Plastic lens, method for manufacturing same, and eye glasses

Abstract

Provided is a plastic lens which comprises a lens base material and a cured coating layer that is formed on one surface of the lens base material, wherein: the cured coating layer has a primer layer, a photochromic layer, and a protective layer; the surface hardness of the photochromic layer is 2.0 kgf / mm2 or less; and the difference between the prescription of the plastic lens in which the cured coating layer is formed on one surface of the lens base material and the design prescription is less than 0.12. Also provided are: a method for manufacturing the plastic lens; and eye glasses.

Description

Plastic lenses, their manufacturing method, and eyeglasses

[0001] The present disclosure relates to a plastic lens, a manufacturing method thereof, and eyeglasses, and in particular to a plastic lens that has excellent colorfastness and little thermal deformation, a manufacturing method thereof, and eyeglasses equipped with the plastic lens.

[0002] Eyeglasses equipped with plastic lenses that exhibit a property (photochromic property) of developing a color under light in a predetermined wavelength range (e.g., outdoors) and fading under light outside the predetermined wavelength range (e.g., indoors) are highly convenient in that they eliminate the need to change glasses when moving between indoors and outdoors. One method for imparting photochromic property to a plastic lens involves applying a layer of a composition (polymerizable composition for forming a photochromic layer) containing a photochromic compound and a polymerizable compound having photochromic property to the surface of a lens substrate, irradiating the applied polymerizable composition for forming a photochromic layer with light to cure it, and forming a cured coating layer (photochromic layer) having photochromic property (see, for example, Patent Document 1).

[0003] International Publication No. 2003 / 011967

[0004] It is desirable for the above-mentioned photochromic plastic lenses that develop color when exposed to light outdoors or the like and then quickly fade (fading) after the lens is no longer exposed to light indoors or the like. Furthermore, a large amount of light irradiation is usually required to cure the photochromic layer-forming polymerizable composition, and the heat generated by the light irradiation can significantly deform the lens substrate, making it unsuitable for use. Therefore, it is desirable for the photochromic plastic lenses to exhibit minimal thermal deformation while still allowing the formation of a photochromic layer.

[0005] An object of one aspect of the present disclosure is to provide a plastic lens that has excellent color fading resistance and little thermal deformation, a method for manufacturing the same, and eyeglasses equipped with the plastic lens.

[0006] The embodiments of the present disclosure relate to the following [1] to [8]: [1] A lens substrate comprising: a lens substrate; and a cured coating layer formed on one surface of the lens substrate, wherein the cured coating layer has a primer layer, a photochromic layer, and a protective layer, and the surface hardness of the photochromic layer is 2.0 kgf / mm ２

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[290] [310 ２ or more. [5] The plastic lens according to any one of [1] to [4] above, wherein the thickness of the cured coating layer is 40 to 100 μm. [6] The plastic lens according to any one of [1] to [5] above, wherein the lens substrate has a thickness of less than 2 mm in a central portion and a peripheral portion that is thicker than the central portion. [7] Eyeglasses equipped with the plastic lens according to any one of [1] to [6] above. [8] A method for producing the plastic lens according to any one of [1] to [6] above, comprising: a primer layer forming step of forming a primer layer on one surface of the lens substrate; a photochromic layer forming step of applying a photochromic layer-forming polymerizable composition on the surface of the primer layer and curing the photochromic layer-forming polymerizable composition by light irradiation to form a photochromic layer; and a protective layer forming step of forming a protective layer on the surface of the photochromic layer, wherein the light irradiation intensity is 150 to 350 mW / cm ２ the light irradiation time is 1 to 90 seconds, and the light irradiation exposure dose is 0.15 to 31.5 J / cm ２This is a method for manufacturing a plastic lens.

[0007] As a result of extensive research into solving the above-mentioned problems, the inventors discovered that the above-mentioned problems can be solved by setting the surface hardness of the photochromic layer and the difference between the power of a plastic lens having a cured coating layer formed on one surface of a lens substrate and the design power within a specified range, and thus completed the present invention.

[0008] According to one aspect of the present disclosure, it is possible to provide a plastic lens that has excellent color fading resistance and little thermal deformation, a method for manufacturing the same, and eyeglasses equipped with the plastic lens.

