Polymerizable composition for optical article and optical article

Abstract

Provided is a polymerizable composition for an optical article, said composition including component A and component B below. Component A: A polyfunctional (meth)acrylate having a molecular weight of 500 or more and containing a polyalkylene glycol moiety. Component B: A monofunctional (meth)acrylate represented by formula 1. Component C: A photochromic compound. (In formula 1, R10 represents a hydrogen atom or a methyl group, and R11 represents a straight chain alkyl group with three or more carbon atoms or a branched alkyl group with three or more carbon atoms.)

Description

[Technical Field]

[0001] The present invention relates to a polymerizable composition for an optical article and an optical article. [Background technology]

[0002] A photochromic compound is a compound that exhibits a property (photochromic property) of developing a color when irradiated with light in a photoresponsive wavelength range and fading when not irradiated with light. One method of imparting photochromic property to optical articles such as eyeglass lenses is to provide a coating containing a photochromic compound and a polymerizable compound on a substrate, and then harden this coating to form a hardened layer (photochromic layer) having photochromic property (see, for example, Patent Document 1). [Prior art documents] [Patent documents]

[0003] [Patent Document 1] WO2003 / 011967 Summary of the Invention [Problem to be solved by the invention]

[0004] It is desirable for the above-described photochromic optical article to have a high color density when exposed to light outdoors or the like. Another desirable performance of the optical article is a fast color fading rate after color development by light exposure. However, according to the inventors' investigations, there is a trade-off between color density and color fading rate, and it has been difficult to achieve both a high color density and a fast color fading rate.

[0005] An object of one aspect of the present invention is to provide a polymerizable composition for an optical article that can form a photochromic layer that develops color in high density when irradiated with light and fades rapidly. [Means for solving the problem]

[0006] One aspect of the present invention relates to a polymerizable composition for an optical article (hereinafter also simply referred to as "composition") comprising the following components A, B, and C. Component A: Polyfunctional (meth)acrylate containing a polyalkylene glycol moiety and having a molecular weight of 500 or more Component B: Monofunctional (meth)acrylate represented by the following formula 1 [ka] (In formula 1, R 10 represents a hydrogen atom or a methyl group, and R 11 represents a linear alkyl group having 3 or more carbon atoms or a branched alkyl group having 3 or more carbon atoms. Component C: Photochromic compound

[0007] For example, a photochromic compound undergoes a structural change upon irradiation with light such as sunlight, passing through an excited state. The structure after structural change upon irradiation with light can be called a "colored body." In contrast, the structure before irradiation with light can be called a "colorless body." Note that "colorless" in a colorless body does not necessarily mean completely colorless, but also includes a case where the color is lighter than the colored body. After structural change to a colored body upon irradiation with light and color development occurs, the faster the rate of structural change from the colored body to the colorless body, the faster the fading rate. In the photochromic layer, the easier the molecular movement of the photochromic compound in the matrix formed by the polymerization reaction of the polymerizable compound is, the faster the rate of the structural change. From the perspective of increasing this rate, a flexible matrix is ​​considered desirable. On the other hand, with regard to color density, it is presumed that in order to increase the color density, it is desirable that the intermolecular interaction between the photochromic compound whose structure has changed to a colored body and the matrix is ​​strong. In relation to the above points, the present inventors speculate that Component A can contribute to making the matrix flexible. Specifically, it is believed that the molecular weight of Component A is 500 or more, and Component A has a polyalkylene glycol moiety, which are the reasons why Component A can form a flexible matrix. In addition, the "-CH2-R 11The present inventors believe that the "-CH2-R" moiety can exhibit strong intermolecular interaction with the photochromic compound whose structure has changed to a colored body. 11 However, since component B is a monofunctional (meth)acrylate having such a rigid functional group, in the matrix formed using component B, the "-CH2-R 11 The " " portion is thought to be easily movable. Therefore, it is speculated that the use of component B ensures the flexibility of the matrix. Thus, the present inventors believe that the above composition containing components A and B together with a photochromic compound (component C) makes it possible to form a photochromic layer that exhibits high color density and a rapid color fading rate when colored by exposure to light. However, the present invention is not limited to the speculations described in this specification. [Effects of the Invention]

