Plastic ophthalmic lens and method of manufacturing same, and eyeglasses

Abstract

A plastic lens, a manufacturing method thereof, and eyeglasses, the plastic lens having a lens base material and a cured coating layer formed on one side surface of the lens base material, the cured coating layer having a primer layer, a photochromic layer, and a protective layer, a surface hardness of the photochromic layer being 2.0 kgf / mm 2 Hereinafter, a plastic lens having a cured coating layer formed on one side surface of a lens base material has a difference between a power and a design power of less than 0.12.

Description

Technical Field

[0001] This disclosure relates to plastic lenses and methods for manufacturing the same, as well as eyeglasses, and more particularly, to plastic lenses with excellent fading properties and low heat deformation, methods for manufacturing the same, and eyeglasses having the aforementioned plastic lenses. Background Technology

[0002] From the perspective of not needing to change glasses when moving between indoors and outdoors, eyeglasses with plastic lenses that exhibit photochromic properties (color rendering) under light within a given wavelength range (e.g., outdoors) and fade under light outside the given wavelength range (e.g., indoors) are highly convenient. One method for imparting photochromic properties to plastic lenses is to coat a layer containing a photochromic compound and a polymeric compound (a polymeric composition for forming a photochromic layer) onto the surface of a lens substrate, and then irradiate the coated photochromic layer polymeric composition with light to cure it, thereby forming a cured coating layer (photochromic layer) with photochromic properties (for example, see Patent Document 1).

[0003] Existing technical documents

[0004] Patent documents

[0005] Patent Document 1: International Publication No. 2003 / 011967 Summary of the Invention

[0006] The problem that the invention aims to solve

[0007] For the photochromic plastic lenses described above, it is desirable that plastic lenses that show color when exposed to light, such as outdoors, fade rapidly when not exposed to light, such as indoors (fading property).

[0008] Furthermore, the curing of the polymeric composition to form the photochromic layer typically requires extensive light exposure, which can cause significant deformation of the lens substrate due to the heat generated by the light, sometimes rendering it unsuitable for use. Therefore, for photochromic plastic lenses, it is desirable to form a photochromic layer with minimal thermal deformation.

[0009] One aspect of this disclosure is to provide a plastic lens with excellent fading properties and low heat deformation, a method for manufacturing the same, and eyeglasses having the aforementioned plastic lens.

[0010] Problem Solving Methods

[0011] The embodiments of this disclosure relate to the following [1] to [8].

[0012] [1] A plastic lens comprising a lens substrate and a cured coating layer formed on one side surface of the lens substrate.

[0013] The aforementioned cured coating layer comprises a base layer, a photochromic layer, and a protective layer.

[0014] The surface hardness of the aforementioned photochromic layer is 2.0 kgf / mm. 2 the following,

[0015] The difference between the power of a plastic lens with a cured coating layer formed on one side of the lens substrate and the designed power is less than 0.12.

[0016] [2] According to the plastic lens described in [1] above, wherein,

[0017] The aforementioned photochromic layer is a layer formed by curing a polymeric composition.

[0018] The above-mentioned polymeric composition for forming a photochromic layer comprises:

[0019] Two or more (meth)acrylates, and

[0020] Photochromic compounds.

[0021] [3] According to the plastic lens described in [2] above, wherein,

[0022] The two or more of the above-mentioned (meth)acrylates contain at least a polyfunctional (meth)acrylate with a molecular weight of 500 or more.

[0023] [4] The plastic lens according to any one of [1] to [3] above, wherein,

[0024] The surface hardness of the aforementioned photochromic layer is 0.5 kgf / mm. 2 above.

[0025] [5] The plastic lens according to any one of [1] to [4] above, wherein,

[0026] The thickness of the above-mentioned cured coating layer is 40~100μm.

[0027] [6] The plastic lens according to any one of [1] to [5] above, wherein,

[0028] The thickness of the central portion of the above-mentioned lens substrate is less than 2 mm, and the peripheral portion is thicker than the central portion.

[0029] [7] A pair of eyeglasses having any one of the plastic lenses described in any one of [1] to [6] above.

[0030] [8] A method for manufacturing a plastic lens according to any one of [1] to [6] above, the method comprising:

[0031] The process of forming a base coating on one side surface of a lens substrate;

[0032] A photochromic layer forming process involves coating a polymeric composition for forming a photochromic layer onto the surface of the aforementioned base layer, curing the polymeric composition for forming a photochromic layer by light irradiation, and forming the photochromic layer.

[0033] The protective layer forming process for forming a protective layer on the surface of the aforementioned photochromic layer.

[0034] The intensity of the aforementioned light irradiation is 150~350mW / cm. 2 ,

[0035] The duration of the light irradiation mentioned above is 1 to 90 seconds.

[0036] The exposure to the aforementioned light irradiation ranged from 0.15 to 31.5 J / cm². 2 .

[0037] In order to solve the above-mentioned problems, the inventors conducted in-depth research and found that by setting the surface hardness of the photochromic layer and the difference between the power of the plastic lens with a cured coating layer formed on one side of the lens substrate and the designed power within a given range, the above-mentioned problems can be solved, and thus the present invention is completed.

[0038] The effects of the invention

[0039] According to one aspect of this disclosure, a plastic lens with excellent fading properties and low heat deformation, a method for manufacturing the same, and eyeglasses having the aforementioned plastic lens can be provided. Detailed Implementation

[0040] The following description is based on an example of an embodiment of the present disclosure. However, the embodiment shown below is an example used to embody the technical concept of the present disclosure, and the present disclosure is not limited to the following description.

[0041] This disclosure also includes any manner obtained by selecting or combining any of the matters described in this disclosure and this specification.

[0042] In this disclosure and specification, any preferred provision may be selected, and a combination of preferred provisions may be considered more preferred.

[0043] In this disclosure and specification, the phrase “XX~YY” refers to “XX and above and YY and below”.

[0044] In this disclosure and specification, regarding preferred numerical ranges (e.g., ranges in content, etc.), the lower and upper limits described in stages can be combined independently. For example, based on the description of "preferably 10 to 90, more preferably 30 to 60", the "preferable lower limit (10)" and the "more preferably upper limit (60)" can be combined to "10 to 60". In addition, in the numerical ranges described in this disclosure and specification, the upper or lower limit of the numerical range can be replaced with the values ​​shown in the embodiments.

[0045] In this disclosure and specification, a polymerizable composition refers to a composition comprising a polymerizable compound. Furthermore, a polymerizable compound refers to a compound having polymerizable groups.

[0046] In this disclosure and specification, "design power" refers to the ideal power of the plastic lens during the design phase. "The difference between the power of the plastic lens with a cured coating layer formed on one surface of the lens substrate and the design power" refers to the difference between the actual power of the manufactured plastic lens (plastic with a cured coating layer formed on one surface of the lens substrate) and the ideal power of the plastic lens during the design phase. It should be noted that the aforementioned design power may or may not be the power of the lens substrate before the cured coating layer is formed.

[0047] In this disclosure and specification, "on the surface of X" means not only "on the surface of X (in contact state)" but also "above the surface of X (in non-contact state)".

[0048] In this disclosure and specification, "(meth)acrylate" refers to a compound including acrylates and methacrylates. "Acrylate" refers to a compound having one or more acryloyl groups in one molecule. "Methacrylate" refers to a compound having one or more methacryloyl groups in one molecule. Regarding (meth)acrylates, the functional number is the number of groups selected from acryloyl and methacryloyl groups contained in one molecule. Furthermore, "methacrylate" refers to a compound containing only a methacryloyl group as a (meth)acryloyl group; compounds containing both acryloyl and methacryloyl groups as (meth)acryloyl groups are called (meth)acrylates. Acryloyl groups may be contained in the form of acryloyloxy groups, and methacryloyl groups may be contained in the form of methacryloyloxy groups.

[0049] In this disclosure and specification, "(meth)acryloyl" means to include both acryloyl and methacryloyl, and "(meth)acryloyloxy" means to include both acryloyloxy and methacryloyloxy.

[0050] In this disclosure and specification, unless otherwise specified, the described functional groups may have substituents or be unsubstituent. When a functional group has substituents, examples of substituents include alkyl groups (e.g., straight-chain alkyl groups with 1 to 6 carbon atoms or branched alkyl groups with 1 to 6 carbon atoms), hydroxyl groups, alkoxy groups (e.g., alkoxy groups with 1 to 6 carbon atoms), halogen atoms (e.g., fluorine, chlorine, bromine), cyano groups, amino groups, nitro groups, acyl groups, carboxyl groups, aryl groups, and polyether groups. Furthermore, regarding substituent groups, "number of carbon atoms" refers to the number of carbon atoms in the portion not containing the substituent.

[0051] In this disclosure and specification, "straight-chain alkyl or branched alkyl" does not include cycloalkyl. Straight-chain alkyl or branched alkyl may be unsubstituted or without substituents. Straight-chain alkyl or branched alkyl may have cycloalkyl (e.g., cyclohexyl) as a substituent. As an alternative, it is preferred that straight-chain alkyl or branched alkyl does not have cycloalkyl as a substituent.

[0052] In this disclosure and specification, "viscosity" refers to the value measured by a vibratory viscometer in an atmospheric environment at 25°C.

[0053] Regarding the inclusion of solvents, the term "total" in this disclosure and specification refers to the total amount of all components excluding solvents.

[0054] In this disclosure and specification, "central portion of the lens substrate" refers to the portion with a radius of less than 5 mm from the center of the lens substrate.

[0055] In this disclosure and specification, "peripheral portion of the lens substrate" refers to the portion with a radius of 15 mm or more from the center of the lens substrate.

[0056] In this disclosure and specification, "the central peripheral portion of the lens substrate" refers to the portion with a radius exceeding 5 mm and less than 15 mm from the center of the lens substrate.

[0057] The term "plastic lens" in this disclosure and specification can refer to either a finished lens or a semi-finished lens. It should be noted that semi-finished lenses can be processed into lenses for actual use through grinding and polishing.

[0058] In this disclosure and specification, "finished lens" refers to a lens obtained by processing a semi-finished lens into a lens for actual use through grinding or polishing, or a lens obtained by molding a lens into a lens for actual use.

[0059] The "thickness of the lens substrate" in this disclosure and specification refers to the value obtained by measuring the thickness of the lens substrate using a high-performance ABS digital display indicator (Mitutoyo Corporation, ID-FNX series) connected to the convex and concave terminals of the lens substrate.

[0060] The "thickness of the cured coating" in this disclosure and specification refers to the value obtained by measuring the reflectivity (interference waveform) of the sample using a non-contact film thickness measuring instrument (System Road Corporation, FF8 series) and calculating the film thickness using FFT (High-Speed ​​Fourier Transform).

[0061] In this disclosure and specification, "light intensity" refers to a value measured as follows: using a light meter (USHIO Corporation, UIT-250), the light is illuminated at a lens stage 300 mm from the center of the light source to the light-receiving part (center wavelength 365 mm).

