Source: https://patents.google.com/patent/US8367211B2/en
Timestamp: 2018-03-24 08:59:52
Document Index: 479093697

Matched Legal Cases: ['Application No. 96908587', 'Application No. 96', 'Application No. 04', 'Application No. 03', 'Application No. 04009085', 'Application No. 96', 'Application No. 96', 'Application No. 96', 'Application No. 04', 'Application No. 03', 'Application No. 03', 'Application No. 03744674', 'Application No. 06816842', 'Application No. 06815842', 'Application No. 2004270746', 'Application No. 2003225785', 'Application No. 2004270746']

US8367211B2 - Photochromic lens - Google Patents
Photochromic lens Download PDF
US8367211B2
US8367211B2 US12959201 US95920110A US8367211B2 US 8367211 B2 US8367211 B2 US 8367211B2 US 12959201 US12959201 US 12959201 US 95920110 A US95920110 A US 95920110A US 8367211 B2 US8367211 B2 US 8367211B2
US12959201
US20110070432A1 (en )
This application is a divisional of U.S. patent application Ser. No. 11/537,571 filed Sep. 29, 2006 now U.S. Pat. No. 7,858,001 entitled Photochromic Lens, which claims the benefit of priority from U.S. Provisional Application Ser. No. 60/722,848 filed on Sep. 29, 2005 entitled Photochromic Lens; and which is a Continuation-In-Part of U.S. application Ser. No. 10/938,275 filed on Sep. 9, 2004 entitled Photochromic Polyurethane Laminate, which claims the benefit of priority from U.S. Provisional Application Ser. No. 60/501,819 filed Sep. 9, 2003 entitled Photochromic Film and Method of Manufacture, and which claims the benefit of priority from U.S. Provisional Application Ser. No. 60/501,820 filed on Sep. 9, 2003 entitled Photochromic Laminate which are hereby incorporated herein by reference.
Often bleeding occurs due to the deformation of the photochromic layer under the high temperature and pressure used during the injection molding process. This is thought to occur due to either an excess amount of functional layer material and/or inadequate softening properties of the functional layer material. Further, this bleeding can interfere with any additional coating layers that are applied to the lens after injection-molding. The Bhalakia patent adequately addresses the issue of making laminates used in injection-molding, through improvement of laminate materials and properties. However, the issues addressed by Bhalakia do not include providing a laminate or insert that may be used in a cast- lens manufacturing process.
As seen in FIG. 1, one embodiment according to the present invention relates to a photochromic lens comprising a front cast resin layer 1, a photochromic film 2, and a back cast resin layer 3. Specifically, a preferred embodiment would include a photochromic lens made from a cast resin that is either thermoset or radiation-set. The photochromic lens may be either a finished product or a semi-finished product. In one embodiment (as shown in FIG. 2), a photochromic lens may include a photochromic film 2 including at least one protective layer 4 and a photochromic layer 5 (as shown in FIG. 2, examples (A),(B) and (C)). In another embodiment, the photochromic film may include just a photochromic layer 5 (as shown in FIG. 2, example (D)). In each of these embodiments, the photochromic film 2 is bonded or adhered strongly to a casting resin layer 1, 3 during a casting process (as shown in FIG. 1). The photochromic film 2 in the form of a laminate may be optimized as a host for a photochromic dye to provide for maximum performance of the dye.
Preferred materials for the photochromic layer 5 of the present invention would include, for example, plastic host resins having a glass transition temperature, Tg, of less than 50° C., and more preferably, below 30° C. These plastics tend to be mechanically soft which is ideal for the photochromes to activate and de-activate. When the photochromic dyes absorb UV light, typically a carbon-oxygen bond in the photochromic dye molecule is broken and the dye molecule rotates into a form that absorbs visible light. A soft plastic host for the dye that would facilitate this action preferably would include a class of plastic hosts, such as polyurethanes. However, historically, this mechanical softness of plastic hosts has been shown deficient when such materials are used as ophthalmic lens materials. Therefore, a preferred embodiment of an ophthalmic lens contemplated for use with the present invention would include encapsulation of a host urethane resin, such as a photochromic layer 5, within an ophthalmic lens. A preferred thickness of the photochromic layer 5, namely the photochromic urethane layer 5, would preferably be 10 mil or less, more preferably 4 mil or less and most preferably, to 2 mil or less.
