# US 2014/0154612 A1 · Polymer-electrolyte membrane, electrochemical fuel cell, and related method > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2014/0154612 A1 - Document ID: US20140154612A1 - Status: Published application - Kind: A1 - Application number: 13/690,721 - Filed: 2012-11-30 - Published: 2014-06-05 - Earliest claimed: 2012-11-30 - Assignees: General Electric Company - Applicants: General Electric Company - Inventors: Lakshmi Krishnan; Gary William Yeager; Grigorii Lev Soloveichik - Web page: https://patentgrep.com/patent/US20140154612A1 ## CPC - H01M 8/1023: having only carbon, e.g. polyarylenes, polystyrenes or polybutadiene-styrenes - H01M 8/1039: halogenated, e.g. sulfonated polyvinylidene fluorides - H01M 8/1051: Non-ion-conducting additives, e.g. stabilisers, SiO2 or ZrO2 - H01M 8/1086: After-treatment of the membrane other than by polymerisation - H01M 2008/1095: {Fuel cells with polymeric electrolytes} - 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 - 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 A polymer-electrolyte membrane is presented. The polymer-electrolyte membrane comprises an acid-functional polymer, and an additive incorporated in at least a portion of the membrane. The additive comprises a fluorinated cycloaliphatic additive, a hydrophobic cycloaliphatic additive, or combinations thereof, wherein the additive has a boiling point greater than about 120° C. An electrochemical fuel cell including the polymer-electrolyte membrane, and a related method, are also presented. ## Claims ### Claim 1 A polymer-electrolyte membrane, comprising: an acid-functional polymer; and an additive incorporated in at least a portion of the membrane; wherein the additive comprises a fluorinated cycloaliphatic additive, a hydrophobic cycloaliphatic additive, or combinations thereof, and wherein the additive has a boiling point greater than about 120° C. ### Claim 2 (depends on 1) The polymer-electrolyte membrane of claim 1, wherein the fluorinated cycloaliphatic additive comprises a fluorinated cycloaliphatic compound selected from the group consisting of cis-perfluorodecalin, trans-perfluorodecalin, perfluoro-1-methyldecalin, perfluoroisopentyl-tetrahydropyran, perfluorobicyclohexane, perfluorohydrophenanthrene, tetracosafluorotetradecahydroanthracene, perfluoro-1,4,5,8-dimethanodecalin, and combinations thereof. ### Claim 3 (depends on 1) The polymer-electrolyte membrane of claim 1, wherein the hydrophobic cycloaliphatic additive comprises a cycloaliphatic moiety selected from the group consisting of cis-decalin, trans-decalin, octahydro-1H-indene, tetrahydrodicyclopentadiene, 1,4,5,8-dimethanodecalin, tetradecahydroanthracene, dodecahydro-1H-phenanthrenene, and combinations thereof. ### Claim 4 (depends on 1) The polymer-electrolyte membrane of claim 1, wherein the additive is present in the membrane in an amount of at least about 0.5 weight percent of the total weight of the membrane. ### Claim 5 (depends on 1) The polymer-electrolyte membrane of claim 1, wherein the additive is present in the membrane in an amount in a range from about 0.5 weight percent to about 10 weight percent of the total weight of the membrane. ### Claim 6 (depends on 1) The polymer-electrolyte membrane of claim 1, wherein the acid-functional polymer comprises a plurality of acid functional groups selected from the group consisting of a sulfonic acid moiety, a phosphoric acid moiety, a phosphonic acid moiety, a sulfonylimide moiety, and combinations thereof. ### Claim 7 (depends on 1) The polymer-electrolyte membrane of claim 1, wherein the acid-functional polymer comprises an acid functional fluoropolymer. ### Claim 8 (depends on 1) The polymer-electrolyte membrane of claim 1, further comprising an electrolyte comprising water, an oxo-acid, a nitrogen heterocyclic base, or combinations thereof. ### Claim 9 (depends on 1) A membrane electrode assembly comprising the polymer-electrolyte membrane of claim 1. ### Claim 10 A polymer-electrolyte membrane, comprising: an acid-functional polymer; and a fluorinated cycloaliphatic additive incorporated in at least a portion of the