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 int
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.
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1. A process for producing a transparent photochromic polyurethane laminate, comprising: a) preparing a solvent casting solution by dissolving a solid thermoplastic polyurethane having a molecular weight in a range of about 9,000 to 100,000 grams per mole, at least one isocyanate polyurethane prepol
1. A process for producing a transparent photochromic polyurethane laminate, comprising: a) preparing a solvent casting solution by dissolving a solid thermoplastic polyurethane having a molecular weight in a range of about 9,000 to 100,000 grams per mole, at least one isocyanate polyurethane prepolymer, and at least one photochromic compound, in a solvent;b) casting the solution on a release liner film to form a cast film;c) evaporating the solvent from the cast film to a substantially dry state to form a photochromic polyurethane film;d) transfer-laminating the photochromic polyurethane film between two transparent resin sheets;e) curing the photochromic polyurethane film, thereby forming a photochromic polyurethane laminate. 2. A process for producing a transparent photochromic polyurethane laminate according to claim 1, wherein step d) comprises transfer-laminating the photochromic polyurethane film between two transparent resin sheets through a sequential process. 3. A process for producing a transparent photochromic polyurethane laminate according to claim 1, wherein step d) comprises transfer-laminating the photochromic polyurethane film between two transparent resin sheets through an in-line process. 4. A process for producing a transparent photochromic polyurethane laminate, comprising: a) preparing a solvent casting solution by dissolving a solid thermoplastic polyurethane having a molecular weight in a range of about 9,000 to 100,000 grams per mole, at least one isocyanate polyurethane prepolymer, and at least one photochromic compound in a solvent;b) casting the solution on a first transparent resin sheet to form a cast film;c) evaporating the solvent from the cast film to a substantially dry state to form a photochromic polyurethane film;d) laminating the photochromic polyurethane film to a second transparent resin sheet to form a photochromic polyurethane laminate;e) curing the photochromic polyurethane laminate. 5. A process for producing a transparent photochromic polyurethane laminate according to claim 4 wherein steps b) through d) are carried out through a sequential process. 6. A process for producing a transparent photochromic polyurethane laminate according to claim 4 wherein step a) comprises forming the solid thermoplastic polyurethane by reacting: 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;b) with a diisocyanate in an equivalent ratio of diisocyanate to polyol in the range of about 1.2:1.0 to 8.0:1.0; andc) with a diol as a chain extender having a molecular weight in the range of about 62 to 499 g/mol;wherein the theoretical NCO index of the thermoplastic polyurethane is in a range of 90 to 105. 7. A process for producing a transparent photochromic polyurethane laminate according to claim 6 wherein the step of forming the solid thermoplastic polyurethane comprises selecting a polyester polyol from a group consisting of polycaprolactone polyol and poly(butylene adipate) polyol. 8. A process for producing a transparent photochromic polyurethane laminate according to claim 6 wherein the step of forming the solid thermoplastic polyurethane comprises selecting a polyether polyol from a group consisting of polypropylene glycol and polytetramethylene glycol. 9. A process for producing a transparent photochromic polyurethane laminate according to claim 6 wherein the step of forming the solid thermoplastic polyurethane comprises selecting a diisocyanate from a group consisting of hexamethylene diisocyanate, isophorone diisocyanate, cyclohexane diisocyanate, methylcyclohexane diisocyanate, and dicyclohexylmethane diisocyanate. 10. A process for producing a transparent photochromic polyurethane laminate according to claim 6 wherein the step of forming the solid thermoplastic polyurethane comprises selecting a diol from a group consisting of propane diol, butane diol, pentane diol, hexane diol, diethylene glycol, dipropylene glycol, and cyclohexane diol. 11. A process for producing a transparent photochromic polyurethane laminate according to claim 4 wherein step a) comprises employing a isocyanate polyurethane prepolymer having a molecular weight in the range of about 1,000 to 6,000 grams per mole. 12. A process for producing a transparent photochromic polyurethane laminate according to claim 4 wherein step a) comprises forming the isocyanate polyurethane prepolymer by reacting: 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) with an aliphatic diisocyanate, a cycloaliphatic diisocyanate, or both, in an equivalent ratio of diisocyanate to polyol in a range of about 1.2:1.0 to 8.0:1.0. 13. A process for producing a transparent photochromic polyurethane laminate according to claim 12 wherein the step of forming the isocyanate polyurethane prepolymer comprises selecting a polyester polyol from a group consisting of polycaprolactone polyol and poly(butylene adipate) polyol. 14. A process for producing a transparent photochromic polyurethane laminate according to claim 12 wherein the step of forming the isocyanate polyurethane prepolymer comprises selecting a polyether polyol from a group consisting of polypropylene glycol and polytetramethylene glycol. 