Method of fabricating plastic lens

Abstract

To provide a plastic lens fabrication method which enables fabrication of a plastic lens with less thermal deformation by reducing the temperature gradient in the inner and outer circumferential directions of the plastic lens.SOLUTION: A method of fabricating a plastic lens having a cured coating layer provided on one surface of a lens base material is provided, the method comprising a heat dissipation sheet covering step of covering at least a portion of the other surface of the lens base material with a heat dissipation sheet, a coating step of coating the one surface of the lens base material with a photocurable composition, and a light irradiation step of irradiating the photocurable composition with light to form the cured coating layer. The heat dissipation sheet contains at least one of a metal compound and a metal.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present disclosure relates to a method for manufacturing a plastic lens, and more particularly to a method for manufacturing a plastic lens that can suppress a temperature gradient in the inner and outer periphery directions of the plastic lens and produce a plastic lens with little thermal deformation. [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 composition containing a photochromic compound and a polymerizable compound (a photochromic layer-forming polymerizable composition) to the surface of a lens substrate, irradiating the applied photochromic layer-forming polymerizable composition with light to cure it, and forming a photochromic cured coating layer (a photochromic layer) (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] However, heat generated by light irradiation when the applied polymerizable composition for forming a photochromic layer is cured generates a temperature gradient in the inner and outer periphery of the plastic lens, causing the base lens to soften locally, resulting in the problem that the plastic lens cannot withstand the stress generated when the applied polymerizable composition for forming a photochromic layer is cured, and is thermally deformed.

[0005] An object of one aspect of the present disclosure is to provide a method for manufacturing a plastic lens that can suppress the temperature gradient in the inner and outer periphery directions of the plastic lens and produce a plastic lens with little thermal deformation. [Means for solving the problem]

[0006] The embodiments of the present disclosure relate to the following [1] to [9]. [1] A method for manufacturing a plastic lens having a cured coating layer on one surface of a lens substrate, the method comprising: a heat dissipation sheet coating step of coating at least a portion of the other surface of the lens substrate with a heat dissipation sheet; a coating step of applying a photocurable composition to one surface of the lens substrate; and a light irradiation step of irradiating the photocurable composition with light to form the cured coating layer, wherein the heat dissipation sheet contains at least one of a metal compound and a metal. [2] The thermal conductivity of at least one of the metal compound and the metal is 1.0 to 500 Wm -1 K -1 The method for producing a plastic lens according to [1] above, [3] The method for producing a plastic lens according to [1] or [2] above, wherein at least one of the metal compound and the metal is at least one selected from the group consisting of aluminum oxide, aluminum hydroxide, bismuth, indium, tin, zinc, gallium, lead, cadmium, copper, and silver. [4] The method for producing a plastic lens according to any one of [1] to [3] above, wherein the content of at least one of the metal compound and the metal in the heat dissipation sheet is 65 to 100 mass %. [5] The method for producing a plastic lens according to any one of [1] to [4] above, wherein the lens substrate has a central portion having a thickness of less than 2 mm and a peripheral portion having a thickness greater than that of the central portion. [6] The method for manufacturing a plastic lens according to [5] above, wherein the central portion is covered with the heat dissipation sheet. [7] The method for producing a plastic lens according to any one of the above [1] to [6], wherein the cured coating layer has a primer layer, a photochromic layer, and a protective layer. [8] The method for producing a plastic lens according to any one of the above [1] to [7], wherein the coating is spin coating, and the rotation speed in the spin coating is 100 rpm or more. [9] The method for producing a plastic lens according to any one of the above [1] to [8], wherein the thickness of the cured coating layer is 5 to 100 μm.

