Cross-linked mixed-matrix membranes, composition and method

Patent metadata

Field	Value
Publication number	US-2024342662-A1
Application number	US-202118292758-A
Country	US
Kind code	A1
Filing date	Jul 29, 2021
Priority date	Jul 29, 2021
Publication date	Oct 17, 2024
Grant date	—

Abstract

The invention relates to a composition comprising: at least one porous solid additive having a charged surface; an IL; a polymerizable IL; and a cross-linker; wherein the cross-linker wherein the cross-linker has a high affinity to CO 2 over other light gas and comprises at least two polymerizable groups configured to react, in a radical polymerization reaction, with the polymerizable ionic liquid, said polymerizable groups preferably containing double bond.

First claim

1 . A composition comprising:
a porous solid additive having a charged surface; an ionic liquid; a polymerizable ionic liquid; and a cross-linker;
wherein the cross-linker has a high affinity to CO 2 over other light gas and comprises at least two polymerizable groups configured to react, in a radical polymerization reaction, with the polymerizable ionic liquid, said polymerizable groups containing a double bond.

2 . The composition according to claim 1 , wherein the cross-linker comprises a functional group having high affinity to CO 2 .

3 . The composition according to claim 2 , wherein the functional group having high affinity to CO 2 comprise at least a functional group selected from:
phosphonium; ammonium; imidazolium; and pyridinium.

4 . The composition according to claim 1 , wherein the cross-linker is selected from:

Wherein
R1 comprises a radically polymerizable double bond group;
R2 comprises a functional group having a high affinity for CO 2 over other light gases;
L refers to any carbon containing group capable of being a central point for a functional group having a high affinity for CO 2 to bond with;
n is an integer equal to or greater than 1.

5 . The composition according to claim 2 , wherein the functional group having high affinity to CO 2 comprise an imidazolium functional group, the cross-linker being selected from:

Wherein
R1 is independently selected from at least one radically polymerizable double bond group;
L is independently selected from an organyl group, a hydrocarbyl group; an alkyl group; an aliphatic group; a cycloalkyl group; an alkenyl group; an alkynyl group; an aromatic group; an aryl group; a heterocyclyl group; a cycloheteryl group; a heteroaryl group; an arylheteryl group; an organoheteryl group; an aralkyl group; a heteroaralkyl group; a halide; substituted or not;
n is an integer from 1 to 10.

6 . The composition according to claim 2 , wherein the functional group having high affinity to CO 2 comprise an ammonium functional group, the cross-linker being selected from:
R1-L-(AMO-L-R1)n
Wherein
R1 is independently selected from at least one radically polymerizable double bond group;
L is independently selected from an organyl group, a hydrocarbyl group; an alkyl group; an aliphatic group; a cycloalkyl group; an alkenyl group; an alkynyl group; an aromatic group; an aryl group; a heterocyclyl group; a cycloheteryl group; a heteroaryl group; an arylheteryl group; an organoheteryl group; an aralkyl group; a heteroaralkyl group; a halide; substituted or not;
AMO is independently selected from N, NR, NR 2 , wherein R is a hydrogen or is independently selected from: an organyl group, a hydrocarbyl group; an alkyl group; an aliphatic group; a cycloalkyl group; an alkenyl group; an alkynyl group; an aromatic group; an aryl group; a heterocyclyl group; a cycloheteryl group; a heteroaryl group; an arylheteryl group; an organoheteryl group; an aralkyl group; a heteroaralkyl group; a halide; substituted or not;
n is an integer from 1 to 10.

7 . The composition according to claim 2 , wherein the functional group having high affinity to CO 2 comprise an imidazolium functional group and an ammonium functional group.

