JP2011215245A - Photochromic lens - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a photochromic lens which has a photochromic layer with desired properties.SOLUTION: The photochromic lens has the photochromic layer, containing a photochromic dye and a resin component, on a plastic lens base. Further, the photochromic lens has an intermediate layer made of an inorganic substance between the plastic lens base and photochromic layer.

Description

  The present invention relates to a photochromic lens, and more particularly to a photochromic lens having excellent optical characteristics.

  In recent years, photochromic lenses using organic photochromic dyes are commercially available for eyeglasses (see, for example, Patent Document 1). They develop colors in bright outdoors and have the same anti-glare effect as high-density color lenses, and recover high transmittance when moving indoors.

  As a method for producing the photochromic lens, a method of providing a resin coating containing a photochromic dye on a lens substrate (coating method), a method of impregnating a lens substrate with a photochromic dye (impregnation method), or a method of kneading (kneading method) ) Etc. are used. Among the above production methods, in the impregnation method or kneading method, an appropriate substrate should be selected in order to exhibit good photochromic properties, but the coating method is preferable because there is no restriction on such a substrate. .

WO2005 / 014717A1

  Therefore, when the inventor of the present application manufactured a photochromic lens by a coating method, the photochromic layer was poorly cured and the photoresponsiveness (reaction speed of color generation) was reduced, and a photochromic lens having desired physical properties was not necessarily obtained. It turns out that there are cases where it is not possible.

  Therefore, an object of the present invention is to provide a photochromic lens having a photochromic layer having desired physical properties.

In order to achieve the above object, the present inventors have repeatedly studied the cause of poor curing of the photochromic layer and a decrease in the reaction rate of the color fading, and as a result, in a photochromic lens manufactured using a polycarbonate substrate or a polyurethane substrate. Since the above phenomenon becomes apparent, the inventors have come to know that the leaching component from the base material located in the lower layer of the photochromic layer is mixed into the photochromic layer. This point will be described in more detail. The plastic lens base material contains various additives such as a mold release agent, an ultraviolet absorber, a heat stabilizer, an antioxidant, and various dyes. Since the base material is a thermoplastic resin, it is considered that the additive is leached when a heat history such as heating is applied in the manufacturing process of the photochromic lens. Furthermore, the polycarbonate base material may leach out residues such as phenol derived from the monomer component to the upper layer. Similarly, the above-mentioned various additives are used for the polyurethane base material. However, when a thermal history such as heating is applied in the manufacturing process, the additive is easily leached. This is presumably because the polyurethane resin, which is a thermosetting resin, is leached so that the additive is squeezed out as the polymerization progresses because the polymerization progresses with heating and becomes dense due to the crosslinking reaction. The Since various defects of the photochromic layer are remarkably generated in such a base material, it has been found that the leaching component from the lens base material is the cause of the defect.
Therefore, as a result of further investigation based on the above knowledge, the inventor of the present application can suppress the occurrence of various defects in the photochromic layer by providing an intermediate layer made of an inorganic substance between the plastic lens substrate and the photochromic layer. Newly found. This is because the leaching component from the plastic lens substrate is mainly organic, so it is easy to mix into the photochromic layer, which is an organic layer. By forming an inorganic layer as a protective layer, the component from the substrate The inventors of the present application speculate that it is possible to block leaching.
The present invention has been completed based on the above findings.

That is, the above object has been achieved by the following means.
[1] A photochromic lens having a photochromic layer containing a photochromic dye and a resin component on a plastic lens substrate,
A photochromic lens comprising an intermediate layer made of an inorganic substance between the plastic lens substrate and the photochromic layer.
[2] The photochromic lens according to [1], wherein the intermediate layer is a vapor deposition film made of an inorganic oxide.
[3] The photochromic lens according to [1] or [2], which has an organic hard coat layer between the intermediate layer and the plastic lens substrate.
[4] The photochromic lens according to any one of [1] to [3], which has a primer layer between the photochromic layer and the intermediate layer.
[5] The photochromic lens according to any one of [1] to [4], wherein the plastic lens base material has a polycarbonate resin or a polyurethane resin as a main component.