[0009] The following description is based on an example of an embodiment of the present disclosure. However, the embodiments described below are merely examples for embodying the technical concept of the present disclosure, and the present disclosure is not limited to the following description. The present disclosure also includes any embodiment or combination of any of the features described herein. In the present disclosure and this specification, preferred specifications can be selected arbitrarily, and combinations of preferred specifications are considered more preferable. In the present disclosure and this specification, the expression "XX to YY" means "XX or more and YY or less." In the present disclosure and this specification, for preferred numerical ranges (e.g., ranges of content, etc.), lower and upper limits described in stages can be independently combined. For example, the expression "preferably 10 to 90, more preferably 30 to 60" can be combined with the "preferable lower limit (10)" and the "more preferable upper limit (60)" to form "10 to 60." Furthermore, in the numerical ranges described in the present disclosure and this specification, the upper or lower limit of the numerical range may be replaced with a value shown in the examples. In the present disclosure and this specification, a polymerizable composition refers to a composition containing a polymerizable compound. Furthermore, a polymerizable compound refers to a compound having a polymerizable group. In this disclosure and this specification, "design power" refers to the ideal power of a plastic lens at the design stage. The "difference between the power of a plastic lens with a cured coating layer formed on one surface of a lens substrate and the design power" refers to the difference between the power of an actually manufactured plastic lens (a plastic lens with a cured coating layer formed on one surface of a lens substrate) and the ideal power of the plastic lens at the design stage. The design power may be the power of the lens substrate before the cured coating layer is formed, or it may not be the power of the lens substrate before the cured coating layer is formed. In this disclosure and this specification, "on the surface of X" refers to not only "on the surface of X (contact state)" but also "above the surface of X (non-contact state)." In this disclosure and this specification, "(meth)acrylate" refers to both acrylate and methacrylate. An "acrylate" is a compound having one or more acryloyl groups per molecule.A "methacrylate" is a compound having one or more methacryloyl groups in one molecule. The functionality of a (meth)acrylate is the number of groups selected from the group consisting of acryloyl groups and methacryloyl groups contained in one molecule. Furthermore, a "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, the term "total amount" refers to the total amount of all components excluding the solvent, when the solvent is included.In this disclosure and this specification, the term "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 the portion within 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 the portion within a radius of more than 5 mm but less than 15 mm from the center of the lens substrate. In this disclosure and this specification, a "plastic lens" may be a finished lens or a semi-finished lens. A semi-finished lens is a lens that is processed into a lens for actual use by polishing or grinding. In this disclosure and this specification, a "finished lens" refers to a semi-finished lens that has been processed into a lens for actual use by polishing or grinding, or a lens that is molded into a lens for actual use. In this disclosure and this specification, the term "lens substrate thickness" refers to a value measured using a high-performance ABS Digimatic Indicator (ID-FNX series, manufactured by Mitutoyo Corporation) with terminals connected to the convex and concave surfaces of the lens substrate. The term "thickness of the cured coating layer" used in this disclosure and this specification 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 measuring instrument (FF8 series, manufactured by System Road Co., Ltd.). The term "intensity of light irradiation" used in this disclosure and this specification refers to a value measured using an actinometer (UIT-250, manufactured by USHIO Co., Ltd.) by lighting a lens base 300 mm away from the center of the light source to the light receiving unit (center wavelength 365 mm). The term "exposure amount of light irradiation" used in this disclosure and this specification refers to the integrated value of irradiation time (light irradiation intensity (mW / cm)) measured using an actinometer (UIT-250, manufactured by USHIO Co., Ltd.) by lighting a lens base 300 mm away from the center of the light source to the light receiving unit (center wavelength 365 mm). ２ ) × irradiation time (seconds).

[0010] [Plastic Lens] The plastic lens according to one aspect of the present disclosure will be described in further detail below.

[0011] In the present disclosure and this specification, the plastic lens is not particularly limited as long as it comprises a lens substrate and a cured coating layer formed on one surface of the lens substrate, and may or may not comprise another cured coating layer formed on the other surface of the lens substrate. The other cured coating layer may be a primer layer, a protective layer, a hard coat layer, or another functional layer, as described below.

[0012] The surface hardness of the photochromic layer is 2.0 kgf / mm ２ There is no particular limitation as long as it is below 0.5 to 1.5 kgf / mm ２ , more preferably 0.5 to 1.2 kgf / mm ２ When the hardness is equal to or greater than the lower limit of the above range, the photochromic layer is less likely to become gel or liquid and is more likely to maintain its shape, while when the hardness is equal to or less than the upper limit of the above range, the photochromic layer exhibits better fading resistance. The surface hardness of the photochromic layer can be measured by the method described in the Examples.

[0013] From the viewpoint of optical quality, the difference between the power of the plastic lens having a cured coating layer formed on one surface of the lens substrate and the design power is not particularly limited as long as it is less than 0.12, but is preferably 0.00 to 0.09, more preferably 0.00 to 0.06, and particularly preferably 0.00 to 0.03. The difference between the power of the plastic lens and the design power can be measured by the method described in the Examples.

[0014] <Lens Substrate> The lens substrate will now be described in more detail.

[0015] 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; etc. These may be used alone or in combination of two or more.

[0016] The type of the lens substrate is not particularly limited, and examples thereof include lens substrates used in spectacles and lens substrates used in goggles.

[0017] The color of the lens substrate is not particularly limited, and it may be colorless (an undyed lens) or dyed.

[0018] 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.

[0019] The focal point of the lens substrate is not particularly limited, and examples thereof include single-focus, multi-focus, and progressive-addition lenses.

[0020] 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 a convex surface and the eyeball-side surface is a concave surface, but the present disclosure is not limited to this.

[0021] 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.

[0022] <Cured Coating Layer> The cured coating layer will be described in more detail below.

