Ionic polyimide materials and methods of use

Patent metadata

Field	Value
Publication number	US-9845380-B2
Application number	US-201514982386-A
Country	US
Kind code	B2
Filing date	Dec 29, 2015
Priority date	Dec 30, 2014
Publication date	Dec 19, 2017
Grant date	Dec 19, 2017

Abstract

Disclosed are compositions and methods of preparing ionic polyimides. Also disclosed are methods to tune the properties of the ionic polyimide by designing the components of the ionic polyimide. Additionally, disclosed herein is a composition comprising an ionic polyimide. Also disclosed herein is a composition comprising an ionic polyimide and an ionic liquid. The disclosed compositions can be utilized to capture gases.

First claim

What is claimed is:

1. A composition, comprising an ionic polyimide having the formula:

wherein,
Y is selected from the group consisting of null, hydrogen, halogen, hydroxyl, carbonyl, O, S, SO 2 , cyano, C(CF 3 ) 2 , substituted or unsubstituted C 1-20 alkyl, substituted or unsubstituted C 2-20 alkenyl, substituted or unsubstituted C 2-20 alkynyl, substituted or unsubstituted C 1-20 heteroalkyl, substituted or unsubstituted C 2-20 heteroalkenyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl;
Z is selected from the group consisting of CH, CH 2 , carbonyl, O, S, SO 2 , cyano, C(CF 3 ) 2 , substituted or unsubstituted C 1-20 alkyl, substituted or unsubstituted C 2-20 alkenyl, substituted or unsubstituted C 2-20 alkynyl, substituted or unsubstituted C 1-20 heteroalkyl, substituted or unsubstituted C 2-20 heteroalkenyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl;
L 1 and L 2 are selected from the group consisting of branched and unbranched alkyl, alkenyl, and alkynyl groups having 1 to 12 carbon atoms, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl, and mixture thereof;
Q is an ionized heteroaryl;
A is an anion; and
n is an integer from 1 to 100,000.

2. The composition of claim 1 , wherein Q is selected from the group consisting of substituted or unsubstituted pyrazolium, substituted or unsubstituted pyridinium, substituted or unsubstituted pyrazinium, substituted or unsubstituted pyrimidinium, substituted or unsubstituted pryidazinium, substituted or unsubstituted piperidinium, substituted or unsubstituted pyrrolidinium, substituted or unsubstituted indolizinium, substituted or unsubstituted isoindolium, substituted or unsubstituted indolium, substituted or unsubstituted indazolium, substituted or unsubstituted imidazolium, substituted or unsubstituted oxazolium, substituted or unsubstituted triazolium, substituted or unsubstituted tetrazolium, substituted or unsubstituted thiazolium, substituted or unsubstituted purinium, substituted or unsubstituted isoquinolinium, substituted or unsubstituted quinolinium, substituted or unsubstituted phthalazinium, substituted or unsubstituted quinooxalinium, substituted or unsubstituted phenazinium, and substituted or unsubstituted morpholininium.

3. The composition of claim 1 , wherein Q is substituted with a functional group selected from the group consisting of alkyl, halogen, alkoxyl, alkenyl, alkynyl, aryl, heteroaryl, aldehyde, amino, carboxylic acid, ester, ether, halide, hydroxy, ketone, nitro, silyl, sulfo-oxo, sulfonyl, sulfone, sulfoxide, and thiol.

4. The composition of claim 1 , wherein Q is imidazolium.

5. The composition of claim 1 , wherein A is selected from the group consisting of chloride, bromide, iodide, nitrate, dicyanamide, acetate, bis(trifluoromethane)sulfonamide, hexafluorophosphate, tetrafluoroborate, sulfate, phosphate, tris(perfluoroalkyl)trifluorophosphatemesylate, aluminum chloride, thiocyanide, mesylate, triflate, and tosylate.

6. The composition of claim 1 , wherein Y and Z together with the atoms to which they are attached form a substituted or unsubstituted triptycene.

