JP5961437B2 - Plastic eyeglass lenses - Google Patents

Description

 The present invention relates to a plastic spectacle lens dyed with a dye that absorbs light of a specific wavelength.

In recent years, plastic lenses are frequently used as spectacle lenses because of their advantages of being lightweight, excellent in impact resistance and easy to dye.
The purpose of using the spectacle lens includes, in addition to correcting visual acuity, reducing glare for visible light, accompanying discomfort, reduction in contrast, visual fatigue, and the like.
Ultraviolet rays are said to have various adverse effects on the human body. Accordingly, various UV-cut plastic lenses are manufactured and sold in eyeglass lenses in order to protect the eyes from UV rays.

However, recent research has shown that not only ultraviolet rays but also light in the blue region of visible light (380 nm to 500 nm) has a strong energy, causing damage to the retina, eye diseases, flickering of vision, and a decrease in contrast. It has been broken. This damage caused by light in the blue region of visible light is said to be “blue light hazard”. It has been shown that by cutting light in the blue region, glare is reduced and visibility and contrast are improved.
Furthermore, it is generally known that the energy of light is half proportional to the wavelength of light, and the scattered light energy of Rayleigh scattering is known to be half proportional to the fourth power of the wavelength. Therefore, it is considered that by cutting light in the blue region of 380 nm to 500 nm and reducing the light energy received by the eyes, damage to the retina, eye diseases, flickering of the visual field, and reduction in contrast can be prevented.

Further, as one of the countermeasures against visible light other than blue, there is a method of imparting a so-called anti-glare property to the spectacle lens. For example, visible light near 585 nm can be selectively absorbed. A method of incorporating a neodymium compound into an eyeglass lens (for example, see Patent Documents 1 and 2) and a method of incorporating an organic dye into an eyeglass lens (for example, see Patent Document 3) are known.
Furthermore, as a method of imparting anti-glare property to a plastic lens using a variety of coloring methods and selectively shielding as much as possible in a specific wavelength range, it is molded into an aqueous dye solution. A method of immersing and dyeing a later plastic lens (for example, see Patent Document 4), or a coating solution in which a cobalt compound or a specific organic dye is blended in a monomer is applied onto the plastic lens, and the coating solution is applied. A method of forming a coating film on a plastic lens by curing (see, for example, Patent Documents 5 to 7) is known.
As described above, the spectacle lens has an appropriate light-shielding property while maintaining a satisfactory visibility as much as possible by avoiding excessive or inappropriate light-shielding that degrades the visibility more than necessary. Is required to be granted.

Japanese Patent No. 3044017 International Publication No. 96/00247 JP 2008-134618 A Japanese Patent Publication No.53-39910 Japanese Patent Laid-Open No. 5-5860 Japanese Patent Laid-Open No. 5-45610 JP-A-2-254401

 The present invention has been made in view of the above circumstances, and an object of the present invention is to provide a plastic spectacle lens excellent in absorption performance of visible light having a specific wavelength.

According to the first aspect of the present invention, a plastic substrate composed of a thermosetting resin or a thermoplastic resin, and a pigment that absorbs light in a specific wavelength region are included on at least one surface of the plastic substrate. A plastic spectacle lens comprising: a dyeing layer containing the dye formed by applying and heating a dyeing solution, wherein the dyeing layer comprises at least one surface of the plastic substrate and the surface thereof A layer composed of the plastic base material and the dye dispersed in the plastic base material in a uniform depth range, and the dye absorbs visible light measured as a chloroform solution or a toluene solution. In the spectroscopic spectrum, a plastic having a main absorption peak with a half-value width of 40 nm to 140 nm between wavelengths of 380 nm to 650 nm. Click spectacle lens is provided.

According to the second aspect of the present invention, there is provided a plastic spectacle lens in which one or two or more component layers are formed on at least one surface of the plastic substrate.

 According to the third aspect of the present invention, the dye has a main absorption peak having a half-value width of 40 nm to 60 nm between wavelengths of 380 nm to 480 nm in a visible light absorption spectrum measured as a chloroform solution or a toluene solution. A plastic spectacle lens is provided.