15. A process for producing a transparent photochromic polyurethane laminate according to claim 12 wherein the step of forming the isocyanate polyurethane prepolymer comprises selecting a diisocyanate from a group consisting of hexamethylene diisocyanate, isophorone diisocyanate, cyclohexane diisocyanate, methylcyclohexane diisocyanate, and dicyclohexylmethane diisocyanate. 16. A process for producing a transparent photochromic polyurethane laminate according to claim 4 wherein the step of preparing a solvent casting solution comprises selecting a photochromic compound from the group consisting essentially of naphtho[2,1b]pyrans and naphtho[1,2b]pyrans. 17. A process for producing a transparent photochromic polyurethane laminate according to claim 4 wherein the step of preparing a solvent casting solution comprises combining said solid thermoplastic polyurethane with said isocyanate-terminated polyurethane prepolymer at a ratio in a range of about 9:1 to 1:9, by weight. 18. A process for producing a transparent photochromic polyurethane laminate according to claim 4 wherein step c) comprises forming a photochromic polyurethane film having a thickness in a range of about 10 μm to about 100 μm. 19. A process for producing a transparent photochromic polyurethane laminate according to claim 1 wherein step a) comprises forming the solid thermoplastic polyurethane by reacting: 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;b) with a diisocyanate in an equivalent ratio of diisocyanate to polyol in the range of about 1.2:1.0 to 8.0:1.0; andc) with a diol as a chain extender having a molecular weight in the range of about 62 to 499 g/mol;wherein the theoretical NCO index of the thermoplastic polyurethane is in a range of 90 to 105. 20. A process for producing a transparent photochromic polyurethane laminate according to claim 19 wherein the step of forming the solid thermoplastic polyurethane comprises selecting a polyester polyol from a group consisting of polycaprolactone polyol and poly(butylene adipate) polyol. 21. A process for producing a transparent photochromic polyurethane laminate according to claim 19 wherein the step of forming the solid thermoplastic polyurethane comprises selecting a polyether polyol from a group consisting of polypropylene glycol and polytetramethylene glycol. 22. A process for producing a transparent photochromic polyurethane laminate according to claim 19 wherein the step of forming the solid thermoplastic polyurethane comprises selecting a diisocyanate from a group consisting of hexamethylene diisocyanate, isophorone diisocyanate, cyclohexane diisocyanate, methylcyclohexane diisocyanate, and dicyclohexylmethane diisocyanate. 23. A process for producing a transparent photochromic polyurethane laminate according to claim 19 wherein the step of forming the solid thermoplastic polyurethane comprises selecting a diol from a group consisting of propane diol, butane diol, pentane diol, hexane diol, diethylene glycol, dipropylene glycol, and cyclohexane diol. 24. A process for producing a transparent photochromic polyurethane laminate according to claim 1 wherein step a) comprises employing a isocyanate polyurethane prepolymer having a molecular weight in the range of about 1,000 to 6,000 grams per mole. 25. A process for producing a transparent photochromic polyurethane laminate according to claim 1 wherein step a) comprises forming the isocyanate polyurethane prepolymer by reacting: 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) with an aliphatic diisocyanate, a cycloaliphatic diisocyanate, or both, in an equivalent ratio of diisocyanate to polyol in a range of about 1.2:1.0 to 8.0:1.0. 26. A process for producing a transparent photochromic polyurethane laminate according to claim 25 wherein the step of forming the isocyanate polyurethane prepolymer comprises selecting a polyester polyol from a group consisting of polycaprolactone polyol and poly(butylene adipate) polyol. 27. A process for producing a transparent photochromic polyurethane laminate according to claim 25 wherein the step of forming the isocyanate polyurethane prepolymer comprises selecting a polyether polyol from a group consisting of polypropylene glycol and polytetramethylene glycol. 28. A process for producing a transparent photochromic polyurethane laminate according to claim 25 wherein the step of forming the isocyanate polyurethane prepolymer comprises selecting a diisocyanate from a group consisting of hexamethylene diisocyanate, isophorone diisocyanate, cyclohexane diisocyanate, methylcyclohexane diisocyanate, and dicyclohexylmethane diisocyanate. 29. A process for producing a transparent photochromic polyurethane laminate according to claim 1 wherein the step of preparing a solvent casting solution comprises selecting a photochromic compound from the group consisting essentially of naphtho[2,1b]pyrans and naphtho[1,2b]pyrans. 30. A process for producing a transparent photochromic polyurethane laminate according to claim 1 wherein the step of preparing a solvent casting solution comprises combining said solid thermoplastic polyurethane with said isocyanate-terminated polyurethane prepolymer at a ratio in a range of about 9:1 to 1:9, by weight. 31. A process for producing a transparent photochromic polyurethane laminate according to claim 1 wherein step c) comprises forming a photochromic polyurethane film having a thickness in a range of about 10 μm to about 100 μm.
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