Method of polyarylene sulfide crystallization

Patent metadata

Field	Value
Publication number	US-9868824-B2
Application number	US-201615202730-A
Country	US
Kind code	B2
Filing date	Jul 6, 2016
Priority date	Sep 25, 2013
Publication date	Jan 16, 2018
Grant date	Jan 16, 2018

Abstract

A method for formation of a semi-crystalline polyarylene sulfide is described. The method can include reaction of sulfur-containing monomer with a dihaloaromatic monomer in an organic amide solvent to form a polymer following by combination of the polymer with a crystallization solution. The crystallization solution is pre-heated and the mixture formed is slowly cooled to crystallize the polymer.

First claim

What is claimed is:

1. A method for forming a semi-crystalline polyarylene sulfide comprising:
polymerizing a first sulfur-containing monomer and a first dihaloaromatic monomer in an organic amide solvent to form a polyarylene sulfide prepolymer;
polymerizing the polyarylene sulfide prepolymer with a second dihaloaromatic monomer and a second sulfur-containing monomer;
combining the polyarylene sulfide with a crystallization solution to form a polymer mixture, the mixture including the crystallization solution in an amount of about 5 wt.% or greater by weight of the mixture, wherein the crystallization solution is pre-heated prior to combination with the polyarylene sulfide, the polymer mixture being at a temperature of about 230° C. or greater upon formation; and
cooling the polymer mixture at a rate of about 0.5° C. per minute or less until the polymer mixture reaches a temperature of about 190° C. or less, the polyarylene sulfide crystallizing during the cooling to form the semi-crystalline polyarylene sulfide.

2. The method of claim 1 , wherein the crystallization solution is pre-heated to a temperature of from about 50° C. to about 200° C.

3. The method of claim 1 , wherein the crystallization solution comprises water.

4. The method of claim 3 , wherein the mixture includes the crystallization solution in an amount of from about 3 wt. % to about 10 wt. % of the mixture.

5. The method of claim 1 , wherein the crystallization solution includes an acid.

6. The method of claim 5 , wherein the method comprises formation of a hydrogen sulfide by-product, the molar amount of acid in the crystallization solution being equivalent to the molar amount of the hydrogen sulfide by-product.

7. The method of claim 1 , wherein the crystallization solution comprises an organic amide solvent.

8. The method of claim 7 , wherein the polymer mixture includes the organic amide solvent in an amount of from about 60 wt. % to about 90 wt. % of the mixture.

9. The method of claim 1 , wherein the first sulfur-containing monomer is a complex of sodium methylaminobutyrate and sodium hydrogen sulfide.

10. The method of claim 9 , wherein the second sulfur-containing monomer is a complex of sodium methylaminobutyrate and sodium hydrogen sulfide.

11. The method of claim 1 , wherein the organic amide solvent is N-methyl-2-pyrrolidone.

12. The method of claim 1 , wherein the first sulfur-containing monomer is sodium hydrogen sulfide or sodium sulfide.

13. The method of claim 1 , wherein the dihaloaromatic monomer includes a mixture of different dihaloaromatic monomers.

14. The method of claim 1 , wherein the dihaloaromatic monomer comprises dichlorobenzene.

15. The method of claim 1 , wherein the prepolymer has a weight average molecular weight of from about 500 grams per mole to about 30,000 grams per mole.

16. The method of claim 1 , wherein the polymerization that forms the polyarylene sulfide prepolymer also forms a salt, the method further comprising separating the salt from the prepolymer.

17. The method of claim 1 , wherein the second dihaloaromatic monomer is the same as the first dihaloaromatic monomer.

18. The method of claim 1 , wherein the second dihaloaromatic monomer is different than the first dihaloaromatic monomer.

19. The method of claim 1 , wherein the second sulfur-containing monomer is the same as the first sulfur-containing monomer.

20. The method of claim 1 , wherein the second sulfur-containing monomer is different than the first sulfur-containing monomer.

21. The method of claim 1 , wherein the polyarylene sulfide prepolymer is polymerized with the second dihaloaromatic monomer and the second sulfur-containing monomer in near-anhydrous conditions.

22. The method of claim 1 , further comprising purifying the semi-crystalline polyarylene sulfide.

23. The method of claim 1 , further comprising combining the semi-crystalline polyarylene sulfide with one or more additives.

24. A molded product comprising the polyarylene sulfide of claim 1 .

Assignees

• Ticona Llc

Inventors

• Chiong Hendrich
• Haubs Michael
• Feord Damian
• Leonard Stanley
• Grayson Jacob
• Nekkanti Venkata

Classifications

• C08J3/203

  Solid polymers with solid and/or liquid additives · CPC title

• C08G75/16 Primary

  by polycondensation of organic compounds with inorganic polysulfides · CPC title

• C08J2381/04

  Polysulfides · CPC title