Photochromic composition, photochromic article, and spectacles

Abstract

To provide a photochromic article with a high coloring concentration in a visible range during coloring and a high fade rate.SOLUTION: A photochromic composition is provided that comprises one or more specific spirofluorenopyran compounds having an electron-withdrawing group and one or more specific spirofluorenopyran compounds having an electron-donating group.SELECTED DRAWING: None

Description

Technical Field

[0001] The present invention relates to a photochromic composition, a photochromic article, and glasses.

Background Art

[0002] A photochromic compound is a compound having a property (photochromism) of coloring under irradiation with light in a wavelength range having photoreactivity and fading in the absence of irradiation. For example, Patent Document 1 discloses a naphthopyran-based compound having photochromism.

Prior Art Documents

Patent Documents

[0003]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0004] As a method for imparting photochromism to an optical article such as a spectacle lens, there are a method of incorporating a photochromic compound into a substrate and a method of forming a layer containing a photochromic compound. Desirable performances for an optical article thus imparted with photochromism include a high coloring density during coloring in the visible region (wavelength 380 to 780 nm) and a fast fading rate after coloring by light irradiation.

[0005] One aspect of the present invention aims to provide a photochromic article having a high coloring density during coloring in the visible region and a fast fading rate.

Means for Solving the Problems

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

[0007] One aspect of the present invention also relates to 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.

[0008]

Chemical formula

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

[0010]

Chemical formula

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

[0012] As a result of intensive studies, the present inventors have newly found that by combining a compound represented by general formula A and 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 region. 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 region, and thus by combining these compounds, it becomes possible to color at a high concentration in a wide wavelength range. However, the present invention is not limited by the speculation described herein. Furthermore, it has also been newly found that by combining a compound represented by general formula A and a compound represented by general formula B, it is possible to provide a photochromic article that can exhibit a fast fading rate.

Advantages of the Invention

[0013] According to one aspect of the present invention, it is possible to provide a photochromic article having a high coloring density and a fast fading rate during coloring in the visible region.

Embodiments for Carrying Out the Invention

[0014] As an example, a photochromic compound is excited through irradiation with light such as sunlight and undergoes a structural conversion into a colored form. The structure after the structural conversion through light irradiation can be referred to as the "colored form". In contrast, the structure before light irradiation can be referred to as the "colorless form". However, the term "colorless" for the colorless form is not limited to complete colorlessness, but also includes cases where the color is faint compared to the colored form. The structures of general formula A and general formula B are each the structure of the colorless form.

[0015] In the present invention and this specification, the "photochromic article" refers to an article containing a photochromic compound. The photochromic article according to one aspect of the present invention contains, as the photochromic compound, 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 base material of the photochromic article and / or can be contained in the photochromic layer in a photochromic article having a base material and a photochromic layer. The "photochromic layer" is a layer containing a photochromic compound.

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

[0017] In the present invention and this specification, various substituents, namely, R in general formula A 1 , R 2 , B 1 , B 2 , R in general formula B 7 ~R 12 , B 3 and B 4 Any substituent that can be represented by, and further, when each of the groups described later has a substituent, the substituents are each independently A straight-chain or branched alkyl group having 1 to 18 carbon atoms such as a hydroxy group, methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, etc., a monocyclic or bicyclic cyclic aliphatic alkyl group having 5 to 18 carbon atoms such as a cyclopentyl group, cyclohexyl group, etc., a straight-chain or branched alkoxy group having 1 to 24 constituent atoms such as a methoxy group, ethoxy group, butoxy group, etc., a non-aromatic cyclic substituent having 1 to 24 constituent atoms, a straight-chain or branched perfluoroalkyl group having 1 to 18 carbon atoms such as a trifluoromethyl group, a straight-chain or branched perfluoroalkoxy group such as a trifluoromethoxy group, a straight-chain or branched alkyl sulfide group having 1 to 24 constituent atoms such as a methyl sulfide group, ethyl sulfide group, butyl sulfide group, etc., an aryl group such as a phenyl group, naphthyl group, anthracenyl group, fluoranthenyl group, phenanthryl group, pyranyl group, perylenyl group, styryl group, fluorenyl group, etc., an aryloxy group such as a phenyloxy group, an aryl sulfide group such as a phenyl sulfide group, a heteroaryl group such as a pyridyl group, furanyl group, thienyl group, pyrrolyl group, benzofuranyl group, benzothiophenyl group, indolyl group, dibenzofuranyl group, dibenzothiophenyl group, carbazolyl group, diazolyl group, triazolyl group, quinolinyl group, phenothiazinyl group, phenoxazinyl group, phenazinyl group, thianthrenyl group, acridinyl group, etc., an amino group (-NH 2 ), a monoalkylamino group such as a monomethylamino group, a dialkylamino group such as a dimethylamino group, a monoarylamino group such as a monophenylamino group, a diarylamino group such as a diphenylamino group, a cyclic amino group such as a piperidino group, morpholino group, thiomorpholino group, tetrahydroquinolino group, tetrahydroisoquinolino group, etc., 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, chlorine atom, bromine atom, iodine atom, etc., a substituent R selected from the group consisting of m ; or, R m further substituted with one or more identical or different R m ; It can be.

