Epoxy/acrylate based primer coating compositions and their use in the optical field
View Patent ↗The invention relates to primer coating compositions exhibiting very good adhesion properties on a large variety of substrates, in particular plastic substrates such as ophthalmic lenses made of organic glasses and which also impart good impact resistance properties to the thus coated substrates. The invention also concerns substrates coated with these primer coating compositions as well as a method for making such coated substrates.
1. An impact-resistant primer coating composition comprising:
at least one non-hydrophilic acrylate monomer;
at least one epoxy monomer; and
at least one photoactivable cationic catalyst,
wherein said at least one non-hydrophilic acrylate monomer comprises a mixture of:
(a) at least one acrylate monomer selected from the group consisting of mono and diacrylate monomers, and
(b) at least one acrylate monomer selected from the group consisting of tri to hexaacrylate monomers.
2. The primer coating composition of claim 1 , further comprising a radical photoinitiator.
3. The primer coating composition of claim 1 , wherein the epoxy monomer is selected from glycidylethers of polyhydric alkanols.
4. The primer coating composition of claim 1 , wherein the photoactivable cationic catalyst is selected from the group consisting of aromatic onium salts and iron arene salt complexes.
5. The primer coating composition of claim 2 , wherein the radical photoinoitiator is selected from benzophenone and acetophenone compounds.
6. A plastic material substrate having at least one face coated with a primer coating made of a primer coating composition as set forth in claim 1 .
7. The plastic material substrate of claim 6 , wherein the substrate is selected from carbonate, (meth)acrylic, thio(meth)acrylic, (diethyleneglycol bisallylcarbonate), urethane, thiourethane homo and copolymers and mixtures thereof.
8. The plastic material substrate of claim 6 , wherein the substrate is polycarbonate and the primer coating composition comprises a penta or hexaacrylate monomer.
9. The plastic material substrate of claim 6 , wherein the substrate is a (meth)acrylic polymer and the primer coating composition comprises a mono or diacrylate monomer.
10. The plastic material substrate of claim 6 consisting of an ophthalmic lens.
11. A method for making a plastic material substrate having at least one face coated with an impact-resistant primer coating which comprises:
providing a two-part mold having optical surfaces defining a molding cavity;
forming on at least one optical surface a layer of the primer coating composition as set forth in claim 1 and optionally fully or partially curing it;
filling the molding cavity with a substrate precursor liquid curable monomer composition;
curing the substrate precursor composition and the primer layer if not already fully cured; and
disassembling the mold to recover the impact-resistant primer coated substrate.
12. The method of claim 11 , wherein the primer coating composition does not contain radical photoinitiator and the substrate precursor composition comprises a (meth)acrylic monomer and at least one radical photoinitiator.
13. The primer coating composition of claim 1 , wherein the at least one acrylate monomer is present in an amount of 10% to 50% by weight based on the total weight of the acrylate and epoxy monomers present in the composition.
14. The primer coating composition of claim 13 , wherein the at least one acrylate monomer is present in an amount of 20% to 35% by weight based on the total weight of the acrylate and epoxy monomers present in the composition.
15. The primer coating composition of claim 1 , wherein the at least one epoxy monomer is present in an amount of 50% to 90% by weight based on the total weight of the acrylate and epoxy monomers present in the composition.
16. The primer coating composition of claim 15 , wherein the at least one epoxy monomer is present in an amount of 70% to 85% by weight based on the total weight of the acrylate and epoxy monomers present in the composition.
17. The primer coating composition of claim 1 , wherein the at least one cationic catalyst is present in an amount of 0.01% to 5% by weight based on the total weight of the epoxy monomers present in the composition.
18. The primer coating composition of claim 1 , wherein the at least one cationic catalyst is present in an amount of 1% to 3% by weight based on the total weight of the epoxy monomers present in the composition.