Curable composition for forming protective layer for photochromic article, photochromic article, and eyeglasses

Abstract

Provided is a curable composition for forming a protective layer for a photochromic article, the curable composition containing component A and component B. Component A: polysilsesquioxane having a (meth)acryloyl group, component B: one or more polyfunctional (meth)acrylates selected from the group consisting of polyfunctional (meth)acrylates having an oxyalkylene structure and polyfunctional (meth) acrylates having an epoxy ester structure

Description

Curable composition for forming a protective layer on photochromic articles, photochromic articles and eyeglasses Cross-reference of related applications

[0001] This application claims priority to Japanese Patent Application No. 2025-055429, filed on 28 March 2025, the entirety of which is incorporated herein by reference as a particular disclosure.

[0002] The present invention relates to a curable composition for forming a protective layer on a photochromic article, a photochromic article, and eyeglasses.

[0003] Photochromic compounds are compounds that exhibit the property of becoming colored under irradiation with light in a photoresponsive wavelength range and fading under non-irradiation conditions (photochromicity). Hereinafter, articles containing photochromic compounds will be referred to as photochromic articles. For example, WO2003 / 011967 (the entire description thereof is incorporated herein by reference as particularly disclosed) discloses a photochromic article having a layer containing a photochromic compound (photochromic layer) provided on a substrate.

[0004] The inventors of this invention considered providing a protective layer to photochromic articles in order to improve their performance. Through repeated consideration, the inventors came to believe that the following properties are desirable for photochromic articles having a protective layer: Firstly, the protective layer should be resistant to cracking. Cracks in the protective layer can cause clouding and / or optical defects in the photochromic article. Secondly, even if scratches occur on the photochromic article, these scratches should be difficult to see. If easily visible scratches are present on the photochromic article, the appearance quality of the photochromic article will deteriorate. Thirdly, the photochromic article should have excellent weather resistance. Fourthly, the reduction in the photochromic performance of the photochromic article due to the provision of the protective layer should be minimal.

[0005] In view of the above, one aspect of the present invention aims to provide a photochromic article having a protective layer that is resistant to cracking, in which scratches are difficult to see, which has excellent weather resistance, and which has little reduction in photochromic performance due to the provision of the protective layer.

[0006] One aspect of the present invention is as follows: [1] A curable composition for forming a protective layer on a photochromic article (hereinafter also simply referred to as "composition"), comprising the following components A and B. Component A: Polysilsesquioxane having a (meth)acryloyl group Component B: One or more polyfunctional (meth)acrylates selected from the group consisting of polyfunctional (meth)acrylates having an oxyalkylene structure and polyfunctional (meth)acrylates having an epoxy ester structure [2] The curable composition for forming a protective layer on a photochromic article according to [1], wherein component B contains at least a polyfunctional (meth)acrylate having an oxyalkylene structure. [3] The curable composition for forming a protective layer on a photochromic article according to [2], wherein the polyfunctional (meth)acrylate having an oxyalkylene structure is one or more selected from the group consisting of polyfunctional (meth)acrylates represented by the following formula 1 and polyfunctional (meth)acrylates represented by the following formula 2. (In Formula 1, X represents an oxyalkylene structure, and multiple Xs within the molecule are either the same or different oxyalkylene structures. Z represents a hydrogen atom or a methyl group, and multiple Zs within the molecule are either the same or different. a to f are each independently one or more, and the sum of a to f is the total number of oxyalkylene structures within the molecule.) (In formula 2, R represents an oxyalkylene structure, and multiple Rs in the molecule are the same or different oxyalkylene structures. Z represents a hydrogen atom or a methyl group, and multiple Zs in the molecule are the same or different. l to n are each independently 1 or more, and the sum of l to n is the total number of oxyalkylene structures in the molecule.) [4] A curable composition for forming a protective layer for a photochromic article according to any one of [1] to [3], wherein component B contains at least a polyfunctional (meth)acrylate having an epoxy ester structure. [5] A curable composition for forming a protective layer for a photochromic article according to any one of [1] to [4], wherein the content of component A is 5 parts by mass or more and 80 parts by mass or less per 100 parts by mass of the total amount of components A and B. [6] A curable composition for forming a protective layer for a photochromic article according to any one of [1] to [5], further containing the following component C. Component C: Polyester (meth)acrylate [7] A curable composition for forming a protective layer for a photochromic article according to [6], wherein the content of component C is 5 parts by mass or more and 40 parts by mass or less per 100 parts by mass of the total amount of components A, B and C. [8] A photochromic article having a protective layer which is a cured layer obtained by curing the curable composition according to any one of [1] to [7], and a photochromic layer containing a photochromic compound. [9] A photochromic article according to [8], wherein the thickness of the protective layer is 1 μm or more and 50 μm or less.

[10] A photochromic article according to [8] or [9], having a substrate, the photochromic layer and the protective layer in this order.

[11] A photochromic article according to any one of [8] to

[10] , having a substrate, the photochromic layer, the protective layer and an organosilicon-based cured layer in this order.

[12] A photochromic article according to any one of [8] to

[11] , which is an eyeglass lens.

[13] A photochromic article according to any one of [8] to

[11] , which is a lens for goggles, a visor portion of a sun visor, or a shield component of a helmet.

[14] Eyeglasses equipped with the spectacle lenses according to

[12] .

[0007] According to one aspect of the present invention, it is possible to provide a photochromic article having a protective layer that is resistant to cracking, in which scratches are difficult to see, which has excellent weather resistance, and which has little reduction in photochromic performance due to the provision of the protective layer.

[0008] [Curable composition for forming a protective layer on photochromic articles] The above composition will be described in more detail below.

[0009] The above composition is a curable composition for forming a protective layer on a photochromic article. In the present invention and this specification, "photochromic article" refers to an article containing a photochromic compound. In a photochromic article, the photochromic compound is included, for example, in a layer (photochromic layer) provided on a substrate. The photochromic layer will be described in detail later. The protective layer formed from the above composition can be provided, for example, on top of the photochromic layer, thereby contributing to improving the durability of the photochromic article.

