Method for making a photochromic optical article

Abstract

A method for making an optical article, such as an ophthalmic lens, having photochromic and UV protection properties and an optical article having such properties are provided.

Description

Technical Field

[0001] The present invention relates to a method for producing an optical article, such as an ophthalmic lens, having photochromic and UV protection properties, and to an optical article having said properties.

[0002] More specifically, the present invention relates to a method for producing an optical article comprising a laminate embedded in a substrate, the laminate comprising at least a photochromic film and an ultraviolet radiation protective film, and to an optical article having said structure. Background Art

[0003] Photochromic lenses are optical lenses with variable tint. Photochromic lenses are well known in the art, and various processes for their manufacture have been described. The manufacture of optical lenses, such as photochromic lenses, typically requires combining multiple layers, each of which provides specific properties to the optical lens. For example, a specific layer may provide UV protection or polarization to the optical lens. Manufacturing the layer stack typically involves a series of deposition steps.

[0004] Existing methods for embedding a specific layer or film in a lens comprising a thermosetting substrate comprise the steps of inserting the film into a mold cavity of a mold assembly, pouring a polymerizable composition into the mold cavity, and curing the polymerizable composition. Thus, a sandwich is obtained in which the specific film is embedded in the cured lens material. This method is disclosed, for example, in U.S. Patent No. 4,873,029. The embedded film is typically a polarizing film as described in patent applications WO 0191994 and WO 200796425, but can also be a photochromic film as described in patent documents EP 2040099 and US 7858001. One advantage of this process is that a film embedded in a substrate is less susceptible to damage, such as scratches, than a film deposited on the surface of the lens.

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

[0006] Therefore, there remains a need for methods that allow for imparting multiple functionalities to cast optical articles in a single step. Summary of the Invention

[0007] Therefore, a first object of the present invention is a method for producing an optical article, comprising:

[0008] (a) forming a laminate by laminating a photochromic film comprising at least one photochromic dye, an optional polarizing film, and an ultraviolet radiation protective film,

[0009] (b) positioning the laminate obtained in step (a) or a portion thereof in a mold cavity of a two-part mold assembly,

[0010] (c) pouring a polymerizable composition comprising at least one polymerizable monomer into the mold cavity,

[0011] (d) curing the polymerizable composition comprising at least one polymerizable monomer poured in step (c) to form a substrate, and

[0012] (e) removing the optical article from the mold cavity,

[0013] The optical product comprises, in this order:

[0014] - a first substrate layer,

[0015] - a photochromic film comprising at least one photochromic dye,

[0016] - UV radiation protection film,

[0017] - a second substrate layer, and

[0018] - an optional functional film, such as a polarizing 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.

[0019] The method of the present invention is a cost-effective method for manufacturing photochromic optical articles, providing a combination of photochromism with UV protection and optional polarization without adding process steps or complexity.

[0020] In particular, photochromism, UV protection and optional polarization are implemented during the casting step, without the need for additional steps.

[0021] A second object of the present invention is an optical product comprising, in this order:

[0022] - a first substrate layer,

[0023] - Protective film,

[0024] - a photochromic film comprising at least one photochromic dye,

[0025] - UV radiation protection film,

[0026] - a second substrate layer, and

[0027] - an optional functional film, such as a polarizing 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. DETAILED DESCRIPTION

[0028] The following description will make clear what the present invention includes and how to implement the present invention.

[0029] method

[0030] A first object of the present invention is a method for producing an optical article, comprising:

[0031] (a) forming a laminate by laminating a photochromic film comprising at least one photochromic dye, an optional polarizing film, and an ultraviolet radiation protective film,

[0032] (b) positioning the laminate obtained in step (a), or a portion thereof, in a mold cavity of a two-part mold assembly,

[0033] (c) pouring a polymerizable composition comprising at least one polymerizable monomer into the mold cavity,

[0034] (d) curing the polymerizable composition comprising at least one polymerizable monomer poured in step (c) to form a substrate, and

[0035] (e) removing the optical article from the mold cavity,

[0036] Among them, optical products include in this order:

[0037] - a first substrate layer,

[0038] - a photochromic film comprising at least one photochromic dye,

[0039] - UV radiation protection film,

[0040] - a second substrate layer, and

[0041] - Inclusion of an optional functional film, such as a polarizing film, 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.

[0042] 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.