 According to the fourth aspect of the present invention, the dye has a main absorption peak having a half-value width of 40 nm to 90 nm between wavelengths of 500 nm to 560 nm in a visible light absorption spectrum measured as a chloroform solution or a toluene solution. A plastic spectacle lens is provided.

 According to the fifth aspect of the present invention, the dye has a main absorption peak having a half-value width of 40 nm to 140 nm between wavelengths 590 nm to 650 nm in a visible light absorption spectrum measured as a chloroform solution or a toluene solution. A plastic spectacle lens is provided.

 According to a sixth aspect of the present invention, there is provided a plastic spectacle lens in which the dyeing layer contains a dye.

 According to a seventh aspect of the present invention, there is provided a plastic spectacle lens in which at least one of the component layers is formed from an organic resin coating agent.

 According to an eighth aspect of the present invention, there is provided a plastic spectacle lens in which the organic resin coating agent is a thermoplastic organic resin coating agent or a thermosetting organic resin coating agent.

 According to a ninth aspect of the present invention, there is provided a plastic spectacle lens in which at least one of the component layers is a hard coat layer.

 According to a tenth aspect of the present invention, there is provided a plastic spectacle lens in which at least one of the component layers is a primer layer in contact with the hard coat layer.

 According to an eleventh aspect of the present invention, there is provided a plastic spectacle lens in which the dyeing layer contains at least one organic dye different from the dye.

 ADVANTAGE OF THE INVENTION According to this invention, the plastic spectacle lens excellent in the absorption performance of the visible light of a specific wavelength can be provided.

It is the transmittance | permeability curve which shows the result of having measured the spectral transmittance in the center part of the plastic spectacle lens of Examples 1-3 and Comparative Examples 1 and 2. FIG.

An embodiment of a plastic spectacle lens will be described.
Note that this embodiment is specifically described in order to better understand the gist of the invention, and does not limit the present invention unless otherwise specified.

[First embodiment]
The plastic spectacle lens of this embodiment contains a plastic substrate and a dye that is formed on at least one surface of the plastic substrate (one surface or both surfaces of the plastic substrate) and absorbs light in a specific wavelength range. And a dyed layer.

The plastic substrate has a predetermined refractive index and power adjusted according to the user of the spectacles, and determines the optical characteristics of the plastic spectacle lens.
As a material constituting the plastic substrate, a thermosetting resin or a thermoplastic resin is used. For example, acrylic resin, thiourethane resin, methacrylic resin, allyl resin, episulfide resin, polycarbonate resin, polyurethane Resin, polyester resin, polystyrene resin, polyether sulfone resin, poly-4-methylpentene-1 resin, diethylene glycol bisallyl carbonate resin (CR-39), polyvinyl chloride resin, allyl diglycol carbonate resin, halogen -Containing copolymers, sulfur-containing copolymers, and the like.

 The refractive index (nd) of the plastic substrate is selected from, for example, 1.50, 1.60, 1.67, and 1.74. When the refractive index of the plastic substrate is 1.60 or more, an acrylic resin, a methacrylic resin, a thiourethane resin, an episulfide resin, or the like is preferably used as the plastic substrate.

 The thickness of a plastic base material is not specifically limited, Usually, center thickness is 0.7 mm-17.0 mm.

 The dyeing layer is formed by applying and heating a dyeing solution containing a dye that absorbs light in a specific wavelength region on at least one surface of a plastic substrate. It is a layer in which a dye is dispersed in at least one surface and a range of a uniform depth from the surface. That is, the dyeing layer is a layer composed of a plastic base material as a main material and a pigment dispersed in the plastic base material within a range of a uniform depth from at least one surface of the plastic base material. is there.