[0010] The above composition is a curable composition. In the present invention and this specification, "curable composition" means a composition containing one or more polymerizable compounds, and may also be called a "polymerizable composition." "Polymerizable compound" means a compound having one or more polymerizable groups in one molecule. "(meth)acrylate" is a polymerizable compound. In the present invention and this specification, "(meth)acrylate" is used to encompass both acrylate and methacrylate. "Acrylate" is a compound having one or more acryloyl groups in one molecule. "Methacrylate" is a compound having one or more methacryloyl groups in one molecule. For (meth)acrylate, the functional number is the number of groups selected from the group consisting of acryloyl groups and methacryloyl groups contained in one molecule. In this invention and specification, "methacrylate" refers to a material containing only a methacryloyl group as the (meth)acryloyl group, while a material containing both an acryloyl group and a methacryloyl group as the (meth)acryloyl group is called an acrylate. The acryloyl group may be contained in the form of an acryloyloxy group, and the methacryloyl group may be contained in the form of a methacryloyloxy group. In this invention and specification, "(meth)acryloyl group" is used to encompass both an acryloyl group and a methacryloyl group, and "(meth)acryloyloxy group" is used to encompass both an acryloyloxy group and a methacryloyloxy group. Unless otherwise specified, the groups described may have substituents or may be unsubstituted. When a group has substituents, examples of substituents include alkyl groups (e.g., alkyl groups having 1 to 6 carbon atoms), hydroxyl groups, alkoxy groups (e.g., alkoxy groups having 1 to 6 carbon atoms), halogen atoms (e.g., fluorine atoms, chlorine atoms, bromine atoms), cyano groups, amino groups, nitro groups, acyl groups, carboxyl groups, etc. For groups having substituents, "number of carbon atoms" refers to the number of carbon atoms in the part that does not contain substituents.

[0011] The above composition comprises component A and component B. The above composition may contain only one or more types of component A, and may contain only one or more types of component B. The inventors surmise that component A may contribute to making scratches on the photochromic article difficult to see and to enabling it to exhibit excellent weather resistance. Regarding component B, the inventors believe that component B may contribute to suppressing crack formation in the protective layer and to suppressing the deterioration of the photochromic performance of the photochromic article due to the provision of the protective layer. However, the present invention is not limited to the surmise described herein.

[0012] The following provides a more detailed explanation of components A and B.

[0013] <Component A> Component A is a polysilsesquioxane having a (meth)acryloyl group. "Polysilsesquioxane" is defined as [R-Si-O ３／２ This is a compound containing multiple units in one molecule. R represents an organic group. Component A is [R-Si-O ３／２ The ] unit contains one or more R-parts containing (meth)acryloyl groups. The functional group equivalent of the polysilsesquioxane having (meth)acryloyl groups, which is component A, can be, for example, 100 g / eq or more and 300 g / eq or less. The functional group that defines the above functional group equivalent is the (meth)acryloyl group. Known structures of polysilsesquioxane include random structures, cage structures and ladder structures. The structure of the polysilsesquioxane of component A included in the above composition is not particularly limited and can take any structure. For example, the above composition may include a mixture of two or more polysilsesquioxanes having different structures as component A.

[0014] Component A, a polysilsesquioxane having a (meth)acryloyl group, is [R-SiO-O ３／２ One or more R units can be organic groups selected from the group consisting of (1) and (2) below. In (1) and (2) below, n is an integer of 1 or more, for example, an integer between 1 and 5.

[0015]

[0016] <Component B> Component B is one or more polyfunctional (meth)acrylates selected from the group consisting of polyfunctional (meth)acrylates having an oxyalkylene structure and polyfunctional (meth)acrylates having an epoxy ester structure. The composition may comprise, as Component B, only one or two or more of polyfunctional (meth)acrylates having an oxyalkylene structure, or may comprise only one or two or more of polyfunctional (meth)acrylates having an epoxy ester structure. Alternatively, the composition may comprise one or more polyfunctional (meth)acrylates having an oxyalkylene structure and one or more polyfunctional (meth)acrylates having an epoxy ester structure.

[0017] (Polyfunctional (meth)acrylate having an oxyalkylene structure) In the present invention and the present specification, the "oxyalkylene structure" is a structure formed by bonding an alkylene group and an oxygen atom, which is "-R １ -O-" represented structure. Here, R １ represents an alkylene group. R １ The alkylene group represented by can be, for example, an alkylene group having 2 or more carbon atoms. The number of carbon atoms of the alkylene group can be, for example, 6 or less, 5 or less, 4 or less, or 3 or less. When a polyfunctional (meth)acrylate having an oxyalkylene structure has two or more oxyalkylene structures in the molecule, the alkylene groups in these oxyalkylene structures are the same or different alkylene groups. In one embodiment, the polyfunctional (meth)acrylate having an oxyalkylene structure can have one oxyalkylene structure or a structure in which two or more oxyalkylene structures are consecutive only at one position in the molecule. When a structure in which two or more oxyalkylene structures are consecutive is referred to as a polyoxyalkylene structure, the polyoxyalkylene structure is "-(R １ -O) ｎ１ -" can be represented by, R １has the same definition as above, n1 is the number of repetitions, and can be, for example, 2 or more and 15 or less. In another embodiment, the polyfunctional (meth)acrylate having an oxyalkylene structure may have one oxyalkylene structure or a structure in which two or more oxyalkylene structures are continuous (polyoxyalkylene structure) at two or more plural positions in a molecule. In this case, the total number of oxyalkylene structures at the plurality of positions can be, for example, 2 or more and 15 or less.

[0018] The functional number of the polyfunctional (meth)acrylate having an oxyalkylene structure is 2 or more, and can be, for example, 2 or more and 6 or less. As described above, the functional number of a (meth)acrylate is the number of groups selected from the group consisting of acryloyl groups and methacryloyl groups contained in one molecule.

[0019] As specific examples of the polyfunctional (meth)acrylate having an oxyalkylene structure, pentafunctional or hexafunctional (meth)acrylates represented by the following Formula 1 can be exemplified. In Formula 1, X is "-R １ -O-" (oxyalkylene structure), and a plurality of X present in the molecule are the same or different oxyalkylene structures. Z represents a hydrogen atom or a methyl group, and a plurality of Z present in the molecule are the same or different. a to f are each independently 1 or more, and the sum of a to f is the total number of oxyalkylene structures in the molecule, and can be, for example, 6 or more and 15 or less.

[0020]

[0021] As specific examples of the polyfunctional (meth)acrylate having an oxyalkylene structure, trifunctional (meth)acrylates represented by the following Formula 2 can also be exemplified. In Formula 2, R is "-R １ -O-" (oxyalkylene structure), and a plurality of R present in the molecule are the same or different oxyalkylene structures. Z represents a hydrogen atom or a methyl group, and a plurality of Z present in the molecule are the same or different. l to n are each independently 1 or more, and the sum of l to n is the total number of oxyalkylene structures in the molecule, and can be, for example, 3 or more and 25 or less.

