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Title:
PHOTOCHROMIC LENS WITH LAMINATED FILM, METHOD FOR PRODUCING A PHOTOCHROMIC LENS, AND A SPECTACLE FRAME
Document Type and Number:
WIPO Patent Application WO/2020/132822
Kind Code:
A1
Abstract:
An optical lens comprising a laminated film, said laminated film containing an adhesive layer (1), a barrier layer (2), a photochromic layer (3), a barrier layer (4), and an adhesive layer (5), wherein said layers (1) to (5) are arranged in succession and wherein said laminated film is substantially incorporated within an optical lens body.

Inventors:
LIANG JINGYE (CN)
OUYANG LIU (CN)
BROWN STEPHEN (AU)
TIAN YONG (CN)
Application Number:
PCT/CN2018/123150
Publication Date:
July 02, 2020
Filing Date:
December 24, 2018
Export Citation:
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Assignee:
CARL ZEISS VISION TECHNICAL SERVICES GUANGZHOU LTD (CN)
ZEISS CARL VISION INT GMBH (DE)
International Classes:
G02C7/10; B29D11/00
Domestic Patent References:
WO2018019806A12018-02-01
Foreign References:
CN207096604U2018-03-13
CN107861263A2018-03-30
CN205539780U2016-08-31
US20150049303A12015-02-19
Attorney, Agent or Firm:
CHINA PATENT AGENT (H.K.) LTD. (CN)
Download PDF:
Claims:
Claims

1. A photochromic lens comprising a laminated film, said laminated film comprising at least

an adhesive layer (a),

a barrier layer (b),

a photochromic layer (c),

a barrier layer (d), and

an adhesive layer (e),

wherein said layers (a) to (e) are arranged in succession and wherein said laminated film is substantially incorporated within an optical lens body.

2. The photochromic lens according to claim 1 ,

wherein in said laminated film at least one additional layer is arranged at least between layer (a) and (b); layer (b) and (c); layer (c) and (d); and/or layer (d) and (e).

3. The photochromic lens according to claim 1 ,

wherein in said laminated film layers (a) to (e) are arranged in succession and directly on each other.

4. The photochromic lens according to claim 1 ,

wherein said adhesive layer(s) comprises or consists of compound(s) selected from the group consisting of epoxy monomer, acrylate monomer, methacrylate monomer, methacrylate, acrylate oligomer, methacrylate oligomer, polyurethane, polyepoxy, polyacrylate, polymethacrylate, polyvinyl alcohol (PVA), polyvinyl formal (PVF), polyvinyl acetate (PVAc), saponified (ethylene, vinyl acetate) copolymer, silicone, natural and/or synthetic rubber, styrene block copolymers, and mixtures thereof.

5. The photochromic lens according to claim 1 ,

wherein said the barrier layer(s) comprise or consists of compounds selected from the group consisting of cellulose based polymers; polycarbonate (PC) based polymer; polyester based polymers; acrylate based polymers;

methacrylate polymers; thermoplastic urethane polymers (TPU);

polythiourethane based polymers; vinyl based polymers; styrene based polymers; olefin based polymers; amide based polymers; imide based polymers; polyether imide based polymers; polysulfone based polymers; polyether sulfone based polymers; polyether ether ketone based polymers; polyphenylene sulfide based polymers; polyoxymethylene based polymers; and epoxy based, polymers, or any blend thereof.

6. The photochromic lens according to claim 1 ,

wherein said barrier layer (d) provides additional optical functions.

7. The photochromic lens according to claim 6,

wherein said optical functions are selected from the group consisting of UV protection, light polarization, base coloration, and mixtures thereof.

8. The photochromic lens according to claim 1 ,

wherein said photochromic layer comprises at least one photochromic dye.

9. The photochromic lens according to claim 8,

wherein said at least one photochromic dye is selected from the group

consisting of naphthopyrans, spironaphthopyrans, oxazines,

spironaphthoxazines, benzopyrans, spirobenzoxzines, spirobenzopyrans, spiropyrans, chromenes, fulgides, fulgimides, spirooxazines, organo-metal dithiozonates, triarylmethanes, stilbenes, azastilbenes, nitrones, quinones, and mixtures thereof.

10. The photochromic lens according to claim 1 ,

wherein said photochromic layer comprises cellulose ester.

11. The photochromic lens according to claim 1 ,

wherein said optical lens body comprises or consists of organic glass. 12. The photochromic lens according to claim 10,

wherein said organic glass comprises or consists of a polymeric material selected from the group consisting of polythiourethane, polyepisulphide, polymethyl methacrylate, polycarbonate, polyallyldiglycolcarbonate, polyacrylate, polyurethane, polyurea, polyamide, polysulphone, polyallyl, fumaric acid polymer, polystyrene, polymethyl acrylate, biopolymers, and mixtures and combinations thereof. 13. A spectacle frame comprising a photochromic lens according to any one of claims 1 to 12.

14. A method for producing a photochromic lens according to any one of claims 1 to 12,

comprising the steps of:

arranging layers (a) to (e) in succession in order to provide a laminated film, applying an optical lens material to that said laminated film to provide said optical lens material substantially incorporating said laminated film. 15. The method according to claim 14,

further comprising the steps of

arranging said laminated film in a casting mold for casting an optical lens, providing said casting mold with a liquid or molten optical lens material and substantially encapsulating said laminated film within said liquid or molten optical lens material, and

solidifying said liquid or molten optical lens material.

Description:
Photochromic lens with laminated film, method for producing a photochromic lens, and a spectacle frame

The present invention relates to a photochromic lens, and to a method for producing said photochromic lens, as well as to a spectacle frame comprising said photochromic lens.

Photochromic lenses are optical lenses that darken or color depending on the intensity and/or brightness of the incident light, such as sunlight and/or UV light. In the absence of sunlight and/or UV light, the photochromic lenses return to its clear state. That is to say, the darkness or coloration induced in the

photochromic lenses fade if the exposure to sunlight and/or UV light is reduced or absent. The color changing function of these photochromic lenses is due to the presence of photochromic dyes in the optical lens. The darkening or coloration of the photochromic lenses takes place quickly, for example, within about a minute after exposure to bright sunlight. The recovery of the

photochromic lenses to a clear state takes somewhat longer when the exposure to bright sunlight or UV light is reduced or absent.

This reversible color change is also designated as photochromism.

Photochromism is the reversible transformation of a photochromic dye between two isomeric forms by the absorption of electromagnetic radiation, which is also designated as photoisomerisation. The two photoisomeric forms have different absorption spectra, leading to the reversible change of color upon exposure to light.

Thus, photochromic lenses are especially useful in spectacles for outdoor use or combined indoor and outdoor use or for spectacle wearers whose eyes have an increased sensitivity to sunlight.

Photochromic lenses can be produced by incorporation of at least one photochromic dye in a polymerizable composition comprising radically

polymerizable monomers, wherein said polymerizable composition is

subsequently injected into a lens mold and cured to produce the photochromic lens. This production method is simple.

A photochromic dye can be sensitive to the radically polymerizable monomer(s), i.e. can be damaged by the radically polymerizable monomer(s) by unwanted chemical side reactions. In view of that photochromic dye(s) compatible with the radically polymerizable monomer(s) to be used for producing the photochromic lens have to be carefully selected or developed in order to provide

photochromic lenses with a good photochromic performance and durability. Especially, when using a mixture of photochromic dyes, all of these dyes must necessarily be compatible with the radically polymerizable monomer(s) to be used.

Another disadvantage of this approach is that a photochromic dye or mixture of photochromic dyes developed for specific radically polymerizable monomer(s) may not be used for other species of radically polymerizable monomer(s).

