POLYARAMID COMPRISING FLUOROVINYLETHER FUNCTIONALIZED AROMATIC MOIETIES

• US 20110213118A1
• Filed: 09/01/2010
• Published: 09/01/2011
• Est. Priority Date: 09/02/2009
• Status: Abandoned Application

• Current Assignee: E. I. du Pont de Nemours and Company (Corteva, Inc.)
• Original Assignee: E. I. du Pont de Nemours and Company (Corteva, Inc.)
• Inventors: Ritter, Joachim C., Moloy, Kenneth Gene, Drysdale, Neville Everton, Pollino, Joel M., Nederberg, Fredrik
• Application Number:
  US12/873,396
• Publication Number:
  US 20110213118A1
• Time in Patent Office: Days
• US Class Current: 528/372
• CPC Class Codes: C08G 69/265 from at least two different diamines or at least two different dicarboxylic acids
• CPC Class Codes: C08G 69/28 Preparatory processes
• CPC Class Codes: C08G 69/32 from aromatic diamines and aromatic dicarboxylic acids with both amino and carboxylic groups aromatically bound
• CPC Class Codes: C08G 69/42 Polyamides containing atoms other than carbon, hydrogen, oxygen, and nitrogen C08G69/12, C08G69/32 take precedence
• CPC Class Codes: D01F 6/605 from aromatic polyamides
• CPC Class Codes: D01F 6/805 from aromatic copolyamides

Abstract

The invention is directed to polyaramid polymers, comprising repeat units of the condensation product of a fluorovinylether functionalized aromatic diacid chloride and an aromatic diamine, and methods to make said polyaramid polymers. The polymers of this invention are useful as high strength fibers or solution cast films with reduced surface susceptibility to oil.

Claims

1. a polymer comprising a fluorovinyl ether functionalized aromatic repeat unit represented by the structure (I)

2. The polymer of claim 1 wherein, Ar is a benzene radical.

3. The polymer of claim 1 wherein, each R is H.

4. The polymer of claim 1 wherein, one R is reperesented by the structure (II) and the remaining two Rs are each H.

5. The polymer of claim 1 wherein, each R¹ is H.

6. The polymer of claim 1 wherein, X is O.

7. The polymer of claim 1 wherein, X is CF₂.

8. The polymer of claim 1 wherein, Y is O.

9. The polymer of claim 1 wherein, Y is CF₂.

10. The polymer of claim 1 wherein Z is Cl.

11. The polymer of claim 1 wherein one R is represented by the structure (II), one Z is H, and one Z is Cl.

12. The polymer of claim 1 wherein, Rf¹ is CF₂.

13. The polymer of claim 1 wherein, Rf² is CF₂.

14. The polymer of claim 1 wherein p=0 and Y is CF₂.

15. The polymer of claim 1 wherein, Ar is a benzene radical, each R is H, Z is Cl, each R¹ is H, X is O, Y is O, Rf¹ is CF₂, and Rf² is perfluoropropenyl, and q=1.

16. The polymer of claim 1 further comprising aramid repeat units represented by the structure (V),

17. The polymer of claim 1 wherein all the R²s are H, and all the R³s are H.

18. A process, comprising combining a fluorovinyl ether functionalized aromatic diacid chloride with an aromatic diamine to form a reaction mixture, heating to a temperature between 180-240°

C. followed by heating to 250-300°

C., and, extracting volatiles by subjecting said mixture to evacuation;

wherein the fluorovinyl ether functionalized aromatic diacid chloride is represented by the structure (III),

19. In one embodiment of the process hereof, each R is H.

20. In one embodiment of the process hereof, one R is reperesented by the structure (II) and the remaining two Rs are each H.

21. In one embodiment of the process hereof, X is O.

22. In an alternative embodiment, X is CF₂.

23. In one embodiment of the process hereof, Y is O.

24. In an alternative embodiment, Y is CF₂.

25. In a further embodiment, Z is Cl.

26. In an alternative embodiment one R is represented by the structure (II), one Z is H, and one Z is Cl.

27. In one embodiment of the process hereof, Rf¹ is CF₂.

28. In one embodiment of the process hereof, Rf² is CF₂.

29. In one embodiment of the process hereof, p=0 and Y is CF₂.

30. In one embodiment of the process hereof, the aromatic diamine is 1,4-diaminobenzene, Ar is a benzene radical, each R is H, Z is Cl, X is O, Y is O, Rf¹ is CF₂, and Rf² is perfluoropropenyl, and q=1.

31. In another embodiment the reaction mixture further comprises an aromatic diacid chloride represented by the structure (VI)

32. In a further embodiment, each R is H.

33. In one embodiment Ar is a benzene radical.