IP Library Granted Patent US 9,783,714
Granted Patent B2
US 9,783,714 · App. 13/838,303 · Granted Oct 10, 2017

Cyanoacrylate compositions

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Quick Facts
Patent No.
US 9,783,714
App. No.
13/838,303
Granted
Oct 10, 2017
Kind
B2
Abstract

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

Claims (31)

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.

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 9, 2022
From: HENKEL IP & HOLDING GMBH
To: HENKEL AG & CO. KGAA
Reel/Frame 059357/0267 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 10, 2016
From: HENKEL AG & CO. KGAA
To: HENKEL IP & HOLDING GMBH
Reel/Frame 039391/0421 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 28, 2014
From: HENKEL IRELAND OPERATIONS & RESEARCH LIMITED
To: HENKEL AG & CO. KGAA
Reel/Frame 033398/0985 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 25, 2014
From: GOFF, CIARA; PHELAN, MARISA; GUTHRIE, JOHN; DUFFY, CORMAC; HORN, SABINE; DESPOTOPOULOU, CHRISTINA
To: HENKEL IRELAND OPERATIONS & RESEARCH LIMITED
Reel/Frame 033390/0863 →