  According to the present invention, a photochromic lens having excellent photochromic characteristics can be provided.

It is the schematic which shows an example of the layer structure of the photochromic lens of this invention.

The present invention relates to a photochromic lens having a photochromic layer containing a photochromic dye and a resin component on a plastic lens substrate (hereinafter also simply referred to as “lens substrate” or “substrate”). The photochromic lens of the present invention has an intermediate layer made of an inorganic substance (hereinafter also referred to as “inorganic intermediate layer”) between the plastic lens substrate and the photochromic layer.
As described above, the photochromic lens of the present invention suppresses the occurrence of defects in the photochromic layer by having an intermediate layer made of an inorganic material between the organic layer photochromic layer and the plastic lens substrate. As a result, excellent photochromic characteristics can be realized.
Hereinafter, the photochromic lens of the present invention will be described in more detail.

Plastic lens base material Examples of the plastic lens base material include methyl methacrylate homopolymer, copolymer of methyl methacrylate and one or more other monomers, diethylene glycol bisallyl carbonate homopolymer, diethylene glycol bisallyl carbonate and one or more. Copolymers with other monomers, sulfur-containing copolymers, halogen copolymers, polycarbonate, polystyrene, polyvinyl chloride, unsaturated polyester, polyethylene terephthalate, polyurethane, polythiourethane, compounds having an epithio group Polymer, a homopolymer of a monomer having a sulfide bond, a copolymer of sulfide and one or more other monomers, a copolymer of polysulfide and one or more other monomers, polydisulfide and one or more monomers Copolymers of monomers and the like. As described above, since the occurrence of defects in the photochromic layer is remarkable when using a polycarbonate base material and a polyurethane base material, the present invention is particularly applicable to a lens using a base material mainly composed of a polycarbonate resin or a polyurethane resin. It is effective to apply. Regarding the applicable polycarbonate substrate, paragraphs [0037] to [0088] of JP-A-2006-154783, paragraphs [0009] to [0035] of JP-A-2009-251330, and examples of the same can be referred to. Applicable polyurethane base materials include polyurea urethane base materials and polyurethane urea base materials. For example, paragraphs [0008] to [0062] of Japanese Patent Publication No. 2005-520034, paragraphs [0023] to [0036] of Japanese Patent No. 4156846, and examples of the publication can be referred to. Since both polycarbonate and polyurethane substrates contain various organic additives as described in the above publication, they are leached from the substrate by heating or the like and mixed into the photochromic layer, which is an organic layer. This is considered to cause poor curing of the photochromic layer and a decrease in the photochromic characteristics (reaction speed of color fading). On the other hand, in this invention, since an inorganic intermediate | middle layer is formed between a photochromic layer and a base material, the organic leaching component can be interrupted | blocked by the said intermediate | middle layer. This is considered to contribute to suppressing the occurrence of various defects in the photochromic layer.
Although the thickness of a base material is not specifically limited, Usually, it is about 1-30 mm. Moreover, the surface shape of the base material on which the photochromic layer is formed is not particularly limited, and may be any shape such as a flat surface, a convex surface, or a concave surface.

  The photochromic lens of the present invention can be produced by forming a photochromic layer on a lens substrate through an inorganic intermediate layer, preferably by a coating method. In the coating method, the photochromic layer is usually provided directly on the lens substrate or indirectly through another layer. Here, as an example of the layer that can be formed between the photochromic layer and the base material, a primer layer formed for improving the adhesion can be mentioned. It can be formed between the layers or between the inorganic intermediate layer and the photochromic layer. As such a primer layer, a known resin such as polyurethane that can function as an adhesive layer can be used. Details thereof will be described later. Although the thickness of the primer layer formed between a lens base material and an inorganic intermediate | middle layer is not specifically limited, For example, it is about 0.5-20 micrometers. Since the primer layer is usually an organic layer, it is difficult to completely block the component leached from the lens substrate with the primer layer. On the other hand, if an inorganic intermediate layer is formed on the above layer, it is possible to prevent the components that have been leached out through the primer layer from being mixed into the photochromic layer.