The dye that absorbs light in a specific wavelength region contained in the dyed layer is a main absorption peak having a half-value width of 40 nm to 140 nm between wavelengths of 380 nm to 650 nm in a visible light absorption spectrum measured as a chloroform solution or a toluene solution. What has is used. Note that the phrase “the dye is a chloroform solution or a toluene solution” means that the dye is dissolved in chloroform or toluene to prepare a chloroform solution or a toluene solution of the dye.
Specifically, the dye contained in the staining layer includes (a) a main absorption peak having a half-value width of 40 nm to 60 nm between wavelengths 380 nm to 480 nm in a visible light absorption spectrum measured as a chloroform solution or a toluene solution. (B) having a main absorption peak with a full width at half maximum of 40 nm to 90 nm between wavelengths 500 nm to 560 nm (hereinafter referred to as “dye (b)”). And (c) those having a main absorption peak with a half-value width of 40 nm to 140 nm (hereinafter referred to as “dye (c)”) between wavelengths 590 nm to 650 nm.

Examples of the dye (a) include benzylidene compounds (manufactured by Orient Chemical Industries, SOM-5-0098), monoazo compounds, disazo compounds, indole compounds, azomethine compounds, and the like.
Examples of the dye (b) include oil-soluble phthalein dyes and other mixtures (manufactured by Orient Chemical Industries, SOC-5-0002), monoazo compounds, disazo compounds, xanthene compounds, and the like.
Examples of the dye (c) include oil-soluble triallylmethane dye derivatives (manufactured by Orient Chemical Industries, SOM-5-0100), phthalocyanine compounds, triphenylmethane compounds, anthraquinone compounds, and the like.

The thickness of the dyed layer, that is, the depth from the surface of the plastic substrate is preferably 0.1 μm to 200 μm, and more preferably 0.2 μm to 130 μm.
When the thickness of the dye layer is less than 0.1 μm, the dye layer may not be able to obtain visible light absorption performance in the target wavelength region. On the other hand, if the thickness of the dyed layer exceeds 200 μm, the transmittance of visible light in the dyed layer may be too low, making it unsuitable for use as a spectacle lens.

Moreover, the dyeing | staining layer may contain dye other than said pigment | dye.
The dye is not particularly limited, and examples thereof include disperse dyes, reactive dyes, direct dyes, composite dyes, acid dyes, metal complex dyes, vat dyes, sulfur dyes, azo dyes, fluorescent dyes, and resin coloring dyes. And other functional dyes. These dyes may be used alone or in a combination of two or more. When two or more dyes are used in combination, the combination and ratio may be appropriately selected according to the purpose.

Moreover, the dyeing | staining layer may contain at least 1 sort (s) of organic type pigments different from the pigment | dye which absorbs light of said specific wavelength range.
Examples of organic dyes include organic cyan, cyanine, coumarin, anthraquinone, phthalocyanine, methine, azomethine, polymethine, oxazine, azo, styryl, porphyrin, pyromethene, oxonol And squarylium-based compounds.

 As the dyeing solution used for forming the dyed layer, a solution containing at least a dye that absorbs light in the specific wavelength region, a binder resin, and a solvent is used. Further, the dye may contain the above dye.

Content of the pigment | dye in a dyeing | staining liquid is not specifically limited, It is preferable that it is 0.001-10 mass%, and it is more preferable that it is 0.005-5 mass%.
When the content of the dye in the dyeing liquid is less than 0.001% by mass, the finally obtained dyeing layer may not obtain visible light absorption performance in the target wavelength region. On the other hand, if the content of the dye in the dyeing liquid exceeds 10% by mass, the visible light transmittance in the dyed layer finally obtained may be too low, making it unsuitable for use as a spectacle lens.

 Examples of the binder resin include vinyl chloride resin, vinyl acetate resin, polyamide, polyethylene, polycarbonate, polystyrene, phenol resin, polypropylene, fluororesin, butyral resin, melamine resin, polyvinyl alcohol, cellulose resin, alkyd resin, acrylic resin, epoxy Resins, urethane resins, polyester resins, silicon resins and the like can be mentioned. These resin may be used individually by 1 type, and 2 or more types may be mixed and used for it. Furthermore, a copolymer of these resins can also be used.

The content of the binder resin in the dyeing liquid is not particularly limited, and is preferably 0.01 to 5% by mass, and more preferably 0.05 to 3% by mass.
By setting the content of the binder resin in the dyeing liquid in the above range, when dyeing at least one surface of the plastic base material to be the lens base material, that is, at least one surface of the plastic base material is dyed. Workability at the time of forming is improved.

