Stable poly(imidazolium) hydroxides

Patent metadata

Field	Value
Publication number	US-11299464-B2
Application number	US-201716321414-A
Country	US
Kind code	B2
Filing date	Jul 29, 2017
Priority date	Jul 29, 2016
Publication date	Apr 12, 2022
Grant date	Apr 12, 2022

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.

First claim

The embodiments of the disclosure in which an exclusive property or privilege is claimed are defined as follows:

1. A polymer comprising a repeating unit of Formula (I):

wherein:
R 1 , R 2 , R 4 , and R 5 are each independently selected from absent, alkyl, perfluoroalkyl, heteroalkyl, aryl, and aralkyl;
provided that
at least one of R 1 and R 2 is selected from alkyl, perfluoroalkyl, heteroalkyl, aryl, and aralkyl,
when one of R 1 and R 2 is absent, the imidazolyl group to which the absent R 1 or R 2 is connected is neutral; and
at least one of R 4 and R 5 is selected from alkyl, perfluoroalkyl, heteroalkyl, aryl, and aralkyl; and
when one of R 4 and R 5 is absent, the imidazolyl group to which the absent R 4 or R 5 is connected is neutral;

R 3 and R 6 are each independently selected from alkyl, perfluoroalkyl, heteroalkyl, aryl, aralkyl, and heteroaryl;
R 15 is arylene optionally substituted with 1, 2, 3, or 4 substituents independently selected from alkyl, perfluoroalkyl, heteroalkyl, and halo;
R 16 is arylene optionally substituted with 1, 2, 3, or 4 substituents independently selected from alkyl, perfluoroalkyl, heteroalkyl, and halo;
R 7 , R 10 , R 11 , and R 14 are each independently selected from alkyl, perfluoroalkyl, and heteroalkyl; and
R 8 , R 9 , R 12 , and R 13 are each independently selected from hydrogen, alkyl, perfluoroalkyl, and heteroalkyl.

2. The polymer of claim 1 , wherein the polymer comprises a repeating unit of Formula (I-A):

wherein:
R 1 , R 2 , R 4 , and R 5 are each independently selected from absent, alkyl, perfluoroalkyl, heteroalkyl, aryl, and aralkyl;
provided that
at least one of R 1 and R 2 is selected from alkyl, perfluoroalkyl, heteroalkyl, aryl, and aralkyl,
when one of R 1 and R 2 is absent, the imidazolyl group to which the absent R 1 or R 2 is connected is neutral;
at least one of R 4 and R 5 is selected from alkyl, perfluoroalkyl, heteroalkyl, aryl, and aralkyl; and
when one of R 4 and R 5 is absent, the imidazolyl group to which the absent R 4 or R 5 is connected is neutral;

R 3 and R 6 are each independently selected from alkyl, perfluoroalkyl, heteroalkyl, aryl, aralkyl, and heteroaryl;
R 15 is arylene optionally substituted with 1, 2, 3, or 4 substituents independently selected from alkyl, perfluoroalkyl, heteroalkyl, and halo;
R 16 is arylene optionally substituted with 1, 2, 3, or 4 substituents independently selected from alkyl, perfluoroalkyl, heteroalkyl, and halo;
R 7 , R 10 , R 11 , and R 14 are each independently selected from alkyl, perfluoroalkyl, and heteroalkyl; and
R 8 , R 9 , R 12 , and R 13 are each independently selected from hydrogen, alkyl, perfluoroalkyl, and heteroalkyl.

3. The polymer of claim 1 , wherein the polymer comprises a repeating unit of Formula (I-B):

wherein:
R 1 , R 2 , R 4 , and R 5 are each independently selected from absent, alkyl, perfluoroalkyl, heteroalkyl, aryl, and aralkyl;
provided that
at least one of R 1 and R 2 is selected from alkyl, perfluoroalkyl, heteroalkyl, aryl, and aralkyl,
when one of R 1 and R 2 is absent, the imidazolyl group to which the absent R 1 or R 2 is connected is neutral; and
at least one of R 4 and R 5 is selected from alkyl, perfluoroalkyl, heteroalkyl, aryl, and aralkyl; and
when one of R 4 and R 5 is absent, the imidazolyl group to which the absent R 4 or R 5 is connected is neutral;

R 3 and R 6 are each independently selected from alkyl, perfluoroalkyl, heteroalkyl, aryl, aralkyl, and heteroaryl;
R 15 is arylene optionally substituted with 1, 2, 3, or 4 substituents independently selected from alkyl, perfluoroalkyl, heteroalkyl, and halo;
R 16 is arylene optionally substituted with 1, 2, 3, or 4 substituents independently selected from alkyl, perfluoroalkyl, heteroalkyl, and halo;
R 7 , R 10 , R 11 , and R 14 are each independently selected from alkyl, perfluoroalkyl, and heteroalkyl; and
R 8 , R 9 , R 12 , and R 13 are each independently selected from hydrogen, alkyl, perfluoroalkyl, and heteroalkyl.