[0022]

[0023] However, in the present invention, polyfunctional (meth)acrylates having an oxyalkylene structure are not limited to the examples given above.

[0024] <Polyfunctional (meth)acrylates having an epoxy ester structure> The "epoxy ester structure" is a structure produced by the reaction of an epoxy group and a carboxyl group, and is "-CH(OH)-CH ２ It can be represented as -O-C(=O)-. The number of functions of a polyfunctional (meth)acrylate having an epoxy ester structure is 2 or more, for example, 2 to 6. A polyfunctional (meth)acrylate having an epoxy ester structure contains one or more epoxy ester structures in one molecule, and may contain two or more (for example, two or three). Component B, a polyfunctional (meth)acrylate having an epoxy ester structure, may contain, for example, two epoxy ester structures in one molecule.

[0025] For example, polyfunctional (meth)acrylates containing two epoxy ester structures in one molecule include the difunctional (meth)acrylate represented by formula 3 below and the difunctional (meth)acrylate represented by formula 4 below.

[0026]

[0027] In equations 3 and 4, Z １ Z ２ and Z ３ Each of these independently represents a hydrogen atom or a methyl group. In formula 4, Z ４ n represents a hydrogen atom, a methyl group, or a hydroxyl group. n1 in formula 3 and n2 in formula 4 each independently represent an integer between 1 and 3. In formulas 3 and 4, the ester group (-C(=O)O-) contained in the (meth)acryloyloxy group constitutes part of the epoxy ester structure. Examples of commercially available bifunctional (meth)acrylates represented by formula 3 or 4 include epoxy ester 40EM (manufactured by Kyoeisha Chemical Co., Ltd.), epoxy ester 70PA (manufactured by Kyoeisha Chemical Co., Ltd.), epoxy ester 80MFA (manufactured by Kyoeisha Chemical Co., Ltd.), epoxy ester 200PA (manufactured by Kyoeisha Chemical Co., Ltd.), and the like.

[0028] One form of component B is a (meth)acrylate generally called bisphenol A type epoxy (meth)acrylate or bisphenol A type epoxy resin. Such (meth)acrylate has the following bisphenol A structure, for example, one of the following bisphenol A structures in one molecule. Specific examples of commercially available products include epoxy ester 3002M(N) (manufactured by Kyoeisha Chemical Co., Ltd.), epoxy ester 3002A(N) (manufactured by Kyoeisha Chemical Co., Ltd.), epoxy ester 3000MK (manufactured by Kyoeisha Chemical Co., Ltd.), epoxy ester 3000A (manufactured by Kyoeisha Chemical Co., Ltd.), etc.

[0029]

[0030] The above composition may contain, for example, 80% or more, 85% or more, 90% or more or 95% or more by mass of (meth)acrylate, with the total amount of polymerizable compound being 100% by mass, and the total amount of polymerizable compound (i.e., 100% by mass) may be (meth)acrylate.

[0031] Regarding the blending ratio of component A and component B in the above composition, the content of component A relative to 100 parts by mass of the total amount of component A and component B is preferably 5 parts by mass or more, in the order of 10 parts by mass or more, 15 parts by mass or more, 20 parts by mass or more, 25 parts by mass or more, 30 parts by mass or more, and 35 parts by mass or more, from the viewpoint of making scratches on the photochromic article less visible and further improving the weather resistance of the photochromic article. From the viewpoint of further suppressing crack occurrence in the protective layer and further suppressing the deterioration of the photochromic performance of the photochromic article due to the provision of a protective layer, the above content of component A is preferably 80 parts by mass or less, in the order of 75 parts by mass or less, 70 parts by mass or less, 65 parts by mass or less, 60 parts by mass or less, 55 parts by mass or less, and 50 parts by mass or less.

[0032] <Other (meth)acrylates> In one embodiment, the total amount of (meth)acrylates contained in the above composition may be component A and component B. In another embodiment, the (meth)acrylates contained in the above composition may be one or more of component A, component B, and (meth)acrylates other than component A and component B (referred to as "other (meth)acrylates"). When the above composition contains other (meth)acrylates, the content of other (meth)acrylates relative to 100 parts by mass of the total amount of component A, component B, and other (meth)acrylates may be, for example, 1 part by mass or more, 5 parts by mass or more, 10 parts by mass or more, 15 parts by mass or more, 20 parts by mass or more, or 25 parts by mass or more. The above content of other (meth)acrylates may be, for example, 50 parts by mass or less, 45 parts by mass or less, 40 parts by mass or less, or 35 parts by mass or less.

[0033] (Component C) Another example of (meth)acrylate is polyester (meth)acrylate (component C). "Polyester (meth)acrylate" is a (meth)acrylate having multiple ester bonds in one molecule, and can have a structure in which multiple (meth)acryloyl groups are introduced into one polyester molecule. Polyester (meth)acrylate can be monofunctional (meth)acrylate or difunctional (meth)acrylate. For example, commercially available difunctional polyester (meth)acrylates include Arronix M-6100 (manufactured by Toagosei Co., Ltd.), Arronix M-6250 (manufactured by Toagosei Co., Ltd.), Arronix M-6500 (manufactured by Toagosei Co., Ltd.), etc.

[0034] If the above composition contains one or more types of component C, the content of component C relative to 100 parts by mass of the total amount of components A, B, and C may be, for example, 1 part by mass or more, 5 parts by mass or more, 10 parts by mass or more, 15 parts by mass or more, 20 parts by mass or more, or 25 parts by mass or more. The above content of component C may be, for example, 50 parts by mass or less, 45 parts by mass or less, 40 parts by mass or less, or 35 parts by mass or less.

[0035] The above composition may contain one or more of the various additives that can be included in a curable composition in any amount. Examples of such additives include known additives such as polymerization initiators for promoting polymerization reactions and leveling agents for improving the coating suitability of the composition. Additives can be used in any amount.