[0018] The above R m with one or more identical or different R m substituted thereon, examples of the substituent include a structure in which an alkoxy group is further substituted on the terminal carbon atom of an alkoxy group, and an alkoxy group is further substituted on the terminal carbon atom of this alkoxy group. Also, the above R m with one or more identical or different R m substituted thereon, another example of the substituent includes a structure in which the same or different R m is substituted at two or more positions among the five substitutable positions of a phenyl group. However, it is not limited to such examples.

[0019] In the present invention and this specification, "the number of carbon atoms" and "the number of constituent atoms" mean numbers including the number of carbon atoms or atoms of substituents for groups having substituents.

[0020] Also, in the present invention and this specification, various substituents, namely, R 1 in general formula A, R 2 , B 1 , B 2 , R 7 ~R 12 in general formula B, B 3 and B 4A substituent that can be represented by any of the following, and further, when each of the groups described below has a substituent, the substituent can independently be a solubilizing group. In the present invention and this specification, the "solubilizing group" refers to a substituent that can contribute to enhancing the compatibility with any liquid or a specific liquid. Examples of the solubilizing group include 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 by a silicon atom, a sulfur atom, a nitrogen atom, a phosphorus atom, etc., a combination of two or more of the above groups, etc. A substituent having such a substituent is preferably a substituent that can contribute to promoting the thermal motion of the molecules of the compound. A compound having a solubilizing group as a substituent can prevent solidification of the solute by inhibiting the approach of the solute molecules to 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 the solute or enhance the solubility of the compound having this substituent in a liquid. In one form, as the solubilizing group, an n-butyl group, an n-pentyl group, an n-hexyl group, an n-octyl group which are linear alkyl groups, a tert-butyl group which is a branched alkyl group, and a cyclopentyl group and a cyclohexyl group which are cyclic alkyl groups are preferable.

[0021] The above substituent can preferably be a substituent selected from the group consisting of a methoxy group, an ethoxy group, a phenoxy group, a methyl sulfide group, an ethyl sulfide group, a phenyl sulfide 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 morpholinyl group, a thiomorpholinyl 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 methyl sulfide group, a phenyl sulfide group, a trifluoromethyl group, a phenyl group, a dimethylamino group, a diphenylamino group, a piperidino group, a morpholinyl group, a thiomorpholinyl group, a cyano group and a solubilizing group.

[0022] In the present invention and this specification, the "electron-withdrawing group" refers to a substituent that is more likely to attract electrons from the bonded atom side compared to a hydrogen atom. Due to substituent effects such as the inductive effect and the mesomeric effect (or resonance effect), the electron-withdrawing group can attract electrons. Specific examples of the electron-withdrawing group include a halogen atom (fluorine atom: -F, chlorine atom: -Cl, bromine atom: -Br, iodine atom: -I), trifluoromethyl group: -CF 3 , nitro group: -NO 2 , cyano group: -CN, formyl group: -CHO, acyl group: -COR (R is a substituent), alkoxycarbonyl group: -COOR, carboxy group: -COOH, substituted sulfonyl group: -SO 2 R (R is a substituent), sulfo group: -SO 3 H, etc. can be mentioned. Preferred electron-withdrawing groups include a fluorine atom, which is an electron-withdrawing group with a high electronegativity, and an electron-withdrawing group whose para-position substituent constant σ p based on the Hammett rule has a positive value, etc. can be mentioned.