[0062] In this disclosure and specification, "exposure to light" refers to the value measured as follows: the cumulative value of irradiation time (light intensity (mW / cm²)) measured using a light meter (USHIO Corporation, UIT-250), at a lens stage 300 mm from the center of the light source to the light-receiving part (center wavelength 365 mm). 2 () × irradiation time (seconds)).

[0063] [Plastic lenses]

[0064] The following describes one aspect of the plastic lens of this disclosure in more detail.

[0065] In this disclosure and specification, a plastic lens only needs to have a lens substrate and a cured coating layer formed on one surface of the lens substrate. There are no particular limitations. It may have another cured coating layer formed on the other surface of the lens substrate, or it may not have one. It should be noted that the other cured coating layer may be the base coating layer described later, a protective layer, a hard coating layer, or other functional layers.

[0066] The surface hardness of the aforementioned photochromic layer only needs to be 2.0 kgf / mm. 2 The following values ​​are acceptable, with no particular restrictions, but 0.5~1.5 kgf / mm is preferred. 2 More preferably, it is 0.5~1.2 kgf / mm 2 If the value is above the lower limit of the above range, it is not easy to turn into a gel or liquid, and it is easy to maintain its shape in the form of a layer. If the value is below the upper limit of the above range, the fading properties are even better.

[0067] It should be noted that the surface hardness of the aforementioned photochromic layer can be determined using the method described in the examples.

[0068] From an optical quality point of view, the difference between the power of the plastic lens with a cured coating layer formed on one side of the lens substrate and the designed power is acceptable as long as it is less than 0.12, and there are no particular limitations. It is preferably 0.00 to 0.09, more preferably 0.00 to 0.06, and particularly preferably 0.00 to 0.03.

[0069] It should be noted that the difference between the power of the plastic lens and the designed power can be determined using the method described in the examples.

[0070] Lens substrate

[0071] The lens substrate will now be described in more detail.

[0072] In this disclosure and specification, there are no particular limitations on the raw materials used as lens substrates. Examples include: (meth)acrylic resin; styrene resin; polycarbonate resin; allyl resin; allyl carbonate resins such as diethylene glycol dielyl carbonate resin (CR-39); vinyl resin; polyester resin; polyether resin; urethane resin obtained by reacting an isocyanate compound with a hydroxyl compound such as diethylene glycol; thiourethane resin 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)epoxide compound having one or more disulfide bonds within the molecule. One or more of these materials may be used alone.

[0073] There are no particular limitations on the types of lens substrates mentioned above; for example, lens substrates for eyeglasses and lens substrates for safety goggles can be cited.

[0074] There are no particular restrictions on the color of the lens substrate; it can be colorless (undyed) or dyed.

[0075] There are no particular limitations on the refractive index of the aforementioned lens substrate; for example, 1.50 to 1.75 are possible values. It should be noted that, in this disclosure and specification, the refractive index refers to the refractive index of mercury e-rays at 546.07 nm.

[0076] There are no particular limitations on the focal point of the aforementioned lens substrate; for example, monofocal, multifocal, and progressive lenses can be used.

[0077] The surface of the aforementioned lens substrate is not particularly limited, and examples include convex surfaces, concave surfaces, and flat surfaces. In typical lens substrates, the object-side surface is convex and the eyeball-side surface is concave, but this disclosure is not limited to this.

[0078] There is no particular limitation on the thickness of the central portion of the aforementioned lens substrate. From the point of view of optical design, it is preferably less than 9.1 mm, more preferably 0.8 to 2.4 mm, and particularly preferably 0.8 mm or more but less than 2.0 mm.

[0079] There is no particular limitation on the thickness of the peripheral portion of the aforementioned lens substrate. From the point of view of optical design, it is preferable to be thicker than the central portion, more preferably 0.8 to 16.5 mm, and particularly preferably 1.6 to 13.0 mm.

[0080] <Cure Coating Layer>

[0081] The cured coating layer will be explained in more detail below.

[0082] In this disclosure and specification, the cured coating layer is formed on one side surface of the lens substrate. It is only necessary to have a base coating, a photochromic layer, and a protective layer. There are no particular restrictions. It may have a hard coating, other functional layers, etc., or it may not have them.

[0083] The thickness of the cured coating layer is not particularly limited, but is preferably 40 to 100 μm, more preferably 45 to 95 μm, and particularly preferably 50 to 90 μm. If the thickness is above the lower limit of the above range, it is easy to maintain adhesion, and if the thickness is below the upper limit of the above range, it is easy to maintain the translucency (transparency) of the cured coating layer.

[0084] (Base coating)

[0085] The base coat is described in more detail below.

[0086] In this disclosure and specification, the primer layer refers to a layer formed by curing a polymeric composition (hereinafter sometimes simply referred to as "composition for primer layer") to form the primer layer.

[0087] There are no particular restrictions on the location of the aforementioned base coating layer, but from the viewpoint of improving the adhesion between the lens substrate and the photochromic layer, it is preferable to place it between the lens substrate and the photochromic layer.

[0088] The thickness of the aforementioned base coating 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 it is above the lower limit of the above range, the adhesion to the lens substrate and the photochromic layer becomes good, and if it is below the upper limit of the above range, it is easy to suppress the invasion of the photochromic layer.

[0089] As one example of the above-mentioned primer coating composition, a primer coating composition comprising a polyisocyanate, a hydroxyl-containing polymeric compound, and at least one polymeric compound selected from (meth)acrylates and vinyl ethers with a viscosity of less than 100 cP can be provided.

[0090] It should be noted that there are no particular limitations on the components contained in the composition for the primer coating. However, from the viewpoint of suppressing the attenuation of photochromic properties caused by the primer coating and the viewpoint of good adhesion to the photochromic layer, it is preferable to include the above three components.

[0091] The various components contained in the above-mentioned primer coating composition will be described in more detail below.

[0092] -Polyisocyanate-

[0093] The aforementioned polyisocyanates refer to compounds having two or more isocyanate groups in one molecule.

[0094] The number of isocyanate groups contained in the aforementioned polyisocyanate 1 molecule is not particularly limited, but is preferably 2 to 6, more preferably 3 to 5, and particularly preferably 3 to 4. If the value is above the lower limit of the above range, the water resistance of the base coating is easily improved, and if the value is below the upper limit of the above range, it is easy to bond with the lens substrate.

[0095] The molecular weight of the aforementioned polyisocyanate is not particularly limited, but is preferably 200 to 800, more preferably 300 to 700, and particularly preferably 400 to 600. If it is above the lower limit of the above range, it is easy to adhere to the lens substrate; if it is below the upper limit of the above range, the water resistance of the base coating is easily improved.

[0096] Specific examples of the aforementioned polyisocyanates are not particularly limited, and examples include: aromatic diisocyanates such as diphenylene diisocyanate, phenylene diisocyanate, toluene diisocyanate, diphenylmethane diisocyanate, and naphthalene diisocyanate; and aliphatic or alicyclic diisocyanates such as hexamethylene diisocyanate, lysine diisocyanate, cyclohexane diisocyanate, isophorone diisocyanate, 4,4'-dicyclohexylmethane diisocyanate, 1,3-diisocyanate-methylcyclohexane, and tetramethylphenylene diisocyanate. They can be used alone or in combination with more than one type.

[0097] Furthermore, the polyisocyanates mentioned above can be urea carbamates, adducts, biuret bodies, or isocyanurates. They can be used individually or in combination.

[0098] Furthermore, there are no particular restrictions on commercially available polyisocyanates, such as: CORONATE HX, CORONATE HXR, CORONATE HXLV, CORONATE HK, CORONATE 2715, CORONATE HL, CORONATE L, CORONATE 2037, HDI, TDI, MDI, etc., manufactured by Tosoh Corporation; Takenate 500, Takenate 600, DURANATE 24A-100, TPA-100, TKA-100, P301-75E, Takenate... These are commercially available products manufactured by Mitsui Chemicals Co., Ltd., including D-110N, D-120N, D-127N, D-140N, D-160N, D15N, D-170N, D-170HN, D-172N, D-177N, D-178N, and D-101E. They can be used individually or in combination.

[0099] -Hydroxy-containing polymeric compounds-

[0100] The number of hydroxyl groups contained in the molecule of the aforementioned hydroxyl-containing polymeric compound 1 is not particularly limited, but is preferably 1 to 6, more preferably 1 to 5, and particularly preferably 2 to 4. If the number is above the lower limit of the above range, the reaction efficiency with the polyisocyanate tends to be good, and if the number is below the upper limit of the above range, it tends to adhere well to the photochromic layer.

[0101] It should be noted that the inventors speculate that the urethane bonds formed by reacting the isocyanate groups of the polyisocyanate with the hydroxyl groups of the hydroxyl-containing polymeric compound can help improve the adhesion of the base coating.

[0102] There is no particular limitation on the number of polymerizable groups contained in the molecule of the above-mentioned hydroxyl-containing polymeric compound 1, but from the viewpoint of polymerization efficiency, it is preferable to have 2 or more.

[0103] As one example of the aforementioned hydroxyl-containing polymeric compounds, (meth)acrylates can be cited.

[0104] When the hydroxyl-containing polymeric compound is a (meth)acrylate, the number of functional groups in the (meth)acrylate is not particularly limited, but from the viewpoint of adhesion, 1 (monofunctional) to 3, more preferably 2 to 3, is preferred. It should be noted that the aforementioned functional group, i.e., the (meth)acryloyl group, may contain only an acryloyl group, or only a methacryloyl group, or may contain both an acryloyl group and a methacryloyl group. As an option, from the viewpoint of adhesion, it is preferred that the hydroxyl-containing polymeric compound contains only an acryloyl group as the (meth)acryloyl group.

[0105] There are no particular limitations on the molecular weight of the hydroxyl-containing polymeric compound, but it is preferably 100 to 600, more preferably 200 to 500, and particularly preferably 300 to 400. If the molecular weight is above the lower limit of the above range, the reaction efficiency with the polyisocyanate tends to be good, and if the molecular weight is below the upper limit of the above range, it tends to adhere well to the photochromic layer.

[0106] Specific examples of the aforementioned (meth)acrylates are not particularly limited, and examples include: 2-hydroxyethyl (meth)acrylate, hydroxypropyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, 1,4-cyclohexanediethanol monoacrylate, 2-hydroxy-1-acryloyloxy-3-methacryloyloxypropane, 2-hydroxy-1,3-dimethacryloyloxypropane, pentaerythritol tetraacrylate, 2-hydroxy-3-phenoxypropyl acrylate, hexahydrophthalic acid monoacryloyloxyethyl ester, 2-acryloyloxyethyl phthalate, 2-(acryloyloxyoxy)ethyl 2-hydroxyethyl phthalate, and compounds represented by the following formula (1). They may be used individually or in combination.

[0107] [Chemical Formula 1]

[0108] ···(1)

[0109] As one example of the aforementioned hydroxyl-containing polymeric compounds, hydroxyl-containing polymeric compounds having amide groups can be cited.

[0110] There are no particular limitations on the hydroxyl-containing polymeric compounds with amide groups mentioned above; for example, N-(2-hydroxyethyl)acrylamide, etc., can be cited.