The content of the dye in the dyeing liquid is not particularly limited, and is preferably 0.001 to 10% by mass, and more preferably 0.005 to 5% by mass.
When the content of the dye in the dyeing liquid is less than 0.001% by mass, it may be difficult to obtain a sufficiently dyed dyeing layer. On the other hand, when the content of the dye in the dyeing liquid exceeds 5% by mass, aggregation may occur depending on the dye, which may make it difficult to use.

 The solvent is not particularly limited as long as it can sufficiently dissolve the above-mentioned pigment, binder and dye. For example, methanol, ethanol, methyl ethyl ketone, ethylene glycol monoethyl ether, acetone, isobutyl alcohol , Ethyl ether, chlorobenzene, isobutyl acetate, isopropyl acetate, isopentyl acetate, ethyl acetate, butyl acetate, pentyl acetate, methyl acetate, cyclohexanol, 1,4-dioxane, N, N-dimethylformamide, tetrahydrofuran, 1,1,1 -Trichloroethane (methyl chloroform), toluene, 1-butanol, 2-butanol, methyl isobutyl ketone, methyl cyclohexanone, methyl butyl ketone, acetophenone, benzoate, methyl ester Rohekisan and the like. These solvents may be used alone or in combination of two or more.

 You may add various additives, such as a pH adjuster, a viscosity modifier, a leveling agent, a matting agent, a stabilizer, a ultraviolet absorber, antioxidant, to a dyeing liquid as needed.

Examples of methods for forming a dyed layer on at least one surface of a plastic substrate using a dyeing solution containing a dye that absorbs light in a specific wavelength range include the following two methods.
(1) Method of forming a dye layer on at least one surface of a plastic substrate by applying a dye solution on at least one surface of the plastic substrate to form a coat layer and then heating (coat method)
(2) A method in which a plastic substrate is immersed in a heated dyeing solution to form a dyed layer on at least one surface of the plastic substrate (dip method)
Of these two methods, the coating method (1) is preferred because the amount of dyeing solution used is small and the production cost can be reduced.

In the coating method, as a method for coating (coating) the dyeing liquid onto the surface of the plastic substrate, a normal coating method such as brush coating, dip coating, spin coating, roll coating, spray coating, flow coating, or ink jet coating is used. .
The staining solution may be applied to one surface of the plastic substrate, but may be applied to both surfaces of the plastic substrate in order to increase the dyeing concentration.
The coating thickness of the dyeing liquid on the surface of the plastic substrate is not particularly limited and can be adjusted as appropriate, for example, in the range of 0.01 μm to 500 μm.

In the coating method, when dyeing at a uniform dye density (formation of a dye layer) on the entire surface of at least one surface of the plastic substrate, a coating solution is applied to at least one surface of the plastic substrate by applying a dye solution. After the formation, heat treatment is performed to penetrate and diffuse the pigment and dye in the dyeing liquid (coat layer) from the surface of the plastic substrate to the inside.
As for the heating conditions of the plastic substrate after the dyeing solution is applied and the coating layer is formed, the heating temperature is preferably 70 to 180 ° C., and the heating time is preferably 10 minutes to 180 minutes.
As a heating method, heating by an air oven, heating by far infrared irradiation, heating by UV irradiation, or the like is used.

 In the coating method, when dyeing with a gentle concentration gradient (formation of a dye layer) along at least one surface of a plastic substrate, a staining solution is applied to at least one surface of the plastic substrate. After forming the coating layer, the surface on which the coating layer is formed is heated while gradually changing the heating region, so that the dye is formed so as to form a gentle concentration gradient inside the plastic substrate. Can penetrate.

 A coating layer is formed by applying a dyeing solution to at least one surface of the plastic substrate, and after heat treatment, the plastic substrate is washed, and the coating layer on at least one surface of the plastic substrate ( By removing the applied dyeing solution), the plastic spectacle lens of the present embodiment, which is composed of a plastic substrate and a dyed layer formed on at least one surface of the plastic substrate, is obtained.