7. The composition of claim 1 , wherein the ionic polyimide is selected from the group consisting of:

wherein n is an integer from 1 to 100,000.

8. The composition of claim 1 , wherein n is an integer from 10 to 5,000.

9. The composition of claim 1 , further comprising an ionic liquid having the formula:

wherein,
R 1 , R 2 , R 3 , R 4 , and R 5 are, independent of one another, selected from the group consisting of hydrogen, branched or unbranched C 1-12 alkyl, branched or unbranched C 2-12 alkenyl, and branched or unbranched C 2-12 alkynyl; and
A 1 is an anion.

10. The composition of claim 9 , wherein A and A 1 are independently selected from the group consisting of chloride, bromide, iodide, nitrate, dicyanamide, acetate, bis(trifluoromethane)sulfonamide, hexafluorophosphate, tetrafluoroborate, sulfate, phosphate, tris(perfluoroalkyl)trifluorophosphatemesylate, aluminum chloride, thiocyanide, mesylate, triflate, and tosylate.

11. The composition of claim 9 , wherein the ionic liquid is 1-ethyl-3-methylimidazolium bis(trifluoromethane)sulfonamide.

12. The composition of claim 11 , wherein the ionic polyimide is selected from the group consisting of:

wherein n is an integer from 1 to 100,000.

13. The composition of claim 9 , wherein n is an integer from 10 to 5,000.

14. A method for capturing carbon dioxide from a gas stream, comprising:
feeding the gas stream through a membrane, wherein the membrane comprises an ionic polyimide having the following structure:

wherein,
Y is selected from the group consisting of null, hydrogen, halogen, hydroxyl, carbonyl, O, S, SO 2 , cyano, C(CF 3 ) 2 , substituted or unsubstituted C 1-20 alkyl, substituted or unsubstituted C 2-20 alkenyl, substituted or unsubstituted C 2-20 alkynyl, substituted or unsubstituted C 1-20 heteroalkyl, substituted or unsubstituted C 2-20 heteroalkenyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted triptycene, and substituted or unsubstituted heteroaryl;
Z is selected from the group consisting of CH, CH 2 , carbonyl, O, S, SO 2 , cyano, C(CF 3 ) 2 , substituted or unsubstituted C 1-20 alkyl, substituted or unsubstituted C 2-20 alkenyl, substituted or unsubstituted C 2-20 alkynyl, substituted or unsubstituted C 1-20 heteroalkyl, substituted or unsubstituted C 2-20 heteroalkenyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted triptycene, and substituted or unsubstituted heteroaryl;
L 1 and L 2 are selected from the group consisting of branched and unbranched alkyl, alkenyl, and alkynyl groups having 1 to 12 carbon atoms, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl, and mixture thereof;
Q is an ionized heteroaryl;
A is an anion; and
n is an integer from 1 to 100,000.

15. The method of claim 14 , wherein Q is selected from the group consisting of substituted or unsubstituted pyrazolium, substituted or unsubstituted pyridinium, substituted or unsubstituted pyrazinium, substituted or unsubstituted pyrimidinium, substituted or unsubstituted pryidazinium, substituted or unsubstituted piperidinium, substituted or unsubstituted pyrrolidinium, substituted or unsubstituted indolizinium, substituted or unsubstituted isoindolium, substituted or unsubstituted indolium, substituted or unsubstituted indazolium, substituted or unsubstituted imidazolium, substituted or unsubstituted oxazolium, substituted or unsubstituted triazol

Assignees

• Univ Alabama

Inventors

• Bara Jason Edward
• Shannon Matthew S
• Roveda Jr John David
• Wallace David A
• Mittenthal Max Simon

Classifications

• B01D2252/30

  Ionic liquids and zwitter-ions · CPC title

• B01D53/1475

  Removing carbon dioxide · CPC title

• B01D2257/504

  Carbon dioxide · CPC title

• C08L79/08

  Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors · CPC title

• Y02C10/10

  Cross-Sectional Technologies · mapped topic