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Method and composition for producing activating light absorbing lenses

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Publication number
WO1999006887A1
WO1999006887A1 PCT/US1998/015959 US9815959W WO1999006887A1 WO 1999006887 A1 WO1999006887 A1 WO 1999006887A1 US 9815959 W US9815959 W US 9815959W WO 1999006887 A1 WO1999006887 A1 WO 1999006887A1
Authority
WO
Grant status
Application
Patent type
Prior art keywords
lens
light
mold
composition
activating
Prior art date
Application number
PCT/US1998/015959
Other languages
French (fr)
Inventor
Omar M. Buazza
Stephen C. Luetke
Galen R. Powers
Original Assignee
Q2100, Inc.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date

Links

Classifications

    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/0005Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B29WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE, IN GENERAL
    • B29CSHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C35/00Heating, cooling or curing, e.g. crosslinking, vulcanising; Apparatus therefor
    • B29C35/02Heating or curing, e.g. crosslinking, vulcanising during moulding, e.g. in a mould
    • B29C35/0288Controlling heating or curing of polymers during moulding, e.g. by measuring temperatures or properties of the polymer and regulating the process
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B29WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE, IN GENERAL
    • B29CSHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C35/00Heating, cooling or curing, e.g. crosslinking, vulcanising; Apparatus therefor
    • B29C35/02Heating or curing, e.g. crosslinking, vulcanising during moulding, e.g. in a mould
    • B29C35/08Heating or curing, e.g. crosslinking, vulcanising during moulding, e.g. in a mould by wave energy or particle radiation
    • B29C35/0888Heating or curing, e.g. crosslinking, vulcanising during moulding, e.g. in a mould by wave energy or particle radiation using transparant moulds
    • B29C35/0894Heating or curing, e.g. crosslinking, vulcanising during moulding, e.g. in a mould by wave energy or particle radiation using transparant moulds provided with masks or diaphragms
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B29WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE, IN GENERAL
    • B29DPRODUCING PARTICULAR ARTICLES FROM PLASTICS OR FROM SUBSTANCES IN A PLASTIC STATE
    • B29D11/00Producing optical elements, e.g. lenses or prisms
    • B29D11/00009Production of simple or compound lenses
    • B29D11/00432Auxiliary operations, e.g. machines for filling the moulds
    • B29D11/00442Curing the lens material
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B29WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE, IN GENERAL
    • B29CSHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C35/00Heating, cooling or curing, e.g. crosslinking, vulcanising; Apparatus therefor
    • B29C35/02Heating or curing, e.g. crosslinking, vulcanising during moulding, e.g. in a mould
    • B29C35/08Heating or curing, e.g. crosslinking, vulcanising during moulding, e.g. in a mould by wave energy or particle radiation
    • B29C35/0805Heating or curing, e.g. crosslinking, vulcanising during moulding, e.g. in a mould by wave energy or particle radiation using electromagnetic radiation
    • B29C2035/0827Heating or curing, e.g. crosslinking, vulcanising during moulding, e.g. in a mould by wave energy or particle radiation using electromagnetic radiation using UV radiation
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B29WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE, IN GENERAL
    • B29CSHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C35/00Heating, cooling or curing, e.g. crosslinking, vulcanising; Apparatus therefor
    • B29C35/02Heating or curing, e.g. crosslinking, vulcanising during moulding, e.g. in a mould
    • B29C35/08Heating or curing, e.g. crosslinking, vulcanising during moulding, e.g. in a mould by wave energy or particle radiation
    • B29C35/0805Heating or curing, e.g. crosslinking, vulcanising during moulding, e.g. in a mould by wave energy or particle radiation using electromagnetic radiation
    • B29C2035/0833Heating or curing, e.g. crosslinking, vulcanising during moulding, e.g. in a mould by wave energy or particle radiation using electromagnetic radiation using actinic light
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B29WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE, IN GENERAL
    • B29CSHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C35/00Heating, cooling or curing, e.g. crosslinking, vulcanising; Apparatus therefor
    • B29C35/16Cooling
    • B29C2035/1658Cooling using gas
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B29WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE, IN GENERAL
    • B29CSHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C37/00Component parts, details, accessories or auxiliary operations, not covered by group B29C33/00 or B29C35/00
    • B29C2037/90Measuring, controlling or regulating
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B29WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE, IN GENERAL
    • B29KINDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS
    • B29K2105/00Condition, form or state of moulded material or of the material to be shaped
    • B29K2105/0002Condition, form or state of moulded material or of the material to be shaped monomers or prepolymers
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S425/00Plastic article or earthenware shaping or treating: apparatus
    • Y10S425/808Lens mold

Abstract

An eyeglass lens forming composition containing light absorbing compounds which may undergo light initiated polymerization is provided. Typically, lens forming compositions that absorb light do not permit enough activating radiation to penetrate into the depths of the lens cavity to adequately initiate polymerization of the lens forming composition. An embodiment of the invention provides a system and method for curing such a lens forming composition to form a lens that does not transmit activating light. Activating light is used having a wavelength greater than the wavelengths of light which the light absorbing compounds absorb. The power of the formed lenses may be controlled by varying the lens forming conditions. Additionally, the lens forming process may be controlled using a microprocessor based control system.

Description

TITLE: METHOD AND COMPOSITION FOR PRODUCING ACTIVATING LIGHT ABSORBING LENSES

BACKGROUND OF THE INVENTION

1 Field of the Invention

The present invention relates generally to eyeglass lenses More particularly, the invention relates to a lens forming composition and method for making activating light absorbmg plastic lenses by curing the lens forming composition using activating light

2 Description of Related Art

It is conventional in the art to produce optical lenses by thermal curmg techniques from the polymer of diethylene glycol bιs(allyl)-carbonate (DEG-BAC) In addition, optical lenses may also be made usmg ultraviolet ("UV") light curing techniques See, for example, U S Patent Nos 4,728,469 to Lipscomb et al , 4,879,318 to Lipscomb et al , 5,364,256 to Lipscomb et al , 5,415,816 to Buazza et al , 5,529,728 to Buazza et al , 5,514,214 to Joel et al , U S patent application serial nos 07/425,371 filed October 26, 1989, 08/454,523 filed May 30, 1995, 08/453,770 filed May 30, 1995, 07/932,812 filed August 18, 1992, 08/636,510 filed April 19, 1996, 08/844,557 filed April 18, 1997, 08/904,289 filed July 31, 1997, and 08/959,973 all of which are hereby specifically incorporated by reference

Curing of a lens by ultraviolet light tends to present certain problems that must be overcome to produce a viable lens Such problems mclude yellowing of the lens, cracking of the lens or mold, optical distortions in the lens, and premature release of the lens from the mold In addition, many of the useful UV-curable lens formmg compositions exhibit certain characteristics which mcrease the difficulty of a lens curmg process For example, due to the relatively rapid nature of ultraviolet light initiated reactions, it is a challenge to provide a composition which is UV curable to form an eyeglass lens Excessive exothermic heat tends to cause defects m the cured lens To avoid such defects, the level of photoinitiator may be reduced to levels below what is customarily employed in the ultraviolet curing art

While reducing the level of photoinitiator addresses some problems, it may also cause others For mstance, lowered levels of photoinitiator may cause the material in regions near an edge of the lens and proximate a gasket wall in a mold cavity to incompletely cure due to the presence of oxygen in these regions (oxygen is believed to inhibit curmg of many lens formmg compositions or materials) Uncured lens forming composition tends to result in lenses with "wet" edges covered by sticky uncured lens forming composition Furthermore, uncured lens formmg composition may migrate to and contammate the optical surfaces of the lens upon demoldmg The contaminated lens is then often unusable

Uncured lens formmg composition has been addressed by a variety of methods (see, e g , the methods described in U S Patent No 5,529,728 to Buazza et al) Such methods may mclude removing the gasket and applymg either an oxygen barrier or a photoinitiator enriched liquid to the exposed edge of the lens, and then re- lrradiating the lens with a dosage of ultraviolet light sufficient to completely dry the edge of the lens pπor to demolding During such irradiation, however, higher than desirable levels of irradiation, or longer than desirable periods of irradiation, may be required The additional ultraviolet irradiation may in some circumstances cause defects such as yellowing in the lens

The low photoinitiator levels utilized in many ultraviolet curable lens formmg compositions may produce a lens which, while fully-cured as measured by percentage of remammg double bonds, may not possess sufficient crosslink density on the lens surface to provide desirable dye absorption characteristics duπng the tinting process

Vaπous methods of increasing the surface density of such UV curable lenses are descnbed m U.S Patent No 5,529,728 to Buazza et al. In one method, the lens is demolded and then the surfaces of the lens are exposed directly to ultraviolet light. The relatively short wavelengths (around 254 nm) provided by some UV sources (e.g., a mercury vapor lamp) tend to cause the material to crosslink quite rapidly. An undesirable effect of this method, however, is that the lens tends to yellow as a result of such exposure. Further, any contaminants on the surface of the lens which are exposed to short wavelengths of high intensity UV light may cause tint defects. Another method involves exposing the lens to relatively high intensity ultraviolet radiation while it is still within a mold cavity formed between glass molds. The glass molds tend to absorb the more effective short wavelengths, while transmitting wavelengths of about 365 nm This method generally requires long exposure times and often the infrared radiation absorbed by the lens mold assembly will cause premature release of the lens from a mold member. The lens mold assembly may be heated prior to exposure to high intensity ultraviolet light, thereby reducing the amount of radiation necessary to attain a desired level of crosslink density This method, however, is also associated with a higher rate of premature release.

It is well known m the art that a lens mold/gasket assembly may be heated to cure the lens formmg composition from a liquid monomer to a solid polymer. It is also well known that such a lens may be thermally postcured by applymg convective heat to the lens after the molds and gaskets have been removed from the lens. In this application the terms "lens forming material" and "lens forming compositions" are used interchangeably SUMMARY OF THE INVENTION

One aspect of the invention relates to applymg an oxygen barrier around the exposed edges of a lens to initiate the reaction of mcompletely cured lens formmg material proximate the lens edges. In an embodiment, a liquid polymerizable lens formmg composition is placed m a mold cavity having at least two molds and/or a gasket. Activating light rays may be directed toward at least one of the mold members to substantially cure the lens formmg composition to a lens havmg material proximate the edges of the lens that is not fully cured. The gasket may be removed to expose the edges of the lens, and an oxygen barrier compπsmg a photoinitiator may be placed around the exposed edges of the lens such that at least a portion of the oxygen barrier photomitiator is proximate lens formmg composition that is not fully cured. A portion of the mcompletely cured material may be removed manually pπor to the application of the oxygen barrier. Subsequently another set of activatmg light rays may be directed towards the lens such that at least a portion of the oxygen barrier photomitiator initiates reaction of lens forming composition while the oxygen barrier substantially prevents oxygen from outside the oxygen barrier from contacting at least a portion of the lens forming composition. The lens may be allowed to cool and the oxygen barrier may be removed. The lens may be tinted after the cure is completed.

The oxygen barrier may include a flexible, stretchable, self-sealing film that is at least partially transparent to activating light rays. The oxygen barrier may include polyethylene impregnated with a photoinitiator. The film may include a strip of high density polyethylene that is about 0.01-1.0 mm thick, and more preferably about 0.01-0.10 mm thick. Thicker films tend to be less conformable and stretchable. The oxygen barrier may include a plastic film that is less than about 0.025 mm thick, (e.g., about 0.0127 mm thick) and that was made by (a) immersing or running a plastic film in or through a solution comprising a photoinitiator and an etching agent (b) removing the plastic film from the solution, and (c) drying the plastic film. A surface on the plastic film may be chemically etched prior to or while immersing the plastic film in the solution.

Another aspect of the invention relates to applying conductive heat to the face of a lens. In an embodiment of the invention, a liquid polymerizable lens forming composition is placed in a mold cavity having a first mold member and a second mold member. First activating light rays may be directed toward at least one of the mold members to cure the lens forming composition to a lens. A mold member may be applied to a substantially solid conductive heat source. Heat may be conductively applied to a face of the lens by (a) conductively transferring heat to a face of a mold member from the conductive heat source, and (b) conductively transferring heat through such mold member to the face of the lens. In an embodiment, a flexible heat distributor may be placed between the heat source and the mold member to partially insulate the mold member and to slowly and uniformly transfer heat to the face of the mold member. The distributor may be shaped to conform to the face of a mold member. The heat source may include a concave element that may conform to the convex face of a mold member. The heat source may include a convex element that may conform to the concave face of a mold member. The temperature of the heat source may be thermostatically controlled. Heat may be conductively applied through a mold member to the back face of the lens, thereby enhancing the cross-linking and tintability of the lens forming material proximate to the surface of the back face of the lens (e.g., when an untintable scratch resistant coating is on the front face of the lens).

In an embodiment of the invention an eyeglass lens may be formed by (a) placing a liquid, polymerizable lens-forming composition in a mold cavity defined by at least a first mold member and a second mold member, (b) applying a plurality of preferably high intensity activating light light pulses to the lens forming composition, at least one of the pulses having a duration of less than about one second (more preferably less than about 0.1 seconds, and more preferably between 0.1 and 0.001 seconds), and (c) curing the lens forming composition to form a substantially clear eyeglass lens in a time period of less than 30 minutes (more preferably less than 20 minutes, and more preferably still less than 15 minutes).

The pulses preferably have a sufficiently high intensity such that reaction is initiated in substantially all of the lens forming composition that is exposed to pulses in the mold cavity. In one embodiment reaction is initiated in substantially all of any cross section of the lens forming composition that is exposed to pulses in the mold cavity Preferably the temperature of the lens forming composition begms to rise after such application of activatmg light

The lens formmg composition may be exposed to activating light from one, two, or multiple sources Two sources may be applied on opposite sides of the mold cavity to apply light to the lens formmg composition from two sides In an alternate embodiment, the lens forming composition is exposed to a relatively low intensity activating light before or while the pulses are applied Such pulses are preferably relatively high in intensity, and are preferably applied to the other side of the mold cavity than the relatively low intensity light

The lens formmg composition is preferably contmuously exposed to a relatively low intensity activatmg light either before, while, or after pulses of relatively high intensity are applied, the relatively low intensity light having an intensity of less than 1000 microwatts/ cm2 (and more preferably less than 100 microwatts/ cm2, and more preferably still 2-30 microwatts/ cm2), as measured on an outside surface of a mold member of the mold cavity The relatively low intensity light tends to provide a low amount of light to keep the reaction going m a more steady or even manner between pulses

Preferably at least one or even all of the pulses has an intensity of at least 01 watt/ cm2, as measured on an outside surface of a mold member of the mold cavity Alternately at least one or even all of the pulses have an intensity of at least 0 1 or 1 watt/ cm2

Sufficient activating light can be applied such that the temperature of the lens formmg composition begms to increase Then in one embodiment at least 5 minutes of waiting or darkness occurs before applymg additional light (e g , pulses) The waiting or darkness allows heat to dissipate, thus tendmg to prevent excessive heat buildup m the mold cavity In one embodiment at least 5, 10, or 20 pulses are applied to the lens formmg composition before waitmg for about 5-8 minutes and then additional light is applied

The eyeglass lens has an average minimum thickness of at least about 1 5-2 0 mm Thicker lenses tend to be more difficult to cure with contmuous non-pulsed light

The mold cavity is preferably cooled with air or cooled air One significant advantage of light pulses is that ambient air may be used to cool the mold cavity, mstead of cooled air Thus significant lens curing costs may be avoided since air coolers tend to be costly to purchase and operate

The pulses preferably emanate from a flash source of light (l e , "a flash light") such as a xenon light source Preferably pulses are applied such that the lens formmg composition is oversaturated with activatmg light durmg at least one pulse. Flash lights are advantageous in that they have a short "warm-up" time (as opposed to contmuous lights that tend to require 5-60 minutes to stabilize)

Lenses may be formed with pulsed light that have more difficult to cure prescriptions such as lenses with a power greater than positive 2 diopters, or lenses with a power less than minus 4 diopters

One advantage of pulsed light application via flash lights is that even though higher intensities of light are applied, because the duration of the pulses is so short the total amount of light energy applied to cure the lens formmg composition is lessened Thus less radiant heat is applied to the mold cavity, thereby reducmg coolmg requirements Moreover, energy is saved. In one embodiment less than 20, 10, 5, or 1 Joule/ cm2 of energy is applied to cure the lens forming composition mto a lens

Preferably the activating light is applied as a function of the temperature of the lens formmg composition, as measured directly or indirectly by measuring a temperature within the chamber (e.g., a temperature of at least a portion of the mold cavity) or by measuring a temperature of air in or exiting the chamber.

In another embodiment of the invention, an eyeglass lens may be cured by (a) placing a liquid, polymerizable lens forming composition in a mold cavity defined by at least a first mold member and a second mold member, the lens forming composition comprising a photoinitiator, (b) applying activating light at an intensity to the lens forming composition through at least one of the mold members for a selected period of time such that a temperature of the composition begins to increase, (c) decreasing the intensity of the activating light to inhibit the temperature of the lens forming composition from increasing to a selected first temperature, (d) allowing an exothermic reaction of the lens formmg composition to increase the temperature of the lens forming composition to a second temperature, the second temperature being less than the selected first temperature, (e) curing the lens forming composition to form a substantially clear eyeglass lens by: (i) applying activating light at an intensity to the lens forming composition through at least one of the mold members, and (ii) decreasing the intensity of the activating light; and (f) wherein the eyeglass lens is formed from the lens forming composition in a time period of less than about 30 minutes.

In another embodiment of the invention an eyeglass lens may be made by (a) placing a liquid, polymerizable lens-forming composition in a mold cavity defined by at least a first mold member and a second mold member, the lens forming composition comprising a photoinitiator, (b) applying first activating light to at least one of the mold members for a selected first period of time such that a temperature of the lens forming composition begins to increase, (c) removing the first activating light from at least one of the mold members, thereby inhibiting the temperature of the composition from increasing to a selected first temperature, (d) repeatedly and alternately performing the following steps to complete the formation of a lens: (i) applying second activating light to at least one of the mold members for a selected second period of time and (ii) removing the second activating light from at least one of the mold members for a selected third period of time. In an alternate embodiment of the invention an eyeglass lens may be made by (a) placing a liquid, polymerizable lens forming composition in a mold cavity defined by at least a first mold member and a second mold member, the lens forming composition comprising a photoinitiator, (b) directing activating light at a first intensity toward at least one of the mold members for a selected first period of time such that a temperature of the composition begins to increase, (c) decreasing the first intensity of activating light from at least one of the mold members, (d) repeatedly directing a plurality of pulses of activating light to the lens forming composition through at least one of the mold members to complete formation of a substantially clear eyeglass lens, at least one of the pulses lasting for a second period of time, and wherein a third period of time exists between application of at least two of the pulses.

An apparatus of the invention may include: (a) a first mold member having a casting face and a non- casting face, (b) a second mold member having a casting face and a non-casting face, the second mold member being spaced apart from the first mold member during use such that the casting faces of the first mold member and the second mold member at least partially define a mold cavity, (c) a first pulse light generator adapted to generate and direct a pulse of activating light toward at least one of the first and second mold members during use, and (d) a controller adapted to control the first pulse light generator such that activating light is directed in a plurality of pulses toward at least one of the first and second mold members, at least one of the pulses having a duration of less than one second.

A system of the invention may include (a) a lens forming composition comprising a photoinitiator, (b) a first mold member having a casting face and a non-casting face, (c) a second mold member having a casting face and a non-casting face, the second mold member being spaced apart from the first mold member during use such that the casting faces of the first mold member and the second mold member at least partially define a mold cavity for the lens forming composition, (d) a first pulse light generator adapted to generate and direct a pulse of activating light toward at least one of the first and second mold members during use, (e) a controller adapted to control the first pulse light generator such that activating light is directed in a plurality of pulses toward at least one of the first and second mold members, at least one of the pulses having a duration of less than one second, and (f) wherein the system is adapted to cure the lens forming composition to form a substantially clear eyeglass lens in less than 30 minutes.

The lens forming composition preferably comprises at least one polyethylenic-functional monomer containing at least two ethylenically unsaturated groups selected from acrylyl and methacrylyl, at least one polyethylenic-functional monomer containing at least three ethylenically unsaturated groups selected from acrylyl and methacrylyl, and/or an aromatic containing bis(allyl carbonate)-functional monomer.

A system of the invention may include: (a) a lens forming composition comprising a photoinitiator, (b) a mold cavity chamber comprising a first mold member having a casting face and a non-casting face, a second mold member having a casting face and a non-casting face, the second mold member being spaced apart from the first mold member during use such that the casting faces of the first mold member and the second mold member at least partially define a mold cavity for the lens forming composition, (c) a first light generator adapted to generate and direct activating light in a first intensity toward at least one of the first and second mold members during use, (d) a temperature sensor adapted to sense a temperature in the chamber or a temperature of air exiting the chamber, (e) a controller coupled to the temperature sensor and adapted to control the first light generator such that the first intensity of activating light directed toward at least one of the first and second mold members is decreased when a temperature measured by the temperature sensor substantially increases, and (f) wherein the system is adapted to cure the lens forming composition to form a substantially clear eyeglass lens in less than 30 minutes. An apparatus of the invention may include (a) a first mold member having a casting face and a non- casting face, (b) a second mold member having a casting face and a non-casting face, the second mold member being spaced apart from the first mold member during use such that the casting faces of the first mold member and the second mold member at least partially define a mold cavity for a lens forming composition, (c) an activating light generator adapted to generate and direct activating light toward at least one of the first and second mold members during use, (e) a controller for controlling the intensity of light directed by the light generator, (f) a light sensor adapted to measure the intensity of light directed by the activating light generator, the light sensor being adapted to signal the light generator to vary the intensity of the activatmg light being produced, and (g) a filter adapted to inhibit light other than activating light from impinging upon the light sensor.

In an alternate embodiment, a system for making an eyeglass lens may include (a) a first mold member having a casting face and a non-casting face, (b) a second mold member having a casting face and a non-casting face, the second mold member being spaced apart from the first mold member during use such that the casting faces of the first mold member and the second mold member at least partially define a mold cavity for a lens forming composition, (c) an activating light generator adapted to generate and direct activating light toward at least one of the first and second mold members during use, (d) a distributor adapted to direct air toward the non- casting face of at least one of the mold members, (e) a thermoelectric cooling system adapted to cool the air, and (f) a first blower adapted to receive effluent air that has contacted the non-casting face of the mold member and to recycle the effluent air to the distributor.

In an embodiment, an eyeglass lens may be made by (a) placing a liquid, polymerizable lens forming composition in a mold cavity defined at least partially by a first mold member and a second mold member, the lens forming composition comprising a photoinitiator; (b) directing a plurality of pulses of activating light toward the lens forming composition through at least one of the mold members to initiate reaction of the lens forming composition, at least one of the pulses having an intensity of at least about 10 milliwatts/cm2; (c) subsequent to the step of directing the plurality of pulses toward the lens forming composition, directing activating light of a second intensity toward the lens forming composition through at least one of the mold members to form a substantially clear eyeglass lens, the second intensity being less than about 350 microwatts/cm2; and (d) substantially simultaneously with the step of directing activating light of a second intensity toward the lens forming composition, directing air onto a non-casting face of at least one of the mold members to remove heat from the lens forming composition.

A lens having a scratch resistant coating may be formed by: placing a first coating composition within a mold member, the mold member comprising a casting face and a non-casting face, the coating composition comprising a photoinitiator and being curable upon exposure to activating light; (a) placing a first coating composition within a mold member, the mold member comprising a casting face and a non-casting face, the coating composition comprising a photoinitiator and being curable upon exposure to activating light; (b) spinning the mold member to distribute the first coating composition over the casting face; (c) directing activating light at the mold member to cure at least a portion of the first coating composition; (d) placing a second coating composition within the mold member, the second coating composition comprising a photoinitiator and being curable upon exposure to activating light; (e) spinning the mold member to distribute the second coating composition over the portion of the first coating composition that has been cured; (f) directing activating light at the mold member, thereby curing at least a portion of the second coating composition and forming a substantially clear combination coat comprising at least a portion of each of the first and second coating compositions; (g) assembling the mold member with a second mold member to form a mold having a cavity between the mold members; (h) placing a lens-forming composition within the cavity, the lens- forming composition comprising a photoinitiator and being curable upon exposure to activating light; and (i) directing activating light at the mold to cure at least a portion of the lens-forming material to form a lens, and wherein the combination coat adheres to the cured portion of the lens-forming material.

In an embodiment, a lens forming composition containing the following components may be used to cure an eyeglass lens that does not transmit a potion of activating light. The composition preferably comprises (a) a monomer capable of being cured to form an eyeglass lens, (b) an activating light absorbing compound for inhibiting at least a portion of activating light from being transmitted through the eyeglass lens, (c) a co-initiator adapted to activate curing of the monomer to form the eyeglass lens, and (d) a photoinitiator adapted to activate the co-initiator in response to being exposed to activating light.

In another embodiment, a lens forming composition containing the following components may be used to cure an eyeglass lens that does not transmit a potion of activating light. The composition preferably comprises (a) a monomer capable of being cured to form an eyeglass lens, (b) an activating light absorbing compound for inhibiting at least a portion of activating light from being transmitted through the eyeglass lens, and (c) a photoinitiator adapted to activate curing of the monomer to form the eyeglass lens. The monomer may be cured by treatment with activating light. The activating light preferably includes light having a wavelength substantially greater than about 380 nm.

In an embodiment, the conditions whereby a lens is formed from a lens forming composition may be altered such that the formed lens has a power substantially different from the targeted power of the lens. The peak temperature of the composition may be preferably altered such that lenses formed at elevated peak temperatures may have a lens power lower than targeted from the shape of the mold cavity. Alternatively, the time at which the lenses are removed from the lens forming mold may be altered such that lenses that are released at an earlier time from the mold may have a power substantially greater than targeted from the shape of the mold cavity.

In an embodiment, the lens forming process may be controlled using a microprocessor based controller. The controller preferably monitors the response of the lens forming composition to a pulse of activating light. The controller preferably measures the temperature and the rate of temperature change during the process. While the lens is no longer being irradiated with activating light, the controller preferably monitors the temperature curves and performs a mathematical analysis of the temperature curve profile. Dosages of activating light, based on the response of the composition to the last activating light applied, may be determined and applied. This process may be repeated until the lens is substantially cured.

BRIEF DESCRIPTION OF THE DRAWINGS

The above brief description as well as further objects, features and advantages of the methods and apparatus of the present invention will be more fully appreciated by reference to the following detailed description of presently preferred but nonetheless illustrative embodiments in accordance with the present invention when taken in conjunction with the accompanying drawings in which:

Fig. 1 is a perspective view of an apparatus for producing a plastic lens. Fig. 2 is a cross-sectional view of the apparatus taken along line 2-2 of Fig. 1.

Fig. 3 is a cross-sectional view of the apparatus taken along line 3-3 of Fig. 2.

Fig. 4 is a detail view of a component of the apparatus.

Fig. 5 is a detail view of a component of the apparatus. Fig. 6 is a cross-sectional view of a lens cell for use in an apparatus of the invention.

Fig. 7 is a view of an embodiment of a shutter system.

Fig. 8 is a top and side view of an embodiment of a heat distributor to be placed between a heat source and a mold surface.

Fig. 9 is a schematic block diagram of an alternate process and system for making and postcuring a plastic lens.

Fig. 10 is a schematic diagram of an apparatus to apply activatmg light to a lens or mold assembly.

Fig. 11 is a view of an embodiment of a lens.

Fig. 12 is a view of an embodiment of an oxygen barrier with photoinitiator.

Fig. 13 is a schematic diagram of a lens curing apparatus with a light sensor and controller. Fig. 14 is a schematic view of the front of a lens curing apparatus.

Fig. 15 is a schematic view of the side of a lens curing apparatus.

Fig. 16 is a view of an embodiment of a heat source and a heat distributor.

Fig. 17 is a view of various embodiments of a heat source and heat distributors.

Fig. 18 is a view of an embodiment of a heat source and a heat distributor. Fig. 19 is a view of an embodiment of two mold members and a gasket.

Fig. 20 is a graph illustrating a temperature profile of a continuous radiation cycle.

Fig. 21 is a graph illustrating temperature profiles for a continuous irradiation cycle and a pulse irradiation cycle employed with a mold gasket set having a 3.00D base curve, and while applying cooled air at 58 ° F to the mold/gasket set. Fig. 22 is a chart illustrating qualitative relationships among curing cycle variables.

Fig. 23 is a graph illustrating temperature profiles for one curing cycle for a mold/gasket set having a 6.00D base curve and used with three different light levels.

Fig. 24 is a graph illustrating continuous and pulsed temperature profiles for a curing cycle employing a mold/gasket set with a 6.00D base curve. Fig. 25 is a graph illustrating continuous and pulsed temperature profiles for a curing cycle employing a mold/gasket set with a 4.50D base curve.

Fig. 26 is a graph illustrating contmuous and pulsed temperature profiles for a curing cycle employing a mold/gasket set with a 3.00D base curve.

Fig. 27 is a view of an embodiment of a system simultaneously employing both a flash light source and a continuous activating (e.g., fluorescent) source.

Fig. 28 is an embodiment of a system simultaneously employing two flash light sources.

Fig. 29 is an embodiment of a system employing an ultraviolet light controller.

Fig. 30 depicts a schematic view of a lens curing apparatus. Fig. 31 depicts a detail view of a thermoelectric cooling system.

Fig. 32 depicts a cross sectional view of a thermoelectric cooling system.

Fig. 33 depicts a thermoelectric module.

Fig. 34 depicts a flash lamp curing cycle. Fig. 35 depicts a cross sectional view of a flat-top bifocal mold.

Fig. 36 depicts a cross sectional view of a filter disposed directly adjacent to a mold member.

Fig. 37 depicts a plot of % transmittance of light versus wavelength for a photochromic lens.

Fig. 38 depicts a plot of % transmittance of light versus wavelength for both a colorless lens containing ultraviolet absorbers and a lens containing no ultraviolet absorbers. Fig. 39 depicts a plot of % transmittance of light versus wavelength for a colored lens containing fixed pigments.

Fig. 40 depicts a plot of the temperature of the lens forming composition versus time during the application of activating light pulses.

DESCRIPTION OF A PREFERRED EMBODIMENTS

Apparatus, operating procedures, equipment, systems, methods, and compositions for lens curing using ultraviolet light are available from Rapid Cast, Inc., Q2100, Inc., and Fast Cast, Inc. in Louisville, Kentucky. The Fast Cast, Inc. publication entitled "Operation Manual For The FastCast LenSystem" is hereby incorporated by reference.

Referring now to Fig. 1, a plastic lens curing chamber of the present invention is generally indicated by reference numeral 10. The lens curing chamber 10 preferably communicates through a plurality of pipes 12 with an air source (not shown), the purpose of which will be discussed below.

As shown in Fig. 2, the plastic lens curing chamber 10 may include an upper lamp chamber 14, an irradiation chamber 16, and a lower lamp chamber 18. The upper lamp chamber 14 may be separated from the irradiation chamber 16 by a plate 20. The lower lamp chamber may be separated from the irradiation chamber 16 by a plate 22. The upper lamp chamber 14, the irradiation chamber 16, and the lower lamp chamber 18 may be isolated from ambient air by upper lamp chamber doors 24, irradiation chamber doors 26, and lower lamp chamber doors 28, respectively. While the upper lamp chamber doors 24, the irradiation chamber doors 26 and the lower lamp chamber doors 28 are shown in Fig. 1 as including two corresponding door members, those of ordinary skill in the art will recognize that the doors 24, 26 and 28 may include single or multiple door members. The upper lamp chamber doors 24, the irradiation chamber doors 26 and the lower lamp chamber doors 28 may be slidingly mounted in guides 30. As shown in Fig. 2, vents 32 may communicate with upper lamp chamber 14 and lower lamp chamber 18 by way of corresponding vent chambers 34 and openings 36 disposed in plate 20 and plate 22. Each vent 32 may be shielded by a vent cover 38.

As shown in Fig. 3, vents 33 may be disposed in the irradiation chamber doors 26 and communicate with irradiation chamber 16. Each vent 33 may be shielded by a vent cover 35.

As shown in Figs. 2 and 3, a plurality of light generating devices or lamps 40 may be disposed within each of upper lamp chamber 14 and lower lamp chamber 18. Preferably, upper lamp chamber 14 and lower lamp chamber 18 each include three lamps 40 that are arranged in a triangular fashion in which the lamps 40 in the upper lamp chamber 14 are disposed with the point of the triangle pointing upwards whereas the lamps 40 in the lower lamp chamber 18 are disposed with the point of the triangle pointing downward. The lamps 40 preferably generate activating light. As used herein "activating light" means light that may affect a chemical change. Activating light may include ultraviolet light, visible light or infrared light. Generally, any wavelength of light capable of affecting a chemical change may be classified as activating. Chemical changes may be manifested in a number of forms. A chemical change may include, but is not limited to, any chemical reaction which causes a polymerization to take place. Preferably the chemical change causes the formation of an initiator species within the lens forming composition, the initiator species being capable of initiating a chemical polymerization reaction. The lamps 40, in one embodiment, generate ultraviolet light having a wavelength in the range of at least approximately 300 nm to 400 nm since the effective wavelength spectrum for curing the lens forming material lies in the 300 nm to 400 nm region. The lamps 40 may be supported by and electrically connected to suitable fixtures 42. An exhaust fan 44 may communicate with upper lamp chamber 14 while an exhaust fan 46 may communicate with lower lamp chamber 18.

As noted above, the upper lamp chamber 14 may be separated from the irradiation chamber 16 by plate 20. Similarly, lower lamp chamber 18 may be separated from the irradiation chamber 16 by plate 22. The plates 20 and 22 may mclude apertures 48 and 50, respectively, through which the light generated by lamps 40 may be directed so as to impinge upon a lens cell 52 (shown in phantom in Fig. 2). The diameter of the lens cell 52 is preferably approximately 74 mm. The apertures 48 and 50 preferably range from about 70 mm to about 140 mm.

In one embodiment an upper light filter 54 rests upon plate 20 while a lower light filter 56 rests upon plate 22 or is supported by brackets 57. The upper light filter 54 and lower light filter 56 are shown in Fig. 2 as being made of a single filter member, however, those of ordinary skill in the art will recognize that each of the upper light filter 54 and lower light filter 56 may include two or more filter members. The components of upper light filter 54 and lower light filter 56 preferably are modified depending upon the characteristics of the lens to be molded. For instance, in a preferred embodiment for making negative lenses, the upper light filter 54 includes a plate of Pyrex glass that is frosted on both sides resting upon a plate of clear Pyrex glass. The lower light filter 56 includes a plate of Pyrex glass frosted on one side resting upon a plate of clear Pyrex glass with a device for reducing the intensity of activating light incident upon the center portion in relation to the edge portion of the lens being disposed between the plate of frosted Pyrex and the plate of clear Pyrex glass.

Conversely, in a preferred arrangement for producing positive lenses, the upper light filter 54 includes a plate of Pyrex glass frosted on one or both sides and a plate of clear Pyrex glass resting upon the plate of frosted Pyrex glass with a device for reducing the intensity of activating light incident upon the edge portion in relation to the center portion of the lens being disposed between the plate of clear Pyrex glass and the plate of frosted Pyrex glass. The lower light filter 56 includes a plate of clear Pyrex glass frosted on one side resting upon a plate of clear Pyrex glass with a device for reducing the intensity of activating light incident upon the edge portion m relation to the center portion of the lens bemg disposed between the plates of clear Pyrex glass In this arrangement, in place of a device for reducmg the relative intensity of activatmg light mcident upon the edge portion of the lens, the diameter of the aperture 50 can be reduced to achieve the same result, 1 e to reduce the relative intensity of activatmg light incident upon the edge portion of the lens It will be apparent to those skilled in the art that each filter 54 or 56 could be composed of a plurality of filter members or include any other means or device effective to reduce the light to its desired intensity, to diffuse the light and/or to create a light intensity gradient across the lens cell 52 Alternately, in certain embodiments no filter elements may be used

Preferably, the upper light filter 54 or the lower light filter 56 each mclude at least one plate of Pyrex glass havmg at least one frosted surface Also, either or both of the upper light filter 54 and the lower light filter 56 may mclude more than one plate of Pyrex glass each frosted on one or both surfaces, and/or one or more sheets of tracing paper After passmg through frosted Pyrex glass, the activating light is believed to have no sharp intensity discontinuities which is believed to lead to a reduction in optical distortions m the finished lens m some mstances Those of ordinary skill m the art will recognize that other means may be used to diffuse the activatmg light so that it has no sharp intensity discontinuities

Preferably disposed within the irradiation chamber 16 are a left stage 58, a center stage 60, and a πght stage 62, each of which preferably mcludes a plurality of steps 64 The left stage 58 and center stage 60 define a left irradiation chamber 66 while the right stage 62 and center stage 60 define a πght irradiation chamber 68 A cell holder 70, shown in phantom m Fig 2 and m detail in Fig 4, may be disposed within each of left irradiation chamber 66 and right irradiation chamber 68 The cell holder 70 may mclude a peπpheral step 72 that is designed to allow a cell holder 70 to be supported upon complementary steps 64 of left stage 58 and center stage 60, and center stage 60 and right stage 62, respectively As shown m Fig 4, each cell holder 70 also may mclude a central bore 74 to allow the passage therethrough of activatmg light from the lamps 40 and an annular step 76 which is designed to support a lens cell 52 m a manner descπbed below As shown in Fig 6, each lens cell 52 may mclude opposed mold members 78, separated by an annular gasket 80 to define a lens molding cavity 82 The opposed mold members 78 and the annular gasket 80 may be shaped and selected m a manner to produce a lens havmg a desired diopter

The mold members 78 are preferably formed of any suitable material that will permit rays of activating light to pass therethrough The mold members 78 are preferably formed of glass Each mold member 78 has an outer peπpheral surface 84 and a pair of opposed surfaces 86 and 88 with the surfaces 86 and 88 bemg precision ground Preferably the mold members 78 have desirable activatmg light transmission characteπstics and both the castmg surface 86 and non-castmg surface 88 preferably have no surface aberrations, waves, scratches or other defects as these may be reproduced m the finished lens

As noted above, the mold members 78 are adapted to be held m spaced apart relation to define a lens moldmg cavity 82 between the facmg surfaces 86 thereof The mold members 78 are preferably held m a spaced apart relation by a T-shaped flexible annular gasket 80 that seals the lens moldmg cavity 82 from the exterior of the mold members 78 In use, the gasket 80 may be supported on the annular step 76 of the cell holder 70 In this manner, the upper or back mold member 90 has a convex inner surface 86 while the lower or front mold member 92 has a concave inner surface 86 so that the resulting lens moldmg cavity 82 is shaped to form a lens with a desired configuration Thus, by selectmg the mold members 78 with a desired surface 86, lenses with different characteπstics, such as focal lengths, may be made by the apparatus 10 Rays of activatmg light emanating from lamps 40 pass through the mold members 78 and act on a lens formmg material disposed m the mold cavity 82 in a manner discussed below so as to form a lens As noted above, the rays of activatmg light may pass through a suitable filter 54 or 56 to impmge upon the lens cell 52

The mold members 78, preferably, are formed from a material that will not allow activatmg light radiation havmg a wavelength below approximately 300 nm to pass therethrough Suitable materials are Schott Crown, S-l or S-3 glass manufactured and sold by Schott Optical Glass Ine , of Duryea, Pennsylvania or

Corning 8092 glass sold by Corning Glass of Corning, New York A source of flat-top or smgle vision molds may be Augen Lens Co in San Diego, California

The annular gasket 80 may be formed of vinyl material that exhibits good lip finish and mamtams sufficient flexibility at conditions throughout the lens curing process In a preferred embodiment, the annular gasket 80 is formed of silicone rubber material such as GE SE6035 which is commercially available from

General Electπc In another preferred embodiment, the annular gasket 80 is formed of copolymers of ethylene and vmyl acetate which are commercially available from E I DuPont de Nemours & Co under the trade name ELVAX7 Preferred ELVAX7 resins are ELVAX7 350 havmg a melt index of 17 3-20 9 dg/mm and a vmyl acetate content of 24 3-25 7 wt %, ELVAX7 250 havmg a melt mdex of 22 0-28 0 dg/mm and a vmyl acetate content of 27 2-28 8 wt %, ELVAX7 240 havmg a melt mdex of 38 0-48 0 dg/mm and a vmyl acetate content of 27 2-28 8 wt %, and ELVAX7 150 havmg a melt mdex of 38 0-48 0 dg/mm and a vmyl acetate content of 32 0-34 0 wt % Regardless of the particular mateπal, the gaskets 80 may be prepared by conventional injection moldmg or compression moldmg techniques which are well-known by those of ordinary skill m the art As shown m phantom m Fig 2, in section in Fig 3, and m detail in Fig 5, an upper and lower air distribution device 94 is disposed in each of left irradiation chamber 66 and right irradiation chamber 68 Each air distπbunon device 94 is connected to a pipe 12 As shown m Fig 5, each air distribution device 94 includes a plenum portion 95 and a substantially cylindrical opening 96 having oπfices 98 disposed therein to allow for the expulsion of air from the air distribution device 94 The diameter of the oπfices 98 may be constant, or may vary around the circumference of cylindrical openmg 96 preferably reachmg a maximum when directly opposite the plenum portion 95 of air distribution device 94 and preferably reachmg a minimum immediately adjacent the plenum portion 95 In addition, the oπfices 98 are designed to blow air toward a lens cell 52 that may be disposed m a lens cell holder 70 and installed m left irradiation chamber 66 or right irradiation chamber 68 In operation, the apparatus of the present mvention may be appropriately configured for the production of positive lenses which are relatively thick at the center or negative lenses which are relatively thick at the edge To reduce the likelihood of premature release, the relatively thick portions of a lens preferably are polymerized at a faster rate than the relatively thm portions of a lens The rate of polymerization taking place at various portions of a lens may be controlled by varying the relative intensity of activating light incident upon particular portions of a lens. The rate of polymerization taking place at various portions of a lens may also be controlled by directing air across the mold members 78 to cool the lens cell 52. For positive lenses the intensity of incident activating light is preferably reduced at the edge portion of the lens so that the thicker center portion of the lens polymerizes faster than the thinner edge portion of the lens. Conversely, for a negative lens, the intensity of incident activating light is preferably reduced at the center portion of the lens so that the thicker edge portion of the lens polymerizes faster than the thinner center portion of the lens. For either a positive lens or a negative lens, air may be directed across the faces of the mold members 78 to cool the lens cell 52. As the overall intensity of incident activating light is increased, more cooling is needed which can be accomplished by either or both of increasing the velocity of the air and reducing the temperature of the air.

It is well known by those of ordinary skill in the art that lens forming materials having utility in the present invention tend to shrink as they cure. If the relatively thin portion of a lens is allowed to polymerize before the relatively thick portion, the relatively thin portion will tend to be rigid at the time the relatively thick portion cures and shrinks and the lens will either release prematurely from or crack the mold members 78. Accordingly, when the relative intensity of activating light incident upon the edge portion of a positive lens is reduced relative to the center portion, the center portion polymerizes faster and shrinks before the edge portion is rigid so that the shrinkage is more uniform. Conversely, when the relative intensity of activating light incident upon the center portion of a negative lens is reduced relative to the edge portion, the edge portion polymerizes faster and shrinks before the center becomes rigid so that the shrinkage is more uniform.

The variation of the relative intensity of activating light incident upon a lens may be accomplished in a variety of ways. According to one method, in the case of a positive lens, a ring of opaque material may be placed between the lamps 40 and the lens cell 52 so that the incident activating light falls mainly on the thicker center portion of the lens. Conversely, for a negative lens, a disk of opaque material may be placed between the lamps 40 and the lens cell 52 so that the incident activating light falls mainly on the edge portion of the lens.

According to another method, in the case of a negative lens, a sheet material having a variable degree of opacity ranging from opaque at a central portion to transparent at a radial outer portion is disposed between the lamps 40 and the lens cell 52. Conversely, for a positive lens, a sheet material having a variable degree of opacity ranging from transparent at a central portion to opaque at a radial outer portion is disposed between the lamps 40 and the lens cell 52.

Those of ordinary skill in the art will recognize that there are a wide variety of techniques other than those enumerated above for varying the intensity of the activating light incident upon the opposed mold members 78. In some embodiments, the intensity of the incident light has been measured and determined to be approximately 3.0 to 5.0 milliwatts per square centimeter (mW/cm2) prior to passing through either the upper light filter 54 or the lower light filter 56 and the total intensity at the thickest part of the lens ranges from 0.6 to 2.0 mW/cm2 while the intensity at the thinnest portion of the lens ranges from 0.1 to 1.5 mW/cm2. In some embodiments the overall light intensity incident on the lens cell 52 has less of an impact on the final product than the relative light intensity incident upon the thick or thin portions of the lens so long as the lens cell 52 is sufficiently cooled to reduce the polymerization rate to an acceptable level.

In addition, as described below, in certain embodiments heat may be conductively applied to the molds and/or lens, thereby enhancing the quality of the cured lenses.

The activating light lamps 40 preferably are maintained at a temperature at which the lamps 40 deliver maximum output. The lamps 40, preferably, are cooled because the intensity of the light produced by the lamps 40 fluctuates when the lamps 40 are allowed to overheat. In the apparatus depicted in Fig. 2, the cooling of the lamps 40 is accomplished by sucking ambient air into the upper lamp chamber 14 and lower lamp chamber 18 through vent 32, vent chambers 34 and openings 36 by means of exhaust fans 44 and 46, respectively.

Excessive cooling of the lamps 40 should be avoided, however, as the intensity of the light produced by the lamps 40 is reduced when the lamps 40 are cooled to an excessive degree.

As noted above, the lens cell 52 is preferably cooled during curing of the lens forming material as the overall intensity of the incident activating light is increased. Cooling of the lens cell 52 generally reduces the likelihood of premature release by slowing the reaction and improving adhesion. There are also improvements in the optical quality, stress characteristics and impact resistance of the lens. Cooling of the lens cell 52 is preferably accomplished by blowing air across the lens cell 52. The air preferably has a temperature ranging between 15 and 85°F (about -9.4°C to 29.4°C) to allow for a curing time of between 30 and 10 minutes. The air distribution devices 94 depicted in Fig. 5 have been found to be particularly advantageous as they are specifically designed to direct air directly across the surface of the opposed mold members 78. After passing across the surface of the opposed mold members 78, the air emanating from the air distribution devices 94 is vented through vents 33. Alternately the air emanating from the air distribution devices 94 may be recycled back to an air cooler.

The lens cell 52 may also be cooled by disposing the lens cell in a liquid cooling bath. The opposed mold members 78 are preferably thoroughly cleaned between each curing run as any dirt or other impurity on the mold members 78 may cause premature release. The mold members 78 are cleaned by any conventional means well known to those of ordinary skill in the art such as with a domestic cleaning product, i.e., Mr. Clean™ available from Proctor and Gamble. Those of ordinary skill in the art will recognize, however, that many other techniques may also be used for cleaning the mold members 78. Yellowing of the finished lens may be related to the monomer composition, the identity of the photoinitiator, and the concentration of the photoinitiator.

When casting a lens, particularly a positive lens that is thick in the center, cracking may be a problem. Addition polymerization reactions, including photochemical addition polymerization reactions, are exothermic. During the process, a large temperature gradient may build up and the resulting stress may cause the lens to crack.

