Granted Patent B2

US 8,075,812 · App. 11/696,539 · Granted Dec 13, 2011

Abstract

Claims (66)

1. A method of separating a poly(arylene ether) from a solvent, comprising:

removing volatiles from a mixture comprising a poly(arylene ether) and a solvent by devolatilizing extrusion to form an extruded composition comprising the poly(arylene ether); wherein the devolatilizing extrusion comprises adding a solid poly(arylene ether) to a first section of an extruder, and adding the mixture to a second section of the extruder downstream of the first section; and

cooling the extruded composition with a cooling device; wherein the cooling device cools the extruded composition without water immersion of the extruded composition;

wherein the poly(arylene ether) comprises, on average, at least 1.5 hydroxy groups per molecule.

2. The method of claim 1 , wherein the cooling device is maintained at a temperature of about −30 to about 150° C.

3. The method of claim 1 , wherein the cooling the extruded composition comprises cooling the extruded composition to a temperature of about 20° C. to the glass transition temperature of the poly(arylene ether).

4. The method of claim 1 , wherein the cooling device comprises a cooling belt.

5. The method of claim 1 , wherein the cooling device comprises a belt cooled with a liquid selected from the group consists of water, glycol, liquid brine, and mixture thereof.

6. The method of claim 1 , wherein the cooling device comprises an air-cooled belt.

7. The method of claim 1 , wherein the cooling the extruded composition comprises spraying the extruded composition with a water mist.

8. The method of claim 1 , wherein the extruded composition is extruded in the form of a sheet, a strand, or a film; and wherein the cooling device comprises a flaker and a cooling belt.

9. The method of claim 1 , wherein the cooling device comprises a die face pelletizer and a cooling belt.

10. The method of claim 1 , wherein the cooling device comprises an apparatus for pastille formation and a cooling belt.

11. The method of claim 1 , wherein the cooling the extruded composition is conducted in a clean room.

12. The method of claim 1 , wherein the mixture comprising the poly(arylene ether) and the solvent is a solution.

13. The method of claim 1 , wherein the devolatilizing extrusion comprises introducing the mixture to an extruder in a superheated state.

14. The method of claim 1 , wherein the extruded composition is transferred to the cooling device in a form selected from the group consisting of strands, pellets, prills, pastilles, films, sheets, and flakes.

15. The method of claim 1 , wherein the cooling device is a cooling belt, wherein the extruded composition is deposited on the cooling belt in the form of a film, a strand, or a sheet, and wherein the method further comprises breaking the film, strand, or sheet into flakes or irregular particles.

16. The method of claim 15 , further comprising packaging the flakes or irregular particles in a container selected from the group consisting of reinforced paper bags, boxes, and fiber drums.

17. The method of claim 1 , wherein the extruded composition consists essentially of a poly(arylene ether), and wherein the poly(arylene ether) comprises less than 2,000 parts per million by weight of an antisolvent for the poly(arylene ether).

18. The method of claim 1 , wherein the weight ratio of the mixture to the solid poly(arylene ether) is about 1:50 to about 50:1.

19. The method of claim 1 , wherein the mixture is added to the extruder downstream of at least one vacuum vent.

20. The method of claim 1 , wherein the extruded composition comprises a poly(arylene ether) comprising repeating structural units having the formula

wherein for each structural unit, each occurrence of Z 1 is independently halogen, unsubstituted or substituted C 1 -C 12 hydrocarbyl provided that the hydrocarbyl group is not tertiary hydrocarbyl, C 1 -C 12 hydrocarbylthio, C 1 -C 12 hydrocarbyloxy, or C 2 -C 12 halohydrocarbyloxy wherein at least two carbon atoms separate the halogen and oxygen atoms; and each occurrence of Z 2 is independently hydrogen, halogen, unsubstituted or substituted C 1 -C 12 hydrocarbyl provided that the hydrocarbyl group is not tertiary hydrocarbyl, C 1 -C 12 hydrocarbylthio, C 1 -C 12 hydrocarbyloxy, or C 2 -C 12 halohydrocarbyloxy wherein at least two carbon atoms separate the halogen and oxygen atoms.

