Thermally curable compositions and method

• US 8,048,981 B2
• Filed: 08/25/2006
• Issued: 11/01/2011
• Est. Priority Date: 09/20/2005
• Status: Expired due to Fees

• Current Assignee: General Electric Company
• Original Assignee: General Electric Company
• Inventors: Furuta, Paul Takao, O'Brien, Michael Joseph
• Primary Examiner(s): Figueroa; John J
• Application Number:
  US11/509,965
• Publication Number:
  US 20080051553A1
• Time in Patent Office: 1,894 Days
• Field of Search: None
• US Class Current: 528/403
• CPC Class Codes: C08G 59/68 characterised by the catalysts used
• CPC Class Codes: C08G 65/105 Onium compounds
• CPC Class Codes: C08G 65/18 Oxetanes
• CPC Class Codes: C08G 65/22 Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring
• CPC Class Codes: C08G 65/226 containing fluorine

Abstract

Disclosed are thermally curable compositions comprising at least one cyclic ether, an initiator selected from the group consisting of an iodonium salt, a sulfonium salt, an acylium salt, a tropylium salt, an oxonium salt, and combinations thereof, and a catalyst having structure Pd(Q)₂, wherein Q is at least one ligand selected from the group consisting of a carboxylate, a halide, a ketoester, an ester, a ketone, an hydroxyl, and combinations thereof. Disclosed also are methods of curing the thermally curable compositions, and articles made therefrom. Curing methods comprise heating the composition to a suitable temperature for a period of time. Articles may comprise coated articles, shaped articles or shaped components. Compositions and methods may also be used for composite repair applications.

Claims

1. A thermally curable composition comprising:

(i) a cyclic ether;

(ii) an initiator selected from the group consisting of an iodonium salt, a sulfonium salt, an acylium salt, a tropylium salt, an oxonium salt, and combinations thereof; and

(iii) a catalyst having structure Pd(Q)₂,

wherein Q is at least one ligand selected from the group consisting of a carboxylate, a halide, a ketoester, an ester, a ketone, an hydroxyl, and combinations thereof.

2. The thermally curable composition of claim 1, wherein the cyclic ether comprises at least one epoxy group, at least one oxetane group, or combinations thereof.

3. The thermally curable composition of claim 1, wherein the catalyst is selected from the group consisting of palladium(II) acetylacetonate, palladium(II) chloride, palladium(II) isopropyl acetylacetonate, palladium(II) acetate, and combinations thereof.

4. The thermally curable composition of claim 1, wherein the catalyst is substantially soluble or at least partially soluble in the cyclic ether.

5. The thermally curable composition of claim 1, wherein the catalyst is insoluble in the cyclic ether.

6. The thermally curable composition of claim 1, further comprising a vinyl ether.

7. The thermally curable composition of claim 6, wherein the vinyl ether is selected from the group consisting of 2-ethylhexyl vinyl ether, methyl vinyl ether, 2-methoxy propene, ethyl vinyl ether, butyl vinyl ether, and combinations thereof.

8. A partially cured composition of claim 1.

9. A cured composition of claim 1.

10. A coated article made from the composition of claim 9.

11. A method of curing an epoxy composition comprising the steps of:

(A) providing a curable composition comprising

(i) a cyclic ether,

(ii) an initiator selected from the group consisting of an iodonium salt, a sulfonium salt, an acylium salt, a tropylium salt, an oxonium salt, and combinations thereof, and

(iii) a catalyst having structure Pd(Q)₂,

wherein Q is at least one ligand selected from the group consisting of a carboxylate, a halide, a ketoester, an ester, a ketone, an hydroxyl, and combinations thereof; and

(B) heating the curable composition at a temperature and for a period of time to effect curing.

12. The method of claim 11, wherein the cyclic ether comprises at least one epoxy group, at least one oxetane group, or combinations thereof.

13. The method of claim 11, wherein the catalyst is selected from the group consisting of palladium(II) acetylacetonate, palladium(II) chloride, palladium(II) isopropyl acetylacetonate, palladium(II) acetate, and combinations thereof.

14. The method of claim 11, wherein the curable composition is coated onto a substrate.

15. The method of claim 11, wherein the temperature is in a range of from about 40°

C. to about 200°

C.

16. The method of claim 11, wherein the temperature is in a range of from about 50°

C. to about 150°

C.

17. The method of claim 11, wherein the time of curing is in a range of from about 5 minutes to about 60 minutes.

18. The method of claim 11, wherein the time of curing is in a range of from about 10 minutes to about 40 minutes.

19. A partially cured composition made by the method of claim 11.

20. A cured composition made by the method of claim 11.

21. An article made from the composition of claim 20.

22. An article made by the method of claim 11.

23. A thermally curable coating composition consisting essentially of:

(i) a cyclic ether that comprises at least one epoxy group, at least one oxetane group, or combinations thereof;

(ii) a catalyst selected from the group consisting of palladium(II) acetylacetonate, palladium(II) chloride, palladium(II) isopropyl acetylacetonate, palladium(II) acetate, and combinations thereof; and

(iii) an initiator selected from the group consisting of an iodonium salt, a sulfonium salt, an acylium salt, a tropylium salt, an oxonium salt, and combinations thereof.

24. The thermally curable coating composition of claim 23, wherein the catalyst is substantially soluble or at least partially soluble in the cyclic ether.

25. The thermally curable coating composition of claim 23, wherein the catalyst is insoluble in the cyclic ether.

26. The thermally curable coating composition of claim 23, further comprising a vinyl ether.

27. The thermally curable coating composition of claim 26, wherein the vinyl ether is selected from the group consisting of 2-ethylhexyl vinyl ether, methyl vinyl ether, 2-methoxy propene, ethyl vinyl ether, butyl vinyl ether, and combinations thereof.