[0023] In the present disclosure and this specification, the cured coating layer is not particularly limited as long as it is formed on one surface of the lens substrate and has a primer layer, a photochromic layer, and a protective layer, and may or may not have a hard coat layer, other functional layers, etc.

[0024] The thickness of the cured coating layer is not particularly limited, but is preferably 40 to 100 μm, more preferably 45 to 95 μm, and particularly preferably 50 to 90 μm. If the thickness is equal to or greater than the lower limit of the above range, adhesion is more easily maintained, and if the thickness is equal to or less than the upper limit of the above range, the transmittance (transparency) of the cured coating layer is more easily maintained.

[0025] (Primer Layer) The primer layer will be described in more detail below.

[0026] In this disclosure and this specification, the primer layer refers to a cured polymerizable composition for forming a primer layer (hereinafter, sometimes simply referred to as a "primer layer composition.") The location of the primer layer is not particularly limited, but is preferably between the lens substrate and the photochromic layer from the viewpoint of improving adhesion between the lens substrate and the photochromic layer.

[0027] 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.

[0028] One example of the primer layer composition is a primer layer composition containing a polyisocyanate, a hydroxyl group-containing polymerizable compound, and at least one polymerizable compound selected from the group consisting of (meth)acrylates and vinyl ethers, the polymerizable compound having a viscosity of 100 cP or less. While there are no particular limitations on the components contained in the primer layer composition, it is preferable for the primer layer composition to contain the above three components from the viewpoints of suppressing attenuation of photochromic properties due to the primer layer and of adhesion to the photochromic layer. The various components contained in the primer layer composition are described in more detail below.

[0029] -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.

[0030] 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.

[0031] 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.

[0032] -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.

[0033] 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.

[0034] 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.

[0035] 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.

[0036] 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.

[0037] ...(1)

[0038] 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.

[0039] 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.

[0040] -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.

[0041] 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.

[0042] 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.

[0043] 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.

[0044] 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.

[0045] 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 a primer layer composition containing the low-viscosity polymerizable compound, polyisocyanate, and hydroxy group-containing polymerizable compound.

[0046] 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.

[0047] 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.

[0048] 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.

[0049] 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 polymerizable composition for forming a photochromic layer described below.

[0050] 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 polymerizable 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.

[0051] 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.

[0052] 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).

[0053] The primer layer composition can be prepared by mixing the various components described above simultaneously or sequentially in any order.

[0054] (Photochromic Layer) The photochromic layer will be described in more detail below.

[0055] In this disclosure and this specification, the photochromic layer refers to a cured product of a photochromic layer-forming polymerizable composition (hereinafter, sometimes simply referred to as a "photochromic layer composition.") The location of the photochromic layer is not particularly limited, but from the viewpoints of adhesion to the lens substrate and protection of the photochromic layer, it is preferably between the primer layer described above and the protective layer described below.

[0056] The thickness of the photochromic layer is not particularly limited, but is preferably 5 to 80 μm, more preferably 10 to 70 μm, and particularly preferably 15 to 60 μm. If the thickness is equal to or greater than the lower limit of the above range, the color density tends to become high, while if the thickness is equal to or less than the upper limit of the above range, transparency tends to be maintained.

[0057] One embodiment of the composition for photochromic layer includes a composition for photochromic layer containing two or more (meth)acrylates and a photochromic compound. The two or more (meth)acrylates function as polymerizable compounds in the composition for photochromic layer. The various components contained in the composition for photochromic layer will be described in more detail below.

[0058] -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.

[0059] --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.

[0060] 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.

[0061] 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.

[0062] ... (2)

[0063] In formula (2), R １ and R ２ each 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.

[0064] 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.

[0065] ...(3)

[0066] 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 OR ４８ The number of repetitions of the alkoxy group represented by the formula (I) is 2 or more.

[0067] 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.

[0068] 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.

[0069] 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. ４３The 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.

[0070] R in formula (3) ４０ , R ４４ and R ４７ R in formula (3) each independently represents an alkylene group. ４０ , R ４４ and R ４７ The number of carbon atoms of the alkylene group represented by the formula (3) is not particularly limited, but is preferably 1 to 5, and more preferably 1 to 4. ４０ , R ４４ and R ４７ Specific examples of the alkylene group represented by the formula (I) are not particularly limited, and include, for example, a methylene group, an ethylene group, a propylene group, and a tetramethylene group.

[0071] 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.

[0072] --Component B-- Component B is a monofunctional (meth)acrylate represented by the following formula (4).

[0073] ...(4)

[0074] 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.

[0075] 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.

[0076] 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.

[0077] 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.

[0078] 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.

[0079] --Component C-- Component C is a polyfunctional (meth)acrylate having neither a cyclic structure nor a branched structure, represented by the following formula (5).

[0080] ...(5)

[0081] In formula (5), R ３ and R ４each 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.

[0082] 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.

[0083] 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.

[0084] --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.

[0085] 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.

[0086] 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.

[0087] 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.

[0088] 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.

[0089] The component D may contain only acryloyl groups, only methacryloyl groups, or both acryloyl groups and methacryloyl groups as (meth)acryloyl groups.