The formation of optical distortions usually occurs during the early stages of the polymerization reaction during the transformation of the lens forming composition from the liquid to the gel state. Once patterns leading to optical distortions form they are difficult to eliminate. When gelation occurs there typically is a rapid temperature rise The exothermic polymerization step causes a temperature mcrease, which m turn causes an increase m the rate of polymerization, which causes a further mcrease m temperature If the heat exchange with the surroundings is not sufficient enough there will be a runaway situation that leads to premature release, the appearance of thermally caused stπations and even breakage Accordmgly, when contmuous activating light is applied, it is preferred that the reaction process be smooth and not too fast but not too slow Heat is preferably not generated by the process so fast that it cannot be exchanged with the surroundings The incident activatmg light intensity preferably is adjusted to allow the reaction to proceed at a desired rate It is also preferred that the seal between the annular gasket 80 and the opposed mold members 78 be as complete as possible Factors that have been found to lead to the production of lenses that are free from optical distortions are (1) achievmg a good seal between the annular gasket 80 and the opposed mold members 78, (2) using mold members 78 having surfaces that are free from defects, (3) usmg a formulation having an appropnate type and concentration of photomitiator that will produce a reasonable rate of temperature rise, and (4) usmg a homogeneous formulation Preferably, these conditions are optimized Premature release of the lens from the mold will result in an incompletely cured lens and the production of lens defects Factors that contribute to premature release are (1) a poorly assembled lens cell 52, (2) the presence of air bubbles around the sample edges, (3) imperfection m gasket lip or mold edge, (4) mappropriate formulation, (5) uncontrolled temperature rise, and (6) high or nonumform shrinkage Preferably, these conditions are minimized Premature release may also occur when the opposed mold members 78 are held too rigidly by the armular gasket 80 Preferably, there is sufficient flexibility m the annular gasket 80 to permit the opposed mold members 78 to follow the lens as it shrinks Indeed, the lens must be allowed to shrink m diameter slightly as well as m thickness The use of an annular gasket 80 that has a reduced degree of stickiness with the lens durmg and after curmg is therefore desirable In a preferred technique for filling the lens moldmg cavity 82, the annular gasket 80 is placed on a concave or front mold member 92 and a convex or back mold member 90 is moved mto place The annular gasket 80 is then pulled away from the edge of the back mold member 90 at the uppermost pomt and a lens formmg composition is injected mto the lens moldmg cavity 82 until a small amount of the lens formmg composition is forced out around the edge The excess is then removed, preferably, by vacuum Excess liquid that is not removed could spill over the face of the back mold member 90 and cause optical distortion m the finished lens

Despite the above problems, the advantages offered by d e radiation cured lens moldmg system clearly outweigh the disadvantages The advantages of a radiation cured system mclude a significant reduction m energy requirements, curmg time and other problems normally associated with conventional thermal systems The lens formmg material may mclude any suitable liquid monomer or monomer mixture and any suitable photosensitive initiator As used herem "monomer" is taken to mean any compound capable of undergomg a polymerization reaction Monomers may mclude non-polymerized material or partially polymerized material When partially polymerized matenal is used as a monomer, the partially polymerized material preferably contains functional groups capable of undergomg further reaction to form a new polymer The lens formmg material, preferably, does not include any component, other than a photomitiator, that absorbs activatmg light havmg a wavelength m the range of 300 to 400 nm The liquid lens forming matenal is preferably filtered for quality control and placed in the lens moldmg cavity 82 by pulling the annular gasket 80 away from one of the opposed mold members 78 and mjectmg the liquid lens formmg material mto the lens moldmg cavity 82 Once the lens molding cavity 82 is filled with such material, the annular gasket 80 is replaced mto its sealmg relation with the opposed mold members 78

Those skilled in the art will recognize that once the cured lens is removed from the lens molding cavity 82 by disassembling the opposed mold members 78, the lens can be further processed m a conventional manner, such as by grmdmg its peripheral edge

According to the present invention a polymerizable lens formmg composition includes an aromatic-contammg bιs(allyl carbonate)-functιonal monomer and at least one polyethylenic-functional monomer contammg two ethylenically unsaturated groups selected from acrylyl and methacrylyl In a preferred embodiment, the composition further includes a suitable photomitiator In other prefened embodiments, the composition may mclude one or more polyethylenic-functional monomers contammg three ethylenically unsaturated groups selected from acrylyl and methacrylyl, and a dye

Aromatic-contammg bιs(allyl carbonate)-functιonal monomers which can be utilized m the practice of the present mvention are bιs(allyl carbonates) of dihydroxy aromatic-contammg matenal The dihydroxy aromatic-contammg material from which me monomer is derived may be one or more dihydroxy aromatic-contammg compounds Preferably the hydroxyl groups are attached directly to nuclear aromatic carbon atoms of the dihydroxy aromatic-contammg compounds The monomers are themselves known and can be prepared by procedures well known m the art

The aromatic-contammg bιs(allyl carbonate)-functιonal monomers can be represented by the formula

m which A, is the divalent radical derived from the dihydroxy aromatic-contammg material and each g is mdependently hydrogen, halo, or a C C4 alkyl group The alkyl group is usually methyl or ethyl Examples of Ro mclude hydrogen, chloro, bromo, fluoro, methyl, ethyl, n-propyl, isopropyl and n-butyl Most commonly o is hydrogen or methyl, hydrogen is preferred A subclass of the divalent radical A, which is of particular usefulness is represented by the formula:

in which each R, is independently alkyl containing from 1 to about 4 carbon atoms, phenyl, or halo; the average value of each a is independently in the range of from 0 to 4; each Q is independently oxy, sulfonyl, alkanediyl having from 2 to about 4 carbon atoms, or alkylidene having from 1 to about 4 carbon atoms; and the average value of n is in the range of from 0 to about 3. Preferably Q is methylethylidene, viz., isopropylidene. Preferably the value of n is zero, in which case A, is represented by the formula:

in which each R„ each a, and Q are as discussed in respect of Formula II. Preferably the two free bonds are both in the ortho or para positions. The para positions are especially preferred.

The dihydroxy aromatic-containing compounds from which A, is derived may also be polyol-fiinctional chain extended compounds. Examples of such compounds include alkaline oxide extended bisphenok. Typically the alkaline oxide employed is ethylene oxide, propylene oxide, or mixtures thereof. By way of exemplification, when para, para-bisphenols are chain extended with ethylene oxide, the bivalent radical A, may often be represented by the formula:

where each R„ each a, and Q are as discussed in respect of Formula II, and the average values of j and k are each independently in the range of from about 1 to about 4. A preferred aromatic-contammg bιs(allyl carbonate)-functιonal monomer is represented by the formula

and is commonly known as bisphenol A bιs(allyl carbonate)

A wide variety of compounds may be used as the polyethylenic functional monomer containing two or three ethylenically unsaturated groups A preferred polyethylenic functional compounds contammg two or three ethylenically unsaturated groups may be generally descπbed as the acrylic acid esters and the methacrylic acid esters of aliphatic polyhydπc alcohols, such as, for example, the di- and tnacrylates and the di- and tπmethacrylates of ethylene glycol, triethylene glycol, tetraethylene glycol, tetramethylene glycol, glycidyl, diethyleneglycol, butyleneglycol, propyleneglycol, pentanediol, hexanediol, tnmethylolpropane, and tnpropyleneglycol Examples of specific suitable polyethylenic - functional monomers contammg two or three ethylenically unsaturated groups mclude tπmethylolpropanetπacrylate (TMPTA), tetraethylene glycol diacrylate (TTEGDA), tnpropylene glycol diacrylate (TRPGDA), 1,6 hexanedioldimethacrylate (HDDMA), and hexanedioldiacrylate (HDD A)

In general, a photomitiator for initiating the polymerization of the lens formmg composition of the present invention, preferably, exhibits an activatmg light absorption spectrum over the 300-400 nm range High absorptivity of a photomitiator m this range, however, is not desirable, especially when castmg a thick lens

The following are examples of illustrative photomitiator compounds within the scope of the invention methyl benzoylformate, 2-hydroxy-2-methyl-l-phenylpropan-l-one, 1-hydroxycyclohexyl phenyl ketone, 2,2-dι-sec- butoxyacetophenone, 2,2-dιethoxyacetoρhenone, 2,2-dιethoxy-2-phenyl-acetophenone, 2,2-dιmethoxy-2- phenyl-acetophenone, benzoin methyl ether, benzoin lsobutyl ether, benzoin, benzil, benzyl disulfide, 2,4-dιhydroxybenzophenone, benzyhdeneacetophenone, benzophenone and acetophenone Preferred photomitiator compounds are 1-hydroxycyclohexyl phenyl ketone (which is commercially available from Ciba-Geigy as Irgacure 184), methyl benzoylformate (which is commercially available from Polysciences, Ine ), or mixtures thereof.

Methyl benzoylformate is a generally preferred photomitiator because it tends to provide a slower rate of polymerization The slower rate of polymerization tends to prevent excessive heat buildup (and resultant crackmg of the lens) during polymerization In addition, it is relatively easy to mix liquid methyl benzoylformate (which is liquid at ambient temperatures) with many acrylates, diacrylates, and allyl carbonate compounds to form a lens formmg composition The lenses produced with the methyl benzoylformate photomitiator tend to exhibit more favorable stress patterns and uniformity A strongly absorbmg photomitiator will absorb most of the mcident light m the first millimeter of lens thickness, causing rapid polymerization in that region. The remaining light will produce a much lower rate of polymerization below this depth and will result in a lens that has visible distortions. An ideal photoinitiator will exhibit high activity, but will have a lower extinction coefficient in the useful range. A lower extinction coefficient of photo initiators at longer wavelengths tends to allow the activating light radiation to penetrate deeper into the reaction system. This deeper penetration of the activating light radiation allows photoinitiator radicals to form uniformly throughout the sample and provide excellent overall cure. Since the sample can be irradiated from both top and bottom, a system in which appreciable light reaches the center of the thickest portion of the lens is preferred. The photoinitiator solubility and compatibility with the monomer system is also an important requirement. An additional consideration is the effect of the photoinitiator fragments in the finished polymer. Some photoinitiators generate fragments that impart a yellow color to the finished lens. Although such lenses actually absorb very little visible light, they are cosmetically undesirable.

Photoinitiators are often very system specific so that photoinitiators that are efficient in one system may function poorly in another. In addition, the initiator concentration to a large extent is dependent on the incident light intensity and the monomer composition. The identity of the initiator and its concentration are important for any particular formulation. A concentration of initiator that is too high tends to lead to cracking and yellowing of the lens. Concentrations of initiator tiiat are too low tend to lead to incomplete polymerization and a soft material.

Dyes and/or pigments are optional materials that may be present when high transmission of light is not necessary.

The listing of optional ingredients discussed above is by no means exhaustive. These and other ingredients may be employed in their customary amounts for their customary purposes so long as they do not seriously interfere with good polymer formulating practice.

According to a preferred embodiment of the present invention, a preferred aromatic-containing bis(allyl carbonate) functional monomer, bisphenol A bis(allyl carbonate) is admixed with one or more faster reacting polyethylenic functional monomers containing two aery late or methacrylate groups such as 1,6 hexanediol dimethacrylate (HDDMA), 1,6 hexanediol diacrylate (HDD A), tetraethylene glycol diacrylate (TTEGDA), and tripropylene glycol diacrylate (TRPGDA) and optionally a polyethylenic functional monomer containing three acrylate groups such as trimethylolpropane triacrylate (TMPTA). Generally, compounds containing acrylate groups polymerize much faster than those containing allyl groups.

In one embodiment, the lamps 40 generate an intensity at d e lamp surface of approximately 4.0 to 7.0 mW/cm2 of activating light having wavelengtiis between 300 and 400 nm, which light is very uniformly distributed without any sharp discontinuities throughout the reaction process. Such bulbs are commercially available from Sylvania under the trade designation Sylvania Fluorescent (F15T8/2052) or Sylvania Fluorescent (F15T8/350BL/18") GTE.

As noted above, activating light having wavelengths between 300 and 400 nm is preferred because the photoinitiators according to the present invention, preferably, absorb most efficiently at this wavelength and the mold members 78, preferably, allow maximum transmission at this wavelength. It is preferred that there be no sharp intensity gradients of activating light radiation either horizontally or vertically through the lens composition durmg the curmg process Sharp intensity gradients through the lens may lead to defects m the finished lens

Accordmg to one embodiment of the present mvention, the liquid lens formmg composition includes bisphenol A bιs(allyl carbonate) m place of DEG-BAC The bisphenol A bιs(allyl-carbonate) monomer has a higher refractive index than DEG-BAC which allows the production of thinner lenses which is important with relatively thick positive or negative lenses The bisphenol A bιs(allyl-carbonate) monomer is commercially available from PPG Industnes under the trade name HIRI I or CR-73 Lenses made from this product sometimes have a very slight, barely detectable, degree of yellowing A small amount of a blue dye consistmg of 9, 10-anthracenedιone, l-hydroxy-4-[(4-methylphenyl)ammo] available as Thermoplast Blue 684 from BASF Wyandotte Corp is preferably added to the composition to counteract the yellowing In addition, the yellowing tends to disappear if the lens is subjected to the above-descnbed post-cure heat treatment Moreover, if not post-cured the yellowing tends to disappear at ambient temperature after approximately 2 months

TTEGDA, available from Sartomer and Radcure, is a diacrylate monomer that, preferably, is included m the composition because it is a fast polymerizing monomer that reduces yellowing and yields a very clear product If too much TTEGDA is mcluded m the more preferred composition, I e greater than about 25% by weight, however, the finished lens may be prone to crackmg and may be too flexible as this matenal softens at temperatures above 40NC If TTEGDA is excluded altogether, the finished lens may to be bnttle

HDDMA, available from Sartomer, is a dimethacrylate monomer that has a very stiff backbone between the two methacrylate groups HDDMA, preferably, is included m the composition because it yields a stiffer polymer and mcreases the hardness and strength of the finished lens This material is quite compatible with the bisphenol A bιs(allyl carbonate) monomer HDDMA contributes to high temperature stiffness, polymer claπty and speed of polymerization

TRPGDA, available from Sartomer and Radcure, is a diacrylate monomer that, preferably, is mcluded m the composition because it provides good strength and hardness without adding bnttleness to the finished lens This material is also stiffer than TTEGDA

TMPTA, available from Sartomer and Radcure, is a tπacrylate monomer that, preferably, is included m the composition because it provides more crosslinking m the finished lens than the difunctional monomers TMPTA has a shorter backbone than TTEGDA and mcreases the high temperature stiffness and hardness of the finished lens Moreover, this material contributes to the prevention of optical distortions m the finished lens

TMPTA also contributes to high shrinkage durmg polymerization The inclusion of too much of this matenal m the more preferred composition may make the finished lens too bnttle

Certain of the monomers that are preferably utilized m the composition of the present mvention, such as TTEGDA, TRPGDA and TMPTA, mclude impunties and have a yellow color m certain of their commercially available forms The yellow color of these monomers is preferably reduced or removed by passing them through a column of alumina (basic) which mcludes aluminum oxide powder - basic After passage through the alumina column, the monomers absorb almost no activatmg light Also after passage through the alumina column differences between monomers obtamed from different sources are substantially eliminated. It is prefened, however, that the monomers be obtained from a source which provides the monomers with the least amount of impurities contained therein. The composition preferably is filtered prior to polymerization thereof to remove suspended particles.

The composition of the present invention, preferably, may be prepared according to the following protocol. Appropriate amounts of HDDMA, TTEGDA, TMPTA and TRPGDA are mixed and stirred thoroughly, preferably with a glass rod. The acrylate/methacrylate mixture may then be passed through a purification column.

A suitable purification column may be disposed within a glass column having a fitted glass disk above a teflon stopcock and having a top reservoir with a capacity of approximately 500 ml and a body with a diameter of 22 mm and a length of about 47 cm. The column may be prepared by placing on the fitted glass disk approximately 35 g. of activated alumina (basic), available from ALFA Products, Johnson Matthey, Danvers, MA in a 60 mesh form or from Aldrich in a 150 mesh form. Approximately 10 g. of an inhibitor remover (hydroquinone/methylester remover) available as HR-4 from Scientific Polymer Products, Inc., Ontario, NY then may be placed on top of the alumina and, finally, approximately 35 g. of activated alumina (basic) may be placed on top of the inhibitor remover.

Approximately 600 g. of the acrylate/methacrylate mixture may then be added above the column packing. An overpressure of 2-3 psi may then be applied to the top of the column resulting in a flow rate of approximately 30 to 38 grams per hour. Parafilm may be used to cover the junction of the column tip and the receiving bottle to prevent the infiltration of dust and water vapor. The acrylate/methacrylate mixture, preferably, may be received in a container that is opaque to activating light radiation.

An appropriate amount of bisphenol A bis(allyl carbonate) may then be added to the acrylate/methacrylate mixture to prepare the final monomer mixture.

An appropriate amount of a photoinitiator may then be added to the final monomer mixture. The final monomer mixture, with or without photoinitiator, may then be stored in a container that is opaque to activating light radiation.

An appropriate amount of a dye may also be added to the final monomer mixture, with or without photoinitiator.

After edging, the activating light cured lenses of the present invention demonstrate excellent organic solvent resistance to acetone, methylethyl ketone, and alcohols. For best results, both the casting surfaces 86 and non-casting surfaces 88 of the mold members 78 are finished to optical quality. For instance, a wave on the non-casting surface 88 may be reproduced in the finished lens as a result of the distortion of the incident light.

Mold markings cause differential light intensity conditions under the marking, even when the mark is on the non-casting surface 88 of the mold members 78. The fully exposed region of the lens will tend to be harder, and the lens may have stresses because of this. The portion of the lens under the mark will also tend to be weaker at the end of the curing period. This effect has been observed and may cause premature release or induce cracking.

Mold defects at the edges interfere with the sealing conditions and frequently induce premature release. It is believed that as the reaction proceeds, the heat generated tends to reduce the adhesion between the shrinking lens and the mold face. This reduction in adhesion tends to cause the lens to pull away from the mold. In high curvature (i.e. high power) lenses this problem tends to be even more pronounced because of two factors: (1) these lenses have more thickness and thus more material that is generating heat (which thus speeds up the reaction and generates more heat), and (2) these lenses have a greater thickness differential between the thick and thin portions of the lens, which tends to cause stress on the molds due to differential shrinkage. It is also possible that the temperatures generated relatively deep inside a thick lens may cause some vaporization of the monomer. The vaporized monomer may then migrate to the lens/mold interface, breaking the vacuum between the two. Because of the problem of premature release, preferably high power lenses are cured to maintain adhesion to the molds. Preferably the molds flex and accommodate stress.

Preferably the cooling fluid used is air at a temperature of less than 50°C. The fluid may be below 0°C, however in a prefened embodiment the fluid was at a temperature of between 0°C and less than 20°C, preferably about 0-15°C, more preferably about 0-10°C, more preferably still about 3-8°C. In one preferred embodiment the fluid temperature was about 5°C. As shown in Figure 9, a lens forming apparatus 300 for making a plastic lens may include a cooler 312 for supplying cool fluid to the apparatus 300 via conduit 314. The fluid may be supplied to the apparatus 300 and then discharged via conduit 320. The fluid discharged via conduit 320 may be vented via conduit 318 or it may alternately be recirculated via conduit 316 to the cooler 312. The cooler 312 preferably includes a Neslab CFT-50 water/antifreeze chiller (Newington, N.H., U.S.A.). A Neslab-built blower box designed for a minimum temperature of 3°C and 8 cubic feet (about 0.224 cubic meters) per minute of air per air distributor 94 was used with the chiller. The blower box included a heat exchanger coil through which chilled water was circulated, a blower, and a plenum-type arrangement for supplying air to the conduit 314.

If lenses are produced with continuous activating light without any mold cooling, the temperature of the mold-lens assembly may rise to above 50°C. Low diopter lenses may be prepared in this fashion, but higher plus or minus diopter lenses may fail. Certain lenses may be made by controlling (e.g., cooling) the temperature of the lens material during cure with circulating uncooled fluid (i.e., fluid at ambient temperatures). The ambient fluid in these systems is directed towards the mold members in the same manner as described above. Circulating ambient temperature fluid permits manufacture of a wider range of prescriptions than manufacture of the lenses without any mold cooling at all.

Most polymerization factors are intenelated. The ideal temperature of polymerization is related to the diopter and thickness of the lens being cast. Thermal mass is a factor. Lower temperatures (below about 10°C) are prefened to cast higher + or - diopter lenses when using continuous activating light. These lower temperatures tend to permit an increase in photoinitiator concentration, which in turn may speed up the reaction and lower curing time.

Preventing premature release when using continuous activating light is also somewhat dependent upon the flowrates of cooling fluid, as well as its temperature. For instance, if the temperature of the cooling fluid is decreased it may also be possible to decrease the flowrate of cooling fluid. Similarly, the disadvantages of a higher temperature cooling fluid may be somewhat offset by higher flowrates of cooling fluid.

In one embodiment the air flow rates for a dual distributor system (i.e., an air distributor above and below d e lens composition) are about 1-30 standard cubic feet ("scf ') (about 0.028 - 0.850 standard cubic meters) per minute per distributor, more preferably about 4-20 cubic feet (about 0.113-0.566 standard cubic meters) per minute per distributor, and more preferably still about 9-15 (about 0.255-0.423 standard cubic meters) cubic feet per minute per distributor. "Standard conditions," as used herein, means 60 °F (about 15.556°C) and one atmosphere pressure (about 101.325 kilopascals).

The thickness of the glass molds used to cast polymerized lenses may affect the lenses produced. A thinner mold tends to allow more efficient heat transfer between the polymerizing material and the cooling air, thus reducing the rate of premature release. In addition, a thinner mold tends to exhibit a greater propensity to flex. A thinner mold tends to flex during the relatively rapid differential shrinkage between die thick and thin portions of a polymerized lens, again reducing the incidence of premature release. In one embodiment the first or second mold members have a thickness less tiian about 5.0 mm, preferably about 1.0-5.0 mm, more preferably about 2.0-4.0 mm, and more still about 2.5-3.5 mm. "Front" mold or face means the mold or face whose surface ultimately forms the surface of an eyeglass lens that is furthest from the eye of an eyeglass lens wearer. "Back" mold or face means the mold or face whose surface ultimately forms the surface of an eyeglass lens that is closest to the eye of a eyeglass lens wearer.

In one embodiment the lens forming material is preferably cured to form a solid lens at relatively low temperatures, relatively low continuous activating light intensity, and relatively low photoinitiator concentrations. Lenses produced as such generally have a Shore D hardness of about 60-78 (for prefened compositions) when cured for about 15 minutes as described above. The hardness may be improved to about 80-81 Shore D by postcure heating the lens in a conventional oven for about 10 minutes, as described above. In a prefened embodiment, activating light may be provided with mercury vapor lamps provided in UVEXS, Inc. Model CCU or 912 curing chambers (Sunnyvale, CA, U.S.A.). In an alternate method for making a lens, the desired curvature (i.e., power) of the lens may be varied using the same molds, but with different light distributions. In this manner one mold may be used to prepare different lenses with different curvatures. The method includes the steps of: (1) placing a polymerizable lens forming material in a mold cavity defined in part between a first mold member and a second mold member, and wherein the cavity defines a theoretical curvature that is different from die desired curvature, (2) directing activating light rays towards at least one of the first and second mold members, and wherein the activating light rays are directed towards the first or second mold member such that the material cures to form a lens with the desired curvature, and (3) contacting fluid against the first or second mold member to cool the first or second mold member. The resulting lens curvature may vary depending on the way the activating light is directed towards the first or second mold members. That is, by varying the relative intensity of the light across the lens material radii, it is possible to vary the curvature of the resulting lens. EXAMPLE 1

Formulation: 17% Bisphenol A BisAllyl Carbonate

10% 1,6 Hexanediol dimefhacrylate

20% Trimethylolpropane triacrylate

21% Tetraethyleneglycol diacrlate

32% Tripropyleneglycol diacrlyate

0.012%) 1 Hydroxycyclohexyl phenyl ketone 0.048 Methylbenzoylformate

<10PPMHydroquinone & Metiiylethylhydroquinone

Hydroquinone and Methylethylhydroquinone were stabilizers present in some of the diacrylate and/or triacrylate compounds obtained from Sartomer. Preferably the amount of stabilizers is minimized since the stabilizers affect the rate and amount of curing. If larger amounts of stabilizers are added, then generally larger amounts of photoinitiators must also be added.

Light Condition: mW/cm2 measured at plane of sample with Specfroline DM 365N Meter from Spectionics Corp. (Westbury, N.Y.)

Center Edge

Top: 0.233 0.299

Bottom: 0.217 0.248

ir Flow: 9.6 standard cubic feet ("CFM") per manifold - 19.2 CFM total on sample

Air Temperature: 4.4 degrees Centigrade

Molds: 80 mm diameter Corning #8092 glass

Radius Thickness

Concave: 170.59 2.7

Convex: 62.17 5.4

Gasket: General Electric SE6035 silicone rubber with a 3 mm thick lateral lip dimension and a vertical lip dimension sufficient to provide an initial cavity center thickness of 2.2 mm.

Filling: The molds were cleaned and assembled into the gasket. The mold/gasket assembly was then temporarily positioned on a fixture which held the two molds pressed against the gasket lip with about 1 kg. of pressure. The upper edge of the gasket was peeled back to allow about 27.4 grams of the monomer blend to be charged into die cavity. The upper edge of the gasket was then eased back into place and d e excess monomer was vacuumed out with a small aspirating device. It is preferable to avoid having monomer drip onto the noncasting surface of the mold because a drop tends to cause the activating light to become locally focused and may cause an optical distortion in the final product.

Curing: The sample was irradiated for fifteen minutes under the above conditions and removed from the "FC-104" curing chamber (i.e., the chamber shown in Figures 14 and 15). The molds were separated from the cured lens by applying a sharp impact to the junction of the lens and the convex mold. The sample was then postcured at 110 °C in a conventional gravity type thermal oven for an additional ten minutes, removed and allowed to cool to room temperature.

Results: The resulting lens measured 72 mm in diameter, with a central thickness of 2.0 mm, and an edge thickness of 9.2 mm. The focusing power measured ~5.05 diopter. The lens was water clear ("water-white"), showed negligible haze, exhibited total visible light transmission of about 94%, and gave good overall optics. The Shore D hardness was about 80. The sample withstood the impact of a 1 inch steel ball dropped from fifty inches in accordance with ANSI 280.1-1987, 4.6.4 test procedures.

ADDITIONAL IMPROVEMENTS

POSTCURE WITH AN OXYGEN BARRIER ENRICHED WITH PHOTOINITIATOR

In certain applications, all of the lens forming composition may fail to completely cure by exposure to activating light rays when forming the lens. In particular, a portion of the lens forming composition proximate die gasket often remains in a liquid state following formation of the lens. It is believed that die gaskets are often somewhat permeable to air, and, as a result, oxygen permeates them and contacts die portions of the lens forming material that are proximate the gasket. Since oxygen tends to inhibit die photocuring process, portions of the lens forming composition proximate the gasket tend to remain uncured as the lens is formed.

Uncured lens forming composition proximate the gasket is a problem for several reasons. First, the liquid lens forming composition leaves the edges of the cured lens in a somewhat sticky state, which makes die lenses more difficult to handle. Second, the liquid lens forming composition is somewhat difficult to completely remove from the surface of the lens. Third, liquid lens forming composition may flow and at least partially coat the surface of lenses when such lenses are removed from the molds. This coating is difficult to remove and makes application of scratch resistant coatings or tinting dyes more difficult. This coating tends to interfere with the interaction of scratch resistant coatings and tinting dyes with d e cured lens surface. Fourth, if droplets of liquid lens forming material form, these droplets may later cure and form a ridge or bump on the surface of the lens, especially if the lens undergoes later postcure or scratch resistant coating processes. As a result of the above problems, often lenses must be tediously cleaned or recast when liquid lens forming composition remains after the lens is formed in an initial cure process.

The problems outlined above can be mitigated if less liquid lens forming composition remains proximate the gasket after the lens is formed. One method of lessening this "wet edge" problem relates to increasing the amount of photoinitiator present in the lens forming composition (i.e., increasing the amount of photoiniator in the lens forming composition above about 0.15 percent). Doing so, however, tends to create other problems. Specifically, increased photoinitiator levels tend to cause exothermic heat to be released at a relatively high rate during the reaction of the composition. Premature release and/or lens cracking tends to result. Thus it is believed tiiat lower amounts of photoinitiator are prefened.

The wet edge problem has been addressed by a variety of methods described in U.S. patent application serial number 07/931,946. Such methods relate to removing the gasket and applying eitiier an oxygen banier or a photoinitiator enriched liquid to the exposed edge of the lens. The lens is tiien re-irradiated with sufficient activating light to completely dry the edge of the lens prior to demolding.

An embodiment of the invention relates to improving the methods described in the 07/931,946 application. This embodiment relates to combining an oxygen barrier witii a photoinitiator. Specifically, in one embodiment an oxygen barrier 970 (e.g., a thin strip of polyethylene film or the like as shown in Fig. 12) is embedded or impregnated witii a photoinitiator 972. The oxygen barrier is then wrapped around the edge of a cured lens which is still encased between two molds (but with the gasket removed). While still "in die mold," the lens is then exposed to activating light, thereby drying its edge. An improvement of this memod over those previously disclosed is that there is a significant reduction in the activating dosage necessary to bring the lens edge to dryness. A plastic oxygen banier film which includes a photoinitiator may be made by: (a) immersing a plastic film in a solution comprising a photoinitiator, (b) removing the plastic film from the solution, and (c) drying the plastic film. The solution may include an etching agent. Preferably a surface of the plastic film is etched prior to or while immersing the plastic film in the solution.

In one example, thin strips (e.g., about 10 mm wide) of high density polyethylene film (approximately 0.013 mm thick) may be soaked in a solution of 97% acetone and 3% Irgacure 184 (a photoinitiator commercially available from Ciba Geigy located in Farmingdale, New Jersey) for about five minutes. The polyethylene film may be obtained from Tape Solutions, Inc. (Nashville, Tennessee). In a more prefened embodiment, 0.5% Byk 300 (a flow agent commercially available from Byk Chemie located in Wallingford, Connecticut) may be included in the soaking solution. It is believed that xylene in the Byk 300 tends to etch the surface of d e film and make the film more receptive to absorption of the Irgacure 184. In a still more prefened embodiment, the treated polyethylene strips may be dipped in acetone for about ten seconds to remove excess Irgacure 184. Excess photoinitiator may be seen as a white powder which coats the strips after drying. In either case, the strips are then allowed to air dry before applying them to the edge of die lens as described above. In one alternate embodiment of the invention, a plastic eyeglass lens may be made by the following steps: (1) placing a liquid polymerizable lens forming composition in a mold cavity defined by a gasket, a first mold member, and a second mold member; (2) directing first activating light rays toward at least one of die mold members to cure the lens forming composition so that it forms a lens with a back face, edges, and a front face, and wherein a portion of the lens forming composition proximate the edges of the lens is not fully cured; (3) removing the gasket to expose the edges of the lens; (4) applying an oxygen banier which includes a photoinitiator around the exposed edges of d e lens such that at least a portion of the oxygen barrier photoinitiator is proximate lens forming composition that is not fully cured; and (5) directing second activating light rays towards the lens such tiiat at least a portion of the oxygen banier photoinitiator initiates reaction of lens forming composition while the oxygen barrier substantially prevents oxygen from outside the oxygen barrier from contacting at least a portion of the lens forming composition. The first and second activating light rays may (a) be at the same or different wavelengths and/or intensities , (b) be continuous or pulsed, and (c) be from the same or different light source.

A purpose of the steps 4-5 is to reduce the amount of uncured liquid lens forming composition that is present when the lens is separated from the molds and/or gasket. It has been found that reducing the amount of liquid lens forming composition is especially advantageous if such reduction occurs before d e molds are separated from the cured lens. Separating the molds from d e cured lens may cause uncured liquids to at least partially coat the lens faces. This coating occurs because uncured liquid lens forming composition tends to get swept over the faces when the molds are separated from the lens. It is believed that curing of the lens tends to create a vacuum between the lens and the mold. Air may sweep over the mold faces to fill this vacuum when the molds are separated from the lens. This air tends to take liquid lens forming composition into the vacuum with it.

In step 4 above, an oxygen barrier which includes a photoinitiator is applied to the edges or sides of the lens after the gasket is removed. Preferably this oxygen barrier is applied while the lens are still attached to the molds. In an alternate embodiment tins oxygen barrier is also applied to the edges or sides of the molds at die same time it is applied to the sides of the lens. In a prefened embodiment, the sides of the lenses are first cleaned or wiped to remove at least a portion of the uncured liquid lens forming composition before the oxygen barrier is applied.

After the oxygen barrier is applied, second activating light rays are directed towards the lens. After the second activating light rays are directed toward die lens, at least a portion of the liquid lens forming composition which was not cured in die initial cure steps is cured. It is believed that die photoinitiator embedded in the oxygen barrier facilitates faster and more complete curing of the uncured lens forming composition. As such, less second activating light rays are employed, thereby lessening the time and energy required in this step. Furthermore, lens quality tends to be enhanced since a lower application of the second activating light rays tends to reduce the potential for lens yellowing.

In a prefened embodiment, substantially all of the remaining liquid lens forming composition is cured after the second activating light rays are directed toward the lens. More preferably, the lens is substantially dry after the second activating light rays are directed towards the lens. After the second activating light rays are directed toward the lens, the lens may en be demolded. The lens may then be tinted. After the lens is demolded, a scratch resistant coating may be applied to the lens. In one embodiment, a scratch resistant coating is applied to the demolded lens by applying a liquid scratch resistant coating composition to a face of the lens and then applying activating light rays to this face to cure the liquid scratch resistant coating to a solid.

In an embodiment, d e intensity of the activating light rays applied to die face of the lens to cure the liquid scratch resistant coating composition to a solid is about 150-300 mW/cm2 at a wave length range of about 360-370 nm, and about 50-150 mW/cm2 at a wave length range of about 250-260 nm. The lens may be heated after removal from the molds, or after application of a scratch resistant coating to the lens. In a prefened embodiment, the total mtensity of the first activating light rays directed toward the mold members is less than about 10 mW/cm2

In an embodiment, the intensity of the second activating light rays directed toward die lens is about 150-300 mW/cm2 at a wave length range of about 360-370 nm, and about 50-150 mW/cm2 at a wave length range of about 250-260 nm. Preferably the second activating light rays are directed towards the lens for less than about 1 minute.

In a prefened embodiment, the above method may further include die additional step of directing third activating light rays towards the lens before the oxygen barrier is applied. These tiiird activating light rays are preferably applied before the gasket is removed. Preferably, the second and third activating light rays are directed toward the back face of die lens (as stated above, the second and tiiird activating light rays are preferably applied while this lens is in the mold cavity). The third activating light rays are preferably about the same range of intensity as the second activating light rays. The same apparatus may be used for both the second and third activating light rays.

In a prefened embodiment, the metiiod described above also includes the step of removing the oxygen barrier from the edges of die lens. The second and third activating light rays may be repeatedly directed towards the lens. For instance, these activating light rays may be applied via a light assembly whereby the lens passes under a light source on a movable stand. The lens may be repeatedly passed under the lights. Repeated exposure of the lens to the activating light rays may be more beneficial than one prolonged exposure.

Preferably the oxygen barrier includes a film, and more preferably a plastic, flexible, and/or elastic film. In addition, the oxygen barrier is preferably at least partially transparent to activating light rays so tiiat activating light rays may penetrate the oxygen barrier to cure any remaining liquid lens forming composition. Preferably the oxygen barrier is stretchable and self-sealing. These features make the film easier to apply. Preferably the oxygen barrier is resistant to penetration by liquids, thus keeping any liquid lens forming composition in the mold assembly. Preferably, the oxygen banier includes a thermoplastic composition. It is anticipated that many different oxygen baniers may be used (e.g., saran wrap, polyethylene, etc.). In one prefened embodiment, the film is "Parafilm M Laboratory Film" which is available from American National Can (Greenwich, CT, U.S.A.). The oxygen barrier may also include aluminum foil.

Preferably the oxygen barrier is less than about 1.0 mm thick. More preferably the oxygen barrier is 0.01 to 0.10 mm thick, and more preferably still the oxygen barrier is less than 0.025 mm thick. If the oxygen barrier is too thick, then it may not be readily stretchable and/or conformable, and it may not allow a sufficient amount of light to pass through it. If the oxygen banier is too thin, then it may tend to tear.

An apparatus for applying a scratch resistant coating composition to a lens and then curing the scratch resistant coating composition is described in U.S. patents 4,895,102 to Kachel et al. and 3,494,326 to Upton (botii of which are incorporated herein by reference). In addition, the apparatus schematically shown in Figure 10 may also be used to apply the scratch resistant coating.

Figure 10 depicts an apparatus 600 with a first chamber 602 and a second chamber 604. This apparatus can be used to apply scratch resistant coating to a lens, to postcure a lens, or to apply activating light to a lens mold assembly. The first chamber 602 includes an opening 606 through which an operator can apply lenses and lens mold assemblies to the lens holder 608. Lens holder 608 is partially sunounded by barrier 614. First chamber 602 may include an inspection light 610, and an opening 618 in the floor of the chamber.

Lens holder 608 is attached to device 612. It is envisioned that device 612 may be a spinning device which would permit the apparatus 600 to be used to apply scratch resistant coatings to lenses. In such case device 612 would connect directly to lens holder 608 through a hole in the bottom of barrier 614. In a prefened embodiment, however, device 612 just connects the lens holder 608 or banier 614 to moving device 616. It has been found that a separate spinner (not shown) may provide better results for application of scratch resistant coatings to lenses.

Preferably barrier 614 has an interior surface that is made or lined with an absorbant material such as foam rubber. Preferably tins absorbant material is disposable and removable. The absorbant material absorbs any liquids that fall off the lens holder 608, keeping in the interior surface of the banier 614 clean.

In an embodiment, shutter 621 is used to inhibit the activating light from light assembly 622 from contacting banier 614. It is prefened that lens holder 608 be exposed to the activating light from light assembly 622 while shutter 621 blocks at least a portion of the light from contacting barrier 614. Shutter 621 may also inhibit any liquid lens foπning material that falls from lens holder 606 from curing on banier 614. Shutter 621 thus tends to inhibit the formation of flakes on die surface of banier 614. Shutter 621 operates after barrier 614 drops, thus shielding banier 614 while allowing activating light to contact die sample.

In an embodiment, apparatus 600 may be used to apply a precoat to lens before the hardcoat is applied. The precoat may serve to increase the "wettability" of the surface to which the hardcoat is to be applied. A surfactant has been conventionally employed for this purpose, however surfactants tend to affect the volatility and flow characteristics of lens coatings in an unfavorable manner. The precoat may include acetone and/or Byk 300. Upon even distribution of the hardcoat onto a lens in lens holder 608, the coating may be wiped near the edges of the lens to prevent the formation of excessive flakes during curing.

In another embodiment, the precoat and hardcoat are distributed onto lens holder 608. Activating light is directed toward die coatings at least until a gel is formed. A lens forming material may be placed on top of the gel and cured.

Second chamber 604 includes an opening 620 in its floor. It also includes an activating light assembly 622, which may include multiple lights and a light reflector. The apparatus 600 includes an air filtering and distribution system. Air is pulled into a chamber 628 by fans 626 through a filter 624 (the quantity and locations of the fans and filters may vary). The filtered air is distributed by die fans 626 throughout chambers 602, 604, and 617. Air flows from point 613 to point 615 via air ducts (not shown) to reach chamber 617. The temperature of the lights and/or the second chamber may be controlled by turning various fans 629 on and off as needed to suck air out of chamber 604. Air is distributed from chamber 617 through holes 636 that are proximate the lower part of the opening 606 in the first chamber 602. Air is also sucked by fans 627 from the first chamber 602 to chamber 630 through holes 634 tiiat are proximate the top part of the opening 606 in the first chamber 602. This aπangement tends to prevent contaminants from entering first chamber 606. Air is discharged from chamber 630 to the surroundings via fans 627.

During use a lens or lens mold assembly may be placed on die lens holder 608. A button can be pressed, causing die moving device 616 to move device 612, lens holder 604, and the barrier 614 so that they are under the opening 620 in the second chamber 604. Light is thus applied to the lens or lens mold assembly from light assembly 622. After a set period of time, the moving device 616 moves everything back to a location underneath the opening 618 in the first chamber 602.

The lens holder 608 may include a suction cup connected to a metal bar. The concave surface of the suction cup may be attachable to a face of a mold or lens, and the convex surface of die suction cup may be attached to a metal bar. The metal bar may be attachable to a lens spinner.

The lens holder may also alternately mclude movable arms and a spring assembly which are togetiier operable to hold a lens against the lens holder with spring tension during use.

In an alternate method of the mvention, a lens may be cured between two mold members. The gasket may be removed and any remaining liquid lens composition may be removed. At this point a mold member may be applied to a substantially solid conductive heat source. Heat may then be conductively applied to a face of the lens by (a) conductively transferring heat to a face of a mold member from the conductive heat source, and (b) conductively transferring heat through such mold member to the face of the lens. The oxygen barrier enriched with photoinitiator may then be applied, and second activating rays may be directed towards the lens to cure the remaining lens forming composition.

OXYGEN BARRIER EXAMPLE #1

A liquid lens forming composition was initially cured as in a process and apparatus similar to that specified in Example 1. The composition was substantially the same as specified in Example 1, with the exception that hydroquinone was absent, die concentration of methylethylhydroquinone was about 25-45 ppm, the concentration of 1 hydroxycyclohexyl phenyl ketone was 0.017 percent, and the concentration of meuiylbenzoylformate was 0.068 percent. The composition underwent the initial 15 minute cure under the "1st activating light." The apparatus was substantially d e same as described for the above Example 1, with the following exceptions: 1. The air flowrate on each side of the lens mold assembly was estimated to be about 18-20 cubic feet per minute.

2. The apparatus was modified in that air flowed to and from the openings 96 and orifices 98 (which were themselves substantially unchanged) through a duct behind the lens forming chamber, instead of through pipes (e.g. pipe 12 in Figure 5). Essentially plenum portion 95 was expanded so that the walls of the chamber are the walls of the plenum portion 95. Figure 14 depicts a front view of this lens curing apparatus 800. Air in apparatus 800 flows from the orifices 98, over the lens mold assembly 802, through ducts 804, through fan 806, through heat exchanger 808, and then tiirough ducts 810 and back to orifices 98 via air return conduits 824 (shown on Figure 15). Figure 14 also shows a water chiller 812 which cools water and then sends it through conduits 814 and through heat exchanger 808. Figure 14 also shows lights 816 and frosted glass 818. The chamber 820 sunounding lights 816 is not connected to the chamber 822 around the mold assembly 802. In this manner chilled air from orifices 98 does not contact and cool die lights 816 (such cooling tends to cause excessive changes in light output). The chamber 820 is cooled by fans (not shown) which turn on and off depending on die temperature of the surface of the lights 816. Figure 15 shows a side view of apparatus 800.

3. The air flowrate in and out of the chamber sunounding the lights was varied in accordance with the surface temperature of lights. The air flowrate was varied in an effort to keep the temperature on the surface of one of the lights between 104.5 ° F and 105 ° F.

4. The activating light output was controlled to a set point by varying the power sent to the lights as the output of the lights varied.

5. Frosted glass was placed between the lights and the filters used to vary the intensity of the ultraviolet light across the face of the molds. Preferably the glass was frosted on both sides.

The frosted glass acts as a diffuser between the lights and these filters. This frosted glass tended to yield better results if it was placed at least about 2 mm from the filter, more preferably about 10-15 mm, more preferably still about 12 mm, from the filter. Frosted glass was found to dampen the effect of die filters. For instance, the presence of the frosted glass reduced the systems' ability to produce different lens powers by varying the light (see Example 1 and Figure 1).

In Figure 3 the center lights 40 are shown in a triangular arrangement when viewed from the side. These lights were reananged to provide an in-line anangement. After initial cure, the lens mold assembly was removed from the curing chamber. The lens mold assembly included a lens sunounded by a front mold, a back mold, and a gasket between the front and back molds (see, e.g., the assembly in Figure 6).

At this point the protocol in Example 1 stated that the lens was demolded (see above). While demolding at this point is possible, as stated above generally some liquid lens forming composition remained, especially in areas of the lens proximate the gasket. Therefore the lens was not demolded as stated in Example 1. Instead, the gasket was removed, liquid lens forming composition was wiped off the edges of the lens, and a layer of oxygen banier (Parafilm M) with photoinitiator was wrapped around the edges of the lens while the lens was still between the molds. The Parafilm M was wrapped tightly around the edges of the lens and then stretched so tiiat it would adhere to the lens and molds (i.e. in a manner similar to that of Saran wrap). The lens mold assembly was then placed in apparatus 600 so that the back face of the lens (while between the molds) could then be exposed to second activating light.

This second activating light was at a substantially higher intensity than the initial cure light, which was directed at an mtensity of less than 10 mW/cm2. The mold assembly was passed in and out of second chamber 604 in Figure 10 (i.e., a UVEXS Model 912) when the light was set at the high setting. Passing in and out of the chamber took about 22 seconds. The total light energy applied during these 22 seconds was about 4500 millijoules per square centimeter ("mJ/cm2").

Preferably the total light energy applied per pass under the second and third activating light ray lights was in the range of about 500-10,000 mJ/cm2, more preferably about 3000-6000 mJ/cm2, and more preferably still 4000-5000 mJ/cm2. Light energy may be varied by varying die time of exposure, or the intensity of the light. Light energy was measured with a Model IL390B Light Bug from International Light, Inc. (Newburyport, MA, U.S.A.). The total light energy represents the total amount of activating light over the range of 250 to 400 nm.

It has been found that applying activating light at this point helped to cure some or all of the remaining liquid lens forming composition. The second activating light step may be repeated. In this example the second activating light step was repeated once. It is also possible to expose the front or both sides of the lens to the second activating light.

After the second activating light was applied, the mold assembly was allowed to cool. The reactions caused by exposure to activating light are exothermic. The activating lights also tend to emit infra-red light which in turn heats the mold assembly. The lens was then demolded. The demolded lens was substantially drier and harder than lenses that are directly removed from mold assemblies after the initial cure step.

OXYGEN BARRIER EXAMPLE #2

The protocol of Oxygen Banier Example #1 was repeated except that prior to removal of the gasket the lens mold assembly was positioned so that the back face of the lens was exposed to third activating light. In this case d e third activating light was at the same mtensity and for the same time period as one pass of the second activating light. It has been found that applying tiiird activating light at this point helped to cure some or all of the remammg liquid lens formmg composition so that when the gasket was removed less liquid lens formmg composition was present All of the remammg steps in Oxygen Banier Example #1 were applied, and the resultant lens was substantially dry when removed from the molds

CONDUCTIVE HEATING

An embodiment of the mvention relates to postcurmg a polymerized lens contained m a mold cavity by applymg conductive heat to at least one of the molds that form the mold cavity, prior to demolding the lens

More particularly, one embodiment of the mvention includes die following (1) placing a liquid lens forming composition m a mold cavity defined by at least a first mold member and a second mold member, (2) directing activatmg light rays toward at least one of the mold members to cure the lens forming composition so that it forms a lens with a back face, edges, and a front face, (3) applymg a mold member of the mold cavity to a substantially solid conductive heat source, and (4) conductively applymg heat to a face of the lens by (a) conductively transfeπrng heat to a face of a mold member from the conductive heat source, and (b) conductively transfemng heat through such mold member to the face of the lens

In an embodiment described as follows, a lens cured by exposure to activating light is further processed by conductive heating Such conductive heatmg tends to enhance the degree of cross-linking in the lens and to increase the tintability of the lens A lens formmg material is placed in mold cavity 900 (illustrated m Fig 19), which is defined by at least first mold member 902 and second mold member 904 Activating light rays are directed toward at least one of the mold members, thereby curmg the lens forming material to a lens Heat distributor 910 (shown m Fig 16) may be adapted to distribute conductive heat from conductive heat source 912 to at least one mold member Heat distributor 910 is preferably flexible such that at least a portion of it may be shaped to substantially conform to the shape of face 906 or face 907 of first mold member 902 or second mold member 904, respectively Heat distributor 910 is preferably placed m contact with conductive heat source 912, and mold member 902 is placed on heat distπbutor 910 such that face 906 of the mold member rests on top of the heat distπbutor 910 Heat distπbutor 910 may be coupled to heat source 912 Heat is conductively applied to the heat distributor 910 by the heat source 912 Heat is conducted from the heat distributor 910 through the mold member to a face of die lens The heat distπbutor may be shaped to accommodate face 906 of first mold member 902 or face 907 of second mold member 904 such that the heat is applied to front face 916 or back face 915 of the lens (shown in Fig 11) The temperature of heat source 912 may be thermostatically controlled

In an embodiment, hot plate 918 (shown in Fig 17) is used as a heat source to provide conductive heat to the lens A number of other heat sources may be used In an embodiment, heat distributor 910 may mclude countershape 920 Countershape 920 may be placed on top of the hot plate to distπbute conductive heat from die hot plate The countershape is preferably flexible such that at least a portion of it may substantially conform to the shape of an outside face of a mold member The countershape may be hemispherical and either convex or concave dependmg upon whether the surface of the mold assembly to be placed upon it is convex or concave For example, when the concave surface of the back mold is utilized to conduct heat mto the lens assembly, a convex countershape is provided to rest the assembly on.

Countershape 920 may include a glass mold, a metal optical lap, a pile of hot salt and/or sand, or any of a number of other devices adapted to conduct heat from heat source 912. It should be understood that Figure 17 includes combinations of a number of embodiments for illustrative purposes. Any number of identical or distinct countershapes may be used in combination on top of a heat source. In an embodiment, a countershape includes a container 922 filled with particles 924. The particles preferably include metal or ceramic material. Countershape 920 may include heat distributor 910. A layer 914 of material may be placed over the countershape 920 or heat distributor 910 to provide slow, smooth, uniform heat conduction into the lens mold assembly. This layer preferably has a relatively low heat conductivity and may be made of rubber, cloth, Nomex fabric or any other suitable material that provides slow, smooth, uniform conduction.

In an embodiment, countershape 920 includes layer 914 (e.g., a bag or container) filled with particles 924 such that the countershape may be conveniently shaped to conform to the shape of face 906 or face 907. In an embodiment, the countershape is essentially a "beanbag" that contains particles 924 and is conformable to the shape of a mold face placed on top of it. Particles 924 may include ceramic material, metal material, glass beads, sand and or salt. The particles preferably facilitate conductive heat to be applied to face 906 or face 907 substantially evenly.

In an embodiment, die countershape 920 is placed on top of heat source 912 for a sufficient time for a portion of the countershape to attain a temperature substantially near or equal to the temperature on the surface of the heat source. The countershape may then be "flipped over" such that the heated portion of the countershape that has a temperature substantially near or equal to that of the surface of the heat source is exposed. A mold may be placed on top of the heated portion of the countershape, and the countershape is preferably conformed to d e shape of the face of die mold. In this manner, the rate of conductive heat transfer to the lens may begin at a maximum. Heat is preferably conductively transfened through the countershape and the mold face to a face of the lens. The temperature of the heated portion of the countershape may tend to decrease after the mold is placed onto the countershape.

In an embodiment, heat distributor 910 may partially insulate a mold member from conductive heat source 912. The heat distributor preferably allows a gradual, uniform transfer of heat to the mold member. The heat distributor is preferably made of rubber and/or another suitable material. The heat distributor may include countershapes of various shapes (e.g., hemispherically concave or convex) and sizes that are adapted to contact and receive mold members.

