Adhesive compositions based on grafted resins

Patent metadata

Field	Value
Publication number	US-11279861-B2
Application number	US-201816486262-A
Country	US
Kind code	B2
Filing date	Feb 20, 2018
Priority date	Feb 20, 2017
Publication date	Mar 22, 2022
Grant date	Mar 22, 2022

Abstract

A curable adhesive that is particularly well suited for use in an injection or compression molding operation. The adhesive is based on polymeric resins having carboxylic acid and acrylate ester functionality, such as grafted phenoxy resin, and further constituents such as organic carbonates, blocked isocyanates, catalysts, maleimide compounds, hydride sources, and a carrier fluid. The curable adhesives are particularly well suited for bonding liquid injectable substrates such as liquid silicone rubber, or polyamides to rigid substrates, such as aluminum, stainless steel, or glass.

First claim

What is claimed is:

1. A curable adhesive comprising a grafted phenoxy resin, an organic carbonate, and a solvent, wherein the grafted phenoxy resin comprises carboxylic acid and acrylate ester functionality.

2. The adhesive of claim 1 , wherein the carboxylic acid functionality comprises a —COOH moiety.

3. The adhesive of claim 1 , wherein the acrylate ester functionality comprises a —COOCH3 moiety.

4. The adhesive of claim 1 , further comprising an isocyanate.

5. The adhesive of claim 4 , wherein the isocyanate comprises a blocked isocyanate.

6. The adhesive of claim 5 , wherein the blocked isocyanate comprises a MDI-uretdione.

7. The adhesive of claim 1 , wherein the organic carbonate comprises propylene carbonate.

8. The adhesive of claim 1 , further comprising a catalyst.

9. The adhesive of claim 8 , provided in two parts wherein the grafted resin is provided in a first part separate from the catalyst in the second part.

10. The adhesive of claim 8 , wherein the catalyst comprises a platinum catalyst.

11. The adhesive of claim 1 , further comprising a maleimide compound.

12. The adhesive of claim 1 further comprising a metal acetylacetonate.

13. The adhesive of claim 12 , wherein the metal acetylacetonate comprises zinc acetylacetonate.

14. The adhesive of claim 1 , further comprising a hydride source.

15. The adhesive of claim 13 , wherein the hydride source comprises polymethylhydrosiloxane.

16. The adhesive of claim 1 , further comprising a benzoxazine resin and a catalyst for the benzoxazine resin.

17. The adhesive of claim 16 , wherein the catalyst comprises an amine salt of trifluoromethanesulfonic acid.

18. The adhesive of claim 16 , wherein the organic carbonate comprises diphenyl carbonate.

19. The adhesive of claim 16 , disposed between a thermoplastic substrate and a metal substrate.

20. The adhesive of claim 19 , wherein the thermoplastic substrate comprises polybutylene terephthalate and the metal substrate comprises aluminum.

21. The adhesive of claim 1 , employed to bond a liquid-introduced substrate to a rigid substrate.

22. The adhesive of claim 21 , wherein the liquid introduced substrate comprises liquid silicone rubber.

23. The adhesive of claim 22 , wherein the liquid introduced substrate comprises a peroxide cured elastomer.

24. The adhesive of claim 23 , wherein the peroxide cured elastomer comprises at least one of hydrogenated nitrile butadiene rubber (HNBR), ethylene propylene diene monomer rubber (EPDM), fluoroelastomers (FKM), or fluorosilicones (FVMQ).

25. The adhesive of claim 21 , wherein the rigid substrate comprises at least one of stainless steel, aluminum, polycarbonate or polyamide.

26. The adhesive of claim 1 , wherein the adhesive is free of any materials containing isocyanate functionality.

27. A bonded assembly comprising a liquid introduced substrate bonded to a rigid substrate with a curable adhesive of claim 1 .

28. The bonded assembly of claim 27 , wherein the liquid introduced substrate comprises a liquid silicone rubber, polybutylene terephthalate, a thermoplastic urethane, a castable urethane, or a peroxide cured elastomer.

29. The bonded assembly of 28 , wherein the peroxide cured elastomer comprises at least one of hydrogenated nitrile butadiene rubber (HNBR), fluoroelastomers (FKM), or fluorosilicones (FVMQ).

30. The bonded assembly of claim 27 , wherein the rigid substrate comprises at least one of polycarbonate, polyamide, stainless steel, or aluminum.

31. A method of bonding two dissimilar materials in an injection or compression molding process comprising:
selecting a rigid substrate,
selecting a liquid introduced substrate, and
providing a curable adhesive comprising a grafted phenoxy resin, an organic carbonate, and a solvent, wherein the grafted phenoxy resin comprises carboxylic acid and acrylate ester functionality.

32. The method of claim 31 , wherein the curable adhesive further comprises a maleimide compound.

33. The method of claim 31 , wherein the curable adhesive further comprises a benzoxazine resin.

34. The method of claim 31 , wherein the curable adhesive further comprises at least one of a blocked isocyanate, a catalyst, a maleimide compound, and a hydride source.

35. The method of claim 31 , wherein the grafted phenoxy resin comprises at least one of a copolymer of bisphenol A and a Bisphenol A/F epoxy.

36. A method of preparing an adhesive comprising:
reacting a phenoxy resin with at least one of methyl methacrylate, butyl acrylate, hydroxyl ethyl methacrylate, phenoxy ethyl acrylate, butyl acrylate, ethyl acrylate, hydroxyethyl acrylate, or mono-methacryloxypropyl terminated polydimethylsiloxane, and at least one of methacrylic acid, maleic anhydride, or itaconic acid, to produce a grafted phenoxy resin comprising carboxylic acid functionality and acrylate ester functionality, and
mixing the grafted phenoxy resin with an organic carbonate and a solvent to produce an adhesive.

37. The method of claim 36 , wherein the phenoxy resin comprises at least one of a copolymer of bisphenol A and a Bisphenol A/F epoxy.

38. The method of claim 36 , wherein the adhesive further comprises a hydride source and a non-platinum containing catalyst.

39. The method of claim 36 , wherein the hydride source comprises polymethylhydrosiloxane and the non-platinum catalyst comprises a zinc salt.

Assignees

• Lord Corp

Inventors

• Carney Brian
• Mowrey Douglas
• Wheeler Paul
• Cowles Rebecca
• Agag Tarek
• Perry Brian
• Heidenreich Andrew
• Kurniawan Dodik
• Phelps Jerry

Classifications

• B29K2667/006

  PBT, i.e. polybutylene terephthalate · CPC title

• B32B37/1284

  Application of adhesive · CPC title

• B32B15/18

  comprising iron or steel {(B32B15/011, B32B15/012 and B32B15/013 take precedence)} · CPC title

• C09J171/00

  Adhesives based on polyethers obtained by reactions forming an ether link in the main chain (based on polyacetals C09J159/00; based on epoxy resins C09J163/00; based on polythioether-ethers C09J181/02; based on polyethersulfones C09J181/06); Adhesives based on derivatives of such polymers · CPC title

• B32B15/08

  of synthetic resin · CPC title