Optical article and method for producing the same

Abstract

The present invention provides an optical article, which comprises, in order: a substrate, a primer layer formed by curing a polymerizable composition for primer layer formation, and a photochromic layer containing a photochromic compound, wherein the polymerizable composition for primer layer formation comprises: component A: polyisocyanate, component B: a hydroxyl-containing polymerizable compound, and component C: a polymerizable compound selected from (meth)acrylates and vinyl ethers, and the viscosity of the polymerizable composition is 100 cP or less.

Description

Technical Field

[0001] The present invention relates to optical articles. Background Art

[0002] A photochromic compound is a compound having photochromic properties, which is a property of developing color under irradiation with light in a wavelength region having photoresponsiveness and fading under no irradiation. Hereinafter, an article containing a photochromic compound is referred to as a photochromic article. For example, Patent Document 1 discloses an optical article in which a layer (photochromic layer) containing a photochromic compound is provided on a substrate.

[0003] Prior art literature

[0004] Patent Literature

[0005] Patent Document 1: WO2003 / 011967 Summary of the invention

[0006] Problems to be solved by the invention

[0007] The present inventors have repeatedly conducted studies to improve the performance of an optical article having a photochromic layer and to improve the optical uniformity thereof.

[0008] That is, an object of one embodiment of the present invention is to provide an optical article having a photochromic layer and excellent in optical uniformity.

[0009] Solutions to the problem

[0010] One embodiment of the present invention relates to an optical article, which comprises:

[0011] Base material,

[0012] A primer layer formed by curing a primer layer-forming polymerizable composition, and

[0013] a photochromic layer comprising a photochromic compound,

[0014] The above-mentioned polymerizable composition for forming a primer layer comprises:

[0015] Ingredient A: Polyisocyanate,

[0016] Component B: a hydroxyl-containing polymerizable compound, and

[0017] Component C: a polymerizable compound selected from (meth)acrylates and vinyl ethers, and having a viscosity of 100 cP or less.

[0018] In an optical article having a photochromic layer on a substrate, in order to improve the adhesion between the substrate and the photochromic layer, a primer layer is preferably provided between the substrate and the photochromic layer. Therefore, the present inventors have studied the primer layer provided between the substrate and the photochromic layer, and found that the reduction in optical uniformity caused by the primer layer may occur. In addition, the present inventors have further repeatedly conducted in-depth studies and have newly discovered that by making the above-mentioned primer-forming polymerizable composition contain component C in addition to component A and component B, the generation of optical defects caused by the primer layer can be suppressed, thereby providing an optical article with excellent optical uniformity.

[0019] Effects of the Invention

[0020] According to one embodiment of the present invention, an optical article having a photochromic layer and excellent optical uniformity can be provided. DETAILED DESCRIPTION

[0021] [Optical items]

[0022] Hereinafter, the optical article according to one embodiment of the present invention will be described in more detail.

[0023] The optical article comprises: a substrate, a primer layer, and a photochromic layer in sequence.

[0024] <Base material>

[0025] The above-mentioned optical article can have a photochromic layer through a primer layer on a substrate selected corresponding to the type of optical article. As an example of a substrate, a spectacle lens substrate can be a plastic lens substrate or a glass lens substrate. The glass lens substrate can be, for example, a lens substrate made of inorganic glass. As a lens substrate, from the viewpoint of being light, not easy to break and easy to handle, a plastic lens substrate is preferred. As a plastic lens substrate, styrene resins represented by (meth) acrylic resins, polycarbonate resins, allyl resins, allyl carbonate resins such as diethylene glycol bisallyl carbonate resin (CR-39), vinyl resins, polyester resins, polyether resins, carbamate resins obtained by reacting isocyanate compounds with hydroxyl compounds such as diethylene glycol, thiocarbamate resins obtained by reacting isocyanate compounds with polythiol compounds, and a cured product (generally referred to as a transparent resin) formed by curing a curable composition containing a (thio) epoxy compound having more than one disulfide bond in the molecule. As a lens substrate, an undyed substrate (colorless lens) can be used, and a dyed substrate (dyed lens) can also be used. The refractive index of the lens substrate can be, for example, about 1.60 to 1.75, but the refractive index of the lens substrate is not limited to the above range, and can be within the above range or deviate from the above range. In the present invention and this specification, the refractive index refers to the refractive index relative to light with a wavelength of 500nm. In addition, the lens substrate can be a lens with refractive power (so-called diopter lens) or a lens without refractive power (so-called non-diopter lens).

[0026] The spectacle lens may be a single-focus lens, a multi-focus lens, a progressive refractive lens, or other lenses. The type of lens is determined by the surface shapes of the two sides of the lens substrate. In addition, the surface of the lens substrate may be any of a convex surface, a concave surface, and a flat surface. For a common lens substrate and a spectacle lens, the object-side surface is a convex surface and the eyeball-side surface is a concave surface, but the present invention is not limited thereto. The photochromic layer may be generally disposed on the object-side surface of the lens substrate, or may be disposed on the eyeball-side surface.

[0027] <Base coating>

[0028] The primer layer is a cured layer formed by curing a primer layer-forming polymerizable composition comprising component A, component B, and component C. In the present invention and this specification, a polymerizable composition refers to a composition comprising a polymerizable compound, and a polymerizable compound refers to a compound having a polymerizable group.

