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US 11,299,464 B2Granted
Stable poly(imidazolium) hydroxides
AssigneeSimon Fraser University
InventorsSteven Holdcroft, Jiantao Fan, Andrew Wright, Benjamin Britton, Thomas Weissbach, Timothy James Peckham, Jonathan William Ward
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Abstract
Provided herein are imidazolium polymers having steric hindrance at the 4-position of the imidazole moieties in the polymeric chain. The sterically-protected, N-methylated imidazolium polymers exhibit hydroxide stability in concentrated caustic solutions at elevated temperatures, such as at 100° C. and higher.
Claims20
A polymer comprising a repeating unit of Formula (I):
- wherein:
- R1, R2, R4, and R5 are each independently selected from absent, alkyl, perfluoroalkyl, heteroalkyl, aryl, and aralkyl;
- provided that
- at least one of R1 and R2 is selected from alkyl, perfluoroalkyl, heteroalkyl, aryl, and aralkyl,
- when one of R1 and R2 is absent, the imidazolyl group to which the absent R1 or R2 is connected is neutral;
- and
- at least one of R4 and R5 is selected from alkyl, perfluoroalkyl, heteroalkyl, aryl, and aralkyl;
- and
- when one of R4 and R5 is absent, the imidazolyl group to which the absent R4 or R5 is connected is neutral;
- R3 and R6 are each independently selected from alkyl, perfluoroalkyl, heteroalkyl, aryl, aralkyl, and heteroaryl;
- R15 is arylene optionally substituted with 1, 2, 3, or 4 substituents independently selected from alkyl, perfluoroalkyl, heteroalkyl, and halo;
- R16 is arylene optionally substituted with 1, 2, 3, or 4 substituents independently selected from alkyl, perfluoroalkyl, heteroalkyl, and halo;
- R7, R10, R11, and R14 are each independently selected from alkyl, perfluoroalkyl, and heteroalkyl;
- and
- R8, R9, R12, and R13 are each independently selected from hydrogen, alkyl, perfluoroalkyl, and heteroalkyl.
12 more elements
A polymer comprising a repeating unit of Formula (II):
- wherein:
- R1, R2, R4, and R5 are each independently selected from absent, alkyl, perfluoroalkyl, heteroalkyl, aryl, and aralkyl;
- provided that
- at least one of R1 and R2 is selected from alkyl, perfluoroalkyl, heteroalkyl, aryl, and aralkyl,
- when one of R1 and R2 is absent, the imidazolyl group to which the absent R1 or R2 is connected is neutral;
- and
- at least one of R4 and R5 is selected from alkyl, perfluoroalkyl, heteroalkyl, aryl, and aralkyl;
- and
- when one of R4 and R5 is absent, the imidazolyl group to which the absent R4 or R5 is connected is neutral;
- R3 and R6 are each independently selected from alkyl, perfluoroalkyl, heteroalkyl, aryl, aralkyl, and heteroaryl;
- R7, R10, R11, and R14 are each independently selected from alkyl, perfluoroalkyl, and heteroalkyl;
- and
- R8 and R12 are each independently selected from hydrogen, alkyl, perfluoroalkyl, and heteroalkyl.
10 more elements
A random polymer, comprising repeating units of Formula (IV-A), (IV-B), and (IV-C):
- wherein
- one of R1a and R2a is absent and the remaining R1a or R2a is selected from alkyl, perfluoroalkyl, heteroalkyl, aryl, and aralkyl;
- one of R4a and R5a is absent and the remaining R4a or R5a is selected from alkyl, perfluoroalkyl, heteroalkyl, aryl, and aralkyl;
- one of R1b, R2b, R4b, and R5b is absent and the imidazolyl group to which the absent R1b, R2b, R4b, or R5b is connected is neutral, and the remaining three of R1b, R2b, R4b, and R5b are each independently selected from alkyl, perfluoroalkyl, heteroalkyl, aryl, and aralkyl;
- R1c, R2c, R4c, and R5c are each independently selected from alkyl, perfluoroalkyl, heteroalkyl, aryl, and aralkyl;
- R3a, R6a, R3b, R6b, R3c, and R6c are each independently selected from alkyl, perfluoroalkyl, heteroalkyl, aryl, aralkyl, and heteroaryl;
- R7a, R10a, R11a, R14a, R7b, R10b, R11b, R14b, R7c, R10c, R11c, and R14c are each independently selected from alkyl, perfluoroalkyl, and heteroalkyl;
- and
- R8a, R12a, R8b, R12b, R8c, and R12c are each independently selected from hydrogen, alkyl, perfluoroalkyl, and heteroalkyl;
- wherein the polymer comprises m mole percentage repeating units of Formula (IV-A), n mole percentage repeating units of Formula (IV-B), and p mole percentage repeating units of Formula (IV-C), and
- m is from 0 mole percent to 60 mole percent,
- n+p is 40 mole percent to 100 mole percent, and
- m+n+p=100%.
10 more elements
Dependencies are inferred from the claim text.