Plastic lens, method for manufacturing the same, and eyeglasses

Abstract

To provide a plastic lens and a method for manufacturing the plastic lens, as well as eyeglasses including the plastic lens, the lens having excellent resistance to discoloration and being changed less by heat.SOLUTION: The plastic lens includes a lens base material and a hardened coating layer formed on one surface of the lens base material, the hardened coating layer having 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 power of the plastic lens having the hardened coating layer formed on one surface of the lens substrate and a design power is less than 0.12.SELECTED DRAWING: None

Description

[Technical Field]

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

[0002] Eyeglasses equipped with plastic lenses that exhibit photochromic properties (i.e., develop color under light in a specific wavelength range (e.g., outdoors) and fade under light outside that wavelength range (e.g., indoors) are highly convenient because they eliminate the need to change glasses when moving between indoors and outdoors. One method for imparting photochromic properties to plastic lenses involves applying a layer of a composition (polymerizable composition for forming a photochromic layer) containing a photochromic compound and a polymerizable compound, and then irradiating the applied polymerizable composition for forming a photochromic layer with light to cure it, thereby forming a cured coating layer (photochromic layer) with photochromic properties (see, for example, Patent Document 1). [Prior art documents] [Patent documents]

[0003] [Patent Document 1] International Publication No. 2003 / 011967 Summary of the Invention [Problem to be solved by the invention]

[0004] It is desirable for the above-mentioned photochromic plastic lenses to develop color when exposed to light outdoors, etc., and then quickly fade (fading) after the lens is no longer exposed to light indoors, etc. Furthermore, curing the photochromic layer-forming polymerizable composition usually requires irradiation with a large amount of light, and the heat generated by the irradiation light can significantly deform the lens substrate, making it unsuitable for use. Therefore, it is desirable for a photochromic plastic lens to have 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. [Means for solving the problem]

[0006] The embodiments of the present disclosure relate to the following [1] to [8]. [1] A lens substrate and a cured coating layer formed on one surface of the lens substrate, 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 / mm 2 is as follows: A plastic lens having a cured coating layer formed on one surface of the lens substrate, wherein the difference between the power of the plastic lens and the design power is less than 0.12. [2] The photochromic layer is a layer obtained by curing a photochromic layer-forming polymerizable composition, The photochromic layer-forming polymerizable composition is two or more (meth)acrylates; a photochromic compound; The plastic lens according to [1] above, comprising: [3] The plastic lens according to [2] above, wherein the two or more types of (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 any one of the above [1] to [3]. [5] The plastic lens according to any one of the above [1] to [4], 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 thickness of the central portion of the lens substrate is less than 2 mm, and the peripheral portion 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 a plastic lens according to any one of [1] to [6] above, 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; a protective layer forming step of forming a protective layer on the surface of the photochromic layer, The intensity of the light irradiation is 150 to 350 mW / cm 2 and The light irradiation time is 1 to 90 seconds, The exposure dose of the light irradiation is 0.15 to 31.5 J / cm 2 This 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. [Effects of the 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. DETAILED DESCRIPTION OF THE INVENTION

