IP Library Granted Patent US 8,846,857
Granted Patent B2
US 8,846,857 · App. 13/644,524 · Granted Sep 30, 2014

Solution phase processing of polyarylene sulfide

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Quick Facts
Patent No.
US 8,846,857
App. No.
13/644,524
Granted
Sep 30, 2014
Kind
B2
Abstract

Provided are methods for obtaining modified polyarylene sulfide compositions having improved thermal and thermo-oxidative stability, the compositions so obtained, and articles comprising the compositions. The method comprises the steps of contacting, in the presence of a suitable solvent, a polyarylene sulfide with at least one reducing agent and at least base to form a first mixture. The reducing agent comprises zinc(0), tin(0), tin(II), bismuth (0), bismuth(III), or a combination thereof. The first mixture is heated to form a second mixture in which the polyarylene sulfide is dissolved. The polyarylene sulfide is then precipitated to obtain a modified polyarylene sulfide.

Claims (21)

1. A modified polyphenylene sulfide obtained by a method comprising the steps of:

a) contacting, in the presence of a suitable solvent, a polyphenylene sulfide with at least one reducing agent and at least one base to form a first mixture, wherein the reducing agent comprises zinc(0), tin(0), tin(II), bismuth (0), bismuth(III), or a combination thereof, and the ratio of the reducing agent to the polyphenylene sulfide is from about 0.0001:1 to about 0.5:1 on a weight basis;

b) heating the first mixture to a sufficient temperature and for a sufficient time to form a second mixture wherein the polyphenylene sulfide is dissolved in the solvent; and

c) precipitating the dissolved polyphenylene sulfide from the second mixture to obtain a modified polyphenylene sulfide having improved thermo-oxidative stability relative to the thermo-oxidative stability of the polyphenylene sulfide of step a) measured under the same conditions.

2. The modified polyphenylene sulfide of claim 1 having a decrease in melting point after exposure to air for 10 days at 250° C. of less than 10° C. as measured by DSC analysis.

3. The modified polyphenylene sulfide of claim 1 having a volatile content which is at least 10% reduced in comparison to the volatile content of the polyphenylene sulfide before modification.

4. The modified polyphenylene sulfide of claim 1 containing 200 ppm or less of phenol+thiophenol+p-chlorothiophenol as determined using the Volatiles Test.

5. The modified polyphenylene sulfide of claim 1 , wherein the base comprises bicarbonate, carbonate, hydroxide, oxide, sulfide, a carboxylate, or a mixture thereof.

6. The modified polyphenylene sulfide of claim 1 , wherein the base comprises zinc(II), tin(II), bismuth(III), Li + , Na + , K + , Rb + , Cs + , or a mixture thereof.

7. The modified polyphenylene sulfide of claim 1 , wherein the solvent comprises N-methyl-2-pyrrolidone, 1-cyclohexyl-2-pyrrolidinone, or mixtures thereof.

8. The modified polyphenylene sulfide of claim 1 , wherein the reducing agent comprises tin(II).

9. The modified polyphenylene sulfide of claim 1 , wherein the reducing agent comprises zinc(0), the base comprises sodium bicarbonate, and the solvent comprises N-methyl-2-pyrrolidone.

10. The modified polyphenylene sulfide of claim 1 , wherein in step a) the polyphenylene sulfide is additionally contacted with at least one compound comprising zinc(II), tin(II), tin(IV), bismuth(V), antimony(III), antimony(V), or a combination thereof, and wherein the ratio of the compound to the polyphenylene sulfide is from about 0.0001:1 to about 0.5:1 on a weight basis.

11. The modified polyphenylene sulfide of claim 10 , wherein the compound comprises zinc(II), tin(II), or a combination thereof.

12. The modified polyphenylene sulfide of claim 1 , wherein the method further comprises a step of compounding the modified polyphenylene sulfide with an additive comprising zinc(II), tin(II), or a combination thereof.

13. An article comprising the modified polyphenylene sulfide of claim 1 .

14. The article of claim 13 , wherein the article is a fiber, a felt, a bag filter, a nonwoven fabric, a film, a coating, or a molded part.

15. A method comprising the steps of:

a) contacting, in the presence of a suitable solvent, a polyarylene sulfide with at least one reducing agent and at least one base to form a first mixture, wherein the reducing agent comprises zinc(0), tin(0), tin(II), bismuth (0), bismuth(III), or a combination thereof, and the ratio of the reducing agent to the polyarylene sulfide is from about 0.0001:1 to about 0.5:1 on a weight basis;

b) heating the first mixture to a sufficient temperature and for a sufficient time to form a second mixture wherein the polyarylene sulfide is dissolved in the solvent; and

c) precipitating the dissolved polyarylene sulfide from the second mixture to obtain a modified polyarylene sulfide having improved thermo-oxidative stability relative to the thermo-oxidative stability of the polyarylene sulfide of step a) measured under the same conditions.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 26, 2019
From: E. I. DU PONT DE NEMOURS AND COMPANY
To: DUPONT POLYMERS, INC.
Reel/Frame 049590/0650 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 9, 2014
From: DUFF, ROBERT JOHN; HUANG, ZHENG-ZHENG; RITTER, JOACHIM C; POLLINO, JOEL M
To: E. I. DU PONT DE NEMOURS AND COMPANY
Reel/Frame 031924/0388 →