Epoxy functionalized poly(aryl ether sulfones) copolymers

Patent metadata

Field	Value
Publication number	US-12384887-B2
Application number	US-202117790150-A
Country	US
Kind code	B2
Filing date	Jan 4, 2021
Priority date	Jan 7, 2020
Publication date	Aug 12, 2025
Grant date	Aug 12, 2025

Abstract

The invention pertains to a side-chain epoxy-functionalized copolymer (P1) and to the process for preparing this copolymer (P1). The present invention also pertains to the use of the copolymer (P1) in the preparation of a membrane, a composite material or a coating. The present invention also relates to a resin composition comprising at least the copolymer (P1) according to the present invention.

First claim

The invention claimed is:

1. A copolymer (P1) comprising:
recurring units (R P1 ) of formula (M):

and
recurring units (R* P1 ) of formula (N):

wherein
each R 1 is independently selected from the group consisting of a halogen, alkyl, alkenyl, alkynyl, aryl, ether, thioether, carboxylic acid, ester, amide, imide, alkali metal sulfonate, alkaline earth metal sulfonate, alkyl sulfonate, alkali metal phosphonate, alkaline earth metal phosphonate, alkyl phosphonate, amine and quaternary ammonium;
each i is independently selected from 0 to 4;
G N is selected from the group consisting of the following formulas:

each k is independently selected from 0 to 4;
each j is independently selected from 3 to 7;
T and Q are independently selected from the group consisting of a bond, —O—; —SO 2 —; —S—; —C(O)—; —C(CH 3 ) 2 —; —C(CF 3 ) 2 —; —C(═CCl 2 )—; —C(CH 3 )(CH 2 CH 2 COOH)—; —N═N—; —R a C═CR b —; —(CH 2 ) m —; —(CF 2 ) m —; a linear aliphatic divalent group of up to 6 carbon atoms, a branched aliphatic divalent group of up to 6 carbon atoms; and combinations thereof, in which each R a and R b , independently of one another, is hydrogen, a C1-C12-alkyl, a C1-C12-alkoxy, or a C6-C18-aryl group; and in which m is an integer from 1 to 6.

2. The copolymer (P1) of claim 1 , wherein T in the recurring units (R P1 ) is selected from the group consisting of a bond, —SO 2 — and —C(CH 3 ) 2 —.

3. The copolymer (P1) of claim 1 , wherein Q in the formulas (G N1 ), (G N2 ) and/or (G N3 ) of the recurring units (R* P1 ) is selected from the group consisting of a bond, —SO 2 — and —C(CH 3 ) 2 —.

4. The copolymer (P1) of claim 1 , wherein i is zero for each R 1 of the recurring units (R P1 ) and the recurring units (R* P1 ).

5. The copolymer (P1) of claim 1 , wherein k is 0 and j is 3 in the recurring units (R* P1 ).

6. The copolymer (P1) of claim 1 , wherein the molar ratio of the recurring units (R P1 )/recurring units (R* P1 ) varies between 0.01/100 and 100/0.01.

7. The copolymer (P1) of claim 1 , wherein the recurring units (R P1 ) are of formula (M1):

8. The copolymer (P1) of claim 1 , comprising collectively at least 50 mol. % of the recurring units (R P1 ) and (R* P1 ), based on the total moles of the recurring units in the copolymer (P1).

9. The copolymer (P1) of claim 1 , having a number average molecular weight (Mn) of less than 20,000 g/mol, as determined by GPC.

10. A process for preparing copolymer (P1) comprising at least partially epoxidizing a copolymer (P0) comprising:
recurring units (R P0 ) of formula (M):

and
recurring units (R* P0 ) of formula (P):

wherein
each R 1 is independently selected from the group consisting of a halogen, alkyl, alkenyl, alkynyl, aryl, ether, thioether, carboxylic acid, ester, amide, imide, alkali metal sulfonate, alkaline earth metal sulfonate, alkyl sulfonate, alkali metal phosphonate, alkaline earth metal phosphonate, alkyl phosphonate, amine and quaternary ammonium;
each i is independently selected from 0 to 4;
G P is selected from the group consisting of the following formulas:

each k is independently selected from 0 to 4,
T and Q are independently selected from the group consisting of a bond, —O—; —SO 2 —; —S—; —C(O)—; —C(CH 3 ) 2 —; —C(CF 3 ) 2 —; —C(═CCl 2 )—; —C(CH 3 )(CH 2 CH 2 COOH)—; —N═N—; —R a C═CR b —; —(CH 2 ) m —; —(CF 2 ) m —; a linear aliphatic divalent group of up to 6 carbon atoms, a branched aliphatic divalent group of up to 6 carbon atoms; and combinations thereof, in which each R a and R b , independently of one another, is hydrogen, a C1-C12-alkyl, a C1-C12-alkoxy, or a C6-C18-aryl group, and in which m is an integer from 1 to 6.

11. The process of claim 10 , being carried out:
in the presence of a peroxy acid, or
with at least one hydrogen peroxide precursor and at least one carboxylic acid or derivative thereof in the presence of water.

12. The process of claim 10 , wherein the copolymer (P0) comprises collectively at least 50 mol. % of the recurring units (R P0 ) and (R* P0 ), based on the total moles of the recurring units in the copolymer (P0).

13. A method for the preparation of a membrane, a composite material or a coating, comprising using the copolymer (P1) of claim 1 .

14. An epoxy resin composition comprising at least one epoxy compound and at least one of the copolymer (P1) according to claim 1 .

Assignees

• Solvay Specialty Polymers Usa

Inventors

• Nair Kamlesh
• Pollino Joel

Classifications

• C09D181/06

  Polysulfones; Polyethersulfones · CPC title

• C08K5/1515

  Three-membered rings · CPC title

• Y02E60/50

  Fuel cells · CPC title

• B01D71/46

  Epoxy resins · CPC title

• B01D71/76

  Macromolecular material not specifically provided for in a single one of groups B01D71/08 - B01D71/74 (rubbers in general B01D71/24) · CPC title