[0036] For example, as the polymerization initiator, a known polymerization initiator capable of functioning as a polymerization initiator for (meth)acrylate can be used, with radical polymerization initiators being preferred, and more preferably containing only radical polymerization initiators as the polymerization initiator. In addition, a photopolymerization initiator or a thermal polymerization initiator can be used as the polymerization initiator, with photopolymerization initiators being preferred from the viewpoint of proceeding the polymerization reaction in a short time. Examples of photoradical polymerization initiators include benzoin ketals such as 2,2-dimethoxy-1,2-diphenylethane-1-one; α-hydroxyketones such as 1-hydroxycyclohexylphenyl ketone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, and 1-[4-(2-hydroxyethoxy)phenyl]-2-hydroxy-2-methyl-1-propan-1-one; α-aminoketones such as 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one and 1,2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one; oxime esters such as 1-[(4-phenylthio)phenyl]-1,2-octadione-2-(benzoyl)oxime; bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, and bis(2,6-dimethoxybenzo Phosphine oxides such as 2,4,4-trimethylpentylphosphine oxide and 2,4,6-trimethylbenzoyldiphenylphosphine oxide; 2,4,5-triarylimidazole dimers such as 2-(o-chlorophenyl)-4,5-diphenylimidazole dimer, 2-(o-chlorophenyl)-4,5-di(methoxyphenyl)imidazole dimer, 2-(o-fluorophenyl)-4,5-diphenylimidazole dimer, 2-(o-methoxyphenyl)-4,5-diphenylimidazole dimer, and 2-(p-methoxyphenyl)-4,5-diphenylimidazole dimer; benzophenone compounds such as benzophenone, N,N'-tetramethyl-4,4'-diaminobenzophenone, N,N'-tetraethyl-4,4'-diaminobenzophenone, and 4-methoxy-4'-dimethylaminobenzophenone;Quinone compounds such as 2-ethylanthraquinone, phenanthrenequinone, 2-tert-butylanthraquinone, octamethylanthraquinone, 1,2-benzanthraquinone, 2,3-benzanthraquinone, 2-phenylanthraquinone, 2,3-diphenylanthraquinone, 1-chloroanthraquinone, 2-methylanthraquinone, 1,4-naphthoquinone, 9,10-phenantraquinone, 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 benzyldimethylketal; acridine compounds such as 9-phenylacridine and 1,7-bis(9,9'-acridinylheptane); N-phenylglycine, coumarin, etc. Furthermore, in the 2,4,5-triarylimidazole dimer, the substituents on the aryl groups of the two triarylimidazole moieties may be identical and symmetric, or they may be different and asymmetric. Also, a thioxanthone compound may be combined with a tertiary amine, such as the combination of diethylthioxanthone and dimethylaminobenzoic acid. Among these, α-hydroxyketones and phosphine oxides are preferred from the viewpoint of curability, transparency, and heat resistance. The content of the polymerization initiator can be, for example, in the range of 0.1 to 5.0% by mass, with the total amount of polymerizable compounds in the composition being 100% by mass.

[0037] In one embodiment, the above composition may contain an ultraviolet absorber. As UV absorbers, one or more of the following UV absorbers can be used: for example, hydroxyphenyl triazine compounds such as 2,4-bis(2,4-dimethylphenyl)-6-(2-hydroxy-4-n-octyloxyphenyl)-s-triazine, 2,4,6-tris(2-hydroxy-4-hexyloxy-3-methylphenyl)-s-triazine, 2-[2-hydroxy-4-(2-ethylhexyloxy)phenyl]-4,6-dibiphenyl-s-triazine, 2-[[2-hydroxy-4-[1-(2-ethylhexyloxycarbonyl)ethyloxy]phenyl]]-4,6-diphenyl-s-triazine, and benzotriazole-based UV absorbers such as 2-(5-chloro-2H-benzotriazole-2-yl)-6-tert-butyl-4-methylphenol and 2-(5-chloro-2-benzotriazolyl)-6-tert-butyl-p-cresol. The inclusion of an ultraviolet absorber in the above composition may contribute to improving the weather resistance of a photochromic article having a protective layer formed from this composition. When the above composition contains an ultraviolet absorber, the content of the ultraviolet absorber can be in the range of, for example, 0.1 to 1.0% by mass, with the total amount of polymerizable compounds contained in the composition being 100% by mass.

[0038] The above composition can be prepared by mixing the various components described above simultaneously or sequentially in any order.

[0039] [Photochromic Articles] One aspect of the present invention relates to a photochromic article having a photochromic layer containing a photochromic compound and a protective layer which is a cured layer obtained by curing the above composition. The above photochromic article will be described in more detail below.

[0040] <Photochromic Layer> (Photochromic Compound) As the photochromic compound, any known compound exhibiting photochromic properties can be used. The photochromic compound can exhibit photochromic properties, for example, to ultraviolet light. Examples of photochromic compounds include compounds having a known photochromic skeleton such as azobenzenes, spiropyrans, spirooxazines, naphthopyrans, indenonaphthopyrans, phenantropyrans, hexaarylbisimidazoles, donor-acceptor Stenhaus adducts (DASAs), salicylideneanilines, dihydropyrenes, anthracene dimers, flugides, diarylethenes, phenoxynaphthacenones, and stilbenes. Preferred photochromic compounds include flugimide compounds, spirooxazine compounds, chromene compounds, and indenocondensed naphthopyran compounds. Furthermore, the photochromic compound may be one or more selected from the group consisting of photochromic compounds represented by general formula A, general formula B, and general formula C, as described in WO2022 / 138966. The photochromic compound can be used alone or in mixture of two or more. The content of the photochromic compound in the above composition can be, for example, about 0.1 to 15% by mass, with the mass of the photochromic layer being 100% by mass, but is not limited to this range.

[0041] (Components for forming the photochromic layer) The photochromic layer may be a cured layer obtained by curing a curable composition containing one or more photochromic compounds. Regarding the various components, such as polymerizable compounds, contained in the curable composition for forming the photochromic layer, known technologies related to photochromic articles can be applied. From the viewpoint of adhesion to the protective layer, it is preferable that the photochromic layer is a cured layer obtained by curing a curable composition containing (meth)acrylate as a polymerizable compound.

[0042] In one embodiment, the photochromic layer can be a cured layer formed by curing a coating layer, which is created by directly applying a curable composition containing one or more photochromic compounds to the surface of a substrate or by applying it to the surface of a layer provided on the substrate. Known coating methods such as spin coating and dip coating can be used as coating methods, and spin coating is preferred from the viewpoint of uniformity of coating. The polymerization treatment can be light irradiation and / or heat treatment, and light irradiation is preferred from the viewpoint of proceeding the polymerization reaction in a short time. The polymerization conditions should be determined according to the types and compositions of various components contained in the curable composition. The above description of the coating method and polymerization treatment also applies to curable compositions for forming protective layers. The thickness of the photochromic layer is preferably in the range of 1 to 50 μm, more preferably in the range of 5 to 50 μm, and even more preferably in the range of 20 to 50 μm.

