Plastic lens and eye glasses

Abstract

Provided are: a plastic lens having a lens base material, a photochromic layer that is formed on one surface of the lens base material and is obtained by curing a polymerizable composition for forming a photochromic layer sensitive to light in a specific wavelength region, and a coating material that covers an edge surface of the lens base material and inhibits light, which is within at least a partial region of the specific wavelength region, from entering the lens base material; and eye glasses.

Description

Plastic lenses and eyeglasses

[0001] The present disclosure relates to plastic lenses and eyeglasses, and more particularly to a plastic lens having photochromic properties that make it less likely for arc-shaped color unevenness to occur at the periphery of the plastic lens, and eyeglasses equipped with the plastic lens.

[0002] Eyeglasses equipped with plastic lenses that exhibit a property of developing a color under light in a predetermined wavelength range (e.g., outdoors) and fading under light outside the predetermined wavelength range (e.g., indoors) (photochromic properties) are highly convenient because they eliminate the need to change glasses when moving between indoors and outdoors. The photochromic plastic lenses are required to have minimal color unevenness in order to maintain a good field of vision even after color development.

[0003]

[0004] A method for imparting photochromic properties to a plastic lens includes applying a layer of a composition (polymerizable composition for forming a photochromic layer) containing a photochromic compound and a polymerizable compound having photochromic properties to the surface of a lens substrate, and curing the applied polymerizable composition for forming a photochromic layer by irradiating it with light to form a cured coating layer (photochromic layer) having photochromic properties. Patent Document 1 discloses a polymerizable composition for forming a photochromic layer, which has an absorbance of 0.100 or more at 420 nm and an absorbance of 0.015 or more at 430 nm, and in which, when measuring the color density, the value of the color density measured with light of wavelengths of 380 nm or shorter blocked by the value of the color density measured without blocking light of wavelengths of 380 nm or shorter is 0.60 or more.

[0004] Japanese Patent Application Laid-Open No. 2018-097173

[0005] However, Patent Document 1 does not particularly consider the suppression of color unevenness in a plastic lens having photochromic properties, and plastic lenses having a photochromic layer formed by curing the polymerizable composition for forming a photochromic layer disclosed in Patent Document 1 are sometimes found to have arc-shaped color unevenness in their peripheral portions, and it cannot necessarily be said that the suppression of color unevenness is sufficient.

[0006] An object of one aspect of the present disclosure is to provide a plastic lens having photochromic properties that make it less likely to develop arc-shaped color unevenness at the peripheral edge of the plastic lens, and eyeglasses equipped with the plastic lens.

[0007] Embodiments of the present disclosure relate to the following [1] to [8]. [1] A plastic lens comprising: a lens substrate; a photochromic layer formed on one surface of the lens substrate and cured from a polymerizable composition for forming a photochromic layer that is sensitive to light in a specific wavelength range; and a coating material that covers an edge surface of the lens substrate and suppresses the incidence of light in at least a portion of the specific wavelength range onto the lens substrate. [2] The plastic lens according to [1] above, wherein the polymerizable composition for forming a photochromic layer is sensitive to light in a wavelength range of 280 to 780 nm, and the coating material has a maximum transmittance of 35% or less for light in a wavelength range of 280 to 450 nm. [3] The plastic lens according to [2] above, wherein the polymerizable composition for forming a photochromic layer contains a plurality of photochromic compounds, has an absorbance at 420 nm of 0.100 or more, and an absorbance at 430 nm of 0.015 or more, and, when measuring the color density, a value obtained by dividing the color density measured with light of wavelengths of 380 nm or less blocked by the color density measured with light of wavelengths of 380 nm or less not blocked is 0.60 or more. [4] The plastic lens according to [1] above, wherein the polymerizable composition for forming a photochromic layer is sensitive to light in a wavelength range of 280 to 380 nm, the covering material has a transmittance of 15% or less for light of a wavelength of 365 nm, and the lens substrate has a transmittance of 10% or more for light of a wavelength of 365 nm. [5] The plastic lens according to [4] above, wherein the polymerizable composition for forming a photochromic layer contains: (meth)acrylate; and a photochromic compound. [6] The plastic lens according to any one of [1] to [5] above, further comprising a primer layer between the lens substrate and the photochromic layer. [7] The plastic lens according to any one of [1] to [6] above, wherein the lens substrate has a thickness of less than 2.2 mm in a central portion and a peripheral portion that is thicker than the central portion. [8] Eyeglasses comprising the plastic lens according to any one of [1] to [7] above.

[0008] As a result of extensive research to solve the above-mentioned problems, the inventors discovered that by coating the edge surface of a lens substrate with a coating material that has a predetermined range of transmittance for light in a predetermined wavelength range, arc-shaped color unevenness is less likely to occur around the periphery of a plastic lens, leading to the completion of the present invention. While the detailed mechanism by which arc-shaped color unevenness occurs around the periphery of a plastic lens is unknown, the inventors speculate that it is because light incident from the edge surface of the lens substrate is reflected off the other surface of the lens substrate that does not have a photochromic layer, and this reflected light strikes the photochromic layer (Figure 2). Therefore, the inventors speculate that by coating the edge surface of the lens substrate and preventing light from entering, arc-shaped color unevenness is less likely to occur around the periphery of a plastic lens.

[0009] According to one aspect of the present disclosure, it is possible to provide a photochromic plastic lens that is less likely to develop arc-shaped color unevenness at the peripheral edge of the plastic lens, and eyeglasses equipped with the plastic lens.

[0010] 1 is a schematic diagram showing arc-shaped color unevenness occurring in the peripheral portion of a plastic lens, and FIG. 2 is a schematic diagram explaining the principle of occurrence of arc-shaped color unevenness occurring in the peripheral portion of a plastic lens, and FIG. 3 is a schematic diagram explaining a plastic lens according to one embodiment of the present disclosure.

[0011] The following description is based on an example of an embodiment of the present disclosure. However, the embodiments described below are merely examples for embodying the technical concept of the present disclosure, and the present disclosure is not limited to the following description. The present disclosure also includes any embodiment or combination of any of the features described herein. In the present disclosure and this specification, preferred specifications can be selected arbitrarily, and combinations of preferred specifications are considered more preferable. In the present disclosure and this specification, the expression "XX to YY" means "XX or more and YY or less." In the present disclosure and this specification, for preferred numerical ranges (e.g., ranges of content, etc.), lower and upper limits described in stages can be independently combined. For example, the expression "preferably 10 to 90, more preferably 30 to 60" can be combined with the "preferable lower limit (10)" and the "more preferable upper limit (60)" to form "10 to 60." Furthermore, in the numerical ranges described in the present disclosure and this specification, the upper or lower limit of the numerical range may be replaced with a value shown in the examples. In the present disclosure and this specification, a polymerizable composition refers to a composition containing a polymerizable compound. Furthermore, a polymerizable compound refers to a compound having a polymerizable group. In this disclosure and this specification, a "cured coating layer" refers to a cured polymerizable composition. For example, a cured coating layer obtained by curing a polymerizable composition for forming a primer layer is referred to as a primer layer, a cured coating layer obtained by curing a polymerizable composition for forming a photochromic layer is referred to as a photochromic layer, a cured coating layer obtained by curing a polymerizable composition for forming a protective layer is referred to as a protective layer, and a cured coating layer obtained by curing a polymerizable composition for forming a hardcoat layer is referred to as a hardcoat layer. In this disclosure and this specification, "on the surface of X" refers not only to "on the surface of X (contact state)" but also to "above the surface of X (non-contact state)." In this disclosure and this specification, "(meth)acrylate" refers to both acrylate and methacrylate. "Acrylate" refers to a compound having one or more acryloyl groups in one molecule. "Methacrylate" refers to a compound having one or more methacryloyl groups in one molecule.For (meth)acrylates, the functionality is the number of groups selected from the group consisting of acryloyl groups and methacryloyl groups contained in one molecule. Furthermore, "methacrylate" refers to a compound containing only methacryloyl groups as (meth)acryloyl groups, while a compound containing both acryloyl and methacryloyl groups as (meth)acryloyl groups is referred to as a (meth)acrylate. The acryloyl group may be contained in the form of an acryloyloxy group, and the methacryloyl group may be contained in the form of a methacryloyloxy group. In this disclosure and this specification, the term "(meth)acryloyl group" is used to encompass both acryloyl groups and methacryloyl groups, and the term "(meth)acryloyloxy group" encompasses both acryloyloxy groups and methacryloyloxy groups. In this disclosure and this specification, unless otherwise specified, the groups described may be substituted or unsubstituted. When a group has a substituent, examples of the substituent include an alkyl group (e.g., a linear alkyl group having 1 to 6 carbon atoms or a branched alkyl group having 1 to 6 carbon atoms), a hydroxyl group, an alkoxy group (e.g., an alkoxy group having 1 to 6 carbon atoms), a halogen atom (e.g., a fluorine atom, a chlorine atom, or a bromine atom), a cyano group, an amino group, a nitro group, an acyl group, a carboxy group, an aryl group, and a polyether group. Furthermore, the "carbon number" of a substituted group refers to the number of carbon atoms in the portion excluding the substituent. In the present disclosure and this specification, "linear alkyl group or branched alkyl group" does not include a cycloalkyl group. A linear alkyl group or branched alkyl group may be unsubstituted or may have a substituent. It is acceptable for a linear alkyl group or branched alkyl group to have a cycloalkyl group (e.g., a cyclohexyl group) as a substituent. In one embodiment, the linear alkyl group or branched alkyl group preferably does not have a cycloalkyl group as a substituent. In the present disclosure and this specification, "at least a portion of a specific wavelength range" may refer to either a portion or the entirety of the specific wavelength range. When the specific wavelength range is 280 to 380 nm, "at least a portion of the specific wavelength range" may be 365 nm, 300 to 360 nm, or 280 to 380 nm.In this disclosure and this specification, "viscosity" refers to a value measured using a vibration viscometer in an ambient atmosphere at 25°C. In this disclosure and this specification, "total amount" refers to the total amount of all components excluding the solvent, if a solvent is included. In this disclosure and this specification, "central portion of the lens substrate" refers to the portion within a radius of 5 mm from the center of the lens substrate. In this disclosure and this specification, "peripheral portion of the lens substrate" refers to the portion within a radius of 15 mm or more from the center of the lens substrate. In this disclosure and this specification, "mid-peripheral portion of the lens substrate" refers to the portion within a radius of more than 5 mm but less than 15 mm from the center of the lens substrate. In this disclosure and this specification, "plastic lens" may be a finished lens or a semi-finished lens. Semi-finished lenses are processed by polishing and grinding into lenses for actual use. In this disclosure and this specification, "finished lens" refers to a semi-finished lens that has been processed by polishing and grinding into a lens for actual use, or a lens molded into a lens for actual use. In this disclosure and this specification, the term "lens substrate thickness" refers to a value measured using a high-performance ABS Digimatic Indicator (ID-FNX series, manufactured by Mitutoyo Corporation) with terminals connected to the convex and concave surfaces of the lens substrate. In this disclosure and this specification, the term "cured coating layer thickness" refers to a value calculated from the analysis of film thickness values ​​using FFT (fast Fourier transform) after measuring the reflectance (interference waveform) of a sample using a non-contact film thickness measurement system (FF8, manufactured by System Road Corporation). In this disclosure and this specification, the term "solids content" refers to non-volatile content excluding volatile substances such as solvents, and includes liquid, starch syrup-like, and wax-like substances at room temperature. The total solid content can also be calculated from the charge amount. In this disclosure and this specification, the term "light irradiation intensity" refers to a value measured using an actinometer (UIT-250, manufactured by USHIO Corporation) by lighting a lens base 300 mm away from the center of the light source to the light receiving unit (center wavelength 365 mm).The term "exposure amount of light irradiation" in this disclosure and this specification refers to a value measured using an actinometer (UIT-250, manufactured by USHIO Corporation) by lighting a lens base 300 mm away from the center of the light source to the light receiving unit (center wavelength 365 mm), or the intensity of light irradiation (mW / cm. ２ ) × irradiation time (seconds). In this disclosure and this specification, "transmittance" refers to a value measured using a spectrophotometer (UH4150, manufactured by Hitachi High-Tech Corporation) by transmitting light separated by wavelength through a glass substrate on which a lens substrate or a coating material is disposed (dyed). "Maximum transmittance" refers to the transmittance value of the wavelength at which the transmittance is maximum within a specific wavelength range. In this disclosure and this specification, "room temperature" refers to the ambient temperature without temperature control such as heating or cooling, and is generally around 20°C, but is not limited to the above range as this may vary depending on the weather and season. In the present disclosure and this specification, the "absorbance at 420 nm and 430 nm" of a photochromic compound refers to a value measured at 23°C using a spectrophotometer (UV-1900i, manufactured by Shimadzu Corporation) and a quartz cell with a 10 mm optical path length (S15-UV-10, manufactured by GL Sciences Inc.) on a toluene solution of the photochromic compound (1.0 mM (millimolar)). Note that the absorbance at 420 nm and 430 nm in the case of a polymerizable composition for forming a photochromic layer is a value measured in the same manner as when the absorbance at 420 nm and 430 nm of the photochromic compound is measured, with the blending ratios of components other than the photochromic compound unchanged and the concentration of the photochromic compound in the composition for forming a photochromic layer adjusted to 1.0 mM. In the present disclosure and this specification, the "visible light sensitivity" of the photochromic compound and the polymerizable composition for forming a photochromic layer refers to the same value as the "visible light sensitivity" of a plastic lens provided with a photochromic layer. The "visible light sensitivity" of a plastic lens having a photochromic layer is the value of the color density of the plastic lens (ε ｃ) was measured in a state where light in the wavelength range of 380 nm or less was not blocked, and the color density (ε ｎ ) divided by (ε ｃ / ε ｎ ) of the plastic lens provided with the photochromic layer in the present disclosure and the present specification. ｃ and ε ｎ " was a plastic lens with a photochromic layer as a sample, and a xenon lamp capable of coloring the plastic lens was used at 23°C through an Aeromass filter AM2.0 and a UV cut filter capable of blocking 99.8% of light with wavelengths of 380 nm or less, with a beam intensity of 365 nm = 10 μW / cm on the sample surface. ２ , 245nm=24μW / cm ２ The color density at the maximum absorption wavelength was measured, and the color density when a UV cut filter was used was ε ｃ , the color density without a UV cut filter is ε ｎ It was decided.

[0012] [Plastic Lens] The plastic lens according to one aspect of the present disclosure will be described in further detail below.

[0013] In the present disclosure and this specification, a plastic lens is not particularly limited as long as it comprises a lens substrate, a photochromic layer formed on one surface of the lens substrate and obtained by curing a photochromic layer-forming polymerizable composition that is sensitive to light in a specific wavelength range, and a coating material that covers the edge surface of the lens substrate and suppresses the incidence of light in a partial region within the specific wavelength range onto the lens substrate, and may or may not comprise a cured coating layer other than the photochromic layer. The cured coating layer other than the photochromic layer is not particularly limited, and examples include a primer layer, which will be described later. Furthermore, a cured coating layer other than the photochromic layer may or may not be present on the surface of the lens substrate opposite to the surface having the photochromic layer (hereinafter sometimes simply referred to as the "other surface of the lens substrate").

[0014] In one embodiment of the plastic lens of the present disclosure and this specification, the photochromic layer-forming polymerizable composition is sensitive to light in a wavelength range of 280 to 780 nm, and the covering material has a maximum transmittance of 35% or less for light in a wavelength range of 280 to 450 nm (hereinafter, this may be simply referred to as "plastic lens (1)"). In another embodiment of the plastic lens of the present disclosure and this specification, the photochromic layer-forming polymerizable composition is sensitive to light in a wavelength range of 280 to 380 nm, the covering material has a transmittance of 15% or less for light with a wavelength of 365 nm, and the lens substrate has a transmittance of 10% or more for light with a wavelength of 365 nm (hereinafter, this may be simply referred to as "plastic lens (2)"). Hereinafter, the plastic lens (1) and the plastic lens (2) will be described in more detail.

[0015] <Plastic Lens (1)> The plastic lens (1) comprises a lens substrate, a photochromic layer formed on one surface of the lens substrate and cured from a photochromic layer-forming polymerizable composition that is sensitive to light in a specific wavelength range, and a coating material that coats the edge surface of the lens substrate and suppresses the incidence of light in at least a portion of the specific wavelength range onto the lens substrate. The photochromic layer-forming polymerizable composition is sensitive to light in a wavelength range of 280 to 780 nm, and the coating material is not particularly limited as long as it has a maximum transmittance of 35% or less for light in a wavelength range of 280 to 450 nm. The coating material may or may not have a cured coating layer other than the photochromic layer. The cured coating layer other than the photochromic layer is not particularly limited, and examples include a primer layer, a protective layer, a hard coat layer, and other functional layers, as described below. Furthermore, the surface of the lens substrate opposite the surface having the photochromic layer (hereinafter sometimes simply referred to as the "other surface of the lens substrate") may or may not have a cured coating layer other than the photochromic layer.

[0016] (Lens Substrate) The lens substrate (hereinafter sometimes simply referred to as "lens substrate (1)") included in the plastic lens (1) will be described in more detail below.

[0017] The material for the lens substrate (1) is not particularly limited and includes, for example, (meth)acrylic resins; styrene resins; polycarbonate resins; allyl resins; allyl carbonate resins such as diethylene glycol bisallyl carbonate resin (CR-39); vinyl resins; polyester resins; polyether resins; urethane resins obtained by reacting an isocyanate compound with a hydroxy compound such as diethylene glycol; thiourethane resins obtained by reacting an isocyanate compound with a polythiol compound; cured products (generally referred to as transparent resins) obtained by curing a curable composition containing a (thio)epoxy compound having one or more disulfide bonds in the molecule; and oxides such as boric oxide, aluminum oxide, and silicon oxide. These may be used alone or in combination of two or more.