[0023] In the present invention and this specification, the "electron-donating group" refers to a substituent that is more likely to donate electrons to the bonded atom side compared to a hydrogen atom. Due to the sum of substituent effects such as the inductive effect and the mesomeric effect (or resonance effect), the electron-donating group can be a substituent that is more likely to donate electrons. Specific examples of the electron-donating group include a hydroxy group: -OH, thiol group: -SH, alkoxy group: -OR (R is an alkyl group), alkyl sulfide group: -SR (R is an alkyl group), aryl sulfide group, acetyl group: -OCOCH 3 , amino group: -NH 2 , alkylamide group: -NHCOCH 3 , dialkylamino group: -N(R) 2 (the two Rs are the same or different alkyl groups, aryl groups, and R may be bonded to each other to form a ring structure), methyl group, etc. can be mentioned. Preferred electron-donating groups include an electron-donating group whose para-position substituent constant σ p based on the Hammett rule has a negative value, etc. can be mentioned.

[0024] Para-substituent constant σ based on Hammett's rule p Specific examples from (Source: Hideaki Iwamura, Ryoji Noyori, Takeshi Nakai, Isao Kitagawa, Graduate School Organic Chemistry (Part 1) (1988)) are shown below. -N(CH 3 ) 2 : -0.83 -OCH3: -0.27 -t-C 4 H 9 : -0.20 -CH 3 : -0.17 -C 2 H 5 : -0.15 -C 6 H 5 : -0.01 (-H: 0) -F: +0.06 -Cl: +0.27 -Br: +0.23 -CO 2 C 2 H 5 : +0.45 -CF 3 : +0.54 -CN: +0.66 -SO 2 CH 3 : +0.72 -NO 2 : +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>

Chemical formula

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

[0028] R1 and R 2 each independently preferably represents a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, more preferably represents a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group or a hexyl group. R 1 and R 2 more preferably each independently represents a methyl group or an ethyl group, and even more preferably R 1 and R 2 both represent a methyl group or both represent an ethyl group.

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

[0030]

Chemical formula

[0031] In general formula A, R 3 to R 6 each independently represents a hydrogen atom or an electron-withdrawing group. However, R 3 to R 6One or more of them represent 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 form, the compound represented by the general formula A can be the following compound. R 3 ~R 6 Among them, only R 4 is an electron-withdrawing group, and R 3 , R 5 and R 6 are hydrogen atoms. R 3 ~R 6 Among them, R 4 and R 6 are the same or different electron-withdrawing groups, and R 3 and R 5 are hydrogen atoms. R 3 ~R 6 Among them, R 3 and R 5 are the same or different electron-withdrawing groups, and R 4 and R 6 are hydrogen atoms.

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

[0034]

Chemical formula

[0035]

Chemical formula

[0036]

Chemical formula

[0037]

Chem.

[0038]

Chem.

[0039]

Chem.

[0040]

Chem.

[0041]

Chem.

[0042]

Chem.

[0043]

Chem.

[0044]

Chem.

[0045]

Chem.

[0046]

Chem.

[0047] [Chemical]

[0048] [Chemical]

[0049] [Chemical]

[0050] [Chemical]

[0051] [Chemical]

[0052] [Chemical]

[0053] [Chemical]

[0054] [Chemical]

[0055] [Chemical]

[0056] [Chemical]

[0057] [Chemical]

[0058] <Compound represented by General Formula B>

Chem.

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

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

[0062]

Chem.

[0063] R 9 ~R 12 each independently represents a hydrogen atom or a substituent. In one form, R 9 ~R 12 can all be hydrogen atoms. In another form, R 10 is an electron-withdrawing group, and R 9 , R 11 and R 12 can all be hydrogen atoms. Also, in another form, R 9 and R 11 are each independently an electron-withdrawing group, and R 10 and R 12 can be hydrogen atoms. Preferred electron-withdrawing groups include a halogen atom, a C1-6 perfluoroalkyl group, a perfluorophenyl group, a perfluoroalkylphenyl group, or a cyano group. A fluorine atom is preferred as the halogen atom. A trifluoromethyl group is preferred as the C1-6 perfluoroalkyl group.

