Curable composition, cured product, laminate, lens, and eyewear

Abstract

The purpose of the present invention is to provide a curable composition, a cured product, a laminate, a lens, and eyeglasses which are capable of achieving a cured product having excellent performance of a functional dye. According to one embodiment, a curable composition is provided. The curable composition contains a first radically polymerizable monomer represented by formula (1) and a functional dye. The content of the first radically polymerizable monomer is 15 mass% or more. According to other embodiments, a cured product is provided. The cured product is obtained by curing the curable composition according to the embodiment.

Description

Technical Field

[0001] The present invention relates to a curable composition, a cured product, a laminate, a lens, and glasses. Background Art

[0002] Photochromic compounds typified by naphthopyran compounds, fulgide compounds, spirooxazine compounds, etc. are compounds that can reversibly obtain two isomers with different absorption spectra by irradiating light containing ultraviolet rays such as sunlight or the light of a mercury lamp. Generally, they have the following characteristics: when ultraviolet rays are irradiated on a colorless decolored-state compound, the color rapidly changes and isomerizes into a colored developed state (development reaction), and when the light irradiation is stopped and placed in the dark, it returns to the original color (hereinafter, also referred to as photochromism). Utilizing this characteristic, they are used for various applications, particularly for optical materials.

[0003] For example, photochromic spectacle lenses imparted with photochromism by using a photochromic compound rapidly color in the outdoor under sunlight irradiation containing ultraviolet rays and function as sunglasses, and fade indoors without such light irradiation and function as transparent ordinary glasses. In recent years, the demand for them has increased.

[0004] As specific methods for imparting photochromism to optical materials, the following means (A) to (C) are known.

[0005] (A) A method of directly molding an optical material such as a lens by mixing a photochromic compound in a polymerizable monomer and polymerizing it.

[0006] (B) A method of providing a resin layer in which a photochromic compound is dispersed on the surface of a plastic molded product such as a lens by coating or casting polymerization.

[0007] (C) A method of bonding two optical sheets with an adhesive layer formed of an adhesive material resin in which a photochromic compound is dispersed.

[0008] Among them, in particular, as shown in Patent Document 1, a coating method in which a photochromic curable composition is coated on a plastic lens by spin coating or the like and photocured to form a photochromic coating layer is an effective means because it can be applied to various existing lenses.

[0009] In addition, a compound that can return to the original decolored state not only by light of a specific wavelength but also by heat when isomerizing from the developed state to the decolored state in a photochromic compound used in a photochromic optical article is called a T-type photochromic compound. T-type photochromic compounds have been widely studied and developed as materials for photochromic lenses.

[0010] In T-type photochromic compounds, the following characteristics (1) to (5) are generally required.

[0011] (1) The coloring degree in the visible light region before ultraviolet irradiation (hereinafter referred to as initial coloring) is small.

[0012] (2) The rate from the start of ultraviolet irradiation to the saturation of the coloring concentration is high (hereinafter also referred to as high coloring sensitivity).

[0013] (3) The rate from the stop of ultraviolet irradiation to the restoration to the original state (hereinafter referred to as fading rate) is high.

[0014] (4) The repeated durability of the reversible action of (2) and (3) above is good.

[0015] (5) It is highly soluble in the monomer composition and has high dispersibility in the cured product of the monomer composition.

[0016] As T-type photochromic compounds satisfying these characteristics, chromene compounds have been extensively studied. Chromene compounds exhibit excellent photochromism in an environment where structural changes are likely to occur, such as in solution. However, in an environment where structural changes are less likely to occur, such as in a polymer solid matrix, there is a tendency for the fading half-life to become longer, that is, the fading rate decreases. It is considered that the reason is that the free space in the polymer solid matrix is overwhelmingly smaller than that in solution, and thus the reversible structural change of the chromene compound is restricted. Thus, when a chromene compound is dispersed in a polymer solid matrix such as various plastic materials, the chromene compound cannot fully exhibit its originally excellent photochromic characteristics, and in particular, the fading rate may decrease. Therefore, in order to form free space even in a polymer solid matrix, various photochromic curable compositions have been studied so far.

