Method for producing a photochromic optical article

Abstract

The present invention relates to a method for producing optical articles, such as ophthalmic lenses, that have both photochromic and UV protection properties, and to optical articles with said properties.

Description

[Technical Field]

[0001] The present invention relates to a method for producing optical articles, such as ophthalmic lenses, that have both photochromic and UV protection properties, and to optical articles with said properties.

[0002] More precisely, the invention relates to a method for manufacturing an optical article comprising a laminate including at least a photochromic film and an ultraviolet radiation protection film embedded in a substrate, and to an optical article having said structure. [Background technology]

[0003] Photochromic lenses are optical lenses that change color. Photochromic lenses are well known in the art, and different processes for their manufacture have been described. The manufacture of optical lenses, such as photochromic lenses, classically requires the combination of several layers, each of which provides the optical lens with specific properties. For example, a specific layer can provide the optical lens with UV protection or polarization. The manufacture of a layer stack classically involves successive deposition steps.

[0004] Existing methods for embedding a specific layer or film in a lens containing a thermosetting substrate include inserting the film into a mold cavity of a mold assembly, pouring a polymerizable composition into the mold cavity, and curing the polymerizable composition. This results in a sandwich of the specific film embedded within the cured lens material. Such a method is disclosed, for example, in U.S. Pat. No. 4,873,029. The embedded film is typically a polarizing film, as described in International Patent Applications Nos. 0191994 and 200796425, but may also be a photochromic film, as described in patent documents EP 2040099 and U.S. Pat. No. 7,858,001. One advantage of such a process is that films embedded in a substrate are less susceptible to degradation, such as scratches, than films deposited on the lens surface.

[0005] The disclosed process allows embedding a film with one specific property (polarizing, photochromic) between two substrate layers. However, a combination of different properties imparted to the same optical article requires an additional coating step of the cured substrate / film / substrate sandwich or the inclusion of specific additives in the liquid curable composition (bulk casting).

[0006] Therefore, there remains a need for a method that allows for imparting several functions to a cast optical article in a single step. Summary of the Invention [Means for solving the problem]

[0007] Therefore, a first object of the present invention is a method for producing an optical article, the method comprising the steps of: (a) laminating a photochromic film containing at least one photochromic dye, optionally a polarizing film, and an ultraviolet radiation protection film to form a laminate; (b) placing the laminate obtained in step (a) or a portion thereof into a mold cavity of a two-part mold assembly; (c) pouring a polymerizable composition comprising at least one polymerizable monomer into the mold cavity; (d) curing the polymerizable composition comprising at least one polymerizable monomer poured in step (c) to form a substrate; and (e) removing the optical article from the mold cavity; The optical article comprises, in this order: - a first substrate layer; - a photochromic film containing at least one photochromic dye, - UV radiation protection film, a second substrate layer, and - optionally a functional film, such as a polarizing film, included between the first substrate layer and the photochromic film, between the photochromic film and the UV radiation protective film, or between the UV radiation protective film and the second substrate layer; Equipped with.

[0008] The method of the present invention is a cost-effective method for producing photochromic optical articles that provide a combination of photochromism and UV protection, and optionally polarization, without additional process steps or complexity.

[0009] In particular, photochromization, UV protection, and optionally polarization are performed in the casting step, with no additional steps required.

[0010] A second object of the invention is an optical article comprising, in this order: - a first substrate layer; - protective film, - a photochromic film containing at least one photochromic dye, - UV protection film, a second substrate layer, and - optionally a functional film, such as a polarizing film, included between the first substrate layer and the photochromic film, between the photochromic film and the UV radiation protective film, or between the UV radiation protective film and the second substrate layer; Equipped with. DETAILED DESCRIPTION OF THE INVENTION

[0011] The following description will make it clear what the invention consists of and how it can be achieved.

