Photochromic compositions, photochromic articles and glasses

Abstract

Provided is a photochromic composition comprising one or more types of compounds represented by general formula A and one or more types of compounds represented by general formula B. In general formula A, R1, R2, B1, and B2 each independently represent a hydrogen atom or a substituent, and R3 to R6 each independently represent a hydrogen atom or an electron-withdrawing group, where one or more of R3 to R6 represents an electron-withdrawing group. In general formula B, R7 to R12, B3, and B4 each independently represent a hydrogen atom or a substituent, and R13 and R14 each independently represent a hydrogen atom or an electron-donating group, where one or more of R13 and R14 represents an electron-donating group.

Description

[Technical field]

[0001] The present invention relates to photochromic compositions, photochromic articles and eyeglasses. [Background technology]

[0002] A photochromic compound is a compound that has a property (photochromic property) of coloring when irradiated with light in a wavelength range having photoresponsiveness and fading when not irradiated. For example, Patent Document 1 discloses a naphthopyran-based compound having photochromic property. [Prior art documents] [Patent documents]

[0003] [Patent Document 1] WO2000 / 15631 Summary of the Invention [Problem to be solved by the invention]

[0004] Methods for imparting photochromic properties to optical articles such as eyeglass lenses include a method of incorporating a photochromic compound into a substrate and a method of forming a layer containing a photochromic compound. The desired performance of optical articles imparted with photochromic properties in this way includes a high coloring density when colored in the visible range (wavelength 380 to 780 nm) and a fast fading speed after coloring by light irradiation.

[0005] An object of one aspect of the present invention is to provide a photochromic article that exhibits high coloring density and rapid fading speed when colored in the visible range. [Means for solving the problem]

[0006] One aspect of the present invention relates to a photochromic article comprising one or more compounds represented by the following general formula A and one or more compounds represented by the following general formula B:

[0007] Another aspect of the present invention relates to a photochromic composition containing one or more compounds represented by the following general formula A and one or more compounds represented by the following general formula B:

[0008] [ka]

[0009] In general formula A, R 1 , R 2 , B 1 and B. 2 each independently represents a hydrogen atom or a substituent; R 3 ~R 6 each independently represents a hydrogen atom or an electron-withdrawing group, provided that R 3 ~R 6 One or more of represents an electron withdrawing group.

[0010] [ka]

[0011] In general formula B, R 7 ~R 12 , B 3 and B. 4 each independently represents a hydrogen atom or a substituent; R 13 and R 14 each independently represents a hydrogen atom or an electron-donating group, provided that R 13 and R 14 At least one of represents an electron donating group.

[0012] As a result of intensive research, the present inventors have newly discovered that by combining a compound represented by general formula A with a compound represented by general formula B, it is possible to provide a photochromic article that can be colored at a high concentration in the visible range. This is presumably because the compound represented by general formula A and the compound represented by general formula B have different absorption peak positions in the visible range, and therefore, by combining these compounds, it is possible to color at a high concentration in a wide wavelength range. However, the present invention is not limited by the presumption described in this specification. Furthermore, it has also been newly discovered that by combining a compound represented by general formula A with a compound represented by general formula B, it is possible to provide a photochromic article that can exhibit a fast fading speed. Effect of the Invention

[0013] According to one aspect of the present invention, a photochromic article can be provided that exhibits high coloring density and rapid fading speed when colored in the visible range. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0014] For example, a photochromic compound undergoes structural transformation into a colored body through an excited state upon irradiation with light such as sunlight. The structure after structural transformation through light irradiation can be called a "colored body". In contrast, the structure before light irradiation can be called a "colorless body". However, the term "colorless" in the case of a colorless body does not mean that it is completely colorless, but also includes cases where the color is lighter than that of the colored body. The structure of general formula A and the structure of general formula B are each a colorless body structure.

[0015] In the present invention and this specification, the term "photochromic article" refers to an article containing a photochromic compound. A photochromic article according to one embodiment of the present invention contains, as photochromic compounds, one or more compounds represented by general formula A and one or more compounds represented by general formula B. The photochromic compound can be contained in the substrate of the photochromic article, and / or in the photochromic layer of a photochromic article having a substrate and a photochromic layer. The term "photochromic layer" refers to a layer containing a photochromic compound.

[0016] In the present invention and this specification, the term "photochromic composition" refers to a composition containing a photochromic compound. The photochromic composition according to one embodiment of the present invention contains, as photochromic compounds, one or more compounds represented by general formula A and one or more compounds represented by general formula B, and can be used for producing the photochromic article according to one embodiment of the present invention.

[0017] In the present invention and the present specification, various substituents, i.e., R 1 , R 2 , B 1 , B 2 R in general formula B 7 ~R 12 , B 3 and B. 4 In addition, when each group described later has a substituent, the substituent can be independently represented by any one of the following: linear or branched alkyl groups having 1 to 18 carbon atoms, such as a hydroxy group, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, or a hexyl group; a monocyclic or bicyclic aliphatic alkyl group having 5 to 18 carbon atoms, such as a cyclopentyl group or a cyclohexyl group; linear or branched alkoxy groups having 1 to 24 constituent atoms, such as a methoxy group, an ethoxy group, or a butoxy group; a non-aromatic cyclic substituent having 1 to 24 constituent atoms; linear or branched alkyl groups having 1 to 18 carbon atoms, such as a trifluoromethyl group. perfluoroalkyl groups such as the above, linear or branched perfluoroalkoxy groups such as trifluoromethoxy group, linear or branched alkylsulfide groups having 1 to 24 constituent atoms such as methylsulfide group, ethylsulfide group, butylsulfide group, etc., aryl groups such as phenyl group, naphthyl group, anthracenyl group, fluoranthenyl group, phenanthryl group, pyranyl group, perylenyl group, styryl group, fluorenyl group, etc., aryloxy groups such as phenyloxy group, and phenylsulfide group. heteroaryl groups such as a pyridyl group, a furanyl group, a thienyl group, a pyrrolyl group, a benzofuranyl group, a benzothiophenyl group, an indolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, a diazolyl group, a triazolyl group, a quinolinyl group, a phenothiazinyl group, a phenoxazinyl group, a phenazinyl group, a thianthryl group, and an acridinyl group; an amino group (-NH2); a monoalkylamino group such as a monomethylamino group; and a dimethylamino group. a dialkylamino group such as a monophenylamino group, a diarylamino group such as a diphenylamino group, a piperidino group, a morpholino group, a thiomorpholino group, a tetrahydroquinolino group, a tetrahydroisoquinolino group, a cyclic amino group, an ethynyl group, a mercapto group, a silyl group, a sulfonic acid group, an alkylsulfonyl group, a formyl group, a carboxy group, a cyano group, and a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, or the like; m or R m and one or more identical or different R m Substituents substituted with; It can be.

[0018] The above Rm and one or more identical or different R m An example of a substituent substituted with R is a structure in which an alkoxy group is further substituted at the terminal carbon atom of the alkoxy group, and the terminal carbon atom of this alkoxy group is further substituted with an alkoxy group. m and one or more identical or different R m Another example of a substituent substituted with R is a phenyl group having the same or different R m However, the present invention is not limited to such examples.

