Method for manufacturing spectacle lens

Abstract

This method for manufacturing a spectacle lens having a cured coating layer on one surface of a lens base material includes: a covering step for covering at least a portion of the other surface of the lens base material with a covering material having one or more through-holes; a pressure reduction step for reducing the pressure between the other surface of the lens base material and a spin coating mechanism that rotates the lens base material, through the through-holes in the covering material, to secure the other surface of the lens base material to the spin coating mechanism; and a spin coating step for spin-coating the one surface of the lens base material with a curable composition.

Description

Eyeglass lens manufacturing method

[0001] The present disclosure relates to a method for manufacturing an eyeglass lens, and in particular to a simple method for manufacturing an eyeglass lens that reduces the thickness of a cured coating layer formed on one surface of a lens substrate and provides excellent antifouling properties to the other surface of the lens substrate.

[0002] In the field of lenses used in eyeglasses (hereinafter sometimes simply referred to as "eyeglass lenses"), lenses having one or more properties may be used, such as photochromic properties, anti-reflection properties, anti-fouling properties, and scratch resistance.

[0003] A method for imparting the above properties to a spectacle lens includes applying a curable composition that exhibits one or more of the above properties (e.g., a curable composition for forming a photochromic layer containing a photochromic compound and a polymerizable compound) to the surface of a lens substrate, and curing the applied curable composition by irradiating it with light to form a cured coating layer having the above properties. This method can be repeated multiple times to produce spectacle lenses with multiple cured coating layers, i.e., spectacle lenses with multiple properties. An example of a method for applying the above curable composition to the surface of a lens substrate is spin coating. Spin coating is a known application method in which the center of the other surface of the lens substrate is fixed to a spin coating mechanism (a mechanism capable of rotating the lens substrate), a curable composition is supplied to one surface of the lens substrate (the surface not fixed to the spin coating mechanism), and the spin coating mechanism is then rotated to spread the curable composition over the entire surface of the one surface of the lens substrate.

[0004] However, in the spin coating method, excess curable composition is removed from the lens substrate by the centrifugal force of rotation, and the removed curable composition may find its way around to the other surface of the lens substrate (the side fixed to the spin coating mechanism) and contaminate the other surface of the lens substrate. Contamination of the other surface of the lens substrate necessitates cleaning, polishing, grinding, and other operations, resulting in an increase in production man-hours. Therefore, a method for manufacturing an eyeglass lens that provides excellent antifouling properties for the other surface of the lens substrate is desired. Furthermore, since a thinner cured coating layer often provides better transmittance (transparency), a manufacturing method that is excellent at reducing the thickness of the cured coating layer is desired from the perspective of maintaining the transmittance (transparency) of the eyeglass lens, i.e., a method for manufacturing an eyeglass lens that allows the spin coating mechanism to rotate at a higher speed.

[0005] Patent Document 1 discloses a method for preventing a photocurable composition (a curable composition that is cured by light) from spreading over to the other surface of the lens substrate (the side fixed to the spin coating mechanism) by tilting the upper part of a spatula toward the center of the lens substrate and abutting the side edge of the spatula against the upper part of the edge surface of the lens substrate and then spin coating.

[0006] International Publication No. 2008 / 093613

[0007] However, the method disclosed in Patent Document 1 requires that the tip of the spatula be positioned so as to contact the entire surface of the side surface (edge ​​surface) of the lens substrate, and excessive contact between the tip of the spatula and the side surface (edge ​​surface) of the lens substrate is thought to hinder the rotation of the spin coating mechanism.Furthermore, the method disclosed in Patent Document 1 is thought to be unable to prevent the photocurable composition (a curable composition that is cured by light) from spreading over to the other surface of the lens substrate, so the method of Patent Document 1 cannot be said to be necessarily simple and convenient.Furthermore, Patent Document 1 does not particularly consider reducing the thickness of the cured coating layer, so it cannot be said to be necessarily an excellent method for reducing the thickness of the cured coating layer.

[0008] An object of one aspect of the present disclosure is to provide a simple method for manufacturing a spectacle lens that reduces the thickness of a cured coating layer formed on one surface of a lens substrate and provides excellent antifouling properties to the other surface of the lens substrate.

[0009] Embodiments of the present disclosure relate to the following [1] to [7]. [1] A method for manufacturing an eyeglass lens having a cured coating layer on one surface of a lens substrate, comprising: a coating step of coating at least a portion of the other surface of the lens substrate with a coating material having one or more through holes; a depressurizing step of applying a pressure between the other surface of the lens substrate and a spin coating mechanism that rotates the lens substrate via the through holes in the coating material, thereby fixing the other surface of the lens substrate to the spin coating mechanism; and a spin coating step of spin-coating one surface of the lens substrate with a curable composition. [2] The method for manufacturing an eyeglass lens according to [1] above, wherein the rotation speed in the spin coating is 2500 rpm or higher. [3] The method for manufacturing an eyeglass lens according to [1] or [2] above, wherein the thickness of the cured coating layer is 5 to 100 μm. [4] The method for manufacturing an eyeglass lens according to any of [1] to [3] above, wherein the coating material is at least one type selected from the group consisting of a sheet and a plate. [5] The method for manufacturing an eyeglass lens according to any one of [1] to [4] above, wherein the lens substrate is a convex lens having a thicker center portion than the peripheral portion, a concave lens having a thicker peripheral portion than the center portion, or a flat lens having the same thickness at the center and peripheral portion. [6] The method for manufacturing an eyeglass lens according to any one of [1] to [5] above, wherein the lens substrate is a cylindrical lens having a non-uniform thickness at the peripheral portion. [7] The method for manufacturing an eyeglass lens according to any one of [1] to [6] above, wherein the cured coating layer has a primer layer, a photochromic layer, and a protective layer.

[0010] As a result of intensive research into solving the above-mentioned problems, the inventors have found that the above-mentioned problems can be solved by covering at least a portion of the other surface of the lens substrate, on which the curable composition is not applied, with a coating having one or more through holes, reducing the pressure between the other surface of the lens substrate and a spin coating mechanism via the through holes in the coating, fixing the other surface of the lens substrate to the spin coating mechanism, and then spin coating, thereby completing the present invention.

[0011] According to one aspect of the present disclosure, it is possible to provide a simple method for manufacturing a spectacle lens in which a cured coating layer formed on one surface of a lens substrate is thinned and the other surface of the lens substrate has excellent antifouling properties.

[0012] Fig. 10 is a cross-sectional view of the other surface of the lens substrate coated with a coating having through holes and when a spin coating mechanism is fixed. Fig. 11 is a schematic diagram illustrating a coating having one through hole. Fig. 12 is a schematic diagram illustrating a coating having one through hole in the center and rubber in the peripheral portion. Fig. 13 is a schematic diagram illustrating a coating having a plurality of through holes from the center to the peripheral portion and rubber in the peripheral portion. Fig. 14 is a schematic diagram illustrating a coating having a plurality of through holes from the center to the peripheral portion and no rubber in the peripheral portion.

