Two part-cyanoacrylate/free radically curable adjesive systems

Patent metadata

Field	Value
Publication number	US-9371470-B2
Application number	US-201414333921-A
Country	US
Kind code	B2
Filing date	Jul 17, 2014
Priority date	Jan 23, 2012
Publication date	Jun 21, 2016
Grant date	Jun 21, 2016

Abstract

Two part cyanoacrylate/free radical curable adhesive systems, are provided.

First claim

What is claimed is:

1. A two part curable composition comprising:
(a) a first part comprising a cyanoacrylate component and t-butyl perbenzoate as a peroxide catalyst present in an amount from about 0.01% to about 10%, by weight of the cyanoacrylate component; and
(b) a second part comprising a free radical curable component and a transition metal,

wherein the cyanoacrylate component comprises H 2 C═C(CN)—COOR, wherein R is selected from alkyl, alkoxyalkyl, cycloalkyl, alkenyl, aralkyl, aryl, allyl and haloalkyl groups, and wherein when mixed together the peroxide catalyst initiates cure of the free radical curable component and the transition metal initiates cure of the cyanoacrylate component.

2. The composition of claim 1 , wherein at least one of the first part or the second part further comprises an organic acid having a pK a of about 12 or less.

3. The composition of claim 1 , wherein the free radical curable component is selected from a (meth)acrylate component, maleimide-, itaconamide- or nadimide-containing compounds, and combinations thereof.

4. The composition of claim 1 , wherein the free radical curable component is a (meth)acrylate component selected from the group consisting of polyethylene glycol di(meth)acrylates, tetrahydrofuran (meth)acrylates and di(meth)acrylates, hydroxypropyl (meth)acrylate, hexanediol di(meth)acrylate, trimethylol propane tri(meth)acrylate, diethylene glycol dimethacrylate, triethylene glycol dimethacrylate, benzylmethacrylate, tetraethylene glycol dimethacrylate, dipropylene glycol dimethacrylate, di-(pentamethylene glycol) dimethacrylate, tetraethylene diglycol diacrylate, diglycerol tetramethacrylate, tetramethylene dimethacrylate, ethylene dimethacrylate, neopentyl glycol diacrylate, trimethylol propane triacrylate and bisphenol-A mono and di(meth)acrylates.

5. The composition of claim 1 , wherein the transition metal comprises a member selected from the group consisting of copper, vanadium, cobalt and iron.

6. 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.

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

8. The composition of claim 6 , wherein the toughener is a member selected from the group consisting of (a) reaction products of the combination of ethylene, methyl acrylate and monomers having carboxylic acid cure sites, (b) dipolymers of ethylene and methyl acrylate, (c) 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.

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

10. 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.

11. The composition of claim 2 , wherein at least one of the first part or the second part further comprises a member selected from the group consisting of sulfimides, sulfonamides, citric acid, maleic acid, succinic acid, phthalic acid, di-carboxylic acid, maleic anhydride, maleic dianhydride, succinic anhydride, phthalic anhydride, and combinations thereof.

12. The composition of claim 4 , wherein the free radical curable component is a (meth)acrylate component selected from the group consisting of ethoxylated bisphenol-A (meth)acrylate, ethoxylated bisphenol-F (meth)acrylate, methacrylate-functional urethanes, and combinations thereof.

13. The composition of claim 5 , wherein the transition metal comprises copper in the form of a member selected from the group consisting of copper (II) 3,5-diisopropylsalicylate hydrate, copper bis(2,2,6,6-tetramethyl-3,5-heptanedionate), copper (II) hydroxide phosphate, copper (II) chloride, copper (II) acetate monohydrate, tetrakis(acetonitrile)copper (I) hexafluorophosphate, copper (II) formate hydrate, tetrakisacetonitrile copper (I) triflate, copper(II)tetrafluoroborate, copper (II) perchlorate, tetrakis(acetonitrile)copper (I) tetrafluoroborate, copper (II) hydroxide, copper (II) hexafluoroacetylacetonate hydrate and copper (II) carbonate.

Assignees

• Barnes Rory B
• Burns Barry N
• Wigham Jonathan P
• Hersee Rachel M
• Ward Emer
• Henkel IP & Holding GmbH

Inventors

• Barnes Rory B
• Burns Barry N
• Wigham Jonathan P
• Hersee Rachel M
• Ward Emer

Classifications

• C09J4/06 Primary

  {Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond} in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00 · CPC title

• C09J4/00 Primary

  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} · CPC title