[0009] Hereinafter, an example of an embodiment of the present disclosure will be described. However, the embodiment described below is an example for embodying the technical idea of ​​the present disclosure, and the present disclosure is not limited to the following description. Any selected or combined embodiment of the present disclosure and the matters described in this specification is also included in the present disclosure. In the present disclosure and specification, preferred definitions can be selected arbitrarily, and combinations of preferred definitions can be considered more preferred. In this 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.), the lower and upper limits described in stages can be independently combined. For example, the description "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. Also, a polymerizable compound refers to a compound having a polymerizable group. In this disclosure and this specification, "design power" means the ideal power of a plastic lens at the design stage. "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" means the difference between the power of an actually manufactured plastic lens (a plastic lens having a cured coating layer formed on one surface of a lens substrate) and the ideal power of the plastic lens at the design stage. Note that the design power may be the power of the lens substrate before the cured coating layer is formed, or may not be the power of the lens substrate before the cured coating layer is formed. In this disclosure and this specification, "(meth)acrylate" encompasses acrylate and methacrylate. An "acrylate" is a compound having one or more acryloyl groups in one 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, "methacrylate" refers to a compound containing only methacryloyl groups as (meth)acryloyl groups, and a compound containing both acryloyl and methacryloyl groups as (meth)acryloyl groups is called 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 the present 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" is used to encompass both acryloyloxy groups and methacryloyloxy groups. In this disclosure and this specification, unless otherwise specified, the groups described may have a substituent or may be 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, a bromine atom), a cyano group, an amino group, a nitro group, an acyl group, a carboxy group, an aryl group, a polyether group, etc. Furthermore, with respect to a group having a substituent, the "number of carbon atoms" refers to the number of carbon atoms in the portion excluding the substituent. In the present disclosure and this specification, the term "straight-chain alkyl group or branched alkyl group" does not include a cycloalkyl group. The straight-chain alkyl group or branched alkyl group may be unsubstituted or may have a substituent. It is acceptable for the straight-chain alkyl group or branched alkyl group to have a cycloalkyl group (e.g., a cyclohexyl group) as a substituent. In one embodiment, it is preferable that the straight-chain alkyl group or branched alkyl group does not have a cycloalkyl group as a substituent. In this disclosure and this specification, the "viscosity" is a value measured by 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 specification, the term "central portion of the lens substrate" refers to the portion of the lens substrate having a radius of 5 mm or less from the center thereof. In this disclosure and specification, the term "peripheral portion of the lens substrate" refers to a portion of the lens substrate having a radius of 15 mm or more from the center thereof. In this disclosure and the present specification, the term "mid-peripheral portion of the lens substrate" refers to a portion of the lens substrate having a radius of more than 5 mm and less than 15 mm from the center of the lens substrate. The term "plastic lens" used in this disclosure and this specification may be a finished lens or a semi-finished lens. Note that a semi-finished lens is processed by polishing or grinding into a lens for actual use. In this disclosure and this specification, the term "finished lens" refers to a semi-finished lens that has been processed by polishing or grinding into a lens for actual use, or a lens molded into a lens for actual use. In this disclosure and this specification, the "thickness of the lens substrate" refers to the value measured by connecting terminals to the convex and concave surfaces of the lens substrate using a high-performance ABS Digimatic Indicator (ID-FNX series, manufactured by Mitutoyo Corporation). In this disclosure and this specification, the "thickness of the cured coating layer" refers to a value calculated by measuring the reflectance (interference waveform) of a sample using a non-contact film thickness measuring device (FF8 series, manufactured by System Road Co., Ltd.) and analyzing the film thickness value using FFT (fast Fourier transform). The "intensity of light irradiation" in this disclosure and this specification is a value measured using a light meter (UIT-250, manufactured by USHIO Corporation) by lighting a lens base 300 mm away from the center of the light source to the light receiving unit (center wavelength 365 mm). The term "exposure amount of light irradiation" in this disclosure and this specification refers to 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 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, but preferably 0.5 to 1.5 kgf / mm 2 , more preferably 0.5 to 1.2 kgf / mm 2 When the content is equal to or greater than the lower limit of the above range, the layer is less likely to become gel or liquid and is more likely to maintain its shape, and when the content is equal to or less than the upper limit of the above range, the layer is more resistant to fading. The surface hardness of the photochromic layer can be measured by the method described in the examples.

[0013] From the viewpoint of optical quality, there is no particular restriction on the difference between the dioptric power of the plastic lens having a cured coating layer formed on one surface of the lens substrate and the design dioptric power, as long as it is less than 0.12, but it 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 be described in more detail below.

[0015] In the present disclosure and 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, etc. 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] There are no particular restrictions on the thickness of the central portion of the lens substrate, 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 to less than 2.0 mm. There are no particular restrictions on the thickness of the peripheral portion of the lens substrate, 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 the present disclosure and this specification, the primer layer refers to a cured product of a polymerizable composition for forming a primer layer (hereinafter, sometimes simply referred to as a "primer layer composition"). The position of the primer layer is not particularly limited, but it is preferably between the lens substrate and the photochromic layer from the viewpoint of improving the 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, invasion of 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 hydroxy 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. The components contained in the composition for the primer layer are not particularly limited, but it is preferable that the composition contains the above three components from the viewpoint of suppressing attenuation of photochromic properties caused by the primer layer and from the viewpoint of adhesion to the photochromic layer. The various components contained in the primer layer composition will be described in more detail below.

[0029] -Polyisocyanate- The polyisocyanate is a compound having two or more isocyanate groups in one 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] The molecular weight of the polyisocyanate is not particularly limited, but is preferably 200 to 800, more preferably 300 to 700, and particularly preferably 400 to 600. If the molecular weight is equal to or greater than the lower limit of the above range, adhesion to the lens substrate is facilitated, and if the molecular weight is equal to or less than the upper limit of the above range, the water resistance of the primer layer is likely to be improved.

[0031] Specific examples of the polyisocyanate are not particularly limited and include, for example, aromatic diisocyanates such as xylylene diisocyanate, phenylene diisocyanate, tolylene diisocyanate, diphenylmethane diisocyanate, and naphthalene diisocyanate; aliphatic or alicyclic diisocyanates such as hexamethylene diisocyanate, lysine diisocyanate, cyclohexane diisocyanate, isophorone diisocyanate, 4,4'-dicyclohexylmethane diisocyanate, 1,3-bisisocyanatomethylcyclohexane, and tetramethylxylylene diisocyanate; etc. These may be used alone or in combination of two or more. The polyisocyanates exemplified above may be allophanate, adduct, biuret, or isocyanurate, and these may be used alone or in combination of two or more. Furthermore, commercially available polyisocyanates include, but are not limited to, Coronate HX, Coronate HXR, Coronate HXLV, Coronate HK, Coronate 2715, Coronate HL, Coronate L, Coronate 2037, HDI, TDI, and MDI (manufactured by Tosoh Corporation), Takenate 500, Takenate 600, Duranate 24A-100, TPA-100, TKA-100, P301-75E, and 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 (manufactured by Mitsui Chemicals, Inc.). 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 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 improving the 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 example 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] [ka] ···(1)