[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 covering at least a portion of the other surface of the lens substrate with a heat dissipation sheet containing at least one of a metal compound and a metal, 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 method for manufacturing a plastic lens that can suppress a temperature gradient in the plastic lens and manufacture a plastic lens that is less thermally deformed. 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 provisions can be selected arbitrarily, and combinations of preferred provisions 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, "(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 mean both an acryloyl group and a methacryloyl group, and the term "(meth)acryloyloxy group" is used to mean both an acryloyloxy group and a methacryloyloxy group. 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, the "number of carbon atoms" in a substituted group 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 this specification, the term "temperature gradient in the inner and outer circumferential direction of a plastic lens" refers to the temperature difference between each region of a plastic lens (such as the central portion, peripheral portion, and middle portion), and there is a tendency for the temperature difference (i.e., the temperature gradient) to increase from the central portion to the middle portion of a plastic lens. 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). In this disclosure and this specification, the "content of at least one of a metal compound and a metal" is a value calculated as a content by quantitatively analyzing the metal content using X-ray fluorescence analysis, a common analytical method. In this disclosure and this specification, the term "metal" also includes metalloids. 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 manufacturing method] The method for producing a 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 method for producing a plastic lens is a method for producing a plastic lens having a cured coating layer on one surface of a lens substrate, and includes a heat dissipation sheet coating step of covering at least a portion of the other surface of the lens substrate with a heat dissipation sheet, a coating step of applying a photocurable composition to one surface of the lens substrate, and a light irradiation step of irradiating the photocurable composition with light to form a cured coating layer, and may further include other steps as necessary.

[0012] <Plastic lens> There are no particular restrictions on the plastic lens as long as it comprises a lens substrate and a cured coating layer formed on one surface of the lens substrate. However, since it is necessary to cover at least a portion of the other surface of the lens substrate with a heat dissipation sheet, it is preferable that no other cured coating layer be formed on the other surface of the lens substrate.

[0013] (lens substrate) The lens substrate will be described in more detail below.

[0014] In the present disclosure and specification, the material of the lens substrate is not particularly limited, and examples thereof include (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, and 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. These may be used alone, or two or more may be used.

[0015] 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.

[0016] The color of the lens substrate is not particularly limited, and it may be colorless (an undyed lens) or dyed.

[0017] 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.

[0018] The focal point of the lens substrate is not particularly limited, and examples thereof include single-focus, multi-focus, and progressive-addition lenses.

[0019] 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.

[0020] 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.

[0021] (cured coating layer) The cured coating layer will be described in more detail below.

[0022] In the present disclosure and this specification, the cured coating layer is not particularly limited as long as it is a layer formed on one surface of the lens substrate, and examples thereof include a primer layer, a photochromic layer, a protective layer, a hard coat layer, and other functional layers. These layers may be present alone or in combination of two or more. Among these, from the viewpoint of adhesion of the coating layer, a three-layer cured coating layer having a primer layer, a photochromic layer, and a protective layer, or a two-layer cured coating layer having a primer layer and a photochromic layer is preferred, and a three-layer cured coating layer having a primer layer, a photochromic layer, and a protective layer is more preferred.

[0023] The thickness of the cured coating layer is not particularly limited, but is preferably 5 to 100 μm, more preferably 10 to 95 μm, and particularly preferably 15 to 90 μm. If the thickness is equal to or greater than the lower limit of the above range, adhesion is easily maintained, and if the thickness is equal to or less than the upper limit of the above range, the transmittance (transparency) of the coating layer is easily maintained.

[0024] ((Primer layer)) The primer layer will be described in more detail below.

[0025] 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 primer layer can be formed on one surface of the lens substrate, for example, by applying a primer layer composition to one surface of the lens substrate and irradiating the applied primer layer composition with light. 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.

[0026] 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.

[0027] 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.

[0028] -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.

[0029] 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.

[0030] 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.

[0031] -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.

[0032] 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.

[0033] 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.

[0034] 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.

[0035] 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.

[0036] [ka] ···(1)

[0037] 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.

[0038] 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.

[0039] -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.

[0040] 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.

[0041] 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.

[0042] 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.

[0043] 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.

[0044] 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.

[0045] 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.

[0046] 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.

[0047] 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.

[0048] 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.

[0049] 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.

[0050] 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.

[0051] 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).

[0052] The primer layer composition can be prepared by mixing the various components described above simultaneously or sequentially in any order.

[0053] ((Photochromic layer)) The photochromic layer will be described in more detail below.

[0054] 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 photochromic layer can be formed on the surface of the primer layer, for example, by applying a composition for a photochromic layer onto the surface of the primer layer and irradiating the applied composition for a photochromic layer with light. 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.

[0055] 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.

[0056] 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.

[0057] -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.

[0058] --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.