[0018] The type of the lens substrate (1) is not particularly limited, and examples thereof include a lens substrate (1) used for spectacles, a lens substrate (1) used for goggles, and the like.

[0019] The color of the lens substrate (1) is not particularly limited, and it may be colorless (an undyed lens) or dyed.

[0020] The refractive index of the lens substrate (1) is not particularly limited and may be, for example, 1.50 to 1.75. In this disclosure and this specification, the refractive index refers to the refractive index for light of mercury e-line at 546.07 nm.

[0021] The focal point of the lens substrate (1) is not particularly limited, and examples thereof include single-focus, multi-focus, and progressive-addition lenses.

[0022] The surface of the lens substrate (1) is not particularly limited and may be, for example, a convex, concave, or flat surface. In a typical lens substrate (1), the object-side surface is convex and the eyeball-side surface is concave, but the present disclosure is not limited thereto. One surface of the lens substrate (1) is not particularly limited and may be, for example, a convex, concave, or flat surface. The other surface of the lens substrate (1) is not particularly limited and may be, for example, a convex, concave, or flat surface.

[0023] The thickness of the central portion of the lens substrate (1) is not particularly limited, but from the viewpoint of optical design, it is preferably less than 9.1 mm, more preferably 0.8 to 2.4 mm, and particularly preferably 0.8 mm or more and less than 2.2 mm. The thickness of the peripheral portion of the lens substrate (1) is not particularly limited, but from the viewpoint of optical design, it is preferably thicker than the central portion, more preferably 0.8 to 16.5 mm, and particularly preferably 1.6 to 13.0 mm.

[0024] The maximum transmittance of the lens substrate (1) for light in the wavelength range of 280 to 780 nm is not particularly limited, but from the viewpoint of fully exhibiting the effects of the present disclosure, it is preferably 10% or more, more preferably 30% or more, even more preferably 50% or more, and particularly preferably 70% or more.

[0025] (Primer Layer) The plastic lens (1) may further include a primer layer, if necessary. The primer layer that the plastic lens (1) may include (hereinafter, may be simply referred to as "primer layer (1)") will be described in more detail below. In this disclosure and this specification, the primer layer means one that has the function of adhering (bonding) substances (e.g., a lens substrate and a cured coating layer) located on both surfaces of the primer layer. The primer layer (1) also has this function. There are no particular restrictions on the location of the primer layer (1), but from the viewpoint of improving adhesion between the lens substrate and the photochromic layer, it is preferably between the lens substrate (1) described above and the photochromic layer (1) described below.

[0026] The thickness of the primer layer (1) is not particularly limited, but is preferably 1 to 20 μm, more preferably 3 to 15 μm, and particularly preferably 4 to 10 μm. If the thickness is equal to or greater than the lower limit of the above range, good adhesion between the lens substrate and the photochromic layer is achieved, while if the thickness is equal to or less than the upper limit of the above range, a good appearance is more easily achieved.

[0027] The primer layer (1) is a cured coating layer obtained by curing a polymerizable composition for forming a primer layer (hereinafter, sometimes simply referred to as the "primer layer composition"). One form of the primer layer composition used to form the primer layer (1) can be a primer layer composition prepared from a known adhesive (hereinafter, sometimes simply referred to as the "primer layer composition (1)"). The adhesive is not particularly limited, and examples thereof include moisture-curing polyurethane-based adhesives, polyisocyanate-polyester two-component adhesives, polyisocyanate-polyether two-component adhesives, polyisocyanate-polyacrylic two-component adhesives, polyisocyanate-polyurethane elastomer two-component adhesives, epoxy-based adhesives, epoxy-polyurethane two-component adhesives, polyester-based adhesives, polyurethane urea-based one-component adhesives, and water-dispersible polyurethane-based adhesives. These may be used alone or in combination of two or more. The primer layer composition (1) may or may not contain a solvent.

[0028] The commercially available product of the primer layer composition (1) is not particularly limited, and examples thereof include TR-SC-P (manufactured by Tokuyama Corporation) and NJ321A (manufactured by Tokuyama Corporation). These may be used alone or in combination of two or more.

[0029] The primer layer (1) is obtained by drying and curing the primer layer composition (1). The primer layer (1) can be formed on the lens substrate by applying an adhesive to the lens substrate and drying the applied adhesive. The application method is not particularly limited, and known application methods can be used, such as spin coating and dip coating. These methods may be used alone or in combination. Of these, spin coating is preferred from the viewpoint of uniformity of application. The drying treatment is not particularly limited, and can be carried out, for example, by placing the lens substrate in an atmosphere of room temperature to 100°C for 5 minutes to 24 hours.

[0030] (Photochromic Layer) The photochromic layer of the plastic lens (1) is a cured coating layer obtained by curing a photochromic layer-forming polymerizable composition that is sensitive to light in a specific wavelength range. Hereinafter, the photochromic layer of the plastic lens (1) (hereinafter, sometimes simply referred to as "photochromic layer (1)") will be described in more detail.

[0031] One form of the photochromic layer (1) can be a cured polymerizable composition for forming a photochromic layer (hereinafter, sometimes simply referred to as a "photochromic layer composition") that responds to light in the wavelength range of 280 to 780 nm and exhibits photochromic properties. The position of the photochromic layer (1) is not particularly limited, but is preferably on the above-mentioned primer layer (1) from the viewpoint of adhesion to the lens substrate.

[0032] The wavelength range to which the photochromic layer (1) is sensitive is not particularly limited as long as it is 280 to 780 nm, depending on the type of polymerization initiator, and is preferably 280 to 600 nm, more preferably 280 to 500 nm, and particularly preferably 280 to 430 nm. If the wavelength is equal to or greater than the lower limit of the above range, destruction of the photochromic compound by ultraviolet rays is easily suppressed, and if the wavelength is equal to or less than the upper limit of the above range, the photochromic layer (1) is easily sensitive in the visible light region.

[0033] The thickness of the photochromic layer (1) is not particularly limited, but is preferably 5 to 80 μm, more preferably 10 to 70 μm, and particularly preferably 15 to 60 μm. If the thickness is equal to or greater than the lower limit of the above range, a good appearance is easily ensured, and if the thickness is equal to or less than the upper limit of the above range, color development at a high density is easily achieved.

[0034] ((Photochromic Layer Composition)) One embodiment of the photochromic layer composition sensitive to light in the wavelength range of 280 to 780 nm can be a photochromic layer composition (hereinafter sometimes simply referred to as "photochromic layer composition (1)") that contains a plurality of photochromic compounds, has an absorbance at 420 nm of 0.100 or more, an absorbance at 430 nm of 0.015 or more, and, when measuring the color density, the value of the color density measured with light of wavelengths of 380 nm or less blocked by the value of the color density measured with light of wavelengths of 380 nm or less not blocked is 0.60 or more. Furthermore, the photochromic layer composition (1) may further contain a polymerizable compound, a polymerization initiator, a dye, etc., as necessary. The various components contained in the photochromic layer composition (1) will be described in more detail below.

[0035] —Plural Photochromic Compounds— The plural photochromic compounds contained in the composition for photochromic layer (1) are not particularly limited, so long as the composition for photochromic layer (1) has an absorbance at 420 nm of 0.100 or more and an absorbance at 430 nm of 0.015 or more, and, when measuring the color density, the value obtained by dividing the color density measured in a state where light with a wavelength of 380 nm or less is blocked by the color density measured in a state where light with a wavelength of 380 nm or less is not blocked is 0.60 or more. All of the photochromic compounds contained in the composition for photochromic layer (1) may be photochromic compounds having an absorbance at 420 nm of 0.100 or more, an absorbance at 430 nm of 0.015 or more, and a visible light sensitivity of 0.60 or more (hereinafter, these may be simply referred to as “first photochromic compounds”). The photochromic compounds contained in the photochromic layer composition (1) may include a first photochromic compound and a photochromic compound that does not satisfy at least one of the following conditions: an absorbance at 420 nm of 0.100 or more, an absorbance at 430 nm of 0.015 or more, and a visible light sensitivity of 0.60 or more. Furthermore, the photochromic compounds contained in the photochromic layer composition (1) may include a first photochromic compound and a compound that has an absorbance at 420 nm of less than 0.100, an absorbance at 430 nm of less than 0.015, and a visible light sensitivity of less than 0.60 (hereinafter, sometimes simply referred to as a "second photochromic compound"). Among these, from the viewpoint of excellent antiglare properties and transmittance, a compound that includes a second photochromic compound with low visible light responsiveness and high transmittance and a first photochromic compound with high visible light responsiveness and excellent antiglare properties is preferred.

[0036] --First Photochromic Compound-- The first photochromic compound is not particularly limited, and examples thereof include fulgide compounds, chromene compounds, spirooxazine compounds, and the like. These may be used alone or in combination of two or more. Among these, a chromene compound having an indeno[2,1-f]naphtho[1,2-b]pyran skeleton represented by the following formula (11) is preferably used, particularly from the viewpoint of absorption characteristics in a colorless state (state before color development):

[0037] ...(11)

[0038] In formula (11), R １ and R ２ are each independently a hydrogen atom, a hydroxyl group, a cyano group, a nitro group, an alkyl group, a haloalkyl group, a cycloalkyl group, an alkoxy group, an amino group, a heterocyclic group containing a nitrogen ring atom and bonded to the aromatic hydrocarbon ring or aromatic heterocyclic ring via the nitrogen atom, a formyl group, a hydroxycarbonyl group, an alkylcarbonyl group, an alkoxycarbonyl group, a halogen atom, an aralkyl group, an aralkoxy group, an aryloxy group, or an aryl group, provided that R １ , and R ２ cannot both be hydrogen atoms.

[0039] In formula (11), R ３ is a hydroxyl group, a nitro group, an alkyl group, a cycloalkyl group, an alkoxy group, an amino group, a heterocyclic group that contains a nitrogen atom and is bonded to the aromatic hydrocarbon ring or aromatic heterocyclic ring at the nitrogen atom, a formyl group, a hydroxycarbonyl group, an alkylcarbonyl group, an alkoxycarbonyl group, a halogen atom, an aralkyl group, an aralkoxy group, an aryloxy group, or an aryl group.

[0040] The alkyl group is not particularly limited, but is preferably an alkyl group having 1 to 6 carbon atoms. Examples of the alkyl group having 1 to 6 carbon atoms include, but are not limited to, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, and a hexyl group.

[0041] The haloalkyl group is not particularly limited, but is preferably an alkyl group having 1 to 6 carbon atoms substituted with a fluorine atom, a chlorine atom, or a bromine atom. The alkyl group having 1 to 6 carbon atoms substituted with a fluorine atom, a chlorine atom, or a bromine atom is not particularly limited, and examples thereof include a trifluoromethyl group, a tetrafluoroethyl group, a chloromethyl group, a 2-chloroethyl group, and a bromomethyl group.

[0042] The cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 8 carbon atoms. The cycloalkyl group having 3 to 8 carbon atoms is not particularly limited, and examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group.

[0043] The alkoxy group is not particularly limited, but is preferably an alkoxy group having 1 to 6 carbon atoms. Examples of the alkoxy group having 1 to 6 carbon atoms are not particularly limited, and include, for example, a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, a sec-butoxy group, and a tert-butoxy group.

[0044] The amino group may be an amino group (—NH ２ ), and one or two hydrogen atoms may be substituted. The substituent on the amino group is not particularly limited, and examples thereof include an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 7 carbon atoms, an aryl group having 6 to 14 carbon atoms, and a heteroaryl group having 4 to 14 carbon atoms. Among these, an amino group, a methylamino group, a dimethylamino group, an ethylamino group, a diethylamino group, a phenylamino group, and a diphenylamino group are preferred.

[0045] The heterocyclic group containing a ring-membered nitrogen atom and bonded to the aromatic hydrocarbon ring or aromatic heterocyclic ring via the nitrogen atom is not particularly limited, but suitable examples include aliphatic heterocyclic groups such as a morpholino group, piperidino group, pyrrolidinyl group, piperazino group, and N-methylpiperazino group; and aromatic heterocyclic groups such as an indolinyl group. Furthermore, the heterocyclic group may have a substituent. The substituent is not particularly limited, but suitable examples include an alkyl group. The heterocyclic group having a substituent is not particularly limited, but suitable examples include a 2,6-dimethylmorpholino group, a 2,6-dimethylpiperidino group, and a 2,2,6,6-tetramethylpiperidino group.

[0046] The alkylcarbonyl group is not particularly limited, but suitable examples include alkylcarbonyl groups having 2 to 7 carbon atoms. The alkylcarbonyl group having 2 to 7 carbon atoms is not particularly limited, and examples include an acetyl group and an ethylcarbonyl group.

[0047] The alkoxycarbonyl group is not particularly limited, but suitable examples include alkoxycarbonyl groups having 2 to 7 carbon atoms. The alkoxycarbonyl group having 2 to 7 carbon atoms is not particularly limited, and examples include a methoxycarbonyl group and an ethoxycarbonyl group.

[0048] The halogen atom is not particularly limited, and examples thereof include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0049] The aralkyl group is not particularly limited, but suitable examples include aralkyl groups having 7 to 11 carbon atoms. The aralkyl group having 7 to 11 carbon atoms is not particularly limited, and examples include a benzyl group, a phenylethyl group, a phenylpropyl group, a phenylbutyl group, and a naphthylmethyl group.

[0050] The aralkoxy group is not particularly limited, but suitable examples include aralkoxy groups having 7 to 11 carbon atoms. The aralkoxy group having 7 to 11 carbon atoms is not particularly limited, and examples include a benzyloxy group and a naphthylmethoxy group.

[0051] The aralkyl group and aralkoxy group are not particularly limited, but preferably 1 to 7 hydrogen atoms on the benzene or naphthalene ring are substituted with any of the above-mentioned hydroxyl groups, alkyl groups, haloalkyl groups, cycloalkyl groups, alkoxy groups, amino groups, cyano groups, nitro groups, and halogen atoms, and more preferably 1 to 4 hydrogen atoms on the benzene or naphthalene ring are substituted with any of the above-mentioned hydroxyl groups, alkyl groups, haloalkyl groups, cycloalkyl groups, alkoxy groups, amino groups, cyano groups, nitro groups, and halogen atoms.

[0052] The aryloxy group is not particularly limited, but suitable examples include aryloxy groups having 6 to 12 carbon atoms. The aryloxy group having 6 to 12 carbon atoms is not particularly limited, and examples include a phenyloxy group and a naphthyloxy group.

[0053] The aryl group is not particularly limited, but suitable examples include aryl groups having 6 to 14 carbon atoms. The aryl group having 6 to 14 carbon atoms is not particularly limited, and examples include a phenyl group, a 1-naphthyl group, and a 2-naphthyl group.

[0054] The aryloxy group is not particularly limited, but preferably has 1 to 7 hydrogen atoms on the benzene or naphthalene ring substituted with any of the alkyl, haloalkyl, cycloalkyl, alkoxy, amino, and halogen atoms, and more preferably has 1 to 4 hydrogen atoms on the benzene or naphthalene ring substituted with any of the alkyl, haloalkyl, cycloalkyl, alkoxy, amino, and halogen atoms.

[0055] One form of the above formula (11) can be a formula (11) having the following groups:

[0056] In formula (11), R １ , R ２ and R ３From the viewpoint of shifting the wavelength of the absorption edge of the photochromic compound to a longer wavelength and improving absorbance, at least two of the groups are preferably the alkyl group, cycloalkyl group, alkoxy group, amino group, heterocyclic group containing a ring-membered nitrogen atom and bonded to the aromatic hydrocarbon ring or aromatic heterocyclic ring via the nitrogen atom, aralkyl group, aralkoxy group, aryloxy group, or aryl group. The remaining group may be any of the groups exemplified above. １ is an alkoxy group, an aryloxy group, or an aryl group, and R ２ is an alkoxy group, an amino group, a heterocyclic group containing a nitrogen atom and bonded to the aromatic hydrocarbon ring or aromatic heterocyclic ring at the nitrogen atom, an aryloxy group, or an aryl group, and R ３ is more preferably an alkoxy group, an amino group, an aryloxy group, or an aryl group. １ is at least one group selected from the group consisting of an alkoxy group, an aryloxy group, and an aryl group, and R ２ is an alkoxy group, an amino group, an aryloxy group, or an aryl group, and R ３ However, an alkoxy group is particularly preferred.

[0057] In formula (11), R ４ and R ５ are each independently an aryl group, a heteroaryl group, or an alkyl group. Among these, from the viewpoint of exhibiting excellent photochromic properties and fading speed, the above R ４ and R ５ Preferably, at least one of the R ４ and R ５ and R are more preferably both an aryl group or a heteroaryl group. ４ and R ５ It is more preferable that at least one of the R ４ and R ５ It is particularly preferred that both groups are any of the groups shown in (i) to (iii) below.

[0058] (i) an aryl group or heteroaryl group having an alkyl group or an alkoxy group as a substituent, (ii) an aryl group or heteroaryl group having an amino group as a substituent, (iii) an aryl group or heteroaryl group having a heterocyclic group having a nitrogen atom as a ring-member heteroatom and bonding to the aryl group or heteroaryl group at the nitrogen atom as a substituent. The positions and total number of substituents substituting the aryl group or heteroaryl group in the above (i) to (iii) are not particularly limited, but from the viewpoint of exhibiting excellent photochromic properties, when the aryl group is a phenyl group, the substitution position is preferably the 3- or 4-position, and the number of substituents in this case is preferably 1.