Therefore, the design of a specific photochromic or photochromatic color and the use of specific polymeric materials in the optical lens body can be an unsolvable problem.

A further disadvantage of this approach is the nonuniform coloration or clarity, respectively, of the photochromic lens from the lens edge to the center, e.g. the geometrical centre, which is according to DIN EN ISO 13666:2013-10, section 5.5, defined as the intersection of the horizontal and vertical centrelines of the rectangular box, which circumscribes the shape of the lens blank or uncut lens, due to the thickness difference. The thickness difference in the photochromic lens leads to a different amount of photochromic dye(s), depending on the specific position within the photochromic lens. This gradient of photochromic dye(s) is unwanted by the spectacle wearer.

Another method of producing photochromic lenses is to coat the surface, preferably the front surface, i.e. according to DIN EN ISO 13666:2013-10, section 5.8, that surface of the spectacle lens intended to be fitted away from the eye, of the spectacle lens with a curable layer that contains photochromic dye(s). A disadvantage of this approach is that the photochromic layer can delaminate from the surface from the spectacle lens or that the photochromic layer is damaged due to mechanical impacts, such as scratches.

US 2008/0187749 A1 is directed to an optical element comprising at least a support polymeric film layer and a second polymeric film layer which exhibits photochromic and/or linearly polarizing light influencing properties/property. This polymeric film layer can be mounted on the surface of an optical lens.

US 2011/0116151 A1 discloses a photochromic multilayer structure, wherein a photochromic host matrix is formed between two supports, at least one of which is a plastic support. This photochromic multilayer structure is mounted on the surface on an optical lens.

US 2015/0098057 A1 is directed to a photochromic polyurethane laminate which can be applied to polymeric surfaces or can be used by itself as a photochromic element. The photochromic polyurethane laminate can also be incorporated into plastic lenses by means of injection molding. The

photochromic polyurethane laminate is produced by preparing a casting solution, containing thermoplastic polyurethane, at least one isocyanate polyurethane prepolymer, and at least one photochromic compound, in a solvent. This casting solution is cast to produce a cast film which is transferred after evaporation of the solvent between two transparent resin sheets. Finally, the photochromic polyurethane film is cured forming the polyurethane laminate.

Disadvantageously, the photochromic compounds are exposed to the

isocyanate polyurethane prepolymers leading to a damaging of the

photochromic compounds by chemical side reactions. In view of that only photochromic compounds can be used having a certain compatibility or resistance against the reactive polyurethane prepolymers. EP 1 560 060 A1 discloses a polarizing and/or photochromic plastic lens which comprises a laminate with a photochromic layer formed of a polyurethane- based resin. Disadvantageously, the photochromic compounds are exposed to the isocyanate polyurethane prepolymers leading to a damaging of the photochromic compounds. In view of that only photochromic compounds can be used having a certain compatibility or resistance against the reactive isocyanate polyurethane prepolymers. Consequently, there is a need of photochromic lenses, wherein photochromic dye(s) can be generally used irrespective of consideration of the monomeric or prepolymeric starting compounds used to produce the photochromic lens or the layer containing the photochromic dye(s). It is therefore an object of the invention, to provide a respective photochromic lens, wherein photochromic dye(s) can be used independently from the specific composition of the monomeric or (pre)polymeric compounds used to

manufacture the optical lens body. It is furthermore an object, to provide a respective method for producing said photochromic lens as well as to provide a spectacle frame comprising said photochromic lens.

The object of the invention is solved by providing a photochromic lens comprising a laminated film and an optical lens body, said laminated film comprising at least an adhesive layer (a),

a barrier layer (b),

a photochromic layer (c), a barrier layer (d), and

an adhesive layer (e), wherein said layers (a) to (e) are arranged in succession or in a layer sequence (a) to (e) and wherein said laminated film is substantially incorporated, preferably completely, within the optical lens body.

Preferred embodiments are specified in claims 2 to 12. The object of the invention is also solved by providing a spectacle frame comprising a photochromic lens according to any one of claims 1 to 12.

The object of the invention is also solved by providing a method for producing a photochromic lens according to any one of claims 1 to 12, comprising the steps of:

arranging layers (a) to (e) in succession or in a layer sequence (a) to (e) in order to provide a laminated film,

applying an optical lens material to that said laminated film to provide said optical lens material substantially incorporating said laminated film. The laminated film is at least a five-layered laminated film, preferably a five-layered laminated film.

Preferred embodiments of the method are specified in claims 14 and 15. According to the invention the terms“photochromic” and“photochromatic” have the same meaning and can be used interchangeably. According to DIN EN ISO 13666:2013-10, section 6.4, a photochromic material or a photochromatic material (deprecated) is a material which reversibly changes its luminous transmittance characteristics depending upon the intensity and wavelength of the radiation falling upon it.

According to the invention, the term“optical lens” preferably relates to an ophthalmic lens, i.e. according to DIN EN ISO 13666:2013-10, section 8.1.1 , a lens intended to be used for purposes of measurement, correction and/or protection of the eye, or for changing its appearance or to an optical lens to be mounted in a spectacle frame, i.e. a spectacle lens which is according to DIN EN ISO 13666:2013-10, section 8.1.2, defined as an ophthalmic lens worn in front of, but not in contact with, the eyeball, or a spectacle glass. According to another embodiment of the invention, the term“optical lens” does not relate to a lens of a photographic camera or a telescope or a microscope or binoculars. According to another embodiment of the invention the term“optical lens” does not relate to an intraocular lens or a contact lens.

According to the invention the optical lens is most preferably a photochromic lens which is defined in accordance with DIN EN ISO 13666:2013-10, section 8.1.11 , as a lens which reversibly changes its luminous transmittance characteristics depending upon the intensity and wavelength of the radiation falling upon it.

According to the invention the optical lens, preferably the photochromic lens, is further preferably a finished lens, i.e. according to DIN EN ISO 13666:2013-10, section 8.4.6, a lens of which both sides have their final optical surface. The optical lens may be either an uncut lens or an uncut finished spectacle lens, respectively, i.e. according to DIN EN ISO 13666:2013-10, section 8.4.7, a lens of which both sides are optically finished prior to edging or an edged lens, i.e. according to DIN EN ISO 13666:2013-10, section 8.4.8, a finished lens edged to the final size and shape.

According to the invention the optical lens, preferably the photochromic lens, is further preferably a single-vision lens, i.e. according to DIN EN ISO

13666:20013-10, section 8.3.1 , a lens designed to provide a single dioptric power, a multifocal lens, i.e. according to DIN EN ISO 13666:2013-10, section 8.3.2, a lens designed to provide two or more visibly divided portions of different focal powers, a bifocal lens, i.e. according to DIN EN ISO 13666:2013-10, section 8.3.3, a multifocal lens having two portions, usually for distance and near vision, a trifocal lens, i.e. according to DIN EN ISO 13666:2013-10, section 8.3.4, a multifocal lens having three portions, usually for distance, intermediate and near vision, a progressive-power lens, i.e. according to DIN EN ISO

13666:2013-10, section 8.3.5, a lens with at least one progressive surface, that provides increasing (positive) addition power as the wearer looks down or a degressive-power lens, i.e. according to DIN EN ISO 13666:2013-10, section 8.3.6, a lens with at least one progressive surface, that provides decreasing power (i.e. a negative change of power) as the wearer looks up.