[0013] 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, a description of "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 obtain "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 curable 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 product obtained by curing a curable composition with light or heat. For example, a cured coating layer obtained by curing a curable composition for forming a primer layer is referred to as a primer layer, a cured coating layer obtained by curing a curable composition for forming a photochromic layer is referred to as a photochromic layer, a cured coating layer obtained by curing a curable composition for forming a protective layer is referred to as a protective layer, and a cured coating layer obtained by curing a curable 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 this 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 this disclosure and this specification, "viscosity" refers to a value measured using a vibration viscometer in an atmospheric atmosphere at a temperature of 25°C. In this disclosure and this specification, "total amount" refers to the total amount of all components excluding the solvent, if the 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, the term "peripheral portion of the lens substrate" refers to a portion having a radius of 15 mm or more from the center of the lens substrate. In this disclosure and this specification, the term "mid-circumferential portion of the lens substrate" refers to a portion having 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, the term "central portion of the coating" refers to a portion having a radius of 5 mm or less from the center of the lens substrate. In this disclosure and this specification, the term "peripheral portion of the coating" refers to a portion having a radius of 5 mm or less from the outer periphery of the coating. Note that when the radius of the coating is less than 10 mm, the peripheral portion of the coating may be included in the central portion of the coating, but the portion having a radius of 5 mm or less from the outer periphery of the coating is referred to as the "peripheral portion of the coating." Furthermore, when the radius of the coating is less than 5 mm, the peripheral portion of the coating and the central portion of the coating refer to the same portion. In this disclosure and this specification, the term "mid-circumferential portion of the coating" refers to a portion that does not belong to the central portion of the coating or the peripheral portion of the coating. Note that when the radius of the coating is 10 mm or less, the "mid-circumferential portion of the coating" does not exist. In this disclosure and this specification, the term "eyeglass 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, the term "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 "thickness of the cured coating layer" of a lens substrate refers to a value calculated from the analysis of the film thickness value by 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 Co., Ltd.). In this disclosure and this specification, the term "thickness of the lens substrate" refers to a value measured by connecting terminals to the convex and concave surfaces of the lens substrate using a high-performance ABS Digimatic Indicator (ID-FNX series, manufactured by Mitutoyo Corporation).The "intensity 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 (central wavelength 365 mm). The "amount of light irradiation exposure" in this disclosure and this specification refers to the integrated value of irradiation time (intensity of light irradiation (mW / cm)) 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 (central wavelength 365 mm). ２ ) × irradiation time (seconds). In this disclosure and this specification, "one surface" of the lens substrate refers to the surface that is spin-coated with the curable composition in the spin-coating process, and "the other surface" of the lens substrate refers to the surface that is not spin-coated with the curable composition in the spin-coating process and is fixed to the spin-coating mechanism. In this disclosure and this specification, "spin-coating mechanism" refers to a mechanism provided in a spin-coating device that has the function of rotating the lens substrate. In this disclosure and this specification, "plate" refers to a plate with a thickness of 2.0 mm or more, and "sheet" refers to a plate with a thickness of less than 2.0 mm. 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 can vary depending on the weather and season.

[0014] [Method for Manufacturing Spectacle Lens] A method for manufacturing a spectacle lens according to one aspect of the present disclosure is a method for manufacturing a spectacle lens having a cured coating layer on one surface of a lens substrate, and is not particularly limited as long as it includes: a coating step of coating at least a portion of the other surface of the lens substrate with a coating having one or more through holes; a depressurizing step of reducing the pressure between the other surface of the lens substrate and a spin coating mechanism that rotates the lens substrate via the through holes in the coating, thereby fixing the other surface of the lens substrate to the spin coating mechanism; and a spin coating step of spin-coating one surface of the lens substrate with a curable composition, and may further include other steps as necessary.

[0015] (Eyeglass Lenses) Eyeglass lenses that can be manufactured by the eyeglass lens manufacturing method of the present disclosure have a lens substrate and a cured coating layer on one surface of the lens substrate, and are endowed with special properties (e.g., photochromic properties) based on the cured coating layer, making them suitable for use in eyeglasses. The eyeglass frames to which the above-mentioned eyeglass lenses can be applied are not particularly limited, and publicly known techniques can be applied, and may be full-rim frames that surround the entire eyeglass lens, half-rim frames (nylon frames) that surround only the upper half of the eyeglass lens, under-rim frames (reverse nylon frames) that surround only the lower half of the eyeglass lens, or rimless frames (rimless frames) that only comprise eyeglass lenses.

[0016] Hereinafter, each step included in the method for manufacturing a spectacle lens according to one aspect of the present disclosure will be described in more detail.

[0017] <Coating Step> The coating step in the method for manufacturing a spectacle lens according to one aspect of the present disclosure is a step of coating at least a portion of the other surface of the lens substrate with a coating having one or more through holes before the decompression step described below, and may or may not include other treatments.

[0018] The coating method for the coating material is not particularly limited, and may simply involve covering the lens substrate with the coating material, or may involve covering the lens substrate with the coating material and then fixing the coating material and the lens substrate together using a known adhesive tape, etc. Of these, from the viewpoint of work efficiency, it is preferable to simply cover the lens substrate with the coating material.

[0019] The coverage ratio of the coating to the other surface of the lens substrate is not particularly limited as long as it can cover at least a portion of the other surface of the lens substrate, but from the viewpoint of preventing the curable composition from adhering to the other surface of the lens substrate, it is preferably 30% or more, more preferably 50% or more, even more preferably 70% or more, and particularly preferably 100% of the other surface of the lens substrate. The coverage ratio of the coating to the surface area of ​​the other surface of the lens substrate is a value calculated as follows: (surface area of ​​the portion of the other surface of the lens substrate covered by the coating (including the surface area of ​​the through-hole diameter) / surface area of ​​the other surface of the lens substrate)×100%

[0020] (Lens Substrate) The lens substrate will be described in more detail below.

[0021] In the present disclosure and this specification, the material for the lens substrate 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; oxides such as boric oxide, aluminum oxide, and silicon oxide; and the like. These may be used alone or in combination of two or more.

[0022] The color of the lens substrate is not particularly limited, and it may be colorless (an undyed lens) or dyed.

[0023] The refractive index of the lens substrate is not particularly limited and may be, for example, 1.50 to 1.75. Note that in this disclosure and this specification, the refractive index refers to the refractive index for light of mercury e-line at 546.07 nm.

[0024] The focal point of the lens substrate is not particularly limited, and examples thereof include single-focus, multi-focus, and progressive-addition lenses.

[0025] The surface of the lens substrate is not particularly limited, and examples thereof include a convex surface, a concave surface, a flat surface, etc. In a typical lens substrate, 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 is not particularly limited, and examples thereof include a convex surface, a concave surface, a flat surface, etc. The other surface of the lens substrate is not particularly limited, and examples thereof include a convex surface, a concave surface, a flat surface, etc.

[0026] The thickness of the central portion of the lens substrate 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 2.0 mm. The thickness of the peripheral portion of the lens substrate 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. The peripheral portion does not have to have a uniform thickness, or it may have a uniform thickness.

[0027] The shape of the lens substrate is not particularly limited, and examples thereof include a convex lens whose central portion is thicker than the peripheral portion, a concave lens whose peripheral portion is thicker than the central portion, a flat lens whose central portion and peripheral portion have the same thickness, etc. Furthermore, the shape of the lens substrate may or may not be a cylindrical lens whose peripheral portion has a non-uniform thickness.

[0028] The radius of the lens substrate is not particularly limited, but is preferably 20 to 50 mm, more preferably 25 to 45 mm, and particularly preferably 30 to less than 40 mm. If the radius is equal to or greater than the lower limit of the above range, the lens will be more easily applicable to various eyeglass frames, while if the radius is equal to or less than the upper limit of the above range, the amount of polishing and grinding work required on the outer periphery of the eyeglass lens will be reduced.

[0029] (Coating) The coating will be described in more detail below.

