Photochromic polyurethane laminate
View Patent ↗Photochromic polyurethane laminates and methods for the formation of same wherein the photochromic polyurethane layer of the laminate has been crosslinked with a isocyanate-active prepolymer using a crosslinking agent. The crosslinking agent is formulated to have at least three functional groups that are reactive with functional groups of the polyurethane or of the isocyanate-active prepolymer.
1. A photochromic polyurethane laminate for use in an optical article comprising:
a first resin sheet;
a second resin sheet; and
a photochromic polyurethane layer disposed between said first and second resin sheet;
said photochromic polyurethane layer formed from a composition initially comprising a prepolymer, a crosslinking agent, a chain extender, and one or more photochromic compounds;
said prepolymer formed from a composition comprising:
a polycarbonate polyol; and
an aliphatic diisocyanate;
a molar ratio of the crosslinking agent and the chain extender in the range of 0.10 to 1.15.
2. The photochromic polyurethane laminate according to claim 1 wherein said polycarbonate polyol has a formula:
where n is equal to an integer from 3 to 6 or a combination thereof, and “x” is an integer that makes the molecular weight of the polycarbonate polyol approximately equal to 500 to 2,500 grams per mole.
3. The photochromic polyurethane laminate according to claim 1 wherein the crosslinking agent comprises di(trimethylolpropane).
4. The photochromic polyurethane laminate according to claim 1 wherein said chain extender comprises 1,4-butanediol.
5. The photochromic polyurethane laminate according to claim 1 wherein said aliphatic diisocyanate comprises 4,4′-dicyclohexylmethanediisocyanate.
6. The photochromic polyurethane laminate according to claim 1 wherein the prepolymer is formed from a composition further comprising a polyether polyol.
7. The photochromic polyurethane laminate according to claim 6 wherein the polyether polyol has a formula:
HO—[(CR1R2M) n O] x H
where R1 and R2 are hydrogen or an alkyl group, where “n” is equal to an integer from 3 to 6, and “x” is an integer that makes the molecular weight of said polyether polyol approximately equal to 1000 and where “M” has a formula:
(CH2) y
where “y” is an integer from 1 to 6.
8. The photochromic polyurethane laminate according to claim 6 wherein a molar ratio of the polycarbonate polyol to the polyether polyol is in the range of 0.5 to 1.5.
9. The photochromic polyurethane laminate according to claim 1 wherein the first resin sheet comprises polycarbonate.
10. The photochromic polyurethane laminate according to claim 1 wherein the first resin sheet and the second resin sheet comprise polycarbonate.
11. The photochromic polyurethane laminate according to claim 1 wherein the first resin sheet comprises cellulose acylate.
12. A photochromic polyurethane laminate for use in an optical article comprising:
a first resin sheet;
a second resin sheet;
a photochromic polyurethane layer disposed between said first and second resin sheet; and
said photochromic polyurethane layer formed from a composition comprising a prepolymer, a crosslinking agent, a chain extender, and one or more photochromic compounds;
said prepolymer formed from a composition comprising:
a polycarbonate polyol;
a polyether polyol; and
an aliphatic diisocyanate;
a molar ratio of the crosslinking agent and the chain extender in the range of 0.10 to 1.15.
13. The photochromic polyurethane laminate according to claim 12 wherein said polycarbonate polyol has a formula:
where n is equal to an integer from 3 to 6 or a combination thereof, and “x” is an integer that makes the molecular weight of the polycarbonate polyol approximately equal to 500 to 2,500.
14. The photochromic polyurethane laminate according to claim 12 wherein said polyether polyol has a formula:
HO—[(CR1R2M) n O] x H
where R1 and R2 are hydrogen or an alkyl group, where “n” is equal to an integer from 3 to 6, and “x” is an integer that makes the molecular weight of said polyether polyol approximately equal to 1000 and where “M” has a formula:
(CH2) y
where “y” is an integer from 1 to 6.
15. The photochromic polyurethane laminate according to claim 12 wherein the crosslinking agent comprises di(trimethylolpropane).
16. The photochromic polyurethane laminate according to claim 12 wherein said chain extender comprises 1,4-butanediol.
17. The photochromic polyurethane laminate according to claim 12 wherein said aliphatic diisocyanate comprises 4,4′-dicyclohexylmethanediisocyanate.
18. The photochromic polyurethane laminate according to claim 12 wherein the first resin sheet comprises a polycarbonate.
19. The photochromic polyurethane laminate according to claim 12 wherein the first resin sheet and the second resin sheet comprise polycarbonate.
20. The photochromic polyurethane laminate according to claim 12 wherein a molar ratio of the polycarbonate polyol to the polyether polyol is in the range of 0.5 to 1.5.
21. The photochromic polyurethane laminate according to claim 12 wherein the first resin sheet comprises cellulose acylate.
22. A photochromic cast lens comprising:
a cast monomer; and
a photochromic laminate disposed within the cast monomer;
the photochromic laminate comprising;
a first resin sheet;
a second resin sheet;
a photochromic polyurethane layer disposed between the first and second resin sheet;
the photochromic polyurethane layer formed from a composition comprising a prepolymer, a crosslinking agent, a chain extender, and one or more photochromic compounds;
the prepolymer formed from a composition comprising:
a polycarbonate polyol; and
an aliphatic diisocyanate;
a molar ratio of the crosslinking agent and the chain extender in the range of 0.10 to 1.15.
23. The photochromic cast lens according to claim 22 wherein the polycarbonate polyol has a formula:
where n is equal to an integer from 3 to 6 or a combination thereof, and “x” is an integer that makes the molecular weight of the polycarbonate polyol approximately equal to 500 to 2,500.
24. The photochromic cast lens according to claim 22 wherein the prepolymer is formed from a composition further comprising a polyether polyol.
25. The photochromic cast lens according to claim 24 wherein the polyether polyol has a formula:
HO—[(CR1R2M) n O] x H
where R1 and R2 are hydrogen or an alkyl group, where “n” is equal to an integer from 3 to 6, and “x” is an integer that makes the molecular weight of the polyether polyol approximately equal to 1000 and where “M” has a formula:
(CH2) y
where “y” is an integer from 1 to 6.
26. The photochromic cast lens according to claim 24 wherein a molar ratio of the polycarbonate polyol to the polyether polyol is in the range of 0.5 to 1.5.
27. The photochromic cast lens according to claim 22 wherein the crosslinking agent comprises di(trimethylolpropane).
28. The photochromic cast lens according to claim 22 wherein the chain extender comprises 1,4-butanediol.
29. The photochromic cast lens according to claim 22 wherein the aliphatic diisocyanate comprises 4,4′-dicyclohexylmethanediisocyanate.
30. The photochromic cast lens according to claim 22 wherein the first resin sheet comprises polycarbonate.
31. The photochromic cast lens according to claim 22 wherein the first resin sheet comprises cellulose acylate.
32. The photochromic cast lens according to claim 22 wherein the first resin sheet and the second resin sheet comprise polycarbonate.