JP2014106516A - Photochromic lens, and manufacturing method for the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a photochromic lens that has a photochromic layer having desired physical properties.SOLUTION: A manufacturing method of a photochromic lens that includes a photochromic layer containing photochromic dye and a resin component over a plastic lens base material comprises: formation of an aqueous resin layer over the plastic lens base material by coating the base material with an aqueous resin composition containing the resin component and an aqueous solvent and drying the coat; and formation of the photochromic layer by coating the aqueous resin layer with a photochromic liquid containing the photochromic dye, a polymerizable component, and a polymerization initiator and subjecting the coated layer to polymerization. The aqueous resin composition contains a polymerization initiator of the same type as the polymerization initiator contained in the photochromic liquid.

Description

  The present invention relates to a method for producing a photochromic lens, and a photochromic lens that can be obtained by the above method.

  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

  Then, when this inventor manufactured the photochromic lens by the coating method, it turned out that the curing defect of a photochromic layer is seen and the photochromic lens which has a desired physical property may not necessarily be obtained.

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

As a result of repeated investigations on the cause of poor curing of the photochromic layer in order to achieve the above object, the present inventors reveal that the above phenomenon becomes apparent in a photochromic lens manufactured using a polycarbonate substrate or a polyurethane substrate. Thus, the inventors have found that the leaching component from the base material located in the lower layer of the photochromic layer inhibits the polymerization of the photochromic layer, which is the cause of the above phenomenon.
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 In such a base material, the photochromic layer is not sufficiently hardened. Thus, 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 studies based on the above findings, the present inventors have determined that a primer layer formed between the plastic lens substrate and the photochromic layer is a polymerization initiator contained in the photochromic liquid used for photochromic layer formation. It was newly found that the occurrence of various defects in the photochromic layer can be suppressed by forming from an aqueous resin composition containing the same kind of polymerization initiator. This is because radicals and other active components generated from the polymerization initiator contained in the primer layer (aqueous resin layer) formed from the aqueous resin composition affect the photochromic layer, and polymerization (curing) in the vicinity of the interface with the primer layer The present inventors speculate that this is due to the promotion of In addition, simply increasing the amount of polymerization initiator added to the photochromic liquid may cause yellowing of the photochromic layer due to unreacted polymerization initiator, so add a part of the polymerization initiator to the primer layer. Is advantageous in obtaining a high-quality photochromic lens. In particular, when a photochromic layer is formed by a photopolymerization reaction, light is less likely to reach the portion farther from the incident surface due to the photoresponsiveness of the photochromic dye, and curing is likely to be insufficient near the interface with the primer layer. As a result, the leaching component from the plastic lens substrate is likely to be mixed in by the photochromic layer, and it is considered that poor curing occurs remarkably. In contrast, the polymerization initiator added to the primer layer improves the reactivity in the vicinity of the interface with the primer layer in the photochromic layer, thereby reducing polymerization inhibition due to components leached from the substrate, resulting in poor curing of the photochromic layer. The present inventor speculates that it contributes to the suppression of the above.
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 method for producing a photochromic lens having a photochromic layer containing a photochromic dye and a resin component on a plastic lens substrate,
Forming an aqueous resin layer on a plastic lens substrate by applying and drying an aqueous resin composition containing a resin component and an aqueous solvent; and
Forming a photochromic layer on the aqueous resin layer by applying a photochromic liquid containing a photochromic dye, a polymerizable component and a polymerization initiator, and then performing a polymerization treatment; and
The method for producing a photochromic lens, wherein the aqueous resin composition contains a polymerization initiator of the same type as a polymerization initiator contained in the photochromic liquid.
[2] The method for producing a photochromic lens according to [1], wherein the polymerization initiator is a radical photopolymerization initiator.
[3] The method for producing a photochromic lens according to [1] or [2], wherein the water-based resin composition contains a polymerizable component having the same type of polymerization reaction as the polymerizable component contained in the photochromic liquid.
[4] The method for producing a photochromic lens according to [3], wherein the polymerizable component contained in the aqueous resin composition is a resin component contained in the composition.
[5] A photochromic lens having a photochromic layer containing a photochromic dye and a resin component on a plastic lens substrate,
A photochromic lens having an aqueous resin layer between the plastic lens substrate and the photochromic layer, wherein the aqueous resin layer and the photochromic layer contain the same kind of polymerization initiator.