[0017] As representatives of photochromic coating agents applicable to spectacle lenses, the following (a) to (d) have been proposed.

[0018] (a) A photochromic compound is dissolved in a urethane oligomer (see Patent Document 1).

[0019] (b) A polymerizable monomer having one (meth)acryloyl group, a polymerizable monomer having two (meth)acryloyl groups, and a polymerizable monomer having three or more (meth)acryloyl groups are combined in a specific ratio, and a photochromic compound is dissolved therein (see Patent Document 2).

[0020] (c) As the polymerizable monomer component, only various ones selected from polymerizable monomers having 2 (meth)acryloyl groups are used, and a photochromic compound is dissolved in such a polymerizable monomer component (see Patent Document 3).

[0021] (d) A curable composition containing a photochromic compound, an amine compound, a radically polymerizable monomer having a silanol group, and / or a radically polymerizable monomer having an isocyanate group (see Patent Document 4).

[0022] Prior art documents

[0023] Patent documents

[0024] Patent Document 1: WO 98 / 37115

[0025] Patent Document 2: US Patent No. 5,914,174 Specification

[0026] Patent Document 3: WO 01 / 02449

[0027] Patent Document 4: WO 03 / 11967

[0028] Patent Document 5: WO 2015 / 054036

[0029] Patent Document 6: WO 2009 / 075388

[0030] Patent Document 7: EP 3,418,347 Specification Summary of the invention

[0031] Problems to be solved by the invention

[0032] An object of the present invention is to provide a curable composition, a cured product, a laminate, a lens, and glasses that can achieve a cured product having excellent performance, appearance, and adhesion of a functional pigment.

[0033] Solutions to the problems

[0034] The present disclosure relates to a curable composition. The curable composition contains a first radically polymerizable monomer represented by the following formula (1) and a functional pigment. The content of the first radically polymerizable monomer is 15% by mass or more and 34% by mass or less.

[0035]

[0036] In the formula, R 1 is a hydrogen atom or a methyl group. R 2 is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. R 3 is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. R 4 is a linear or branched alkylene group having 1 to 7 carbon atoms which may optionally have a substituent. R 5 is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. R 6 is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. R 7is a hydrogen atom or a methyl group. a is from 0 to 10. b is from 0 to 20. c is from 2 to 20. c is a number greater than each of a, b, d, and e. d is from 0 to 20. e is from 0 to 10.

[0037] Further, according to the present disclosure, there is provided a cured product. The cured product is obtained by curing the curable composition of the embodiment.

[0038] Further, according to the present disclosure, there is provided a laminate. The laminate includes an optical substrate and the cured product of the embodiment located on the surface of the optical substrate.

[0039] Further, according to the present disclosure, there is provided a lens. The lens includes a lens substrate and the cured product of the embodiment located on the surface of the optical substrate.

[0040] Further, according to the present disclosure, there is provided a pair of glasses. The pair of glasses includes the lens of the embodiment.

[0041] Effects of the Invention

[0042] According to the present invention, there are provided a curable composition, a cured product, a laminate, a lens, and a pair of glasses that can achieve a cured product having excellent functionality, appearance, and adhesion of a functional pigment. BRIEF DESCRIPTION OF THE DRAWINGS

[0043] Figure 1 is a cross-sectional view schematically showing an example of the laminate of the embodiment. DETAILED DESCRIPTION OF THE INVENTION

[0044] The curable composition of the embodiment uses the (A-1) first radically polymerizable monomer represented by the formula (1) as the (A) radically polymerizable component in combination with the (B) functional pigment. The content of the (A-1) first radically polymerizable monomer is 15% by mass or more and 34% by mass or less. When such a curable composition is used, a cured product having excellent functionality of the functional pigment, and also excellent appearance and adhesion can be achieved. The reason is not clear yet, but the present inventors presume as follows.

