Curable polyphenylene ether-thermosetting resin composition and process

• US 5,834,565 A
• Filed: 11/12/1996
• Issued: 11/10/1998
• Est. Priority Date: 11/12/1996
• Status: Expired due to Fees

• Current Assignee: Sabic Innovative Plastics IP BV (Government of Saudi Arabia)
• Original Assignee: General Electric Company
• Inventors: Yeager, Gary William, Tracy, James E.
• Primary Examiner(s): BUTTNER, DAVID J
• Application Number:
  US08/747,535
• Time in Patent Office: 728 Days
• Field of Search: 525/391, 525/393, 525/395, 525/396, 525/397, 525/390, 523/433, 524/540
• US Class Current: 525/391
• CPC Class Codes: C08G 65/485 Polyphenylene oxides
• CPC Class Codes: C08L 2666/14 Macromolecular compounds according to C08L59/00 - C08L87/00; Derivatives thereof
• CPC Class Codes: C08L 61/00 Compositions of condensation polymers of aldehydes or ketones with polyalcohols C08L59/00; with polynitriles C08L77/00; Compositions of derivatives of such polymers
• CPC Class Codes: C08L 67/00 Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain of polyester-amides C08L77/12; of polyester-imides C08L79/08; Compositions of derivatives of such polymers
• CPC Class Codes: C08L 71/126 modified by chemical after-treatment
• CPC Class Codes: C08L 75/04 Polyurethanes
• CPC Class Codes: C08L 83/04 Polysiloxanes
• CPC Class Codes: H05K 1/0326 containing O

Abstract

Polyphenylene ether-thermosetting resin compositions are provided that are useful as dielectrics, particularly printed circuit boards having improved processability, good solvent and solder resistance, as well as improved morphology as compared to other polyphenylene ether-thermosetting resin compositions. More specifically, the particular polyphenylene ether resin component of this invention has a molecular weight of less than about 3,000 number average in contrast to higher molecular weight polyphenylene ethers employed in other polyphenylene ether-thermosetting resin compositions for use in preparing printed circuit boards.

Claims

1. A curable resin composition comprising:

(a) at least one polyphenylene ether resin having a number average molecular weight between about 500 to about 2,900 wherein said polyphenylene ether resin comprises a functionalized polyphenylene ether resin and wherein said functionalized polyphenylene ether resin contains at least one species of the group consisting of acid, anhydride, amine, epoxy, oxazoline, orthoester, hydroxyl, phosphate, and phosphonate, and

(b) at least one thermosetting resin selected from the group consisting of phenolic, alkyds, polyester, polyurethane, mineral filled silicone, cyanate esters, vinyl, and benzocyclobutene resins.

2. The curable resin composition of claim 1, wherein said polyphenylene ether resin has a number average molecular weight between about 800 to about 2,200.

3. The curable resin composition of claim 1, wherein said functionalized polyphenylene ether resin is the reaction product of at least one polyphenylene ether resin with a peroxide or with a peroxide and a phenol.

4. The curable resin composition of claim 3, wherein said phenol is a bisphenol.

5. The curable resin composition of claim 1, wherein said functionalized polyphenylene ether resin is a reaction product of at least one polyphenylene ether resin with benzoyl peroxide or a mixture of benzoyl peroxide and a phenol.

6. The curable resin composition of claim 5, wherein said phenol is a bisphenol.

7. The curable resin composition of claim 1, further comprising at least one additional component of the group consisting of catalysts, fibrous substrates, reinforcing agents, flame retardants, organic solvents, and curing agents.

8. A thermoset composition made from the curable resin composition of claim 1.

9. The thermoset composition of claim 8, wherein the thermoset composition is reinforced with a fibrous substrate.

10. The thermoset composition of claim 8, wherein the average polyphenylene ether resin particle size diameter, as measured by microscopy, is less than 5 microns.