[0090] 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% by mass, and more preferably 80 to 95% by mass, relative to 100% by 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 polymerizable composition.

[0091] 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.

[0092] 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.

[0093] 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.

[0094] 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.

[0095] 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.

[0096] 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.

[0097] -Other Components- In addition to the two or more (meth)acrylates and the photochromic compound, the composition for photochromic layer may contain, as necessary, one or more of various additives that may be typically contained in polymerizable compositions, in any amount. The additives that may be contained in the composition for photochromic layer are not particularly limited, and examples thereof include a polymerization initiator for promoting a polymerization reaction.

[0098] 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.

[0099] 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.

[0100] 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.

[0101] The composition for the photochromic layer can be prepared by mixing the various components described above simultaneously or sequentially in any order.

[0102] (Protective Layer) The protective layer will be described in more detail below.

[0103] In the present disclosure and this specification, the term "protective layer" refers to a cured polymerizable composition for forming a protective layer (hereinafter, sometimes simply referred to as "protective layer composition"). The location of the protective layer is not particularly limited, but is preferably on the photochromic layer from the viewpoint of protecting the photochromic layer. From this viewpoint, the protective layer preferably has high hardness. The protective layer is not particularly limited, but preferably has excellent solvent resistance. In the manufacturing process of optical articles, after the protective layer is formed, a wiping process with a solvent is usually performed to clean the surface of the formed protective layer. However, if the protective layer is damaged during this wiping process, it can cause clouding or optical defects in the plastic lens.

[0104] The thickness of the protective layer is not particularly limited, but is preferably 10 to 50 μm, more preferably 12 to 45 μm, and particularly preferably 15 to 40 μm. If the thickness is equal to or greater than the lower limit of the above range, the durability of the plastic lens will be improved, and if the thickness is equal to or less than the upper limit of the above range, the transmittance (transparency) of the cured coating layer will be easily maintained.

[0105] One embodiment of the protective layer composition is a polymerizable composition containing one or more (meth)acrylates and containing 70.0 mass% or more of an alicyclic bifunctional (meth)acrylate relative to 100 mass% of all (meth)acrylates. While there are no particular limitations on the components contained in the protective layer composition, it is preferable that the protective layer composition contain an alicyclic bifunctional (meth)acrylate component from the viewpoints of hardness and solvent resistance of the protective layer.

[0106] 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 polymerizable composition for forming a photochromic layer. The content of the alicyclic bifunctional (meth)acrylate is not particularly limited relative to 100% by mass of all (meth)acrylates, but from the viewpoint of achieving higher hardness and superior solvent resistance in the protective layer, it is preferably 70.0% by mass or more, more preferably 75.0% by mass or more, even more preferably 85.0% by mass or more, and particularly preferably 95.0% by mass or more. As one embodiment of the content of the alicyclic bifunctional (meth)acrylate, the total amount of (meth)acrylate may be the alicyclic bifunctional (meth)acrylate.

[0107] 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.

[0108] 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).

[0109] 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.

[0110] 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 polymerizable composition.

[0111] 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.

[0112] The polymerization initiator is not particularly limited, and examples thereof include photoradical polymerization initiators and thermal polymerization initiators. These may be used alone or in combination of two or more. Among these, photoradical polymerization initiators are preferred from the viewpoint of progressing the polymerization reaction in a short time. Specific examples of photoradical polymerization initiators can be found in the polymerization initiators that can be contained in the polymerizable composition for forming a photochromic layer described above. The content of the polymerization initiator is not particularly limited, and from the viewpoint of the efficiency of forming the protective layer, it is preferably 0.1 to 5.0% by mass relative to 100% by mass of the composition for forming the protective layer.

[0113] 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.

[0114] The composition for the protective layer can be prepared by mixing the various components described above simultaneously or sequentially in any order.

[0115] A plastic lens according to one embodiment of the present disclosure may have a layer structure of "photochromic layer / protective layer." Regarding the layer structure, " / " is used to encompass both a structure in which the layers are in direct contact without any other layer interposed therebetween and a structure in which the layers are provided via one or more other layers. Furthermore, in one embodiment, the optical article may have a layer structure of "photochromic layer / protective layer / other cured coating layer." The other cured coating layer is not particularly limited, and examples thereof include a cured layer generally referred to as a hard coat layer. These may be used alone or in combination of two or more. Providing a hard coat layer in addition to the protective layer can further enhance the durability of the optical article. Furthermore, in one embodiment, providing a hard coat layer can also enhance the impact resistance of the optical article. In one embodiment, the other cured coating layer may be in direct contact with the protective layer without any other layer interposed therebetween.

[0116] 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. In one embodiment, the other cured coating layer can be thinner than the protective layer. The other cured coating layer is not particularly limited, and examples thereof include organosilicon-based cured layers. Organosilicon-based cured layers are generally preferred because they have excellent impact resistance. Furthermore, in one embodiment, when an antireflection layer is further provided, organosilicon-based cured layers are generally preferred because they have excellent adhesion to the antireflection layer.