According to the invention the optical lens, preferably the photochromic lens, may also be a lens blank, i.e. according to DIN EN ISO 13666:2013-10, section 8.4.1 , a piece of material, usually preformed, for the making of a lens at any stage before completion of the surfacing processes, a semi-finished lens blank, i.e. according to DIN EN ISO 13666:2013-10, section 8.4.2, a lens blank having only one optically finished surface, a single-vision semi-finished lens blank, i.e. according to DIN EN ISO 13666:2013-10, section 8.4.3, a semi-finished lens blank which, after surfacing, is designed to provide a lens with a single dioptric power, a multifocal semi-finished lens blank, i.e. according to DIN EN ISO 13666:2013-10, section 8.4.4, a semi-finished lens blank which, after surfacing, is designed to provide a lens with two or more visibly divided portions of different dioptric powers, a progressive-power semi-finished lens blank, progressive-addition semi-finished lens blank or varifocal semi-finished lens blank, respectively, i.e. according to DIN EN ISO 13666:2013-10, section 8.4.5, a semi-finished lens blank which, after surfacing, is designed to provide a continuous change of dioptric power over a part or all of the lens. The lens blanks mentioned before may have a circular circumferential shape having preferably a diameter between 40 mm and 100 mm.

According to the invention the optical lens, preferably the photochromic lens, may be a corrective lens, i.e. according to DIN EN ISO 13666:2013-10, section 8.1.3, a spectacle lens with dioptric power or an afocal lens or piano lens respectively, i.e. according to DIN EN ISO 13666:2013-10, section 8.2.3, a lens with nominally zero dioptric power.

According to the invention the term“optical lens body” means the polymerized optical lens material used to manufacture the optical lens, preferably the photochromic lens. The material of the optical lens body incorporates the laminated film comprising at least or consisting of layers (a) to (e). Phrased differently, the term“optical lens body” means the optical lens without the incorporated laminated film. The lens body as well as the optical lens, preferably photochromic lens, of the invention can be designed to be, for example, of a single vision type, bifocal type, trifocal type, progressive type, multifocal type, adjustable focus type, or piano type. According to the invention the term“optical lens material” means a material usable to manufacture a spectacle lens and to be usable as optical lens body of the inventive photochromic lens incorporating the laminated film.

According to the invention the term“laminated film” means a multilayered film comprising at least one photochromic layer. In particular the laminated film is a five layered film comprising the layer sequence adhesive layer (a)/ barrier layer (b )/ photochromic layer (c )/ barrier layer (d )/ adhesive layer (e).

According to the invention the term“barrier layer” means that this layer represents a barrier against reactive compounds, such as polymerizable monomer(s) or reactive species in order to protect the photochromic dye(s) in the photochromic layer. That is to say, the barrier layer prevents a diffusion of reactive compounds, such as polymerizable monomer(s) and/or of other reactive species, such as, starter compounds, e.g., photoinitiators, etc., into the photochromic layer. The barrier layer may also be described as“protective layer”. Thus, the barrier layer(s) protect(s) the photochromic layer, in particular the photochromic dye(s), against the material(s) used to produce, in particular to cast, the optical lens body. These materials are by nature very reactive and, thus, aggressive against the photochromic dye(s). Moreover, the barrier layer(s) also protect the photochromic layer, in particular the photochromic dye(s), against the adhesive(s) used in the adhesive layer(s). The adhesive(s) can also be reactive with the photochromic layer, in particular the photochromic dye(s).

In the laminated film, the at least one barrier layer may be arranged directly adjacent to the at least one photochromic layer. Alternatively, at least one further layer may be arranged between the at least one barrier layer and the at least one photochromic layer. Preferably, in the laminated film, the at least one photochromic layer is sandwiched between two barrier layers. These two barrier layers may be identical or different with respect to their chemical composition and/or their layer thickness. Preferably, these two barrier layers are identical with respect to their chemical composition and/or their layer thickness. Further preferably, in the laminated film, the at least one barrier layer is arranged directly adjacent to the at least one photochromic layer.

According to the invention the“photochromic layer” is a layer containing at least one photochromic dye. In an embodiment of the invention the photochromic layer may contain only one photochromic dye. According to another

embodiment of the invention the photochromic layer may contain a mixture of two or three different photochromic dyes. Of course, the photochromic layer may also contain more than three photochromic dyes, such as, for example, four to six photochromic dyes. Preferably, the laminated film comprises at least one photochromic layer. In case, the laminated film comprises at least two photochromic layers, those two photochromic layers may be identical or different with respect to the at least one photochromic dye, their chemical composition and/or their layer thickness. In the laminated film, those two photochromic layers are preferably separated by at least one barrier layer and arranged between two further barrier layers, the barrier layers being identical, preferably identical, or different with respect to their chemical composition and/or their layer thickness.

According to a preferred embodiment the photochromic dye(s) are not chemically reacted with other chemical species in the photochromic layer.

Preferably, the photochromic layer is comprised of a substrate layer containing the photochromic dye(s), wherein preferably said photochromic dye(s) are not chemically reacted with and/or not chemically bonded to the substrate layer. According to another preferred embodiment of the invention the photochromic dye(s) are preferably physically retained, preferably only physically retained, in and/or on the substrate layer. Thus, the photochromic dye(s) are preferably not chemically reacted within the substrate layer of the photochromic layer and preferably also not reacted at the interfaces between photochromic layer and barrier layer(s) or another directly adjacent layer to the photochromic layer.

The photochromic layer can be produced by a cast process, using, for example, a rotary drum or strip casting equipment. In a first step, preferably the

compounds making up the substrate layer of the photochromic layer are solved or solubilized in a solvent, preferably an organic solvent, which can optionally also contain water. Simultaneously or preferably subsequently the photochromic dye(s) is/are added to the solved substrate compounds. The photochromic dye(s) can be added in a solubilized state. The thus obtained solution can then be cast in a second step into a film, using, for example, a film casting device, which can be, for example, a rotary drum or strip casting device.

The at least one photochromic layer has preferably a layer thickness within a range of 80 pm to 320 pm, preferably of 120 pm to 280 pm, preferably from 160 pm to 240 pm. In case, the laminated film comprises at least two

photochromic layers, the before mentioned values apply accordingly for each photochromic layer.

According to the invention, in the laminated film, the barrier layers (b) and (d) are arranged over both surfaces of the photochromic layer (c) or are directly applied on both surfaces of the photochromic layer (c). According to a preferred embodiment of the invention, a barrier layer is directly applied on each of the two sides of the photochromic layer. The two sides of the photochromic layer are the upper surface and the lower surface of the photochromic layer, which IB are intended to be incorporated into the optical lens body to have the upper surface directed to the front surface and the lower surface directed to the back surface of the photochromic lens or vice versa. The upper surface and the lower surface of the photochromic layer are the two sides of the photochromic layer each with the largest surface, not the sides of the photochromic layer.

Preferably, the barrier layer(s) and the photochromic layer are in direct physical contact. Thus, the photochromic layer is protected against any detrimental impact of reactive or aggressive chemicals, such as reactive monomers, starter compounds, etc., especially when producing, in particular casting, the optical lens, preferably photochromic lens.

The barrier layers (b) and (d) can be applied by laminating the barrier layer(s) onto the photochromic layer (c). For example, the barrier layer can be produced separately by casting and, preferably curing, a barrier film or barrier layer.

The barrier layer, which can also be designated as barrier foil, can be produced by extrusion, blow molding, or calendering.

The, preferably cured or dried, barrier film or barrier layer can then be

subsequently laminated, preferably directly laminated or fused or adhesively bonded, on both sides of the photochromic layer. Preferably, the, preferably cured or dried, barrier layer is directly laminated completely on each of the supper surface and on the lower surface of the photochromic layer. By laminating the, preferably cured or dried, barrier layer to each of the upper surface and lower surface of the photochromic layer, the photochromic dye(s) are not exposed to reactive or aggressive chemical compounds, such as initiators as benzoyl peroxide, di-t-butyl peroxide, diisopropyl peroxy

dicarbonate, methyl ethyl ketone peroxide, acetylacetone peroxide, dibenzoyl peroxide, cumyl hydroperoxide, tert-butyl hydroperoxide, neither within the photochromic layer nor at the interface to the barrier layer(s) and/or any other layer directly adjacent to the photochromic layer.