[0012] method A first object of the present invention is a method for producing an optical article, the method comprising the steps of: (a) laminating a photochromic film containing at least one photochromic dye, optionally a polarizing film, and an ultraviolet radiation protection film to form a laminate; (b) placing the laminate obtained in step (a) or a portion thereof into a mold cavity of a two-part mold assembly; (c) pouring a polymerizable composition comprising at least one polymerizable monomer into the mold cavity; (d) curing the polymerizable composition comprising at least one polymerizable monomer poured in step (c) to form a substrate; and (e) removing the optical article from the mold cavity; The optical article comprises, in this order: - a first substrate layer; - a photochromic film containing at least one photochromic dye, - UV radiation protection film, a second substrate layer, and - optionally a functional film, such as a polarizing film, included between the first substrate layer and the photochromic film, between the photochromic film and the UV radiation protective film, or between the UV radiation protective film and the second substrate layer; Equipped with.

[0013] The term "in this order" means that incident light reaching the optical article passes through the layers in this order. In particular, incident light on the optical article passes through the photochromic film before passing through the ultraviolet radiation protective film.

[0014] The term "between" with respect to different films or layers does not necessarily mean that the layers are in contact with one another. An intermediate layer may be present between the layers involved. In one embodiment, the term "between" means that the layers involved are in contact with one another and that no intermediate layer is present.

[0015] Step (a) The laminate according to the invention is obtained by laminating a film comprising at least one photochromic dye, an ultraviolet radiation protective film, and optionally a functional film, such as a polarizing film. The laminate may comprise additional films laminated with the photochromic and ultraviolet radiation protective film, and optionally additional active layers, such as a polarizing film, such as a color layer.

[0016] The laminate can be manufactured according to conventional processes. For example, the laminate can be manufactured by blow molding or thermoforming. The lamination process can include the use of at least one adhesive, for example, to improve the adhesion of the two films of the laminate to each other or to improve the adhesion of at least one side of the laminate to a substrate. Adhesives or adhesive substances that can be used in the lamination process of the present invention are well known in the art. The chemical structure of the adhesive will depend on the properties of the films and polymerizable composition to be laminated and the compatibility of the adhesive therewith. Preferably, the adhesive is an optically clear or transparent adhesive. The adhesive can be a thermosetting adhesive, especially when the laminate is manufactured by thermoforming. The adhesive can be, for example, a (meth)acrylate-based adhesive.

[0017] The layers (photochromic film, ultraviolet radiation protective film, and optionally a functional film, such as a polarizing film) may be laminated in any order. Preferably, when present, the functional film, such as a polarizing film, is laminated between the photochromic film and the ultraviolet radiation protective film. Thus, in a preferred embodiment, the laminate obtained in step (a) comprises, in this order, a photochromic film comprising at least one photochromic dye, a polarizing film, and an ultraviolet radiation protective film.

[0018] According to the present invention, the "photochromic dye" can be any known optically photochromic dye. For example, naphthopyrans, fulgides, benzopyrans, fulgimides, spironaphthopyrans, spirobenzoxazines, spironaphthoxazines, spirobenzopyrans, and combinations thereof can be used. Photochromic dyes can be blended to achieve different performance and / or cosmetic properties. Preferably, the photochromic dye is a naphthopyran, particularly an indenonaphthopyran.

[0019] A "photochromic film" is a film containing at least one photochromic dye as defined above. The photochromic film may be, for example, a cellulose triacetate film or a cellulose acetate butyrate film, preferably a cellulose triacetate film containing at least one photochromic dye, preferably a naphthopyran, especially an indenonaphthopyran.

[0020] "Film" refers to a simple monolayer or a laminated or layered film comprising multiple layers with a single functionality, preferably a simple monolayer.

[0021] A "functional film" is a film that imparts at least one property or functionality to an optical article. A functional film can be, for example, a polarizing film, an infrared protection film, or a blue light blocking film.

[0022] The term "polarizing film" is well known in the art and can be any polarizing film commonly used to make polarized optical articles such as ophthalmic lenses. Preferably, the polarizing film is based on polyvinyl alcohol (PVA), typically having a thickness of 5 to 200 microns. In particular, the polarizing film is a uniaxially stretched PVA film. Alternatively, the polarizing film can be based on polyethylene terephthalate (PET), typically having a thickness of 50 to 500 microns. Such polarizing films, which can have high polarization efficiency, are commercially available. Other polarizing films can include thin multilayer polymer materials, combinations of reflective and dichroic polarizers, or mixed polymer phase films, such as those described in U.S. Pat. Nos. 5,882,774, 6,096,375, and 5,867,316. ​​In one embodiment, the polarizing film is a polyvinyl alcohol film.