[0043] The term "between" with respect to different films or layers does not necessarily mean that the layers are in contact with each other. There may be an intervening layer between the relevant layers. In an embodiment, the term "between" means that the relevant layers are in contact with each other and there is no intervening layer.

[0044] Step (a)

[0045] The laminate according to the present invention is obtained by laminating a film containing at least one photochromic dye, an ultraviolet radiation protective film, and optionally a functional film (e.g., a polarizing film). The laminate may include an additional film (e.g., an additional active layer) to be laminated together with the photochromic film, the ultraviolet radiation protective film, and optionally the polarizing film, for example as a color layer.

[0046] The laminate can be manufactured according to conventional processes. For example, the laminate can be manufactured by blow molding or thermoforming. The lamination process may include the use of at least one glue, for example, for improving the adhesion of the two films of the laminate to each other, or for improving the adhesion of at least one side of the laminate to the substrate. The glue or adhesive that can be used in the lamination process of the present invention is well known in the art. The chemical structure of the glue will depend on the properties of the film to be laminated and the polymerizable composition, as well as the compatibility of the glue with them. Preferably, the glue is an optically clear or transparent glue. The glue can be a heat-curable glue, particularly when the laminate is manufactured by thermoforming. The glue can be, for example, a glue based on (meth)acrylate.

[0047] These layers (the photochromic film, the UV radiation protective film, and the optional functional film, such as a polarizing film) are laminated in any order. Preferably, when present, the functional film (such as a polarizing film) is laminated between the photochromic film and the UV radiation protective film. Thus, in a preferred embodiment, the laminate obtained in step (a) comprises, in this order, a photochromic film containing at least one photochromic dye, a polarizing film, and a UV radiation protective film.

[0048] According to the present invention, a "photochromic dye" can be any known optical photochromic dye. For example, naphthopyrans, fulgides, benzopyrans, fulgimides, spironaphthopyrans, spirobenzoxazines, spironaphthooxazines, spirobenzopyrans, and combinations thereof can be used. Photochromic dyes can be mixed to obtain different performance and / or aesthetic properties. Preferably, the photochromic dye is a naphthopyran, in particular an indenonaphthopyran.

[0049] A "photochromic film" is a film comprising 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, comprising at least one photochromic dye, preferably a naphthopyran, in particular an indenonaphthopyran.

[0050] "Film" refers to a simple single layer, or a laminated film or a layered film comprising a plurality of layers having a single function, preferably a simple single layer.

[0051] A "functional film" is a film that imparts at least one characteristic or function to an optical article. The functional film may be, for example, a polarizing film, an infrared protection film, or a blue light cutoff film.

[0052] "Polarizing film" is well known in the art and can be any polarizing film typically used to make polarized optical products (such as ophthalmic lenses). Preferably, the polarizing film is based on polyvinyl alcohol (PVA), typically with a thickness between 5 and 200 microns. In particular, the polarizing film is a uniaxially stretched PVA film. Alternatively, the polarizing film can be based on polyethylene terephthalate or PET, typically with a thickness between 50 and 500 microns. Such polarizing films that can have high polarization efficiency are commercially available. Other polarizing films can include thin multilayer polymer materials, reflective and dichroic combination polarizers, or films of mixed polymer phases, such as those described in US 5,882,774, US 6,096,375, and US 5,867,316. ​​In an embodiment, the polarizing film is a polyvinyl alcohol film.

[0053] "Infrared protective film" is a film comprising at least one infrared absorber additive. The infrared protective film is capable of reducing light transmission in the infrared range (e.g., 750 nm and above). Preferably, the infrared protective film is capable of reducing light transmission in the near-infrared range (e.g., from 780 nm to 1400 nm). Typical examples of infrared absorber additives that can be included in the infrared protective film of the present invention are near-infrared absorbers from different chemical families, such as phthalocyanines, naphthalocyanines, azo compounds, polymethines, porphyrins, triphenylmethanes, iminiums, squaric acid compounds (e.g., squaric acid cyanines, crotonic acid cyanines), disulfides (e.g., nickel disulfides), quinones (e.g., anthraquinones), perylenes (e.g., polyperylenes), pyryliums, thiopyryliums, and cyanines. The near infrared absorber is preferably a polymethine, phthalocyanine, porphyrin, triphenylmethane, iminium, squarylium, cretonium, dithiol, quinone, polyperylene, pyrylium, thiopyrylium or cyanine near infrared absorber. Suitable examples of additional near infrared absorbers are described, for example, in Matsuoka, M. "Infrared Absorbing Dyes", Plainium 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 and Both are available from QCR Solutions.

