Photochromic polyurethane laminate

Patent metadata

Field	Value
Publication number	US-10052849-B2
Application number	US-201414563985-A
Country	US
Kind code	B2
Filing date	Dec 8, 2014
Priority date	Sep 9, 2003
Publication date	Aug 21, 2018
Grant date	Aug 21, 2018

Abstract

A photochromic polyurethane laminate that is constructed to solve certain manufacturing difficulties involved in the production of plastic photochromic lenses is disclosed. The photochromic laminate includes at least two layers of a resinous material and a photochromic polyurethane layer that is interspersed between the two resinous layers and which contains photochromic compounds. The polyurethane layer is formed by curing a mixture of a solid thermoplastic polyurethane, at least one isocyanate prepolymer, at least one photochromic compound, and a stabilizing system.

First claim

What is claimed is:

1. An optical lens comprising:
a concave lens surface;
a convex lens surface opposite the concave lens surface; and
a photochromic layer prepared from a solvent-based reaction solution comprising a solid thermoplastic polyurethane, a first isocyanate polyurethane prepolymer, and at least one photochromic compound, a weight ratio of the thermoplastic polyurethane to the first isocyanate polyurethane prepolymer in a range of 1:9 to 9:1.

2. The optical lens of claim 1 wherein said solid thermoplastic polyurethane is prepared from a reaction solution comprising a second isocyanate polyurethane prepolymer having a percent isocyanate content greater than a percent isocyanate content of the first isocyanate polyurethane prepolymer and a chain extender;
the second isocyanate polyurethane prepolymer prepared from a reaction solution comprising:
a) a polyol selected from a group consisting of polyester polyols and polyether polyols, having a molecular weight in the range of about 500 to 6,000 g/mol, and a functionality of 2; and
b) an aliphatic diisocyanate, a cycloaliphatic diisocyanate, or both;

the chain extender comprising a diol having a molecular weight in a range of about 62 to 499 g/mol.

3. The optical lens of claim 2 wherein said polyol comprises a polyester polyol from a group consisting of polycaprolactone polyol and poly(butylene adipate) polyol.

4. The optical lens of claim 2 wherein said polyol comprises a polyether polyol from a group consisting of polypropylene glycol and polytetramethylene glycol.

5. The optical lens of claim 2 wherein said aliphatic diisocyanate comprises a diisocyanate from a group consisting of: hexamethylene diisocyanate, isophorone diisocyanate, cyclohexane diisocyanate, methylcyclohexane diisocyanate, and dicyclohexylmethane diisocyanate.

6. The optical lens of claim 2 wherein said diol comprises a diol from a group consisting of: propane diol, butane diol, pentane diol, hexane diol, diethylene glycol, dipropylene glycol, and cyclohexane diol.

7. The optical lens of claim 1 wherein said first isocyanate polyurethane prepolymer comprises an isocyanate polyurethane prepolymer having a molecular weight in a range of about 1,000 to 6,000 grams per mole.

8. The optical lens of claim 1 wherein said first isocyanate polyurethane prepolymer is formed of a composition comprising:
a) a polyol selected from a group consisting of polyester polyols and polyether polyols having a molecular weight in a range of about 500 to 3000 g/mol and a functionality of 2;
b) an aliphatic diisocyanate, a cycloaliphatic diisocyanate, or both.

9. The optical lens of claim 8 wherein said polyester polyols comprises a polycaprolactone polyol or a poly(butylene adipate) polyol.

10. The optical lens of claim 8 wherein said polyether polyols comprises a polypropylene glycol or a polytetramethylene glycol.

11. The optical lens of claim 8 wherein said diisocyanate comprises a diisocyanate from a group consisting of: hexamethylene diisocyanate, isophorone diisocyanate, cyclohexane diisocyanate, methylcyclohexane diisocyanate, and dicyclohexylmethane diisocyanate.

12. The optical lens of claim 1 wherein said optical lens comprises a plurality of focal powers.

13. The optical lens of claim 1 wherein said optical lens comprises a plurality of focal powers that change in continuous increments.

14. The optical lens of claim 1 wherein said optical lens comprises an injection molded optical lens.

15. The optical lens of claim 1 wherein said optical lens comprises a cast molded optical lens.

16. The optical lens of claim 1 further comprising a first transparent resin sheet attached to a first side of the photochromic layer and a second transparent resin sheet attached to a second side of the photochromic layer.

17. The optical lens of claim 1 wherein the photochromic layer comprises an NCO:OH ratio greater than 3.

18. An optical lens comprising:
a back lens surface;
a front lens surface opposite the back lens surface; and
a photochromic layer interposed between the front lens surface and the back lens surface, the photochromic layer prepared from a reaction solution comprising a thermoplastic polyurethane, an isocyanate polyurethane prepolymer having a percent isocyanate content less than a percent isocyanate content of an isocyanate polyurethane prepolymer employed to form the thermoplastic polyurethane, and at least one photochromic compound.

19. The optical lens of claim 18 further comprising a first transparent resin sheet attached to a first side of the photochromic layer and a second transparent resin sheet attached to a second side of the photochromic layer.

20. The optical lens of claim 19 wherein the first transparent resin sheet and the second transparent resin sheet comprise polycarbonate.

21. The optical lens of claim 18 wherein the lens comprises more than one focal power.

22. The optical lens of claim 18 wherein said thermoplastic polyurethane is prepared from a reaction solution comprising the isocyanate polyurethane prepolymer employed to form the thermoplastic polyurethane and a chain extender;
the isocyanate polyurethane prepolymer employed to form the thermoplastic polyurethane prepared from a reaction solution comprising:
a) a polyol selected from a group consisting of polyester polyols and polyether polyols, having a molecular weight in a range of about 500 to 6,000 g/mol, and a functionality of 2; and
b) an aliphatic diisocyanate, a cycloaliphatic diisocyanate, or both

the chain extender comprising a diol having a molecular weight in a range of about 62 to 499 g/mol.

23. The optical lens of claim 18 wherein the photochromic layer comprises an NCO:OH ratio greater than 3.

Assignees

• Vision Ease Lp

Inventors

• Qin Xuzhi
• Sugimura Hideyo
• Boulineau Michael S

Classifications

• C08L2666/20

  Macromolecular compounds having nitrogen in the main chain according to C08L75/00 - C08L79/00; Derivatives thereof · CPC title

• B29D11/00009

  Production of simple or compound lenses · CPC title

• C08L75/04

  Polyurethanes · CPC title

• C08G18/4277

  Caprolactone and/or substituted caprolactone · CPC title

• B32B2551/00

  Optical elements · CPC title