Free-radical polymerization methods and articles thereby

Patent metadata

Field	Value
Publication number	US-10413935-B2
Application number	US-201515509351-A
Country	US
Kind code	B2
Filing date	Sep 14, 2015
Priority date	Sep 16, 2014
Publication date	Sep 17, 2019
Grant date	Sep 17, 2019

Abstract

A method of curing a curable composition includes: providing the curable composition; providing a substrate having a primer disposed on at least a portion thereof, wherein the primer comprises at least one immobilized polyvalent metal compound for free-radically curing the curable composition; and contacting the curable composition with the primer, thereby causing at least partial curing of the curable composition. The curable composition includes at least one free-radically polymerizable compound and a beta-dicarbonyl compound. 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:
at least one free-radically polymerizable compound;
a quaternary ammonium halide; and
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; and

b) providing a glass substrate having a primer layer disposed on at least a portion thereof, wherein the primer layer comprises at least one polyvalent metal compound for free-radically curing the curable composition immobilized in a binder material;
c) contacting the curable composition with at least a portion of the primer layer, thereby causing at least partial curing of the curable composition.

2. The method of claim 1 , wherein the curable composition is essentially free of organic peroxide.

3. The method of claim 1 , wherein the curable composition further comprises an organic peroxide.

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

5. The method of claim 1 , wherein the at least one polyvalent metal compound comprises at least one of copper (II), iron (II), iron (III), cobalt (II), cobalt (III), manganese (II), and manganese (III).

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

7. The method of claim 1 , wherein the primer layer comprises an organic polymer.

8. The method of claim 1 , wherein the substrate comprises a polarizer.

9. An article comprising:
a glass substrate having a surface having a primer layer disposed on at least a portion thereof, wherein the primer layer comprises at least one polyvalent metal compound for free-radically curing a curable composition, and wherein the at least one polyvalent metal compound is immobilized in a binder material;
a polymerized reaction product of the at least one polyvalent metal compound and the curable composition, wherein the curable composition comprises:
a) at least one free-radically polymerizable compound;
b) 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; and

c) a quaternary ammonium halide.

10. The article of claim 9 , wherein the reaction product contacts a second substrate, and wherein the reaction product is at least partially disposed between the glass substrate and the second substrate.

11. The article of claim 10 , wherein the second substrate comprises glass.

12. The article of claim 10 , wherein the second substrate comprises a polarizer.

13. The article of claim 9 , wherein the curable composition is essentially free of organic peroxide.

14. The article of claim 9 , wherein the curable composition further comprises an organic peroxide.

15. The article of claim 9 , wherein the beta-dicarbonyl compound comprises 1,3-dialkylbarbituric acid or a derivative thereof.

16. The article of claim 9 , wherein the at least one polyvalent metal compound comprises at least one of copper (II), iron (II), iron (III), cobalt (II), cobalt (III), manganese (II), and manganese (III).

17. The article of claim 9 , wherein the at least one free-radically polymerizable compound comprises a free-radically polymerizable polyfunctional (meth)acrylate.

Assignees

• 3M Innovative Properties Co

Inventors

• Thompson Zachary J
• Tasaka Yoshihiko

Classifications

• C08F220/54

  Amides {, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide} · CPC title

• C08F4/26

  of manganese, iron group metals or platinum group metals · CPC title

• C08F220/343

  in the form of urethane links · CPC title

• C08F222/102

  of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate · CPC title

• C08F220/1812

  C12-(meth)acrylate, e.g. lauryl (meth)acrylate · CPC title