[0059] 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.

[0060] 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.

[0061] [ka] ···(2)

[0062] 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.

[0063] 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.

[0064] [ka] ···(3)

[0065] 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.

[0066] R in Equation (3) 41 , R 45 and R 48 The n1, n2, and n3 in formula (3) are as described above for n in formula (2). In formula (3), R 41 , R 45 and R 48 may be the same, or two or three may be different. This also applies to n1, n2, and n3.

[0067] 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.

[0068] 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.

[0069] 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 47 Specific examples of the alkylene group represented by the formula (I) are not particularly limited, and include, for example, a methylene group, an ethylene group, a propylene group, and a tetramethylene group.

[0070] 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.

[0071] --Component B-- Component B is a monofunctional (meth)acrylate represented by the following formula (4).

[0072] [ka] ···(4)

[0073] 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.

[0074] 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. When the content is equal to or less than the upper limit of the above range, the photochromic compound becomes more soluble in the composition for photochromic layer.

[0075] 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.

[0076] 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.

[0077] 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.

[0078] --Component C-- Component C is a polyfunctional (meth)acrylate having neither a cyclic structure nor a branched structure, represented by the following formula (5).

[0079] [ka] ···(5)

[0080] 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.

[0081] 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.

[0082] 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.

[0083] --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.

[0084] 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.

[0085] 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.

[0086] 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.

[0087] The molecular weight of the component D is not particularly limited, but is preferably 200-400.

[0088] The above-mentioned component D may contain only acryloyl groups, only methacryloyl groups, or both acryloyl groups and methacryloyl groups as (meth)acryloyl groups.

[0089] 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.

[0090] 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.

[0091] 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.

[0092] 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.

[0093] The content of the component D is not particularly limited, but is preferably 1 to 30% by mass, and more preferably 5 to 27% by mass, based on 100% by mass of all polymerizable compounds contained in the composition for photochromic layer. 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 above is the total content of the two or more types.

[0094] 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.

[0095] -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.

[0096] -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.

[0097] 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.

[0098] 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.

[0099] 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.

[0100] The composition for the photochromic layer can be prepared by mixing the various components described above simultaneously or sequentially in any order.

[0101] ((protective layer)) The protective layer will be described in more detail below.

[0102] 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 protective layer can be formed on the surface of the photochromic layer, for example, by applying a composition for a protective layer onto the surface of the photochromic layer and irradiating the applied composition for a protective layer with light. 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 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 a layer is formed, a wiping treatment with a solvent is usually carried out to clean the surface of the formed layer, but if the protective layer is damaged in this wiping treatment, it may cause clouding or optical defects in the plastic lens.

[0103] 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 coating layer will be easily maintained.

[0104] 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.

[0105] 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.

[0106] 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 mass%, more preferably 1.0 to 25.0 mass%, and particularly preferably 5.0 to 20.0 mass% of all (meth)acrylates (100 mass%).

[0107] 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).

[0108] 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.

[0109] 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.

[0110] 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.

[0111] The polymerization initiator is not particularly limited, and any known polymerization initiator can be used. Preferably, a photoradical polymerization initiator is used, and more preferably, only a photoradical polymerization initiator can be used as the polymerization initiator. 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.

[0112] 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 the protective layer contains an ultraviolet absorber, the content of the ultraviolet absorber is not particularly limited, but 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 the protective layer.

[0113] The composition for the protective layer can be prepared by mixing the various components described above simultaneously or sequentially in any order.

[0114] 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.

[0115] 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.

[0116] 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.

[0117] 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.

[0118] 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.

[0119] ((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.

[0120] Hereinafter, each step (heat dissipation sheet covering step, coating step, light irradiation step, and other steps) in the method for producing a plastic lens of the present disclosure will be described in further detail.

[0121] <Heat dissipation sheet coating process> The heat dissipation sheet covering step will be described in more detail below.

