TWO-PART, CYANOACRYLATE/CATIONICALLY CURABLE ADHESIVE SYSTEMS

• US 20140275419A1
• Filed: 03/15/2013
• Published: 09/18/2014
• Est. Priority Date: 03/15/2013
• Status: Active Grant

• Current Assignee: Henkel AG & Co KGaA
• Original Assignee: Henkel Ireland Ltd (Henkel AG & Co KGaA)
• Inventors: Ward, Emer, Hedderman, Patricia A., Moore, Deborah A., Reilly, Susan, Hersee, Rachel
• Granted Patent: US 8,981,027 B2
• Time in Patent Office: Days
• US Class Current: 524/879
• CPC Class Codes: C08F 222/322 Alpha-cyano-acrylic acid ethyl ester, e.g. ethyl-2-cyanoacrylate
• CPC Class Codes: C09J 135/04 Homopolymers or copolymers of nitriles C09J135/06, C09J135/08 take precedence
• CPC Class Codes: C09J 4/00 Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16

Abstract

Two part cyanoacrylate/cationically curable adhesive systems are provided.

Claims

1. A two part curable composition comprising:

(a) a first part comprising a cyanoacrylate component and a cationic catalyst; and

(b) a second part comprising a cationic curable component and an initiator component,

wherein when mixed together the cationic catalyst initiates cure of the cationic curable component.

2. The composition of claim 1, wherein the cyanoacrylate component comprises H₂C═

C(CN)—

COOR, wherein R is selected from alkyl, alkoxyalkyl, cycloalkyl, alkenyl, aralkyl, aryl, allyl and haloalkyl groups.

3. The composition of claim 1, wherein the cationic catalyst comprises salts of lithium and metals from Group II of the Periodic Table, and non-nucleophilic acids.

4. The composition of claim 1, wherein the cationic catalyst is a non-nucleophilic acid having a pH of less than 1.0 when measured as a 10% by weight solution in water.

5. The composition of claim 1, wherein the cationic catalyst is a member selected from the group consisting of fluoroboric, fluoroarsenic, fluoroantimonic and fluorophosphoric acids;

lithium tetrafluoroborate, calcium di-tetrafluoroborate, magnesium di-tetrafluoroborate, lithium hexafluorophosphate, calcium di-hexafluorophosphate, magnesium di-hexafluorophosphate, lithium hexafluoroantimonate and lithium hexafluoroarsenate;

lanthanide triflate salts, aryl iodonium salts, aryl sulfonium salts, lanthanum triflate, ytterbium triflate, trimethoxyboroxine, trimethoxyboroxine-aluminum acetyl acetonate, amine-boron trihalide complexes, quaternary ammonium salts, quaternary phosphonium salts, tri-aryl sulfonium salts, di-aryl iodonium salts, and diazonium salts;

trialkoxyboroxine curing agents; and

combinations thereof.

6. The composition of claim 1, wherein the cationic curable component is selected from an epoxy component, an episulfide component, an oxetane component, a vinyl ether component and combinations thereof.

7. The composition of claim 1, wherein the cationic curable component is an epoxy component selected from the group consisting of cycloaliphatic epoxy, aromatic epoxy, aliphatic epoxy and hydrogenated aromatic epoxy.

8. The composition of claim 1, wherein the epoxy component comprises a member selected from the group consisting of epoxy-functionalized hydrogenated bisphenol-A, bisphenol-F, bisphenol-E, bisphenol-S and biphenyl.

9. The composition of claim 1, wherein the first part is, housed in a first chamber of a dual chamber syringe and the second part is housed in a second chamber of the dual chamber syringe.

10. The composition of claim 1, wherein the first part further comprises phosphoric acid.

11. The composition of claim 1, wherein the second part further comprises at least one of a plasticizer, a filler and a toughener.

12. The composition of claim 11, wherein the toughener is a member selected from the group consisting of (1) (a) reaction products of the combination of ethylene, methyl acrylate and monomers having carboxylic acid cure sites, (2) (b) dipolymers of ethylene and methyl acrylate, (3) combinations of (a) and (b), (4) vinylidene chloride-acrylonitrile copolymers, (5) and vinyl chloride/vinyl acetate copolymer, (6) copolymers of polyethylene and polyvinyl acetate, and combinations thereof.

13. The composition of claim 1, wherein the first part and the second part are present in a ratio of about 1:

1 by volume.

14. The composition of claim 1, wherein the first part and the second part are each housed in a separate chamber of a dual chambered container.

15. The composition of claim 1, wherein the initiator component is a member selected from the group consisting of heterocycles, pyridines, benzothiazoles, toluidines, and phenolics.

16. The composition of claim 1, wherein the initiator component is a member selected from the group consisting of 3,5-dibromopyridine, 3,5-dichloropyridine, N,N-dimethyl-p-toluidine, 2,2-dipyridyl disulphide, 5-chloro-2-methyl benzothiazole, 2-methyl-mercaptobenzothiazole, N,N-dihydroethyl-p-toluidine, t-butylbenzothiazole sulphonamide, 4-methyl-2,2-ditertiarybutylphenol and 4-methoxyphenol.