  According to the present invention, it is possible to provide a high-quality photochromic lens in which poor curing of the photochromic layer is suppressed.

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 method for producing 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 production method of the present invention includes forming a water-based resin layer on a plastic lens substrate by applying and drying a water-based resin composition containing a resin component and a water-based solvent, and on the water-based resin layer, It includes forming a photochromic layer by applying a photochromic liquid containing a photochromic dye, a polymerizable component and a polymerization initiator, and then performing a polymerization treatment. Here, as the aqueous resin composition, one containing a polymerization initiator of the same type as the polymerization initiator contained in the photochromic liquid is used. Thus, as described above, the reactivity of the vicinity of the interface with the primer layer in the photochromic layer, that is, the portion on the lens base material side can be improved, so that polymerization inhibition due to the leaching component from the base material can be reduced. it is conceivable that. In the present invention, “the same kind of polymerization initiator” means that the energy required for the function of the polymerization initiator to be the same. For example, if the polymerization initiator contained in the photochromic liquid is a photopolymerization initiator, an aqueous system is used. The polymerization initiator contained in the resin composition is also a photopolymerization initiator, and if the former is a thermal polymerization initiator, the latter is also a thermal polymerization initiator. The “same type of polymerization reaction” described later means that the polymerization initiator capable of initiating polymerization is the same type of polymerization initiator.
Hereinafter, the manufacturing method of 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 the polycarbonate base material and the polyurethane base material contain various organic additives as described in the above publication, they are leached from the base material by heating or the like and inhibit the polymerization reaction of the photochromic layer. This is considered to cause poor curing of the photochromic layer. On the other hand, in the present invention, the reactivity in the vicinity of the interface with the primer layer in the photochromic layer, that is, the portion on the lens substrate side can be improved, so that the leaching component from the lens substrate inhibits the polymerization of the photochromic layer. It can be inferred that the ability to suppress this contributes to suppressing the occurrence of poor curing of 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 by a coating method. In the coating method, the photochromic layer is usually provided directly on the lens substrate or indirectly through another layer. In the present invention, a primer layer (aqueous resin layer) formed from an aqueous resin composition is provided between the lens substrate and the photochromic layer, but a hard coat layer can also be provided in addition to the primer layer. In this case, it is preferable to provide a hard coat layer between the lens substrate and the aqueous resin layer in order to obtain the effect of providing the aqueous resin layer satisfactorily. The hard coat layer formed here is as described later for the hard coat layer (organic hard coat layer) formed on the photochromic layer. Or in order to provide abrasion resistance on a base material, it is also possible to provide the hard-coat layer formed from the composition described in the Japanese translations of PCT publication No. 2001-520699. The thickness of the hard coat layer formed here is, for example, about 0.5 to 10 μm. Some lens substrates are commercially available with a hard coat, and in the present invention, a photochromic layer can be formed on such a lens substrate. Although the organic hard coat layer is easy to form and desirable from the viewpoint of durability, the organic components that have leached from the lens substrate can be removed with this organic hard coat layer or the upper aqueous resin layer. It is difficult to completely shut off. In contrast, in the present invention, the components that have been leached out through these layers prevent the photochromic layer from being inhibited by improving the reactivity of the photochromic layer on the lens substrate side as described above. Can do.

Water-based resin layer (primer layer)
In the production method of the present invention, an aqueous resin layer is formed by applying and drying an aqueous resin composition containing a resin component and an aqueous resin solvent on the lens substrate. The photochromic layer is provided on the formed aqueous resin layer. The thickness of the aqueous resin layer formed here is preferably 0.05 μm or more from the viewpoint of maintaining adhesion with the photochromic layer, and 20 μm or less from the viewpoint of the optical characteristics of the resulting photochromic lens. Preferably, it is more preferably in the range of 0.10 to 10 μm from the viewpoint of achieving both optical properties and adhesion.

