Adhesive compositions with durability under conditions of high humidity

• US 5,883,193 A
• Filed: 07/01/1997
• Issued: 03/16/1999
• Est. Priority Date: 07/01/1997
• Status: Expired due to Fees

• Current Assignee: 3M Company
• Original Assignee: 3M Company
• Inventors: Karim, Naimul
• Primary Examiner(s): Szekely, Peter A.
• Application Number:
  US08/886,750
• Time in Patent Office: 623 Days
• Field of Search: 525/113, 525/529, 525/531
• US Class Current: 525/113
• CPC Class Codes: C09J 4/06 Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00

Abstract

A thermosettable adhesive composition that includes a monomeric or partially polymerized composition that includes at least one polymerizable acrylic or methacrylic acid ester of a non-tertiary alcohol, a thermosettable epoxy resin, an amine curative, a silane coupling agent, and a chelating agent.

Claims

1. A thermosettable adhesive composition comprising:

a monomeric or partially polymerized composition comprising at least one polymerizable acrylic or methacrylic acid ester of a non-tertiary alcohol;

a thermosettable epoxy resin;

an amine curative;

a silane coupling agent; and

a chelating agent.

2. The thermosettable adhesive composition of claim 1, further comprising an ethylenically unsaturated monomer different from said polymerizable acrylic or methacrylic acid ester.

3. The thermosettable adhesive composition of claim 1, further comprising a hydroxy acrylate.

4. The thermosettable adhesive composition of claim 1, wherein said chelating agent comprises aminocarboxylates, crown ethers, 1,3-diketones, imines, oximes, phenols, or polyols.

5. The thermosettable adhesive composition of claim 1, wherein said chelating agent comprises dibenzo-18-crown-6, ethylenebis(salicylimine), catechol, 8-hydroxyquinoline, salicylaldehyde, or glycerol.

6. The thermosettable adhesive composition of claim 1, wherein said chelating agent comprises glycerol.

7. The thermosettable adhesive composition of claim 1, wherein said chelating agent is present in said composition in an amount in the range of between about 0.25 to about 4% by weight of said thermosettable adhesive composition.

8. The thermosettable adhesive composition of claim 1, wherein said silane coupling agent is selected from the group consisting of epoxy silanes, alkoxy silanes, aminosilanes, and combinations thereof.

9. The thermosettable adhesive composition of claim 1, wherein said silane coupling agent is present in said composition in an amount in the range of between about 0.25 to 5% by weight of said thermosettable adhesive composition.

10. The thermosettable adhesive composition of claim 1, wherein said silane coupling agent is present in said composition in an amount in the range of between about 0.25 to 1% by weight of said thermosettable adhesive composition.

11. The thermosettable adhesive composition of claim 1, wherein said epoxy resin is present in said composition in an amount of no greater than about 150 parts per 100 parts of said monomeric or partially polymerized composition.

12. The thermosettable adhesive composition of claim 1, wherein said epoxy resin is present in said composition in an amount in the range of between 50 and 110 parts per 100 parts of said monomeric or partially polymerized composition.

13. The thermosettable adhesive composition of claim 1, wherein the ratio of amine equivalents of the amine curative to epoxy equivalents is in the range of about 0.8:

1 to about 1.5;

1.

14. The thermosettable adhesive composition of claim 1, wherein said amine curative comprises dicyandiamide.

24. The thermosettable adhesive composition of claim 1, further comprising a photoinitiator.

15. A thermosettable adhesive composition comprising:

a polyacrylate or a polymethacrylate;

a thermosettable epoxy resin;

an amine curative;

a silane coupling agent; and

a chelating agent.

16. A method of bonding a first substrate to a second substrate, said method comprising:

providing one of said substrates with a thermosettable adhesive composition comprising

(a) a monomeric or partially polymerized composition comprising at least one polymerizable acrylic or methacrylic acid ester of a non-tertiary alcohol,

(b) a thermosettable epoxy resin,

(c) an amine curative,

(d) a silane coupling agent, and

(e) a chelating agent;

contacting said thermosettable adhesive composition with the other of said substrates; and

thermally curing said thermosettable adhesive composition.

17. The method of claim 16, wherein said substrates comprise glass.

18. The method of claim 16, wherein one of said substrates comprises glass and the other of said substrates comprises metal.

19. The method of claim 16, wherein one of said substrates comprises glass and the other of said substrates comprises ceramic.

20. The method of claim 16, wherein one of said substrates comprises glass and the other of said substrates comprises painted metal.

21. A method of bonding a first substrate to a second substrate, said method comprising:

providing one of said substrates with a thermosettable adhesive composition comprising

(a) an polyacrylate or a polymethacrylate,

(b) a thermosettable epoxy resin,

(c) an amine curative,

(d) a silane coupling agent, and

(e) a chelating agent;

contacting said thermosettable adhesive composition with the other of said substrates; and

thermally curing said thermosettable adhesive composition.

22. A method of bonding a mirror button to a windshield comprising:

providing one of the mirror button or the windshield with a thermosettable adhesive composition comprising

(a) a polyacrylate or a polymethacrylate,

(b) a thermosettable epoxy resin,

(c) an amine curative,

(d) a silane coupling agent, and

(e) a chelating agent;

contacting said thermosettable adhesive composition with the other of the mirror button or the windshield; and

thermally curing said thermosettable adhesive composition.

23. A thermosettable adhesive composition comprising:

a monomeric or partially polymerized composition comprising at least one polymerizable acrylic or methacrylic acid ester of a non-tertiary alcohol;

a thermosettable epoxy resin;

an amine curative;

2-hydroxy-3-phenoxypropyl acrylate;

a silane coupling agent; and

a chelating agent.