[0111] As one example of the aforementioned hydroxyl-containing polymeric compounds, hydroxyl-containing polymeric compounds with an epoxy ester structure can be cited. An epoxy ester structure refers to a structure formed by the reaction of an epoxy group and a carboxyl group, which can be represented by "-CH(OH)-CH2-OC(=O)-".

[0112] There are no particular restrictions on commercially available hydroxyl-containing polymeric compounds with an epoxy ester structure. Examples include: epoxy ester 40EM (Kyoeisha Chemical), epoxy ester 70PA (Kyoeisha Chemical), epoxy ester 80MFA (Kyoeisha Chemical), epoxy ester 200PA (Kyoeisha Chemical), epoxy ester 3002M(N) (Kyoeisha Chemical), epoxy ester 3002A(N) (Kyoeisha Chemical), epoxy ester 3000MK (Kyoeisha Chemical), and epoxy ester 3000A (Kyoeisha Chemical). They can be used individually or in combination.

[0113] - At least one polymeric compound selected from (meth)acrylates and vinyl ethers with a viscosity of less than 100 cP-

[0114] Preferably, the above-mentioned primer composition comprises at least one polymeric compound selected from (meth)acrylates and vinyl ethers with a viscosity of 100 cP (centipoise) or less (hereinafter, sometimes simply referred to as "low-viscosity polymeric compound"). The inventors hypothesize that the primer composition comprising the above-mentioned low-viscosity polymeric compound can suppress the fading of photochromic properties caused by the primer.

[0115] The viscosity of the aforementioned low-viscosity polymerizable compound can be as low as 100 cP or less, and there are no particular limitations. From the viewpoints of processability and suppressing the generation of optical defects, it is preferably 5 to 70 cP, and more preferably 10 to 50 cP.

[0116] The number of functional groups in the (meth)acrylate, which is one of the aforementioned low-viscosity polymerizable compounds, is not particularly limited, but from the viewpoint of adhesion, it is preferably 1 (monofunctional) to 3, more preferably 1 (monofunctional) to 2.

[0117] As one type of the aforementioned low-viscosity polymerizable compound, (meth)acrylates may contain aryl (e.g., phenyl), amide, etc. In this disclosure and specification, "ethylene ether" refers to a compound having one or more vinyl groups and one or more ether bonds per molecule, preferably having two or more vinyl groups per molecule, more preferably having two to four. Furthermore, the number of ether bonds contained in an ethylene ether is preferably two to four per molecule.

[0118] The molecular weight of the aforementioned low-viscosity polymeric compound is not particularly limited, but is preferably 100 to 300, more preferably 150 to 250. If it is above the lower limit of the above range, the generation of optical defects is easily suppressed, and if it is below the upper limit of the above range, it is easily bonded to the photochromic layer.

[0119] Specific examples of the aforementioned low-viscosity polymerizable compounds are not particularly limited, and examples include: 2-phenoxyethyl (meth)acrylate, acrylamide, methoxy polyethylene glycol (meth)acrylate, phenoxy polyethylene 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, etc. Methacrylate, phenoxyethyl methacrylate, ethylene glycol dimethacrylate, diethylene glycol dimethacrylate, triethylene glycol dimethacrylate, tricyclodecanediethanol dimethacrylate, ethoxylated polypropylene glycol dimethacrylate, trimethylolpropane trimethacrylate, ethyl methacrylate, butyl methacrylate, isobutyl methacrylate, tert-butyl methacrylate, 2-ethylhexyl methacrylate, isodecanyl methacrylate, ( Dodecyl methacrylate, tridecyl methacrylate, diethylene glycol butyl ether (meth)acrylate, cyclohexyl methacrylate, tetrahydrofurfuryl methacrylate, benzyl methacrylate, 2-phenoxyethyl methacrylate, isobornyl methacrylate, 2-(dimethylamino)ethyl methacrylate, 2-(diethylamino)ethyl methacrylate, glycidyl methacrylate, ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethyl... Glycol di(meth)acrylate, polyethylene glycol di(meth)acrylate, tetramethylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, hexanediol di(meth)acrylate, nonanediol di(meth)acrylate, isoamyl (meth)acrylate, ethylene glycol monovinyl ether, tetramethylene glycol monovinyl ether, diethylene glycol monovinyl ether, 2-ethylhexyl vinyl ether, 2-[2-(vinyloxy)ethoxy]ethyl 2-acrylate, 2-methyl-2-acrylate 2-(2-vinyloxyethoxy)ethyl ester, etc. They can be used alone or in combination.

[0120] There are no particular limitations on the content of the aforementioned low-viscosity polymeric compound. It is preferred to be 30.0 to 90.0% by mass, more preferably 35.0 to 80.0% by mass, and particularly preferably 40.0 to 70.0% by mass, out of a total of 100% by mass of the low-viscosity polymeric compound, polyisocyanate, and hydroxyl-containing polymeric compound.

[0121] If the value is above the lower limit of the above range, it is easy to process; if the value is below the upper limit of the above range, it is easy to seal with the lens substrate.

[0122] One way to measure the content of the aforementioned low-viscosity polymeric compound is to use it as the component with the highest content in a primer composition containing the low-viscosity polymeric compound, polyisocyanate, and hydroxyl-containing polymeric compound.

[0123] There are no particular limitations on the content of the aforementioned polyisocyanate, but it is preferably 10.0 to 70.0% by mass, more preferably 20.0 to 60.0% by mass, and particularly preferably 30.0 to 50.0% by mass, in a total of 100% by mass of the low-viscosity polymerizable compound, the polyisocyanate, and the hydroxyl-containing polymerizable compound.

[0124] If the value is above the lower limit of the above range, the water resistance of the base coating is easily improved; if the value is below the upper limit of the above range, it is easy to bond tightly with the lens substrate.

[0125] There are no particular limitations on the content of the aforementioned hydroxyl-containing polymeric compound. It is preferred to be 3.0 to 30.0% by mass, more preferably 5.0 to 25.0% by mass, and particularly preferably 7.0 to 20.0% by mass, in a total of 100% by mass of the low-viscosity polymeric compound, the polyisocyanate, and the hydroxyl-containing polymeric compound.

[0126] If the value is above the lower limit of the above range, the reaction efficiency with polyisocyanates tends to be good; if the value is below the upper limit of the above range, it tends to adhere well to the photochromic layer.

[0127] The above-mentioned primer composition may further include a polymerization initiator as needed.

[0128] There are no particular limitations on the amount of the polymerization initiator used, but from the viewpoint of the efficiency of the base coating formation, it is preferably 0.01 to 3.0 parts by mass relative to a total of 100 parts by mass of the low-viscosity polymerizable compound, the polyisocyanate, and the hydroxyl-containing polymerizable compound.

[0129] There are no particular restrictions on the polymerization initiator used; any known polymerization initiator may be used.

[0130] There are no particular limitations on the aforementioned known polymerization initiators; examples include photoradical polymerization initiators and thermal polymerization initiators. They can be used individually or in combination. Among these, from the viewpoint of enabling the polymerization reaction to proceed in a short time, photoradical polymerization initiators are preferred.

[0131] For specific examples of photoradical polymerization initiators, refer to the polymerization initiators that may be included in polymeric compositions for forming photochromic layers, as described later.

[0132] The above-mentioned primer coating composition may or may not contain a solvent.

[0133] When the above-mentioned primer coating composition contains a solvent, any solvent can be used as long as it does not hinder the polymerization reaction of the polymerizable composition. There are no particular restrictions, and any solvent can be used.

[0134] When the above-mentioned composition for the base coating contains a solvent, there is no particular limitation on the amount of solvent. From the viewpoint of suppressing the generation of optical defects, it is preferably 10.0 parts by mass or less, more preferably 5.0 parts by mass or less, and particularly preferably 3.0 parts by mass or less, relative to a total of 100 parts by mass of the low-viscosity polymeric compound, the polyisocyanate, and the hydroxyl-containing polymeric compound.

[0135] The above-mentioned primer composition may further include, as needed, known additives that can be typically added to the composition used to form the primer.

[0136] The amount of the additives mentioned above is not particularly limited as long as they achieve the effect of the base coating. It 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 a total of 100 parts by mass of the low-viscosity polymeric compound, the polyisocyanate, and the hydroxyl-containing polymeric compound.

[0137] The content of the aforementioned low-viscosity polymeric compound, polyisocyanate, and hydroxyl-containing polymeric compound is not particularly limited as long as it achieves the effect of the primer coating. In 100% by mass of the primer coating composition (excluding the polymerization initiator), it is preferably 80.0 to 100.0% by mass, more preferably 85.0 to 100.0% by mass, and even more preferably 90.0 to 100.0% by mass.

[0138] The above-described primer coating composition can be prepared by mixing the various components described above simultaneously or in any order.

[0139] (Photochromic layer)

[0140] The photochromic layer will now be explained in more detail.

[0141] In this disclosure and specification, a photochromic layer refers to a layer formed by curing a polymeric composition (hereinafter sometimes simply referred to as "composition for photochromic layer") to form a photochromic layer.

[0142] There are no particular restrictions on the location of the photochromic layer, but from the viewpoint of good adhesion to the lens substrate and protection of the photochromic layer, it is preferable to place it between the base layer and the protective layer described later.

[0143] The thickness of the photochromic layer is not particularly limited, but is preferably 5 to 80 μm, more preferably 10 to 70 μm, and especially preferably 15 to 60 μm. If the thickness is above the lower limit of the above range, the color concentration tends to become darker, and if the thickness is below the upper limit of the above range, the transparency tends to be maintained.

[0144] As one embodiment of the aforementioned photochromic layer composition, a photochromic layer composition comprising two or more (meth)acrylates and a photochromic compound can be provided. The aforementioned two or more (meth)acrylates function as polymerizable compounds within the photochromic layer composition.

[0145] The various components contained in the above-mentioned photochromic layer composition will be described in more detail below.

[0146] -Two or more (meth)acrylates-

[0147] There are no particular limitations on the two or more (meth)acrylates mentioned above. From the viewpoint of fading speed, it is preferred to include at least a polyfunctional (meth)acrylate with a molecular weight of 500 or more (hereinafter, sometimes referred to as "component A").

[0148] There are no particular limitations on the (meth)acrylates other than component A among the two or more (meth)acrylates mentioned above. Examples include: monofunctional (meth)acrylates (hereinafter, sometimes referred to as "component B"), polyfunctional (meth)acrylates that do not have a cyclic structure or a branched structure (hereinafter, sometimes referred to as "component C"), and difunctional (meth)acrylates that contain at least one structure selected from cyclic structures and branched structures (hereinafter, sometimes referred to as "component D"). They can be used alone or in combination.

[0149] --ingredient A--

[0150] The molecular weight of component A is only required to be 500 or higher, with no particular limitation. It is preferably 600 to 2000, more preferably 650 to 1500, and particularly preferably 700 to 1300. If it is above the lower limit of the above range, the fading rate is easily increased. If it is below the upper limit of the above range, the photochromic layer is easily made to have high hardness.

