Photochromic polyurethane laminate
View Patent ↗Photochromic polyurethane laminates and methods for the formation of same wherein a photochromic polyurethane layer of the laminate is interposed between two primer coated transparent resin sheets.
1. A method of making a photochromic polyurethane laminate comprising:
(a) forming a photochromic polyurethane composition from the steps comprising:
forming an isocyanate-terminated prepolymer by reacting a polyol with an aliphatic diisocyanate or an cycloaliphatic diisocyanate;
forming a hydroxyl-terminated polyurethane by reacting a polyol with an aliphatic diisocyanate or a cycloaliphatic diisocyanate and a chain extender; and
reacting the isocyanate-terminated prepolymer and the hydroxyl-terminated polyurethane to form a reaction mixture;
adding one or more photochromic compounds to the reaction mixture;
(b) forming a photochromic polyurethane film from said photochromic polyurethane composition;
(c) forming a polyurethane primer by reacting an isocyanate-terminated prepolymer that is distinct from the isocyanate-terminated prepolymer employed to form the photochromic polyurethane composition with at least one component selected from a group consisting of a hydroxyl-terminated chain extender and a hydroxyl-terminated crosslinking agent;
(d) coating a first side of a first transparent resin sheet and a first side of a second transparent resin sheet with the polyurethane primer; and
(e) laminating said photochromic polyurethane film between the first sides of said first and said second transparent resin sheets.
2. The method of claim 1 wherein the step of forming the polyurethane primer by reacting the isocyanate-terminated prepolymer that is distinct from the isocyanate-terminated prepolymer employed to form the photochromic polyurethane composition with at least one component selected from the group consisting of the hydroxyl-terminated chain extender and the hydroxyl-terminated crosslinking agent comprises forming the isocyanate-terminated prepolymer that is distinct from the isocyanate-terminated prepolymer employed to form the photochromic polyurethane composition by reacting at least one diisocyanate selected from a group consisting of an aliphatic diisocyanate and a cycloaliphatic diisocyanate with a polyol comprising;
where n is equal to an integer from 3 to 6 or a combination thereof, and x is an integer that makes a molecular weight of the polyol approximately equal to 500-2500 Daltons.
3. A method of making a photochromic polyurethane laminate comprising:
(a) forming a photochromic polyurethane composition from the steps comprising:
forming an isocyanate-terminated prepolymer by reacting a polyol with an aliphatic diisocyanate or a cycloaliphatic diisocyanate;
forming a hydroxyl-terminated polyurethane by reacting a polyol with an aliphatic diisocyanate or a cycloaliphatic diisocyanate and a chain extender; and
reacting the isocyanate-terminated prepolymer and the hydroxyl-terminated polyurethane to form a reaction mixture;
adding one or more photochromic compounds to the reaction mixture;
(b) forming a photochromic polyurethane film from said photochromic polyurethane composition;
(c) forming a polyurethane primer by reacting a hydroxyl-terminated prepolymer and at least one component selected from a group consisting of an isocyanate-terminated chain extender and an isocyanate-terminated crosslinking reagent;
(d) coating a first side of a first transparent resin sheet and a first side of a second transparent resin sheet with the polyurethane primer; and
(e) laminating said photochromic polyurethane film between the first sides of said first and said second transparent resin sheets.
4. The method of claim 3 wherein the step of forming the polyurethane primer by reacting the hydroxyl-terminated prepolymer and at least one component selected from the group consisting of the isocyanate-terminated chain extender and the isocyanate-terminated crosslinking reagent comprises forming the hydroxyl-terminated prepolymer by reacting at least one diisocyanate selected from a group consisting of an aliphatic diisocyanate and a cycloaliphatic diisocyanate with a polyol comprising;
where n is equal to an integer from 3 to 6 or a combination thereof, and x is an integer that makes a molecular weight of the polyol approximately equal to 500-2500 Daltons.
5. The method of claim 1 wherein the step of forming the hydroxyl-terminated polyurethane by reacting a polyol with the aliphatic diisocyanate or the cycloaliphatic diisocyanate and the chain extender further comprises reacting:
(a) at least one polyol selected from a group consisting of:
(i) a polycarbonate polyol having a Formula I:
where n is equal to an integer from 3 to 6 or a combination thereof, and x is an integer that makes a molecular weight of the polycarbonate polyol approximately equal to 500-2500;
(ii) a polyether polyol having a molecular weight approximately equal to 500 to 2500 Daltons; and
(iii) a polyester polyol having a Formula III:
wherein x is an integer that makes a molecular weight of the polyester polyol approximately equal to 500 to 2500 Daltons; and
(b) a chain extender having a functionality of 2.