[0030] In the present disclosure and this specification, the material of the coating is not particularly limited and known materials can be used, such as acrylic resin, polyacetal resin, polycarbonate resin, ABS resin, PA resin, PLA resin, carbon, ultraviolet curable resin, silicone resin, acrylic resin, polyurethane resin, epoxy resin, polyamide resin, vinyl chloride resin, phenolic resin, etc. These may be used alone or in combination of two or more. Among these, polyacetal resin is preferred from the viewpoints of high resistance to solvents used for cleaning and ease of recycling and cleaning.

[0031] The coating material is not particularly limited as long as it can cover at least a portion of the other surface of the lens substrate, and the other surface of the lens substrate may be coated with one layer or two or more layers. Furthermore, when multiple coating materials are used, all of the coating materials may be the same type, or two or more types may be used.

[0032] The state of the covering is not particularly limited, and examples thereof include a sheet, a plate, etc. These may be used alone or in combination of two or more. Among these, a plate is preferred from the viewpoint of ease of attachment and detachment of the covering.

[0033] The thickness of the coating in the plate state is not particularly limited, but is preferably 2.0 to 20.0 mm, more preferably 2.5 to 15.0 mm, and particularly preferably 3.0 to 10.0 mm. A thickness equal to or greater than the lower limit of the above range makes it easier to maintain durability, while a thickness equal to or less than the upper limit of the above range makes it easier to stabilize high-speed rotation. Furthermore, the thickness of the coating may or may not be uniform, and may vary depending on the thickness of the peripheral portion of the lens substrate.

[0034] The thickness of the covering in the sheet state is not particularly limited, but is preferably 0.1 to 2.0 mm, more preferably 0.3 to 1.8 mm, and particularly preferably 0.5 to 1.5 mm. If the thickness is equal to or greater than the lower limit of the above range, durability is easily maintained, and if the thickness is equal to or less than the upper limit of the above range, high-speed rotation is easily stabilized.

[0035] The shape of the coating is not particularly limited, but from the viewpoint of preventing decentering of the lens substrate and coating during rotation in spin coating, a perfect circle; or a point-symmetric polygon such as an equilateral triangle, square, rectangle, rhombus, parallelogram, regular hexagon, or regular octagon; and from the viewpoint of availability and ease of formation, a perfect circle is more preferable.

[0036] The dimensions of the coating are not particularly limited as long as they are large enough to cover at least a portion of the other surface of the lens substrate. However, from the viewpoint of preventing the curable composition from adhering to the other surface of the lens substrate, the coating is preferably large enough to cover 30% or more of the surface area of ​​the other surface of the lens substrate, more preferably 50% or more, even more preferably 70% or more, and particularly preferably 100%. The coating may also be large enough to cover 100% or more of the other surface of the lens substrate, i.e., larger than the outer periphery of the lens substrate. In one embodiment of the dimensions of the coating, if the lens substrate is a perfect circle with a radius of 35 mm, the coating can be a perfect circle with a radius of 35 mm, i.e., the lens substrate and the coating can be the same size (covering 100% of the other surface of the lens substrate). In another embodiment, if the lens substrate is a perfect circle with a radius of 35 mm, the coating can be a perfect circle with a radius of 30 mm, i.e., covering 73% of the other surface of the lens substrate. The coverage ratio of the coating to the surface area of ​​the other surface of the lens substrate is calculated as follows: (surface area of ​​the portion of the lens substrate where the coating is covering the other surface (including the surface area of ​​the through-hole diameter) / surface area of ​​the other surface of the lens substrate)×100%

[0037] The peripheral edge of the covering is not particularly limited, but is preferably provided with adhesive rubber to prevent the lens substrate and covering from slipping apart before carrying out the decompression step described below (rubber 2 in Figures 1 and 3).The material of the rubber is not particularly limited as long as it has enough adhesiveness to prevent the lens substrate and covering from slipping apart, and known materials can be used, such as urethane resin, silicone resin, Teflon, nitrile, and neoprene.These may be used alone or in combination of two or more.Of these, urethane resin is preferred.

[0038] The number of through holes in the covering is not particularly limited as long as it is one or more, and may be one, two or more, ten or more, or twenty or more. When one through hole is provided, it is preferable that the center of the through hole is positioned at the center of the covering, from the viewpoint of avoiding decentering of the lens and covering during rotation. Furthermore, when two or more through holes are provided, it is preferable that the through holes be provided so as to be point-symmetric, from the viewpoint of avoiding decentering of the lens and covering during rotation.

[0039] The diameter of the through-holes in the coating is not particularly limited as long as they fit within the coating, and any diameter can be used. When two or more through-holes are provided, the diameters of the through-holes may be the same or different, but it is preferable to design them so that the lens and coating do not become decentered during rotation.

[0040] The position of the through hole in the coating is not particularly limited, as long as it is a position where the pressure can be reduced between the lens substrate and the spin coating through the through hole in the decompression step described below, that is, as long as the through hole is located within the area where the lens substrate and the coating are in contact and the outer periphery of the area does not come into contact with the outer periphery of the through hole; the through hole may be located in the central part of the coating, in the peripheral part of the coating, or in the middle part of the coating.

[0041] The method for producing the above-mentioned coated material is not particularly limited, and may be, for example, a method in which a coating having the desired shape is cut from a plate or sheet made of the above-mentioned material and which is larger than the desired coated material, through holes are formed, and the coated material is obtained; or a method in which a composition which hardens by light, heat, drying, etc. to form a plate or sheet of the above-mentioned material is poured into a mold for the coated material having the desired shape, the coated material is formed, through holes are formed, and the coated material is obtained.

[0042] The coating step may or may not include other treatments as necessary in addition to coating at least a portion of the other surface of the lens substrate with a coating material having one or more through holes. One form of other treatment in the coating step is not particularly limited, and examples include pretreatment of the lens substrate, which is carried out prior to coating the other surface of the lens substrate with a coating material. Pretreatment is preferably carried out from the viewpoint of improving adhesion between the cured coating layer of the curable composition and the lens substrate.

[0043] One form of the pretreatment is not particularly limited, and examples thereof include chemical treatment with a basic aqueous solution or an acidic aqueous solution, polishing treatment using an abrasive, plasma treatment using atmospheric pressure plasma or low pressure plasma, corona discharge treatment, UV ozone treatment, etc. These may be used alone or in combination of two or more.

[0044] <Decompression Step> The coating step in the method for manufacturing an eyeglass lens according to one aspect of the present disclosure is a step of reducing the pressure between the other surface of the lens substrate and a spin-coating mechanism that rotates the lens substrate via a through-hole in a coating material, prior to the spin-coating step described below, to fix the other surface of the lens substrate to the spin-coating mechanism, and may or may not include other processes.

[0045] The above-mentioned decompression method is not particularly limited as long as it can reduce the pressure between the other surface of the lens substrate and the spin-coating mechanism through the through-holes in the coating material. For example, a mechanism for reducing the pressure and fixing the sample (the object to be rotated) and the spin-coating mechanism, which is provided in a spin-coating device of known technology, can be used.

[0046] (Spin-coating mechanism) One form of the spin-coating mechanism can be one that includes a V-ring (V-ring 41 in FIG. 1) and a fixing table (fixing table 42 in FIG. 1) for fixing a sample (object to be rotated), which is provided in a spin-coating device of the known art (spin-coating mechanism 40 in FIG. 1). Because the spin-coating mechanism includes the V-ring between the object to be coated and the fixing table, it is possible to efficiently reduce the pressure between the other surface of the lens substrate and the spin-coating mechanism.

