IP Library Granted Patent US 9,732,257
Granted Patent B2
US 9,732,257 · App. 14/852,751 · Granted Aug 15, 2017

Curable acrylate or methacrylate compositions

Inventors: James Houlihan (County Dublin, IE); Brendan Kneafsey (County Dublin, IE); Nigel Sweeney (Dublin, IE)
Assignee: Henkel IP & Holding GmbH
C09J133/14C08K5/55C09D133/14C09J4/00C08F216/125C08F220/28
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Quick Facts
Patent No.
US 9,732,257
App. No.
14/852,751
Granted
Aug 15, 2017
Kind
B2
Abstract

A curable composition based on a curable acrylate or methacrylate component; an organoborane initiator component; a vinyl ether component; and an activator for the organoborane component. The composition exhibits good storage stability and good bonding properties when used to bond low surface energy substrates.

Claims (22)

1. A curable composition comprising:

a curable (meth)acrylate component comprising the combination of at least two (meth)acrylate monomers, at least one of which is tetrahydrofurfuryl (meth)acrylate;

an organoborane:triethylene diamine complex;

an initiator component for the organoborane component comprising a vinyl ether component; and

an activator for the organoborane component, wherein the vinyl ether component is present in an amount of 0.25 to 5% weight based on the total composition and is a member selected from the group consisting of bis[4-(vinyloxy)butyl]isophthalate, ethyl vinyl ether, n-butyl vinyl ether, iso-butyl vinyl ether, t-butyl vinyl ether, cyclohexyl vinyl ether, 1,4-cyclohexanedimethanol divinyl ether, 1,4-cyclohexanedimethanol mono vinyl ether, 2-ethylhexyl vinyl ether, dodecyl vinyl ether, octadecyl vinyl ether, 1,4-butanediol divinyl ether, diethyleneglycol divinyl ether, triethyleneglycol divinyl ether, hydroxybutyl vinyl ether,

and combinations thereof, wherein the curable composition is in a two-part form with the curable (meth)acrylate component present in at least one of Part A or Part B, wherein

Part A comprises the organoborane:triethylene diamine complex and the vinyl ether initiator component; and Part B comprises the activator for the organoborane component and wherein the curable composition is substantially free of added anti-oxidants, free radical stabilizers or organo aluminum compounds.

2. A composition according to claim 1 wherein the organoborane:triethylene diamine complex is present in an amount from about 0.1 to about 10% weight percentage based on the total weight of the composition.

3. A composition according to claim 1 wherein the activator for the organoborane compound is selected from the group consisting of Lewis acids, carboxylic acids, phosphoric acids, anhydrides and isocyanates and combinations thereof.

4. A composition according to claim 1 wherein the activator is present in an amount from about 1 to about 40% weight percentage based on the total weight of the composition.

5. A composition according to claim 1 wherein the (meth)acrylate component is present in an amount from about 10 to about 95% weight percentage based on the total weight of the composition.

6. A composition according to claim 1 wherein the second part comprises a curable maleate, fumarate or maleimide component.

7. A composition according to claim 6 wherein the maleate, fumarate or maleimide component is present in an amount from about 1 to about 20% weight percentage based on the total weight of the composition.

8. A composition according to claim 1 further comprising a toughener component.

9. A composition according to claim 8 wherein the toughener component is present in an amount from about 5 to about 50% weight percentage based on the total weight of the composition.

10. A curable composition consisting of:

a curable (meth)acrylate component comprising the combination of at least two (meth)acrylate monomers, at least one of which is tetrahydrofurfuryl (meth)acrylate;

an organoborane:triethylene diamine complex;

an initiator component for the organoborane component comprising a vinyl ether component; and

an activator for the organoborane component, wherein the vinyl ether component is present in an amount of 0.25 to 5% weight based on the total composition and is a member selected from the group consisting of bis[4-(vinyloxy)butyl]isophthalate, ethyl vinyl ether, n-butyl vinyl ether, iso-butyl vinyl ether, t-butyl vinyl ether, cyclohexyl vinyl ether, 1,4-cyclohexanedimethanol divinyl ether, 1,4-cyclohexanedimethanol mono vinyl ether, 2-ethylhexyl vinyl ether, dodecyl vinyl ether, octadecyl vinyl ether, 1,4-butanediol divinyl ether, diethyleneglycol divinyl ether, triethyleneglycol divinyl ether, hydroxybutyl vinyl ether,

and combinations thereof, wherein the curable composition is in a two-part form with the curable (meth)acrylate component present in at least one of Part A or Part B, wherein

Part A comprises the organoborane:triethylene diamine complex and the vinyl ether initiator component; and Part B comprises the activator for the organoborane component and wherein the curable composition is substantially free of added anti-oxidants, free radical stabilizers or organo aluminum compounds.

Assignments (2)
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 Oct 16, 2015
From: HOULIHAN, JAMES; KNEAFSEY, BRENDAN; SWEENEY, NIGEL
To: HENKEL IP & HOLDING GMBH
Reel/Frame 036807/0015 →
Priority Claims (1)
GB 1304624.8 · Mar 14, 2013 · national
Continuity (2)
Continuation PCTEP2014054896 · Mar 12, 2014
Related Publication 20160002507A1 · Jan 7, 2016