[0043] <Protective Layer> The above photochromic article has a protective layer which is a cured layer obtained by curing the above curable composition for forming the protective layer. The protective layer can be provided directly on the surface of the photochromic layer, or it can be provided on the surface of a layer located above the photochromic layer. Examples of layers that can be located between the photochromic layer and the protective layer include a primer layer. The thickness of the protective layer is preferably 1 μm or more, more preferably 5 μm or more, even more preferably 10 μm or more, and even more preferably 15 μm or more. Furthermore, the thickness of the protective layer is preferably 50 μm or less, and more preferably in the order of 45 μm or less, 40 μm or less, 35 μm or less, 30 μm or less, 25 μm or less, and 20 μm or less. The above protective layer can contribute to improving the durability of the photochromic article. It can also protect the photochromic layer until further processing (for example, the formation of the cured layer described later) is performed, preventing scratches from occurring on the photochromic layer.

[0044] <Substrate> In one embodiment, the above-mentioned photochromic article may be an optical article. Optical articles include various articles such as eyeglass lenses, goggle lenses, visor portions of sun visors, and shield components of helmets. For example, the above-mentioned photochromic article may have a photochromic layer and a protective layer on a substrate selected according to the type of optical article. As an example of a substrate, an eyeglass lens substrate may be a plastic lens substrate or a glass lens substrate. A glass lens substrate may be, for example, a lens substrate made of inorganic glass. As a lens substrate, a plastic lens substrate is preferred from the viewpoint of being lightweight, less prone to breakage, and easy to handle. Examples of plastic lens substrates include (meth)acrylic resin, styrene resin, polycarbonate resin, allyl resin, allyl carbonate resin such as diethylene glycol bisallyl carbonate resin (CR-39), vinyl resin, polyester resin, polyether resin, urethane resin obtained by the reaction of an isocyanate compound with a hydroxyl compound such as diethylene glycol, thiourethane resin obtained by the reaction of an isocyanate compound with a polythiol compound, and cured products (generally called transparent resins) obtained by curing a curable composition containing a (thio)epoxy compound having one or more disulfide bonds in the molecule. The lens substrate may be undyed (colorless lens) or dyed (dyed lens). The refractive index of the lens substrate can be, for example, about 1.50 to 1.76. However, the refractive index of the lens substrate is not limited to the above range, and may be within the above range or outside of it. In the present invention and this specification, refractive index refers to the refractive index for light with a wavelength of 500 nm. Furthermore, the lens base material may be a lens with refractive power (a so-called prescription lens) or a lens without refractive power (a so-called non-prescription lens).

[0045] Eyeglass lenses can be various types of lenses, such as single-vision lenses, multi-vision lenses, and progressive lenses. The type of lens is determined by the surface shape of both sides of the lens substrate. The surface of the lens substrate may be convex, concave, or flat. In typical lens substrates and eyeglass lenses, the object-side surface is convex, and the eye-side surface is concave. However, the present invention is not limited to this. The photochromic layer can usually be provided on the object-side surface of the lens substrate, but it may also be provided on the eye-side surface.

[0046] The photochromic layer may be provided directly on the surface of the substrate, or indirectly via one or more other layers. Examples of other layers include primer layers to improve adhesion between the photochromic layer and the substrate. Such primer layers are well known. The thickness of the primer layer can be, for example, 0.1 to 20 μm.

[0047] <Optional Layers> The above-mentioned photochromic article may have a layer configuration of "substrate / photochromic layer / protective layer". Regarding the layer configuration, " / " is used to encompass both a form in which the layers are in direct contact without other layers and a form in which they are provided via one or more layers of other layers. For example, a primer layer may exist between the substrate and the photochromic layer as described above, but the substrate and the photochromic layer may also be in direct contact. In one embodiment, the above-mentioned photochromic article may have a layer configuration of "substrate / photochromic layer / protective layer / other curing layer". In such a layer configuration, the other curing layer may be a curing layer generally called a hard coat layer. By providing a hard coat layer in addition to the protective layer, the durability of the photochromic article can be further enhanced. In one embodiment, the impact resistance of the photochromic article can also be enhanced by providing a hard coat layer. In one embodiment, the above-mentioned other curing layer may be in direct contact with the protective layer without other layers.

[0048] The thickness of the other cured layer can be, for example, in the range of 0.1 to 10 μm, preferably in the range of 1 to 10 μm, more preferably in the range of 1 to 8 μm, and even more preferably in the range of 1 to 5 μm. In one embodiment, the other cured layer can be a thinner layer than the protective layer. An example of the other cured layer is an organosilicon-based cured layer. Organosilicon-based cured layers are preferred because they generally have excellent impact resistance. Furthermore, if an anti-reflective film is provided, for example, the organosilicon-based cured layer is also preferred because it generally has excellent adhesion to the anti-reflective film.

[0049] An organosilicon-based cured layer is a cured layer obtained by curing a curable composition containing an organosilicon compound. Examples of organosilicon compounds include organosilicon compounds that can generate silanol groups by polymerization treatment, and organopolysiloxanes having reactive groups such as halogen atoms or amino groups that condense with silanol groups. Other examples of organosilicon compounds include silane coupling agents having polymerizable groups such as vinyl groups, allyl groups, (meth)acryloyl groups, and (meth)acryloyloxy groups, and hydrolyzable groups such as alkoxy groups. The curable composition containing the organosilicon compound may contain particles of inorganic substances such as silicon oxides and titanium oxides for purposes such as adjusting the refractive index. For details of the curable composition containing the organosilicon compound, known technologies relating to organosilicon-based cured layers that can function as a hard coat layer can be applied. Such a curable composition can be cured by proceeding with a polymerization reaction by light irradiation and / or heat treatment, depending on the type of components contained in the composition.

[0050] The above-mentioned photochromic articles may have one or more additional layers in addition to the various layers described above. Examples of such layers include layers known as functional layers for optical articles, such as anti-reflective layers, water-repellent or hydrophilic anti-fouling layers, and anti-fogging layers.

[0051] One form of the above-mentioned photochromic article is an eyeglass lens. Other forms of the above-mentioned photochromic article include lenses for goggles, visors for sun visors, and shield components for helmets. The above-mentioned photochromic article can be suitably used as an optical article having an anti-glare function.