In an embodiment, hot plate cover 930 (shown in Fig. 8) is used to distribute conductive heat to face 906 of mold member 902. Cover 930 is adapted to rest directly upon hot plate 918 (or any other heat source). Cover 930 preferably includes portion 932, which is substantially conformed to the shape of face 906. Portion 932 preferably includes a convex surface or a concave surface (not shown) adapted to receive face 906. Portion 932 is preferably made of rubber and causes slow, uniform transfer of conductive heat to face 906. In an embodiment, a hot plate cover having concave indentations substantially conformed to the shape of face 907 is used to distribute heat through a mold member to a lens.

In an embodiment, heat is conductively applied by the heat source to only one outside face of one mold member. This outside face may be face 906 or face 907. Heat may be applied to back face 915 of the lens to enhance crosslinking and/or tintability of the lens material proximate to the surface of the back face of the lens.

In a prefened embodiment, thermostatically controlled hot plate 918 is used as a heat source. Glass optical mold 928 is preferably placed convex side up on hot plate 918 to serve as a countershape. The glass optical mold preferably has about an 80 mm diameter and a radius of curvature of about 93mm. Rubber disc 929 may be placed over this mold 928 to provide uniform conductive heat to die lens mold assembly. The rubber disc is preferably made of silicone and preferably has a diameter of approximately 74 mm and a thickness of about 3 mm. The lens mold assembly preferably is placed on mold 928 so tiiat outside face 906 of a mold member of the assembly rests on top of mold 928. It is prefened that the edge of the lens mold assembly not directly contact the hot plate. The lens mold assembly preferably receives heat through the rubber disc and not through its mold edges.

To achieve good yield rates and reduce the incidence of premature release while using the conductive heat method, it may be necessary for the edge of the lens be completely cured and dry before conductive heat is applied. If the lens edge is incompletely cured (i.e., liquid or gel is still present) while conductive heat is applied, there may be a high incidence of premature release of the lens from the heating unit.

In an embodiment, the edges of a lens are treated to cure or remove incompletely cured lens forming material (see above description) before conductive heat is applied. The mold cavity may be defined by at least gasket 908, first mold member 902, and second mold member 904. Activating light rays are directed toward at least one of the mold members, thereby curing the lens forming material to a lens preferably having front face 916, a back face 915, and edges. Upon the formation of the lens, the gasket may be removed from the mold assembly. An oxygen barrier may be used to cure any remaining liquid or gel on the lens edge according to any of the methods of the above-detailed embodiments. An oxygen barrier treated with photoinitiator is preferably employed. Alternatively, any remaining liquid or gel may be removed manually. Once die edge of the lens is dry, a face of die lens may be conductively heated using any of the meti ods described herein. In an embodiment, a lens is tinted after receiving conductive heat postcure treatment in a mold cavity. During tinting of the lens, the lens is preferably immersed in a dye solution.

CONDUCTIVE HEATING EXAMPLE

A liquid lens forming composition was initially cured in a process and apparatus similar to that specified in Example 1 except for post-cure treatment which was conducted as follows:

After the sample was irradiated for 15 minutes, the lens was removed from the FC-104 chamber and then passed through the above-mentioned UVEXS Model 912 curing chamber (see Figure 10) to receive a dose of about

2 1500 mJ/cm (+/- 100 mJ) of activating light per pass. The gasket was then removed from the mold assembly and the edges of the mold were wiped with an absorbent tissue to remove incompletely cured lens forming material proximate the mold edges. A strip of plastic material impregnated with photoinitiator was wrapped around the edges of the molds that were exposed when die gasket was removed. Next, the mold assembly was passed through the UVEXS curing chamber once to expose the front surface of the mold to a dose of about 2 1500 mJ/cm . The mold assembly was then passed through the UVEXS four more times, with the back surface of the mold receivmg a dose of about 1500mJ/cm per pass A hot plate was operated such that the surface of the hot plate reached a temperature of 340 degrees F (+/- 50 degrees F). A conformable "beanbag" contamer havmg a covermg made of Nomex fabric was placed on the hot plate The contamer contamed glass beads and was turned over such that the portion of the container that had directly contacted the hot plate (i.e., the hottest portion of the contamer) faced upward and away from the hot plate. The mold assembly was then placed onto the heated, exposed portion of the contamer that had been m direct contact with the hot plate The concave, non-casting face of the mold was placed onto the exposed surface of the contamer which substantially conformed to the shape of the face Heat was conducted through the contamer and the mold member to the lens for 13 minutes. A lens havmg a Shore D hardness of 84 was formed. PULSED ACTIVATING LIGHT APPLICATION

A polymerizable lens forming composition may be placed m a mold/gasket assembly and contmuously exposed to appropriate levels of activating light to cure the composition to an optical lens The progress of the curmg reaction may be determined by momtormg the internal temperature of the composition The lens formmg composition may be considered to pass through three stages as it is cured- (1) Induction, (2) Gel Formation & Exotherm, and (3) Extinction These stages are illustrated in Fig. 20 for a -.75 -1.00 power lens cured by contmuous application of activating light. Figure 20 shows temperature within die mold cavity as a function of time throughout a contmuous radiation curing cycle. The induction stage occurs at the beginning of the curmg cycle and is typically characterized by a substantially steady temperature (or falling temperature when the curmg chamber temperature is below that of the composition) of the lens forming composition as it is irradiated with activatmg light. Durmg die induction peπod, the lens formmg composition remams in a liquid state as die photomitiator breaks down and consumes inhibitor and dissolved oxygen present in die composition As die inhibitor content and oxygen content of the composition fall, decomposmg photomitiator and the composition begm to form chams to produce a pourable, "syrup-iike" material.

As irradiation continues, the "syrup" proceeds to develop mto a soft, non-pourable, viscous, gel. A noticeable quantity of heat will begm to be generated durmg this soft gel stage. The optical quality of the lens may be affected at tins po t. Should tiiere be any sharp discontinuities m die mtensity of the activating light (for example, a drop of composition on the exterior of a mold which focuses light mto a portion of the lens formmg composition proximate the drop), a local distortion will tend to be created m the gel structure, likely causing an abenation m the final product The lens forming composition will pass through this very soft gel state and through a firm gel state to become a crystalline structure When usmg OMB-91 lens formmg composition, a haze tends to form momentarily durmg the transition between the gel and crystalline stages. As the reaction contmues and more double bonds are consumed, the rate of reaction and d e rate of heat generated by the reaction will slow, which may cause the internal temperature of the lens formmg composition to pass through a maximum at the pomt where the rate of heat generation exactly matches the heat removal capacity of the system By the time the maximum temperature has been reached and die lens forming composition begins to cool, the lens will typically have achieved a crystalline form and will tend to crack rather than crumble if it is broken. The rate of conversion will slow dramatically and the lens may begin to cool even tiiough some reaction still may be occurring. Irradiation may still be applied through this extinction phase. Generally, the curing cycle is assumed to be complete when the temperature of the lens forming composition falls to a temperature near its temperature at the beginning of exotherm (i.e., the point where the temperature of the composition increased due to die heat released by the reaction).

The continuous inadiation method tends to work well for relatively low mass lenses (up to about 20- 25 grams) under the FC-104 curing chamber conditions (see, e.g., U.S. Patents 5,364,256 and 5,415,816). As the amount of material being cured increases, problems may be encountered. The total amount of heat generated during the exothermic phase is substantially proportional to the mass of the lens forming material. During curing of relatively high mass lenses, a greater amount of heat is generated per a given time than during curing of lower mass lenses. The total mold gasket surface area available for heat transfer (e.g., heat removal from the lens forming composition), however, remains substantially constant. Thus the internal temperature of a relatively high mass of lens forming material may rise to a higher temperature more rapidly than typically occurs with a lower mass of lens forming material. For example, the internal temperature of a low minus cast- to-finish lens typically will not exceed about 100 F, whereas certain thicker semi-finished lens "blanks" may attain temperatures greater than about 350 F when continually exposed to radiation. The lens forming material tends to shrink as curing proceeds and the release of excessive heat during curing tends to reduce the adhesion between the mold and the lens forming material. These factors may lead to persistent problems of premature release and/or cracking during the curing of lens forming material having a relatively high mass.

A significant advantage of the present invention is the production of relatively high-mass, semifinished lens blanks and high power cast-to-finish lenses without the above-mentioned problems of premature release and cracking. Methods of the present invention as described below allow even more control over the process of curing ophthalmic lenses with activating light-initiated polymerization than previous methods. By interrupting or decreasing the activating light at the proper time during the cycle, die rate of heat generation and release can be controlled and the incidence of premature release can be reduced. An embodiment of the invention relates to a method of controlling the rate of reaction (and therefore the rate of heat generation) of a activating light-curable, lens forming material by applying selected intermittent doses (e.g., pulses) of radiation followed by selected periods of decreased activating light or "darkness". It is to be understood that in the description that follows, "darkness" refers to the absence of activating radiation, and not necessarily the absence of visible light.

More particularly, an embodiment of the invention relates to: (a) an initial exposure period of the lens forming material to radiation (e.g., continuous or pulsed radiation) extending through the induction period, (b) interrupting or decreasing the inadiation before the material reaches a first temperature (e.g., the maximum temperature the composition could reach if inadiation were continued) and allowing the reaction to proceed to a second temperature lower than the first temperature, and (c) applying a sufficient number of alternating periods of exposure and decreased activating light or darkness to the lens forming material to complete the cure while controlling the rate of heat generation and or dissipation via manipulation of the timing and duration of the radiation, or the cooling m the curing chamber. Figure 21 shows the temperature within the mold cavity as a function of time for both (a) continuous activatmg light exposure and (b) pulsed activatmg light exposure

In the context of this application, a "gel" occurs when the liquid lens formmg composition is cured to die extent that it becomes substantially non-pourable, yet is still substantially deformable and substantially not crystallized.

In the following description, it is to be understood that the term "first period" refers to the lengtii of time of the initial exposure peπod where radiation (e.g., m pulses) is applied to die lens formmg composition, preferably to form at least a portion of the composition mto a gel "First activating light" rays or light refers to the radiation applied to the lens forming composition dunng the initial exposure period "Second activating light" rays or light refers to the radiation that is applied to die lens formmg composition (e.g., m pulses) after the composition has been allowed to cool to d e "tiiird temperature" mentioned above. "Second period" refers to the duration of time that second activatmg light rays are directed to the lens formmg composition "Third period" refers to the duration of decreased activatmg light or darkness than ensues after activating light has been delivered in the second peπod

In an embodiment of the mvention, the lens formmg material is placed m a mold cavity defined m part between a first mold member and a second mold member. The first mold member and/or second mold member may or may not be continuously cooled as the formation of the lens is completed duπng the second period and or third period One method of removmg heat from the lens forming material is to continuously direct air at a non-casting face of at least one of the mold members. It is preferred that air be directed at both the first and second mold members. A cooler may be used to cool the temperature of the air to a temperature below ambient temperature, more preferably between about 0 C and about 20 C, and more preferably still between about 3 C and about 15 C. Air may also be used to cool at least one of die mold members (m any of the manners described previously) durmg the first penod In an embodiment of the invention, the first period ends when at least a portion of the lens formmg composition begins to mcrease m temperature or form a gel, and die first activatmg light rays are decreased or removed (e g., blocked) such that tiiey cease to contact the first or second mold members. It is prefened tiiat the first period be sufficient to allow the lens formmg matenal to gel m the mold cavity such tiiat tiiere is substantially no liquid present (except small amounts proximate the edge of the material). The interruption of irradiation prior to complete gelation may m some circumstances produce optical distortions. It is prefened that the length of the first period be selected to inhibit d e lens formmg composition from reachmg a first temperature The first temperature is preferably the maximum temperature that die lens formmg composition could reach if it was irradiated under the system conditions (e.g., flow rate and temperature of any coolmg air, wavelength and mtensity of radiation) until the "exothermic potential" (i.e., ability to evolve heat through reaction) of the composition was exhausted.

Accordmg to an embodiment of the mvention, the reactions withm the composition are allowed to proceed after the first activating light rays are removed until the composition reaches a second temperature The second temperature is preferably less than the first temperature. The first temperature is preferably never reached by the composition. Thus, preferably the composition is prevented from achieving the first temperature and then cooling to the second temperature. The composition preferably is allowed to cool from the second temperature to the third temperature. This cooling may occur "inactively" by allowing heat to transfer to the ambient sunoundings, or at least one of the mold members may be cooled by any of the methods described above.

In an embodiment of the invention, the curing of the lens forming material is completed by directing second activating light rays (e.g., in pulses) toward at least one of the mold members. The second activating light rays may be directed toward the mold member(s) for a second period that may be determined according to the rate of reaction of the lens forming composition. The change in temperature of the composition or a portion of the mold cavity, or the air in or exiting the chamber is an indicator of the rate of reaction, and the second period may be determined accordingly. The second period may be varied such tiiat subsequent pulses have a longer or shorter duration than previous pulses. The time between pulses (i.e., die third period) may also be varied as a function of the temperature and/or reaction rate of the composition. To achieve a light pulse, (a) the power to a light source may be turned on and tiien off, (b) a device may be used to alternately transmit and then block die passage of light to die lens forming composition, or (c) the light source and/or mold assembly may be moved to inhibit activating light from contacting the lens forming material. The second and/or third periods are preferably controlled to allow rapid formation of a lens while reducing the incidence of (a) premature release of the lens from the first and/or second mold member and/or (b) cracking of the lens.

In an embodiment, the second period is preferably controlled to inhibit the temperature of the composition from exceeding die second temperature. The temperature of the lens forming composition may continue to increase after radiation is removed from the first and/or second mold members due to the exothermic nature of reactions occuning within the composition. The second period may be sufficiently brief such that the pulse of second activating light rays is removed while the temperature of the composition is below the second temperature, and die temperature of the composition increases during the third period to become substantially equal to the second temperature at the point that the temperature of the composition begins to decrease.

In an embodiment, the third period extends until die temperature of the composition becomes substantially equal to the third temperature. Once the temperature of the composition decreases to the tiiird temperature, a pulse of second activating light rays may be delivered to the composition. In an embodiment, the second period remains constant, and die tiiird period is controlled to maintain the temperature of the composition below the second temperature. The third period may be used to lower the temperature of the composition to a temperature that is expected to cause the composition to reach but not exceed the second temperature after a pulse is delivered to the composition.

In an embodiment, shutter system 950 (shown in Fig. 7) is used to control the application of first and/or second activating light rays to the lens forming material. Shutter system 950 preferably includes air- actuated shutter plates 954 that may be inserted into the curing chamber to prevent activating light from reaching the lens forming material. Shutter system 950 may include programmable logic controller 952, which may actuate air cylinder 956 to cause shutter plates 954 to be inserted or extracted from the curing chamber. Programmable logic controller 952 preferably allows the insertion and extraction of shutter plates 954 at specified time intervals. Programmable logic controller 952 may receive signals from thermocouple(s) located inside chamber, proximate at least a portion die mold cavity, or located to sense the temperature of air in or exiting the chamber, allowing the time intervals in which the shutters are inserted and/or extracted to be adjusted as a function of a temperature within the curing chamber. The thermocouple may be located at numerous positions proximate the mold cavity and/or casting chamber.

The wavelength and intensity of the second activating light rays are preferably substantially equal to those of the first activating light rays. It may be desirable to vary the intensity and or wavelength of die radiation (e.g, first or second activating light rays). The particular wavelength and intensity of the radiation employed may vary among embodiments according to such factors as the identity of the composition and curing cycle variables.

Numerous curing cycles may be designed and employed. The design of an optimal cycle should include consideration of a number of interacting variables. Significant independent variables include: 1) the mass of the sample of lens forming material, 2) the intensity of the light applied to die material, 3) the physical characteristics of the lens forming material, and 4) the cooling efficiency of the system. Significant curing cycle (dependent) variables include: 1) the optimum initial exposure time for induction and gelling, 2) the total cycle time, 3) the time period between pulses, 4) the duration of the pulses, and 5) the total exposure time.

Most of the experiments involving methods of the present invention were conducted using below described OMB-91 monomer and the above-mentioned FC-104 curing chamber set at an operating temperature of 55 degrees F, although tests have been performed using other lens forming materials and curing chamber temperatures. The OMB-91 formulation and properties are listed below.

OMB-91 FORMULATION:

INGREDIENT WEIGHT PERCENT

Sartomer SR 351 (Trimethylolpropane Triacrylate) 20.0 +/- 1.0

Sartomer SR 268 (Tetraethylene Glycol Diacrylate) 21.0 +/- 1.0

Sartomer SR 306 (Tripropylene Glycol Diacrylate) 32.0 +/- 1.0

Sartomer SR 239 (1,6 Hexanediol Dimethacrylate) 10.0 +/- 1.0 (Bisphenol A Bis(Allyl Carbonate)) 17.0 +/- 1.0

Irgacure 184 (1-Hydroxycyclohexyl Phenyl Keytone) 0.017 +/- 0.0002

Methyl Benzoyl Formate 0.068 +/- 0.0007

Methyl Ester of Hydroquinone ("MeHQ") 35 ppm +/- 10 ppm

Thermoplast Blue P (9,10 - Anthracenedione, 0.35 ppm +/- 0.1 ppm l-hydroxy-4-((4-methyl phenyl) Amino) MEASUREMENTS/PROPERTIES:

PROPERTY PROPOSED SPECIFICATION

Appearance Clear Liquid Color

(APHA) 50 maximum

(Test Tube Test) Match Standard Acidity (ppm as Acrylic Acid) 100 maximum Refractive Index 1.4725 +/- 0.002 Density 1.08 +/- 0.005 gm cc. at 23 degrees C.

Viscosity @ 22.5 Degrees C. 27.0 +/- 2 centipoise Solvent Weight (wt %) 0.1 Maximum Water (wt %) 0.1 Maximum MeHQ (from HPLC) 35 ppm +/- 10 ppm

It is recognized that methods and systems of the present invention could be applied to a large variety of radiation-curable, lens forming materials in addition to those mentioned herein. It should be understood tiiat adjustments to curing cycle variables (particularly the initial exposure time) may be required even among lens foπning compositions of the same type due to variations in inhibitor levels among batches of the lens forming compositions. In addition, changes in the heat removal capacity of the system may require adjustments to the curing cycle variables (e.g. duration of the cooling periods between radiation pulses). Changes in the cooling capacity of the system and/or changes in compositions of the lens forming material may require adjustments to curing cycle variables as well. Significant variables impacting the design of a pulsed curing cycle include (a) the mass of the material to be cured and (b) the intensity of the light applied to the material. A significant aspect of methods of the present invention is the initial exposure period. If a sample is initially overdosed with radiation, the reaction may progress too far and increase the likelihood of premature release and/or cracking. If a sample is underdosed initially in a fixed (i.e., preset) curing cycle, subsequent exposures may cause too great a temperature rise later in the cycle, tending to cause premature release and/or cracking. Additionally, if the light intensity varies more than about +/- 10% in a cycle that has been designed for a fixed light intensity level and/or fixed mass of lens forming material, premature release and/or cracking may result.

An embodiment of die present invention involves a curing cycle having two processes. A first process relates to forming a dry gel by continuously inadiating a lens forming composition for a relatively long period. The material is then cooled down to a lower temperature under darkness. A second process relates to controllably discharging the remaining exothermic potential of the material by alternately exposing the material to relatively short periods of inadiation and longer periods of decreased inadiation (e.g., dark cooling). The behavior of the lens forming material during the second process will depend upon die degree of reaction of the lens forming material that has occuned during the first process. For a fixed curing cycle, it is preferable tiiat the extent of reaction occuning in the first process consistently fall within a specified range. If the progress of reaction is not controlled well, the incidence of cracking and/or premature release may rise. For a curing cycle involving a composition having a constant level of inhibitor and initiator, the intensity of the radiation employed is the most likely source of variability in the level of cure attained in the first process. Generally, a fluctuation of +/- 5% in the intensity tends to cause observable differences in the cure level achieved in the first process. Light intensity variations of +/- 10% may significantly reduce yield rates.

The effect of various light intensities on the material being cured depends upon whether the intensity is higher or lower than a prefened intensity for which the curing cycle was designed. Fig. 23 shows temperature profiles for three embodiments in which different light levels were employed. If the light intensity to which die material is exposed is higher than a prefened intensity, the overdosage may cause the reaction to proceed too far. In such a case, excessive heat may be generated, increasing the possibility of cracking and/or premature release during the first process of the curing cycle. If premature release or cracking of the overdosed material does not occur in the first process, then subsequent pulses administered during the second process may create very little additional reaction.

If the light intensity is lower than a prefened intensity and the lens forming material is underdosed, other problems may arise. The material may not be driven to a sufficient level of cure in die first process. Pulses applied during the second process may then cause relatively high amounts of reaction to occur, and the heat generated by reaction may be much greater than the heat removal capacity of the system. Thus the temperature of the lens forming material may tend to excessively increase. Premature release may result. Otherwise, undercured lenses that continue generating heat after the end of die cycle may be produced.

The optimal initial radiation dose to apply to the lens forming material may depend primarily upon its mass. The initial dose is also a function of the light intensity and exposure time. A method for designing a curing cycle for a given mold/gasket/monomer combination may involve selecting a fixed light intensity.

Methods of the present invention may involve a wide range of light intensities. Using a relatively low intensity may allow for the length of each cooling step to be decreased such that shorter and more controllable pulses are applied. Where a fluorescent lamp is employed, the use of a lower intensity may allow the use of lower power settings, thereby reducing the load on the lamp cooling system and extending the life of d e lamp. A disadvantage of using a relatively low light mtensity is that the initial exposure period tends to be somewhat longer. Relatively high intensity levels tend to provide shorter initial exposure times while placing more demand upon d e lamp drivers and/or lamp cooling system, either of which tends to reduce the life of the lamp.

In an embodiment, General Electric F15T8BL lamps powered by Mercron HR0696-4 drivers may be used in conjunction witii an FC 104 curing chamber having one piece of double-frosted diffusing glass and one

2 piece of clear PO-4 acrylic plate. The light intensity settings may be 760 microwatts/cm for the top lamps and

2

950 microwatts/cm for the bottom lamps. Once a light mtensity is selected, the initial exposure time may be determined A convenient method of monitormg the reaction during the cycle mvolves fashionmg a fine gage thermocouple, positioning it mside the mold cavity, and connecting it to an appropriate data acquisition system A prefened thermocouple is Type J, 0 005 mch diameter, Teflon-insulated wire available from Omega Engmeermg The insulation is stripped back about 30 to 50 mm and each wire is passed tiirough the gasket wall via a fine bore hypodermic needle The needle is then removed and the two wires are twisted together to form a thermocouple junction inside the inner circumference of the gasket The other ends of the leads are attached to a miniature connector which can be plugged mto a permanent thermocouple extension cord leadmg to the data acquisition unit after the mold set is filled The data acquisition unit may be a Hydra 2625A Data Logger made by John Fluke Mfg Company It is connected to an IBM compatible personal computer running Hydra Data Logger software The computer is configured to display a trend plot as well as numeric temperature readmgs on a monitor The scan interval may be set to any convenient time period and a period of five or ten seconds usually provides good resolution The position of the thermocouple junction m the mold cavity may affect its readmg and behavior through the cycle When the junction is located between the front and back molds, relatively high temperatures may be observed compared to the temperatures at or near the mold face The distance from the edge of die cavity to the junction may affect both absolute temperature readmgs as well as the shape of the curing cycles' temperature plot The edges of the lens formmg matenal may begm to mcrease m temperature slightly later than other portions of the material Later in the cycle, the lens formmg matenal at the center may be somewhat ahead of the material at the edge and will tend to respond little to die radiation pulses, whereas the material near d e edge may tend to exhibit significant activity When performing experiments to develop curmg cycles, it is prefened to insert two probes mto the mold cavity, one near the center and one near the edge The center probe should be relied upon early in the cycle and the edge probe should guide the later stages of the cycle

Differmg rates of reaction among vaπous regions of the lens formmg material may be achieved by applymg a differential light distribution across the mold face(s) Tests have been performed where "minus type" light distributions have caused die edge of die lens formmg material to begm reactmg before the center of the material The potential advantages of usmg light distributing filters to cure high mass semi-finished lenses may be offset by nonuniformity of total light transmission that tends to occur across large numbers of filters The activating light transmission of die PO-4 acrylic plates (Cyro Industπes, Piano, Texas) used over the apertures m the FC-104 curing chamber tends to be considerably more consistent than that of silk-screened filter plates

After the selection and/or configuration of (a) the radiation mtensity, (b) die radiation-curable, lens formmg matenal, (c) the mold gasket set, and (d) the data acquisition system, the optimum initial exposure peπod may be determined It is useful to expose a sample of lens formmg matenal to continuous radiation to obtam a temperature profile This will provide an identifiable range of elapsed time withm which the optimal initial exposure time will fall Two pomts of mterest are the time where the temperature rise in the sample is first detected ("T initial" or "Ti"), and the time where the maximum temperature of the sample is reached ("Tmax"). Also of interest is the actual maximum temperature, an indication of the "heat potential" of the sample under the system conditions (e.g., in the presence of cooling).

As a general rule, die temperature of high mass lenses (i.e., lenses greater tiian about 70 grams) should remain under about 200 F and preferably between about 150 F and about 180 F. Higher temperatures are typically associated with reduced lens yield rates due to cracking and/or premature release. Generally, the lower mass lenses (i.e., lenses no greater than about 45 grams) should be kept under about 150 F and preferably between about 110 F and about 140 F.

The first period may be selected according to the mass of the lens forming material. In an embodiment, the lens forming material has a mass of between about 45 grams and about 70 grams and die selected second temperature is a temperature between about 150 F and about 200 F. According to anotiier embodiment, the lens forming material has a mass no greater than about 45 grams and a second temperature less than about 150 F. In yet another embodiment of the invention, the lens forming material has a mass of at least

° about 70 grams, and a second temperature between about 170 F and about 190 F.

An experiment may be performed in which the radiation is removed from the mold members slightly before one-half of the time between T initial and Tmax. The initial exposure time may be interatively reduced or increased according to die results of die above experiment in subsequent experiments to provide a Tmax in a prefened range. This procedure may allow die determination of the optimal initial exposure time for any given mold/gasket set and light intensity.

A qualitative summary of relationships among system variables related to die above-described methods is shown in Fig. 22.

After the initial exposure period, a series of irradiation pulse/cooling steps may be performed to controllably discharge the remaining exothermic potential of the material and tiius complete the cure. There are at least two approaches to accomplish this second process. The first involves applying a large number of very short pulses and short cooling periods. The second approach involves applying a fewer number of longer pluses with conespondingly longer cooling periods. Either of these two methods may produce a good product and many acceptable cycles may exist between these extremes.

A significant aspect of the invention relates to using pulsed application of light to produce a large range (e.g., from -6 to +4 diopter) of lenses without requiring refrigerated cooling fluid (e.g., cooled air). With proper light application, air at ambient may be used as a cooling fluid, thus significantly reducing system costs. Some established cycles are detailed in die table below for three semifinished mold gasket sets: a

6.00D base curve, a 4.50D base curve, and a 3.00D base curve. These cycles have been performed using an FC-104 curing chamber in which cooling air at a temperature of about 56 degrees F was directed at the front and back surfaces of a mold assembly. Frosted diffusing window glass was positioned between d e samples and the lamps, with a layer of PO-4 acrylic material approximately 1 inch below the glass. A top light intensity was adjusted to 760 microwatts/cm2 and a bottom light intensity was adjusted to 950 microwatts/cm2, as measured at about the plane of the sample. A Spectroline meter DM365N and standard detector stage were used. An in- mold coating as described in U.S. application serial no. 07/931,946 was used to coat botii the front and back molds.

Figures 24, 25, and 26 each show temperature profiles of the above-detailed cycles for a case where the activating light exposure is continuous and a case where the activating light delivery is pulsed. In Figures 23- 26, "lo" denotes die initial intensity of the activating light rays used in a curing cycle. The phrase "Io=760/950"

2 means that the light intensity was adjusted to initial settings of 760 microwatts/cm for the top lamps and 950

2 microwatts/cm for the bottom lamps. The "interior temperature" of Figures 23-26 refers to a temperature of the lens forming material as measured by a tiiermocouple located within die mold cavity.

The following general rules for die design of pulse/cooling cycles may be employed to allow rapid curing of a lens while inhibiting premature release and/or cracking of the lens. The duration of the pulses preferably does not result in a temperature that exceeds the maximum temperature attained in die initial exposure period. The length of the cooling period may be determined by the length of time necessary for the internal temperature of the lens forming material to return to near the temperature it had immediately before it received a pulse. Following tiiese general rules during routine experimentation may permit proper curing cycles to be established for a broad range of lens forming materials, light intensity levels, and cooling conditions. Preferably light output is measured and controlled by varying the amount of power applied to the lights in response to changes in light output. Specifically, a prefened embodiment of die invention includes a light sensor mounted near the lights. This light sensor measures the amount of light, and then a controller increases the power supplied to maintain the first activating light rays as the intensity of the first activating light rays decreases during use, and vice versa. Specifically, the power is varied by varying the electric frequency supplied to the lights. A filter is preferably applied to die light sensor so tiiat light waves other than activating light impinge less, or not at all, on the light sensor. In one embodiment, a piece of 365N Glass made by Hoya Optics (Fremont, California) was applied to a light sensor to filter out visible rays.

One "lamp driver" or light controller was a Mercron Model FX0696-4 and Model FX06120-6 (Mercron, Inc., Dallas, Texas, U.S.A.). These light controllers may be described in U.S. patents 4,717,863 and 4,937,470.

Figure 13 schematically depicts die light control system described above. The lights 40 in apparatus 10 apply light towards the lens holder 70. A light sensor 700 is located adjacent die lights 40. Preferably the light sensor 700 is a photoresistor light sensor (photodiodes or otiier light sensors may also be usable in tins application). The light sensor 700 witii a filter 750 is connected to lamp driver 702 via wires 704. Lamp driver 702 sends a cunent through the light sensor 700 and receives a return signal from the light sensor 700. The return signal is compared against an adjustable set point, and tiien the electrical frequency sent to the activating lights 40 via wires 706 is varied depending on the differences between die set point and die signal received from the light sensor 700. Preferably the light output is maintained witiiin about +/- 1.0 percent.

In an embodiment of die invention, a medium pressure mercury vapor lamp is used to cure the lens forming material and the lens coating. This lamp and many conventional light sources used for activating light curing may not be repeatedly turned on and off since a several minute warm-up period is generally required prior to operation. Mercury vapor light sources may be idled at a lower power setting between exposure periods (i.e., second periods), however, die light source will still generate significant heat and consume electricity while at the lower power setting. In an embodiment, a flash lamp emits activatmg light pulses to cure the lens forming material. It is believed that a flash lamp would provide a smaller, cooler, less expensive, and more reliable light source than other sources. The power supply for a flash lamp tends to draw relatively minimal cunent while charging its capacitor bank. The flash lamp discharges the stored energy on a microsecond scale to produce very high peak intensities from the flash tube itself. Thus flash lamps tend to require less power for operation and generate less heat than other light sources used for activating light curing. A flash lamp may also be used to cure a lens coating.

In an embodiment, die flash lamp used to direct activating light rays toward at least one of me mold members is a xenon light source. The lens coating may also be cured using a xenon light source. Referring to Fig. 29, xenon light source 980 preferably contains photostrobe 992 having a tube 996 and electrodes to allow die transmission of activating light rays. The tube may include borosilicate glass or quartz. A quartz tube will generally withstand about 3 to 10 times more power than a hard glass tube. The tube may be in die shape of a ring, U, helix, or it may be linear. The tube may include capacitive trigger electrode 995. The capacitive trigger electrode may include a wire, silver strip, or conductive coating located on the exterior of tube 996. The xenon light source is preferably adapted to deliver pulses of light for a duration of less than about 1 second, more preferably between about 1/10 of a second and about 1/1000 of a second, and more preferably still between about 1/400 of a second and 1/600 of a second. The xenon source may be adapted to deliver light pulses about every 4 seconds or less. The relatively high intensity of the xenon lamp and short pulse duration may allow rapid curing of d e lens formmg composition without imparting significant radiative heat to the composition.

In an embodiment, controller 990 (shown in Fig. 29) controls the intensity and duration of activating light pulses delivered from activating light source 980 and the time interval between pulses. Activating light source 980 may include capacitor 994, which stores the energy required to deliver the pulses of activating light. Capacitor 994 may be adapted to allow pulses of activating light to be delivered as frequently as desired.

Temperature monitor 997 may be located at a number of positions within mold chamber 984. The temperature monitor may measure the temperature within the chamber and/or the temperature of air exiting the chamber. The system may be adapted to send a signal to cooler 988 and/or distributor 986 (shown in Fig. 27) to vary die amount and/or temperature of the cooling air. The temperature monitor may also determine the temperature at any of a number of locations proximate the mold cavity and send a signal to controller 990 to vary the pulse duration, pulse intensity, or time between pulses as a function of a temperature within mold chamber 984.

In an embodiment, light sensor 999 is used to determine the intensity of activating light emanating from source 980. The light sensor is preferably adapted to send a signal to controller 990, which is preferably adapted to maintain the intensity of die activating light at a selected level. Filter 998 may be positioned between activating light source 980 and light sensor 999 and is preferably adapted to inhibit visible rays from contacting light sensor 999, while allowing activating light rays to contact the sensor. The filter may include 365 N glass or any otiier material adapted to filter visible rays and transmit ultraviolet rays.

In an embodiment, a cooling distributor is used to direct air toward the non-casting face of at least one of the mold members to cool the lens forming composition. The air may be cooled to a temperature of below ambient temperature prior to being directed toward at least one of the mold members to cool the composition.

In an embodiment, air at ambient temperature may be used to cool die lens forming composition. Since the xenon flash generally has a duration of much less than about one second, considerably less radiative heat tends to be transfened to the lens forming composition compared to curing methods employing other activating light sources. Thus, die reduced heat imparted to the lens forming composition may allow for air at ambient temperature to remove sufficient heat of exotiierm to substantially inhibit premature release and/or cracking of die lens. In an embodiment, the xenon source is used to direct first activating light rays toward d e first and second mold members to the point that a temperature increase is measured and/or the lens forming composition begins to or forms a gel. It is prefened that the gel is formed with less than 15 pulses of radiation, and more preferably with less tiian about 5 pulses. It is prefened tiiat the gel is formed before the total time to which the composition has been exposed to die pulses exceeds about 1/10 or 1/100 of a second.

In an embodiment, a reflecting device is employed in conjunction witii the xenon light source. The reflecting device is positioned behind the flash source and preferably allows an even distribution of activating light rays from the center of the composition to the edge of the composition.

In an embodiment, a xenon light flash lamp is used to apply a plurality of activating light pulses to the lens forming composition to cure it to an eyeglass lens in a time period of less than 30 minutes, or more preferably, less than 20 or 15 minutes.

The use of a xenon light source also may allow the formation lenses over a wider range of diopters. Higher power lenses exhibit greatest thinnest to thickest region ratios, meaning that more shrinkage-induced stress is created, causing greater mold flexure and thus increased tendency for premature release. Higher power lenses also possess thicker regions. Portions of lens forming material within these thicker regions may receive less light man regions closer to die mold surfaces. Continuous inadiation lens forming techniques typically require the use of relatively low light intensities to control the heat generated during curing. The relatively low light intensities used tends to result in a long, slow gelation period. Optical distortions tend to be created when one portion of the lens is cured at a different rate than another portion. Methods characterized by non-uniform curing are typically poorly suited for die production of relatively high power lenses, since the deeper regions (e.g.,, regions within a thick portion of a lens) tend to gel at a slower rate than regions closer to the mold surfaces.

The relatively high intensity attainable with the xenon source may allow deeper penetration into, and/or saturation of, the lens forming material, thereby allowing uniform curing of thicker lenses than in conventional radiation-initiated curing. More uniform gelation tends to occur where the lens forming material is dosed with a high intensity pulse of activating light and then subjected to decreased activating light or darkness as the reaction proceeds without activating radiation. Lenses having a diopter of between about +5.0 and about -6.0 and greater may be cured. It is believed tiiat light distribution across the sample is less critical when curing and especially when gelation is induced with relatively high intensity light. The lens forming material may be capable of absorbing an amount of energy per time that is below that delivered during a relatively high intensity pulse. The lens forming material may be "oversaturated" with respect to the light delivered via a high intensity flash source. In an embodiment, the xenon source is used to cure a lens having a diopter between about -4.0 and about -6.0. In an embodiment, the xenon source is used to cure a lens having a diopter between about +2.0 and about +4.0. In an embodiment, more than one xenon light source is used simultaneously to apply activating light pulses to the lens formmg composition. Such an embodiment is shown in Fig. 28. Xenon light sources 980a and 980b may be positioned around mold chamber 985 so that pulses may be directed toward the front face of a lens and d e back face of a lens substantially simultaneously. Mold chamber 985 is preferably adapted to hold a mold in a vertical position such tiiat pulses from xenon source 980a may be applied to the face of a first mold member, while pulses from source 980b may be applied to die face of a second mold member. In an embodiment, xenon source 980b applies activating light pulses to a back surface of a lens more frequently tiian xenon source 980a applies activating light pulses to a front surface of a lens. Xenon sources 980a and 980b may be configured such that one source applies light to mold chamber 984 from a position above the chamber while the other xenon source applies light to the mold chamber from a position below the chamber.

In an embodiment, a xenon light source and a relatively low mtensity (e.g., fluorescent) light source are used to simultaneously apply activating light to a mold chamber. As illustrated in Fig. 27, xenon source 980 may apply activating light to one side of mold chamber 984 while low intensity fluorescent source 982 applies activating light to another side of die mold chamber. Fluorescent source 982 may include a compact fluorescent "light bucket" or a diffused fluorescent lamp. The fluorescent light source may deliver continuous or substantially pulsed activating light rays as the xenon source delivers activating light pulses. The fluorescent source may deliver continuous activating light rays having a relatively low intensity of less than about 100 nicrowatts/cm . Methods of the present invention allow curing of high-mass semi-finished lens blanks from the same material used to cure cast-to-finish lenses. Both are considered to be "eyeglass lenses" for the purposes of this patent. These methods may also be used to cure a variety of other lens forming materials. Methods of die present invention have been successfully used to make cast-to-finish lenses in addition to semi-finished lenses.

PULSE METHOD EXAMPLE 1; USE OF A MEDIUM PRESSURE VAPOR LAMP

An eyeglass lens was successfully cured witii activating light utilizing a medium pressure mercury vapor lamp as a source of activating radiation (i.e., die UVEXS Model 912 previously described herein). The curing chamber included a six inch medium pressure vapor lamp operating at a power level of approximately 250 watts per inch and a defocused dichroic reflector that is highly reflective of activating light. A high percentage of infrared radiation was passed tiirough the body of the reflector so that it would not be directed toward the material to be cured. The curing chamber further included a conveyer mechanism for transporting the sample underneath the lamp. With this curing chamber, the transport mechanism was set up so that a carriage would move the sample from the front of the chamber to the rear such that the sample would move completely through an inadiation zone under the lamp. The sample would then be transported through the zone again to die front of the chamber. In tiiis manner the sample was provided witii two distinct exposures per cycle. One pass, as defined hereinafter, consists of two of these distinct exposures. One pass provided a dosage of approximately 275 milliJoules measured at the plane of the sample using an International Light IL 1400 radiometer equipped witii a XRL 340 B detector.

A lens cavity was created using the same molds lens forming composition, and gasket of Pulsed Method Example 2 below. The reaction cell containing die lens forming material was placed on a supporting stage such that the plane of the edges of the convex mold were at a distance of approximately 75 mm from the plane of the lamp. The lens cavity was then exposed to a series of activating doses consisting of two passes directed to die back surface of the mold followed immediately by one pass directed to the front surface of die mold. Subsequent to these first exposures, the reaction cell was allowed to cool for 5 minutes in die absence of any activating radiation in an FC-104 chamber as described in Pulsed Method Example 1 at an air temperature of 74.6 degrees F and at an air flow rate of approximately 15 to 25 scf per minute to the back surface and 15 to 25 scf to the front surface of the cell. The lens cavity was then dosed with one pass to the front mold surface and returned to the cooling chamber for 6 minutes. Then the back surface was exposed in one pass and tiien was cooled for 2 minutes. Next, the front surface was exposed in two passes and then cooled for 3.5 minutes. The front surface and die back surface were then each exposed to two passes, and die gasket was removed to expose the edges of die lens. A strip of polyethylene film impregnated with photoinitiator was then wrapped around the edge of the lens and the front and back surfaces were exposed to another 3 passes each. The back surface of the cell was then placed on the conductive thermal in-mold postcure device using "bean-bag" container filled with glass beads on a hot plate at about 340 F described previously (see conductive heating example 1) for a time period of 13 minutes, after which the glass molds were removed from the finished lens. The finished lens exhibited a distance focusing power of -6.09 diopters, had excellent optics, was abenation- free, was 74 mm in diameter, and had a center tiiickness of 1.6 mm. During the cooling steps , a small surface probe thermistor was positioned against the outside of the gasket wall to monitor the reaction. The results are summarized below.

PULSE METHOD EXAMPLE 2: USE OF A SINGLE XENON FLASH LAMP

An eyeglass lens was successfully cured with activating light utilizing a xenon flash lamp as a source of activating radiation. The flash lamp used was an Ultra 1800 White Lightning photographic strobe, commercially available from Paul C. Buff Incorporated of Nashville, Tennessee. This lamp was modified by replacing the standard borosilicate flash tubes with quartz flash tubes. A quartz flash tube is prefened because some of die activating light generated by d e arc inside die tube tends to be absorbed by borosilicate glass. The strobe possessed two semicircular flash tubes that trigger simultaneously and are positioned to form a ring approximately 73 millimeters in diameter. The hole in the reflector behind die lamps, which normally contains a modeling lamp for photographic purposes, was covered with a flat piece of highly-polished activating light reflective material, which is commercially available under the trade name of Alzac from Ultra Violet Process Supply of Chicago, Illinois. The power selector switch was set to full power. The activating light energy generated from one flash was measured using an International Light IL 1700 Research Radiometer available from International Light, Incorporated of Newburyport, Massachusetts. The detector head was an International Light XRL 340 B, which is sensitive to radiation in the 326 nm to 401 nm region. The window of die detector head was positioned approximately 35 mm from the plane of the flash tubes and was approximately centered within the ring formed by the tubes.

A mold cavity was created by placing two round 80 mm diameter crown glass molds into a silicone rubber ring or gasket, which possessed a raised lip around its inner circumference. The edges of the glass molds rested upon die raised lip to form a sealed cavity in the shape of the lens to be created. The inner circumference of the raised lip conesponded to the edge of die finished lens. The concave surface of the first mold conesponded to die front surface of the finished lens and the convex surface of the second mold conesponded to die back surface of the finished lens. The height of die raised lip of the rubber ring into which the two glass molds are inserted controls the spacing between the two glass molds, thereby controlling the thickness of the finished lens. By selecting proper gaskets and first and second molds tiiat possess various radii of curvature, lens cavities can be created to produce lenses of various powers.

A lens cavity was created by placing a concave glass mold with a radius of curvature of 407.20 mm and a convex glass mold with a radius of curvature of 65.26 mm into a gasket which provided spacing between the molds of 1.8 mm measured at the center of the cavity. Approximately 32 grams of a lens forming monomer was charged into me cavity. The lens forming material used for this test was OMB-91 lens monomer. The reaction cell containing the lens formmg material was placed horizontally on a supporting stage such that the plane of the edges of die convex mold were at a distance of approximately 30 mm from the plane of the flash tubes and die cell was approximately centered under die light source.

The back surface of the lens cavity was then exposed to a first series of 5 flashes, witii an interval of approximately 4 seconds in between each flash. The cell was then turned over and the front surface was exposed to anoti er 4 flashes with intervals of about 4 seconds in between each flash. It is preferable to apply the first set of flashes to the back surface to start to cure the material so that any air bubbles in the liquid monomer will not migrate from die edge of die cavity to the center of the optical zone of the lens. Subsequent to these first nine flashes, die reaction cell was allowed to cool for five minutes in die absence of any activating radiation in die above-described FC-104 chamber. To cool the reaction cell, air at a temperature of 71.4 degrees F and at a flow rate of approximately 15 to 25 scf per minute was applied to the back surface and air at a temperature of 71.4 degrees F and at a flow rate of approximately 15 to 25 scf per minute was applied to die front surface of the cell. The back surface of the lens cavity was then dosed with one more flash and returned to the cooling chamber for four minutes.

Next, the cell was exposed to one flash on the front surface and cooled in the cooling chamber for seven minutes. Then the cell was exposed to one flash on the front surface and one flash on the back surface and cooled for three minutes. Next, the cell was exposed to two flashes on die front surface and two flashes on the back surface and cooled for four and a half minutes. The cell was men exposed to five flashes each to d e back surface and front surface, and the gasket was removed to expose the edges of the lens. A strip of polyethylene film impregnated with photoinitiator (Irgacure 184) was then wrapped around the edge of the lens, and d e cell was exposed to anotiier five flashes to the front surface and fifteen flashes to die back surface. The back surface of the cell was then placed on die conductive thermal in-mold postcure device (i.e., "bean bags" filled witii glass beads sitting on a hot plate at approx. 340 ° F) as described previously (see conductive heating example above) for a time period of 13 minutes, after which the glass molds were removed from die finished lens. The finished lens exhibited a distance focusing power of -6.16 diopters and a +2.55 bifocal add power, had excellent optics, was abenation-free, was 74 mm in diameter, and had a center of thickness of 1.7 mm. During the cooling steps , a small surface probe thermistor was positioned against the outside of the gasket wall to monitor the reaction. The results are summarized in die table on the following page.

IMPROVED ACTIVATING LIGHT LENS CURING APPARATUS

FIG. 30 depicts a schematic view of an embodiment of an activating light lens curing apparatus 400.

The apparatus preferably includes a first light generator 402 and a second light generator 404 for generating and directing activating light towards lens cell 52. First light generator 402 is preferably configured to direct activating light toward a first mold member of the lens cell, and second light generator 404 is preferably configured to direct activating light toward a second mold member of the lens cell. The light generators 402 and 404 may be medium pressure mercury lamps for continuously directing activating light towards the lens cell or may be strobe light sources for delivering pulses of activating light to die lens cell. In an embodiment, the strobe light source is a xenon source having a flash tube made of quartz. In an alternate embodiment, the strobe light source is a xenon source having a flash tube made from, for example, borosilicate. The apparatus may include shutter system 950 (shown in Fig. 7) and programmable logic controller 952. The shutter system is preferably operable to block at least a portion of the activating light directed toward at least one of the mold members. Programmable logic controller 952 is preferably coupled to the shutter and adapted to activate the shutter system. The shutters are preferably adapted to extend to block passage of activating light toward the lens cell and are preferably adapted to retract to allow passage of the activating light toward die lens cell.

Apparatus 400 preferably includes an air manifold 406 that may substantially sunound inadiation chamber 407. Air distribution device 94 is preferably disposed on die surface of the air manifold to direct air toward die non-casting face of at least one of the mold members. The irradiation chamber preferably communicates with air plenum 412, which directs "effluent air" away from the irradiation chamber. As described herein, "effluent air" is taken to mean air that has contacted at least one of the mold members to remove heat from the lens forming material contained within the mold cavity. The lens cell is preferably secured within a lens holder of lens drawer 410 prior to being inserted into the inadiation chamber. The lens drawer may be inserted within and removed from the irradiation chamber and is preferably adapted to form a substantially airtight seal with the air manifold when inserted into the inadiation chamber.

Apparatus 400 preferably includes a first cooling assembly 414 and a second cooling assembly 416 for reducing the temperature of the air (and preferably cooling the air to a temperature below ambient temperature) before it is passed from air distribution device 94 to die lens cell. FIG. 32 depicts a cross-sectional view of the inadiation chamber and the cooling assemblies. Inadiation chamber 408 is preferably enclosed with substantially airtight seals to inhibit or prevent cooling air from escaping from the chamber. In an embodiment, members 420 and 422 may be positioned on the air distribution devices to form a substantially airtight seal. Member 420 is preferably disposed between light generator 402 and the first mold member, and member 422 is preferably disposed between light generator 404 and the second mold member. Members 420 and 422 may be plates and are preferably substantially transparent to the activating light delivered from light generators 402 and 404, respectively. In an embodiment, members 402 and 404 are substantially clear borosilicate glass. In an alternate embodiment, members 402 and 404 are light diffusers for diffusing the activating light directed to the lens cell. The light diffusers are preferably made of borosilicate glass that has been sandblasted to "frost" the glass. In an alternate embodiment, member 402 and 404 may be made from quartz glass.

In an embodiment, cooling assemblies 414 and 416 are thermoelectric cooling systems. Cooling assembly 414 may be used to cool air directed toward the first mold member, and cooling assembly 416 may be used to cool air directed toward the second mold member. The cooling assemblies are preferably sized to cool the air to a temperature between about 0°C and about 20°C.

