Photochromic Polyurethane Laminate
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 - 15 . (canceled)
16 . A photochromic polyurethane laminate for use in an optical article comprising:
a first transparent resin sheet coated with a polyurethane primer on a first side;
a second transparent resin sheet coated with said polyurethane primer on a first side;
a photochromic polyurethane film having a first side laminated to said first side of said first transparent resin sheet and a second side laminated to said first side of said second transparent resin sheet, said photochromic polyurethane film formed from a composition comprising:
an isocyanate-terminated prepolymer formed by reacting a polyol with an aliphatic diisocyanate or a cycloaliphatic diisocyanate;
a hydroxyl-terminated polyurethane formed by reacting a polyol with an aliphatic diisocyanate or a cycloaliphatic diisocyanate and a chain extender; and
one or more photochromic compounds;
wherein said polyurethane primer is formed by reacting an isocyanate-terminated prepolymer that is distinct from said isocyanate-terminated prepolymer employed to form said 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.
17 . The photochromic polyurethane laminate of claim 16 , wherein said polyurethane primer, formed by reacting 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 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.
18 . A photochromic polyurethane laminate for use in an optical article comprising:
a photochromic polyurethane film laminated between a first side of a first transparent resin sheet coated with a primer and a first side of a second transparent resin sheet coated with said primer;
the photochromic polyurethane film formed from a composition comprising:
an isocyanate-terminated prepolymer formed by reacting a polyol with an aliphatic diisocyanate or a cycloaliphatic diisocyanate;
a hydroxyl-terminated polyurethane formed by reacting a polyol with an aliphatic diisocyanate or a cycloaliphatic diisocyanate and a chain extender; and
one or more photochromic compounds;
wherein the polyurethane primer is formed 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 agent.
19 . The photochromic polyurethane laminate of claim 18 , wherein the polyurethane primer, formed 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 agent, comprises 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.
20 . The photochromic polyurethane laminate of claim 16 , wherein the hydroxyl-terminated polyurethane formed by reacting the polyol with the aliphatic diisocyanate or the cycloaliphatic diisocyanate and the chain extender further comprises:
(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.
21 . The photochromic polyurethane laminate of claim 16 , wherein the isocyanate-terminated prepolymer formed 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.
22 . The photochromic polyurethane laminate of claim 16 , wherein the isocyanate-terminated prepolymer reacts with a cured form of the hydroxyl-terminated polyurethane dissolved in a solvent.
23 . The photochromic polyurethane laminate of claim 16 , wherein the photochromic polyurethane laminate is cured in a two-step curing process comprising a curing at ambient temperature followed by a curing at 50 to 130 degrees Celsius.
24 . A photochromic polyurethane laminate for use in an optical article comprising:
a transparent first resin sheet coated with a polyurethane primer on a first side;
a transparent second resin sheet coated with said polyurethane primer on a first side;
a photochromic polyurethane film formed from a coating solution of said photochromic polyurethane and laminated between the first sides of said first and said second transparent resin sheets, wherein a composition of said photochromic polyurethane coating solution comprises:
a hydroxyl-terminated polyurethane formed by reacting a diisocyanate with a polyol;
an isocyanate-terminated prepolymer; and
one or more photochromic compounds;
wherein said polyurethane primer is formed by reacting an aliphatic diisocyanate or a cycloaliphatic diisocyanate with the polyol employed for forming said hydroxyl-terminated polyurethane.
25 . The photochromic polyurethane laminate of claim 24 further comprises 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.
26 . The photochromic polyurethane laminate of claim 24 , wherein the hydroxyl-terminated polyurethane is having a molecular weight of at least 66,210 Daltons.
27 . The photochromic polyurethane laminate of claim 24 , wherein the hydroxyl-terminated polyurethane formed by reacting a diisocyanate with a polyol, comprises:
(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.
28 . The photochromic polyurethane laminate of claim 24 , wherein a reaction between the hydroxyl-terminated polyurethane with the isocyanate-terminated prepolymer comprises dissolving a cured form of the hydroxyl-terminated polyurethane.
29 . The photochromic polyurethane laminate of claim 24 , wherein the isocyanate-terminated prepolymer further comprises:
(a) an aliphatic diisocyanate or a 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.
30 . The photochromic polyurethane laminate of claim 24 , wherein the polyurethane primer, formed by reacting the aliphatic diisocyanate or the cycloaliphatic diisocyanate with the polyol employed for forming said hydroxyl-terminated polyurethane, is having a molecular weight of 59,995 Daltons.
31 . The photochromic polyurethane laminate of claim 24 , wherein a composition of said polyurethane primer comprises:
(a) the aliphatic diisocyanate or the cycloaliphatic diisocyanate;
(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 forming said 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.
32 . The photochromic polyurethane laminate of claim 24 , wherein a composition of said polyurethane primer comprises:
(a) the aliphatic diisocyanate or the cycloaliphatic diisocyanate;
(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 forming said 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.
33 . The photochromic polyurethane laminate of claim 24 , wherein a reaction between the hydroxyl-terminated polyurethane with the isocyanate-terminated prepolymer further comprises reacting the hydroxyl-terminated polyurethane and the isocyanate-terminated prepolymer with a crosslinking agent.
34 . The photochromic polyurethane laminate of claim 33 , wherein the crosslinking agent is di(trimethylolpropane).
35 . The photochromic polyurethane laminate of claim 16 , wherein a reaction between the hydroxyl-terminated polyurethane with the isocyanate-terminated prepolymer further comprises reacting the hydroxyl-terminated polyurethane and the isocyanate-terminated prepolymer with a crosslinking agent.
36 . The photochromic polyurethane laminate of claim 35 , wherein the crosslinking agent is di(trimethylolpropane).
37 . The photochromic polyurethane laminate of claim 18 , wherein the polyurethane primer, formed 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:
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.
38 . The photochromic polyurethane laminate of claim 18 , wherein the hydroxyl-terminated polyurethane, formed by reacting the polyol with the aliphatic diisocyanate or the cycloaliphatic diisocyanate and the chain extender, further comprises:
(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.
39 . The photochromic polyurethane laminate of claim 18 , wherein the isocyanate-terminated prepolymer formed 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.
40 . The photochromic polyurethane laminate of claim 18 , wherein reacting the isocyanate-terminated prepolymer and the hydroxyl-terminated polyurethane to form a reaction mixture comprises dissolving a cured form of the hydroxyl-terminated polyurethane.
41 . The photochromic polyurethane laminate of claim 18 , wherein the photochromic polyurethane laminate is cured in a two-step curing process comprising a curing at ambient temperature followed by a curing at 50 to 130 degrees Celsius.
42 . The photochromic polyurethane laminate of claim 18 , wherein a reaction between the isocyanate-terminated prepolymer with the hydroxyl-terminated polyurethane further comprises reacting the isocyanate-terminated prepolymer and the hydroxyl-terminated polyurethane with a crosslinking agent.
43 . The photochromic polyurethane laminate of claim 42 , wherein the crosslinking agent comprises di(trimethylolpropane).