Each barrier layer has preferably a layer thickness within a range of 10 pm to 200 pm, preferably of 80 pm to 190 pm, further preferred from 120 to 180 pm.

The adhesive layers (a) and (e) are arranged or applied over both surfaces of the barrier layers (b) and (d) or directly arranged or applied to both surfaces of the barrier layer(s) (b) and (d), both surfaces of the barrier layers (b) and (d) being not next of not adjacent to the photochromic layer. The adhesive layer(s) (a) and (e) serve to provide a stable bonding to the lens material in the optical lens body.

The adhesive layer(s) (a) and (e) can be applied by laminating or coating, for example by spin coating, the adhesive layer(s) onto the surface of the barrier layer(s) which is/are intended to be incorporated in direct contact to the optical lens body.

For example, the adhesive layer(s) (a) and (e) can be a tape casted on the barrier layer(s), and then dried. Alternatively, the adhesive layer(s) can be produced separately by casting or extruding, preferably curing, and then laminating to the surface of the barrier layer(s), each surface of the barrier layer(s) not being next or adjacent to the photochromic layer.

The coating can be carried out, for example, by spraying or coating, for example by spin coating technology, a solution containing the compounds of the adhesive layer on both surfaces of the barrier layers which are in the layer sequence (a) to (e) of the laminated film not adjacent to the photochromic layer (c). Optionally, the solvent, preferably an organic solvent, can be vaporized to provide the adhesive layer.

Each adhesive layer has preferably a layer thickness within a range of 2 pm to 120 pm. The adhesive layer can be a pressure sensitive layer.

The inventors have found a unique solution, so that advantageously the photochromic dye(s) are not exposed to a chemically aggressive surrounding when providing and producing a photochromic lens. This approach allows to use any photochromic dye or any mixture of photochromic dyes independently of the fact, whether or not the used photochromic dye(s) are compatible with or sensitive to reactive or aggressive chemicals, such as, e.g., polymerizable monomer(s), polymerizable prepolymers and/or starter compounds, such as peroxides and photoinitiators, etc., used for producing the polymeric lens material of the optical lens body. That is to say, the present invention even allows to use very sensitive photochromic dye(s) which would be damaged or destroyed by polymerizable monomer(s) during the manufacture of an optical lens, such as, a lens casting polymerization, for example in an injection molding process. The laminated film comprising or consisting of layers (a) to (e), can be arranged in an optical lens mold, into which the optical lens material can be filled, for example, injected or pumped, so that the laminated film, containing or consisting of layers (a) to (e), is substantially incorporated, preferably

completely incorporated, within the optical lens body.

According to a preferred embodiment of the invention, the laminated film, containing or consisting of the five layers (a) to (e), has a symmetrical structure. Thus, preferably the barrier layers (b) and (d) each have an identical chemical composition and preferably also an identical layer thickness, within the usual fabrication tolerances.

Moreover, preferably the adhesive layers (a) and (e) each have an identical chemical composition and preferably also an identical layer thickness, within the usual fabrication tolerances.

According to another preferred embodiment of the invention at least one additional layer is arranged at least between layer (a) and (b); layer (b) and (c); layer (c) and (d); and/or layer (d) and (e).

For example, according to an embodiment of the invention, one or more additional optical layers may be arranged between layer (a) and (b); layer (b) and (c); layer (c) and (d); and/or layer (d) and (e). For example, the at least one additional optical layer may be selected from the group consisting of a polarization layer, UV protection layer, coloration layer, mechanical stabilization layer, and combinations thereof.

According to another embodiment of the invention a UV protection layer is arranged between layer (b) and (c) and a UV protection layer is arranged between layer (c) and (d). These two UV protection layers may be identical or different with respect to their chemical composition and/or their layer thickness. According to another preferred embodiment of the invention a UV protection layer is arranged between layer (b) and (c).

According to another preferred embodiment of the invention layers (a) to (e) are arranged in succession and directly on each other, preferably in physical contact to each other. In this preferred embodiment of the invention the laminated film consists of adhesive layer (a), barrier layer (b), photochromic layer (c), barrier layer (d), and adhesive layer (e). Thus, preferably

photochromic layer (c) is directly arranged between the two barrier layers (b) and (d), respectively, so that barrier layer (b) and barrier layer (d) are in physical contact with photochromic layer (c). Each of the two barrier layers (b) and (d) is preferably directly provided with the adhesive layer (a) and (e), respectively, on the side of each barrier layer (b) and (d), respectively, opposite to photochromic layer (c). Thus, adhesive layer (a) is in physical contact with barrier layer (b); and adhesive layer (e) is in physical contact with layer barrier (d). Consequently, in a preferred embodiment of the invention, layers (a) to (e) are arranged in succession or in a layer sequence, wherein the layers are in physical contact with each other in the indicated order.

According to another preferred embodiment of the invention, the adhesive layer(s) comprises or consists of compound(s) selected from the group consisting of epoxy monomer, acrylate monomer, acrylate oligomer,

polyurethane, polyepoxy, polyacrylate, polymethacrylate, polyvinyl alcohol (PVA), polyvinyl formal (PVF), polyvinyl acetate (PVAc), saponified (ethylene, vinyl acetate) copolymer, silicone, natural and/or synthetic rubber, styrene block copolymers, and mixtures thereof, and optionally one or more solvent(s), preferably organic solvent(s).

According a preferred embodiment of the invention, the adhesive layer(s) comprises or consists of compound(s) selected from the group consisting of acrylate monomer, acrylate oligomer, and mixtures thereof, and optionally one or more solvent(s), preferably organic solvent(s). The solvent(s) is/are preferably organic solvent(s), more preferably volatile organic solvent(s).

Particular useful organic solvents are ethanol, ethyl acetate, and mixtures thereof.

According to a preferred embodiment of the invention the adhesive layer(s) comprises or consists of acrylate monomer, acrylate oligomer, or mixtures thereof and further comprises or consists of organic solvent(s) of ethanol, ethyl acetate, or mixtures thereof.

According to a preferred embodiment of the invention, the barrier layer comprises or consists of a polymeric film.

According to a preferred embodiment of the invention, the barrier layer(s) comprise(s) or consist(s) of compounds selected from the group consisting of cellulose based polymers, such as diacetylcellulose and triacetyl cellulose (TAC), cellulose acetate butyrate (CAB); polycarbonate (PC) based polymer; polyester based polymers, such as polyethyleneterephthalate (PET), polyethyleneterephthalate glycol (PETG), polyethylene naphthenate, and dimethyl terephthalate (DMT); acrylate based polymers, such as

polymethacrylate (PMA), polyethylacrylate; methacrylate polymers, such as polymethyl methacrylate (PMMA), polyethyl methylacrylate; thermoplastic urethane polymers (TPU); polythiourethane based polymers; vinyl based polymers, such as polyvinyl chloride, polyvinyl alcohol, polyvinylidene chloride, polyvinyl butyral; styrene based polymers, such as polystyrene, styrene methylmethacrylate copolymers (SMMA), styrene maleic anhydride polymers (SMA), acrylonitrile-styrene (ANS) copolymers, acrylonitrile butadiene styrene (ABS) terpolymers, (meth)acrylate butadiene styrene (MBS) terpolymers; olefin based polymers, such as polyethylene, polypropylene, polymethylpentene (PMP), cyclic (COC) or norbornene structure-containing polyolefins, and ethylene-propylene copolymers; amide based polymers, such as nylon and aromatic polyamide; imide based polymers; polyether imide based polymers; polysulfone based polymers; polyether sulfone based polymers; polyether ether ketone based polymers; polyphenylene sulfide based polymers;

polyoxymethylene based polymers; and epoxy based polymers, and any blend or mixture thereof.