[0052] [Eyeglasses] One aspect of the present invention relates to eyeglasses equipped with the above-mentioned photochromic article, which is an eyeglass lens. Details of the eyeglass lens included in these eyeglasses are as described above. By being equipped with such eyeglass lenses, the eyeglasses can, for example, exert an anti-glare effect like sunglasses outdoors as the photochromic compound contained in the photochromic layer is colored by sunlight irradiation, and when returning indoors, the photochromic compound fades, restoring transparency. Regarding the structure of the frame and other components of the eyeglasses, known technologies can be applied.

[0053] The present invention will be further described below with reference to examples. However, the present invention is not limited to the embodiments shown in the examples. Unless otherwise specified, the processes and evaluations described below were carried out in air at room temperature (20°C ± 5°C).

[0054] Details of the various components shown in the table below are as follows:

[0055] [Component A] MAC-SQ™-100: Silsesquioxane derivative MAC-SQ™-100 manufactured by Toagosei Co., Ltd. (R is as follows (2) (n=3) [R-SiO ３／２ [Having units, a mixture of random structure, cage structure and ladder structure, functional group equivalent: 179 g / eq) AC-SQ SI-20: Silsesquioxane derivative AC-SQ SI-20 (R is as follows (1) (n=3) [R-Si-O ３／２ (Contains units, functional group equivalent: 207 g / eq)

[0056]

[0057] [Component B] <Polyfunctional (meth)acrylate having an oxyalkylene structure> NK Ester A-DPH-12E: NK Ester A-DPH-12E manufactured by Shin Nakamura Chemical Industry Co., Ltd. (NK Ester A-DPH-12E manufactured by Shin Nakamura Chemical Industry Co., Ltd. is an ethoxylated dipentaerythritol polyacrylate represented by formula 1, where X is ethylene oxide (having an ethylene group as an alkylene group), Z is a hydrogen atom, and the sum of a to f is approximately 12.) NK Ester A-TMPT-9EO: NK Ester A-TMPT-9EO manufactured by Shin Nakamura Chemical Industry Co., Ltd. (NK Ester A-TMPT-9EO manufactured by Shin Nakamura Chemical Industry Co., Ltd. is an (alkoxylated) trimethylolpropane acrylate represented by formula 2, where R is ethylene oxide (having an ethylene group as an alkylene group), Z is a hydrogen atom, and the sum of l to n is approximately 9.) NK Ester AT-20E: NK Ester AT-20E manufactured by Shin-Nakamura Chemical Industry Co., Ltd. (NK Ester AT-20E manufactured by Shin-Nakamura Chemical Industry Co., Ltd. is an (alkoxylated) trimethylolpropane acrylate represented by formula 2, where R is ethylene oxide (having an ethylene group as an alkylene group), Z is a hydrogen atom, and the sum of l to n is approximately 20.)

[0058] <Polyfunctional (meth)acrylate having an epoxy ester structure> Epoxy ester 40EM: Epoxy ester 40EM manufactured by Kyoeisha Chemical Co., Ltd. (Epoxy ester 40EM manufactured by Kyoeisha Chemical Co., Ltd. is a bifunctional methacrylate represented by formula 3, in formula 3, Z １ and Z ２ is a methyl group, Z ３ (where is a hydrogen atom, and n1 is 1.)

[0059] [Other (meth)acrylates] Arronix M-6500 (component C): Arronix M-6500 manufactured by Toagosei Co., Ltd. (bifunctional polyester acrylate) EBECRYL 4740: (allophanate type, trifunctional urethane acrylate) NK Ester A-TMPT: (trimethylolpropane triacrylate)

[0060] [Photopolymerization initiator] Omnirad 819: IGM Resins B. V. Manufactured by Omnirad 819

[0061] [Leveling agent] DOWSIL L-7001: DOWSIL L-7001 manufactured by Dow-Toray Corporation

[0062] [Example 1] <Preparation of eyeglass lenses (photochromic articles)> A plastic lens substrate (HOYA Corporation product name EYAS: 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, then washed with pure water and dried. After that, a primer layer was formed on the convex surface (object-side surface) of the plastic lens substrate. Specifically, a water-based polyurethane resin liquid (polycarbonate polyol-based polyurethane emulsion; viscosity 100 CPS, solid content concentration 38% by mass) was applied to the convex surface of the plastic lens substrate by spin coating in an environment of 25°C and 50% relative humidity, and then air-dried for 15 minutes to form a primer layer with a thickness of 10 μm. On the above primer layer, a polymerizable composition for photochromic layer formation, prepared as follows, was applied by spin coating to form a coating layer. The surface of this coating layer was irradiated with ultraviolet light (wavelength 405 nm) in a nitrogen atmosphere (oxygen concentration 500 ppm or less) to cure the coating layer and form a photochromic layer. The thickness of the formed photochromic layer was 25 μm. On the above photochromic layer, a polymerizable composition for forming a protective layer, prepared as follows, was applied by spin coating to form a coating layer. The surface of this coating layer was irradiated with ultraviolet light (wavelength 405 nm) in a nitrogen atmosphere (oxygen concentration 500 ppm or less) to cure the coating layer and form a protective layer. The thickness of the formed protective layer was 15 μm.

[0063] <Preparation of Polymerizable Composition for Photochromic Layer Formation> A curable composition was prepared in a plastic container consisting of 20 parts by mass of trimethylolpropane trimethacrylate, 35 parts by mass of BPE oligomer (2,2-bis(4-methacryloyloxypolyethoxyphenyl)propane), 10 parts by mass of EB6A (polyester oligomer hexaacrylate), 10 parts by mass of polyethylene glycol diacrylate with an average molecular weight of 532, and 10 parts by mass of glycidyl methacrylate. To 100 parts by mass of the above curable composition, the following photochromic compound (an indeno-condensed naphthopyran compound represented by the structural formula described in U.S. Patent No. 6,296,785), a photoradical polymerization initiator (bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide (Omnirad 819, manufactured by IGM Resin B.V.)), an antioxidant (bis[3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propionic acid][ethylenebis(oxyethylene)]), and a light stabilizer (bis(1,2,2,6,6-pentamethyl-4-piperidyl) sebacate) were mixed and thoroughly stirred. Then, the mixture was degassed using a rotation-and-revolution type stirring and degassing apparatus. In this way, a curable composition for photochromic layer formation was prepared.

[0064]

[0065] <Preparation of Polymerizable Composition for Protective Layer Formation> In a plastic container, components A and B shown in the table below were mixed with a photopolymerization initiator (Omnirad 819, manufactured by IGM Resins B.V.) and a leveling agent (Dowsil L-7001, manufactured by Dow-Toray), and thoroughly stirred. Then, the mixture was degassed using a rotation-and-revolution type stirring and degassing apparatus. In this way, the curable composition for protective layer formation of Example 1 was prepared.