  The aqueous solvent contained in the aqueous resin composition is, for example, a mixed solvent with water or a polar solvent, and is preferably water. In addition, the solid content concentration in the aqueous resin composition is preferably 1 to 60% by mass, more preferably 5 to 50% by mass, from the viewpoint of liquid stability and film forming property. The aqueous resin composition may contain additives such as an antioxidant, a dispersant, and a plasticizer as necessary in addition to the resin component. 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 aqueous resin composition is desirably a dispersion in which a resin component is dispersed in a fine particle form in an aqueous solvent (preferably in water). In this case, the particle size of the resin component is the dispersion stability of the composition. From the viewpoint, it is preferably 0.3 μm or less. 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 10-150 mPa * s.

  As said aqueous resin composition, what contains a polyurethane resin, an acrylic resin, an epoxy resin etc. as a resin component is mentioned. The resin component is preferably a polyurethane resin from the viewpoint of adhesion. A water-based resin composition containing a polyurethane resin, that is, a water-based 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 and having an affinity for water. It can be prepared by making a prepolymer by urethanization in a large solvent and dispersing the prepolymer in an aqueous 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.

The aqueous resin layer is formed by removing the solvent in the aqueous resin composition.
Therefore, since a layer can be formed without a curing reaction by light or heat, a polymerization initiator is not required for forming an aqueous resin layer. In contrast, in the present invention, a polymerization initiator is added to the aqueous resin composition in order to use the aqueous resin layer as a supply source of active components such as radicals to the photochromic layer. The polymerization initiator added here is the same kind as that contained in the photochromic liquid used for photochromic layer formation as mentioned above. It is desirable that the photochromic layer is formed by photopolymerization, preferably photoradical polymerization, because the reaction is completed in a short time. For this reason, the polymerization initiator contained in the photochromic layer is preferably a photopolymerization initiator, and more preferably a radical photopolymerization initiator. Therefore, the polymerization initiator contained in the aqueous resin composition is also preferably a photopolymerization initiator, and more preferably a radical photopolymerization initiator. As described above, the formation of the photochromic layer by photopolymerization tends to reduce the amount of light transmitted toward the layer because of the photoresponsiveness of the photochromic dye. Therefore, in photopolymerization, the photochromic layer is harder to be cured toward the lens base material side, and this is considered to cause various defects due to a leaching component from the lens base material. In contrast, according to the present invention, since active components such as radicals can be supplied from the lens substrate side (aqueous resin layer) to the photochromic layer, it is assumed that the polymerization reaction can proceed well even with a small amount of light transmission. Is done. The content of the polymerization initiator in the aqueous resin composition is preferably 1% by mass or more from the viewpoint of effectively promoting curing in the vicinity of the interface of the photochromic layer. On the other hand, from the viewpoint of preventing precipitation of the polymerization initiator and maintaining the liquid stability of the aqueous resin composition, the content of the polymerization initiator in the aqueous resin composition is preferably 15% by mass or less, and preferably 10% by mass or less. More preferably.
In addition, foreign matter mixing into the photochromic layer causes a decrease in photochromic properties, but even if a polymerization initiator is mixed into the photochromic layer from the aqueous resin composition, this polymerization initiator is contained in the photochromic layer. Therefore, the effect can be exhibited without causing deterioration of the photochromic characteristics due to mixing. From the viewpoint of better maintaining the photochromic properties, the photochromic layer and the aqueous resin layer preferably contain the same polymerization initiator or a polymerization initiator applicable to the photochromic layer.