 The method of cleaning the plastic substrate after the heat treatment is not particularly limited as long as the coating layer on at least one surface of the plastic substrate can be removed, or a method of wiping with an organic solvent, or an alkaline cleaner The method of washing by is preferred. Among these, a method of wiping with acetone or methyl ethyl ketone as the organic solvent is more preferable.

In the dip method, when a dyeing layer is formed on at least one surface of a plastic substrate, the plastic substrate is immersed in a heated dyeing solution, and the dye and dye in the dyeing solution are placed on the surface of the plastic substrate. Penetration and diffusion from inside to inside.
In the dip method, it is preferable to immerse the plastic substrate in a staining solution heated to 80 to 95 ° C. in order to permeate and diffuse the pigment and dye in the staining solution from the surface of the plastic substrate to the inside.

 After immersing the plastic substrate in the heated dyeing solution, the plastic substrate is washed, and the dyeing solution on at least one surface of the plastic substrate is removed. The plastic spectacle lens of this embodiment, which is composed of a dyed layer formed on at least one surface, is obtained.

 The method for washing the plastic substrate after the immersion of the plastic substrate in the staining solution is not particularly limited as long as the staining solution on at least one surface of the plastic substrate can be removed. A method of washing with an organic solvent or a method of wiping with an organic solvent is preferred.

 As described above, in a plastic spectacle lens manufactured by applying a dyeing solution containing a dye that absorbs light in a specific wavelength range to at least one surface of a plastic substrate and heating it, at least one of the plastic substrate In the range of the surface and a uniform depth from the surface, the dye penetrates and diffuses to form a dyed layer.

[Second Embodiment]
The plastic spectacle lens of this embodiment is formed on the surface of at least one of the plastic substrate, one or more component layers formed on at least one surface of the plastic substrate, and the plastic substrate and component layers. And a dyeing layer containing a dye that absorbs light in a specific wavelength range.
That is, in the plastic spectacle lens of this embodiment, when the component layer is formed on one surface of the plastic substrate, one surface of the plastic substrate (interface between the plastic substrate and the component layer), the plastic substrate A dyed layer is formed on at least one of the other surface (the surface on which the component layer is not formed) and the surface of the component layer (the surface of the component layer that is not in contact with the plastic substrate). In addition, when component layers are formed on both surfaces of the plastic substrate, one surface of the plastic substrate (interface between the plastic substrate and the component layer) and the other surface of the plastic substrate (plastic substrate and component) A dyed layer is formed on at least one of the layer interface), the surface of the component layer on one surface of the plastic substrate, and the surface of the component layer on the other surface of the plastic substrate.

At least one of the component layers may be formed from an organic resin coating agent.
As the organic resin coating agent, a thermoplastic organic resin coating agent or a thermosetting organic resin coating agent is used. For example, (meth) acrylic resin, polyether resin, polyurethane resin, melamine resin, polyester resin And silicon-based resin. This organic resin coating agent is used for the purpose of improving impact resistance and the like, for example, when the plastic substrate is brittle.

Further, at least one of the component layers may be composed of a hard coat layer.
Examples of the material for forming the hard coat layer include acrylic resins, polyurethane resins, melamine resins, and silicon resins.
The hard coat layer includes composite oxide particles mainly composed of titanium oxide and an organosilicon compound for imparting abrasion resistance, moisture resistance, hot water resistance, heat resistance, weather resistance, etc. to the surface of the optical lens. And as a main component.
The composite oxide particles are composed of inorganic oxide fine particles having a high refractive index such as titanium oxide and zirconium oxide.

Further, at least one of the component layers may be composed of a primer layer in contact with the hard coat layer. Thereby, the adhesive strength with respect to other members (layers), such as a plastic base material of a hard-coat layer, can be raised.
Examples of the material for forming the primer layer include acrylic resins, polyurethane resins, polyester resins, polyvinyl alcohol resins, melamine resins, and polyvinyl acetals.
The materials for forming the primer layer include various leveling agents for improving coating properties, ultraviolet absorbers and antioxidants for improving weather resistance, dyes and pigments, and others. Well-known additives for adding functions such as improving the membrane performance can be used in combination.

