Adhesives and adhesive compositions containing thioether groups

• US 20030017341A1
• Filed: 03/07/2001
• Published: 01/23/2003
• Est. Priority Date: 03/07/2001
• Status: Active Grant

• Current Assignee: 3M Innovative Properties Company (3M Company)
• Original Assignee: 3M Innovative Properties Company (3M Company)
• Inventors: Gross, Kathleen B., Thompson, Wendy L., Schultz, William J., Pocius, Alphonsus V., Noe, Susan C.
• Granted Patent: US 6,800,371 B2
• Time in Patent Office: Days
• US Class Current: 428/413
• CPC Class Codes: C08G 59/302 containing sulfur
• CPC Class Codes: C08G 59/38 together with di-epoxy compounds
• CPC Class Codes: C08L 63/00 Compositions of epoxy resins; Compositions of derivatives of epoxy resins
• CPC Class Codes: C09J 163/00 Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
• CPC Class Codes: C09J 2400/163 in the substrate
• CPC Class Codes: C09J 2400/226 in the substrate
• CPC Class Codes: C09J 2463/00 Presence of epoxy resin
• CPC Class Codes: C09J 2479/086 in the substrate
• CPC Class Codes: C09J 2483/006 in the substrate
• CPC Class Codes: C09J 5/06 involving heating of the applied adhesive
• CPC Class Codes: Y10T 428/31511 Of epoxy ether

Abstract

In one aspect, the invention provides a curable composition comprising a mixture of epoxy resin, catalyst and an epoxy reactive thioether-containing compound and the resulting adhesives. The resulting adhesives are water and/or solvent resistant and bond to plastics such as ABS, polycarbonate, and PMMA; polyimide; noble metals such as gold and palladium; and silicon-containing materials such as silicon wafer die and silicon dioxide.

Claims

1. An article of manufacture comprising:

a substrate comprising silicon, noble metal, plastics, polyimide, or combinations thereof; and

an adhesive comprising the reaction product of;

epoxy resin;

catalyst or curative; and

epoxy reactive thioether-containing compound, adhesively bonded to the substrate.

2. The article of claim 1 wherein the plastic is selected from the group consisting of acrylonitrile-butadiene-styrene, poly(methyl methacrylate), polycarbonate, or mixtures thereof, and wherein the epoxy reactive thioether-containing compound has a molecular weight of from about 320 to about 650.

3. The article of claim 1 wherein the noble metal is selected from the group consisting of gold, platinum, palladium, silver, iridium, and combinations thereof.

4. The article of claim 1 wherein the silicon is selected from the group consisting of silicon dioxide, silicon die, and combinations thereof.

5. The article of claim 1 wherein the epoxy reactive thioether-containing compound comprises a thioether di-epoxide.

6. The article of claim 1 wherein the epoxy resin comprises a polyfunctional phenolic glycidyl ether epoxy resin.

7. The article of claim 1 wherein the epoxy reactive thioether-containing compound is selected from the group consisting of 2-{[3-({2-[(2-{[3-(2-oxiranylmethoxy)propyl]sulfanyl}ethyl)sulfanyl]ethyl}sulfanyl)propoxy]methyl}oxirane;

2({3-[(6-{[3-(2-oxiranylmethoxy)propyl]sulfanyl}hexyl)sulfanyl]propoxy}methyl)oxirane; and

2-({3-[(2-{[3-(2-oxiranylmethoxy)propyl]sulfanyl}ethoxyethoxyethyl)sulfanyl]propoxy}methyl)oxirane, and combinations thereof.

34. The article of claim 1 wherein the substrate comprises polyimide.

8. A method of bonding a substrate comprising the steps of:

contacting the substrate with an adhesive composition comprising a mixture of;

epoxy resin;

catalyst or curative; and

epoxy reactive thioether-containing compound; and

curing the adhesive composition, wherein the substrate comprises silicon, noble metal, plastics, polyimide, or combinations thereof.

9. The method of claim 8 wherein the plastic is selected from the group consisting of acrylonitrile-butadiene-styrene, poly(methyl methacrylate), polycarbonate, or mixtures thereof, and wherein the epoxy reactive thioether-containing compound has a molecular weight of from about 320 to about 650.

10. The method of claim 8 wherein the substrate is a print head or an inkjet cartridge.

35. The method of claim 8 wherein the epoxy reactive thioether-containing compound has a molecular weight of from about 320 to about 650.

11. A curable adhesive composition useful for bonding substrates comprising silicon, noble metal, plastics, polyimide, or a combination thereof comprising a mixture of:

epoxy resin;

catalyst or curative; and

epoxy reactive thioether-containing compound.