[0059] The aryl group in the above (i) to (iii) is not particularly limited, and examples thereof include a 4-methylphenyl group, a 4-methoxyphenyl group, a 3,4-dimethoxyphenyl group, a 4-n-propoxyphenyl group, a 4-(N,N-dimethylamino)phenyl group, a 4-(N,N-diethylamino)phenyl group, a 4-(N,N-diphenylamino)phenyl group, a 4-morpholinophenyl group, a 4-piperidinophenyl group, a 3-(N,N-dimethylamino)phenyl group, and a 4-(2,6-dimethylpiperidino)phenyl group.

[0060] The total number of substituents on the heteroaryl group in the above (i) to (iii) is not particularly limited, but is preferably 1. Such heteroaryl groups are not particularly limited, and examples thereof include a 4-methoxythienyl group, a 4-(N,N-dimethylamino)thienyl group, a 4-methylfuryl group, a 4-(N,N-diethylamino)furyl group, a 4-(N,N-diphenylamino)thienyl group, a 4-morpholinopyrrolinyl group, a 6-piperidinobenzothienyl group, and a 6-(N,N-dimethylamino)benzofuranyl group.

[0061] The above R ４ and R ５are each independently selected from the above (i) to (iii), the chromene compound (photochromic compound) becomes a double-peak compound having two absorption peaks. This double-peak compound is suitable for use because it allows for easy color adjustment and there is little change in color over time due to deterioration. In particular, it is suitable for use when mixing with other photochromic compounds to adjust the color.

[0062] In formula (11), R ６ and R ７ are each independently a hydrogen atom, a hydroxyl group, an alkyl group, a haloalkyl group, a cycloalkyl group, an alkoxy group, an alkoxyalkyl group, a formyl group, a hydroxycarbonyl group, an alkylcarbonyl group, an alkoxycarbonyl group, a halogen atom, an aralkyl group, an aralkoxy group, an aryloxy group, or an aryl group. Among these, a hydroxyl group, an alkyl group such as a methyl group, or an alkoxy group such as a methoxy group is preferred. ６ and R ７ The alkyl group, haloalkyl group, cycloalkyl group, alkoxy group, alkylcarbonyl group, alkoxycarbonyl group, halogen atom, aralkyl group, aralkoxy group, aryloxy group and aryl group represented by the above R １ , R ２ and R ３ The same groups as those described above under R ６ and R ７ The alkoxyalkyl group represented by is not particularly limited, but suitable examples include alkoxyalkyl groups having 2 to 7 carbon atoms. The alkoxyalkyl group having 2 to 7 carbon atoms is not particularly limited, and examples include a methoxymethyl group, a methoxyethyl group, a methoxy n-propyl group, a methoxy n-butyl group, an ethoxyethyl group, and an n-propoxypropyl group. ６ and R ７ may, together with the carbon atom at position 13 to which they are bonded, form an aliphatic ring having 3 to 20 ring carbon atoms, a condensed polycycle in which an aromatic ring or an aromatic heterocycle is condensed to the aliphatic ring, a heterocycle having 3 to 20 ring atoms, or a condensed polycycle in which an aromatic ring or an aromatic heterocycle is condensed to the heterocycle.

[0063] The aliphatic ring is not particularly limited, and examples thereof include a cyclopentane ring, a cyclohexane ring, a cyclooctane ring, a cycloheptane ring, a norbornane ring, a bicyclononane ring, and an adamantane ring.

[0064] The condensed polycyclic ring in which an aromatic ring or an aromatic heterocyclic ring is condensed with the aliphatic ring is not particularly limited, and examples thereof include a phenanthrene ring.

[0065] The fused polycyclic ring in which an aromatic ring or an aromatic heterocyclic ring is fused to the heterocyclic ring is not particularly limited, and examples thereof include a phenylfuran ring and a biphenylthiophene ring.

[0066] In formula (11), R ６ and R ７ In order to increase the fading rate while maintaining high double peak properties, ６ and R ７ is bonded to forms a ring together with the carbon atom at position 13, more preferably forms an aliphatic ring or a condensed polycycle in which an aromatic ring or an aromatic heterocycle is condensed to an aliphatic ring, and from the viewpoint of reducing initial coloration due to thermochromism, it is particularly preferable that it forms an aliphatic ring.

[0067] The above R ６ and R ７ The aliphatic ring formed by is not particularly limited, and suitable examples thereof include an unsubstituted aliphatic hydrocarbon ring; an aliphatic hydrocarbon ring having at least one substituent selected from the group consisting of an alkyl group, a haloalkyl group, a cycloalkyl group, an alkoxy group, an amino group, an aralkyl group, an aryl group, and a halogen atom; and the like. The alkyl group, haloalkyl group, cycloalkyl group, alkoxy group, amino group, aralkyl group, aryl group, and halogen atom are the same as those of the above-mentioned R １ , R ２ and R ３ The same groups as those described above under R ６ and R ７The aliphatic hydrocarbon ring formed by is not particularly limited, and examples thereof include monocyclic rings such as a cyclohexane ring, a cyclooctane ring, and a cycloheptane ring; bicyclic rings such as a norbornane ring, a bicyclo[3,2,1]octane ring, a bicyclo[4,2,0]octane ring, a bicyclo[3,3,0]octane ring, a bicyclo[3,3,1]nonane ring, a bicyclo[4,3,0]nonane ring, and a bicyclo[6,3,0]undecane ring; tricyclic rings such as an adamantane ring; and rings substituted with at least one lower alkyl group having 4 or less carbon atoms, such as a methyl group. Among these, a monocyclic ring or a bicyclic ring is preferred from the viewpoint of minimizing initial coloration due to thermochromism while maintaining high double peak properties and a fast fading rate. ６ and R ７ Specific examples of the monocyclic or bicyclic ring formed by the formula (12) include those represented by the following formula (12): In the following formula (12), the carbon atom marked with 13 is the carbon atom at the 13th position.

[0068] ...(12)

[0069] Among the above monocyclic or bicyclic rings, a cyclooctane ring, a 3,3,5,5-tetramethylcyclohexane ring, a 4,4-diethylcyclohexane ring, a 4,4-dimethylcyclohexane ring, and a bicyclo[4,3,0]nonane ring are preferred.

[0070] --Second Photochromic Compound-- The second photochromic compound is not particularly limited, and examples thereof include fulgide compounds, chromene compounds, and spirooxazine compounds. These compounds are disclosed in many documents, such as JP-A Nos. 2-28154, 62-288830, WO 94 / 22850, and WO 96 / 14596. The second photochromic compound is not particularly limited, but from the viewpoint of photochromic properties such as color density, initial coloring, durability, and fading rate, it is preferably a chromene compound having an indeno[2,1-f]naphtho[1,2-b]pyran skeleton other than the chromene compound represented by formula (1). From the viewpoint of color density and fading rate, it is more preferably a chromene compound having an indeno[2,1-f]naphtho[1,2-b]pyran skeleton having a molecular weight of 540 or more, and particularly preferably a chromene compound represented by formula (21):

[0071] ...(21)

[0072] In formula (21), R ３０ is a hydrogen atom.

[0073] In formula (21), R １０ and R ２０ are each independently a hydrogen atom, a hydroxyl group, a cyano group, a nitro group, an alkyl group, a haloalkyl group, a cycloalkyl group, an alkoxy group, an amino group, a heterocyclic group that contains a nitrogen ring atom and is bonded to the aromatic hydrocarbon ring or aromatic heterocyclic ring at the nitrogen atom, a formyl group, a hydroxycarbonyl group, an alkylcarbonyl group, an alkoxycarbonyl group, a halogen atom, an aralkyl group, an aralkoxy group, an aryloxy group, an arylthio group, or an aryl group.

[0074] The chromene compound (second photochromic compound) represented by the above formula (21) has a substituent (R ３０ ) is a hydrogen atom, and is therefore a compound different from the chromene compound represented by the formula (1). １０ and R ２０ is as described above, and the groups exemplified above are R １ , R２ , and R ３ The same groups as those mentioned in the above are exemplified, and the preferred groups are also the same.

[0075] The above R １０ and R ２０ The arylthio group represented by is not particularly limited, but suitable examples include arylthio groups having 6 to 12 carbon atoms. The arylthio group having 6 to 12 carbon atoms is not particularly limited, and examples include a phenylthio group and a naphthylthio group. When the arylthio group is a phenylthio group, it preferably has a substituent at at least one ortho position, and the substituent is preferably an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, or an aryl group having 6 to 14 carbon atoms.

[0076] The above R １０ and R ２０ Although there are no particular limitations on R, from the viewpoint of achieving a high level of both transparency and antiglare properties, R are preferably each independently a hydrogen atom, an alkyl group, an alkoxy group, an amino group, an aryloxy group, an arylthio group, or an aryl group. １０ and R ２０ In the formula, the groups other than hydrogen atoms are as described above, and the groups exemplified above are R １ , R ２ , and R ３ The same groups as those mentioned in the above are exemplified, and the preferred groups are also the same.

[0077] In formula (21), R ４０ and R ５０ are each independently R in the above formula (1). ４ and R ５ The groups are the same as those shown above, and the preferred groups are also the same.

[0078] In formula (21), R ６０ and R ７０ is R in the formula (1). ６ and R ７ is the same group as ６０ and R ７０From the viewpoint of imparting excellent antiglare properties and transparency to the photochromic layer, it is preferable that R, together with the carbon atom at the 13th position to which they are bonded, form an aliphatic ring having 3 to 20 ring carbon atoms, a condensed polycyclic ring in which an aromatic ring or an aromatic heterocyclic ring is condensed to the aliphatic ring, a heterocyclic ring having 3 to 20 ring atoms, or a condensed polycyclic ring in which an aromatic ring or an aromatic heterocyclic ring is condensed to the heterocyclic ring. When forming such a cyclic group, preferred groups are R ６ , and R ７ Further, the same groups as those described in R ６０ , and R ７０ is R ６ and R ７ In the above, it is preferably a monocyclic or bicyclic ring as exemplified as a preferred group.

[0079] Examples of the second photochromic compound include compounds of the following formula (22) and formula (23).

[0080] ...(22)

[0081] ...(23)

[0082] The multiple photochromic compounds contained in the composition for photochromic layer (1) are not particularly limited, but from the viewpoint of excellent antiglare properties and transmittance, it is preferable that the composition contain a second photochromic compound having low visible light responsiveness and high transmittance, and a first photochromic compound having high visible light responsiveness and excellent antiglare properties.

[0083] When the plurality of photochromic compounds include first and second photochromic compounds, the first photochromic compound is not particularly limited, but preferably has an absorbance at 420 nm of 0.150 to 0.800, an absorbance at 430 nm of 0.020 to 0.500, and a visible light sensitivity of 0.61 to 1.0, more preferably an absorbance at 420 nm of 0.200 to 0.700, an absorbance at 430 nm of 0.050 to 0.300, and a visible light sensitivity of 0.65 to 0.95, and particularly preferably an absorbance at 420 nm of 0.300 to 0.600, an absorbance at 430 nm of 0.070 to 0.200, and a visible light sensitivity of 0.70 to 0.90.

[0084] When the plurality of photochromic compounds include a first and a second photochromic compound, the second photochromic compound is not particularly limited, but preferably has an absorbance at 420 nm of 0.001 or more and less than 0.120, an absorbance at 430 nm of 0.000 or more and less than 0.015, and a visible light sensitivity of 0.10 or more and less than 0.60, more preferably an absorbance at 420 nm of 0.005 to 0.100, an absorbance at 430 nm of 0.001 to 0.013, and a visible light sensitivity of 0.20 to 0.55, and particularly preferably an absorbance at 420 nm of 0.02 to 0.095, an absorbance at 430 nm of 0.005 to 0.012, and a visible light sensitivity of 0.30 to 0.55.

[0085] The amount of the second photochromic compound to be blended is not particularly limited as long as the composition for photochromic layer (1) has an absorbance at 420 nm of 0.0100 or more, an absorbance at 430 nm of 0.015 or more, and a visible light sensitivity of 0.60 or more. However, from the viewpoint of ease of adjusting the color tone of the resulting photochromic layer, the amount is preferably 1 to 100 parts by mass, more preferably 10 to 50 parts by mass, per 100 parts by mass of the first photochromic compound.

[0086] The content of the plurality of photochromic compounds is not particularly limited, but is preferably 0.5 to 5.0 parts by mass per 100 parts by mass of the polymerizable compound described below, from the viewpoint of making the composition for photochromic layer (1) have an absorbance at 420 nm of 0.0100 or more, an absorbance at 430 nm of 0.015 or more, and a visible light sensitivity of 0.60 or more.

[0087] -Polymerizable Compound- The photochromic layer composition (1) may further contain, as necessary, a polymerizable compound that contributes to the curing of the photochromic layer composition (1). The polymerizable compound that may be contained in the photochromic layer composition (1) is not particularly limited, and examples thereof include the polymerizable compounds that may be contained in the primer layer composition (3), photochromic layer composition (2), and protective layer composition (2) described below. The content of the polymerizable compound is not particularly limited, but is preferably 70 to 99% by mass relative to 100% by mass of the photochromic layer composition (1).

[0088] -Polymerization initiator- The photochromic layer composition (1) may further contain, as necessary, a polymerization initiator that contributes to the curing of the photochromic layer composition (1). The polymerizable compound that may be contained in the photochromic layer composition (1) is not particularly limited, and known compounds can be used, including, for example, polymerization initiators that may be contained in the primer layer composition (3), photochromic layer composition (2), and protective layer composition (2) described below. The content of the polymerization initiator is not particularly limited, but is preferably 0.1 to 10 parts by mass per 100 parts by mass of the photochromic layer composition (1).

[0089] -Dye- The photochromic layer composition (1) may further contain, if necessary, a dye that contributes to improving the antiglare properties of the photochromic layer. While the dye is not particularly limited, from the above viewpoint, dyes having an absorption peak in the range of 550 to 600 nm are preferred. The dye having an absorption peak in the range of 550 to 600 nm is also not particularly limited, and examples thereof include known compounds such as nitro-based compounds, azo-based compounds, anthraquinone-based compounds, threne-based compounds, porphyrin-based compounds, and rare earth metal compounds. These compounds may be used alone or in combination. Among these, porphyrin-based compounds and rare earth-based compounds are preferred from the viewpoint of antiglare properties and visibility, and porphyrin-based compounds are more preferred from the viewpoint of dispersion stability in plastic materials. The content of the dye is not particularly limited, but is preferably 0.01 to 20.00 parts by mass, more preferably 0.05 to 5.00 parts by mass, per 100 parts by mass of the photochromic layer composition.

[0090] The photochromic layer composition (1) may further contain, if necessary, any amount of known additives that can be commonly added, such as surfactants, antioxidants, radical scavengers, light stabilizers, ultraviolet absorbers, color inhibitors, antistatic agents, fluorescent dyes, pigments, fragrances, plasticizers, silane coupling agents, etc. These may be used alone or in combination of two or more.

[0091] The composition (1) for photochromic layer can be prepared by mixing the various components described above simultaneously or sequentially in any order.

[0092] The commercially available photochromic layer composition (1) (which may contain a polymerizable compound) is not particularly limited, and examples thereof include Transshade-SC (manufactured by Tokuyama Corporation, TRANSSHADE (registered trademark)). The photochromic layer composition (1) may be used singly or in combination of two or more.

[0093] The photochromic layer (1), which is a cured coating layer, is obtained by irradiating the photochromic layer composition (1) with light and curing it. The photochromic layer (1) can be formed on the surface of the primer layer by applying the photochromic layer composition (1) to the surface of the primer layer (1) and curing the applied photochromic layer composition (1). The application method is not particularly limited, and known application methods can be used, such as spin coating and dip coating. These methods may be used alone or in combination of two or more. Among these, spin coating is preferred from the viewpoint of uniformity of application. The curing treatment is not particularly limited, and examples include light irradiation and heat treatment. These methods may be used alone or in combination of two or more. Among these, light irradiation is preferred from the viewpoint of progressing the curing reaction in a short time. The intensity of the light irradiation is not particularly limited, but is preferably 50 to 350 mW / cm from the viewpoint of suppressing thermal deformation of the plastic lens and the curing reaction of the photochromic layer composition. ２ , more preferably 100 to 300 mW / cm ２ , particularly preferably 150 to 250 mW / cm ２ The irradiation time of the light irradiation is not particularly limited, but from the viewpoint of suppressing thermal deformation of the plastic lens and the curing reaction of the composition for the photochromic layer, it is preferably 10 to 200 seconds, more preferably 25 to 150 seconds, and particularly preferably 40 to 100 seconds. The exposure dose of the light irradiation is not particularly limited, but from the viewpoint of suppressing thermal deformation of the plastic lens and the curing reaction of the composition for the photochromic layer, it is preferably 0.5 to 70.0 J / cm. ２ , more preferably 2.5 to 45.0 J / cm ２ , particularly preferably 6.0 to 25.0 J / cm ２ After the hardening treatment, an annealing treatment (heat treatment) can be carried out as necessary. The conditions for the annealing treatment are not particularly limited, but it is preferable to carry out the annealing treatment in a heat treatment furnace with an atmospheric temperature of about 80 to 130°C.

[0094] The plastic lens (1) may further include known cured coating layers such as a protective layer, a hard coat layer, and other functional layers, as needed. These may be used alone or in combination of two or more. The protective layer, hard coat layer, and other functional layers are not particularly limited and known layers may be used, such as the protective layer (2), hard coat layer (2), and other functional layers (2) that may be included in the plastic lens (2) described below.

