IP Library Granted Patent US 8,303,705
Granted Patent B2
US 8,303,705 · App. 13/270,263 · Granted Nov 6, 2012

Cyanoacrylate compositions

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Quick Facts
Patent No.
US 8,303,705
App. No.
13/270,263
Granted
Nov 6, 2012
Kind
B2
Abstract

This invention relates to cyanoacrylate compositions that include, in addition to the cyanoacrylate component, a compound embraced by structure A: where D is independently a member selected from O or S, and A is independently a member selected from hydrogen, linear, branched or cyclic alkyl groups having from 1 to about 20 carbon atoms, alkenyl groups having from 2 to about 20 carbon atoms, alkynyl groups having from 2 to about 20 carbon atoms, and aryl groups having from 6 to about 20 carbon atoms, with or without interruption or substitution by a member selected from halogen, silicon, hydroxy, ester, and sulfate, provided that at least one A is not H and that at least one A has at least one carboxyl group attached thereto.

Claims (23)

1. A cyanoacrylate composition comprising:

(a) a cyanoacrylate component; and

(b) a compound embraced within structure A:

wherein D is independently a member selected from the group consisting of O and S, and

A is independently a member selected from the group consisting of hydrogen, linear, branched or cyclic alkyl groups having from 1 to about 20 carbon atoms, alkenyl groups having from 2 to about 20 carbon atoms, alkynyl groups having from 2 to about 20 carbon atoms, and aryl groups having from 6 to about 20 carbon atoms, with or without interruption or substitution by a member selected from the group consisting of halogen, silicon, hydroxy, ester, and sulfate, provided that at least one A is not H and that at least one A has at least one carboxyl group attached thereto.

2. The composition of claim 1 , further comprising an accelerator.

3. The composition of claim 2 , wherein the accelerator is a member selected from the group consisting of calixarenes and oxacalixarenes, silacrowns, crown ethers, cyclodextrins, poly(ethyleneglycol) di(meth)acrylates, ethoxylated hydric compounds and combinations thereof.

4. The composition of claim 1 , further comprising a thickener.

5. The composition of claim 1 , further comprising a thixotrope.

6. The composition of claim 1 , wherein in the compound D is O and A is ethylene carboxylic acid.

7. The composition of claim 1 , wherein the compound is present in an amount between about 0.01 and about 10 percent by weight.

8. The composition of claim 1 , further comprising a filler.

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

10. The composition of 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.

11. The composition of claim 1 , wherein the cyanoacrylate component comprises ethyl-2-cyanoacrylate.

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

13. A method of bonding together two substrates, comprising the steps of:

applying a cyanoacrylate composition of claim 1 , to at least one of the substrates and

mating together the substrates for a time sufficient to permit the composition to fixture.

14. A method of preparing a cyanoacrylate composition of claim 1 , comprising the steps of:

providing a cyanoacrylate component, and combining therewith with mixing a compound embraced by structure A:

wherein D is independently a member selected from the group consisting of O and S, and

A is independently a member selected from the group consisting of hydrogen, linear, branched or cyclic alkyl groups having from 1 to about 20 carbon atoms, alkenyl groups having from 2 to about 20 carbon atoms, alkynyl groups having from 2 to about 20 carbon atoms, and aryl groups having from 6 to about 20 carbon atoms, with or without interruption or substitution by a member selected from the group consisting of halogen, silicon, hydroxy, ester, and sulfate, provided that at least one A is not H and that at least one A has at least one carboxyl group attached thereto.

Assignments (8)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 9, 2022
From: HENKEL IP & HOLDING GMBH
To: HENKEL AG & CO. KGAA
Reel/Frame 059357/0267 →
MERGER Recorded Feb 24, 2014
From: HENKEL IRELAND LIMITED
To: HENKEL AG & CO. KGAA
Reel/Frame 032329/0132 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 24, 2014
From: HENKEL AG & CO. KGAA
To: HENKEL IP & HOLDING GMBH
Reel/Frame 032329/0172 →
CHANGE OF ADDRESS Recorded Feb 21, 2014
From: HENKEL IRELAND LIMITED
To: HENKEL IRELAND LIMITED
Reel/Frame 032319/0955 →
MERGER Recorded Feb 1, 2013
From: HENKEL IRELAND HOLDING B.V.
To: HENKEL IRELAND LIMITED
Reel/Frame 029741/0205 →
MERGER Recorded Feb 1, 2013
From: LOCTITE (R&D) LIMITED
To: HENKEL IRELAND HOLDING B.V.
Reel/Frame 029741/0063 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 9, 2012
From: HENKEL IRELAND LIMITED
To: LOCTITE (R&D) LIMITED
Reel/Frame 029268/0178 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 8, 2012
From: BARNES, RORY R.; BURNS, BARRY N.; HERSEE, RACHEL M.
To: HENKEL IRELAND LIMITED
Reel/Frame 029266/0349 →