[0047] The V-ring is not particularly limited, and known materials can be used. The diameter of the V-ring is not particularly limited, but from the viewpoint of vacuum efficiency and maintaining vacuum, it is preferably large enough to cover all of the through-holes provided within the area where the lens substrate and the covering are in contact. Commercially available V-rings are not particularly limited, and examples include silicone resin, Teflon, nitrile, and neoprene. These may be used alone or in combination of two or more types.

[0048] <Spin Coating Step> The spin coating step in the method for producing a spectacle lens according to one embodiment of the present disclosure is a step of spin coating a curable composition onto one surface of the lens substrate after the aforementioned decompression step, and may or may not include other treatments.

[0049] (Spin coating) The spin coating is a known coating method, and in one embodiment of the present disclosure, it can be a coating method in which a curable composition is supplied to one surface of a lens substrate, and then a spin coating mechanism is rotated to spread the curable composition over the entire surface of one surface of the lens substrate.

[0050] The rotation speed of the spin coating mechanism in the spin coating is not particularly limited, but is preferably 2500 rpm or higher, more preferably 2700 to 5000 rpm, and particularly preferably 3000 to 4000 rpm. If the rotation speed is higher than the lower limit of the above range, the cured coating layer tends to become thinner, while if the rotation speed is lower than the upper limit of the above range, high-speed rotation tends to be stable.

[0051] The conditions for performing the spin coating are not particularly limited, and known conditions can be used. One example of the conditions for performing the spin coating is an environment at a temperature of 25° C. and a relative humidity of 50%.

[0052] (Curable Composition) The curable composition will be described in more detail below.

[0053] In the present disclosure and this specification, the curable composition refers to, for example, a curable composition that has the property of being cured by irradiation with light, a curable composition that has the property of being cured by the application of heat, or a curable composition that has the property of being cured by absorbing moisture, and is a composition that, after curing, exhibits one or more properties such as adhesion, photochromic properties, antireflection properties, antifouling properties, scratch resistance, etc. By forming one or more cured coating layers, which are cured products of the above-mentioned curable compositions, on the surface of a lens substrate, the spectacle lens can acquire properties such as adhesion, photochromic properties, antireflection properties, antifouling properties, scratch resistance, etc.

[0054] The curable composition is not particularly limited, and examples thereof include a curable composition for forming a primer layer, a curable composition for forming a photochromic layer, a curable composition for forming a protective layer, and a curable composition for forming a hard coat layer. These may be used alone or in combination of two or more. The curable composition for forming a primer layer, the curable composition for forming a photochromic layer, and the curable composition for forming a protective layer will be described in more detail below.

[0055] ((Curable composition for forming primer layer)) One form of the curable composition for forming a primer layer (hereinafter sometimes simply referred to as "primer layer composition") is, for example, a primer layer composition 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. There are no particular restrictions on the components contained in the primer layer composition, but it is preferable that the primer layer composition contain the above three components from the viewpoint of suppressing attenuation of photochromic properties caused by the primer layer, which is a cured product of the primer layer composition, and from the viewpoint of improving adhesion. Hereinafter, the various components contained in the primer layer composition will be described in more detail.

[0056] -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.

[0057] 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.

[0058] 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.

[0059] -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.

[0060] 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.

[0061] 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.

[0062] 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.

[0063] 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.

[0064] ...(1)

[0065] 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.

[0066] 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.

[0067] -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 preferably contains at least one polymerizable compound, being 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 a primer layer composition containing the low-viscosity polymerizable compound suppresses attenuation of photochromic properties caused by the primer layer.

[0068] 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.

[0069] 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.

[0070] 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.

[0071] 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.

[0072] 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.

[0073] The content of the polyisocyanate is not particularly limited, but is preferably 10.0 to 70.0% by mass, more preferably 20.0 to 60.0% by mass, and particularly preferably 30.0 to 50.0% 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.

[0074] 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.

[0075] The primer layer composition may further contain a polymerization initiator, if necessary. The amount of the polymerization initiator to be added is not particularly limited, and from the viewpoint of primer layer formation efficiency, 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.

[0076] 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 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 curable composition described below.

[0077] The primer layer composition may or may not contain a solvent. When the primer layer composition 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 curable composition, and any solvent can be used. When the primer layer composition contains a solvent, the amount of the solvent is not particularly limited, but from the viewpoint of suppressing the occurrence of 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.

[0078] The primer layer composition may further contain, as necessary, known additives that are typically added to compositions for forming a primer layer. The amount of the known additives to be added is not particularly limited as long as the effect of the primer layer is exhibited, and is preferably 1.0 to 20.0 parts by mass, more preferably 1.5 to 10.0 parts by mass, and particularly preferably 2.0 to 5.0 parts by mass, per 100 parts by mass of the total of the low-viscosity polymerizable compound, polyisocyanate, and hydroxy group-containing polymerizable compound.

[0079] 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 (excluding the polymerization initiator).

[0080] The primer layer composition can be prepared by mixing the various components described above simultaneously or sequentially in any order.

[0081] The primer layer can be formed on one surface of the lens substrate by spin-coating the primer layer composition onto one surface of the lens substrate and then curing the spin-coated primer layer composition. The primer layer has the function of adhering (bonding) materials (e.g., lens substrate, cured coating layer, etc.) located on both surfaces of the primer layer. There are no particular restrictions on the location of the primer layer, but from the perspective of improving adhesion between the lens substrate and the cured coating layer (e.g., photochromic layer), it is preferably between the lens substrate and the cured coating layer (e.g., photochromic layer).

[0082] The curing treatment is not particularly limited, and examples thereof include light irradiation and heat treatment. These 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 curing treatment conditions can be determined depending on the types of various components contained in the primer layer composition and the composition of the primer layer composition. After the curing treatment, 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.

[0083] The thickness of the primer layer is not particularly limited, but is preferably 1 to 20 μm, more preferably 3 to 15 μm, and particularly preferably 5 to 10 μm. If the thickness is at least the lower limit of the above range, adhesion between the lens substrate and the photochromic layer will be good, and if the thickness is at most the upper limit of the above range, attack on the photochromic layer will be more easily suppressed.

[0084] ((Curable Composition for Forming Photochromic Layer)) One form of the curable composition for forming a photochromic layer (hereinafter, sometimes simply referred to as "composition for photochromic layer") is a composition for photochromic layer containing two or more types of (meth)acrylates and a photochromic compound. The two or more types of (meth)acrylates function as polymerizable compounds in the composition for photochromic layer. Hereinafter, the various components contained in the composition for photochromic layer will be described in more detail.

[0085] -Two or more types of (meth)acrylates- The two or more types of (meth)acrylates are not particularly limited, but from the viewpoint of fading rate, it is preferable to include at least a polyfunctional (meth)acrylate having a molecular weight of 500 or more (hereinafter, also referred to as "component A"). The (meth)acrylate other than component A among the two or more types of (meth)acrylates is not particularly limited, but examples thereof include a monofunctional (meth)acrylate (hereinafter, also referred to as "component B"), a polyfunctional (meth)acrylate having no cyclic structure or branched structure (hereinafter, also referred to as "component C"), and 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"). These may be used alone, or two or more types may be used.

[0086] --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.

[0087] 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.

[0088] 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.

[0089] ...(2)

[0090] 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 repetitions of the alkoxy group 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.

[0091] 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.

[0092] ...(3)

[0093] 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 ４５ In formula (3), n3 represents the number of repeating alkoxy groups represented by OR４８ The number of repetitions of the alkoxy group represented by the formula (I) is 2 or more.