Examples of manufacturing the photochromic lens as contemplated in the present invention would include, for instance, a cast molding process, in which a photochromic film 2 is first placed into a cast mold. Thereafter, a cast resin 1,3 may also be introduced into the cast mold and the lens would be cured, forming an integrate photochromic cast lens. The photochromic film 2 may be placed in any number of orientations within the mold, depending upon desired results and lens processing applications.
A photochromic film was prepared according to the examples in U.S. patent application Ser. No. 10/938,275. The polyurethane layer is 40 μm thick, and the protective layers are 76 μm cellulose acetate butyrate (CAB) films (K-Mac). The polyurethane layer and protective layers were bonded together to form a photochromic laminate. The laminate was masked with a 3M film (24S56W). A 70-mm disk was die-cut off from the above laminate, and formed into a 6-base laminate wafer through a thermo-vacuum forming process. The temperature was 255° F., and the forming time was 200 seconds. A 70-mm lens cast gasket and two 6-base glass molds (front and back) were used to cast the photochromic lens. The masked film is thereafter removed prior to placement of the laminate wafer into the gasket. The laminate wafer was fixed in the gasket about 1 mm away from the front mold surface with help of a spacer. A clear UV-curable cast resin from OptiCast was injected into the front and back cavities. The front cavity is formed by the front mold and the photochromic film. The cast resin in the above setup was cured under a 12-mW/m2 exposure for 10 minutes. The result was a cast resin lens having the photochromic film embedded in it. The unactivated transmission of the lens was measured as 70%. The activated transmission after exposure to a Xenon lamp under 20 W/m2 intensity of UV was measured to be 19%. This demonstrated good photochromic activity.
To a solution of 18% by weight of a polyester urethane (Tecoflex CLC-93A from Thermedics) in THF solvent was added 2% each of Tinuvins 765, 144, and Irganox 1010 (all from CIBA Corporation), and 0.8% of naphthopyran photochromic dye VP0762 (Proprietary Vision-Ease Dye). The mixture was then cast on a flat borosilicate glass plate and the solvent allowed to evaporate. A photochromic film of about 0.2 mm thick was obtained. The photochromic film was then placed between two glass molds held together with a standard casting gasket. A mixture of 58.3 grams of casting monomer P11 (NOF Corporation), 0.6 gram of Tinuvin 765, 0.26 gram of Trigonox 23 catalyst and 0.37 gram of Trigonox 21 catalyst was introduced between the glass molds and around the polyurethane film. The mold and gasket assembly was placed in a water bath and cured in a cycle that ramps the lens up to 90oC over a 20 hour period. The resultant thermoset, cast lens is then separated from the glass molds. The lens had a refractive index of 1.55. The lens sample was then fatigued by exposure to a Xenon lamp with an ultraviolet light output of 30 Watts/Square Meter for 144 hours. This simulates actual wear of the lens by someone for a two year wear period. After the 144 hours, the photochromic performance remaining was 97%. This compares to the performance of the commercial photochromic polycarbonate Quantum (Transitions Optical, Inc.) lens product that is believed to be only a 65% remaining performance. Thus, the photochromic film in the cast lens was very fatigue resistant and had longer life than the prior art.