[0095] The total thickness of the cured coating layers (excluding the hard coat layer) included in the plastic lens (1) is not particularly limited, but is preferably 1 to 100 μm, more preferably 5 to 95 μm, and particularly preferably 10 to 90 μm. If the thickness is equal to or greater than the lower limit of the above range, weather resistance and adhesion are easily maintained, and if the thickness is equal to or less than the upper limit of the above range, the transmittance (transparency) of the cured coating layer is easily maintained.

[0096] (Coating Material) In the present disclosure and this specification, the term "coating material" refers to a material that suppresses the incidence of light in at least a part of a specific wavelength range, and the specific wavelength range refers to a wavelength range to which the polymerizable composition for forming a photochromic layer used in the construction of the plastic lens is sensitive. Hereinafter, the coating material provided in the plastic lens (1) will be described in more detail.

[0097] As one form of the covering material provided in the plastic lens (1), when the photochromic layer-forming polymerizable composition is sensitive to light in the wavelength range of 280 to 780 nm, the covering material may have a maximum transmittance of 35% or less for light in the wavelength range of 280 to 450 nm (hereinafter, this may be simply referred to as "covering material (1)").

[0098] The maximum transmittance of the covering material (1) for light in the wavelength range of 280 to 450 nm is not particularly limited as long as it is 35% or less. However, from the viewpoint of preventing light from entering through the edge surface of the lens substrate and making it difficult for arc-shaped color unevenness to occur in the peripheral portion of the plastic lens, the maximum transmittance is preferably 25% or less, more preferably 15% or less, even more preferably 5% or less, and particularly preferably 0%.

[0099] The thickness of the covering material (1) is not particularly limited, but is preferably 5 to 150 μm, more preferably 10 to 100 μm, and particularly preferably 15 to 50 μm. If the thickness is equal to or greater than the lower limit of the above range, light incidence from the edge surface is likely to be hindered, while if the thickness is equal to or less than the upper limit of the above range, a good appearance is likely to be ensured.

[0100] Specific examples of the coating material (1) are not particularly limited as long as the maximum transmittance of light in the wavelength range of 280 to 450 nm is 35% or less, and examples thereof include adhesive tape, ink, resin film, rubber, and a cured coating layer formed by curing a polymerizable composition. These may be used alone or in combination of two or more. Among these, adhesive tape and ink are preferred from the viewpoint of ease of coating.

[0101] The covering material (1) is not particularly limited as long as it covers the edge surface of the lens substrate, and the edge surface of the lens substrate may be covered with one layer or with two or more layers.

[0102] Commercially available products of the covering material (1) are not particularly limited, and examples thereof include UNI Posca Black (manufactured by Mitsubishi Pencil Co., Ltd.), UNI Posca White (manufactured by Mitsubishi Pencil Co., Ltd.), Macky Black (manufactured by Zebra Corporation), Polyimide Tape (manufactured by AS ONE Corporation), and Black Whiteboard Marker (Kokuyo Co., Ltd.). These may be used alone or in combination of two or more.

[0103] The timing of coating with the coating material (1) is not particularly limited, and may be at the very beginning of the production of the plastic lens (1), during the production (for example, before or after the formation of a primer layer, before or after the formation of a photochromic layer, etc.), or after the production of the plastic lens (1). Among these, coating after the production of the plastic lens (1) is preferred, from the viewpoint that the peripheral portion of the plastic lens (1) on which the cured coating layer has been formed may be polished and ground in order to adapt the plastic lens (1) to the size of an eyeglass frame or the like.

[0104] <Plastic Lens (2)> The plastic lens (2) includes a lens substrate, a photochromic layer formed on one surface of the lens substrate and cured from a photochromic layer-forming polymerizable composition that is sensitive to light in a specific wavelength range, and a coating material that coats the edge surface of the lens substrate and suppresses the incidence of light in at least a portion of the specific wavelength range onto the lens substrate, where the photochromic layer-forming polymerizable composition is sensitive to light in a wavelength range of 280 to 380 nm, the coating material has a transmittance of 15% or less for light with a wavelength of 365 nm, and the lens substrate has a transmittance of 10% or more for light with a wavelength of 365 nm. There are no particular limitations on the type of cured coating layer other than the photochromic layer, and the cured coating layer other than the photochromic layer may or may not be present. Examples of the cured coating layer other than the photochromic layer include a primer layer, a protective layer, a hard coat layer, and other functional layers, as described below. Furthermore, the surface of the lens substrate opposite to the surface having the photochromic layer (hereinafter sometimes simply referred to as the "other surface of the lens substrate") may or may not have a cured coating layer other than the photochromic layer.

[0105] (Lens Substrate) The lens substrate of the plastic lens (2) will be described in more detail below.

[0106] One form of lens substrate provided in the plastic lens (2) can be a lens substrate having a transmittance of 10% or more for light with a wavelength of 365 nm (hereinafter, sometimes simply referred to as "lens substrate (2)").

[0107] The transmittance of the lens substrate (2) for light with a wavelength of 365 nm is not particularly limited as long as it is 10% or more, but from the viewpoint of fully exerting the effects of the present disclosure, it is preferably 20% or more, and more preferably 30% or more.

[0108] For the material, color, refractive index, focal point, surface, thickness, and one surface of the lens substrate (2), reference can be made to the description of the lens substrate (1) above.

[0109] (Primer Layer) The plastic lens (2) may further include a primer layer, if necessary. The primer layer that the plastic lens (2) may include (hereinafter, may be simply referred to as "primer layer (2)") will be described in more detail below.

[0110] The position of the primer layer (2) is not particularly limited, but from the viewpoint of improving the adhesion between the lens substrate and the photochromic layer, it is preferably between the lens substrate (2) described above and the photochromic layer (2) described below.

[0111] The thickness of the primer layer (2) is not particularly limited, but is preferably 0.1 to 20.0 μm, more preferably 0.3 to 15 μm, and particularly preferably 0.5 to 10 μm. If the thickness is equal to or greater than the lower limit of the above range, good adhesion between the lens substrate and the photochromic layer is achieved, while if the thickness is equal to or less than the upper limit of the above range, a good appearance is more easily achieved.

[0112] The primer layer (2) is a cured coating layer obtained by curing a polymerizable composition for forming a primer layer (hereinafter, sometimes simply referred to as a "primer layer composition").

[0113] One form of the primer layer composition used to form the primer layer (2) can be a primer layer composition prepared from a known pressure-sensitive adhesive (hereinafter, sometimes simply referred to as "primer layer composition (2)"). For the primer layer composition (2), the description of the primer layer composition (1) above can be referenced.

[0114] Another form of the primer layer composition used to form the primer layer (2) can be a primer layer composition (hereinafter sometimes simply referred to as "primer layer composition (3)") containing a polyisocyanate, a hydroxy group-containing polymerizable compound, and at least one polymerizable compound selected from the group consisting of (meth)acrylates and vinyl ethers, having a viscosity of 100 cP or less. The components contained in the primer layer composition (3) are not particularly limited, but it is preferable that the primer layer composition (3) contain the above three components from the viewpoints of suppressing attenuation of photochromic properties due to the primer layer and of adhesion to the photochromic layer. The various components contained in the primer layer composition (3) will be described in more detail below.

[0115] -Polyisocyanate- The polyisocyanate is a compound having two or more isocyanate groups per molecule. The number of isocyanate groups contained in one molecule of the polyisocyanate is not particularly limited, but is preferably 2 to 6, more preferably 3 to 5, and particularly preferably 3 to 4. When the number is equal to or greater than the lower limit of the above range, the water resistance of the primer layer is likely to be improved, and when the number is equal to or less than the upper limit of the above range, adhesion to the lens substrate is likely to be improved.

[0116] There are no particular restrictions on the molecular weight of the polyisocyanate, but it is preferably 200 to 800, more preferably 300 to 700, and particularly preferably 400 to 600. If it is at least the lower limit of the above range, adhesion to the lens substrate will be facilitated, and if it is at most the upper limit of the above range, the water resistance of the primer layer will be likely to be improved.

[0117] Specific examples of the polyisocyanate are not particularly limited, and include aromatic diisocyanates such as xylylene diisocyanate, phenylene diisocyanate, tolylene diisocyanate, diphenylmethane diisocyanate, and naphthalene diisocyanate; and aliphatic or alicyclic diisocyanates such as hexamethylene diisocyanate, lysine diisocyanate, cyclohexane diisocyanate, isophorone diisocyanate, 4,4'-dicyclohexylmethane diisocyanate, 1,3-bisisocyanatomethylcyclohexane, and tetramethylxylylene diisocyanate. These may be used alone or in combination of two or more. The polyisocyanates exemplified above may be in the form of an allophanate, adduct, biuret, or isocyanurate. These may be used alone or in combination of two or more. Furthermore, commercially available polyisocyanates are not particularly limited, and examples thereof include those manufactured by Tosoh Corporation such as Coronate HX, Coronate HXR, Coronate HXLV, Coronate HK, Coronate 2715, Coronate HL, Coronate L, Coronate 2037, HDI, TDI, and MDI; and those manufactured by Mitsui Chemicals, Inc. such as Takenate 500, Takenate 600, Duranate 24A-100, TPA-100, TKA-100, P301-75E, Takenate D-110N, D-120N, D-127N, D-140N, D-160N, D15N, D-170N, D-170HN, D-172N, D-177N, D-178N, and D-101E. These may be used alone or in combination of two or more.

[0118] -Hydroxy Group-Containing Polymerizable Compound- The number of hydroxy groups contained in one molecule of the hydroxy group-containing polymerizable compound is not particularly limited, but is preferably 1 to 6, more preferably 1 to 5, and particularly preferably 2 to 4. When the number is equal to or greater than the lower limit of the above range, the reaction efficiency with the polyisocyanate tends to be good, and when the number is equal to or less than the upper limit of the above range, adhesion to the photochromic layer tends to be good. The present inventors speculate that the urethane bond formed by reacting the isocyanate group of the polyisocyanate with the hydroxy group of the hydroxy group-containing polymerizable compound contributes to improved adhesion of the primer layer.

[0119] The number of polymerizable groups contained in one molecule of the hydroxy group-containing polymerizable compound is not particularly limited, but is preferably 2 or more from the viewpoint of the efficiency of the polymerization reaction.

[0120] One embodiment of the hydroxy group-containing polymerizable compound is a (meth)acrylate. When the hydroxy group-containing polymerizable compound is a (meth)acrylate, the number of functional groups of the (meth)acrylate is not particularly limited, but from the viewpoint of adhesion, it is preferably 1 (monofunctional) to 3, more preferably 2 to 3. The (meth)acryloyl group, which is the functional group, may contain only an acryloyl group, may contain only a methacryloyl group, or may contain an acryloyl group and a methacryloyl group. In one embodiment, from the viewpoint of adhesion, it is preferable that the hydroxy group-containing polymerizable compound contains only an acryloyl group as the (meth)acryloyl group.

[0121] The molecular weight of the hydroxy group-containing polymerizable compound is not particularly limited, but is preferably 100 to 600, more preferably 200 to 500, and particularly preferably 300 to 400. When the molecular weight is equal to or greater than the lower limit of the above range, the reaction efficiency with the polyisocyanate tends to be good, and when the molecular weight is equal to or less than the upper limit of the above range, adhesion to the photochromic layer tends to be good.

[0122] Specific examples of the (meth)acrylate are not particularly limited and include, for example, 2-hydroxyethyl (meth)acrylate, hydroxypropyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, 1,4-cyclohexanedimethanol monoacrylate, 2-hydroxy-1-acryloxy-3-methadryloxypropane, 2-hydroxy-1-3-dimethacryloxypropane, pentaerythritol tetraacrylate, 2-hydroxy-3-phenoxypropyl acrylate, monoacryloxyethyl hexahydrophthalate, 2-acryloyloxyethyl phthalate, 2-(acryloxyoxy)ethyl 2-hydroxyethyl phthalate, and compounds represented by the following formula (1): These may be used alone or in combination of two or more.

[0123] ...(1)

[0124] One example of the hydroxy group-containing polymerizable compound is a hydroxy group-containing polymerizable compound having an amide group. The hydroxy group-containing polymerizable compound having an amide group is not particularly limited, and examples thereof include N-(2-hydroxyethyl)acrylamide.

[0125] One example of the hydroxyl group-containing polymerizable compound is a hydroxyl group-containing polymerizable compound having an epoxy ester structure. The epoxy ester structure is a structure formed by the reaction of an epoxy group with a carboxyl group, and is represented by the formula "-CH(OH)-CH ２ -O-C(=O)-". Commercially available hydroxy group-containing polymerizable compounds having an epoxy ester structure are not particularly limited, and examples include Epoxy Ester 40EM (manufactured by Kyoeisha Chemical Co., Ltd.), Epoxy Ester 70PA (manufactured by Kyoeisha Chemical Co., Ltd.), Epoxy Ester 80MFA (manufactured by Kyoeisha Chemical Co., Ltd.), Epoxy Ester 200PA (manufactured by Kyoeisha Chemical Co., Ltd.), Epoxy Ester 3002M(N) (manufactured by Kyoeisha Chemical Co., Ltd.), Epoxy Ester 3002A(N) (manufactured by Kyoeisha Chemical Co., Ltd.), Epoxy Ester 3000MK (manufactured by Kyoeisha Chemical Co., Ltd.), and Epoxy Ester 3000A (manufactured by Kyoeisha Chemical Co., Ltd.). These may be used alone or in combination of two or more types.

[0126] -Polymerizable Compound, Being At Least One Type Selected from the Group Consisting of (Meth)acrylates and Vinyl Ethers, Having a Viscosity of 100 cP or Less- The primer layer composition (3) preferably contains at least one polymerizable compound selected from the group consisting of (meth)acrylates and vinyl ethers, having a viscosity of 100 cP (centipoise) or less (hereinafter, sometimes simply referred to as a "low-viscosity polymerizable compound"). The present inventors speculate that the primer layer composition (3) containing the low-viscosity polymerizable compound suppresses attenuation of photochromic properties caused by the primer layer.

[0127] The viscosity of the low-viscosity polymerizable compound is not particularly limited as long as it is 100 cP or less. From the viewpoint of ease of handling and suppression of the occurrence of optical defects, the viscosity is preferably 5 to 70 cP, more preferably 10 to 50 cP.

[0128] The number of functional groups in the (meth)acrylate, which is one form of the low-viscosity polymerizable compound, is not particularly limited, but from the viewpoint of adhesion, it is preferably 1 (monofunctional) to 3, more preferably 1 (monofunctional) to 2. The (meth)acrylate, which is one form of the low-viscosity polymerizable compound, may contain an aryl group (e.g., a phenyl group), an amide group, or the like. In the present disclosure and this specification, a "vinyl ether" refers to a compound having one or more vinyl groups and one or more ether bonds in one molecule, preferably two or more vinyl groups in one molecule, and more preferably two to four vinyl groups in one molecule. Furthermore, the number of ether bonds contained in the vinyl ether is preferably two to four in one molecule.

[0129] The molecular weight of the low-viscosity polymerizable compound is not particularly limited, but is preferably 100 to 300, and more preferably 150 to 250. When the molecular weight is equal to or greater than the lower limit of the above range, the occurrence of optical defects is easily suppressed, and when the molecular weight is equal to or less than the upper limit of the above range, adhesion to the photochromic layer is easily achieved.

[0130] Specific examples of the low viscosity polymerizable compound are not particularly limited, and include, for example, 2-phenoxyethyl (meth)acrylate, acrylamide, methoxypolyethylene glycol (meth)acrylate, phenoxypolyethylene glycol (meth)acrylate, stearyl (meth)acrylate, 1,10-decanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,9-nonanediol di(meth)acrylate, dipropylene glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, phenoxyethyl (meth)acrylate, ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, tricyclodecane dimethanol di(meth)acrylate, ethoxylated polypropylene glycol di(meth)acrylate, Trimethylolpropane tri(meth)acrylate, ethyl (meth)acrylate, butyl (meth)acrylate, isobutyl (meth)acrylate, tert-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, isodecyl (meth)acrylate, dodecyl (meth)acrylate, tridecyl (meth)acrylate, diethylene glycol butyl ether (meth)acrylate, cyclohexyl (meth)acrylate, tetrahydrofurfuryl (meth)acrylate, benzyl (meth)acrylate acrylate, 2-phenoxyethyl (meth)acrylate, isobornyl (meth)acrylate, 2-(dimethylamino)ethyl (meth)acrylate, 2-(diethylamino)ethyl (meth)acrylate, glycidyl (meth)acrylate, ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, polyethylene glycol di(meth)acrylate, tetramethylene glycol di(meth)acrylate, neopentyl glycol Examples of such vinyl ethers include hexanediol di(meth)acrylate, hexanediol di(meth)acrylate, nonamethylene glycol di(meth)acrylate, isoamyl (meth)acrylate, ethylene glycol monovinyl ether, tetramethylene glycol monovinyl ether, diethylene glycol monovinyl ether, 2-ethylhexyl vinyl ether, 2-propenoic acid, 2-[2-(ethenyloxy)ethoxy]ethyl ester, and 2-(2-ethenoxyethoxy)ethyl 2-methylprop-2-enoate. These may be used alone or in combination of two or more.

[0131] The content of the low-viscosity polymerizable compound is not particularly limited, but is preferably 30.0 to 90.0 mass%, more preferably 35.0 to 80.0 mass%, and particularly preferably 40.0 to 70.0 mass%, based on 100 mass% of the total of the low-viscosity polymerizable compound, polyisocyanate, and hydroxy group-containing polymerizable compound. When the content is equal to or greater than the lower limit of the above range, handling becomes easier, while when the content is equal to or less than the upper limit of the above range, adhesion to the lens substrate becomes easier. In one embodiment of the content of the low-viscosity polymerizable compound, the compound is the component contained in the largest amount in the primer layer composition (3) containing the low-viscosity polymerizable compound, polyisocyanate, and hydroxy group-containing polymerizable compound.