[0094] 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.

[0095] 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.

[0096] 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.

[0097] 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 ４７Specific 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.

[0098] 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.

[0099] --Component B-- Component B is a monofunctional (meth)acrylate represented by the following formula (4).

[0100] ...(4)

[0101] 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.

[0102] 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.

[0103] 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. As described above, 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.

[0104] The polyfunctional (meth)acrylate other than Component A that may be contained in the two or more (meth)acrylates is not particularly limited. However, from the viewpoint of increasing the (meth)acryloyl group content in the photochromic layer composition 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 viewpoint described above, 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 may 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.

[0105] 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.

[0106] --Component C-- Component C is a polyfunctional (meth)acrylate having neither a cyclic structure nor a branched structure, represented by the following formula (5).

[0107] ...(5)

[0108] 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.

[0109] 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.

[0110] 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.

[0111] --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 composition for photochromic layer contributes to improving the color density of the photochromic layer formed from the composition for photochromic layer. 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 still 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.

[0112] 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.

[0113] 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.

[0114] 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.

[0115] 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.

[0116] The component D may contain only acryloyl groups, only methacryloyl groups, or both acryloyl groups and methacryloyl groups as (meth)acryloyl groups.

[0117] 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. 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 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 progress of the polymerization reaction of the curable composition.

[0118] 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. When the content is equal to or greater than the lower limit of the above range, the fading rate is likely to be improved, and 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 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.

[0119] 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. 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 of the composition for photochromic layer, only one type of Component B may be contained, and in another embodiment, two or more types of Component B may be contained. 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.

[0120] 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, relative to 100% by mass of all polymerizable compounds contained in the composition for photochromic layer. If the content is equal to or greater than the lower limit of the above range, the color density tends to be high, and 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 of the composition for photochromic layer, only one type of Component C may be contained, and in another embodiment, two or more types of Component C may be contained. 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.

[0121] 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, relative to 100% by mass of all polymerizable compounds contained in the composition for photochromic layer. 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 may contain only one type of Component D, and 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.

[0122] The composition for photochromic layer may, if necessary, contain another (meth)acrylate other than components A to D. When the composition contains another (meth)acrylate other than components A to D, the content of the other (meth)acrylate 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 for photochromic layer. The composition for photochromic layer may, if necessary, contain another polymerizable compound other than (meth)acrylate.

[0123] Photochromic Compound—One embodiment of the composition for photochromic layer may contain a photochromic compound together with the polymerizable compound. The photochromic compound is not particularly limited, and for example, a known compound that exhibits photochromic properties when exposed to ultraviolet light can be used. Specific examples of the photochromic compound are not particularly limited and include 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, photochromic compounds represented by general formula B, and photochromic compounds represented by general formula C, as described in WO 2022 / 138966. 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 about 0.1 to 15% by mass relative to 100% by mass of the composition for the photochromic layer.

[0124] -Other Components- In addition to the two or more types of (meth)acrylate and the photochromic compound, the composition for photochromic layer may contain, as necessary, one or more types of additives that may be typically contained in curable compositions, in any amount. The additives that may be contained in the composition for photochromic layer are not particularly limited, and examples thereof include a polymerization initiator for promoting a polymerization reaction.

[0125] 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.

[0126] 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 for the photochromic layer.

[0127] If necessary, the composition for the photochromic layer may further contain 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, etc. These may be used alone or in combination of two or more.

[0128] The composition for the photochromic layer can be prepared by mixing the various components described above simultaneously or sequentially in any order.

[0129] A photochromic layer can be formed on one surface of a lens substrate by spin-coating the photochromic layer composition onto one surface of the lens substrate and then curing the spin-coated photochromic layer composition. The photochromic layer exhibits photochromic properties, i.e., develops color under light in a specific wavelength range (e.g., outdoors) and fades under light outside the specific wavelength range (e.g., indoors). The location of the photochromic layer is not particularly limited, but is preferably between the primer layer described above and the protective layer described below from the viewpoints of adhesion to the lens substrate and protection of the photochromic layer.

[0130] The curing treatment is not particularly limited, and examples thereof include light irradiation and heat treatment. These 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 150 to 350 mW / cm. ２ However, from the viewpoint of suppressing thermal deformation of the eyeglass lens and the curing reaction of the composition for the photochromic layer, it is preferably 160 to 340 mW / cm ２ , more preferably 190 to 310 mW / cm ２ , particularly preferably 220 to 280 mW / cm ２ The irradiation time of the light irradiation is not particularly limited as long as it is 1 to 90 seconds, but from the viewpoint of suppressing thermal deformation of the spectacle lens and the curing reaction of the composition for the photochromic layer, it is preferably 5 to 80 seconds, more preferably 10 to 60 seconds, and particularly preferably 15 to 40 seconds. The exposure dose of the light irradiation is 0.15 to 31.5 J / cm. ２ However, from the viewpoint of suppressing thermal deformation of the eyeglass lens and the curing reaction of the composition for the photochromic layer, it is preferably 0.8 to 27.2 J / cm ２ , more preferably 1.9 to 18.6 J / cm ２ , particularly preferably 3.3 to 11.2 J / cm ２After 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.

[0131] The thickness of the photochromic layer is not particularly limited, but is preferably 5 to 40 μm, more preferably 10 to 35 μm, and particularly preferably 15 to 30 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.

[0132] ((Curable composition for forming protective layer)) One embodiment of the above-mentioned curable composition for forming a protective layer (hereinafter sometimes simply referred to as "protective layer composition") is a curable 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. Note that there are no particular restrictions on the components contained in the protective layer composition, but from the viewpoint of the hardness and solvent resistance of the protective layer, it is preferable that the composition contain an alicyclic bifunctional (meth)acrylate.

[0133] The alicyclic bifunctional (meth)acrylate contained in the protective layer composition can be the alicyclic bifunctional (meth)acrylate described above as an example of the photochromic layer-forming curable composition. 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 better 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 one embodiment of the content of the alicyclic bifunctional (meth)acrylate, the total amount of (meth)acrylate may be the alicyclic bifunctional (meth)acrylate.

[0134] In one embodiment, the protective layer composition 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 of the present disclosure, 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.

[0135] The protective layer composition contains at least one (meth)acrylate as a polymerizable compound, and in one embodiment, may contain one or more polymerizable compounds other than (meth)acrylate. In another embodiment, the protective layer composition 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 (100% by mass).

[0136] In one embodiment, the content of the above (meth)acrylate (the total amount when two or more types of (meth)acrylates are included) is preferably 80.0 mass% or more, more preferably 90.0 mass% or more, and particularly preferably 95.0 mass% or more, based on 100 mass% of the composition for the protective layer.

[0137] The composition for a protective layer may or may not contain a solvent. When the composition for a protective 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 curable composition.

[0138] The protective layer composition may further contain one or more additives at any content, 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 and a leveling agent for improving the coating suitability of the composition. These may be used alone or in combination of two or more.

[0139] 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. For specific examples of photoradical polymerization initiators, see the polymerization initiators that can be contained in the curable composition for forming a photochromic layer described above. The content of the polymerization initiator is not particularly limited, but 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 composition for the protective layer.

[0140] The composition for the protective layer 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 can contribute to improving the weather resistance of the protective layer by being contained in the composition for protective layer. When the composition for protective layer contains an ultraviolet absorber, the content of the ultraviolet absorber is not particularly limited, and is preferably 0.1 to 1.0 mass % relative to 100 mass % of the composition for protective layer from the viewpoint of optical properties such as transparency.