[0023] An "infrared protective film" is a film containing at least one infrared absorbing additive. The infrared protective film can reduce light transmittance in the infrared range, for example, 750 nm or higher. Preferably, the infrared protective film can reduce light transmittance in the near-infrared range, for example, 780 nm to 1400 nm. Typical examples of infrared absorbing additives that can be included in the infrared protective film of the present invention are near-infrared absorbers from various chemical families, such as phthalocyanines, naphthalocyanines, azo compounds, polymethines, porphyrins, triphenylmethanes, iminiums, squarylic acid compounds such as squaric acid, croconiums, dithiolenes such as nickel dithiolenes, quinones such as anthraquinones, perylenes such as polyperylenes, pyryliums, thiopyryliums, and cyanines. The near-infrared absorber is preferably a polymethine, phthalocyanine, porphyrin, triphenylmethane, iminium, squarylium, croconium, dithiolenes, quinones, polyperylenes, pyryliums, thiopyrylium, or cyanine near-infrared absorber. Suitable examples of additional near-infrared absorbers are described, for example, in Matsuoka, M., Infrared Absorbing Dyes, Plenum Press, New York, 1990, and Fabian, J., Nakazumi, H., Matsuoka, M., Near Infrared Absorbing Dyes, Chem. Rev. 1992, 92, 1197-1226. Specific examples of suitable near-infrared absorbers are NIR-920A® and NIR-1031A®, both available from QCR Solutions Corp.

[0024] A "blue light blocking film" is a film that at least partially blocks potentially harmful blue light, particularly in wavelength bands where a high risk exists (see, in particular, Table B1, ISO 8980-3 Standard:2003(E), which refers to the B(λ) blue light hazard function). Many means for producing such blue light blocking films are known in the art, including absorption, reflection, and interference techniques, or a combination of these techniques. In one embodiment, the blue light blocking film contains organic or inorganic compounds that absorb and / or reflect and / or interfere with blue light wavelengths. The film can be made from multiple thin films of organic and / or inorganic materials. Each layer, in combination with the other layers, can have the property of absorbing, reflecting, or interfering with blue light wavelengths. Among blue light blocking substances, perylenes, porphyrin-based molecules, coumarins, and acridines can be mentioned. In one embodiment of the present invention, the blue light blocking film is comprised of a multilayer, optionally a "pleated filter," of thin, preferably inorganic, dielectric layers with alternating low and high refractive indices, such as SiO2 and TiO2. The performance of the multilayer can be determined by design parameters such as the thickness of each thin layer, the refractive index of each layer, and the number of layers. This type of filter is described, inter alia, in U.S. Patent Nos. 6,984,038 and 7,066,596. Generally, blue light blocking filters are described in U.S. Patent No. 8,360,574.

[0025] An "ultraviolet radiation protective film" is a film containing at least one ultraviolet absorber additive. The ultraviolet protective film can reduce light transmission in the ultraviolet range below 400 nm, for example. Preferably, the ultraviolet radiation protective film is a UV400 protective film, which means that, based on its transmission curve, the ultraviolet cutoff of the film is 400 nm or the film transmits less than 1% of light up to 400 nm. Typical examples of ultraviolet absorber additives that can be included in the ultraviolet radiation protective film of the present invention are oxanilide, benzophenone, dihydroxybenzophenone, benzotriazole, benzoate, phenylbenzoate, benzimidazole, hydroxyphenyltriazine, and sterically hindered amines (HALS). Such ultraviolet absorbers are commercially available, in particular, under the trade names UVINUL® (BASF) and PARSOL® (GIVAUDAN). Preferably, the ultraviolet absorber additive is benzotriazole. The ultraviolet radiation protective film may be, for example, a cellulose triacetate film or a cellulose acetate butyrate film, preferably a cellulose triacetate film containing at least one ultraviolet absorber additive, especially a benzotriazole.

[0026] The photochromic dyes and / or UV-absorbing additives of the present invention can be independently incorporated into their respective film host materials by various methods described in the art. Such methods include immersing the host material in a hot solution of the photochromic dye or UV-absorbing additive to absorb the photochromic dye or UV-absorbing additive into the host material. In one embodiment, at least one photochromic dye is incorporated into the photochromic film at a temperature of 80°C or less. Once incorporated into the photochromic film, the at least one photochromic dye preferably can withstand exposure to an oxidative environment and / or temperatures up to 130°C.