[0151] There are no particular limitations on the composition A mentioned above, and examples include: difunctional (meth)acrylates, trifunctional (meth)acrylates, tetrafunctional (meth)acrylates, and pentafunctional (meth)acrylates. One or more of these can be used. From the viewpoint of weather resistance, difunctional or trifunctional (meth)acrylates are preferred.

[0152] The (meth)acryloyl group in component A may contain only an acryloyl group, only a methacryloyl group, or both an acryloyl group and a methacryloyl group. That is, component A may be an acrylate or a methacrylate.

[0153] As one embodiment of component A mentioned above, acyclic polyfunctional (meth)acrylates can be cited. In this disclosure and specification, "acyclic" means that which does not contain a cyclic structure. Conversely, "cyclic" means that which contains a cyclic structure. Acyclic polyfunctional (meth)acrylates refer to (meth)acrylates with two or more functions that do not contain a cyclic structure.

[0154] There are no particular limitations on specific examples of ingredient A, such as polyalkylene glycol di(meth)acrylate represented by formula (2) below. They can be used alone or in combination or in more than one form.

[0155] [Chemical Formula 2]

[0156] ···(2)

[0157] In equation (2), R 1 and R 2 Each can be represented independently by 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, which is 2 or more.

[0158] The number of carbon atoms of the alkylene group represented by R in formula (2) is not particularly limited, but is preferably 1 to 5, more preferably 2 to 4.

[0159] The alkylene group represented by R in formula (2) is not particularly limited, and examples include ethylene, propyleneene, tetramethylene, etc.

[0160] The value of n in equation (2) is not particularly limited, but is preferably 2 to 30, more preferably 2 to 25, and especially preferably 2 to 20.

[0161] There are no particular limitations on the polyalkylene glycol di(meth)acrylate represented by formula (2), and examples include: polyethylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, polytetramethylene glycol di(meth)acrylate, etc. They can be used alone or in combination.

[0162] In addition, as a specific example of component A, tri(meth)acrylate represented by the following formula (3) can also be cited.

[0163] The (meth)acryloyl group of the tri(meth)acrylate represented by formula (3) may contain only an acryloyl group, or only a methacryloyl group, or may contain both an acryloyl group and a methacryloyl group.

[0164] [Chemical Formula 3]

[0165] ···(3)

[0166] In equation (3), R 40 R 41 R 44 R 45 R 47 and R 48 Each independently represents an alkylene group, R 43 R represents an alkyl group. 42 R 46 and R 49 Each can be used independently to represent a hydrogen atom or a methyl group.

[0167] In equation (3), n1 represents OR 41 The number of repeats of the alkoxy group shown is 2 or more.

[0168] In equation (3), n2 represents OR 45 The number of repeats of the alkoxy group shown is 2 or more.

[0169] In equation (3), n3 represents OR 48 The number of repeats of the alkoxy group shown is 2 or more.

[0170] Regarding R in equation (3) 41 R 45 and R 48 As stated above regarding R in equation (2). Regarding n1, n2, and n3 in equation (3), as stated above regarding n in equation (2). In equation (3), R... 41 R 45 and R 48 They can be the same, and two or three can be different. This also applies to n1, n2, and n3.

[0171] R in equation (3) 42 R 46 and R 49 Each can be used to represent a hydrogen atom or a methyl group independently.

[0172] As a (meth)acryloyl group, the tri(meth)acrylate represented by formula (3) may contain only an acryloyl group, or only a methacryloyl group, or may contain both an acryloyl group and a methacryloyl group.

[0173] As R in equation (3) 43 The number of carbon atoms in the alkyl group is not particularly limited, but is preferably 1 to 5, more preferably 1 to 4.

[0174] R in equation (3)43 The alkyl group represented is either a straight-chain alkyl group or a branched alkyl group.

[0175] As R in equation (3) 43 There are no particular limitations on the specific examples of alkyl groups, such as methyl, ethyl, etc.

[0176] R in equation (3) 40 R 44 and R 47 Each can be used independently to represent an alkylene group.

[0177] As R in equation (3) 40 R 44 and R 47 The number of carbon atoms in the alkylene group is not particularly limited, but is preferably 1 to 5, more preferably 1 to 4.

[0178] As R in equation (3) 40 R 44 and R 47 There are no particular limitations on the specific examples of the alkylene groups represented; for example, methylene, ethylene, propylene, tetramethylene, etc.

[0179] There are no particular limitations on the tri(meth)acrylate represented by formula (3), for example, trimethylolpropane polyoxyethylene ether tri(meth)acrylate, etc. They can be used alone or in more than two types.

[0180] --Ingredient B--

[0181] Component B is a monofunctional (meth)acrylate represented by the following formula (4).

[0182] [Chemical Formula 4]

[0183] ···(4)

[0184] In equation (4), R 10 It represents a hydrogen atom or a methyl group.

[0185] The monofunctional (meth)acrylate represented by formula (4) can be either an acrylate or a methacrylate.

[0186] In equation (4), R 11 It refers to a straight-chain alkyl group with 3 or more carbon atoms, or a branched alkyl group with 3 or more carbon atoms.

[0187] R in equation (4) 11 The alkyl group can be unsubstituted or substituented. There are no particular limitations on the substituents; for example, the various substituents described above can be cited.

[0188] As R in equation (4) 11 The number of carbon atoms in the straight-chain or branched alkyl group is not particularly limited, but is preferably 3 to 15, more preferably 3 to 14, and particularly preferably 3 to 12.

[0189] If the value is above the lower limit of the above range, the color concentration of the photochromic layer tends to be higher; if the value is below the upper limit of the above range, the photochromic compound tends to dissolve in the composition for the photochromic layer.

[0190] The molecular weight of the monofunctional (meth)acrylate represented by formula (4) can 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) can be a monofunctional (meth)acrylate with a molecular weight of 150 or less.

[0191] There are no particular limitations on specific examples of monofunctional (meth)acrylates represented by formula (4), such as n-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, isodecyl (meth)acrylate, and n-laurate (meth)acrylate. They can be used alone or in combination or in more than one form.

[0192] There are no particular limitations on the types of multifunctional (meth)acrylates that can be included in the composition of photochromic layers other than component A. However, from the viewpoint of increasing the (meth)acryloyl group content in the composition and forming a rigid polymer network between molecules, (meth)acrylates with a high proportion of (meth)acryloyl groups in the molecule are preferred. From this point of view, multifunctional (meth)acrylates with a smaller molecular weight than component A are preferred.

[0193] There are no particular limitations on the molecular weight of the polyfunctional (meth)acrylates other than component A, but from the above perspective, a molecular weight of 100 or more and less than 500 is preferred, 100 to 400 is more preferred, and 100 to 350 is particularly preferred.

[0194] There are no particular restrictions on the number of functional groups in the polyfunctional (meth)acrylate other than component A mentioned above. However, from the viewpoint of weather resistance, it is preferable to use a polyfunctional (meth)acrylate with a larger number of functional groups than the polyfunctional (meth)acrylate used as component A. Furthermore, the number of functional groups in the polyfunctional (meth)acrylate can be, for example, set to 10 to 15. There are no particular restrictions on the number of functional groups in the polyfunctional (meth)acrylate (10 to 15), and examples include poly[(3-methacryloyloxypropyl)silsesquioxane] derivatives, etc. They can be used alone or in combination with more than one type.

[0195] There are no particular limitations on the use of polyfunctional (meth)acrylates. Examples include: polyfunctional (meth)acrylates (component C) that do not have a cyclic structure or a branched structure, and difunctional (meth)acrylates (component D) that contain at least one structure selected from cyclic structures and branched structures. They can be used alone or in combination or in more than one form.

[0196] The following provides a more detailed explanation of components C and D.

[0197] --Ingredient C--

[0198] Component C is a polyfunctional (meth)acrylate without cyclic or branched structures, represented by the following formula (5).

[0199] [Chemical Formula 5]

[0200] ···(5)

[0201] In equation (5), R 3 and R 4 Each can be used to represent a hydrogen atom or a methyl group independently.

[0202] In equation (5), m represents an integer greater than or equal to 1, which can be less than or equal to 10, less than or equal to 9, less than or equal to 8, less than or equal to 7, or less than or equal to 6.

[0203] In the case that component C has a methacryloyl group, the branched structure contained in the methacryloyl group is not considered.

[0204] The molecular weight of component C is not particularly limited, but is preferably 100 to 400, more preferably 140 to 350, and particularly preferably 160 to 300. If it is above the lower limit of the above range, the fading rate is easily increased; if it is below the upper limit of the above range, the color rendering concentration of the photochromic layer is easily increased.

[0205] As (meth)acryloyl, component C may contain only acryloyl, only methacryloyl, or both acryloyl and methacryloyl.

[0206] Specific examples of component C mentioned above are not particularly limited, such as 1,9-nonanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,10-decanediol di(meth)acrylate, etc. They can be used alone or in combination with more than one other.

[0207] --Ingredient D--

[0208] Component D is a difunctional (meth)acrylate containing at least one structure selected from cyclic and branched structures.

[0209] It is speculated that including the above-mentioned component D in the composition for photochromic layers helps to increase the color rendering concentration of the photochromic layer formed by the composition for photochromic layers.

[0210] In one manner, component D contains one or more cyclic structures and no branched structures in one molecule; in another manner, one molecule contains one or more branched structures and no cyclic structures in one molecule; and in yet another manner, one molecule may contain one or more cyclic structures and one or more branched structures.

[0211] The number of at least one structure selected from cyclic and branched structures contained in the above-mentioned component D is not particularly limited, but is preferably 1 to 3, more preferably 1 to 2, and particularly preferably 1.

[0212] In the case that component D has a methacryloyl group, the branched structure contained in the methacryloyl group is not considered.

[0213] As a way of including component D containing one or more cyclic structures, examples include alicyclic difunctional (meth)acrylates.

[0214] As an alicyclic difunctional (meth)acrylate, there are no particular limitations; for example, those having R... 111 -(L 11 ) n11 -Q-(L 22 ) n22 -R 222 Compounds with structures represented, etc.

[0215] Here, Q represents a divalent alicyclic group, and R 111 and R 222 Each independently represents (meth)acryloyl or (meth)acryloyloxy, L 11 and L 22 Each of these groups independently represents a linking group, and n11 and n22 independently represent 0 or 1, respectively.

[0216] There are no particular limitations on the divalent alicyclic group represented by Q. Examples suitable for reference include alicyclic hydrocarbon groups with 3 to 20 carbon atoms, such as cyclopentylene, cyclohexylene, cycloheptylene, cyclooctylene, tricyclodecylene, and adamantylene.

[0217] As L 11 and L 22 The linking group can be specified without particular limitation; for example, alkylene groups with 1 to 6 carbon atoms can be included.