[0038] One embodiment 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, which is a structure formed by the reaction of an epoxy group with a carboxyl group and can be represented by "-CH(OH)-CH-OC(=O)-". Commercially available hydroxyl group-containing polymerizable compounds having an epoxy ester structure are not particularly limited, and examples thereof include Epoxy Ester 40EM (Kyoeisha Chemical Co., Ltd.), Epoxy Ester 70PA (Kyoeisha Chemical Co., Ltd.), Epoxy Ester 80MFA (Kyoeisha Chemical Co., Ltd.), Epoxy Ester 200PA (Kyoeisha Chemical Co., Ltd.), Epoxy Ester 3002M(N) (Kyoeisha Chemical Co., Ltd.), Epoxy Ester 3002A(N) (Kyoeisha Chemical Co., Ltd.), Epoxy Ester 3000MK (Kyoeisha Chemical Co., Ltd.), Epoxy Ester 3000A (Kyoeisha Chemical Co., Ltd.), etc. These may be used alone or in combination of two or more.

[0040] -A polymerizable compound which is at least one selected from the group consisting of (meth)acrylates and vinyl ethers and has a viscosity of 100 cP or less- The primer layer composition preferably contains at least one polymerizable compound selected from the group consisting of (meth)acrylates and vinyl ethers, and 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, but from the viewpoint of ease of handling and suppression of the occurrence of optical defects, it 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 is preferably 1 (monofunctional) to 3, more preferably 1 (monofunctional) to 2, from the viewpoint of adhesion. The (meth)acrylate, which is one form of the low-viscosity polymerizable compound, can contain an aryl group (e.g., a phenyl group), an amide group, etc. 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. In addition, 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 suitable vinyl ethers include butyl 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%, relative to 100 mass% of the total of the low-viscosity polymerizable compound, polyisocyanate, and hydroxy group-containing polymerizable compound. When the thickness is equal to or greater than the lower limit of the above range, the film is easy to handle, and when the thickness is equal to or less than the upper limit of the above range, the film is easily adhered to the lens substrate. In one embodiment of the content of the low-viscosity polymerizable compound, the low-viscosity polymerizable compound is the component that is contained in the largest amount in the composition for primer layer that contains 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 mass%, more preferably 20.0 to 60.0 mass%, and particularly preferably 30.0 to 50.0 mass%, relative to 100 mass% of the total of the low-viscosity polymerizable compound, polyisocyanate, and hydroxy group-containing polymerizable compound. When the thickness 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 thickness is equal to or less than 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, and 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, thermal polymerization initiators, etc. These may be used alone or in combination of two or more. Among these, photoradical polymerization initiators are preferred from the viewpoint of progressing the polymerization reaction in a short time. For specific examples of the photoradical polymerization initiator, reference can be made to the polymerization initiators that can be contained in the polymerizable composition for forming a photochromic layer, which will be described later.

[0050] The primer layer composition may or may not contain a solvent. When the primer layer composition contains a solvent, any solvent can be used without any particular limitation as long as it does not inhibit the progress of the polymerization reaction of the polymerizable composition. 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, the amount of the solvent 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, per 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 can usually be added to compositions for forming primer layers. 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, relative to 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%, based on 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 polymerizable composition for forming a photochromic layer (hereinafter, sometimes simply referred to as a "photochromic layer composition"). The location of the photochromic layer is not particularly limited, but from the viewpoint 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, wherein the two or more (meth)acrylates function as polymerizable compounds in the composition for photochromic layer. The various components contained in the composition for the photochromic layer will be described in more detail below.

[0058] -Two or more types of (meth)acrylate- The two or more (meth)acrylates are not particularly limited, but from the viewpoint of fading speed, it is preferable to include at least a polyfunctional (meth)acrylate having a molecular weight of 500 or more (hereinafter, sometimes referred to as "component A"). The (meth)acrylate other than Component A among the two or more (meth)acrylates is not particularly limited, and examples thereof include a monofunctional (meth)acrylate (hereinafter sometimes referred to as "Component B"), a polyfunctional (meth)acrylate having neither a cyclic structure nor a branched structure (hereinafter sometimes referred to as "Component C"), a bifunctional (meth)acrylate having at least one structure selected from the group consisting of a cyclic structure and a branched structure (hereinafter sometimes referred to as "Component D"), etc. These may be used alone or in combination of two or more.

[0059] --Component A-- The molecular weight of the above 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 it is equal to or greater than the lower limit of the above range, the fading speed tends to be improved, and if it is equal to or less than the upper limit of the above range, the photochromic layer tends 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 above-mentioned component A may contain only acryloyl groups, only methacryloyl groups, or both acryloyl groups and methacryloyl groups. That is, component A can be an acrylate or a methacrylate.

