Granted Patent B2

US 12,398,238 · App. 17/613,862 · Granted Aug 26, 2025

Inventors: Rajesh Chowdhury (Bangalore, IN); Senthil Tk (Bangalore, IN)

Assignee: SHPP GLOBAL TECHNOLOGIES B.V.

C08G65/485B01D3/143B01D71/5223C08J5/2256C08J2371/12H01M8/1025H01M2008/1095

Abstract

Claims (56)

1. A method for sulfonation of poly(phenylene ether), comprising

dissolving a poly(phenylene ether) comprising 2,6-dimethyl-1,4-phenylene ether units, 2,3,6-trimethyl-1,4-phenylene ether units, 3,3′,5,5′-tetramethyl-4,4′-dihydroxybiphenyl ether units, or a combination thereof, in 1,2-dichloroethane and a cosolvent to form a solvent mixture in a mixing vessel, wherein the cosolvent comprises methyl ethyl ketone, diethyl ether, methyl ethyl sulfone, ethyl acetate, tetramethylene sulfone, or a combination thereof;

combining a sulfonating agent with the solvent mixture, wherein the sulfonating agent reacts with the poly(phenylene ether) to form sulfonated poly(phenylene ether);

precipitating the sulfonated poly(phenylene ether); and

filtering the precipitated sulfonated poly(phenylene ether) to form a sulfonated poly(phenylene ether) precipitate and a filtrate;

wherein the sulfonated poly(phenylene ether) has a sulfonation level of 20 to 50%.

2. A method for sulfonation of poly(phenylene ether), comprising:

determining the desired sulfonation level;

if the desired sulfonation level is greater than 20% then dissolving a poly(phenylene ether) comprising 2,6-dimethyl-1,4-phenylene ether units, 2,3,6-trimethyl-1,4-phenylene ether units, 3,3′,5,5′-tetramethyl-4,4′-dihydroxybiphenyl ether units, or a combination thereof, in 1,2-dichloroethane and a cosolvent to form a solvent mixture in a mixing vessel, wherein the cosolvent comprises methyl ethyl ketone, diethyl ether, methyl ethyl sulfone, ethyl acetate, tetramethylene sulfone, or a combination thereof;

combining a sulfonating agent with the solvent mixture, wherein the sulfonating agent reacts with the poly(phenylene ether) to form sulfonated poly(phenylene ether);

precipitating the sulfonated poly(phenylene ether); and

filtering the precipitated sulfonated poly(phenylene ether) to form a sulfonated poly(phenylene ether) precipitate and a filtrate, and

if the desired sulfonation level is less than or equal to 20% then dissolving poly(phenylene ether) in a solvent mixture comprising 1,2-dichloroethane and greater than 1 to 10 wt % of a cosolvent, wherein the weight percentages are based upon 100 wt % of the solvent mixture, to form a solvent mixture in a mixing vessel; then combining a sulfonating agent with the solvent mixture, wherein the sulfonating agent reacts with the poly(phenylene ether) to form sulfonated poly(phenylene ether); precipitating the sulfonated poly(phenylene ether); and filtering the precipitated sulfonated poly(phenylene ether) to form a sulfonated poly(phenylene ether) precipitate and a filtrate.

3. The method of claim 1 , wherein the cosolvent comprises ethyl acetate, tetramethylene sulfone, or a combination thereof.

4. The method of claim 1 , wherein the cosolvent comprises ethyl acetate.

5. The method of claim 1 , wherein the cosolvent is ethyl acetate.

6. The method of claim 1 , wherein the dissolving is at a temperature of 30° C. to 60° C.

7. The method of claim 1 , wherein the solvent mixture comprised:

1 to 20 wt % of the poly(phenylene ether);

80 to 99 wt % of the 1,2-dichloroethane; and

1 to 10 wt % of the cosolvent;

wherein the weight percentages are based upon 100 wt % of the solvent mixture.

8. The method of claim 1 , wherein the solvent mixture comprised:

1 to 10 wt % of the poly(phenylene ether);

70 to 90 wt % of the 1,2-dichloroethane; and

1 to 10 wt % of the cosolvent;

wherein the weight percentages are based upon 100 wt % of the solvent mixture.