According to a preferred embodiment, the barrier layer(s) comprise(s) or consist(s) of compounds selected from the group consisting of cellulose triacetate (TAC), polycarbonate (PC), cellulose acetate butyrate (CAB), poly(methyl methacrylate) PMMA, poly(ethylene terephthalate) (PET), and mixtures thereof.

TAC, PET and PC are preferred, with TAC most preferred as barrier layer.

According to another preferred embodiment of the invention, the barrier layer(s) can provide additional optical functions. These optical functions are preferably selected from the group consisting of UV protection, light polarization, preferably linear light polarization, base coloration, and combinations thereof.

Preferably, the barrier layer(s) has/have a UV protection function.

According to another preferred embodiment of the invention, the barrier layer contains permanent dye(s) as described further below.

According to an embodiment of the invention, the photochromic layer comprises at least one photochromic dye. The photochromic layer may comprise a mixture of two or three photochromic dyes. The photochromic dye(s) can be combined so that, for example, by color mixing, any desired photochromic color can be produced. It is, however, also within the scope of this invention to incorporate more than three photochromic dye(s) in the photochromic layer, for example, four to six photochromic dye(s).

Preferably, the at least one photochromic dye is selected from the group consisting of naphthopyrans, spironaphthopyrans, oxazines,

spironaphthoxazines, benzopyrans, spirobenzoxzines, spirobenzopyrans, spiropyrans, chromenes, fulgides, fulgimides, spirooxazines, organo-metal dithiozonates, triarylmethanes, stilbenes, azastilbenes, nitrones, quinones, and mixtures thereof.

According to another preferred embodiment of the invention, the at least one photochromic dye is preferably selected from the group consisting of naphthopyrans, spironaphthopyrans, oxazines, spironaphthoxazines, benzopyrans, spirobenzoxazines, spirobenzopyrans, spiropyrans, chromenes, fulgides, fulgimides, spirooxazines, organo-metal dithiozonates, and mixtures thereof.

According to another preferred embodiment of the invention, the at least one photochromic dye is preferably selected from the group consisting of benzopyrans, naphthopyrans, spirobenzopyrans, spironaphthopyrans, spirobenzoxazines, spironaphthoxazines, fulgides, fulgimides, and mixtures thereof.

Preferably, naphthopyrans and/or spironaphthopyrans are used as

photochromic dyes. According to another embodiment of the invention the photochromic dye(s) are selected from the group consisting of:

1 ,3-dihydrospiro[2H-anthra[2,3-d]imidazole-2, 1 '-cyclohexane]-5, 10-dione;

1.3-dihydrospiro[2H-anthra[2,3-d]imidazole-2, 1 '-cyclohexane]-6, 11 -dione;

1.3-dihydro-4-(phenylthio)spiro[2H-anthra-1 ',2-diimidazole-2,1 '-cyclohexane]- 6,11 -dione;

1.3-dihydrospiro[2-H-anthra[1 ,2-d]im idazole-2, 1’-cycloheptane]-6, 11 -dione-

1.3.3-trimethylspiroindole-2,3'[3H]naphtho[2,1 -b]-1 ,4-oxazine]2-methyl-3,3'- spiro-bi-[3H-naphtho[2, 1 -bipyran](2-Me);

2-phenyl-3-methyl-7-methoxy-8'-nitrospiro[4H]-1 -benzopyran-4,3'-[3H]- naphtho[2, 1 -bipyran];

spiro[2H-1 -benzopyran-2,9'-xanthene];

8-methoxy-1 ',3'-dimethylspiro(2H-1 -benzopyran-2,2'-(1 'H)-quinoline;

2,2'-spiro-bi-[2H-1 -benzopyran];

5'-amino-1 ',3',3'-trimethylspiro[2H-1 -benzopyran-2,2'-indoline;

ethyl-beta-methyl-beta-(3',3'-dimethyl-6-nitrospiro(2H-1 -benzopyran-2,2'-indolin-

1'-yl))-propenoate;

(1 ,3-propanediyl)bis[3',3'-dimethyl-6-nitrospiro[2H-1 -benzopyran-2,2'-indoline]]; 3,3'-dimethyl-6-nitrospiro[2H-1-benzopyrao-2,2'-benzoxazolin e];

6'-methylthio-3,3'-dimethyl-8-methoxy-6-nitrospiro[2H-1 -benzopyran-2,2'- benzothiozoline];

(1 ,2-ethanediyl)bis[8-methoxy-3-methyl-6-nitrospiro[2H-1-benzo pyran-2,2'- benzothiozoline]];

N-N'-bis(3,3'-dimethyl-6-nitrospiro[2H-1 -benzopyran-2,2'(3'H)-benzothioazol-6'- yl)decanediamide];

alpha.-(2,5-dimethyl-3-furyl)ethylidene(Z)-ethylidenesucc inicanhydride;

alpha-(2,5-dimethyl-3-furyl)-alpha'-delta-dimethylfulgide ; 2,5-diphenyl-4-(2'-chlorophenyl)imidazole;

(2',4'-dinitrophenyl)methyl-1 H-benzimidazole;

N-N-diethyl-2-phenyl-2H-phenanthro[9,10-d]imidazol-2-amin e;

2-nitro-3-aminofluoren-2-amino-4-(2'-furanyl)-6H-1 ,3-thiazine-6-thione, and mixtures thereof.

According to another embodiment of the invention, the photochromic dye(s) can be selected from the group consisting of: Reversacol Midnight Gray, Reversacol Pacific Blue, Reversacol Sunflower, Reversacol Corn Yellow (James Robinson, Ltd., Huddersfield, England), and mixtures thereof.

Preferably, the photochromic dye(s) is/are present in an amount of 0.001 to 0.5 wt.-%, preferably of 0.01 to 0.1 wt.-%, based on the total weight of the

photochromic layer. In case, the laminated film comprises at least two

photochromic layers, the before mentioned values for the photochromic dye(s) apply to each the photochromic dye(s) in each photochromic layer.

According to a preferred embodiment of the invention, the photochromic layer comprises cellulose ester. The cellulose ester preferably forms the substrate layer of the photochromic layer. The photochromic dye(s) is/are incorporated into the cellulose substrate layer. The photochromic dye(s) are non-covalently retained in the cellulose substrate layer.

Preferably, the cellulose ester is selected from the group consisting of cellulose acetate, cellulose acetate butyrate, cellulose acetate propionate, and mixtures thereof. Preferably, the cellulose acetate is selected from the group consisting of cellulose diacetate, cellulose triacetate, and mixtures thereof.

According to another preferred embodiment of the invention, the cellulose ester is cellulose triacetate.

Cellulose ester, in particular cellulose acetate, further in particular, cellulose triacetate, can be readily solubilized in an organic solvent. After having

solubilized the cellulose ester, preferably cellulose triacetate, at least one photochromic dye is added to the solution. If desired, further additive(s) may be added. The obtained solution can then be cast and dried to produce the photochromic layer or film.

A process to produce highly transparent films or layers on the basis of cellulose ester(s) containing photochromic dye(s) is disclosed in WO 2016/134688 A1 , the disclosure of which is incorporated herewith by reference. The photochromic dye(s) is/are retained in the produced layer, preferably only, by physical interaction, for example, by caging or trapping the photochromic dye(s) in the structure of the cellulose ester layer or film.