[0027] In one embodiment, the photochromic film is a cellulose triacetate film containing a photochromic dye, such as a naphthopyran dye, and the ultraviolet radiation protective film is a cellulose triacetate film containing an ultraviolet absorber additive, such as benzotriazole. The resulting laminate in this embodiment exhibited high thermal stability, which enhanced the laminate's ability to withstand the casting process.

[0028] In a further embodiment, a protective film is inserted between the first substrate layer and the photochromic film. The protective film is particularly intended to protect the photochromic film, particularly the photochromic dye contained therein, from any oxidizing species contained in the polymerizable composition (such as a catalyst, resin, and / or initiator) that may damage the photochromic elements contained in the film during the production of the optical article. The protective film can be inserted especially when no other layers are present between the first substrate layer and the photochromic film. For example, the protective film can be laminated onto the photochromic film in step (a), optionally in the presence of an adhesive or adhesive substance as described above. Alternatively, the protective film can be placed in the mold cavity in step (b) in contact with the laminate, preferably in contact with the side of the laminate containing the photochromic film.

[0029] Examples of materials suitable for the protective film include acrylate resins, cellulose esters, and polycarbonate resins. In particular, the protective film comprises, and preferably consists of, cellulose triacetate film. The casting resin for the protective film preferably does not contain UV absorbers that significantly absorb or block the activation wavelength of the photochromic dye.

[0030] The insertion of a protective film into an optical article obtained by the manufacturing method of the present invention can impart interesting properties to the optical article, for example, with respect to activation and / or transmission. For example, an optical article according to the present invention comprising a protective film can have better activation properties, for example, a shorter activation time, and / or improved transmittance, than an optical article not comprising such a protective film. For example, an optical article obtained by the manufacturing method of the present invention comprising a protective film, such as a TAC protective film, can have a transmittance that is up to 20% darker after activation compared to a similar article not comprising a protective film.

[0031] The protective film, photochromic film, and / or UV protective film may independently have a thickness of at least 80 microns, particularly if they contain cellulose triacetate. Those skilled in the art will generally know the appropriate thickness to use for each layer, particularly as a function of the desired properties and / or materials contained in the layer.

[0032] Step (b) In some embodiments, for example when the optical article is a lens, the casting mold for the optical article generally comprises two substantially disc-shaped glass molds held together by an annular closure such as a gasket or tape, preferably a gasket. The laminate can be mounted in the mold cavity at a fixed distance from two opposing surfaces of the molds, with the laminate surface parallel to the inner surface of the mold on the front facing surface.

[0033] The laminate can be placed in the mold cavity as a whole, or it can be cut into wafers before being placed in the mold cavity to provide the wafers with an appropriate shape and / or size to fit within the mold cavity or taking into account the desired properties of the optical article to be obtained.

[0034] Prior to placement in the mold cavity, the laminate, or a portion thereof, may be formed to a desired curvature.

[0035] Step (c) The polymerizable composition according to the present invention is a liquid composition comprising at least one polymerizable monomer. Preferably, the polymerizable composition comprises a thermosetting material. In one embodiment, the polymerizable composition comprises only one polymerizable monomer.

[0036] The polymerizable monomers included in the polymerizable composition are described below in the section relating to the substrate in step (d). In one embodiment, the at least one polymerizable monomer included in the polymerizable composition is selected from the group consisting of diethylene glycol bis(allyl carbonate), thiourethane, and thermosetting urethane. In particular, the polymerizable monomer is diethylene glycol bis(allyl carbonate).

[0037] The polymerizable compositions according to the present invention may also contain additives conventionally used in polymerizable compositions intended for casting optical articles, in particular ophthalmic lenses, in conventional proportions, namely, inhibitors, dyes, UV absorbers, perfumes, deodorants, antioxidants, anti-yellowing agents, and mold release agents.

[0038] The fragrance makes it possible to mask the odor of the composition, especially during surface treatment or routing operations.

