Cyanoacrylate compositions

Patent metadata

Field	Value
Publication number	US-9783714-B2
Application number	US-201313838303-A
Country	US
Kind code	B2
Filing date	Mar 15, 2013
Priority date	Mar 15, 2013
Publication date	Oct 10, 2017
Grant date	Oct 10, 2017

Abstract

Allyl-cyanoacrylate-containing compositions with an anhydride aromatic component, which when cured confers improved moisture resistance, are provided.

First claim

What is claimed is:

1. A cyanoacrylate adhesive composition, comprising:
(a) a cyanoacrylate component comprising allyl-2-cyanoacrylate and another cyanoacrylate monomer, and
(b) in an amount up to about 1% by weight based on the total composition, an aromatic anhydride component selected from the group consisting of phthalic anhydride, 4,4′-(4,4′-isopropylidone diphenoxy)bis(phthalic anhydride), and combinations thereof,

wherein said allyl-2-cyanoacrylate is present in an amount of at least 40% by weight, based on the cyanoacrylate component.

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

3. The composition according to claim 1 , wherein the another cyanoacrylate monomer is (a) represented by H 2 C═C(CN)—COOR, wherein R is selected from C 1-15 alkyl, alkoxyalkyl, cycloalkyl, alkenyl, aralkyl, aryl and haloalkyl groups, or (b) a biscyanoacrylate.

4. 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.

5. The composition according to claim 4 , 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-cyclonexyl-18-crown-6, asym-dibenzo-22-crown-6, and 1,2-benzo-1,4-benzo-5-oxygen-20-crown-7 and combinations thereof.

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

7. The composition according to claim 1 , wherein said allyl-2-cyanoacrylate is present in an amount of up to about 90% by weight of the cyanoacrylate component.

8. The composition according to claim 1 , wherein cured products of which show improved moisture resistance at a temperature of 65° C. and 95% relative humidity.

9. A cyanoacrylate adhesive composition, comprising
(a) a cyanoacrylate component comprising allyl-2-cyanoacrylate and another cyanoacrylate monomer,
(b) an aromatic anhydride component selected from the group consisting of phthalic anhydride, 4,4′-(4,4′-isopropylidone diphenoxy)bis(phthalic anhydride), and combinations thereof, and
(c) a hydrogenated aromatic anhydride component, wherein said allyl-2-cyanoacrylate is present in an amount of at least 50% by weight, based on the cyanoacrylate component.

10. The composition according to claim 9 , wherein cured products of which show improved moisture resistance at a temperature of 65° C. and 95% relative humidity.

11. A cyanoacrylate adhesive composition, comprising:
(a) a cyanoacrylate component comprising in an amount of at least 40% by weight, allyl-2-cyanoacrylate, and in an amount of at least 60% by weight, ethyl-2-cyanoacrylate, each based on the total cyanoacrylate component, and
(b) in an amount of about 0.5% by weight, phthalic anhydride, based on the total composition.

12. The composition according to claim 11 , wherein cured products of which show improved moisture resistance at a temperature of 65° C. and 95% relative humidity.

13. The composition according to claim 11 , wherein said allyl-2-cyanoacrylate is present in an amount of at least 40% by weight to about 90% by weight.

14. 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.

15. A method of preparing a cyanoacrylate adhesive composition according to claim 1 , comprising the steps of:
providing allyl-2-cyanoacrylate and another cyanoacrylate, and
combining therewith with mixing an aromatic anhydride component.

16. A method of improving moisture resistance at a temperature of 65° C. and 95% relative humidity of cured cyanoacrylate compositions on assemblies having at least one substrate constructed from steel, comprising the steps of:
applying a cyanoacrylate adhesive composition according to claim 1 , to at least one of the substrates;
mating together the substrates for a time sufficient to permit the cyanoacrylate adhesive composition to fixture and form assemblies; and
exposing the assemblies to a temperature of 65° C. and 95% relative humidity.

Assignees

• Henkel Ireland Ltd
• Henkel IP & Holding GmbH

Inventors

• Goff Ciara
• Phelan Marisa
• Guthrie John
• Duffy Cormac
• Horn Sabine
• Despotopoulou Christina

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

• C08F220/66

  Anhydrides · CPC title

• C08F222/06

  Maleic anhydride · CPC title

• C09J167/06 Primary

  Unsaturated polyesters having carbon-to-carbon unsaturation · CPC title

• C08F222/32

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