[0132] The content of the polyisocyanate is not particularly limited, but is preferably 5.0 to 75.0% by mass, more preferably 10.0 to 55.0% by mass, and particularly preferably 15.0 to 35.0% by mass, relative to 100% by mass of the total of the low-viscosity polymerizable compound, polyisocyanate, and hydroxy group-containing polymerizable compound. If the content is at least the lower limit of the above range, the water resistance of the primer layer is likely to be improved, while if it is at most the upper limit of the above range, adhesion to the lens substrate is likely to be improved.

[0133] The content of the hydroxy group-containing polymerizable compound is not particularly limited, but is preferably 3.0 to 30.0 mass%, more preferably 5.0 to 25.0 mass%, and particularly preferably 7.0 to 20.0 mass%, relative to 100 mass% of the total of the low-viscosity polymerizable compound, polyisocyanate, and hydroxy group-containing polymerizable compound. When the content is equal to or greater than the lower limit of the above range, the reaction efficiency with the polyisocyanate tends to be good, while when the content is equal to or less than the upper limit of the above range, adhesion to the photochromic layer tends to be good.

[0134] The primer layer composition (3) may further contain a polymerization initiator, if necessary. The amount of the polymerization initiator to be added is not particularly limited, and from the viewpoints of the efficiency of primer layer formation and adhesion to the photochromic layer, it is preferably 0.01 to 3.0 parts by mass per 100 parts by mass of the total of the low-viscosity polymerizable compound, polyisocyanate, and hydroxy group-containing polymerizable compound.

[0135] The polymerization initiator is not particularly limited, and known polymerization initiators can be used. The known polymerization initiator is not particularly limited, and examples thereof include photoradical polymerization initiators, thermal polymerization initiators, and the like. These may be used alone or in combination of two or more. Among these, photoradical polymerization initiators are preferred from the viewpoint of progressing the polymerization reaction in a short time. Specific examples of photoradical polymerization initiators can be found in the polymerization initiators that can be contained in the photochromic layer composition (2) described below.

[0136] The primer layer composition (3) may or may not contain a solvent. When the primer layer composition (3) contains a solvent, the solvent that can be used is not particularly limited as long as it does not inhibit the progress of the polymerization reaction of the polymerizable composition, and any solvent can be used. When the primer layer composition (3) contains a solvent, the amount of the solvent is not particularly limited, but from the viewpoint of suppressing optical defects, it is preferably 10.0 parts by mass or less, more preferably 5.0 parts by mass or less, and particularly preferably 3.0 parts by mass or less, relative to 100 parts by mass of the total of the low-viscosity polymerizable compound, polyisocyanate, and hydroxy group-containing polymerizable compound.

[0137] If necessary, the primer layer composition (3) may further contain any amount of known additives that are typically added to compositions for forming a primer layer, such as silicone surfactants, antioxidants, radical scavengers, light stabilizers, UV absorbers, color inhibitors, antistatic agents, fluorescent dyes, dyes, pigments, fragrances, plasticizers, silane coupling agents, leveling agents for improving the coatability of the composition, and inorganic oxide particles that contribute to improving the weather resistance of plastic lenses. These additives may be used alone or in combination of two or more. The amount of the known additives is not particularly limited as long as they exhibit the effect of forming a primer layer. The amount is preferably 1.0 to 20.0 parts by weight, more preferably 1.5 to 10.0 parts by weight, and particularly preferably 2.0 to 5.0 parts by weight, per 100 parts by weight of the total of the low-viscosity polymerizable compound, polyisocyanate, and hydroxyl group-containing polymerizable compound.

[0138] The contents of the low-viscosity polymerizable compound, polyisocyanate, and hydroxy group-containing polymerizable compound are not particularly limited as long as they exhibit the effect of the primer layer, and are preferably 80.0 to 100.0 mass%, more preferably 85.0 to 100.0 mass%, and more preferably 90.0 to 100.0 mass%, relative to 100 mass% of the primer layer composition (3) (excluding the polymerization initiator).

[0139] The primer layer composition (3) can be prepared by mixing the various components described above simultaneously or sequentially in any order.

[0140] The primer layer (2) can be formed on one surface of the lens substrate by applying primer layer composition (2) or (3) to one surface of the lens substrate and then curing the applied primer layer composition. The application method is not particularly limited, and known application methods can be used, such as spin coating and dip coating. These methods may be used alone or in combination. Among these, spin coating is preferred from the viewpoint of uniformity of application. A curing treatment for curing the primer layer composition (2) can be a drying treatment. The drying treatment is not particularly limited, and can be carried out, for example, by placing the lens in an atmosphere at room temperature to 100°C for 5 minutes to 24 hours. The curing treatment for curing the primer layer composition (3) is not particularly limited, and examples include light irradiation and heat treatment. These methods may be used alone or in combination. Among these, light irradiation is preferred from the viewpoint of progressing the curing reaction in a short time. The conditions for the curing treatment by light irradiation can be determined depending on the types of components contained in the primer layer composition (3) and the composition of the primer layer composition (3). After the curing treatment by light irradiation, an annealing treatment (heat treatment) can also be performed as necessary. The conditions for the annealing treatment are not particularly limited, but it is preferable to perform the annealing treatment in a heat treatment furnace with an atmospheric temperature of about 90 to 130°C.

[0141] (Photochromic Layer) The photochromic layer provided in the plastic lens (2) is a cured coating layer obtained by curing a photochromic layer-forming polymerizable composition that is sensitive to light in a specific wavelength range. Hereinafter, the photochromic layer provided in the plastic lens (2) (hereinafter, sometimes simply referred to as "photochromic layer (2)") will be described in more detail.

[0142] One form of the photochromic layer (2) can be a cured polymerizable composition for forming a photochromic layer (hereinafter, sometimes simply referred to as a "photochromic layer composition") that responds to light in the wavelength range of 280 to 380 nm and exhibits photochromic properties. The location of the photochromic layer (2) is not particularly limited, but from the viewpoints of adhesion to the lens substrate and protection of the photochromic layer, it is preferably between the primer layer (2) described above and the protective layer (2) described below.

[0143] The wavelength range to which the photochromic layer (2) is sensitive is not particularly limited as long as it is 280 to 380 nm, depending on the type of polymerization initiator, and is preferably 310 to 380 nm, more preferably 340 to 375 nm, and particularly preferably 350 to 370 nm. If the wavelength is equal to or greater than the lower limit of the above range, destruction of the photochromic compound by ultraviolet rays is easily suppressed, and if it is equal to or less than the upper limit of the above range, it becomes easy to be sensitive.

[0144] The thickness of the photochromic layer (2) is not particularly limited, but is preferably 5 to 80 μm, more preferably 10 to 70 μm, and particularly preferably 15 to 60 μm. If the thickness is equal to or greater than the lower limit of the above range, the color density tends to become high, while if the thickness is equal to or less than the upper limit of the above range, transparency tends to be maintained.

[0145] ((Photochromic Layer Composition)) One form of the photochromic layer composition sensitive to light in the wavelength range of 280 to 380 nm can be a photochromic layer composition containing a (meth)acrylate and a photochromic compound (hereinafter, sometimes simply referred to as "photochromic layer composition (2)"). Furthermore, the photochromic layer composition (2) may further contain a polymerizable compound, a polymerization initiator, etc., as necessary. Hereinafter, the various components contained in the photochromic layer composition (2) will be described in more detail.

[0146] -(Meth)acrylate- The (meth)acrylate contained in the composition for photochromic layer (2) is not particularly limited and includes, for example, a polyfunctional (meth)acrylate having a molecular weight of 500 or more (hereinafter also referred to as "component A"), a monofunctional (meth)acrylate (hereinafter also referred to as "component B"), a polyfunctional (meth)acrylate having neither a cyclic structure nor a branched structure (hereinafter also referred to as "component C"), a bifunctional (meth)acrylate having at least one structure selected from the group consisting of a cyclic structure and a branched structure (hereinafter also referred to as "component D"), etc. These may be used alone or in combination of two or more types.

[0147] --Component A-- The molecular weight of Component A is not particularly limited as long as it is 500 or more, but is preferably 600 to 2000, more preferably 650 to 1500, and particularly preferably 700 to 1300. If the molecular weight is equal to or greater than the lower limit of the above range, the fading rate is likely to be improved, while if the molecular weight is equal to or less than the upper limit of the above range, the photochromic layer is likely to have a high hardness.

[0148] The component A is not particularly limited, and examples thereof include bifunctional (meth)acrylates, trifunctional (meth)acrylates, tetrafunctional (meth)acrylates, and pentafunctional (meth)acrylates. These may be used alone or in combination of two or more. Among these, from the viewpoint of weather resistance, bifunctional or trifunctional (meth)acrylates are preferred. The (meth)acryloyl group of the component A may contain only acryloyl groups, may contain only methacryloyl groups, or may contain both acryloyl and methacryloyl groups. That is, component A may be an acrylate or methacrylate.

[0149] One form of the above-mentioned component A includes a non-cyclic polyfunctional (meth)acrylate. In the present disclosure and this specification, "non-cyclic" means not containing a cyclic structure. In contrast, "cyclic" means containing a cyclic structure. The non-cyclic polyfunctional (meth)acrylate refers to a bifunctional or higher functional (meth)acrylate that does not contain a cyclic structure. Specific examples of component A are not particularly limited, and include, for example, polyalkylene glycol di(meth)acrylate represented by the following formula (2). These may be used alone or in combination of two or more.

[0150] ... (2)

[0151] In formula (2), R １ and R ２each independently represents a hydrogen atom or a methyl group, R represents an alkylene group, and n represents the number of repeating alkoxy groups represented by RO, and is 2 or more. The number of carbon atoms of the alkylene group represented by R in formula (2) is not particularly limited, but is preferably 1 to 5, more preferably 2 to 4. The alkylene group represented by R in formula (2) is not particularly limited, but examples include an ethylene group, a propylene group, and a tetramethylene group. The value of n in formula (2) is not particularly limited, but is preferably 2 to 30, more preferably 2 to 25, and particularly preferably 2 to 20. The polyalkylene glycol di(meth)acrylate represented by formula (2) is not particularly limited, but examples include polyethylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, and polytetramethylene glycol di(meth)acrylate. These may be used alone or in combination of two or more.

[0152] A specific example of Component A is a tri(meth)acrylate represented by the following formula (3): The (meth)acryloyl group of the tri(meth)acrylate represented by formula (3) may contain only an acryloyl group, may contain only a methacryloyl group, or may contain both an acryloyl group and a methacryloyl group.

[0153] ...(3)

[0154] In formula (3), R ４０ , R ４１ , R ４４ , R ４５ , R ４７ and R ４８ each independently represents an alkylene group; R ４３ represents an alkyl group, and R ４２ , R ４６ and R ４９ In formula (3), n1 represents a hydrogen atom or a methyl group. ４１ In formula (3), n2 represents the number of repeating alkoxy groups represented by OR ４５In formula (3), n3 represents the number of repeating alkoxy groups represented by OR ４８ The number of repetitions of the alkoxy group represented by the formula (I) is 2 or more.

[0155] R in formula (3) ４１ , R ４５ and R ４８ The n1, n2, and n3 in formula (3) are as described above for n in formula (2). In formula (3), R ４１ , R ４５ and R ４８ may be the same, or two or three may be different. This also applies to n1, n2, and n3.

[0156] R in formula (3) ４２ , R ４６ and R ４９ each independently represents a hydrogen atom or a methyl group. The tri(meth)acrylate represented by formula (3) may contain only acryloyl groups, only methacryloyl groups, or both acryloyl groups and methacryloyl groups as (meth)acryloyl groups.

[0157] R in formula (3) ４３ The number of carbon atoms in the alkyl group represented by the formula (3) is not particularly limited, but is preferably 1 to 5, and more preferably 1 to 4. ４３ The alkyl group represented by the formula (3) is a linear alkyl group or a branched alkyl group. ４３ Specific examples of the alkyl group represented by the formula (I) are not particularly limited, and include, for example, a methyl group and an ethyl group.

[0158] R in formula (3) ４０ , R ４４ and R ４７ R in formula (3) each independently represents an alkylene group. ４０ , R ４４ and R ４７ The number of carbon atoms of the alkylene group represented by the formula (3) is not particularly limited, but is preferably 1 to 5, and more preferably 1 to 4.４０ , R ４４ and R ４７ Specific examples of the alkylene group represented by the formula (I) are not particularly limited, and include, for example, a methylene group, an ethylene group, a propylene group, and a tetramethylene group.

[0159] The tri(meth)acrylate represented by formula (3) is not particularly limited, and examples thereof include trimethylolpropane polyoxyethylene ether tri(meth)acrylate, etc. These may be used alone or in combination of two or more.

[0160] --Component B-- Component B is a monofunctional (meth)acrylate represented by the following formula (4).

[0161] ...(4)

[0162] In formula (4), R １０ represents a hydrogen atom or a methyl group. The monofunctional (meth)acrylate represented by formula (4) may be an acrylate or a methacrylate.

[0163] In formula (4), R １１ represents a linear alkyl group having 3 or more carbon atoms or a branched alkyl group having 3 or more carbon atoms. １１ The alkyl group represented by the formula (4) may be unsubstituted or may have a substituent. The substituent is not particularly limited, and examples thereof include the various substituents described above. １１ The number of carbon atoms in the linear or branched alkyl group represented by the formula (I) is not particularly limited, but is preferably 3 to 15, more preferably 3 to 14, and particularly preferably 3 to 12. If the number is equal to or greater than the lower limit of the above range, the color density of the photochromic layer tends to be high, whereas if the number is equal to or less than the upper limit of the above range, the photochromic compound tends to be soluble in the composition for photochromic layer.

[0164] The molecular weight of the monofunctional (meth)acrylate represented by formula (4) may be, for example, 100 to 300. However, it is not limited to the above range. In one embodiment, the monofunctional (meth)acrylate represented by formula (4) may be a monofunctional (meth)acrylate having a molecular weight of 150 or less. Specific examples of the monofunctional (meth)acrylate represented by formula (4) are not particularly limited, and include, for example, n-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, isodecyl (meth)acrylate, n-lauryl (meth)acrylate, etc. These may be used alone or in combination of two or more.

[0165] The polyfunctional (meth)acrylate other than Component A that can be contained in the (meth)acrylate is not particularly limited. However, from the viewpoint of increasing the (meth)acryloyl group content in the photochromic layer composition (2) and forming a rigid polymer network between molecules, a (meth)acrylate with a high proportion of (meth)acryloyl groups in the molecule is preferred. From this viewpoint, a polyfunctional (meth)acrylate with a lower molecular weight than Component A is preferred. The molecular weight of the polyfunctional (meth)acrylate other than Component A is not particularly limited. From the above viewpoint, it is preferably 100 or more but less than 500, more preferably 100 to 400, and particularly preferably 100 to 350. The number of functional groups of the polyfunctional (meth)acrylate other than Component A is not particularly limited. However, from the viewpoint of weather resistance, a polyfunctional (meth)acrylate with a higher functionality than the polyfunctional (meth)acrylate used as Component A is preferred. The number of functional groups of the polyfunctional (meth)acrylate can be, for example, 10 to 15. The polyfunctional (meth)acrylate having 10 to 15 functional groups is not particularly limited, and examples thereof include poly[(3-methacryloyloxypropyl)silsesquioxane] derivatives, etc. These may be used alone or in combination of two or more.

[0166] The polyfunctional (meth)acrylate is not particularly limited, and examples thereof include a polyfunctional (meth)acrylate (component C) having no cyclic structure or branched structure, and a bifunctional (meth)acrylate (component D) having at least one structure selected from the group consisting of a cyclic structure and a branched structure. These may be used alone or in combination of two or more. Component C and component D will be described in more detail below.

[0167] --Component C-- Component C is a polyfunctional (meth)acrylate having neither a cyclic structure nor a branched structure, represented by the following formula (5).

[0168] ...(5)

[0169] In formula (5), R ３ and R ４ each independently represents a hydrogen atom or a methyl group. In formula (5), m represents an integer of 1 or more, and may be 10 or less, 9 or less, 8 or less, 7 or less, or 6 or less. When component C has a methacryloyl group, the branched structure contained in the methacryloyl group is not taken into consideration.

[0170] The molecular weight of Component C is not particularly limited, but is preferably 100 to 400, more preferably 140 to 350, and particularly preferably 160 to 300. If the molecular weight is equal to or greater than the lower limit of the above range, the fading rate tends to be improved, whereas if the molecular weight is equal to or less than the upper limit of the above range, the color density of the photochromic layer tends to be high.

[0171] Component C may contain only acryloyl groups, only methacryloyl groups, or both acryloyl and methacryloyl groups as (meth)acryloyl groups. Specific examples of component C are not particularly limited, and include, for example, 1,9-nonanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, and 1,10-decanediol di(meth)acrylate. These may be used alone, or two or more may be used.

[0172] --Component D-- Component D is a bifunctional (meth)acrylate containing at least one structure selected from the group consisting of a cyclic structure and a branched structure. It is presumed that the inclusion of Component D in the photochromic layer composition (2) contributes to improving the color density of the photochromic layer formed from the photochromic layer composition (2). One embodiment of Component D contains one or more cyclic structures and no branched structures per molecule; another embodiment contains one or more branched structures and no cyclic structures per molecule; and another embodiment contains one or more cyclic structures and one or more branched structures per molecule. The number of at least one structure selected from the group consisting of cyclic structures and branched structures contained in Component D is not particularly limited, but is preferably 1 to 3, more preferably 1 to 2, and particularly preferably 1. When Component D contains a methacryloyl group, the branched structure contained in the methacryloyl group is not taken into consideration.