[0122] The heat dissipation sheet covering step is a step of covering at least a portion of the other surface of the lens substrate with a heat dissipation sheet. There are no particular restrictions on the covering portion of the heat dissipation sheet, but from the viewpoint of efficiently suppressing the temperature gradient of the plastic lens, it preferably includes at least the central portion of the other surface of the lens substrate, and from the viewpoint of preventing splashes of the photocurable composition from adhering to the other surface of the lens substrate, it preferably includes at least the peripheral portion of the other surface of the lens substrate, and further from the viewpoint of efficiently suppressing the temperature gradient of the plastic lens and preventing splashes of the photocurable composition from adhering to the other surface of the lens substrate, it is more preferable that the covering portion cover the entire other surface of the lens substrate.

[0123] (heat dissipation sheet) The heat dissipation sheet is not particularly limited as long as it contains at least one of a metal compound and a metal, and may or may not contain, for example, a resin, an inorganic compound, or other components.

[0124] The heat dissipation sheet may have a two-layer structure consisting of an adhesive layer and a heat dissipation layer (metal layer) formed on the adhesive layer, or may have a single-layer structure consisting of a heat dissipation layer containing at least one of a metal compound and a metal, or may have a single-layer structure consisting of a heat dissipation layer containing at least one of metal compound particles and metal particles and a resin.

[0125] ((Metal compounds, metals (elementary metals)) The term "metal compound" does not include "elemental metals" such as bismuth, but includes "metal-containing compounds" such as aluminum oxide.

[0126] The thermal conductivity of at least one of the metal compound and the metal is not particularly limited, but is preferably 1.0 to 500 Wm -1 K -1 , more preferably 10 to 430 Wm -1 K -1 , particularly preferably 15 to 100 Wm -1 K -1 When the temperature is equal to or higher than the lower limit of the above range, heat dissipation becomes easier, and when the temperature is equal to or lower than the upper limit of the above range, the temperature becomes more easily stabilized. The thermal conductivity can be measured by the method described in the examples.

[0127] The metal compound and / or metal is not particularly limited, and examples thereof include aluminum oxide, aluminum hydroxide, bismuth, indium, tin, zinc, gallium, lead, cadmium, copper, silver, etc. These may be used alone or in combination of two or more. Among these, aluminum oxide is preferred from the viewpoint of toxicity.

[0128] The content of at least one of the metal compound and the metal in the heat dissipation sheet is preferably 65 to 100 mass%, more preferably 65 to 95 mass%, and particularly preferably 70 to 85 mass%. When the content is equal to or greater than the lower limit of the above range, heat dissipation becomes easier, and when the content is equal to or less than the upper limit of the above range, flexibility is easier to maintain.

[0129] ((resin)) The resin is not particularly limited, and examples thereof include silicone resin, acrylic resin, polyurethane resin, epoxy resin, polyamide resin, vinyl chloride resin, phenol, etc. These may be used alone or in combination of two or more. Among these, silicone resin is preferred from the viewpoint of durability. These resins are usually contained in the heat dissipation layer.

[0130] ((Inorganic compound)) Examples of inorganic compounds include nitrides such as boron nitride, oxides, and carbides. These may be used alone or in combination of two or more. Among these, boron nitride is preferred from the viewpoint of thermal conductivity.

[0131] <Coating process> The coating step will be described in more detail below.

[0132] The coating step is a step of coating one surface of the lens substrate with a photocurable composition. 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.

[0133] The maximum rotation speed in spin coating is not particularly limited, and is preferably 100 rpm or higher, more preferably 500 to 3000 rpm, and particularly preferably 1000 to 2500 rpm. If the rotation speed is equal to or higher than the lower limit of the above range, thin film formation becomes easier, and if the rotation speed is equal to or lower than the upper limit of the above range, rotation becomes more stable.

[0134] ((Photocurable composition)) The photocurable composition is not particularly limited, and examples thereof include the above-mentioned primer layer composition, the above-mentioned photochromic layer composition, the above-mentioned protective layer composition, etc. These may be used alone or in combination of two or more.

[0135] <Light irradiation process> The light irradiation step will be described in more detail below.

[0136] The light irradiation step is a step of irradiating the photocurable composition with light to form a cured coating layer. The light irradiation conditions can be determined depending on the types of components contained in the photocurable composition and the composition of the photocurable composition.