[0061] One embodiment of the above-mentioned component A includes acyclic polyfunctional (meth)acrylates. In this disclosure and this specification, "acyclic" means not containing a cyclic structure. In contrast, "cyclic" means containing a cyclic structure. The acyclic 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)acrylates represented by the following formula (2): These may be used alone or in combination of two or more.

[0062] [ka] ···(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 in the alkylene group represented by R in formula (2) is not particularly limited, but is preferably 1 to 5, and more preferably 2 to 4. The alkylene group represented by R in formula (2) is not particularly limited, and examples thereof include an ethylene group, a propylene group, and a tetramethylene group. Although n in formula (2) is not particularly limited, it is preferably 2-30, more preferably 2-25, and particularly preferably 2-20. The polyalkylene glycol di(meth)acrylate represented by formula (2) is not particularly limited, and examples thereof include polyethylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, polytetramethylene glycol di(meth)acrylate, etc. These may be used alone or in combination of two or more.

[0064] Furthermore, 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 acryloyl groups, may contain only methacryloyl groups, or may contain acryloyl groups and methacryloyl groups.

[0065] [ka] ···(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 each independently represents a hydrogen atom or a methyl group. In formula (3), n1 is OR 41 The number of repetitions of the alkoxy group represented by the formula (I) is 2 or more. In formula (3), n2 is OR 45 The number of repetitions of the alkoxy group represented by the formula (I) is 2 or more. In formula (3), n3 is OR 48 The number of repetitions of the alkoxy group represented by the formula (I) is 2 or more.

[0067] R in Equation (3) 41 , R 45 and R 48The 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 Equation (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 Equation (3) 43 The number of carbon atoms in the alkyl group represented by the formula (I) is not particularly limited, but is preferably 1 to 5, and more preferably 1 to 4. R in Equation (3) 43 The alkyl group represented by the formula (I) is a straight-chain alkyl group or a branched alkyl group. R in Equation (3) 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 Equation (3) 40 , R 44 and R 47 each independently represents an alkylene group. R in Equation (3) 40 , R 44 and R 47 The number of carbon atoms in the alkylene group represented by the following formula is not particularly limited, but is preferably 1 to 5, and more preferably 1 to 4. R in Equation (3) 40 , R 44 and R 47Specific examples of the alkylene group represented by the formula (I) are not particularly limited, and include, for example, a methylene group, an ethylene group, a propylene group, and a tetramethylene group.

[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] [ka] ···(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. R in Equation (4) 11 The alkyl group represented by the formula (I) may be unsubstituted or may have a substituent. The substituent is not particularly limited, and examples thereof include the various substituents described above. R in Equation (4) 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 content 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 content is equal to or less than the upper limit of the above range, the photochromic compound tends to dissolve in the composition for the 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, but from the viewpoint of increasing the (meth)acryloyl group content in the composition for photochromic layer 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 smaller molecular weight than Component A is preferred. The molecular weight of the polyfunctional (meth)acrylate other than the above component A is not particularly limited, but from the above viewpoint, it is preferably 100 or more and less than 500, more preferably 100 or more and 400 or less, and particularly preferably 100 or more and 350 or less. The number of functional groups of the polyfunctional (meth)acrylate other than Component A is not particularly limited, but from the viewpoint of weather resistance, a polyfunctional (meth)acrylate having a larger number of functional groups than the polyfunctional (meth)acrylate used as Component A is preferred. The number of functional groups of the polyfunctional (meth)acrylate can be, for example, 10 to 15. There is no particular limit to the polyfunctional (meth)acrylate having 10 to 15 functional groups, and examples thereof include poly[(3-methacryloyloxypropyl)silsesquioxane] derivatives. 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 having neither a cyclic structure nor a branched structure (component C), a bifunctional (meth)acrylate having at least one structure selected from the group consisting of a cyclic structure and a branched structure (component D), etc. These may be used alone or in combination of two or more. Components C and 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] [ka] ···(5)

[0081] In formula (5), R 3 and R 4 each independently represents a hydrogen atom or a methyl group. In formula (5), m represents an integer of 1 or more, and may be 10 or less, 9 or less, 8 or less, 7 or less, or 6 or less. When the above component C has a methacryloyl group, the branched structure contained in the methacryloyl group is not taken into consideration.

[0082] The molecular weight of the above-mentioned component C is not particularly limited, but is preferably 100 to 400, more preferably 140 to 350, and particularly preferably 160 to 300. If it is equal to or greater than the lower limit of the above-mentioned range, the fading speed tends to be improved, and if it is equal to or less than the upper limit of the above-mentioned range, the color density of the photochromic layer tends to be increased.

[0083] The above-mentioned component C may contain only acryloyl groups, only methacryloyl groups, or both acryloyl groups and methacryloyl groups as (meth)acryloyl groups. Specific examples of the component C are not particularly limited and include, for example, 1,9-nonanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,10-decanediol di(meth)acrylate, etc. These may be used alone or in combination of two or more.

