Adhesive compositions comprising maleic acid peroxy compounds as adhesive promoters

• US 4,916,184 A
• Filed: 05/24/1989
• Issued: 04/10/1990
• Est. Priority Date: 01/13/1988
• Status: Expired due to Fees

• Current Assignee: Loctite Corporation (Henkel AG & Co KGaA)
• Original Assignee: Loctite Corporation (Henkel AG & Co KGaA)
• Inventors: Clark, Paul J.
• Primary Examiner(s): Schofer, Joseph L.
• Assistant Examiner(s): SAROFIM, NABIL F
• Application Number:
  US07/356,167
• Time in Patent Office: 321 Days
• Field of Search: 526/232.5, 525/27, 525/262, 525/303, 525/386, 528/173, 528/364, 523/176
• US Class Current: 525/27
• CPC Class Codes: C08G 75/045 from mercapto compounds and unsaturated compounds
• CPC Class Codes: C08G 75/12 Polythioether-ethers C08G75/0245 takes precedence

Abstract

An adhesive composition comprising a component which is polymerizable or cross-linkable with a peroxy initator, e.g., a (meth)acrylic ester monomer, thiolene resin, or tough acrylic copolymer, and an initiator of the formula: ##STR1## wherein: R₁ is H or lower alkyl; and R₂ is H or --OR₃, where R₃ is H or lower alkyl.

An appertaining method of bonding substrates, and bonded articles formed thereby, are also disclosed. The adhesive composition of the invention is particularly advantageous in bonding of metal substrates, on which the maleic acid peroxy compounds of the invention produce surface bonding enhancement of the adhesive composition, relative to the use of conventional polymerization/crosslinking peroxy initiators such as t-butyl perbenzoate.

Claims

1. A curable adhesive composition comprising (i) a crosslinkable component containing ethylenic unsaturation and (ii) from about 0.1 to about 10 percent by weight, based on the combined weight of (i) and (ii) of an initiator of the formula:

##STR4## wherein R₁ is H or lower alkyl and R₂ is H or --OR₃, where R₃ is H or lower alkyl.

3. A bonded article comprising surfaces bonded to one another with a cured adhesive composition formed by curing of the adhesive composition of claim 1.

4. A bonded article according to claim 3, wherein said initiator is t-butyl peroxy maleic acid.

5. A bonded article according to claim 4, comprising in the cured adhesive composition a polymerized (meth)acrylic ester.

6. The curable adhesive composition of claim 1 wherein the crosslinkable component is selected from the group consisting of

(a) (meth)acrylic esters;

(b) thiolene systems;

(c) copolymer systems including elastomeric repeating units and non-elastomeric repeating units and comprising crosslinkable ethylenically unsaturated moieties; and

(d) unsaturated polyesters.

7. The curable adhesive composition of claim 6 wherein the crosslinkable component is a (meth)acrylic ester selected from the group consisting of

(a) (meth)acrylate monomers;

(b) (meth)acrylic functional polymers; and

(c) blends of (a) or (b) with rubber monomer or polymers.

8. The curable adhesive composition of claim 1 wherein the initiator (i) is employed in an amount of the about 0.5 to about 4 percent by weight based on the combined weight of (i) and (ii).

9. The curable adhesive composition of claim 1 wherein R₁ is lower alkyl and R₂ is H.

10. The curable adhesive composition of claim 9 wherein R₁ is t-butyl.

11. The curable adhesive composition of claim 1 wherein R₁ is H and R₂ is lower alkoxy.

19. The curable adhesive composition of claim 1 further comprising a cure promoter or accelerator.

2. An adhesive composition comprising an anaerobically curable ethylenically unsaturated monomer, and a polymerization initiator for said monomer, of the formula:

##STR5## wherein;

R₁ is H or lower alkyl; and

R₂ is H or --OR₃, where R₃ is H or lower alkyl.

12. An improved adhesive composition comprising (i) a curable component containing ethylenic unsaturation and (ii) an effective amount of an initiator therefor wherein the improvement comprises employing as the initiator (ii) a compound of the formula ##STR6## wherein R₁ is H or lower alkyl and R₂ is H or --OR₃, wherein R₃ is H or lower alkyl for enhanced adhesion of the cured adhesive composition to metal substrates.

13. The improved composition of claim 12 wherein the initiator is employed in an amount of from about 0.5 to about 10 percent by weight based on the combined weight of the curable component (i) and the initiator (ii).

14. The improved composition of claim 12 wherein the initiator is employed in an amount of from about 0.5 to about 4 percent by weight based on the combined weight of the curable component (i) and the initiator (ii).

15. The improved composition of claim 12 wherein R₁ is lower alkyl and R₂ is H.

16. The improved composition of claim 15 wherein R₂ is t-butyl.

17. The improved composition of claim 12 wherein the curable component (ii) is selected from the group consisting of

(a) crosslinkable (meth)acrylic esters;

(b) thiolene resin systems;

(c) copolymer systems including elastomeric repeating units and non-elastomeric repeating units and comprising crosslinkable ethylenically unsaturated moieties; and

(d) unsaturated polyesters stabilized in vinyl monomers.

18. The improved composition of claim 12 further comprising a cure promoter or accelerator.