IP Library Granted Patent US 11,434,365
Granted Patent B2
US 11,434,365 · App. 16/763,725 · Granted Sep 6, 2022

Use of a sulfonated polyaryl ether ketone or of a sulfonated non-polymeric aryl ether ketone as a dispersant

Inventors: Guillaume Le (Herouville Saint Clair, FR); Fabien Sguerra (Saint Laurent du Var, FR); Julien Jouanneau (Bryn Mawr, PA)
Assignee: ARKEMA FRANCE
C08L71/00C08J5/243C08L71/08D06M15/53D06M15/63D06M15/705C08J2371/08C08J2471/08C08L2201/54C08L2205/025D06M2101/40
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Quick Facts
Patent No.
US 11,434,365
App. No.
16/763,725
Granted
Sep 6, 2022
Kind
B2
Abstract

The use of a sulfonated polyaryl ether ketone or of a sulfonated non-polymeric aryl ether ketone as a dispersant for a polyaryl ether ketone resin powder in an aqueous solution, and also to a corresponding composition, and to a process for preparing a semifinished product comprising a polyaryl ether ketone resin and reinforcing fibers.

Claims (38)

1. A method comprising dispersing a polyaryl ether ketone resin powder in an aqueous solution with a sulfonated polyaryl ether ketone.

2. The method as claimed in claim 1 , in which the polyaryl ether ketone is chosen from the group consisting of polyether ketones (PEK), polyether ether ketones (PEEK), polyether ether ketone ketones (PEEKK), polyether ketone ketones (PEKK), polyether ketone ether ketone ketones (PEKEKK), polyether ether ketone ether ketones (PEEKEK), polyether ether ether ketones (PEEEK), polyether diphenyl ether ketones (PEDEK), mixtures thereof and copolymers comprising same.

3. The method as claimed in claim 1 , in which the sulfonated polyaryl ether ketone is chosen from the group consisting of sulfonated polyether ketones (PEK), sulfonated polyether ether ketones (PEEK), sulfonated polyether ether ketone ketones (PEEKK), sulfonated polyether ketone ketones (PEKK), sulfonated polyether ketone ether ketone ketones (PEKEKK), sulfonated polyether ether ketone ether ketones (PEEKEK), sulfonated polyether ether ether ketones (PEEEK), sulfonated polyether diphenyl ether ketones (PEDEK), mixtures thereof and copolymers comprising same.

4. The method as claimed in claim 1 , in which the sulfonated polyaryl ether ketone has a degree of sulfonation of from 0.01 to 4.

5. The method as claimed in claim 1 , in which the sulfonated polyaryl ether ketone includes sulfonated groups chosen from sulfonic acid groups and/or sulfonate groups, the molar proportion of sulfonate groups in the sulfonated polyaryl ether ketone, relative to the total amount of sulfonated groups, being greater than or equal to 50%.

6. A composition comprising a polyaryl ether ketone resin powder suspended in an aqueous solution, the composition also comprising a sulfonated polyaryl ether ketone.

7. The composition as claimed in claim 6 , in which the polyaryl ether ketone is chosen from the group consisting of polyether ketones (PEK), polyether ether ketones (PEEK), polyether ether ketone ketones (PEEKK), polyether ketone ketones (PEKK), polyether ketone ether ketone ketones (PEKEKK), polyether ether ketone ether ketones (PEEKEK), polyether ether ether ketones (PEEEK), polyether diphenyl ether ketones (PEDEK), mixtures thereof and copolymers comprising same.

8. The composition as claimed in claim 6 , in which the sulfonated polyaryl ether ketone is chosen from the group consisting of sulfonated polyether ketones (PEK), sulfonated polyether ether ketones (PEEK), sulfonated polyether ether ketone ketones (PEEKK), sulfonated polyether ketone ketones (PEKK), sulfonated polyether ketone ether ketone ketones (PEKEKK), sulfonated polyether ether ketone ether ketones (PEEKEK), sulfonated polyether ether ether ketones (PEEEK), sulfonated polyether diphenyl ether ketones (PEDEK), mixtures thereof and copolymers comprising same.

9. The composition as claimed in claim 6 , in which the sulfonated polyaryl ether ketone has a degree of sulfonation of from 0.01 to 4.

10. The composition as claimed in claim 6 , in which the sulfonated polyaryl ether ketone includes sulfonated groups chosen from sulfonic acid groups and/or sulfonate groups, the molar proportion of sulfonate groups in the sulfonated polyaryl ether ketone, relative to the total amount of sulfonated groups, being greater than or equal to 50%.