[0019] In the present invention and this specification, the terms "number of carbon atoms" and "number of constituent atoms" refer to the numbers including the number of carbon atoms or atoms of the substituent in a group having a substituent.

[0020] In the present invention and this specification, various substituents, i.e., R 1 , R 2 , B 1 , B 2 R in general formula B 7 ~R 12 , B 3 and B. 4In addition, when each group described later has a substituent, the substituent may be independently a solubilizing group. In the present invention and this specification, the term "solubilizing group" refers to a substituent that can contribute to increasing compatibility with any liquid or a specific liquid. As the solubilizing group, a substituent that can contribute to promoting the thermal motion of the molecules of the compound by having this substituent, such as an alkyl group having a linear, branched or cyclic structure with 4 to 50 carbon atoms, a linear, branched or cyclic alkoxy group having 4 to 50 constituent atoms, a linear, branched or cyclic silyl group having 4 to 50 constituent atoms, a group in which a part of the above groups is replaced with a silicon atom, a sulfur atom, a nitrogen atom, a phosphorus atom, or the like, or a combination of two or more of the above groups, is suitable. A compound having a solubilizing group as a substituent can prevent the solute from solidifying by inhibiting the distance between solute molecules from approaching each other, or can create a molecular aggregation state close to a liquid by lowering the melting point and / or glass transition temperature of the solute. Thus, the solubilizing group can liquefy a solute or increase the solubility of a compound having this substituent in a liquid. In one embodiment, the solubilizing group is preferably a linear alkyl group such as n-butyl, n-pentyl, n-hexyl, or n-octyl, a branched alkyl group such as tert-butyl, or a cyclic alkyl group such as cyclopentyl or cyclohexyl.

[0021] The above-mentioned substituent may be preferably a substituent selected from the group consisting of a methoxy group, an ethoxy group, a phenoxy group, a methylsulfide group, an ethylsulfide group, a phenylsulfide group, a trifluoromethyl group, a phenyl group, a naphthyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, a phenothiazinyl group, a phenoxazinyl group, a phenazinyl group, an acridinyl group, a dimethylamino group, a diphenylamino group, a piperidino group, a morpholyl group, a thiomorpholino group, a cyano group, and a solubilizing group, and more preferably a substituent selected from the group consisting of a methoxy group, a phenoxy group, a methylsulfide group, a phenylsulfide group, a trifluoromethyl group, a phenyl group, a dimethylamino group, a diphenylamino group, a piperidino group, a morpholyl group, a thiomorpholino group, a cyano group, and a solubilizing group.

[0022] In the present invention and this specification, the term "electron-withdrawing group" refers to a substituent that is more likely to attract electrons from the atom to which it is bonded than a hydrogen atom. The electron-withdrawing group can attract electrons as a result of substituent effects such as inductive effect and mesomeric effect (or resonance effect). Specific examples of the electron-withdrawing group include halogen atoms (fluorine atom: -F, chlorine atom: -Cl, bromine atom: -Br, iodine atom: -I), trifluoromethyl group: -CF3, nitro group: -NO2, cyano group: -CN, formyl group: -CHO, acyl group: -COR (R is a substituent), alkoxycarbonyl group: -COOR, carboxy group: -COOH, substituted sulfonyl group: -SOR (R is a substituent), sulfo group: -SOH, etc. Suitable electron-withdrawing groups include fluorine atoms, which are electron-withdrawing groups with high electronegativity, and para-position substituent constant σ based on Hammett's rule. p can be exemplified by electron-withdrawing groups in which

[0023] In the present invention and this specification, the term "electron-donating group" refers to a substituent that is more likely to donate electrons to the atom to which it is bonded than a hydrogen atom. The electron-donating group can be a substituent that is more likely to donate electrons as a sum of inductive effect, mesomeric effect (or resonance effect), and the like. Specific examples of the electron-donating group include a hydroxy group: -OH, a thiol group: -SH, an alkoxy group: -OR (R is an alkyl group), an alkylsulfide group: -SR (R is an alkyl group), an arylsulfide group, an acetyl group: -OCOCH3, an amino group: -NH2, an alkylamide group: -NHCOCH3, a dialkylamino group: -N(R)2 (two Rs may be the same or different alkyl groups or aryl groups, and Rs may be bonded to each other to form a ring structure), and a methyl group. Suitable electron-donating groups include those having a para-position substituent constant σ based on the Hammett rule. p can be exemplified by electron donating groups in which the value of

[0024] Para-position substituent constant σ based on Hammett's rule p (Source: Graduate School Organic Chemistry (Vol. 1) (1988) edited by Iwamura Hide, Noyori Ryoji, Nakai Takeshi, and Kitagawa Isao) A specific example is shown below. -N(CH3)2:-0.83 -OCH3:-0.27 -t-C4H9:-0.20 -CH3:-0.17 -C2H5:-0.15 -C6H5:-0.01 (-H:0) -F:+0.06 -Cl: +0.27 -Br:+0.23 -CO2C2H5:+0.45 -CF3: +0.54 -CN:+0.66 -SO2CH3:+0.72 -NO2:+0.78

[0025] The compounds represented by general formula A and the compounds represented by general formula B will be described in more detail below.

[0026] <Compound represented by general formula A> [ka]

[0027] In general formula A, R 1 , R 2 , B 1 and B. 2 each independently represents a hydrogen atom or a substituent.

[0028] R 1 and R 2 R preferably each independently represents a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and more preferably represents a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, or a hexyl group. 1 and R 2 more preferably each independently represents a methyl group or an ethyl group, and R 1 and R 2 More preferably, both represent a methyl group or both represent an ethyl group.

[0029] B1 and B. 2 Each of B independently represents a substituted or unsubstituted phenyl group. When the phenyl group has a plurality of substituents, two or more of these substituents may be bonded to form a ring. Specific examples of the ring formed include the rings contained in the exemplary compounds shown below. The substitution position of the substituent in the substituted phenyl group is 1 and B 2 and is preferably in the para position relative to the carbon atom to which they are bonded. Specific examples of the substituent of the substituted phenyl group include a morpholino group, a piperidino group, a halogen atom, an alkoxy group, and the following substituents contained in the exemplary compounds shown below. In the present invention and this specification, "*" regarding a partial structure of a compound indicates the bonding position with the atom to which such partial structure is bonded.

[0030] [ka]

[0031] In general formula A, R 3 ~R 6 each independently represents a hydrogen atom or an electron-withdrawing group. 3 ~R 6 At least one of the groups represents an electron-withdrawing group. As the electron-withdrawing group, a halogen atom, a perfluoroalkyl group having 1 to 6 carbon atoms, a perfluorophenyl group, a perfluoroalkylphenyl group, or a cyano group is preferable. As the halogen atom, a fluorine atom is preferable. As the perfluoroalkyl group having 1 to 6 carbon atoms, a trifluoromethyl group is preferable.