Cooling assembly 414 preferably includes a thermoelectric module 422 for creating a temperature differential to allow the air to be cooled to below ambient temperature. An exemplary thermoelectric module is shown in FIG. 33. The tiiermoelectric module is preferably connected to a DC power source 440. The thermoelectric module is preferably a semiconductor wafer and preferably includes a plurality of semiconductor pn-couples disposed between a pair of ceramic plates 448 and 450 containing metallization 446. The pn- couples are preferably connected thermally in parallel and electrically in series. The thermoelectric module may be a single-stage or cascade module. When the thermoelectric module is connected to die DC power source, a phenomenon (i.e., "die Peltier effect") occurs whereby heat is absorbed on cold side 448 and heat is dissipated from hot side 450. It is to be understood tiiat the flow of cunent may be reversed to cause side 448 to dissipate heat while side 450 absorbs heat. The publication entitled "An Introduction to Thermoelectrics", available from Tellurex Corp. of

Traverse City, Michigan discusses such thermoelectric modules and is incorporated by reference as if fully set forth herein. The pamphlet entitled "A Thermoelectric Bible on How to Keep Cool", available from Supercool Corp. of Minneapolis, Minnesota also describes a thermoelectric module and is incorporated by reference as if fully set forth herein. In FIG. 31 , the side of the thermoelectric module facing upwards is the hot side. Cooling assembly

414 preferably includes a heat sink 428 coupled to the hot side to facilitate the dissipation of heat from the thermoelectric module. The heat sink may be directly coupled to the hot side or the heat sink may be indirectly coupled to the hot side via a member having a relatively high thermal conductivity. In FIG. 31, the heat sink is indirectly coupled to die hot side by conductive block 424. Insulation 426 preferably substantially sunounds the thermoelectric module and the conductive block. In an embodiment, a fan 434 is used to direct air across heat sink 428 to increase the rate of heat dissipation from the thermoelectric module. The heat sink preferably includes a plurality of fins which serve as a heat transfer surface.

The cold side of die thermoelectric module is preferably coupled to a cold side heat sink 430 serving to absorb heat to cool the air directed toward the lens cell. The cold side heat sink may be located within air conduit 453 and preferably contains a plurality of fins tiirough which the air is passed to cool it.

Cooling assembly 416 preferably includes second thermoelectric module 423, second conductive block 425, second hot side heat sink 429, and second fan 435, each of which may operate in the manner as described above for die elements included within cooling assembly 414. In an alternate embodiment, cooling assemblies 414 and 416 may be independently operable to allow air directed toward the first mold member to have a different temperature tiian air directed toward the second mold member.

A first blower 432 is preferably configured to direct air through air conduit 453, which communicates with air distribution device 94a. Second blower 433 is preferably configured to direct air through air conduit 454, which communicates with air distribution device 94b. As described herein, a "blower" is taken to mean any device operable to drive a fluid such as air through a conduit. The first blower preferably drives air tiiat is distributed across the non-casting face of the first mold member. The second blower preferably drives air that is distributed across the non-casting face of the second mold member. Effluent air that has contacted die non- casting face of at least one of the mold members is preferably passed through air plenum 412 and to blowers 432 and 433 for recycling to air distribution devices 94a and 94b. Each of d e tiiermoelectric modules is preferably sized to cool about 1-30 cubic feet per minute of heated effluent air to a temperature of about 0- 20°C.

In an alternate embodiment, the cooling assemblies may be used to reduce the temperature of the recirculated air to ambient temperature or a temperature above ambient temperature. The cooling assemblies may be activated when the cooling air exceeds a predetermined temperature level above ambient temperature. The thermoelectric cooling system has been found to operate more quietly, efficiently, and reliably than some conventional cooling systems. Recirculating the effluent air through the closed cooling loop tends to reduce the heat duty on the cooling system, since the effluent air in air plenum 412 preferably has a temperature less than ambient temperature. In an embodiment, a control panel 418 is operable to manually or automatically control operation of apparatus 400. The control panel may include an electronic controller for automatic control of system variables and a digital display 415 indicating the temperature of the coolmg air at various locations in the air conduits, irradiation chamber, and air plenum. The control panel is preferably adapted to receive electronic signals from temperature sensors 460, 462, and 464. Cavities may also be formed in conductive blocks 424 and 425 to hold temperature sensors placed therein. The blowers 432 and 433 may be activated or deactivated and die cooling assemblies may be engaged or disengaged by switches on die control panel or by a programmable logic controller. The flow rate of air passed across the mold members may be adjusted via die control panel, or the flow rate may be maintained at a constant rate during operation of blowers 432 and 433.

A programmable logic controller 417 may be housed witiiin the control panel. Controller 417 is preferably adapted to independently control operation of the light generators 402 and 404 such that activating light is directed in a plurality of pulses toward at least one of die mold members. The controller 417 is preferably programmable such that a predetermined time elapses between each of the pulses to optimize the curing cycle. The controller 417 may be adapted to cause die strobes to fire at predetermined times through the curing cycle, thereby controlling the rate of polymerization and exothermic heat generation of the lens forming composition. One programmable logic controller that has been found to perform adequately is the Little Star Microcontroller combined witii a Relay Six relay board, both commercially available from Z- World Engineering of Davis, California. The strobe firing sequence may be written in Dynamic C programming language. The Ultra 1800 White Lightning photographic strobes, commercially available from Paul C. Buff, Incorporated of Nashville, Tennessee, have been found to perform adequately. It is to be understood tiiat embodiments of apparatus 400 may be combined witii the methods and apparatus of prefened embodiments described above in previous sections.

IMPROVED LENS CURING APPARATUS EXAMPLE

An 80 mm diameter glass 28 flattop bifocal mold witii a distance radius of curvature of -5.98 diopters and a +2.50 diopter bifocal add power was sprayed with a mixture of isopropyl alcohol and distilled water in equal parts and wiped dry witii a lint free paper towel. The mold was assembled into a silicone rubber gasket in combination with a cleaned convex mold possessing a radius of curvature of +4.11 diopters. A raised lip present on the inner circumference of the rubber gasket provided a spacing of 4.2 mm between die two molds at the center point.

The mold/gasket assembly was positioned on a filling stage and die edge of the gasket was peeled back to permit the cavity to be filled with 14.4 grams of OMB-91 lens forming composition, commercially available from the FastCast Corporation of Louisville, Kentucky. The edge of the gasket was returned to its sealing relationship with the edges of the molds and excess lens forming composition was vacuumed off the non- casting surface of the back mold witii a suction device. The filled mold/gasket assembly was transfened from the filling stage to a stage incorporated into a lens drawer of a strobe curing chamber. The assembly was irradiated on both its sides according to the exposure cycle shown in FIG. 34, which was controlled by a programmable logic controller. The power settings on the strobes were adjusted to maximum power.

During the irradiation, the lens cell was continuously exposed to streams of recirculated air directed by the blower and cooled by die tiiermoelectric cooling module shown in Figs. 31 and 32. At die beginning of die cycle, die air temperature was 68 degrees F and at the end of die cycle is was measured at 73 degrees F. The air temperature varied during the rest of the cycle up to temperatures as high as 90 degrees F, primarily as a result of the heat added to die system from both the strobe flash lamps and the exotiiermic heat generated by the lens forming composition. It is anticipated that d e operating temperatures of the air could be reduced to well below ambient temperature and die curing cycle could be shortened by use of thermoelectric coolers having a greater capacity than those used in tins experiment.

The casting cell was turned over in the chamber so that its convex surface faced upwards and was dosed with 13 flashes to the convex surface and 10 flashes to the concave surface. The casting cell was removed from the strobe chamber, the gasket was stripped from the assembly, and residual uncured material was wiped from the exposed edge of die lens. The cell was returned to the chamber with its concave side facing up and was dosed with an additional 13 flashes to die concave surface and 10 flashes to the convex surface. The non-casting surfaces of both the front and the back molds were placed in contact with thermal transfer pads, commercially available from the FastCast Corporation of Louisville, Kentucky, at temperatures of approximately 150 to 200 degrees F as measured on top of die pad for ten minutes. The assembly was removed from the tiiermal transfer pad and die back mold was removed with a slight impact from an appropriately sized wedge. The lens with the front mold attached was placed in a container of water at room temperature and die lens separated from the front mold. The now finished lens was sprayed with a mixture of isopropyl alcohol and water in equal parts and wiped dry. The finished lens was 4.0 mm tiiick at the center and was 74 mm in diameter. The lens exhibited a focusing power of +1.98 -0.02D with a bifocal addition power of +2.54D, provided good optical quality, and was non-yellow.

IMPROVED LENS CURING PROCESS

When casting an eyeglass lens with activating light, the gelation pattern of the lens forming composition may affect the resultant optical quality of the lens. If there are localized discontinuities in the light intensities received by die monomer contained in the casting cavity during the early stages of the polymerization process, optical distortions may be seen in the finished product. Higher power lenses are, by definition, thicker in certain regions than relatively lower power lenses of the same diameter. The layers of a lens closest to die mold faces of d e casting cavity tend to receive a higher light intensity tiian the deeper layers because the lens forming composition absorbs some of the incident light. This causes the onset of polymerization to be delayed in die deeper layers relative to the outer layers, which may cause optical distortions in the finished product. It is believed tiiat concunent with this differential curing rate, there is a difference in the rate of exothermic heat generation, specifically, the deeper regions will begin to generate heat after the outer regions in the cavity have already cured and the effectiveness of the heat removal may be impaired, contributing to optical waves and distortions in the finished product. This phenomena is particularly observable in high powered positive lenses due to the magnification of such defects.

In an embodiment, the lens forming composition contained within the casting cavity is exposed to relatively high intensity activating light for a time period sufficient to initialize the reaction. Inadiation is terminated before the polymerization of the lens forming composition proceeds far enough to generate a substantial amount of heat. This initial relatively high intensity dose preferably substantially uniformly gels the material within the casting cavity such that the difference in the rate of reaction between the inner and outer layers of the lens being cured is reduced, thereby eliminating the waves and distortions often encountered when using continuous low intensity irradiation to initialize the reaction, particularly with high dioptric power positive lenses.

In an embodiment, the relatively high intensity dose of activating light is applied to d e lens forming composition in the form of pulses. The pulses preferably have a duration of less than about 10 seconds, preferably less than about 5 seconds, and more preferably less than about 3 seconds. The pulses preferably have an intensity of at least about 10 milliwatts/cm2, more preferably at least about 100 milliwatts/cm2, and more preferably still between about 150 milliwatts/cm2 and about 250 milliwatts/cm2. It is prefened tiiat substantially all of the lens forming composition forms into a gel after the initial application of the relatively high intensity activating light. In an embodiment, no more than an insubstantial amount of heat is generated by exotiiermic reaction of the lens foπning composition during the initial application of the relatively high intensity activating light.

Subsequent to this initial high intensity dose, a second inadiation step is performed in which the material contained within the casting cell is preferably irradiated for a relatively longer time at a relatively lower mtensity while cool fluid is directed at the non-casting surface of at least one of the molds forming the cavity. The cooling fluid preferably removes the exotiiermic heat generated by die polymerization of the lens forming composition. If the intensity of the activating light is too great during this second irradiation step, the rate of heat generation will tend to be too rapid and the lens may release prematurely from the casting face of the mold and/or crack. Similarly, should the rate of heat removal from the lens forming composition be too slow, the lens may release prematurely and/or crack. It is prefened that the mold/gasket assembly containing die lens forming composition be placed within the cooling environment as shortly after d e initial dose of activating light as possible.

In an embodiment, the activating light applied to die lens forming composition during the second irradiation step is less about 350 microwatts/cm2, more preferably less than about 150 microwatts/cm2, and more preferably still between about 90 microwatts/cm2 and about 100 microwatts/cm2. During the second irradiation step, the activating light may be applied to die lens forming composition continuously prefened or in pulses. A translucent high density polyethylene plate may be positioned between the activating light generator and at least one of the mold members to reduce the intensity of the activating light to witiiin a prefened range. In an embodiment, relatively high mtensity activating light is applied to the lens curing composition m a thud irradiation step to post cure the lens subsequent to the second relatively low mtensity inadiation step In the third irradiation step, pulses of activatmg light are preferably directed toward die lens formmg composition, although the composition may be continuously inadiated mstead The pulses preferably have an mtensity of at least about 10 milliwatts/cm2, more preferably at least about 100 milhwatts/cm2, and more preferably still between about 100 milhwatts/cm2 and about 150 milliwatts/cm2

Each of the above-mentioned irradiation steps is preferably performed by directmg the activatmg light through each of the first and second mold members The eyeglass lens is preferably cured m a total time of less than 30 minutes and is preferably free of cracks, stπations, distortions, haziness, and yellowness It is believed tiiat the above-described methods enable the production of whole lenses m prescπption ranges beyond those cunently attamable with continuous low mtensity irradiation The method can be practiced m the curmg of relatively high or low power lenses with a reduced incidence of optical distortions m the finished lens as compared to conventional methods It is to be understood that the above-descπbed metiiods may be used mdependently or combmed with die methods and apparatus of prefened embodiments descnbed above m the previous sections

IMPROVED CURING PROCESS EXAMPLE

An 80 mm diameter glass progressive addition mold with a nominal distance radius of curvature of - 6 00 diopters and a +2 50 diopter bifocal add power was sprayed with a mixture of isopropyl alcohol and distilled water m equal parts and wiped dry with a lmt free paper towel The progressive mold was lenticulanzed to provide an optical zone 68 mm m diameter along the 180 degree meπdian and 65 mm m diameter along the 90 degree meridian The non-casting face of the mold was mounted to a suction cup, which was attached to a spmdle The spmdle was placed on a spinning device provided m die FastCast UX-462 FlashCure Unit, commercially available from the FastCast Corporation of Louisville, Kentucky A one mch diameter pool of liquid Primer was dispensed mto the center of the horizontally positioned glass mold from a soft polyethylene squeeze bottle equipped with a nozzle with an orifice diameter of approximately 0 040 mches The composition of the Pπmer is discussed m detail below (see Scratch Resistant Lens Formation Process Example) The spm motor was engaged to rotate the mold at a speed of approximately 850 to 900 revolutions per minute, which caused the liquid material to spread out over the face of the mold Immediately thereafter, a steady stream of an additional 1 5 to 2 0 grams of Primer material was dispensed onto the castmg face of the spinning mold with the nozzle tip positioned at a 45 degree angle approximately 12 mm from the mold face such tiiat the stream was flowing with die direction of rotation of the mold The stream of Primer matenal was directed first at the center of the mold face and then dispensed along the radius of the mold face in a direction from the center toward the edge of the mold face The solvent present m the Pπmer was allowed to evaporate off for 8 to 10 seconds while the mold was rotated The rotation was stopped and the Pπmer coat present on the mold was cured via two exposures to the activating light output from the medium pressure mercury vapor lamp contained in the UX-462 FlashCure unit, totaling approximately 300 mJ/cm2.

The spin motor was again engaged and approximately 1.5 to 2.0 grams of HC8-H Hard Coat (see description below), commercially available from the FastCast Corporation of Louisville, Kentucky was dispensed onto the spinning mold in a similar fashion as the Primer coat. The solvent present in the HC8-H was allowed to evaporate off for 25 seconds while the mold was rotated. The rotation was stopped and the HC8-H coat was cured in the same manner as the Primer coat.

The mold was removed from the FlashCure unit and assembled into a silicone rubber gasket in combination with a cleaned convex mold possessing a radius of curvature of +2.00 diopters. The raised lip present on the inner circumference of the rubber gasket provided a spacing of 6.3 mm between die two molds at the center point. The mold/gasket assembly was positioned on a filling stage and the edge of die gasket was peeled back to permit the cavity to be filled with OMB-91 lens forming composition, commercially available from the FastCast Corporation of Louisville, Kentucky. The edge of the gasket was returned to its sealing relationship with the edges of the molds and die excess lens forming composition was vacuumed off the non- casting surface of the back mold witii a suction device. The filled mold gasket assembly was placed on a stage in die UX-462 FlashCure unit and subjected to four exposures of the activating light output from the six inch medium pressure mercury vapor lamp, totaling approximately 600 mJ/cm2.

Immediately following this initial dose of high intensity activating light, the assembly was transfened to the FC-132 curing chamber where the casting cell was continuously exposed to streams of air having a temperature of 42 degrees F while being irradiated with very low intensity activating light for eight minutes. The light intensity measured approximately 90 microwatts/cm2 from above plus approximately 95 microwatts/cm2 from below, according to the plus lens light distribution pattern called for by the manufacturer. The lamp racks are typically configured to deliver activating light having an intensity of about 300 microwatt/cm2 for the standard fifteen minute curing cycle. The reduction in activating light intensity was accomplished by inserting a translucent high density polyethylene plate into the light distribution filter plate slot along with the plus lens light distribution plate. A translucent high density polyetiiylene plate was positioned between the front mold member and one light distribution plate and between the back mold member and die otiier light distribution plate.

The assembly was subsequently returned to the UX-462 FlashCure unit and the non-casting surface of the back mold was exposed to four doses of high intensity activating light totaling approximately 1150 mJ/cm2. The gasket was stripped from the assembly and residual uncured material wiped from die exposed edge of die lens. An oxygen barrier strip (polyethylene) was wrapped around the edge of the lens and the mold was exposed to two more doses of high intensity activating light totaling 575 mJ/cm2 to the non-casting surface of the front mold followed by eight more flashes to the non-casting surface of the back mold totaling 2300 mJ/cm2.

The non-casting surface of the back mold was placed in contact with a tiiermal transfer pad, commercially available from e FastCast Corporation of Louisville, Kentucky, at a temperature of approximately 150 to 200 degrees F for thirteen minutes. The assembly was removed from the thermal transfer pad and die back mold was removed with a slight impact from an appropriately sized wedge The front mold with the lens attached tiiereto was placed in a contamer of room temperature water and the lens separated from die front mold The now- finished lens was sprayed with a mixture of isopropyl alcohol and water m equal parts and wiped dry The lens read +3 98 D with an addition power of +2 50, was clear , non-yellow, and exhibited good optics

IMPROVED SCRATCH RESISTANT LENS FORMATION PROCESS

The "ln-mold" method involves forming a scratch resistant coating over an eyeglass lens by placing the liquid coatmg m a mold and subsequently curing it The m-mold method is advantageous to "out-of-mold" methods smce the m-mold method exhibits less occunences of coatmg defects manifested as lnegulaπties on the anterior surface of the coatmg Usmg the m-mold method produces a scratch resistant coatmg that replicates the topography and smoothness of the mold castmg face However, a problem encountered when usmg conventional m-mold scratch resistant coatings is that minute "pinholes" often form m the coatmg It is believed that the pinholes are caused by either contaminants on the mold, airborne particles falling on the coating before it is cured, or bubbles formed durmg the application of the coating which burst afterwards The formation of such pinholes is especially prevalent when usmg a flat-top bifocal mold, such as the one depicted in Fig 35 As illustrated, the segment lme 454 of a bifocal segment 452 below the mam surface 456 of the mold reduces the smoothness of the castmg face When a coatmg is spm-coated over the mold face, tins mdentation becomes an obstacle to the even flow of the castmg face The pinhole defects are mamly a problem m tmted lenses because the dye used to tmt a lens can penetrate through the pinholes, resulting m a tiny speck of dye visible m die lens

Accordmg to an embodiment of the mvention, a first coating composition, I e , a polymerizable "primer" material is passed through a filter and then placed withm a mold member having a casting face and a non-casting face The first coatmg composition preferably contains a photomitiator to make it curable upon exposure to activatmg light The mold member may then be spun so that the first composition becomes distπbuted over the castmg face The mold member is preferably rotated about a substantially vertical axis at a speed between about 750 and about 1000 revolutions per minute Further, a dispensmg device may be used to direct an additional amount of the first composition onto the castmg face while the mold member is spinning The dispensmg device preferably moves from the center of the mold member to an edge of d e mold member so that the additional amount is directed along a radius of the mold member Activating light is preferably directed at the mold member to cure at least a portion of the first composition

A second coatmg composition may then be placed upon die first composition in the mold member The second coatmg is also preferably curable when exposed to activating light because it contams a photomitiator The mold member is agam spun to distribute the second coatmg composition over the cured portion of die first coating composition The mold member may also be spun simultaneously while addmg the second composition to the mold member Activating light is then preferably directed at the mold member to simultaneously cure at least a portion of the second coatmg composition and form a transparent combination coat havmg both coatmg compositions The combination coat is preferably a substantially scratch-resistant coatmg. The mold member may then be assembled with a second mold member by positioning a gasket between the members to seal them. Therefore, a mold having a cavity shared by the oπgmal two mold members is formed. An edge of the gasket may be displaced to insert a lens-formmg composition mto the cavity. The combmation coat and the lens-formmg material preferably adhere well to each other This lens- forming composition preferably comprises a photomitiator and is preferably cured using activating light. Air which preferably has a temperature below ambient temperature may be directed toward a non-casting face of the second mold member to cool the lens-formmg composition while it is bemg cured

The pπmer coat preferably compnses a mixture of high viscosity monomers, a low viscosity, low flashpoint organic solvent, and a suitable photomitiator system. The solvent may make up about more than 80 % of the mixture, preferably about 93% to 96% This mixture preferably has low viscosity and preferably covers any surface irregulanty durmg the spm application, for example the segment lme of a flat-top bifocal mold The low flashpoint solvent preferably evaporates off relatively quickly, leaving a thin layer of high viscosity monomer, contammg photomitiator, which coats the casting face of the mold The cured primer coat is preferably soft to allow it to adhere well to the glass mold face. Since the primer coat is soft, it may not possess scratch resistant characteristics. However, applying a high scratch resistance hard coatmg (l e., the second coating composition) to the pπmer coat preferably results m a scratch resistant combination coat. The hard coat preferably contams a solvent which evaporates when the mold member is rotated to distribute the hard coating over the pπmer coat In general, the ideal pnmer material preferably possesses the following characteristics: exhibits chemical stability at normal storage conditions, e.g. at room temperature and m the absence of activating light; flows well on an irregular surface, especially over a flat-top bifocal segment; when cured with a specified ultraviolet dose, leaves a crack-free coatmg, with a high double bond conversion (approximately greater than 80%), mamtams adhesion witii die mold face through the lens formmg curmg cycle, especially the segment part of the flat-top bifocal mold, and is chemically compatible witii the hard coat which is subsequently applied on top of it, e.g. forms an optically clear combmation coat Even though pinhole defects may be present in either the pπmer coat or the hard coat, it is highly unlikely that defects m one coat would comcide with defects of anotiier coat. Each coat preferably covers the holes of the other coat, resulting m less pinholes m the combmation coat Thus, the finished m-mold coated lens may be tmted usmg dye witiiout problems created by pinholes. It is also preferably free of cracks, yellowness, haziness, and distortions.

In an embodiment, the gasket between the first mold member and the second mold member may be removed after a portion of the lens-formmg material has been cured. The removal of the gasket preferably exposes an edge of the lens. An oxygen banier havmg a photomitiator may be placed around the exposed edge of the lens, wherein the oxygen banier photomitiator is preferably near an uncured portion of the lens-formmg composition Additional activating light rays may then be directed towards the lens to cause at least a portion of the oxygen banier photomitiator to initiate reaction of the lens-formmg material. The oxygen banier preferably prevents oxygen from contacting at least a portion of the lens forming composition duπng exposure of the lens to the activating light rays Accordmg to one embodiment, a substantially solid conductive heat source is applied to one of the mold members Heat may be conductively transfened from die heat source to a face of die mold member Further, the heat may be conductively transfened through the mold member to the face of the lens

SCRATCH RESISTANT LENS FORMATION PROCESS EXAMPLE

A first coating composition, hereinafter refened to as "Primer", was prepared by mixmg the following components by weight

93 87% acetone,

3 43%o SR-399 (dipentaerythπtol pentaacrylate), available from Sartomer, 2 14%) CN-104 (epoxy acrylate), available from Sartomer,

0 28% Irgacure 184 (1-hydroxycyclohexylphenylketone), available from Ciba-Geigy, and

0 28% Darocur 1173 (2-hydroxy-2-methyl-l-phenyl-propan-l-one) available from Ciba-Geigy

A second coatmg composition, hereinafter refened to as "HC8-H" was prepared by mixmg the following components by weight

84 69% 1 -methoxy 2-propanol, 9 45%> SR-399 (dipentaerytiiritol pentaacrylate), available from Sartomer,

4 32%o SR601 (ethoxylated bisphenol A diacrylate), available from Sartomer, and

1 54% Irgacure 184 (1-hydroxycyclohexyl- phenyl ketone), available from Ciba-Geigy

Each of these coatmg compositions was prepared by first dissolving the monomers mto the solvent, then addmg the photomitiators, mixmg well, and finally passing the composition through a one micron filter pnor to use

An 80 mm diameter glass 28 mm flattop mold with a distance radius of curvature of -6 00 diopters and a +2 00 diopter bifocal add power were sprayed with a mixture of isopropyl alcohol and distilled water m equal parts The flattop mold was wiped dry with a lmt free paper towel The non-casting face of the mold was mounted to a suction cup, which was attached to a spmdle The spmdle was placed on die spinning device provided in d e FastCast UX-462 FlashCure Unit, commercially available from the FastCast Corporation of Louisville, Kentucky

A one mch diameter pool of liquid Primer was dispensed mto the center of the horizontally positioned glass mold The Pπmer was dispensed from a soft polyethylene squeeze bottle equipped witii a nozzle havmg an oπfice diameter of approximately 0 040 mches A spm motor of the spinning device was engaged to rotate the mold at a speed of approximately 850 to 900 revolutions per mmute, causmg the liquid Primer to spread out over the face of the mold Immediately thereafter, a steady stream of an additional 1 5 to 2 0 grams of Primer material was dispensed onto the castmg face of the spinning mold The stream of Pπmer material was directed onto the casting face with the nozzle tip positioned at a 45 degree angle approximately 12 mm from the mold face. This positioning of the nozzle tip made die stream to flow with the direction of rotation of the mold. The stream of Primer material was directed first at the center of the mold face and then dispensed along the radius of die mold face in a direction from the center toward the edge of d e mold face.

The solvent present in the Primer was allowed to evaporate off for 8 to 10 seconds during rotation of die mold. The rotation was stopped and die Primer coat which remained on d e mold was cured via two exposures to the activating light output from the medium pressure mercury vapor lamp contained in me UX-462 FlashCure unit, totaling approximately 300 mJ/cm2. All light intensity/dosage measurements cited herein were taken with an International Light IL-1400 Radiometer equipped with an XLR-340B Detector Head, both commercially available from International Light, Inc. of Newburyport, Massachusetts. Upon exposure to the activating light, the spin motor was again engaged and approximately 1.5 to 2.0 grams of HC8-H Hard Coat, commercially available from the FastCast Corporation of Louisville, Kentucky was dispensed onto the spinning mold in a similar fashion as the Primer coat. The solvent present in d e HC8-H was allowed to evaporate off for 25 seconds while the mold was spinning. The rotation was stopped, and die HC8- H coat was cured in the same manner as the Primer coat. The mold was removed from the FlashCure unit and assembled into a silicone rubber gasket in combination with a cleaned convex mold possessing a radius of curvature of +7.50 diopters. The raised lip present on die inner circumference of die rubber gasket provided a spacing of 1.8 mm between the two molds at the center point. At this point, the mold/gasket assembly was positioned on a filling stage and d e edge of the gasket was peeled back to permit the cavity to be filled with OMB-91 lens forming composition, commercially available from the FastCast Corporation of Louisville, Kentucky. The edge of the gasket was returned to its sealing relationship with the edges of die molds and d e excess lens forming composition was vacuumed off the non-casting surface of the back mold witii a suction device.

The filled mold/gasket assembly was transfened from the filling stage to an FC-132 curing chamber, commercially available from the FastCast Corporation of Louisville, Kentucky. While in the chamber, the assembly was continuously inadiated from both sides for a period of 15 minutes at approximately 300 microwatts/cm2 from above and at approximately 350 microwatts/cm2 from below, according to die minus lens light distribution pattern called for by the manufacturer. During the irradiation, the casting cell was continuously exposed to streams of air having a temperature of 42° F.

The mold/gasket assembly was subsequently returned to the UX-462 FlashCure unit. The non-casting surface of the back mold was exposed to four doses of high intensity activating light totaling approximately 1150 mJ/cm2. The gasket was stripped from the assembly and residual uncured material was wiped from the exposed edge of the lens. An oxygen banier strip (polyethylene) was wrapped around the edge of d e lens. The mold/gasket assembly was exposed to two more doses of high intensity activating light, wherein 575 mJ/cm2 total was directed to the non-casting surface of the front mold. Subsequently, eight more flashes of the activating light were directed to the non-casting surface of the back mold, totaling 2300 mJ/cm2.

The non-casting surface of the back mold was placed in contact witii a thermal transfer pad, commercially available from the FastCast Corporation of Louisville, Kentucky, at a temperature of approximately 150 to 200° F for thirteen minutes. The mold/gasket assembly was removed from the thermal transfer pad, and the back mold was removed witii a slight impact from an appropriately sized wedge. The front mold witii the lens attached thereto was placed in a container of room temperature water. While within the water, the lens became separated from the front mold. The now-finished lens was sprayed with a mixture of isopropyl alcohol and water in equal parts and wiped dry. The lens was positioned in a holder and placed into a heated dye pot for 5 minutes. The dye pot contained a solution of BPI Black, commercially available from Brain Power, Inc. of Miami, Florida, and distilled water at a temperature of approximately 190 degrees F. The lens was removed from the dye pot, rinsed with tap water, and wiped dry. The lens exhibited a total visible light absorbance of approximately 80%. When inspected for cosmetic defects on a light table, no pinhole defects were observed. Further, the tint which had been absorbed by the back surface of the lens was found to be smooth and even.

NON-POLYMERIZABLE SCRATCH RESISTANT COATING PROCESS EXAMPLE

A non-polymeπzable coatmg composition, heremafter refened to as "Precoat", was prepared by mixing the following matenals by weight 99 80% acetone, and 0 20% BYK-300, a slip agent commercially available from BykChemie

An 80 mm diameter glass 28 mm flattop mold with a distance radius of curvature of -6 00 diopters and a +2 00 diopter bifocal add power was sprayed with a mixture of isopropyl alcohol and distilled water m equal parts The mold was subsequently wiped dry with a lint free paper towel The non-casting face of die mold was mounted to a suction cup, which was attached to a spmdle The spmdle was placed on the spinning device provided m die FastCast UX-462 FlashCure Unit, commercially available from the FastCast Corporation of Louisville, Kentucky

A spm motor of the spinning device was engaged to rotate the mold at a speed of approximately 850 to 900 revolutions per mmute A steady stream of approximately 2 0 to 3 0 grams of Precoat matenal was dispensed onto the casting face of the spinning mold with die nozzle tip positioned at a 45 degree angle approximately 12 mm from the mold face, thereby causing the stream to flow with the direction of rotation of the mold The stream of Precoat material was directed first at the center of the mold face The stream was then dispensed along the radius of the mold face m a direction from the center toward the edge of the mold face The mtended purpose of the Precoat was to improve the wetting characteristics of the glass mold so tiiat the HC8-H matenal would flow over it more evenly The solvent present m the Precoat evaporated off the spinning mold almost mstantly, and approximately 1 5 to 2 0 grams of HC8-H Hard Coat was dispensed onto the casting face of the spinning mold The HC8-H Hard Coat was directed onto the castmg face along the radius of the mold face m a direction from the center toward the edge The nozzle tip was positioned at a 45 degree angle approximately 12 mm from the mold face such that the stream was flowing with the direction of rotation of the mold The solvent present m the HC8-H was allowed to evaporate off for 25 seconds while d e mold was spinning The rotation was stopped, and the HC8-H coat was cured via two exposures to the activating light output from the medium pressure mercury vapor lamp contained m the UX-462 FlashCure unit, totalmg approximately 300 mJ/cm2

The mold was removed from the FlashCure unit and assembled mto a silicone rubber gasket m combmation with a cleaned convex mold possessmg a radius of curvature of +7 50 diopters The raised lip present on the inner cucumference of the rubber gasket provided a spacmg of 1 8 mm between the two molds at die center pomt The mold/gasket assembly was positioned on a filling stage, and die edge of the gasket was peeled back to permit the cavity to be filled with OMB-91 lens formmg composition, commercially available from the FastCast Corporation of Louisville, Kentucky The edge of the gasket was returned to its sealmg relationship with the edges of the molds The excess lens formmg composition was vacuumed from die non- castmg surface of the back mold with a suction device The filled mold gasket assembly was transfened from the filling stage to an FC-132 curing chamber, commercially available from the FastCast Corporation of Louisville, Kentucky The assembly was contmuously madiated from both sides for a period of 15 mmutes at approximately 300 microwatts/cm2 from above and approximately 350 microwatts/cm2 from below, accordmg to the minus lens light distribution pattern called for by the manufacturer. During the irradiation, the casting cell was continuously exposed to streams of air having a temperature of 42° F.

The assembly was subsequently returned to the UX-462 FlashCure unit. The non-casting surface of the back mold was exposed to four doses of high intensity activatmg light, totaling approximately 1150 mJ/cm2. The gasket was stripped from the assembly, and residual uncured material was wiped from the exposed edge of die lens. An oxygen banier strip (i.e., polyethylene) was wrapped around the edge of die lens and die cell was exposed to two more doses of high intensity activating light, wherein 575 mJ/cm2 total were directed to the non- casting surface of the front mold. Eight more flashes of high intensity activating light followed. The eight flashes exposed d e non-casting surface of the back mold to a total of 2300 mJ/cm2. The non-casting surface of the back mold was placed in contact with a tiiermal transfer pad at a temperature of approximately 150 to 200° F for thirteen minutes. The assembly was removed from die thermal transfer pad, and die back mold was removed witii a slight impact from an appropriately sized wedge. The front mold with the lens attached tiiereto was placed in a container of room temperature water in order to cause the lens to be separated from the front mold. The now-finished lens was sprayed with a mixture of isopropyl alcohol and water in equal parts and wiped dry.

The lens was positioned in a holder and placed into a heated dye pot for 5 minutes. The dye pot contained a solution of BPI Black, commercially available from Brain Power, Inc. of Miami, Florida, and distilled water at a temperature of approximately 190° F. The lens was removed from the dye pot, rinsed with tap water and wiped dry. The lens exhibited a total visible light absorbance of approximately 80%. When inspected for cosmetic defects on a light table, several pinhole tint defects were observed. They appeared to be in die range of 0.2 mm to 0.05 mm in diameter. However, die tint which had been absorbed by die back surface of the lens was found to be smooth and even.

ACTIVATING LIGHT INITIATED POLYMERIZATION OF A LENS FORMING COMPOSITION CONTAINING ACTIVATING LIGHT ABSORBING MATERIALS

Materials (hereinafter refened to as "activating light absorbing compounds") tiiat absorb various degrees of activating light may be used in an eyeglass lens to inhibit activating light from being transmitted through the eyeglass lens. Preferably, the activating light absorbing compounds inhibit ultraviolet light from being transfened through the eyeglass lens. Such an eyeglass lens advantageously inhibits activating light from being transmitted to the eye of a user wearing the lens. Thus eyeglass lenses containing activating light absorbing compounds may function to protect the eyes of a person from damaging ultraviolet light. Photochromic pigments are one type of activating light absorbing compounds. Photochromic inorganic lenses which contain silver halide particles or cuprous halide particles suspended throughout the body of die lens are well known and have been commercially available for decades. Such inorganic lenses, however, suffer the disadvantage of being relatively heavy and less comfortable to the wearer when compared to organic lenses. Consequently, the majority of the eyeglass lenses produced today are formed from organic materials rattier ti an inorganic materials. Accordingly, photochromic plastic eyeglass lenses have been the subject of considerable attention in recent years. Efforts to provide a plastic eyeglass lens which demonstrates photochromic performance have primarily centered around permeating and or covering the surface(s) of an already formed lens with photochromic pigments. This general technique may be accomplished by a number of specific methods. For example, (a) the lens may be soaked in a heated bath which contains photochromic pigments, (b) photochromic pigments may be transfened into the surface of a plastic lens via a solvent assisted transfer process, or (c) a coating containing photochromic pigments may be applied to the surface of a lens. A problem with such methods is that the lens often might not absorb enough of the photochromic pigments at low temperatures, resulting in an eyeglass lens which does not exhibit acceptable photochromic performance. Unfortunately, increasing the temperature used during absorption of die photochromic pigments is not a solution to this problem since at high temperatures degradation of die polymer contained within the lens may occur.

Attempts have also been made to incorporate photochromic pigments into the liquid monomer from which plastic lenses are thermally polymerized. See U.S. Patent No. 4,913,544 to Rickwood et al., wherein it is disclosed that triethyleneglycol dimethacrylate monomer was combined witii 0.2% by weight of various spiro- oxazine compounds and 0.1% benzoyl peroxide and subsequently thermally polymerized to form non- prescription eyeglass lenses. Generally, efforts to incorporate photochromic pigments into the liquid monomer from which die lenses are polymerized have been unsuccessful. It is believed tiiat the organic peroxide catalysts utilized to initiate die tiiermal polymerization reaction tend to damage die photochromic pigments, impairing their photochromic response.

Curing of an eyeglass lens using activating light to initiate the polymerization of a lens forming composition generally requires that the composition exhibit a high degree of activating light transmissibility so that the activating radiation can penetrate to the deeper regions of the lens cavity. Otherwise the resulting cast lens may possess optical aberrations and distortions. The cast lens may also contain layers of cured material in the regions closest to the transparent mold faces, sandwiching inner layers which are eitiier incompletely cured, gelled, barely gelled, or even liquid. Often, when even small amounts of activating light absorbing compounds of the types well known in die art are added to a normally activating light curable lens forming composition, substantially the entire amount of lens forming composition contained within the lens cavity may remain liquid in the presence of activating radiation.

Photochromic pigments which have utility for photochromic eyeglass lenses absorb activating light strongly and change from an unactivated state to an activated state when exposed to light. The presence of photochromic pigments, as well as other activating light absorbing compounds within a lens forming composition, generally does not permit enough activating radiation to penetrate into the depths of die lens cavity sufficient to cause activating light photoinitiators to break down and initiate polymerization of the lens forming composition. Thus, it is difficult to cure a lens forming composition containing activating light absorbing compounds using activating light. It is tiierefore desirable to provide a method for using activating light to initiate polymerization of an eyeglass lens forming monomer which contains activating light absorbing compounds, in spite of the high activating light absorption characteristics of the activating light absorbing compounds. Examples of such activating light absorbing compounds otiier than photochromic pigments are fixed dyes and colorless additives. In an embodiment of die present invention, an ophthalmic eyeglass lens may be made from a lens forming composition comprising a monomer, an activating light absorbing compound, an ultraviolet photoinitiator, and a co-initiator. Herein, an "ophthalmic eyeglass lens" is taken to mean any plastic eyeglass lens, including a prescription lens, a non-prescription lens, a sunglass lens, and a bifocal lens. The lens forming composition, in liquid form, is preferably placed in a mold cavity defined by a first mold member and a second mold member. It is believed that activating light which is directed toward die mold members to activate the photoinitiator causes the photoinitiator to form a polymer chain radical. The polymer chain radical preferably reacts with the co-initiator more readily tiian with the monomer. The co-initiator may react with a fragment or an active species of either the photomitiator or the polymer chain radical to produce a monomer initiating species in the regions of the lens cavity where the level of activating light is either relatively low or not present. The co-initiator is preferably activated only in the presence of the photoinitiator. Further, without the co-initiator, the photoinitiator may exclusively be activated near the surface of the lens formmg composition but not within die middle portion of die composition. Therefore, using a suitable photoinitiator combined witii a co-initiator permits polymerization of the lens foiming composition to proceed through the depths of die lens cavity. A cured, clear, abenation free lens is preferably formed in less than about 30 minutes, more preferably in less tiian about 10 minutes. Herein, a "clear lens" is taken to mean a lens that transmits visible light witiiout scattering so that objects beyond die lens are seen clearly. Herein, "abenation" is taken to mean the failure of a lens to produce point-to-point conespondence between an object and its image. The lens, when exposed to activating light preferably inhibits at least a portion of the activating light from being transmitted tiirough d e lens tiiat is preferably formed. A lens tiiat permits no activating light from passing through the lens (at least with respect to certain activating wavelengths) is more prefened.

In an embodiment, die lens forming composition which contams an activating light absorbing compound may be cured witii activating light utilizing the UVEXS curing apparatus previously described herein and depicted in Fig. 10. In anotiier embodiment, the lens forming composition may be cured witii activating light supplied from the FC-104 curing chamber which is depicted in Figs. 14 and 15. Alternately, the lens forming composition may be cured by exposing the composition to activating light multiple times using both the UVEXS and the FC-104. Preferably, all activating light directed toward the mold members is at a wavelength of 400 nm or below. The above-mentioned embodiments which describe various methods for forming eyeglass lenses may also be utilized to form the eyeglass lens hereof. The identity of the major polymerizable components of die lens forming composition tends to affect die optimal curing process. It is anticipated tiiat the identity of die activating light absorbing compound present in the monomer or blend of monomers may affect the optimal photoinitiator/co-initiator system used as well as d e optimal curing process used to initiate polymerization. Also, varying the identities or die proportions of die monomer(s) in die lens forming composition may require adjustments to various production process variables including, but not limited to, exposure times, exposure intensities, cooling times and temperatures, activating light and thermal postcure procedures and the like. For example, compositions comprising relatively slow reacting monomers, such as bisphenol A bis allyl carbonate or hexanediol dimetiiacrylate, or compositions comprising relatively higher proportions of such monomers may require either longer exposure times, higher intensities, or both. It is postulated tiiat increasing the amount of either fast reacting monomer or the initiator levels present in a system will require reduced exposure times, more rigidly controlled light doses, and more efficient exothermic heat removal.

Preferably, the monomers selected as components of die lens forming composition are capable of dissolving the activating light absorbing compounds added to tiiem. Herein, "dissolving" is taken to mean being substantially homogeneously mixed with". For example, monomers may be selected from a group including polyol (allyl carbonate) monomers, multi-functional acrylate monomers, and multi-functional methacrylic monomers for use in an activatmg light absorbing lens forming composition.

In an embodiment, die following mixture of monomers, hereinafter refened to as PRO-629, may be blended together before addition of other components required to make the lens forming composition. This blend of monomers is preferably used as die basis for a lens forming composition to which activating light absorbing compounds are added.

32% Tripropyleneglycol diacrylate (SR-306) 21 % Tetraethyleneglycol diacrylate (SR-268)

20% Trimethylolpropane triacrylate (SR-351)

17% Bisphenol A bis allyl carbonate (HiRi)

10% Hexanediol dimetiiacrylate (SR-239)

The acrylic and methacrylic monomers listed above are commercially available from Sartomer

Company in Exton, Pennsylvania. The bisphenol A bis allyl carbonate is commercially available from PPG in Pittsburgh, Pennsylvania. The hexanediol dimetiiacrylate is hereinafter refened to as HDDMA.

A polymerization inhibitor may be added to die monomer mixture at relatively low levels to inhibit polymerization of the monomer at inappropriate times (e.g., during storage). Preferably about 0 to 50 ppm of monomethylether hydroquinone (MEHQ) are added to die monomer mixture. It is also prefened that the acidity of die monomer mixture be as low as possible. Preferably less than about 100 ppm residual acrylic acid exists in the mixture. It is also prefened tiiat the water content of the monomer mixture be relatively low, preferably less than about 0.15 %.

Activating light photoinitiators include: 1-hydroxycyclohexylphenyl ketone commercially available from Ciba Additives under die trade name of Irgacure 184; mixtures of bis(2,6-dimetiιoxybenzoyl) (2,4,4- trimethyl phenyl) phosphine oxide and 2-hydroxy-2-mefhyl-l-phenyl-propan-l-one commercially available from Ciba Additives under the trade name of Irgacure 1700; mixtures of bis(2,6-dimetiιoxybenzoyl) (2,4,4 trimethyl phenyl) phosphine oxide and 1-hydroxycyclohexylphenyl ketone commercially available from Ciba Additives under the trade names of Irgacure 1800 and Irgacure 1850; 2,2-dimetiιoxy-2-phenyl acetophenone commercially available from Ciba Additives under the trade name of Irgacure 651; 2-hydroxy-2-methyl-l- phenyl-propan-1-one commercially available from Ciba Additives under the trade names of Darocur 1173; mixtures of 2,4,6-trimethylbenzoyl-diphenylphoshine oxide and 2-hydroxy-2-methyl-l-phenyl-propan-l-one commercially available from Ciba Additives under the trade name of Darocur 4265; 2,2-dietiιoxyacetophenone (DEAP) commercially available from First Chemical Corporation of Pascagoula, Mississippi, benzil dimetiiyl ketal commercially available from Sartomer Company under the trade name of KB-1; an alpha hydroxy ketone initiator commercially available from Sartomer company under the trade name of Esacure KIP 1 OOF; 2-methyl thioxanthone (MTX), 2-chloro-thioxantiιone (CTX), thioxanthone (TX), and xanthone, all commercially available from Aldrich Chemical; 2-isopropyl-thioxantiιone (ITX) commercially available from Aceto Chemical in Flushing, New York; mixtures of triaryl sulfonium hexafluoroantimonate and propylene carbonate commercially available from Sartomer Company under the trade names of SarCat CD 1010, SarCat 1011, and SarCat KI85; diaryl iodinium hexafluoroantimonate commercially available from Sartomer Company under the trade name of SarCat CD- 1012; mixtures of benzophenone and 1-hydroxycyclohexylphenyl ketone commercially available from Ciba Additives under the trade name of Irgacure 500; 2-benzyl-2-N,N- dimethylamino-l-(4-moφholinophenyl)-l-butanone commercially available from Ciba Additives under the trade name of Irgacure 369; 2-methyl-l-[4-(metiiyltiiio)phenyl]-2-morpholino-propan-l-one commercially available from Ciba Additives under the trade name of Irgacure 907; bis(η5-2,4-cyclopentadien-l-yl)-bis-[2,6- difluoro-3-(lH-pyrrol-l-yl) phenyl] titanium commercially available from Ciba Additives under die trade name of Irgacure 784 DC; mixtures of 2,4,6-trimethyl-benzophenone and 4-methyl-benzophenone commercially available from Sartomer Company under the trade name of EsaCure TZT; and benzoyl peroxide and meti yl benzoyl formate both available from Aldrich Chemical in Milwaukee, Wisconsin.

A prefened activating light photoinitiator is bis(2,6 dimethoxybenzoyl) (2,4,4 trimethyl phenyl) phosphine oxide, commercially available from Ciba Additives in Tarrytown, New York under the trade name of CGI-819. The amount of CGI-819 present in a lens forming composition containing photochromic compounds preferably ranges from about 30 ppm by weight to about 2000 ppm by weight.

Co-initiators which may have utility in the present invention include reactive amine co-initiators commercially available from Sartomer Company under the trade names of CN-381, CN-383, CN-384, and CN- 386, where tiiese co-initiators are monoacrylic amines, diacrylic amines, or mixtures thereof. Other co-initiators include N,N-dimethyldiethanolamine (N,NMDEA), triethanolamine (TEA), ethyl-4-dimethylamino benzoate (E-4-DMAB), ethyl-2-dimethylamino benzoate (E-2-DMAB), all commercially available from Aldrich Chemicals. Co-initiators which may also be used include n-butoxyetiιyl-4-dimetiιyl amino benzoate, P- dimethyl amino benzaldehyde. Otiier co-initiators include N, N-dimetiiyl-para-toluidine, octyl-para- (dimediylamino) benzoate commercially available from The First Chemical Group of Pascagoula, Mississippi. Preferably, the co-initiator is N-methyldietiianolamine (NMDEA) commercially available from Aldrich

Chemical in Milwaukee, Wisconsin, CN-384 commercially available from Sartomer Company, or CN-386 also commercially available from Sartomer Company. The quantity of NMDEA present in a lens forming composition containing photochromic pigments is preferably between about 1 ppm by weight and 7% by weight and more preferably between about 0.3% and 2%> by weight. Further, certain fixed pigments which may be added to die lens forming composition to create a background color within the lens (i.e., to tint the lens), may also function as co-initiators. Examples of such fixed pigments include Thermoplast Blue P, Oil Soluble Blue II, Thermoplast Red 454, Thermoplast Yellow 104, Zapon Brown 286, Zapon Brown 287, all commercially available from BASF Corporation in Holland, Michigan. Activating light absorbing compounds which may be added to a normally activating light transmissible lens forming composition include 2-(2H benzotriazole-2-yl)4-(l,l,3,3 tetramethyl butyl) phenol and 2-hydroxy- 4-medιoxybenzophenone, both commercially available from Aldrich Chemical as well as mixtures of 2-[4-((2- hydroxy-3-dodecyloxypropyl)-oxy] 2-2 hydroxyphenyl]-4,6-bis(2,4-dimethylphenyl)-l,3,5-ttiazine and 2-[4- ((2-hydroxy-3-tridecyloxypropyl)-oxy]-2-hydroxyphenyl]-4,6-bis(2,4-dimethylpheyl- 1 ,3,5-triazine commercially available from Ciba Additives under the trade name of Tinuvin 400, mixtures of poly (oxy-1,2- edianediyl), a-(3-(3-(2H-benzotriazol-2-yl)-5-(l,l-dimethylethyl)-4-hydroxyphenyl)-l-oxopropyl)-w-hydroxy and poly (oxy- 1 ,2-etiιanediyl), a-(3-(3-(2H-benzotriazol-2-yl)-5-( 1 , 1 -dimethylethyl)-4-hydroxyphenyl)- 1 - oxopropyl)-w-(3-(3-(2H-benzotriazol-2-yl)-5-l,l-dimethylethyl)-4-hydroxyphenyl)-l-oxopropoxy) commercially available from Ciba Additives under the trade name of Tinuvin 1130. Otiier activating light absorbers may include Tinuvin 328, Tinuvin 900, 2(2 hydroxy-5-mefhyl phenyl) benzotriazole, ethyl-2-cyano 3,3 diphenyl acrylate, and phenyl salicylate.