[0117] The organosilicon-based cured layer is a cured layer obtained by curing a polymerizable composition containing an organosilicon compound. The organosilicon compound is not particularly limited, and examples thereof include organosilicon compounds capable of generating silanol groups by polymerization; organopolysiloxanes having reactive groups such as halogen atoms or amino groups that undergo condensation reaction with silanol groups; silane coupling agents having polymerizable groups such as vinyl groups, allyl groups, (meth)acryloyl groups, and (meth)acryloyloxy groups and hydrolyzable groups such as alkoxy groups; and the like. These may be used alone or in combination of two or more. The polymerizable composition containing an organosilicon compound may further contain silicon oxide; particles of inorganic substances such as titanium oxide; etc., as necessary, for adjusting the refractive index, etc. For details of the polymerizable composition containing an organosilicon compound, known techniques related to organosilicon-based cured layers that can function as hard coat layers can be applied. The polymerizable composition containing an organosilicon compound can be cured by promoting a polymerization reaction through light irradiation and / or heat treatment, depending on the types of components contained in the composition.

[0118] When the other cured coating layer is provided on the protective layer, there is no particular limitation, but from the viewpoint of preventing foreign matter from being interposed between the protective layer and the other cured coating layer, it is preferable to perform a solvent wiping treatment on the surface of the protective layer. However, if the protective layer has poor solvent resistance, the solvent wiping treatment will damage the protective layer (for example, cause surface roughness), which will cause clouding or optical defects in the plastic lens including the protective layer. In contrast, the protective layer 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.

[0119] 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.

[0120] (Other Functional Layers) The coated cured layer may or may not further include other functional layers as needed in addition to the above-mentioned primer layer, photochromic layer, and protective layer. The other functional layers are not particularly limited, and examples thereof include an anti-reflection layer, a water-repellent or hydrophilic anti-fouling layer, an anti-fogging layer, etc. These may be used alone or in combination of two or more.

[0121] [Eyeglasses] One aspect of the present disclosure relates to eyeglasses equipped with the plastic lenses. Details of the plastic lenses equipped in the eyeglasses are as described above. By including the plastic lenses, the eyeglasses can exhibit an anti-glare effect similar to sunglasses, for example, outdoors, as the photochromic compound contained in the photochromic layer changes color when irradiated with sunlight, and once indoors, the photochromic compound fades, allowing transparency to be restored. There are no particular limitations on the configuration of the eyeglasses' frames, and known techniques can be applied.

[0122] [Method for manufacturing plastic lens] One aspect of the present disclosure is a method for manufacturing the above-mentioned plastic lens, comprising: a primer layer forming step of forming a primer layer on one surface of a lens substrate; a photochromic layer forming step of applying a photochromic layer-forming polymerizable composition on the surface of the primer layer and curing the photochromic layer-forming polymerizable composition by light irradiation to form a photochromic layer; and a protective layer forming step of forming a protective layer on the surface of the photochromic layer, and may further comprise other steps as necessary.

[0123] <Primer Layer Forming Step> The primer layer forming step will be described in further detail below.

[0124] The primer layer can be formed on one surface of the lens substrate by applying a primer layer composition to one surface of the lens substrate and then curing the applied primer layer composition. The application method is not particularly limited, and known application methods can be used, such as spin coating and dip coating. These methods may be used alone or in combination. Among these, spin coating is preferred from the viewpoint of uniformity of application. The curing treatment is not particularly limited, and examples include light irradiation and heat treatment. These methods may be used alone or in combination. Among these, light irradiation is preferred from the viewpoint of progressing the curing reaction in a short time. The curing treatment conditions can be determined depending on the types of 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 be performed as necessary. The annealing conditions are not particularly limited, but it is preferable to perform the annealing treatment in a heat treatment furnace at an atmospheric temperature of approximately 90 to 130°C.

[0125] <Photochromic Layer Forming Step> Hereinafter, the photochromic layer forming step will be described in more detail.

[0126] The photochromic layer can be formed on the surface of the primer layer by applying a photochromic layer composition to the surface of the primer layer and curing the applied photochromic layer composition. The application method is not particularly limited, and known application methods can be used, such as spin coating and dip coating. These methods may be used alone or in combination of two or more. Of these, spin coating is preferred from the viewpoint of uniformity of application. The curing treatment is not particularly limited, and examples include light irradiation and heat treatment. These methods may be used alone or in combination of two or more. Of 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 plastic 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 plastic 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 plastic 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 ２ After the hardening treatment, an annealing treatment (heat treatment) can be carried out as necessary. The conditions for the annealing treatment are not particularly limited, but it is preferable to carry out the annealing treatment in a heat treatment furnace with an atmospheric temperature of about 90 to 130°C.

[0127] <Protective Layer Forming Step> The protective layer forming step will be described in more detail below.