[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 the above 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. In one embodiment, the component D may contain one or more cyclic structures and no branched structures in one molecule, in another embodiment, one or more branched structures and no cyclic structures in one molecule, and in still another embodiment, one or more cyclic structures and one or more branched structures in one molecule. The number of at least one structure selected from the group consisting of cyclic structures and branched structures contained in the above component D is not particularly limited, but is preferably 1 to 3, more preferably 1 to 2, and particularly preferably 1. When the above-mentioned component D has 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 Examples of the compound include compounds having a structure represented by the following formula: where 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 11and L 22 each independently represents a linking group; n11 and n22 each independently represents 0 or 1; The divalent alicyclic group represented by Q is not particularly limited, and suitable examples thereof 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. L 11 and L 22 The linking group represented by the following formula 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] One 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 the 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, propoxylated neopentyl glycol di(meth)acrylate, etc. These may be used alone or in combination of two or more.

[0088] The molecular weight of the above-mentioned component D is not particularly limited, but is preferably 200 to 400. When it is equal to or greater than the lower limit of the above-mentioned range, the color density of the photochromic layer is likely to be improved, and when it is equal to or less than the upper limit of the above-mentioned range, the photochromic compound is likely to be dissolved in the composition for the photochromic layer.

[0089] The above-mentioned 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 mass %, more preferably 80 to 95 mass %, relative to 100 mass % of the composition for photochromic layer. If the content is equal to or greater than the lower limit of the above range, the photochromic compound becomes more easily soluble in the composition for photochromic layer, and if the content is equal to or less than the upper limit of the above range, the photochromic properties tend to be improved. The composition for photochromic layer may or may not contain a solvent. When the composition for photochromic layer contains a solvent, 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 form, Component A can be the component that accounts for the largest proportion of multiple polymerizable compounds contained in the composition. In one embodiment, the composition for photochromic layer may contain only one type of component A, and 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 mentioned above is the total content of the two or more types. This also applies to the contents of other components.

[0092] The content of Component B is not particularly limited, but is preferably 1 to 30 mass %, more preferably 5 to 27 mass %, and particularly preferably 10 to 25 mass %, relative to 100 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, and when the content is equal to or less than the upper limit of the above range, the fading rate is likely to be improved. In one embodiment, the composition for photochromic layer may contain only one type of component B, and in another embodiment, it may contain two or more types of component B. When two or more types of component B are contained, the content of component B mentioned above 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 mass %, more preferably 3 to 27 mass %, based on 100 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 increase, and if it is equal to or less than the upper limit of the above range, the fading rate tends to increase. In one embodiment, the composition for photochromic layer may contain only one type of component C, and in another embodiment, it may contain two or more types of component C. When two or more types of component C are contained, the content of component C mentioned above 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 mass %, and more preferably 5 to 27 mass %, relative to 100 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 of the photochromic layer is likely to be improved, and if 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 or may not contain, as necessary, other (meth)acrylates other than Components A to D. When the composition contains other (meth)acrylates other than Components A to D, the content of the other (meth)acrylates other than Components A to D is not particularly limited, but from the viewpoint of the fading rate, it is preferably 10.0% by mass or less, and more preferably 5.0% by mass or less, relative to 100% by mass of all (meth)acrylates contained in the composition for photochromic layer. The composition for photochromic layer may or may not contain a polymerizable compound other than (meth)acrylate, as necessary.

[0096] -Photochromic Compounds- One embodiment of the composition for the photochromic layer may contain a photochromic compound together with the polymerizable compound. The photochromic compound is not particularly limited, and for example, any known compound that exhibits photochromic properties when exposed to ultraviolet light can be used. Specific examples of the photochromic compound include, but are not limited to, compounds having a known skeleton exhibiting photochromic properties, such as azobenzenes, spiropyrans, spirooxazines, naphthopyrans, indenonaphthopyrans, phenanthropyrans, hexaallylbismidazoles, donor-acceptor Stenhouse adducts (DASA), salicylideneanilines, dihydropyrenes, anthracene dimers, fulgides, diarylethenes, phenoxynaphthacenequinones, and stilbenes; fulgimide compounds; spirooxazine compounds; chromene compounds; indeno-fused naphthopyran compounds; and at least one compound selected from the group consisting of photochromic compounds represented by general formula A, general formula B, and general formula C, as described in WO2022 / 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 photochromic layer.

[0097] -Other ingredients- The composition for photochromic layer may contain, in addition to two or more types of (meth)acrylate and a photochromic compound, one or more of various additives that may be typically contained in a polymerizable composition, in any amount, as needed. 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 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 of the aryl groups of the two triarylimidazole moieties may be the same, making the compound symmetrical, or different, making the compound asymmetrical.Furthermore, a thioxanthone compound may be combined with a tertiary amine, such as the 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 photochromic layer.