Further, at least the component layer may be composed of an antireflection coating layer.
The material for forming the antireflection coating layer is not particularly limited, and examples thereof include known materials used for spectacle lenses.

 Hereinafter, the present embodiment will be described more specifically with reference to examples and comparative examples, but the present embodiment is not limited to the following examples.

"Example 1"
A benzylidene compound (manufactured by Orient Chemical Industry Co., Ltd., SOM-5-0098) having a main absorption peak with a half-value width of 45 nm between wavelengths of 430 nm to 440 nm in a visible light absorption spectrum measured as a chloroform solution as a dye. A dyeing solution was prepared by blending 0.05% by mass, 20% by mass of polyvinyl alcohol as a binder resin, and 79.95% by mass of methyl ethyl ketone as a solvent, and stirring them all day and night.

Next, the above-described staining solution is applied to the entire surface of one side of a plastic lens (Nikon Essilor, Nikonlite 3AS, size 80φ, center thickness 2 mm) having a refractive index of 1.60 by spin coating. A 0.3 mm coat layer was formed.
Next, the plastic lens with the coating layer formed on the surface is heated by an air oven at 140 ° C. for 1 hour, and the benzylidene compound contained in the dyeing liquid (coating layer) is introduced from the surface of the plastic lens. The surface of the plastic lens was stained by penetrating and diffusing.
Next, the plastic lens was cooled, and the surface on which the coating layer was formed was wiped with acetone, thereby removing the coating layer on the surface of the plastic lens.

Next, a coating solution is applied to the surface of the dyed plastic lens by an immersion method, and is cured by heating. A urethane-based impact-resistant coating having a thickness of about 1 μm and a silicone-based scratch resistance having a thickness of about 2 μm. The improvement hard coat was laminated in this order.
Next, a multilayer antireflection coating made of an inorganic oxide having a thickness of about 0.3 μm was formed on the silicone-based scratch-resistant hard coat by vacuum deposition, and the plastic spectacle lens of Example 1 was formed. Obtained.

The spectral transmittance at the central portion of the plastic spectacle lens of Example 1 was measured, and the transmittance curve thereof is shown in FIG. 1 together with Comparative Example 1 described later.
The spectral transmittance was measured using a Hitachi High-Technologies U-4100 spectrophotometer with a slit width of 5 nm and a scan speed of 300 nm / min.
As a result, the plastic spectacle lens of Example 1 effectively cuts short-wavelength light with a wavelength of 380 nm to 460 nm.

Further, the time for reading 63 words with different shades was measured through the plastic spectacle lens of Example 1. The results are shown in Table 1.
From the results in Table 1, it was confirmed that when the object (word) was viewed through the plastic spectacle lens of Example 1, the visibility and contrast were improved.

"Example 2"
In a visible light absorption spectrum measured as a chloroform solution as a dye, an oil-soluble phthalein dye having a main absorption peak with a half width of 48 nm between wavelengths 540 nm to 550 nm, and other mixtures (manufactured by Orient Chemical Industry Co., Ltd.) , SOC-5-0002), 0.3% by mass, 20% by mass of polyvinyl alcohol as a binder resin, and 79.7% by mass of methyl ethyl ketone as a solvent, and stirring them all day and night, A staining solution was prepared.

Next, the above-described staining solution is applied to the entire surface of one side of a plastic lens (Nikon Essilor, Nikonlite 3AS, size 80φ, center thickness 2 mm) having a refractive index of 1.60 by spin coating. A 0.3 mm coat layer was formed.
Next, an air oven is used to heat the plastic lens having a coating layer formed on the surface at 140 ° C. for 1 hour, and the oil-soluble phthalein dye contained in the dyeing liquid (coating layer) and other mixtures. Was permeated and diffused from the surface of the plastic lens to dye the surface of the plastic lens.
Next, the plastic lens was cooled, and the surface on which the coating layer was formed was wiped with acetone, thereby removing the coating layer on the surface of the plastic lens.