Inorganic Intermediate Layer In the present invention, the intermediate layer provided between the lens substrate and the photochromic layer is not particularly limited as long as it is made of an inorganic substance. By providing a layer made of an inorganic substance between the base material and the photochromic layer, it is possible to suppress the mixing of organic components leached from the base material into the photochromic layer, which is an organic layer. It is because it is thought that it contributes to suppression.

Examples of the inorganic substances include metals, metal or metalloid oxides, fluorides, silicides, borides, carbides, nitrides, sulfides, and the like. Specifically, it is a metal oxide such as SiO ₂ , SiO, ZrO ₂ , Al ₂ O ₃ , TiO ₂ , Sb ₂ O ₃ , Sb ₂ O ₅ , tantalum oxide, fluoride such as MgF _2, and the like. From the viewpoint of film formation ease and refractive index, an oxide is preferable. Among them, silicon is generally used because it has a refractive index close to that of a general photochromic layer and can suppress the occurrence of interference due to the difference in refractive index between layers. Oxides are preferred.

  The inorganic intermediate layer composed of the inorganic substance can be formed by a known film formation method. As a film forming method, a vapor deposition method is preferable because a uniform film can be easily formed. Examples of the vapor deposition method include a vacuum vapor deposition method, a CVD method, a PVD method, a sputtering method, an ion plating method, and an ion beam assist method.

  The thickness of the inorganic intermediate layer is preferably 10 nm or more from the viewpoint of forming a uniform film on the substrate. Regarding the upper limit, if it exceeds 200 nm, it takes time to form a film, which is not preferable. From the above viewpoint, the thickness of the inorganic intermediate layer is preferably in the range of 10 nm to 200 nm, and more preferably 10 nm to 100 nm. Note that at least one inorganic intermediate layer may be provided, but it is also possible to provide two or more layers made of different inorganic substances. In this case, the thickness means the total thickness of a plurality of layers.

  A photochromic layer can be directly formed on the inorganic intermediate layer, or a photochromic layer can be formed on a primer layer for improving adhesion. As the primer layer formed here, a resin layer formed from a coating composition containing a resin component and an aqueous resin solvent is preferable from the viewpoint of adhesion. In addition, when a primer layer is provided in a state where the inorganic intermediate layer is not formed, it is considered that a leaching component from the lens base material is mixed into the primer layer which is an organic layer. Here, for example, if the mixed component is a release agent, the effect of improving the adhesion of the primer layer may be reduced by the action of the release agent. On the other hand, if the primer layer is formed on the inorganic intermediate layer, it is possible to suppress the leaching component from the lens base material from being mixed into the primer layer, so that the effect of improving the adhesion of the primer layer can be maintained well. It becomes possible.

  The thickness of the primer layer formed here is preferably 0.05 μm or more from the viewpoint of maintaining the adhesion between the photochromic layer and the inorganic intermediate layer, and is 15 μm or less from the viewpoint of the optical characteristics of the resulting photochromic lens. It is preferable that it is in the range of 3 to 10 μm from the viewpoint of achieving both optical properties and adhesion.

  The aqueous solvent contained in the coating composition is, for example, a mixed solvent with water or a polar solvent, and is preferably water. Moreover, the solid content concentration in the coating composition is preferably 1 to 62% by mass, more preferably 25 to 50% by mass, from the viewpoint of liquid stability and film-forming property. In addition to the resin component, the coating composition may contain additives such as an antioxidant, a dispersant, and a plasticizer as necessary. A commercially available aqueous resin composition may be diluted with a solvent such as water, alcohol, propylene glycol monomethyl ether (PGM), or the like.