[0032] In one embodiment, the compound represented by formula A can be the following compound: R 3 ~R 6 Among them, R 4 Only R is an electron-withdrawing group. 3 , R 5 and R 6 is a compound where the atom is hydrogen. R 3 ~R 6 Among them, R4 and R 6 are the same or different electron withdrawing groups, R 3 and R 5 is a compound where the atom is hydrogen. R 3 ~R 6 Among them, R 3 and R 5 are the same or different electron withdrawing groups, R 4 and R 6 is a compound where the atom is hydrogen.

[0033] Examples of the compound represented by general formula A include the following compounds. However, the present invention is not limited to the compounds exemplified below.

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[0058] <Compound represented by general formula B> [ka]

[0059] In general formula B, R 7 ~R 12 , B 3 and B. 4 each independently represents a hydrogen atom or a substituent.

[0060] R 7 and R 8 R preferably each independently represents a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and more preferably represents a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, or a hexyl group.7 and R 8 more preferably each independently represents a methyl group or an ethyl group, and R 7 and R 8 More preferably, both represent a methyl group or both represent an ethyl group.

[0061] B 3 and B. 4 Each of B independently represents a substituted or unsubstituted phenyl group. When the phenyl group has a plurality of substituents, two or more of these substituents may be bonded to form a ring. Specific examples of the ring formed include the rings contained in the exemplary compounds shown below. The substitution position of the substituent in the substituted phenyl group is 3 and B 4 Specific examples of the substituent of the substituted phenyl group include a morpholino group, a piperidino group, a halogen atom, an alkoxy group, and the substituents contained in the exemplary compounds shown below, such as the following substituents.

[0062] [ka]

[0063] R 9 ~R 12 each independently represents a hydrogen atom or a substituent. 9 ~R 12 can all be hydrogen atoms. 10 is an electron withdrawing group, R 9 , R 11 and R 12 In another embodiment, R 9 and R 11 are each independently an electron-withdrawing group, R 10 and R 12can be a hydrogen atom. As the electron-withdrawing group, a halogen atom, a perfluoroalkyl group having 1 to 6 carbon atoms, a perfluorophenyl group, a perfluoroalkylphenyl group, or a cyano group is preferred. As the halogen atom, a fluorine atom is preferred. As the perfluoroalkyl group having 1 to 6 carbon atoms, a trifluoromethyl group is preferred.

[0064] In one form, R 10 can be a substituted or unsubstituted phenyl group, preferably R 10 is a substituted or unsubstituted phenyl group, and R 9 , R 11 and R 12 Specific examples of such a substituted phenyl group include a phenyl group substituted with one or more halogen atoms and / or one or more cyano groups, for example, a phenyl group substituted with a halogen atom (preferably a fluorine atom) at all five substitution positions of the phenyl group, and R 10 and a mono-substituted phenyl group in which a cyano group is substituted at the para-position relative to the carbon atom to which the carbon atom is bonded.

[0065] R 13 and R 14 each independently represents a hydrogen atom or an electron-donating group. 13 and R 14 At least one of R represents an electron donating group. 13 and R 14 each independently represents an electron-donating group selected from the group consisting of a methoxy group, an ethoxy group, a phenoxy group, a methylsulfide group, a phenylsulfide group, a dimethylamino group, a pyrrolidino group, a piperidino group, a morpholino group, and a thiomorpholino group.

[0066] R 13 and R 14 In one embodiment, one of R can be a hydrogen atom and the other can be an electron donating group, and in another embodiment, both can be independently an electron donating group. 13 and R 14 are preferably electron donating groups. 13and R 14 can be the same or different electron donating groups. 13 and R 14 About R 13 is a morpholino group and R 14 is an alkoxy group (preferably a methoxy group); R 13 is a morpholino group and R 14 is a methyl sulfide group (-S-CH3), R 13 and R 14 are each an alkoxy group (preferably a methoxy group), and R 13 and R 14 are preferably methyl sulfide groups (-S-CH3).

[0067] Examples of the compound represented by formula B include the following compounds. However, the present invention is not limited to the compounds exemplified below.

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[0086] The compounds represented by the general formula A and the compounds represented by the general formula B can be synthesized by known methods. For the synthesis method, the following documents can be referred to: Japanese Patent No. 4884578, US2006 / 0226402A1, US2006 / 0228557A1, US2008 / 0103301A1, US2011 / 0108781A1, US2011 / 0108781A1, US7527754, US7556751, WO2001 / 60811A1, WO2013 / 086248A1, WO1996 / 014596A1 and WO2001 / 019813A1.

[0087] The photochromic article according to one embodiment of the present invention and the photochromic composition according to one embodiment of the present invention contain one or more compounds represented by general formula A and one or more compounds represented by general formula B. The compound represented by general formula A contained in the photochromic article and the photochromic composition may be of only one type, or may be of two or more types (for example, two or more and four or less). The compound represented by general formula B contained in the photochromic article and the photochromic composition may be only one type, or may be two or more types, preferably two or more types, and may be, for example, four or less types or three or less types. The photochromic article and the photochromic composition preferably contain more compounds represented by general formula B than compounds represented by general formula A on a mass basis. The total of the compounds represented by general formula A and the compounds represented by general formula B is 100 mass%, and the content of the compounds represented by general formula B is preferably more than 50 mass%, more preferably 60 mass% or more, even more preferably 70 mass% or more, even more preferably 80 mass% or more, and even more preferably 90 mass% or more. The content of the compounds represented by general formula B relative to the total (100 mass%) of the compounds represented by general formula A and the compounds represented by general formula B can be less than 100 mass%, and can be 99 mass% or less, 98 mass% or less, 97 mass% or less, 96 mass% or less, or 95 mass% or less. When the photochromic article and the photochromic composition contain two or more compounds represented by general formula B, the content of the compounds represented by general formula B is the total content of the compounds. This also applies to the content of various components in the present invention and this specification. The photochromic article and the photochromic composition may contain, for example, about 0.1 to 15.0% by mass of the compound represented by general formula A and the compound represented by general formula B in total, with the total amount taken as 100% by mass. However, the amount is not limited to this range.

[0088] [Photochromic articles and photochromic compositions] The photochromic article may have at least a substrate. In one embodiment, the compound represented by general formula A and the compound represented by general formula B may be included in the substrate of the photochromic article. The photochromic article may have a substrate and a photochromic layer, and the substrate and / or the photochromic layer may contain the compound represented by general formula A and the compound represented by general formula B. In one embodiment, the compound represented by general formula A and the compound represented by general formula B may be included only in the substrate, in another embodiment, or in the photochromic layer, in another embodiment. In addition, the substrate and the photochromic layer may contain only the compound represented by general formula A and the compound represented by general formula B as photochromic compounds, or may contain one or more other photochromic compounds. Other photochromic compounds include azobenzenes, spiropyrans, spirooxazines, naphthopyrans, indenonaphthopyrans, phenanthropyrans, hexaarylbisimidazoles, donor-acceptor Stenhouse adducts (DASA), salicylideneanilines, dihydropyrenes, anthracene dimers, fulgides, diarylethenes, phenoxynaphthacenequinones, and stilbenes.