6. The method of claim 1 wherein the step of forming the isocyanate-terminated prepolymer by reacting the polyol with the aliphatic diisocyanate or the cycloaliphatic diisocyanate further comprises reacting at least one polyol selected from a group consisting of:
(i) a polycarbonate polyol having a Formula I:
where n is equal to an integer from 3 to 6 or a combination thereof, and x is an integer that makes a molecular weight of the polycarbonate polyol approximately equal to 500-2500;
(ii) a polyether polyol having a molecular weight approximately equal to 500 to 2500 Daltons; and
(iii) a polyester polyol having a Formula III:
wherein x is an integer that makes a molecular weight of the polyester polyol approximately equal to 500 to 2500 Daltons.
7. The method of claim 1 wherein the step of reacting the isocyanate-terminated prepolymer with the hydroxyl-terminated polyurethane comprises dissolving a cured form of the hydroxyl-terminated polyurethane.
8. The method of claim 1 further comprising the step of curing the photochromic polyurethane laminate in a two-step curing process comprising a curing at ambient temperature followed by a curing at 50 to 130 degrees Celsius.
9. A method of making a photochromic polyurethane laminate comprising:
(a) forming a photochromic polyurethane coating solution from the steps comprising:
forming a hydroxyl-terminated polyurethane by reacting a diisocyanate with a polyol;
reacting the hydroxyl-terminated polyurethane with an isocyanate-terminated prepolymer; and
mixing one or more photochromic compounds with the reacted hydroxyl-terminated polyurethane and isocyanate-terminated prepolymer;
(b) forming a photochromic polyurethane film from said photochromic polyurethane coating solution;
(c) forming a polyurethane primer by reacting an aliphatic diisocyanate or a cycloaliphatic diisocyanate with the polyol employed for said step of forming a hydroxyl-terminated polyurethane;
(d) coating a first side of a first transparent resin sheet and a first side of a second transparent resin sheet with the polyurethane primer; and
(e) laminating said photochromic polyurethane film between the first sides of said first and said second transparent resin sheets.
10. The method of claim 9 further comprising the step of (f) curing the photochromic polyurethane laminate in a two-step curing process comprising a curing at ambient temperature followed by a curing at 50 to 130 degrees Celsius.
11. the method of claim 9 wherein the step of forming the hydroxyl-terminated polyurethane by reacting a diisocyanate with a polyol comprises forming a hydroxyl-terminated polyurethane having a molecular weight of at least 66,210 Daltons.
12. The method of claim 9 wherein the step of forming the hydroxyl-terminated polyurethane by reacting a diisocyanate with a polyol comprises forming the hydroxyl-terminated polyurethane by reacting:
(a) at least one diisocyanate selected from a group consisting of aliphatic diisocyanate and cycloaliphatic diisocyanate with;
(b) at least one polyol selected from a group consisting of:
(i) a polycarbonate polyol having a Formula I:
where n is equal to an integer from 3 to 6 or a combination thereof, and x is an integer that makes a molecular weight of the polycarbonate polyol approximately equal to 500-2500;
(ii) a polyether polyol having a molecular weight approximately equal to 500 to 2500 Daltons; and
(iii) a polyester polyol having a Formula III:
wherein x is an integer that makes a molecular weight of the polyester polyol approximately equal to 500 to 2500 Daltons; and
(c) a chain extender.
13. The method of claim 9 wherein the step of reacting the hydroxyl-terminated polyurethane with the isocyanate-terminated prepolymer comprises dissolving a cured form of the hydroxyl-terminated polyurethane.
14. The method of claim 9 wherein the step of reacting the hydroxyl-terminated polyurethane with the isocyanate-terminated prepolymer further comprises forming the isocyanate-terminated prepolymer by reacting:
(a) an aliphatic diisocyanate or an cycloaliphatic diisocyanate; with
(b) at least one polyol selected from a group consisting of:
(i) a polycarbonate polyol having a Formula I:
where n is equal to an integer from 3 to 6 or a combination thereof, and x is an integer that makes a molecular weight of the polycarbonate polyol approximately equal to 500-2500;
(ii) a polyether polyol having a molecular weight approximately equal to 500 to 2500 Daltons; and
(iii) a polyester polyol having a Formula III:
wherein x is an integer that makes a molecular weight of the polyester polyol approximately equal to 500 to 2500 Daltons.
15. the method of claim 9 wherein the step of forming the polyurethane primer by reacting the aliphatic diisocyanate or the cycloaliphatic diisocyanate with the polyol employed for said step of forming the hydroxyl-terminated polyurethane comprises forming the polyurethane primer having a molecular weight of 59,995 Daltons.
16. the method of claim 9 wherein the step of forming the polyurethane primer by reacting the aliphatic diisocyanate or the cycloaliphatic diisocyanate with the polyol employed for said step of forming the hydroxyl-terminated polyurethane comprises forming a polyurethane primer by reacting:
(a) the aliphatic diisocyanate or the cycloaliphatic diisocyanate with;
(b) an isocyanate-terminated prepolymer that is the same as the isocyanate prepolymer employed to form the photochromic polyurethane coating solution or distinct from the isocyanate prepolymer employed to form the photochromic polyurethane coating solution and that is formed of the polyol employed for said step of forming a hydroxyl-terminated polyurethane; and
(c) at least one component selected from a group consisting of hydroxyl-terminated chain extender and a hydroxyl-terminated crosslinking agent.