[0039] Conventional ultraviolet absorbers, such as those commercially available under the trade names UV5411®, UV9®, Tinuvin400®, TinuvinP®, Tinuvin312®, Seesorb701®, and Seesorb707®, can generally be used in amounts of up to 2% by weight of the total weight of polymerizable monomers. Preferably, the ultraviolet absorber included in the polymerizable composition does not substantially absorb light at wavelengths greater than 360 nm.

[0040] The release agent may be included in the polymerizable composition in an amount of up to 0.1% by weight based on the total weight of the polymerizable monomers. Among the release agents, mono- and di-alkyl phosphates, silicones, fluorinated hydrocarbons, fatty acids, and ammonium salts may be mentioned. Preferred release agents are mono- and di-alkyl phosphates and mixtures thereof. Such release agents are disclosed, for example, in patent documents U.S. Pat. No. 4,975,328 and European Patent No. EP 271839.

[0041] The polymerizable composition is cured in step (d) to form the substrate. Preferably, the polymerizable composition is self-supporting, i.e., able to hold its own shape without deformation, within the mold assembly when the annular closure of the two-part mold assembly (gasket or tape) is removed.

[0042] The monomer liquid for the polymerizable composition is poured into the mold onto either side of the laminate or a portion thereof.

[0043] Step (d) "Substrate" in the sense of the present invention should be understood to mean an uncoated substrate, generally having two main surfaces. The substrate may in particular be an optically transparent material having the shape of an optical article, for example an ophthalmic lens, to be attached to glass. In this context, the term "substrate" is understood to mean the base component material of an optical lens, in particular an ophthalmic lens. This material can serve as a support for one or more functional coatings or layer stacks.

[0044] The first and second substrate layers are preferably made from the same substrate.

[0045] The substrate may be made of a thermosetting (crosslinked) organic glass. Suitable thermosetting materials include diethylene glycol bis(allyl carbonate) polymers and copolymers (especially PPG Industries' CR-39®, EssilorOrma® lenses), polyurethanes, polythiourethanes, polyepoxides, polyepisulfides, poly(meth)acrylates, and copolymer-based substrates such as substrates comprising copolymers derived from (meth)acrylic polymers and bisphenol A, polythio(meth)acrylates, and substrates comprising copolymers and blends thereof.

[0046] Additional examples of substrates suitable for the present invention are those derived from the thermosetting polythiourethane resins sold by Mitsui Toatsu Chemicals company under the MR series, particularly MR6®, MR7®, and MR8® resins. These substrates and the monomers used in their production are described, inter alia, in U.S. Pat. Nos. 4,689,387, 4,775,733, 5,059,673, 5,087,758, and 5,191,055. Examples of polymerizable compositions containing poly(thio)urethane resins that can be used in the present invention are disclosed in International Application No. 2007096425.

[0047] A preferred material for the substrate is diethylene glycol bis(allyl carbonate) polymer. In a preferred embodiment, the substrate comprises, and is preferably made of, diethylene glycol bis(allyl carbonate) polymer, such as that sold by PPG Industries under the trademark CR-39®.

[0048] The polymerization conditions for the polymerizable composition vary depending on the composition of the polymerizable composition, the type and amount of catalyst used, and the shape of the mold; however, polymerization can be carried out at a temperature of 5°C to 140°C for 1 to 50 hours. In some cases, it is preferable to maintain or gradually increase the temperature within a temperature range of 5°C to 130°C and cure the polymerizable composition for 1 to 25 hours. Those skilled in the art can determine appropriate conditions for polymerizing the polymerizable composition depending on the composition of the polymerizable composition, the type and amount of catalyst used, and / or the shape of the mold. For example, if the material to be polymerized is diethylene glycol-bis(allyl carbonate), polymerization can be carried out by heating the mold to a maximum temperature of about 60°C to about 90°C for about 20 hours. Unless otherwise specified, the term "about" in the present invention refers to an interval of ±10% of the value.

[0049] Step (e) The polymerized and cured optical article is released from the mold to obtain the optical article of the present invention. The optical article is a photochromic and UV protective article that durably incorporates a photochromic film, a UV protective film, and optionally a functional film, such as a polarizing film, through its thickness. In one embodiment, the optical article removed in step (e) is an ophthalmic lens.