11. The composition as claimed in claim 6 , in which the mass content of sulfonated polyaryl ether ketone, relative to the polyaryl ether ketone resin powder, is from 0.1% to 20%.

12. A process for preparing a semifinished product comprising a polyaryl ether ketone resin and reinforcing fibers, comprising:

the provision of a composition as claimed in claim 6 , and the impregnation of reinforcing fibers with this composition;

drying of the impregnated reinforcing fibers;

heating of the impregnated reinforcing fibers so as to melt the polyaryl ether ketone; and

optionally, a calendering step.

13. The preparation process as claimed in claim 12 , in which the reinforcing fibers are carbon fibers.

14. The preparation process as claimed in claim 12 , in which the semifinished product is chosen from a prepreg or a tape.

15. A semifinished product which is prepared according to the process of claim 12 .

16. A process comprising manufacturing a composite material, the method comprising manufacturing with the semifinished product as claimed in claim 15 .

17. A method comprising dispersing a polyaryl ether ketone resin powder in an aqueous solution with a sulfonated non-polymeric aryl ether ketone.

18. The method as claimed in claim 17 , in which the sulfonated non-polymeric aryl ether ketone is sulfonated 1,4-bis(4-phenoxybenzoyl)benzene.

19. The method as claimed in claim 17 , in which the polyaryl ether ketone is chosen from the group consisting of polyether ketones (PEK), polyether ether ketones (PEEK), polyether ether ketone ketones (PEEKK), polyether ketone ketones (PEKK), polyether ketone ether ketone ketones (PEKEKK), polyether ether ketone ether ketones (PEEKEK), polyether ether ether ketones (PEEEK), polyether diphenyl ether ketones (PEDEK), mixtures thereof and copolymers comprising same.

20. The method as claimed in claim 17 , in which the sulfonated non-polymeric aryl ether ketone includes sulfonated groups chosen from sulfonic acid groups and/or sulfonate groups, the molar proportion of sulfonate groups in the sulfonated non-polymeric aryl ether ketone, relative to the total amount of sulfonated groups, being greater than or equal to 50%.

21. A composition comprising a polyaryl ether ketone resin powder suspended in an aqueous solution, the composition also comprising a sulfonated non-polymeric aryl ether ketone.

22. The composition as claimed in claim 21 , in which the sulfonated non-polymeric aryl ether ketone is sulfonated 1,4-bis(4-phenoxybenzoyl)benzene.

23. The composition as claimed in claim 21 , in which the polyaryl ether ketone is chosen from the group consisting of polyether ketones (PEK), polyether ether ketones (PEEK), polyether ether ketone ketones (PEEKK), polyether ketone ketones (PEKK), polyether ketone ether ketone ketones (PEKEKK), polyether ether ketone ether ketones (PEEKEK), polyether ether ether ketones (PEEEK), polyether diphenyl ether ketones (PEDEK), mixtures thereof and copolymers comprising same.

24. The composition as claimed in claim 21 , in which the sulfonated non-polymeric aryl ether ketone includes sulfonated groups chosen from sulfonic acid groups and/or sulfonate groups, the molar proportion of sulfonate groups in the sulfonated non-polymeric aryl ether ketone, relative to the total amount of sulfonated groups, being greater than or equal to 50%.

25. The composition as claimed in claim 21 , in which the mass content of sulfonated non-polymeric aryl ether ketone, relative to the polyaryl ether ketone resin powder, is from 0.1% to 20%.

26. A process for preparing a semifinished product comprising a polyaryl ether ketone resin and reinforcing fibers, comprising:

the provision of a composition as claimed in claim 21 , and the impregnation of reinforcing fibers with this composition;

drying of the impregnated reinforcing fibers;

heating of the impregnated reinforcing fibers so as to melt the polyaryl ether ketone; and

optionally, a calendering step.

27. The preparation process as claimed in claim 26 , in which the reinforcing fibers are carbon fibers.

28. The preparation process as claimed in claim 26 , in which the semifinished product is chosen from a prepreg or a tape.

29. A semifinished product which is prepared according to the process of claim 26 .

30. A process comprising manufacturing a composite material, the method comprising manufacturing with the semifinished product as claimed in claim 29 .

Assignments (2)
CHANGE OF ADDRESS Recorded Jul 4, 2025
From: ARKEMA FRANCE
To: ARKEMA FRANCE
Reel/Frame 071814/0739 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 6, 2022
From: LE, GUILLAUME; SGUERRA, FABIEN; JOUANNEAU, JULIEN
To: ARKEMA FRANCE
Reel/Frame 059835/0341 →