[0218] Specific examples of alicyclic difunctional (meth)acrylates are not particularly limited, and examples include: cyclohexanediethanol di(meth)acrylate, ethoxylated cyclohexanediethanol di(meth)acrylate, propoxylated cyclohexanediethanol di(meth)acrylate, ethoxylated propoxylated cyclohexanediethanol di(meth)acrylate, tricyclodecanediethanol di(meth)acrylate, ethoxylated tricyclodecanediethanol di(meth)acrylate, propoxylated tricyclodecanediethanol di(meth)acrylate, ethoxylated propoxylated tricyclodecanediethanol di(meth)acrylate, etc. They can be used alone or in combination.

[0219] As a way to include component D with one or more branched structures, examples include difunctional (meth)acrylates containing branched alkylene groups. 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, further preferably 3 to 8, and particularly preferably 4 to 7. As a way to include branched alkylene groups, a quaternary carbon (i.e., a carbon bonded to four carbons) may be included.

[0220] There are no particular limitations on specific examples of component D containing one or more branched structures; for example, neopentyl glycol di(meth)acrylate, ethoxylated neopentyl glycol di(meth)acrylate, propoxylated neopentyl glycol di(meth)acrylate, etc. They can be used alone or in combination with more than one type.

[0221] The molecular weight of component D is not particularly limited, but is preferably 200 to 400. If it is above the lower limit of the above range, the color rendering concentration of the photochromic layer can be easily increased; if it is below the upper limit of the above range, the photochromic compound can be easily dissolved in the composition for the photochromic layer.

[0222] As (meth)acryloyl, the above component D may contain only acryloyl, or only methacryloyl, or may contain both acryloyl and methacryloyl.

[0223] There is no particular limitation on the content of the polymeric compound (i.e., the total content of multiple polymeric compounds), but it is preferably 70 to 99% by mass, more preferably 80 to 95% by mass, in 100% by mass of the composition for photochromic layer. If the content is above the lower limit of the above range, the photochromic compound is easily soluble in the composition for photochromic layer, and if the content is below the upper limit of the above range, the dimming characteristics are easily improved.

[0224] The above-mentioned photochromic layer composition may or may not contain a solvent. When a solvent is included, any solvent may be used as long as it does not hinder the polymerization reaction of the polymerizable composition, and any amount of any solvent may be used.

[0225] The content of component A is not particularly limited, but it is preferably 50-95% by mass, more preferably 55-92% by mass, and particularly preferably 60-90% by mass, out of 100% by mass of all polymeric compounds contained in the composition for photochromic layers. If the content is above the lower limit of the above range, the fading rate is easily increased; if the content is below the upper limit of the above range, the weather resistance is easily improved. It should be noted that in this disclosure and specification, a component that simultaneously conforms to components A and C, or simultaneously conforms to components A and D, is considered component A. One way to include component A is as the component that constitutes the largest proportion among the multiple polymeric compounds contained in the composition.

[0226] As one embodiment of the composition for the aforementioned photochromic layer, it may contain only one component A; in another embodiment, it may contain two or more components A. When two or more components A are contained, the content of component A is the total content of the two or more components. This also applies to the content of other components.

[0227] The content of component B is not particularly limited, but is preferably 1 to 30% by mass, more preferably 5 to 27% by mass, and particularly preferably 10 to 25% by mass, out of 100% by mass of all polymeric compounds contained in the composition for photochromic layers. If the content is above the lower limit of the above range, the weather resistance is easily improved; if the content is below the upper limit of the above range, the fading rate is easily improved.

[0228] As one embodiment of the composition for the aforementioned photochromic layer, it may contain only one component B; in another embodiment, it may contain two or more components B. When two or more components B are contained, the content of component B is the total content of the two or more components.

[0229] There is no particular limitation on the content of component C mentioned above, but it is preferably 1 to 30% by mass of 100% by mass of all polymeric compounds contained in the composition for photochromic layers, and more preferably 3 to 27% by mass. If the content is above the lower limit of the above range, the color concentration tends to be higher, and if the content is below the upper limit of the above range, the fading rate tends to be higher.

[0230] As one embodiment of the composition for the aforementioned photochromic layer, it may contain only one component C; in another embodiment, it may contain two or more components C. When two or more components C are contained, the content of component C is the total content of the two or more components.

[0231] There is no particular limitation on the content of component D, but it is preferably 1 to 30% by mass, more preferably 5 to 27% by mass, out of 100% by mass of all polymeric compounds contained in the composition for photochromic layers. If the content is above the lower limit of the above range, the color rendering concentration of the photochromic layer is easily increased; if the content is below the upper limit of the above range, the photochromic compound is easily soluble in the composition for photochromic layers.

[0232] As one embodiment of the composition for the aforementioned photochromic layer, it may contain only one component D; in another embodiment, it may contain two or more components D. When two or more components D are contained, the content of component D is the total content of the two or more components.

[0233] The above-described photochromic layer composition may or may not contain other (meth)acrylates besides components A to D, depending on need. When the above composition contains other (meth)acrylates besides components A to D, there is no particular limitation on the content of these other (meth)acrylates. From the viewpoint of fading speed, it is preferable that 10.0% by mass or less, more preferably 5.0% by mass or less, of all 100% by mass of (meth)acrylates contained in the above-described photochromic layer composition.

[0234] The above-mentioned photochromic layer composition may or may not contain polymeric compounds other than (meth)acrylates, depending on the need.

[0235] -Photochromic compounds-

[0236] As one way to use the above-mentioned photochromic layer composition, a photochromic compound may be included in addition to the above-mentioned polymeric compound.

[0237] There are no particular limitations on the aforementioned photochromic compounds; for example, well-known compounds that exhibit photochromic properties under ultraviolet light can be used.

[0238] As specific examples of the aforementioned photochromic compounds, there are no particular limitations; for example, compounds selected from azobenzenes, spiropyrans, and spiropyrans can be cited. Compounds with known skeletons exhibiting photochromic properties, such as azines, naphthopyrans, indo-naphthopyrans, phenanthrenepyrans, hexallyl diimidazoles, donor-acceptor Steinhaus adducts (DASAs), salicylanilines, dihydropyrene compounds, anthracene dimers, fulgimides, diarylethylene compounds, phenoxynaphthoquinones, and stilbenes; fulgimide compounds; spiro compounds. Azide compounds; chromene compounds; indene-fused naphthopyran compounds; at least one compound selected from the general formula A, general formula B, and general formula C described in WO2022 / 138966. These compounds may be used individually or in combination.

[0239] There is no particular limitation on the content of the aforementioned photochromic compound, but it is preferably about 0.1 to 15% by mass in 100% by mass of the composition for photochromic layer.

[0240] -Other ingredients-

[0241] In addition to two or more (meth)acrylates and a photochromic compound, the above-mentioned photochromic layer composition may contain one or more additives that are commonly found in polymerizable compositions, in any amount as needed. There are no particular limitations on the additives that may be included in the above-mentioned photochromic layer composition; examples include polymerization initiators used to initiate polymerization reactions.

[0242] There are no particular limitations on the polymerization initiators mentioned above; examples include photoradical polymerization initiators and thermal polymerization initiators. One or more of these can be used. From the viewpoint of enabling the polymerization reaction to proceed in a short time, photoradical polymerization initiators are preferred.

[0243] There are no particular limitations on photoradical polymerization initiators; examples include: benzoin ketals such as 2,2-dimethoxy-1,2-diphenylethane-1-one; α-hydroxy ketones such as 1-hydroxycyclohexylphenyl ketone, 2-hydroxy-2-methyl-1-phenylpropane-1-one, and 1-[4-(2-hydroxyethoxy)phenyl]-2-hydroxy-2-methyl-1-propane-1-one; and 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butane-1-one and 1,2-methyl-1-[4-(methylthio)phenyl]-2-morpholinophenyl. α-amino ketones such as linopropane-1-one; oxime esters such as 1-[(4-phenylthio)phenyl]-1,2-octanedione-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-trimethylbenzoyl diphenylphosphine oxide; phosphine oxides such as 2-(o-chlorophenyl)-4,5-diphenylimidazolium dimer, 2-(o-chlorophenyl)-4,5-di(methoxyphenyl)imidazolium dimer, and 2-(o-fluorophenyl)-4... 2,4,5-triarylimidazolium dimers, such as 5-diphenylimidazolium dimer, 2-(o-methoxyphenyl)-4,5-diphenylimidazolium dimer, and 2-(p-methoxyphenyl)-4,5-diphenylimidazolium dimer; benzophenone compounds, such as N,N'-tetramethyl-4,4'-diaminobenzophenone, N,N'-tetraethyl-4,4'-diaminobenzophenone, and 4-methoxy-4'-dimethylaminobenzophenone; 2-ethylanthraquinone, phenanthraquinone, 2-tert-butylanthraquinone, octamethylanthraquinone, 1,2-benzoanthraquinone, and 2, Quinone compounds such as 3-benzanthraquinone, 2-phenylanthraquinone, 2,3-diphenylanthraquinone, 1-chloroanthraquinone, 2-methylanthraquinone, 1,4-naphthoquinone, 9,10-phenanthroquinone, 2-methyl-1,4-naphthoquinone, and 2,3-dimethylanthraquinone; 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'-acridylheptane); N-phenylglycine; and coumarin. These can be used alone or in combination. Among these, α-hydroxyketone and phosphine oxide are preferred from the viewpoints of curability, transparency, and heat resistance.

[0244] It should be noted that in 2,4,5-triarylimidazolium dimers, the compounds can be symmetrical compounds with identical substituents at the two triarylimidazolium sites, or they can be asymmetrical compounds with different substituents. Furthermore, thioxanthone compounds can be combined with tertiary amines, similar to the combination of diethylthioxanthone and dimethylaminobenzoic acid.

[0245] There is no particular limitation on the content of the polymerization initiator, but it is preferably about 0.1 to 5.0% by mass in 100% by mass of the composition for photochromic layer.

[0246] The above-mentioned photochromic layer composition may be further supplemented with surfactants, antioxidants, free radical scavengers, light stabilizers, ultraviolet absorbers, anti-coloring agents, antistatic agents, fluorescent dyes, dyes, pigments, fragrances, plasticizers, silane coupling agents, and other commonly known additives in any amount as needed. These additives may be used alone or in combination with two or more.

[0247] The above-described photochromic layer composition can be prepared by mixing the various components described above simultaneously or in any order.

[0248] (protective layer)

[0249] The protective layer will now be explained in more detail.

[0250] In this disclosure and specification, a protective layer refers to a layer formed by curing a polymeric composition (hereinafter sometimes simply referred to as a "composition for protective layer") to form a protective layer.

[0251] The location of the aforementioned protective layer is not particularly limited, but from the viewpoint of protecting the photochromic layer, it is preferably located on the photochromic layer. Furthermore, from the above viewpoint, it is preferable that the protective layer has high hardness.

[0252] There are no particular limitations on the aforementioned protective layer, but excellent solvent resistance is preferred. In the manufacturing process of optical articles, after the protective layer is formed, it is usually wiped with a solvent to clean the surface of the formed protective layer. This is because if the protective layer is damaged during the wiping process, it will cause blurring and optical defects in the plastic lens.