[0141] The composition for the protective layer can be prepared by mixing the various components described above simultaneously or sequentially in any order.

[0142] A protective layer can be formed on one surface of a lens substrate by spin-coating the protective layer composition and curing the spin-coated protective layer composition. The protective layer has scratch resistance. The position of the protective layer is not particularly limited, but is preferably formed on a cured coating layer (e.g., a photochromic layer) from the viewpoint of protecting the cured coating layer (e.g., a 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 process with a solvent is usually performed to clean the surface of the formed layer. However, if the protective layer is damaged during this wiping process, it can cause fogging or optical defects in the eyeglass lens.

[0143] The curing treatment is not particularly limited, and examples thereof include light irradiation and heat treatment. These 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 curing treatment conditions can be determined depending on the types of various components contained in the protective layer composition and the composition of the protective layer composition. After the curing treatment, an annealing treatment (heat treatment) can also be performed as necessary. The annealing treatment conditions 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.

[0144] The thickness of the protective layer is not particularly limited, but is preferably 5 to 40 μm, more preferably 10 to 35 μm, and particularly preferably 15 to 30 μm. If the thickness is equal to or greater than the lower limit of the above range, the durability of the eyeglass lens will be good, 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.

[0145] One embodiment of the spectacle lens manufactured by the spectacle lens manufacturing method according to one aspect of the present disclosure can have a layer structure of "photochromic layer / protective layer." With regard to the layer structure, " / " is used to mean 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, but examples include a cured coating layer generally referred to as a hard coat layer. These may be used alone or in combination of two or more. By providing a hard coat layer in addition to the protective layer, the durability of the optical article can be further improved. Furthermore, in one embodiment, the impact resistance of the optical article can be improved by providing a hard coat layer. In one embodiment, the other cured coating layer can be in direct contact with the protective layer without any other layer interposed therebetween.

[0146] The thickness of the other cured coating layer is not particularly limited, but is preferably 1 to 10 μm, more preferably 1 to 8 μm, and particularly preferably 1 to 5 μm, from the viewpoint of optical properties such as refractive index, etc. In one embodiment, the other cured coating layer can be a layer thinner than the protective layer.

[0147] In one embodiment, the hard coat layer can be formed by irradiating and / or heating a curable 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.

[0148] 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 curable 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 curable 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.

[0149] 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 curable composition.

[0150] When providing the other cured coating layer on the protective layer, there are no particular limitations, 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), causing clouding or optical defects in the eyeglass lens including the protective layer. In contrast, the protective layer formed from the above-mentioned protective layer composition exhibits excellent solvent resistance, and therefore can be said to be suitable for providing the other cured coating layer on the protective layer.

[0151] 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.

[0152] ((Other Curable Compositions)) The curable composition may or may not further contain other curable compositions, as necessary, in addition to the above-mentioned primer layer composition, photochromic layer composition, and protective layer composition. The other curable compositions are not particularly limited, and examples thereof include a composition that exhibits antireflection properties, a composition that exhibits antifouling properties, and a curable composition that exhibits antifogging properties after curing. These may be used alone or in combination of two or more.

[0153] The cured coating layer, which is a cured product of the curable composition, is not particularly limited, and examples thereof include the above-mentioned primer layer, photochromic layer, protective layer, hard coat layer, and other cured coating layers formed by curing a curable composition. These may be used alone or in combination of two or more. One embodiment of the cured coating layer may have a primer layer, a photochromic layer, and a protective layer.

[0154] The thickness of the cured coating layer is not particularly limited, but is preferably 5 to 100 μm, more preferably 5 to 70 μm, and particularly preferably 5 to 50 μm. When the thickness is equal to or greater than the lower limit of the above range, adhesion is easily maintained, while when 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 and the effect of the present disclosure (reduced thickness of the cured coating layer) is easily achieved. When the cured coating layer has multiple cured coating layers, the thickness of the cured coating layer is the total thickness of the primer layer, the photochromic layer, and the protective layer.

[0155] 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.

[0156] [Preparation of Photochromic Layer Composition 1] In a plastic container, 65 parts by mass of trimethylolpropane polyoxyethylene ether trimethacrylate (molecular weight 1264), 5 parts by mass of n-lauryl methacrylate (molecular weight 254), 5 parts by mass of 1,9-nonanediol dimethacrylate (molecular weight 296), 20 parts by mass of n-butyl methacrylate (molecular weight 142), and 5 parts by mass of a poly[(3-methacryloyloxypropyl)silsesquioxane] derivative (a compound represented by the structural formula (7) below) were mixed to obtain a mixture of polymerizable compounds. The thus-obtained mixture of polymerizable compounds 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 composition for photochromic layer 1 was obtained. The contents of the various components were as follows, relative to 100% by mass of the composition 1 for photochromic layer: the mixture of polymerizable compounds was 94.9% by mass, the photochromic compound was 3.0% by mass, the photoradical polymerization initiator was 0.3% by mass, the antioxidant was 0.9% by mass, and the light stabilizer was 0.9% by mass.

[0157] ...(6)

[0158] ... (7)

[0159] [Preparation of Primer Layer Composition 1] In a plastic container, 10 parts by mass of a hydroxyl group-containing bifunctional acrylate having a compound represented by the following structural formula (1), 40 parts by mass of a polyisocyanate (Coronate 2715, manufactured by Tosoh Corporation), and 50 parts by mass of 2-phenoxyethyl acrylate (viscosity: 13 cP) were mixed. To the mixture thus obtained, 0.02 parts by mass of a photoradical polymerization initiator (bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, Omnirad 819, manufactured by IGM Resin B.V.) was added relative to the total amount of 100 parts by mass of the mixture, and the mixture was thoroughly stirred. The mixture was then degassed using a rotation-revolution type stirring / degassing apparatus. Thus, primer layer composition 1 was obtained.

[0160] ...(1)

[0161] [Preparation of Protective Layer Composition 1] 99.0 parts by mass of tricyclodecane dimethanol diacrylate (alicyclic bifunctional (meth)acrylate) and 1.0 part by mass of a photoradical polymerization initiator (bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, Omnirad 819, manufactured by IGM Resin B.V.) were mixed in a plastic container and thoroughly stirred, and then degassed using a rotation-revolution type stirring degasser. In this way, Protective Layer Composition 1 was obtained. Note that in the Protective Layer Composition 1, the only (meth)acrylate was the alicyclic bifunctional (meth)acrylate, and therefore the content of the alicyclic bifunctional (meth)acrylate was 100% by mass, with the total (meth)acrylate being 100% by mass.

[0162] [Production of Coated Material] (Coated Material 1: Figure 3) A cylindrical block of polyacetal resin (DuPont, Delrin) was cut by lathe processing, and through-holes were formed by milling to obtain a coated material. In this way, coated material 1 (state: plate, material: polyacetal resin, thickness: 5.0 mm, shape: perfect circle, radius: 35.0 mm, number of through-holes: 1 (located at the center of coated material 3 in Figure 3), through-hole diameter: 3.0 mm, with rubber (urethane resin) on the periphery (see rubber 2 on the periphery in Figure 3)) was obtained.

[0163] (Coating 2: Figure 4) Coating 2 (state: plate, material: polyacetal resin, thickness: 5.0 mm, shape: perfect circle, radius: 35.0, number of through holes: 19 (position: see through hole 5 in Figure 4), through hole diameter (diameter of one through hole 5 located at the center of coating 2 in Figure 4): diameter 3.0 mm, through hole diameter (diameter of 18 through holes 5 located in the central portion of coating 2 in Figure 4): diameter 1.0 mm, with rubber (urethane resin) on the peripheral portion (see rubber 2 on the peripheral portion in Figure 4)) was obtained in the same manner as coating 1, except that a plurality of through holes (see through hole 5 in Figure 4) were provided in coating 1.

