IP Library Granted Patent US 11,555,135
Granted Patent B2
US 11,555,135 · App. 16/670,074 · Granted Jan 17, 2023

Cyanoacrylate compositions

Inventors: Raymond P. Tully (Slane County, IE); Rory Barnes (Lucan County, IE); Mark Loane (Naas County, IE); Deborah Coleman (Drogheda County, IE)
Assignee: Henkel AG & Co. KGaA
C09J4/06C09J5/00C09J11/08C09J133/14C09J2423/04C09J2431/00C09J2433/00
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Quick Facts
Patent No.
US 11,555,135
App. No.
16/670,074
Granted
Jan 17, 2023
Kind
B2
Abstract

Cyanoacrylate compositions, methods for forming same, and applications thereof are disclosed. The compositions demonstrate improved thermal ageing performance, including improved tensile strength performance after heat ageing in high humidity.

Claims (25)

1. A cyanoacrylate composition comprising:

(a) a cyanoacrylate component;

(b) a toughening agent comprising a copolymer of ethylene and vinyl acetate, wherein the vinyl acetate content in the copolymer is in an amount of about 50 wt % to about 95 wt %, based on the total weight of the copolymer, and wherein the toughening agent is present in the composition in an amount of about 2 wt % to about 25 wt %, based on the total weight of the cyanoacrylate composition;

(c) a component having at least two (meth)acrylate functional groups having the formula:

wherein R 1 and R 2 are the same or different and are selected from the group consisting of H or Me; and wherein X is a C 4 to C 30 alkyl chain and wherein said chain is optionally substituted with one or more acrylate and/or methacrylate functional groups, and/or one or more C 1 -C 10 alkyl groups;

(d) a benzonitrile component; and

(e) an anhydride component.

2. The cyanoacrylate composition according to claim 1 , wherein the toughening agent comprises an ethylene-vinyl acetate copolymer comprising 70 wt % vinyl acetate to 95 wt % vinyl acetate based on the total weight of the copolymer.

3. The cyanoacrylate composition according to claim 1 , wherein the toughening agent is present in an amount of from about 4 wt % to about 25 wt % based on the total weight of the cyanoacrylate composition.

4. The cyanoacrylate composition according to claim 1 , wherein the component having at least two (meth)acrylate functional groups is present in an amount of from about 1.5 wt % to about 20 wt % based on the total weight of the cyanoacrylate composition.

5. The cyanoacrylate composition according to claim 1 , wherein the benzonitrile component is present in an amount of from about 0.01 wt % to about 10 wt % based on the total weight of the cyanoacrylate composition.

6. The cyanoacrylate composition according to claim 1 , wherein the anhydride component is present in an amount of from about 0.05 wt % to about 5 wt % based on the total weight of the cyanoacrylate composition.

7. The cyanoacrylate composition according to claim 1 , wherein the cyanoacrylate component comprises ethyl-2-cyanoacrylate or allyl-2-cyanoacrylate.

8. The cyanoacrylate composition according to claim 1 , wherein the cyanoacrylate component comprises a combination of ethyl-2-cyanoacrylate and allyl-2-cyanoacrylate.

9. The cyanoacrylate composition according to claim 1 , wherein the component having at least two (meth)acrylate functional groups is selected from:

10. The cyanoacrylate composition according to claim 9 wherein the component having at least two (meth)acrylate functional groups is hexanediol diacrylate.

11. The cyanoacrylate composition according to claim 1 , wherein the benzonitrile component is a member selected from the group consisting of 3,5-dinitrobenzonitrile, 2-chloro-3,5-dinitrobenzonitrile, pentafluorobenzonitrile, 2-fluoro-4-(trifluoromethyl)benzonitrile, tetrachloroterephthalonitrile, tetrafluorophthalonitrile and tetrafluoroisophthalonitrile.

12. The cyanoacrylate composition according to claim 1 , wherein the anhydride component is an aromatic anhydride.

13. The cyanoacrylate composition according to claim 1 , wherein the anhydride is a hydrogenated anhydride.

14. The cured cyanoacrylate composition according to claim 1 .

15. A method of bonding together two substrates, comprising the steps of applying a cyanoacrylate composition according to claim 1 , to at least one of the substrates, and mating together the substances for a time sufficient to permit an adhesive bond to form from the cyanoacrylate composition between the mated substrates.

16. A bonded assembly comprising:

a first substrate having a first surface;

a second substrate having a second surface; and

a cured cyanoacrylate composition disposed between said first and second surfaces, said composition, prior to cure, comprising a cyanoacrylate composition according to claim 15 .

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 22, 2022
From: HENKEL IP & HOLDING GMBH
To: HENKEL AG & CO. KGAA
Reel/Frame 059207/0627 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 17, 2021
From: TULLY, PAYMOND P.; BARNES, RORY; LOANE, MARK; COLEMAN, DEBORAH
To: HENKEL IRELAND OPERATIONS & RESEARCH LIMITED
Reel/Frame 058136/0304 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 17, 2021
From: HENKEL IRELAND OPERATIONS & RESEARCH LIMITED
To: HENKEL IP & HOLDING GMBH
Reel/Frame 058136/0369 →