8 . The composition according to claim 2 , wherein the functional group having high affinity to CO 2 comprise a phosphonium functional group, the cross-linker being selected from:
R1-L-(PHOS-L-R1)n
Wherein
R1 is independently selected from at least one radically polymerizable double bond group;
L is independently selected from an organyl group, a hydrocarbyl group; an alkyl group; an aliphatic group; a cycloalkyl group; an alkenyl group; an alkynyl group; an aromatic group; an aryl group; a heterocyclyl group; a cycloheteryl group; a heteroaryl group; an arylheteryl group; an organoheteryl group; an aralkyl group; a heteroaralkyl group; a halide; substituted or not;
PHOS is independently selected from P, PR, PR 2 wherein R is a hydrogen or is independently selected from: an organyl group, a hydrocarbyl group; an alkyl group; an aliphatic group; a cycloalkyl group; an alkenyl group; an alkynyl group; an aromatic group; an aryl group; a heterocyclyl group; a cycloheteryl group; a heteroaryl group; an arylheteryl group; an organoheteryl group; an aralkyl group; a heteroaralkyl group; a halide; substituted or not; and
n is an integer from 1 to 10.

9 . The composition according to claim 2 , wherein the functional group having high affinity to CO 2 comprises a pyridinium functional group, the cross-linker being selected from:
R1-L-(PYR-L-R1)n
Wherein
R1 is independently selected from at least one radically polymerizable double bond group;
L is independently selected from an organyl group, a hydrocarbyl group; an alkyl group; an aliphatic group; a cycloalkyl group; an alkenyl group; an alkynyl group; an aromatic group; an aryl group; a heterocyclyl group; a cycloheteryl group; a heteroaryl group; an arylheteryl group; an organoheteryl group; an aralkyl group; a heteroaralkyl group; a halide; substituted or not;
PYR is independently selected from C 5 H 5 N, R-C 5 H 4 N, R 2 C 5 H 3 N, R 3 C 5 H 2 N, R 4 -C 5 HN, R 5 C 5 N, wherein R is a hydrogen or is independently selected from: an organyl group, a hydrocarbyl group; an alkyl group; an aliphatic group; a cycloalkyl group; an alkenyl group; an alkynyl group; an aromatic group; an aryl group; a heterocyclyl group; a cycloheteryl group; a heteroaryl group; an arylheteryl group; an organoheteryl group; an aralkyl group; a heteroaralkyl group; a halide; substituted or not;
n is an integer from 1 to 10.

10 . The composition according to claim 1 , wherein the cross-linker further comprises a polar group selected from: ether, ethylene glycol, fluoroalkyl, aromatic ring, and nitrile.

11 . The composition according to claim 1 , wherein the cross-linker comprises a region of overlapping p orbitals allowing a delocalization of π electrons across all adjacent p orbitals.

12 . The composition according to claim 1 , wherein the cross-linker comprises two radically polymerizable double bonds groups, three radically polymerizable double bonds groups or four radically polymerizable double bonds groups.

13 . The composition according to claim 1 , wherein the porous solid additive is selected from zeolites, metal peroxides, zeolitic imidazolate frameworks and metal organic frameworks.

14 . The composition according to claim 1 , wherein the ionic liquid comprises a functional group selected from:
phosphonium; ammonium; imidazolium; and pyridinium.

15 . The composition according to claim 1 , wherein the polymerizable ionic liquid comprises a polymerizable group configured to react in a radical polymerization reaction with a polymerizable group of another polymerizable ionic liquid to form a polymer, and a group having high affinity to CO 2 over other light gas, said group having high affinity to CO 2 comprises phosphonium; ammonium; imidazolium; and/or pyridinium.

16 . A mixed-matrix membrane formed from the composition of claim 1 .

17 . A mixed-matrix membrane comprising:
a porous solid additive having a charged surface; an ionic liquid; and a polymerized matrix comprising an ionic liquid polymer covalently linked with a crosslinker;
wherein the cross linker has a high

Assignees

• Univ Colorado Regents
• Totalenergies Onetech

Inventors

• Gin Douglas L
• Dunn Collin A
• Noble Richard D
• Ben Hassine Haïfa

Classifications

• B01D2323/30

  Cross-linking · CPC title

• B01D2257/504

  Carbon dioxide · CPC title

• B01D71/40

  Polymers of unsaturated acids or derivatives thereof, e.g. salts, amides, imides, nitriles, anhydrides, esters · CPC title

• B01D53/228

  characterised by specific membranes · CPC title

• B01D71/0281

  Zeolites · CPC title