  The coating composition may include a resin component in a state dissolved in an aqueous solvent or dispersed as fine particles (preferably colloidal particles). Among these, a dispersion in which the resin component is dispersed in fine particles in a solvent (preferably in water) is desirable. In this case, the particle size of the resin component is 0.3 μm or less from the viewpoint of dispersion stability of the composition. It is preferable that Further, the pH of the aqueous resin composition is preferably about 5.5 to 9.0 at 25 ° C. from the viewpoint of stability, and the viscosity at 25 ° C. is 5 to 500 mPa from the point of coating suitability. * It is preferable that it is s, and it is more preferable that it is 50-150 mPa * s.

  As said coating composition, what contains a polyurethane resin, an acrylic resin, an epoxy resin etc. as a resin component is mentioned. The use of a resin component having a (meth) acryl group as the resin component is particularly preferable from the viewpoint of adhesion to a photochromic layer containing an acrylic resin. Here, “(meth) acrylic group” includes an acrylic group and a methacrylic group.

  The resin component is preferably a polyurethane resin from the viewpoint of adhesion. A coating composition containing a polyurethane resin, that is, an aqueous (preferably water-dispersed) polyurethane resin composition is, for example, a high molecular weight polyol compound and an organic polyisocyanate compound, together with a chain extender, if necessary, inert to the reaction. It can be prepared by urethanizing in a solvent having a high affinity with water to form a prepolymer, neutralizing the prepolymer, and then dispersing in a water-based solvent containing a chain extender to increase the molecular weight. . Regarding such an aqueous polyurethane resin composition and a method for preparing the same, for example, paragraphs [0009] to [0013] of Japanese Patent No. 3588375, paragraphs [0012] to [0021] of JP-A-8-34897, Reference can be made to paragraphs [0010] to [0033] of JP-A-11-92653, paragraphs [0010] to [0033] of JP-A-11-92655, and the like. Moreover, as said aqueous polyurethane resin composition, it is also possible to use commercially available aqueous urethane as it is or after diluting with an aqueous solvent as needed. Commercially available water-based polyurethanes include, for example, “Adekabon titer” series manufactured by Asahi Denka Kogyo Co., Ltd., “Olestar” series manufactured by Mitsui Toatsu Chemical Co., Ltd., Dainippon Ink & Chemicals, Inc. "Bondic" series, "Hydran" series, Bayer's "Imperil" series, Sofran Japan's "Sofuranato" series, Kao's "Poise" series, Sanyo Chemical Industries, Ltd. "Samprene" series manufactured by Hodogaya Chemical Co., Ltd., "Izelux" series manufactured by Hodogaya Chemical Co., Ltd., "Superflex" series manufactured by Daiichi Kogyo Seiyaku Co., Ltd. be able to.

  The aqueous polyurethane resin composition is obtained as a result of dispersing a terminal isocyanate prepolymer having a polyol such as polyester polyol or polyether polyol in the basic skeleton and an anionic group such as carboxyl group or sulfone group in an aqueous solvent. Are preferred.

  As a coating method of the aqueous resin composition, a known coating method such as a dipping method or a spin coating method can be used. The application conditions may be set as appropriate so that a resin layer having a desired film thickness can be formed. After application of the aqueous resin composition, the aqueous resin layer can be formed by drying the composition. The said drying can be performed by arrange | positioning the lens which apply | coated the aqueous resin composition in the atmosphere of room temperature-100 degreeC for 1 minute-5 hours, for example.

In the photochromic layer coating method, a photochromic layer containing a photochromic dye is contained in a cured body (resin component) by applying a photochromic liquid containing a photochromic dye and a curable component directly or indirectly on a substrate and then performing a curing treatment. Can be formed. More specifically, the photochromic liquid can be formed from a curable component, a photochromic dye, a polymerization initiator, and an additive that is optionally added. Below, each component is demonstrated.

(I) Curable component The curable component that can be used for forming the photochromic layer is not particularly limited, and radical polymerization such as (meth) acryloyl group, (meth) acryloyloxy group, vinyl group, allyl group, styryl group, etc. Known photopolymerizable monomers and oligomers having a functional group, and prepolymers thereof can be used. Among these, a compound having a (meth) acryloyl group or a (meth) acryloyloxy group as a radically polymerizable group is preferable because of easy availability and curability. That is, the resin component contained in the photochromic layer is preferably a resin (acrylic resin) formed by a polymerization reaction of an acrylic monomer. The (meth) acryloyl refers to both acryloyl and methacryloyl, and (meth) acryloyloxy refers to both acryloyloxy and methacryloyloxy. For details, WO2008 / 001578A1 paragraphs [0050] to [0075] can be referred to.

