Method of thiophenol removal from poly(arylene sulfide) polymer compositions

Patent metadata

Field	Value
Publication number	US-9388282-B2
Application number	US-201314066063-A
Country	US
Kind code	B2
Filing date	Oct 29, 2013
Priority date	Oct 29, 2013
Publication date	Jul 12, 2016
Grant date	Jul 12, 2016

Abstract

A process comprising contacting a reaction product composition comprising a poly(arylene sulfide) composition and a polar organic compound, wherein the polar organic compound comprises greater than or equal to about 1 wt. % thiophenol, with a C 4 -C 30 α,β-unsaturated ketone, a C 4 -C 30 α,β-unsaturated ester, a C 4 -C 30 α,β-unsaturated amide, or any combination thereof, wherein after the contacting, the polar organic compound comprises less than about 1 wt. % thiophenol. A process comprising contacting a composition comprising a polar organic compound and greater than or equal to about 1 wt. % thiophenol with a C 4 -C 30 α,β-unsaturated ketone, a C 4 -C 30 α,β-unsaturated ester, a C 4 -C 30 α,β-unsaturated amide, or any combination thereof, to form a composition comprising the polar organic compound and less than about 1 wt. % thiophenol.

First claim

What is claimed is:

1. A process comprising:
contacting a reaction product composition comprising a poly(arylene sulfide) composition and a polar organic compound, wherein the polar organic compound comprises greater than or equal to about 1 wt. % thiophenol, with a compound consisting of at least one C 4 -C 30 α,β-unsaturated ketone, at least one C 4 -C 30 α,β-unsaturated ester, at least one C 4 -C 30 α,β-unsaturated amide, or any combination thereof, wherein after the contacting, the polar organic compound comprises less than about 1 wt. % thiophenol.

2. The process of claim 1 , wherein the reaction product composition is produced by contacting:
i) at least one halogenated aromatic compound having two halogens,
ii) a sulfur compound, and
iii) the polar organic compound.

3. The process of claim 1 , wherein the poly(arylene sulfide) composition is a poly(phenylene sulfide) composition.

4. The process of claim 2 , wherein the halogenated aromatic compound comprises p-dichlorobenzene and the sulfur compound comprises sodium sulfide, sodium hydrosulfide, or any combination thereof.

5. The process of claim 2 , wherein the polar organic compound comprises N-methyl-2-pyrrolidone.

6. The process of claim 1 , wherein the poly(arylene sulfide) composition is contacted with the C 4 -C 30 α,β-unsaturated ester.

7. The process of claim 6 , wherein the C 4 -C 30 α,β-unsaturated ester comprises 2-ethylhexyl acrylate.

8. The process of claim 6 , wherein the C 4 -C 30 α,β-unsaturated ester comprises an ester of acrylic acid with a fatty alcohol.

9. The process of claim 6 , wherein the C 4 -C 30 α,β-unsaturated ester comprises an ester of methacrylic acid with a fatty alcohol.

10. The process of claim 1 , wherein the reaction product composition is contacted with at least one stoichiometric equivalent of the C 4 -C 30 α,β-unsaturated ketone, the C 4 -C 30 α,β-unsaturated ester, the C 4 -C 30 α,β-unsaturated amide, or any combination thereof, per equivalent of thiophenol.

11. The process of claim 1 , wherein the contacting occurs at a temperature less than or equal to about 200° C.

12. The process of claim 1 , wherein the polar organic compound comprising less than 1 wt. % thiophenol is separated from the reaction product composition.

13. The process of claim 12 , wherein the separated polar organic compound is used in a process for producing a poly(arylene sulfide) composition.

14. The process of claim 1 , wherein the polar organic compound is an amide, a lactam, a sulfone, or any combination thereof.

15. The process of claim 1 , wherein the C 4 -C 30 α,β-unsaturated ketone, C 4 -C 30 α,β-unsaturated ester, C 4 -C 30 α,β-unsaturated amide, or any combination thereof, is contacted with the reaction product composition at a temperature from about 20° C. to about 50° C.

Assignees

• Solvay
• Solvay Specialty Polymers Usa

Inventors

• Matson Michael S
• Soules David A

Classifications

• C08G75/14 Primary

  Polysulfides · CPC title

• C08G79/04 Primary

  Phosphorus linked to oxygen or to oxygen and carbon · CPC title

• C08L81/00

  Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen or carbon only; Compositions of polysulfones; Compositions of derivatives of such polymers · CPC title

• C08L81/02

  Polythioethers; Polythioether-ethers · CPC title

• C08K5/3417

  condensed with carbocyclic rings · CPC title