Free-radical polymerization methods and articles thereby

Patent metadata

Field	Value
Publication number	US-10344169-B2
Application number	US-201515508360-A
Country	US
Kind code	B2
Filing date	Sep 28, 2015
Priority date	Sep 30, 2014
Publication date	Jul 9, 2019
Grant date	Jul 9, 2019

Abstract

A method of curing a curable composition includes contacting the free-radically curable composition with the solid primer layer thereby causing at least partial curing of the curable composition. The solid primer layer includes a binder material, optional beta-dicarbonyl compound, and an organic peroxide. The curable composition includes at least one free-radically polymerizable compound, a polyvalent metal compound, and a quaternary ammonium halide. The method can be used for adhesive bonding of substrates and preparation of various articles.

First claim

What is claimed is:

1. A method of curing a curable composition, the method comprising:
a) providing the curable composition, wherein the curable composition comprises:
a free-radically polymerizable compound; and
a quaternary ammonium halide;
a polyvalent metal compound for free-radically curing the curable composition; and

b) providing a substrate having a solid primer layer disposed on at least a portion thereof, wherein the solid primer layer comprises:
a binder material; and
an organic peroxide; and

c) contacting the curable composition with at least a portion of the solid primer layer, thereby causing at least partial curing of the curable composition.

2. The method of claim 1 , wherein the organic peroxide comprises cumene hydroperoxide.

3. The method of claim 1 , wherein the solid primer layer further comprises a beta-dicarbonyl compound represented by the formula

or a salt thereof, wherein:
X 1 and X 2 independently represent a covalent bond, O, S,

 wherein each R 4 independently represents H or alkyl having from 1 to 18 carbon atoms,
R 1 and R 2 independently represent a hydrocarbyl or substituted-hydrocarbyl group having from 1 to 18 carbon atoms,
R 3 represents hydrogen, or a hydrocarbyl or substituted-hydrocarbyl group having from 1 to 18 carbon atoms,
or taken together any two of R 1 , R 2 , or R 3 form a five-membered or six-membered ring.

4. The method of claim 3 , wherein the beta-dicarbonyl compound comprises a dialkyl 2-acetylsuccinate diester having from 8 to 14 carbon atoms.

5. The method of claim 3 , wherein the beta-dicarbonyl compound comprises 1,3-dialkylbarbituric acid or a derivative thereof.

6. The method of claim 1 , wherein the curable composition further comprises a photoinitiator for free-radical polymerization.

7. The method of claim 1 , wherein the polyvalent metal compound comprises a copper (II) compound, an iron (II) compound, an iron (III) compound, a cobalt (II) compound, a cobalt (III) compound, a manganese (II) compound, or a manganese (III) compound.

8. The method of claim 1 , wherein the free-radically polymerizable compound comprises a free-radically polymerizable polyfunctional (meth)acrylate.

9. The method of claim 1 , wherein the binder material comprises an organic polymer.

Assignees

• 3M Innovative Properties Co

Inventors

• Tasaka Yoshihiko
• Thompson Zachary J
• Fujita Jun
• Kasahara Takahiro
• Endo Sotaro

Classifications

• C08F20/18

  with acrylic or methacrylic acids · CPC title

• C09D133/08 Primary

  Homopolymers or copolymers of acrylic acid esters · CPC title

• C08K5/14

  Peroxides · CPC title

• C08F220/343

  in the form of urethane links · CPC title

• B05D1/28

  performed by transfer from the surfaces of elements carrying the liquid or other fluent material, e.g. brushes, pads, rollers · CPC title