Cyanoacrylate compositions

Patent metadata

Field	Value
Publication number	US-11299652-B2
Application number	US-202016858666-A
Country	US
Kind code	B2
Filing date	Apr 26, 2020
Priority date	Oct 27, 2017
Publication date	Apr 12, 2022
Grant date	Apr 12, 2022

Abstract

This invention relates to cyanoacrylate-containing compositions that include (a) a beta-alkoxy cyanoacrylate component, (b) a cyanoacrylate component selected from butyl cyanoacrylates, octyl cyanoacrylates, and combinations thereof; (c) a rubber toughening component (d) a surface modified component; and (e) an adhesion promoter. Cured products of the inventive cyanoacrylate compositions demonstrate improved toughness without an odor typically found with cyanoacrylate-containing compositions.

First claim

What is claimed is:

1. A cyanoacrylate composition, comprising:
(a) a β-alkoxyalkyl cyanoacrylate component;
(b) a cyanoacrylate component selected from the group consisting of butyl cyanoacrylates, octyl cyanoacrylates and combinations thereof;
(c) a rubber toughening component;
(d) a surface modified component; and
(e) an adhesion promoter.

2. The cyanoacrylate composition according to claim 1 , wherein the β-alkoxyalkyl cyanoacrylate component (a) and the cyanoacrylate component (b) are present in the composition in a weight ratio of from about 55 to about 85:about 5 to about 30.

3. The cyanoacrylate composition according to claim 1 , wherein the β-alkoxyalkyl cyanoacrylate component (a) and the cyanoacrylate component (b) are present in a weight ratio of about 70:30, the surface modified component (d) is a polyolefin in particulate form having an average particle size of 500 μm or less, whose surface has been modified through oxidation of the outermost surface thereof, and the adhesion promoter (e) is at least one of phosphoric acid or itaconic anhydride.

4. The cyanoacrylate composition according to claim 1 , wherein the β-alkoxyalkyl cyanoacrylate component is selected from β-methoxy ethyl cyanoacrylate, β-ethoxy ethyl cyanoacrylate, or combinations thereof.

5. The cyanoacrylate composition according to claim 1 , wherein the rubber toughening component is selected from the group consisting of (a) reaction products of the combination of ethylene, methyl acrylate and monomers having carboxylic acid cure sites, (b) dipolymers of ethylene and methyl acrylate, (c) vinylidene chloride-acrylonitrile copolymers, (d) vinyl chloride/vinyl acetate copolymer, (e) copolymers of polyethylene and polyvinyl acetate, and combinations thereof.

6. The cyanoacrylate composition according to claim 1 , wherein the rubber toughening component is a reaction product of the combination of ethylene, methyl acrylate and monomers having carboxylic acid cure sites, wherein the reaction product is free of release agents, anti-oxidants, stearic acid and polyethylene glycol ether wax.

7. The cyanoacrylate composition according to claim 1 , further comprising one or more of a thixotrope, a gelling agent, a thickener, an accelerator and a shock resistance conferring agent.

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

9. The cyanoacrylate composition according to claim 8 , wherein the calixarene is tetrabutyl tetra[2-ethoxy-2-oxoethoxy]calix-4-arene.

10. The cyanoacrylate composition according to claim 8 , 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.

11. The cyanoacrylate composition according to claim 8 , wherein the poly(ethyleneglycol) di(meth)acrylate has the following structure:

wherein n is greater than 3.

12. The cyanoacrylate composition according to claim 7 , wherein the shock resistance conferring agent is citric acid.

13. The cyanoacrylate composition according to claim 1 , wherein the β-alkoxyalkyl cyanoacrylate component (a) and the cyanoacrylate component (b) are present in the composition in a weight ratio of from about 55 to about 75: about 20 to about 35.

14. The cyanoacrylate composition according to claim 1 , wherein the 3-alkoxyalkyl cyanoacrylate component (a) is present in an amount of from about 55% to about 80% by weight, and the cyanoacrylate component is present in an amount of from about 7% to about 27% by weight, based on a total weight of the composition.

15. The cyanoacrylate composition according to claim 1 , wherein the β-alkoxyalkyl cyanoacrylate component (a) and the cyanoacrylate component (b) are present in the composition in a weight ratio in the range of about 70:30.

16. The cyanoacrylate composition according to claim 1 , further comprising a stabilizing amount of an acidic stabilizer and a free radical inhibitor.

17. Reaction products of the cyanoacrylate composition according to claim 1 .

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

19. A method of preparing a cyanoacrylate composition according to claim 1 , comprising the steps of:
providing a rubber toughening component dissolved in a cyanoacrylate component selected from the group consisting of butyl cyanoacrylates, octyl cyanoacrylates, and combinations thereof, and
combining therewith with mixing a β-alkoxyalkyl cyanoacrylate component, a surface modified component; and an adhesion promoter.

Assignees

• Henkel IP & Holding GmbH
• Henkel Ag & Co Kgaa

Inventors

• Barnes Rory B
• Hersee Rachel
• Burns Barry N

Classifications

• C08F222/04

  Anhydrides, e.g. cyclic anhydrides · CPC title

• C08F222/326

  Alpha-cyano-acrylic acid longer chain ester · CPC title

• C08F222/324

  Alpha-cyano-acrylic acid butyl ester · CPC title

• C08F222/327

  Alpha-cyano-acrylic acid alkoxy ester · CPC title

• C08F291/02 Primary

  on to elastomers · CPC title