[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 can be hydrogen atoms. Specific examples of such substituted phenyl groups 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 halogen atoms (preferably fluorine atoms) at all five substitution positions of the phenyl group, and a monosubstituted phenyl group substituted with a cyano group at the position para to the carbon atom to which R 10 is attached.

[0065] R 13 and R 14 each independently represents a hydrogen atom or an electron-donating group. However, one or more of R 13 and R 14 represent an electron-donating group. R 13 and R 14Each independently preferably 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 form, one can be a hydrogen atom and the other can be an electron-donating group, and in another form, both can independently be electron-donating groups. R 13 and R 14 are preferably both electron-donating groups. In this case, R 13 and R 14 can be the same or different electron-donating groups. Among them, for R 13 and R 14 , it is preferable that R 13 is a morpholino group and R 14 is an alkoxy group (preferably a methoxy group), that R 13 is a morpholino group and R 14 is a methylsulfide group (-S-CH 3 ), that R 13 and R 14 are both alkoxy groups (preferably methoxy groups), and that R 13 and R 14 are both methylsulfide groups (-S-CH 3 ).

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

[0068]

Chemical formula

[0069]

Chemical formula

[0070] [Chemical]

[0071] [Chemical]

[0072] [Chemical]

[0073] [Chemical]

[0074] [Chemical]

[0075] [Chemical]

[0076] [Chemical]

[0077] [Chemical]

[0078] [Chemical]

[0079] [Chemical]

[0080] [Chemical]

[0081]

Chem.

[0082]

Chem.

[0083]

Chem.

[0084]

Chem.

[0085]

Chem.

[0086] The compounds represented by General Formula A and the compounds represented by General Formula B can be synthesized by known methods. For the synthesis methods, for example, the following documents can be referred to. Japanese Patent No. 4884578, US2006 / 0226402A1, US2006 / 0228557A1, US2008 / 0103301A1, US2011 / 0108781A1, US2011 / 0108781A1, US Patent No. 7527754, US Patent No. 7556751, WO2001 / 60811A1, WO2013 / 086248A1, WO1996 / 014596A1 and WO2001 / 019813A1.

[0087] The photochromic article according to one aspect of the present invention and the photochromic composition according to one aspect 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 above photochromic article and the above photochromic composition can be only one kind, or can be two or more kinds (for example, two or more kinds and four or less kinds). The compound represented by general formula B contained in the above photochromic article and the above photochromic composition can be only one kind, or can be two or more kinds, preferably two or more kinds, and can be, for example, four or less kinds or three or less kinds. The above photochromic article and the above photochromic composition preferably contain more of the compound represented by general formula B than the compound represented by general formula A on a mass basis. Taking the total of the compound represented by general formula A and the compound represented by general formula B as 100% by mass, the content of the compound represented by general formula B is preferably more than 50% by mass, more preferably 60% by mass or more, still more preferably 70% by mass or more, even more preferably 80% by mass or more, and even more preferably 90% by mass or more. With respect to the total (100% by mass) of the compound represented by general formula A and the compound represented by general formula B, the content of the compound represented by general formula B can be less than 100% by mass, and can be 99% by mass or less, 98% by mass or less, 97% by mass or less, 96% by mass or less, or 95% by mass or less. The content of the above compound represented by general formula B is the total content when two or more kinds of the compound represented by general formula B are contained in the above photochromic article and the above photochromic composition. This also applies to the content of various components in the present invention and this specification. The above photochromic article and the above photochromic composition can contain, for example, about 0.1 to 15.0% by mass in total of the compound represented by general formula A and the compound represented by general formula B, taking their total amount as 100% by mass. However, it is not limited to this range.

[0088] [Photochromic article, photochromic composition] The above photochromic article can have at least a substrate. In one form, the compound represented by general formula A and the compound represented by general formula B can be included in the substrate of the above photochromic article. The above photochromic article can have a substrate and a photochromic layer, and the substrate and / or the photochromic layer can contain the compound represented by general formula A and the compound represented by general formula B. The compound represented by general formula A and the compound represented by general formula B can be contained only in the substrate in one form, only in the photochromic layer in another form, or in both the substrate and the photochromic layer in yet another form. Also, the substrate and the photochromic layer can contain only the compound represented by general formula A and the compound represented by general formula B as the photochromic compound, or can also contain one or more other photochromic compounds. Examples of other photochromic compounds include azobenzenes, spiropyrans, spirooxazines, naphthopyrans, indenonaphthopyrans, phenanthropyrans, hexaallylbisimidazoles, donor-acceptor Stenhouse adducts (DASAs), salicylideneanilines, dihydropyrenes, anthracene dimers, fulgides, diarylethenes, phenoxynaphthacenequinones, stilbenes, and the like.