(Ii) Photochromic dye As the photochromic dye that can be added to the photochromic liquid, known ones can be used, and examples include photochromic compounds such as fulgimide compounds, spirooxazine compounds, and chromene compounds. In the present invention, These photochromic compounds can be used without particular limitation. For details, WO2008 / 001578A1 paragraphs [0076] to [0088] can be referred to. The concentration of the photochromic dye in the photochromic liquid is preferably 0.01 to 20 parts by mass, and more preferably 0.1 to 10 parts by mass with respect to 100 parts by mass of the curable component.

(Iii) Polymerization initiator The polymerization initiator added to the photochromic liquid can be appropriately selected from known thermal polymerization initiators and photopolymerization initiators according to the polymerization method. For details thereof, WO2008 / 001578A1 paragraphs [0089] to [0090] can be referred to.

(Iv) Additives The photochromic liquid contains surfactants, antioxidants, radical scavengers, ultraviolet rays for the purpose of improving the durability of the photochromic dye, improving the color development speed, improving the fading speed and improving the moldability. You may add additives, such as a stabilizer, a ultraviolet absorber, a mold release agent, an anti-coloring agent, an antistatic agent, a fluorescent dye, a dye, a pigment, a fragrance | flavor, a plasticizer. As these additives, known compounds can be used without any limitation. For details, WO2008 / 001578A1 paragraphs [0092] to [0097] can be referred to.

  A photochromic layer can be formed by applying and curing a photochromic liquid containing the components described above. In the present invention, the method for preparing the photochromic liquid is not particularly limited, and can be performed by weighing and mixing a predetermined amount of each component. The order of addition of each component is not particularly limited, and all the components may be added simultaneously, or only the monomer component is mixed in advance, and a photochromic dye or other additive may be added and mixed immediately before polymerization. Good. The photochromic liquid preferably has a viscosity at 25 ° C. of 20 to 500 mPa · s, more preferably 50 to 300 mPa · s, and particularly preferably 60 to 200 mPa · s. By setting it as this viscosity range, application | coating of a photochromic liquid becomes easy and the photochromic layer of desired thickness can be obtained easily. The photochromic liquid can be applied by a known application method such as a spin coating method or a dipping method.

  After applying the photochromic liquid on the substrate, a photochromic layer can be formed by applying a curing treatment (heating, light irradiation, etc.) according to the type of curable component contained in the photochromic liquid. The curing treatment can be performed by a known method. The thickness of the photochromic layer is preferably 10 μm or more, more preferably 20 to 60 μm, from the viewpoint of satisfactorily expressing the photochromic characteristics.

In order to protect the photochromic layer and improve the scratch resistance, various organic layers generally used as a hard coat layer (organic hard coat layer) can be applied to the organic hard coat layer photochromic lens. From the viewpoint of achieving both improvement in lens durability and optical characteristics, the thickness is preferably in the range of 0.5 to 10 μm.

  The hard coat layer preferably contains an organosilicon compound and metal oxide particles from the viewpoint of improving the durability of the lens. In addition, since the hard coat layer containing an organosilicon compound is preferable in terms of adhesion with the intermediate layer made of the above-described silicon oxide and a refractive index close to the intermediate layer, the inorganic intermediate layer and the lens substrate It is also suitable as a hard coat layer provided between the two. As an example of a hard coat composition capable of forming such a hard coat layer, there can be mentioned those described in JP-A-63-1640.