[0050] In certain embodiments, the optical article removed in step (e) has at least one, and preferably all, of the following characteristics: - the substrate of the first and second substrate layers is selected from the group consisting of diethylene glycol bis(allyl carbonate) polymers and copolymers; - the photochromic film containing at least one photochromic dye is a cellulose triacetate film containing at least one photochromic dye, - The ultraviolet radiation protection film is a UV400 protection film, the optical article comprises a protective film between the first substrate layer and the photochromic film comprising at least one photochromic dye; Optionally, a functional film, such as a polarizing film, is included between the photochromic film and the UV radiation protection film.

[0051] optical articles Another object of the invention is an optical article comprising, in this order: - a first substrate layer; - protective film, - a photochromic film containing at least one photochromic dye, - UV radiation protection film, a second substrate layer, and - optionally a functional film, such as a polarizing film, included between the first substrate layer and the photochromic film, between the photochromic film and the UV radiation protective film, or between the UV radiation protective film and the second substrate layer; Equipped with.

[0052] The compositions of the different layers of the optical article of the present invention and their preferred forms are as described above in the "Method" section.

[0053] In one embodiment, the optical article includes a functional film, such as a polarizing film, between the photochromic film and the ultraviolet radiation protective film. Preferably, the polarizing film is a polyvinyl alcohol film.

[0054] In one embodiment, the protective film included in the optical article is a cellulose triacetate film.

[0055] In one embodiment, the substrate of the first and second substrate layers of the optical article is selected from the group consisting of diethylene glycol bis(allyl carbonate) polymers and copolymers.

[0056] In one embodiment, the optical article is obtainable or obtained by a manufacturing method according to the present invention.

[0057] The optical article according to the present invention is preferably a transparent optical article, preferably an optical lens or lens blank, and more preferably an ophthalmic lens or lens blank, especially an ophthalmic lens.

[0058] As used herein, the term "lens" refers to an organic or inorganic glass lens comprising a lens substrate that may be coated with one or more coatings of various natures.

[0059] The term "ophthalmic lens" is used to mean a lens fitted to a spectacle frame, for example to protect the eyes and / or correct vision. Said lens may be chosen from afocal, unifocal, bifocal, trifocal and progressive lenses. Although ophthalmic optical systems are the preferred field of the invention, it will be understood that the invention may be applied to other types of optical articles, such as lenses for optical instruments in photography or astronomy, optical aiming lenses, eye visors, optical systems for lighting systems, etc.

[0060] In this specification, unless otherwise specified, an optical article / material is understood to be transparent when the observation of an image through said optical article is perceived without significant loss of contrast, i.e., when the formation of an image through said optical article is obtained without adversely affecting the quality of the image.This definition of the term "transparent" can be applied to all such modified in the description, unless otherwise specified.Preferably, each film or layer of the present invention is transparent.

[0061] The following examples are provided as illustrative, but not limiting, embodiments of the present invention. [Example]

[0062] Example 1 In accordance with the method of the present invention, a photochromic lens blank was prepared having the following structure: - a layer of diethylene glycol-bis(allyl carbonate) CR-39® resin - Photochromic cellulose triacetate layer - A layer of UV400 cellulose triacetate with benzotriazole - A layer of diethylene glycol-bis(allyl carbonate) CR-39® resin.

[0063] Example 2 In accordance with the method of the present invention, a photochromic polar lens blank was prepared having the following structure: - a layer of diethylene glycol-bis(allyl carbonate) CR-39® resin - Photochromic cellulose triacetate layer - Polyvinyl alcohol layer - A layer of UV400 cellulose triacetate with benzotriazole - A layer of diethylene glycol-bis(allyl carbonate) CR-39® resin.