[0089] <substrate> The above photochromic article can include a substrate selected according to the type of the photochromic article. As an example of the substrate, as the spectacle lens substrate, a plastic lens substrate or a glass lens substrate can be mentioned. The glass lens substrate can 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 cured products of curable compositions containing a (thio)epoxy compound having one or more disulfide bonds in the molecule (generally called transparent resins). As the lens substrate, an undyed one (colorless lens) may be used, or a dyed one (dyed lens) may be used. 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 it may be within the above range or deviate above or below the above range. Here, the refractive index refers to the refractive index with respect to light having a wavelength of 500 nm. Also, the lens substrate may be a lens having a refractive power (so-called powered lens) or a lens without refractive power (so-called non-powered lens).

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

[0091] The spectacle lens can be various lenses such as a single-focus lens, a multi-focus lens, a progressive power lens, etc. The type of the lens is determined by the surface shape of both surfaces of the lens base material. Also, the surface of the lens base material can be any of a convex surface, a concave surface, and a flat surface. In a normal lens base material and a spectacle lens, the object-side surface is convex and the eyeball-side surface is concave. However, it is not limited thereto. The photochromic layer can usually be provided on the object-side surface of the lens base material, but can 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, at least one compound represented by general formula B, and at least one polymerizable compound. For example, such a polymerizable composition is directly applied onto the surface of the substrate or applied onto the surface of a layer provided on the substrate, and the applied polymerizable composition is subjected to a curing treatment, whereby a photochromic layer can be formed as a cured layer containing at least one compound represented by general formula A and at least one compound represented by general formula B. As the coating method, known coating methods such as spin coating method, dip coating method, spray coating method, inkjet method, nozzle coating method, slit coating method, etc. can be adopted. The curing treatment can be light irradiation and / or heat treatment. The polymerizable composition can further contain one or more additives (such as a polymerization initiator, etc.) in addition to one or more polymerizable compounds. The polymerizable composition can be cured and a cured layer can be formed as the polymerization reaction of the polymerizable compound proceeds.

[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 also 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, the polymerizable compound refers to a compound having one or more polymerizable groups in one molecule, and the "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, an isocyanate group, etc.

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

[0096] (Episulfide compound) An episulfide compound is a compound having two or more episulfide groups in one molecule. An episulfide group is a polymerizable group that can undergo 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-tetrakis(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-epithiopropyldithiomethylthio) ethane, 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-dithiane, 2-[1,1-bis(2,3-epithiopropyldithiomethylthio) methyl]-1,3-dithiane, etc.

[0097] (Ethynyl compound) A thietanyl compound is a thiethane compound having two or more thietanyl groups in one molecule. A thietanyl group is a polymerizable group capable of ring-opening polymerization. Among thietanyl compounds, some have an episulfide group together with a plurality of thietanyl groups. Such compounds are listed as examples of the above episulfide compounds. Other thietanyl compounds include a metal-containing thiethane compound having a metal atom in the molecule and a non-metal-based thiethane compound not containing a metal.

[0098] Specific examples of the non-metallic thiethane 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-trithia butane, 1,5-bis(3-thietanyl)-1,2,4,5-tetrathia pentane, 1,6-bis(3-thietanyl)-1,3,4,6-tetrathia hexane, 1,6-bis(3-thietanyl)-1,3,5,6-tetrathia hexane, 1,7-bis(3-thietanyl)-1,2,4,5,7-pentathia heptane, 1,7-bis(3-thietanylthio)-1,2,4,6,7-pentathia heptane, 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-dithia octane, 1,11-bis(3-thietanylthio)-4,8-bis(3-thietanylthiomethyl)-3,6,9-trithia undecane, 1,11-bis(3-thietanylthio)-4,7-bis(3-thietanylthiomethyl)-3,6,9-trithia undecane, 1,11-bis(3-thietanylthio)-5,7-bis(3-thietanylthiomethyl)-3,6,9-trithia undecane, 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) methylthio> methylthio] thietane, bisthietanyl disulfide, bisthietanyl trisulfide, bisthietanyl tetrasulfide, bisthietanyl pentasulfide, 1,4-bis(3-thietanyldithio)-2,3-dithia butane, 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, etc.