[0164] (Coated object 3: Figure 2) Using common tools such as a cutter and an awl, coated object 3 (state: sheet, material: silicone resin, thickness: 1.0 mm, shape: perfect circle, radius: 35.0 mm, number of through-holes: 1 (located at the center of coated object 3 in Figure 3), through-hole diameter: 3.0 mm, no rubber on the periphery) was obtained from PT-CUS (manufactured by Sekisui Chemical Co., Ltd.).

[0165] (Coating 4: Figure 5) Coating 4 (state: sheet, material: silicone resin, thickness: 1.0 mm, shape: perfect circle, radius: 35 mm, number of through holes: 19 (position: see through hole 5 in Figure 5), through hole diameter (diameter of one through hole 5 located at the center of coating 4 in Figure 5): diameter 3.0 mm, through hole diameter (diameter of 18 through holes 5 located in the central portion of coating 4 in Figure 5): diameter 1.0 mm, no rubber on the peripheral portion) was obtained in the same manner as coating 3, except that a plurality of through holes (see through hole 5 in Figure 5) were provided in coating 3.

[0166] (Coating 5: Figure 4) Coating 5 (state: plate, material: polyacetal resin, thickness: 5.0 mm, shape: circle, number of through holes: 19 (see through hole 5 in Figure 4 for location), through hole diameter (diameter of one through hole 5 located in the center of coating 5 in Figure 4): diameter 3.0 mm, through hole diameter (diameter of 18 through holes 5 located in the central portion of coating 5 in Figure 4): diameter 1.0 mm, rubber (urethane resin) present in the peripheral portion (see rubber 2 in the peripheral portion in Figure 4)) was obtained in the same manner as coating 2, except that the radius of the coating was 30.0 mm.

[0167] (Coating 6: Figure 5) Coating 6 (state: sheet, material: silicone resin, thickness: 1.0 mm, shape: circular, number of through holes: 19 (for positions, see through hole 5 in Figure 5), through hole diameter (diameter of one through hole 5 located in the center of coating 6 in Figure 5): diameter 3.0 mm, through hole diameter (diameter of 18 through holes 5 located in the central portion of coating 6 in Figure 5): diameter 1.0 mm, no rubber on the peripheral portion) was obtained in the same manner as coating 4, except that the radius of the coating was 30.0 mm.

[0168] (Coating 7) Coating 7 (state: plate, material: polyacetal resin, thickness: 5.0 mm, shape: perfect circle, radius: 35.0 mm, number of through holes: 0, rubber (urethane resin) present on the periphery (see rubber 2 on the periphery in Figure 3 )) was obtained in the same manner as coating 1, except that no through holes were provided.

[0169] (Coating 8) Coating 8 (state: plate, thickness: 5.0 mm, shape: perfect circle, radius: 35.0 mm, number of through holes: 0, no rubber on the peripheral portion) was obtained in the same manner as Coating 7, except that acrylic resin was used as the material.

[0170] [Manufacture of Eyeglass Lenses] (Example 1) A lens substrate (manufactured by HOYA Corporation, HILUX 1.67, 1.0 mm central thickness, 9.1 mm peripheral thickness, 35.0 mm radius) was immersed in a 10% by weight aqueous solution of sodium hydroxide (liquid temperature 60°C) for 5 minutes, then washed with pure water and dried. The other surface (concave surface) of the lens substrate was covered with a coating 1, and the lens substrate was placed in the spin coating mechanism (see spin coating mechanism 40 in Figure 1) of a spin coating device (manufactured by MIKASA, MS-B150) (hereinafter, the same spin coating device and spin coating mechanism will be used). As shown in Figure 1, the lens substrate was placed, from top to bottom, in the order of lens substrate 1 (Figure 1), coating 1 (coating 3 in Figure 1), V-ring 41 (Figure 1), and fixed stage 42 (Figure 1) of the spin coating device (hereinafter, the same method of placement will be used). The other surface of the lens substrate 1 ( FIG. 1 ) and the spin-coating mechanism 40 ( FIG. 1 ) were then vacuum-fixed via the through-holes 5 ( FIG. 1 ) in the coating 1 (coating 3 in FIG. 1 ). This vacuum was achieved by utilizing a mechanism provided in the spin-coating device of the above-mentioned known technology (hereinafter, vacuum application will be performed in the same manner). Primer layer composition 1 was then supplied to one surface (convex surface) of the lens substrate 1 ( FIG. 1 ). The spin-coating mechanism 40 ( FIG. 1 ) was then rotated at a rotation speed of 3000 rpm for 10 seconds in an environment of 25° C. and 50% relative humidity, and spin-coated. After this, the primer layer composition 1 applied to the lens substrate 1 ( FIG. 1 ) was irradiated with light (wavelength of light: 405 nm, intensity of light irradiation: 250 mW / cm ) in a nitrogen atmosphere (oxygen concentration of 500 volume ppm or less) at room temperature. ２ , light irradiation time: 5 seconds, light irradiation exposure amount: 1.25 J / cm ２), and this composition was cured to form a primer layer. The thickness of the formed primer layer was 10 μm. The other surface (concave surface) of lens substrate 1 ( FIG. 1 ) provided with the primer layer was coated with coating 1 (coating 3 in FIG. 1 ), which was then placed in spin coating mechanism 40 ( FIG. 1 ). The other surface of lens substrate 1 ( FIG. 1 ) and spin coating mechanism 40 ( FIG. 1 ) were vacuum-fixed together in the same manner as above. Then, photochromic layer composition 1 was supplied onto the primer layer, and the spin coating mechanism 40 ( FIG. 1 ) was rotated at a rotation speed of 1000 rpm for 5 seconds in an environment of a temperature of 25° C. and a relative humidity of 50%, thereby spin-coating. After that, the photochromic layer composition 1 applied onto the primer layer was irradiated with light (light wavelength: 405 nm, light irradiation intensity: 250 mW / cm ) in a nitrogen atmosphere (oxygen concentration of 500 volume ppm or less) at room temperature. ２ , light irradiation time: 25 seconds, light irradiation exposure amount: 6.25 J / cm ２ ), and the composition was cured to form a photochromic layer. The thickness of the formed photochromic layer was 25 μm. The other surface (concave surface) of lens substrate 1 ( FIG. 1 ) provided with the photochromic layer was coated with coating 1 (coating 3 in FIG. 1 ), which was then placed in spin coating mechanism 40 ( FIG. 1 ). The other surface of lens substrate 1 ( FIG. 1 ) and spin coating mechanism 40 ( FIG. 1 ) were vacuum-fixed together in the same manner as above. Protective layer composition 1 was then supplied onto the photochromic layer, and spin coating was performed by rotating spin coating mechanism 40 ( FIG. 1 ) at a rotation speed of 1600 rpm for 15 seconds in an environment of a temperature of 25° C. and a relative humidity of 50%, after which the protective layer composition 1 applied onto the photochromic layer 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: 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 15 μm. After forming the three layers, a heat treatment was performed in a heat treatment device (PH series, manufactured by Espec Corporation) at an ambient temperature of 90°C for 2 hours to strengthen the adhesion of each cured coating layer. The thickness of the cured coating layer was calculated from the analysis of the film thickness value using 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 "light irradiation intensity" was 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" is the integrated value of irradiation time (intensity of light irradiation (mW / cm)) measured by using a light meter (UIT-250, manufactured by USHIO Corporation) to illuminate a lens base 300 mm away from the center of the light source to the light receiving part (central wavelength 365 mm). ２ ) × irradiation time (seconds) In this way, the eyeglass lens of Example 1 was obtained.