4. The polymer of claim 1 , wherein the polymer comprises a repeating unit of Formula (I-C):

wherein:
R 1 , R 2 , R 4 , and R 5 are each independently selected from absent, alkyl, perfluoroalkyl, heteroalkyl, aryl, and aralkyl;
provided that
at least one of R 1 and R 2 is selected from alkyl, perfluoroalkyl, heteroalkyl, aryl, and aralkyl,
when one of R 1 and R 2 is absent, the imidazolyl group to which the absent R 1 and R 2 is connected is neutral; and
at least one of R 4 and R 5 is selected from alkyl, perfluoroalkyl, heteroalkyl, aryl, and aralkyl; and
when one of R 4 and R 5 is absent, the imidazolyl group to which the absent R 4 or R 5 is connected is neutral;

R 3 and R 6 are each independently selected from alkyl, perfluoroalkyl, heteroalkyl, aryl, aralkyl, and heteroaryl;
R 15 is arylene optionally substituted with 1, 2, 3, or 4 substituents independently selected from alkyl, perfluoroalkyl, heteroalkyl, and halo;
R 16 is arylene optionally substituted with 1, 2, 3, or 4 substituents independently selected from alkyl, perfluoroalkyl, heteroalkyl, and halo;
R 7 , R 10 , R 11 , and R 14 are each independently selected from alkyl, perfluoroalkyl, and heteroalkyl; and
R 8 , R 9 , R 12 , and R 13 are each independently selected from hydrogen, alkyl, perfluoroalkyl, and heteroalkyl.

5. The polymer of claim 1 , wherein the polymer comprises a repeating unit of Formula (I-D):

wherein:
R 1 , R 2 , R 4 , and R 5 are each independently selected from absent, alkyl, perfluoroalkyl, heteroalkyl, aryl, and aralkyl;
provided that
at least one of R 1 and R 2 is selected from alkyl, perfluoroalkyl, heteroalkyl, aryl, and aralkyl,
when one of R 1 and R 2 is absent, the imidazolyl group to which the absent R 1 or R 2 is connected is neutral; and
at least one of R 4 and R 5 is selected from alkyl, perfluoroalkyl, heteroalkyl, aryl, and aralkyl; and
when one of R 4 and R 5 is absent, the imidazolyl group to which the absent R 4 or R 5 is connected is neutral;

R 3 and R 6 are each independently selected from alkyl, perfluoroalkyl, heteroalkyl, aryl, aralkyl, and heteroaryl;
R 15 is arylene optionally substituted with 1, 2, 3, or 4 substituents independently selected from alkyl, perfluoroalkyl, heteroalkyl, and halo;
R 16 is arylene optionally substituted with 1, 2, 3, or 4 substituents independently selected from alkyl, perfluoroalkyl, heteroalkyl, and halo;
R 7 , R 10 , R 11 , and R 14 are each independently selected from alkyl, perfluoroalkyl, and heteroalkyl; and
R 8 , R 9 , R 12 , and R 13 are each independently selected from hydrogen, alkyl, perfluoroalkyl, and heteroalkyl.

6. The polymer of claim 1 , wherein R 1 , R 2 , R 4 , and R 5 are each independently selected from absent, methyl, and trifluoromethyl; provided that
at least one of R 1 and R 2 is selected from methyl and trifluoromethyl; and
at least one of R 4 and R 5

Assignees

• Univ Fraser Simon

Inventors

• Holdcroft Steven
• Fan Jiantao
• Wright Andrew
• Britton Benjamin
• Weissbach Thomas
• Peckham Timothy James
• Ward Jonathan William

Classifications

• A61P31/00 Primary

  Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics · CPC title

• C07D233/64 Primary

  with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine · CPC title

• C08G73/0616

  with only two nitrogen atoms in the ring · CPC title

• C08G12/06

  Amines · CPC title