IP Library Granted Patent US 9,528,034
Granted Patent B2
US 9,528,034 · App. 14/867,132 · Granted Dec 27, 2016

Cyanoacrylate compositions

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Quick Facts
Patent No.
US 9,528,034
App. No.
14/867,132
Granted
Dec 27, 2016
Kind
B2
Abstract

This invention relates to flexible cyanoacrylate-containing compositions, having improved torsion stress resistance particularly when bonded to plastic substrates.

Claims (20)

1. A cyanoacrylate composition, comprising:

(a) a cyanoacrylate component comprising the combination of ethyl-2-cyanoacrylate and about 20 weight percent to about 45 weight percent octyl-2-cyanoacrylate; and

(b) acetyl triethyl citrate in an amount of from about 5 weight percent to less than about 15 weight percent.

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

3. The composition according to claim 1 , further comprising an accelerator component.

4. The composition according to claim 3 , wherein the accelerator component is 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 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, 8-crown-6, 1,2-vinylbenzo-15-crown-5, 1,2-vinylbenzo-18-crown-6, 1,24-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.

6. The composition according to claim 1 , further comprising additives selected from the group consisting of tougheners, shock resistant additives, thixotropy conferring agents, thickeners, dyes, and combinations thereof.

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

8. A method of bonding together two substrates, at least one of which being constructed from a thermoplastic material, comprising the steps of:

applying a cyanoacrylate-containing 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 cure.

9. The composition according to claim 1 , wherein the acetyl triethyl citrate is present in an amount of about 5 weight percent to about 12 weight percent.

10. The composition according to claim 1 , wherein the octyl cyanoacrylate and acetyl triethyl citrate together are present in an amount within the range of from about 30 weight percent to about 65 weight percent.

11. The composition according to claim 1 , wherein the octyl cyanoacrylate and acetyl triethyl citrate together are present in an amount within the range of from about 40 weight percent to about 55 weight percent.

12. A method of conferring improved torsional stress resistance to a cured product of a cyanoacrylate composition, comprising the steps of:

providing a cyanoacrylate component comprising the combination of ethyl-2-cyanoacrylate and about 20 weight percent to about 45 weight percent octyl-2-cyanoacrylate;

mixing acetyl triethyl citrate in an amount of from about 5 weight percent to less than about 15 weight percent with the cyanoacrylate component to form a cyanoacrylate composition; and

providing two or more substrates, at least one of which is constructed of a thermoplastic, wherein the substrates have matable surfaces, whereupon mating the matable surfaces of the substrates with the cyanoacrylate composition disposed therebetween forms an assembly; and

exposing the assembly to torsional stress.

Assignments (3)
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 Nov 4, 2015
From: LI, LING; SCHULZ, JOSEPH B.; LU, ZHENG; SCOTT, ANDREW
To: HENKEL CORPORATION
Reel/Frame 036958/0143 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 4, 2015
From: HENKEL CORPORATION
To: HENKEL IP & HOLDING GMBH
Reel/Frame 036958/0262 →