[0008] According to one aspect of the present invention, there is provided a polymerizable composition for an optical article that can form a photochromic layer that exhibits high color density and a fast color fading rate when colored by light irradiation. Also, according to another aspect of the present invention, there is provided an optical article having a photochromic layer that exhibits high color density and a fast color fading rate when colored by light irradiation. DETAILED DESCRIPTION OF THE INVENTION

[0009] [Polymerizable composition for optical articles] The polymerizable composition for an optical article according to one embodiment of the present invention will be described in further detail below.

[0010] In the present invention and this specification, a polymerizable composition refers to a composition containing a polymerizable compound. A polymerizable compound is a compound having a polymerizable group. A polymerizable composition for an optical article according to one embodiment of the present invention is a polymerizable composition used for producing an optical article, and can be a coating composition for an optical article, more specifically, a coating composition for forming a photochromic layer of an optical article. A coating composition for an optical article refers to a composition that is applied to a substrate or the like for producing an optical article. Examples of optical articles include various lenses such as eyeglass lenses and goggle lenses, visors for sun visors, and helmet shields. For example, eyeglass lenses produced by applying the above composition to a lens substrate have a photochromic layer and can exhibit photochromic properties.

[0011] In the present invention and this specification, the term "(meth)acrylate" is used to encompass both acrylate and methacrylate. An "acrylate" is a compound having one or more acryloyl groups in one molecule. A "methacrylate" is a compound having one or more methacryloyl groups in one molecule. The functionality of a (meth)acrylate is the number of groups selected from the group consisting of acryloyl groups and methacryloyl groups contained in one molecule. In the present invention and this specification, a "methacrylate" refers to a compound containing only methacryloyl groups as (meth)acryloyl groups, and a compound containing both acryloyl and methacryloyl groups as (meth)acryloyl groups is called 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. The term "(meth)acryloyl group" used below encompasses both acryloyl and methacryloyl groups, and the term "(meth)acryloyloxy group" encompasses both acryloyloxy and methacryloyloxy groups. Unless otherwise specified, the groups described herein may be substituted or unsubstituted. When a group has a substituent, examples of the substituent include an alkyl group (e.g., a linear alkyl group having 1 to 6 carbon atoms or a branched alkyl group having 1 to 6 carbon atoms), a hydroxyl group, an alkoxy group (e.g., an alkoxy group having 1 to 6 carbon atoms), a halogen atom (e.g., a fluorine atom, a chlorine atom, or a bromine atom), a cyano group, an amino group, a nitro group, an acyl group, a carboxy group, an aryl group, and a polyether group. Regarding a substituted group, the "carbon number" refers to the number of carbon atoms in the portion excluding the substituent. In the present invention and this specification, the term "linear alkyl group or branched alkyl group" does not encompass cycloalkyl groups. The linear alkyl group or branched alkyl group may be unsubstituted or may have a substituent. It is permissible for a linear or branched alkyl group to have a cycloalkyl group (e.g., a cyclohexyl group) as a substituent. In one embodiment, it is preferred that a linear or branched alkyl group does not have a cycloalkyl group as a substituent.

[0012] <Polymerizable compound> The composition contains, as polymerizable compounds, at least Component A and Component B. Component A and Component B will be described below.

[0013] (Component A) Component A is a polyfunctional (meth)acrylate containing a polyalkylene glycol moiety and having a molecular weight of 500 or more. In the present invention and this specification, the term "polyalkylene glycol moiety" refers to a polyfunctional (meth)acrylate having a molecular weight of 500 or more and having a molecular weight of 500 or more. [ka] In formula 2, R represents an alkylene group, n represents the number of repeating alkoxy groups represented by RO and is 2 or more. * represents the bonding position where the partial structure represented by formula 2 is bonded to an adjacent atom. The number of carbon atoms in the alkylene group represented by R can be 1 or more or 2 or more, and can be, for example, 5 or less or 4 or less. Specific examples of the alkylene group represented by R include an ethylene group, a propylene group, and a tetramethylene group. n is 2 or more and can be, for example, 30 or less, 25 or less, or 20 or less. In one embodiment, component A can have the above partial structure in which R represents an ethylene group, i.e., a polyethylene glycol moiety.