17. the method of claim 9 wherein the step of forming the polyurethane primer by reacting the aliphatic diisocyanate or the cycloaliphatic diisocyanate with the polyol employed for said step of forming a hydroxyl-terminated polyurethane comprises forming a polyurethane primer by reacting:
(a) the aliphatic diisocyanate or the cycloaliphatic diisocyanate with;
(b) an hydroxyl-terminated prepolymer formed of the polyol employed for said step of forming a hydroxyl-terminated polyurethane; and
(c) at least one component selected from a group consisting of isocyanate-terminated chain extender and an isocyanate-terminated crosslinking agent.
18. The method of claim 9 wherein the step of reacting the hydroxyl-terminated polyurethane with the isocyanate-terminated prepolymer further comprises reacting the hydroxyl-terminated polyurethane with the isocyanate-terminated prepolymer and a crosslinking agent.
19. The method of claim 18 wherein the step of reacting the hydroxyl-terminated polyurethane with the isocyanate-terminated prepolymer and the crosslinking agent comprises reacting the hydroxyl-terminated polyurethane with the isocyanate-terminated prepolymer and di(trimethylolpropane) as the crosslinking agent.
20. The method of claim 1 wherein the step of reacting the isocyanate-terminated prepolymer and the hydroxyl-terminated polyurethane to form a reaction mixture further comprises reacting the isocyanate-terminated prepolymer and the hydroxyl-terminated polyurethane with a crosslinking agent.
21. The method of claim 20 wherein the step of reacting the isocyanate-terminated prepolymer and the hydroxyl-terminated polyurethane with the crosslinking agent comprises reacting the isocyanate-terminated prepolymer, the hydroxyl-terminated polyurethane, and di(trimethylolpropane) as the crosslinking agent.
22. The method of claim 3 wherein the step of forming a polyurethane primer by reacting a hydroxyl-terminated prepolymer and at least one component selected from a group consisting of an isocyanate-terminated chain extender and an isocyanate-terminated crosslinking reagent comprises forming the hydroxyl-terminated prepolymer by reacting at least one diisocyanate selected from a group consisting of an aliphatic diisocyanate and a cycloaliphatic diisocyanate with a polyol comprising;
where n is equal to an integer from 3 to 6 or a combination thereof, and x is an integer that makes a molecular weight of the polyol approximately equal to 500-2500 Daltons.
23. The method of claim 3 wherein the step of forming the hydroxyl-terminated polyurethane by reacting the polyol with the aliphatic diisocyanate or the cycloaliphatic diisocyanate and the chain extender further comprises reacting:
(a) at least one polyol selected from a group consisting of:
(i) a polycarbonate polyol having a Formula I:
where n is equal to an integer from 3 to 6 or a combination thereof, and x is an integer that makes a molecular weight of the polycarbonate polyol approximately equal to 500-2500;
(ii) a polyether polyol having a molecular weight approximately equal to 500 to 2500 Daltons; and
(iii) a polyester polyol having a Formula III:
wherein x is an integer that makes a molecular weight of the polyester polyol approximately equal to 500 to 2500 Daltons; and
(b) a chain extender having a functionality of 2.
24. The method of claim 3 wherein the step of forming the isocyanate-terminated prepolymer by reacting the polyol with the aliphatic diisocyanate or the cycloaliphatic diisocyanate further comprises reacting at least one polyol selected from a group consisting of:
(i) a polycarbonate polyol having a Formula I:
where n is equal to an integer from 3 to 6 or a combination thereof, and x is an integer that makes a molecular weight of the polycarbonate polyol approximately equal to 500-2500;
(ii) a polyether polyol having a molecular weight approximately equal to 500 to 2500 Daltons; and
(iii) a polyester polyol having a Formula III:
wherein x is an integer that makes a molecular weight of the polyester polyol approximately equal to 500 to 2500 Daltons.
25. The method of claim 3 wherein the step of reacting the isocyanate-terminated prepolymer and the hydroxyl-terminated polyurethane to form the reaction mixture comprises dissolving a cured form of the hydroxyl-terminated polyurethane.
26. The method of claim 3 further comprising the step of curing the photochromic polyurethane laminate in a two-step curing process comprising a curing at ambient temperature followed by a curing at 50 to 130 degrees Celsius.
27. The method of claim 3 wherein the step of reacting the isocyanate-terminated prepolymer and the hydroxyl-terminated polyurethane to form the reaction mixture further comprises reacting the isocyanate-terminated prepolymer and the hydroxyl-terminated polyurethane with a crosslinking agent.
28. The method of claim 27 wherein the step of reacting the isocyanate-terminated prepolymer and the hydroxyl-terminated polyurethane with the crosslinking agent comprises reacting the isocyanate-terminated prepolymer, the hydroxyl-terminated polyurethane, and di(trimethylolpropane) as the crosslinking agent.