12. The curable adhesive composition of claim 11 wherein the epoxy reactive thioether-containing compound has a molecular weight of from about 320 to about 650.

13. The curable adhesive composition of claim 12 wherein the epoxy reactive thioether-containing compound comprises a thioether di-epoxide.

14. The curable adhesive composition of claim 11 wherein the epoxy resin comprises a polyfunctional phenolic glycidyl ether epoxy resin.

15. The curable adhesive composition of claim 11 wherein the epoxy reactive thioether-containing compound is selected from the group consisting of 2-{[3-({2-[(2-{[3-(2-oxiranylmethoxy)propyl]sulfanyl}ethyl)sulfanyl]ethyl}sulfanyl)propoxy]methyl}oxirane;

2({3-[(6-{[3-(2-oxiranylmethoxy)propyl]sulfanyl}hexyl)sulfanyl]propoxy}methyl)oxirane; and

2-({3-[(2-{[3-(2-oxiranylmethoxy)propyl]sulfanyl}ethoxyethoxyethyl)sulfanyl]propoxy}methyl)oxirane, and combinations thereof.

16. The curable adhesive composition of claim 11 wherein the epoxy reactive thioether-containing compound is present in the adhesive composition at a level of from about 10 to about 80 parts by weight.

17. The curable adhesive composition of claim 16 wherein the epoxy resin is present in the adhesive composition at a level of from about 20 to about 80 parts by weight.

18. The curable adhesive composition of claim 17 wherein the curative comprises a poly(oxyhydrocarbolene) diamine.

19. The curable adhesive composition of claim 11 further comprising a coupling agent, a filler, or a combination thereof.

20. The curable adhesive composition of claim 17 wherein the catalyst comprises an imidazole.

21. An adhesive useful for bonding substrates comprising silicon, noble metal, plastics, polyimide, or a combination thereof comprising the reaction product of:

epoxy resin;

catalyst or curative; and

epoxy reactive thioether-containing compound.

22. The adhesive of claim 21 wherein the epoxy reactive thioether-containing compound has a molecular weight of from about 320 to about 650.

23. The adhesive of claim 21 wherein the epoxy reactive thioether-containing compound is selected from the group consisting of 2-{[3-({2-[(2-{[3-(2-oxiranylmethoxy)propyl]sulfanyl}ethyl)sulfanyl]ethyl}sulfanyl)propoxy]methyl}oxirane;

2({3-[(6-{[3-(2-oxiranylmethoxy)propyl]sulfanyl }hexyl)sulfanyl]propoxy methyl)oxirane; and

2-({3-[(2-{[3-(2-oxiranylmethoxy)propyl]sulfanyl}ethoxyethoxyethyl)sulfanyl]propoxy}methyl)oxirane, and combinations thereof.

24. The adhesive of claim 21 wherein the catalyst is an imidazole.

25. The adhesive of claim 21 wherein the curative is a polyamine.

26. The adhesive of claim 21 further comprising an additive comprisin silicon atoms.

27. The adhesive of claim 21 having low-stress and water and solvent resistance.

29. The method of claim 28 wherein the epoxy reactive thioether-containing compound is a thioether di-epoxide.

30. The method of claim 28 wherein the epoxy reactive thioether-containing compound is selected from the group consisting of 2-{[3-({2-[(2-{[3-(2-oxiranylmethoxy)propyl]sulfanyl}ethyl)sulfanyl]ethyl}sulfanyl)propoxy]methyl}oxirane;

2({3-[(6-{[3-(2-oxiranylmethoxy)propyl]sulfanyl}hexyl)sulfanyl]propoxy}methyl)oxirane; and

2-({3-[(2-{[3-(2-oxiranylmethoxy)propyl]sulfanyl}ethoxyethoxyethyl)sulfanyl]propoxy}methyl)oxirane, and combinations thereof.

31. The method of claim 28 wherein the epoxy resin comprises a polyfunctional phenolic glycidyl ether epoxy resin.

32. The method of claim 28 wherein the curative comprises an epoxy reactive amine.

33. The method of claim 28 wherein the catalyst comprises an imidazole.

28. A method of flexibilizing and improving the solvent and/or water resistance of an epoxy resin adhesive comprising the steps of:

adding from about 10 to about 80 parts by weight of epoxy reactive thioether-containing compound to a curable epoxy resin adhesive composition; and

curing the epoxy resin adhesive composition to form the solvent and/or water resistant epoxy resin adhesive.