11. An article made from the thermoset composition of claim 8.

12. The thermoset composition of claim 8, wherein said thermosetting resin is a phenolic resin.

13. The thermoset composition of claim 8, wherein said thermosetting resin is an alkyd resin.

14. The thermoset composition of claim 8, wherein said thermosetting resin is a polyester resin.

15. The thermoset composition of claim 8, wherein said thermosetting resin is a polyurethane resin.

16. The thermoset composition of claim 8, wherein said thermosetting resin is a mineral filled silicone resin.

17. The thermoset composition of claim 8, wherein said thermosetting resin is a cyanate ester resin.

18. The thermoset composition of claim 8, wherein said thermosetting resin is a vinyl resin.

19. The thermoset composition of claim 8, wherein said thermosetting resin is a benzocyclobutene resin.

20. The curable resin composition of claim 1, wherein said thermosetting resin is a phenolic resin.

21. The curable resin composition of claim 1, wherein said thermosetting resin is an alkyd resin.

22. The curable resin composition of claim 1, wherein said thermosetting resin is a polyester resin.

23. The curable resin composition of claim 1, wherein said thermosetting resin is a polyurethane resin.

24. The curable resin composition of claim 1, wherein said thermosetting resin is a mineral filled silicone resin.

25. The curable resin composition of claim 1, wherein said thermosetting resin is a cyanate ester resin.

26. The curable resin composition of claim 1, wherein said thermosetting resin is a vinyl resin.

27. The curable resin composition of claim 1, wherein said thermosetting resin is a benzocyclobutene resin.

28. A thermoset composition made from a curable resin composition consisting essentially of:

(a) at least one polyphenylene ether resin having a number average molecular weight between about 500 to about 2,900 wherein said polyphenylene ether resin comprises a functionalized polyphenylene ether resin and wherein said functionalized polyphenylene ether resin contains at least one species of the group consisting of acid, anhydride, amine, epoxy, oxazoline, orthoester, hydroxyl, phosphate, and phosphonate, and

(b) at least one thermosetting resin selected from the group consisting of phenolic, alkyds, polyester, polyurethane, mineral filled silicone, cyanate esters, vinyl, and benzocyclobutene resins.

29. The thermoset composition of claim 28, wherein the curable resin composition further consists essentially of at least one additional component of the group consisting of fibrous substrates, reinforcing agents, catalysts, flame retardants, organic solvents, and curing agents.

30. The thermoset composition of claim 28, wherein said thermosetting resin is a phenolic resin.

31. The thermoset composition of claim 28, wherein said thermosetting resin is an alkyd resin.

32. The thermoset composition of claim 28, wherein said thermosetting resin is a polyester resin.

33. The thermoset composition of claim 28, wherein said thermosetting resin is a polyurethane resin.

34. The thermoset composition of claim 28, wherein said thermosetting resin is a mineral filled silicone resin.

35. The thermoset composition of claim 28, wherein said thermosetting resin is a cyanate ester resin.

36. The thermoset composition of claim 28, wherein said thermosetting resin is a vinyl resin.

37. The thermoset composition of claim 28, wherein said thermosetting resin is a benzocyclobutene resin.

38. The thermoset composition of claim 28, wherein said polyphenylene ether resin has a number average molecular weight between about 800 to about 2,200.

39. A reaction product of a curable resin composition comprising:

(a) at least one polyphenylene ether resin having a number average molecular weight between about 500 to about 2,900 wherein said polyphenylene ether resin comprises a functionalized polyphenylene ether resin and wherein said functionalized polyphenylene ether resin contains at least one species of the group consisting of acid, anhydride, amine, epoxy, oxazoline, orthoester, hydroxyl, phosphate, and phosphonate, and

(b) at least one thermosetting resin selected from the group consisting of phenolic, alkyds, polyester, polyurethane, mineral filled silicone, cyanate esters, vinyl, and benzocyclobutene resins.

40. The reaction product of claim 39, wherein said thermosetting resin is a phenolic resin.

41. The reaction product of claim 39, wherein said thermosetting resin is an alkyd resin.

42. The reaction product of claim 39, wherein said thermosetting resin is a polyester resin.

43. The reaction product of claim 39, wherein said thermosetting resin is a polyurethane resin.

44. The reaction product of claim 39, wherein said thermosetting resin is a mineral filled silicone resin.

45. The reaction product of claim 39, wherein said thermosetting resin is a cyanate ester resin.

46. The reaction product of claim 39, wherein said thermosetting resin is a vinyl resin.

47. The reaction product of claim 39, wherein said thermosetting resin is a benzocyclobutene resin.

48. The reaction product of claim 39, wherein said polyphenylene ether resin has a number average molecular weight between about 800 to about 2,200.

49. A curable composition for impregnating and preparing cured fibrous substrates and which composition when dissolved in an inert solvent is free of gelation at room temperature, said composition comprising in admixture:

(a) the reaction product of at least one polyphenylene ether resin in an inert organic solvent with a co-reactant that is selected from the group consisting of an oxidizing agent and mixtures of an oxidizing agent with a phenol to afford a polyphenylene ether resin having a number average molecular weight between about 500 to about 2,900;

(b) at least one polyepoxide composition comprising;

(i) a tetrabromo bisphenol diglycidyl ether, and

(ii) an epoxy novolak resin;

wherein the polyepoxy composition further comprises a condensation product of a bisphenol diglycidyl ether with a tetrabromo bisphenol, and

(c) a catalytic amount of a catalyst.

50. The curable composition of claim 49, wherein said composition has a bromine content of at least about 15% by weight based upon the weight of the curable composition without a fibrous substrate.

51. The curable resin composition of claim 49, wherein said polyphenylene ether resin has a number average molecular weight between about 800 to about 2,200.