[0054] A "blue-light cut-off film" is a film that at least partially blocks potentially harmful blue light, in particular with respect to wavelength bands that present an increased risk (see, in particular, Table B1 of ISO 8980-3 standard: 2003 (E), reference B(λ) blue light hazard function). Many means for producing such blue-light cut-off films are known in the art, including absorption, reflection and interference techniques or combinations of these techniques. In an embodiment, the blue-light cut-off film comprises an organic or inorganic compound that absorbs and / or reflects and / or interferes with wavelengths of blue light. The film may be composed of a multilayer thin film of organic and / or inorganic substances. Each layer, in combination with the other layers, may have the property of absorbing, reflecting or interfering with wavelengths of blue light. Among the blue-light blocking substances, mention may be made of dinaphthylene, molecular-based porphyrins, coumarins and acridines. In an embodiment of the invention, the blue-light cut-off film is composed of a thin multilayer (optional "comb filter"), preferably an inorganic dielectric layer with alternating low and high refractive indices (such as SiO2 and TiO2). Design parameters such as the thickness of each layer, the refractive index of each layer, and the number of layers determine the performance of the multilayer. Filters of this type are 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.

[0055] "Ultraviolet radiation protective film" is a film comprising at least one ultraviolet absorber additive. The ultraviolet radiation protective film is capable of reducing the transmission of light in the ultraviolet range (e.g., 400 nm and below). Preferably, the ultraviolet radiation protective film is a UV400 protective film, meaning that the ultraviolet cutoff wavelength of the film is 400 nm, or the film transmits less than 1% of light up to 400 nm based on its transmission curve. Typical examples of ultraviolet absorber additives that can be included in the ultraviolet radiation protective film of the present invention are oxalanilide, benzophenone, dihydroxybenzophenone, benzotriazole, benzoate, phenyl benzoate, benzimidazole, hydroxyphenyl triazine, and sterically hindered amines (HALS). Such ultraviolet absorbers can be found in particular under the trade name (BASF) and (GIVAUDAN) is commercially available. Preferably, the UV absorber additive is benzotriazole. The UV radiation protection film can be, for example, a cellulose triacetate film or a cellulose acetate butyrate film, preferably a cellulose triacetate film, containing at least one UV absorber additive, in particular benzotriazole.

[0056] The photochromic dye and / or UV absorber additive of the present invention can be independently incorporated into the corresponding film matrix material by various methods described in the art. Such methods include imbibing the photochromic dye or UV absorber additive into the matrix material by immersing the matrix material in a hot solution of the photochromic dye or UV absorber additive. In an embodiment, the 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 can preferably be subjected to an oxidizing environment and / or exposed to temperatures up to 130°C.

[0057] In an embodiment, the photochromic film is a cellulose triacetate film containing a photochromic dye (e.g., a naphthopyran dye), and the ultraviolet radiation protective film is a cellulose triacetate film containing an ultraviolet absorber additive (e.g., benzotriazole). The laminate obtained in this embodiment exhibits high thermal stability, which enhances the ability of the laminate to withstand the casting process.

[0058] In another 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, especially the photochromic dye contained in the photochromic film, from any oxidizing substances (such as catalysts, resins and / or initiators) contained in the polymerizable composition that may damage the photochromic elements contained in the film during the manufacture of the optical article. In particular, the protective film can be inserted when no other layers are present between the first substrate layer and the photochromic film. The protective film can, for example, be optionally laminated on the photochromic film in step (a) in the presence of the above-mentioned glue or adhesive. Alternatively, the protective film can be positioned in the mold cavity in step (b) in contact with the laminate, preferably in contact with the side of the laminate that includes the photochromic film.

[0059] Examples of preferred materials for the protective film include acrylate resins, cellulose esters, and polycarbonate resins. In particular, the protective film includes, or preferably consists of, a cellulose triacetate film. Preferably, the casting resin used for the protective film does not contain a UV absorber that would significantly absorb or block the activation wavelength of the photochromic dye.

