Cyanoacrylate compositions

Patent metadata

Field	Value
Publication number	US-9550883-B2
Application number	US-201414333952-A
Country	US
Kind code	B2
Filing date	Jul 17, 2014
Priority date	Jan 25, 2012
Publication date	Jan 24, 2017
Grant date	Jan 24, 2017

Abstract

Cyanoacrylate-containing compositions that include, in addition to the cyanoacrylate component, an anhydride and a maleimide-, itaconimide-, or nadimide-containing compound, are provided. Cured products of the inventive cyanoacrylate compositions demonstrate improved moisture and/or heat resistance.

First claim

What is claimed is:

1. A cyanoacrylate adhesive composition, comprising:
(a) a cyanoacrylate component,
(b) an anhydride in an amount within the range of about 0.01% to about 1% by weight, wherein the anhydride is dimethyl maleic anhydride, and
(c) a maleimide-, itaconimide-, or nadimide-containing compound in an amount within the range of about 0.01% to about 3% by weight.

2. The composition according to claim 1 , wherein the anhydride is a phthalic anhydride.

3. The composition of claim 1 , further comprising a stabilizing amount of an acidic stabilizer and a free radical inhibitor.

4. The composition according to claim 1 , wherein the cyanoacrylate component is selected from materials within the structure H 2 C═C(CN)—COOR, wherein R is selected from C 1-15 alkyl, alkoxyalkyl, cycloalkyl, alkenyl, aralkyl, aryl, allyl and haloalkyl groups.

5. The composition according to claim 1 , wherein the cyanoacrylate component comprises β-methoxyethyl-2-cyanoacrylate.

6. The composition according to claim 1 , further comprising an accelerator component selected from the group consisting of calixarene, oxacalixarene, silacrown, cyclodextrin, crown ether, poly(ethyleneglycol) di(meth)acrylate, ethoxylated hydric compound, and combinations thereof.

7. The composition according to claim 6 , wherein the calixarene is tetrabutyl tetra[2-ethoxy-2-oxoethoxy]calix-4-arene.

8. The composition according to claim 6 , wherein the crown ether is selected from members within 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 composition according to claim 6 , wherein the poly(ethyleneglycol) di(meth)acrylate is within the following structure:

wherein n is greater than 3.

10. The composition according to claim 1 , further comprising additives selected from the group consisting of shock resistant additives, thixotropy conferring agents, thickeners, dyes, and combinations thereof.

11. Reaction products of the composition according to claim 1 .

12. A method of bonding together two substrates, comprising the steps of:
applying a cyanoacrylate adhesive composition according to claim 1 , to at least one of the substrates and
mating together the substrates for a time sufficient to permit the adhesive to fixture.

13. A method of preparing a cyanoacrylate-adhesive composition according to claim 1 , comprising the steps of:
providing a cyanoacrylate component, and
combining therewith with mixing an anhydride in an amount within the range of about 0.01% to about 1% by weight and a maleimide-, itaconimide-, or nadimide-containing compound in an amount within the range of about 0.01% to about 3% by weight, wherein the anhydride is dimethyl maleic anhydride.

14. A method of conferring improved humidity and/or thermal resistance to a cured product of a cyanoacrylate composition, comprising the steps of:
providing a cyanoacrylate composition; and
providing thereto with mixing an anhydride in an amount within the range of about 0.01% to about 1% by weight and a maleimide-, itaconimide-, or nadimide-containing compound in an amount within the range of about 0.01% to about 3% by weight, wherein the anhydride is dimethyl maleic anhydride.

15. In a cyanoacrylate composition comprising a cyanoacrylate component, wherein the improvement comprises adding to the cyanoacrylate component an anhydride in an amount within the range of about 0.01% to about 1% by weight and a maleimide-, itaconimide-, or nadimide-containing compound in an amount within the range of about 0.01% to about 3% by weight to improve the humidity and/or heat resistance of cured reaction products thereof, wherein the anhydride is dimethyl maleic anhydride.

16. The composition according to claim 1 , wherein the anhydride is present in amount within the range of about 0.05 to about 0.2% by weight.

17. The composition according to claim 1 , wherein the maleimide-, itaconimide-, or nadimide-containing compound is present in amount within the range of about 0.1% to about 2% by weight.

18. The composition according to claim 1 , wherein the anhydride present in an amount of up to about 0.01% by weight to about 0.5% by weight and the maleimide-, itaconimide-, or nadimide-containing compound is present in an amount of about 0.1% to about 2% by weight.

19. The composition according to claim 1 , wherein the anhydride present in an amount of about 0.1% by weight and the maleimide-, itaconimide-, or nadimide-containing compound is present in an amount of about 2% by weight.

Assignees

• Henkel IP & Holding GmbH

Inventors

• Li Ling

Classifications

• C09J4/00

  Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond {; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16} · CPC title

• C08L35/04

  Homopolymers or copolymers of nitriles (C08L35/06, C08L35/08 take precedence) · CPC title

• C08K5/3415

  Five-membered rings · CPC title

• C08K5/1539 Primary

  Cyclic anhydrides · CPC title

• C08F222/32

  Alpha-cyano-acrylic acid; Esters thereof · CPC title