Ionic polyesters, polyethers, poly(ether sulfones), and related materials

Patent metadata

Field	Value
Publication number	US-11034794-B2
Application number	US-201916544137-A
Country	US
Kind code	B2
Filing date	Aug 19, 2019
Priority date	Oct 19, 2018
Publication date	Jun 15, 2021
Grant date	Jun 15, 2021

Abstract

Disclosed herein are ionic polymers incorporating an cationic atom in the polymer backbone.

First claim

What is claimed is:

1. An ionic polymer having the formula:

wherein L 1 and L 2 are independently selected from a chemical bond, C 1-4 alkyl, O, or S;
X 1 and X 2 are independently selected from O and S;
Z is selected from C(O), S(O), SO 2 , or P(O)(OR p ), wherein R p is selected from hydrogen, C 1-8 alkyl, aryl, C 1-8 heteroaryl, C 3-8 cycloalkyl, and C 1-8 heterocyclyl;
Cy 1 , Cy 2 , Cy 3 , and Cy 4 are independently selected from aryl, C 1-8 heteroaryl, C 3-8 cycloalkyl, or C 1-8 heterocyclyl;
Q 1 and Q 2 are independently selected from C 1-8 alkyl, C 2-8 alkyl, C 2-8 alkyl, aryl, C 1-8 heteroaryl, C 3-8 cycloalkyl, or C 1-8 heterocyclyl; wherein each of Q 1 and Q 2 comprise at least one cationic Group 15 atom that is not bonded to a hydrogen atom;
L 3 is a linker group; and
each A comprises at least one anionic group, and m is a integer such that the polymer is electrically balanced.

2. The polymer of claim 1 , wherein Q 1 and Q 2 independently comprise a group having the formula:

wherein each R is independently selected from C 1-8 alkyl, C 2-8 alkyl, C 2-8 alkyl, aryl, C 1-8 heteroaryl, C 3-8 cycloalkyl, or C 1-8 heterocyclyl, and two or more R groups may together form a ring.

3. The polymer of claim 1 , wherein Q 1 comprises a group having the formula:

wherein R Q1a and R Q1b are independently selected from C 1-8 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, aryl, C 1-8 heteroaryl, C 3-8 cycloalkyl, or C 1-8 heterocyclyl;
R Q1c and R Q1d are independently selected from null, C 1-8 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, aryl, C 1-8 heteroaryl, C 3-8 cycloalkyl, or C 1-8 heterocyclyl;
wherein any two or more of R Q1a , R Q1b , R Q1c , and R Q1d may together form a ring.

4. The polymer of claim 1 , wherein Q 2 comprises a group having the formula:

wherein R Q2a and R Q2b are independently selected from C 1-8 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, aryl, C 1-8 heteroaryl, C 3-8 cycloalkyl, or C 1-8 heterocyclyl;
R Q2c and R Q2d are independently selected from null, C 1-8 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, aryl, C 1-8 heteroaryl, C 3-8 cycloalkyl, or C 1-8 heterocyclyl;
wherein any two or more of R Q2a , R Q2b , R Q2c , and R Q2d may together form a ring.

5. The polymer of claim 1 , wherein Q 1 and Q 2 independently comprise a cationic heterocyclic selected from the group consisting of pyrazolium, pyridinium, pyrazinium, pyrimidinium, pryidazinium, piperidinium, pyrrolidinium, indolizinium, isoindolium, indolium, indazolium, imidazolium, oxazolium, triazolium, tetrazolium, thiazolium, purinium, isoquinolinium, quinolinium, phthalazinium, quinooxalinium, phenazinium, morpholininium, and mixtures thereof.

6. The polymer of claim 1 , wherein Q 1 comprises a cationic heterocycle having the formula:

wherein
each R is independently selected from L 1 , L 3 , F, Cl, Br, I, NO 2 , CN, R a , OR a , N(R a ) 2 , SO 2 R a , SO 2 N(R a ) 2 , C(O)R a ; C(O)OR a , OC(O)R a ; C(O)N(R a ) 2 , N(R a )C(O)R a , OC(O)N(R a ) 2 , N(R a )C(O)N(R a ) 2 , wherein R a is in each case independently selected from hydrogen, C 1-8 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, aryl, C 1-8 heteroaryl, C 3-8 cycloalkyl, or C 1-8 heterocyclyl;
each R 1 is independently selected from L 1 , L 3 , R a′ , OR a , N(R a ) 2 , SR a , SO 2 R a , SO 2 N(R a ) 2 , C(O)R a ; C(O)OR a , OC(O)R a ; C(O)N(R a ) 2 , N(R a )C(O)R a , OC(O)N(R a ) 2 , N(R a )C(O)N(R a ) 2 , wherein R a is in each case independently selected from hydrogen, C 1-8 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, aryl, C 1-8 heteroaryl, C 3-8 cycloalkyl, or C 1-8 heterocyclyl, and R a′ is in each case independently selected from C 1-8 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, aryl, C 1-8 heteroaryl, C 3-8 cycloalkyl, or C 1-8 heterocyclyl,
each R 1a is selected from null, L 1 , L 3 , R a′ , OR a , N(R a ) 2 , SR a , SO 2 R a , SO 2 N(R a ) 2 , C(O)R a ; C(O)OR a , OC(O)R a ; C(O)N(R a ) 2 , N(R a )C(O)R a , OC(O)N(R a ) 2 , N(R a )C(O)N(R a ) 2 , wherein R a is in each case independently selected from hydrogen, C 1-8 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, aryl, C 1-8 heteroaryl, C 3-8 cycloalkyl, or C 1-8 heterocyclyl; R a′ is in each case independently selected from C 1-8 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, aryl, C 1-8 heteroaryl, C 3-8 cycloalkyl, or C 1-8 heterocyclyl,
wherein any two or more R, R 1 and R 1a groups may together form a ring, and
wherein no Q 1 group contains more than one R 1a , L 1 and L 3 groups.