[0128] The protective layer can be formed on the surface of the photochromic layer by applying a protective layer composition to the surface of the photochromic layer and curing the applied protective layer composition. If necessary, a primer layer or the like may be further formed between the photochromic layer and the protective layer to improve adhesion between the photochromic layer and the protective layer. The coating method is not particularly limited, and known coating methods can be used, such as spin coating and dip coating. These methods may be used alone or in combination. Among these, spin coating is preferred from the viewpoint of uniformity of coating. The curing treatment is not particularly limited, and examples include light irradiation and heat treatment. These methods may be used alone or in combination. Among these, light irradiation is preferred from the viewpoint of progressing the curing reaction in a short time. The curing treatment conditions can be determined depending on the types of 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 conditions for the annealing treatment are not particularly limited, but it is preferable to perform the treatment in a heat treatment furnace with an atmospheric temperature of about 90 to 130°C.

[0129] 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.

[0130] [Preparation of Polymerizable Composition for Forming Photochromic Layer] Photochromic layer compositions 1 to 3, which are polymerizable compositions for forming photochromic layers, were prepared as follows.

[0131] (Photochromic layer composition 1) In a plastic container, polyethylene glycol dimethacrylate ((in the above formula (2), n=14, R=ethylene group, R １ and R ２90 parts by mass of methyl acrylate (number average molecular weight 726) and 10 parts by mass of tricyclodecane dimethanol dimethacrylate (molecular weight 332) were mixed together 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 90.0% by mass, the photochromic compound was 5.7% by mass, the photoradical polymerization initiator was 0.7% by mass, the antioxidant was 2.7% by mass, and the light stabilizer was 0.9% by mass.

[0132] ...(6)

[0133] (Photochromic layer composition 2) Photochromic layer composition 2 was obtained by the same production method as for "photochromic layer composition 1", except that the compounds used in preparing the polymerizable compound mixture for photochromic layer composition 2 (see below) were used instead. The contents of the various components were as follows, relative to 100% by mass of photochromic layer composition 2: 94.9% by mass of the polymerizable compound mixture, 3.0% by mass of the photochromic compound, 0.3% by mass of the photoradical polymerization initiator, 0.9% by mass of the antioxidant, and 0.9% by mass of the light stabilizer. The mixture of polymerizable compounds for photochromic layer composition 2 was prepared by mixing, 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).

[0134] ... (7)

[0135] (Photochromic Layer Composition 3) In a plastic container, 20 parts by mass of trimethylolpropane trimethacrylate (molecular weight 338), 35 parts by mass of 2,2-bis(4-methacryloyloxypolyethoxyphenyl)propane) (molecular weight 541), 10 parts by mass of polyester oligomer hexaacrylate (manufactured by Daicel Corporation, EBECRYL1830, molecular weight 1500), 10 parts by mass of polyethylene glycol diacrylate (average molecular weight 532), and 10 parts by mass of glycidyl methacrylate (molecular weight 142) were mixed to obtain a polymerizable compound mixture. To 100 parts by mass of the mixture of polymerizable compounds thus obtained, 3 parts by mass of a photochromic compound (chromene compound (A) represented by the structural formula (8) below), 0.6 parts by mass of a photoradical polymerization initiator (CGI-1870, manufactured by Ciba Specialty Chemicals), 5 parts by mass of an antioxidant (Irgacure 245, manufactured by Ciba Specialty Chemicals), and 5 parts by mass of 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) were added and thoroughly mixed with stirring. Then, 6 parts by mass of γ-methacryloyloxypropyltrimethoxysilane (KBM503, manufactured by Shin-Etsu Chemical Co., Ltd.) was added dropwise with stirring. The mixture was then degassed for 2 minutes using a rotation-revolution type stirring and degassing apparatus, and 40 parts by mass of polyethylene glycol diacrylate (average molecular weight 708) was added. In this way, a composition 3 for photochromic layer was obtained.

[0136] ...(8)

[0137] [Preparation of Polymerizable Composition for Forming Primer Layer] 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 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.

[0138] ...(1)

[0139] [Preparation of Polymerizable Composition for Forming Protective Layer] In a plastic container, 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 and thoroughly stirred, and then degassed using a rotation-revolution type stirring and degassing apparatus. In this way, protective layer composition 1 was obtained. Note that in the above 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.

