Hybrid epoxy-acrylic with zirconium oxide nanocomposite for curable coatings

Patent metadata

Field	Value
Publication number	US-9638834-B2
Application number	US-201314908046-A
Country	US
Kind code	B2
Filing date	Jul 25, 2013
Priority date	Jul 25, 2013
Publication date	May 2, 2017
Grant date	May 2, 2017

Abstract

A composition includes: a continuous liquid phase including an acrylic monomer and an epoxy monomer; and a dispersed nanoparticulate including ZrO 2 modified with an acrylic silane; and wherein the composition is transparent to visible light when coated on a lens. In addition, a method including the steps of: mixing an acrylic silane and a methanol-based ZrO 2 sol to create a methanol-based silane-modified ZrO 2 sol; then mixing at least an acrylic monomer, an epoxy monomer, and the methanol-based silane-modified ZrO 2 sol to obtain the composition. The composition can be adapted for coating and curing onto another substrate, such as an ophthalmic lens.

First claim

The invention claimed is:

1. A method comprising the steps of:
mixing an acrylic silane and a methanol-based ZrO 2 sol to create a methanol-based silane-modified ZrO 2 sol; then
mixing at least an acrylic monomer, an epoxy monomer, and the methanol-based silane-modified ZrO 2 sol to obtain a composition comprising:
a continuous liquid phase comprising an acrylic monomer and an epoxy monomer; and
a dispersed nanoparticulate comprising ZrO 2 modified with an acrylic silane; and
wherein the composition is transparent to visible light.

2. The method of claim 1 , further comprising the step of: forming the methanol-based ZrO 2 sol.

3. The method of claim 2 , wherein the step of forming the methanol-based ZrO 2 sol comprises the step of: dialyzing a water-based ZrO 2 sol in a methanol bath.

4. The method of claim 1 , wherein the molar ratio of the acrylic silane to ZrO 2 is in the range of 0.1:1 to 0.2:1.

5. The method of claim 1 , wherein the ratio of the acrylic monomer to the epoxy monomer is in the wt % range of approximately 10:90 to 90:10.

6. The method of claim 1 , wherein the dispersed nanoparticulate is in the range of 10 to 70 wt % of the composition.

7. The method of claim 1 , further comprising the step of: removing essentially all the methanol from the composition.

8. The method of claim 1 , wherein the composition further comprises at least one photo-polymerization initiator for polymerizing the acrylic and epoxy monomers.

9. The method of claim 1 , wherein the composition further comprises a surfactant.

10. The method of claim 1 , further comprising the step of coating the composition onto an ophthalmic substrate.

11. A composition comprising:
a continuous liquid phase comprising an acrylic monomer and an epoxy monomer; and
a dispersed nanoparticulate comprising ZrO 2 modified with an acrylic silane; and
wherein the composition is transparent to visible light.

12. The composition of claim 11 , wherein the acrylic silane is 3-methacryloxypropyltrimethoxysilane (“MPS”).

13. The composition of claim 11 , wherein the molar ratio of the acrylic silane to ZrO 2 is in the range of 0.1:1 to 0.2:1.

14. The composition of claim 11 , wherein the ratio of the acrylic monomer to the epoxy monomer is in the wt % range of approximately 10:90 to 90:10.

15. The composition of claim 11 , wherein the acrylic monomer is a difunctional (meth)acrylic monomer(s) or a multifunctional (meth)acrylic monomer(s).

16. The composition of claim 11 , wherein the acrylic monomer is 1,6-hexandiol diacrylate (HDDA).

17. The composition of claim 11 , wherein the epoxy monomer is a difunctional epoxy monomer(s) or a multifunctional epoxy monomer(s).

18. The composition of claim 11 , wherein the epoxy monomer is 1,4-butanediol diglycidyl ether (BDDGE).

19. The composition of claim 11 , wherein the dispersed nanoparticulate is in the range of 10 to 70 wt % of the wet composition.

20. An optical article comprising:
an ophthalmic lens substrate; and
a transparent, cured coating on the ophthalmic lens substrate, wherein the coating comprises:
a continuous solid phase comprising an acrylic-epoxy copolymer; and
a dispersed nanoparticulate of ZrO 2 modified with an acrylic silane.

Assignees

• Essilor Int
• Univ Shanghai

Inventors

• Jiang Peiqi
• Shi Liyi
• Zhang Dengsong
• Yan Tingting
• Li Hongrui
• Zhao Jian

Classifications

• G02B1/10 Primary

  Optical coatings produced by application to, or surface treatment of, optical elements (G02B1/08 takes precedence) · CPC title

• G02C2202/16

  Laminated or compound lenses · CPC title

• G02B1/14 Primary

  Protective coatings, e.g. hard coatings · CPC title

• C08F230/08

  containing silicon · CPC title

• C09D163/00

  Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins · CPC title