Multi-stage process for forming polyarylene sulfides

Patent metadata

Field	Value
Publication number	US-9587074-B2
Application number	US-201414481257-A
Country	US
Kind code	B2
Filing date	Sep 9, 2014
Priority date	Sep 25, 2013
Publication date	Mar 7, 2017
Grant date	Mar 7, 2017

Abstract

A multi-stage process and system for formation of a polyarylene sulfide is described. The multi-stage process can include at least three separate formation stages that can take place in three different reactors. The first stage of the formation process can include reaction of an alkali metal sulfide with an organic amide solvent to form a complex including a hydrolysis product of the solvent and an alkali metal hydrogen sulfide. The second stage of the formation process can include reaction of the complex formed in the first stage with a dihaloaromatic monomer to form a prepolymer, and the third stage can include further polymerization of the prepolymer with additional monomers to form the final product.

First claim

What is claimed is:

1. A multi-stage method for forming a polyarylene sulfide comprising:
providing a complex that includes an alkali metal organic amine carboxylic acid salt and an alkali metal hydrogen sulfide;
carrying out a first polymerization reaction in a first reactor during which the complex is reacted with a dihaloaromatic monomer in the presence of an organic amide solvent to form a polyarylene sulfide prepolymer, wherein the first reactor is maintained at a pressure of from about 500 to about 1,600 kilopascals for at least a portion of the first polymerization reaction;
thereafter, carrying out a second polymerization reaction in a second reactor during which the polyarylene sulfide prepolymer is reacted with a dihaloaromatic monomer and a sulfur-containing monomer to form the polyarylene sulfide; and
removing vapor from the second reactor to maintain a pressure of less than about 1,500 kilopascals for at least a portion of the second polymerization reaction.

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

3. The method of claim 1 , wherein the dihaloaromatic monomer in the first polymerization reaction, the second polymerization reaction, or both comprises dichlorobenzene.

4. The method of claim 1 , further comprising reacting a monomer having three or more reactive functional groups with the dihaloaromatic monomer and the complex to form the polyarylene sulfide prepolymer.

5. The method of claim 1 , the method further comprising removing vapor from the first reactor during the formation of the polyarylene sulfide prepolymer.

6. 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.

7. The method of claim 1 , wherein the reaction forming the polyarylene sulfide prepolymer also forms a salt, the method further comprising separating the salt from the prepolymer.

8. The method of claim 1 , wherein the amount of the sulfur-containing monomer combined with the polyarylene sulfide prepolymer is about 10% or less of the total amount required to form an amount of the polyarylene sulfide.

9. The method of claim 1 , wherein the amount of the dihaloaromatic monomer combined with the polyarylene sulfide prepolymer is about 2% or less with respect to the weight of the polyarylene sulfide.

10. The method of claim 1 , wherein a first amount of the complex is reacted with the dihaloaromatic monomer during the first polymerization reaction and a second amount of the complex is reacted with the prepolymer and the dihaloaromatic monomer during the second polymerization reaction, wherein the sulfur-containing monomer comprises the second amount of the complex.

11. The method of claim 1 , further comprising purifying the polyarylene sulfide.

12. The method of claim 1 , further comprising combining the polyarylene sulfide with one or more additives.

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

14. The method of claim 1 , wherein the polyarylene sulfide has a yellowness index of about 15 or less.

15. The method of claim 1 , wherein the organic amide solvent in the first polymerization reaction is N-methylpyrrolidone.

16. The method of claim 1 , wherein the second polymerization reaction occurs in the presence of an organic amide solvent.

17. The method of claim 16 , wherein the organic amide solvent in the second polymerization reaction is N-methylpyrrolidone.

18. The method of claim 16 , wherein the molar ratio of the organic amide solvent to the sulfur-containing monomer in the second polymerization reaction is from about 2 to about 4.

19. The method of claim 1 , wherein the molar ratio of the dihaloaromatic monomer to sulfur charged during the first polymerization reaction is from about 1.0 to about 1.2.

20. The method of claim 1 , wherein the complex is formed by reacting an organic amide solvent, alkali metal sulfide, and water.

21. The method of claim 20 , wherein the organic amide solvent used to form the complex is N-methylpyrrolidone.

22. The method of claim 20 , wherein the alkali metal sulfide is formed from the reaction of sodium hydrogen sulfide and sodium hydroxide.

23. The method of claim 20 , wherein the complex is formed in a third reactor.

24. The method of claim 20 , wherein a stoichiometric excess of the alkali metal sulfide is provided to the reaction to form the complex.

25. The method of claim 1 , wherein the complex includes sodium methylaminobutyrate and sodium hydrogen sulfide.

26. The method of claim 1 , wherein the polyarylene sulfide is a linear polyphenylene sulfide.

27. The method of claim 1 , wherein the molar ratio of any water present in the second polymerization reaction to the sulfur-containing monomer is less than about 0.2.

28. The method of claim 1 , wherein the vapor removed from the second reactor is condensed.

29. The method of claim 1 , wherein the vapor removed from the second reactor includes water.

Assignees

• Ticona Llc

Inventors

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

Classifications

• B01J2208/00274

  involving reactant vapours · CPC title

• B01J19/1862 Primary

  placed in series · CPC title

• B01J2219/0013

  by condensation of reactants · CPC title

• B01J2208/00539

  Pressure · CPC title

• C08G75/14 Primary

  Polysulfides · CPC title