A photochromic film was prepared according to the examples in U.S. patent application Ser. No. 10/938,275. The polyurethane layer is 40 μm thick, and the protective layers are 350 μm thick polycarbonate films. The polyurethane layer and protective layers were bonded together to form a photochromic laminate. The laminate was masked with a 3M film (24S56W). A 70-mm disk was die-cut off from the above laminate, and formed into a 6-base laminate wafer through a thermo-vacuum forming process. The temperature was 255° F., and the forming time was 200 seconds. A 70-mm lens cast gasket and two 6-base glass molds (front and back) were used to cast the photochromic lens. The masked film is thereafter removed prior to placement of the laminate wafer into the gasket. The laminate wafer was placed against the front mold surface and placed into the gasket with the back mold. A clear UV-curable cast resin from OptiCast (OPIV-B) was injected into the back cavity. The cast resin in the above setup was cured under a 12-mW/m2 UV exposure for 7 minutes. The result was a cast resin lens having the photochromic laminate fused to the front of it. The unactivated transmission of the lens was measured as 79%. The activated transmission after exposure to a Xenon lamp under 12 W/m2 intensity of UV was measured to be 19%. This demonstrated good photochromic activity.
A photochromic film was prepared by laminating 13.5 mil thick CAB film (Kodacel K7896, made by Eastman Kodak) for both top and bottom protective layers and 38 micron photochromic layer (polyurethane). The laminate was masked with 3M protective masking film (24S56W) on both sides then a 86 mm disk in diameter was cut-out from the above laminate. It was formed into a 6 base laminate wafer through a thermo-vacuum forming process. The forming temperature was 235° F. and forming time was 150 seconds. It was further cut to 72.6 mm in diameter to fit the size of casting mold. It was further cut by 3 mm on two locations to allow flow of the cast resin around it. A 73 mm casting mold and two 6 base glass molds were used for front and back to cast a photochromic lens. The masked film is thereafter removed prior to placement of the laminate wafer into the gasket. Said formed photochromic film was placed in the mold about 1 mm away from the front mold surface with help of a spacer. Thermo-set resin RAV-7 (made by Great Lakes Chemical) without UV absorbing agent was injected to fill both front cavity and back cavity which were separated by the photochromic film. The cast resin in above setup was thermally cure in normal condition. The result was a cast resin lens having the photochromic laminate fused to the front of it. The unactivated transmission of the lens was measured as 82.4%. The activated transmission after exposure to a Xenon lamp under 12 W/m2 intensity of UV was measured to be 16%. This demonstrated good photochromic activity.
A photochromic film was prepared by laminating 12 mil thick polycarbonate film (1151 by Teijin Kasei America) for both top and bottom protective layers and 38 micron photochromic layer (polyurethane). The polycarbonate film was applied with UV curable hardcoat as barrier coating on one side in advance. The hardcoated side was placed outside of lamination that later contacts casting resin. Without this barrier coating, this casting resin monomer has been shown to cause the polycarbonate film to turn white and, therefore, usable. The laminate was masked with 3M protective masking film (24S56W) on both sides then a 86 mm disk in diameter was cut-out from the above laminate. It was formed into a 6 base laminate wafer through a thermo-vacuum forming process. The forming temperature was 285° F. and forming time was 250 seconds. It was further cut to 72.6 mm in diameter to fit the size of casting mold. It was further cut by 3 mm on two locations to allow flow of the cast resin around it. A 73 mm casting mold and two 6 base glass molds were used for front and back to cast a photochromic lens. The masked film is thereafter removed prior to placement of the laminate wafer into the gasket. Said formed photochromic film was placed in the mold about 1 mm away from the front mold surface with help of a spacer. Thermo-set resin RAV-7 (made by Great Lakes Chemical) without UV absorbing agent was injected to fill both front cavity and back cavity which were separated by the photochromic film. The cast resin in above setup was thermally cure in normal condition. The result was a cast resin lens having the photochromic laminate fused to the front of it. The unactivated transmission of the lens was measured as 90.0%. The activated transmission after exposure to a Xenon lamp under 12 W/m2 intensity of UV was measured to be 19%. This demonstrated good photochromic activity.
1. A cast photochromic lens comprising:
a photochromic film interposed between two portions of a single cast resin substrate;
wherein said photochromic film comprises at least one protective layer distinct from said cast resin substrate and a photochromic polyurethane layer, said photochromic polyurethane layer prepared from a composition comprising:
a solid thermoplastic polyurethane prepared from a composition comprising at least one diisocyanate;
an isocyanate-terminated polyurethane prepolymer; and
a photochromic compound;
said photochromic polyurethane layer having a top side and a bottom side, said at least one protective layer being bonded to at least one side of said photochromic polyurethane layer.