While any number of families of photochromic pigments may be incorporated into the blend of monomers, either individually or in combination, spiropyrans, spironapthoxazines, spiropyridobenzoxazines, spirobenzoxazines, napthopyrans benzopyrans, spiro-oxazines, spironapthopyrans, indolinospironapthoxazmes, indolinospironaptiiopyrans, diarylnapthopyrans, and organometallic materials, such as phenylmercury compounds are of particular interest. A phenylmercury compound available from Marks Polarized Corporation in Hauppauge, New York under the trade name of A241 may be an appropriate organometallic material. The quantity of photochromic pigments present in the lens forming composition is preferably sufficient to provide observable photochromic effect. The amount of photochromic pigments present in the lens forming composition may widely range from about 1 ppm by weight to 5% by weight. In prefened compositions the photochromic pigments are present in ranges from about 30 ppm to 2000 ppm. In the more prefened compositions the photochromic pigments are present in ranges from about 150 ppm to 1000 ppm. The concentration may be adjusted depending upon die thickness of die lens being produced to obtain optimal visible light absorption characteristics.

In an embodiment, hindered amine light stabilizers may be added to the lens forming composition. It is believed tiiat these materials act to reduce die rate of degradation of the cured polymer caused by exposure to activating light by deactivating harmful polymer radicals. These compounds may be effective in terminating oxygen and carbon free radicals, and tiius interfering with the different stages of auto-oxidation and photo- degradation. A useful hindered amine light stabilizer is bis(l,2,2,6,6-pentamethyl-4-piperidinyl) sebacate commercially available from Ciba Additives under the trade name of Tinuvin 292. Hindered phenolic antioxidants and thermal stabilizers may also be added to a lens forming composition. The hindered phenolic compounds hereof include tiiiodietiiylene bis-(3,5,-di-tert-butyl-4-hydroxy)hydrocinnamate commercially available from Ciba Additives under the trade name of Irganox 1035 and octadecyl 3,5-bis(l,l-dimethylethyl)- 4-hydroxybenzene-propanoate commercially available from Ciba Additives under the trade name of Irganox 1076.

Preferably, more than one monomer and more than one initiator are used in a lens forming composition to ensure that die initial polymerization of the lens forming composition with activating light does not occur over too short a period of time. The use of such a lens forming composition may allow greater control over the gel formation, resulting in better control of the optical quality of the lens. Further, greater control over the rate of exothermic heat generation may be achieved. Thus, cracking of die lens and premature release of the lens from the mold which are typically caused by die release of heat may be prevented. An example of a poor initiator system was observed when CGI-819 was used alone as a photoinitiator in combination with the PRO- 629 monomer blend to which activating light absorbing compounds had been added. When such an initiator system was used, a fast rate of reaction occuned near die surface of die lens cavity while a very slow rate of reaction occurred in die deeper regions of die cavity. The resultant lens exhibited unwanted waves and distortions. In anotiier example, a small amount of a co-initiator, i.e., NMDEA was added to the above lens forming composition. During the curing process, two separate waves of heat were generated when the composition was irradiated continuously at about 600 microwatts/cm2. One possible explanation of this phenomena is that the first wave resulted from reaction of the NMDEA and the second wave resulted from the reaction of the unconsumed portion of the CGI-819. Another possible explanation is that the rate of reaction was faster in the top portion than in the bottom portion of the lens forming composition since activating light was separately directed toward botii the bottom and die top mold members. A third wave of heat generation may also occur if the rate of reaction at the middle portion of the lens forming composition is different from the rates at die bottom and top portions. Unfortunately, the resulting lens possessed waves and distortions. It is postulated, however, that as the amounts of both CGI-819 and NMDEA are increased, the two waves of exothermic heat will move closer together in time, causing the optical quality of die lens to improve, the hardness of die lens to increase, and die rate of heat generation to be slow enough to prevent cracking and premature release of the lens from the mold.

It is anticipated that the optimal amounts of the lens forming composition components is where the total amount of both initiators are minimized subject to the constraint of complete polymerization and production of a rigid, abenation free lens. The relative proportions of the photoinitiator to the co-initiator may be optimized by experimentation. For example, an activating light absorptive lens forming composition that includes a photoinitiator with no co-initiator may be cured. If waves and distortions are observed in die resulting lens, a co-initiator may tiien be added to the lens forming composition by increasing amounts until a lens having the best optical properties is formed. It is anticipated tiiat excess co-initiator in the lens forming composition should be avoided to inhibit problems of too rapid polymerization, yellowing of the lens, and migration of residual, unreacted co-initiator to the surface of the finished lens.

The following charts may be used as a guide in d e selection of an appropriate photoinitiator/co- initiator system for various activating light absorbtive lens forming compositions. Photoinitiator Guide

Co-initiator Guide

Lens Forming Composition Type Good, Less Preferred

As mentioned above, exotiiermic reactions occur during the curing process of the lens forming composition. The thicker portions of the lens forming composition may generate more heat than the thinner portions of the composition as a result of the exothermic reactions taking place. It is believed tiiat the speed of reaction in the thicker sections is slower than in the thinner sections. Thus, in a positive lens a "donut effect" may occur in which the relatively thin outer portion of the lens forming composition reaches its fully cured state before die relatively thick inner portion of the lens forming composition. Conversely, in a negative lens the relatively thin inner portion of the lens forming composition may reach its fully cured state before the relatively thick outer portion of the lens formmg composition.

Accordingly, it is prefened tiiat a greater amount of activating light is applied to the thicker sections of the composition than to die tiiinner sections. Fig. 36 depicts one embodiment in which a pair of mold members 500 are held togetiier by a gasket 502 such that members 500 define a cavity to make a positive lens. A filter 506 may be placed directly adjacent to at least one of die mold members 500. Filter 506 may further be disposed between an activating light source (not shown) and die mold member. Alternately, filters may be placed adjacent to both mold members (not shown). In one embodiment, as shown in Fig. 36, the thickness of die filter preferably varies so that a thinner section of the filter conesponds to an adjacent tiiicker section of the mold cavity and a tiiicker section of the filter conesponds to an adjacent thinner section of die mold cavity. In otiier words, me thickness of the filter may be varied according to d e varying thickness of die lens forming composition disposed witiiin die mold cavity. The filter is preferably a hazy filter that may be formed by a variety of means. The filter may be polymerized from a hazy material or any combination of materials which create haze. More specifically, the filter may be a "lens" (i.e., a piece of plastic shaped like a lens) made by adding an incompatible chemical to a typical lens forming composition. For example, a bisphenol compound may be added to a lens forming composition and polymerized, resulting in a cloudy filter in the shape of a lens tiiat separates light into numerous (e.g., millions) of fragments. The filter may be injection molded from polyethylene or any suitable thermoplastic.

A purpose of the filter is to simultaneously diffuse light and provide differential light distribution between die thin and thick sections of the mold cavity. See U.S. Patent No. 5,415,816 for a discussion of die importance of differential light distribution with respect to the activating light initiated polymerization of eyeglass lenses. See U.S. Patent No. 4,728,469 for a discussion of the importance of light diffusion with respect to the activating light initiated polymerization of eyeglass lenses. The filter is preferably translucent to activating light. When a hazy filter is used, die activating light may be broken up into a relatively large number of fragments. It is believed tiiat the amount of light attenuation created by such a filter is proportional to the diickness of the filter. The diffusing characteristics of the filter tends to impact the occunence of optical abenations and distortions in the finished lens.

In general, when curing a minus (negative) lens which is thin in the center and thick on die edge, it is preferable to use a filter which is tiiick in die center and tiiin at the edge adjacent to the mold members. When curing a plus (positive) lens which is thick in the center and tiiin on the edge, it is preferable to use a filter which is thin in the center and tiiick at d e edge adjacent to die mold members. The location of the filter is preferably chosen to be near the mold cavity so that the differential light distribution of the filter tends to be maximized. Thus, the activating light intensity directed toward the thick and thin regions of the mold cavity may be controlled more readily than if the filter is further away from the mold members.

A flat-top bifocal mold, such as the one depicted in Fig. 35 reflects light in different regions with different light intensities. Particularly, the segment line 454 of the bifocal segment 452 reflects light more than other areas of the mold, increasing die amount of activating light that the lens forming composition is exposed to in the region near segment line 454. It is believed that tiiis region of the lens forming composition will gel more rapidly state tiian other portions of die lens forming composition. Thus, when using a flat-top bifocal mold to form a lens, it is desirable to diffuse activating light before it reaches the segment line of the mold, and tiiereby reduce die amount of light tiiat is reflected at die segment line. In an embodiment in which a flat-top bifocal mold is being utilized, the use of a hazy filter as described above is preferred.

In one embodiment, after the lens forming composition has been placed in the mold cavity, it may be pre-cooled 3 to 7 minutes before being exposed to activating light. Thus, the lens forming composition may be cooled to below ambient temperature prior to polymerization of the lens forming composition. Advantageously, die heat released by the reaction within the composition may be balanced by the coolness of the composition so tiiat the composition is not exposed to extreme amounts of thermal radiation. Thus, exposing the lens forming composition to below ambient temperatures before the reaction is initiated may inhibit undesirable effects resulting from the exotiiermic nature of the reaction. For example, cooling the lens forming composition might help prevent the loss of process control caused by variations in the rate of reaction that result from temperature changes of the lens forming composition.

In an embodiment, d e activating light is directed toward the mold members until at least a portion of the lens forming composition is a gel. At this point, application of the activating light is preferably terminated to inhibit die polymerization reaction from proceeding too rapidly, thereby inhibiting the rate of heat generation from increasing so rapidly tiiat premature release of the lens from the mold cavity and/or cracking of die lens results. After termination of the light, the gasket holding the two mold members together is preferably removed to expose die lens forming composition to air while the reaction is allowed to continue at a desired rate. The air may advantageously help cool die lens forming composition. In an embodiment, die lens forming composition may be exposed to ambient conditions for about 5 to 15 minutes, depending on die mass of the composition. Since die amount of heat released during reaction tends to be proportional to the mass of the composition, the more mass the composition has, the longer it may be cooled. After cooling the composition, it may be exposed to activating light again if desired.

In an embodiment, die inner surface, i.e., the casting face, of the front mold member may be coated witii one or more hardcoat layers before the lens forming composition is placed within the mold cavity.

Preferably, two hardcoat layers are used so tiiat any imperfections, such as pin holes in the first hardcoat layer, are covered by die second hardcoat layer. The resulting double hardcoat layer is preferably scratch resistant and protects die subsequently formed eyeglass lens to which the double hardcoat layer adheres. In an embodiment, the casting face of the back mold member may be coated with a material mat is capable of being tinted witii dye prior to filling die mold cavity with die lens forming composition. This tintable coat preferably adheres to the lens forming composition so that dyes may later be added to the resulting eyeglass lens for tinting the lens.

In an embodiment, dyes may be added to die lens forming composition. It is believed tiiat certain dyes may be used to attack and encapsulate ambient oxygen so tiiat the oxygen cannot react with free radicals formed during the curing process. Also, dyes may be added to die composition to alter the color of an unactivated photochromic lens. For instance, a yellow color that sometimes results after a lens is formed may be "hidden" if a blue-red or blue-pink dye is present in die lens forming composition. The unactivated color of a photochromic lens may also be adjusted by the addition of non-photochromic pigments to the lens forming composition.

In an embodiment, the eyeglass lens that is formed may be coated witii a hydrophobic layer, e.g. a hardcoat layer. The hydrophobic layer preferably extends the life of the photochromic pigments near the surfaces of the lens by preventing water and oxygen molecules from degrading the photochromic pigments.

In a preferred embodiment, boti mold members are coated with a cured adhesion-promoting composition prior to placing die lens forming composition into the mold cavity. Providing the mold members witii such an adhesion-promoting composition is prefened to increase the adhesion between the casting surface of the mold and die lens forming composition. The adhesion-promoting composition thus reduces the possibility of premature release of the lens from the mold. Further, it is believed that such a coating also provides an oxygen and moisture barrier on the lens which serves to protect the photochromic pigments near the surface of the lens from oxygen and moisture degradation. Yet further, the coating provides abrasion resistance, chemical resistance, and improved cosmetics to the finished lens.

An eyeglass lens formed using the lens forming composition of the present invention is not only applicable for use as a prescription lens and may be used for a non-prescription lens as well. Particularly, such a lens may be used in sunglasses. Advantageously, photochromic sunglass lenses would remain light enough in color to allow a user to see ti rough them clearly while at the same time prohibiting activating light from passing through the lenses. In one embodiment, a background dye may be added to die photochromic lens to make the lens appear to be a dark shade of color at all times like typical sunglasses.

Each of the embodiments described above may be combined or used individually.

CASTING A PLASTIC LENS CONTAINING PHOTOCHROMIC MATERIAL PROCESS EXAMPLE

A polymerizable mixture of PRO-629 (see above for a description of the components of PRO-629), photochromic pigments, and an activating light photoinitiator/co-initiator system was prepared according to the following procedure. A photochromic stock solution was prepared by dissolving die following pigments into 484 grams of HDDMA.

Pigment grams % by wt.

Dye #94 1.25 0.250%

Dye # 266 0.45 0.090%

Variacrol Red PNO 2.66 0.532%

Variacrol Yellow L 1.64 0.328%

Reversacol Corn Yellow 3.58 0.716%

Reversacol Berry Red 2.96 0.590%

Reversacol Sea Green 2.17 0.434%

Reversacol Palatinate Purple 1.29 0.258%

Total 16.0 3.200%

Dye #94 and Dye #266 are indilino spiropyrans commercially available from Chroma Chemicals, Inc. in Dayton, Ohio. Variacrol Red PNO is a spiro-napthoxazine material and Variacrol Yellow L is a naptiiopyran material, botii commercially available from Great Lakes Chemical in West Lafayette, Indiana. Reversacol Com Yellow and Reversacol Berry Red are naptiiopyrans and Reversacol Sea Green, and Reversacol Palatinate Purple are spiro-napthoxazine materials commercially available from Keystone Analine Corporation in Chicago, Illinois. The powdered pigments were weighed and placed in a beaker. The HDDMA was added to die powdered pigments, and the entire mixture was heated to a temperature in the range from about 50°C to 60°C and stirred for two hours. Subsequently, the photochromic stock solution was cooled to room temperature and tiien gravity fed tiirough a four inch deep bed of aluminum oxide basic in a one inch diameter column. Prior to passing die stock solution through the alumina, the alumina was washed with acetone and dried witii air. The remaining HDDMA was forced out of the alumina with pressurized air. It is believed tiiat this filtration step removes any degradation by-products of the photochromic pigments and or any impurities present in the mixture. After the filtration step, the stock solution was passed tiirough a 1 micron filter to remove any alumina particles which may have passed out of the column witii the stock solution.

A photoinitiator stock solution containing an activating light photoinitiator combined witii an activating light absorber was also prepared by mixing 2.56 grams of CGI-819 and 0.2 grams of Tinuvin 400, an activating light absorber commercially available from Ciba Additives of Tarrytown, New York, with 97.24 grams of PRO-629. The stock solution was stirred for two hours at room temperature in the absence of light. The photoinitiator stock solution was tiien filtered by passing it tiirough a layer of alumina and a one micron filter. The stock solution was placed in an opaque polyethylene container for storage.

A background dye stock solution was prepared by mixing 50 grams of a 422 ppm solution of A241/HDDMA, 50 grams of a 592 ppm solution of Thermoplast Red 454/HDDMA, 50 grams of 490 ppm solution of Zapon Brown 286/HDDMA, 50 grams of 450 ppm solution of Zapon Brown 287/HDDMA, 50 grams of 1110 ppm solution of Oil Soluble Blue II/HDDMA, and 50 grams of a 1110 ppm solution of

Thermoplast Blue P/HDDMA, all with 700 grams of PRO-629. The entire mixture was heated to a temperature ranging from about 50°C to 60°C and subsequently stined for two hours.

A lens forming composition was prepared by adding 12.48 grams of the above described photochromic stock solution, 10 grams of the photoinitiator stock solution, 27 grams of the background dye stock solution, and 7.3 grams of the NMDEA co-initiator to 943.22 grams of PRO-629. The components of the lens forming composition were stined at room temperature for several minutes until well mixed. This composition is hereafter refened to as PC #1 . The PC#1 contained the following amounts of components.

Component Amount Tripropyleneglycol diacrylate 31.16 %

Tetraethyleneglycol diacrylate 20.45 %

Trimethylopropane triacrylate 19.47 %

Bispenol A bis allyl carbonate 16.55 %

Hexanediol dimetiiacrylate 11.56 % Dye #94 31.20 ppm

Dye # 266 11.20 ppm

Variacrol Red PNO 66.40 ppm

Variacrol Yellow L 40.90 ppm

Reversacol Corn Yellow 89.30 ppm Reversacol Berry Red 73.60 ppm

Reversacol Sea Green 54.20 ppm

Reversacol Palatinate Purple 32.20 ppm

A241 0.57 ppm Thermoplast Red 454 0.80 ppm

Zapon Brown 286 0.66 ppm

Zapon Brown 287 0.61 ppm

Oil Soluble Blue II 1.50 ppm Thermoplast Blue 1.50 ppm

CGI-819 255.90 ppm

NMDEA 0.73 %

Tinuvin 400 20.00 ppm

An 80mm diameter concave glass progressive addition mold having a distance radius of curvature of

6.00 diopters and a +1.75 diopter bifocal add power was sprayed with a mixture of isopropyl alcohol and distilled water in equal parts and wiped dry witii a lint free paper towel. The mold was tiien mounted witii its casting face upward on die center of a stage. The mold was fixed securely to the stage using three equidistant clip-style contact points to hold die periphery of the mold. The mold stage had a spindle attached to it which was adapted to connect to a spinning device of a FastCast UX-462 Flashcure Unit, commercially available from the FastCast Corporation of Louisville, Kentucky. The mold stage, witii die mold affixed, was placed on die spinning device in the FlashCure unit. The mold was rotated at approximately 750 to 900 revolutions per minute. A stream of isopropyl alcohol was directed at die casting surface while the casting surface was simultaneously brushed with a soft camel hair brush to clean the suface. After the cleaning step, the mold surface was dried by directing a stream of reagent grade acetone over the surface and allowing it to evaporate off, all while continuing the rotation of the mold.

The rotation of the mold was then terminated and a one inch diameter pool of a liquid coatmg composition was dispensed into the center of the horizontally positioned glass mold from a soft polyethylene squeeze bottle equipped witii a nozzle having an orifice diameter of approximately 0.040 inches. The spin motor was engaged to rotate the mold at a speed of approximately 750 to 900 revolutions per minute, causing the liquid material to spread out over die face of die mold. Immediately thereafter, a steady stream of an additional 1.5 to 2.0 grams of die coating composition was dispensed onto die casting face of die spinning mold. The stream was moved from the center to die edge of die casting face with a nozzle tip positioned at a 45° angle approximately 12 mm from the mold face. Thus, the stream was flowing with the direction of rotation of the mold.

The solvent present in the coating composition was allowed to evaporate while rotating die mold for 10 to 15 seconds. The rotation was stopped, and tiien the coating composition on the mold was cured via totalling exposures of approximately 300 mJ/cm2 of activating light. The light was provided from a medium pressure mercury vapor lamp contained in the UX-462 FlashCure unit. All light intensity/dosage measurements cited herein were taken with an International Light IL-1400 Radiometer equipped with an XLR-340B Detector Head, botii commercially available from International Light, Inc. of Newburyport, Massachusetts. At this point, the spin motor was again engaged and approximately 1.5 to 2.0 grams of additional coating composition was dispensed onto the spinning mold. The solvent of the composition was allowed to evaporate, and the composition was cured in a similar fashion to the first layer of coating composition. The above described coating composition comprised the following materials:

Material % by wt.

Irgacure 184 0.91 %

Dye Absorption 0.80 %

Stabilizer

CN-104 2.00 %

SR-601 1.00 %

SR-399 8.60 %

Acetone 26.00 %

Ethanol 7.00 %

1 -Methoxypropanol 53.69 %

Irgacure 184 is a activating light photoinitiator commercially available from Ciba Additives, Inc. CN-104 is an epoxy acrylate oligomer, SR-601 is an ethoxylated bisphenol A diacrylate, and SR-399 is dipentaerythritol pentaacrylate, all available from Sartomer Company in Exton, Pennsylvania. The acetone, the ethanol, and the 1 -methoxypropanol were all reagent grade solvents. The dye absorption accelerator improves the impact resistance of the lens and is available from Crs di Claudio Crose in Milan, Italy.

An 80 mm diameter convex mold with radii of curvature of 6.80/7.80 diopters was cleaned and coated using die same procedure described above except tiiat no pooling of the coating composition occurred in the center of die mold when the composition was dispensed thereto.

The concave and convex molds were tiien assembled togetiier with a silicone rubber gasket. A raised lip on the inner circumference of the rubber gasket provided a spacing of 2.8 mm between the two molds at die center point. At this point the mold/gasket assembly was positioned on a filling stage. The edge of the gasket was peeled back to permit the cavity to be filled with PC #1 lens forming composition. The edge of the gasket was returned to its sealing relationship with the edges of the molds, and the excess lens forming composition was vacuumed from the non-casting surface of the back mold with a suction device. The filled mold gasket assembly was tiien transferred from the filling stage to the UX-462 curing chamber. The assembly was placed witii the back mold facing upward on a black stage configured to hold die mold/gasket assembly.

An activating light filter was then placed on top of the back mold. The filter was approximately 80 mm in diameter which is the same as the mold diameter. The filter also had a spherical configuration with a center thickness of 6.7 mm and an edge thickness of 5.5 mm. The filter was taken from a group of previously made filters. These filters were formed by using eyeglass lens casting molds and gaskets to create cavities that were thickest in the center (a plus spherical cavity) and cavities that were thinnest in the center (a minus spherical cavity). A toric component was also incorporated with some of these cavities to form compound cavities. The filter cavities were filled with an activating light curable composition comprising by weight: 99.37% PRO-629, 0.35 % K-Resin, 0.27% NMDEA, 121 ppm CGI-819, and 10 ppm Tinuvin 400. K-resin is a styrene-butadiene copolymer commercially available from Phillips Chemical Company. To form this composition, the K-resin was first dissolved in toluene. An appropriate amount of die K-resin toluene solution was added to the PRO-629, and then the toluene was evaporated off by heat and stirring. The NMDEA, CGI- 19, and the Tinuvin 400 were then added to die PRO-629/K-Resin solution. The compositions contained in die cavities were cured by exposure to activating radiation. When die cured article was removed from die mold cavity, it exhibited a high degree of haze caused by the incompatibility of the PRO-629. and the K-Resin. In the strictest sense of the word, it should be noted that these filters were not "lenses" because their function was not to focus light but rather to scatter and diffuse light.

The mold/gasket assembly and the filter were tiien irradiated witii four consecutive doses of activating light totaling approximately 1150 mJ/cm2, as previously measured at the plane of the mold cavity witii no filter or any other intervening media between the light source and die plane. The mold/gasket assembly was then turned over on the stage so that the front mold was facing upward. The mold/gasket assembly was further rotated 90 degrees around the paraxial axis from its original position. The light filter was then placed over the front mold. The entire assembly was then exposed to two more doses of activating light totaling approximately 575 mJ/cm2. The mold/gasket assembly was removed from the curing chamber. The gasket was removed from die molds, and the exposed edge of die lens was wiped to remove any residual liquid. The molds witii lens were tiien placed in a vertical orientation in a rack, and die non-casting faces of both the front and back molds were exposed to ambient room temperature air for a period of approximately ten minutes. At this point, the entire mold assembly was returned to the UX-462 chamber. Then, without the aforementioned light filter in place, the mold assembly was dosed with four exposures totaling 600 mJ/cm2 directed toward die back mold and two exposures totaling 300 mJ/cm2 directed toward die front mold.

Subsequent to tiiese exposures, the junction of the back mold and d e lens was scored with die edge of a brass spatula. The back mold was then removed from the lens by positioning an appropriate sized Delrin wedge between the front and back molds and applying a sharp impact to die wedge. The lens, along with the front mold to which it was attached, was held under running tap water and simultaneously brushed witii a soft brush to remove any flakes or particles of polymer from the edges and surface of the lens. The front mold was tiien separated from the lens by breaking the seal between the two with the point of a pin pressed against the junction of the front mold and the lens. The lens was tiien placed concave side upward on a lens stage of similar design to die mold stage, except that the peripheral clips were configured to secure a smaller diameter workpiece. The lens stage, with the lens affixed, was positioned on the spinning device of the UX-462 unit and rotated at about 750 to 900 revolutions per minute. A stream of isopropyl alcohol was directed at the concave surface while simultaneously brushing the surface with a soft, clean brush. After brushing, a stream of isopropyl alcohol was directed at the surface of the lens, and d e rotation was continued for a period of approximately 30 seconds until the lens was dry. The lens was turned over on the stage so that the convex surface of the lens faced upward. Then the cleaning procedure was repeated on die convex surface. With the convex surface facing upward, the lens was dosed with four exposures of activating light totaling approximately 1150 mJ/cm2. The lens was again turned over on the stage such that the concave surface was upward. The lens was subjected to an additional two exposures totaling 300 mJ/cm2. The lens was removed from the stage and placed in a convection oven at 115°C for five minutes. After annealing the lens, it was removed from the oven and allowed to cool to room temperature. At this point the lens was ready for shaping by conventional means to fit into an eyeglass frame.

The resulting lens was approximately 72 mm in diameter. The lens had a center thickness of 2.6 mm, a distance focusing power of -0.71 -1.00 diopters, and a bifocal addition strength of 1.74 diopters. The lens appeared to have a bleached color of tan. Also, the lens tiiat was formed exhibited approximately 75 % visible transmittance as measured with a Hoya ULT-3000 meter. The lens was exposed to midday sunlight at a temperature of approximately 75 ° F for 3 minutes. After being exposed to sunlight, the lens exhibited a grey color and a visible light transmittance of approximately 15 %. The optics of the lens appeared to be crisp, without abenated areas in either the distance or the bifocal segment regions. The same lens forming composition was cured to form a piano lens so that d e lens could be scanned witii a Hewlitt Packard Model 8453 UV-Vis spectrophotometer. See Fig. 37 for a plot of % transmittance versus wavelength (nm), as exhibited by the piano lens in its lightened state (i.e., without sunlight exposure). The lens exhibited very little transmittance of light at wavelengths below about 370 nm.

The eyeglass lens of this example was cured using activating light even though the lens forming composition included activating light absorbing photochromic pigments. Since photochromic pigments tend to absorb activating light strongly, the activating light might not have penetrated to the depths of the lens forming composition. The lens forming composition, however, contained a co-initiator in conjunction with a photoinitiator to help promote the curing of the entire lens forming composition. The present example thus demonstrates tiiat a photochromic lens containing both a photoinitiator and a co-initiator may be cured using activating light to initiate polymerization of the lens forming composition.

CASTING A COLORLESS LENS CONTAINING ACTIVATING ABSORBERS EXAMPLE

According to a preferred embodiment, a polymerizable mixture of PRO-629 (see above for a description of the components of PRO-629), colorless activating light absorbing compounds, an ultraviolet stabilizer, background dyes, and an activating light photoinitiator/co-initiator package was prepared according to die following procedure. Six separate stock solutions were prepared. One stock solution contained die photoinitiator, two stock solutions contained activating light absorbing compounds, one stock solution contained co-initiators, one stock solution contained an activating light stabilizer, and one stock solution contained a background dye package. Each of these stock solutions were treated by passing them through a one inch diameter column packed with approximately 30 grams of alumina basic. It is believed that this step reduced die impurities and trapped the acidic byproducts present in each of the additives to the PRO-629. The following is a detailed description of die preparation of the polymerizable mixture mentioned above. About 500 grams of a photoinitiator stock solution was prepared by dissolving 2.5%> by weight of bis(2,6-dimetoxybenzoyl)(2,4,4 trimethyl phenyl) phosphine oxide (CGI-819 commercially available from Ciba Additives) in Pro-629. This mixture was passed through an alumina basic column in the dark.

About 500 grams of die activating light absorber stock solution was prepared by dissolving 2.5%) by weight of 2(2H-benzotriazol-2-yl)-4-(l, 1,3,3 tetramethyl)phenol (98% purity) in PRO-629. This mixture was also passed tiirough an alumina basic column.

About 500 grams of a co-initiator stock solution was prepared by mixing 70% by weight of CN-384 (a reactive amine co-initiator commercially available from Sartomer Company) in Pro- 629. This mixture was passed through an alumina basic column. About 271 grams of an activating light stabilizer stock solution was prepared by mixing 5.55% by weight of Tinuvin 292 in PRO-629. This mixture was passed through an alumina basic column.

About 250 grams of a activating light absorber stock solution was prepared by mixing 5.0% Tinuvin 400 (i.e., a mixture of 2-[4-((2-hydroxy-3-dodecyloxypropyl)-oxy] 2-2 hydroxyphenyl]-4,6-bis(2,4- dimetiiylphenyl)- 1 ,3,5-triazine and 2-[4-((2-hydroxy-3-tridecyloxyρropyl)-oxy]-2-hydroxyphenyl]-4,6-bis(2,4- dimethylpheyl- 1 ,3,5-triazine)) by weight in PRO-629. This mixture was passed through an alumina basic column.

About 1000 grams of a background dye stock solution was prepared by mixing about 50 grams of a 592 ppm solution of Thermoplast Red 454/HDDMA, 50 grams of 490 ppm solution of Zapon Brown 286/HDDMA, 50 grams of 450 ppm solution of Zapon Brown 287/HDDMA, 50 grams of 1110 ppm solution of Oil Soluble Blue II/HDDMA, and 50 grams of a 1110 ppm solution of Thermoplast Blue P/HDDMA, all with 750 grams of PRO-629. The entire mixture was heated to a temperature between about 50° and 60° C and stirred for two hours. This mixture was passed through an alumina basic column.

About 250 grams of CN-386 (a reactive amine co-initiator commercially available from Sartomer Company) was passed tiirough an alumina basic column. A lens forming composition was prepared by mixing 967.75 grams of Pro-629 with 12.84 grams of the

2.5% 2(2H-benzotriazol-2-yι)-4-(l,l,3,3 teteamethyl)phenol activating light absorber stock solution, 4.3 grams of the 70% CN-384 co-initiator stock solution, 8.16 grams of the 2.5% CGI-819 photoinitiator stock solution, 0.53 grams of the CN-386, 1.54 grams of the Tinuvin 400 activating light absorber stock solution, 0.92 grams of the Tinuvin 292 activating light stabilizer stock solution, and 4.0 grams of the background dye stock solution. The resulting lens forming composition contained the following components:

Material % by weight

PRO-629 99.10%

2(2H-benzotriazol-2-yl)-4-( 1,1,3,3 tetramethyl)ρhenol 321 ppm

Tinuvin 400 77 ppm

Tinuvin 292 51 ppm

CN-384 0.3%

CN-386 0.53% CGI-819 204 ppm Thermoplast Red 0.12 ppm Zapon Brown 286 0.10 ppm Zapon Brown 287 0.10 ppm Oil Soluble Blue II 0.22 ppm Thermoplast Blue 0.22 ppm

An 80mm diameter 28 flattop concave glass mold witii a distance radius of curvature of 2.85 diopters and a +3.00 diopter bifocal add power was sprayed witii a mixture of isopropyl alcohol and distilled water in equal parts and wiped dry with a lint free paper towel. The mold was then mounted witii its casting face upward on a stage. The mold was fixed securely to the center of the stage using three equidistant clip-style contact points at the periphery of the mold. The mold stage had a spindle attached to it which was adapted to fit into die spinning device provided in the FastCast UX-462 FlashCure Unit, commercially available from the FastCast Corporation of Louisville, Kentucky. The mold stage, with the mold affixed, was placed on the spinning means in the FlashCure unit. The mold was rotated at approximately 750 to 900 revolutions per minute. A stteam of the isopropyl alcohol was directed at the casting surface while the casting surface was simultaneously brushed with a soft camel hair brush to clean the surface. After the cleaning step, the mold surface was dried by directing a stream of reagent grade acetone over die surface and allowing it to evaporate off, all while continuing the rotation of the mold. The rotation of the mold was then terminated and one inch diameter pool of a liquid coating composition was dispensed into the center of the horizontally positioned glass mold from a soft polyethylene squeeze bottle equipped with a nozzle with an orifice diameter of approximately 0.040 inches. The spin motor was engaged to begin to rotate the mold at a speed of approximately 750 to 900 revolutions per minute, causing the liquid material to be spread out over the face of the mold. Immediately thereafter, a steady stream of an additional 1.5 to 2.0 grams of the coating composition was dispensed onto the casting face of the spinning mold. The stream was moved from the center to the edge of the casting face witii a nozzle tip positioned at a 45 degree angle, approximately 12 mm from the mold face. Thus, the stream was flowing with the direction of rotation of the mold.

The solvent present in the coating composition was allowed to evaporate off for 10 to 15 seconds while rotating. The rotation was stopped, and then the coating composition present on the mold was cured via two exposures to the activating light output from the medium pressure mercury vapor lamp contained in me UX-462 FlashCure unit, totaling approximately 300 mJ/cm2. All light intensity/dosage measurements cited herein were taken with an International Light IL-1400 Radiometer equipped with an XLR-340B Detector Head, botii commercially available from International Light, Inc. of Newburyport, Massachusetts. The above described coating composition comprised the following materials:

Material % by wt.

Irgacure 184 0.91 %

Dye Absorption 0.80 %

Accelerator

CN-104 2.00 %

SR-601 1.00 %

SR-399 8.60 %

Acetone 26.00 %

Ethanol 7.00 %

1 -Methoxypropanol 53.69 %

Irgacure 184 is an activating light photoinitiator commercially available from Ciba Additives, Inc. CN-104 is an epoxy acrylate oligomer, SR-601 is an ethoxylated bisphenol A diacrylate, and SR-399 is dipentaerythritol pentaacrylate, all available from Sartomer Company in Exton, Pennsylvania. The acetone, the etiianol, and the 1 -methoxypropanol were all reagent grade solvents. The dye absorption accelerator improves the impact resistance of the lens and is available from Crs di Crose in Milan, Italy.

An 80 mm diameter convex mold with radii of curvature of 7.05 diopters was cleaned and coated in die same fashion described above except that no pooling of the coating composition occuned in the center of the mold when the composition was dispensed thereto.

Both the concave and convex molds were then provided with a cured adhesion-promoting coating composition. By providing such a coating, the adhesion between the casting surface of the glass mold and the lens forming composition was increased, thereby reducing die possibility of premature release of the lens from the mold. The coating further provided abrasion resistance, chemical resistance, and improved cosmetics to the finished lens.

The concave and convex molds were then assembled into a silicone rubber gasket. A raised lip present on the inner circumference of the rubber gasket provided a spacing of 1.7 mm between the two molds at the center point. At tins point the mold/gasket assembly was positioned on a filling stage. The edge of d e gasket was peeled back to permit the cavity to be filled witii the above described colorless lens forming composition containing the activating light absorbing compounds. The edge of the gasket was returned to its sealing relationship with the edges of the molds, and the excess lens forming composition was vacuumed off the non- casting surface of the back mold witii a suction device. The filled mold/gasket assembly was then transfened from the filling stage to the UX-462 curing chamber and placed back mold upward on a black stage configured to hold the mold/gasket assembly.

An activating light filter was then placed on top of the back mold. The filter was approximately 80 mm in diameter which is the same as the mold diameter. It had a piano configuration with a thickness of 3.1 mm. This filter transmitted approximately 30% of the incident activating light from the source as measured usmg the IL1400 radiometer with a XRL-340B detector head. The filter was taken from a group of previously made filters The fabrication of these filters was discussed m the Castmg A Plastic Lens Contammg Photochromic Material Example (see above)

The mold/gasket assembly m which the lens formmg composition had been placed and which had been covered by the above descπbed filter was then madiated with four consecutive doses of activatmg light totalmg approximately 600 mJ/cm2, as measured using the IL-1400 Radiometer equipped with the XLR-340B detector This measurement was taken at the plane of the mold cavity while no filter or any intervening media was present between the light source and the plane The mold/gasket assembly was then turned over on the stage so that the front mold was facmg upward. The mold gasket assembly was further rotated 90 degrees around die paraxial axis from its onginal position The light filter was then replaced over the front mold The entire assembly was exposed to two more doses of activating light totaling approximately 300 mJ/cm2

The mold gasket assembly was then removed from the curing chamber, and die gasket was removed from the assembly The mold with lens was then returned to the UX-462 curmg chamber such that the back mold was facmg upward An opaque rubber disc, approximately 80 mm in diameter was placed over the back mold. This disc had the function of preventmg activating light from impinging on the major portion of the matenal contamed within the cavity. With the disc m position, the cell was exposed to two more exposures at 300 mJ/ cm2. This subsequent exposure was used to cure the residual liquid around the edges of d e lens, particularly around the junction between the front mold and the lens and to help seal the periphery. The mold assembly was removed from the curmg chamber and placed m a vertical orientation m a rack. The non-casting faces of botii the front and back molds were then exposed to ambient room temperature air for a penod of approximately fifteen minutes. At this pomt, the entire mold assembly was returned to the UX-462 chamber and, without die aforementioned light filter or opaque disc m place, was dosed with two exposures totaling 300 mJ/cm2 directed toward the back mold and two exposures totalmg 300 mJ/cm2 directed toward die front mold Subsequent to these exposures, the junction of the back mold and the lens was scored with die edge of a brass spatula. The back mold was then removed from the lens by positioning an appropriate sized Delrm wedge between the front and back mold and applymg a sharp impact to the wedge. The lens, with the front mold attached, was held under running tap water and simultaneously brushed with a soft brush to remove any flakes or particles of polymer from the edges and surface of the lens. The front mold was tiien separated from the lens by breakmg the seal between the two with the pomt of a pm pressed agamst the junction of the front mold and die lens. The lens was tiien placed concave side upward on a lens stage of similar design to die mold stage except that die peripheral clips were configured to secure a smaller diameter workpiece. The lens stage, with the lens affixed, was positioned on die spmmng device of the UX-462 unit and rotated at 750 to 900 revolutions per mmute. A stream of isopropyl alcohol was directed at die concave surface while simultaneously brushing with a soft, clean brush After brushing, a stream of isopropyl alcohol was directed at the surface of the lens, and the rotation was continued for a peπod of approximately 30 seconds until the lens was dry The lens was turned over on the stage so that the convex surface of the lens was upward. Then the cleaning procedure was repeated on the convex surface. With the convex surface upward, the lens was dosed with four exposures of activatmg light totaling approximately 1150 mJ/cm2. The lens was turned over on the stage so that the concave surface faced upward. The lens was subjected to an additional two exposures totaling 300 mJ/cm2. The lens was removed from the stage and placed in a convection oven at 115°C for five minutes. The lens was then removed from the oven and allowed to cool to room temperature. At this point, the lens was ready for shaping by conventional means to fit into an eyeglass frame.

The resulting lens was approximately 72 mm in diameter, had a center tiiickness of 1.5 mm, a distance focusing power of -4.08 diopters, and a bifocal addition strength of 3.00 diopters. The resultant lens was water white. The optics of the lens were crisp, without abenated areas in either the distance or the bifocal segment regions. The same lens forming composition was cured to form a piano lens. The piano lens was scanned with a Hewlitt Packard Model 8453 UV-Vis spectrophotometer. See Fig. 38 for a plot of % transmittance versus wavelength (nm), as exhibited by the photochromic lens when exposed to sunlight. The lens exhibited virtually no transmittance of light at wavelengths below about 370 nm. Also shown in Fig. 38 is the results of a similar scan made on a piano lens formed using the OMB-91 lens forming composition (see Pulsed Activating Light Application section above for components of OMB-91). The OMB-91 lens, which has no activating light absorbing compounds, appears to transmit light at wavelengths shorter than 370 nm, unlike the colorless lens that contained activating light absorbing compounds.

The eyeglass lens of this example was cured using activating light even though the lens forming composition included activating light absorbing compounds. Since activating light absorbing compounds tend to absorb activating light strongly, the activating light might not have penetrated to die depths of the lens forming composition. The lens forming composition, however, contained a co-initiator in conjunction with a photoinitiator to help promote the curing of the entire lens forming composition. The present example thus demonstrates that a lens containing activating light absorbing compounds may be cured using activating light to initiate polymerization of a lens forming composition which contains a photoinitiator/co-initiator system.

CASTING A COLORED LENS CONTAINING ACTIVATING ABSORBERS EXAMPLE

According to a prefened embodiment, a polymerizable mixture of PRO-629 (see above for a description of the components of PRO-629), fixed pigments, and an activating light photoinitiator/co-initiator package was prepared according to the following procedure. Nine separate stock solutions were prepared. Seven of the stock solutions contained fixed pigments, one of die stock solutions contained an activating light absorbing compound, and one of the stock solutions contained a photoinitiator. Each of these stock solutions were treated by passing them through a one inch diameter column packed with approximately 30 grams of alumina basic. It is believed mat this step reduces the impurities and traps the acidic byproducts present in each of the additives to die PRO-629. For each of the following fixed pigments, a stock solution was prepared by the following procedure.

The pigments used were Thermoplast Red 454, Thermoplast Blue P, Oil Soluble Blue II, Zapon Green 936, Zapon Brown 286, Zapon Brown 287, Thermoplast Yellow 284. One gram of each pigment was dissolved in 499 grams of HDDMA. Each mixture was heated to a temperature in the range from about 50°C to 60°C for approximately two hours This mixture was passed through an alumina basic column The alumina was men washed with 200 grams of HDDMA at a temperature of 50°C to 60°C followed by 300 grams of PRO-629 at a temperature of 50°C to 60°C This washing step ensured that any pigments trapped m d e alumina were washed mto die stock solution. This resulted m stock solutions which contamed a 0 1% concentration of each pigment m 29.97% PRO-629 and 69 93% HDDMA.

About 250 grams of the activating light absorber stock solution was prepared by dissolving 5.0% Tinuvin 400 (a mixture of 2-[4-((2-hydroxy-3-dodecyloxypropyl)-oxy] 2-2 hydroxyphenyl]-4,6-bιs(2,4- dιmefhylphenyl)-l,3,5-tπazιne and 2-[4-((2-hydroxy-3-tπdecyloxypropyl)-oxy]-2-hydroxyphenyl]-4,6-bιs(2,4- dιmetiιylpheyl-l,3,5-tπazιne) by weight in PRO-629. This mixture was passed through an alumina basic column

About 500 grams of the photomitiator stock solution was prepared by dissolving 2.5% by weight of bιs(2,6-dιmetoxybenzoyl)(2,4,4 trimethyl phenyl) phosphme oxide (CGI-819 commercially available from Ciba Additives) m Pro-629. This mixture was passed through an alumina basic column m the dark.

A lens forming composition was prepared by mixmg 685.3 grams of Pro-629 with 10 48 grams of the 2.5% CGI-819 photomitiator stock solution, 5.3 grams of NMDEA (N -methyldiethanolamme is commercially available from Aldrich Chemicals), 0.6 grams of Tinuvin 400 activatmg light absorber stock solution, 7 grams of the Thermoplast Red stock solution, 58.3 grams of the Thermoplast Blue stock solution, 55.5 of die Oil Soluble Blue II stock solution, 29.2 grams of the Zapon Green 936 stock solution, 68.1 grams of the Zapon Brown 286 stock solution, 38 9 grams of the Zapon Brown 287 stock solution, and 41.3 grams of the Thermoplast Yellow 104 stock solution. The resulting lens formmg composition contamed the followmg components- Material % by weight Bisphenol A bis allyl carbonate 13.35% Tπpropyleneglycol diacrylate 25.13% Tetraethyleneglycol diacrylate 16.49% Tnmethylopropane triacrylate 15.71% Hexanediol dimetiiacrylate 28.75% Thermoplast Red 7.0 ppm Zapon Brown 286 68.1 ppm Zapon Brown 287 38.9 ppm Oil Soluble Blue II 55.5 ppm Thermoplast Blue 58.3 ppm Zapon Green 936 29.2 ppm Thermoplast Yellow 104 41.3 ppm NMDEA 0 53% CGI-819 262 ppm Tmuvm 400 30 ppm An 80mm diameter single vision concave glass mold with a distance radius of curvature of 6.00 diopters was sprayed with a mixture of isopropyl alcohol and distilled water in equal parts and wiped dry with a lint free paper towel. The mold was then mounted with its casting face upward on the center of a stage. The mold was fixed securely to the stage with three equidistant clip-style contact points at the periphery of the mold. This mold stage had a spindle attached to it which was sized to fit into a spinning device of a FastCast UX-462 FlashCure Unit, commercially available from the FastCast Corporation of Louisville, Kentucky. The mold stage, with the mold affixed, was placed on die spinning device in the FlashCure unit. The mold was rotated at approximately 750 to 900 revolutions per minute. A stream of the isopropyl alcohol was directed at the casting surface while the casting surface was simultaneously brushed witii a soft camel hair brush. After the cleaning step, the mold surface was dried by directing a stream of reagent grade acetone over the surface and allowing it to evaporate off, all while continuing the rotation of the mold.

The rotation of the mold was tiien terminated. A one inch diameter pool of a liquid coating composition was dispensed into the center of the horizontally positioned glass mold from a soft polyethylene squeeze bottle equipped with a nozzle with an orifice diameter of approximately 0.040 inches. The spin motor was engaged to begin to rotate the mold at a speed of approximately 750 to 900 revolutions per minute, which caused the liquid material to be spread out over the face of the mold. Immediately thereafter, a steady stream of an additional 1.5 to 2.0 grams of the said coating composition was dispensed onto die casting face of the spinning mold. The stream was moved from the center to me edge of the casting face with a nozzle tip positioned at a 45° angle approximately 12 mm from the mold face. Thus, die stream was flowing with the direction of rotation of the mold.

The solvent present in die coating composition was allowed to evaporate off for 10 to 15 seconds while rotating the mold. The rotation was stopped, and tiien the coating composition present on the mold was cured via two exposures to the activating light output from the medium pressure mercury vapor lamp contained in die UX-462 FlashCure unit, totaling approximately 300 mJ/cm2. All light intensity/dosage measurements cited herein were taken with an International Light IL-1400 Radiometer equipped witii an XLR-340B Detector Head, both commercially available from International Light, Inc. of Newburyport, Massachusetts. The above described coating composition comprised die following materials:

Material % by wt.

Irgacure 184 0.91 %

Dye Absorption 0.80 %

Accelerator

CN-104 2.00 %

SR-601 1.00 %

SR-399 8.60 %

Acetone 26.00 %

Ethanol 7.00 %

1 -Methoxypropanol 53.69 % Irgacure 184 is an activating light photoinitiator commercially available from Ciba Additives, Inc. CN-104 is an epoxy acrylate oligomer, SR-601 is an ethoxylated bisphenol A diacrylate, and SR-399 is dipentaerythritol pentaacrylate, all available from Sartomer Company in Exton, Pennsylvania. The acetone, the etiianol, and die 1 -methoxypropanol were all reagent grade solvents. The dye absorption accelerator improves the impact resistance of the lens and is available from Crs di Claudio Crose in Milan, Italy.

An 80 mm diameter convex mold with radii of curvature of 6.05 diopters was cleaned and coated in the same fashion except that no pooling of the coating composition occuned in the center of the mold when the composition was dispensed thereto.

The concave and convex molds were then coated with a cured adhesion-promoting coating composition. By providing such a coating, die adhesion between die casting surface of the glass mold and the curing lens forming composition wsa increased, thereby reducing the possibility of premature release of the lens from the mold. The coating also provided abrasion resistance, chemical resistance, and improved cosmetics to the finished lens.

The concave and convex molds were then assembled together with an ethylene vinyl acetate gasket. A raised lip on the inner circumference of the rubber gasket provided a spacing of 3.0 mm between die two molds at the center point. At this point the mold/gasket assembly was fixtured on a filling stage. The edge of die gasket was peeled back to permit die cavity to be filled with the above described colorless lens forming composition which contained activating light absorbing compounds. The edge of die gasket was returned to its sealing relationship with the edges of the molds, and the excess lens forming composition was vacuumed off the non-casting surface of the back mold with a suction device. The filled mold gasket assembly was transfened from the filling stage to die UX-462 curing chamber. The assembly was placed back mold upward on a black stage configured to hold the mold/gasket assembly.

An activating light filter was then placed on top of the back mold. The filter was approximately 80 mm in diameter which is die same as die mold diameter. It had a piano configuration with a thickness of 3.1 mm. This filter transmitted approximately 30% of the incident activating light from the source as measured using the IL1400 radiometer with a XRL-340B detector head. The filter was taken from a group of previously made filters. The fabrication of these filters was discussed in the Casting A Plastic Lens Containing Photochromic Material Example.

The mold/gasket assembly, containing the lens forming composition was then irradiated with six consecutive doses of activating light totaling approximately 1725 mJ/cm2, as previously measured using die IL- 1400 Radiometer equipped witii the XLR-340B detector at die plane of the mold cavity with no filter or any intervening media between d e light source and the plane. The mold/gasket assembly was then turned over on the stage so that the front mold was facing upward. The entire assembly was then exposed to six more doses of activating light totaling approximately 1725 mJ/cm2. The mold/gasket assembly was removed from the curing chamber. The gasket was removed from the molds, and the assembly was placed in a vertical orientation in a rack such that the non-casting faces of botii the front and back molds were exposed to ambient room temperature air for a period of approximately ten minutes. At this point, the assembly was returned to die UX- 462 chamber and was dosed with four exposures totaling 600 mJ/cm2 directed toward the back mold and four exposures totaling 600 mJ/cm2 directed toward the front mold.