[0089] <Base material> The photochromic article may include a substrate selected according to the type of the photochromic article. As an example of the substrate, a plastic lens substrate or a glass lens substrate may be used as a spectacle lens substrate. The glass lens substrate may be, for example, a lens substrate made of inorganic glass. Examples of the plastic lens substrate include styrene resins such as (meth)acrylic resins, polycarbonate resins, allyl resins, allyl carbonate resins such as diethylene glycol bisallyl carbonate resin (CR-39), vinyl resins, polyester resins, polyether resins, 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 a cured product (generally called a transparent resin) 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 uncolored (colorless lens) or colored (dyed lens). The refractive index of the lens substrate may 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 be above or below the above range. Here, the refractive index refers to the refractive index for light with a wavelength of 500 nm. The lens substrate may be a lens with refractive power (so-called prescription lens) or a lens without refractive power (so-called non-prescription lens).

[0090] For example, the photochromic composition may be a polymerizable composition. In the present invention and this specification, a "polymerizable composition" is a composition containing one or more polymerizable compounds. A polymerizable composition containing at least one compound represented by general formula A, one or more compounds represented by general formula B, and one or more polymerizable compounds is molded by a known molding method to produce a cured product of the polymerizable composition. Such a cured product may be included as a substrate in the photochromic article and / or may be included as a photochromic layer. The curing treatment may be light irradiation and / or heat treatment. A polymerizable compound is a compound having a polymerizable group, and the polymerizable composition may be cured to form a cured product by the progress of a polymerization reaction of the polymerizable compound. The polymerizable composition may further contain one or more additives (e.g., a polymerization initiator, etc.).

[0091] The spectacle lens can be various lenses such as a single-focus lens, a multifocal lens, a progressive power lens, etc. 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 a normal lens substrate and a spectacle lens, the object side surface is convex, and the eyeball side surface is concave. However, this is not limited thereto. The photochromic layer can usually be provided on the object side surface of the lens substrate, but may also be provided on the eyeball side surface.

[0092] <Photochromic layer> The photochromic layer can be a layer provided directly on the surface of the substrate or indirectly via one or more other layers. The photochromic layer can be, for example, a cured layer obtained by curing a polymerizable composition. The photochromic layer can be formed as a cured layer obtained by curing a polymerizable composition containing at least one compound represented by general formula A, one or more compounds represented by general formula B, and one or more polymerizable compounds. For example, the photochromic layer can be formed as a cured layer containing one or more compounds represented by general formula A and one or more compounds represented by general formula B by directly applying the polymerizable composition onto the surface of the substrate or applying the polymerizable composition onto the surface of a layer provided on the substrate and subjecting the applied polymerizable composition to a curing treatment. As the application method, known application methods such as spin coating, dip coating, spray coating, inkjet, nozzle coating, and slit coating can be adopted. The curing treatment can be light irradiation and / or heat treatment. The polymerizable composition can further contain one or more additives (e.g., polymerization initiators, etc.) in addition to one or more polymerizable compounds. As the polymerization reaction of the polymerizable compound progresses, the polymerizable composition can be cured to form a cured layer.

[0093] The thickness of the photochromic layer can be, for example, 5 μm or more, 10 μm or more, or 20 μm or more, and can be, for example, 80 μm or less, 70 μm or less, or 50 μm or less.

[0094] <Polymerizable compound> In the present invention and this specification, a polymerizable compound refers to a compound having one or more polymerizable groups in one molecule, and a "polymerizable group" refers to a reactive group capable of undergoing a polymerization reaction. Examples of the polymerizable group include an acryloyl group, a methacryloyl group, a vinyl group, a vinyl ether group, an epoxy group, a thiol group, an oxetane group, a hydroxy group, a carboxy group, an amino group, and an isocyanate group.

[0095] Examples of the polymerizable compound that can be used to form the substrate and the photochromic layer include the following compounds.

[0096] (Episulfide compounds) An episulfide compound is a compound having two or more episulfide groups in one molecule. The episulfide group is a polymerizable group capable of ring-opening polymerization. Specific examples of episulfide compounds include bis(1,2-epithioethyl)sulfide, bis(1,2-epithioethyl)disulfide, bis(2,3-epithiopropyl)sulfide, bis(2,3-epithiopropylthio)methane, bis(2,3-epithiopropyl)disulfide, bis(2,3-epithiopropyldithio)methane, bis(2,3-epithiopropyldithio)ethane, bis(6,7-epithio-3,4-dithiaheptyl)sulfide, bis(6,7-epithio-3,4-dithiaheptyl) disulfide, 1,4-dithiane-2,5-bis(2,3-epithiopropyldithiomethyl), 1,3-bis(2,3-epithiopropyldithiomethyl)benzene, 1,6-bis(2,3-epithiopropyldithiomethyl)-2-(2,3-epithiopropyldithioethylthio)-4-thiahexane, 1,2,3-tris(2,3-epithiopropyldithio)propane, 1,1,1,1-tetrathiazol-1-yl rakis(2,3-epithiopropyldithiomethyl)methane, 1,3-bis(2,3-epithiopropyldithio)-2-thiapropane, 1,4-bis(2,3-epithiopropyldithio)-2,3-dithiabutane, 1,1,1-tris(2,3-epithiopropyldithio)methane, 1,1,1-tris(2,3-epithiopropyldithiomethylthio)methane, 1,1,2,2-tetrakis(2,3-epithiopropyldithio)ethane, 1,1,2,2-tetrakis(2,3-epithiopropyldithio)ethane, Examples of such tetrakis(2,3-epithiopropyldithiomethylthio)ethane include 1,1,3,3-tetrakis(2,3-epithiopropyldithio)propane, 1,1,3,3-tetrakis(2,3-epithiopropyldithiomethylthio)propane, 2-[1,1-bis(2,3-epithiopropyldithio)methyl]-1,3-dithietane, and 2-[1,1-bis(2,3-epithiopropyldithiomethylthio)methyl]-1,3-dithietane.

[0097] (Thietanyl compounds) A thietanyl compound is a thietanyl compound having two or more thietanyl groups in one molecule. The thietanyl group is a polymerizable group that can undergo ring-opening polymerization. Some thietanyl compounds have episulfide groups in addition to multiple thietanyl groups. Such compounds are listed as examples of episulfide compounds above. Other thietanyl compounds include metal-containing thietanyl compounds that have metal atoms in the molecule and non-metal thietanyl compounds that do not contain metals.