[0100] If necessary, the composition for the photochromic layer may further contain any amount of known additives that are commonly added, such as surfactants, antioxidants, radical scavengers, light stabilizers, ultraviolet absorbers, color inhibitors, antistatic agents, fluorescent dyes, dyes, pigments, fragrances, plasticizers, and silane coupling agents. 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 protective layer refers to a cured polymerizable composition for forming a protective layer (hereinafter, sometimes simply referred to as a "protective layer composition"). The position of the protective layer is not particularly limited, but it 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 an optical article, after forming a protective layer, a wiping treatment with a solvent is usually carried out to clean the surface of the formed protective layer, but if the protective layer is damaged in this wiping treatment, it may 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 composition for the protective layer is a polymerizable composition containing one or more (meth)acrylates and containing 70.0% by mass or more of an alicyclic bifunctional (meth)acrylate relative to 100% by mass of all (meth)acrylates. The components contained in the protective layer composition are not particularly limited, but from the viewpoint of hardness and solvent resistance of the protective layer, it is preferable that the composition contains an alicyclic bifunctional (meth)acrylate component.

[0106] As the alicyclic bifunctional (meth)acrylate contained in the composition for protective layer, reference can be made to the alicyclic bifunctional (meth)acrylate as an example of the polymerizable composition for forming a photochromic layer described above. The content of the alicyclic bifunctional (meth)acrylate is not particularly limited, but from the viewpoint of obtaining higher hardness and better solvent resistance of the protective layer, it is preferably 70.0 mass % or more, more preferably 75.0 mass % or more, even more preferably 85.0 mass % or more, and particularly preferably 95.0 mass % or more, based on 100 mass % of all (meth)acrylates. As one embodiment of the content of the alicyclic bifunctional (meth)acrylate, the total amount of (meth)acrylate may be alicyclic bifunctional (meth)acrylate.

[0107] In one embodiment of the protective layer composition, the (meth)acrylate may contain one or more other (meth)acrylates in addition to an alicyclic bifunctional (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 may 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% of all (meth)acrylates (100 mass%).

[0108] The composition for the protective layer 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, or in another embodiment, may contain only (meth)acrylate as the polymerizable compound. The other polymerizable compound is not particularly limited, and one or more known polymerizable compounds may be used. The content of the above (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 all polymerizable compounds in the composition for the protective layer (100% by mass).

[0109] In one embodiment, the content of the above (meth)acrylate (the total amount if two or more types of (meth)acrylates are included) is preferably 80.0% by mass or more, more preferably 90.0% by mass or more, and particularly preferably 95.0% by mass or more, based on 100% by mass of the composition for 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 composition for a protective layer may further contain one or more additives in any content, as required. The additives are not particularly limited and include, for example, various known additives such as a polymerization initiator for promoting a polymerization reaction, a leveling agent for improving the coating suitability of the composition, etc. 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 in 100% by mass of the composition for 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 contained in the composition for a protective layer can contribute to improving the weather resistance of the protective layer. When the composition for a protective layer contains an ultraviolet absorber, the content of the ultraviolet absorber is not particularly limited, and from the viewpoint of optical properties such as transparency, it is preferably 0.1 to 1.0 mass % in 100 mass % of the composition for a protective layer.

[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 form in which the layers are in direct contact without any other layer interposed therebetween and a form 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, etc. In one embodiment, the other cured coating layer can be a layer thinner than the protective layer. The other cured coating layer is not particularly limited, and examples thereof include an organosilicon-based cured layer. An organosilicon-based cured layer is generally preferred because it has excellent impact resistance. In addition, when an antireflection layer is further provided as one embodiment, an organosilicon-based cured layer is generally preferred because it has 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; etc. 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 an inorganic substance 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 subject the surface of the protective layer to a wiping treatment with a solvent. However, if the protective layer has poor solvent resistance, the solvent wiping treatment will damage the protective layer (for example, cause surface roughness), which will cause clouding or optical defects in the plastic lens including the protective layer. In contrast, the protective layer 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 necessary in addition to the above-mentioned primer layer, photochromic layer, and protective layer. The other functional layer is not particularly limited and examples thereof include an antireflection layer, a water-repellent or hydrophilic antifouling layer, an antifogging layer, etc. These may be used alone or in combination of two or more.

[0121] [glasses] One aspect of the present disclosure relates to eyeglasses equipped with the above-described plastic lenses. Details of the plastic lenses equipped in the eyeglasses are as described above. By including the above-described plastic lenses, the eyeglasses can, for example, exhibit an anti-glare effect like sunglasses outdoors by a photochromic compound contained in a photochromic layer that changes color when irradiated with sunlight, and when the eyeglasses return indoors, the photochromic compound fades, allowing the eyeglasses to regain their transparency. The structure of the frame of the above-mentioned eyeglasses is not particularly limited, and known techniques can be applied.

[0122] [Plastic lens manufacturing method] One aspect of the present disclosure is a method for producing 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 formation process> The primer layer forming step will be described in more 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 subjecting the applied primer layer composition to a curing treatment. 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 thereof include light irradiation and heat treatment. These may be used alone or in combination of two or more. Among these, light irradiation is preferred from the viewpoint of progressing the curing reaction in a short time. The curing treatment conditions can be determined depending on the types of various components contained in the primer layer composition and the composition of the primer layer composition. After the 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.

