Polymers having stable cationic pendant groups for use as anion exchange membranes

Yan, Yushan; Hu, Keda; Wang, Junhua; Wang, Lan; Rojas-Carbonell, Santiago; Setzler, Brian

Title: Polymers having stable cationic pendant groups for use as anion exchange membranes

Patent · Tue Nov 28 00:00:00 EST 2023

OSTI ID:2293910

Yan, Yushan; Hu, Keda; Wang, Junhua; Wang, Lan; Rojas-Carbonell, Santiago; Setzler, Brian

Poly(aryl alkylene) polymers or poly(aryl-crown ether-alkylene) polymers with pendant cationic groups are provided which have an alkaline-stable cation, such as imidazolium, introduced into a rigid aromatic polymer backbone free of ether bonds. Hydroxide exchange membranes or hydroxide exchange ionomers formed from these polymers exhibit superior chemical stability, hydroxide conductivity, decreased water uptake, good solubility in selected solvents, and improved mechanical properties in an ambient dry state as compared to conventional hydroxide exchange membranes or ionomers. Hydroxide exchange membrane fuel cells and hydroxide exchange membrane electrolyzers comprising the poly(aryl alkylene) polymers or poly(aryl-crown ether-alkylene) polymers with pendant cationic groups exhibit enhanced performance and durability at relatively high temperatures.

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Research Organization:: Univ. of Delaware, Newark, DE (United States)

Sponsoring Organization:: USDOE

DOE Contract Number:: AR0000814

Assignee:: University of Delaware (Newark, DE)

Patent Number(s):: 11,827,743

Application Number:: 16/833,312

OSTI ID:: 2293910

Resource Relation:: Patent File Date: 03/27/2020

Country of Publication:: United States

Language:: English

References (25)