[0253] 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 it is above the lower limit of the above range, the durability of the plastic lens becomes good, and if it is below the upper limit of the above range, it is easy to maintain the transmittance (transparency) of the cured coating layer.

[0254] As one example of the composition for the protective layer described above, a polymeric composition comprising one or more (meth)acrylates, and comprising at least 70.0% by mass of an alicyclic difunctional (meth)acrylate in 100% by mass of all (meth)acrylates.

[0255] It should be noted that there are no particular limitations on the components contained in the composition used as a protective layer. However, from the viewpoint of the hardness and solvent resistance of the protective layer, it is preferable to include alicyclic difunctional (meth)acrylates.

[0256] As the alicyclic difunctional (meth)acrylate contained in the above-mentioned protective layer composition, the alicyclic difunctional (meth)acrylate can be referred to as an example of the above-mentioned polymeric composition for forming photochromic layer.

[0257] Regarding the content of the aforementioned alicyclic difunctional (meth)acrylate, there is no particular limitation within 100% by mass of all (meth)acrylates. However, from the viewpoint of obtaining higher hardness and better solvent resistance in the protective layer, it is preferably 70.0% by mass or more, more preferably 75.0% by mass or more, further preferably 85.0% by mass or more, and particularly preferably 95.0% by mass or more. As one way to determine the content of the aforementioned alicyclic difunctional (meth)acrylate, the total amount of (meth)acrylate can be any amount of alicyclic difunctional (meth)acrylate.

[0258] As one embodiment of the composition for the aforementioned protective layer, the (meth)acrylate may contain one or more other (meth)acrylates besides alicyclic difunctional (meth)acrylates. In another embodiment, the (meth)acrylate may contain only alicyclic difunctional (meth)acrylates. In the former case, there are no particular limitations on the other (meth)acrylates contained together with the alicyclic difunctional (meth)acrylate; one or more various (meth)acrylates may be used. Specific examples of other (meth)acrylates are not particularly limited; for example, monofunctional, difunctional, trifunctional, tetrafunctional, and pentafunctional (meth)acrylates may be cited, and they may be acyclic or cyclic. As for (meth)acrylates containing a cyclic structure, they may have an alicyclic structure as a cyclic structure, or they may have other cyclic structures as a cyclic structure. Regarding the alicyclic structure, refer to the above description related to alicyclic difunctional (meth)acrylates.

[0259] There are no particular limitations on the content of the other (meth)acrylates mentioned above. From the viewpoint of obtaining high hardness and excellent solvent resistance in the protective layer of this disclosure, it is preferred to be 0 to 30.0% by mass of all (meth)acrylates in 100% by mass, more preferably 1.0 to 25.0% by mass, and particularly preferably 5.0 to 20.0% by mass.

[0260] The above-described protective layer composition contains at least one (meth)acrylate as a polymerizable compound. In one embodiment, it may contain more than one polymerizable compound other than (meth)acrylate; in another embodiment, it may contain only (meth)acrylate as a polymerizable compound. There are no particular limitations regarding the other polymerizable compounds; more than one known polymerizable compound may be used.

[0261] There is no particular limitation on the content of the aforementioned (meth)acrylate. From the viewpoint of durability, it is preferable to have 80.0% or more, more preferably 90.0% or more, and particularly preferably 100% by mass of all polymeric compounds in the protective layer composition out of 100% by mass.

[0262] In one embodiment, the content of the aforementioned (meth)acrylate (or the total amount thereof in the case of containing two or more (meth)acrylates) in the protective layer composition 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, in 100% by mass of the composition.

[0263] The above-mentioned protective layer composition may or may not contain a solvent. When a solvent is included, any solvent may be used as long as it does not hinder the polymerization reaction of the polymerizable composition; there are no particular restrictions, and any solvent may be used in any amount.

[0264] The above-mentioned protective layer composition may further contain one or more additives in any amount as needed.

[0265] There are no particular limitations on the additives mentioned above; for example, various known additives can be used, such as polymerization initiators for initiating polymerization reactions and leveling agents for improving the coatability of the composition. They can be used alone or in combination.

[0266] There are no particular limitations on the polymerization initiators mentioned above; examples include photoradical polymerization initiators and thermal polymerization initiators. One or more of these can be used. From the viewpoint of enabling the polymerization reaction to proceed in a short time, a photoradical polymerization initiator is preferred. For specific examples of photoradical polymerization initiators, refer to the polymerization initiators that can be included in the polymerizable composition for forming the photochromic layer described above.

[0267] There is no particular limitation on the content of the above-mentioned polymerization initiator, but from the viewpoint of the formation efficiency of the protective layer, it is preferably 0.1 to 5.0% by mass in 100% by mass of the composition for the protective layer.

[0268] The composition for the above-mentioned protective layer may further include an ultraviolet absorber as needed.

[0269] There are no particular limitations on the ultraviolet absorbers mentioned above. Examples include: 2,4-bis(2,4-dimethylphenyl)-6-(2-hydroxy-4-n-octyloxyphenyl)triazine, 2,4,6-tris(2-hydroxy-4-hexyloxy-3-methylphenyl)triazine, 2-[2-hydroxy-4-(2-ethylhexyloxy)phenyl]-4,6-biphenyltriazine, and 2-[[2-hydroxy-4-[1-(2-ethylhexyloxycarbonyl)ethoxy]phenyl]]-4,6-diphenyltriazine, etc.; 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, etc. They can be used alone or in combination.

[0270] By including the aforementioned ultraviolet absorber in the composition for the protective layer, the weather resistance of the protective layer can be improved.

[0271] When the above-mentioned protective layer composition contains an ultraviolet absorber, the content of the ultraviolet absorber is not particularly limited. From the viewpoint of optical properties such as transparency, it is preferably 0.1 to 1.0% by mass in 100% by mass of the protective layer composition.

[0272] The above-described protective layer composition can be prepared by mixing the various components described above simultaneously or in any order.

[0273] One aspect of the disclosed plastic lens can have a layer structure of "photochromic layer / protective layer". Regarding the layer structure, the " / " indicates whether it is a form where the layers are directly connected without any other layers in between, or a form where one or more other layers are in between. Furthermore, in one aspect, the optical article can have a layer structure of "photochromic layer / protective layer / other cured coating layer". There are no particular limitations on the other cured coating layer; for example, a cured layer commonly referred to as a hard coating layer can be used. One or more of these can be used. By providing a hard coating layer in addition to the protective layer, the durability of the optical article can be further improved. Additionally, in one aspect, providing a hard coating layer can also improve the impact resistance of the optical article. In one aspect, the other cured coating layer can be directly connected to the protective layer without any other layers in between.

[0274] The thickness of the other cured coating layers described above is not particularly limited, but from the viewpoint of optical properties such as refractive index, it is preferably 1 to 10 μm, more preferably 1 to 8 μm, and particularly preferably 1 to 5 μm. In one embodiment, the other cured coating layers described above may be thinner than the protective layer described above.

[0275] There are no particular limitations on other curing coatings mentioned above; for example, silicone-based curing layers are also possible. Generally, silicone-based curing layers have excellent impact resistance and are therefore preferred. Furthermore, as an alternative to further providing an anti-reflective layer, silicone-based curing layers are generally preferred due to their excellent adhesion to the anti-reflective layer.

[0276] The aforementioned organosilicon-based curing layer refers to a curing layer formed by curing a polymeric composition containing organosilicon compounds.

[0277] There are no particular limitations on organosilicon compounds. Examples include: organosilicon compounds that can be polymerized to form silanol groups; organopolysiloxanes having reactive groups such as halogen atoms and amino groups that undergo condensation reactions with silanol groups; and silane coupling agents having polymerizable groups such as vinyl, allyl, (meth)acryloyl, and (meth)acryloyloxy groups, and hydrolyzable groups such as alkoxy groups. They can be used individually or in combination.

[0278] For purposes such as adjusting the refractive index, particles of inorganic substances such as silicon oxide and titanium oxide may be further included in the polymerizable composition containing organosilicon compounds, as needed. Details regarding the polymerizable composition containing organosilicon compounds can be obtained using known techniques related to organosilicon-based cured layers that function as hard coatings. Depending on the types of components contained in the composition, the polymerizable composition containing organosilicon compounds can be cured by a polymerization reaction through light irradiation and / or heat treatment.

[0279] When the aforementioned other cured coating layers are provided on the protective layer, there are no particular limitations. From the viewpoint of preventing foreign matter from getting trapped between the protective layer and the other cured coating layers, it is preferable to wipe the surface of the protective layer with a solvent. However, if the protective layer has poor solvent resistance, it may be damaged by solvent wiping (e.g., surface roughness may occur), which can cause blurring and optical defects in plastic lenses containing the protective layer. In contrast, the protective layer formed from the aforementioned protective layer composition exhibits excellent solvent resistance, and therefore is considered suitable for providing the aforementioned other cured coating layers on the protective layer.

[0280] As for the solvent-based wiping treatment, there are no particular limitations, and it can be carried out by known methods, such as wiping the surface of the protective layer with a cloth soaked in solvent. There are no particular limitations on the solvents mentioned above; for example, ketone solvents such as acetone, and alcohol solvents such as ethanol and isopropanol can be used. One or more of them can be used. In one embodiment, the protective layer preferably has high resistance to ketone solvents commonly used as wiping solvents in the manufacture of optical articles.

[0281] (Other functional layers)

[0282] In addition to the base layer, photochromic layer and protective layer mentioned above, the above-mentioned coating and curing layer may include other functional layers as needed, or may not include them.

[0283] There are no particular limitations on other functional layers mentioned above. Examples include anti-reflective layers, water-repellent or hydrophilic anti-fouling layers, and anti-fog layers. One or more of these can be used.

[0284] [Glasses]

[0285] One aspect of this disclosure relates to eyeglasses comprising the aforementioned plastic lens. Details regarding the plastic lens of the eyeglasses are as described above. By equipping the eyeglasses with the aforementioned plastic lens, for example outdoors, the photochromic compound contained in the photochromic layer changes color upon exposure to sunlight, thereby providing an anti-glare effect similar to sunglasses. Upon returning indoors, the photochromic compound fades, thereby restoring transmittance.

[0286] There are no particular restrictions on the components such as the frames of the aforementioned eyeglasses, and known technologies can be applied.

[0287] [Manufacturing method of plastic lenses]

[0288] One aspect of this disclosure relates to a method for manufacturing the aforementioned plastic lens, the method comprising: a base coating forming step of forming a base coating on one side surface of a lens substrate; a photochromic layer forming step of coating a polymeric composition for forming a photochromic layer onto the surface of the base coating, curing the polymeric composition for forming a photochromic layer by light irradiation to form a photochromic layer; and a protective layer forming step of forming a protective layer on the surface of the photochromic layer, and, if necessary, may further include other steps.

[0289] <Undercoat Formation Process>

[0290] The following is a more detailed explanation of the base coat formation process.

[0291] By applying the primer coating composition to one side surface of a lens substrate and then curing the applied primer coating composition, the aforementioned primer coating can be formed on one side surface of the lens substrate.