[0066] In the table below, the values ​​listed in the columns for Component A, Component B, and other (meth)acrylates represent the content of each component (in parts by mass) relative to 100 parts by mass of the total polymerizable compound. In the examples and comparative examples shown in the table below, the polymerizable compounds contained in the polymerizable composition for forming the protective layer are only those listed in the table. In the table below, the values ​​listed in the columns for photopolymerization initiator and leveling agent represent the content (in mass%) of the photopolymerization initiator and leveling agent, respectively, when the total amount of polymerizable compound is 100% by mass.

[0067] The following evaluations (1) to (6) were performed using eyeglass lenses with a protective layer formed using the method described above.

[0068] A hard coat layer was then formed on the spectacle lens that had a protective layer formed using the method described above, using the method described below. The evaluation described in (7) below was then performed using the spectacle lens with the hard coat layer formed in this way.

[0069] <Formation of Hard Coat Layer> 17 parts by mass of γ-glycidoxypropyltrimethoxysilane, 30 parts by mass of methanol, and 28 parts by mass of water-dispersed colloidal silica (solid content 40% by mass, average particle size 15 nm) were added to a glass container equipped with a magnetic stirrer and thoroughly mixed, and stirred at 5°C for 24 hours. Next, 15 parts by mass of propylene glycol monomethyl ether, 0.05 parts by mass of a silica-based surfactant, and 1.5 parts by mass of aluminum acetylacetonate as a curing agent were added and thoroughly stirred, and then filtered to prepare a hard coating solution (polymerizable composition for hard coat layer formation). The hard coating solution was coated onto the surface of the protective layer of the spectacle lens prepared above using the dip-coating method (pulling speed 20 cm / min). Subsequently, a hard coat layer (organosilicon-based cured layer) with a thickness of 3 μm was formed by heating and curing in a heat treatment furnace at a furnace temperature of 100°C for 60 minutes.

[0070] [Evaluation Method] (1) Eyeglass lenses with a crack-resistant protective layer were annealed for 2 hours in an annealing furnace at a furnace temperature of 90°C. The eyeglass lenses removed from the annealing furnace were visually inspected to evaluate the presence or absence of cracks in the protective layer. Five eyeglass lenses were evaluated, and the number of lenses in which no cracks were found was counted. (Evaluation Criteria) A: Five eyeglass lenses (5 / 5) showed no cracks out of five. B: Four eyeglass lenses (4 / 5) or three eyeglass lenses (3 / 5) showed no cracks out of five. C: Two eyeglass lenses (2 / 5), one eyeglass lens (1 / 5), or zero eyeglass lenses (0 / 5) showed no cracks out of five.

[0071] (2) Photochromic performance (T with respect to the reference lens) ＤＲ The difference ΔT ＤＲ Except for the absence of a protective layer, the spectacle lens prepared by the method described in Example 1 was used as the "reference lens." For both Example 1 and the reference lens, the change range T from the initial luminous transmittance to the luminous transmittance after coloring was measured using the following method. ＤＲ The (initial luminous transmittance - luminous transmittance after coloring) was calculated. The T of the spectacle lens in Example 1 ＤＲ to "T ＤＲ (c) , T of the reference lens ＤＲ to "T ＤＲ (d) is called. T with respect to the reference lens ＤＲ The difference ΔT ＤＲ ΔT ＤＲ = T ＤＲ (c)-T ＤＲ (d) was calculated as ΔT. ＤＲ This shows the difference in the above range of change depending on the presence or absence of the protective layer. ΔT ＤＲ The smaller the absolute value of [the protective layer], the less the photochromic performance will degrade due to the addition of the protective layer.

[0072] <Initial Luminous Transmittance> The luminous transmittance of each spectacle lens was determined according to JIS T 7333:2005 before the following light irradiation. The luminous transmittance determined in this way is called the "initial luminous transmittance".

[0073] <Luminous Transmittance During Coloring> Each spectacle lens was irradiated with light from a xenon lamp through an aeromass filter for 15 minutes (900 seconds) to color the photochromic compound in the photochromic layer. The luminous transmittance during this coloring process was determined in accordance with JIS T 7333:2005. The above light irradiation was carried out so that the irradiance and tolerance of irradiance were the values ​​shown in Table 1 below, as specified in JIS T 7333:2005. The luminous transmittance thus determined is called the "luminous transmittance during coloring."

[0074]

[0075] (3) Photochromic performance (difference in fading rate ΔS from the reference lens) ｆａｄｉｎｇ The fading rate of the eyeglass lens and the reference lens of Example 1 was determined by the following method. The fading rate of the eyeglass lens of Example 1 was S ｆａｄｉｎｇ (c) The fading rate of the reference lens is S ｆａｄｉｎｇ (d) The difference in fading rate with respect to the reference lens ΔS ｆａｄｉｎｇ ΔS ｆａｄｉｎｇ = S ｆａｄｉｎｇ (c)-S ｆａｄｉｎｇ (d) was calculated as ΔS. ｆａｄｉｎｇ This shows the difference in fading rate with and without a protective layer.

[0076] <Fading Rate> Each spectacle lens was irradiated with light from a xenon lamp through an aeromass filter for 15 minutes (900 seconds) to color the photochromic compound in the photochromic layer. The transmittance at this coloring stage (measurement wavelength: 550 nm) was measured using a spectrophotometer manufactured by Otsuka Electronics Industry Co., Ltd. The above light irradiation was carried out so that the irradiance and tolerance of irradiance were the values ​​shown in Table 1 above, as specified in JIS T7333:2005. The transmittance measured in this way is called the "transmittance at coloring stage". After measuring the transmittance at coloring stage, the transmittance 60 seconds after the light irradiation was stopped was measured (hereinafter referred to as the "60s faded transmittance"). The fading rate (unit: % / sec) is calculated using the formula: Fading rate = [(60s faded transmittance - Transmittance at coloring stage) / 60]. The larger the value of the fading rate obtained in this way, the faster the fading rate can be said to be.

[0077] (4) Photochromic performance (difference Δt in time to reach 70% luminous transmittance with the reference lens) ７０％Ｔ For each of the eyeglass lens and reference lens in Example 1, the time to reach 70% transmittance was determined by the following method. The time to reach 70% transmittance for the eyeglass lens in Example 1 was t ７０％ (c) Time to reach 70% transmittance of the reference lens ７０％ (d) The difference Δt in the time to reach 70% transmittance with the reference lens. ７０％Ｔ Δt ７０％Ｔ = t ７０％ (c)-t ７０％ (d) was calculated as Δt. ７０％Ｔ This shows the difference in the time it takes to reach 70% visible transmittance with and without a protective layer.