7. The polymer of claim 1 , wherein Q 2 comprises a cationic heterocycle having the formula:

wherein each R is independently selected from L 2 , L 3 , F, Cl, Br, I, NO 2 , CN, R a , OR a , N(R a ) 2 , SR a , SO 2 R a , SO 2 N(R a ) 2 , C(O)R a ; C(O)OR a , OC(O)R a ; C(O)N(R a ) 2 , N(R a )C(O)R a , OC(O)N(R a ) 2 , N(R a )C(O)N(R a ) 2 , wherein R a is in each case independently selected from hydrogen, C 1-8 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, aryl, C 1-8 heteroaryl, C 3-8 cycloalkyl, or C 1-8 heterocyclyl;
each R 1 is independently selected from L 2 , L 3 , R a′ , OR a , N(R a ) 2 , SR a , SO 2 R a , SO 2 N(R a ) 2 , C(O)R a ; C(O)OR a , OC(O)R a ; C(O)N(R a ) 2 , N(R a )C(O)R a , OC(O)N(R a ) 2 , N(R a )C(O)N(R a ) 2 , wherein R a is in each case independently selected from hydrogen, C 1-8 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, aryl, C 1-8 heteroaryl, C 3-8 cycloalkyl, or C 1-8 heterocyclyl; and R a′ is in each case independently selected from C 1-8 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, aryl, C 1-8 heteroaryl, C 3-8 cycloalkyl, or C 1-8 heterocyclyl,
each R 1a is either absent or independently selected from L 2 , L 3 , R a′ , OR a , N(R a ) 2 , SR a , SO 2 R a , SO 2 N(R a ) 2 , C(O)R a ; C(O)OR a , OC(O)R a ; C(O)N(R a ) 2 , N(R a )C(O)R a , OC(O)N(R a ) 2 , N(R a )C(O)N(R a ) 2 , wherein R a is in each case independently selected from hydrogen, C 1-8 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, aryl, C 1-8 heteroaryl, C 3-8 cycloalkyl, or C 1-8 heterocyclyl;
R a′ is in each case independently selected from C 1-8 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, aryl, C 1-8 heteroaryl, C 3-8 cycloalkyl, or C 1-8 heterocyclyl,
wherein any two or more R, R 1 and R 1a groups may together form a ring, and
wherein no Q 2 group contains more than one R 1a , L 2 and L 3 groups.

8. The polymer of claim 1 , wherein Q 1 is

wherein R is in each case independently selected from F, Cl, Br, I, NO 2 , CN, R a , OR a , N(R a ) 2 , SR a , SO 2 R a , SO 2 N(R a ) 2 , C(O)R a ; C(O)OR a , OC(O)R a ; C(O)N(R a ) 2 , N(R a )C(O)R a , OC(O)N(R a ) 2 , N(R a )C(O)N(R a ) 2 , wherein R a is in each case independently selected from hydrogen, C 1-8 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, aryl, C 1-8 heteroaryl, C 3-8 cycloalkyl, or C 1-8 heterocyclyl, wherein any two or more R groups may together form a ring.

9. The polymer of claim 1 , wherein Q 2 is

Assignees

• Univ Alabama

Inventors

• Bara Jason Edward
• O'Harra Kathryn Elizabeth
• Dennis Grayson Patrick

Classifications

• C08G73/0616

  with only two nitrogen atoms in the ring · CPC title

• C08G63/6856 Primary

  Dicarboxylic acids and dihydroxy compounds · CPC title

• C08G73/00

  Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00 {(polycarbodiimides prepared from isocyanates C08G18/025, C08G18/797)} · CPC title

• C08G63/6886

  Dicarboxylic acids and dihydroxy compounds · CPC title

• C08G65/325

  containing nitrogen · CPC title