IP Library Granted Patent US 7,687,561
Granted Patent B1
US 7,687,561 · App. 11/538,970 · Granted Mar 30, 2010

Toughened cyanoacrylate compositions

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Quick Facts
Patent No.
US 7,687,561
App. No.
11/538,970
Granted
Mar 30, 2010
Kind
B1
Abstract

The present invention relates to toughened cyanoacrylate compositions.

Claims (21)

1. A cyanoacrylate composition comprising:

at least one α-cyanoacrylate; and

a polyketone material within the following structure:

wherein ′R is

R is linear or branched C 1 to C 7 alkyl, C 2 to C 7 alkenyl, or C 3 to C 7 cycloalkyl or cycloalkenyl, interrupted or substituted by carbonyl functionality and/or functionalized with a C 1 to C 3 alkoxy group; and the sum of m, n and p is 100 percent.

2. The composition of claim 1 , wherein said polyketone material is a member selected from the group consisting of terpolymers of carbon monoxide, unsaturated ester and ethylene; and poly(ethylene-co-butylacrylate-co-carbon monoxide).

3. The composition of claim 1 , wherein said polyketone material is poly(ethylene-co-vinylacetate-co-carbon monoxide).

4. The composition of claim 1 , wherein said polyketone material is present in an amount sufficient to toughen said composition once cured.

5. The composition of claim 1 , wherein the α-cyanoacrylate is represented by compounds of the formula:

wherein R 1 represents a straight chain or branched chain substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, a straight chain or branched chain substituted or unsubstituted alkenyl group having 2 to 12 carbon atoms, a straight chain or branched chain substituted or unsubstituted alkynyl group having 2 to 12 carbon atoms, a substituted or unsubstituted cycloalkyl group, an substituted or unsubstituted aralkyl group or a substituted or unsubstituted aryl group.

6. The composition of claim 5 , wherein R 1 is selected from the group consisting of a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a pentyl group, a hexyl group, an allyl group, a methallyl group, a crotyl group, a propargyl group, a cyclohexyl group, a benzyl group, a phenyl group, a cresyl group, a 2-chloroethyl group, a 3-chloropropyl group, a 2-chlorobutyl group, a trifluoroethyl group, a 2-methoxyethyl group, a 3-methoxybutyl group, a 2-ethoxyethyl group and combinations thereof.

7. The composition of claim 1 , wherein said α-cyanoacrylate is an ethyl cyanoacrylate monomer.

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

9. The composition of claim 1 , wherein said polyketone material is present in amounts of about 0.5% to about 30% by weight of the composition.

10. The composition of claim 1 , wherein said α-cyanoacrylate compound comprises an ethyl cyanoacrylate monomer and said polyketone material comprises poly(ethylene-co-vinylacetate-co-carbon monoxide).

11. The composition of claim 1 , further comprising a co-toughener.

12. The composition of claim 11 , wherein the co-toughener is a member selected from the group consisting of acrylic rubbers; polyester urethanes; ethylene-vinyl acetates; fluorinated rubbers; isoprene-acrylonitrile polymers; chlorosulfonated polyethylenes; homopolymers of polyvinyl acetate; and reaction products of the combination of ethylene, methyl acrylate and monomers having carboxylic acid cure sites, which once formed are then substantially free of processing aids and anti-oxidants; and combinations thereof.

13. A cyanoacrylate composition comprising:

at least one α-cyanoacrylate; and

a ketone containing material within the following structure:

wherein R is linear or branched C 1 to C 7 alkyl, C 2 to C 7 alkenyl, or C 3 to C 7 cycloalkyl or cycloalkenyl, interrupted or substituted by carbonyl functionality and/or functionalized with a C 1 to C 3 alkoxy group; R* is H, methyl, or ethyl; and n is 100 percent.

Assignments (6)
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 →
MERGER Recorded Oct 29, 2013
From: LOCTITE (R&D) LIMITED
To: HENKEL IRELAND HOLDING B.V.
Reel/Frame 031496/0233 →
MERGER Recorded Oct 29, 2013
From: HENKEL IRELAND HOLDING B.V.
To: HENKEL IRELAND LIMITED
Reel/Frame 031496/0560 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 9, 2009
From: MISIAK, HANNS R.
To: LOCTITE (R&D) LIMITED
Reel/Frame 023205/0187 →