[0125] <Photochromic layer formation process> The photochromic layer forming step will be described in more detail below.

[0126] The photochromic layer can be formed on the surface of the primer layer by applying a composition for a photochromic layer onto the surface of the primer layer and then subjecting the applied composition for a photochromic layer to a curing treatment. 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 thereof include light irradiation, heat treatment, etc. These may be used alone or in combination of two or more. Among these, light irradiation is preferred from the viewpoint of progressing the curing reaction in a short time. The intensity of the light irradiation is 150 to 350 mW / cm 2 However, from the viewpoint of suppressing thermal deformation of the 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 , and particularly preferably 220 to 280 mW / cm 2 is. The irradiation time for 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 above 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 , and particularly preferably 3.3 to 11.2 J / cm 2 is. 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 formation process> 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 in order 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 thereof include light irradiation and heat treatment. These may be used alone or in combination of two or more. Among these, light irradiation is preferred from the viewpoint of progressing the curing reaction in a short time. The curing treatment conditions can be determined depending on the types of various components contained in the composition for protective layer and the composition of the composition for protective layer. 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. [Example]

[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] As shown below, photochromic layer compositions 1 to 3, which are polymerizable compositions for forming a photochromic layer, were produced.

[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 2 90 parts by mass of methyl group (number average molecular weight 726) and 10 parts by mass of tricyclodecane dimethanol dimethacrylate (molecular weight 332) were mixed to obtain a mixture of polymerizable compounds. The resulting 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 BV, 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 device. Photochromic layer composition 1 was thus obtained. The contents of the various components are as follows: 90.0% by mass of the mixture of polymerizable compounds, 5.7% by mass of the photochromic compound, 0.7% by mass of the photoradical polymerization initiator, 2.7% by mass of the antioxidant, and 0.9% by mass of the light stabilizer, based on 100% by mass of the composition 1 for photochromic layer.

[0132] [ka] ···(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 mixture of polymerizable compounds for photochromic layer composition 2 (see below) were used. 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 mixture of polymerizable compounds, 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 the 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] [ka] ···(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 mixture of polymerizable compounds. To 100 parts by weight of the resulting polymerizable compound mixture, 3 parts by weight of a photochromic compound (chromene compound (A) represented by the structural formula (8) below), 0.6 parts by weight of a photoradical polymerization initiator (CGI-1870, manufactured by Ciba Specialty Chemicals), 5 parts by weight of an antioxidant (Irgacure 245, manufactured by Ciba Specialty Chemicals), and 5 parts by weight 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. Then, 6 parts by weight 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 weight of polyethylene glycol diacrylate (average molecular weight 708) was added. In this way, a composition 3 for photochromic layer was obtained.

[0136] [ka] ···(8)

[0137] [Preparation of polymerizable composition for forming primer layer] In a plastic container, 10 parts by mass of a hydroxyl-containing bifunctional acrylate having a compound represented by the following structural formula (1), 40 parts by mass of a polyisocyanate (Tosoh Corporation, Coronate 2715), and 50 parts by mass of 2-phenoxyethyl acrylate (viscosity: 13 cP) were mixed. To the resulting mixture, 0.02 parts by mass of a photoradical polymerization initiator (bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, IGM Resin BV, Omnirad 819) was added and thoroughly stirred. The mixture was then degassed using a rotation-revolution type stirring and degassing device. Primer layer composition 1 was thus obtained.

[0138] [ka] ···(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, manufactured by IGM Resin BV, Omnirad819) were mixed and thoroughly stirred, and then degassed using a rotation-revolution type stirring and degassing device. Thus, protective layer composition 1 was obtained. In the above-mentioned composition for protective layer 1, the (meth)acrylate is only an alicyclic bifunctional (meth)acrylate, and therefore the content of the alicyclic bifunctional (meth)acrylate is 100% by mass of the total (meth)acrylates (100% by mass).