Next, a coating solution is applied to the surface of the dyed plastic lens by an immersion method, and is cured by heating. A urethane-based impact-resistant coating having a thickness of about 1 μm and a silicone-based scratch resistance having a thickness of about 2 μm. The improved hard coat was laminated in this order to obtain the plastic spectacle lens of Example 2.
Next, a multilayer antireflection coating made of an inorganic oxide having a thickness of about 0.3 μm was formed on the silicone-based scratch-resistant hard coat by vacuum deposition, and the plastic spectacle lens of Example 2 was formed. Obtained.

The spectral transmittance at the center of the plastic spectacle lens of Example 2 was measured, and the transmittance curve thereof is shown in FIG. 1 together with Comparative Example 1 described later.
The method for measuring the spectral transmittance was the same as in Example 1.
As a result, the plastic spectacle lens of Example 2 effectively cuts short wavelength light having a wavelength of 540 nm to 580 nm.

Further, the time for reading 63 words with different shades was measured through the plastic spectacle lens of Example 2. The results are shown in Table 1.
From the results in Table 1, it was confirmed that when the object (word) was viewed through the plastic spectacle lens of Example 2, the visibility and contrast were improved.

"Example 3"
In the visible light absorption spectrum measured as a chloroform solution as a dye, an oil-soluble triallylmethane dye derivative having a main absorption peak with a full width at half maximum of 139 nm between wavelengths of 620 nm to 630 nm (SOM- manufactured by Orient Chemical Co., Ltd.) 5-0100), 0.1% by mass of polyvinyl alcohol as a binder resin, 20% by mass of polyvinyl alcohol, and 79.9% by mass of methyl ethyl ketone as a solvent. Prepared.

Next, the above-described staining solution is applied to the entire surface of one side of a plastic lens (Nikon Essilor, Nikonlite 3AS, size 80φ, center thickness 2 mm) having a refractive index of 1.60 by spin coating. A 0.3 mm coat layer was formed.
Next, the plastic lens with the coating layer formed on the surface is heated by an air oven at 140 ° C. for 1 hour, and the benzylidene compound contained in the dyeing liquid (coating layer) is introduced from the surface of the plastic lens. The surface of the plastic lens was stained by penetrating and diffusing.
Next, the plastic lens was cooled, and the surface on which the coating layer was formed was wiped with acetone, thereby removing the coating layer on the surface of the plastic lens.

Next, a coating solution is applied to the surface of the dyed plastic lens by an immersion method, and is cured by heating. A urethane-based impact-resistant coating having a thickness of about 1 μm and a silicone-based scratch resistance having a thickness of about 2 μm. The improvement hard coat was laminated in this order.
Next, a multilayer antireflection coating made of an inorganic oxide having a thickness of about 0.3 μm was formed on the silicone-based scratch-resistant hard coat by vacuum deposition, and the plastic spectacle lens of Example 3 was formed. Obtained.

The spectral transmittance at the center of the plastic spectacle lens of Example 3 was measured, and the transmittance curve thereof is shown in FIG. 1 together with Comparative Example 1 described later.
The method for measuring the spectral transmittance was the same as in Example 1.
As a result, the plastic spectacle lens of Example 3 effectively cuts short-wavelength light with a wavelength of 560 nm to 660 nm.

Further, the time for reading 63 words with different shades was measured through the plastic spectacle lens of Example 3. The results are shown in Table 1.
From the results in Table 1, it was confirmed that when the object (word) was viewed through the plastic spectacle lens of Example 3, the visibility and contrast were improved.

"Comparative Example 1"
In the same manner as in Example 1, the surface of the plastic lens (Nikon Essilor, Nikonlite 3AS, size 80φ, center thickness 2 mm) with a refractive index of 1.60 was used without staining. Comparative example of forming a urethane anti-impact coating having a thickness of about 1 μm, a hard coating having a silicone-based scratch resistance having a thickness of about 2 μm, and a multilayer antireflection coating made of an inorganic oxide having a thickness of about 0.3 μm 1 plastic spectacle lens was obtained.