[0098] Specific examples of non-metallic thietanyl compounds include bis(3-thietanyl) disulfide, bis(3-thietanyl) sulfide, bis(3-thietanyl) trisulfide, bis(3-thietanyl) tetrasulfide, 1,4-bis(3-thietanyl)-1,3,4-trithiabutane, 1,5-bis(3-thietanyl)-1,2,4,5-tetrathiapentane, 1,6-bis(3-thietanyl)-1,3,4,6-tetrathiahexane, 1,6-bis(3-thietanyl)-1,3,5,6-tetrathiahexane, 1,7-bis(3-thietanyl)- 1,2,4,5,7-pentathiaheptane, 1,7-bis(3-thietanylthio)-1,2,4,6,7-pentathiaheptane, 1,1-bis(3-thietanylthio)methane, 1,2-bis(3-thietanylthio)ethane, 1,2,3-tris(3-thietanylthio)propane, 1,8-bis(3-thietanylthio)-4-(3-thietanylthiomethyl)-3,6-dithiaoctane, 1,11-bis(3-thietanylthio)-4,8-bis(3-thietanylthiomethyl)-3,6,9-trithiaundecane, 1,11-bis(3-thietanylthio) thio)-4,7-bis(3-thietanylthiomethyl)-3,6,9-trithiaundecane, 1,11-bis(3-thietanylthio)-5,7-bis(3-thietanylthiomethyl)-3,6,9-trithiaundecane, 2,5-bis(3-thietanylthiomethyl)-1,4-dithiane, 2,5-bis[[2-(3-thietanylthio)ethyl]thiomethyl]-1,4-dithiane, 2,5-bis(3-thietanylthiomethyl)-2,5-dimethyl-1,4-dithiane, bisthietanyl sulfide, bis(thietanylthio)methane, 3-[<(thietanylthio)methyl]thiomethyl]-1,4-dithiane [thietanylthio)methylthio>methylthio]thietane, bisthietanyl disulfide, bisthietanyl trisulfide, bisthietanyl tetrasulfide, bisthietanyl pentasulfide, 1,4-bis(3-thietanyldithio)-2,3-dithiabutane, 1,1,1-tris(3-thietanyldithio)methane, 1,1,1-tris(3-thietanyldithiomethylthio)methane, 1,1,2,2-tetrakis(3-thietanyldithio)ethane, 1,1,2,2-tetrakis(3-thietanyldithiomethylthio)ethane, and the like.

[0099] Examples of metal-containing thietane compounds include those that contain, as metal atoms in the molecule, atoms of Group 14 such as Sn atom, Si atom, Ge atom, Pb atom, etc., elements of Group 4 such as Zr atom, Ti atom, etc., atoms of Group 13 such as Al atom, etc., atoms of Group 12 such as Zn atom, etc. Specific examples include alkylthio(thietanylthio)tin, bis(alkylthio)bis(thietanylthio)tin, alkylthio(alkylthio)bis(thietanylthio)tin, bis(thietanylthio)cyclic dithiotin compounds, alkyl(thietanylthio)tin compounds, etc.

[0100] Specific examples of alkylthio(thietanylthio)tin include methylthiotris(thietanylthio)tin, ethylthiotris(thietanylthio)tin, propylthiotris(thietanylthio)tin, and isopropylthiotris(thietanylthio)tin.

[0101] Specific examples of bis(alkylthio)bis(thietanylthio)tin include bis(methylthio)bis(thietanylthio)tin, bis(ethylthio)bis(thietanylthio)tin, bis(propylthio)bis(thietanylthio)tin, and bis(isopropylthio)bis(thietanylthio)tin.

[0102] Specific examples of alkylthio(alkylthio)bis(thietanylthio)tin include ethylthio(methylthio)bis(thietanylthio)tin, methylthio(propylthio)bis(thietanylthio)tin, isopropylthio(methylthio)bis(thietanylthio)tin, ethylthio(propylthio)bis(thietanylthio)tin, ethylthio(isopropylthio)bis(thietanylthio)tin, and isopropylthio(propylthio)bis(thietanylthio)tin.

[0103] Specific examples of the bis(thietanylthio)cyclic dithiotin compound include bis(thietanylthio)dithiastannetane, bis(thietanylthio)dithiastannolane, bis(thietanylthio)dithiastanninane, and bis(thietanylthio)trithiastannocane.

[0104] Specific examples of the alkyl(thietanylthio)tin compound include methyltris(thietanylthio)tin, dimethylbis(thietanylthio)tin, butyltris(thietanylthio)tin, tetrakis(thietanylthio)tin, tetrakis(thietanylthio)germanium, and tris(thietanylthio)bismuth.

[0105] (Polyamine compounds) A polyamine compound is a compound having two or more NH2 groups in one molecule, and can form a urea bond by reacting with a polyisocyanate, and can form a thiourea bond by reacting with a polyisothiocyanate. Specific examples of polyamine compounds include ethylenediamine, hexamethylenediamine, isophoronediamine, nonamethylenediamine, undecamethylenediamine, dodecamethylenediamine, metaxylenediamine, 1,3-propanediamine, putrescine, 2-(2-aminoethylamino)ethanol, diethylenetriamine, p-phenylenediamine, m-phenylenediamine, melamine, and 1,3,5-benzenetriamine.

[0106] (Epoxy compounds) Epoxy compounds are compounds having an epoxy group in the molecule. The epoxy group is a polymerizable group capable of ring-opening polymerization. Epoxy compounds are generally classified into aliphatic epoxy compounds, alicyclic epoxy compounds, and aromatic epoxy compounds.

[0107] Specific examples of the aliphatic epoxy compound include ethylene oxide, 2-ethyloxirane, butyl glycidyl ether, phenyl glycidyl ether, 2,2'-methylenebisoxirane, 1,6-hexanediol diglycidyl ether, ethylene glycol diglycidyl ether, diethylene glycol diglycidyl ether, triethylene glycol diglycidyl ether, tetraethylene glycol diglycidyl ether, nonaethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, dipropylene glycol diglycidyl ether, tripropylene glycol diglycidyl ether, tetrapropylene glycol diglycidyl ether, nonapropylene glycol diglycidyl ether, neopentyl glycol diglycidyl ether, trimethylolpropane triglycidyl ether, glycerol triglycidyl ether, diglycerol tetraglycidyl ether, pentaerythritol tetraglycidyl ether, and triglycidyl ether of tris(2-hydroxyethyl)isocyanurate.

[0108] Specific examples of the alicyclic epoxy compound include isophoronediol diglycidyl ether, bis-2,2-hydroxycyclohexylpropane diglycidyl ether, and the like.

[0109] Specific examples of aromatic epoxy compounds include resorcinol diglycidyl ether, bisphenol A diglycidyl ether, bisphenol F diglycidyl ether, bisphenol S diglycidyl ether, orthophthalic acid diglycidyl ester, phenol novolac polyglycidyl ether, and cresol novolac polyglycidyl ether.

[0110] In addition to the above, epoxy compounds having a sulfur atom in the molecule as well as an epoxy group can also be used. Such sulfur-containing epoxy compounds include linear aliphatic and cyclic aliphatic compounds.