[0029] (ingredient A)

[0030] Component A is a polyisocyanate. Polyisocyanate refers to a compound having two or more isocyanate groups in one molecule. The number of isocyanate groups contained in one molecule of the polyisocyanate is 2 or more, preferably 3 or more. In addition, the number of isocyanate groups contained in one molecule of the polyisocyanate may be, for example, 6 or less, 5 or less, or 4 or less. The molecular weight of the polyisocyanate may be, for example, in the range of 100 to 500, but is not limited to this range. Specific examples of polyisocyanates include aromatic diisocyanates such as xylene diisocyanate, phenylene diisocyanate, toluene diisocyanate, diphenylmethane diisocyanate, and naphthalene diisocyanate, hexamethylene diisocyanate, lysine diisocyanate, cyclohexane diisocyanate, isophorone diisocyanate, 4,4'-dicyclohexylmethane diisocyanate, 1,3-bis(isocyanatomethyl)cyclohexane, tetramethylxylene diisocyanate, and aliphatic or alicyclic diisocyanates. In addition, allophanate forms, adducts, biuret forms, isocyanurate forms, and the like of the polyisocyanates exemplified above may also be mentioned. Examples of commercially available polyisocyanates include Coronate HX, Coronate HXR, Coronate HXLV, Coronate HK, Coronate 2715, Coronate HL, Coronate L, Coronate 2037, HDI, TDI, and MDI (manufactured by Tosoh Corporation), Takenate 500, Takenate 600, Duranate 24A-100, TPA-100, TKA-100, P301-75E, and Takenate D-110N, D-120N, D-127N, D-140N, D-160N, D15N, D-170N, D-170HN, D-172N, D-177N, D-178N, and D-101E (manufactured by Mitsui Chemicals, Inc.).

[0031] (ingredient B)

[0032] Component B is a hydroxyl-containing polymerizable composition. The number of hydroxyl groups contained in one molecule of component B is 1 or more, preferably 2 or more. In addition, the number of hydroxyl groups contained in one molecule of component B is preferably 4 or less, more preferably 3 or less. By reacting the isocyanate group of component A with the hydroxyl group of component B, a urethane bond can be formed. The inventors speculate that the urethane bond helps the primer layer to function as a layer for improving adhesion.

[0033] Component B is a polymerizable compound and may have one or more polymerizable groups in one molecule, preferably two or more polymerizable groups. In one embodiment, component B may be a (meth)acrylate. In the present invention and this specification, "(meth)acrylate" is used to include acrylate and methacrylate. "Acrylate" refers to a compound having one or more acryloyl groups in one molecule. "Methacrylate" refers to a compound having one or more methacryloyl groups in one molecule. With respect to (meth)acrylate, the number of functional groups is the number of groups selected from acryloyl and methacryloyl contained in one molecule. In the present invention and this specification, "methacrylate" refers to a compound containing only methacryloyl as a (meth)acryloyl group, and a compound containing both acryloyl and methacryloyl as a (meth)acryloyl group is referred to as an acrylate. Acryloyl may be contained in the form of an acryloyloxy group, and methacryloyl may be contained in the form of a methacryloyloxy group. The "(meth)acryloyl" described below is used to include acryloyl and methacryloyl, and the "(meth)acryloyloxy" is used to include acryloyloxy and methacryloyloxy. In addition, unless otherwise specified, the group described may have a substituent or may be unsubstituted. In the case where a certain group has a substituent, the substituent may include an alkyl group (for example, an alkyl group having 1 to 6 carbon atoms), a hydroxyl group, an alkoxy group (for example, an alkoxy group having 1 to 6 carbon atoms), a halogen atom (for example, a fluorine atom, a chlorine atom, a bromine atom), a cyano group, an amino group, a nitro group, an acyl group, a carboxyl group, and the like. In addition, with respect to a group having a substituent, the "number of carbon atoms" refers to the number of carbon atoms of the portion not including the substituent.

[0034] When component B is a (meth)acrylate, the number of functional groups as the (meth)acrylate is 1 or more (i.e., monofunctional or more), preferably 2 or more. In addition, the number of functional groups is preferably 3 or less. Component B may contain only an acryloyl group as a (meth)acryloyl group, may contain only a methacryloyl group as a (meth)acryloyl group, or may contain an acryloyl group and a methacryloyl group. In one embodiment, it is preferred that component B contains only an acryloyl group as a (meth)acryloyl group. The molecular weight of component B may be, for example, in the range of 300 to 400, but is not limited to this range. As specific examples of component B, 2-hydroxyethyl (meth)acrylate, hydroxypropyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, 1,4-cyclohexanedimethanol 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-(acryloyloxy)ethyl 2-hydroxyethyl phthalate, etc. can be cited. In addition, in one embodiment, component B may have an amide group. As specific examples of component B having an amide group, for example, N-(2-hydroxyethyl)acrylamide, etc. can be cited. In addition, in one embodiment, component B may have an epoxy ester structure. The epoxy ester structure refers to a structure generated by the reaction of an epoxy group and a carboxyl group, and can be represented by "-CH(OH)-CH2-OC(=O)-". Examples of commercially available products of component B having an epoxy ester structure include Epoxy Ester 40EM (manufactured by Kyoeisha Chemical), Epoxy Ester 70PA (manufactured by Kyoeisha Chemical), Epoxy Ester 80MFA (manufactured by Kyoeisha Chemical), Epoxy Ester 200PA (manufactured by Kyoeisha Chemical), Epoxy Ester 3002M (N) (manufactured by Kyoeisha Chemical), Epoxy Ester 3002A (N) (manufactured by Kyoeisha Chemical), Epoxy Ester 3000MK (manufactured by Kyoeisha Chemical), and Epoxy Ester 3000A (manufactured by Kyoeisha Chemical).