[0060] Inserting a protective film into an optical article obtained by the manufacturing method of the present invention can impart interesting properties to the optical article, such as in terms of activation and / or transmission. For example, an optical article according to the present invention including a protective film can have better activation properties, such as a shorter activation time and / or improved transmission, than an optical article not including such a protective film. For example, an optical article obtained by the manufacturing method of the present invention including a protective film (e.g., a TAC protective film) can have a darker transmission of up to 20% after activation compared to a similar article not including such a protective film.

[0061] The protective film, photochromic film and / or UV protective film can independently have a thickness of at least 80 microns, especially when they comprise cellulose triacetate. Those skilled in the art generally know the appropriate thickness to use for each layer, particularly depending on the desired properties and / or the materials contained in the layer.

[0062] Step (b)

[0063] In some embodiments, for example, when the optical article is a lens, the optical article casting mold typically comprises two generally disc-shaped glass molds held by an annular closure member (such as a gasket or tape, preferably a gasket). The laminate can be mounted in the cavity of the mold parallel to the mold inner surface on the front side facing the laminate surface, at a distance from the two opposing surfaces of the mold.

[0064] The laminate may be positioned in the mold cavity as a whole or, before being positioned in the mold cavity, may be cut into wafers to provide a suitable shape and / or size for fitting into the mold cavity or taking into account the desired properties of the optical article to be obtained.

[0065] The laminate or a portion thereof may be pre-formed to a desired curvature prior to positioning in the mold cavity.

[0066] Step (c)

[0067] 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 an embodiment, the polymerizable composition comprises only one polymerizable monomer.

[0068] The polymerizable monomers included in the polymerizable composition are described in the following step (d) in relation to the substrate. In an embodiment, the at least one polymerizable monomer included in the polymerizable composition is selected from the group consisting of diethylene glycol bis(allyl carbonate), thiourethanes, and thermosetting urethanes. In particular, the polymerizable monomer is diethylene glycol bis(allyl carbonate).

[0069] The polymerizable composition according to the invention may also contain conventionally used additives, which are usually used in conventional proportions in polymerizable compositions intended for molding optical articles, in particular ophthalmic lenses, namely inhibitors, dyes, UV absorbers, fragrances, deodorants, antioxidants, anti-yellowing agents and release agents.

[0070] The fragrance allows to mask the odor of the composition, especially during surface treatment or grooving operations.

[0071] Common ultraviolet absorbers, such as those sold under the trade name UV UV Tinuvin Tinuvin Tinuvin Seesorb and Seesorb Commercially available ones may generally be used in amounts up to 2% by weight based on the total weight of the polymerizable monomers. Preferably, the UV absorber included in the polymerizable composition does not substantially absorb light having a wavelength exceeding 360 nm.

[0072] The amount of release agent included in the polymerizable composition can be up to 0.1% by weight based on the total weight of the polymerizable monomers. Among release agents, monoalkyl and dialkyl phosphates, siloxanes, fluorinated hydrocarbons, fatty acids, and ammonium salts can be cited. Preferred release agents are monoalkyl and dialkyl phosphates and mixtures thereof. Such release agents are disclosed, for example, in patent documents US 4,975,328 and EP 271839.

[0073] In step (d) the polymerisable composition is cured to form the substrate. Preferably, the polymerisable composition is self-supporting in the mould assembly, ie is able to take on its own shape without deformation, when the annular closure (gasket or band) of the two-part mould assembly has been removed.

[0074] The monomer liquid for the polymerizable composition is poured into the mold, on both sides of the laminate or a portion thereof.

[0075] Step (d)

[0076] In the sense of the present invention, "substrate" is understood to mean an uncoated substrate and generally has two main faces. The substrate can be, in particular, an optically transparent material in the shape of an optical article (e.g., an ophthalmic lens intended to be mounted on spectacles). In this context, the term "substrate" is understood to mean the basic building block of an optical lens, and more particularly an ophthalmic lens. This material can serve as a support for a stack of one or more coatings or layers.

[0077] The first substrate layer and the second substrate layer are preferably made of the same substrate.

[0078] The substrate may be made of thermosetting (crosslinked) organic glass. Among suitable thermosetting materials, there may be mentioned diethylene glycol bis (allyl carbonate) polymers and copolymers (particularly those from PPG Industries). Essilor lenses), polyurethanes, polythiourethanes, polyepoxides, polyepisulfides, poly(meth)acrylates, and copolymer-based substrates, such as substrates comprising (meth)acrylic polymers and copolymers derived from bisphenol A, polythio(meth)acrylates, and copolymers thereof and blends thereof.