[0137] The intensity of the light irradiation is not particularly limited, but is preferably 150 to 350 mW / cm from the viewpoint of the curing reaction of the photocurable composition. 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, but from the viewpoint of the curing reaction of the photocurable composition, it is preferably 1 to 180 seconds, more preferably 3 to 120 seconds, and particularly preferably 5 to 60 seconds. The exposure dose of the light irradiation is not particularly limited, but is preferably 0.1 to 63.0 J / cm from the viewpoint of the curing reaction of the photocurable composition. 2 , more preferably 0.5 to 37.2 J / cm 2 , particularly preferably 1.1 to 16.8 J / cm 2 is.

[0138] <Other processes> The other steps are not particularly limited, and examples thereof include an annealing step (heat treatment step) carried out after the light irradiation step, a cleaning step before the coating step, an alkali treatment step, a plasma pretreatment step, and the like. The conditions for the annealing treatment are not particularly limited, but it is preferable to perform the treatment in a heat treatment furnace with an atmospheric temperature of about 90 to 130°C. [Example]

[0139] 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.

[0140] [Preparation of polymerizable composition for forming photochromic layer] As shown below, photochromic layer compositions 1 and 2, which are polymerizable compositions for forming a photochromic layer, were produced. (Photochromic layer composition 1) In a plastic container, 65 parts by mass of trimethylolpropane polyoxyethylene ether trimethacrylate (molecular weight 1264), 5 parts by mass of n-lauryl methacrylate (molecular weight 254), 5 parts by mass of 1,9-nonanediol dimethacrylate (molecular weight 296), 20 parts by mass of n-butyl methacrylate (molecular weight 142), and 5 parts by mass of a poly[(3-methacryloyloxypropyl)silsesquioxane] derivative (a compound represented by the structural formula (6) below) 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 structural formula (7) below, as 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: 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, based on 100% by mass of the composition 1 for photochromic layer.

[0141] [ka] ···(6)

[0142] [ka] ···(7)

[0143] (Photochromic layer composition 2) 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 (number 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 (number average molecular weight 708) was added. In this way, a composition 2 for photochromic layer was obtained.

[0144] [ka] ···(8)

[0145] [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.

[0146] [ka] ···(1)

[0147] [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).

[0148] [Preparing heat dissipation sheets 1 to 4] The following four types of heat dissipation sheets 1 to 4 were prepared. (1) Heat dissipation sheet 1: PT-CUS (product name) manufactured by Sekisui Chemical Co., Ltd.: Two-layer structure (adhesive layer, heat dissipation layer (mixture of silicone resin and aluminum oxide) 1.0 mm ± 0.1 mm): Thermal conductivity of aluminum oxide 37 Wm -1 K -1:Thermal conductivity of the heat dissipation sheet is 2.2Wm -1 K -1 : Metal compound (aluminum oxide) content 85% by mass : Silicone resin content 15% by mass (2) Heat dissipation sheet 2: 1-layer structure (heat dissipation layer (metal alloy 1 (Bi 32.5 mass%, In 51.0 mass%, Sn 16.5 mass%) layer) 1.0 mm): Thermal conductivity of metal alloy 1 (heat dissipation sheet) 57 Wm -1 K -1 : Metal (metal alloy 1) content 100% by mass (3) Heat dissipation sheet 3: Nilaco U Alloy 58 (product name): 1-layer structure (heat dissipation layer (metal alloy 2 (Bi, Pb, Cd, Sn, In) layer) 1.0 mm): Metal alloy 2 (heat dissipation sheet) thermal conductivity 16 Wm -1 K -1 : Metal (Metal Alloy 2) content 100% by mass (4) Heat dissipation sheet 4: FEATHER-S3S (product name) manufactured by Sekisui Chemical Co., Ltd.: Two-layer structure (adhesive layer, heat dissipation layer (mixture of silicone resin and aluminum oxide) 0.5 mm ± 0.05 mm): Thermal conductivity of aluminum oxide 37 Wm -1 K -1 :Thermal conductivity of the heat dissipation sheet is 1.4Wm -1 K -1 : Metal compound (aluminum oxide) content 70% by mass : Silicone resin content 30% by mass The thermal conductivity, metal compound content, and metal content were measured using the methods described below, and the thickness of the heat dissipation sheet (heat dissipation layer) was calculated as the average thickness of five points in the central and peripheral parts of the heat dissipation sheet using a commercially available contact-type thickness measuring device.