[0099] Examples of the metal-containing thietane compounds include those containing, within the molecule, as the metal atom, a Group 14 atom such as a Sn atom, a Si atom, a Ge atom, or a Pb atom, a Group 4 element such as a Zr atom or a Ti atom, a Group 13 atom such as an Al atom, or a Group 12 atom such as a Zn atom. Specific examples include alkylthio(thietanylthio)tin, bis(alkylthio)bis(thietanylthio)tin, alkylthio(alkylthio)bis(thietanylthio)tin, bis(thietanylthio)cyclic dithiostannane compounds, alkyl(thietanylthio)tin compounds, and the like.

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

[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, bis(isopropylthio)bis(thietanylthio)tin, and the like.

[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, isopropylthio(propylthio)bis(thietanylthio)tin, and the like.

[0103] Specific examples of the bis(thietanylthio)cyclic dithiostannane compounds include bis(thietanylthio)dithiastanetane, bis(thietanylthio)dithiastanonane, bis(thietanylthio)dithianonanane, bis(thietanylthio)trithiastanonane, and the like.

[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, tris(thietanylthio)bismuth, etc.

[0105] (Polyamine compound) The polyamine compound is a compound having two or more NH 2 groups in one molecule, capable of forming a urea bond by reaction with a polyisocyanate and capable of forming a thiourea bond by reaction with a polyisothiocyanate. Specific examples of the polyamine compound include ethylenediamine, hexamethylenediamine, isophoronediamine, nonamethylenediamine, undecamethylenediamine, dodecamethylenediamine, metaxylylenediamine, 1,3-propanediamine, putrescine, 2-(2-aminoethylamino)ethanol, diethylenetriamine, p-phenylenediamine, m-phenylenediamine, melamine, 1,3,5-benzenetriamine, etc.

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

[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, triglycidyl ether of tris(2-hydroxyethyl) isocyanurate, and the like.

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

[0109] Specific examples of the aromatic epoxy compound include resorcin diglycidyl ether, bisphenol A diglycidyl ether, bisphenol F diglycidyl ether, bisphenol S diglycidyl ether, orthophthalic acid diglycidyl ester, phenol novolak polyglycidyl ether, cresol novolak polyglycidyl ether, and the like.

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

[0111] Specific examples of the chain aliphatic sulfur atom-containing epoxy compounds 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-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 compounds 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, 2,5-bis(2,3-epoxypropylthiomethyl)-2,5-dimethyl-1,4-dithiane, and the like.

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

[0114] Hereinafter, a compound having a polymerizable group selected from the group consisting of an acryloyl group and a methacryloyl group is 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)acryloxyethoxyphenyl)propane, 2,2-bis(4-(meth)acryloxydiethoxyphenyl)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)acryloxyethoxyphenyl)methane, 1,1-bis(4-(meth)acryloxydiethoxyphenyl)methane, dimethyloltricyclodecane di(meth)acrylate, trimethylolpropane tri(meth)acrylate, ditrimethylolpropane 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, bifunctional urethane (meth)acrylate, and the like.

[0115] Specific examples of the compound having an allyl group (allyl compound) 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, methacryloyloxypolyethylene glycol allyl ether, and the like.

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

[0117] The above - mentioned photochromic article can include at least one layer known as a functional layer of a photochromic article, such as a protective layer for improving the durability of the photochromic article, an antireflection layer, a water - repellent or hydrophilic antifouling layer, an anti - fogging layer, a primer layer for improving the adhesion between layers, at an arbitrary position.

[0118] The above - mentioned photochromic article can be an optical article. One form of the optical article is an eyeglass lens. Such an eyeglass lens can also be called a photochromic lens or a photochromic eyeglass lens. Further, as one form of the optical article, a lens for goggles, the visor (hisaashi) part of a sun visor, a shield member of a helmet, etc. can also be mentioned. By applying the above - mentioned photochromic composition, which is a polymerizable composition, onto a substrate for these optical articles and subjecting the applied composition to a curing treatment to form a photochromic layer, an optical article having an antiglare function can be obtained.