[0079] Other examples of substrates suitable for the present invention are those obtained from thermosetting polythiourethane resins marketed by Mitsui Toatsu Chemicals company as the MR series, specifically and These substrates and the monomers used to prepare them are described in patents US 4,689,387, US 4,775,733, US 5,059,673, US 5,087,758 and US 5,191,055. Patent application WO 2007096425 discloses examples of polymerizable compositions comprising poly(thio)urethane resins that can be used in the present invention.

[0080] The preferred material for the substrate is diethylene glycol bis(allyl carbonate) polymer. In a preferred embodiment, the substrate comprises diethylene glycol bis(allyl carbonate) polymer, such as available from PPG Industries and Sold, preferably made from.

[0081] The polymerization conditions of the polymerizable composition vary depending on the composition of the polymerizable composition, the type and amount of the catalyst, and the shape of the mold, but polymerization can be carried out at a temperature of 5°C to 140°C for 1 to 50 hours. In some cases, it is preferred to maintain or gradually increase the temperature within a temperature range of 5°C to 130°C, and the polymerizable composition is cured for 1 to 25 hours. Those of ordinary skill in the art can determine the appropriate conditions for the polymerization of the polymerizable composition based on the composition of the polymerizable composition, the type and amount of the catalyst, and / or the shape of the mold. For example, when the polymerizable material is diethylene glycol-bis(allyl carbonate), polymerization can be carried out by heating the mold to a maximum temperature between about 60°C and about 90°C for about 20 hours. Unless otherwise indicated, the term "about" value in the present invention refers to an interval included between ±10% of the value.

[0082] Step (e)

[0083] The optical article cured by polymerization is demolded from the mold to obtain an optical article according to the present invention. The optical article is a photochromic and UV protective article that permanently incorporates a photochromic film, a UV protective film, and an optional functional film (e.g., a polarizing film) throughout its thickness. In an embodiment, the optical article removed in step (e) is an ophthalmic lens.

[0084] In particular embodiments, the optical article removed in step (e) has at least one, and preferably all, of the following characteristics:

[0085] - the substrates of the first and second substrate layers are selected from the group consisting of diethylene glycol bis(allyl carbonate) polymers and copolymers;

[0086] - the photochromic film comprising at least one photochromic dye is a cellulose triacetate film comprising at least one photochromic dye;

[0087] -Ultraviolet radiation protection film is UV400 protection film;

[0088] - the optical article comprises a protective film between the first substrate layer and the photochromic film comprising at least one photochromic dye; and

[0089] - An optional functional film (eg a polarizing film) is included between the photochromic film and the UV radiation protection film.

[0090] Optical products

[0091] Another object of the invention is an optical article comprising, in this order:

[0092] - a first substrate layer,

[0093] - Protective film,

[0094] - a photochromic film comprising at least one photochromic dye,

[0095] - UV radiation protection film,

[0096] - a second substrate layer, and

[0097] - Inclusion of an optional functional film, such as a polarizing film, 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.

[0098] The composition of the different layers of the optical article of the present invention and their preferred forms are as described above in the "Method" section.

[0099] In an embodiment, the optical article comprises a functional film, such as a polarizing film, between the photochromic film and the ultraviolet radiation protection film. Preferably, the polarizing film is a polyvinyl alcohol film.

[0100] In an embodiment, the protective film included in the optical article is a cellulose triacetate film.

[0101] In an embodiment, the substrate of the first substrate layer and the second substrate layer of the optical article is selected from the group consisting of diethylene glycol bis(allyl carbonate) polymers and copolymers.

[0102] In an embodiment, the optical article is obtainable or obtained by the manufacturing method according to the invention.

[0103] The optical article according to the present invention is preferably a transparent optical article, preferably an optical lens or a lens blank, more preferably an ophthalmic lens or a lens blank, in particular an ophthalmic lens.

[0104] As used herein, the term "lens" refers to an organic or inorganic glass lens comprising a lens substrate which may be coated with one or more coatings of varying properties.

[0105] The term "ophthalmic lens" is used to refer to a lens that fits into a spectacle frame, for example, to protect the eyes and / or correct vision. The lens may be selected from afocal lenses, single-focal lenses, bifocal lenses, trifocal lenses, and progressive lenses. While ophthalmic optics is a preferred field of the present invention, it should be understood that the present invention may be applied to other types of optical articles, such as lenses for optical instruments used in photography or astronomy, optical sights, eye goggles, optical components for lighting systems, and the like.