  The polymerization initiator in the aqueous resin composition is thought to be able to exert the effect of improving the reactivity in the vicinity of the interface with the primer layer of the photochromic layer by generating an active component such as a radical. It is considered that the function of increasing the hardness of the water-based resin layer can be exhibited by functioning in the layer. The fact that the polymerization initiator in the aqueous resin composition exerts the above action in the aqueous resin layer is advantageous in suppressing the leaching component from the lens substrate from being mixed into the photochromic layer. For this purpose, it is preferable to add a polymerizable component having the same type of polymerization reaction as the polymerizable component contained in the photochromic liquid to the aqueous resin composition. As an example of such a polymerizable component, a resin component contained in an aqueous resin composition can be exemplified. That is, the resin component containing a polymerizable group having the same type of polymerization reaction as that of the polymerizable component contained in the photochromic liquid can be used. As said resin component, it is preferable to use the resin component which has a (meth) acryl group from a reactive point. Here, the “(meth) acryl group” includes an acryl group and a methacryl group. In addition, the resin component which has a (meth) acryl group is preferable also from the point of adhesiveness with the photochromic layer containing acrylic resin. The content of the polymerizable component in the aqueous resin composition is preferably about 1 to 50% by mass. The polymerizable component contained in the aqueous resin composition has a polymerizable group in one molecule. Mention may also be made of components generally referred to as crosslinkers having two or more. When the crosslinking agent crosslinks the resin components in the aqueous resin composition, the hardness of the aqueous resin layer can be improved. Moreover, the adhesiveness of both layers can be further improved by exhibiting the action of the crosslinking agent at the interface between the aqueous resin layer and the photochromic layer. In the water-based resin layer in the present invention, after the water-based resin layer is formed by applying and drying the water-based resin composition, an aspect in which the polymerizable component causes a polymerization reaction by light irradiation or the like and contributes to improvement in hardness or the like is also possible. Shall be included.

  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 example for 5 minutes-24 hours.

Photochromic layer A photochromic film containing a photochromic dye in a polymer (resin component) is obtained by directly or indirectly applying a photochromic liquid containing a photochromic dye and a polymerizable component onto the water-based resin layer formed above, and then performing a polymerization treatment. Can be formed. More specifically, the photochromic liquid can be formed from a polymerizable component, a photochromic dye, a polymerization initiator, and an additive that is optionally added. Below, each component is demonstrated.

(I) Polymerizable component The polymerizable 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, more preferably 0.1 to 10 parts by mass with respect to 100 parts by mass of the polymerizable 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. As described above, in the present invention, it is preferable to use a photopolymerization initiator, and it is more preferable to use a photoradical polymerization initiator. As a compounding quantity with respect to the photochromic liquid whole quantity of a photoinitiator, it is 0.001-5 mass parts normally with respect to 100 mass parts of said polymeric components (radical polymerizable monomer etc.), and 0.1-1 It is preferable that it is a mass part. Moreover, although the usage-amount of a thermal-polymerization initiator changes with polymerization conditions, the kind of initiator, and the kind and composition of a polymerizable monomer, Usually, 0.01-10 mass with respect to 100 mass parts of said polymeric components. It is preferable to set the range of parts.

(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 cps, more preferably 50 to 300 cps, and particularly preferably 60 to 200 cps. 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. Application of the photochromic liquid can be performed by a known application method such as a spin coating method.

  After applying the photochromic liquid on the substrate, a photochromic layer can be formed by performing a polymerization process (heating, light irradiation, etc.) according to the type of polymerizable component contained in the photochromic liquid. As described above, in the present invention, polymerization treatment (photopolymerization) by light irradiation is preferable. The polymerization treatment can be performed by a known method. The thickness of the photochromic layer is preferably 10 μm or more, more preferably 20 μm or more, from the viewpoint of satisfactorily expressing the photochromic properties, and the viewpoint of favorably proceeding the polymerization reaction in the vicinity of the interface with the aqueous resin layer. To 60 μm or less.

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. Examples of the hard coat composition capable of forming such a hard coat layer include those described in JP-A No. 63-10640 and Japanese Patent No. 3956043.

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), antimony oxide (Sb ₂ O ₅ ), cerium oxide (CeO ₂ ), etc., 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 conventional method such as a dipping method, a spin coating method, or a spray method can be applied, but a dipping method or a spin coating method is preferable in terms of surface accuracy.

  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.

  Further, the present invention is a photochromic lens having a photochromic film containing a photochromic dye and a resin component on a plastic lens substrate, and having a water-based resin layer between the plastic lens substrate and the photochromic film, and The water-based resin layer and the photochromic film contain a polymerization initiator of the same kind, and relate to a photochromic lens. The photochromic lens of the present invention can be obtained by the production method of the present invention. The details are as described above.

  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.

