Proton exchange membrane material and methods of making the same

    公开(公告)号:US11621433B2

    公开(公告)日:2023-04-04

    申请号:US16471358

    申请日:2017-12-20

    Abstract: Hydrocarbon proton exchange membranes are disclosed that are composed of a material including a hydrophobic main chain, and acidic side chains. The main chain includes a polyaryl structure that is substantially free of ether linkages and also includes a fluoromethyl substituted carbon. The acidic side chains include a hydrocarbon tether terminated by a strongly acidic group, such as a fluoroalkyl sulfonate group. Chemical stability of the material is increased by removing the ether linkages from the main chain. The hydrophobic main chain and substantially hydrophilic side chains create a phase-separated morphology that affords enhanced transport of protons and water across the membrane even at low relative humidity levels. These materials are advantageous as membranes for use in fuel cells, redox flow batteries, water hydrolysis systems, sensors, electrochemical hydrogen compressors, actuators, water purifiers, gas separators, etc.

    IONIC FUNCTIONALIZATION OF AROMATIC POLYMERS FOR ION EXCHANGE MEMBRANES

    公开(公告)号:US20220266239A1

    公开(公告)日:2022-08-25

    申请号:US17658627

    申请日:2022-04-08

    Abstract: The electrochemical energy conversion system of the present disclosure includes an anode, a cathode, and an ion exchange membrane including a polymer having an aromatic polymer chain and an alkylated substrate including an alkyl chain, and at least one ionic group. The alkylated substrate is bound to at least one aromatic group in the polymer chain via Friedel-Crafts alkylation of the at least one aromatic group. The alkylation reaction utilizes a haloalkylated tertiary alcohol or a haloalkylated alkene as a precursor. In the presence of an acid catalyst, a carbocation is generated in the precursor which reacts with the aromatic rings of the polymer chain. The at least one ionic group is then replaced with a desired cationic or anionic group using a substitution reaction. The membranes exhibit advantageous stability achieved through a simplified and scalable reaction scheme.

    Thermally stable hydrocarbon-based anion exchange membrane and ionomers

    公开(公告)号:US12220691B2

    公开(公告)日:2025-02-11

    申请号:US18607624

    申请日:2024-03-18

    Abstract: An anion exchange membrane is composed of a copolymer of 1,1-diphenylethylene and one or more styrene monomers, such as 4-tert-butylstyrene. The copolymer includes a backbone substituted with a plurality of ionic groups coupled to phenyl groups on the backbone via hydrocarbyl tethers between about 1 and about 7 carbons in length. High-temperature conditions enabled by these copolymers enhance conductivity performance, making them particularly suitable for use in anion exchange membranes in fuel cells, electrolyzers employing hydrogen, ion separations, etc. The properties of the membranes can be tuned via the degree of functionalization of the phenyl groups and selection of the functional groups, such as quaternary ammonium groups. Several processes can be used to incorporate the desired ionic functional groups into the polymers, such as chloromethylation, radical bromination, Friedel-Crafts acylation and alkylation, sulfonation followed by amination, or combinations thereof.

    Phosphate anion-quaternary ammonium ion pair coordinated polymer membranes

    公开(公告)号:US12027731B2

    公开(公告)日:2024-07-02

    申请号:US17309401

    申请日:2019-11-26

    Abstract: Ion exchange membranes materials according to the present disclosure exhibit improved conductivity at low and intermediate relative humidity without sacrificing mechanical strength. Polymers are provided that include a backbone with one or more aryl groups, a halocarbyl group, and a halocarbyl side chain attached to the backbone, wherein the halocarbyl side chain includes a halide separated from the backbone by a hydrocarbyl chain, a hydrocarbyl ring, or combinations thereof. The halide is substituted with a tertiary amine and halide anions are then exchanged with hydroxide anions. The polymers are then contacted with phosphoric acid, which is deprotonated by the hydroxide ions, forming anions which enhance interactions with adjacent quaternary ammonium groups and induce excess phosphoric acid molecules to cluster around those quaternary ammonium groups. The membranes exhibit negligible dopant leaching even at high relative humidity.

    Thermally stable hydrocarbon-based anion exchange membrane and ionomers

    公开(公告)号:US11969723B2

    公开(公告)日:2024-04-30

    申请号:US17901985

    申请日:2022-09-02

    Abstract: An anion exchange membrane is composed of a copolymer of 1,1-diphenylethylene and one or more styrene monomers, such as 4-tert-butylstyrene. The copolymer includes a backbone substituted with a plurality of ionic groups coupled to phenyl groups on the backbone via hydrocarbyl tethers between about 1 and about 7 carbons in length. High-temperature conditions enabled by these copolymers enhance conductivity performance, making them particularly suitable for use in anion exchange membranes in fuel cells, electrolyzers employing hydrogen, ion separations, etc. The properties of the membranes can be tuned via the degree of functionalization of the phenyl groups and selection of the functional groups, such as quaternary ammonium groups. Several processes can be used to incorporate the desired ionic functional groups into the polymers, such as chloromethylation, radical bromination, Friedel-Crafts acylation and alkylation, sulfonation followed by amination, or combinations thereof.

    ANION-SOLVATING POLYMER MEMBRANES

    公开(公告)号:US20230096778A1

    公开(公告)日:2023-03-30

    申请号:US17758767

    申请日:2021-01-22

    Abstract: The present disclosure relates, in part, to polymers having a graft chain and/or a cyclic amino group. In particular examples, the graft chain and/or the cyclic amino group provides enhanced hydrophilicity, alkaline stability, and/or anion solvation. Compounds, compositions, and methods are described herein.

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