[0149] <Thermal conductivity of metal compounds and metals> The thermal conductivity of metal compounds and metals was measured using the hot disk thermal conductivity measurement method (in accordance with ISO / CD 22007-2). The results are shown in Table 1.

[0150] <Metal compound content and metal content> The metal compound content and metal content were measured by X-ray fluorescence analysis. The total metal compound content and metal content are shown in Table 1.

[0151] [Plastic lens manufacturing] Example 1 A lens substrate (manufactured by HOYA Corporation, HILUX1.67 (trade name), 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. Next, the entire concave surface (eyeball side surface) of the lens substrate was covered with a heat dissipation sheet 1. Thereafter, primer layer composition 1 was applied to the convex surface (object-side surface) of the lens substrate by spin coating at a maximum speed of 2500 rpm 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. Onto the primer layer, composition 1 for photochromic layer was applied by spin coating at a maximum speed of 1000 rpm. 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 25 μm. The protective layer composition 1 was applied onto the photochromic layer by spin coating at a maximum speed of 1500 rpm 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 15 μm. In this way, the plastic lens of Example 1 was obtained. The "thickness" of the central part of the lens substrate was measured at one point in the central part of the lens substrate using a contact-type lens center thickness measuring device, and the "thickness" of the peripheral part was measured using a vernier caliper.

[0152] Examples 2 to 4 Plastic lenses of Examples 2 to 4 were obtained in the same manner as in Example 1, except that heat dissipation sheets 2 to 4 were used instead of heat dissipation sheet 1, respectively.

[0153] Example 5 The plastic lens of Example 5 was obtained in the same manner as Example 1, except that instead of covering the entire concave surface (eyeball-side surface) of the lens substrate with heat dissipation sheet 1 in Example 1, only the central portion of the concave surface (eyeball-side surface) of the lens substrate was covered with heat dissipation sheet 1 (leaving the peripheral portion uncovered).

[0154] Example 6 The plastic lens of Example 6 was obtained in the same manner as Example 1, except that instead of covering the entire concave surface (eyeball-side surface) of the lens substrate with heat dissipation sheet 1 in Example 1, only the peripheral portion of the concave surface (eyeball-side surface) of the lens substrate was covered with heat dissipation sheet 1 (leaving the central portion uncovered).

[0155] Example 7 A plastic lens of Example 7 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 in Example 1, the thickness of the primer layer was 6 μm, the thickness of the photochromic layer was 40 μm, and no protective layer was provided.

[0156] (Comparative Example 1) A plastic lens of Comparative Example 1 was obtained in the same manner as in Example 1, except that the concave surface (eyeball side surface) of the lens substrate was not covered with the heat dissipation sheet 1 .

[0157] (Comparative Example 2) In Example 7, instead of covering the entire concave surface (eyeball-side surface) of the lens substrate with heat dissipation sheet 1, an acrylic plate was used as a holder, and 5% by mass of agar was filled and fixed over the entire concave surface (eyeball-side surface) of the lens substrate with tape (Scotch 600 (trade name) manufactured by 3M Co.). A plastic lens of Comparative Example 2 was obtained in the same manner as in Example 7.

[0158] (Comparative Example 3) A plastic lens of Comparative Example 3 was obtained in the same manner as in Example 1, except that instead of covering the entire concave surface (eyeball-side surface) of the lens substrate with heat dissipation sheet 1, an acrylic plate was used as a holder and silicone rubber (KS609 (product name) manufactured by Shin-Etsu Chemical Co., Ltd.) was filled and fixed over the entire concave surface (eyeball-side surface) of the lens substrate with tape (Scotch 600 (product name) manufactured by 3M Corporation).

[0159] [Evaluation of plastic lenses] The following evaluations were carried out using each of the obtained plastic lenses. The evaluation results are shown in Table 1.

[0160] <Temperature gradient> The temperature difference between a portion 5 mm in radius from the center of the lens substrate and a portion 15 mm in radius from the center of the lens substrate was measured within a 10 mm range immediately after the photochromic layer composition was irradiated with light. The temperature distribution of the lens substrate was measured using a commercially available thermography camera. The measured temperature gradient of the plastic lens was evaluated according to the following evaluation criteria. A: 1.00℃ / mm or less B: More than 1.00℃ / mm and less than 1.25℃ / mm C: More than 1.25℃ / mm and less than 1.50℃ / mm D: Over 1.50℃ / mm In the cases of ratings A to C, it can be said that the temperature gradient is small. On the other hand, in the case of rating D, it cannot be said that the temperature gradient is small.