[Example 1-1]
(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 water-based resin layer (primer layer) The following photochromic coating is applied to an aqueous dispersion of polyurethane (polycarbonate polyol-based polyurethane emulsion, viscosity 100 CPS, solid content concentration 38% by mass) in which an acrylic group is introduced into a polyurethane skeleton as a primer liquid. What added the ultraviolet polymerization initiator (photoradical polymerization initiator) contained in the liquid was prepared. The concentration of the ultraviolet polymerization initiator in the prepared primer solution was 10% by mass.
The primer solution was applied onto a lens substrate by spin coating, and then air-dried for 15 minutes in an atmosphere of a temperature of 25 ° C. and a humidity of 50% RH to form an aqueous resin layer having a thickness of about 7 μm.

(3) Preparation of photochromic coating solution 20 parts by mass of trimethylolpropane trimethacrylate, 35 parts by mass of BPE oligomer (2,2-bis (4-methacryloyloxypolyethoxyphenyl) propane), EB6A (polyester oligomer hexaacrylate) in a plastic container ) A radical polymerizable composition comprising 10 parts by mass, 10 parts by mass of polyethylene glycol diacrylate having an average molecular weight of 532, and 10 parts by mass of glycidyl methacrylate was prepared. 3 parts by mass of the following chromene 1 as a photochromic dye, a light stabilizer LS765 (bis (1,2,2,6,6-pentamethyl-4-piperidyl) sebacate, methyl) with respect to 100 parts by mass of the radical polymerizable composition 5 parts by mass of (1,2,2,6,6-pentamethyl-4-piperidyl) sebacate), 5 parts by mass of hindered phenol antioxidant (Irgacure 245 manufactured by Ciba Specialty Chemicals), and CGI as an ultraviolet polymerization initiator -1870 (manufactured by Ciba Specialty Chemicals) was added with 0.6 parts by mass and sufficiently stirred and mixed, while stirring γ-methacryloyloxypropyltrimethoxysilane (KBM503 manufactured by Shin-Etsu Chemical Co., Ltd.). 6 mass parts was dripped. Then, the curable composition which has photochromic property was obtained by defoaming for 2 minutes with a rotation-revolution system stirring defoaming apparatus.

(4) Formation of photochromic layer The curable composition prepared in (3) was coated on the aqueous resin layer formed in (2) above by a spin coating method. Thereafter, this lens was irradiated with 1800 mJ / cm ² (100 mW / cm ² , 3 minutes) of UV light having a wavelength of 405 nm with a UV lamp in a nitrogen atmosphere (oxygen concentration of 500 ppm or less), and further at 100 ° C., 60 Curing treatment was performed for a minute to form a photochromic layer having a thickness of 40 μm.

  The photochromic lens which has a water-system resin layer and a photochromic layer in this order on the lens base material by the above process was obtained.

[Comparative Example 1-1]
A photochromic lens was obtained by the same method as in the above example except that the ultraviolet polymerization initiator was not added to the aqueous resin layer.

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.
(2) Evaluation of photochromic characteristics (fading speed) The transmittance at a wavelength of 550 nm (hereinafter referred to as “initial transmittance”) in the uncolored state of the photochromic lenses obtained in Examples and Comparative Examples is spectrophotometric made by Otsuka Electronics. It was measured by a meter. Next, the photochromic layer surface of each photochromic lens is irradiated with light through an aeromass filter using a xenon lamp, and the photochromic layer is colored to transmit the transmittance at a wavelength of 550 nm (hereinafter referred to as “transmission during color development”). Rate ")). Thereafter, from the time when the light irradiation was stopped, the time required for the transmittance to reach [(initial transmittance−transmittance during color development) / 2] (hereinafter referred to as “half-life”) was determined. The results are shown in Table 1. The slower the half-life, the higher the film hardness (polymerization proceeds).