[0140] [Production of Plastic Lens] (Example 1) A lens substrate (manufactured by HOYA Corporation, HILUX1.67, central thickness 1.0 mm, peripheral thickness 9.1 mm) was immersed in a 10% by mass aqueous solution of sodium hydroxide (liquid temperature 60°C) for 5 minutes, then washed with pure water and dried. Thereafter, primer layer composition 1 was applied to the convex surface (object-side surface) of the lens substrate by spin coating in an environment of a temperature of 25°C and a relative humidity of 50%, and the primer layer composition 1 applied to the lens substrate was then irradiated with light (light wavelength: 405 nm, light irradiation intensity: 250 mW / cm) in a nitrogen atmosphere (oxygen concentration 500 volume ppm or less). ２ , light irradiation time: 5 seconds, light irradiation exposure amount: 1.25 J / cm ２ ) and curing this composition to form a primer layer. The formed primer layer had a thickness of 10 μm. Photochromic layer composition 1 was applied onto the primer layer by spin coating. Spin coating was performed according to the method described in JP-A-2005-218994. Thereafter, the photochromic layer composition 1 applied onto the primer layer was irradiated with light (wavelength of light: 405 nm, intensity of light irradiation: 250 mW / cm) in a nitrogen atmosphere (oxygen concentration: 500 volume ppm or less). ２ , light irradiation time: 25 seconds, light irradiation exposure amount: 6.25 J / cm ２ ) and curing the composition to form a photochromic layer. The thickness of the formed photochromic layer was 40 μm. Onto the photochromic layer, protective layer composition 1 was applied by spin coating to form a coating layer. The surface of this coating layer was irradiated with light (wavelength of light: 405 nm, intensity of light irradiation: 250 mW / cm) in a nitrogen atmosphere (oxygen concentration: 500 volume ppm or less). 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 protective layer was 38 μm. After forming the three layers, the lens substrate was heat-treated for two hours at an ambient temperature of 90°C in a heat treatment device (PH series, manufactured by Espec Corporation) to strengthen the adhesion of each cured coating layer. The thickness of the cured coating layer was calculated by subtracting the thickness of the central portion of the lens substrate before and after the formation of the cured coating layer from the thickness of the central portion of the lens substrate after the formation of the cured coating layer. The thickness of the lens substrate before and after the formation of the cured coating layer was measured using a high-performance ABS Digimatic Indicator (ID-FNX series, manufactured by Mitutoyo Corporation) by connecting terminals to the convex and concave surfaces of the central portion of the lens substrate. 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 plastic lens of Example 1 was obtained.

[0141] (Example 2) A plastic lens of Example 2 was obtained in the same manner as in Example 1, except that composition 2 for photochromic layer was used instead of composition 1 for photochromic layer, the thickness of the photochromic layer was set to 25 μm, and the thickness of the protective layer was set to 15 μm.

[0142] Comparative Example 1 In Example 2, light irradiation (light wavelength: 405 nm, light irradiation intensity: 250 mW / cm ２ , light irradiation time: 25 seconds, light irradiation exposure amount: 6.25 J / cm ２ ) was irradiated with light (wavelength of light: 405 nm, intensity of light irradiation: 250 mW / cm ２ , light irradiation time: 40 seconds, light irradiation exposure dose: 10.0 J / cm ２ A plastic lens of Comparative Example 1 was obtained in the same manner as in Example 2, except that the above-mentioned compound was replaced with the compound 1.

[0143] Comparative Example 2 A plastic lens of Comparative Example 2 was obtained in the same manner as in Example 1, except that composition 3 for photochromic layer was used instead of composition 1 for photochromic layer, the thickness of the primer layer was 6 μm, the thickness of the photochromic layer was 40 μm, and no protective layer was provided.

[0144] (Comparative Example 3) In Comparative Example 2, light irradiation (light wavelength: 405 nm, light irradiation intensity: 250 mW / cm ２ , light irradiation time: 25 seconds, light irradiation exposure amount: 6.25 J / cm ２ ) was irradiated with light (wavelength of light: 405 nm, intensity of light irradiation: 250 mW / cm ２ , light irradiation time: 60 seconds, light irradiation exposure amount: 15.0 J / cm ２ A plastic lens of Comparative Example 3 was obtained in the same manner as in Comparative Example 2, except that the resin composition was changed to .

[0145] [Evaluation of Plastic Lenses] The following evaluations were carried out using each of the obtained plastic lenses. The evaluation results are shown in Table 2.

[0146] <Surface Hardness of Photochromic Layer> Using an ultra-microindentation hardness tester (ENT-2100, manufactured by Elionix Co., Ltd.), the indentation depth h (nm) corresponding to the indentation load P (kgf) was continuously measured throughout the entire process from the start of loading to unloading at the measurement point, and a P-h curve was created. From the created P-h curve, the indentation hardness H was calculated using the following formula: H (kgf / mm ２ ) = Pmax / A (where Pmax is the maximum load (kgf) and A is the indenter projected area (mm ２ ) The indentation hardness here is a value determined from the displacement-load curve from loading to unloading of the measuring indenter, and is specified in ISO 14577:2015.

[0147] <Outermost surface scratch resistance> The surface of the photochromic lens is scratched with steel wool (standard #0000, manufactured by Japan Steel Wool Co., Ltd.) at 1 kgf / cm ２The lens surface was rubbed while being pressed against the lens with a cloth, and the scratch resistance was visually judged. The measured scratches on the outermost surface were evaluated according to the following evaluation criteria. [Evaluation criteria] UA: Almost no scratches. A: A few thin scratches, or about 2 deep but thin scratches. B: About 20 thin scratches, or about 10 thin but deep scratches. C: Many deep scratches (regardless of thickness) occurred, resulting in a state close to cloudiness, or shallow scratches but no coating (weak film). In the cases of ratings UA and A, the photochromic layer is resistant to scratches and deterioration of the photochromic properties of the plastic lens is suppressed, so it can be said that the outermost surface scratch resistance is sufficiently excellent. On the other hand, in the cases of ratings B and C, it cannot be said that the outermost surface scratch resistance is excellent.