[0111] Specific examples of the chain aliphatic sulfur atom-containing epoxy compound include bis(2,3-epoxypropyl)sulfide, bis(2,3-epoxypropyl)disulfide, bis(2,3-epoxypropylthio)methane, 1,2-bis(2,3-epoxypropylthio)ethane, 1,2-bis(2,3-epoxypropylthio)propane, 1,3-bis(2,3-epoxypropylthio)propane, 1,3-bis(2,3-epoxypropylthio)-2-methylpropane, 1,4-bis(2,3-epoxypropylthio)butane, 1,4-bis(2,3-epoxypropylthio)-2-methylbutane, 1,3-bis(2,3-epoxypropylthio)butane, 1,5 ... 1,5-bis(2,3-epoxypropylthio)pentane, 1,5-bis(2,3-epoxypropylthio)-2-methylpentane, 1,5-bis(2,3-epoxypropylthio)-3-thiapentane, 1,6-bis(2,3-epoxypropylthio)hexane, 1,6-bis(2,3-epoxypropylthio)-2-methylhexane, 3,8-bis(2,3-epoxypropylthio)-3,6-dithiaoctane, 1,2,3-tris(2,3-epoxypropylthio)propane, 2,2-bis(2,3-epoxypropylthio)-1,3-bis(2,3-epoxypropylthiomethyl)propane, 2,2-bis(2,3-epoxypropylthiomethyl)-1-(2,3-epoxypropylthio)butane, and the like.

[0112] Specific examples of the cyclic aliphatic sulfur atom-containing epoxy compound include 1,3-bis(2,3-epoxypropylthio)cyclohexane, 1,4-bis(2,3-epoxypropylthio)cyclohexane, 1,3-bis(2,3-epoxypropylthiomethyl)cyclohexane, 1,4-bis(2,3-epoxypropylthiomethyl)cyclohexane, 2,5-bis(2,3-epoxypropylthiomethyl)-1,4-dithiane, 2,5-bis[<2-(2,3-epoxypropylthio)ethyl>thiomethyl]-1,4-dithiane, and 2,5-bis(2,3-epoxypropylthiomethyl)-2,5-dimethyl-1,4-dithiane.

[0113] (Compound having a radically polymerizable group) The compound having a radical polymerizable group is a polymerizable group capable of undergoing radical polymerization. Examples of the radical polymerizable group include an acryloyl group, a methacryloyl group, an allyl group, and a vinyl group.

[0114] Hereinafter, a compound having a polymerizable group selected from the group consisting of an acryloyl group and a methacryloyl group will be referred to as a "(meth)acrylate compound". Specific examples of the (meth)acrylate compound include ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, polyethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, dipropylene glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, ethylene glycol bisglycidyl (meth)acrylate, bisphenol A di(meth)acrylate, 2,2-bis(4-(meth)acryloyloxyethoxyphenyl)propane, 2,2-bis(4-(meth)acryloyloxyethoxyphenyl)propane, 2,2-bis(3,5-dibromo -4-(meth)acryloyloxyethoxyphenyl)propane, 2,2-bis(4-(meth)acryloyloxydipropoxyphenyl)propane, bisphenol F di(meth)acrylate, 1,1-bis(4-(meth)acryloyloxyethoxyphenyl)methane, 1,1-bis(4-(meth)acryloyloxydiethoxyphenyl)methane, dimethyloltricyclodecane di(meth)acrylate, trimethylolpropane tri(meth)acrylate, ditrimethylol Examples of the methacrylates include diolpropane tetra(meth)acrylate, glycerol di(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, methylthio(meth)acrylate, phenylthio(meth)acrylate, benzylthio(meth)acrylate, xylylenedithiol di(meth)acrylate, mercaptoethyl sulfide di(meth)acrylate, and bifunctional urethane (meth)acrylate.

[0115] Specific examples of compounds having an allyl group (allyl compounds) include allyl glycidyl ether, diallyl phthalate, diallyl terephthalate, diallyl isophthalate, diallyl carbonate, diethylene glycol bisallyl carbonate, methoxypolyethylene glycol allyl ether, polyethylene glycol allyl ether, methoxypolyethylene glycol-polypropylene glycol allyl ether, butoxypolyethylene glycol-polypropylene glycol allyl ether, methacryloyloxypolyethylene glycol-polypropylene glycol allyl ether, phenoxypolyethylene glycol allyl ether, and methacryloyloxypolyethylene glycol allyl ether.

[0116] Examples of compounds having a vinyl group (vinyl compounds) include α-methylstyrene, α-methylstyrene dimer, styrene, chlorostyrene, methylstyrene, bromostyrene, dibromostyrene, divinylbenzene, and 3,9-divinylspirobi(m-dioxane).

[0117] The photochromic article may include, at any position, one or more layers known as functional layers for photochromic articles, such as a protective layer for improving the durability of the photochromic article, an antireflection layer, a water-repellent or hydrophilic antifouling layer, an antifogging layer, and a primer layer for improving adhesion between layers.

[0118] The photochromic article can be an optical article. One form of the optical article is a spectacle lens. Such spectacle lenses can also be called photochromic lenses or photochromic spectacle lenses. In addition, one form of the optical article can also include a lens for goggles, a visor (peak) part of a sun visor, a shielding member of a helmet, etc. By applying the photochromic composition, which is a polymerizable composition, onto a substrate for such optical articles and subjecting the applied composition to a curing treatment to form a photochromic layer, an optical article having an anti-glare function can be obtained.

[0119] [glasses] One aspect of the present invention relates to glasses having a spectacle lens which is one form of the photochromic article. Details of the spectacle lens included in the glasses are as described above. By including such a spectacle lens, the glasses can exhibit an anti-glare effect like sunglasses, for example, outdoors, when the photochromic compound is irradiated with sunlight and colored, and when returning indoors, the photochromic compound fades, thereby recovering transparency. For the configuration of the frame, etc. of the glasses, known techniques can be applied. EXAMPLES

[0120] 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. "%" in the following descriptions indicates % by mass.

[0121] [Synthesis of Compounds] Compounds 1 to 15 shown below were synthesized with reference to the reference documents shown above regarding the synthesis method of the compounds. The compounds were identified in the same manner as the method described in the reference publication, and it was confirmed that the compounds shown below were synthesized. Compounds 1 to 7 are compounds represented by general formula A, and compounds 8 to 15 are compounds represented by general formula B.

[0122] [ka]

[0123] [ka]

[0124] [Examples 1 to 28, Comparative Examples 1 to 3] <Preparation of Photochromic Composition (Polymerizable Composition)> In a plastic container, 68 parts by weight of polyethylene glycol diacrylate, 12 parts by weight of trimethylolpropane trimethacrylate, and 20 parts by weight of neopentyl glycol dimethacrylate were mixed with respect to a total of 100 parts by weight of (meth)acrylate to prepare a (meth)acrylate mixture. A photochromic compound was mixed with 100 parts by weight of this (meth)acrylate mixture so that the amount of the compound was 2.5 parts by weight. For compositions containing multiple photochromic compounds, the mass ratio of each photochromic compound when the total amount of the photochromic compounds is 10 is shown in Table 2. Furthermore, a photopolymerization initiator (phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide), an antioxidant [bis(3-tert-butyl-4-hydroxy-5-methylphenyl)propionic acid)] [ethylene bis(oxyethylene) and a light stabilizer (bis(1,2,2,6,6-pentamethyl-4-piperidyl) sebacate) were mixed and thoroughly stirred, after which a silane coupling agent (γ-methacryloxypropyltrimethoxysilane) was added dropwise while stirring. The mixture was then defoamed using an automatic revolution type stirring and defoaming device. By the above method, a photochromic composition was prepared.

