Alkaline anion exchange membranes derived from diphenylethylene and co-monomer feedstock

Patent metadata

Field	Value
Publication number	US-11938472-B2
Application number	US-202117527652-A
Country	US
Kind code	B2
Filing date	Nov 16, 2021
Priority date	Oct 22, 2018
Publication date	Mar 26, 2024
Grant date	Mar 26, 2024

Abstract

The anion exchange membranes exhibit enhanced chemical stability and ion conductivity when compared with traditional styrene-based alkaline anion exchange membranes. A copolymer backbone is polymerized from a reaction medium that includes a diphenylalkylene and an alkadiene. The copolymer includes a plurality of pendant phenyl groups. The diphenyl groups on the polymer backbone are functionalized with one or more haloalkylated precursor substrates. The terminal halide from the precursor substrate can then be substituted with a desired ionic group. The diphenylethylene-based alkaline anion exchange membranes lack the α-hydrogens sharing tertiary carbons with phenyl groups from polystyrene or styrene-based precursor polymers, resulting in higher chemical stability. The ionic groups are also apart from each other by about 3 to 6 carbons in the polymer backbone, enhancing ion conductivity. These membrane are advantageous for use in fuel cells, electrolyzers employing hydrogen, ion separations, etc.

First claim

What is claimed is:

1. A method of making an ion exchange membrane material, comprising:
providing a reaction medium including a diphenylalkylene and an alkadiene;
copolymerizing a polymer from the diphenylalkylene and alkadiene, the polymer including a backbone having a plurality of pendant phenyl groups;
hydrogenating one or more unsaturated carbons of the polymer backbone;
functionalizing the polymer backbone with one or more haloalkylated precursor substrates; and
substituting a halide from the one or more haloalkylated precursor substrates with an ionic group.

2. The method according to claim 1 , wherein the diphenylalkylene is diphenylethylene.

3. The method according to claim 1 , wherein the alkadiene includes butadiene, isoprene, or combinations thereof.

4. The method according to claim 1 , wherein the plurality of pendant phenyl groups are diphenyl groups.

5. The method according to claim 1 , wherein the one or more haloalkylated precursor substrates include a tertiary alcohol and a halogenated hydrocarbon.

6. The method according to claim 5 , wherein the one or more haloalkylated precursor substrates include 7-bromo-2-methyl-2-heptan-ol, 6-bromo-2-methylhexan-2-ol, 5-bromo-2-methylpentan-2-ol, or combinations thereof.

7. The method according to claim 1 , wherein functionalizing the polymer backbone with one or more functional groups includes:
reacting the one or more haloalkylated precursor substrates with the phenyl groups.

8. The method according to claim 1 , wherein substituting a halide from the one or more haloalkylated precursor substrates with an ionic group includes:
reacting the one or more haloalkylated precursor substrates with trimethylamine.

9. A method of making an ion exchange membrane, comprising:
providing a reaction medium including a diphenylethylene and alkadiene monomers;
copolymerizing a polymer from the diphenylethylene and alkadiene monomers;
grafting one or more haloalkylated precursor substrates to the polymer;
substituting a halide from the one or more haloalkylated precursor substrates with an amine functional group to form an ion exchange membrane material; and
casting the ion exchange membrane material as an ion exchange membrane.

10. The method according to claim 9 , wherein the alkadiene monomers include butadiene, isoprene, or combinations thereof.

11. The method according to claim 9 , wherein the one or more haloalkylated precursor substrates include 7-bromo-2-methyl-2-heptan-ol, 6-bromo-2-methylhexan-2-ol, 5-bromo-2-methylpentan-2-ol, or combinations thereof.

12. The method according to claim 9 , wherein the amine functional group includes at least one alkyl group, aryl group, or combinations thereof.

Assignees

• Rensselaer Polytech Inst

Inventors

• Lee Sangwoo
• Bae Chulsung
• Briem Musashi J
• Park Sungmin

Classifications

• B01J41/07 Primary

  in the weakly basic form · CPC title

• B01D61/44

  Ion-selective electrodialysis · CPC title

• B01D71/06

  Organic material · CPC title

• B01J41/14

  obtained by reactions only involving unsaturated carbon-to-carbon bonds · CPC title

• B01J47/12

  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) · CPC title