9. The method of claim 1 , further comprising recovering the solvent and the cosolvent.

10. The method of claim 9 , wherein recovering the solvent and the cosolvent comprises decantation of the filtrate, to form an organic stream, and distilling the organic stream.

11. The method of claim 9 , further comprising recycling the solvent and the cosolvent to the mixing vessel.

12. The method of claim 1 , wherein the sulfonation level is 25% to 50% as determined by NMR.

13. The method of claim 1 , wherein the sulfonated poly(phenylene ether) has a uniform sulfonation level of 20 to 50% as determined by NMR.

14. The method of claim 11 ,

wherein greater than 97 wt % of the 1,2-dichloroethane is recycled; and/or

wherein greater than 95 wt % of the cosolvent is recycled.

15. The method of claim 1 , wherein the cosolvent is present from greater than 1 to 10 wt % wherein the weight percentage are based upon 100 wt % of the solvent mixture.

16. The method of claim 1 , wherein the cosolvent is present from greater than 2 to 6 wt % wherein the weight percentage are based upon 100 wt % of the solvent mixture.

17. The method of claim 1 , wherein the solvent mixture comprised:

5 to 10 wt %, of the poly(phenylene ether);

80 to 90 wt % of the 1,2-dichloroethane; and

2 to 6 wt % of the cosolvent;

wherein the weight percentages are based upon 100 wt % of the solvent mixture.

18. A method for sulfonation of poly(phenylene ether), comprising

dissolving a poly(phenylene ether) comprising 2,6 dimethyl 1,4-phenylene ether units, 2,3,6 trimethyl-1,4-phenylene ether units, 3,3′,5,5′-tetramethyl-4,4′-dihydroxybiphenyl ether units, or a combination thereof, in 1,2-dichloroethane and optionally a cosolvent to form a solvent mixture in a mixing vessel;

combining a sulfonating agent with the solvent mixture, wherein the sulfonating agent reacts with the poly(phenylene ether) to form sulfonated poly(phenylene ether);

precipitating the sulfonated poly(phenylene ether); and

filtering the precipitated sulfonated poly(phenylene ether) to form a sulfonated poly(phenylene ether) precipitate and a filtrate;

wherein the sulfonated poly(phenylene ether) has a uniform sulfonation level of 20 to 50% as determined by NMR.

19. A method for sulfonation of poly(phenylene ether), comprising:

determining a desired sulfonation level;

if the desired sulfonation level is greater than 20% then dissolving a poly(phenylene ether) comprising 2,6 dimethyl 1,4-phenylene ether units, 2,3,6 trimethyl-1,4-phenylene ether units, 3,3′,5,5′-tetramethyl-4,4′-dihydroxybiphenyl ether units, or a combination thereof, in 1,2-dichloroethane and optionally a cosolvent to form a solvent mixture in a mixing vessel;

combining a sulfonating agent with the solvent mixture, wherein the sulfonating agent reacts with the poly(phenylene ether) to form sulfonated poly(phenylene ether);

precipitating the sulfonated poly(phenylene ether); and

filtering the precipitated sulfonated poly(phenylene ether) to form a sulfonated poly(phenylene ether) precipitate and a filtrate, and

if the desired sulfonation level is less than or equal to 20% then dissolving poly(phenylene ether) in 1,2-dichloroethane and optionally a cosolvent to form a solvent mixture in a mixing vessel; then combining a sulfonating agent with the solvent mixture, wherein the sulfonating agent reacts with the poly(phenylene ether) to form sulfonated poly(phenylene ether); precipitating the sulfonated poly(phenylene ether); and filtering the precipitated sulfonated poly(phenylene ether) to form a sulfonated poly(phenylene ether) precipitate and a filtrate;

wherein the sulfonated poly(phenylene ether) has a uniform sulfonation level as determined by NMR.

Assignments (2)

Priority Claims (1)

Continuity (1)

References Cited (52)