[0078] <Time to Reach 70% Transmittance> After stopping the light irradiation for measuring the transmittance during coloring as described above, the time required for the lens transmittance to recover to 70% (the lens to fade) was calculated, with the initial transmittance set at 100%. This calculated time is defined as the "time to reach 70% transmittance". The smaller the value of the time to reach 70% transmittance calculated in this way, the faster the fading rate can be said to be.

[0079] (5) Weather resistance (ΔTd) The eyeglass lens of Example 1 was subjected to accelerated testing by the following method. Accelerated testing apparatus: Suntest CPS+ manufactured by Toyo Seiki Seisakusho Co., Ltd. Light source: Air-cooled xenon lamp Output: 450W Irradiation time: 50 hours Ambient temperature: 28℃ The luminous transmittance when colored was determined for the eyeglass lens before and after the accelerated testing by the method described above. ΔTd was calculated from the following formula: ΔTd = {(luminous transmittance when colored after accelerated testing) - (luminous transmittance when colored before accelerated testing)} The smaller the value of ΔTd, the better the weather resistance.

[0080] (6) Weather resistance (ΔY.I.) The eyeglass lens of Example 1 was subjected to accelerated weathering using the method described above. The Y.I. (Yellow Index: degree of yellowing) was measured for the eyeglass lens before and after the accelerated weathering test. The Y.I. (degree of yellowing) was measured using a DOT-3 spectrophotometer manufactured by Murakami Color Technology Laboratory Co., Ltd. in accordance with JIS K 7373:2006. From the measurement results, ΔY.I. was calculated using the following formula: ΔY.I. = {(Y.I. after accelerated weathering test) - (Y.I. before accelerated weathering test)} The smaller the value of ΔY.I., the better the weather resistance.

[0081] (7) Scratch Visibility A scratch test was conducted on the surface of the hard coat layer by sliding a 0.7 mm diameter metal indenter at a speed of 25 mm / min while applying a load of 750 g. After the scratch test, the surface of the spectacle lens (hard coat layer surface) was visually observed and the degree of visibility of scratches (scratch marks) was evaluated in three stages from A to C. An evaluation result of "A" means that no scratches were visible, an evaluation result of "B" means that scratches were slightly visible, and an evaluation result of "C" means that scratches were clearly visible.

[0082] [Examples 2-6, Comparative Examples 1-4] Except for the changes shown in the table below, eyeglass lenses were manufactured and various evaluations were performed using the method described for Example 1.

[0083] The results are shown in the table below.

[0084]

[0085]

[0086]

[0087]

[0088]

[0089] From the results shown in the table above, it can be confirmed that the eyeglass lenses of Examples 1 to 6 have a protective layer that is resistant to cracking, scratches are difficult to see, they have excellent weather resistance, and the photochromic performance is not significantly reduced by the presence of the protective layer.

[0090] The various embodiments and forms described herein can be combined in any combination of two or more.

[0091] The embodiments disclosed herein should be considered in all respects to be illustrative and not restrictive. The scope of the invention is indicated by the claims rather than by the foregoing description, and all modifications within the meaning and scope of equivalents of the claims are intended.

[0092] This invention is useful in the technical fields of eyeglasses, goggles, sun visors, helmets, and the like.

Claims

1. A curable composition for forming a protective layer on photochromic articles, comprising the following components A and B: Component A: Polysilsesquioxane having a (meth)acryloyl group Component B: One or more polyfunctional (meth)acrylates selected from the group consisting of polyfunctional (meth)acrylates having an oxyalkylene structure and polyfunctional (meth)acrylates having an epoxy ester structure 2. A curable composition for forming a protective layer on a photochromic article according to claim 1, comprising at least a polyfunctional (meth)acrylate having an oxyalkylene structure as component B.

3. The curable composition for forming a protective layer for a photochromic article according to claim 2, wherein the polyfunctional (meth)acrylate having an oxyalkylene structure is one or more selected from the group consisting of polyfunctional (meth)acrylates represented by the following formula 1 and polyfunctional (meth)acrylates represented by the following formula 2. (In Formula 1, X represents an oxyalkylene structure, and multiple Xs within the molecule are either the same or different oxyalkylene structures. Z represents a hydrogen atom or a methyl group, and multiple Zs within the molecule are either the same or different. a to f are each independently one or more, and the sum of a to f is the total number of oxyalkylene structures within the molecule.) (In Equation 2, R represents an oxyalkylene structure, and multiple Rs in the molecule are either the same or different oxyalkylene structures. Z represents a hydrogen atom or a methyl group, and multiple Zs in the molecule are either the same or different. l to n are each independently one or more, and the sum of l to n is the total number of oxyalkylene structures in the molecule.) 4. A curable composition for forming a protective layer on a photochromic article according to claim 1, comprising at least a polyfunctional (meth)acrylate having an epoxy ester structure as component B.

5. The curable composition for forming a protective layer on a photochromic article according to claim 1, wherein the content of component A is 5 parts by mass or more and 80 parts by mass or less per 100 parts by mass of the total amount of component A and component B.

6. A curable composition for forming a protective layer on a photochromic article according to claim 1, further comprising the following component C: Polyester (meth)acrylate 7. The curable composition for forming a protective layer on a photochromic article according to claim 6, wherein the content of component C is 5 parts by mass or more and 40 parts by mass or less, relative to 100 parts by mass of the total amount of component A, component B, and component C.

8. A photochromic article comprising: a protective layer which is a cured layer obtained by curing the curable composition according to any one of claims 1 to 7; and a photochromic layer which contains a photochromic compound.

9. The photochromic article according to claim 8, wherein the thickness of the protective layer is 1 μm or more and 50 μm or less.

10. The photochromic article according to claim 8, comprising a substrate, the photochromic layer, and the protective layer in this order.

11. The photochromic article according to claim 8, comprising a substrate, the photochromic layer, the protective layer, and an organosilicon-based curing layer in this order.

12. The photochromic article according to claim 8, which is an eyeglass lens.

13. The photochromic article according to claim 8, which is a lens for goggles, a visor portion of a sun visor, or a shield member of a helmet.

14. Eyeglasses equipped with the eyeglass lenses described in claim 12.

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