[0125] The comparative compounds used in Comparative Example 3 are as follows: [ka]

[0126] <Deposition of primer layer> A plastic lens substrate (manufactured by HOYA under the trade name EYAS: center thickness 2.5 mm, diameter 75 mm, spherical lens power -4.00) was immersed in a 10% by mass aqueous solution of sodium hydroxide (liquid temperature 60°C) for 5 minutes for alkaline cleaning, and then washed with pure water and dried. After that, a water-based polyurethane resin liquid (polycarbonate polyol 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 at 1500 rpm for 1 minute using a Mikasa spin coater MS-B150 in an environment of room temperature and relative humidity 40 to 60%, and then naturally dried for 15 minutes to form a primer layer with a thickness of 5.5 μm.

[0127] <Photochromic layer formation> The photochromic composition prepared above was dropped onto the primer layer, and coated by spin coating using a program that changes the rotation speed from 500 rpm to 1500 rpm in slope mode over 1 minute, and then rotates at 1500 rpm for 5 seconds using MS-B150 manufactured by Mikasa Co., Ltd. Then, the photochromic composition coated on the primer layer formed on the plastic lens substrate was irradiated with ultraviolet light (dominant wavelength 405 nm) for 40 seconds in a nitrogen atmosphere (oxygen concentration 500 ppm or less), and the composition was cured to form a photochromic layer. The thickness of the formed photochromic layer was 45 μm. In this manner, a photochromic article (eyeglass lens) was produced.

[0128] [Evaluation method] <Evaluation of color density> The luminous reflectance was determined by the following method in accordance with JIS T7333:2005. The convex surface of each of the eyeglass lenses of the Examples and Comparative Examples was irradiated with light from a xenon lamp through an aeromass filter for 15 minutes to color the photochromic layer. The irradiance and the tolerance of the irradiance were set to the values ​​shown in Table 1, as specified in JIS T7333:2005. The transmittance during coloring was measured using a spectrophotometer manufactured by Otsuka Electronics. The luminous transmittance T (%) calculated from the measurement results in the wavelength range of 380 nm to 780 nm is shown in Table 2. The smaller the value of T (%), the higher the concentration of color development of the photochromic compound.

[0129] [Table 1]

[0130] <Evaluation of fading speed> The fading rate was evaluated by the following method. The transmittance (measurement wavelength: 550 nm) of each of the eyeglass lenses of the Examples and Comparative Examples before light irradiation (uncolored state) was measured using a spectrophotometer manufactured by Otsuka Electronics Co., Ltd. The transmittance measured here is referred to as the "initial transmittance." Each eyeglass lens was irradiated with light from a xenon lamp through an aeromass filter for 15 minutes to color the photochromic layer. This irradiation light was set so that the irradiance and irradiance tolerance were the values ​​shown in Table 1, as specified in JIS T7333:2005. The transmittance after coloring was measured in the same manner as the initial transmittance. The transmittance measured here is called the "transmittance after coloring." After that, the time required from the time when the light irradiation was stopped until the transmittance reached [(initial transmittance - transmittance when colored) / 2] was measured. This time is called the "half-life time." The shorter the half-life time, the faster the fading rate. The calculated half-life times are shown in Table 2.

[0131] [Table 2]

[0132] From the results shown in Table 2, it can be seen that by combining a compound represented by general formula A with a compound represented by general formula B, it is possible to provide a photochromic article that is highly colored in the visible range and exhibits a fast fading rate.

[0133] Finally, the above-mentioned aspects will be summarized.

[0134] According to one embodiment, photochromic articles and compositions are provided that include one or more compounds represented by general formula A and one or more compounds represented by general formula B:

[0135] In one embodiment, in the general formula A, R 1 and R 2 may each independently represent a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

[0136] In one embodiment, in the general formula A, R 1 and R 2 may each independently represent a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, or a hexyl group.

[0137] In one embodiment, B in the general formula A 1 and B. 2 and B in general formula B 3 and B. 4 may each independently represent a substituted or unsubstituted phenyl group. When the phenyl group has a plurality of substituents, these substituents may be bonded to form a ring.

[0138] In one embodiment, the electron-withdrawing group in general formula A can be a halogen atom, a perfluoroalkyl group having 1 to 6 carbon atoms, a perfluorophenyl group, a perfluoroalkylphenyl group, or a cyano group.

[0139] In one embodiment, the halogen atom can be a fluorine atom.

[0140] In one form, the perfluoroalkyl group can be a trifluoromethyl group.

[0141] In one embodiment, R in formula A 1 , R 2 , B 1 , B 2 R in general formula B 7 ~R 12 , B 3 and B. 4 One or more selected from the group consisting of: a substituent R selected from the group consisting of a hydroxy group, a linear or branched alkyl group having 1 to 18 carbon atoms, a monocyclic or polycyclic aliphatic alkyl group having 5 to 18 carbon atoms such as a bicyclic ring, a linear or branched alkoxy group having 1 to 24 constituent atoms, a non-aromatic cyclic substituent having 1 to 24 constituent atoms, a linear or branched perfluoroalkyl group having 1 to 18 carbon atoms, a linear or branched perfluoroalkoxy group, a linear or branched alkylsulfide group having 1 to 24 constituent atoms, an aryl group, an aryloxy group, an arylsulfide group, a heteroaryl group, an amino group, a monoalkylamino group, a dialkylamino group, a monoarylamino group, a diarylamino group, a piperidino group, a morpholino group, a thiomorpholino group, a tetrahydroquinolino group, a tetrahydroisoquinolino group, or other cyclic amino group, an ethynyl group, a mercapto group, a silyl group, a sulfonic acid group, an alkylsulfonyl group, a formyl group, a carboxy group, a cyano group, and a halogen atom; m ; R m and one or more identical or different R m or solubilizing group It can be.

[0142] In one embodiment, in the general formula B, R 7 and R 8 may each independently represent a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

[0143] In one embodiment, in the general formula B, R 7 and R 8may each independently represent a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, or a hexyl group.

[0144] In one embodiment, in the general formula B, R 13 and R 14 may each independently represent an electron donating group selected from the group consisting of a methoxy group, an ethoxy group, a phenoxy group, a methylsulfide group, a phenylsulfide group, a dimethylamino group, a pyrrolidino group, a piperidino group, a morpholino group, and a thiomorpholino group.

[0145] In one embodiment, the photochromic article and the photochromic composition can contain more of the compound represented by formula B than the compound represented by formula A, by weight.

[0146] In one embodiment, the photochromic article and the photochromic composition can include one compound represented by general formula A and two compounds represented by general formula B.

[0147] In one embodiment, the photochromic article can be a photochromic article having a substrate and a photochromic layer, the photochromic layer containing one or more compounds represented by general formula A and one or more compounds represented by general formula B.

[0148] In one embodiment, the photochromic layer can be a cured layer obtained by curing a polymerizable composition.

[0149] In one aspect, the photochromic composition can include a polymerizable compound.