[0014] The molecular weight of component A is 500 or more. In the present invention and this specification, the molecular weight of the multimer is determined by the structural formula determined by structural analysis of the compound or the theoretical molecular weight calculated from the raw material charging ratio during production. The molecular weight of component A is 500 or more, preferably 510 or more, more preferably 520 or more, preferably 550 or more, more preferably 570 or more, even more preferably 600 or more, even more preferably 630 or more, and even more preferably 650 or more. From the viewpoint of increasing the hardness of the photochromic layer, the molecular weight of component A is preferably, for example, 2000 or less, 1500 or less, 1200 or less, 1000 or less, or 800 or less.

[0015] Component A is a polyfunctional (meth)acrylate, and may be, for example, a difunctional, trifunctional, tetrafunctional, or pentafunctional (meth)acrylate, and is preferably a difunctional or trifunctional (meth)acrylate. Component A may contain only acryloyl groups, only methacryloyl groups, or both acryloyl and methacryloyl groups as (meth)acryloyl groups. That is, Component A may be an acrylate or methacrylate.

[0016] In one embodiment, component A can be an acyclic polyfunctional (meth)acrylate. In the present invention and this specification, "acyclic" means not containing a cyclic structure. In contrast, "cyclic" means containing a cyclic structure. An acyclic polyfunctional (meth)acrylate refers to a bifunctional or higher functional (meth)acrylate that does not contain a cyclic structure. A specific example of such component A is a polyalkylene glycol di(meth)acrylate represented by the following formula 3.

[0017] [ka]

[0018] In formula 3, R 1 and R 2 each independently represents a hydrogen atom or a methyl group, R represents an alkylene group, and n represents the number of repetitions of the alkoxy group represented by RO and is 2 or more. R and n are as described above for the partial structure represented by formula 2. The polyalkylene glycol di(meth)acrylate represented by formula 3 may contain only acryloyl groups, only methacryloyl groups, or both acryloyl and methacryloyl groups as (meth)acryloyl groups. Specific examples of the polyalkylene glycol di(meth)acrylate represented by formula 3 include polyethylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, and polytetramethylene glycol di(meth)acrylate.

[0019] Specific examples of component A include tri(meth)acrylates represented by the following formula 4. The tri(meth)acrylates represented by formula 4 may contain only acryloyl groups, only methacryloyl groups, or both acryloyl and methacryloyl groups as (meth)acryloyl groups.

[0020] [ka]

[0021] In formula 4, R 40 , R 41 , R 44 , R 45 , R 47 and R 48 each independently represents an alkylene group, R 43 represents an alkyl group, and R 42 , R 46 and R 49 each independently represents a hydrogen atom or a methyl group; 41 n2 represents the number of repeating alkoxy groups represented by the formula: 45 n3 represents the number of repeating alkoxy groups represented by the formula: 48 The number of repetitions of the alkoxy group represented by the formula (I) is 2 or more.

[0022] Equation 4 will be explained in more detail below.

[0023] R in Equation 4 41 , R 45 and R 48 In Formula 4, n1, n2, and n3 are as described above for n in Formula 2. In Formula 4, R 41 , R 45 and R 48 may be the same, or two or three may be different. The same applies to n1, n2, and n3.

[0024] R42 , R 46 and R 49 each independently represents a hydrogen atom or a methyl group. The tri(meth)acrylate represented by formula 4 may contain only acryloyl groups, only methacryloyl groups, or both acryloyl groups and methacryloyl groups as (meth)acryloyl groups.

[0025] R 43 The number of carbon atoms in the alkyl group represented by R can be 1 or more, or 2 or more, and can be, for example, 5 or less, or 4 or less. 43 The alkyl group represented by R can be a straight chain alkyl group or a branched alkyl group. 43 Specific examples of the alkyl group represented by the formula include a methyl group and an ethyl group.