[0161] <Thermal deformation> The change in power of the central part of the lens substrate (within a 5 mm radius from the center) before and after the coating process was taken as the "thermal deformation of the plastic lens." The power was calculated using a Topcon CL-300 (product name) to calculate the difference in the sum of the spherical refractive index S and the add power C, S+C. The thermal deformation of the measured plastic lenses was evaluated according to the following evaluation criteria. [Evaluation criteria] A: 0.06 or less B: More than 0.06 and less than 0.09 C: More than 0.09 and less than 0.12 D: over 0.12 In the cases of evaluations A to C, it can be said that the thermal deformation is small. On the other hand, in the case of evaluation D, it cannot be said that the thermal deformation is small.

[0162] <Splash> The composition adhered to the peripheral portion of the concave surface side of the lens substrate (a portion having a radius of 15 mm or more from the center) at the time of application was evaluated visually and under magnification of up to 10 times. The splashing of the measured plastic lenses was evaluated according to the following criteria. A: No adhesion at all B: Level at which adhesions can be confirmed at maximum magnification C: Level at which adhesions can be confirmed by magnification D: Level where adhesions can be confirmed visually only In the cases of ratings A to C, it can be said that the splash suppression effect is great. On the other hand, in the case of rating D, it cannot be said that the splash suppression effect is great.

[0163] [Table 1]

[0164] The results shown in Table 1 confirm that the plastic lenses of Examples 1 to 7 suppress the temperature gradient in the inner and outer periphery directions of the plastic lenses and experience less thermal deformation than the plastic lenses of Comparative Examples 1 to 3.

[0165] Two or more of the various aspects and configurations described herein may be combined in any combination.

[0166] 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]

[0167] Plastic lenses manufactured by the method for manufacturing a plastic lens according to the present disclosure are useful in the technical fields of spectacles, goggles, etc. By including the above-mentioned plastic lenses, the eyeglasses can exhibit an anti-glare effect like sunglasses when outdoors, for example, as the photochromic compound contained in the photochromic layer changes color when exposed to 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.

Claims

1. A method for producing a plastic lens having a cured coating layer on one surface of a lens substrate, comprising: a heat dissipation sheet covering step of covering at least a portion of the other surface of the lens substrate with a heat dissipation sheet; a coating step of coating one surface of the lens substrate with a photocurable composition; a light irradiation step of irradiating the photocurable composition with light to form the cured coating layer, The method for manufacturing a plastic lens, wherein the heat dissipation sheet contains at least one of a metal compound and a metal.

2. At least one of the metal compound and the metal has a thermal conductivity of 1.0 to 500 Wm －１ K －１ The method for producing a plastic lens according to claim 1, wherein

3. 3. The method for producing a plastic lens according to claim 1, wherein at least one of the metal compound and the metal is at least one selected from the group consisting of aluminum oxide, aluminum hydroxide, bismuth, indium, tin, zinc, gallium, lead, cadmium, copper, and silver.

4. 3. The method for producing a plastic lens according to claim 1, wherein the content of at least one of the metal compound and the metal in the heat dissipation sheet is 65 to 100% by mass.

5. The method for manufacturing a plastic lens according to claim 1 or 2, wherein the lens substrate has a central portion having a thickness of less than 2 mm and a peripheral portion having a thickness greater than that of the central portion.

6. The method for manufacturing a plastic lens according to claim 5 , wherein the central portion is covered with the heat dissipation sheet.

7. 3. The method for producing a plastic lens according to claim 1, wherein the cured coating layer comprises a primer layer, a photochromic layer, and a protective layer.

8. The coating is a spin coating, The method for producing a plastic lens according to claim 1 or 2, wherein the maximum rotation speed in the spin coating is 100 rpm or more.

9. 3. The method for producing a plastic lens according to claim 1, wherein the thickness of the cured coating layer is 5 to 100 μm.

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