[0173] One example of component D containing one or more cyclic structures is an alicyclic bifunctional (meth)acrylate. The alicyclic bifunctional (meth)acrylate is not particularly limited, and examples thereof include R １１１ - (L １１ ) ｎ１１ -Q-(L ２２ ) ｎ２２ -R ２２２ Here, Q represents a divalent alicyclic group, and R １１１ and R ２２２ each independently represents a (meth)acryloyl group or a (meth)acryloyloxy group, L １１ and L ２２ each independently represents a linking group, and n11 and n22 each independently represent 0 or 1. The divalent alicyclic group represented by Q is not particularly limited, and suitable examples include alicyclic hydrocarbon groups having 3 to 20 carbon atoms, such as a cyclopentylene group, a cyclohexylene group, a cycloheptylene group, a cyclooctylene group, a tricyclodecanylene group, and an adamantylene group. １１ and L ２２ The linking group represented by the formula (I) is not particularly limited, and examples thereof include alkylene groups having 1 to 6 carbon atoms.

[0174] Specific examples of alicyclic bifunctional (meth)acrylates are not particularly limited and include, for example, cyclohexanedimethanol di(meth)acrylate, ethoxylated cyclohexanedimethanol di(meth)acrylate, propoxylated cyclohexanedimethanol di(meth)acrylate, ethoxylated propoxylated cyclohexanedimethanol di(meth)acrylate, tricyclodecane dimethanol di(meth)acrylate, ethoxylated tricyclodecane dimethanol di(meth)acrylate, propoxylated tricyclodecane dimethanol di(meth)acrylate, ethoxylated propoxylated tricyclodecane dimethanol di(meth)acrylate, etc. These may be used alone or in combination of two or more.

[0175] An example of component D containing one or more branched structures is a bifunctional (meth)acrylate containing a branched alkylene group. The number of carbon atoms in the branched alkylene group is not particularly limited, but is preferably 1 to 10, more preferably 2 to 9, even more preferably 3 to 8, and particularly preferably 4 to 7. One form of branched alkylene group may contain a quaternary carbon (i.e., a carbon bonded to four carbons). Specific examples of component D containing one or more branched structures are not particularly limited, and include, for example, neopentyl glycol di(meth)acrylate, ethoxylated neopentyl glycol di(meth)acrylate, and propoxylated neopentyl glycol di(meth)acrylate. These may be used alone, or two or more may be used.

[0176] The molecular weight of Component D is not particularly limited, but is preferably 200 to 400. When the molecular weight is equal to or greater than the lower limit of the above range, the color density of the photochromic layer is likely to be improved, and when the molecular weight is equal to or less than the upper limit of the above range, the photochromic compound is likely to be dissolved in the composition for photochromic layer.

[0177] The component D may contain only acryloyl groups, only methacryloyl groups, or both acryloyl groups and methacryloyl groups as (meth)acryloyl groups.

[0178] The content of the polymerizable compound (i.e., the total content of multiple polymerizable compounds) is not particularly limited, but is preferably 70 to 99 mass %, more preferably 80 to 95 mass %, relative to 100 mass % of the composition for photochromic layer (2). When the content is equal to or greater than the lower limit of the above range, the photochromic compound is more likely to dissolve in the composition for photochromic layer, and when the content is equal to or less than the upper limit of the above range, the photochromic properties are more likely to be improved. The composition for photochromic layer (2) may or may not contain a solvent. When a solvent is contained, any solvent can be used in any amount as long as it does not inhibit the polymerization reaction of the polymerizable composition.

[0179] The content of Component A is not particularly limited, but is preferably 50 to 95% by mass, more preferably 55 to 92% by mass, and particularly preferably 60 to 90% by mass, based on 100% by mass of all polymerizable compounds contained in the composition for photochromic layer (2). When the content is equal to or greater than the lower limit of the above range, the fading rate is likely to be improved, while when the content is equal to or less than the upper limit of the above range, weather resistance is likely to be improved. In this disclosure and this specification, a component that corresponds to both Component A and Component C, or Component A and Component D, is considered to be Component A. In one embodiment, Component A may be the component that accounts for the largest proportion of the multiple polymerizable compounds contained in the composition. In one embodiment, the composition for photochromic layer (2) may contain only one type of Component A, while in another embodiment, it may contain two or more types of Component A. When two or more types of Component A are contained, the content of Component A is the total content of the two or more types. This also applies to the contents of the other components.

[0180] The content of Component B is not particularly limited, but is preferably 1 to 30% by mass, more preferably 5 to 27% by mass, and particularly preferably 10 to 25% by mass, based on 100% by mass of all polymerizable compounds contained in the composition for photochromic layer (2). When the content is equal to or greater than the lower limit of the above range, weather resistance is likely to be improved, while when the content is equal to or less than the upper limit of the above range, the fading rate is likely to be improved. In one embodiment, the composition for photochromic layer (2) may contain only one type of Component B, while in another embodiment, it may contain two or more types of Component B. When two or more types of Component B are contained, the content of Component B is the total content of the two or more types.

[0181] The content of Component C is not particularly limited, but is preferably 1 to 30% by mass, and more preferably 3 to 27% by mass, based on 100% by mass of all polymerizable compounds contained in the composition for photochromic layer (2). If the content is equal to or greater than the lower limit of the above range, the color density tends to be high, while if the content is equal to or less than the upper limit of the above range, the color fading rate tends to be improved. In one embodiment, the composition for photochromic layer (2) may contain only one type of Component C, while in another embodiment, it may contain two or more types of Component C. When two or more types of Component C are contained, the content of Component C is the total content of the two or more types.

[0182] The content of Component D is not particularly limited, but is preferably 1 to 30% by mass, and more preferably 5 to 27% by mass, based on 100% by mass of all polymerizable compounds contained in the composition for photochromic layer (2). When the content is equal to or greater than the lower limit of the above range, the color density of the photochromic layer is likely to be improved, while when the content is equal to or less than the upper limit of the above range, the photochromic compound is likely to dissolve in the composition for photochromic layer. In one embodiment, the composition for photochromic layer (2) may contain only one type of Component D, while in another embodiment, it may contain two or more types of Component D. When two or more types of Component D are contained, the content of Component D is the total content of the two or more types.

[0183] The composition (2) for photochromic layer may, if necessary, contain (meth)acrylates other than components A to D. When the composition contains (meth)acrylates other than components A to D, the content of the (meth)acrylates other than components A to D is not particularly limited, but from the viewpoint of the fading rate, it is preferably 10.0 mass% or less, and more preferably 5.0 mass% or less, relative to 100 mass% of all (meth)acrylates contained in the composition (2) for photochromic layer. The composition (2) for photochromic layer may, if necessary, contain (meth)acrylates or no polymerizable compounds other than (meth)acrylates.

[0184] -Photochromic Compound- The photochromic compound contained in the composition for photochromic layer (2) (hereinafter, sometimes simply referred to as "photochromic compound (2)") is not particularly limited, and any known compound can be used, as long as the composition for photochromic layer (2) is sensitive to light in a wavelength range of 280 to 380 nm and exhibits photochromic properties. Specific examples of the photochromic compound (2) are not particularly limited and include, for example, compounds having a known skeleton that exhibits photochromic properties, such as azobenzenes, spiropyrans, spirooxazines, naphthopyrans, indenonaphthopyrans, phenanthropyrans, hexaallylbismidazoles, donor-acceptor Stenhouse adducts (DASA), salicylideneanilines, dihydropyrenes, anthracene dimers, fulgides, diarylethenes, phenoxynaphthacenequinones, and stilbenes; fulgimide compounds; spirooxazine compounds; chromene compounds; indeno-fused naphthopyran compounds; and at least one compound selected from the group consisting of photochromic compounds represented by general formula A, general formula B, and general formula C described in WO 2022 / 138966; and the like. These compounds may be used alone or in combination of two or more. The content of the photochromic compound is not particularly limited, but is preferably 0.1 to 15% by mass relative to 100% by mass of the composition (2) for photochromic layer.

[0185] -Other Components- In addition to the (meth)acrylate and the photochromic compound, the composition (2) for photochromic layer may contain, as necessary, one or more of various additives that may be typically contained in polymerizable compositions, in any amount. The additives that may be contained in the composition (2) for photochromic layer are not particularly limited, and examples thereof include a polymerization initiator for promoting the polymerization reaction and inorganic oxide particles that contribute to improving the weather resistance of the photochromic layer.

[0186] The polymerization initiator is not particularly limited, and examples thereof include a photoradical polymerization initiator and a thermal polymerization initiator. These may be used alone or in combination of two or more. Among these, a photoradical polymerization initiator is preferred from the viewpoint of progressing the polymerization reaction in a short time.

[0187] The photoradical polymerization initiator is not particularly limited, and examples thereof include benzoin ketals such as 2,2-dimethoxy-1,2-diphenylethan-1-one; α-hydroxyketones such as 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, and 1-[4-(2-hydroxyethoxy)phenyl]-2-hydroxy-2-methyl-1-propan-1-one; 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one, and 1,2-methyl-1-[4-(methyl α-aminoketones such as 1-[(4-phenylthio)phenyl]-2-morpholinopropan-1-one; oxime esters such as 1-[(4-phenylthio)phenyl]-1,2-octadione-2-(benzoyl)oxime; phosphine oxides such as bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, bis(2,6-dimethoxybenzoyl)-2,4,4-trimethylpentylphosphine oxide, and 2,4,6-trimethylbenzoyldiphenylphosphine oxide; 2-(o-chlorophenyl)-4,5-diphenylimidazole 2,4,5-triarylimidazole dimers such as 2-(o-chlorophenyl)-4,5-di(methoxyphenyl)imidazole dimer, 2-(o-fluorophenyl)-4,5-diphenylimidazole dimer, 2-(o-methoxyphenyl)-4,5-diphenylimidazole dimer, and 2-(p-methoxyphenyl)-4,5-diphenylimidazole dimer; benzophenone, N,N'-tetramethyl-4,4'-diaminobenzophenone, N,N'-tetraethyl-4,4'-diaminobenzophenone, 4-methoxyphenyl benzophenone compounds such as 4'-dimethylaminobenzophenone; quinone compounds such as 2-ethylanthraquinone, phenanthrenequinone, 2-tert-butylanthraquinone, octamethylanthraquinone, 1,2-benzanthraquinone, 2,3-benzanthraquinone, 2-phenylanthraquinone, 2,3-diphenylanthraquinone, 1-chloroanthraquinone, 2-methylanthraquinone, 1,4-naphthoquinone, 9,10-phenanthraquinone, 2-methyl-1,4-naphthoquinone, and 2,3-dimethylanthraquinone;Examples of suitable benzoin compounds include benzoin ethers such as benzoin methyl ether, benzoin ethyl ether, and benzoin phenyl ether; benzoin compounds such as benzoin, methylbenzoin, and ethylbenzoin; benzyl compounds such as benzyl dimethyl ketal; acridine compounds such as 9-phenylacridine and 1,7-bis(9,9'-acridinylheptane); N-phenylglycine; and coumarin. These compounds may be used alone or in combination of two or more. Among these, α-hydroxyketones and phosphine oxides are preferred from the viewpoints of curability, transparency, and heat resistance. In the 2,4,5-triarylimidazole dimer, the substituents on the aryl groups of the two triarylimidazole moieties may be the same and form a symmetrical compound, or different and form an asymmetrical compound. Furthermore, a thioxanthone compound may be combined with a tertiary amine, such as a combination of diethylthioxanthone and dimethylaminobenzoic acid. The content of the polymerization initiator is not particularly limited, but is preferably about 0.1 to 5.0% by mass relative to 100% by mass of the composition (2) for photochromic layer.

[0188] The inorganic oxide particles are not particularly limited, and examples thereof 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 (SnO ２ ), beryllium oxide (BeO), antimony oxide (Sb ２ O ５ ) and other metal oxide particles. These may be used alone or in combination of two or more. In the present disclosure and specification, "metal" also encompasses metalloids. Although the composition formula of an oxide with a stoichiometric composition is shown in parentheses above, the oxide constituting the inorganic oxide particles is not limited to an oxide with a stoichiometric composition.

[0189] The photochromic layer composition (2) may further contain, as needed, any amount of known additives that can be commonly added, such as surfactants, antioxidants, radical scavengers, light stabilizers, ultraviolet absorbers, color inhibitors, antistatic agents, fluorescent dyes, dyes, pigments, fragrances, plasticizers, silane coupling agents, and leveling agents for improving the coating suitability of the composition. These may be used alone or in combination of two or more.

[0190] The composition (2) for photochromic layer can be prepared by mixing the various components described above simultaneously or sequentially in any order.

[0191] The commercially available product of the composition (2) for photochromic layer is not particularly limited, and examples thereof include Transhade-SC (manufactured by Tokuyama Corporation, TRANSHADE (registered trademark)). These may be used alone or in combination of two or more.

[0192] The photochromic layer (2), which is a cured coating layer, is obtained by irradiating the photochromic layer composition (2) with light and curing it. The photochromic layer (2) can be formed on the surface of the primer layer by applying the photochromic layer composition (2) to the surface of the primer layer and then curing the applied photochromic layer composition (2). The application method is not particularly limited, and known application methods can be used, such as spin coating and dip coating. These methods may be used alone or in combination of two or more. Among these, spin coating is preferred from the viewpoint of uniformity of application. The curing treatment is not particularly limited, and examples include light irradiation and heat treatment. These methods may be used alone or in combination of two or more. Among these, light irradiation is preferred from the viewpoint of progressing the curing reaction in a short time. The intensity of the light irradiation is not particularly limited, but is preferably 50 to 350 mW / cm from the viewpoint of suppressing thermal deformation of the plastic lens and the curing reaction of the photochromic layer composition. ２ , more preferably 100 to 300 mW / cm ２ , particularly preferably 150 to 250 mW / cm２ The irradiation time of the light irradiation is not particularly limited, but from the viewpoint of suppressing thermal deformation of the plastic lens and the curing reaction of the composition for the photochromic layer, it is preferably 10 to 200 seconds, more preferably 25 to 150 seconds, and particularly preferably 40 to 100 seconds. The exposure dose of the light irradiation is not particularly limited, but from the viewpoint of suppressing thermal deformation of the plastic lens and the curing reaction of the composition for the photochromic layer, it is preferably 0.5 to 70.0 J / cm. ２ , more preferably 2.5 to 45.0 J / cm ２ , particularly preferably 6 to 25.0 J / cm ２ After the hardening treatment, an annealing treatment (heat treatment) can be carried out as necessary. The conditions for the annealing treatment are not particularly limited, but it is preferable to carry out the annealing treatment in a heat treatment furnace with an atmospheric temperature of about 80 to 130°C.

[0193] (Protective Layer) The plastic lens (2) may further include a protective layer, if necessary. Hereinafter, the protective layer that the plastic lens (2) may include (hereinafter, may be simply referred to as "protective layer (2)") will be described in more detail.

[0194] The position of the protective layer (2) is not particularly limited, but is preferably on the photochromic layer (2) from the viewpoint of protecting the photochromic layer. From this viewpoint, the protective layer preferably has high hardness. The protective layer is not particularly limited, but preferably has excellent solvent resistance. In the manufacturing process of an optical article, after a layer is formed, a wiping treatment with a solvent is usually performed to clean the surface of the formed layer. If the protective layer is damaged during this wiping treatment, it can cause clouding or optical defects in the plastic lens.

[0195] The thickness of the protective layer (2) is not particularly limited, but is preferably 10 to 50 μm, more preferably 12 to 45 μm, and particularly preferably 15 to 40 μm. If the thickness is equal to or greater than the lower limit of the above range, the weather resistance of the plastic lens will be improved, and if the thickness is equal to or less than the upper limit of the above range, the transmittance (transparency) of the cured coating layer will be easily maintained.

[0196] The protective layer (2) is a cured coating layer obtained by curing a polymerizable composition for forming a protective layer (hereinafter, sometimes simply referred to as a "protective layer composition").

[0197] One form of the protective layer composition used to form the protective layer (2) can be a polymerizable composition containing one or more (meth)acrylates and containing 70.0 mass% or more of an alicyclic bifunctional (meth)acrylate relative to 100 mass% of all (meth)acrylates (hereinafter, sometimes simply referred to as "protective layer composition (2)"). Note that there are no particular restrictions on the components contained in the protective layer composition (2), but from the viewpoints of hardness and solvent resistance of the protective layer, it is preferable that the composition contain an alicyclic bifunctional (meth)acrylate component.

[0198] The alicyclic bifunctional (meth)acrylate contained in the protective layer composition (2) can be exemplified by the alicyclic bifunctional (meth)acrylate described above as an example of the photochromic layer composition (2). The content of the alicyclic bifunctional (meth)acrylate is not particularly limited relative to 100% by mass of all (meth)acrylates, but from the viewpoint of achieving higher hardness and superior solvent resistance in the protective layer, it is preferably 70.0% by mass or more, more preferably 75.0% by mass or more, even more preferably 85.0% by mass or more, and particularly preferably 95.0% by mass or more. As an example of the content of the alicyclic bifunctional (meth)acrylate, the total amount of (meth)acrylate may be alicyclic bifunctional (meth)acrylate.