[0106] In this specification, unless otherwise specified, an optical article / material is understood to be transparent when no significant loss of contrast is perceived when viewing an image through the optical article, i.e., when image formation through the optical article is achieved without adversely affecting the quality of the image. This definition of the term "transparent" applies to all objects defined in this specification, unless otherwise specified. Preferably, in the present invention, each film or layer is transparent.

[0107] The following examples are provided as illustrative, non-limiting embodiments of the invention.

[0108] Example

[0109] Example 1

[0110] According to the method of the present invention, a photochromic lens blank having the following structure is prepared:

[0111] -Diethylene glycol-bis(allyl carbonate) Resin layer

[0112] - Photochromic triacetate cellulose layer

[0113] - UV400 cellulose triacetate layer containing benzotriazole

[0114] -Diethylene glycol-bis(allyl carbonate) Resin layer.

[0115] Example 2

[0116] According to the method of the present invention, a photochromic polarizing lens blank having the following structure is prepared:

[0117] -Diethylene glycol-bis(allyl carbonate) Resin layer

[0118] - Photochromic triacetate cellulose layer

[0119] -Polyvinyl alcohol layer

[0120] - UV400 cellulose triacetate layer containing benzotriazole

[0121] -Diethylene glycol-bis(allyl carbonate) Resin layer.

[0122] In Examples 1 and 2, the photochromic dye was based on indenonaphthopyran and each cellulose triacetate layer had a minimum thickness of 80 microns.

Claims

1. A method for manufacturing an optical product, the method comprising: (a) forming a laminate by laminating a photochromic film comprising at least one photochromic dye, a polarizing film, and an ultraviolet radiation protective film comprising at least one ultraviolet absorber additive, (b) positioning the laminate obtained in step (a) or a portion thereof in a mold cavity of a two-part mold assembly, (c) pouring a polymerizable composition comprising at least one polymerizable monomer into the mold cavity, the polymerizable composition being a liquid composition and pouring a monomer liquid for the polymerizable composition into the mold, on both sides of the laminate or a portion thereof, (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 product comprises, in this order: - a first substrate layer, - Protective film, - a photochromic film comprising at least one photochromic dye, - polarizing film, - a UV radiation protective film comprising at least one UV absorber additive, - a second substrate layer, and - wherein a polarizing film is included between said photochromic film and said ultraviolet radiation protective film, The protective film is laminated on the photochromic film in step (a).

2. The method for manufacturing an optical product according to claim 1, wherein: The polarizing film is a polyvinyl alcohol film.

3. The method for manufacturing an optical product according to claim 1, wherein: The photochromic film comprising at least one photochromic dye is a cellulose triacetate film comprising at least one photochromic dye.

4. The method for manufacturing an optical product according to claim 1, wherein: The photochromic dye is a naphthopyran.

5. The method for manufacturing an optical product according to claim 1, 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.

6. The method for manufacturing an optical product according to claim 1, wherein: The UV absorber additive is benzotriazole.

7. The method for manufacturing an optical product according to claim 1, wherein: At least one polymerizable monomer included in the polymerizable composition is diethylene glycol bis(allyl carbonate).

8. The method of manufacturing an optical article according to claim 1, wherein: - the substrates of the first substrate layer and the second substrate layer are 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 at least one photochromic dye; as well as - a polarizing film included between the photochromic film and the ultraviolet radiation protective film.

9. The method for manufacturing an optical product according to claim 1, wherein: The optical article is an ophthalmic lens.

10. An optical product comprising, in this order: - a first substrate layer, - Protective film, - a photochromic film comprising at least one photochromic dye, - polarizing film, - UV radiation protection film, - a second substrate layer, and The first substrate layer and the second substrate layer are made of thermosetting organic glass or diethylene glycol bis(allyl carbonate) polymer and copolymer.

11. The optical article according to claim 10, wherein the material for the protective film comprises an acrylate resin, a cellulose ester, or a polycarbonate resin, and the material for the protective film does not contain an ultraviolet absorber.

12. The optical article according to claim 10, wherein The polarizing film is a polyvinyl alcohol film.

13. The optical article according to claim 10, wherein The protective film is a cellulose triacetate film.