Curable acrylate or methacrylate compositions

Patent metadata

Field	Value
Publication number	US-9732257-B2
Application number	US-201514852751-A
Country	US
Kind code	B2
Filing date	Sep 14, 2015
Priority date	Mar 14, 2013
Publication date	Aug 15, 2017
Grant date	Aug 15, 2017

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.

First claim

The invention claimed is:

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.

Assignees

• Henkel IP & Holding GmbH

Inventors

• Houlihan James
• Kneafsey Brendan
• Sweeney Nigel

Classifications

• C09J4/00

  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} · CPC title

• C08F216/125

  Monomers containing two or more unsaturated aliphatic radicals, e.g. trimethylolpropane triallyl ether or pentaerythritol triallyl ether · CPC title

• C08K5/55

  Boron-containing compounds {(C08K5/0091 takes precedence)} · CPC title

• C09J133/10

  Homopolymers or copolymers of methacrylic acid esters · CPC title

• C09J133/08

  Homopolymers or copolymers of acrylic acid esters · CPC title