[0035] (Ingredient C)

[0036] Component C is a polymerizable compound selected from (meth)acrylates and vinyl ethers, and its viscosity is 100 cP (centipoise) or less. The inventors speculate that the inclusion of such a low-viscosity polymerizable compound helps to suppress the generation of optical defects in the primer layer formed by the primer layer-forming polymerizable composition comprising components A and B. The "viscosity" in the present invention and this specification is a value measured by a vibration viscometer in an atmospheric atmosphere at a temperature of 25°C. The viscosity of component C is 100 cP or less, preferably 70 cP or less, and more preferably 50 cP or less. In addition, the viscosity of component C can be, for example, 5 cP or more or 10 cP or more. As one form of component C, the (meth)acrylate can be monofunctional to trifunctional, preferably monofunctional to difunctional. In addition, as one form of component C, the (meth)acrylate can contain aromatic groups (such as phenyl), amide groups, and the like. In the present invention and this specification, "vinyl ether" refers to a compound having one or more vinyl groups and one or more ether bonds in one molecule, preferably having two or more vinyl groups in one molecule, and more preferably having 2 to 4 vinyl groups. In addition, the number of ether bonds contained in the vinyl ether is preferably 2 to 4 in one molecule. The molecular weight of component C can be, for example, in the range of 150 to 250, but is not limited to this range.Specific examples of component C include 2-phenoxyethyl (meth)acrylate, acrylamide, methoxypolyethylene glycol (meth)acrylate, phenoxypolyethylene glycol (meth)acrylate, stearyl (meth)acrylate, 1,10-decanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,9-nonanediol di(meth)acrylate, dipropylene glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, phenoxy (meth)acrylate, Ethyl (meth)acrylate, ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, tricyclodecane dimethanol di(meth)acrylate, ethoxylated polypropylene glycol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, ethyl (meth)acrylate, butyl (meth)acrylate, isobutyl (meth)acrylate, tert-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, isodecyl (meth)acrylate, propylene (meth)acrylate dodecyl (meth)acrylate, tridecyl (meth)acrylate, diethylene glycol butyl ether (meth)acrylate, cyclohexyl (meth)acrylate, tetrahydrofurfuryl (meth)acrylate, benzyl (meth)acrylate, 2-phenoxyethyl methacrylate, isobornyl (meth)acrylate, 2-(dimethylamino)ethyl (meth)acrylate, 2-(diethylamino)ethyl (meth)acrylate, glycidyl (meth)acrylate, ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate Acrylate, polyethylene glycol di(meth)acrylate, tetramethylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, hexanediol di(meth)acrylate, nonamethylene glycol di(meth)acrylate, isoamyl (meth)acrylate, ethylene glycol monovinyl ether, tetramethylene glycol monovinyl ether, diethylene glycol monovinyl ether, 2-ethylhexyl vinyl ether, 2-[2-(acetoxy)ethoxy]ethyl 2-acrylate, 2-(2-vinyloxyethoxy)ethyl 2-methyl-2-acrylate, and the like.

[0037] In the above-mentioned polymerizable composition for forming a primer layer, the total of component A, component B and component C is set to 100% by mass, and the content of component C is preferably 30.0% by mass or more, and more preferably 40.0% by mass or more. The total of component A, component B and component C is set to 100% by mass, and the content of component C can be, for example, 90.0% by mass or less, 80.0% by mass or less, or 70.0% by mass or less. In one embodiment, the above-mentioned polymerizable composition for forming a primer layer may contain only one component C, and in another embodiment, it may contain two or more components C. In the case of containing more than two components C, the content of the above-mentioned component C is the total content of more than two. This is also the same for the content related to other components. In one embodiment, component C is preferably the component with the largest content among components A, component B and component C of the above-mentioned polymerizable composition for forming a primer layer.

[0038] In the above-mentioned polymerizable composition for forming a primer layer, the total of component A, component B and component C is set to 100 mass%, and the content of component A is preferably 70.0 mass% or less, more preferably 60.0 mass% or less, and further preferably 50.0 mass% or less. The total of component A, component B and component C is set to 100 mass%, and the content of component A can be, for example, 10.0 mass% or more, 20.0 mass% or more, or 30.0 mass% or more.

[0039] In the above-mentioned polymerizable composition for forming a primer layer, the total of component A, component B and component C is set to 100 mass%, and the content of component A is preferably 3.0 mass% or more, more preferably 5.0 mass% or more, and further preferably 7.0 mass% or more. The total of component A, component B and component C is set to 100 mass%, and the content of component B can be, for example, 30.0 mass% or less or 20.0 mass% or less.

[0040] The polymerizable composition for forming a primer layer may further include a polymerization initiator. The polymerizable composition for forming a primer layer may include the polymerization initiator at a content of, for example, 0.01 to 3.0% by mass, assuming that the total of component A, component B, and component C is 100% by mass.

