Zwitterionic poly(sulfobetaine arylene ether sulfone) polymer synthesis route and applications for desalination membranes

Patent metadata

Field	Value
Publication number	US-11499013-B2
Application number	US-201916374501-A
Country	US
Kind code	B2
Filing date	Apr 3, 2019
Priority date	Apr 3, 2018
Publication date	Nov 15, 2022
Grant date	Nov 15, 2022

Abstract

A zwitterionic polysulfone formed from an allyl-containing monomer, a phenol-containing monomer, and an aryl-halide-containing monomer. The zwitterionic polysulfone may be incorporated into a desalination membrane.

First claim

What is claimed is:

1. A polysulfone represented by the formula:

wherein each Z independently represents a single bond, a substituted carbon atom, or —SO 2 —, and x and y represent mole percent of the arylene ether sulfone component and the sulfobetaine arylene ether sulfone component, respectively, and x+y=100.

2. The polysulfone of claim 1 , wherein 0<y≤100.

3. The polysulfone of claim 2 , wherein 25≤y≤100.

4. The polysulfone of claim 2 , wherein 0<y≤25.

5. The polysulfone of claim 1 , wherein a molar mass of the polymer is in a range of about 5 kDa-35 kDa (Mn).

6. The polysulfone of claim 5 , wherein the molar mass (Mn) of the polymer is in the range of about 5 kDa to about 15 kDa.

7. The polysulfone of claim 5 , wherein the molar mass (Mn) of the polymer is in the range of about 15 kDa to about 35 kDa.

8. The polysulfone of claim 1 , wherein the zwitterionic component comprises about 2 wt % to about 20 wt % of the polymer.

9. The polysulfone of claim 7 , wherein the zwitterionic component comprises about 2 wt % to about 10 wt % of the polymer.

10. A method of synthesizing a polysulfone, the method comprising:
reacting 2,2′-diallylbisphenol A (DABA) with a 4,4′-dihalophenyl sulfone (DXDPS) to yield a poly(arylene ether sulfone) with pendant allyl groups; and reacting the poly(arylene ether sulfone) polymer with 2,2-dimethoxy-2-phenylacetophenone, 2-dimethylamino ethanethiol, and 1,3-propane sultone to yield a zwitterionic poly(sulfobetaine arylene ether sulfone) polymer.

11. The method of claim 10 , wherein reacting the DABA with the DXDPS occurs in the presence of combining an allyl-containing monomer in the presence of potassium carbonate, toluene, and N,N-dimethylacetamide or dimethyl sulfoxide.

12. The method of claim 10 , wherein DXDPS comprises 4,4′-dichlorophenyl sulfone, 4,4′-difluorophenyl sulfone, or a combination thereof.

13. A composition comprising:
the zwitterionic poly(arylene ether sulfone-co-sulfobetaine arylene ether sulfone) copolymer of claim 1 ; and
a polysulfone.

14. The composition of claim 13 , wherein the composition comprises about 2 wt % to about 6 wt % of the sulfobetaine arylene ether sulfone component, wherein the poly(arylene ether sulfone-co-sulfobetaine arylene ether sulfone) copolymer comprises an arylene ether sulfone component and a sulfobetaine arylene ether sulfone component.

15. The composition of claim 14 , wherein the poly(arylene ether sulfone-co-sulfobetaine arylene ether sulfone) copolymer comprises about 10 wt % of the sulfobetaine arylene ether sulfone component.

16. A membrane formed from the composition of claim 13 .

17. The polysulfone of claim 2 , wherein 25≤y≤75.

18. The polysulfone of claim 1 , wherein a molar mass of the polymer is in a range of about about 10 kDa to about 65 kDa (Mw).

Assignees

• Green Matthew
• Yang Yi
• Univ Arizona State

Inventors

• Green Matthew
• Yang Yi

Classifications

• C08G65/4056 Primary

  (I) or (II) containing sulfur (as the sulfone group C08G75/23) · CPC title

• B01D69/02

  characterised by their properties · CPC title

• B01D71/82

  characterised by the presence of specified groups, e.g. introduced by chemical after-treatment · CPC title

• C08L81/06

  Polysulfones; Polyethersulfones · CPC title

• B01D2325/28

  Degradation or stability over time · CPC title