[0026] R 40 , R 44 and R 47 each independently represents an alkylene group. The number of carbon atoms in such an alkylene group can be 1 or more or 2 or more, and can be, for example, 5 or less or 4 or less. Specific examples thereof include an ethylene group, a propylene group, and a tetramethylene group.

[0027] Specific examples of the tri(meth)acrylate represented by formula 4 include trimethylolpropane polyoxyethylene ether tri(meth)acrylate.

[0028] (Component B) Component B is a monofunctional (meth)acrylate represented by the following formula 1.

[0029] [ka]

[0030] Formula 1 will be explained in more detail below.

[0031] In formula 1, R 10represents a hydrogen atom or a methyl group. The monofunctional (meth)acrylate represented by formula 1 may be an acrylate or a methacrylate.

[0032] R 11 R represents a linear alkyl group having 3 or more carbon atoms or a branched alkyl group having 3 or more carbon atoms. These alkyl groups may be unsubstituted or may have a substituent. The substituent is not particularly limited, and examples thereof include the various substituents described above. 11 The number of carbon atoms in the linear or branched alkyl group represented by the formula (I) is 3 or more, and from the viewpoint of increasing the fading rate, it is preferably 4 or more, more preferably 5 or more, and further preferably 6 or more, 7 or more, 8 or more, 9 or more, 10 or more, and 11 or more. On the other hand, from the viewpoint of the solubility of the photochromic compound (component C) in the composition, the number of carbon atoms is preferably 15 or less, more preferably 14 or less, and further preferably 13 or less, and 12 or less.

[0033] The molecular weight of the monofunctional (meth)acrylate represented by Formula 1 can be, for example, in the range of 100 to 300, but is not limited to this range. Specific examples of the monofunctional (meth)acrylate represented by Formula 1 include n-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, isodecyl (meth)acrylate, and n-lauryl (meth)acrylate.

[0034] In the composition, the content of component A is preferably 50% by mass or more, more preferably 55% by mass or more, and even more preferably 60% by mass or more, based on 100% by mass of the total amount of polymerizable compounds contained in the composition. In one embodiment, component A can be the component that accounts for the largest proportion of the multiple polymerizable compounds contained in the composition. Furthermore, the content of component A can be 90% by mass or less, 85% by mass or less, or 80% by mass or less, based on 100% by mass of the total amount of polymerizable compounds contained in the composition. In one embodiment, the composition can contain only one type of component A, and in another embodiment, it can contain two or more types. When two or more types of component A are contained, the content of component A mentioned above is the total content of the two or more types. This also applies to the contents of the other components.

[0035] The content of component B is preferably 5% by mass or more, more preferably 10% by mass or more, and even more preferably 15% by mass or more, based on 100% by mass of the total amount of polymerizable compounds contained in the composition. The content of component B is preferably 30% by mass or less, and more preferably 25% by mass or less, based on 100% by mass of the total amount of polymerizable compounds contained in the composition.

[0036] In one embodiment, the composition may contain only component A and component B as polymerizable compounds. In another embodiment, the composition may contain one or more other polymerizable compounds in addition to component A and component B. The content of the polymerizable compounds in the composition (i.e., the total content of the multiple polymerizable compounds) may be, for example, 80% by mass or more, 85% by mass or more, or 90% by mass or more, based on 100% by mass of the total amount of the composition. Furthermore, the content of the polymerizable compounds in the composition may be, for example, 99% by mass or less, 95% by mass or less, 90% by mass or less, or 85% by mass or less, based on 100% by mass of the total amount of the composition. In the present invention and this specification, with respect to content, the "total amount of the composition" refers to the total amount of all components excluding the solvent in a solvent-containing composition. The composition may or may not contain a solvent. When a solvent is contained, any solvent may be used in any amount as long as it does not inhibit the polymerization reaction of the polymerizable composition.