According to another embodiment of the invention the substrate layer,

preferably cellulose ester, in particular cellulose acetate, further in particular, cellulose triacetate, used for the manufacture of the photochromic layer, can be provided with photochromic dye(s) by dipping the substrate layer into a solution containing the photochromic dye(s). Thus, the substrate layer, preferably cellulose ester, in particular cellulose acetate, further in particular, cellulose triacetate, can imbibe the photochromic dye(s). The concentration of the photochromic dye(s) in the substrate layer can be controlled by the dipping time. According to a preferred embodiment, the optical lens body comprises or consists of organic glass. The organic glass can also be specified as plastic glass. According to a preferred embodiment the optical lens or optical lens body is not made of or based on inorganic glass or mineral glass.

Preferably, said organic glass comprises or consists of a polymeric material selected from the group consisting of polythiourethane, polyepisulphide, polymethyl methacrylate, polycarbonate, polyallyldiglycolcarbonate, polyacrylate, polyurethane, polyurea, polyamide, polysulphone, polyallyl, fumaric acid polymer, polystyrene, polymethyl acrylate, biopolymers, and mixtures and combinations thereof. An organic lens or optical lens body is preferably made of one of the polymeric materials mentioned above or a mixture or combination thereof.

In another preferred embodiment of the invention, the organic lens substrate comprises or consists of a polymeric material selected from the group

consisting of polythiourethane, polyepisulfide, polymethyl methacrylate, polycarbonate, polyallyldiglycolcarbonate, polyacrylate, polyurethane, polyurea, polyamide, polysulfone, polyallyl, fumaric acid polymer, polystyrene, polymethyl acrylate, biopolymers, and mixtures and combinations thereof.

In another preferred embodiment of the invention, the organic glass or optical lens body comprises or consists of a polymeric material selected from the group consisting of polyurethane, polyurea, polythiourethane, polyepisulfide,

polycarbonate, polyallyldiglycolcarbonate, and mixtures and combinations thereof, which are preferably used with a laminated film comprising or

consisting of layers (a) to (e), wherein layer (c) comprises as substrate preferably cellulose ester, in particular cellulose acetate, most preferably, cellulose triacetate.

Polyallyldiglycolcarbonate has proven to be a very suitable polymeric material as organic glass substrate. Polyallyldiglycolcarbonate is preferably used with a laminated film comprising or consisting of layers (a) to (e), wherein layer (c) comprises as substrate preferably cellulose ester, in particular cellulose acetate, most preferably, cellulose triacetate.

The polymeric materials available under the trade names MR6, MR7, MR8, MR10, MR20, MR174, CR39, CR330, CR607, CR630, RAV700, RAV7NG, RAV7AT, RAV710, RAV713, RAV720, Trivex, Panlite, MGC 1.76, RAVolution have also proven to be very suitable as organic glass material.

The base material of CR39, CR330, CR607, CR630, RAV700, RAV7NG, RAV7AT, RAV710, RAV713, and RAV720 is polyallyldiglycolcarbonate.

The base material of RAVolution, and Trivex is polyurea/polyurethane.

The base material of MR6, MR7, MR8, and MR10 is polythiourethane.

The base material of MR 174, and MGC 1.76 is polyepisulfide.

These organic glass materials are preferably used with a laminated film comprising or consisting of layers (a) to (e), wherein layer (c) comprises as substrate preferably cellulose ester, in particular cellulose acetate, most preferably, cellulose triacetate.

The polymeric material available under the designations CR39, MR7, MR8 are very preferably used as organic glass materials according to the invention.

These organic glass materials are preferably used with a laminated film comprising or consisting of layers (a) to (e), wherein layer (c) comprises as substrate preferably cellulose ester, in particular cellulose acetate, most preferably, cellulose triacetate. The organic glass or plastic lens material can be clear, UV tinted or gradient UV tinted, solid tinted or permanently colored, or can have a permanent color gradient. This at least one additional color can be provided by at least one permanent dye. The permanent dye(s) can be contained in the optical lens body and/or the barrier layer.

According to a preferred embodiment of the invention, the barrier layer contains permanent dye(s).

The permanent dye(s) can be selected for from the group consisting of C.l. Disperse Yellow 5, C.l. Disperse Yellow 13, C.l. Disperse Yellow 33, C.l.

Disperse Yellow 42, C.l. Disperse Yellow 51 , C.l. Disperse Yellow 54, C.l.

Disperse Yellow 64, C.l. Disperse Yellow 71 , C.l. Disperse Yellow 86, C.l.

Disperse Yellow 114, C.l. Disperse Yellow 201 , C.l. Disperse Yellow 211 , C.l. Disperse Orange 30, C.l. Disperse Orange 73, C.l. Disperse Red 4, C.l.

Disperse Red 11 , 5 C.l. Disperse Red 15, C.l. Disperse Red 54, C.l. Disperse Red 55, C.l. Disperse Red 58, C.l. Disperse Red 60, C.l. Disperse Red 73, C.l. Disperse Red 86, C.l. Disperse Red 91 , C.l. Disperse Red 92, C.l. Disperse Red 127, C.l. Disperse Red 152, C.l. Disperse Red 189, C.l. Disperse Red 229, C.l. Disperse Red 279, C.l. Disperse Red 302, C.l. Disperse Red 302:1 , C.l. Disperse Red 323, C.l. Disperse Blue 27, C.l. Disperse Blue 54, C.l. Disperse Blue 56, C.l. Disperse Blue 73, C.l. Disperse Blue 280, C.l. Disperse Violet 26, C.l. Disperse Violet 33, C.l. Solvent Yellow 179, C.l. Solvent Violet 36, C.l.

Pigment Blue 15, C.l. Pigment Blue 80, C.l. Pigment Green 7, C.l. Pigment Orange 36, C.l. Pigment Orange 36, C.l. Pigment Yellow 13, C.l. Pigment Violet 23, C.l. Pigment Violet 37, C.l. Pigment Black 1 , C.l. Pigment Black 6, C.l.

Pigment Black 7, and mixtures thereof. The photochromic lens of the present invention preferably has a refractive index in the range of 1.4 to 1.8, preferably 1.45 to 1.78, further preferably of 1.48 to 1.76. A particular useful refractive index is 1.5; 1.56; 1.6; 1.67; and 1.74. The refraction index is based on sodium D-line (589 nm). The spectacle frame of the present invention comprises an optical lens, preferably a photochromic lens, according to any one of claims 1 to 12.

The method for producing a photochromic lens according to any one of claims 1 to 12, comprises the steps of arranging layers (a) to (e) in succession or in a layer sequence in order to provide a laminated film, applying an optical lens material to that said laminated film to provide said photochromic lens

substantially incorporating, preferably completely incorporating, said laminated film. The optical lens body can be provided in the form of a semi-finished product. The semi-finished product can be in the form of a separate front part as well as a separate back part of a spectacle lens. The separate front part and the separate back part of the optical lens body can be combined by adhering to the adhesive layers (a) and (e), respectively, of the laminated film comprising or consisting of layers (a) to (e). The combined front part, laminated film, comprising or consisting of layers (a) to (e), and the back part provide the photochromic lens of the present invention. According to a preferred embodiment said method further comprises the steps of arranging said laminated film in a casting mold for casting an optical lens, preferably a spectacle lens, providing said casting mold with a liquid or molten optical lens material and substantially incorporating or encapsulating, preferably incorporating or encapsulating, said laminated film within said liquid or molten optical lens material, and solidifying said liquid or molten optical lens material.