[0148] <Difference from Design Diopter> Using a diopter measuring device (CL-300, manufactured by Topcon Corporation), the spherical refractive index S and addition power C of the center (within a radius of 5 mm) of the lens substrate, and the spherical refractive index S and addition power C of the center (within a radius of 5 mm) of the plastic lens manufactured as described above were measured. The absolute value of the difference between the total value of the spherical refractive index S and addition power C of the center of the lens substrate and the total value of the spherical refractive index S and addition power C of the center of the plastic lens was then taken as the "difference from design diopter" for each plastic lens. The measured difference from the design diopter was evaluated according to the following evaluation criteria. [Evaluation Criteria] A: 0.06 or less B: More than 0.06 and 0.09 or less C: More than 0.09 and less than 0.12 D: 0.12 or more In the cases of ratings A to C, the difference from the design diopter is sufficiently small, so it can be said that the thermal deformation of the plastic lens is sufficiently small. On the other hand, in the case of rating D, the difference from the design diopter is not small, so it cannot be said that the thermal deformation of the plastic lens is sufficiently small.

[0149] <Fade Rate (Fadeability)> The surface of the photochromic layer (a cured layer obtained by curing the polymerizable composition) of each spectacle lens in the Examples and Comparative Examples was irradiated with light from a xenon lamp through an aeromass filter for 15 minutes (900 seconds) to cause the photochromic compound in the photochromic layer to develop a color. The transmittance (measurement wavelength: 550 nm) upon color development was measured using a spectrophotometer manufactured by Otsuka Electronics Co., Ltd. The light irradiation was carried out so that the irradiance and the tolerance of the irradiance, as specified in JIS T 7333:2005, were the values ​​shown in Table 2 below. The transmittance measured in this manner is referred to as the "transmittance upon color development." After measuring the transmittance during color development, the transmittance was measured 60 seconds after the light irradiation was stopped (hereinafter referred to as "60-second transmittance during fading"). The fading rate (unit: % / second) was calculated using the formula: fading rate = [(60-second transmittance during fading - transmittance during color development) / 60]. The higher the value of the fading rate thus obtained, the faster the fading rate. The measured fading rate values ​​were evaluated according to the following evaluation criteria. [Evaluation criteria] A: More than 0.60% / second B: 0.40 to 0.60% / second C: Less than 0.40% / second In the cases of ratings A and B, the fading properties can be said to be sufficiently excellent. On the other hand, in the case of rating C, the fading properties cannot be said to be excellent.

[0150]

[0151] From the results shown in Table 2, it can be confirmed that the plastic lenses of Examples 1 and 2 have excellent fading resistance and less thermal deformation than the plastic lenses of Comparative Examples 1 to 3. The inventors set the surface hardness of the photochromic layer to 2.0 kgf / mm ２ The inventors believe that the following contributes to the excellent fading resistance of the plastic lenses of Examples 1 and 2. The inventors believe that keeping the difference between the power of the lens substrate after the formation of the cured coating layer and the design power to less than 0.12 means that the plastic lenses of Examples 1 and 2 are less susceptible to thermal deformation.

[0152] Two or more of the various aspects and configurations described herein may be combined in any combination.

[0153] 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.

[0154] The present disclosure is useful in the technical fields of eyeglasses, goggles, and the like.

Claims

1. A lens substrate and a cured coating layer formed on one surface of the lens substrate, wherein the cured coating layer has a primer layer, a photochromic layer, and a protective layer, and the surface hardness of the photochromic layer is 2.0 kgf / mm ２ or less, and the difference between the power of the plastic lens having a cured coating layer formed on one surface of the lens substrate and the design power is less than 0.

12.

2. The plastic lens according to claim 1, wherein the photochromic layer is a layer formed by curing a polymerizable composition for forming a photochromic layer, and the polymerizable composition for forming a photochromic layer contains two or more types of (meth)acrylates and a photochromic compound.

3. The plastic lens according to claim 2, wherein the two or more (meth)acrylates include at least a polyfunctional (meth)acrylate having a molecular weight of 500 or more.

4. The surface hardness of the photochromic layer is 0.5 kgf / mm ２ The plastic lens according to claim 1 .

5. The plastic lens according to claim 1, wherein the thickness of the cured coating layer is 40 to 100 μm.

6. The plastic lens of claim 1, wherein the lens substrate has a central portion less than 2 mm thick and a peripheral portion thicker than the central portion.

7. Eyeglasses equipped with a plastic lens according to any one of claims 1 to 6.

8. A method for producing a plastic lens according to any one of claims 1 to 6, comprising: a primer layer forming step of forming a primer layer on one surface of a lens substrate; a photochromic layer forming step of applying a photochromic layer-forming polymerizable composition on the surface of the primer layer and curing the photochromic layer-forming polymerizable composition by light irradiation to form a photochromic layer; and a protective layer forming step of forming a protective layer on the surface of the photochromic layer, wherein the intensity of the light irradiation is 150 to 350 mW / cm. ２ the light irradiation time is 1 to 90 seconds, and the light irradiation exposure dose is 0.15 to 31.5 J / cm ２ This is a method for manufacturing a plastic lens.

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