[0041] As a polymerization initiator, a known polymerization initiator can be used, preferably a free radical polymerization initiator, and more preferably only a free radical polymerization initiator is included as a polymerization initiator. In addition, as a polymerization initiator, a photopolymerization initiator or a thermal polymerization initiator can be used. From the viewpoint of carrying out the polymerization reaction in a short time, a photopolymerization initiator is preferably used. As a photoradical polymerization initiator, for example: benzoin ketal such as 2,2-dimethoxy-1,2-diphenylethane-1-one; α-hydroxyketones such as 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methyl-1-phenylpropane-1-one, 1-[4-(2-hydroxyethoxy)phenyl]-2-hydroxy-2-methyl-1-propane-1-one; 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butane-1-one, 1,2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropane-1 -ketone and other α-amino ketones; 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, 2,4,6-trimethylbenzoyldiphenylphosphine oxide; 2-(o-chlorophenyl)-4,5-diphenylimidazole dimer, 2-(o-chlorophenyl)-4,5-di(methoxyphenyl)imidazole dimer, 2-(o-fluorophenyl)-4,5-diphenylphosphine oxide 2,4,5-triarylimidazole dimers such as phenylimidazole dimer, 2-(o-methoxyphenyl)-4,5-diphenylimidazole dimer, and 2-(p-methoxyphenyl)-4,5-diphenylimidazole dimer; benzophenone compounds such as benzophenone, N,N'-tetramethyl-4,4'-diaminobenzophenone, N,N'-tetraethyl-4,4'-diaminobenzophenone, and 4-methoxy-4'-dimethylaminobenzophenone; 2-ethylanthraquinone, phenanthrenequinone, 2-tert-butylanthraquinone, octamethylanthraquinone, 1,2-benzanthraquinone, 2,3- Quinone compounds such as benzanthraquinone, 2-phenylanthraquinone, 2,3-diphenylanthraquinone, 1-chloroanthraquinone, 2-methylanthraquinone, 1,4-naphthoquinone, 9,10-phenanthrenequinone, 2-methyl-1,4-naphthoquinone, 2,3-dimethylanthraquinone; benzoin ethers such as benzoin methyl ether, benzoin ethyl ether, benzoin phenyl ether; benzoin compounds such as benzoin, methylbenzoin, ethylbenzoin; benzyl compounds such as benzyl dimethyl ketal; acridine compounds such as 9-phenylacridine, 1,7-bis(9,9'-acridinylheptane); N-phenylglycine, coumarin, etc. In addition, in the 2,4,5-triarylimidazole dimer, the substituents of the aryl groups at the two triarylimidazole sites may be the same to obtain a symmetrical compound, or different to obtain an asymmetrical compound. In addition, a thioxanthone compound and a tertiary amine may be combined, such as a combination of diethylthioxanthone and dimethylaminobenzoic acid. Among these, α-hydroxyketone and phosphine oxide are preferred from the viewpoint of curability, transparency and heat resistance.

[0042] The above-mentioned polymerizable composition for forming a primer layer may contain a solvent or may not contain a solvent. When a solvent is contained, any solvent may be used as long as it does not hinder the polymerization reaction of the polymerizable composition. When a solvent is contained, the total of component A, component B and component C is set to 100% by mass, and the content of the solvent is preferably 10.0% by mass or less, more preferably 5.0% by mass or less, and further preferably 3.0% by mass or less.

[0043] The polymerizable composition for forming the above-mentioned primer layer may further include a known additive that can be generally added to the composition for forming the primer layer in any amount. As an additive, a known compound can be used. The total amount of the composition (excluding a polymerization initiator) is set to 100% by mass, and the polymerizable composition for forming the above-mentioned primer layer may include component A, component B and component C in a total of 80.0% by mass or more, 85.0% by mass or more, 90.0% by mass or more, or 95.0% by mass or more. In addition, in the polymerizable composition for forming the above-mentioned primer layer, the total amount of the composition (excluding a polymerization initiator) is set to 100% by mass, and the total content of component A, component B and component C can be, for example, 100% by mass, 100% by mass or less, less than 100% by mass, 99.0% by mass or less, or 98.0% by mass or less. In the present invention and this specification, with respect to the content rate, "the total amount of the composition" refers to the total amount of all components except the solvent in the composition containing the solvent.

[0044] The above-described undercoat layer-forming composition can be prepared by mixing the various components described above simultaneously or sequentially in any order.

[0045] The above-mentioned polymerizable composition for forming a primer layer can be applied to a substrate, and the applied composition can be cured to form a primer layer on the substrate. The primer layer is a cured layer formed by curing the above-mentioned polymerizable composition for forming a primer layer. As a coating method, a known coating method such as a spin coating method and a dip coating method can be used. From the perspective of uniformity of coating, a spin coating method is preferred. In order to clean the surface of the substrate, etc., the surface of the substrate before coating can be subjected to any one or more known pretreatments such as an alkali treatment and a UV ozone treatment. The curing treatment can be light irradiation and / or a heat treatment. From the perspective of allowing the curing reaction to proceed in a short time, light irradiation is preferred. The curing treatment conditions can be determined according to the types of various components contained in the above-mentioned polymerizable composition for forming a primer layer and the composition of the above-mentioned polymerizable composition for forming a primer layer. After the curing treatment, an annealing treatment (heat treatment) can also be performed as needed. The annealing treatment can be performed, for example, in a heat treatment furnace at an atmospheric temperature of about 90 to 130°C.

[0046] The thickness of the primer layer may be, for example, 3 μm or more, preferably 5 μm or more, and the thickness of the primer layer may be, for example, 15 μm or less, preferably 10 μm or less.