[0037] <Photochromic compound (ingredient C)> The composition contains a photochromic compound (component C) in addition to the polymerizable compound. The photochromic compound contained in the composition can be a known compound exhibiting photochromic properties. The photochromic compound can exhibit photochromic properties, for example, when exposed to ultraviolet light. Examples of photochromic compounds include azobenzenes, spiropyrans, spirooxazines, naphthopyrans, indenonaphthopyrans, phenanthropyrans, hexaarylbisimidazoles, donor-acceptor Stenhouse adducts (DASA), salicylideneanilines, dihydropyrenes, anthracene dimers, fulgides, diarylethenes, phenoxynaphthacenequinones, and stilbenes. Preferred photochromic compounds include fulgimide compounds, spirooxazine compounds, chromene compounds, and indeno-fused naphthopyran compounds. Further, the photochromic compound may be one or more compounds selected from the group consisting of photochromic compounds represented by general formula A, photochromic compounds represented by general formula B, and photochromic compounds represented by general formula C, as described in WO2022 / 138966. The photochromic compounds may be used alone or in combination of two or more. The content of the photochromic compound in the composition may be, for example, about 0.1 to 15% by mass, with the total amount of the composition being 100% by mass, but is not limited to this range.

[0038] <Other ingredients> In addition to the polymerizable compound and the photochromic compound, the composition may contain one or more of various additives that can be usually contained in polymerizable compositions, at any content. Examples of additives that can be contained in the composition include a polymerization initiator for promoting the polymerization reaction.

[0039] For example, a known polymerization initiator can be used as the polymerization initiator, a radical polymerization initiator is preferred, and it is more preferred that the polymerization initiator contains only a radical polymerization initiator. Furthermore, a photopolymerization initiator or a thermal polymerization initiator can be used as the polymerization initiator, and a photopolymerization initiator is preferred from the viewpoint of progressing the polymerization reaction in a short time. Examples of the photoradical polymerization initiator include benzoin ketals such as 2,2-dimethoxy-1,2-diphenylethan-1-one; α-hydroxyketones such as 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, and 1-[4-(2-hydroxyethoxy)phenyl]-2-hydroxy-2-methyl-1-propan-1-one; 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, bis(2,6-dimethoxybenzoyl)phenylphosphine oxide, and the like. phosphine oxides 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-phenanthraquinone, 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 benzil dimethyl ketal; acridine compounds such as 9-phenylacridine and 1,7-bis(9,9'-acridinylheptane); N-phenylglycine, coumarin, and the like. In the 2,4,5-triarylimidazole dimer, the substituents on the aryl groups of the two triarylimidazole moieties may be the same to give a symmetrical compound, or may be different to give an asymmetrical compound. A thioxanthone compound may also 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 viewpoints of curability, transparency, and heat resistance. The content of the polymerization initiator may be, for example, in the range of 0.1 to 5% by mass, with the total amount of the composition being 100% by mass.

[0040] The composition may further contain any amount of known additives that are typically added to compositions containing a photochromic compound, such as surfactants, antioxidants, radical scavengers, light stabilizers, ultraviolet absorbers, color inhibitors, antistatic agents, fluorescent dyes, dyes, pigments, fragrances, plasticizers, and silane coupling agents. Known compounds may be used as these additives.

[0041] The composition can be prepared by mixing the various components described above simultaneously or sequentially in any order.

[0042] [Optical articles] One aspect of the present invention relates to an optical article having a substrate and a photochromic layer formed by curing the above-described composition.

[0043] The optical article will now be described in more detail.

