IP Library › Granted Patent US 9,006,353
Granted Patent B2
US 9,006,353 · App. 14/357,613 · Granted Apr 14, 2015

Crosslinking compounds for high glass transition temperature polymers

Inventors: William Franklin Burgoyne, Jr. (Bethlehem, PA); Andrew Francis Nordquist (Whitehall, PA); Kerry A. Drake (Red Hill, PA); Le Song (North Wales, PA)
Assignee: Delsper LP
C08G16/00C08K5/0025C08G65/48C08G65/485C08L71/00C08G2650/20C08G2650/40C08L81/06
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Quick Facts
Patent No.
US 9,006,353
App. No.
14/357,613
Granted
Apr 14, 2015
Kind
B2
Abstract

A composition having a crosslinking compound that has the following structure (I) wherein R is OH, NH 2 , halide, ester, amine, ether, or amide, and x is 2-6 and A is an arene moiety having a molecular weight of less than about 10,000. A mixture including the composition and a polymer, a method for forming the mixture and a crosslinked polymer are also disclosed.

Claims (48)

1. A composition comprising a crosslinking compound having the following structure:

2. A mixture comprising:

a composition including a crosslinking compound having the following structure:

wherein R is OH, NH 2 , halide, ester, amine, ether, or amide, and x is 2-6 and A is an arene moiety having a molecular weight of less than about 10,000; and

a polymer containing at least one aromatic group;

wherein the mixture is a substantially homogenous blend of the composition and the polymer.

3. The mixture of claim 2 , wherein the polymer is selected from the group consisting of a poly(arylene ether) polymer including polymer repeat units of the following structure:

(—O—Ar 1 —O—Ar 2 —) m (—O—Ar 3 —O—Ar 4 —) n

where Ar 1 , Ar 2 , Ar 3 , and Ar 4 are identical or different aryl radicals, m is 0 to 1, n is 1-m; a polysulfone; a polyimide; a polyamide; a poly(etherketone); a polyurea; a polyurethane; a polyphthalamide; a polyamide-imide; an aramid; a poly(benzimidazole); and combinations thereof.

4. The mixture of claim 2 , wherein the mixture is a co-precipitated blend of the composition and the polymer.

5. The mixture of claim 2 , wherein the mixture is a co-evaporated blend of the composition and the polymer.

6. The mixture of claim 2 , wherein the mixture is a mechanically mixed blend of the composition and the polymer.

7. The mixture of claim 2 , wherein the crosslinking compound has a structure selected from a group consisting of:

8. The mixture of claim 2 , wherein the crosslinking compound has the following structure:

9. The mixture of claim 2 , wherein the crosslinking compound has the following structure:

10. The mixture of claim 2 , wherein the crosslinking compound has the following structure:

11. The mixture of claim 2 , wherein the crosslinking compound has the following structure:

12. A method for making a polymer blend comprising:

providing a composition including a crosslinking compound having the following structure:

wherein R is OH, NH 2 , halide, ester, amine, ether, or amide, and x is 2-6 and A is an arene moiety having a molecular weight of less than about 10,000; and

providing a polymer containing at least one aromatic group;

combining the composition and the polymer to form a substantially homogeneous mixture.

13. The method of claim 12 , wherein the polymer is selected from the group consisting of a poly(arylene ether) polymer including polymer repeat units of the following structure:

(—O—Ar 1 —O—Ar 2 —) m (—O—Ar 3 —O—Ar 4 —) n

where Ar 1 , Ar 2 , Ar 3 , and Ar 4 are identical or different aryl radicals, m is 0 to 1, n is 1-m; a polysulfone; a polyimide; a polyamide; a poly(etherketone); a polyurea; a polyurethane; a polyphthalamide; a polyamide-imide; an aramid; a poly(benzimidazole); and combinations thereof.

14. The method of claim 12 , wherein the combining includes dissolving the composition and the polymer in a solvent to form a solution, adding the solution to a non-solvent, and co-precipitating the composition and the polymer to form the substantially homogenous mixture.

15. The method of claim 12 , wherein the combining includes dissolving the composition and the polymer in a solvent to form a solution, evaporating the solvent from the solution to form the substantially homogenous mixture.

16. The method of claim 12 , wherein the combining includes dissolving the composition and the polymer in a solvent to form a solution, evaporating the solvent from the solution to form the substantially homogenous mixture.

17. The method of claim 12 , wherein the combining includes mechanically blending the composition and the polymer to form the substantially homogenous mixture.

18. The method of claim 17 , wherein the mechanical blending is in an extruder, ball mill, or cyrogrinder.

19. The method of claim 12 , wherein the crosslinking compound has a structure selected from a group consisting of:

20. The method of claim 12 , wherein the crosslinking compound has the following structure:

21. The method of claim 12 , wherein the crosslinking compound has the following structure:

22. The method of claim 12 , wherein the crosslinking compound has the following structure:

23. The method of claim 12 , wherein the crosslinking compound has the following structure:

24. A crosslinked polymer comprising:

a reaction product of a composition including a crosslinking compound having the following structure:

wherein R is OH, NH 2 , halide, ester, amine, ether, or amide, and x is 2-6 and A is an arene moiety having a molecular weight of less than about 10,000; and

a polymer containing at least one aromatic group.

25. The crosslinked polymer of claim 24 , wherein the polymer is selected from the group consisting of a poly(arylene ether) polymer including polymer repeat units of the following structure:

(—O—Ar 1 —O—Ar 2 —) m (—O—Ar 3 —O—Ar 4 —) n

where Ar 1 , Ar 2 , Ar 3 , and Ar 4 are identical or different aryl radicals, m is 0 to 1, n is 1-m; a polysulfone; a polyimide; a polyamide; a poly(etherketone); a polyurea; a polyurethane; a polyphthalamide; a polyamide-imide; an aramid; a poly(benzimidazole); and combinations thereof.

26. The crosslinked polymer of claim 24 , wherein the reaction product is thermally cured.

27. The crosslinked polymer of claim 26 , wherein the reaction product is thermally cured by heating to temperatures greater than about 250° C.

28. The crosslinked polymer of claim 24 , wherein the reaction product is radiation cured.

29. The crosslinked polymer of claim 28 , wherein the reaction product is radiation cured by exposure to radiation selected from the group consisting of microwave, infrared, ultraviolet, and electron beam.

30. The crosslinked polymer of claim 24 , wherein the reaction product is thermally stable at temperature greater than 260° C.

31. The crosslinked polymer of claim 24 , wherein the reaction product is thermally stable at temperature greater than 400° C.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 12, 2014
From: BURGOYNE, WILLIAM FRANKLIN, JR.; NORDQUIST, ANDREW FRANCIS; DRAKE, KERRY A.; SONG, LE
To: GREENE, TWEED & CO.
Reel/Frame 032868/0255 →
Continuity (1)
Related Publication 20140323668A1 · Oct 30, 2014