[Example 2-1]
A photochromic lens was produced in the same manner as in Example 1-1 except that an organic hard coat layer was formed on the lens substrate by the following method, and an aqueous resin layer was formed on the hard coat layer. Thereby, the photochromic lens which has an organic type hard-coat layer, a water-system resin layer, and a photochromic layer in this order on the lens base material was obtained.
(Formation of organic hard coat layer)
In a glass container equipped with a stirrer, 47 parts by mass of γ-glycidoxypropyltrimethoxysilane, thermoplastic polyurethane (trade name “Coatron KYU-1” manufactured by Sanyo Chemical Industries, Ltd., resin content 40% by mass) 32 masses Part, 10 parts by mass of acetic acid, 40 parts by mass of diacetone alcohol (hereinafter abbreviated as DAA), and while stirring, 12 parts by mass of 0.01 N hydrochloric acid was added dropwise in about 2 hours, followed by stirring for 24 hours. γ-Glycidoxypropyltrimethoxysilane was hydrolyzed. Next, 120 parts by mass of isopropyl alcohol (hereinafter abbreviated as IPA) -dispersed colloidal silica (trade name “OSCAL1432”, solid content of 30% by mass) manufactured by Catalyst Chemical Industry Co., Ltd., 10 parts by mass of acetic acid and 56 parts by mass of DAA were added for 2 hours. Stir. Subsequently, 48 parts by mass of propylene glycol monomethyl ether, 24 parts by mass of IPA, 5 parts by mass of aluminum acetylacetone, and 0.3 part by mass of a silicone-based surfactant (trade name “Y-7006” manufactured by Nippon Unicar Co., Ltd.) are sufficiently added. After stirring, aging was performed for 48 hours to prepare a hard coating composition. The average particle size of the silica colloid particles in “OSCAL1432” is 10 to 20 nm.
A polycarbonate substrate is immersed in a 10% by weight sodium hydroxide aqueous solution at 60 ° C. for 5 minutes and sufficiently washed with pure water / dried, and then a dipping method using the hard coating composition prepared above. Coating was performed at a pulling rate of 20 cm / min, and a hard coat layer having a thickness of 3 μm was formed by heating and curing at 100 ° C. for 60 minutes.

[Comparative Example 2-1]
A photochromic lens was obtained by the same method as in the above example except that the ultraviolet polymerization initiator was not added to the aqueous resin layer.

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

[Example 3-1]
A photochromic lens was produced in the same manner as in Example 1-1 except that a polyurethane urea base material (trade name Phoenix, manufactured by HOYA Corporation) was used as the lens base material. Thereby, the photochromic lens which has a water-system resin layer and a photochromic layer in this order on the lens base material was obtained.

[Comparative Example 3-1]
A photochromic lens was obtained by the same method as in the above example except that the ultraviolet polymerization initiator was not added to the aqueous resin layer.

  The obtained photochromic lens was evaluated by the above method. The results are shown in Table 3.

Evaluation Results In all Examples and Comparative Examples, the curability of the photochromic layer was better in the Examples than in the Comparative Examples. From this result, the leaching component from the lens base material causes poor curing in the photochromic layer, and this can be suppressed by including in the aqueous resin layer the same type of polymerization initiator as the polymerization initiator contained in the photochromic layer. Can be confirmed. In addition, poor curing in the photochromic layer also causes poor adhesion between the photochromic layer and the lower primer layer. Therefore, it is advantageous for obtaining a lens having excellent durability to suppress the defective curing.

  The photochromic lens of the present invention is suitable as a spectacle lens that requires excellent photoresponsiveness and durability.

Claims (5)

A method for producing a photochromic lens having a photochromic layer containing a photochromic dye and a resin component on a plastic lens substrate,
Forming an aqueous resin layer on a plastic lens substrate by applying and drying an aqueous resin composition containing a resin component and an aqueous solvent; and
Forming a photochromic layer on the aqueous resin layer by applying a photochromic liquid containing a photochromic dye, a polymerizable component and a polymerization initiator, and then performing a polymerization treatment; and
The method for producing a photochromic lens, wherein the aqueous resin composition contains a polymerization initiator of the same type as a polymerization initiator contained in the photochromic liquid. The method for producing a photochromic lens according to claim 1, wherein the polymerization initiator is a radical photopolymerization initiator. The said aqueous resin composition is a manufacturing method of the photochromic lens of Claim 1 or 2 containing the polymeric component which has the same polymerization reaction format as the polymeric component contained in the said photochromic liquid. The method for producing a photochromic lens according to claim 3, wherein the polymerizable component contained in the aqueous resin composition is a resin component contained in the composition. A photochromic lens having a photochromic layer containing a photochromic dye and a resin component on a plastic lens substrate,
A photochromic lens having an aqueous resin layer between the plastic lens substrate and the photochromic layer, wherein the aqueous resin layer and the photochromic layer contain the same kind of polymerization initiator.