When arranging said laminated film in a casting mold, said step of arranging preferably comprises a bending of said laminated film. Preferably, the step of arranging said laminated film in a casting mold comprises a matching of the shape of said laminated film to the shape of the front surface of a mold, preferably of an optical lens mold, more preferably of an ophthalmic lens mold , more preferably a spectacle lens mold.

The explanations provided above with respect to the photochromic lens apply respectively for the method of the present invention. Thus, the features of the photochromic lens as disclosed above are expressly disclosed in combination with the method of the invention by this reference.

The present invention preferably also provides a method for producing a photochromic lens as described above, said process including the steps of

1. forming a laminated film including;

an adhesive layer (a),

a barrier layer (b),

a photochromic layer (c),

a barrier layer (d), and

an adhesive layer (e),

2. matching the shape of the laminated film to the shape of the front surface of an optical lens, preferably a spectacle lens, by bending in order to provide a bent laminated film in an optical lens mold, preferably a spectacle lens mold;

3. injecting a composition comprising liquid monomer(s) or mixture of

monomers or polymerizable material into the optical lens mold, preferably a spectacle lens mold, around the shaped or bent laminated film;

4. curing or hardening the liquid monomer(s) or mixture of monomers or polymerizable material in order to obtain a photochromic lens wherein the laminated film is substantially, preferably completely, incorporated within the optical lens body.

The monomer(s) or monomeric compound(s) are polymerized, preferably using initiators or starter compounds or UV rays, during the curing or hardening in order to provide the organic glass or polymeric material specified above.

According to a preferred embodiment the shaped or bent laminated film is hold by means, preferably a gasket, within the lens mold, preferably close to the front surface.

According to another preferred embodiment of the invention, the method for producing a photochromic lens according to any one of claims 1 to 12

comprises the steps of:

arranging layers (a) to (e) in succession or in a layer sequence in order to provide a laminated film,

bending the film, preferably in a press machine, preferably with a specific curvature aluminum mold, preferably under a temperature in a range of 80 to 95°C, preferably under a temperature of 90°C; BO arranging the bent laminated film into an optical lens casting assembly, preferably a spectacle lens casting assembly, for the mold, preferably including two glass molds and gaskets;

wherein the bent laminated film is held with the gaskets;

injecting liquid monomeric compound(s), preferably polyallyldiglycolcarbonate liquid monomer, into the lens casting assembly around the bent laminated film; putting the lens casting assembly into an oven under temperature in a range of

40° C to 90°C for an appropriate time, preferably of 6 to 12 hours, preferably 10 hours, to polymerize the monomeric compound(s), preferably the

polyallyldiglycolcarbonate liquid monomer,

opening the assembly and taking out the solid photochromic lens.

Alternatively, an injection molding process can be used.

The liquid or molten material, preferably polymerizable material, is solidified, preferably polymerized, in the casting mold. After having finished the

solidification, preferably polymerization, the obtained cast lens blank is removed from the mold.

Optionally, any necessary finishing steps, in particular prescription grinding, can additionally be carried out for producing the finished photochromic lens.

Advantageously, the method of the present invention allows to process the front surface as well as the back surface of the obtained cast lens blank without damaging the photochromic layer. This is due to the fact that the photochromic layer, as part of the at least five layered laminated film, is arranged within the photochromic lens, i.e. not at a surface of the photochromic lens. Therefore, the surfaces of the obtained photochromic lens can be mechanical treated, for example, ground and/or polished. Moreover, the surface(s) of the thus obtained photochromic lens can be further coated, for example, with an anti-fog layer, an anti-static coating, a hydrophobic layer, an anti-reflective coating, a hard coating and/or a polarization layer.

The invention is further illustrated by the Examples and Figures. The invention, however, is not to be construed to be limited to enclosed examples.

Examples and Figures

Fig.1 shows a schematic view of a laminated film usable within the optical lens body to provide a photochromic lens of the invention.

Fig. 2 shows a schematic view of the laminated film shown in Fig. 1 within an optical lens body.

Figures

Fig. 1 shows a laminated film consisting of five layers 1 to 5. Layers 1 to 5 each have a film-like appearance having two major sides, which can be designated as upper and lower side in the depiction of Fig.1. The upper side of layer 5 is in physical contact with the lower side of layer 4. The upper side of layer 4 is in physical contact with the lower side of layer 3. The upper side of layer 3 is in physical contact with the lower side of layer 2. The upper side of layer 2 is in contact with the lower side of layer 1. The centrally arranged layer 3 is the photochromic layer (c). The layers 2 and 4 enclosing the photochromic layer (c) are the barrier layers (b) and (d), respectively. The barrier layers (b) and (d) are in turn provided each with an adhesive layer (a) and (e), respectively. It is to be noted that the layers 2 and 4 can have an identical chemical composition or can have a different chemical composition. Moreover, the thickness of layers 2 and 4 can be identical or different from each other.

Preferably, layers 2 and 3 have an identical chemical composition and have an identical layer thickness.

It is further to be noted that the layers 1 and 5 can have an identical chemical composition or can have a different chemical composition. Moreover, the thickness of layers 1 and 5 can be identical or different from each other.

Preferably, layers 1 and 5 have an identical chemical composition and have an identical layer thickness.

According to a preferred embodiment of the invention the film laminate comprising or consisting of layers 1 to 5 has a symmetrical structure in particular regarding chemical composition and thickness of layers.

Fig. 2 shows a section of the photochromic lens of the invention, wherein the laminated film of Fig.1 is arranged within an optical lens body of the

photochromic lens. The laminated film consisting of layers 1 to 5 is incorporated within the material 6 of the optical lens body.

Examples

Example 1 according to the invention

1000 g triacetyl cellulose (SICHUAN PUSH ACETATI CO., LTD) were solved in 4000 g dichloromethane at a temperature of 20°C for 24 h. 0.5 g of 3,3- diphenyl-3H-naphtho[2,1 -b]pyran (GANTIAN OPTIC CO., LTD) were added with BB stirring at a temperature of 20°C for 48 hours. The obtained solution was cast into a photochromic layer using a tape casting production line. The organic solvent was vaporized by heating at 110°C for 10 hours so that the obtained photochromic layer had a layer thickness of 180 pm.

The obtained photochromic layer was laminated on each of both major sides with a barrier layer of triacetyl cellulose (Island Polymer Industries GmbH) having each a thickness of 80 pm by lamination using SW-560 Automatic Laminator (GUANGMING PRINTING MACHINERY CO., LTD).

The thus obtained three layer film laminate was coated on both sides with an adhesive layer by spraying/coating using WS-65MZ-23NPPB Spin coater (Laurell Technologies Corporation). The adhesive layer formulation is specified in Table 1 below:

Table 1 :

The thus obtained five layered laminated film was placed in mold for casting spectacle lenses by following steps:

1. the laminated film was bent in a press machine with an specific curvature aluminum mold, under the temperature of 90°C;

2. the bent five layered laminated film was placed into a lens casting

assembly for the mold, which includes two glass molds and gaskets;

3. the bent five layered laminated film was held with the gaskets;

4. polyallyldiglycolcarbonate liquid monomer was injected into the lens

casting assembly around the bent photochromic film;

5. the lens casting assembly was put into an oven under temperature range of 40°C to 90°C for 10 hours; the polyallyldiglycolcarbonate liquid monomer polymerized to solid lens;

6. the assembly was opened and the solid photochromic lens was taken out.

Comparative Example 1

The photochromic lens was produced in accordance with Example 1 , with the exception that no barrier layers were applied to protect the photochromic layer. The adhesive layers was directly applied to the photochromic layer.