Moreover, as a preferable aspect of the said organosilicon compound, the organosilicon compound represented by the following general formula (I) or its hydrolyzate can also be mentioned.
(R ¹ ) _a (R ³ ) _b Si (OR ² ) _{4- (a + b)} (I)

In general formula (I), R ¹ represents an organic group having a glycidoxy group, an epoxy group, a vinyl group, a methacryloxy group, an acryloxy group, a mercapto group, an amino group, a phenyl group, and the like, and R ² represents the number of carbon atoms. Represents an alkyl group having 1 to 4 carbon atoms, an acyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 10 carbon atoms, R ³ represents an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 10 carbon atoms, a and b each represents 0 or 1;

Alkyl group having 1 to 4 carbon atoms represented by R ² is a linear or branched alkyl group. Specific examples include a methyl group, an ethyl group, a propyl group, a butyl group.
Examples of the acyl group having 1 to 4 carbon atoms represented by R ² include an acetyl group, a propionyl group, an oleyl group, and a benzoyl group.
Examples of the aryl group having 6 to 10 carbon atoms represented by R ² include a phenyl group, a xylyl group, and a tolyl group.
The alkyl group having 1 to 6 carbon atoms represented by R ³ is a linear or branched alkyl group. Specific examples thereof include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, and a hexyl group. Is mentioned.
As a C6-C10 aryl group represented by R < ³ >, a phenyl group, a xylyl group, a tolyl group etc. are mentioned, for example.
Specific examples of the compound represented by the general formula (I) include those described in paragraph [0073] of JP-A-2007-077327. Since the organosilicon compound represented by the general formula (I) has a curable group, a hard coat layer can be formed as a cured film by performing a curing treatment after coating.

The metal oxide particles contained in the hard coat layer can contribute to the adjustment of the refractive index and the hardness improvement of the hard coat layer. Specific examples include tungsten oxide (WO ₃ ), zinc oxide (ZnO), silicon oxide (SiO ₂ ), aluminum oxide (Al ₂ O ₃ ), titanium oxide (TiO ₂ ), zirconium oxide (ZrO ₂ ), tin oxide. Examples thereof include particles such as (SnO ₂ ), beryllium oxide (BeO), and antimony oxide (Sb ₂ O ₅ ), and two or more kinds of metal oxide particles can be used in combination. The particle size of the metal oxide particles is preferably in the range of 5 to 30 nm from the viewpoint of achieving both scratch resistance and optical properties. For the same reason, the content of the metal oxide particles in the hard coat layer can be appropriately set in consideration of the refractive index and the hardness, but is usually about 5 to 80% by mass per solid content of the hard coat composition. is there. The metal oxide particles are preferably colloidal particles from the viewpoint of dispersibility in the hard coat layer.

  The organic hard coat layer is prepared by applying a hard coat composition prepared by mixing the above-mentioned components and optional components such as an organic solvent and a surfactant (leveling agent) on the photochromic layer as necessary. It can be formed by applying a suitable curing treatment (thermal curing, photocuring, etc.). As a means for applying the hard coat composition, a commonly performed method such as a dipping method, a spin coating method, or a spray method can be applied.

  An example of the layer structure of the photochromic lens of the present invention described above is shown in FIG. However, the photochromic lens of the present invention is not limited to the embodiment shown in FIG. 1, and can have a functional film such as a known antireflection film at an arbitrary position.

  In the following, the present invention will be further explained by examples. However, this invention is not limited to the aspect shown in the Example.

[Examples 1-1, 1-2, 1-3]
(1) Molding of polycarbonate lens substrate As a plastic lens substrate, Teijin Chemicals polycarbonate (Panlite optical grade) is a meniscus lens substrate (center thickness 2.0 mm, diameter 75 mm, convex surface curve ( The average value was injection molded to about +0.8).

(2) Formation of Silica Vapor Deposition Film (Inorganic Intermediate Layer) A vapor deposition film made of silica (SiO ₂ ) was formed on the convex surface of the lens substrate molded in (1) above by a vacuum vapor deposition method. Here, by changing the film formation time during vapor deposition, silica vapor deposition films having different thicknesses were formed on the respective lenses.

