Flexible interpenetrating networks formed by epoxy-cyanate ester compositions via a polyamide

• US 5,912,316 A
• Filed: 05/19/1997
• Issued: 06/15/1999
• Est. Priority Date: 11/08/1996
• Status: Expired due to Term

• Current Assignee: Henkel IP & Holding GmbH (Henkel AG & Co KGaA)
• Original Assignee: Johnson Matthey Incorporated (Johnson Matthey PLC)
• Inventors: Nguyen, Guy P., Edwards, Carl
• Primary Examiner(s): KRASS, FREDERICK F
• Application Number:
  US08/859,792
• Time in Patent Office: 757 Days
• Field of Search: 528/93, 528/94, 528/99, 528/117, 528/327
• US Class Current: 528/93
• CPC Class Codes: C08G 59/4014 Nitrogen containing compounds
• CPC Class Codes: C08G 59/686 containing nitrogen
• CPC Class Codes: C08G 73/0655 from polycyanurates
• CPC Class Codes: C08L 2666/20 Macromolecular compounds having nitrogen in the main chain according to C08L75/00 - C08L79/00; Derivatives thereof
• CPC Class Codes: C08L 63/00 Compositions of epoxy resins; Compositions of derivatives of epoxy resins
• CPC Class Codes: C08L 79/04 Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
• CPC Class Codes: H01L 2224/73265 Layer and wire connectors
• CPC Class Codes: H01L 2924/00012 Relevant to the scope of the group, the symbol of which is combined with the symbol of this group
• CPC Class Codes: H01L 2924/181 Encapsulation

Abstract

A resin composition, for use as a die attach adhesive, heat sink attach adhesive, encapsulant or underfill, comprises a resin system, including a mixture of an epoxy resin and a cyanate ester resin, and a polyamide catalyst. The composition is curable in one minute at 200° C. and has a pot life of at least 18 hours at room temperature. The resin composition is flexible, develops high adhesion, high moisture resistance, low weight loss during curing and requires no solvents.

Claims

1. A resin composition comprising:

a resin catalyst system including at least one epoxy resin and at least one cyanate ester resin and a catalyst having the formula;

##STR2## wherein m and n are at least 1.

2. A resin composition as claimed in claim 1 wherein the epoxy resin comprises at least one aromatic epoxy resin.

3. A resin composition as claimed in claim 2 comprising at least one of bisphenol F epoxy resin or bisphenol A epoxy resin.

4. A resin composition as claimed in claim 1 wherein the cyanate ester resin comprises a polyfunctional cyanate ester resin.

5. A resin composition as claimed in claim 4 wherein the polyfunctional cyanate ester resin is selected from the group consisting of 1,1'"'"'-bis (4-cyanatophenyl) ethane, bis(4-cyanato-3,5-dimethylphenyl) methane, 2,2'"'"'-bis (4-cyanatophenyl) isopropylidene and mixtures thereof.

6. A resin composition as claimed in claim 1 wherein the epoxy resin is present in an amount of from about 5% to about 95% by weight of the resin system.

7. A resin composition as claimed in claim 1 wherein the epoxy resin is present in an amount of from about 10% to about 70% by weight of the resin system.

8. A resin composition as claimed in claim 1 wherein the epoxy resin is present in an amount of from about 30% to about 60% by weight of the resin system.

9. A resin composition as claimed in claim 1 wherein the cyanate ester resin is present in an amount of from about 5% to about 80% by weight of the resin system.

10. A resin composition as claimed in claim 1 wherein the cyanate ester resin is present in an amount of from about 10% to about 60% by weight of the resin system.

11. A resin composition as claimed in claim 1 wherein the cyanate ester resin is present in an amount of from about 20% to about 40% by weight of the resin system.

12. A resin composition as claimed in claim 1 wherein the catalyst is present in an amount of from about 5 parts to about 30 parts per 100 parts by weight of the resin system.

13. A resin composition as claimed in claim 1 wherein the catalyst is present in an amount of from about 7 parts to about 15 parts per 100 parts by weight of the resin system.