[0064] In both Example 1 and Example 2, the photochromic dye is based on an indenonaphthopyran and each cellulose triacetate layer has a minimum thickness of 80 microns. The present disclosure includes the following inventive aspects: <Aspect 1> 1. A method of making an optical article, comprising: (a) forming a laminate by laminating a photochromic film comprising at least one photochromic dye, optionally a polarizing film, and an ultraviolet radiation protective film comprising at least one ultraviolet absorber additive; (b) placing the laminate obtained in step (a) or a portion thereof into a mold cavity of a two-part mold assembly; (c) pouring a polymerizable composition comprising at least one polymerizable monomer into the mold cavity; (d) curing the polymerizable composition comprising at least one polymerizable monomer poured in step (c) to form a substrate; and (e) removing the optical article from the mold cavity; The optical article comprises, in this order: - a first substrate layer; - a photochromic film containing at least one photochromic dye, - UV radiation protection film, a second substrate layer, and - optionally a functional film, such as a polarizing film, included between the first substrate layer and the photochromic film, between the photochromic film and the UV radiation protective film, or between the UV radiation protective film and the second substrate layer; A method for manufacturing an optical article, comprising: <Aspect 2> 2. The method for producing an optical article of claim 1, wherein the laminate obtained in step (a) comprises, in this order: a photochromic film comprising at least one photochromic dye; a functional film, such as a polarizing film; and an ultraviolet radiation protection film. <Aspect 3> 3. The method for producing an optical article according to claim 2, wherein the functional film is a polarizing film, and the polarizing film is a polyvinyl alcohol film. <Aspect 4> Aspect 4. The method for producing an optical article according to any one of aspects 1 to 3, wherein the photochromic film comprising at least one photochromic dye is a cellulose triacetate film comprising at least one photochromic dye. <Aspect 5> A method for producing an optical article according to any one of aspects 1 to 4, wherein the photochromic dye is naphthopyran. <Aspect 6> 6. The method for producing an optical article of any one of aspects 1 to 5, wherein the optical article further comprises a protective film between the first substrate layer and the photochromic film comprising the at least one photochromic dye. <Aspect 7> 7. The method of making an optical article according to any one of aspects 1 to 6, wherein the ultraviolet radiation protective film comprising at least one ultraviolet absorber additive is a cellulose triacetate film comprising at least one ultraviolet absorber additive. <Aspect 8> A method of making an optical article according to any one of aspects 1 to 7, wherein the UV absorber additive is benzotriazole. <Aspect 9> Aspect 9. The method for producing an optical article according to any one of aspects 1 to 8, wherein the at least one polymerizable monomer contained in the polymerizable composition is diethylene glycol bis(allyl carbonate). <Aspect 10> - the substrate of the first and second substrate layers is selected from the group consisting of diethylene glycol bis(allyl carbonate) polymers and copolymers; - the photochromic film comprising at least one photochromic dye is a cellulose triacetate film comprising at least one photochromic dye; - the ultraviolet radiation protection film is a UV400 protection film; - the optical article comprises a protective film between the first substrate layer and the photochromic film comprising the at least one photochromic dye, - optionally a functional film, such as a polarizing film, is included between said photochromic film and said UV radiation protection film; A method for producing the optical article according to any one of aspects 1 to 9. <Aspect 11> A method for producing an optical article according to any one of aspects 1 to 9, wherein the optical article is an ophthalmic lens. <Aspect 12> Optical articles, in this order: - a first substrate layer; - protective film, - a photochromic film containing at least one photochromic dye, - UV radiation protection film, a second substrate layer, and - optionally a functional film, such as a polarizing film, included between the first substrate layer and the photochromic film, between the photochromic film and the UV radiation protective film, or between the UV radiation protective film and the second substrate layer; An optical article comprising: <Aspect 13> 13. The optical article of embodiment 12, comprising a functional film, such as a polarizing film, between the photochromic film and the ultraviolet radiation protective film. <Aspect 14> 14. The optical article of claim 13, wherein the polarizing film is a polyvinyl alcohol film. <Aspect 15> 15. The optical article according to any one of aspects 12 to 14, wherein the protective film is a cellulose triacetate film.

