H01M 8/1023: having only carbon, e.g. polyarylenes, polystyrenes or polybutadiene-styrenes
- B01J 41/13: obtained otherwise than by reactions only involving unsaturated carbon-to-carbon bonds
- B01J 47/12: characterised by the use of ion-exchange material in the form of ribbons, filaments, fibres or sheets, e.g. membranes (electrodialysis or electro-osmosis B01D61/42)
- C08G 61/10: only aromatic carbon atoms, e.g. polyphenylenes
- C08J 5/2256: {based on macromolecular compounds obtained by reactions other than those involving carbon-to-carbon bonds, e.g. obtained by polycondensation}
- C08G 2261/143: Side-chains containing nitrogen
- C08G 2261/148: Side-chains having aromatic units
- C08G 2261/312: Non-condensed aromatic systems, e.g. benzene
- C08G 2261/51: Charge transport
- C08J 2365/02: Polyphenylenes
- H01M 4/881: {Electrolytic membranes}
- H01M 8/1081: starting from solutions, dispersions or slurries exclusively of polymers
- H01M 2008/1095: {Fuel cells with polymeric electrolytes}
- H01M 2300/0082: Organic polymers
- Y02E 60/50: Fuel cells
- Y02P 70/50: Manufacturing or production processes characterised by the final manufactured product
- H01M: PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08J: WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H (working, e.g. shaping, of plastics B29)
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## 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.

## Claims

### 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 R1, R2, R3, R4, and R6 independently is selected from hydrogen, fluoro, an aliphatic group, an aryl group, or a combination thereof; R7 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.

### Claim 2 (depends on 1)

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

### Claim 3 (depends on 1)

The composition of claim 1, wherein R7 is carbonyl, sulfonyl, alkyl, phenyl, or phenyl alkyl.

### Claim 4 (depends on 1)

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

### Claim 5 (depends on 1)

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.

### Claim 6 (depends on 1)

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.

### Claim 7 (depends on 1)

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

### Claim 8 (depends on 7)

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.

### Claim 9 (depends on 1)

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.

### Claim 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 R1, R2, R3, R4, and R6 independently is selected from hydrogen, fluoro, an aliphatic group, an aryl group, or a combination thereof; R7 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.

### Claim 11 (depends on 10)

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

### Claim 12 (depends on 11)

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

### Claim 13 (depends on 11)

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.

### Claim 14 (depends on 10)

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

### Claim 15 (depends on 10)

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

### Claim 16

An electrochemical device, comprising:
a composition comprising a cationic group-functionalized polyphenylene polymer having a structure satisfying a formula
wherein each of R1, R2, R3, R4, and R6 independently is selected from hydrogen, fluoro, an aliphatic group, an aryl group, or a combination thereof; R7 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.

### Claim 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 R1, R2, R3, R4, and R6 independently is selected from hydrogen, fluoro, an aliphatic group, an aryl group, or a combination thereof; R7 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.