Subsequent to these exposures, the junction of the back mold and die lens was scored witii the edge of a brass spatula. The back mold was removed from the lens by positioning an appropriate sized Delrin wedge between the front and back mold and applying a sharp impact to the wedge. The lens, witii the front mold attached, was held under running tap water and simultaneously brushed with a soft brush to remove any flakes or particles of polymer from the edges and surface of the lens. The front mold was then separated from d e lens by breaking the seal between the two with the point of a pin pressed against the junction of the front mold and the lens. The lens was then placed concave side upward on a lens stage of similar design to the mold stage, except that die peripheral clips were configured to secure a smaller diameter workpiece. The lens stage, witii the lens affixed, was positioned on the spinning device of d e UX-462 unit and rotated at 750 to 900 revolutions per minute. A stream of isopropyl alcohol was directed at the concave surface while simultaneously brushing with a soft, clean brush.

After brushing, a stream of isopropyl alcohol was directed at the surface of the lens, and the rotation was continued for a period of approximately 30 seconds until the lens was dry. The lens was turned over on the stage so that the convex surface of the lens faced upward. Then the cleaning procedure was repeated on die convex surface. Witii the convex surface facing upward, die lens was dosed witii four exposures of activating light totaling approximately 1150 mJ/cm2. The lens was turned over on the stage so that die concave surface was upward. The lens was dosed with an additional two exposures totaling 300 mJ/cm2. The lens was removed from the stage and placed in a convection oven at 115°C for five minutes. The lens was then removed from the oven and allowed to cool to room temperature. At this point the lens was ready for shaping by conventional means to fit into an eyeglass frame.

The resulting lens was approximately 74 mm in diameter, had a center thickness of 2.7 mm, and a distance focusing power of +0.06 diopters. The resultant lens was dark green/greyish in color and could be used as a sunglass lens. The optics of the lens were crisp, without aberrated areas. The lens exhibited visible light transmission of approximately 10%. When scanned with a Hewlett Packard Model UV-Vis spectrophotometer, the lens transmitted virtually no light at wavelengths less than 650 nm.

The sunglass lens of this example was cured using activating light even though the lens forming composition mcluded activating light absorbing fixed pigments. Since such fixed pigments tend to absorb activating light strongly, the activating light might not have penetrated to the depths of die lens forming composition. The lens forming composition, however, contained a co-initiator in conjunction with a photoinitiator to help promote the curing of the entire lens forming composition. The present example thus demonstrates that a sunglass lens containing activating light absorbing fixed pigments may be cured using activating light to initiate polymerization of a lens forming composition which contains a photoinitiator/co- initiator system. FURTHER IMPROVEMENTS

LIGHT INITIATED POLYMERIZATION OF A LENS FORMING COMPOSITION CONTAINING LIGHT ABSORBING MATERIALS

Curing of an eyeglass lens using activating light to initiate the polymerization of a lens forming composition generally requires that the composition exhibit a high degree of activating light transmissibility so that the activating light can penetrate to the deeper regions of the lens cavity. Otherwise the resulting cast lens may possess optical abeπations and distortions. The cast lens may also contain layers of cured material in the regions closest to the transparent mold faces, sandwiching inner layers which are either incompletely cured, gelled, barely gelled, or even liquid. Often, when even small amounts of activating light absorbing compounds have been added to a normally curable lens forming composition, substantially the entire amount of lens forming composition contained within the lens cavity may remain liquid in the presence of activating tight.

Photochromic pigments which have utility for photochromic eyeglass lenses typically absorb activating light strongly and change from an inactivated state to an activated state when exposed to activating light. The presence of photochromic pigments, as well as other activating light absorbing compounds within a lens forming composition, generally does not permit enough activating radiation to penetrate into the deptiis of die lens cavity sufficient to cause photoinitiators to break down and initiate polymerization of the lens forming composition. Examples of such activatmg light absorbing compounds other than photochromic pigments are fixed dyes and colorless additives.

It is therefore difficult to cure a lens forming composition containing activating light absorbing compounds using activating light. One solution to this problem involves the use of a co-initiator. By using a co- initiator, activating light may be used to initiate die polymerization reaction. It is believed tiiat activating light which is directed toward die mold members may cause the photoinitiator to form a polymer chain radical. The polymer chain radical preferably reacts with the co-initiator more readily than witii the monomer. The co- initiator may react with a fragment or an active species of either the photoinitiator or the polymer chain radical to produce a monomer initiating species in the regions of the lens cavity where the level of activating light is either relatively low or not present. It is therefore desirable to provide a method for polymerizing an eyeglass lens forming composition which contains light absorbing compounds by using activating light having a wavelength which is not absorbed by the light absorbing compounds, thus avoiding die need for a co-initiator.

In an embodiment of the present invention, an ophthalmic eyeglass lens may be made from a lens forming composition comprising a monomer, an activating light absorbing compound, and a photoinitiator, by irradiation of the lens forming composition with activating light. As used herein "activating light" means light that may affect a chemical change. Activating light may include ultraviolet light, visible light or infrared light. Generally any wavelength of light capable of affecting a chemical change may be classified as activating.

Chemical changes may be manifested in a number of forms. A chemical change may include, but is not limited to, any chemical reaction which causes a polymerization to take place. Preferably the chemical change causes the formation of a initiator species within the lens forming composition, the initiator species being capable of initiating a chemical polymerization reaction. The lens forming composition, in liquid form, is preferably placed in a mold cavity defined by a first mold member and a second mold member. It is believed that activating light, when directed toward and through the mold members to activate the photoinitiator, causes the photoinitiator to form a polymer chain radical. The polymer chain radical may react with a fragment or an active species of either photoinitiator or the polymer chain radical to produce a monomer initiating species in other regions of the lens cavity.

The use of activating light of the appropriate wavelength preferably prevents the lens from darkening during the curing process. Herein, "darkening" means becoming at least partially non-transparent to the incoming activating light such that the activating light may not significantly penetrate the lens forming composition. Photochromic compounds may cause such darkening. Activating light absorbing compounds present in the lens forming composition may prevent activating light having a wavelength substantially below about 380 nm from penetrating into the lens forming composition. When treated with activating light containing light with wavelengths in the ultraviolet region, e.g. light with wavelengths below about 380 nm, the activating light absorbing compounds darken, preventing further activating light from penetrating the lens forming composition. The darkening of the lens forming composition may also prevent non-ultraviolet activating light from penetrating the composition. This darkening effect may prevent activating light of any wavelength from initiating the polymerization reaction throughout the lens forming composition.

When the activating light absorbing compounds absorb in the ultraviolet region activating light having a wavelength above about 380 nm may be used to prevent die darkening effect. Because the wavelength of the activating light is substantially above the wavelength at which the activating light absorbing compounds absorb, die darkenmg effect may be avoided. Additionally, activating light with a wavelength above about 380 nm may be used to initiate the polymerization of the lens forming material. By the use of such activating light an eyeglass lens containing activating light absorbing compounds may, in some circumstances, be formed without the use of a co-initiator.

In an embodiment the above-described lens forming composition, where the light absorbing compound absorbs activating light light, may be treated with activating light having a wavelength above about 380 nm to activate the photoinitiator. Preferably activating light having a wavelength substantially between about 380 nm to 490 nm is used. By using activating light above about 380 nm the darkening effect caused by the activating light absorbing compounds may be avoided. The activating light may penetrate into the lens forming composition, initiating the polymerization reaction throughout the composition. A filter which blocks light having a wavelength that is substantially below about 380 nm may be used to prevent d e activating light absorbing compounds from darkening.

The use of activating light permits polymerization of the lens forming composition to proceed through the depths of the lens cavity. A cured, clear, abenation free lens is preferably formed in less tiian about 30-60 minutes, more preferably in less than about 20 minutes. As used herein a "clear lens" means a lens that transmits visible light without scattering so that objects beyond the lens are seen clearly. As used herein

"aberration" means the failure of a lens to produce point-to-point conespondence between an object and its image. The lens, when exposed to activating light, preferably inhibits at least a portion of the activating light from being transmitted through the lens. In this manner the eye may be protected from certain light. A lens that inhibits activating light from passing through the lens (at least with respect to certain activating light wavelengths) is more prefened.

In an embodiment, die lens forming composition which contains an activating light absorbing compound may be cured with an activating light. Preferably, the activating light has a wavelength substantially above about 380 nm. In another embodiment, the lens forming composition may be cured with activating light supplied from the FC-104 curing chamber which is depicted in Figs. 14 and 15. The lens forming composition may be cured by exposing the composition to activating light multiple times using both d e UVEXS and the FC- 104. Alternatively, the lens forming composition may be cured by exposing the composition to a plurality of activating light pulses, at least one of the pulses having a duration of less tiian about one second (more preferably less than about 0.1 seconds, and more preferably between 0.1 and 0.001 seconds). Preferably, all activating light directed toward the mold members is at a wavelength between about 380 nm to 490 nm. The previously described embodiments which describe various methods and compositions for forming eyeglass lenses may also be utilized to form an eyeglass lens by using activating light having a wavelength substantially greater than about 380 nm. In an embodiment, die activating light may be generated from a fluorescent lamp. The fluorescent lamp is preferably used to direct activating light rays toward at least one of the mold members. At least one and preferably two fluorescent light sources, witii strong emission spectra in the 380 to 490 nm region may be used. When two light sources are used, tiiey are preferably positioned on opposite sides of the mold cavity. A fluorescent lamp emitting activating light with the described wavelengtiis is commercially available from Voltarc, Inc. of Fairfield, Connecticut as model F20 T12/AQA/BP/65W.

Preferably three or four fluorescent lamps are positioned to provide substantially uniform radiation over the entire surface of the mold assembly to be cured. The activating light source may be turned on and off quickly between exposures. A flasher ballast may be used for this function. A flasher ballast may operate in a standby mode wherein a low cunent is supplied to the lamp filaments to keep d e filaments warm and thereby reduce the strike time of the lamp. Such a ballast is commercially available from Magnatek, Ine of Bridgeport, Connecticut. Alternately, die light source may employ a shutter system to block the light between doses. This shutter system is preferably controlled by a micro-processor based control system in order to provide the necessary doses of light. A feedback loop may be used to control the light intensity so that intensity fluctuations due to environmental variables (e.g. lamp temperature) and lamp aging are rninimized. A light sensor may be incorporated into die control system to minimize variances in dose for a given exposure time. The identity of the major polymerizable components of die lens forming composition tends to affect the optimal curing process. It is anticipated that the identity of the light absorbing compound present in the monomer or blend of monomers may affect die optimal photoinitiator system used as well as die optimal curing process used to initiate polymerization. Also, varying the identities or the proportions of the monomer(s) in die lens forming composition may require adjustments to various production process variables including, but not limited to, exposure times, exposure intensities, cooling times and temperatures, postcure procedures and the like. For example, compositions including relatively slow reacting monomers, such as bisphenol A bis allyl carbonate or hexanediol dimetiiacrylate, or compositions including relatively higher proportions of such monomers may require either longer exposure times, higher intensities, or both. It is postulated tiiat increasing the amount of either fast reacting monomer or the initiator levels present in a system will require reduced exposure times, more rigidly controlled light doses, and more efficient exothermic heat removal.

Preferably, the monomers selected as components of die lens forming composition are capable of dissolving die light absorbing compounds added to them. As used herein "dissolving" means being substantially homogeneously mixed. For example, monomers may be selected from a group including polyol (allyl carbonate) monomers, multi-functional acrylate monomers, and multi-functional methacrylic monomers for use in an activating light absorbing lens forming composition.

In an embodiment, d e mixture of monomers, previously described as PRO-629, may be blended together before addition of other components required to make the lens forming composition. This blend of monomers is preferably used as the basis for a lens forming composition to which activating light absorbing compounds are added.

A polymerization inhibitor may be added to the monomer mixture at relatively low levels to inhibit polymerization of the monomer at inappropriate times (e.g., during storage). Preferably about 0 to 50 ppm of monomethylether hydroquinone (MEHQ) are added to die monomer mixture. It is also prefened tiiat die acidity of die monomer mixture be as low as possible. Preferably less than about 100 ppm residual acrylic acid exists in the mixture. It is also prefened tiiat the water content of the monomer mixture be relatively low, preferably less man about 0.15 percent.

Photoinitiators which have utility in the present invention have been described in previous embodiments. Activating light absorbing compounds which may be added to a normally activating light transmissible lens forming composition have also been described in previous embodiments. The quantity of photochromic pigments present in the lens forming composition is preferably sufficient to provide observable photochromic effect. The amount of photochromic pigments present in the lens forming composition may widely range from about 1 ppm by weight to l-5%> by weight. In prefened compositions the photochromic pigments are present in ranges from about 30 ppm to 2000 ppm. In the more prefened compositions the photochromic pigments are present in ranges from about 150 ppm to 1000 ppm. The concentration may be adjusted depending upon die thickness of the lens being produced to obtain optimal visible light absorption characteristics.

In another embodiment co-initiators may be added to the lens forming composition. As described previously, such compositions may aid die polymerization of the lens forming composition by interacting with the photoinitiator such that d e composition polymerizes in a substantially uniform manner. It is anticipated that die optimal amounts of die lens forming composition components is where the total amount of both initiators are minimized subject to the constraint of complete polymerization and production of a rigid, abenation free lens. The relative proportions of the photomitiator to the co-initiator may be optimized by experimentation. For example, an activating light absorptive lens forming composition that includes a photoinitiator with no co- initiator may be cured. If waves and distortions are observed in the resulting lens, a co-initiator may tiien be added to die lens forming composition by increasing amounts until a lens having the best optical properties is formed. It is anticipated tiiat excess co-initiator in die lens forming composition should be avoided to inhibit problems of too rapid polymerization, yellowing of the lens, and migration of residual, unreacted co-initiator to the surface of the finished lens.

In an embodiment, hindered amine light stabilizers may be added to the lens forming composition. It is believed that tiiese materials act to reduce the rate of degradation of the cured polymer caused by exposure to ultraviolet light by deactivating harmful polymer radicals. These compounds may be effective in terminating oxygen and carbon free radicals, and thus interfering with the different stages of auto- oxidation and photo- degradation. Preferably, more than one monomer and more than one initiator are used in a lens forming composition to ensure that the initial polymerization of the lens formmg composition with activating light does not occur over too short a period of time. The use of such a lens forming composition may allow greater control over the gel formation, resulting in better control of the optical quality of the lens. Further, greater control over the rate of exothermic heat generation may be achieved. Thus, cracking of the lens and premature release of the lens from the mold which are typically caused by die release of heat may be prevented. As mentioned above, exothermic reactions occur during d e curing process of the lens forming composition. As previously described a "donut effect" may occur for positive lens in which the relatively thin outer portion of die lens forming composition reaches its fully cured state before the relatively thick inner portion of the lens forming composition. Conversely, in a negative lens the relatively thin inner portion of the lens forming composition may reach its fully cured state before the relatively thick outer portion of the lens forming composition.

Accordingly, it is prefened tiiat a greater amount of activating light is applied to die thicker sections of the composition than to the tiiinner sections. In one embodiment, as shown in Fig. 36, the thickness of a filter preferably varies so that a thinner section of the filter conesponds to an adjacent tiiicker section of the mold cavity and a tiiicker section of the filter conesponds to an adjacent tiiinner section of the mold cavity. In otiier words, the thickness of die filter may be varied according to the varying thickness of die lens forming composition disposed wititin die mold cavity. The filter is preferably a hazy filter that may be formed by a variety of means. The filter may be polymerized from a hazy material or any combination of materials which create haze. More specifically, the filter may be a "lens" (i.e., a piece of plastic shaped like a lens) made by adding an incompatible chemical to a typical lens forming composition. For example, a bisphenol compound may be added to a lens forming composition and polymerized, resulting in a cloudy filter in the shape of a lens that separates light into numerous (e.g., millions) of fragments. The filter may be injection molded from polyethylene or any suitable thermoplastic.

In one embodiment, after the lens forming composition has been placed in the mold cavity, it may be pre-cooled 3 to 7 minutes before being exposed to activating light. Thus, the lens forming composition may be cooled to below ambient temperature prior to polymerization of the lens forming composition. Advantageously, the heat released by the reaction within the composition may be balanced by die coolness of die composition so mat die composition is not exposed to exfreme amounts of thermal radiation. Thus, exposing die lens forming composition to below ambient temperatures before the reaction is initiated may inhibit undesirable effects resulting from the exothermic nature of the reaction. For example, cooling the lens forming composition might help prevent the loss of process control caused by variations in the rate of reaction that result from temperature changes of the lens forming composition.

In an embodiment, the activating light is directed toward the mold members until at least a portion of the lens forming composition is a gel. At this point, application of the activating light is preferably terminated to inhibit the polymerization reaction from proceeding too rapidly, tiiereby inhibiting the rate of heat generation from increasing so rapidly that premature release of the lens from the mold cavity and/or cracking of the lens results. The heat generated by die polymerization reaction may also be controlled by applying a stream of air to the mold cavity to remove heat from he mold cavity. Cooling of the mold cavity has been previously described. After termination of the activating light, the gasket holding the two mold members together is preferably removed to expose the lens forming composition to air while the reaction is allowed to continue at a desired rate. The air may advantageously help cool the lens forming composition. In an embodiment, die lens forming composition may be exposed to ambient conditions for about 5 to 30 minutes, depending on die mass of the composition. It is believed tiiat approximately one minute of such exposure is prefened for each gram of the composition. Since die amount of heat released during reaction tends to be proportional to the mass of the composition, the more mass the composition has, the longer it may be cooled. After cooling the composition, it may be exposed to activating light again if desired.

In an embodiment, die inner surface, i.e., the casting face, of me front mold member may be coated with one or more hardcoat layers before the lens forming composition is placed within the mold cavity. Preferably, two hardcoat layers are used so tiiat any imperfections, such as pin holes in the first hardcoat layer, are covered by the second hardcoat layer. The resulting double hardcoat layer is preferably scratch resistant and protects the subsequently formed eyeglass lens to which die double hardcoat layer adheres. In an embodiment, the casting face of the back mold member may be coated with a material prior to filling the mold cavity with the lens forming composition. This material may be capable of being tinted witii dye. This tintable coat preferably adheres to the lens forming composition so that dyes may later be added to die resulting eyeglass lens for tinting the lens.

In an embodiment, dyes may be added to d e lens forming composition. It is believed tiiat certain dyes may be used to attack and encapsulate ambient oxygen so tiiat the oxygen cannot react with free radicals formed during the curing process. Also, dyes may be added to the composition to alter the color of an inactivated photochromic lens. For instance, a yellow color tiiat sometimes results after a lens is formed may be "hidden" if a blue-red or blue-pink dye is present in the lens forming composition. The inactivated color of a photochromic lens may also be adjusted by the addition of non-photochromic pigments to the lens forming composition.

In an embodiment, the eyeglass lens that is formed may be coated witii a hydrophobic layer, e.g. a hardcoat layer. The hydrophobic layer preferably extends the life of the photochromic pigments near the surfaces of the lens by preventing water and oxygen molecules from degrading the photochromic pigments. In a prefened embodiment, both mold members are coated witii a cured adhesion-promoting composition prior to placing the lens forming composition into the mold cavity. Providing the mold members with such an adhesion-promoting composition is prefened to increase the adhesion between the casting surface of the mold and the lens forming composition. The adhesion-promoting composition thus reduces die possibility of premature release of the lens from the mold. Further, it is believed tiiat such a coating also provides an oxygen and moisture banier on the lens which serves to protect the photochromic pigments near the surface of the lens from oxygen and moisture degradation. Yet further, the coating provides abrasion resistance, chemical resistance, and improved cosmetics to d e finished lens. An eyeglass lens formed using the lens forming composition of the present invention is not only applicable for use as a prescription lens and may be used for a non-prescription lens as well. Particularly, such a lens may be used in sunglasses. Advantageously, photochromic sunglass lenses would remain light enough in color to allow a user to see through them clearly while at the same time prohibiting ultraviolet light from passing through the lenses. In one embodiment, a background dye may be added to the photochromic lens to make the lens appear to be a dark shade of color at all times like typical sunglasses.

Each of the embodiments described above may be combined or used individually.

PREPARING LENS OF VARIOUS POWERS BY ALTERING THE LENS FORMING CONDITIONS.

It has been determined tiiat in some embodiments the finished power of an activating light polymerized lens may be controlled by manipulating die curing temperature of the lens forming composition. For instance, for an identical combination of mold members and gasket, the focusing power of the produced lens may be increased or decreased by changing die intensity of activating light across the lens mold cavity or die faces of die opposed mold members. As the lens forming material begins to cure, it passes through a gel state, the pattern of which, within the lens cell, leads to die proper distribution of internal stresses generated later in die cure when the lens forming material begins to shrink. As the lens forming material shrinks during die cure, die opposed mold members will preferably flex as a result of the different amounts of shrinkage between the relatively thick and the relatively thin portions of the lens. When a negative lens, for example, is cured, the upper or back mold member will preferably flatten and die lower or front mold member will preferably steepen witii most of the flexing occurring in the lower or front mold member. Conversely, witii a positive lens, the upper or back mold member will preferably steepen and the lower or front mold member will preferably flatten witii most of the flexing occurring in the upper or back mold member.

By varying the intensity of die activating light between the relatively thin and tiie relatively thick portions of the lens in the lens forming cavity, it is possible to create more or less total flexing. Those light conditions which result in less flexing will tend to minimize die possibility of premature release.

The initial curvature of the opposed mold members and the center thickness of die lens produced can be used to compute the targeted power of the lens. Herein, the "targeted power" of a lens is die power a lens may have if the lens were to have a curvature and tiiickness substantially identical to die mold cavity formed by the opposed mold members. The activating light conditions may be manipulated to alter the power of the lens to be more or less than the targeted power.

By varying the amount of activating light reaching the lens mold die polymerization rate, and tiierefore the temperature of the lens forming composition may be controlled. It has been determined that the maximum temperature reached by the lens forming composition during and/or after activation by light may effect the final power of the lens. By allowing the lens forming composition to reach a temperature higher than the typical temperatures described in previous embodiments, but less than the temperature at which the formed lens will crack, die power of the lens may be decreased. Similarly, controlling the polymerization such that the temperature of the lens forming composition remains substantially below the typical temperatures described in previous embodiments, but at a sufficient temperature such that a properly cured lens is formed, die power of d e lens may be increased. Similarly, increasing such lens forming composition temperature during curing may decrease the power of the resulting lens.

In an embodiment, an ophtiialmic eyeglass lens may be made from a lens forming composition comprising a monomer and a photoinitiator, by irradiation of the lens forming composition with activating light. The composition may optionally include one or more of: an activating light absorbing compound, a polymerization inhibitor, a co-initiator, a hindered amine light stabilizer, and a dye. The activating light may include ultraviolet, visible or infrared light. The lens forming composition may be treated with activating light such that an eyeglass is formed which has a power substantially equal to the targeted power for a given mold cavity. The peak temperature of the lens forming process may be the maximum temperature attained after the application of each pulse of activating light. As depicted in Fig. 40, each pulse of activating light may cause the lens forming composition to rise to a peak temperature.

After reaching this peak temperature the lens forming composition may begin to cool until the next application of activating light. If the peak temperature of the lens forming composition is controlled such that the formed lens has a power substantially equal to the targeted power, the peak temperature is refened to as the "matching temperature". The matching temperature may be determined by performing a series of experiments using the same mold cavity. In tiiese experiments the peak temperature attained during die process is preferably varied. By measuring the power of the lenses obtained tiirough this experiment the matching temperature range may be determined. When the temperature of the lens forming composition is allowed to rise above the matching temperature during treatment with activating light, the power of the lens may be substantially less than the targeted power of die lens. Alternatively, when the temperature of the lens forming composition is allowed to remain below the matching temperature, the power of the lens may be substantially greater than the targeted power of the lens. In this manner, a variety of lenses having substantially different lens powers from die targeted power may be produced from the same mold cavity.

When die lenses cured by die activating light are removed from the opposed mold members, they are typically under a stressed condition. It has been determined that the power of the lens can be brought to a final resting power, by subjecting the lenses to a post-curing heat treatment to relieve the internal stresses developed during the cure and cause the curvature of the front and the back of the lens to shift. Typically, the lenses are cured by die activating light in about 10-30 minutes (preferably about 15 minutes). The post-curing heat treatment is conducted at approximately 85-120 °C for approximately 5-15 minutes. Preferably, the post-curing heat treatment is conducted at 100-110 °C for approximately 10 minutes. Prior to the post-cure, die lenses generally have a lower power than d e final resting power. The post-curing heat treatment reduces yellowing of the lens and reduces stress in the lens to alter the power thereof to a final resting power. The post-curing heat treatment can be conducted in a conventional convection oven or any other suitable device.

In an embodiment, an ophthalmic eyeglass lens may be made from a lens forming composition comprising a monomer and a photoinitiator, by irradiation of the lens forming composition with activating light. The composition may optionally include one or more of: an activating light absorbing compound, a polymerization inhibitor, a co-initiator, a hindered amine light stabilizer, and a dye. The activating light may include ultraviolet, visible or infrared light. The lens forming composition may be treated witii activating light such that an eyeglass is formed. The lens may be kept within the mold cavity formed by the mold members until the light has completely cured the lens forming composition. The minimum time which a lens must remain in the mold cavity to produce a lens with d e targeted power, witii respect to die mold cavity, is herein referred to as the "demolding time". The demolding time may be determined by performing a series of experiments using the same mold cavity. In these experiments the time that the lens is released from die mold cavity during the process is preferably varied. By measuring the power of the lenses obtained tiirough this experiment the demolding time range may be determined. When a formed lens is removed prior to the demolding time, the power of the lens may be substantially greater than the targeted power of the lens. By varying the demolding time a variety of lenses having substantially greater lens powers from the targeted power may be produced from the same mold cavity.

MICROPROCESSOR BASED CONTROL SYSTEM

In an embodiment a lens curing apparatus may include a microprocessor based control system. The control system may perform some and/or all of a number of functions during the lens curing process, including: (i) measuring the ambient room temperature; (ii) determining the initial dose of light required to cure die lens forming composition, based on die ambient room temperature; (iii) applying the activating light witii an intensity and duration sufficient to equal the determined dose; (iv) measuring the composition's temperature response during and subsequent to the application of the first dose of light; (v) calculating the dose required for the next application of activating light; (vi) applying the activating light with an intensity and duration sufficient to equal the determined second dose; (vii) repeating these procedures until the lens forming material is substantially cured; (viii) determining when the curing process is complete by monitoring the temperature response of the lens forming composition during die application of activating light; (ix) tracking the usage and maintenance requirements of the system. Herein, "dose" refers to the amount of light energy applied to an object, die energy of the incident light being determined by tiie intensity and duration of the light.

A temperature monitor may be located at a number of positions within a mold chamber. Mold chambers including a temperature monitor have been described in the previous embodiments. In one embodiment an infra-red temperature sensor may be located such tiiat it can measure the temperature of the mold and/or the lens forming composition in the mold cavity. One infra-red temperature sensor may be the Cole-Parmer Model E39669-00 (Vernon Hills, Illinois). The temperature monitor may measure the temperature within the chamber and/or the temperature of air exiting the chamber. The controller may be adapted to send a signal to a cooler and/or distributor to vary the amount and/or temperature of the cooling air. The temperature monitor may also determine the temperature at any of a number of locations proximate the mold cavity. The temperature monitor preferably sends a signal to die controller such that the temperature of mold cavity and or the lens forming composition is known by the controller throughout the curing process.

During the initial set-up the temperature of the lens forming composition within the mold cavity is determined. This initial temperature of the lens forming composition may be about equal to the ambient room temperature. The controller may then determine the initial temperature of the lens forming composition by measuring the ambient room temperature. Alternatively, the initial temperature of the lens forming composition may be measured directly using the aforementioned temperature sensors.

The controller preferably determines the initial dose to be given to the lens forming composition based on die initial temperature of the composition. The controller may use a table to determine die initial dose, the table including a series of values conelating the initial temperature to the initial dose and/or die mass of the lens forming composition. The table may be prepared by routine experimentation. To prepare die table a specific lens forming composition of a specific mass is preferably treated witii a known dose of activating light. The mold cavity is preferably disassembled and die gellation pattern of the lens forming composition observed. This procedure may be repeated, increasing or decreasing the dosage as dictated by die gellation patterns, until the optimal dosage is determined for the specific lens forming composition. During this testing procedure the initial temperature of the lens forming composition may be determined, this temperature being herein refened to as the "testing temperature". In this manner the optimal dose for the lens forming composition at the testing temperature may be determined. When die lens forming material has an initial temperature that is substantially equal to the testing temperature, the initial dosage may be substantially equal to the experimentally determined dosage. When the lens forming material has a temperature that is substantially greater or less than the testing temperature, the initial dose may be calculated based on a function of the experimentally determined initial dose.

In an embodiment, the controller is adapted to control the intensity and duration of activating light pulses delivered from the activating light source and die time interval between the pulses. The activating light source may include a capacitor which stores the energy required to deliver the pulses of activating light. The capacitor may be adapted to allow pulses of activating light to be delivered as frequently as desired. A light sensor may be used to determine the intensity of activating light emanating from the source. The light sensor is preferably adapted to send a signal to die controller, which is preferably adapted to maintain the intensity of the activating light at a selected level. A filter may be positioned between tiie activating light source and die light sensor and is preferably adapted to inhibit a portion of the activating light rays from contacting the light sensor. This filter may be necessary to keep the intensity of the activating light upon the light sensor within the detectable range of the light sensor.

In an embodiment, a shutter system is used to control the application of activating light rays to the lens forming material. The shutter system preferably includes air-actuated shutter plates that may be inserted into the curing chamber to prevent activating light from reaching the lens forming material. The shutter system may be coupled to die controller, which may actuate an air cylinder to cause the shutter plates to be inserted or extracted from the curing chamber. The controller preferably allows the insertion and extraction of the shutter plates at specified time intervals. The controller may receive signals from temperature sensors allowing the time intervals in which the shutters are inserted and/or extracted to be adjusted as a function of a temperature of the lens forming composition and/or the molds. The temperature sensor may be located at numerous positions proximate the mold cavity and/or casting chamber.

In an embodiment a single dose of activating light may be used to cure a lens forming composition. The controller may monitor the change in temperature of the lens forming composition during the application of activating light. The activating light preferably initiates a polymerization reaction such that the temperature of the lens forming composition begins to rise. By monitoring the change in temperature over a time period die controller may determine the rate of temperature change. The controller preferably controls the polymerization of the lens forming composition based on die rate of temperature change. When the temperature is found to be rising at a faster than desired rate, the desired rate being determined based on previous experiments, the temperature controller may alter the intensity or duration of the pulse such that the rate of temperature change is lowered. Typically die duration of the activating light is shortened and/or die intensity of the activating light is diminished to achieve tiiis effect. The controller may also increase the rate of cooling air blowing across the mold to help lower the temperature of the lens forming composition. Alternatively, if the temperature of the reaction is increasing too slowly, the controller may mcrease the intensity of the activating light and/or increase die duration of the pulse. Additionally, the confroller may decrease the rate of cooling air blowing across the mold to allow the temperature of the lens forming composition to rise at a faster rate.

One manner in which the temperature may be controlled is by monitoring die temperature during the application of activating light, as described in U.S. Patent No. 5,422,046 to Tarshiani, et al. During activating light irradiation tiie temperature of the lens forming composition tends to rise. When the temperature reaches a predetermined upper set point the activating light source is preferably turned off. Removal of tiie activating energy may allow the temperature to gradually begin to fall. When the temperature is reduced to a predetermined lower set point the activating light source is turned on. In this way the temperature may be controlled within a desired range. This temperature range tends to be very broad due to die nature of the lens forming polymerization reactions. For example, turning the activating light off at a predetermined upper set point may not insure that the temperature of the lens forming composition will stop at that point. In fact, it is more likely that die temperature may continue to rise after the upper set point has been reached. To offset this effect the upper set point may be set at a temperature lower than the upper temperature desired during die lens forming process. Such a method of temperature control may be insufficient to control the temperature. As shown in Fig. 40, increase in the temperature of a lens forming composition during the lens forming process may not be constant. Since the increase in temperature of the composition changes as the process continues, the use of an upper set point for controlling the temperature may not adequately prevent the composition from reaching greater than desired temperatures. Additionally, near the completion of the process the upper set point may be set too low, thereby preventing the lens forming composition from reaching a temperature that is adequate to maintain the polymerization reaction due to insufficient doses of activating light.

In an embodiment die temperature control process may be described as a modified PID (Proportional, Integral, Derivative) control schema. Preferably the temperature of the lens forming composition is controlled in tins manner with a PID controller. The PID controller may use a number of factors to determine the dose of activating light applied for each pulse. The PID controller preferably measures the temperature as well as the rate of temperature change.

The PID controller uses a method involving die combination of proportional, integral and derivative controlling methods. The first, proportional control, may be achieved by mixing two control factors in such a way as to achieve the desired effect. For lens control die two factors which may have the most effect on temperature control are the dosage of activating light and the flow rate of the cooling air. These two factors may be altered to achieve a desired temperature response. If the temperature must be raised as rapidly as possible a full dosage of light may delivered with no cooling air present. Similarly, if the composition must be rapidly cooled die sample may be treated with cooling air only. Preferably the two factors, application of incident light and cooling, are both applied to achieve die desired temperature response. The mixture, or proportions of tiiese factors may allow the temperature of the composition to be controlled.

The use of proportional control tends to ignore otiier effects that influence the temperature of the lens forming composition. During the lens forming process the temperature of the lens forming composition may vary due to die rate of polymerization of the reaction.. When the composition is undergoing a rapid rate of polymerization, the temperature of the composition may rise beyond tiiat determined by the proportional setting of the activating light and cooling air controls. Toward the end of the process the lens may become too cool due to the a reduction in d e rate of polymerization of the composition. The use of proportional control may tiierefore be inadequate to control this procedure and may lead to greater than desired variations in the temperature of the composition. These limitations may be overcome by altering the proportions of the two components in response to the temperature of the composition. A single set point may be used to control the temperature of a reaction. As the temperature rises above this set point the proportion of the activating light and cooling may be adjusted such that die temperature begins to lower back toward die set point. If the temperature drops below the set point the proportion of activating light and cooling may be adjusted to raise die temperature back to the set point. Typically, to lower the temperature the dose of activating light may be reduced and/or die flow rate of die cooling air may be increased. To raise die temperature the dose of activating light may be increased and/or tiie flow rate of the cooling air may be decreased.

The use of proportional control in this manner may not lead to a steady temperature. Depending on the set point and die response time of the lens forming composition to variations in the dosage of light and/or cooling air, die temperature may oscillate over the set point, never attaining a steady value. To better control such a system the rate of change of the temperature over a predetermined time period is preferably monitored. As the temperature rises the rate at which the temperature rises is preferably noted. Based on this rate of change die controller can then alter the dosage of activating light and/or cooling air such that a temperature much closer to die set point may be achieved. Since the rate will change in response to changes in die rate of polymerization, such a system may better control the temperature of the lens forming composition throughout the process.

In an embodiment d e confroller is a modified PID controller. The controller preferably monitors the temperature of the lens forming composition throughout the process. Additionally, the confroller may monitor the rate of change of temperature throughout the reaction. When a plurality of pulses are being applied to control the polymerization, the confroller preferably controls the duration and intensity of each pulse to control the temperature of the composition. In a typical process the rate of change in temperature is preferably monitored after the application of an activating light pulse. If the temperature is trending in an upward direction, the controller preferably waits for the temperature to crest and start descending, before the application of additional light pulses. This cresting temperature may vary, as depicted in Fig. 40, tiiroughout the lens forming process. After the temperature has passed a predetermined set point, a dose, calculated from the rate of change in temperature caused by the application of the previous pulse, is applied to die lens forming composition. After the light pulse is delivered die controller repeats the procedure. When the reaction nears completion the controller detects die lack of response to the last exposure (i.e. the lens temperature did not increase appreciably). At this point the controller may apply a final dose to assure a substantially complete cure and notify the operator that the mold assembly is ready to be removed form the chamber. Additionally, The microprocessor based confrol system provides system diagnostics and manages an interlock system for safety purposes. The control system will notify the user when routine maintenance is due or when a system enor is detected. The control system will track system usage and lens yield rates.

It is to be understood tiiat embodiments of a microprocessor based control system, as described above, may be combined witii the methods and apparatus of prefened embodiments described above in die previous sections.

Further modifications and alternative embodiments of various aspects of die invention will be apparent to tiiose skilled in the art in view of this description. Accordingly, this description is to be construed as illustrative only and is for the purpose of teaching those skilled in the art the general manner of carrying out the invention. It is to be understood tiiat the forms of the invention shown and described herein are to be taken as die presently preferred embodiments. Elements and materials may be substituted for those illustrated and described herein, parts and processes may be reversed, and certain features of the invention may be utilized independently, all as would be apparent to one skilled in the art after having the benefit of this description of the invention. Changes may be made in die elements and compositions described herein or in the features or in the sequence of features of the methods described herein without departing from the spirit and scope of die invention as described in die following claims.