(3) Formation of primer layer An aqueous dispersion of polyurethane in which an acrylic group is introduced into a polyurethane skeleton as a primer liquid on the silica vapor deposition film formed in (2) above (polycarbonate polyol polyurethane emulsion, viscosity 100 mPa · s, solid content) After application by a spin coating method, it was air-dried for 15 minutes in an atmosphere of a temperature of 25 ° C. and a humidity of 50% RH to form a primer layer having a thickness of about 7 μm.

(4) Preparation of photochromic coating solution A radically polymerizable composition containing a curable component such as trimethylolpropane trimethacrylate, BPE oligomer (2,2-bis (4-methacryloyloxypolyethoxyphenyl) propane) in a plastic container. Prepared. 3 parts by mass of the following chromene 1 as a photochromic pigment, 100 parts by mass of this radical polymerizable composition, a light stabilizer, a hindered phenol-based antioxidant, and a radical polymerization initiator as an ultraviolet polymerization initiator (Irgacure manufactured by BASF) 1870) An appropriate amount of a silane coupling agent was added dropwise to the composition which was sufficiently stirred and mixed by adding 0.6 parts by mass with stirring. Then, the stirring deaeration process was performed and the curable composition which has photochromic property was obtained.

(5) Formation of photochromic layer The curable composition prepared in (4) was coated on the primer layer formed in (3) above by a spin coating method. Thereafter, the lens was irradiated with UV light having a wavelength of 405 nm with a UV lamp in a nitrogen atmosphere, and further heat-cured at 100 ° C. to form a photochromic layer having a thickness of 40 μm.

  By the above process, the photochromic lens which has a silica vapor deposition film | membrane, a primer layer, and a photochromic layer in this order on the lens base material was obtained.

[Comparative Example 1-1]
A photochromic lens was obtained in the same manner as in the above example except that the inorganic intermediate layer (silica vapor deposition film) was not formed.

Evaluation method (1) Confirmation of curability The liquid pool formed on the periphery of the lens of the formed photochromic layer (the portion that is raised compared to the central portion) is a poor curing (radical polymerization caused by ultraviolet irradiation) left on the periphery. This is a region of poor reaction. Therefore, Table 1 shows the result of visual observation of the width of the liquid pool. A larger puddle width indicates that curing is insufficient.

[Examples 2-1, 2-2, 2-3]
Photochromic lenses were produced in the same manner as in Examples 1-1, 1-2, and 1-3 except that a polyurethaneurea substrate (trade name Phoenix manufactured by HOYA Corporation) was used as the lens substrate. Thereby, the photochromic lens which has a silica vapor deposition film | membrane, a primer layer, and a photochromic layer in this order on the lens base material was obtained.

[Comparative Example 2-1]
A photochromic lens was obtained in the same manner as in the above example except that the inorganic intermediate layer (silica vapor deposition film) was not formed.

  The obtained photochromic lens was evaluated by the above method. The results are shown in Table 2.

Evaluation results In any of the examples and comparative examples, the examples showed better results in curability than the comparative examples. From this result, it can be confirmed that the leaching component from the lens substrate causes a decrease in curing failure in the photochromic layer, and that this can be suppressed by the inorganic intermediate layer. In addition, since poor curing in the photochromic layer also causes poor adhesion between the photochromic layer and the lower primer layer, it is advantageous to obtain a lens having excellent durability.

  The photochromic lens of the present invention is suitable as spectacles for which excellent durability is required.

Claims (5)

A photochromic lens having a photochromic layer containing a photochromic dye and a resin component on a plastic lens substrate,
A photochromic lens comprising an intermediate layer made of an inorganic substance between the plastic lens substrate and the photochromic layer. The photochromic lens according to claim 1, wherein the intermediate layer is a vapor deposition film made of an inorganic oxide. The photochromic lens according to claim 1, further comprising an organic hard coat layer between the intermediate layer and the plastic lens substrate. The photochromic lens according to claim 1, further comprising a primer layer between the photochromic layer and the intermediate layer. The photochromic lens according to any one of claims 1 to 4, wherein the plastic lens substrate is mainly composed of a polycarbonate resin or a polyurethane resin.