[0047] <Photochromic layer>

[0048] (Polymerizable compound)

[0049] The optical article has a photochromic layer on the primer layer. In one embodiment, the photochromic layer can be a cured layer formed by curing a (meth)acrylate polymerizable composition. In the present invention and this specification, "(meth)acrylate polymerizable composition" refers to a polymerizable composition containing (meth)acrylate. The inventors speculate that when the polymerizable composition for forming the primer layer is a (meth)acrylate polymerizable composition, from the viewpoint of further improving the adhesion between the primer layer and the photochromic layer, it is preferred that the composition for forming the photochromic layer is also a (meth)acrylate polymerizable composition.

[0050] Hereinafter, a (meth)acrylate polymerizable composition as one embodiment of the polymerizable composition for forming a photochromic layer will be described. However, the following embodiments are merely examples, and the present invention is not limited to these examples.

[0051] In one embodiment, the photochromic layer-forming polymerizable composition may contain Component C described above.

[0052] In addition, in one embodiment, the polymerizable composition for forming a photochromic layer may contain the following component D.

[0053] Component D is a non-cyclic methacrylate having a molecular weight of 500 or more. In the present invention and this specification, "non-cyclic" means not containing a cyclic structure. In contrast, "cyclic" means containing a cyclic structure. Non-cyclic methacrylate refers to a monofunctional or higher methacrylate that does not contain a cyclic structure.

[0054] Component D may be a monofunctional or difunctional or higher functional methacrylate, preferably a difunctional or trifunctional methacrylate, and more preferably a difunctional methacrylate. Component D may include polyalkylene glycol dimethacrylate. Polyalkylene glycol dimethacrylate may be represented by the following formula 1:

[0055] [Chemical formula 1]

[0056] (Formula 1)

[0057]

[0058] R represents an alkylene group, and n represents the number of repeating units of the alkoxy group represented by RO, which is 2 or more. Examples of the alkylene group represented by R include ethylene, propylene, tetramethylene, and the like. n is 2 or more, and may be, for example, 30 or less, 25 or less, or 20 or less. Specific examples of the polyalkylene glycol dimethacrylate include polyethylene glycol dimethacrylate, polypropylene glycol dimethacrylate, polytetramethylene glycol dimethacrylate, and the like.

[0059] The molecular weight of component D is 500 or more. In the present invention and this specification, the molecular weight of the polymer is the structural formula determined by the structural analysis of the compound or the theoretical molecular weight calculated by the raw material feed ratio during production. The molecular weight of component D is 500 or more, preferably 510 or more, more preferably 520 or more, more preferably 550 or more, more preferably 570 or more, further preferably 600 or more, further preferably 630 or more, and further preferably 650 or more. From the viewpoint of increasing the hardness of the photochromic layer, the molecular weight of component D is, for example, preferably 2000 or less, 1500 or less, 1200 or less, 1000 or less, or 800 or less.

[0060] Moreover, in one embodiment, the polymerizable composition for forming a photochromic layer may contain the following component E.

[0061] Component E is a (meth)acrylate having a molecular weight of 400 or less and represented by the following formula 2:

[0062] [Chemical formula 2]

[0063] (Formula 2)

[0064]

[0065] In formula 2, R 1 and R 2 Each independently represents a hydrogen atom or a methyl group, and m represents an integer greater than 1. m is greater than 1, and may be, for example, less than 10, less than 9, less than 8, less than 7, or less than 6.

[0066] The molecular weight of component E is 400 or less, and from the viewpoint of further increasing the color density of the photochromic layer, is preferably 350 or less, more preferably 300 or less, and further preferably 250 or less. The molecular weight of component E may be, for example, 100 or more, 150 or more, or 200 or more.

[0067] As a (meth)acryloyl group, component E may contain only an acryloyl group, may contain only a methacryloyl group, or may contain an acryloyl group and a methacryloyl group. In one embodiment, it is preferred that component B contains only an acryloyl group as a (meth)acryloyl group. Specific examples of component E include 1,9-nonanediol diacrylate, 1,6-hexanediol diacrylate, 1,10-decanediol diacrylate, and the like.

[0068] As the polymerizable compound, the composition may contain only component D and component E in one embodiment, or may contain one or more other polymerizable compounds in addition to component D and component E in another embodiment. The other polymerizable compounds that may be contained in the composition are exemplified below.

[0069] In one embodiment, the polymerizable composition for forming a photochromic layer may contain the component F exemplified below. Component F does not significantly affect the color development of the photochromic layer formed from the composition under light irradiation and the visible light transmittance under no irradiation, and is a preferred component from the perspective of contributing to improving the performance of the composition, such as coating suitability.

[0070] Component F is a non-cyclic trifunctional or higher (meth)acrylate. Component F is preferably a trifunctional to pentafunctional (meth)acrylate, more preferably a trifunctional or tetrafunctional (meth)acrylate, and further preferably a trifunctional (meth)acrylate. Specific examples of component F include, for example, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol tetra(meth)acrylate, trimethylolethane tri(meth)acrylate, trimethylolpropane tri(meth)acrylate, di(trimethylolpropane) tetra(meth)acrylate, tetramethylolmethane tetra(meth)acrylate, tetramethylolmethane tri(meth)acrylate, etc. The molecular weight of component F can be, for example, in the range of 200 to 400, but is not limited to this range. As a (meth)acryloyl group, component C can contain only an acryloyl group, can contain only a methacryloyl group, or can contain an acryloyl group and a methacryloyl group. In one embodiment, the acyclic tri- or higher-functional (meth)acrylate preferably contains only a methacryloyl group as the (meth)acryloyl group, that is, is preferably a methacrylate.