[0292] There are no particular limitations on the coating method described above; any known coating method can be used, such as spin coating or dip coating. One or more of these methods can be used. From the viewpoint of coating uniformity, spin coating is preferred.

[0293] There are no particular limitations on the curing treatments described above; examples include light irradiation and heat treatment. One or more of these can be used. Of these, light irradiation is preferred from the viewpoint of allowing the curing reaction to occur in a short time. The curing conditions can be determined based on the types of components contained in the primer composition and the composition of the primer composition.

[0294] After curing, annealing (heat treatment) can be performed as needed. There are no particular restrictions on the conditions for annealing, but it is preferred to carry out it in a heat treatment furnace with an atmosphere temperature of about 90~130°C.

[0295] <Photochromic layer formation process>

[0296] The following is a more detailed explanation of the photochromic layer formation process.

[0297] The photochromic layer can be formed on the surface of the base layer by applying the photochromic layer composition to the surface of the base layer and then curing the applied photochromic layer composition.

[0298] There are no particular limitations on the coating method described above; any known coating method can be used, such as spin coating or dip coating. One or more of these methods can be used. From the viewpoint of coating uniformity, spin coating is preferred.

[0299] There are no particular limitations on the curing treatments described above; examples include light irradiation and heat treatment. One or more of these can be used. Of these, light irradiation is preferred from the viewpoint of allowing the curing reaction to occur in a short time.

[0300] The intensity of the aforementioned light irradiation only needs to be 150~350mW / cm². 2 There are no particular limitations, but from the viewpoint of suppressing thermal deformation of plastic lenses and the curing reaction of the composition for photochromic layers, a strength of 160~340 mW / cm is preferred. 2 More preferably, it is 190~310mW / cm 2The optimal value is 220~280mW / cm². 2 .

[0301] The irradiation time for the above-mentioned light irradiation can be 1 to 90 seconds, and there is no particular limitation. From the viewpoint of suppressing the thermal deformation of plastic lenses and the curing reaction of the composition for photochromic layer, it is preferred to be 5 to 80 seconds, more preferably 10 to 60 seconds, and particularly preferably 15 to 40 seconds.

[0302] The exposure level for the aforementioned light irradiation should be between 0.15 and 31.5 J / cm². 2 There are no particular limitations, but from the viewpoints of suppressing thermal deformation of plastic lenses and the curing reaction of the photochromic layer composition, a concentration of 0.8 to 27.2 J / cm is preferred. 2 More preferably, it is 1.9~18.6 J / cm. 2 The preferred concentration is 3.3~11.2 J / cm³. 2 .

[0303] After curing, annealing (heat treatment) can be performed as needed. There are no particular restrictions on the conditions for annealing, but it is preferred to carry out it in a heat treatment furnace with an atmosphere temperature of about 90~130°C.

[0304] <Protective Layer Formation Process>

[0305] The protective layer formation process will be explained in more detail below.

[0306] By applying the protective layer composition to the surface of the photochromic layer and then curing the applied protective layer composition, the aforementioned protective layer can be formed on the surface of the photochromic layer. Furthermore, from the viewpoint of improving the adhesion between the photochromic layer and the protective layer, an undercoat layer or similar material can be further formed between the photochromic layer and the protective layer, if necessary.

[0307] There are no particular limitations on the coating method described above; any known coating method can be used, such as spin coating or dip coating. One or more of these methods can be used. From the viewpoint of coating uniformity, spin coating is preferred.

[0308] There are no particular limitations on the curing treatments described above; examples include light irradiation and heat treatment. One or more of these can be used. Of these, light irradiation is preferred from the viewpoint of allowing the curing reaction to occur in a short time. The curing conditions can be determined based on the types of components contained in the protective layer composition and the composition of the protective layer composition.

[0309] After curing, annealing (heat treatment) can be performed as needed. There are no particular restrictions on the conditions for annealing, but it is preferred to carry out it in a heat treatment furnace with an atmosphere temperature of about 90~130°C.

[0310] Example

[0311] The present disclosure will be further illustrated below through embodiments. However, the present disclosure is not limited to the implementation methods shown in the embodiments.

[0312] [Preparation of polymeric compositions for photochromic layer formation]

[0313] As shown below, photochromic layer compositions 1 to 3, which are polymeric compositions for forming photochromic layers, were manufactured.

[0314] (Composition 1 for photochromic layer)

[0315] In a plastic container, polyethylene glycol dimethacrylate (in formula (2) above, n=14, R=ethylene, R...) is placed... 1 and R 2 A mixture of 90 parts by mass of methyl (726) and 10 parts by mass of tricyclodecanediethanol dimethacrylate (332) was obtained to produce a mixture of polymerizable compounds.

[0316] A photochromic compound (an indene-fused naphthopyran compound represented by the structural formula (6) described in U.S. Patent 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(3-(5-tert-butyl-4-hydroxym-tolyl)propionate bis(oxyethylene) ester), 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) were mixed in a rotation-revolutionary stirring degassing device, and the mixture was stirred thoroughly. Degassing was then performed using a rotation-revolutionary stirring degassing device. Thus, composition 1 for a photochromic layer was obtained. Regarding the content of various components, in 100% by mass composition 1 for photochromic layer, the mixture of the above-mentioned polymerizable compounds is 90.0% by mass, the photochromic compound is 5.7% by mass, the photoradical polymerization initiator is 0.7% by mass, the antioxidant is 2.7% by mass, and the light stabilizer is 0.9% by mass.

[0317] [Chemical Formula 6]

[0318] Indene-fused naphthopyran compounds

[0319] ···(6)

[0320] (Composition 2 for photochromic layer)

[0321] Except for the compounds used in the preparation of the mixture of polymeric compounds in the photochromic layer composition 2 (see below), the photochromic layer composition 2 was obtained by the same manufacturing method as "photochromic layer composition 1". Regarding the content of various components, in 100% by mass of the photochromic layer composition 2, the mixture of the aforementioned polymeric compounds is 94.9% by mass, the photochromic compound is 3.0% by mass, the photoradical polymerization initiator is 0.3% by mass, the antioxidant is 0.9% by mass, and the light stabilizer is 0.9% by mass.

[0322] It should be noted that the mixture of polymeric compounds in the photochromic layer composition 2 is obtained by mixing 65 parts by mass of trimethylolpropane polyoxyethylene ether trimethacrylate (molecular weight 1264), 5 parts by mass of methyl 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 poly[(3-methacryloyloxypropyl)silsesquioxane] derivative (the compound represented by the structural formula of formula (7) below) in a plastic container.

[0323] [Chemical Formula 7]

[0324] Poly[(3-methacryloyloxypropyl)silsesquioxane] derivatives

[0325] ···(7)

[0326] (Composition 3 for photochromic layers)

[0327] In a plastic container, 20 parts by weight of trimethylolpropane trimethacrylate (molecular weight 338), 35 parts by weight of 2,2-bis(4-methacryloyloxypolyethoxyphenyl)propane (molecular weight 541), 10 parts by weight of polyester oligomer hexaacrylate (manufactured by Daicel Co., Ltd., EBECRYL1830, molecular weight 1500), 10 parts by weight of polyethylene glycol diacrylate (average molecular weight 532), and 10 parts by weight of glycidyl methacrylate (molecular weight 142) were mixed to obtain a mixture of polymerizable compounds.

[0328] To 100 parts by mass of the resulting polymerizable compound mixture, 3 parts by mass of a photochromic compound (the chromene compound (A) represented by the structural formula of formula (8) below), 0.6 parts by mass of a photoradical polymerization initiator (Ciba Specialty Chemicals, CGI-1870), 5 parts by mass of an antioxidant (Ciba Specialty Chemicals, Irgacure 245), and 5 parts by mass of a light stabilizer (a mixture of bis(1,2,2,6,6-pentamethyl-4-piperidinyl) sebacate and methyl(1,2,2,6,6-pentamethyl-4-piperidinyl) sebacate) were added. After thorough mixing, 6 parts by mass of γ-methacryloyloxypropyltrimethoxysilane (KBM503 manufactured by Shin-Etsu Chemical Co., Ltd.) were added dropwise while stirring. Then, the mixture was degassed for 2 minutes using a rotation-revolution degassing device, and 40 parts by mass of polyethylene glycol diacrylate (average molecular weight 708) were added. Thus, composition 3 for photochromic layer was obtained.

[0329] [Chemical Formula 8]

[0330] Chondrone compound (A)

[0331] ···(8)

[0332] [Preparation of polymeric compositions for base coating formation]

[0333] In a plastic container, a hydroxyl-containing difunctional acrylate (10 parts by mass), a polyisocyanate (manufactured by Tosoh Corporation, CORONATE 2715) (40 parts by mass), and 2-phenoxyethyl acrylate (viscosity: 13 cP) (50 parts by mass) having the structure represented by (1) below are mixed. To the resulting mixture, a photoradical polymerization initiator (bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, manufactured by IGM Resin BV, Omnirad 819) is added in an amount of 0.02 parts by mass relative to 100 parts by mass of the total mixture, and the mixture is stirred thoroughly. Then, degassing is performed using a rotation-revolution stirring and degassing device. Thus, composition 1 for a primer coating is obtained.

[0334] [Chemical Formula 9]

[0335] ···(1)

[0336] [Preparation of polymeric compositions for forming protective layers]

[0337] In a plastic container, 99.0 parts by weight of tricyclodecanediethanol diacrylate (alicyclic difunctional (meth)acrylate) and 1.0 part by weight of photoradical polymerization initiator (bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, manufactured by IGM Resin B.V., Omnirad 819) were mixed and thoroughly stirred. Then, degassing was performed using a rotation-revolutionary stirring and degassing device. Thus, composition 1 for the protective layer was obtained.

[0338] It should be noted that in the above-mentioned protective layer composition 1, the (meth)acrylate is only an alicyclic difunctional (meth)acrylate. Therefore, the content of the alicyclic difunctional (meth)acrylate is 100% by mass of all (meth)acrylates.

[0339] [Manufacturing of Plastic Lenses]

[0340] (Example 1)

[0341] The lens substrate (manufactured by HOYA Co., Ltd., HILUX1.67, with a thickness of 1.0 mm in the center and 9.1 mm in the periphery) was immersed in a 10% sodium hydroxide aqueous solution (at a temperature of 60°C) for 5 minutes, then rinsed with pure water and dried.

[0342] Then, in an environment with a temperature of 25°C and a relative humidity of 50%, the primer coating composition 1 was applied to the convex surface (object side surface) of the lens substrate by spin coating. The primer coating composition 1 applied to the lens substrate was then subjected to light irradiation in a nitrogen atmosphere (oxygen concentration below 500 ppm by volume) (light wavelength: 405 nm, light intensity: 250 mW / cm²). 2 Light exposure time: 5 seconds; Light exposure dose: 1.25 J / cm² 2 The composition is cured to form a base coating. The thickness of the formed base coating is 10 μm.