Claims

What is Claimed:
1. A lens forming composition adapted to cure to form a plastic eyeglass lens upon exposure to activating light during use, comprising:
a monomer capable of being cured to form a plastic eyeglass lens during use;
an activating light absorbing compound for inhibiting at least a portion of activating light from being transmitted through the eyeglass lens during use;
a co-initiator adapted to activate curing of the monomer to form the eyeglass lens during use; and
a photoinitiator adapted to activate the co-initiator in response to being exposed to activating light during use.
2. The lens forming composition of claim 1 wherein the activating light absorbing compound is dissolved in the monomer.
3. The lens forming composition of claim 1, further comprising a hydroquinone compound
4. The lens forming composition of claim 1, further comprising a hydroquinone compounds adapted to inhibit polymerization of the monomer before polymerization is desired.
5. The lens forming composition of claim 1, further comprising between about 0 and 70 ppm of monomethylether hydroquinone.
6. The lens forming composition of claim 1 wherein the activating light absorbing compound comprises a photochromic compound.
7. The lens forming composition of claim 1 wherein the activating light compound comprises a photochromic compound, and wherein the photochromic compound comprises a compound selected from the group consisting of spirooxazine, spiropyrans, spironaphhoxazines, spiropyridobenzoxazines, spirobenzoxazines, napthopyrans benzopyrans, spironapthopyrans, indolinospironapthoxazines, indolrnospironapthopyrans, diarylnaptiiopyrans, organometallic, and phenylmercury.
8. The lens forming composition of claim 1 wherein the activating light absorbing compound comprises a photochromic compound, and wherein an amount of photochromic compound in the lens forming composition ranges from about 1 ppm to about 5%> by weight.
9. The lens forming composition of claim 1 wherein the activating light absorbing compound comprises a photochromic compound, and wherein an amount of photochromic compound in the lens forming composition ranges from about 30 ppm to about 2000 ppm.
10. The lens forming composition of claim 1 wherein the activating light absorbing compound comprises a photochromic compound, and wherein an amount of photochromic compound in the lens forming composition ranges from about 150 ppm to about 1000 ppm.
11. The lens forming composition of claim 1 wherein the activating light absorbing compound comprises a compound selected from die group consisting of 2(2H benzotriazole-2-yl)4-(l,l,3,3 tettamethyl butyl) phenol, 2 hydroxy-4-methoxy benzophenone, mixtures of 2-[4-((2-hydroxy-3-dodecyloxypropyl)-oxy] 2-2- hydroxyphenyl]-4,6-bis(2,4-dimethylphenyl)-l,3,5-triazine and 2-[4-((2-hydroxy-3-tridecyloxypropyl)-oxy]-2- hydroxyphenyl]-4,6-bis(2,4-dimethylpheyl-l,3,5-triazine, mixtures of poly (oxy-l,2-ethanediyl) and a-(3-(3- (2H-benzotriazol-2-yl)-5-( 1 , 1 -dimeti╬╣ylethyl)-4-hydroxyphenyl)- 1 -oxopropyl)-w-hydroxy, a-(3-(3-(2H- benzotriazol-2-yl)-5-( 1 , 1 -dimethyleti╬╣yl)-4-hydroxyphenyl)- 1 -oxopropyl)-w-(3-(3-(2H-benzotriazol-2-yl)-5- (l,l-dimethylethyl)-4-hydroxyphenyl)-l-oxopropoxy), 2(2-hydroxy-5 -methyl phenyl) benzotriazole, ethyl-2- cyano 3,3-diphenyl acrylate, and phenyl salicylate.
12. The lens forming composition of claim 1, further comprising a hindered phenolic compound.
13. The lens forming composition of claim 1, further comprising a hindered phenolic compound selected from the group consisting of thiodiethylene bis-(3,5,-di-tert-butyl-4-hydroxy)hydrocinnamate and octadecyl 3,5-bis(l,l-dimethylethyl)-4-hydroxybenzene-propanoate for inhibiting oxidation of the lens forming composition.
14. The lens forming composition of claim 1 wherein an amount of photoinitiator in the lens forming composition ranges from about 50 ppm to about 2000 ppm.
15. The lens forming composition of claim 1 wherein an amount of co-initiator in the lens forming composition ranges from about 1 ppm to about 7% by weight.
16. The lens foπriing composition of claim 1 wherein an amount of co-initiator in the lens forming composition ranges from about 0.3% to about 2%> by weight.
17. The lens forming composition of claim 1, further comprising less than about 0.15% water.
18. The lens forming composition of claim 1, further comprising less than about 100 ppm residual acrylic acid.
19. The lens forming composition of claim 1 wherein the monomer comprises a polyethylenic-functional monomer containing ethylenically unsaturated groups selected from acrylyl and methacrylyl.
20. The lens forming composition of claim 1 wherein the monomer comprises an aromatic containing bis(allyl carbonate)-functional monomer.
21. The lens forming composition of claim 1 wherein the monomer comprises a compound selected from the group consisting of polyol (allyl carbonate)-functional monomer, acrylic-functional monomer, methacrylic- functional monomer, and mixtures thereof.
22. The lens forming composition of claim 1 wherein the monomer comprises a compound selected from the group consisting of tripropyleneglycol diacrylate, tettaethyleneglycol diacrylate, trimethylolpropane triacrylate, trimethylolpropane triacrylate, bisphenol A bis allyl carbonate, hexanediol dimethacrylate, and mixtures thereof.
23. The lens forming composition of claim 1 wherein the co-initiator comprises an amine.
24. The lens forming composition of claim 1 wherein the co-initiator comprises N-methyldiethanolamine.
25. The lens forming composition of claim 1 wherein the co-initiator comprises a compound selected from the group consisting of N,N-dimethyldiethanolamine, friethanolamine, ethyl-4-dimethylamino benzoate, ethyl- 2-dimetiiylamino benzoate, n-butoxyethyl-4-dimethyl amino benzoate, P-dimethyl amino benzaldehyde, N,N- dimethyl-para-toluidine, and octyl-para (dimethylamino) benzoate.
26. The lens forming composition of claim 1 wherein the photoinitiator comprises a compound selected from the group consisting of 1-hydroxycyclohexylphenyl ketone, mixtures of bis(2,6-dimethoxybenzoyl) (2,4,4,-trimethyl phenyl) phosphine oxide and 2-hydroxy-2methyl-lphenyl-propanl-one, mixtures of bis(2,6 dimethoxybenzoyl) (2,4,4,-trimethyl phenyl) phosphine oxide and 1-hyroxycyclohexylphenyl ketone, 2,2- dimedιoxy-2-phenyl acetophenone, 2-hydroxy-2methyl-lphenyl-proρanl-one, mixtures of 2,4,6- trimethylbenzoyl-diphenylphosphine oxide and 2-hydroxy-2-methyl-lphenyl-propanl, 2,2- diethoxyacetophenone, benzil dimethyl ketal, alpha hydroxy ketone, 2-methyl thioxanthone, 2-chloro thioxanthone, thioxanthone, xanthone, 2-isopropyl thioxanthone, mixtures of triaryl sulfonium hexafluoroantimonate and propylene carbonate, diaryl diodonium hexafluoroantimonate, mixtures of benzophenone and 1-hydroxycyclohexylphenyl ketone, 2-benzyl-2-N,N-dιmethylamιno-l-(4- morpholrnophenyl)- 1 -butanone, 2-methyl- 1 -[4-(methylthιo)phenyl]-2-morpholιno propan- 1 -one, bιs(n5-2,4- cyclopentadιen-lyl)-bιs-[2,6-dιfluoro-3-(lH-pynol-l-yl) phenyl] titanium, mixtures of 2,4,6- trimethyl benzophenone and 4-methylbenzophenone, benzoyl peroxide, and methyl benzoyl formate
27 The lens formmg composition of claim 1 wherem the photoinitiator comprises b╬╣s(2,6 drmethoxybenzoyl) (2,4,4 trimethyl phenyl) phosphine oxide
28 The lens formmg composition of claim 1 , further comprising a dye to form a background color withm die lens
29 The lens forming composition of claim 1 wherein the co-initiator comprises a dye
30 The lens forming composition of claim 1 further comprising bιs(l,2,2,6,6-pentamethyl-4-ριpeπdmyl) sebacate for inhibiting degradation of the cured monomer caused by exposure to activating light
31 The lens formmg composition of claim 1 wherem the photomitiator is adapted to form a polymer cham radical m response to bemg exposed to activatmg light durmg use
32 The lens forming composition of claim 1 wherem the photomitiator is adapted to form a polymer chain radical in response to bemg exposed to activatmg light durmg use, and wherem the polymer cham radical is adapted to react with the co-initiator durmg use
33 The lens forming composition of claiml wherem the co-initiator is adapted to form a polymer cham radical upon bemg activated during use
34 The lens forming composition of claim 1 wherein the co-initiator is adapted to form a polymer cham radical upon bemg activated duπng use, and wherem the polymer cham radical reacts with the monomer to cure the monomer durmg use
35 The lens formmg composition of claim 1, further compπsmg a dye for inhibiting ambient oxygen from reacting with the activatmg light absorbing compound duπng use
36 The lens formmg composition of claim 1, further compπsmg a dye for altermg a background color of die lens duπng use
37. The lens forming composition of claim 1, further comprising a dye for inhibiting the activating light absorbing compound from being exposed to predetermined wavelengths of light that are capable of harming the activating light absorbing compound.
38. The lens foπning composition of claim 1 wherein the lens forming composition is curable to a substantially abenation free lens in less than about 30 minutes.
39. The lens forming composition of claim 1 wherein the lens forming composition is curable to a substantially abenation free lens in less than about 10 minutes.
40. The lens forming composition of claim 1 , wherein the activating light absorbing compound comprises an ultraviolet light absorbing compound, and wherein the photoinitiator is adapted to activate the co-initiator in response to being exposed to ultraviolet light.
41. An ophthalmic eyeglass lens comprising:
an at least partially polymerized monomer, said polymerized monomer having been at least partially polymerized by a metiiod comprising:
directing activating light toward a lens forming composition to activate a photoinitiator within the lens forming composition such that the photoinitiator activates a co-initiator within the lens foπning composition, thereby activating polymerization of the monomer; and
an activating light absorbing compound adapted to inhibit at least a portion of activating light from being transmitted through the eyeglass lens, the activating light absorbing compound being substantially distributed throughout the eyeglass lens.
42. The ophthalmic eyeglass lens of claim 41 , further comprising a hydroquinone compound substantially distributed diroughout the eyeglass lens for inhibiting polymerization of the monomer before polymerization is desired.
43. The ophtiialmic eyeglass lens of claim 41, further comprising between about 0 and 70 ppm of monomethylether hydroquinone substantially distributed diroughout the eyeglass lens.
44. The ophtiialmic eyeglass lens of claim 41 wherein the activating light absorbing compound comprises a photochromic compound.
I l l
45 The ophthalmic eyeglass lens of claim 41 wherem the activating light absorbing compound comprises a photochromic compound, and wherem the photochromic compound comprises a compound selected from the group consisting of spirooxazme, spiropyrans, spironaphthoxazines, spiropyπdobenzoxazmes, spirobenzoxazines, napthopyrans benzopyrans, spironapthopyrans, lndolmospironapthoxazines, lndolinospuonapthopyrans, diary lnapthopyrans, organometallic, and phenylmercury
46 The ophthalmic eyeglass lens of claim 41 wherem the activatmg light absorbing compound comprises a photochromic compound, and wherem an amount of photochromic compound m the lens formmg composition ranges from about 1 ppm to about 5% by weight
47 The ophthalmic eyeglass lens of claim 41 wherem the activatmg light absorbmg compound comprises a photochromic compound, and wherein an amount of photochromic compound m the lens formmg composition ranges from about 30 ppm to about 2000 ppm
48 The ophthalmic eyeglass lens of claim 41 wherem the activating light absorbing compound comprises a photochromic compound, and wherem an amount of photochromic compound m the lens formmg composition ranges from about 150 ppm to about 1000 ppm
49 The ophthalmic eyeglass lens of claim 41 wherem the activatmg light absorbmg compound compnses a photochromic compound, and wherein an amount of photoinitiator m the lens forming composition ranges from about 30 ppm to about 2000 ppm
50 The ophthalmic eyeglass lens of claim 41 further compπsmg less than about 0 15% water
51 The ophthalmic eyeglass lens of claim 41 further comprising less than about 100 ppm residual acrylic acid
52 The ophthalmic eyeglass lens of claim 41 wherein the activating light absorbmg compound comprises a compound selected from the group consistmg of 2(2H benzotπazole-2-yl)4-(l, 1,3,3 teframethyl butyl) phenol, 2 hydroxy-4-methoxy benzophenone, mixtures of 2-[4-((2-hydroxy-3-dodecyloxypropyl)-oxy] 2-2- hydroxyphenyl]-4,6-bιs(2,4-drmethylphenyl)-l,3,5-tπazme and 2-[4-((2-hydroxy-3-tπdecyloxypropyl)-oxy]-2- hydroxyphenyl]-4,6-bιs(2,4-dιmethylpheyl-l,3,5-tπazιne, mixtures of poly (oxy-l,2-ethanedιyl) and a-(3-(3- (2H-benzotπazol-2-yl)-5-( 1 , 1 -dιmethyletiιyl)-4-hydroxyphenyl)- 1 -oxopropyl)-w-hydroxy, a-(3-(3-(2H- benzotπazol-2-yl)-5-( 1 , 1 -dιmethyletiιyl)-4-hydroxyphenyl)- 1 -oxopropyl)-w-(3-(3-(2H-benzotπazol-2-yl)-5- (l,l-dιmethylethyl)-4-hydroxyphenyl)-l-oxopropoxy), 2(2-hydroxy-5-methyl phenyl) benzotπazole, ethyl-2- cyano 3,3-dιρhenyl acrylate, and phenyl sahcylate
53. The ophthalmic eyeglass lens of claim 41, further comprising a hindered phenolic compound selected from the group consisting of thiodiethylene bis-(3,5,-di-tert-butyl-4-hydroxy)hydrocinnamate and octadecyl 3,5-bis(l,l-dimethylethyl)-4-hydroxybenzene-propanoate for inhibiting oxidation of the lens.
54. The ophtiialmic eyeglass lens of claim 41 wherein the monomer is a polyethylenic-functional monomer containing ethylenically unsaturated groups selected from acrylyl and methacrylyl.
55. The ophthalmic eyeglass lens of claim 41 wherein the monomer is an aromatic containing bis(allyl carbonate)-functional monomer.
56. The ophthalmic eyeglass lens of claim 41 wherein the monomer comprises a compound selected from the group consisting of polyol (allyl carbonate)-functional monomer, acrylic-functional monomer, methacrylic- functional monomer, and mixtures thereof.
57. The ophthalmic eyeglass lens of claim 41 wherein the monomer comprises a compound selected from the group consisting of tripropyleneglycol diacrylate, tetraethyleneglycol diacrylate, trimethylolpropane triacrylate, trimethylolpropane triacrylate, bisphenol A bis allyl carbonate, hexanediol dimetiiacrylate, and mixtures thereof.
58. The ophthalmic eyeglass lens of claim 41, further comprising a dye to form a background color within the lens.
59. The ophthalmic eyeglass lens of claim 41 , further comprising bis( 1 ,2,2,6,6-pentamethyl-4-piperidinyl) sebacate for inhibiting degradation of the polymerized monomer caused by exposure to activating light.
60. The ophthalmic eyeglass lens of claim 41, further comprising a dye for inhibiting ambient oxygen from reacting with the activating light absorbing compound during casting of the eyeglass lens, the dye being substantially distributed diroughout the eyeglass lens.
61. The ophtiialmic eyeglass lens of claim 41, further comprising a dye for altering a background color of the lens, the dye being substantially distributed throughout the eyeglass lens
62. The ophtiialmic eyeglass lens of claim 41, further comprising first and second layers of hardcoat disposed across a front edge of the eyeglass lens for protecting the eyeglass lens.
63. The ophtiialmic eyeglass lens of claim 41, further comprising a material capable of being tinted disposed across a back edge of the eyeglass lens.
64. The ophthalmic eyeglass lens of claim 41, further comprising a dye for creating background color in the lens, the dye being substantially distributed throughout the eyeglass lens.
65. The ophthalmic eyeglass lens of claim 41, further comprising a hydrophobic coat disposed across an outer surface of the eyeglass lens for inhibiting the eyeglass lens from being exposed to water and ambient oxygen.
66. A system for making an ophthalmic eyeglass lens, comprising:
a first mold member having a casting face and a non-casting face;
a second mold member having a casting face and a non-casting face, the second mold member being adapted to be spaced apart from the first mold member during use such that the casting faces of the first mold member and die second mold member at least partially define a mold cavity;
a lens forming composition adapted to be disposed within the mold cavity during use, comprising:
a monomer capable of being cured to form the eyeglass lens;
an activating light absorbing compound for inhibiting at least a portion of activating light from being transmitted tiirough the eyeglass lens, the activating light absorbing compound being substantially distributed throughout the eyeglass lens;
a co-initiator adapted to activate curing of the monomer to form the eyeglass lens during use; and
a photoinitiator adapted to activate the co-initiator in response to being exposed to activating light during use; and
a first light generator adapted to generate and direct activating light toward the lens forming composition during use.
67. The system of claim 66, further comprising a controller adapted to control the first light generator such that activating light is directed in a plurality of pulses toward at least one of the first and second mold members, at least one of the pulses having a duration of less than one second.
68 The system of claim 66 wherem the first light generator is adapted to direct activating light toward the first mold member, and further comprismg a second light generator adapted to generate and direct a pulse of activatmg light toward the second mold member
69 The system of claim 66 wherem the first light generator is adapted to direct activating light toward the first mold member, and further comprismg a second light generator adapted to generate and direct a pulse of activatmg light toward the second mold member, and further comprismg a confroller adapted to control the first and second light generators such that activating light is duected m a plurality of pulses toward die first and second mold members, at least one of the pulses having a duration of less than one second
70 The system of claim 66 wherein the first light generator is adapted to generate and direct activating light pulses with a sufficiently high intensity such that the photomitiator forms a first polymer chain radical
71 The system of claim 66 wherem the first light generator is adapted to generate and direct pulses with a sufficiently high intensity such that the photomitiator forms a first polymer cham radical that reacts with the co- lnitiator and the co-mitiator forms a second polymer chain radical that reacts with the monomer to cure the monomer
72 The system of claim 66, further comprismg a hazy filter disposed directly adjacent to at least one of the mold members, the filter bemg adapted to manipulate intensity of activating light directed toward the lens formmg composition
73 The system of claim 66, further comprismg a hazy filter disposed directly adjacent to at least one of die mold members, the filter comprismg a varying thickness such that the filter varies an mtensity distπbution of activatmg light directed across the mold members
74 The system of claim 66, further comprismg a cooler adapted to cool the mold cavity
75 The system of claim 66, further comprismg a distributor adapted to apply air to the mold cavity to remove heat from the mold cavity
76 The system of claim 66 wherem the first light generator comprises a xenon light source
77 The system of claim 66 wherem the first light generator comprises a photosfrobe havmg a quartz tube
78 The system of claim 66, wherein the first light generator is configured to generate ultraviolet light, and wherein the activating light absorbmg compound comprises an ultraviolet light absorbmg compound
79. A system for making a plastic eyeglass lens, comprising:
a first mold member having a casting face and a non-casting face;
a second mold member having a casting face and a non-casting face, the second mold member being adapted to be spaced apart from the first mold member during use such that the casting faces of the first mold member and the second mold member at least partially define a mold cavity;
a filter adapted to be positioned substantially adjacent to at least one of the mold members during use; and
a first light generator adapted to generate and direct activating light toward at least one of die mold members during use.
80. The system of claim 79 wherein the filter comprises:
a polymerized monomer substantially distributed throughout the filter;
a photoinitiator substantially distributed throughout the filter for initiating polymerization of the monomer in response to being exposed to activating light; and
a compound substantially distributed throughout the filter for making the filter hazy.
81. The system of claim 79 wherein the filter comprises a bisphenol compound to make the filter hazy.
82. The system of claim 79 wherein the filter comprises a styrene-butadiene copolymer to make the filter hazy.
83. The system of claim 79 wherein the filter is substantially translucent to light.
84. The system of claim 79 wherein the filter is substantially hazy such that the filter disperses die activating light into a plurality of light rays during use.
85. The system of claim 79 wherein the filter comprises a varying thickness such that the filter varies an intensity distribution of activating light directed across the mold members during use.
86. The system of claim 79 wherein the filter comprises a varying thickness adapted to vary an intensity distribution of activating light directed across the mold members such that a greater amount of light passing though a thick portion of the filter is attenuated than passing through a thin portion of the filter.
87. The system of claim 79, further comprising a controller adapted to control the first light generator such that activating light is directed in a plurality of pulses toward at least one of the first and second mold members, at least one of die pulses having a duration of less than one second.
88. The system of claim 79 wherein the first light generator is adapted to direct light toward die first mold member, and further comprising a second light generator adapted to generate and direct a pulse of light toward the second mold member.
89. The system of claim 79, further comprising a cooler adapted to cool the mold cavity.
90. The system of claim 79, further comprismg a distributor adapted to apply air to the mold cavity to remove heat from die mold cavity.
91. The system of claim 79 wherein the first light generator comprises a xenon light source.
92. The system of claim 79 wherein the first light generator comprises a photostrobe having a quartz tube.
93. A lens forming composition adapted to cure to form a plastic eyeglass lens upon exposure to activating light during use, comprising:
a monomer capable of being cured to form a plastic eyeglass lens during use;
an activating light absorbing compound adapted to inhibit at least a portion of activating light from being transmitted through the eyeglass lens during use, wherein an amount of activating light absorbing compound in the lens forming composition ranges from about 1 ppm to about 5% by weight;
a co-initiator adapted to activate curing of the monomer to form the eyeglass lens during use, wherein an amount of co-initiator in the lens forming composition ranges from about 1 ppm to about 7% by weight; and
a photoinitiator adapted to activate the co-initiator in response to being exposed to activating light during use, wherein an amount of co-initiator in the lens forming composition ranges from about 50 ppm to about 2000 ppm.
94. A lens forming composition adapted to cure to form a plastic eyeglass lens upon exposure to activating light during use, comprising:
one ore more monomers capable of being cured to form a plastic eyeglass lens during use;
one or more activating light absorbing compounds adapted to inhibit at least a portion of activating light from being transmitted through the eyeglass lens during use;
one or more co-initiators adapted to activate curing of the monomer to form the eyeglass lens during use; and
one ore more photoinitiators adapted to activate the co-initiator in response to being exposed to activating light during use, wherein an amount of co-initiator in the lens forming composition ranges from about 50 ppm to about 2000 ppm.
95. A lens forming composition adapted to cure to form a plastic eyeglass lens upon exposure to activating light during use, comprising:
a monomer capable of being cured to form a plastic eyeglass lens during use;
an activating light absorbing compound adapted to inhibit at least a portion of activating light from being transmitted through the eyeglass lens during use;
a co-initiator adapted to activate curing of the monomer to form the eyeglass lens during use; and
a photoinitiator adapted to activate the co-initiator in response to being exposed to activating light during use,
wherein the lens forming composition is curable to a substantially aberration free lens in less than 30 minutes.
96. A lens forming composition adapted to cure to form a plastic eyeglass lens upon exposure to activating light during use, comprising:
a monomer capable of being cured to form a plastic eyeglass lens during use;
an activating light absorbing compound adapted to inhibit at least a portion of activating light from being transmitted through the eyeglass lens during use; a co-initiator adapted to activate curing of the monomer to form the eyeglass lens during use; and
a photoinitiator adapted to activate the co-initiator in response to being exposed to activating light during use;
wherein the lens forming composition is curable to a substantially abenation free lens in less than 10 minutes.
97. A method for making a plastic eyeglass lens, comprising:
placing a liquid lens forming composition in a mold cavity defined by at least a first mold member and a second mold member, the lens formmg composition comprising:
a monomer capable of being cured to form a plastic eyeglass lens;
an activating light absorbing compound adapted to inhibit at least a portion of activating light from being transmitted through the eyeglass lens;
a co-initiator adapted to activate curing of the monomer to form the eyeglass lens; and
a photoinitiator adapted to activate the co-initiator in response to being exposed to activating light; and
directing activating light toward at least one of the mold members to cure the lens forming composition to form the eyeglass lens in less than approximately 30 minutes.
98. A method for making a plastic eyeglass lens, comprising:
placing a liquid lens forming composition in a mold cavity defined by at least a first mold member and a second mold member, the lens forming composition comprising:
a monomer capable of being cured to form a plastic eyeglass lens;
an activating light absorbing compound adapted to inhibit at least a portion of activating light from being transmitted through the eyeglass lens;
a co-initiator adapted to activate curing of the monomer to form the eyeglass lens; and a photoinitiator adapted to activate the co-initiator in response to being exposed to activating light;
cooling the first mold member and the second mold member below ambient temperature; and
directing activating light toward at least one of the mold members to cure the lens forming composition to form the eyeglass lens.
99. A method for making a plastic eyeglass lens, comprising:
placing a liquid lens forming composition in a mold cavity defined by at least a first mold member and a second mold member, the lens forming composition comprising:
a monomer capable of being cured to form a plastic eyeglass lens;
an activating light absorbing compound adapted to inhibit at least a portion of activating light from being transmitted tiirough the eyeglass lens;
a co-initiator adapted to activate curing of the monomer to form the eyeglass lens; and
a photoinitiator adapted to activate the co-initiator in response to being exposed to activating light;
directing activatng light toward at least one of tiie mold members to cure the lens forming composition to form the eyeglass lens in less than approximately 30 minutes; and
applying a hydrophobic coat to the eyeglass lens to inhibit the eyeglass lens from being exposed to water and to ambient oxygen.
100. A method for making a plastic eyeglass lens, comprising:
providing a mold cavity defined by at least a first mold member and a second mold member;
applying an adhesion-promoter coat to an inner surface of the first mold member and an inner surface of the second mold member to substantially adhere d e lens forming composition to the first and second mold members during use; placing a liquid lens forming composition in the mold cavity, the lens forming composition comprising:
a monomer capable of being cured to form a plastic eyeglass lens;
an activating light absorbing compound adapted to inhibit at least a portion of activating light from being transmitted through the eyeglass lens;
a co-initiator adapted to activate curing of the monomer to form the eyeglass lens; and
a photoinitiator adapted to activate the co-initiator in response to being exposed to activating light; and
directing activating light toward at least one of the mold members to cure the lens forming composition to form the eyeglass lens in less than approximately 30 minutes.
101. A method for making a plastic eyeglass lens, comprising:
placing a liquid lens forming composition in a mold cavity defined by at least a first mold member and a second mold member, the lens forming composition comprising:
a monomer capable of being cured to form a plastic eyeglass lens;
an activating light absorbing compound adapted to inhibit at least a portion of activating light from being transmitted through the eyeglass lens;
a co-initiator adapted to activate curing of the monomer to form the eyeglass lens; and
a photoinitiator adapted to activate the co-initiator in response to being exposed to activating light;
placing a substantially hazy filter substantially adjacent to at least one of die mold members; and
directing activating light toward at least one of the mold members to cure the lens forming composition to form the eyeglass lens in less than approximately 30 minutes,
wherein the hazy filter is adapted to vary intensity of the activating light across the lens forming composition.
102. A method for using a plastic eyeglass lens, comprising:
providing a plastic eyeglass lens made by steps comprising:
placing a liquid lens forming composition in a mold cavity defined by at least a first mold member and a second mold member, the lens forming composition comprising:
a monomer capable of being cured to form a plastic eyeglass lens;
an activating light absorbmg compound adapted to inhibit at least a portion of activating light from being transmitted through the eyeglass lens;
a co-initiator adapted to activate curing of the monomer to form the eyeglass lens; and
a photoinitiator adapted to activate the co-initiator in response to being exposed to activating light; and
directing activating light toward at least one of the mold members to cure the lens forming composition to form the eyeglass lens; and
exposing die eyeglass lens to sunlight such that the eyeglass lens at least partially inhibits transmittance of activating light through the lens.
103. A method for using a plastic eyeglass lens, comprising:
providing a plastic eyeglass lens made by steps comprising:
placing a liquid lens forming composition in a mold cavity defined by at least a first mold member and a second mold member, the lens forming composition comprising:
a monomer capable of being cured to form a plastic eyeglass lens;
an activating light absorbing compound adapted to inhibit at least a portion of activating light from being transmitted through the eyeglass lens;
a co-initiator adapted to activate curing of the monomer to form the eyeglass lens; and a photoinitiator adapted to activate the co-initiator in response to being exposed to activating light; and
directing activating light toward at least one of the mold members to cure the lens forming composition to form the eyeglass lens; and
exposing the eyeglass lens to predetermined wavelengths of radiation such that the eyeglass lens inhibits a portion of the predetermined wavelengths of radiation from being transmitted through the lens.
104. The method of claim 103, wherein the predetermined wavelengtiis of radiation range from about 300 nm to about 700 nm.
105. A method for using a plastic eyeglass lens, comprising:
providing a plastic eyeglass lens, comprising:
an at least partially polymerized monomer, said polymerized monomer having been at least partially polymerized by a method comprising:
directing activating light toward a lens forming composition to activate a photoinitiator within the lens forming composition such that d e photoinitiator activates a co- initiator witiiin the lens forming composition, thereby activating polymerization of the monomer; and
an activating light absorbing compound adapted to inhibit at least a portion of activating light from being transmitted through the eyeglass lens, the activating light absorbing compound being substantially distributed throughout the eyeglass lens; and
exposing the eyeglass lens to sunlight such that the eyeglass lens at least partially inhibits transmittance of activating light through the lens.
106. A method for using a plastic eyeglass lens, comprising:
providing a plastic eyeglass lens, comprising: an at least partially polymerized monomer, said polymerized monomer having been at least partially polymerized by a metiiod comprising:
directing activating light toward a lens forming composition to activate a photoinitiator within the lens forming composition such that the photoinitiator activates a co- initiator within the lens forming composition, thereby activating polymerization of the monomer; and
an activating light absorbing compound adapted to inhibit at least a portion of activating light from being fransmitted through the eyeglass lens, the activating light absorbing compound being substantially distributed diroughout the eyeglass lens; and
exposing the eyeglass lens to predetermined wavelengtiis of radiation such tiiat the eyeglass lens inhibits a portion of the predetermined wavelengths of radiation from being transmitted through the lens.
107. The method of claim 106, wherein the predetermined wavelengtiis of radiation range from about 300 nm to about 700 nm.
108. A metiiod for making a plastic eyeglass lens, comprising:
placing a liquid lens forming composition in a mold cavity defined by at least a first mold member and a second mold member, the lens forming composition comprising:
a monomer that cures by exposure to activating light to form the eyeglass lens during use;
a light absorbing compound that absorbs at least a portion of the activating light during use;
a co-initiator that activates curing of the monomer to form the eyeglass lens during use; and
a photoinitiator that activates the co-initiator in response to being exposed to die activating light during use; and
directing activating light toward at least one of die mold members to cure the lens forming composition to form the eyeglass lens.
109. The method of claim 108 wherein curing the lens forming composition comprises polymerizing the monomer.
110. The method of claim 108 wherein directing activating light to the lens forming composition comprises applying a plurality of activating light pulses to the lens forming composition.
111. The method of claim 108 wherein directing activating light to the lens forming composition comprises applying a plurality of activating light pulses to the lens forming composition.
112. The method of claim 108, further comprising applying air to the mold cavity to remove heat from the mold cavity.
113. The method of claim 108, further comprising directing air toward at least one of the mold members to cool the lens forming composition.
114. The method of claim 108, further comprising applying a hydrophobic coating to the eyeglass lens.
115. The method of claim 108, further comprising applying a hydrophobic coating to the eyeglass lens, wherein the hydrophobic coating is adapted to inhibit die eyeglass lens from being exposed to water and to ambient oxygen.
116. The method of claim 108, further comprising inhibiting the eyeglass lens from being exposed to water and to ambient oxygen by applying a coating to die eyeglass lens.
117. The method of claim 108, further comprising cooling the first mold member and die second mold member to below ambient temperature prior to directing activating light toward at least one of the mold members.
118. The method of claim 108 wherein the first mold member comprises a casting face and a non-casting face, and further comprising placing a first hardcoat layer upon said casting face and a second hardcoat layer upon said first hardcoat layer prior to placing the liquid lens forming composition in the mold cavity.
119. The method of claim 108 wherein the second mold member comprises a casting face and a non-casting face, and further comprising placing a material capable of being tinted upon the casting face prior to placing the liquid lens forming composition in the mold cavity.
120. The method of claim 108 wherein the second mold member comprises a casting face and a non-casting face, and further comprising placing a material capable of being tinted upon the casting face prior to placing the liquid lens forming composition in the mold cavity, and further comprising applying dye to die material to tint the lens forming composition.
121. The method of claim 108, further comprising applying an adhesion-promoter coating to an inner surface of the first mold member and an inner surface of the second mold member to substantially adhere die lens forming composition to the first and second mold members during use.
122. The method of claim 108, further comprising placing a substantially hazy light filter substantially adjacent to at least one of the mold members to vary intensity of activating light across the lens forming composition when the light is directed toward at least one of die mold members.
123. The method of claim 108 wherein the first mold member comprises a casting face and a non-casting face, wherein the second mold member comprises a casting face and a non-casting face, and further comprising directing cooled air having a temperature below ambient temperature toward at least one of the non-casting faces of the first and second mold members to remove heat from the lens forming composition.
124. The method of claim 108 wherein the activating light is removed from the mold members when substantially all of the lens forming composition has reached its gel point.
125. The method of claim 108 wherein the activating light comprises a first intensity, and wherein die activating light is directed toward at least one of the mold members until substantially all of the lens forming composition has reached its gel point, and further comprising directing activating light having a second mtensity towards at least one mold member to cure substantially all of the lens forming composition, the first intensity being greater than die second intensity.
126. The metiiod of claim 108 wherein the activating light is directed toward at least one of tiie mold members until substantially all of the lens forming composition has reached its gel point, and further comprising inhibiting the activating light from further being directed toward the mold members, thereby allowing substantially all of the lens forming composition to cure.
127. The method of claim 108 wherein die eyeglass lens is formed from the lens forming composition in a time period of less than about 10 minutes.
128. The method of claim 108 wherein the eyeglass lens is formed from tiie lens forming composition in a time period of less tiian about 30 minutes.
129. The method of claim 108 wherein die first mold member is spaced apart from the second mold member by a gasket, and further comprising removing the gasket subsequent to directing activating light to at least one of the mold members to expose the lens forming composition to ambient air for approximately 5 to 30 minutes, diereby cooling the lens forming composition.
130. The method of claim 108 wherein the first mold member is spaced apart from the second mold member by a gasket, and further comprising removing the gasket subsequent to directing activating light to at least one of die mold members to expose the lens forming composition to ambient air for approximately 5 to 30 minutes, thereby cooling the lens forming composition, and further comprising directing additional activating light toward at least one of the mold members to at least partially cure the lens forming composition.
131. The method of claim 108, further comprising heating the cured lens forming composition to a temperature between approximately 100┬░C to 120┬░C for approximately 3 to 15 minutes subsequent to curing the lens forming composition.
132. The method of claim 108, further comprising placing a filter substantially adjacent to at least one of the mold members, wherein the filter comprises a varying thickness such that the filter varies an intensity distribution of activating light across the mold members.
133. The method of claim 108, further comprising a filter with a pattern printed on it to vary to optical density.
134. The method of claim 108 wherein directing activating light toward at least one of die mold members initiates the photoinitiator proximate a surface of the lens foπning composition such that the photoinitiator initiates the co-initiator proximate a middle of die lens forming composition, the middle of the lens forming composition having insufficient light to initiate the photoinitiator therein.
135. The method of claim 108 wherein the light absorbing compound is dissolved in the monomer.
136. The method of claim 108 wherein the lens forming composition comprises a hydroquinone compound for inhibiting polymerization of the monomer before polymerization is desired.
137. The method of claim 108 wherein the lens forming composition comprises between about 0 and 70 ppm of monomethyletiier hydroquinone.
138. The method of claim 108 wherein the light absorbing compound comprises a photochromic compound.
139. The method of claim 108 wherein the light absorbing compound comprises a photochromic compound, and wherein die photochromic compound comprises a compound selected from the group consisting of spirooxazkies, spiropyrans, spironaphthoxazines, spiropyridobenzoxazines, spirobenzoxazines, naptiiopyrans benzopyrans, spironapthopyrans, indolinospironapthoxazmes, indolinospironapthopyrans, diarylnapthopyrans, organometallics, and phenylmercury.
140. The method of claim 108 wherein the light absorbing compound comprises a compound selected from the group consistmg of 2-(2H-benzotriazole-2-yl)-4-(l,l,3,3 tetramethylbutyl)phenol, 2-hydroxy-4- metiioxybenzophenone, mixtures of 2-[4-((2-hydroxy-3-dodecyloxypropyl)oxy)-2-hydroxyphenyl]-4,6-bis(2,4- dimethylphenyl)-l,3,5-triazine and 2-[4-((2-hydroxy-3-tridecyloxypropyl)oxy)-2-hydroxyphenyl]-4,6-bis(2,4- dimethylpheyl)-l,3,5-rriazine, mixtures of polyoxy-l,2-ethanediyl and ╬▒-(3-(3-(2H-benzotriazol-2-yl)-5-(l,l- dimethylethyl)-4-hydroxyphenyl)- 1 -oxopropyl)-w-hydroxy, a-(3-(3-(2H-benzotriazol-2-yl)-5-( 1,1- dimeti╬╣ylethyl)-4-hydroxyphenyl)- 1 -oxopropyl)-w-(3-(3-(2H-benzotriazol-2-yl)-5-( 1 , 1 -dimethylethyl)-4- hydroxyphenyl)-l-oxopropoxy), 2(2-hydroxy-5 -methyl phenyl) benzotriazole, ethyl-2-cyano 3,3-diphenyl acrylate, and phenyl salicylate.
141. The method of claim 108, wherein the lens forming composition further comprises a hindered phenolic compound selected from the group consisting of thiodiethylene bis-(3,5-di-tert-butyl-4- hydroxy)hydrocinnamate and octadecyl-3,5-bis(l,l-dimethyleti╬╣yl)-4-hydroxybenzene-propanoate for inhibiting oxidation of tiie lens forming composition.
142. The method of claim 108 wherein the light absorbing compound comprises a photochromic compound, and wherein an amount of photochromic compound in the lens forming composition ranges from about 1 ppm to about 5% by weight.
143. The method of claim 108 wherein the light absorbing compound comprises a photochromic compound, and wherein an amount of photochromic compound in die lens forming composition ranges from about 30 ppm to about 2000 ppm.
144. The method of claim 108 wherein the light absorbing compound comprises a photochromic compound, and wherein an amount of photochromic compound in die lens forming composition ranges from about 150 ppm to about 1000 ppm.
145. The method of claim 108 wherein an amount of photoinitiator in the lens forming composition ranges from about 30 ppm to about 2000 ppm.
146. The method of claim 108 wherein an amount of the co-initiator in the lens forming composition ranges from about 1 ppm to about 7% by weight.
147. The method of claim 108 wherein an amount of the co-initiator in the lens foπning composition ranges from about 0.3% to about 2% by weight.
148. The method of claim 108 wherem the lens foπning composition comprises less than about 0.15% water.
149. The metiiod of claim 108 wherein the lens forming composition comprises less than about 100 ppm residual acrylic acid.
150. The method of claim 108 wherein the monomer is a polyethylenic-functional monomer containing ethylenically unsaturated groups selected from acrylyl and metiiacrylyl.
151. The method of claim 108 wherein the monomer is an aromatic containing bis(allyl carbonate)- functional monomer.
152. The method of claim 108 wherein the monomer comprises a compound selected from the group consisting of polyol (allyl carbonate)-functional monomer, acrylic-functional monomer, methacrylic-functional monomer, and mixtures thereof.
153. The method of claim 108 wherein the monomer comprises a compound selected from die group consisting of tripropyleneglycol diacrylate, tetraethyleneglycol diacrylate, trimethylolpropane triacrylate, trimethylolpropane triacrylate, bisphenol A bis allyl carbonate, hexanediol dimethacrylate, and mixtures thereof.
154. The method of claim 108 wherein the co-initiator comprises an amine.
155. The method of claim 108 wherein the lens forming composition comprises an acrylic amine.
156. The method of claim 108 wherein the lens forming composition comprises an diacrylic amine.
157. The method of claim 108 wherein the co-initiator comprises n-methyl diethanol amine.
158. The method of claim 108 wherein the co-initiator comprises a compound selected from the group consisting of N,N-dimethyldiethanolamine, friethanolamine, ethyl-4-dimethylamino benzoate, ethyl-2- dimetiiylamino benzoate, n-butoxyethyl-4-dimethyl amino benzoate, /7-dimeti╬╣yl amino benzaldehyde, N,N- dimethyl-p-toluidine, and octyl/?-dimethylaminobenzoate.
159. The method of claim 108 wherein the photoinitiator comprises a compound selected from the group consisting of 1-hydroxycyclohexylphenyl ketone, mixtures of bis(2,6-dimethoxybenzoyl) (2,4,4,- trimethylphenyl) phosphine oxide and 2-hydroxy-2-meti╬╣yl-l-phenylpropan-l-one, mixtures of (2,6 dimethoxybenzoyl) (2,4,4,-frimethylphenyl) phosphine oxide and 1-hydroxycyclohexylphenylketone, 2,2- dimethoxy-2-phenylacetophenone, 2-hydroxy-2-methyl-lphenylpropan-l-one, mixtures of 2,4,6- trimethylbenzoyldiphenylphosphine oxide and 2-hydroxy-2-methyl-lphenylpropan-l-one, 2,2- diethoxyacetophenone, benzil dimethylketal, ╬▒-hydroxyketone, 2-methyl thioxanthone, 2-chlorothioxanthone, thioxanthone, xanthone, 2-isopropylthioxanthone, mixtures of triaryl sulfonium hexafluoroantimonate and propylene carbonate, diaryl diodonium hexafluoroantimonate, mixtures of benzophenone and 1- hydroxycyclohexylphenyl ketone, 2-benzyl-2-N,N-dimethylamino-l-(4-mo holinophenyl)-l -butanone, 2- methyl- 1 - [4-(methylthio)phenyl] -2-morpholino propan- 1 -one, bis(╬╖ 5 -2,4-cyclopentadien- 1 -yl)-bis- [2,6- difluoro-3-(lH-pyrrol-l-yl) phenyl] titanium, mixtures of 2,4,6- trimethylbenzophenone and 4- methylbenzophenone, benzoyl peroxide, and methyl benzoylformate.
160. The method of claim 108 wherein die photoinitiator comprises bis(2,6-dimethoxybenzoyl)-(2,4,4 frimethylphenyl) phosphine oxide.
161. The metiiod of claim 108 wherein the photoinitiator forms a polymer chain radical in response to being exposed to activating light.
162. The method of claim 108 wherein the photoinitiator forms a first polymer chain radical in response to being exposed to activating light, and wherein the first polymer chain radical reacts with the co-initiator, thereby forming a second polymer chain radical.
163. The method of claim 108 wherein the photoinitiator forms a first polymer chain radical in response to being exposed to activating light, and wherein the first polymer chain radical reacts with the co-initiator, thereby forming a second polymer chain radical, and wherein the second polymer chain radical reacts with the monomer, thereby curing the monomer.
164. The method of claim 108 wherein the lens forming composition comprises bis(l,2,2,6,6-pentamethyl- 4-piperidinyl)sebacate for inhibiting degradation of the cured monomer caused by exposure to activating light.
165. The method of claim 108 wherein the lens forming composition comprises a dye to form a background color widiin the eyeglass lens.
166. The method of claim 108 wherein the lens forming composition further comprises a dye that inhibits ambient oxygen from reacting with the light absorbing compound.
167. The method of claim 108 wherein the lens forming composition further comprises a dye for altering a background color of the lens during use.
168. The method of claim 108 wherein the lens forming composition further comprises a dye for inhibiting die light absorbing compound from being exposed to predetermined wavelengths of light.
169. A lens made by the method of claim 108.
170. The method of claim 108 wherein an amount of activating light is directed towards the mold cavity, and wherein the mold cavity comprises a temperature, and wherein the amount of activating light directed to the mold cavity is a function of the temperature of at least a portion of the mold cavity.
171. The method of claim 108 wherein directing light to the lens forming composition comprises applying a number of activating light pulses to the lens foπning composition, wherein the number of light pulses is a function of a change in a temperature of the lens forming composition over a period of time.
172. The method of claim 108 wherein directing light to the lens forming composition comprises applying a plurality of activating light pulses to the lens forming composition, wherein a duration of the light pulses is a function of a change in a temperature of the lens forming composition over a period of time.
173. The method of claim 108 wherein directing light to the lens forming composition comprises applying a plurality of activating light pulses to the lens forming composition, wherein an intensity of the light pulses is a function of a change in a temperature of the lens forming composition over a predetermined period of time.
174. The metiiod of claim 108, wherein the activating light absorbing compounds
175. A method for making a plastic eyeglass lens that contains a light absorbing compound by exposing a liquid lens forming composition to activating light, comprising:
placing a liquid lens forming composition in a mold cavity defined by at least a first mold member and a second mold member, the lens foπning composition comprising:
a monomer that cures by exposure to activating light to form the eyeglass lens during use;
a light absorbing compound tiiat substantially absorbs light having a wavelength in a first range during use;
a photoinitiator that initiates curing of the monomer in response to being exposed to activating light having a wavelength in a second range during use; and
directing activating light at a wavelength in the second range toward at least one of the mold members to cure the lens forming composition and to form the eyeglass lens.
176. The method of claim 175 wherein the first range is less than 380 nanometers.
177. The method of claim 175 wherein the second range is from about 380 to about 490 nanometers.
178. The method of claim 175 wherein the light absorbing compound is a photochromic compound and the method forms a plastic photochromic eyeglass lens.
179. The method of claim 175 wherein the light absorbing compound is an ultraviolet light absorbing compound, and d e method forms a plastic eyeglass lens that will absorb at least a portion of a spectrum of ultraviolet light during use.
180. A method for making a plastic eyeglass lens that contains a photochromic compound by exposing a liquid lens forming composition to activating light, comprising:
placing a liquid lens forming composition in a mold cavity defined by at least a first mold member and a second mold member, the lens forming composition comprising:
a monomer that cures by exposure to activating light to form the eyeglass lens during use;
a photochromic compound that absorbs light having a wavelength of below about 380 nanometers during use;
a photoinitiator that initiates curing of the monomer in response to being exposed to activating light having a wavelength of between about 380 and 490 nanometers during use; and
directing activating light at a wavelength of between about 380 and 490 nanometers toward at least one of the mold members to cure the lens forming composition and to form a photochromic eyeglass lens.
181. The method of claim 180, further comprising filtering the activating light.
182. The method of claim 180, further comprising filtering d e activating light to apply different intensities of light towards at least one mold.
183. A method for making a plastic eyeglass lens, comprising:
placing a liquid lens forming composition in a mold cavity defined by at least a first mold member and a second mold member, the lens forming composition comprising:
a monomer capable of being cured to form the eyeglass lens during use; a light absorbing compound for lowermg an mtensity of light bemg transmitted through the eyeglass lens when the light absorbing compound is exposed to activating light havmg a wavelength m a first range,
a photomitiator that initiates curmg of the monomer m response to bemg exposed to activating light havmg a wavelength m a second range duπng use, and
duectmg activatmg light at a wavelength m the second range toward at least one of the mold members to cure the lens forming composition and to form the eyeglass lens
184 The method of claim 183 wherem the first range is less than 380 nanometers
185 The method of claim 183 wherem the second range is from about 380 to about 490 nanometers
186 The method of claim 183 wherem the first range is less than 380 nanometers, and wherem the second range is from about 380 to about 490 nanometers
187 The method of claim 183 wherem the light absorbmg compound is a photochromic compound and the method forms a plastic photochromic eyeglass lens
188 The method of claim 183 further comprismg filtering die light such that a minimal dose of activating light m the first range contacts the lens forming composition while activatmg light is bemg applied to the lens forming composition
189 The method of claim 183 wherem die first range is substantially different from the second range
190 A metiiod for making a plastic eyeglass lens, compnsmg
placmg a liquid lens formmg composition m a mold cavity defined by at least a first mold member and a second mold member, the lens formmg composition compπsmg a photomitiator and a monomer tiiat cures to form an eyeglass lens when exposed to activatmg light,
directing activating light toward the mold cavity, the activating light causmg the lens formmg composition to cure durmg use,
monitoring a temperature of the lens forming composition while it is curmg, and varying the temperature of the lens formmg composition while it is curmg to vary a power of the lens that is formed from the lens formmg composition
191 The method of claim 190, further comprismg reducmg the power of the formed lens by increasing the temperature of the lens formmg composition
192 The method of claim 190, further comprismg increasing the power of the formed lens by decreasmg die temperature of the lens formmg composition
193 The method of claim 190 wherem the lens forming composition reaches a peak temperature durmg cure, and further comprismg varying the power of the formed lens by varying tiie peak temperature
194 The method of claim 190 wherem the lens formmg composition reaches a peak temperature duπng cure, and further comprising mcreasmg the power of the formed lens by decreasmg die peak temperature
195 The method of claim 190 wherem the lens formmg composition reaches a peak temperature durmg cure, and further compπsmg decreasmg die power of the formed lens by mcreasmg the peak temperature
196 A method for makmg a plastic eyeglass lens, compπsmg
placmg a liquid lens forming composition m a mold cavity defined by at least a first mold member and a second mold member, the lens formmg composition comprismg a photoinitiator and a monomer that cures to form an eyeglass lens when exposed to activating light,
directmg activating light toward the mold cavity, the activatmg light causing die lens formmg composition to cure durmg use,
monitoring a time period tiiat the lens formmg composition is curing in the mold cavity, and
varying the tune peπod that die lens formmg composition is cuπng m the mold cavity to vary a power of the lens that is formed from the lens formmg composition
197 The method of claim 196, further comprismg mcreasmg the time period to decrease the power of the lens
198 The method of claim 196, further comprismg decreasmg the time period to mcrease the power of the lens
199. A method for making a plastic eyeglass lens, comprising:
placing a liquid lens forming composition in a mold cavity defined by at least a first mold member and a second mold member, the lens forming composition comprising:
a monomer capable of being cured for forming the eyeglass lens; and
a photoinitiator adapted to adapted to undergo a chemical change in response to being exposed to initiating light;
directing light toward at least one of the mold members to cure the lens forming composition to form the eyeglass lens;
removing the formed eyeglass lens from the mold cavity, wherein the lens is removed at a demolding time period; and
adjusting die demolding time period, the demolding time period being the time period after which the lens forming composition was first exposed to die light such tiiat a power of the eyeglass lens is substantially different from a target power, wherein the target power is determined by a shape of the mold cavity.
200. The method of claim 199, further comprising increasing the demolding time period to decrease the power of the lens.
201. The method of claim 199, further comprising decreasing the demolding time period to increase the power of the lens.
202. A method for making a plastic eyeglass lens, comprising:
placing a liquid lens forming composition in a mold cavity defined by at least a first mold member and a second mold member, the lens forming composition comprising a photoinitiator and a monomer tiiat cures to form an eyeglass lens when exposed to activating light;
directing activating light toward the mold cavity, the activating light causing the lens forming composition to cure during use;
automatically monitoring a temperature of the lens forming composition while it is curing; automatically varying the temperature of the lens forming composition while it is curing to vary a power of the lens that is formed from the lens forming composition; and
automatically varying the time period that die lens forming composition is curing to vary a power of the lens that is formed from the lens forming composition.
203. A system for making an ophthalmic eyeglass lens, comprising:
a first mold member having a casting face and a non-casting face;
a second mold member having a casting face and a non-casting face, the second mold member being adapted to be spaced apart from the first mold member during use such that the casting faces of the first mold member and the second mold member at least partially define a mold cavity;
a lens forming composition adapted to be disposed within d e mold cavity during use, comprising:
a monomer tiiat cures by exposure to activating light to form the eyeglass lens during use;
a light absorbing compound that substantially absorbs light having a wavelength in a first range during use;
a photoinitiator that initiates curing of the monomer in response to being exposed to activating light having a wavelength in a second range during use; and
a first light generator adapted to generate and direct activating light at a wavelength in the second range toward at least one of die mold members to cure the lens forming composition and to form the eyeglass lens during use.
204. The system of claim 203, further comprising a controller to control the first light generator during use such tiiat activating light is directed in a plurality of pulses toward at least one of the first and second mold members.
205. The system of claim 203 wherein the first light generator is adapted to direct activating light toward die first mold member, and further comprising a second light generator adapted to generate and direct a pulse of activating light toward the second mold member.
206. The system of claim 203 wherein the first light generator is adapted to direct activating light toward tiie first mold member, and further comprising a second light generator adapted to generate and direct a pulse of activating light toward the second mold member, and further comprising a controller adapted to control the first and second light generators such that activating light is directed in a plurality of pulses toward die first and second mold members.
207. The system of claim 203 wherein the first light generator is adapted to generate and direct activating light pulses with a sufficiently high intensity such that the photoinitiator forms a first polymer chain radical.
208. The system of claim 203 wherein the first light generator is adapted to generate and direct activating light pulses with a sufficiently high intensity such that the photoinitiator forms a first polymer chain radical that reacts with die co-initiator and the co-initiator forms a second polymer chain radical that reacts with the monomer.
209. The system of claim 203, further comprising a hazy filter disposed directly adjacent to at least one of the mold members, the filter being adapted to manipulate intensity of activating directed light toward the lens forming composition during use.
210. The system of claim 203, further comprising a hazy filter disposed directly adjacent to at least one of the mold members, the filter comprismg a varying thickness such that die filter varies an intensity distribution of activating light directed across the mold members during use.
211. The system of claim 203, further comprising a cooler adapted to cool die mold cavity during use.
212. The system of claim 203, further comprising a distributor adapted to apply air to the mold cavity to remove heat from the mold cavity during use.
213. The system of claim 203 wherein the first light generator comprises a fluorescent light source.
214. The system of claim 203 wherein the first light generator comprises a fluorescent light source adapted to emit light at a wavelength of about 385 nanometers to 490 nanometers.
215. A system for making an ophthalmic eyeglass lens, comprising:
a first mold member having a casting face and a non-casting face;
a second mold member having a casting face and a non-casting face, the second mold member being adapted to be spaced apart from the first mold member during use such that the casting faces of the first mold member and the second mold member at least partially define a mold cavity; a lens forming composition adapted to be disposed within the mold cavity during use, comprising:
a monomer that cures by exposure to activating light to form the eyeglass lens during use;
a photoinitiator that initiates curing of the monomer in response to being exposed to activating light during use;
a first light generator adapted to generate and direct activating light toward at least one of die mold members to cure the lens forming composition and to form the eyeglass lens during use;
a temperature sensor adapted to measure changes in the temperature of the lens foπning composition during use; and
a controller coupled to the temperature sensor and the first light confroller, wherein the confroller adjusts a dose of initiating light reaching the cavity as a function of a change in the temperature of the lens forming composition over a period of time during use.
216. The system of claim 215 wherein the light is ultraviolet light.
217. The system of claim 215 wherein the confroller is adapted to adjust the dose of light reaching the cavity as a function of an initial temperature of the mold cavity or as a function of ambient room temperature.
218. The system of claim 215 wherem the confroller is adapted to vary an intensity of the light in response to the difference in die temperature of the lens forming composition over the period of time.
219. The system of claim 215 wherein the confroller is adapted to vary a duration of the light in response to the difference in the temperature of the lens forming composition over the predetermined period of time.
220. The system of claim 215 wherein the controller is adapted to vary an intensity of the light in response to the difference in the temperature of the lens forming composition over the predetermined period of time, and wherein the controller is adapted to vary a duration of the light pulses in response to the difference in the temperature of the lens forming composition over the predetermined period of time.
221. The system of claim 215 wherein the confroller is adapted to determine when substantially all of the lens forming composition has cured.
222. The system of claim 215 wherein the controller is adapted to stop the application of light to the lens forming composition after substantially all of the lens forming composition has been cured.
223. The system of 215 wherein the confroller is a Proportional-Integral-Derivative confroller.
224. The system of 215, further comprising a light sensor adapted to measure the dose of light fransmitted to die mold cavity.
225. The system of 215, further comprising a light sensor adapted to measure the dose of light fransmitted to the mold cavity, and wherein the light sensor is adapted to communicate with the controller, wherein the confroller varies the intensity or duration of light such that a predetermined dose is fransmitted to die mold cavity.
226. The system of claim 215, wherem the confroller is adapted to control the first light generator such that light is directed in a plurality of pulses toward at least one of the first and second mold members.
227. The system of claim 215 wherein the first light generator is adapted to direct light toward the first mold member, and further comprising a second light generator adapted to generate and direct light toward the second mold member.
228. The system of claim 215 wherein the first light generator is adapted to direct light toward die first mold member, and further comprising a second light generator adapted to generate and direct light toward the second mold member, and wherein the confroller is adapted to control the first and second light generators such that light is directed in a plurality of pulses toward the first and second mold members.
229. The system of claim 215 wherein the first light generator is adapted to generate and direct light pulses with a sufficiently high intensity such that the photoinitiator forms a first polymer chain radical.
230. The system of claim 215 wherein the first light generator is adapted to generate and direct light pulses witii a sufficiently high intensity such that the photoinitiator forms a first polymer chain radical that reacts with the co-initiator and the co-initiator forms a second polymer chain radical tiiat reacts with the monomer to cure the monomer.
231. The system of claim 215, further comprising a hazy filter disposed directly adjacent to at least one of the mold members, the filter being adapted to manipulate intensity of directed light toward the lens forming composition.
232. The system of claim 215, further comprising a hazy filter disposed directly adjacent to at least one of the mold members, die filter comprising a varying thickness such that the filter varies an intensity distribution of light directed across the mold members.
233. The system of claim 215, further comprismg a cooler adapted to cool the mold cavity.
234. The system of claim 215, further comprising a distributor adapted to apply air to the mold cavity to remove heat from the mold cavity.
235. The system of claim 215 wherem the first light generator comprises a fluorescent light source.
236. The system of claim 215 wherein the first light generator comprises a fluorescent light source adapted to emit light at a wavelength of about 380 nanometers to 490 nanometers.
237. The system of claim 215 wherein the first light generator comprises a xenon light source.
238. The system of claim 215 wherem the first light generator comprises a photostrobe having a quartz tube.
239. The system of claim 215 wherein the temperature sensor is a infrared temperature sensor.
240. A system for making an ophtiialmic eyeglass lens, comprising:
a first mold member having a casting face and a non-casting face;
a second mold member having a casting face and a non-casting face, the second mold member being adapted to be spaced apart from the first mold member during use such that the casting faces of the first mold member and the second mold member at least partially define a mold cavity;
a lens forming composition adapted to be disposed within the mold cavity during use, comprising:
a monomer that cures by exposure to activating light to form the eyeglass lens during use;
a photoinitiator that initiates curing of the monomer in response to being exposed to activating light during use;
a first light generator adapted to generate and direct activating light toward at least one of the mold members to cure the lens forming composition and to form the eyeglass lens during use;
a temperature sensor adapted to measure changes in the temperature of the lens forming composition during use; and
a controller coupled to the temperature sensor and the first light generator, wherem the controller adjusts a dose of initiating light reaching the cavity during a second light pulse, the second light pulse applied subsequent to a first light pulse, and wherein the controller determines the dose of light to be applied to the lens forming composition from the second light pulse as a function of a change in the temperature of the lens forming composition over a period of time subsequent to the application of a first light pulse.
241. A system for making a plastic eyeglass lens, comprising:
a first mold member having a casting face and a non-casting face;
a second mold member having a casting face and a non-casting face, the second mold member being adapted to be spaced apart from the first mold member during use such tiiat the casting faces of the first mold member and die second mold member at least partially define a mold cavity;
a light filter adapted to be positioned substantially adjacent to at least one of die mold members during use;
a first light generator adapted to generate and direct light toward at least one of die mold members during use; and
a confroller coupled to the temperature sensor, wherem the confroller adjusts a dose of initiating light reaching the cavity as a function of a change in the temperature of the lens forming composition over a period of time during use.
242. The system of claim 241 wherein the filter comprises:
a polymerized monomer substantially distributed throughout the filter;
a photoinitiator substantially distributed diroughout die filter for initiating polymerization of the monomer in response to being exposed to activating light; and
a compound substantially distributed throughout the filter for making the filter hazy.
243. The system of claim 241 wherein the filter comprises a bisphenol compound to make the filter hazy.
244. The system of claim 241 wherein the filter comprises a styrene-butadiene copolymer to make the filter hazy.
245. The system of claim 241 wherein the filter is substantially translucent to light.
246. The system of claim 241 wherein the filter is substantially hazy such that the filter disperses die light into a plurality of light rays during use.
247. The system of claim 241 wherem the filter comprises a varying thickness such that the filter varies an intensity distribution of light directed across the mold members during use.
248. The system of claim 241 wherein the filter comprises a varying thickness adapted to vary an intensity distribution of light directed across the mold members such that a greater amount of light passing though a thick portion of the filter is attenuated than passing through a thin portion of the filter.
249. A lens forming composition comprising:
a monomer capable of being cured upon activation by exposing d e lens forming composition to activating radiation having a wavelength in a first range to form the eyeglass lens during use; and
a compound tiiat substantially absorbs radiation having a wavelength in a second range during use.
250. A method of making a plastic eyeglass lens, comprising:
placing a liquid lens forming composition in a mold cavity defined by at least a first mold member and a second mold member, the liquid lens forming composition comprising:
a monomer that cures upon activation by exposing the lens forming composition to activating radiation having a wavelength in a first range to form the eyeglass lens during use; and
a compound that substantially absorbs radiation having a wavelength in a second range during use; and
directing activating radiation at a wavelength in the first range toward at least one of the mold members to cure the lens forming composition and form tiie eyeglass lens.
251. A plastic eyeglass lens comprising:
a lens foπning composition cured by exposure to activating radiation having a wavelength in a first range; and
a radiation absorbing compound adapted to inhibit at least a portion of radiation having a wavelength in a second range from being transmitted through the eyeglass lens during use.
252. A method for using a plastic eyeglass lens, comprising:
providing a plastic eyeglass lens comprising:
a lens foπning composition cured by exposure to activating radiation having a wavelength in a first range; and
a radiation absorbing compound adapted to inhibit at least a portion of radiation having a wavelength in a second range from being transmitted tiirough the eyeglass lens; and
exposing said plastic eyeglass lens to radiation having a wavelength in said second range such tiiat said eyeglass lens at least partially inhibits transmittance of said radiation having a wavelength in said second range through the lens.
PCT/US1998/015959 1997-07-31 1998-07-31 Method and composition for producing activating light absorbing lenses WO1999006887A1 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
US90428997 true 1997-07-31 1997-07-31
US08959973 US5989462A (en) 1997-07-31 1997-10-29 Method and composition for producing ultraviolent blocking lenses
US08/959,973 1997-10-29
US08/904,289 1997-10-29