[0071] In one embodiment, the polymerizable composition for forming a photochromic layer may contain one or more other polymerizable compounds other than the above-mentioned components as polymerizable compounds. In the polymerizable composition for forming a photochromic layer, the total amount of the polymerizable compounds contained in the composition is set to 100% by mass, and the content of component D is preferably 50.0% by mass or more, more preferably 55.0% by mass or more, and further preferably 60.0% by mass or more. In one embodiment, among the multiple polymerizable compounds contained in the composition, component D may be the component that occupies the largest proportion. In addition, the total amount of the polymerizable compounds contained in the composition is set to 100% by mass, and the content of component D may be 90.0% by mass or less, 85.0% by mass or less, 80.0% by mass or less, or 75.0% by mass or less.

[0072] Regarding component E, according to the research of the present inventors, it was found that the higher the content of component E, the higher the color concentration when it is irradiated with light and colored. On the other hand, according to the research of the present inventors, it was also found that the higher the content of component E, the slower the fading speed, which is one of the indicators representing photoresponsiveness, tends to be. From the viewpoint of color concentration, the total amount of the polymerizable compound contained in the composition is set to 100 mass%, and the content of component E is preferably 5.0 mass% or more, more preferably 10.0 mass% or more, and further preferably 15.0 mass% or more. In addition, from the viewpoint of photoresponsiveness, the total amount of the polymerizable compound contained in the composition is set to 100 mass%, and the content of component E is preferably 30.0 mass% or less, and more preferably 25.0 mass% or less.

[0073] Regarding component F, the content of component F may be 0% by mass, or may be 0% by mass or more, more than 0% by mass, 1.0% by mass or more, 3.0% by mass or more, 5% by mass or more, or 7% by mass or more relative to the total amount of the polymerizable compound contained in the photochromic layer-forming polymerizable composition. The content of component F may be, for example, 20.0% by mass or less or 15.0% by mass or less relative to the total amount of the polymerizable compound contained in the composition.

[0074] Regarding component C, the content of component C may be 0% by mass, or may be 0% by mass or more, more than 0% by mass, 1.0% by mass or more, 3.0% by mass or more, 5.0% by mass or more, or 7.0% by mass or more relative to the total amount of the polymerizable compound contained in the photochromic layer-forming polymerizable composition. The content of component C may be, for example, 20.0% by mass or less or 15.0% by mass or less relative to the total amount of the polymerizable compound contained in the photochromic layer-forming polymerizable composition.

[0075] The total amount of the composition is 100 mass %, and the content of the polymerizable compound in the polymerizable composition for forming a photochromic layer can be, for example, 80.0 mass % or more, 85.0 mass % or more, or 90.0 mass % or more. In addition, the total amount of the composition is 100 mass %, and the content of the polymerizable compound in the polymerizable composition for forming a photochromic layer can be, for example, 99.0 mass % or less, 95.0 mass % or less, 90.0 mass % or less, or 85.0 mass % or less.

[0076] (Photochromic Compounds)

[0077] The polymerizable composition for forming a photochromic layer contains a photochromic compound together with a polymerizable compound. As the photochromic compound contained in the polymerizable composition for forming a photochromic layer, a known compound showing photochromism can be used. The photochromic compound can show photochromism to ultraviolet rays, for example. For example, as the photochromic compound, fulgimide compounds, spiro The photochromic compound may be a compound having a known skeleton showing photochromic properties, such as an oxazine compound, a chromene compound, and an indeno-fused naphthopyran compound. The photochromic compound may be used alone or in combination of two or more. The total amount of the composition is set to 100% by mass, and the content of the photochromic compound in the polymerizable composition for forming a photochromic layer may be set to about 0.1 to 15.0% by mass, but is not limited to this range.

[0078] (Other ingredients)

[0079] The polymerizable composition for forming a photochromic layer may contain one or more of various additives that can be generally contained in a polymerizable composition in addition to the polymerizable compound and the photochromic compound at any content rate. As additives that can be contained in the polymerizable composition for forming a photochromic layer, for example, a polymerization initiator for causing the polymerization reaction to proceed can be cited. Regarding the polymerization initiator, reference can be made to the above description. The total amount of the composition is set to 100% by mass, and the content of the polymerization initiator can be, for example, in the range of 0.1 to 5.0% by mass.

[0080] The polymerizable composition for forming a photochromic layer may further contain any known additives that can be added to a composition containing a photochromic compound, for example, surfactants, antioxidants, free radical scavengers, light stabilizers, ultraviolet absorbers, anti-coloring agents, antistatic agents, fluorescent dyes, dyes, pigments, fragrances, plasticizers, silane coupling agents, etc. As these additives, known compounds can be used.

[0081] The polymerizable composition for forming a photochromic layer can be prepared by mixing the various components described above simultaneously or sequentially in any order.

[0082] The photochromic layer can be formed by coating a polymerizable composition for forming a photochromic layer on the primer layer and subjecting the coated composition to a curing treatment. For the coating method, reference can be made to the above description. The curing treatment may be light irradiation and / or heat treatment. From the viewpoint of allowing the curing reaction to proceed in a short time, light irradiation is preferred. The curing treatment conditions are determined according to the types of various components contained in the above composition (polymerizable compounds, polymerization initiators, etc. described above) and the composition of the above composition. The thickness of the photochromic layer thus formed is, for example, preferably in the range of 5 to 80 μm, and more preferably in the range of 20 to 60 μm. Preferably, the substrate is adjacent to the primer layer, and preferably the primer layer is adjacent to the photochromic layer. Among them, "adjacent" means directly connected without other layers in between.