[0119] [Glasses] One aspect of the present invention relates to glasses provided with spectacle lenses, which are one form of the above photochromic article. Details of the spectacle lenses included in the glasses are as described above. By providing such spectacle lenses, the glasses can exhibit an anti-glare effect like sunglasses, for example, when outdoors, the photochromic compound is irradiated with sunlight and colored, and when returning indoors, the photochromic compound can fade and the transparency can be restored. Regarding the configuration such as the frame of the glasses, known techniques can be applied.

Examples

[0120] Hereinafter, the present invention will be further described with reference to examples. However, the present invention is not limited to the embodiments shown in the examples. The “%” described below indicates mass %.

[0121] [Synthesis of Compounds] With reference to the reference documents shown above regarding the method for synthesizing compounds, Compounds 1 to 15 shown below were synthesized. 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]

Chemical Formula

[0123]

Chemical Formula

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

[0125] The comparative compound used in Comparative Example 3 is the following compound. [Chemical formula]

[0126] <Formation of primer layer> The plastic lens substrate (product name EYAS manufactured by HOYA: center thickness 2.5 mm, diameter 75 mm, spherical lens power -4.00) was alkali-washed by immersing it in an aqueous sodium hydroxide solution with a concentration of 10% by mass (liquid temperature 60 °C) for 5 minutes, and then further washed with pure water and dried. Thereafter, an aqueous polyurethane resin solution (a polycarbonate polyol-based polyurethane emulsion, viscosity 100 cPs, solid content concentration 38% by mass) was applied to the convex surface of this plastic lens substrate in an environment of room temperature and relative humidity of 40 - 60% using a spin coater MS-B150 manufactured by Mikasa at a rotation speed of 1500 rpm for 1 minute by the spin coating method, and then naturally dried for 15 minutes to form a primer layer with a thickness of 5.5 μm.

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

[0128] [Evaluation method] <Evaluation of coloring density> The visual reflectance was determined by the following method in accordance with JIS T7333:2005. For each of the spectacle lenses of the examples and comparative examples, light was irradiated through an aroma mass filter using a xenon lamp as a light source for 15 minutes toward the convex surface to color the photochromic layer. This irradiated light was made to have the irradiance and the tolerance of the irradiance as shown in Table 1 as specified in JIS T7333:2005. The transmittance at the time of this coloring was measured with a spectrophotometer manufactured by Otsuka Electronics Co., Ltd. Table 2 shows the visual transmittance T(%) obtained from the measurement results in the wavelength range from 380 nm to 780 nm. The smaller the value of T(%), the more the photochromic compound is colored at a high concentration.

[0129]

Table 1

[0130] <Evaluation of fading rate> The fading rate was evaluated by the following method. The transmittance (measurement wavelength: 550 nm) of each of the spectacle lenses of the examples and comparative examples before light irradiation (uncolored state) was measured with a spectrophotometer manufactured by Otsuka Electronics Co., Ltd. The transmittance measured here is referred to as the "initial transmittance". For each spectacle lens, light was irradiated through an aroma mass filter using a xenon lamp as a light source for 15 minutes to color the photochromic layer. This irradiated light was made to have the irradiance and the tolerance of the irradiance as shown in Table 1 as specified in JIS T7333:2005. The transmittance at the time of this coloring was measured in the same manner as the initial transmittance. The transmittance measured here is referred to as the "transmittance at the time of coloring". Thereafter, the time required for the transmittance to reach [(initial transmittance - transmittance at the time of coloring) / 2] was measured from the time when the light irradiation was stopped. This time is defined as the "half-life time". It can be said that the shorter the half-life time, the faster the fading rate. The obtained half-life times are shown in Table 2.

[0131]

Table 2

[0132] From the results shown in Table 2, it can be confirmed that by combining the compound represented by the general formula A and the compound represented by the general formula B, it becomes possible to provide a photochromic article that colors at a high concentration in the visible region and exhibits a fast fading rate.

[0133] Finally, the above aspects are summarized.