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EP19980939147 EP1000385B1 (en) 1997-07-31 1998-07-31 Method and system for producing activating light absorbing lenses
CA 2297004 CA2297004A1 (en) 1997-07-31 1998-07-31 Method and composition for producing activating light absorbing lenses
JP2000505552A JP2001512249A (en) 1997-07-31 1998-07-31 Methods and compositions for preparation of activated light-absorbing lens
DE1998623517 DE69823517T2 (en) 1997-07-31 1998-07-31 lentils method and system for the production of active-light-absorbing
DE1998623517 DE69823517D1 (en) 1997-07-31 1998-07-31 lentils method and system for the production of active-light-absorbing

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JP (1) JP2001512249A (en)
CA (1) CA2297004A1 (en)
DE (2) DE69823517T2 (en)
EP (1) EP1000385B1 (en)
WO (1) WO1999006887A1 (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1043365A1 (en) * 1999-04-07 2000-10-11 Hoya Healthcare Corporation Polymerizable 1,2-dipyrazolylethenes as dyes for ophthalmic plastic lenses
WO2001015497A1 (en) * 1999-08-23 2001-03-01 Bausch & Lomb Incorporated Method of and system for controlled curing of polymers used in contact lens manufacture
US6630083B1 (en) 1999-12-21 2003-10-07 Johnson & Johnson Vision Care, Inc. Methods and compositions for the manufacture of ophthalmic lenses
US6936197B1 (en) 1998-07-24 2005-08-30 Duane L. Wires Method and compositions for manufacturing coated photochromatic articles
US7276189B2 (en) 1998-07-24 2007-10-02 Wires Duane L Method and compositions for manufacturing plastic optical lens
EP2960687A1 (en) * 2014-06-24 2015-12-30 Essilor International (Compagnie Generale D'optique) Composition for the manufacture of an ophtalmic lens comprising an uv-absorber and an anti-yellowing additive

Families Citing this family (100)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6022498A (en) 1996-04-19 2000-02-08 Q2100, Inc. Methods for eyeglass lens curing using ultraviolet light
US6673278B1 (en) 1996-04-19 2004-01-06 Q2100, Inc. Methods and apparatus for eyeglass lens curing using ultraviolet light and improved cooling
US6280171B1 (en) 1996-06-14 2001-08-28 Q2100, Inc. El apparatus for eyeglass lens curing using ultraviolet light
US5989462A (en) 1997-07-31 1999-11-23 Q2100, Inc. Method and composition for producing ultraviolent blocking lenses
US20030113640A1 (en) * 1998-07-14 2003-06-19 Sabnis Ram W. Photosensitive black matrix
US6451226B1 (en) 1998-09-25 2002-09-17 Q2100, Inc. Plastic lens compositions
US6419873B1 (en) * 1999-03-19 2002-07-16 Q2100, Inc. Plastic lens systems, compositions, and methods
US6997428B1 (en) * 1999-03-31 2006-02-14 Novartis Ag Contact lens mold
US6528955B1 (en) 2000-03-30 2003-03-04 Q2100, Inc. Ballast system for a fluorescent lamp
US6716375B1 (en) 2000-03-30 2004-04-06 Q2100, Inc. Apparatus and method for heating a polymerizable composition
US6698708B1 (en) 2000-03-30 2004-03-02 Q2100, Inc. Gasket and mold assembly for producing plastic lenses
US6960312B2 (en) * 2000-03-30 2005-11-01 Q2100, Inc. Methods for the production of plastic lenses
US6723260B1 (en) 2000-03-30 2004-04-20 Q2100, Inc. Method for marking a plastic eyeglass lens using a mold assembly holder
US6439870B1 (en) * 2000-05-26 2002-08-27 Johnson & Johnson Vision Care, Inc. Apparatus for automated ophthalmic lens fabrication
US6632535B1 (en) 2000-06-08 2003-10-14 Q2100, Inc. Method of forming antireflective coatings
JP2002200647A (en) * 2000-12-28 2002-07-16 Sony Corp Optical element, mold for optical element, and method for manufacturing optical element
US7139636B2 (en) * 2001-02-20 2006-11-21 Q2100, Inc. System for preparing eyeglass lenses with bar code reader
US6676398B2 (en) 2001-02-20 2004-01-13 Q2100, Inc. Apparatus for preparing an eyeglass lens having a prescription reader
US6702564B2 (en) 2001-02-20 2004-03-09 Q2100, Inc. System for preparing an eyeglass lens using colored mold holders
US6712331B2 (en) 2001-02-20 2004-03-30 Q2100, Inc. Holder for mold assemblies with indicia
US6962669B2 (en) * 2001-02-20 2005-11-08 Q2100, Inc. Computerized controller for an eyeglass lens curing apparatus
US7051290B2 (en) * 2001-02-20 2006-05-23 Q2100, Inc. Graphical interface for receiving eyeglass prescription information
US6758663B2 (en) 2001-02-20 2004-07-06 Q2100, Inc. System for preparing eyeglass lenses with a high volume curing unit
US7045081B2 (en) * 2001-02-20 2006-05-16 Q2100, Inc. Method of monitoring components of a lens forming apparatus
US6840752B2 (en) * 2001-02-20 2005-01-11 Q2100, Inc. Apparatus for preparing multiple eyeglass lenses
US6808381B2 (en) 2001-02-20 2004-10-26 Q2100, Inc. Apparatus for preparing an eyeglass lens having a controller
US6790022B1 (en) 2001-02-20 2004-09-14 Q2100, Inc. Apparatus for preparing an eyeglass lens having a movable lamp mount
US6676399B1 (en) 2001-02-20 2004-01-13 Q2100, Inc. Apparatus for preparing an eyeglass lens having sensors for tracking mold assemblies
US6612828B2 (en) 2001-02-20 2003-09-02 Q2100, Inc. Fill system with controller for monitoring use
US7025910B2 (en) * 2001-02-20 2006-04-11 Q2100, Inc Method of entering prescription information
US7124995B2 (en) * 2001-02-20 2006-10-24 Q2100, Inc. Holder for mold assemblies and molds
US7037449B2 (en) * 2001-02-20 2006-05-02 Q2100, Inc. Method for automatically shutting down a lens forming apparatus
US6726463B2 (en) 2001-02-20 2004-04-27 Q2100, Inc. Apparatus for preparing an eyeglass lens having a dual computer system controller
US7004740B2 (en) * 2001-02-20 2006-02-28 Q2100, Inc. Apparatus for preparing an eyeglass lens having a heating system
US7060208B2 (en) * 2001-02-20 2006-06-13 Q2100, Inc. Method of preparing an eyeglass lens with a controller
US6863518B2 (en) * 2001-02-20 2005-03-08 Q2100, Inc. Mold filing apparatus having multiple fill stations
US6790024B2 (en) 2001-02-20 2004-09-14 Q2100, Inc. Apparatus for preparing an eyeglass lens having multiple conveyor systems
US7052262B2 (en) * 2001-02-20 2006-05-30 Q2100, Inc. System for preparing eyeglasses lens with filling station
US7011773B2 (en) * 2001-02-20 2006-03-14 Q2100, Inc. Graphical interface to display mold assembly position in a lens forming apparatus
US6709257B2 (en) 2001-02-20 2004-03-23 Q2100, Inc. Eyeglass lens forming apparatus with sensor
US6655946B2 (en) 2001-02-20 2003-12-02 Q2100, Inc. Apparatus for preparing an eyeglass lens having a controller for conveyor and curing units
US6752613B2 (en) 2001-02-20 2004-06-22 Q2100, Inc. Apparatus for preparing an eyeglass lens having a controller for initiation of lens curing
US7074352B2 (en) * 2001-02-20 2006-07-11 Q2100, Inc. Graphical interface for monitoring usage of components of a lens forming apparatus
US7083404B2 (en) * 2001-02-20 2006-08-01 Q2100, Inc. System for preparing an eyeglass lens using a mold holder
WO2002066220A1 (en) * 2001-02-21 2002-08-29 Exfo Photonic Solutions Inc. Self-regulated method and system for curing of reactive materials
DE10115066B4 (en) * 2001-03-27 2012-10-04 Leica Biosystems Nussloch Gmbh An apparatus for drying solvent-based ink
WO2002091030A3 (en) * 2001-05-07 2003-03-13 Opticast Inc Method and apparatus for manufacturing plastic optical lenses and molds
WO2002092600A1 (en) * 2001-05-15 2002-11-21 Ardenia Investments Ltd. Retinol derivatives potentiation of active substances by micellar preparation
US20030060878A1 (en) 2001-08-31 2003-03-27 Shadduck John H. Intraocular lens system and method for power adjustment
US6776934B2 (en) * 2001-11-02 2004-08-17 Bausch & Lomb Incorporated Method for polymerizing lenses
US6851804B2 (en) * 2001-12-28 2005-02-08 Jagdish M. Jethmalani Readjustable optical elements
US8048155B2 (en) 2002-02-02 2011-11-01 Powervision, Inc. Intraocular implant devices
US7044429B1 (en) * 2002-03-15 2006-05-16 Q2100, Inc. Methods and systems for coating eyeglass lens molds
US6464484B1 (en) 2002-03-30 2002-10-15 Q2100, Inc. Apparatus and system for the production of plastic lenses
DE10216786C5 (en) * 2002-04-15 2009-10-15 Ers Electronic Gmbh Method and device for conditioning semiconductor wafers and / or hybrids
EP1387054B1 (en) * 2002-07-31 2012-07-25 Canon Kabushiki Kaisha Cooling apparatus for an optical element, exposure apparatus comprising said cooling apparatus, and device fabrication method
US9872763B2 (en) 2004-10-22 2018-01-23 Powervision, Inc. Accommodating intraocular lenses
US7217288B2 (en) 2002-12-12 2007-05-15 Powervision, Inc. Accommodating intraocular lens having peripherally actuated deflectable surface and method
US8328869B2 (en) 2002-12-12 2012-12-11 Powervision, Inc. Accommodating intraocular lenses and methods of use
US8361145B2 (en) 2002-12-12 2013-01-29 Powervision, Inc. Accommodating intraocular lens system having circumferential haptic support and method
CA2517576A1 (en) 2003-03-06 2004-09-23 John H. Shadduck Adaptive optic lens and method of making
US20040185196A1 (en) * 2003-03-21 2004-09-23 Yu Shi Packaged potable liquid with UV absorber for reduced off-taste from closure and method
US8899547B2 (en) 2004-11-18 2014-12-02 Qspex Technologies, Inc. Molds and method of using the same for optical lenses
US20060130881A1 (en) * 2004-12-21 2006-06-22 Sanjay Rastogi Method of cleaning optical tools for making contact lens molds using super-cooled fluids
WO2006069207A1 (en) * 2004-12-22 2006-06-29 Bausch & Lomb Incorporated Pre-polymer extraction using a super-cooled fluid
US7783140B2 (en) * 2005-06-09 2010-08-24 Hewlett-Packard Development Company, L.P. Optically coupled integrated circuit layers
US7638780B2 (en) * 2005-06-28 2009-12-29 Eastman Kodak Company UV cure equipment with combined light path
US20070132120A1 (en) * 2005-12-08 2007-06-14 Bausch & Lomb Incorporated Preferential release of an ophthalmic lens using a super-cooled fluid
US20070132121A1 (en) * 2005-12-08 2007-06-14 Bausch & Lomb Incorporated Method of cleaning molds using super-cooled fluids
US20070132119A1 (en) * 2005-12-08 2007-06-14 Bausch & Lomb Incorporated Use of a super-cooled fluid in the manufacture of contact lenses
US20070132125A1 (en) * 2005-12-08 2007-06-14 Bausch & Lomb Incorporated Use of a super-cooled fluid in lens processing
WO2008103798A3 (en) 2007-02-21 2009-09-11 Powervision, Inc. Polymeric materials suitable for ophthalmic devices and methods of manufacture
US8968396B2 (en) 2007-07-23 2015-03-03 Powervision, Inc. Intraocular lens delivery systems and methods of use
WO2009015240A3 (en) 2007-07-23 2009-06-25 Powervision Inc Lens delivery system
US8314927B2 (en) * 2007-07-23 2012-11-20 Powervision, Inc. Systems and methods for testing intraocular lenses
JPWO2009038134A1 (en) * 2007-09-19 2011-01-06 株式会社ニコン Resin composite-type optical element and a manufacturing method thereof
WO2010071691A1 (en) 2008-12-18 2010-06-24 Novartis Ag Method for making silicone hydrogel contact lenses
US8394906B2 (en) * 2008-02-12 2013-03-12 Aaren Scientific Inc. Ophthalmic lens having a yellow dye light blocking component
WO2009123904A1 (en) * 2008-04-01 2009-10-08 Novartis Ag Ultraviolet output stabilization by fluorescent bulb temperature monitoring
US9072292B2 (en) * 2008-06-06 2015-07-07 T. Brian Cavitt Biofilm resistant polymer materials
KR100993317B1 (en) * 2008-08-26 2010-11-09 삼성전기주식회사 Method of manufacturing lens for light emitting diode package
KR101242989B1 (en) * 2008-11-05 2013-03-12 가부시끼가이샤 도시바 Film-forming apparatus, film-forming method and semiconductor device
WO2010078001A1 (en) * 2008-12-30 2010-07-08 Novartis Ag Tri-functional uv-absorbing compounds and use thereof
WO2011026068A3 (en) 2009-08-31 2011-07-14 Powervision, Inc. Lens capsule size estimation
RU2555704C2 (en) * 2009-09-15 2015-07-10 Новартис Аг Prepolymers, applicable for manufacturing contact lenses, absorbing ultraviolet radiation
JP2013520291A (en) 2010-02-23 2013-06-06 パワーヴィジョン・インコーポレーテッド Liquid for accommodative intraocular lens
WO2012006616A3 (en) 2010-07-09 2012-04-05 Powervision, Inc. Intraocular lens delivery devices and methods of use
CN105601930A (en) 2010-07-30 2016-05-25 诺华股份有限公司 Amphiphilic polysiloxane prepolymers and uses thereof
WO2012047964A1 (en) 2010-10-06 2012-04-12 Novartis Ag Chain-extended polysiloxane crosslinkers with dangling hydrophilic polymer chains
WO2012047961A1 (en) 2010-10-06 2012-04-12 Novartis Ag Polymerizable chain-extended polysiloxanes with pendant hydrophilic groups
RU2576317C2 (en) 2010-10-06 2016-02-27 Новартис Аг Silicone-containing prepolymers subjected to water processing and versions of application thereof
US8513321B2 (en) 2010-11-05 2013-08-20 Ppg Industries Ohio, Inc. Dual cure coating compositions, methods of coating a substrate, and related coated substrates
US8901198B2 (en) 2010-11-05 2014-12-02 Ppg Industries Ohio, Inc. UV-curable coating compositions, multi-component composite coatings, and related coated substrates
US8899745B2 (en) 2010-12-13 2014-12-02 Novartis Ag Ophthalmic lenses modified with functional groups and methods of making thereof
EP2688515A4 (en) 2011-03-24 2015-04-15 Powervision Inc Intraocular lens loading systems and methods of use
US9335443B2 (en) 2011-04-15 2016-05-10 Qspex Technologies, Inc. Anti-reflective lenses and methods for manufacturing the same
US9042019B2 (en) 2011-04-15 2015-05-26 Qspex Technologies, Inc. Anti-reflective lenses and methods for manufacturing the same
JP2013186195A (en) * 2012-03-06 2013-09-19 Toshiba Tec Corp Image forming apparatus, and lens array and manufacturing method of the same
WO2013150891A1 (en) * 2012-04-03 2013-10-10 スタンレー電気株式会社 Strobe light device
DE102013018528B4 (en) * 2013-11-04 2017-02-23 Audi Ag Method and apparatus for automated cleaning of a welding torch head

Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4396737A (en) * 1981-11-19 1983-08-02 Ppg Industries, Inc. Polymerization of polyol allyl carbonate using polymerization initiators of short and long half lives
EP0227337A2 (en) * 1985-12-19 1987-07-01 Pilkington Plc Process for manufacturing photochromic articles
EP0297871A2 (en) * 1987-06-30 1989-01-04 EASTMAN KODAK COMPANY (a New Jersey corporation) Novel polymethine dyes and UV absorbers and imaging materials for their use
EP0341534A2 (en) * 1988-05-07 1989-11-15 Ciba-Geigy Ag Photoinitiator dispersions
WO1990005629A1 (en) * 1988-11-18 1990-05-31 Ophthalmic Research Group International, Inc. Plastic lens compositions and apparatus for the production thereof
DE4010784A1 (en) * 1990-04-04 1991-10-10 Bayer Ag New terpolymer prodn., useful for optical moulding - from acrylated tetra: or hexa:hydro methano:indene cpd., acrylated bis:phenol epoxide and chloro-phenyl acrylate
WO1992012851A2 (en) * 1991-01-17 1992-08-06 Ophthalmic Research Group International Corp. Method and apparatus for the production of plastic lenses
WO1995013567A1 (en) * 1993-11-08 1995-05-18 Alliedsignal Inc. Process for making an array of tapered photopolymerized waveguides
US5514214A (en) * 1993-09-20 1996-05-07 Q2100, Inc. Eyeglass lens and mold spin coater
US5529728A (en) * 1986-01-28 1996-06-25 Q2100, Inc. Process for lens curing and coating
WO1997039880A2 (en) * 1996-04-19 1997-10-30 Q2100, Inc. Methods and apparatus for eyeglass lens curing using ultraviolet light and improved cooling

Family Cites Families (213)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2479934A (en) 1943-08-26 1949-08-23 Gen Motors Corp Heat treating
US2524862A (en) * 1946-07-16 1950-10-10 Ici Ltd Method and apparatus for producing cast synthetic resin structures by photopolymerization of monomeric material
US2479935A (en) 1947-02-11 1949-08-23 Combined Optical Ind Ltd Method for forming coated optical elements from polymerizable materials
US2542386A (en) 1947-12-03 1951-02-20 John O Beattie Manufacture of plastic lenses from monomeric materials
GB636283A (en) * 1947-12-10 1950-04-26 Gadsby John Production of optical elements
CA721243A (en) * 1957-08-01 1965-11-09 E. Amborski Leonard Organic polymeric structures
US3056166A (en) 1959-07-20 1962-10-02 Bausch & Lomb Lens mold and apparatus
US3240854A (en) 1961-09-08 1966-03-15 Laubman & Pank Ltd Manufacture of mouldable plastic articles
FR1334376A (en) 1962-06-08 1963-08-09 Lentilles Ophtalmiques Rationn Machine for filling molds intended in particular for the manufacture of ophthalmic lenses of synthetic resin
US3309219A (en) * 1963-07-12 1967-03-14 Gen Electric Method of producing an ultraviolet resistant polycarbonate article
US3309220A (en) * 1964-04-10 1967-03-14 Gen Electric Method of producing an ultraviolet resistant polycarbonate article
US3485765A (en) * 1966-07-06 1969-12-23 Eastman Kodak Co Azo modifier containing phototropic compositions
US3530075A (en) 1967-11-01 1970-09-22 American Cyanamid Co Photochromic compositions
US3494326A (en) 1968-02-01 1970-02-10 American Optical Corp Spin-coating machine
US3871803A (en) 1971-12-21 1975-03-18 Beattie Dev Company Apparatus for producing an optical molding plaque
US3555611A (en) 1969-12-15 1971-01-19 Armorlite Lens Co Inc Mold for casting optical elements and the like
DE2205740A1 (en) 1971-02-15 1972-08-31
JPS5549626B2 (en) 1972-07-21 1980-12-12
DE2420816A1 (en) 1973-05-02 1974-11-21 Involvo Ag glue applicator
JPS5845445B2 (en) * 1975-03-26 1983-10-11 Japan Atomic Energy Res Inst
US4113224A (en) * 1975-04-08 1978-09-12 Bausch & Lomb Incorporated Apparatus for forming optical lenses
FR2329427B1 (en) * 1975-10-30 1979-05-04 Essilor Int
DE2609273C2 (en) * 1976-03-05 1990-05-10 Maximilian Friedrich Prof. Dr.-Ing. 8000 Muenchen De Mutzhas
US4077858A (en) * 1976-10-04 1978-03-07 Celanese Corporation Completely polymerized ultraviolet cured coatings
US4190621A (en) 1977-03-10 1980-02-26 Martin Greshes Method for molding optical plastic lenses of the standard and bifocal type
US4095772A (en) 1977-05-13 1978-06-20 Weber Hermann P Casting apparatus for plastic lenses
US4166088A (en) * 1977-05-25 1979-08-28 Neefe Charles W Method of making high quality plastic lenses
US4220708A (en) 1977-07-22 1980-09-02 Heller Harold G Photochromic compounds
US4132518A (en) * 1977-10-18 1979-01-02 Realite Optical Company Apparatus for manufacturing plastic lenses
US4252753A (en) * 1977-10-18 1981-02-24 Irving Rips Manufacture of plastic lenses
US4318791A (en) * 1977-12-22 1982-03-09 Ciba-Geigy Corporation Use of aromatic-aliphatic ketones as photo sensitizers
US4257988A (en) 1978-09-12 1981-03-24 Optical Warehouse Showroom And Manufacturing, Inc. Method and assembly for molding optical lenses
FR2442849B1 (en) * 1978-11-28 1981-11-27 France Etat
US4246207A (en) * 1979-05-14 1981-01-20 Corning Glass Works Method for casting glass-plastic lenses comprising allyl diglycol carbonate plastic
US4273809A (en) * 1979-10-25 1981-06-16 American Optical Corporation Method of preparing cast resin lenses
FR2477059B1 (en) * 1980-02-28 1983-04-15 Medicornea Sa
US4297616A (en) 1980-03-17 1981-10-27 Xerox Corporation Fluorescent lamp with incandescent ballasting systems
US4441795A (en) * 1980-03-24 1984-04-10 Camelot Industries Corporation Molded multifocal lens and mold assembly
US4329622A (en) 1980-05-19 1982-05-11 Xerox Corporation Low pressure gas discharge lamp with increased end illumination
US4369298A (en) * 1980-05-27 1983-01-18 Tokuyama Soda Kabushiki Kaisha Novel cured resin, process for production thereof, and lens composed of said resin from bis(alkyleneoxyphenyl)-diacrylate, bis(alkyleneoxyphenyl)diallyl ether, bis(alkyleneoxyphenyl)diallyl carbonate monomers
US4284399A (en) * 1980-06-23 1981-08-18 American Optical Corporation Contact lens mold
CA1224182A (en) 1980-11-05 1987-07-14 Rack H. Chung Abrasion resistant ultraviolet light curable hard coating compositions
JPS5785002A (en) 1980-11-17 1982-05-27 Matsushita Electric Ind Co Ltd Plastic lens
US4640489A (en) * 1981-04-30 1987-02-03 Mia-Lens Production A/S Mold for making contact lenses, either the male or female mold sections being relatively more flexible
JPS5845445A (en) 1981-09-11 1983-03-16 Asahi Tekkosho:Kk Solar heat collector
US4355135A (en) 1981-11-04 1982-10-19 Dow Corning Corporation Tintable abrasion resistant coatings
NL8200634A (en) * 1982-02-18 1983-09-16 Philips Nv Method and device for forming a transparent object.
CA1221795A (en) 1982-02-24 1987-05-12 Bolesh J. Skutnik Optical fiber cladding
US4720356A (en) * 1982-03-22 1988-01-19 American Optical Corporation Photochromic composition resistant to fatigue
US4544572B1 (en) 1982-09-07 1994-01-04 Signet Armorlite, Inc.
US4758448B1 (en) 1982-09-07 1994-01-04 Signet Armorlite, Inc.
US4534915A (en) * 1982-09-13 1985-08-13 Neefe Charles W Method of controlling the ultraviolet polymerization of spin cast lenses
US4561951A (en) * 1982-11-26 1985-12-31 Neckers Douglas C Method for polymerizing a bis(allyl carbonate)
US4512340A (en) * 1983-02-22 1985-04-23 Johnson & Johnson Products, Inc. Visible light cured orthopedic polymer casts
JPH0642002B2 (en) 1983-07-29 1994-06-01 セイコーエプソン株式会社 Plastic lens
FR2550349B1 (en) * 1983-08-03 1985-10-18 Essilor Int Method for the realization of optical lenses and anti-scratch coating obtained lenses
JPS6049038A (en) * 1983-08-29 1985-03-18 Toyobo Co Ltd Surface hardener for nylon lens
DE3331157A1 (en) 1983-08-30 1985-03-14 Basf Ag Photopolymerizable mixtures comprising tertiary amines as photoactivators
US4576766A (en) 1983-09-07 1986-03-18 The Plessey Company Plc Photochromic compounds and their use in photoreactive lenses
US4685783A (en) 1983-09-07 1987-08-11 The Plessey Company P.L.C. Polychromic tetracyclo-spiro-adamatylidene derivatives, and polychromic lens incorporating said compounds
JPH0359085B2 (en) * 1983-11-11 1991-09-09 Mitsui Toatsu Chemicals
DE3583707D1 (en) 1984-06-26 1991-09-12 Asahi Glass Co Ltd Transparent hard-contaminating object with low reflection.
US4557980A (en) 1984-08-21 1985-12-10 Martin Processing, Inc. Radiation curable coating for film structure
US4613656A (en) * 1984-11-23 1986-09-23 Ppg Industries, Inc. Method for polymerizing bis(allyl carbonate) resin
US4623497A (en) * 1984-11-28 1986-11-18 Application Engineering Corporation Passive mold cooling and heating method
US4711379A (en) 1985-04-03 1987-12-08 Nordson Corporation Proportional flow control dispensing gun
US4707076A (en) 1985-04-12 1987-11-17 Ensign-Bickford Industries, Inc. Coating compositions for optical fibers
US4622376A (en) * 1985-06-27 1986-11-11 Ppg Industries, Inc. Composition of aromatic poly(allylcarbonate), styrene materials, and crosslinker containing three or more ethylenically unsaturated groups for producing polymer of high refractive index and low yellowness
DE3525892C1 (en) 1985-07-19 1986-10-02 Rodenstock Optik G Antireflective coating for an optical element of organic material
US4693446A (en) 1985-09-20 1987-09-15 Techna Vision, Inc. Gasket for molding plastic lenses
US4959429A (en) * 1985-11-22 1990-09-25 Ppg Industries, Inc. Cyclohexenic additives for producing polycarbonate polymers of high refractive index and low yellowness
EP0226123A3 (en) * 1985-12-03 1988-08-10 Matsushita Electric Industrial Co., Ltd. Method for producing transparent plastic article
CA1263208A (en) 1985-12-19 1989-11-28 Kirk K.S. Hwang Method and apparatus for making optical devices
US4746716A (en) * 1985-12-27 1988-05-24 Ppg Industries, Inc. Compositions for producing polymers of high refractive index and low yellowness
US4774035A (en) 1986-01-14 1988-09-27 Camelot Industries Corporation Process of coating an ophthalmic lens
FR2598520B1 (en) 1986-01-21 1994-01-28 Seiko Epson Corp Inorganic protective film
DE3602215A1 (en) 1986-01-25 1987-07-30 Hoechst Ag Photopolymerizable mixture and this containing photopolymerizable recording material
US4728469A (en) * 1986-01-28 1988-03-01 Sperti Drug Products, Inc. Method and apparatus for making a plastic lens
US4879318A (en) * 1986-01-28 1989-11-07 Ophthalmic Research Group International, Inc. Plastic lens composition and method for the production thereof
US5364256A (en) * 1986-01-28 1994-11-15 Ophthalmic Research Group International, Inc. Apparatus for the production of plastic lenses
JPH0685002B2 (en) 1986-02-18 1994-10-26 ミノルタ株式会社 Plastic optical component antireflection film
US4985186A (en) 1986-04-11 1991-01-15 Canon Kabushiki Kaisha Process for producing optical element
US4681155A (en) 1986-05-01 1987-07-21 The Garrett Corporation Lightweight, compact heat exchanger
GB8610709D0 (en) * 1986-05-01 1986-06-04 Plinkington Bros Plc Photochromic lenses
JPS62288030A (en) * 1986-06-06 1987-12-14 Matsushita Electric Ind Co Ltd Manufacturing device for composite linse
US4731264A (en) 1986-10-03 1988-03-15 Ppg Industries, Inc. Sol-gel compositions containing silane and alumina
US4842782A (en) 1986-10-14 1989-06-27 Allergan, Inc. Manufacture of ophthalmic lenses by excimer laser
GB8627859D0 (en) * 1986-11-21 1986-12-31 Pilkington Brothers Plc Spiro-oxazine compounds
US4902725A (en) * 1986-12-22 1990-02-20 General Electric Company Photocurable acrylic coating composition
EP0274595A3 (en) * 1986-12-22 1989-11-29 General Electric Company Aromatic carbonate resin articles coated with a photocured acrylic coating
JPH0720670B2 (en) * 1987-02-25 1995-03-08 ホ−ヤ株式会社 A manufacturing method and apparatus of the plastic lens
US4989316A (en) 1987-03-09 1991-02-05 Gerber Scientific Products, Inc. Method and apparatus for making prescription eyeglass lenses
US4800122A (en) 1987-09-22 1989-01-24 Gentex Corporation Siloxane-based tintable coating
US4895102A (en) 1987-10-29 1990-01-23 Techna Vision Incorporated Spin coater
US4873029A (en) * 1987-10-30 1989-10-10 Blum Ronald D Method for manufacturing lenses
US5147585A (en) 1987-10-30 1992-09-15 Blum Ronald D Method for forming plastic optical quality spectacle lenses
US5219497A (en) 1987-10-30 1993-06-15 Innotech, Inc. Method for manufacturing lenses using thin coatings
JPH0541411B2 (en) * 1987-12-21 1993-06-23 Matsushita Electric Ind Co Ltd
US4968454A (en) * 1988-01-25 1990-11-06 Ppg Industries, Inc. Variable-light transmittance article and method for preparing same
US5021196A (en) * 1988-01-25 1991-06-04 Ppg Industries, Inc. Method for preparing variable-light transmittance article
US4929278A (en) 1988-01-26 1990-05-29 United States Department Of Energy Sol-gel antireflective coating on plastics
US4966812A (en) 1988-01-26 1990-10-30 The United States Of America As Represented By The Department Of Energy Sol-gel antireflective coating on plastics
US5049321A (en) 1988-03-25 1991-09-17 Signet Armorlite, Inc. Method for forming coated plastic optical elements
US4919850A (en) * 1988-05-06 1990-04-24 Blum Ronald D Method for curing plastic lenses
US5268196A (en) 1988-05-30 1993-12-07 Ford Motor Company Process for forming anti-reflective coatings comprising light metal fluorides
JP2613436B2 (en) 1988-06-10 1997-05-28 旭光学工業株式会社 Method of forming the antireflection film for a plastic lens
US5173368A (en) 1988-09-14 1992-12-22 Pilkington Visioncare Holdings, Inc. Solution-applied antireflective coatings
US4889664A (en) * 1988-11-25 1989-12-26 Vistakon, Inc. Method of forming shaped hydrogel articles including contact lenses
US4939423A (en) 1988-12-06 1990-07-03 Honeywell Inc. Reduction of effects of beat frequencies in systems with multiple oscillators
US5028358A (en) * 1989-04-17 1991-07-02 Blum Ronald D Method for molding and curing plastic lenses
US5110881A (en) * 1989-04-18 1992-05-05 Ppg Industries, Inc. Polymerizable organic resin composition
US5880171A (en) 1989-05-01 1999-03-09 2C Optics, Inc. Fast curing polymeric compositions for ophthalmic lenses and apparatus for preparing lenses
US5110514A (en) 1989-05-01 1992-05-05 Soane Technologies, Inc. Controlled casting of a shrinkable material
US4955804A (en) * 1989-06-19 1990-09-11 General Motors Corporation Tool for molding plastic articles
US5693366A (en) 1989-06-20 1997-12-02 Nippon Sheet Glass Co., Ltd. Process for producing plastic lens comprising a primer layer, a hard coat layer and an antireflection coating
DE3927667A1 (en) 1989-08-22 1991-02-28 Espe Stiftung Use of photopolymerizable extent than introkularlinsen filler eye diseases in combating cataract and other
JPH0698628B2 (en) * 1989-09-01 1994-12-07 株式会社モリタ東京製作所 Continuous curing method and apparatus for visible light-cured resin
JPH0390319A (en) * 1989-09-01 1991-04-16 Morita Tokyo Seisakusho:Kk Method and apparatus for continuously curing visible ray polymerizable resin
FR2653778B1 (en) 1989-10-30 1994-09-23 Essilor Int Method of preparing a coating composition of a high refractive index based on polysiloxanes and titanates and resulting composition.
US5105126A (en) 1990-01-16 1992-04-14 Cooper Industries, Inc. Brightness control for flashing xenon lamp
US5154861A (en) 1990-03-13 1992-10-13 Bausch & Lomb Incorporated Laser curing of contact lens
US5104692A (en) 1990-04-20 1992-04-14 Pilkington Visioncare Holdings, Inc. Two-layer antireflective coating applied in solution
US5061355A (en) 1990-06-14 1991-10-29 Hewlett-Packard Company Preparation of gel-filled separation columns
US5158718A (en) 1990-08-02 1992-10-27 Pilkington Visioncare, Inc. Contact lens casting
US5224972A (en) 1990-09-11 1993-07-06 Frye Gregory C Coatings with controlled porosity and chemical properties
US5118142A (en) 1990-10-09 1992-06-02 Bish Stephen L Traction device
JP2685980B2 (en) * 1990-11-26 1997-12-08 株式会社メニコン UV absorbing intraocular lens
US5061769A (en) 1990-12-17 1991-10-29 Allied-Signal Inc. Fluoropolymers and fluoropolymer coatings
US5178955A (en) 1990-12-17 1993-01-12 Allied-Signal Inc. Polymeric anti-reflection coatings and coated articles
US5225244A (en) 1990-12-17 1993-07-06 Allied-Signal Inc. Polymeric anti-reflection coatings and coated articles
DE4118184A1 (en) 1991-06-03 1992-12-10 Inst Neue Mat Gemein Gmbh Coating compositions based on fluorine-containing inorganic polycondensates whose production and their use
US5250877A (en) 1991-06-04 1993-10-05 Rockwell International Corporation Method and apparatus for driving a gas discharge lamp
US5153027A (en) 1991-06-10 1992-10-06 Ford Motor Company Preparation of differential thickness coatings by dip coating where the substrate is pivoted
FR2680583B1 (en) 1991-08-22 1993-10-08 Commissariat A Energie Atomique Material having antiglare properties, hydrophobic and abrasion resistance and the process for depositing an antireflective layer, hydrophobic and abrasion resistant on a substrate.
US5716679A (en) 1991-09-13 1998-02-10 Institut Fur Neue Materialien Gemeinnutzige Gmbh Optical elements containing nanoscaled particles and having an embossed surface and process for their preparation
US5238981A (en) * 1992-02-24 1993-08-24 Transitions Optical, Inc. Photochromic naphthopyrans
US5470892A (en) 1992-05-01 1995-11-28 Innotech, Inc. Polymerizable resin for forming clear, hard plastics
FR2693558B1 (en) 1992-07-09 1994-08-19 Commissariat Energie Atomique Process for producing thin coatings having optical properties.
US5689324A (en) 1992-08-18 1997-11-18 Q2100, Inc. Progressive lens
US6074579A (en) 1992-08-19 2000-06-13 Greshes; Martin Lens blanks and method of making a lens therefrom
DE69327410T2 (en) * 1992-09-25 2000-05-11 Ppg Ind Ohio Inc Photochromic compositions with improved light fatigue resistance
US5412016A (en) 1992-09-28 1995-05-02 E. I. Du Pont De Nemours And Company Process for making polymeric inorganic-organic compositions
US5274132A (en) * 1992-09-30 1993-12-28 Transitions Optical, Inc. Photochromic naphthopyran compounds
US5380387A (en) * 1992-10-13 1995-01-10 Loctite Corporation Lens blocking/deblocking method
US5385955A (en) 1992-11-05 1995-01-31 Essilor Of America, Inc. Organosilane coating composition for ophthalmic lens
US5405958A (en) * 1992-12-21 1995-04-11 Transitions Optical, Inc. Photochromic spiro(indoline)naphthoxazine compounds
US5316791A (en) 1993-01-21 1994-05-31 Sdc Coatings Inc. Process for improving impact resistance of coated plastic substrates
US5377032A (en) 1993-02-05 1994-12-27 Osd Envizion Company Electro-optic light shutter and frame assembly with integrated switching mechanism
WO1994020869A1 (en) * 1993-03-12 1994-09-15 Ppg Industries, Inc. Novel benzopyrans
US5698266A (en) 1993-04-05 1997-12-16 Commissariat A L'energie Atomique Process for the production of thin coatings having optical and abrasion resistance properties
US5466398A (en) * 1993-06-21 1995-11-14 Transitions Optical, Inc. Photochromic substituted naphthopyran compounds
US5384077A (en) * 1993-06-21 1995-01-24 Transitions Optical, Inc. Photochromic naphthopyran compounds
DE4325154C1 (en) 1993-07-27 1994-09-29 Rodenstock Optik G Process for the production of a photochromic article
US5422046A (en) * 1993-08-31 1995-06-06 Essilor Of America, Inc. Method for producing optical lenses
US5627434A (en) 1993-10-26 1997-05-06 Canon Kabushiki Kaisha Apparatus for operating a fluorescent lamp of an image forming apparatus
US5483125A (en) 1993-12-06 1996-01-09 General Electric Company Ballast circuit for a gas discharge lamp having a cathode pre-heat arrangement
US5458814A (en) * 1993-12-09 1995-10-17 Transitions Optical, Inc. Substituted naphthopyrans
US5531940A (en) 1993-12-10 1996-07-02 Innotech, Inc. Method for manufacturing photochromic lenses
US5424611A (en) 1993-12-22 1995-06-13 At&T Corp. Method for pre-heating a gas-discharge lamp
US5464567A (en) * 1994-04-08 1995-11-07 Transitions Optical, Inc. Photochromic tetraphenyl naphthodipyrans
US5451344A (en) * 1994-04-08 1995-09-19 Transitions Optical, Inc. Photochromic naphthopyran compounds
JP3471073B2 (en) 1994-04-27 2003-11-25 株式会社トクヤマ Photochromic composition
DE4417405A1 (en) 1994-05-18 1995-11-23 Inst Neue Mat Gemein Gmbh A process for the production of structured inorganic layers
US5667735A (en) 1994-05-23 1997-09-16 2C Optics, Inc. Opthalmic mold coatings
US5597519A (en) 1994-06-10 1997-01-28 Johnson & Johnson Vision Products, Inc. Ultraviolet cycling oven for polymerization of contact lenses
US5836323A (en) 1994-06-10 1998-11-17 Johnson & Johnson Vision Products, Inc. Automated method and apparatus for hydrating soft contact lenses
CA2151341C (en) 1994-06-10 2007-08-14 Wallace Anthony Martin Mold clamping and precure of a polymerizable hydrogel
DE69528668D1 (en) * 1995-12-12 2002-11-28 Nippon Carbide Kogyo Kk reflective foil
DE4423904A1 (en) 1994-07-10 1996-01-11 Rodenstock Optik G Photochromic substances (car)
US5585186A (en) 1994-12-12 1996-12-17 Minnesota Mining And Manufacturing Company Coating composition having anti-reflective, and anti-fogging properties
FR2727894B1 (en) 1994-12-12 1997-02-21
CA2162451A1 (en) 1994-12-22 1996-06-23 John P. Murphy Anti-reflective clarifier film for eyeglasses
DK0800511T3 (en) * 1994-12-30 2000-06-19 Novartis Ag Functionalized photoinitiators, derivatives and macromers and their use
US5733483A (en) 1995-01-13 1998-03-31 Soane Technologies, Inc. Method for formation of on-site coated and tinted optical elements
US5619288A (en) 1995-01-23 1997-04-08 Essilor Of America, Inc. Impact resistant plastic ophthalmic lens
JP3625097B2 (en) * 1995-02-07 2005-03-02 セイコーエプソン株式会社 Colored contact lenses and their preparation
DE69617291T2 (en) * 1995-02-15 2002-05-23 Menicon Co Ltd Water-absorptive soft contact lens
US5623184A (en) 1995-03-03 1997-04-22 Gulton Industries, Inc. Lamp circuit with filament current fault monitoring means
US5580819A (en) 1995-03-22 1996-12-03 Ppg Industries, Inc. Coating composition, process for producing antireflective coatings, and coated articles
US5849209A (en) 1995-03-31 1998-12-15 Johnson & Johnson Vision Products, Inc. Mold material made with additives
US5681871A (en) * 1995-05-24 1997-10-28 Johnson & Johnson Vision Products, Inc. Method for preparing ultraviolet radiation absorbing contact lenses
JPH08319481A (en) 1995-05-26 1996-12-03 Tokuyama Corp Production of photochromic cured material
US5719705A (en) 1995-06-07 1998-02-17 Sola International, Inc. Anti-static anti-reflection coating
US5753301A (en) 1995-06-08 1998-05-19 Essilor Of America, Inc. Method for spin coating a multifocal lens
US5685908A (en) 1995-06-08 1997-11-11 Essilor Of America, Inc. Apparatus for spin coating a multifocal lens
US6253957B1 (en) 1995-11-16 2001-07-03 Nordson Corporation Method and apparatus for dispensing small amounts of liquid material
US5747102A (en) 1995-11-16 1998-05-05 Nordson Corporation Method and apparatus for dispensing small amounts of liquid material
WO1997030362A1 (en) 1996-02-13 1997-08-21 Sola International, Inc. Color-neutral uv blocking coating for plastic lens
DE19610563A1 (en) 1996-03-18 1997-09-25 Bodenseewerk Geraetetech A method for mutual positioning of pairs of opposed shape-determining mold parts and molding tool for the production of precision parts, in particular contact lenses
US5914193A (en) 1996-04-12 1999-06-22 Nikon Corporation Photochromic plastic lens and its method of manufacture
US6280171B1 (en) 1996-06-14 2001-08-28 Q2100, Inc. El apparatus for eyeglass lens curing using ultraviolet light
US5861934A (en) 1996-05-06 1999-01-19 Innotech, Inc. Refractive index gradient lens
US5789015A (en) 1996-06-26 1998-08-04 Innotech, Inc. Impregnation of plastic substrates with photochromic additives
JP3769075B2 (en) * 1996-07-08 2006-04-19 Jsr株式会社 Radiation-curable resin composition
US5914174A (en) 1996-12-05 1999-06-22 Innotech, Inc. Lens or semi-finished blank comprising photochromic resin compositions
JP2001512383A (en) 1997-02-20 2001-08-21 テクノロジー リソース インターナショナル コーポレイション Gasket for lens formation
US5851328A (en) * 1997-03-07 1998-12-22 Kohan; George Wafer deforming composite ophthalmic lens method
US5903105A (en) 1997-07-21 1999-05-11 Samsung Electronics Co., Ltd. Apparatus and method for controlling lighting of fluorescent lamp for refrigerator
US5989462A (en) 1997-07-31 1999-11-23 Q2100, Inc. Method and composition for producing ultraviolent blocking lenses
JPH11197571A (en) 1998-01-12 1999-07-27 Nordson Kk Method for controlling opening and closing speed of valve mechanism of discharge gun, apparatus therefor, and discharge coating method for liquid body
US6103148A (en) 1998-02-19 2000-08-15 Technology Resources International Corporation Method for curing a lens-forming fluid
US6245428B1 (en) 1998-06-10 2001-06-12 Cpfilms Inc. Low reflective films
KR20000015469A (en) * 1998-08-29 2000-03-15 박이순 Photopolymerization type photosensitive phosphor paste composition and production process of fluorescence film
US6451226B1 (en) 1998-09-25 2002-09-17 Q2100, Inc. Plastic lens compositions
US6042754A (en) 1998-10-30 2000-03-28 Optima, Inc. Continuous extrusion-compression molding process for making optical articles
US6218494B1 (en) 1998-11-18 2001-04-17 Essilor International - Compagnie Generale D'optique Abrasion-resistant coating composition process for making such coating composition and article coated therewith
US6419873B1 (en) 1999-03-19 2002-07-16 Q2100, Inc. Plastic lens systems, compositions, and methods
DE19914702A1 (en) * 1999-03-31 2000-10-05 Norbert Hampp Production of crosslinked bacteriorhodopsin in membrane-bound form, useful in photoelectric applications and for data storage, by treatment with transglutaminase
US6682869B2 (en) * 2000-03-07 2004-01-27 Shin-Etu Chemical Co., Ltd. Chemical amplification, positive resist compositions
US6439870B1 (en) 2000-05-26 2002-08-27 Johnson & Johnson Vision Care, Inc. Apparatus for automated ophthalmic lens fabrication
US6709648B2 (en) * 2000-05-30 2004-03-23 The Procter & Gamble Company Hair conditioning composition comprising silicones and frizz control agents
JP4931768B2 (en) 2007-11-01 2012-05-16 京子 杉山 Framework assembly method of the arched wooden bridge model, framework structure and assembly kit
JP5785002B2 (en) 2011-06-28 2015-09-24 トヨタ自動車株式会社 Electromagnetic engagement device

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4396737A (en) * 1981-11-19 1983-08-02 Ppg Industries, Inc. Polymerization of polyol allyl carbonate using polymerization initiators of short and long half lives
EP0227337A2 (en) * 1985-12-19 1987-07-01 Pilkington Plc Process for manufacturing photochromic articles
US5529728A (en) * 1986-01-28 1996-06-25 Q2100, Inc. Process for lens curing and coating
EP0297871A2 (en) * 1987-06-30 1989-01-04 EASTMAN KODAK COMPANY (a New Jersey corporation) Novel polymethine dyes and UV absorbers and imaging materials for their use
EP0341534A2 (en) * 1988-05-07 1989-11-15 Ciba-Geigy Ag Photoinitiator dispersions
WO1990005629A1 (en) * 1988-11-18 1990-05-31 Ophthalmic Research Group International, Inc. Plastic lens compositions and apparatus for the production thereof
DE4010784A1 (en) * 1990-04-04 1991-10-10 Bayer Ag New terpolymer prodn., useful for optical moulding - from acrylated tetra: or hexa:hydro methano:indene cpd., acrylated bis:phenol epoxide and chloro-phenyl acrylate
WO1992012851A2 (en) * 1991-01-17 1992-08-06 Ophthalmic Research Group International Corp. Method and apparatus for the production of plastic lenses
US5514214A (en) * 1993-09-20 1996-05-07 Q2100, Inc. Eyeglass lens and mold spin coater
WO1995013567A1 (en) * 1993-11-08 1995-05-18 Alliedsignal Inc. Process for making an array of tapered photopolymerized waveguides
WO1997039880A2 (en) * 1996-04-19 1997-10-30 Q2100, Inc. Methods and apparatus for eyeglass lens curing using ultraviolet light and improved cooling

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6936197B1 (en) 1998-07-24 2005-08-30 Duane L. Wires Method and compositions for manufacturing coated photochromatic articles
US7276189B2 (en) 1998-07-24 2007-10-02 Wires Duane L Method and compositions for manufacturing plastic optical lens
EP1043365A1 (en) * 1999-04-07 2000-10-11 Hoya Healthcare Corporation Polymerizable 1,2-dipyrazolylethenes as dyes for ophthalmic plastic lenses
WO2001015497A1 (en) * 1999-08-23 2001-03-01 Bausch & Lomb Incorporated Method of and system for controlled curing of polymers used in contact lens manufacture
US6630083B1 (en) 1999-12-21 2003-10-07 Johnson & Johnson Vision Care, Inc. Methods and compositions for the manufacture of ophthalmic lenses
EP2960687A1 (en) * 2014-06-24 2015-12-30 Essilor International (Compagnie Generale D'optique) Composition for the manufacture of an ophtalmic lens comprising an uv-absorber and an anti-yellowing additive

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