2. The lens of claim 1, wherein said photochromic film comprises a thickness of less than 40 mil.
3. The lens of claim 1, wherein said cast resin substrate comprises a thermoset resin.
4. The lens of claim 1, wherein said cast resin substrate comprises a radiation-set resin.
5. The lens of claim 1, wherein said at least one protective layer comprises a resin selected from a group consisting of: acrylate resins, cellulose esters and polycarbonate resins.
6. A cast photochromic lens comprising:
a first cast resin,
a second cast resin; and
a photochromic film placed therebetween, said photochromic film prepared from a composition comprising:
said first cast resin and said second cast resin formed of a same resin.
7. The lens of claim 6, wherein said photochromic film comprises materials having a glass transition temperature of less than 50° C.
8. The lens of claim 6, wherein said photochromic film comprises materials having a glass transition temperatures of less than 30° C.
9. The lens of claim 6, wherein said isocyanate-terminated polyurethane prepolymer has a molecular weight of about 1000 to 6000 g/mol.
10. The lens of claim 6 wherein said thermoplastic polyurethane has a molecular weight of about 9,000 to 100,000 g/mol.
11. A cast photochromic lens comprising:
a photochromic film having a first side and a second side, the photochromic film comprising at least one protective layer and a photochromic layer;
a first cast resin substrate molded to the first side of the photochromic film; and
a second cast resin substrate molded to the second side of the photochromic film;
wherein said first and second cast resin substrates are formed of a same resin and wherein the resin is distinct from said at least one protective layer; and
wherein said photochromic layer is prepared from a composition comprising:
a solid thermoplastic polyurethane;
12. A lens according to claim 11 wherein the photochromic layer comprises a photochromic polyurethane.
13. A lens according to claim 11 wherein the photochromic film has a thickness of no greater than 40 mil.
14. A lens according to claim 11 wherein said first and second cast resin substrates comprise a thermoset resin.
15. A lens according to claim 11 wherein said first and second cast resin substrates comprise a radiation-set resin.
16. A lens according to claim 11 wherein the protective layer comprises a resin selected from a group consisting of: acrylate resins, cellulose esters and polycarbonate resins.
17. A lens according to claim 11 wherein the photochromic film comprises a material having a glass transition temperature of less than 50 degrees Celsius.
18. A lens according to claim 11 wherein the photochromic film comprises a material having a glass transition temperatures of less than 30 degrees Celsius.
19. A lens according to claim 11 wherein the photochromic layer is interposed between two protective layers.
20. A lens according to claim 11 wherein the photochromic lens further comprises a layer selected from a group consisting of: adhesion layer, polarizing layer, hard-coating layer, primer layer, and barrier layer.
US12959201 2003-09-09 2010-12-02 Photochromic lens Active US8367211B2 (en)
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US50181903 true 2003-09-09 2003-09-09
US10938275 US8298671B2 (en) 2003-09-09 2004-09-09 Photochromic polyurethane laminate
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US11537571 US7858001B2 (en) 2003-09-09 2006-09-29 Photochromic lens
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US13741290 US20130127078A1 (en) 2003-09-09 2013-01-14 Photochromic Lens
US11537571 Division US7858001B2 (en) 2003-09-09 2006-09-29 Photochromic lens
US13741290 Division US20130127078A1 (en) 2003-09-09 2013-01-14 Photochromic Lens
US20110070432A1 true US20110070432A1 (en) 2011-03-24
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US11537571 Active 2026-10-30 US7858001B2 (en) 2003-09-09 2006-09-29 Photochromic lens
US12959201 Active US8367211B2 (en) 2003-09-09 2010-12-02 Photochromic lens
US13741290 Pending US20130127078A1 (en) 2003-09-09 2013-01-14 Photochromic Lens
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