[0150] In one form, the photochromic article can be a spectacle lens.

[0151] In one form, the photochromic article can be a lens for goggles.

[0152] In one form, the photochromic article can be the visor portion of a sun visor.

[0153] In one form, the photochromic article can be a shield member of a helmet.

[0154] According to one aspect, eyeglasses are provided that include the above eyeglass lens.

[0155] The various aspects and configurations described in this specification may be combined in any combination of two or more.

[0156] The embodiments disclosed herein should be considered to be illustrative and not restrictive in all respects. The scope of the present invention is defined by the claims, not the above description, and is intended to include all modifications within the meaning and scope of the claims. [Industrial Applicability]

[0157] One aspect of the present invention is useful in the technical fields of glasses, goggles, sun visors, helmets, and the like.

Claims

1. A photochromic composition comprising one or more compounds represented by the following general formula A and one or more compounds represented by the following general formula B: 【Chemistry 1】 In general formula A, R １ , R ２ , B １ and B ２ each independently represents a hydrogen atom or a substituent, R ４ represents an electron-withdrawing group, R ３ , R ５ and R ６ represents a hydrogen atom. 【Chemistry 2】 In general formula B, R ７ ~R １２ , B ３ and B ４ each independently represents a hydrogen atom or a substituent, R １３ and R １４ each independently represents a hydrogen atom or an electron donating group, provided that R １３ and R １４ At least one of represents an electron donating group. In the formula A, R 1 , R 2 , B 1 , and B 2 , and in the formula B, one or more selected from the group consisting of R 7 to R 12 , B 3 , and B 4 represent a substituent, and the substituent is a substituent R m selected from the group consisting of a hydroxy group, a linear or branched alkyl group having 1 to 18 carbon atoms, a monocyclic or polycyclic aliphatic alkyl group having 5 to 18 carbon atoms such as a bicyclic ring, a linear or branched alkoxy group having 1 to 24 constituent atoms, a non-aromatic cyclic substituent having 1 to 24 constituent atoms, a linear or branched perfluoroalkyl group having 1 to 18 carbon atoms, a linear or branched perfluoroalkoxy group, a linear or branched alkylsulfide group having 1 to 24 constituent atoms, an aryl group, an aryloxy group, an arylsulfide group, a heteroaryl group, an amino group, a monoalkylamino group, a dialkylamino group, a monoarylamino group, a diarylamino group, a cyclic amino group such as a piperidino group, a morpholino group, a thiomorpholino group, a tetrahydroquinolino group, or a tetrahydroisoquinolino group, an ethynyl group, a mercapto group, a silyl group, a sulfonic acid group, an alkylsulfonyl group, a formyl group, a carboxy group, a cyano group, and a halogen atom; R m is further substituted with one or more identical or different R m ; or solubilizing group It is.

2. A photochromic composition comprising one or more compounds represented by the following general formula A and one or more compounds represented by the following general formula B: 【Chemistry 3】 In general formula A, R １ , R ２ , B １ and B ２ each independently represents a hydrogen atom or a substituent, R ３ ~R ６ each independently represents a hydrogen atom or an electron-withdrawing group, provided that R ３ ~R ６ represents an electron withdrawing group. 【Chemistry 4】 In general formula B, R ７ , R ８ , B ３ and B ４ each independently represents a hydrogen atom or a substituent, R １０ represents a hydrogen atom or a substituted or unsubstituted phenyl group, R ９ , R １１ and R １２ represents a hydrogen atom, R １３ and R １４ each independently represents a hydrogen atom or an electron donating group, provided that R １３ and R １４ At least one of represents an electron donating group. In the formula A, R 1 , R 2 , B 1 , and B 2 , and in the formula B, one or more selected from the group consisting of R 7 , R 8 , B 3 , and B 4 represent a substituent, and the substituent is a substituent R m selected from the group consisting of a hydroxy group, a linear or branched alkyl group having 1 to 18 carbon atoms, a monocyclic or polycyclic aliphatic alkyl group having 5 to 18 carbon atoms such as a bicyclic ring, a linear or branched alkoxy group having 1 to 24 constituent atoms, a non-aromatic cyclic substituent having 1 to 24 constituent atoms, a linear or branched perfluoroalkyl group having 1 to 18 carbon atoms, a linear or branched perfluoroalkoxy group, a linear or branched alkylsulfide group having 1 to 24 constituent atoms, an aryl group, an aryloxy group, an arylsulfide group, a heteroaryl group, an amino group, a monoalkylamino group, a dialkylamino group, a monoarylamino group, a diarylamino group, a cyclic amino group such as a piperidino group, a morpholino group, a thiomorpholino group, a tetrahydroquinolino group, or a tetrahydroisoquinolino group, an ethynyl group, a mercapto group, a silyl group, a sulfonic acid group, an alkylsulfonyl group, a formyl group, a carboxy group, a cyano group, and a halogen atom; R m is further substituted with one or more identical or different R m ; or solubilizing group It is.

3. B in general formula A １ and B ２ And B in general formula B ３ and B ４ each independently represents a substituted or unsubstituted phenyl group, and when the phenyl group has a plurality of substituents, the substituents may be bonded to form a ring. The photochromic composition according to claim 1 or 2.

4. 4. The photochromic composition according to claim 1, wherein the electron-withdrawing group is a halogen atom, a perfluoroalkyl group having 1 to 6 carbon atoms, a perfluorophenyl group, a perfluoroalkylphenyl group, or a cyano group.

5. The photochromic composition of claim 4 , wherein the halogen atom is a fluorine atom.

6. The photochromic composition of claim 4 , wherein the perfluoroalkyl group is a trifluoromethyl group.

7. In general formula B, R ７ and R ８ The photochromic composition according to any one of claims 1 to 6, wherein each independently represents a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

8. In general formula B, R ７ and R ８ The photochromic composition according to any one of claims 1 to 7, wherein each independently represents a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, or a hexyl group.

9. In general formula B, R １３ and R １４ each independently represents an electron-donating group selected from the group consisting of a methoxy group, an ethoxy group, a phenoxy group, a methylsulfide group, a phenylsulfide group, a dimethylamino group, a pyrrolidino group, a piperidino group, a morpholino group, and a thiomorpholino group. The photochromic composition according to any one of claims 1 to 8.

10. The photochromic composition according to any one of claims 1 to 9, comprising, on a mass basis, a larger amount of the compound represented by general formula B than the compound represented by general formula A.

11. The photochromic composition according to any one of claims 1 to 10, further comprising a polymerizable compound.

12. A photochromic article comprising a cured product obtained by curing the photochromic composition according to claim 11.

13. The photochromic article of claim 12 , comprising a substrate and the cured photochromic layer.

14. 14. The photochromic article of claim 12 or 13, which is a spectacle lens.

15. 14. The photochromic article of claim 12 or 13, which is a lens for goggles.

16. 14. The photochromic article of claim 12 or 13, which is a visor portion of a sun visor.

17. 14. The photochromic article according to claim 12 or 13, which is a shield member of a helmet.

18. A pair of glasses comprising the spectacle lens according to claim 14.

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