[0044] <Base material> The optical article may have a photochromic layer on a substrate selected depending on the type of optical article. As an example of the substrate, a spectacle lens substrate may be a plastic lens substrate or a glass lens substrate. The glass lens substrate may be, for example, a lens substrate made of inorganic glass. A plastic lens substrate is preferred as the lens substrate because it is lightweight, shatter-resistant, and easy to handle. Examples of plastic lens substrates include (meth)acrylic resins, styrene resins, polycarbonate resins, allyl resins, allyl carbonate resins such as diethylene glycol bisallyl carbonate resin (CR-39), vinyl resins, polyester resins, polyether resins, urethane resins obtained by reacting an isocyanate compound with a hydroxy compound such as diethylene glycol, thiourethane resins obtained by reacting an isocyanate compound with a polythiol compound, and cured products (generally referred to as transparent resins) obtained by curing a curable composition containing a (thio)epoxy compound having one or more disulfide bonds in the molecule. The lens substrate may be either undyed (colorless lenses) or dyed (dyed lenses). The refractive index of the lens substrate can be, for example, about 1.50 to 1.75. However, the refractive index of the lens substrate is not limited to the above range, and may be within the above range or may deviate above or below the above range. In the present invention and this specification, the refractive index refers to the refractive index for light with a wavelength of 500 nm. Furthermore, the lens substrate 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] The spectacle lens can be any of various lenses, such as a single-vision lens, a multifocal lens, or a progressive-power lens. The type of lens is determined by the surface shapes of both sides of the lens substrate. The surface of the lens substrate may be convex, concave, or flat. In typical lens substrates and spectacle lenses, the object-side surface is convex and the eyeball-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 eyeball-side surface.

[0046] <Photochromic layer> The photochromic layer of the optical article can be formed by applying the composition directly or indirectly via one or more other layers to the surface of a substrate and then curing the applied composition. Examples of other layers include a primer layer for improving adhesion between the photochromic layer and the substrate. Such primer layers are known. Known coating methods such as spin coating and dip coating can be used as the coating method, with spin coating being preferred from the viewpoint of uniformity of the coating. The curing treatment can be light irradiation and / or heat treatment, with light irradiation being preferred from the viewpoint of progressing the curing reaction in a short period of time. The curing treatment conditions can be determined depending on the types of various components (such as the polymerizable compound and polymerization initiator described above) contained in the composition and the composition of the composition. The thickness of the photochromic layer thus formed is preferably in the range of 5 to 80 μm, and more preferably in the range of 20 to 60 μm.

[0047] The optical article having the photochromic layer may or may not have one or more functional layers in addition to the photochromic layer. Examples of the functional layer include layers known as functional layers for optical articles, such as a protective layer for improving the durability of the optical article, an antireflection layer, a water-repellent or hydrophilic antifouling layer, and an antifogging layer.

[0048] One example of the optical article is a spectacle lens. Other examples of the optical article include a goggle lens, a sun visor, and a helmet shield. The composition is applied to a substrate for these optical articles, and the applied composition is cured to form a photochromic layer, thereby providing an optical article with antiglare properties.

[0049] [glasses] One aspect of the present invention relates to eyeglasses equipped with eyeglass lenses, which are one form of the optical article. Details of the eyeglass lenses included in the eyeglasses are as described above. By including such eyeglass lenses, the eyeglasses can, for example, exhibit anti-glare effects similar to sunglasses outdoors, as the photochromic compound included in the photochromic layer changes color when irradiated with sunlight, and regain transparency when the eyeglasses return indoors as the photochromic compound fades. Known technologies can be applied to the construction of the frames and other components of the eyeglasses. [Example]

[0050] The present invention will be further described below with reference to examples, but the present invention is not limited to the embodiments shown in the examples.

[0051] [Example 1] <Preparation of polymerizable composition for optical article (coating composition for forming photochromic layer)> In a plastic container, 80 parts by mass of polyethylene glycol dimethacrylate (in the above-mentioned formula 3, n = 14, R is an ethylene group, molecular weight 736), which is component A, and 20 parts by mass of a monofunctional (meth)acrylate shown in Table 2 were mixed. The resulting mixture of polymerizable compounds was mixed with the following photochromic compound (an indeno-fused naphthopyran compound represented by the structural formula described in U.S. Pat. No. 6,296,785), a photoradical polymerization initiator (bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide (Omnirad 819, manufactured by IGM Resin BV)), 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) and thoroughly stirred. The mixture was then degassed using a rotation-revolution type stirring and degassing device. This produced a polymerizable composition for optical articles (a coating composition for forming a photochromic layer). The contents of the above components, relative to the total amount of the composition (100% by mass), are 94.9% by mass for the polymerizable compound mixture, 3% by mass for the photochromic compound, 0.3% by mass for the photoradical polymerization initiator, 0.9% by mass for the antioxidant, and 0.9% by mass for the light stabilizer. In the above composition, relative to the total amount of the polymerizable compounds (100% by mass), the contents of component A and component B are 80% by mass and 20% by mass, respectively.