21. The method of claim 1 , wherein the extruded composition comprises a poly(arylene ether) having the structure

wherein L has the structure

wherein each occurrence of R 5 and R 6 is independently selected from the group consisting of hydrogen, halogen, unsubstituted or substituted C 1 -C 12 hydrocarbyl provided that the hydrocarbyl group is not tertiary hydrocarbyl, C 1 -C 12 hydrocarbylthio, C 1 -C 12 hydrocarbyloxy, and C 2 -C 12 halohydrocarbyloxy wherein at least two carbon atoms separate the halogen and oxygen atoms; x is 0 or 1; and Y has a structure selected from the group consisting of

wherein each occurrence of R 7 is independently selected from the group consisting of hydrogen and C 1 -C 12 hydrocarbyl, and each occurrence of R 8 and R 9 is independently selected from the group consisting of hydrogen, C 1 -C 12 hydrocarbyl, and C 1 -C 6 hydrocarbylene wherein R 8 and R 9 collectively form a C 4 -C 12 alkylene group; each occurrence of Z 1 is independently halogen, unsubstituted or substituted C 1 -C 12 hydrocarbyl provided that the hydrocarbyl group is not tertiary hydrocarbyl, C 1 -C 12 hydrocarbylthio, C 1 -C 12 hydrocarbyloxy, or C 2 -C 12 halohydrocarbyloxy wherein at least two carbon atoms separate the halogen and oxygen atoms; each occurrence of Z 2 is independently hydrogen, halogen, unsubstituted or substituted C 1 -C 12 hydrocarbyl provided that the hydrocarbyl group is not tertiary hydrocarbyl, C 1 -C 12 hydrocarbylthio, C 1 -C 12 hydrocarbyloxy, or C 2 -C 12 halohydrocarbyloxy wherein at least two carbon atoms separate the halogen and oxygen atoms; y and z are independently 0 to 100 provided that the sum of y and z is at least one; and each occurrence of Q is hydrogen.

22. The method of claim 1 , wherein the poly(arylene ether) has an intrinsic viscosity of about 0.03 to about 1 deciliter per gram as measured in chloroform at 25° C.

23. The method of claim 1 , wherein the poly(arylene ether) has an intrinsic viscosity of about 0.1 to about 0.25 deciliter per gram as measured in chloroform at 25° C.

24. The method of claim 1 , wherein the poly(arylene ether) has an intrinsic viscosity of about 0.03 to about 0.15 deciliter per gram as measured in chloroform at 25° C.

25. A method of isolating a poly(arylene ether), comprising:

removing volatiles from a mixture comprising a poly(arylene ether) and a solvent by devolatilizing extrusion to form an extruded poly(arylene ether); wherein the devolatilizing extrusion comprises adding a solid poly(arylene ether) to a first section of an extruder, and adding the mixture to a second section of the extruder downstream of the first section; and

cooling the extruded poly(arylene ether) with a cooling belt to form an isolated poly(arylene ether);

wherein the isolated poly(arylene ether) is a polyhydroxy poly(arylene ether) comprising, on average, at least 1.5 hydroxy groups per molecule;

wherein the isolated poly(arylene ether) has an intrinsic viscosity of about 0.04 to about 0.15 deciliter per gram as measured in chloroform at 25° C.;

wherein the mixture comprises about 65 to about 85 weight percent poly(arylene ether) and about 15 to about 35 weight percent solvent; and

wherein devolatilizing extrusion comprises feeding the mixture to an extruder comprising

at least one barrel having a temperature of about 200 to about 235° C., and

at least one vent having a pressure of about 20 to about 40 kilopascals.

26. The method of claim 25 , wherein the mixture comprising the poly(arylene ether) and the solvent is a solution.

27. The method of claim 25 , wherein the devolatilizing extrusion comprises introducing the mixture to an extruder in a superheated state.

