Free-radical polymerization methods and articles thereby

Patent metadata

Field	Value
Publication number	US-9957408-B2
Application number	US-201414776305-A
Country	US
Kind code	B2
Filing date	Mar 13, 2014
Priority date	Mar 19, 2013
Publication date	May 1, 2018
Grant date	May 1, 2018

Abstract

A method of curing a free-radically polymerizable composition includes contacting a curable composition with at least one oxide of copper. The curable composition includes: free-radically polymerizable compound; and a beta-dicarbonyl compound represented by the formula (I) or a salt thereof, wherein: 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; and each X independently represents O, S, formula (II), or formula (III) wherein each R4 independently represents H or alkyl having from 1 to 18 carbon atoms, or taken together any two of R 1 , R 2 , R 3 ; or R 4 form a ring. Articles including the cured compositions are also disclosed.

First claim

What is claimed is:

1. A method comprising:
a) providing a curable composition comprising:
at least one free-radically polymerizable compound; and
a beta-dicarbonyl compound represented by the formula

or a salt thereof, wherein:
R 1 and R 2 independently represent 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; and
each X independently represents O, S,

wherein each R 4 independently represents H or alkyl having from 1 to 18 carbon atoms, or taken together any two of R 1 , R 2 , R 3 , or R 4 form a ring; and

b) contacting the curable composition with at least one oxide of copper, 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 comprises an organic peroxide.

4. The method of claim 1 , wherein the curable composition further comprises a quaternary ammonium halide.

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

6. The method of claim 1 , wherein the beta-dicarbonyl compound comprises at least one of 2-methyl-1,3-cyclohexanedione, dimedone, or dimethyl acetylsuccinate.

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

8. A method of forming an article, the method comprising:
providing a first substrate having a surface, wherein at least a portion of the surface of the first substrate comprises at least one oxide of copper; and
contacting a curable composition with the at least one oxide of copper whereby the curable composition at least partially cures, and wherein the curable composition comprises:
at least one free-radically polymerizable compound; and
a beta-dicarbonyl compound represented by the formula

or a salt thereof, wherein:
R 1 and R 2 independently represent 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; and
each X independently represents O, S,

wherein each R 4 independently represents H or alkyl having from 1 to 18 carbon atoms, or taken together any two of R 1 , R 2 , R 3 , or R 4 form a ring.

9. The method of claim 8 , further comprising: contacting the curable composition with a second substrate such that the curable composition is at least partially disposed between the first substrate and the second substrate.

10. The method of claim 8 , wherein the second substrate comprises glass.

11. The method of claim 8 , wherein the first substrate further comprises glass.

12. The method of claim 8 , wherein the at least one oxide of copper comprises at least a portion of a printed circuit.

13. The method of claim 8 , wherein the at least one oxide of copper is substantially optically transparent.

14. The method of claim 8 , wherein the article comprises an electronic display device.

15. An article comprising:
a first substrate having a surface, wherein at least a portion of the surface of the first substrate comprises at least one oxide of copper; and
a reaction product of components comprising:
the at least one oxide of copper;
at least one free-radically polymerizable compound; and
a beta-dicarbonyl compound represented by the formula

or a salt thereof, wherein:
R 1 and R 2 independently represent 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; and
each X independently represents O, S,

wherein each R 4 independently represents H or alkyl having from 1 to 18 carbon atoms, or taken together any two of R 1 , R 2 , R 3 , or R 4 form a ring.

16. The article of claim 15 , wherein the reaction product contacts a second substrate, and wherein the reaction product is at least partially disposed between the first substrate and the second substrate.

17. The article of claim 15 , wherein the second substrate comprises glass.

18. The article of claim 15 , wherein the at least one oxide of copper comprises at least a portion of a printed circuit.

19. The article of claim 15 , wherein the at least one oxide of copper is substantially optically transparent.

20. The article of claim 15 , wherein the article comprises an electronic display device.

Assignees

• 3M Innovative Properties Co

Inventors

• Thompson Zachary J

Classifications

• C08F222/1006

  of polyhydric alcohols or polyhydric phenols · CPC title

• C08F220/20

  of polyhydric alcohols or phenols {, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate} · CPC title

• C09D133/14 Primary

  of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen · CPC title

• C08K5/14

  Peroxides · CPC title

• C08K3/22

  of metals · CPC title