[0171] Examples 2 to 6 Spectacle lenses of Examples 2 to 6 were obtained in the same manner as in Example 1, except that the coatings shown in Table 1 were used.

[0172] Comparative Example 1 A spectacle lens of Comparative Example 1 was obtained in the same manner as in Example 1, except that the coating 1 in Example 1 was not used.

[0173] Comparative Example 2 was carried out in the same manner as in Example 1, except that coating 7 was used and the edge surface of coating 7 and the edge surface of the lens substrate were fixed with adhesive tape (Scotch 600, manufactured by 3M). However, the lens substrate came off coating 7 during rotation during spin coating of the primer layer, and the eyeglass lens of Comparative Example 2 could not be obtained.

[0174] Comparative Example 3 Comparative Example 3 was carried out in the same manner as Example 1, except that in Example 1, coating 8 was used, 5% by mass of agar was filled between the other surface of the lens substrate and coating 8, and the edge surface of coating 8 and the edge surface of the lens substrate were fixed with adhesive tape (Scotch 600, manufactured by 3M). However, the lens substrate came off coating 8 during rotation during spin coating of the primer layer, and the eyeglass lens of Comparative Example 3 could not be obtained.

[0175] [Evaluation of eyeglass lenses] The following evaluations were carried out using each of the obtained eyeglass lenses and coatings. The evaluation results are shown in Table 1.

[0176] <Evaluation of Durability at High Speed ​​Rotation> The other surface (concave surface) of a lens substrate (manufactured by HOYA Corporation, HILUX 1.67, central thickness 1.0 mm, peripheral thickness 9.1 mm, radius 35.0 mm) was coated with the produced coating and placed in a spin coating mechanism. The other surface of the lens substrate and the spin coating mechanism were then vacuum-fixed via the through-holes in the coating 1. The spin coating mechanism was then rotated, and the feasible rotation speed (rpm) was measured and evaluated according to the following criteria. [Evaluation Criteria] A: Rotation possible at a rotation speed of 2,500 rpm to 5,000 rpm B: The lens substrate came off the coating at a rotation speed of less than 2,500 rpm A rating of A indicates that the lens substrate can be rotated at a sufficiently high speed, i.e., has high durability at high speed rotation, and is suitable for thinning the cured coating layer. On the other hand, a rating of B indicates that the lens substrate has high durability at high speed rotation, but is not suitable for thinning the cured coating layer. When no coating material was used, the above evaluation was A.

[0177] <Thin Film Evaluation of Cured Coating Layer> The thickness of the cured coating layer after curing of each curable composition was evaluated according to the following evaluation criteria. The thickness of the cured coating layer was calculated by measuring the reflectance (interference waveform) of the sample using a non-contact film thickness measurement system (FF8, manufactured by System Road Co., Ltd.) and analyzing the film thickness value using FFT (Fast Fourier Transform). [Evaluation Criteria] A: Less than 30 μm B: 30 to 40 μm C: More than 40 μm D: The lens came off during spin coating, making it impossible to produce an eyeglass lens and therefore measurement was not possible. In the cases of ratings A and B, it can be said that the thickness was sufficiently thin. On the other hand, in the cases of ratings C and D, it cannot be said that the thickness was sufficiently thin.

[0178] <Evaluation of Antifouling Property on the Other Surface of the Lens Substrate> The composition adhered to the peripheral portion of the other surface of the lens substrate (portion having a radius of 15 mm or more from the center) during application was observed visually and with a loupe (Lightscale Loupe, manufactured by Niigata Seiki Co., Ltd.) at a maximum magnification of 10x. The antifouling property of the observed eyeglass lenses was evaluated according to the following evaluation criteria. A: Level where no deposits were found B: Level where deposits could be confirmed with magnification C: Level where deposits could be confirmed only with the naked eye D: Lens came off during spin coating, making it impossible to produce an eyeglass lens and therefore impossible to observe In the cases of ratings A and B, it can be said that the antifouling property on the other surface of the lens substrate is sufficiently excellent. On the other hand, in the cases of ratings C and D, it cannot be said that the antifouling property on the other surface of the lens substrate is excellent.

[0179]

[0180] The results shown in Table 1 confirm that the manufacturing methods for eyeglass lenses of Examples 1 to 7, while not requiring particularly complicated tasks or operations, are capable of carrying out the spin coating step under conditions similar to those of the manufacturing method for eyeglass lenses of Comparative Example 1, and are capable of carrying out the spin coating step at rotational speeds that are not possible with the manufacturing method for eyeglass lenses of Comparative Examples 2 and 3. Because the manufacturing method for eyeglass lenses of the present disclosure is capable of carrying out the spin coating step at rotational speeds, it can be said that it is a manufacturing method for eyeglass lenses that excels in thinning the cured coating layer. The results shown in Table 1 confirm that the eyeglass lenses of Examples 1 to 7 have superior antifouling properties on the other surface of the lens substrate compared to the eyeglass lens of Comparative Example 1 (measurements were not possible for Comparative Examples 2 to 3, as they could not be manufactured). From the above, it can be said that the manufacturing method for eyeglass lenses of the present disclosure is a simple manufacturing method that thins the cured coating layer formed on one surface of the lens substrate and excels in antifouling properties on the other surface of the lens substrate.

[0181] Two or more of the various aspects and configurations described herein may be combined in any combination.

[0182] 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.

[0183] The present disclosure is useful in the technical field of eyeglasses.

[0184] REFERENCE SIGNS LIST 1 Lens substrate 2 Rubber on peripheral edge 3 Coating 40 Spin coating mechanism 41 V-ring 42 Fixing base 5 Through hole

Claims

1. A method for manufacturing an eyeglass lens having a cured coating layer on one surface of a lens substrate, comprising: a coating step of coating at least a portion of the other surface of the lens substrate with a coating material having one or more through holes; a depressurizing step of applying a pressure via the through holes in the coating material between the other surface of the lens substrate and a spin coating mechanism that rotates the lens substrate, thereby fixing the other surface of the lens substrate to the spin coating mechanism; and a spin coating step of spin coating one surface of the lens substrate with a curable composition.

2. The method for manufacturing eyeglass lenses according to claim 1, wherein the rotation speed in the spin coating is 2500 rpm or more.

3. The method for manufacturing eyeglass lenses according to claim 1 or 2, wherein the thickness of the cured coating layer is 5 to 100 μm.

4. The method for manufacturing eyeglass lenses according to claim 1 or 2, wherein the covering is at least one selected from the group consisting of a sheet and a plate.

5. The method for manufacturing eyeglass lenses according to claim 1 or 2, wherein the lens substrate is a convex lens whose central portion is thicker than the peripheral portion, a concave lens whose peripheral portion is thicker than the central portion, or a flat lens whose central portion and peripheral portion are the same thickness.

6. The method for manufacturing eyeglass lenses according to claim 1 or 2, wherein the lens substrate is a cylindrical lens whose peripheral thickness is not uniform.

7. The method for manufacturing a spectacle lens according to claim 1 or 2, wherein the cured coating layer comprises a primer layer, a photochromic layer, and a protective layer.

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