[0199] In one embodiment, the protective layer composition (2) may contain one or more other (meth)acrylates in addition to an alicyclic bifunctional (meth)acrylate as the (meth)acrylate. In another embodiment, the (meth)acrylate may contain only an alicyclic bifunctional (meth)acrylate. In the former embodiment, the other (meth)acrylate contained together with the alicyclic bifunctional (meth)acrylate is not particularly limited, and one or more of various (meth)acrylates can be used. Specific examples of the other (meth)acrylate are not particularly limited, and include, for example, monofunctional, bifunctional, trifunctional, tetrafunctional, and pentafunctional (meth)acrylates, which may be acyclic or cyclic. The (meth)acrylate containing a cyclic structure may have an alicyclic structure as the cyclic structure, or may have another cyclic structure. For the alicyclic structure, see the above description of the alicyclic bifunctional (meth)acrylate. The content of the other (meth)acrylates is not particularly limited, but from the viewpoint of obtaining high hardness and excellent solvent resistance in the protective layer, the content is preferably 0 to 30.0 mass%, more preferably 1.0 to 25.0 mass%, and particularly preferably 5.0 to 20.0 mass%, relative to 100 mass% of all (meth)acrylates.

[0200] The protective layer composition (2) contains at least one (meth)acrylate as a polymerizable compound. In one embodiment, it may contain one or more polymerizable compounds other than (meth)acrylate. In another embodiment, it may contain only (meth)acrylate as the polymerizable compound. The other polymerizable compounds are not particularly limited, and one or more known polymerizable compounds may be used. The content of the (meth)acrylate is not particularly limited, but from the viewpoint of durability, it is preferably 80.0% by mass or more, more preferably 90.0% by mass or more, and particularly preferably 100% by mass, of the total polymerizable compounds in the protective layer composition (2).

[0201] In one embodiment, the content of the (meth)acrylate (when two or more types of (meth)acrylates are contained, the total amount thereof) is preferably 80.0% by mass or more, more preferably 90.0% by mass or more, and particularly preferably 95.0% by mass or more, based on 100% by mass of the composition for protective layer (2).

[0202] The protective layer composition (2) may or may not contain a solvent. When the protective layer composition (2) contains a solvent, any solvent can be used in any amount without any particular limitation as long as it does not inhibit the progress of the polymerization reaction of the polymerizable composition.

[0203] The protective layer composition (2) may further contain one or more additives in any amount as needed. The additives are not particularly limited, and examples thereof include various known additives such as a polymerization initiator for promoting a polymerization reaction; a surfactant such as a silicone surfactant for improving the coating suitability of the composition; and the like. These additives may be used alone or in combination of two or more.

[0204] The polymerization initiator is not particularly limited, and examples thereof include photoradical polymerization initiators and thermal polymerization initiators. These may be used alone or in combination of two or more. Among these, photoradical polymerization initiators are preferred from the viewpoint of progressing the polymerization reaction in a short time. Specific examples of photoradical polymerization initiators can be found in the polymerization initiators that can be contained in the photochromic layer-forming polymerizable composition described above. The content of the polymerization initiator is not particularly limited, and from the viewpoint of the efficiency of forming the protective layer, it is preferably 0.1 to 5.0% by mass relative to 100% by mass of the protective layer composition (2).

[0205] The composition for protective layer (2) may further contain an ultraviolet absorber, if necessary. The ultraviolet absorber is not particularly limited, and examples thereof include hydroxyphenyl triazine compounds such as 2,4-bis(2,4-dimethylphenyl)-6-(2-hydroxy-4-n-octyloxyphenyl)-s-triazine, 2,4,6-tris(2-hydroxy-4-hexyloxy-3-methylphenyl)-s-triazine, 2-[2-hydroxy-4-(2-ethylhexyloxy)phenyl]-4,6-diviphenyl-s-triazine, and 2-[[2-hydroxy-4-[1-(2-ethylhexyloxycarbonyl)ethyloxy]phenyl]]-4,6-diphenyl-s-triazine; and benzotriazole compounds such as 2-(5-chloro-2H-benzotriazol-2-yl)-6-tert-butyl-4-methylphenol and 2-(5-chloro-2-benzotriazolyl)-6-tert-butyl-p-cresol. These may be used alone or in combination of two or more. The ultraviolet absorber, when contained in the composition for protective layer (2), can contribute to improving the weather resistance of the protective layer. When the composition for protective layer (2) contains an ultraviolet absorber, the content of the ultraviolet absorber is not particularly limited, and from the viewpoint of weather resistance, etc., it is preferably 0.1 to 1.0 mass% relative to 100 mass% of the composition for protective layer (2).

[0206] The composition for protective layer (2) can be prepared by mixing the various components described above simultaneously or sequentially in any order.

[0207] The protective layer (2) can be formed on the surface of the photochromic layer (2) by applying the protective layer composition (2) to the surface of the photochromic layer and curing the applied protective layer composition (2). If necessary, a primer layer or the like may be further formed between the photochromic layer (2) and the protective layer (2) to improve adhesion between the photochromic layer (2) and the protective layer (2). The coating method is not particularly limited, and known coating methods can be used, such as spin coating and dip coating. These methods may be used alone or in combination. Among these, spin coating is preferred from the viewpoint of uniformity of coating. The curing treatment is not particularly limited, and examples include light irradiation and heat treatment. These methods may be used alone or in combination. Among these, light irradiation is preferred from the viewpoint of progressing the curing reaction in a short time. The curing treatment conditions can be determined depending on the types of components contained in the protective layer composition (2) and the composition of the protective layer composition (2). After the hardening treatment, an annealing treatment (heat treatment) can be carried out as necessary. The conditions for the annealing treatment are not particularly limited, but it is preferable to carry out the annealing treatment in a heat treatment furnace with an atmospheric temperature of about 90 to 130°C.

[0208] A plastic lens (2) according to one embodiment of the present disclosure can have a layer structure of "photochromic layer / protective layer." Regarding the layer structure, " / " is used to encompass both a structure in which the layers are in direct contact without any other layer interposed therebetween and a structure in which the layers are provided via one or more other layers. Furthermore, in one embodiment, the optical article can have a layer structure of "photochromic layer / protective layer / other cured coating layer." The other cured coating layer is not particularly limited, and examples thereof include a cured layer generally referred to as a hard coat layer. These may be used alone or in combination of two or more. Providing a hard coat layer in addition to the protective layer can further enhance the durability of the optical article. Furthermore, in one embodiment, providing a hard coat layer can also enhance the impact resistance of the optical article. In one embodiment, the other cured coating layer can be in direct contact with the protective layer without any other layer interposed therebetween.

[0209] In one embodiment, the hard coat layer can be formed by irradiating and / or heating a polymerizable composition for forming a hard coat layer (hereinafter, sometimes simply referred to as a "hard coat layer composition"). The hard coat layer is not particularly limited, and examples thereof include an organosilicon-based cured coating layer. An organosilicon-based cured coating layer is generally preferred because it has excellent impact resistance. Furthermore, in one embodiment, when an antireflection layer is further provided, an organosilicon-based cured coating layer is generally preferred because it has excellent adhesion to the antireflection layer.

[0210] The organosilicon-based cured coating layer is a cured coating layer obtained by curing a hard coat layer composition containing an organosilicon compound. The organosilicon compound is not particularly limited, and examples include organosilicon compounds capable of generating silanol groups upon polymerization, such as γ-glycidoxypropyltrimethoxysilane; organopolysiloxanes such as water-dispersed colloidal silica having reactive groups such as halogen atoms or amino groups that undergo condensation reaction with silanol groups; and silane coupling agents having a polymerizable group such as a vinyl group, an allyl group, a (meth)acryloyl group, or a (meth)acryloyloxy group and a hydrolyzable group such as an alkoxy group. These may be used alone or in combination of two or more. The hard coat layer composition containing the organosilicon compound may further contain silicon oxide; particles of an inorganic substance such as titanium oxide; or the like, as necessary, for adjusting the refractive index, etc. In addition to the above, the hard coat layer composition containing an organosilicon compound may further contain, as necessary, a curing agent such as aluminum acetylacetonate to improve the hardness of the hard coat layer; a surfactant such as a silicone surfactant to control liquid dispersibility and interfacial tension; etc. For details of the polymerizable composition containing an organosilicon compound, known techniques related to organosilicon-based cured coating layers that can function as hard coat layers can be applied. The polymerizable composition containing an organosilicon compound can be cured by promoting a polymerization reaction through light irradiation and / or heat treatment, depending on the types of components contained in the composition.

[0211] The composition for a hard coat layer may or may not contain a solvent. When the composition for a hard coat layer contains a solvent, any solvent can be used in any amount without any particular limitation as long as it does not inhibit the progress of the polymerization reaction of the polymerizable composition.

[0212] When the other cured coating layer is provided on the protective layer, there is no particular limitation, but from the viewpoint of preventing foreign matter from being interposed between the protective layer and the other cured coating layer, it is preferable to subject the surface of the protective layer to a wiping treatment with a solvent. However, if the protective layer has poor solvent resistance, the solvent wiping treatment will damage the protective layer (for example, cause surface roughness), which will cause clouding or optical defects in the plastic lens including the protective layer. In contrast, the protective layer (2) formed from the above-mentioned protective layer composition (2) exhibits excellent solvent resistance, and therefore can be said to be suitable for providing the other cured coating layer on the protective layer (2).

[0213] The wiping treatment with a solvent is not particularly limited and can be performed by a known method, for example, wiping the surface of the protective layer with a cloth soaked in the solvent. The solvent is not particularly limited and examples thereof include ketone solvents such as acetone; alcohol solvents such as ethanol and isopropyl alcohol; and the like. These may be used alone or in combination of two or more. In one embodiment, the protective layer preferably has high resistance to ketone solvents that are commonly used as wiping solvents during the production of optical articles.

[0214] (Other Functional Layers) The plastic lens (2) may or may not further include other functional layers in addition to the above-mentioned primer layer, photochromic layer, protective layer, and hard coat layer, as necessary. The other functional layers are not particularly limited, and examples thereof include an anti-reflection layer, a water-repellent or hydrophilic anti-fouling layer, an anti-fogging layer, etc. These may be used alone or in combination of two or more.

[0215] The total thickness of the cured coating layers (excluding the hard coat layer) included in the plastic lens (2) is not particularly limited, but is preferably 1 to 110 μm, more preferably 5 to 100 μm, and particularly preferably 10 to 95 μm. If the thickness is equal to or greater than the lower limit of the above range, weather resistance and adhesion are easily maintained, and if the thickness is equal to or less than the upper limit of the above range, the transmittance (transparency) of the cured coating layer is easily maintained.

[0216] (Coating Material) In the present disclosure and this specification, the term "coating material" refers to a material that suppresses the incidence of light in at least a portion of a specific wavelength range, and the specific wavelength range refers to a wavelength range to which the polymerizable composition for forming a photochromic layer used in the construction of the plastic lens is sensitive. Hereinafter, the coating material provided in the plastic lens (2) will be described in more detail.

[0217] As one form of the covering material provided in the plastic lens (2), when the polymerizable composition for forming a photochromic layer is sensitive to light in the wavelength range of 280 to 380 nm, the covering material may have a transmittance of 15% or less for light with a wavelength of 365 nm (hereinafter, this may be simply referred to as "covering material (2)").

[0218] The transmittance of the covering material (2) for light with a wavelength of 365 nm is not particularly limited as long as it is 15% or less. However, from the viewpoint of preventing light from entering through the edge surface of the lens substrate and making it difficult for arc-shaped color unevenness to occur in the peripheral portion of the plastic lens, the transmittance is preferably 10% or less, more preferably 5% or less, and particularly preferably 0%.

[0219] The thickness of the covering material (2) is not particularly limited, but is preferably 5 to 150 μm, more preferably 10 to 100 μm, and particularly preferably 15 to 50 μm. If the thickness is equal to or greater than the lower limit of the above range, light incidence from the edge surface is likely to be hindered, while if the thickness is equal to or less than the upper limit of the above range, a good appearance is likely to be ensured.

[0220] Specific examples of the covering material (2) are not particularly limited as long as the transmittance of light at a wavelength of 365 nm is 15% or less, and include, for example, adhesive tape, ink, resin film, rubber, and a cured covering layer formed by curing a polymerizable composition. These may be used alone or in combination of two or more. Among these, adhesive tape and ink are preferred from the viewpoint of ease of covering.

[0221] The covering material (2) is not particularly limited as long as it covers the edge surface of the lens substrate, and the edge surface of the lens substrate may be covered with one layer or with two or more layers.

[0222] Commercially available products of the covering material (2) are not particularly limited, and examples thereof include UNI Posca Black (manufactured by Mitsubishi Pencil Co., Ltd.), UNI Posca White (manufactured by Mitsubishi Pencil Co., Ltd.), Macky Black (manufactured by Zebra Corporation), Polyimide Tape (manufactured by AS ONE Corporation), etc. These may be used alone or in combination of two or more.

[0223] The timing of coating with the coating material (2) is not particularly limited, and may be at the very beginning of the production of the plastic lens (2), during the production (for example, before or after the formation of a primer layer, before or after the formation of a photochromic layer, etc.), or after the production of the plastic lens (2). Among these, coating after the production of the plastic lens (2) is preferred, from the viewpoint that the peripheral portion of the plastic lens (2) on which the cured coating layer has been formed may be polished and ground in order to adapt the plastic lens (2) to the size of an eyeglass frame or the like.

[0224] [Eyeglasses] One aspect of the present disclosure relates to eyeglasses equipped with the plastic lenses. Details of the plastic lenses equipped in the eyeglasses are as described above. By including the plastic lenses, the eyeglasses can, for example, exhibit anti-glare effects similar to sunglasses outdoors, as the photochromic compound contained in the photochromic layer changes color when exposed to sunlight. When returning indoors, the photochromic compound fades, restoring transparency. The configuration of the eyeglasses' frames is not particularly limited, and publicly known techniques can be applied. They may be full-rim frames that surround the entire plastic lens, half-rim frames (nylon frames) that surround only the upper half of the plastic lens, under-rim frames (reverse nylon frames) that surround only the lower half of the plastic lens, or rimless frames (rimless frames) that consist only of plastic lenses. Among these, half-rim frames (nylon frames), under-rim frames (reverse nylon frames), and rimless frames (rimless frames) are preferred, from the viewpoint of fully demonstrating the effects of the plastic lenses of the present disclosure, and rimless frames (rimless frames) are more preferred.

[0225] The present disclosure will be further described below with reference to examples, but the present disclosure is not limited to the embodiments shown in the examples.

[0226] [Coating Materials Used] Details of the coating materials used and explanations of their abbreviations are shown below. The transmittance is a value measured by the following measurement method.・Coating material 1: UNI Posca Black (manufactured by Mitsubishi Pencil Co., Ltd.): 0% transmittance for light in the wavelength range of 280 to 450 nm, 0% transmittance for light with a wavelength of 365 nm. ・Coating material 2: Polyimide tape (manufactured by AS ONE Corporation): 2% maximum transmittance for light in the wavelength range of 280 to 450 nm (wavelength at which maximum transmittance is shown: 450 nm), 0% transmittance for light with a wavelength of 365 nm. ・Coating material 3: UNI Posca White (manufactured by Mitsubishi Pencil Co., Ltd.): 16% maximum transmittance for light in the wavelength range of 280 to 450 nm (wavelength at which maximum transmittance is shown: 450 nm), 0% transmittance for light with a wavelength of 365 nm. ・Coating material 4: ZEBRA Macky Black (manufactured by Zebra Corporation): 4% maximum transmittance for light in the wavelength range of 280 to 450 nm (wavelength at which maximum transmittance is shown: 450 nm), 2.6% transmittance for light with a wavelength of 365 nm.

[0227] [Lens substrates used] Details of the lens substrates used and an explanation of their abbreviations are given below. The transmittance values ​​were measured using the following measurement method. Lens substrate 1: Hilux 1.5 (manufactured by HOYA Corporation, central thickness 2.1 mm, peripheral thickness 2.1 mm, refractive index 1.50, maximum transmittance of 93% for light in the wavelength range of 280 to 780 nm (wavelength at which maximum transmittance is shown: 717 nm), transmittance of 34% for light with a wavelength of 365 nm) Lens substrate 2: Hilux 1.6 (manufactured by HOYA Corporation, central thickness 2.0 mm, peripheral thickness 2.0 mm, refractive index 1.60, maximum transmittance of 90% for light in the wavelength range of 280 to 780 nm (wavelength at which maximum transmittance is shown: 773 nm), transmittance of 0% for light with a wavelength of 365 nm) Lens substrate 3: Hilux 1.67 (manufactured by HOYA Corporation, central thickness 1.8 mm, peripheral thickness 1.8 mm, refractive index 1.67, maximum transmittance of light in the wavelength range of 280 to 780 nm 89% (wavelength at which maximum transmittance is shown: 776 nm), transmittance of light with a wavelength of 365 nm 0%)

[0228] <Measurement of Transmittance> In the present disclosure and this specification, the term "transmittance" refers to a value measured using a spectrophotometer (UH4150, manufactured by Hitachi High-Tech Corporation) by placing (dying) a lens substrate or a coating material on a glass substrate (Monitor Glass 70 PHI, manufactured by Senyo Optics Co., Ltd.) and transmitting light for each wavelength. Note that the maximum transmittance refers to the transmittance of the wavelength at which the transmittance is maximum within a specific wavelength range.

[0229] [Commercially available primer layer compositions used] Primer layer composition 1: TR-SC-P (manufactured by Tokuyama Corporation) Primer layer composition 2: NJ321A (manufactured by Tokuyama Corporation)

[0230] [Preparation of polymerizable composition for forming photochromic layer]

[0231] (Preparation of Photochromic Layer Composition 1) In a plastic container, 94.4 parts by mass of Transhade-SC (TRANSSHADE (registered trademark) manufactured by Tokuyama Corporation) containing a photochromic compound and a polymerizable compound and 5.6 parts by mass of a silane coupling agent (TSL8370 manufactured by Momentive Performance Materials) were mixed and thoroughly stirred. The mixture was then degassed using a rotation-revolution type stirring / degassing device. In this way, Photochromic Layer Composition 1, which is Photochromic Layer Composition (1), was obtained.