[0083] The optical article having the above-mentioned photochromic layer may further have one or more functional layers in addition to the above-mentioned various layers, or may not have a functional layer. As the functional layer, a protective layer for improving the durability of the optical article, an antireflection layer, a water-repellent or hydrophilic antifouling layer, an antifogging layer, and other layers known as functional layers of optical articles may be cited.

[0084] One form of the optical article is a spectacle lens. In addition, as one form of the optical article, goggles, a brim (brim) portion of a sun hat, a shielding member of a helmet, etc. can also be cited. By applying the composition on a substrate for these optical articles and curing the applied composition to form a photochromic layer, an optical article with an anti-glare function can be obtained.

[0085] [Glasses]

[0086] One embodiment of the present invention relates to a pair of glasses, which includes a spectacle lens as one embodiment of the optical article. The details of the spectacle lens included in the glasses are as described above. The glasses include the spectacle lens, and can be colored by the photochromic compound contained in the photochromic layer when exposed to sunlight, for example, outdoors, thereby exerting an anti-glare effect like sunglasses, and can restore transmittance by fading the photochromic compound when returning indoors. The glasses, frames, etc. can be constructed using known techniques.

[0087] Example

[0088] Hereinafter, the present invention will be further described by way of examples, but the present invention is not limited to the embodiments shown in the examples.

[0089] [Spectacle lens A]

[0090] <Production of eyeglass lenses>

[0091] A plastic lens substrate (trade name EYAS manufactured by HOYA Corporation; center wall thickness 2.5 mm, radius 75 mm, S-4.00) was immersed in a 10% by mass sodium hydroxide aqueous solution (liquid temperature 60°C) for 5 minutes, washed with pure water, and dried. Then, a primer layer was formed on the convex surface (object side surface) of the plastic lens substrate. Specifically, a hydroxyl-containing bifunctional acrylate having the following structure (10 parts by mass) as component B was mixed with Coronate 2715 (40 parts by mass) manufactured by Tosoh Corporation, a polyisocyanate as component A, and 2-phenoxyethyl acrylate (viscosity: 13 cP) (50 parts by mass) as component C.

[0092] [Chemical formula 3]

[0093]

[0094] The thus obtained mixture was mixed with a photoradical polymerization initiator (bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide (Omnirad819 manufactured by IGM Resin BV)) in an amount of 0.02% by mass relative to 100% by mass of the total amount of the mixture, and stirred sufficiently. Thereafter, degassing was performed using a rotation-revolution stirring degassing apparatus.

[0095] The polymerizable composition for forming a primer layer thus obtained was applied to the convex surface of the plastic lens substrate by spin coating in an environment of a temperature of 25° C. and a relative humidity of 50%, and then the composition for forming a primer layer applied to the plastic lens substrate was irradiated with ultraviolet light (wavelength of 405 nm) in a nitrogen atmosphere (oxygen concentration of 500 ppm or less) to cure the composition to form a primer layer. The thickness of the formed primer layer was 8 μm.

[0096] Next, the laminate of the primer layer and the substrate was subjected to annealing treatment (heat treatment) for 2 hours in a heating furnace at an ambient temperature of 90° C., and then the coating composition for forming a photochromic layer prepared as described below was applied to the primer layer by spin coating. The spin coating was performed by the method described in Japanese Patent Publication No. 2005-218994. Then, the composition applied to the plastic lens substrate was irradiated with ultraviolet rays (wavelength 405 nm) in a nitrogen atmosphere (oxygen concentration 500 ppm or less), and the composition was cured to form a photochromic layer. The thickness of the formed photochromic layer was 25 μm.

[0097] In this way, a spectacle lens A having a photochromic layer was produced.

[0098] <Preparation of polymerizable composition for forming photochromic layer>

[0099] In a plastic container, 61.2 parts by mass of polyethylene glycol dimethacrylate (in the above formula 2, n=14, R is ethylene, molecular weight 736) as component D and 1,9-nonanediol diacrylate (in the above formula 2, R is ethylene) as component E were mixed. 1 and R 2 is a hydrogen atom, m=9, molecular weight 268) 18.0 parts by mass, trimethylolpropane trimethacrylate (molecular weight 296) as component F 10.8 parts by mass and 2-phenoxyethyl acrylate (viscosity 13 cP) as component C 10.0 parts by mass.

[0100] The thus obtained mixture of polymerizable compounds was mixed with a photochromic compound (an indeno-fused naphthopyran compound represented by the structural formula described in the specification of U.S. Patent No. 5,645,767), a photoradical polymerization initiator (bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide (Omnirad819 manufactured by IGM Resin BV)), an antioxidant (bis[3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propionate][ethylenebis(oxyethylene)]ester), and a light stabilizer (bis(1,2,2,6,6-pentamethyl-4-piperidyl)sebacate), and stirred thoroughly. Then, degassing was performed using a degassing device with a rotation-revolution stirring method. In this way, a polymerizable composition for forming a photochromic layer was prepared. The total amount of the composition is set to 100 mass%, and the content of the above components is as follows: the mixture of the above polymerizable compounds is 94.90 mass%, the photochromic compound is 3.00 mass%, the photoradical polymerization initiator is 0.30 mass%, the antioxidant is 0.90 mass%, and the light stabilizer is 0.90 mass%. In the polymerizable composition for forming a photochromic layer prepared here, the total amount of the polymerizable compounds is set to 100 mass%, the content of component D is 61.2 mass%, the content of component E is 18.0 mass%, the content of component F is 10.8 mass%, and the content of component C is 10.0 mass%.