28. The method of claim 25 , wherein the isolated poly(arylene ether) comprises less than 2,000 parts per million by weight of an antisolvent for the poly(arylene ether).

29. The method of claim 25 , wherein the isolated poly(arylene ether) comprises about 0.1 to about 1 weight percent solvent.

30. The method of claim 25 , wherein the isolated poly(arylene ether) is a polyfunctional poly(arylene ether) comprising, on average, at least 1.5 functional groups Q per molecule; and wherein the isolated poly(arylene ether) comprises a poly(arylene ether) having the structure

wherein R is the residue of a polyhydric phenol; each occurrence of Z 1 is independently halogen, unsubstituted or substituted C 1 -C 12 hydrocarbyl provided that the hydrocarbyl group is not tertiary hydrocarbyl, C 1 -C 12 hydrocarbylthio, C 1 -C 12 hydrocarbyloxy, or C 2 -C 12 halohydrocarbyloxy wherein at least two carbon atoms separate the halogen and oxygen atoms; each occurrence of Z 2 is independently hydrogen, halogen, unsubstituted or substituted C 1 -C 12 hydrocarbyl provided that the hydrocarbyl group is not tertiary hydrocarbyl, C 1 -C 12 hydrocarbylthio, C 1 -C 12 hydrocarbyloxy, or C 2 -C 12 halohydrocarbyloxy wherein at least two carbon atoms separate the halogen and oxygen atoms; each occurrence of m is independently 0 to about 12, provided that the sum of all occurrences of m is at least 1; n is at least 2; and each occurrence of Q is hydrogen.

31. The method of claim 25 , wherein the isolated poly(arylene ether) has, on average, at least 1.5 hydroxy groups per molecule and comprises a poly(arylene ether) having the structure

wherein each occurrence of Q 7 and Q 8 is independently methyl or di-n-butylaminomethyl; and each occurrence of a and b is independently 0 to about 12, provided that the sum of a and b is at least 1.

32. The method of claim 25 , wherein the solid poly(arylene ether) is a portion of the isolated poly(arylene ether).

33. The method of claim 25 , wherein the mixture is added to the extruder downstream of at least one vent having a pressure of about 20 to about 40 kilopascals.

34. The method of claim 25 , wherein the cooling belt is maintained at a temperature of about −30 to about 150° C.

35. The method of claim 25 , wherein the isolated poly(arylene ether) is in the form of flakes or irregular particles.

36. A method of isolating a poly(arylene ether), comprising:

removing volatiles from mixture comprising a poly(arylene ether) and a solvent by devolatilizing extrusion to form an extruded poly(arylene ether); wherein the devolatilizing extrusion comprises adding a solid poly(arylene ether) to a first section of an extruder, and adding the mixture to a second section of the extruder downstream of the first section; and

cooling the extruded poly(arylene ether) with a cooling belt to form an isolated poly(arylene ether);

wherein the mixture comprises about 70 to about 80 weight percent poly(arylene ether) and about 20 to about 30 weight percent toluene; and

wherein the isolated poly(arylene ether) has an intrinsic viscosity of about 0.04 to about 0.10 deciliter per gram as measured in chloroform at 25° C.;

wherein the isolated poly(arylene ether) has, on average, at least 1.5 hydroxy groups per molecule;

wherein the isolated poly(arylene ether) comprises a poly(arylene ether) having the structure

wherein each occurrence of Q 7 and Q 8 is independently methyl or di-n-butylaminomethyl; and each occurrence of a and b is independently 0 to about 12, provided that the sum of a and b is at least 1;

wherein devolatilizing extrusion comprises feeding the mixture to an extruder comprising

at least one barrel having a temperature of about 210 to about 230° C., and

at least one vent having a pressure of about 25 to about 35 kilopascals;

wherein the mixture is fed to the extruder downstream of at least one vent; and

wherein a portion of the isolated poly(arylene ether) is recycled for addition to the feed throat of the extruder.

37. The method of claim 36 , wherein the mixture comprising the poly(arylene ether) and the solvent is a solution.

Assignments (8)