[0343] The photochromic layer composition 1 was applied to the aforementioned base layer by spin coating. Spin coating was performed according to the method described in Japanese Patent Application Publication No. 2005-218994. Then, the photochromic layer composition 1 coated on the base layer was subjected to light irradiation (wavelength: 405 nm, intensity: 250 mW / cm²) in a nitrogen atmosphere (oxygen concentration ≤ 500 ppm). 2 Light exposure time: 25 seconds; Light exposure dose: 6.25 J / cm³ 2 The composition is cured to form a photochromic layer. The thickness of the formed photochromic layer is 40 μm.

[0344] Composition 1 for applying a protective layer was coated onto the aforementioned photochromic layer using a spin coating method, thus forming a coating layer. The surface of the coating layer was then irradiated with light (wavelength: 405 nm, intensity: 250 mW / cm²) in a nitrogen atmosphere (oxygen concentration below 500 ppm by volume). 2 Light exposure time: 15 seconds; Light exposure dose: 3.75 J / cm³ 2 The coating layer is cured to form a protective layer. The thickness of the protective layer is 38 μm.

[0345] After the above three layers are formed, the heat treatment device (manufactured by ESPEC Corporation, PH series) is used to perform heat treatment at an atmosphere temperature of 90°C for 2 hours to enhance the adhesion of each cured coating layer.

[0346] The thickness of the cured coating layer is obtained by subtracting the thickness of the center portion of the lens substrate before the cured coating layer is formed from the thickness of the center portion of the lens substrate after the cured coating layer is formed. It should be noted that the thickness of the lens substrate before and after the cured coating layer is measured using a high-performance ABS digital indicator (Mitutoyo Corporation, ID-FNX series) connected to terminals on the convex and concave surfaces of the center portion of the lens substrate.

[0347] The above-mentioned "light intensity" was measured using a light meter (USHIO Corporation, UIT-250) at a lens stage 300mm away from the center of the light source to the light-receiving part (center wavelength 365mm).

[0348] The aforementioned "exposure to light irradiation" is the cumulative value of irradiation time measured using a light meter (USHIO Corporation, UIT-250), at a lens stage 300mm away from the center of the light source (center wavelength 365mm). The light intensity (mW / cm²) is the value of the irradiation time. 2 () × irradiation time (seconds)).

[0349] Thus, the plastic lens of Example 1 was obtained.

[0350] (Example 2)

[0351] In Example 1, photochromic layer composition 2 was used instead of photochromic layer composition 1, the thickness of the photochromic layer was set to 25 μm, and the thickness of the protective layer was set to 15 μm. Otherwise, the plastic lens of Example 2 was obtained by the same method as in Example 1.

[0352] (Comparative Example 1)

[0353] In Example 2, light was applied (wavelength: 405 nm, intensity: 250 mW / cm²). 2 Light exposure time: 25 seconds; Light exposure dose: 6.25 J / cm³ 2 Replace with light irradiation (wavelength: 405nm, intensity: 250mW / cm²). 2 Light exposure time: 40 seconds; Light exposure dose: 10.0 J / cm³ 2 In addition, the plastic lens of Comparative Example 1 was obtained by the same method as in Example 2.

[0354] (Comparative Example 2)

[0355] In Example 1, photochromic layer composition 3 was used instead of photochromic layer composition 1. The thickness of the base layer was set to 6 μm, the thickness of the photochromic layer was set to 40 μm, and no protective layer was provided. Otherwise, the plastic lens of Comparative Example 2 was obtained by the same method as in Example 1.

[0356] (Comparative Example 3)

[0357] In Comparative Example 2, light was applied (wavelength: 405 nm, intensity: 250 mW / cm²). 2 Light exposure time: 25 seconds; Light exposure dose: 6.25 J / cm³ 2 Replace with light irradiation (wavelength: 405nm, intensity: 250mW / cm²). 2 Light exposure time: 60 seconds; Light exposure dose: 15.0 J / cm³ 2 In addition, the plastic lens of Comparative Example 3 was obtained by the same method as Comparative Example 2.

[0358] [Review of Plastic Lenses]

[0359] The obtained plastic lenses were evaluated as follows. The evaluation results are shown in Table 2.

[0360] <Surface hardness of photochromic layer>

[0361] Using an ultra-micro indentation hardness tester (Elionix Co., Ltd., ENT-2100), the indentation depth h (nm) corresponding to the indentation load P (kgf) was continuously measured throughout the entire process from the start of loading to the unloading of the load at the test site, and a Ph curve was generated. The indentation hardness H was calculated from the generated Ph curve using the following formula.

[0362] H(kgf / mm 2 )=Pmax / A

[0363] (Pmax is the maximum load (kgf), and A is the projected area of ​​the pressure head (mm²) 2 ). )

[0364] The indentation hardness referred to herein is the value obtained from the displacement-load curve from the load on the measuring indenter to the unload, as specified in ISO 14577:2015.

[0365] <Surface scratch resistance>

[0366] Using steel wool (specification #0000, manufactured by Japan Steel Wool Co., Ltd.) at 1 kgf / cm² on one side. 2 The difficulty of judging the damage by pressing and rubbing the surface of the dimming lens with the naked eye.

[0367] The measured surface scratches were evaluated according to the following evaluation criteria.

[0368] [Evaluation Criteria]

[0369] UA: Almost no scars.

[0370] A: There are a few shallow scars, or about two deep but thin scars.

[0371] B: There are about 20 shallow scars, or about 10 fine but deep scars.

[0372] C: Multiple deep scratches (regardless of thickness) are produced, resulting in a near-blurred state; or the scratches are shallow but there is no coating (film difference).

[0373] In evaluations of UA and A, the photochromic layer is not easily damaged and can suppress the degradation of the photochromic properties of the plastic lens; therefore, the scratch resistance of the outermost surface is considered sufficiently excellent. On the other hand, in evaluations of B and C, the scratch resistance of the outermost surface cannot be considered excellent.

[0374] <Difference from design degree>

[0375] Using a power meter (TOPCON CL-300, manufactured by TOPCON Co., Ltd.), the spherical refractive index S and additional power C of the center portion (within 5 mm radius) of the lens substrate, as well as the spherical refractive index S and additional power C of the center portion (within 5 mm radius) of the aforementioned manufactured plastic lens, were measured. Then, the absolute value of the difference between the total value of the spherical refractive index S and additional power C of the center portion of the lens substrate and the total value of the spherical refractive index S and additional power C of the center portion of the plastic lens was taken as the "difference from the design power" for each plastic lens.

[0376] The difference between the measured degree and the design degree was evaluated according to the following evaluation criteria.

[0377] [Evaluation Criteria]

[0378] A: Below 0.06

[0379] B: Above 0.06 and below 0.09

[0380] C: Greater than 0.09 and less than 0.12

[0381] D: 0.12 or higher

[0382] In evaluations A through C, the difference from the design power is sufficiently small, therefore the thermal deformation of the plastic lens can be considered sufficiently low. On the other hand, in evaluation D, the difference from the design power is not small, therefore the thermal deformation of the plastic lens cannot be considered sufficiently low.

[0383] <Fading speed (fading property)>

[0384] For the photochromic layers (cured layers formed by curing the above-described polymeric composition) of each spectacle lens in the examples and comparative examples, the surface of the photochromic layer was irradiated with a xenon lamp through an Aeromass filter for 15 minutes (900 seconds) to develop the color of the photochromic compound in the photochromic layer. The transmittance at color development (measurement wavelength: 550 nm) was measured using a spectrophotometer manufactured by Otsuka Electronics Co., Ltd. The irradiation was performed in accordance with JIS T 7333:2005, such that the irradiance and the permissible difference in irradiance were the values ​​shown in Table 2 below. The transmittance obtained by measuring in this manner is referred to as "transmittance at color development".

[0385]

[0386] Following the measurement of transmittance during color development, the transmittance was measured 60 seconds after the light irradiation ceased (hereinafter referred to as "60s fading transmittance"). The fading rate (unit: % / second) was calculated using the formula: fading rate = [(60s fading transmittance - transmittance during color development) / 60]. A higher fading rate value indicates a faster fading rate.

[0387] The measured fading rate values ​​were evaluated according to the following evaluation criteria.

[0388] [Evaluation Criteria]

[0389] A: Exceeding 0.60% / second

[0390] B: 0.40~0.60% / second

[0391] C: Less than 0.40% / second

[0392] When evaluating options A and B, the fading performance is considered sufficiently excellent. However, when evaluating option C, the fading performance cannot be considered excellent.

[0393]

[0394] Based on the results shown in Table 2, it can be confirmed that the plastic lenses of Examples 1 and 2 have excellent fading properties and less thermal deformation compared to the plastic lenses of Comparative Examples 1 to 3.

[0395] The inventors believe that setting the surface hardness of the photochromic layer to 2.0 kgf / mm is appropriate. 2 The following contributes to the excellent fading properties of the plastic lenses in Examples 1 and 2.

[0396] The inventors believe that setting the difference between the power of the lens substrate after the curing coating layer is formed and the designed power to be less than 0.12 means that the plastic lenses of Examples 1 and 2 have less thermal deformation.

[0397] Two or more of the various methods and forms described in this specification can be combined in any combination.

[0398] The embodiments disclosed herein should be considered exemplary in all respects and not limiting. The scope of this disclosure is defined by the claims rather than the foregoing description and is intended to include all modifications within the meaning and scope equivalent to the claims.

[0399] Industrial applicability

[0400] This disclosure is useful in the fields of eyeglasses, goggles, and other related technologies.

Claims

1. A plastic lens comprising: a lens substrate and a cured coating layer formed on one side surface of the lens substrate. The cured coating layer comprises a base layer, a photochromic layer, and a protective layer. The surface hardness of the photochromic layer is 2.0 kgf / mm. 2 the following, The difference between the power of a plastic lens with a cured coating layer formed on one side surface of the lens substrate and the designed power is less than 0.

12.

2. The plastic lens according to claim 1, wherein, The photochromic layer is a layer formed by curing a polymeric composition. The polymeric composition for forming the photochromic layer comprises: Two or more (meth)acrylates, and Photochromic compounds.

3. The plastic lens according to claim 2, wherein, The two or more (meth)acrylates mentioned above contain at least a polyfunctional (meth)acrylate with a molecular weight of 500 or more.

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

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

6. The plastic lens according to claim 1, wherein, The thickness of the central portion of the lens substrate is less than 2 mm, while the peripheral portion is thicker than the central portion.

7. A pair of eyeglasses comprising a plastic lens according to any one of claims 1 to 6.

8. A method for manufacturing a plastic lens according to any one of claims 1 to 6, the method comprising: The process of forming a base coating on one side surface of a lens substrate; A photochromic layer forming process is performed by coating a polymeric composition for forming a photochromic layer onto the surface of the base layer and curing the polymeric composition for forming a photochromic layer by irradiation with light. as well as The protective layer forming process for forming a protective layer on the surface of the photochromic layer. The intensity of the light irradiation is 150 mW / cm². 2 ~350mW / cm 2 , The duration of the light irradiation is from 1 second to 90 seconds. The light exposure was 0.15 J / cm². 2 ~31.5J / cm 2 .

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