The spectral transmittance at the center of the plastic spectacle lens of Comparative Example 1 was measured, and the transmittance curve is shown in FIG.
The method for measuring the spectral transmittance was the same as in Example 1.
As a result, the plastic spectacle lens of Comparative Example 1 hardly cut light with a wavelength of 380 nm to 650 nm.

Further, the time for reading 63 words with different shades was measured through the plastic spectacle lens of Comparative Example 1. The results are shown in Table 1.
From the results in Table 1, it was confirmed that when the object (word) was viewed through the plastic spectacle lens of Comparative Example 1, there was almost no change in visibility and contrast.

"Comparative Example 2"
In the same manner as in Example 1, the surface of the plastic lens having a refractive index of 1.67 (Neop-4, size 75φ, center thickness 2 mm) (both sides) was not stained. Comparative example of forming a urethane anti-impact coating having a thickness of about 1 μm, a hard coating having a silicone-based scratch resistance having a thickness of about 2 μm, and a multilayer antireflection coating made of an inorganic oxide having a thickness of about 0.3 μm Two plastic spectacle lenses were obtained.
In addition, the plastic spectacle lens of Comparative Example 2 is not only excellent in anti-glare property in the above-mentioned Patent Document 3, but also excellent in image and color discrimination in a bright field of view. It is a lens that appears to have a very clear contrast between red, yellow, and green.

The spectral transmittance at the center of the plastic spectacle lens of Comparative Example 2 was measured, and the transmittance curve is shown in FIG.
The method for measuring the spectral transmittance was the same as in Example 1.
As a result, the plastic spectacle lens of Comparative Example 2 cuts light having a wavelength of 570 nm to 605 nm.

Further, the time for reading 63 words with different shades was measured through the plastic spectacle lens of Comparative Example 2. The results are shown in Table 1.
From the results of Table 1, it was confirmed that when the object (word) was viewed through the plastic spectacle lens of Comparative Example 2, the visibility and contrast were not improved so much.

Claims (11)

Formed by applying and heating a plastic substrate composed of a thermosetting resin or thermoplastic resin and a dyeing solution containing a dye that absorbs light in a specific wavelength region on at least one surface of the plastic substrate. A plastic spectacle lens comprising a dyed layer containing the dye,
The dyeing layer is a layer composed of the plastic substrate and the pigment dispersed in the plastic substrate within a range of a uniform depth from at least one surface of the plastic substrate. ,
The plastic spectacle lens, wherein the dye has a main absorption peak having a half-value width of 40 nm to 140 nm between wavelengths of 380 nm to 650 nm in a visible light absorption spectrum measured as a chloroform solution or a toluene solution. The plastic one or more layers of the component layer on at least one surface of the substrate is formed, a plastic spectacle lens according to claim 1.   The plastic according to claim 1, wherein the dye has a main absorption peak having a half-value width of 40 nm to 60 nm between wavelengths of 380 nm to 480 nm in a visible light absorption spectrum measured as a chloroform solution or a toluene solution. Eyeglass lens.   3. The plastic according to claim 1, wherein the dye has a main absorption peak having a half width of 40 nm to 90 nm between wavelengths of 500 nm to 560 nm in a visible light absorption spectrum measured as a chloroform solution or a toluene solution. Eyeglass lens.   The plastic according to claim 1 or 2, wherein the dye has a main absorption peak having a half-value width of 40 nm to 140 nm between wavelengths 590 nm to 650 nm in a visible light absorption spectrum measured as a chloroform solution or a toluene solution. Eyeglass lens.   The plastic spectacle lens according to claim 1, wherein the dye layer contains a dye.   The plastic spectacle lens according to any one of claims 2 to 6, wherein at least one of the component layers is formed of an organic resin coating agent.   The plastic eyeglass lens according to claim 7, wherein the organic resin coating agent is a thermoplastic organic resin coating agent or a thermosetting organic resin coating agent.   The plastic spectacle lens according to claim 2, wherein at least one of the component layers is a hard coat layer.   The plastic spectacle lens according to claim 9, wherein at least one of the component layers is a primer layer in contact with the hard coat layer.   The plastic spectacle lens according to any one of claims 1 to 10, wherein the dye layer contains at least one organic dye different from the dye.

Images