[0101] [Spectacle lens B]

[0102] In the preparation of the primer layer-forming composition, Coronate 2715 (25.0 parts by mass) manufactured by Tosoh Corporation and component C as component A were not used, and instead, a hydroxyl-containing bifunctional acrylate (27.5 parts by mass) having the structure shown above and propylene glycol monomethyl ether acetate (27.5 parts by mass) as component B were mixed. Except for this point, eyeglass lens B was obtained in the same manner as eyeglass lens A.

[0103] [Evaluation of optical uniformity]

[0104] In a dark room, under irradiation with high-brightness light from a zircon lamp, the spectacle lenses A and B were observed with an optical microscope. A large number of optical defects of about several tens of μm were confirmed in the spectacle lens B, whereas no such optical defects were observed in the spectacle lens A. That is, the optical uniformity of the spectacle lens A was superior to that of the spectacle lens B.

[0105] [Evaluation of Adhesion]

[0106] The adhesion of the spectacle lens A was evaluated by the cross-section method according to JIS K5600-5-6: 1999. The evaluation result was "remaining square number / total square number" = "100 / 100", confirming that the adhesion between the substrate and the photochromic layer of the spectacle lens A was excellent.

[0107] The spectacle lens A was immersed in 100° C. warm water for 30 minutes and then subjected to adhesion evaluation by the cross-cut method in the same manner as described above. The result was “number of remaining squares / total number of squares” = “100 / 100”.

[0108] Finally, the above methods are summarized.

[0109] According to one embodiment, an optical article is provided, which comprises, in order: a substrate, a primer layer formed by curing a primer layer-forming polymerizable composition, and a photochromic layer containing a photochromic compound, wherein the primer layer-forming polymerizable composition contains the component A, the component B, and the component C.

[0110] The optical article may be an optical article having excellent optical uniformity.

[0111] In one embodiment, the content of Component C in the primer layer-forming polymerizable composition relative to the total of Component A, Component B, and Component C may be 30.0% by mass or more and 90.0% by mass or less.

[0112] In one embodiment, in the polymerizable composition for forming a primer layer, Component C may be the component with the largest content among Component A, Component B, and Component C.

[0113] In one embodiment, the number of hydroxyl groups contained in one molecule of Component B may be 2 or more.

[0114] In one embodiment, Component B may be a hydroxyl group-containing (meth)acrylate.

[0115] In one embodiment, Component B may be a bifunctional or higher-functional (meth)acrylate.

[0116] In one embodiment, the optical article may be a spectacle lens.

[0117] In one embodiment, the optical article may be a goggle lens.

[0118] In one embodiment, the optical article may be a brim portion of a sun hat.

[0119] In one embodiment, the optical article may be a shielding member of a helmet.

[0120] According to one embodiment, there is provided a pair of glasses including the above-mentioned eyeglass lens.

[0121] The various aspects and forms described in this specification may be combined in any combination of two or more.

[0122] The embodiments disclosed this time are merely illustrative in all aspects and are not intended to limit the scope of the present invention. The scope of the present invention is intended to include all modifications that are not described above but are indicated by the claims and are within the meaning and scope equivalent to the claims.

[0123] Industrial Applicability

[0124] The present invention is useful in the technical fields of glasses, goggles, sun hats, helmets, etc.

Claims

1. An optical article, which comprises: Base material, A primer layer formed by curing a primer layer-forming polymerizable composition, and a photochromic layer comprising a photochromic compound, The polymerizable composition for forming an undercoat layer comprises: Ingredient A: Polyisocyanate, Component B: a hydroxyl-containing polymerizable compound, and Component C: a polymerizable compound selected from (meth)acrylates and vinyl ethers, and having a viscosity of 100 cP or less, In the polymerizable composition for forming a primer layer, the content of component C is 30.0% by mass or more relative to the total of component A, component B, and component C.

2. The optical article according to claim 1, wherein In the polymerizable composition for forming a primer layer, the content of component C relative to the total of component A, component B, and component C is 30.0 mass % or more and 90.0 mass % or less.

3. The optical article according to claim 1, wherein: In the polymerizable composition for forming a primer layer, Component C is the component with the largest content among Component A, Component B, and Component C.

4. The optical article according to claim 1, wherein The number of hydroxyl groups contained in one molecule of component B is 2 or more.

5. The optical article according to claim 1, wherein: Component B is a hydroxyl group-containing (meth)acrylate.

6. The optical article according to claim 5, wherein: Component B is a (meth)acrylate having two or more functional groups.

7. The optical article according to claim 1, wherein: Component C is a monofunctional to trifunctional (meth)acrylate.

8. The optical article according to claim 1, wherein: Component C is a vinyl ether having two or more vinyl groups in one molecule. 9 . The optical article according to claim 1 , which is a spectacle lens. 10 . The optical article according to claim 1 , which is a goggle lens.

11. The optical article according to any one of claims 1 to 8, which is a brim portion of a sun hat.

12. The optical article according to any one of claims 1 to 8, which is a shielding member of a helmet. 13 . A pair of glasses comprising the eyeglass lens according to claim 9 .

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