Novel High Molecular Weight Aromatic Fluorinated Polymers from One-Pot, Metal-Free Step Polymerizations Olvera, Lilian I.; Guzmán-Gutiérrez, Maria T.; Zolotukhin, Mikhail G. Macromolecules, Vol. 46, Issue 18 https://doi.org/10.1021/ma401306s	journal	September 2013
Highly Stable N3-Substituted Imidazolium-Based Alkaline Anion Exchange Membranes: Experimental Studies and Theoretical Calculations Gu, Fenglou; Dong, Huilong; Li, Youyong Macromolecules, Vol. 47, Issue 1 https://doi.org/10.1021/ma402334t	journal	December 2013
Nitroxide radical polymers – a versatile material class for high-tech applications Hansen, Kai-Anders; Blinco, James P. Polymer Chemistry, Vol. 9, Issue 13 https://doi.org/10.1039/C7PY02001E	journal	January 2018
Diamine compounds, methods of making same, method of use of same and intermediates Puckett, Wallace E.; Zollinger, Mark L. https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/5869655 US Patent Document 5,869,655	patent	February 1999
Imidazolium Cations with Exceptional Alkaline Stability: A Systematic Study of Structure–Stability Relationships Hugar, Kristina M.; Kostalik, Henry A.; Coates, Geoffrey W. Journal of the American Chemical Society, Vol. 137, Issue 27 https://doi.org/10.1021/jacs.5b02879	journal	July 2015
Poly(aryl Piperidinium) Polymers for Use as Hydroxide Exchange Membranes and Ionomers Yan, Yushan; Xu, Bingjun; Wang, Junhua https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20190036143 US Patent Application 16/146887; 20190036143	patent-application	January 2019
Anion Exchange Polymers and Anion Exchange Membranes Incorporating Same Bahar, Bamdad; Bae, Chulsung https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20170252707 US Patent Application 15/448734; 20170252707	patent-application	September 2017
Separating membrane of polyion complex Tsuyumoto, Michio; Sugimoto, Masahiko; Maeda, Yasushi https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/5393432 US Patent Document 5,393,432	patent	February 1995
Ion-conducting membranes Masel, Richard I.; Chen, Qingmei; Liu, Zengcai https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/9580824 US Patent Document 9,580,824	patent	February 2017
Robust Hydroxide Ion Conducting Poly(biphenyl alkylene)s for Alkaline Fuel Cell Membranes Lee, Woo-Hyung; Kim, Yu Seung; Bae, Chulsung ACS Macro Letters, Vol. 4, Issue 8 https://doi.org/10.1021/acsmacrolett.5b00375	journal	July 2015
Preparation and Characterization of Tetra-Imidazolium Hydroxide Polyphenylene Membranes via Nickel Catalyzed C–C Coupling Polymerization Jang, Hohyoun; Lee, Soonho; Ha, Jaeseong Energies, Vol. 9, Issue 4 https://doi.org/10.3390/en9040271	journal	April 2016
Certain Azoniaspironortropine Derivatives Pfleger, Robert; Bertholdt, Heinz; Schulz, Wolfram https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/3480626 US Patent Document 3480626	patent	November 1969
Poly(terphenylene) Anion Exchange Membranes: The Effect of Backbone Structure on Morphology and Membrane Property Lee, Woo-Hyung; Park, Eun Joo; Han, Junyoung ACS Macro Letters, Vol. 6, Issue 5 https://doi.org/10.1021/acsmacrolett.7b00148	journal	April 2017
Soluble, polymeric condensate of dibenzo-18-crown-6 and formaldehyde; synthesis, characterization and absorption of anionic copolymers Warshawsky, A.; Deshe, A.; Shechtman, L. Reactive Polymers, Vol. 12, Issue 3 https://doi.org/10.1016/0923-1137(90)90076-G	journal	June 1990
Water-insoluble anion exchanger materials Meier-Haack, Jochen https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/10046319 US Patent Document 10,046,319	patent	August 2018
Remarkable enhancement of reactivity of carbonyl compounds for polymerizations with non-activated aromatic hydrocarbons Zolotukhin, Mikhail; Fomine, Serguei; Salcedo, Roberto Chemical Communications, Issue 8 https://doi.org/10.1039/b317108f	journal	January 2004
Polymers and methods for their manufacture Bae, Chulsung; Lee, Woo Hyung https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/10435504 US Patent Document 10,435,504	patent	October 2019
A Novel, One-Pot Synthesis of Novel 3F, 5F, and 8F Aromatic Polymers Diaz, Adan M.; Zolotukhin, Mikhail G.; Fomine, Serguei Macromolecular Rapid Communications, Vol. 28, Issue 2 https://doi.org/10.1002/marc.200600656	journal	January 2007
Synthesis and gas transport properties of new aromatic 3F polymers Guzmán-Gutiérrez, M. T.; Zolotukhin, M. G.; Fritsch, D. Journal of Membrane Science, Vol. 323, Issue 2 https://doi.org/10.1016/j.memsci.2008.06.041	journal	October 2008
Novel Polymers and Methods for Their Manufacture Bae, Chulsung; Lee, Woo-hyung https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20170355811 US Patent Application 15/527,967; 2017/0355811 Al	patent-application	December 2017
Anion Exchange Membranes and Polymers for Use in Same Bae, Chulsung; Mohanty, Angela Dee https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20170203289 US Patent Application 15/326538; 20170203289	patent-application	July 2017
Functionalizing Polystyrene with N -Alicyclic Piperidine-Based Cations via Friedel–Crafts Alkylation for Highly Alkali-Stable Anion-Exchange Membranes Olsson, Joel S.; Pham, Thanh Huong; Jannasch, Patric Macromolecules, Vol. 53, Issue 12 https://doi.org/10.1021/acs.macromol.0c00201	journal	June 2020
Stabilizing the Imidazolium Cation in Hydroxide-Exchange Membranes for Fuel Cells Wang, Junhua; Gu, Shuang; Kaspar, Robert B. ChemSusChem, Vol. 6, Issue 11 https://doi.org/10.1002/cssc.201300285	journal	August 2013
Anion-Exchange Membranes for Alkaline Fuel-Cell Applications: The Effects of Cations Sun, Zhe; Lin, Bencai; Yan, Feng ChemSusChem, Vol. 11, Issue 1 https://doi.org/10.1002/cssc.201701600	journal	December 2017
A comparative study of anion-exchange membranes tethered with different hetero-cycloaliphatic quaternary ammonium hydroxides Dang, Hai-Son; Jannasch, Patric J. Mater. Chem. A, Vol. 5, Issue 41 https://doi.org/10.1039/C7TA06029G	journal	January 2017

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