The three layered laminated film consisting of an adhesive layer/photochromic layer/adhesive layer structure, was used to produce a photochromic lens as described in Example 1 . Comparative Example 2 The photochromic lens was produced in accordance with Example 1 , with the exception that no adhesive layers were applied to the barrier layers. The three layered laminated film, consisting of a barrier layer/photochromic layer/barrier layer, was used to produce a photochromic lens as described in Example 1.

Results

Table 2

In the Table 2, the transmittance at darkened stage is based on the test method in ISO 8980-3.

The adhesion test was performed by the following steps as set forth below:

1- Putting the lens into a groove machine (Brand: LIANGYOU, Type C); do the grooving on the lens sidewall, where the photochromic

layer/laminated film is located according to the manufacturer’s instructions;

2- Place the lens after grooving into the 3 opening wedges hold in place of an INSTRON 3360 material tester in accordance with the manufacturer’s instructions wherein the wedges hold the position of the slotting area of the lens sidewall; 3- Starting test wherein the INSTRON material tester pulls the lens with 100N load for 5 minutes:

4- If there is a separation between the photochromic layer/laminated film and the optical lens body then the adhesion test is passed otherwise failed.

As can be seen from Table 2, only the photochromic lens containing the five layered film passed the adhesion test and provided a significant reduction of light transmission down to 25 %.

Preferred aspects of the inventions are specified below:

Aspect 1 : An optical lens comprising a laminated film, said laminated film containing

an adhesive layer (a),

a barrier layer (b),

a photochromic layer (c),

a barrier layer (d), and

an adhesive layer (e),

wherein said layers (a) to (e) are arranged in succession or in a layer sequence and wherein said laminated film is substantially incorporated within an optical lens body.

Aspect 2: The optical lens according to aspect 1 ,

wherein in said laminated film at least one additional layer is arranged at least between layer (a) and (b); layer (b) and (c); layer (c) and (d); and layer (d) and (e). Aspect 3: The optical lens according to aspect 1 or 2,

wherein in said laminated film layers (a) to (e) are arranged in succession or in a layer sequence and directly on each other.

Aspect 4: The optical lens according to any one of aspects 1 to 3,

wherein said adhesive layer(s) comprises or consists of compound(s) selected from the group consisting of epoxy monomer, acrylate monomer, methacrylate monomer, acrylate oligomer, methacrylate oligomer, polyurethane, polyepoxy, polyacrylate, polymethacrylate, polyvinyl alcohol (PVA), polyvinyl formal (PVF), polyvinyl acetate (PVAc), saponified (ethylene, vinyl acetate) copolymer, silicone, natural and/or synthetic rubber, styrene block copolymers, and mixtures thereof.

Aspect 5: The optical lens according to any one of aspects 1 to 4,

wherein said the barrier layer(s) comprise or consists of compounds selected from the group consisting of cellulose based polymers, such as diacetylcellulose and triacetyl cellulose (TAC), cellulose acetate butyrate (CAB); polycarbonate (PC) based polymer; polyester based polymers, such as

polyethyleneterephthalate (PET), polyethyleneterephthalate glycol (PETG), polyethylene naphthenate, and dimethyl terephthalate (DMT); acrylate based polymers, such as polymethacrylate (PMA), polyethylacrylate; methacrylate polymers, such as polymethyl methacrylate (PMMA), polyethyl methylacrylate; thermoplastic urethane polymers (TPU); polythiourethane based polymers; vinyl based polymers, such as polyvinyl chloride, polyvinyl alcohol, polyvinylidene chloride, polyvinyl butyral; styrene based polymers, such as polystyrene, styrene methylmethacrylate copolymers (SMMA), styrene maleic anhydride polymers (SMA), acrylonitrile-styrene (ANS) copolymers, acrylonitrile butadiene styrene (ABS) terpolymers, (meth)acrylate butadiene styrene (MBS) terpolymers; olefin based polymers, such as polyethylene, polypropylene, polymethylpentene (PMP), cyclic (COC) or norbornene structure-containing polyolefins, and ethylene-propylene copolymers; amide based polymers, such as nylon and aromatic polyamide; imide based polymers; polyether imide based polymers; polysulfone based polymers; polyether sulfone based polymers; polyether ether ketone based polymers; polyphenylene sulfide based polymers; polyoxymethylene based polymers; and epoxy based, polymers, or any blend thereof, preferably cellulose triacetate (TAC), polycarbonate (PC), cellulose acetate butyrate (CAB), poly(methyl methacrylate) PMMA, polyethylene terephthalate) (PET), and mixtures thereof.

Aspect 6: The optical lens according to any one of aspects 1 to 5,

wherein said barrier layer provides additional optical functions.

Aspect 7: The optical lens according to aspect 6, wherein said optical functions are selected from the group consisting of UV protection, light polarization, base coloration, and mixtures thereof.

Aspect 8: The optical lens according to any one of aspects 1 to 7, wherein said photochromic layer comprises at least one photochromic dye.

Aspect 9: The optical lens according to any one of aspect 8,

wherein said at least one photochromic dye is selected from the group consisting of naphthopyrans, spironaphthopyrans, oxazines,

spironaphthoxazines, benzopyrans, spirobenzoxzines, spirobenzopyrans, spiropyrans, chromenes, fulgides, fulgimides, spirooxazines, organo-metal dithiozonates, triarylmethanes, stilbenes, azastilbenes, nitrones, quinones, and mixtures thereof. Aspect 10: The optical lens according to any one of aspects 1 to 9,

wherein said photochromic layer comprises cellulose ester. Aspect 11 : The optical lens according to any one of aspects 1 to 10, wherein said lens body comprises or consists of organic glass.

Aspect 12: The optical lens according to claim 10, wherein said organic glass comprises or consists of a polymeric material selected from the group consisting of polythiourethane, polyepisulphide, polymethyl methacrylate, polycarbonate, polyallyldiglycolcarbonate, polyacrylate, polyurethane, polyurea, polyamide, polysulphone, polyallyl, fumaric acid polymer, polystyrene, polymethyl acrylate, biopolymers, and mixtures and combinations thereof. Aspect 13: A spectacle comprising an optical lens according to any one of aspects 1 to 12.

Aspect 14: A method for producing an optical lens according to any one of claims 1 to 12,

comprising the steps of:

arranging layers (a) to (e) in succession or in a layer sequence in order to provide a laminated film,

applying an optical lens material to that said laminated film to provide said optical lens substantially incorporating said laminated film.

Aspect 15: The method according to aspect 14,

further comprising the steps of

arranging said laminated film in a casting mold for casting an optical lens, providing said casting mold with a liquid or molten optical lens material and substantially incorporating or encapsulating said laminated film within said liquid or molten optical lens material, and

solidifying said liquid or molten optical lens material.

Aspect 16: A method for producing an optical lens according to any one of aspects 1 to 12

comprises the steps of:

arranging layers (a) to (e) in succession or in a layer sequence in order to provide a laminated film,

bending the film, preferably in a press machine, preferably with a specific curvature aluminum mold, preferably under a temperature in a range of 80 to 95°C, preferably under a temperature of 90°C;

arranging the bent laminated film into an optical lens casting assembly for the mold, preferably including two glass molds and gaskets;

wherein the bent laminated film is held with the gaskets;

injecting liquid monomeric compound(s), preferably polyallyldiglycolcarbonate liquid monomer, into the lens casting assembly around the bent laminated film; putting the lens casting assembly into an oven under temperature in a range of 40°C to 90°C for an appropriate time, preferably of 6 to 12 hours, preferably 10 hours; to polymerize the monomeric compound(s), preferably the

polyallyldiglycolcarbonate liquid monomer,

opening the assembly and taking out the solid optical lens.