Claims

1. 1. A method of making an optical article, comprising: (a) forming a laminate by laminating a photochromic film comprising at least one photochromic dye and an ultraviolet radiation protective film comprising at least one ultraviolet absorber additive, wherein the ultraviolet radiation protective film is a UV400 protective film having a cutoff of 400 nm; (b) placing the laminate obtained in step (a) or a portion thereof into a mold cavity of a two-part mold assembly; (c) pouring a polymerizable composition comprising at least one polymerizable monomer into the mold cavity, wherein the polymerizable composition is a liquid composition, and pouring a monomer liquid for the polymerizable composition into the mold onto either side or a portion thereof of the laminate; (d) curing the polymerizable composition comprising at least one polymerizable monomer poured in step (c) to form a substrate; and (e) removing the optical article from the mold cavity; The optical article comprises, in this order: a first substrate layer, - Protective film - a photochromic film comprising at least one photochromic dye; an ultraviolet radiation protective film comprising at least one ultraviolet absorber additive, the ultraviolet radiation protective film being a UV400 protective film with a cutoff of 400 nm; and a second substrate layer Equipped with the protective film is laminated onto the photochromic film in step (a); the optical article is configured such that light incident on the optical article passes through the photochromic film before passing through the ultraviolet radiation protective film; A method for producing an optical article.

2. 10. The method for manufacturing an optical article according to claim 1, wherein the laminate obtained in step (a) comprises a functional film included between the first substrate layer and the photochromic film, between the photochromic film and the ultraviolet radiation protective film, or between the ultraviolet radiation protective film and the second substrate layer.

3. 2. The method for producing an optical article according to claim 1, wherein the functional film is a polarizing film, and the laminate obtained in step (a) comprises, in this order: a photochromic film comprising at least one photochromic dye, the polarizing film, and an ultraviolet radiation protection film.

4. The method for producing an optical article according to claim 3 , wherein the polarizing film is a polyvinyl alcohol film.

5. The method for producing an optical article according to any one of claims 1 to 3, wherein the photochromic film comprising at least one photochromic dye is a cellulose triacetate film comprising at least one photochromic dye.

6. A method for producing an optical article according to any one of claims 1 to 4, wherein the photochromic dye is a naphthopyran.

7. 7. The method for producing an optical article according to any one of claims 1 to 6, wherein the ultraviolet radiation protective film comprising at least one ultraviolet absorber additive is a cellulose triacetate film comprising at least one ultraviolet absorber additive.

8. A method for producing an optical article according to any one of claims 1 to 7, wherein the UV absorber additive is a benzotriazole.

9. 9. The method for producing an optical article according to any one of claims 1 to 8, wherein the at least one polymerizable monomer included in the polymerizable composition is diethylene glycol bis(allyl carbonate).

10. the substrate of the first and second substrate layers is selected from the group consisting of diethylene glycol bis(allyl carbonate) polymers and copolymers; - said photochromic film containing at least one photochromic dye is a cellulose triacetate film containing at least one photochromic dye; - said ultraviolet radiation protection film is a UV400 protection film; the optical article comprises a protective film between the first substrate layer and the photochromic film comprising at least one photochromic dye; A method for producing an optical article according to any one of claims 1 to 9.

11. The method for producing an optical article according to any one of claims 1 to 9, wherein the optical article is an ophthalmic lens.

12. Optical articles, in this order: a first substrate layer, - protective film, - a photochromic film comprising at least one photochromic dye; - an ultraviolet radiation protective film comprising at least one ultraviolet absorber additive, and a second substrate layer Equipped with the ultraviolet radiation protective film is a UV400 protective film having a cutoff of 400 nm; the materials of the first substrate layer and the second substrate layer used to manufacture the optical article are made of a cured polymerizable composition including at least one polymerizable monomer; the optical article is configured such that light incident on the optical article passes through the photochromic film before passing through the ultraviolet radiation protective film; Optical articles.

13. 13. The optical article of claim 12, comprising a functional film included between the first substrate layer and the photochromic film, between the photochromic film and the ultraviolet radiation protective film, or between the ultraviolet radiation protective film and the second substrate layer.

14. 13. The optical article of claim 12, wherein the functional film is a polarizing film, and the polarizing film is located between the photochromic film and the ultraviolet radiation protective film.

15. 15. The optical article of claim 14, wherein the polarizing film is a polyvinyl alcohol film.

16. The optical article according to any one of claims 12 to 15, wherein the protective film is a cellulose triacetate film.

17. The optical article of claim 12 , wherein the material of the protective film comprises an acrylate resin, a cellulose ester, or a polycarbonate resin, and the material of the protective film does not comprise a UV absorber.

18. The optical article of claim 12 , wherein the polymerizable composition comprises a thermoset material.