[0052] [ka]

[0053] <Production of eyeglass lenses> A plastic lens substrate (manufactured by HOYA Corporation under the trade name HI-LUX; center thickness 2.2 mm, radius 70 mm, S 0.00) was washed with pure water and dried. The above-prepared coating composition for forming a photochromic layer was then applied to the convex surface (object-side surface) of the plastic lens substrate by spin coating. Spin coating was performed using the method described in JP 2005-218994 A. The composition applied to the plastic lens substrate was then irradiated with ultraviolet light (wavelength 405 nm) in a nitrogen atmosphere (oxygen concentration 500 ppm or less), curing the composition and forming a photochromic layer. The photochromic layer thus formed was 40 μm thick. In this way, a spectacle lens having a photochromic layer was produced.

[0054] [Examples 2 to 4, Comparative Examples 1 to 3] Spectacle lenses were produced in the same manner as in Example 1, except that the monofunctional (meth)acrylate was changed to one shown in Table 2.

[0055] [Reference example 1] A spectacle lens was produced in the same manner as in Example 1, except that no monofunctional (meth)acrylate was used and 100 parts by mass of the same component A as in Example 1 was used.

[0056] [Evaluation method] (1) Evaluation of color density The color density was evaluated by the following method in accordance with JIS T7333:2005. The photochromic layer (a cured layer obtained by curing the polymerizable composition) of each eyeglass lens was irradiated with light from a xenon lamp through an aeromass filter for 15 minutes (900 seconds) to cause the photochromic compound in the photochromic layer to develop color. The transmittance (measurement wavelength: 550 nm) during this color development was measured using a spectrophotometer manufactured by Otsuka Electronics Co., Ltd. The light irradiation was carried out so that the irradiance and irradiance tolerance, as specified in JIS T7333:2005, were as shown in Table 1 below.

[0057] [Table 1]

[0058] The smaller the value of the transmittance measured above (hereinafter referred to as "transmittance when colored"), the higher the concentration of color developed by the photochromic compound.

[0059] (2) Evaluation of fading speed After measuring the transmittance at color development in (1) above, the transmittance was measured 60 seconds after light irradiation was stopped (hereinafter referred to as "transmittance at 60 seconds after fading"). The fading rate (unit: % / second) was calculated using the formula: fading rate = [(transmittance at 60 seconds after fading - transmittance at color development) / 60]. The higher the value of the fading rate thus calculated, the faster the fading rate.

[0060] (3) Evaluation of solubility For each of the Examples, Comparative Examples, and Reference Examples, the polymerizable compositions for optical articles (coating compositions for forming photochromic layers) prepared were visually observed. If no residual photochromic compound was found, the solubility was evaluated as "A," and if residual photochromic compound was found, the solubility was evaluated as "B."

[0061] The above results are shown in Table 2.

[0062] [Table 2]

[0063] As shown below, the monofunctional (meth)acrylate used in Examples 1 to 4 is a monofunctional (meth)acrylate represented by Formula 1. In contrast, the monofunctional (meth)acrylate used in Comparative Examples 1 to 3 is a monofunctional (meth)acrylate that does not have the structure of Formula 1. As shown in Table 2, in Comparative Examples 1 to 3, the color density increased but the fading rate slowed down compared to Reference Example 1 due to the addition of monofunctional (meth)acrylate. In contrast to this, in Examples 1 to 4, compared to Reference Example 1, the addition of monofunctional (meth)acrylate increased the color density and accelerated the fading rate. The above results confirm that the polymerizable composition containing Components A to C makes it possible to form a photochromic layer that exhibits high color density when colored by irradiation with light and a rapid color fading rate.

[0064] [ka]

[0065] [ka]

[0066] [ka]

[0067] [ka]

[0068] [ka]

[0069] [ka]

[0070] [ka]

[0071] Finally, the above-mentioned aspects will be summarized.

