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US 11,834,544 B2Granted
Anion exchange membranes based on polymerization of long chain alpha olefins
Assignees3M Innovative Properties Company, The Penn State Research Foundation
InventorsMichael A. Yandrasits, Carl A. Laskowski, Timothy M. Gillard, Michael Hickner, Liang Zhu
Life of this patent
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Abstract
Described herein are cationic polymers having a plurality of quaternary amino groups, methods of making such polymers, and uses of such polymers as ion exchange membranes in electrochemical devices.
Claims15
A method for preparing a cationic polymer having a plurality of quaternary amino groups, the method comprising:
- obtaining or providing a precursor polymer comprising x repeat units of Formula (I) and y repeat units of Formula (II)
- wherein
- each R1 is independently aralkyl or substituted aralkyl;
- each R2 is independently pendant *—R3-L groups,
- R3 is alkylene having at least four carbon atoms;
- L is a leaving group;
- the asterisk (*) represents the point of attachment of R3 to the polymer backbone;
- the variable x represents an overall mole fraction of the repeat units of Formula (I) in the precursor polymer, with random or block repeat unit distribution;
- the variable y represents an overall mole fraction of the repeat units of Formula (II) in the precursor polymer, with random or block monomer repeat unit distribution, wherein y is in a range of about 0.15 to about 0.35;
- and
- reacting the pendant *—R3-L groups of the precursor polymer with a cationic amine compound having at least one tertiary amino group and at least one quaternary amino group to form the cationic polymer having the plurality of pendant quaternary amino groups, wherein the cationic polymer having the plurality of pendant quaternary amino groups comprises x repeat units of Formula (I) and z repeat units of Formula (IV)
- wherein
- each R4 is independently a cationic group of the Formula (V) or Formula (VI)
- *—R3—[N(R5)2]+—R6—{[N(R5)2]+—R6}v—[N(R5)3]+ (V)
- each R5 is independently alkyl;
- each R6 is independently alkylene;
- v is an integer in a range of 0 to 10;
- each R7 is an alkyl;
- each R8 is an alkylene;
- each R9 is an alkyl;
- each q is independently an integer in a range of 1 to 2;
- and
- p is an integer in a range of 0 to 10;
- and
- the variable z represents the overall mole fraction of the repeat units of Formula (IV) in the cationic polymer, with random or block monomer repeat unit distribution, wherein z is in a range of 0.15 to about 0.35;
- and
- the cationic group has corresponding anionic counter ions.
24 more elements
A cationic polymer comprising x repeat units of Formula (I) and z repeat units of Formula (IV)
- wherein
- each R1 is independently aralkyl or substituted aralkyl;
- the variable x represents an overall mole fraction of the repeat units of Formula (I) in the cationic polymer, with random or block repeat unit distribution;
- each R4 is independently a cationic group of the Formula (V) or Formula (VI)
- *—R3—[N(R5)2]+—R6—{[N(R5)2]+—R6}v—[N(R5)3]+ (V)
- each R5 is independently alkyl;
- each R6 is independently alkylene;
- v is an integer in a range of 0 to 10;
- each R7 is an alkyl;
- each R8 is an alkylene;
- each R9 is an alkyl;
- each q is independently an integer in a range of 1 to 2;
- and
- p is an integer in a range of 0 to 10;
- the variable z represents the overall mole fraction of the repeat units of Formula (IV) in the cationic polymer, with random or block monomer repeat unit distribution, wherein z is in a range of 0.15 to about 0.35;
- and
- the cationic group has corresponding anionic counter ions.
14 more elements
Dependencies are inferred from the claim text.