membrane, wherein the fluorinated cycloaliphatic additive has a boiling point greater than about 120° C. ### Claim 11 (depends on 10) The polymer-electrolyte membrane of claim 10, wherein the fluorinated cycloaliphatic additive comprises a fluorinated cycloaliphatic compound selected from the group consisting of cis-perfluorodecalin, trans-perfluorodecalin, perfluoro-1-methyldecalin, perfluoroisopentyl-tetrahydropyran, perfluorobicyclohexane, perfluorohydrophenanthrene, tetracosafluorotetradecahydroanthracene, perfluoro-1,4,5,8-dimethanodecalin, and combinations thereof. ### Claim 12 (depends on 10) The polymer-electrolyte membrane of claim 10, wherein the fluorinated cycloaliphatic additive is present in the membrane in an amount in a range from about 0.5 weight percent to about 10 weight percent of the total weight of the membrane. ### Claim 13 (depends on 10) The polymer-electrolyte membrane of claim 10, wherein the acid-functional polymer comprises an acid functional fluoropolymer. ### Claim 14 An electrochemical fuel cell, comprising: a first electrode; a second electrode; and a polymer-electrolyte membrane disposed between the first electrode and the second electrode, wherein the polymer-electrolyte membrane comprises: an acid-functional polymer; and an additive incorporated in at least a portion of the membrane; wherein the additive comprises a fluorinated cycloaliphatic additive, a hydrophobic cycloaliphatic additive, or combinations thereof, and wherein the additive has a boiling point greater than about 120° C. ### Claim 15 (depends on 14) The electrochemical fuel cell of claim 14, wherein the fluorinated cycloaliphatic additive comprises a fluorinated cycloaliphatic compound selected from the group consisting of cis-perfluorodecalin, trans-perfluorodecalin, perfluoro-1-methyldecalin, perfluoroisopentyl-tetrahydropyran, perfluorobicyclohexane, perfluorohydrophenanthrene, tetracosafluorotetradecahydroanthracene, perfluoro-1,4,5,8-dimethanodecalin, and combinations thereof. ### Claim 16 (depends on 14) The electrochemical cell of claim 14, wherein the hydrophobic cycloaliphatic additive comprises a cycloaliphatic moiety selected from the group consisting of cis-decalin, trans-decalin, octahydro-1H-indene, tetrahydrodicyclopentadiene, 1,4,5,8-dimethanodecalin, tetradecahydroanthracene, dodecahydro-1H-phenanthrene, and combinations thereof. ### Claim 17 (depends on 14) The electrochemical fuel cell of claim 14, further comprising an electrolyte comprising water, an oxo-acid, a nitrogen heterocyclic base, or combinations thereof. ### Claim 18 A method of making an electrochemical fuel cell, comprising: (i) incorporating an additive into at least a portion of the polymer-electrolyte membrane to form an additive-modified polymer-electrolyte membrane, wherein the additive comprises a fluorinated cycloaliphatic additive, a hydrophobic cycloaliphatic additive, or combinations thereof, and wherein the additive has a boiling point greater than about 120° C.; and (ii) assembling a first electrode, the additive-modified polymer-electrolyte membrane, and a second electrode into the electrochemical fuel cell. ### Claim 19 (depends on 18) The method of claim 18, wherein the step (i) comprises contacting at least a portion of the polymer-electrolyte membrane with a solution comprising the additive. ### Claim 20 (depends on 18) The method of claim 18, wherein the fluorinated cycloaliphatic additive comprises a fluorinated cycloaliphatic compound selected from the group consisting of cis-perfluorodecalin, trans-perfluorodecalin, perfluoro-1-methyldecalin, perfluoroisopentyl-tetrahydropyran, perfluorobicyclohexane, perfluorohydrophenanthrene, tetracosafluorotetradecahydroanthracene, perfluoro-1,4,5,8-dimethanodecalin, and combinations thereof. ### Claim 21 (depends on 18) The method of claim 18, wherein the hydrophobic cycloaliphatic additive comprises a cycloaliphatic moiety selected from the group consisting of cis-decalin, trans-decalin, octahydro-1H-indene, tetrahydrodicyclopentadiene, 1,4,5,8-dimethanodecalin, tetradecahydroanthracene, dodecahydro-1H-phenanthrene, and combinations thereof.