[0072] [1] A polymerizable composition for an optical article, comprising the following components A, B, and C: Component A: Polyfunctional (meth)acrylate containing a polyalkylene glycol moiety and having a molecular weight of 500 or more Component B: Monofunctional (meth)acrylate represented by the following formula 1 [ka] (In formula 1, R 10 represents a hydrogen atom or a methyl group, and R 11 represents a linear alkyl group having 3 or more carbon atoms or a branched alkyl group having 3 or more carbon atoms. Component C: Photochromic compound [2] The polymerizable composition for an optical article according to [1], wherein the polyalkylene glycol moiety of Component A is a polyethylene glycol moiety. [3] The polymerizable composition for an optical article according to [1] or [2], wherein component A is a difunctional or trifunctional (meth)acrylate. [4] In formula 1, R 11 The polymerizable composition for an optical article according to any one of [1] to [3], wherein the alkyl group represented by the following formula has 11 or more and 15 or less carbon atoms. [5] a substrate; a photochromic layer obtained by curing the polymerizable composition for an optical article according to any one of [1] to [4]; An optical article having the following: [6] The optical article according to [5], which is a spectacle lens. [7] The optical article according to [5], which is a lens for goggles. [8] The optical article according to [5], which is a visor part of a sun visor. [9] The optical article according to [5], which is a shielding member for a helmet.

[10] Eyeglasses equipped with the eyeglass lenses described in [6].

[0073] Two or more of the various aspects and configurations described herein may be combined in any combination.

[0074] The embodiments disclosed herein should be considered to be illustrative in all respects and not restrictive. The scope of the present invention is defined by the claims, not by the above description, and is intended to include all modifications within the meaning and scope of the claims. [Industrial Applicability]

[0075] The present invention is useful in the technical fields of eyeglasses, goggles, sun visors, helmets, etc.

Claims

1. Contains the following components A, B, and C, A polymerizable composition for optical articles, wherein the content of component A is 60% by mass or more and the content of component B is 15% by mass or more and 25% by mass or less, where the total amount of polymerizable compounds contained in the composition is 100% by mass. Component A: a polyfunctional (meth)acrylate containing a polyalkylene glycol moiety and having a molecular weight of 500 or more Component B: a monofunctional (meth)acrylate represented by the following formula 1 【Chemistry 1】 (In formula 1, R １０ represents a hydrogen atom or a methyl group, R １１ represents a linear alkyl group having 3 to 12 carbon atoms or a branched alkyl group having 3 to 12 carbon atoms. Component C: Photochromic compound

2. The polymerizable composition for an optical article according to claim 1 , wherein the polyalkylene glycol moiety contained in Component A is a polyethylene glycol moiety.

3. 2. The polymerizable composition for an optical article according to claim 1, wherein component A is a difunctional or trifunctional (meth)acrylate.

4. The polymerizable composition for an optical article according to claim 2, wherein component A is a difunctional or trifunctional (meth)acrylate.

5. In formula 1, R １１ The polymerizable composition for an optical article according to claim 1 , wherein the alkyl group represented by the formula (I) has 11 or more and 12 or less carbon atoms.

6. In formula 1, R １１ The polymerizable composition for an optical article according to claim 2 , wherein the alkyl group represented by the formula (I) has 11 or more and 12 or less carbon atoms.

7. In formula 1, R １１ The polymerizable composition for an optical article according to claim 3 , wherein the alkyl group represented by the formula (I) has 11 or more and 12 or less carbon atoms.

8. In formula 1, R １１ The polymerizable composition for an optical article according to claim 4 , wherein the alkyl group represented by the formula (I) has 11 or more and 12 or less carbon atoms.

9. A substrate; A photochromic layer obtained by curing the polymerizable composition for an optical article according to any one of claims 1 to 8; An optical article having the following structure.

10. 10. The optical article according to claim 9, which is a spectacle lens.

11. The optical article according to claim 9, which is a lens for goggles, a visor portion of a sun visor, or a shield member for a helmet.

12. Eyeglasses comprising the eyeglass lens according to claim 10.

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