Process for producing polyether ketone ketone

Patent metadata

Field	Value
Publication number	US-10793669-B2
Application number	US-201816053927-A
Country	US
Kind code	B2
Filing date	Aug 3, 2018
Priority date	Aug 4, 2017
Publication date	Oct 6, 2020
Grant date	Oct 6, 2020

Abstract

Further, a composition including at least 40 wt. % of 1,4-bis(4-phenoxybenzoyl)benzene-Lewis acid complex and an anhydrous aprotic solvent or solvent mixture, characterized in that it includes less than 1 wt. %, preferably less than 0.5 wt. % and in particular less than 0.1 wt. % of molecules including xanthydrol groups and its use for the manufacture of polyether ketone ketone.

First claim

The invention claimed is:

1. A method for the manufacture of polyether ketone ketone (PEKK), comprising:
(i) providing a 1,4-bis(4-phenoxybenzoyl)benzene-Lewis acid complex;
(ii) purifying said 1,4-bis(4-phenoxybenzoyl)benzene-Lewis acid complex;
(iii) reacting said 1,4-bis(4-phenoxybenzoyl)benzene-Lewis acid complex with at least one difunctional aromatic acyl chloride in a reaction solvent and optional additional Lewis acid to obtain a product mixture comprising a PEKK-Lewis acid complex; and
(iv) decomplexing the PEKK-Lewis acid complex to obtain a PEKK polymer.

2. The method of claim 1 , wherein step (i) comprises:
(a) providing a reactant mixture comprising terephthaloyl chloride and diphenyl ether in a reaction solvent;
(b) adding a Lewis acid to the reactant mixture, so as to obtain a product mixture comprising 1,4-bis(4-phenoxybenzoyl)benzene-Lewis acid complex.

3. The method of claim 1 , wherein the 1,4-bis(4-phenoxybenzoyl)benzene-Lewis acid complex is purified using ortho-dichlorobenzene.

4. The method of claim 1 , wherein the ortho-dichlorobenzene is recycled ortho-dichlorobenzene.

5. The method of claim 1 , wherein step (iv) comprises:
(a) contacting the obtained product mixture with a protic solvent so as to decomplex the PEKK-Lewis acid complex, whereby a dispersion is obtained that comprises a liquid phase comprising Lewis acid and a solid phase comprising PEKK; and
(b) separating the solid phase of the dispersion from the liquid phase, so as to recover a crude PEKK and an effluent containing Lewis acid.

6. The method of claim 5 , wherein the effluent containing Lewis acid is recycled.

7. The method of claim 1 , wherein the at least one difunctional aromatic acyl chloride is selected from the group consisting of terephtaloyl chloride, isophtaloyl chloride, and mixtures thereof.

8. The method of claim 2 , wherein the reaction solvent in step (ia) and step (iii) is ortho-dichlorobenzene, respectively.

9. The method of claim 1 , wherein the Lewis acid is aluminum trichloride.

10. The method of claim 5 , wherein the protic solvent in step (iva) is an aqueous solution.

11. The method of claim 1 , further comprising after step (iv) one or more steps of washing the crude PEKK in a protic solvent, and subjecting the resulting mixture to a further solid/liquid separation.

12. The method of claim 1 , further comprising after step (iv) one or more steps of washing the crude PEKK with a protic solvent, and subjecting the resulting mixture to a further solid/liquid separation.

13. The method of claim 1 , wherein step (iv) and each subsequent washing step is performed in a centrifugal filtration device, without removing the PEKK between subsequent steps.

14. The method of claim 1 , further comprising a subsequent step of drying the PEKK.

15. The method of claim 5 , wherein the protic solvent in step (iva) is an aqueous solution, which has a pH of not more than 5.

16. The method of claim 1 , further comprising after step (iv) one or more steps of washing the crude PEKK in methanol, and subjecting the resulting mixture to a further solid/liquid separation.

17. The method of claim 1 , further comprising after step (iv) one or more steps of washing the crude PEKK with water, and subjecting the resulting mixture to a further solid/liquid separation.

Assignees

• Arkema France

Inventors

• Le Guillaume
• Jouanneau Julien

Classifications

• C08G2650/40

  containing ketone groups, e.g. polyarylethylketones, PEEK or PEK · CPC title

• C08G2261/712

  Catalyst removal · CPC title

• C08G2261/45

  Friedel-Crafts-type · CPC title

• C08G2261/3442

  Polyetherketones · CPC title

• C08G65/00

  Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule · CPC title