[0140] [Plastic lens manufacturing] Example 1 A lens substrate (HOYA Corporation, HILUX1.67, 1.0 mm thick at the center and 9.1 mm thick at the periphery) 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 then the primer layer composition 1 applied to the lens substrate was irradiated with light (light wavelength: 405 nm, light irradiation intensity: 250 mW / cm) in a nitrogen atmosphere (oxygen concentration: 500 volume ppm or less). 2 , Light irradiation time: 5 seconds, Light irradiation exposure: 1.25 J / cm 2 ) and the composition was cured to form a primer layer. The primer layer thus formed had a thickness of 10 μm. Composition 1 for photochromic layer was applied onto the primer layer by spin coating. The spin coating was performed according to the method described in JP-A-2005-218994. Thereafter, the composition 1 for photochromic layer 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 ppm by volume or less). 2, Light irradiation time: 25 seconds, Light irradiation exposure: 6.25 J / cm 2 ) and the composition was cured to form a photochromic layer. The thickness of the photochromic layer formed was 40 μm. The protective layer composition 1 was applied onto the photochromic layer 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 ppm by volume or less). 2 , Light irradiation time: 15 seconds, Light irradiation exposure: 3.75 J / cm 2 ) and the coating layer was cured to form a protective layer. The thickness of the protective layer formed was 38 μm. After the above three layers were formed, heat treatment was carried out in a heat treatment device (PH series, manufactured by Espec Corporation) at an atmospheric temperature of 90°C for 2 hours to strengthen the adhesion of each cured coating layer. The thickness of the cured coating layer is the thickness of the central part of the lens substrate after the cured coating layer has been formed minus the thickness of the central part of the lens substrate before the cured coating layer has been formed. The thicknesses of the lens substrate before and after the cured coating layer have been formed were 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 central part of the lens substrate. The "light irradiation intensity" is a value measured using a light meter (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 part (center wavelength 365 mm). The above "light exposure" is the integrated value of the irradiation time (light irradiation intensity (mW / cm)) measured by using a light meter (UIT-250, manufactured by USHIO Co., Ltd.) to illuminate a lens base 300 mm away from the center of the light source to the light receiving part (center 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 (wavelength of light: 405 nm, intensity of light irradiation: 250 mW / cm 2 , Light irradiation time: 25 seconds, Light irradiation exposure: 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: 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: 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: 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 above-mentioned compound was replaced with the compound 1.

[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 Ph curve was created. The indentation hardness H was calculated from the created Ph curve using the following formula. H(kgf / mm 2 )=Pmax / A (Above, Pmax is the maximum load (kgf), and A is the indenter projected area (mm 2 ) The indentation hardness here is the value obtained from the displacement-load curve from loading to unloading of the measuring indenter, and is specified in ISO 14577:2015.

[0147] <Top surface scratch resistance> Apply 1kgf / cm of steel wool (standard #0000, manufactured by Nippon Steel Wool Co., Ltd.) to the surface of the photochromic lens. 2 The lens surface was rubbed while being pressed against the lens, and the scratch resistance was judged visually. The scratches on the outermost surface were evaluated according to the following criteria. [Evaluation criteria] UA: There are barely any scratches. A: A few thin scratches or two deep but thin scratches. B: Approximately 20 thin scratches or 10 thin but deep scratches. C: There are many deep scratches (regardless of thickness) and the surface is almost cloudy, or there are 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 power> 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 above were measured. Then, 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 taken as the "difference from design diopter" of each plastic lens. The difference between the measured power and the design power was evaluated according to the following evaluation criteria. [Evaluation criteria] A: 0.06 or less B: More than 0.06 but less than 0.09 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 power 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 power is not small, so it cannot be said that the thermal deformation of the plastic lens is sufficiently small.

[0149] <Fading speed (fading)> For each spectacle lens photochromic layer (a cured layer obtained by curing the polymerizable composition) in the Examples and Comparative Examples, the surface of the photochromic layer was irradiated with light from a xenon lamp through an aeromass filter for 15 minutes (900 seconds), causing the photochromic compound in the photochromic layer to develop a color. The transmittance (measurement wavelength: 550 nm) during this color development was measured using a spectrophotometer manufactured by Otsuka Electronics Co., Ltd. The light irradiation was carried out so that the irradiance and irradiance tolerance, 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 during color development." [Table 1] After measuring the transmittance at color development, the transmittance was measured 60 seconds after the light irradiation was stopped (hereinafter referred to as "60-second transmittance after fading"). The fading rate (unit: % / second) was calculated using the formula: fading rate = [(60-second transmittance after fading - transmittance at color development) / 60]. The higher the value of the fading rate calculated in this way, the faster the fading rate. The measured values ​​of the fading speed were evaluated according to the following evaluation criteria. [Evaluation criteria] A: More than 0.60% / sec B:0.40~0.60% / sec C: Less than 0.40% / sec In the cases of ratings A and B, the color fading resistance can be said to be sufficiently excellent. On the other hand, in the case of rating C, the color fading resistance cannot be said to be excellent.

[0150] [Table 2]

[0151] From the results shown in Table 2, it can be seen 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 have set the surface hardness of the photochromic layer to 2.0 kgf / mm 2 It is believed that the following factors contribute 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 cured coating layer is formed and the design power to less than 0.12 means that the plastic lenses of Examples 1 and 2 are subject to little 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. [Industrial Applicability]

[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, 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 / mm ２ is as follows: A plastic lens having a hardened coating layer formed on one surface of the lens substrate, wherein the difference between the power of the plastic lens and the design power is less than 0.

12.

2. the photochromic layer is a layer obtained by curing a photochromic-layer-forming polymerizable composition, The photochromic layer-forming polymerizable composition is two or more (meth)acrylates; a photochromic compound; The plastic lens of claim 1 , comprising:

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

6. 2. 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 the 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 the steps of: 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; a protective layer forming step of forming a protective layer on the surface of the photochromic layer, The intensity of the light irradiation is 150 to 350 mW / cm ２ and The light irradiation time is 1 to 90 seconds, The exposure dose of the light irradiation is 0.15 to 31.5 J / cm ２ This is a method for manufacturing a plastic lens.

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