[0232] (Preparation of Photochromic Layer Composition 2) In a plastic container, polyethylene glycol dimethacrylate ((in the above formula (2), n=14, R=ethylene group, R １ and R ２85.0 parts by mass of methyl acrylate (number average molecular weight 726) and 15.0 parts by mass of tricyclodecane dimethanol dimethacrylate (molecular weight 332) were mixed to obtain a mixture of polymerizable compounds. The mixture of polymerizable compounds thus obtained was mixed with a photochromic compound (an indeno-fused naphthopyran compound represented by the following structural formula (6) described in U.S. Pat. No. 5,645,767), a photoradical polymerization initiator (bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, manufactured by IGM Resin B.V., Omnirad 819), an antioxidant (ethylene bis(oxyethylene)bis-(3-(5-tert-butyl-4-hydroxy-m-tolyl)propionate)), and a light stabilizer (a mixture of bis(1,2,2,6,6-pentamethyl-4-piperidinyl)sebacate and methyl(1,2,2,6,6-pentamethyl-4-piperidinyl)sebacate) and thoroughly stirred. The mixture was then degassed using a rotation-revolution type stirring and degassing apparatus. Thus, a photochromic layer composition 2, which is a photochromic layer composition (2), was obtained. The contents of the various components were as follows, relative to 100% by mass of the composition 2 for photochromic layer: 92.0% by mass of the mixture of polymerizable compounds, 5.4% by mass of the photochromic compound, 0.8% by mass of the photoradical polymerization initiator, 0.9% by mass of the antioxidant, and 0.9% by mass of the light stabilizer.

[0233] ...(6)

[0234] (Preparation of Photochromic Layer Composition 3) In a plastic container, 97.0 parts by mass of Transhade-SC (TRANSSHADE (registered trademark) manufactured by Tokuyama Corporation) containing a photochromic compound and a polymerizable compound, 2.9 parts by mass of a silane coupling agent (TSL8370 manufactured by Momentive Performance Materials), and 0.1 parts by mass of a leveling agent (Dow Chemical Japan Co., Ltd.) were mixed and thoroughly stirred. The mixture was then degassed using a rotation-revolution type stirring and degassing apparatus. In this way, Photochromic Layer Composition 3, which is Photochromic Layer Composition (2), was obtained.

[0235] [Preparation of Primer Layer Composition 3] In a plastic container, 10.0 parts by mass of a hydroxy group-containing bifunctional acrylate having a compound represented by the following structural formula (1), 15.0 parts by mass of polyisocyanate (Coronate 2715, manufactured by Tosoh Corporation), and 75.0 parts by mass of 2-phenoxyethyl acrylate (viscosity: 13 cP) were mixed. To the mixture thus obtained, a photoradical polymerization initiator (bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, manufactured by IGM Resin B.V., Omnirad 819) and 0.05 parts by mass of a silicone surfactant (Polyflow KL-402, manufactured by Kyoeisha Chemical Co., Ltd.) were added in an amount of 0.02 parts by mass relative to 100 parts by mass of the total mixture, and the mixture was thoroughly stirred. The mixture was then degassed using a rotation-revolution type stirring / degassing apparatus. In this way, a primer layer composition 3, which is primer layer composition (3), was obtained.

[0236] ...(1)

[0237] [Preparation of protective layer composition 1]

[0238] In a plastic container, 94.9 parts by mass of an alicyclic bifunctional (meth)acrylate (tricyclodecane dimethanol diacrylate), 4.7 parts by mass of a photoradical polymerization initiator (bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, Omnirad 819, manufactured by IGM Resin B.V.), 0.3 parts by mass of an ultraviolet absorber (Tinuvin 479, manufactured by BASF Japan), and 0.1 parts by mass of a silicone surfactant (DOWSIL FZ-2104, manufactured by Dow-Toray Industries, Inc.) were mixed and thoroughly stirred, and then degassed using a rotation-revolution type stirring and degassing apparatus. In this way, composition 1 for protective layer, which is composition (2) for protective layer, was obtained. In addition, in the above-mentioned protective layer composition 1, the (meth)acrylate is only an alicyclic bifunctional (meth)acrylate, and therefore the content of the alicyclic bifunctional (meth)acrylate is 100% by mass out of 100% by mass of all (meth)acrylates.

[0239] [Preparation of Hard Coat Layer Composition 1] 17.00 parts by mass of γ-glycidoxypropyltrimethoxysilane, 30.00 parts by mass of methanol, and 28.00 parts by mass of water-dispersed colloidal silica (solid content 40% by mass, average particle size 15 nm, manufactured by JGC Catalysts and Chemicals Co., Ltd., OPTOLAKE SL-50A) were added to a glass container equipped with a magnetic stirrer, thoroughly mixed, and stirred for 24 hours at 5° C. Next, 15.00 parts by mass of propylene glycol monomethyl ether, 0.05 parts by mass of a silicone surfactant (manufactured by Dow Toray Industries, Inc., DOWSIL FZ-2104), and 1.50 parts by mass of aluminum acetylacetonate as a curing agent were added, thoroughly stirred, and then filtered to prepare Hard Coat Layer Composition 1.

[0240] [Production of plastic lens (1)]

[0241] Example 1: Lens substrate 1 was immersed in a 10% by mass aqueous solution of sodium hydroxide (liquid temperature: 60°C) for 5 minutes, then washed with pure water, and dried. Primer layer composition 1 was then applied to the convex surface (object-side surface) of the lens substrate by spin coating in an environment of 25°C and 50% relative humidity, and then dried at room temperature for 15 minutes. The formed primer layer had a thickness of 4 μm. Photochromic layer composition 1 was applied onto the primer layer by spin coating. Spin coating was performed using the method described in JP-A 2005-218994. The photochromic layer composition 1 applied onto the primer layer was then irradiated with light (light wavelength: 405 nm, light irradiation intensity: 220 mW / cm) in a nitrogen atmosphere (oxygen concentration: 500 volume ppm or less) at room temperature. ２ , light irradiation time: 65 seconds, light irradiation exposure amount: 14.3 J / cm ２), the composition was cured, and heat-treated in a heat treatment device (PH series, manufactured by Espec Corporation) at an atmospheric temperature of 100°C for 1 hour to form a photochromic layer. The thickness of the formed photochromic layer was 40 μm. After the photochromic layer was formed, the edge surface of the lens substrate was dyed (coated) using coating material 1 (thickness of coating material: 30 μm). The "thickness of the cured coating layer" was a value calculated from the analysis of the film thickness value by FFT (fast Fourier transform) after measuring the reflectance (interference waveform) of the sample using a non-contact film thickness measurement system (FF8, manufactured by System Road Co., Ltd.). The "intensity of light irradiation" was a value measured using an actinometer (UIT-250, manufactured by USHIO Corporation) by lighting a lens base 300 mm away from the center of the light source to the light receiving unit (center wavelength 365 mm). The "exposure amount of light irradiation" was a value calculated from the intensity of light irradiation (mW / cm ２ ) × irradiation time (seconds) In this way, the plastic lens of Example 1 was obtained.

[0242] Example 2 A plastic lens of Example 2 was obtained in the same manner as in Example 1, except that no primer layer was formed.

[0243] Example 3 A plastic lens of Example 3 was obtained in the same manner as in Example 1, except that primer layer composition 2 was used instead of primer layer composition 1 in Example 1.

[0244] Example 4 A plastic lens of Example 4 was obtained in the same manner as in Example 1, except that lens substrate 2 was used instead of lens substrate 1 in Example 1.

[0245] Example 5 A plastic lens of Example 5 was obtained in the same manner as in Example 1, except that Lens Substrate 3 was used instead of Lens Substrate 1 in Example 1.

[0246] Example 6 A plastic lens of Example 6 was obtained in the same manner as in Example 1, except that Covering Material 2 was used instead of Covering Material 1 in Example 1, and the edge surface of the lens substrate was covered with polyimide tape.

[0247] Example 7 A plastic lens of Example 7 was obtained in the same manner as in Example 1, except that Coating Material 3 was used instead of Coating Material 1 in Example 1.

[0248] Example 8 A plastic lens of Example 8 was obtained in the same manner as in Example 1, except that Coating Material 4 was used instead of Coating Material 1 in Example 1.

[0249] Comparative Example 1 A plastic lens of Comparative Example 1 was obtained in the same manner as in Example 1, except that no covering material was used.

[0250] Comparative Example 2 A plastic lens of Comparative Example 2 was obtained in the same manner as in Comparative Example 1, except that Lens Substrate 2 was used instead of Lens Substrate 1 in Comparative Example 1.

[0251] [Production of plastic lens (2)]

[0252] (Example 9) Lens substrate 1 was immersed in a 10% by mass aqueous solution of sodium hydroxide (liquid temperature: 60°C) for 5 minutes, then washed with pure water and dried. Thereafter, primer layer composition 3 was applied to the convex surface (object-side surface) of the lens substrate by spin coating in an environment of a temperature of 25°C and a relative humidity of 50%, and then primer layer composition 1 applied to the lens substrate was irradiated with light (light wavelength: 405 nm, light irradiation intensity: 250 mW / cm) in a nitrogen atmosphere (oxygen concentration: 500 volume ppm or less) at room temperature. ２ , light irradiation time: 5 seconds, light irradiation exposure amount: 1.25 J / cm ２ ) and curing this composition to form a primer layer. The formed primer layer had a thickness of 8 μm. Photochromic layer composition 2 was applied onto the primer layer by spin coating. Spin coating was performed according to the method described in JP-A-2005-218994. Thereafter, the photochromic layer composition 1 applied onto the primer layer was irradiated with light (wavelength of light: 405 nm, intensity of light irradiation: 250 mW / cm) in a nitrogen atmosphere (oxygen concentration: 500 volume ppm or less) at room temperature. ２ , light irradiation time: 40 seconds, light irradiation exposure dose: 10 J / cm ２) and curing the composition to form a photochromic layer. The thickness of the formed photochromic layer was 40 μm. Onto the photochromic layer, protective layer composition 1 was applied by spin coating in an environment of a temperature of 25° C. and a relative humidity of 50% to form a coating layer. The surface of this coating layer was irradiated with light (wavelength of light: 405 nm, intensity of light irradiation: 250 mW / cm) in a nitrogen atmosphere (oxygen concentration: 500 volume ppm or less) at room temperature. ２ , light irradiation time: 15 seconds, light irradiation exposure amount: 3.75 J / cm ２ ), and the coating layer was cured to form a protective layer. The thickness of the formed protective layer was 38 μm. After wiping the surface of the protective layer with acetone, hard coat layer composition 1 was applied by dip coating (withdrawal speed 20 cm / min). A heat treatment was performed using a heat treatment device (PH series, manufactured by Espec Corporation) at an atmospheric temperature of 100°C for 1 hour to form a hard coat layer. The thickness of the formed hard coat layer was 3 μm. After forming the hard coat layer, the edge surface of the lens substrate was dyed (coated) using coating material 1 (thickness of coating material: 35 μm). The "thickness of the cured coating layer" was a value calculated from analysis of the film thickness value by FFT (fast Fourier transform) after measuring the reflectance (interference waveform) of the sample using a non-contact film thickness measurement system (FF8, manufactured by System Road Co., Ltd.). The "intensity of light irradiation" is a value measured using an actinometer (UIT-250, manufactured by USHIO Corporation) by lighting a lens base 300 mm away from the center of the light source to the light receiving unit (center wavelength 365 mm). The "amount of light irradiation exposure" is the intensity of light irradiation (mW / cm ２ ) × irradiation time (seconds). In this way, the plastic lens of Example 9 was obtained.

[0253] Example 10 A plastic lens of Example 10 was obtained in the same manner as in Example 9, except that no primer layer was formed.

[0254] (Example 11) A plastic lens of Example 11 was obtained in the same manner as in Example 9, except that primer layer composition 1 was used instead of primer layer composition 3, photochromic layer composition 3 was used instead of photochromic layer composition 2, and a protective layer was not formed. Primer layer composition 1 was dried and cured at room temperature for 15 minutes. The thickness of the obtained primer layer was 4 μm. Photochromic layer composition 3 was also cured by light irradiation (light wavelength: 405 nm, light irradiation intensity: 230 mW / cm ２ , light irradiation time: 60 seconds, light irradiation exposure dose: 13.8 J / cm ２ ) and cured. The resulting photochromic layer had a thickness of 40 μm.

[0255] Example 12 A plastic lens of Example 12 was obtained in the same manner as in Example 11, except that the primer layer composition 2 was used instead of the primer layer composition 1 in Example 11.

[0256] Example 13 A plastic lens of Example 13 was obtained in the same manner as in Example 9, except that Covering Material 2 was used instead of Covering Material 1 in Example 9, and the edge surface of the lens substrate was covered with polyimide tape.

[0257] Example 14 A plastic lens of Example 14 was obtained in the same manner as in Example 9, except that the coating material 3 was used instead of the coating material 1 in Example 9.

[0258] Example 15 A plastic lens of Example 15 was obtained in the same manner as in Example 9, except that Coating Material 4 was used instead of Coating Material 1 in Example 9.

[0259] Comparative Example 3 A plastic lens of Comparative Example 3 was obtained in the same manner as in Example 9, except that no covering material was used.

[0260] Comparative Example 4 A plastic lens of Comparative Example 4 was obtained in the same manner as in Example 11, except that no covering material was used.

[0261] [Evaluation of Plastic Lenses] The following evaluations were carried out using each of the obtained plastic lenses. The evaluation results for Examples 1 to 8 are shown in Table 1, and the results for Examples 9 to 15 are shown in Table 2.

[0262] <Shade of Arc-Shaped Color Unevenness> Each plastic lens was left outdoors for 5 minutes in the morning on a sunny day (when the sun was low in the sky) to allow color to develop, and the occurrence of arc-shaped color unevenness on the periphery of the plastic lens was visually confirmed. The shade of the arc-shaped color unevenness that occurred was evaluated according to the following evaluation criteria. [Evaluation Criteria] A: No arc-shaped unevenness was observed. B: A faint arc-shaped unevenness was observed that was not noticeable. C: A faint arc-shaped unevenness was observed that was noticeable. D: A dark arc-shaped unevenness with an unclear outline was observed. E: A clear arc-shaped unevenness was observed. In the cases of ratings A and B, it can be said that the arc-shaped color unevenness was sufficiently suppressed. On the other hand, in the cases of ratings C to E, it cannot be said that the arc-shaped color unevenness was suppressed to a great extent.

[0263]

[0264]

[0265] The results shown in Table 1 confirm that the plastic lenses of Examples 1 to 8 are less likely to develop arc-shaped color unevenness on the periphery of the plastic lens than the plastic lenses of Comparative Examples 1 and 2. The results shown in Table 2 confirm that the plastic lenses of Examples 9 to 15 are less likely to develop arc-shaped color unevenness on the periphery of the plastic lens than the plastic lenses of Comparative Examples 3 and 4. The inventors believe that the plastic lenses of Examples 1 to 15 are less likely to develop arc-shaped color unevenness on the periphery of the plastic lens because the covering material blocks light from entering through the edge surface of the lens substrate, causing the light entering through the edge surface of the lens substrate to be reflected off the other surface of the lens substrate and making it difficult for this reflected light to hit the photochromic layer.

[0266] Two or more of the various aspects and configurations described herein may be combined in any combination.

[0267] The embodiments disclosed herein should be considered to be illustrative in all respects and not restrictive. The scope of the present disclosure is defined by the claims, not the above description, and is intended to include all modifications within the meaning and scope of the claims.

[0268] The present disclosure is useful in the technical fields of eyeglasses, goggles, and the like.

[0269] REFERENCE SIGNS LIST 1 Plastic lens 2 Color unevenness on an arc 3 Lens substrate 4 Primer layer 5 Photochromic layer 6 Coating material 7 Light

Claims

1. A plastic lens comprising: a lens substrate; a photochromic layer formed on one surface of the lens substrate and formed by curing a polymerizable composition for forming a photochromic layer that is sensitive to light in a specific wavelength range; and a coating material that covers the edge surface of the lens substrate and suppresses the incidence of light in at least a portion of the specific wavelength range onto the lens substrate.

2. The plastic lens according to claim 1, wherein the photochromic layer-forming polymerizable composition is sensitive to light in the wavelength range of 280 to 780 nm, and the coating material has a maximum transmittance of 35% or less for light in the wavelength range of 280 to 450 nm.

3. The plastic lens according to claim 2, wherein the polymerizable composition for forming a photochromic layer contains a plurality of photochromic compounds, has an absorbance of 0.100 or more at 420 nm, and an absorbance of 0.015 or more at 430 nm, and when measuring the color density, the value of the color density measured with light of wavelengths of 380 nm or less blocked by the value of the color density measured without blocking light of wavelengths of 380 nm or less is 0.60 or more.

4. The plastic lens according to claim 1, wherein the photochromic layer-forming polymerizable composition is sensitive to light in the wavelength range of 280 to 380 nm, the coating material has a transmittance of 15% or less for light with a wavelength of 365 nm, and the lens substrate has a transmittance of 10% or more for light with a wavelength of 365 nm.

5. The plastic lens according to claim 4, wherein the polymerizable composition for forming a photochromic layer comprises: a (meth)acrylate; and a photochromic compound.

6. The plastic lens of claim 1, further comprising a primer layer between said lens substrate and said photochromic layer.

7. The plastic lens of claim 1, wherein the lens substrate has a central portion less than 2.2 mm thick and a peripheral portion thicker than the central portion.

8. Eyeglasses comprising a plastic lens according to any one of claims 1 to 7.

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