Photochromic optical article having allophanate protective coating and process for making same

Patent metadata

Field	Value
Publication number	US-9690021-B2
Application number	US-201415026647-A
Country	US
Kind code	B2
Filing date	Oct 3, 2014
Priority date	Oct 11, 2013
Publication date	Jun 27, 2017
Grant date	Jun 27, 2017

Abstract

A photochromic optical article is provided, which includes: an optical substrate; a photochromic layer over a surface of the optical substrate, wherein the photochromic layer includes a photochromic compound; and a protective layer over the photochromic layer, wherein the protective layer includes a matrix that includes residues of an ethylenically unsaturated radically polymerizable material that includes at least one allophanate group. A method of forming the photochromic optical article is also provided.

First claim

What is claimed is:

1. A photochromic optical article comprising:
(i) an optical substrate;
(ii) a photochromic layer over a surface of said optical substrate, wherein said photochromic layer comprises a photochromic compound; and
(iii) a protective layer over said photochromic layer, wherein said protective layer comprises a matrix comprising residues of an ethylenically unsaturated radically polymerizable material comprising at least one allophanate group.

2. The photochromic optical article of claim 1 , wherein the photochromic layer comprises a matrix comprising urethane linkages.

3. The photochromic optical article of claim 1 , wherein said photochromic compound of said photochromic layer is selected from the group consisting of indeno-fused naphthopyrans, naphtho[1,2-b]pyrans, naphtho[2,1-b]pyrans, spirofluoroeno[1,2-b]pyrans, phenanthropyrans, quinolinopyrans, fluoroanthenopyrans, spiropyrans, benzoxazines, naphthoxazines, spiro(indoline)naphthoxazines, spiro(indoline)pyridobenzoxazines, spiro(indoline)fluoranthenoxazines, spiro(indoline)quinoxazines, fulgides, fulgimides, diarylethenes, diarylalkylethenes, and diarylalkenylethenes and combinations of two or more thereof.

4. The photochromic optical article of claim 1 , wherein said matrix of said protective layer further comprises residues of an aminoplast material.

5. The photochromic optical article of claim 1 , wherein said matrix of said protective layer further comprises residues of a second ethylenically unsaturated radically polymerizable material that is free of allophanate groups.

6. The photochromic optical article of claim 1 , further comprising a hard-coat layer over said protective layer.

7. The photochromic optical article of claim 1 , further comprising a polarizing layer that is,
interposed between said surface of said optical substrate and said photochromic layer, or
over said photochromic layer.

8. The photochromic optical article of claim 1 , wherein the photochromic optical article is a photochromic ophthalmic article.

9. A method of preparing a photochromic optical article comprising:
(a) applying a curable photochromic coating composition over a surface of an optical substrate, thereby forming a curable photochromic layer over said surface of said optical substrate, wherein said curable photochromic coating composition comprises a photochromic compound;
(b) at least partially curing said curable photochromic layer, thereby forming an at least partially cured photochromic layer over said surface of said optical substrate;
(c) applying a curable protective coating composition over said at least partially cured photochromic layer, thereby forming a curable protective layer over said at least partially cured photochromic layer, wherein said curable protective coating composition comprises an ethylenically unsaturated radically polymerizable material comprising at least one allophanate group; and
(d) at least partially curing said curable protective layer, thereby forming an at least partially cured protective layer over said at least partially cured photochromic layer.

10. The method of claim 9 , wherein:
said curable photochromic layer is at least partially cured by exposure to elevated temperature, and
said curable protective layer is at least partially cured by exposure to actinic radiation.

11. The method of claim 9 , wherein said at least partially cured photochromic layer comprises a matrix comprising urethane linkages.

12. The method of claim 9 , wherein said photochromic compound of said curable photochromic coating composition is selected from the group consisting of indeno-fused naphthopyrans, naphtho[1,2-b]pyrans, naphtho[2,1-b]pyrans, spirofluoroeno[1,2-b]pyrans, phenanthropyrans, quinolinopyrans, fluoroanthenopyrans, spiropyrans, benzoxazines, naphthoxazines, spiro(indoline)naphthoxazines, spiro(indoline)pyridobenzoxazines, spiro(indoline)fluoranthenoxazines, spiro(indoline)quinoxazines, fulgides, fulgimides, diarylethenes, diarylalkylethenes, and diarylalkenylethenes and combinations of two or more thereof.

13. The method of claim 9 , wherein said curable protective coating composition comprises an aminoplast material, and said curable protective layer is at least partially cured by exposure to actinic radiation and optionally elevated temperature.

14. The method of claim 9 , wherein said curable protective coating composition comprises a second ethylenically unsaturated radically polymerizable material that is free of allophanate groups.

15. The method of claim 9 , wherein said curable protective coating composition has a solids content of 95 percent by weight to 100 percent by weight, based on total weight of said curable protective coating composition.

16. The method of claim 9 , further comprising:
applying a curable hard-coat coating composition over said at least partially cured protective layer, thereby forming a curable hard-coat layer over said at least partially cured protective layer; and
at least partially curing said curable hard-coat layer, thereby forming an at least partially cured hard-coat layer over said at least partially cured protective layer.

17. The method of claim 9 , further comprising forming a polarizing layer, that is,
interposed between said surface of said optical substrate and said at least partially cured photochromic layer, or
over said at least partially cured photochromic layer.

18. The method of claim 9 , wherein said photochromic optical article is a photochromic ophthalmic article.

Assignees

• Transitions Optical Inc

Inventors

• Turpen Joseph David
• Kutchko Cynthia
• Owens Glen Todd
• Lahsangah Vitawat
• Koenig Ii Jerry L

Classifications

• C09K9/02 Primary

  Organic tenebrescent materials · CPC title

• G02B5/223 Primary

  containing organic substances, e.g. dyes, inks or pigments · CPC title

• B05C11/1036

  Means for supplying a selected one of a plurality of liquids or other fluent materials, or several in selected proportions, to the applying apparatus · CPC title

• C09D175/04

  Polyurethanes · CPC title

• C08G18/7831

  containing biuret groups · CPC title