[0134] According to one aspect, there are provided a photochromic article and a photochromic composition containing one or more compounds represented by the general formula A and one or more compounds represented by the general formula B.

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

[0136] In one form, in the general formula A, R 1 and R 2 can 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 form, B 1 and B 2 in the general formula A and B 3 and B 4 in the general formula B can each independently represent a substituted or unsubstituted phenyl group. Here, when the phenyl group has a plurality of substituents, these substituents may combine to form a ring.

[0138] In one form, the electron-withdrawing group in the 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 form, the halogen atom can be a fluorine atom.

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

[0141] In one embodiment, R in general 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 represent a substituent, and such a substituent is a hydroxyl group, a linear or branched alkyl group having 1 to 18 carbon atoms, a cyclic aliphatic alkyl group of a monocyclic or bicyclic ring such as a monocyclic or bicyclic ring having 5 to 18 carbon atoms, 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 alkyl sulfide group having 1 to 24 constituent atoms, an aryl group, an aryloxy group, an aryl sulfide 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 and other cyclic amino groups, 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, a substituent R m ; R m is further substituted with one or more identical or different R m ; or a solubilizing group can be.

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

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

[0144] In one form, in General Formula B, R 13 and R 14 can each independently represent an electron-donating group selected from the group consisting of a methoxy group, an ethoxy group, a phenoxy group, a methyl sulfide group, a phenyl sulfide group, a dimethylamino group, a pyrrolidino group, a piperidino group, a morpholino group, and a thiomorpholino group.

[0145] In one form, the above photochromic article and the above photochromic composition can contain more of the compound represented by General Formula B than the compound represented by General Formula A on a mass basis.

[0146] In one form, the above photochromic article and the above photochromic composition can contain one kind of the compound represented by General Formula A and two kinds of the compound represented by General Formula B.

[0147] In one form, the above photochromic article has a substrate and a photochromic layer, and can be a photochromic article in which the photochromic layer contains one or more kinds of the compound represented by General Formula A and one or more kinds of the compound represented by General Formula B.

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

[0149] In one form, the above photochromic composition can contain a polymerizable compound.

[0150] In one form, the above photochromic article can be an eyeglass lens.

[0151] In one form, the above 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 the shield member of a helmet.

[0154] According to one aspect, glasses provided with the above-described spectacle lenses are provided.

[0155] The various aspects and various forms described herein can be combined in any combination of two or more.

[0156] The embodiments disclosed this time should be considered to be illustrative in all respects and not restrictive. The scope of the present invention is shown not by the above description but by the claims, and it is intended that all modifications within the meaning and scope equivalent to the claims be included.

Industrial Applicability

[0157] One aspect of the present invention is useful in technical fields such as 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 ３ ~R ６ each independently represents a hydrogen atom or an electron-withdrawing group, provided that R ３ ~R ６ At least one of represents an electron-withdrawing group. 【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.

2. In general formula A, R １ and R ２ The photochromic composition according to claim 1, wherein each independently represents a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

3. In general formula A, R １ and R ２ The photochromic composition according to claim 1 or 2, wherein each independently represents a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, or a hexyl group.

4. 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 any one of claims 1 to 3.

5. 5. 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.

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

7. The photochromic composition of claim 5 , wherein the perfluoroalkyl group is a trifluoromethyl group.

8. R in General 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 The photochromic composition according to any one of claims 1 to 7,

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

10. In general formula B, R ７ and R ８ The photochromic composition according to any one of claims 1 to 9, wherein each independently represents a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, or a hexyl group.

11. 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 21 to 30,

12. The photochromic composition according to any one of claims 1 to 11, comprising, on a mass basis, a larger amount of the compound represented by general formula B than the compound represented by general formula A.

13. The photochromic composition according to any one of claims 1 to 12, further comprising a polymerizable compound.

14. A photochromic article comprising a cured product obtained by curing the photochromic composition according to claim 13.

15. 15. The photochromic article of claim 14, comprising a substrate and the cured photochromic layer.

16. 16. The photochromic article of claim 14 or 15, which is a spectacle lens.

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

18. 16. The photochromic article of claim 14 or 15, which is a visor portion of a sun visor.

19. 16. The photochromic article according to claim 14 or 15, which is a shield member of a helmet.

20. A pair of spectacles comprising the spectacle lens according to claim 16.

Images