14. A resin composition as claimed in claim 1 which has a pot life of at least about 18 hours at 25°

C.

15. A resin composition as claimed in claim 1 which is curable in 30 seconds at 200°

C.

16. A resin composition as claimed in claim 1 which is curable in 15 seconds at 200°

C.

17. A resin composition as claimed in claim 1 which is curable in 45 seconds at 200°

C.

18. A resin composition as claimed in claim 1 which is snap curable at 200°

C.

19. A resin composition as claimed in claim 1 which is stable at 25°

C. for at least 24 hours.

20. A resin composition as claimed in claim 1 which is stable at 25°

C. for at least one week.

21. A resin composition as claimed in claim 1 which is stable at 25°

C. for at least two weeks.

38. A method for preparing a die attach adhesive comprising including in the die attach adhesive a resin composition according to claim 1.

40. A method for preparing a heat sink attach adhesive comprising including in the heat sink attach adhesive a resin composition according to claim 1.

42. A method for preparing an encapsulant comprising including in the encapsulant a resin composition according to claim 1.

44. A method for preparing an underfill comprising including in the underfill a resin composition according to claim 1.

22. A resin composition comprising:

a resin system comprising at least one epoxy resin present in an amount of from about 5% to about 95% by weight of the resin system and at least one cyanate ester resin present in an amount of from about 5% to about 80% by weight of the resin system;

a compound having the formula;

##STR3## wherein m and n are at least 1, present in an amount of from about 5 to about 30 parts per 100 parts by weight of the resin system;

wherein the resin composition is stable at room temperature for at least about 18 hours at 25°

C. and is curable in one minute or less at 200°

C.

23. A resin composition as claimed in claim 22 wherein the epoxy resin comprises at least one aromatic epoxy resin.

24. A resin composition as claimed in claim 22, comprising at least one of bisphenol F epoxy resin or bisphenol A epoxy resin.

25. A resin composition as claimed in claim 22 wherein the cyanate ester resin comprises a polyfunctional cyanate ester resin.

26. A resin composition as claimed in claim 25 wherein the polyfunctional cyanate ester resin is selected from the group consisting of 1,1'"'"'-bis (4-cyanatophenyl) ethane, bis (4-cyanato-3,5-dimethylphenyl) methane, 2,2'"'"'-bis (4-cyanatophenyl) isopropylidene and mixtures thereof.

27. A resin composition as claimed in claim 22 wherein the epoxy resin is present in an amount of from about 10% to about 70% by weight of the resin system.

28. A resin composition as claimed in claim 22 wherein the epoxy resin is present in an amount of from about 30% to about 60% by weight of the resin system.

29. A resin composition as claimed in claim 22 wherein the cyanate ester resin is present in an a mount of from about 10% to about 60% by weight of the resin system.

30. A resin composition as claimed in claim 22 wherein the cyanate ester resin is present in an amount of from about 20% to about 40% by weight of the resin system.

31. A resin composition as claimed in claim 22 wherein the catalyst is present in an amount of from about 7 parts to about 15 parts per 100 parts by weight of the resin system.

32. A resin composition as claimed in claim 22 which is curable in 30 seconds at 200°

C.

33. A resin composition as claimed in claim 22 which is curable in 15 seconds at 200°

C.

34. A resin composition as claimed in claim 22 which is curable in 45 seconds at 145°

C.

35. A resin composition as claim 22 which is stable at 25°

C. for at least 24 hours.

36. A resin composition as claimed in claim 22 which is stable at 25°

C. for at least one week.

37. A resin composition as claimed in claim 22 which is stable at 25°

C. for at least two weeks.

39. A method for preparing a die attach adhesive comprising including in the die attach adhesive a resin composition according to claim 22.

41. A method for preparing a heat sink attach adhesive comprising including in the heat sink attach adhesive a resin composition according to claim 22.

43. A method for preparing an encapsulant comprising including in the encapsulant a resin composition according to claim 22.

45. A method for preparing an underfill comprising including in the underfill a resin composition according to claim 22.