Cyanoacrylate compositions

1. A method of conferring improved thermal resistance to a cured product of a cyanoacrylate adhesive composition, comprising the steps of:

providing a cyanoacrylate adhesive composition made from an allyl-2-cyanoacrylate and having added thereto in an amount of about 10 to about 20 weight percent based on the cyanoacrylate adhesive composition a bis-cyanoacrylate to form the cyanoacrylate adhesive composition;

providing at least two substrates;

dispensing the cyanoacrylate adhesive composition onto at least one of the substrates;

joining the substrates in a mating relationship with the cyanoacrylate adhesive composition disposed therebetween and allowing the cyanoacrylate adhesive composition to cure thereby forming an assembly with the cured cyanoacrylate adhesive composition adhesively bonding together the two substrates; and

exposing the assembly to elevated temperature conditions of at least 120° C., said cured cyanoacrylate adhesive composition having improved resistance to thermal degradation at that elevated temperature over an allyl-2-cyanoacrylate-containing cyanoacrylate adhesive composition without the added bis-cyanoacrylate.

2. The method according to claim 1 , wherein the cyanoacrylate adhesive composition further comprises a member selected from the group consisting of methyl cyanoacrylate, ethyl-2-cyanoacrylate, propyl cyanoacrylates, butyl cyanoacrylates, octyl cyanoacrylates, and β-methoxyethyl cyanoacrylate.

3. The method according to claim 1 , wherein the bis-cyanoacrylate is represented by structure I

wherein R in structure I is a linkage selected from (CH 2 ) n , with n being 2, 3, 4, 5, 6, 8, 9, 10, or 12.

4. The method according to claim 1 , wherein the bis-cyanoacrylate is selected from the group consisting of 1,10-decanediol bis-cyanoacrylate, 1,8-octanediol bis-cyanoacrylate, and 1,6-hexanediol bis-cyanoacrylate.

5. The method according to claim 1 , wherein the cyanoacrylate adhesive composition further comprises a stabilizing amount of an anionic stabilizer and a free radical stabilizer.

6. The method according to claim 1 , wherein the cyanoacrylate adhesive composition further comprises an accelerator component.

7. The method according to claim 6 , wherein the accelerator component is selected from the group consisting of calixarene, oxacalixarene, silacrown, cyclodextrin, crown ether, poly(ethyleneglycol) di(meth)acrylate, ethoxylated hydric compound, and combinations thereof.

8. The method according to claim 7 , wherein the crown ether is selected from the group consisting of 15-crown-5, 18-crown-6, dibenzo-18-crown-6, benzo-15-crown-5-dibenzo-24-crown-8, dibenzo-30-crown-10, tribenzo-18-crown-6, asym-dibenzo-22-crown-6, dibenzo-14-crown-4, dicyclohexyl-18-crown-6, dicyclohexyl-24-crown-8, cyclohexyl-12-crown-4, 1,2-decalyl-15-crown-5, 1,2-naphtho-15-crown-5, 3,4,5-naphtyl-16-crown-5, 1,2-methyl-benzo-18-crown-6, 1,2-methylbenzo-5, 6-methylbenzo-18-crown-6, 1,2-t-butyl-18-crown-6, 1,2-vinylbenzo-15-crown-5, 1,2-vinylbenzo-18-crown-6, 1,2-t-butyl-cyclohexyl-18-crown-6, asym-dibenzo-22-crown-6, and 1,2-benzo-1,4-benzo-5-oxygen-20-crown-7 and combinations thereof.

9. The method according to claim 1 , wherein the cyanoacrylate adhesive composition further comprises additives selected from the group consisting of tougheners, shock resistant additives, thixotropy conferring agents, thickeners, dyes, and combinations thereof.

10. A method of conferring improved thermal resistance to a cured product of a cyanoacrylate adhesive composition, comprising the steps of:

dispensing a cyanoacrylate adhesive composition made from an allyl-2-cyanoacrylate and having added thereto in an amount of about 10 to about 20 weight percent based on the cyanoacrylate adhesive composition a bis-cyanoacrylate onto at least one substrate to which another substrate is joined in a mating relationship and allowing the cyanoacrylate adhesive composition to cure thereby forming an assembly with the cured cyanoacrylate adhesive composition adhesively bonding together the two substrates; and

exposing the assembly to elevated temperature conditions of at least 120° C., said cured cyanoacrylate adhesive composition having improved resistance to thermal degradation at that elevated temperature over an allyl-2-cyanoacrylate-containing cyanoacrylate adhesive composition without the added bis-cyanoacrylate.