Free-radical polymerization methods and articles thereby
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.
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.