[0045] First, functional pigments such as photochromic compounds include compounds that develop color, fade, or change color through structural changes caused by energy such as light. In order for such functional pigments to easily undergo structural changes in a polymer solid matrix, the soft segment in the polymer solid matrix is important. The first radically polymerizable monomer has a polyalkylene glycol chain structure with a repeating unit of an alkyleneoxy group having 3 to 10 carbon atoms. It is considered that in the polymer of the curable composition containing the first radically polymerizable monomer, a plurality of alkyleneoxy chain portions aggregate to form a soft segment formed by arranging these alkyleneoxy chain polymers. Moreover, it is considered that the distance between oxygen atoms of the alkyleneoxy chains in this soft segment is greater than the distance between oxygen atoms of the alkyleneoxy chains in the soft segment formed by a radically polymerizable monomer having a polyalkylene glycol chain structure with 2 or fewer carbon atoms. That is, alkyleneoxy chains with a larger number of carbon atoms are less likely to aggregate with each other than alkyleneoxy chains with a smaller number of carbon atoms, so it is considered that the distance between polymer chains is large. When the distance between polymer chains is large, a larger free space is required for the structural change of the functional pigment, so it is considered that the structural change is less likely to be hindered.

[0046] Furthermore, when using the curable composition of the embodiment, a cured product that combines the high functionality and high hardness of the functional pigment can be achieved. That is, in a cured product with high hardness, the softness of the soft segment is low, or the proportion of the soft segment is small, and there is a tendency for the functionality of the functional pigment to decrease. It is considered that the curable composition of the embodiment uses a monomer having an alkyleneoxy chain with a larger number of carbon atoms, so the softness of the alkyleneoxy chain constituting the soft segment is lower than that of the soft segment constituted by an alkyleneoxy chain with 2 or fewer carbon atoms. On the other hand, as described above, the distance between alkyleneoxy chains is large, so the free space in the soft segment is wide, and the functionality of the functional pigment can be improved. Therefore, even if the proportion of the first radically polymerizable monomer in the curable composition is increased to improve the functionality of the functional pigment, a cured product with high hardness can be achieved.

[0047] In addition, if the curable composition of the embodiment is used, the adhesion between the cured product of the curable composition and the substrate on which the cured product is laminated can be improved. That is, the curable composition is coated on an optical substrate such as a lens substrate and cured to form a laminate of the cured product and the lens substrate. In this laminate, in order to improve the adhesion between the optical substrate and the cured product, for example, a primer layer containing a urethane-based resin is sometimes provided. In the case where the primer layer is provided, the laminate becomes a laminate in which the optical substrate, the primer layer, and the cured product are laminated in sequence. Generally, in order to obtain high adhesion in the laminate, it is necessary to balance the adhesion between the optical substrate and the primer layer and the adhesion between the cured product and the primer layer. In order to improve the adhesion between the cured product and the primer layer, it is considered that the curable composition needs to penetrate moderately into the primer layer to form a mixed layer.

[0048] The inventors of the present invention have found that for a curable composition containing a first radically polymerizable monomer, in order to sufficiently form a mixed layer, the proportion of the first radically polymerizable monomer needs to be 34% by mass or less. That is, the first radically polymerizable monomer has lower compatibility with the primer layer than bis(meth)acrylate having an alkyleneoxy chain with 2 or less carbon atoms. Therefore, it is considered that if the content of the first radically polymerizable monomer exceeds 34% by mass, the curable composition is difficult to penetrate into the primer layer, so it is difficult to form a mixed layer with the primer layer, and the adhesion of the laminate decreases. On the other hand, when the amount of the first radically polymerizable monomer is too small, the laminate may become cloudy. It is considered that this is because the polymerizable composition with too small an amount of the first radically polymerizable monomer easily penetrates into the primer layer, so a mixed layer with an excessive thickness is formed. That is, it is considered that within this mixed layer with an excessive thickness, the first radically polymerizable monomer re-aggregates and becomes cloudy. In contrast, the curable composition of the embodiment containing 15 to 34% by mass of the first radically polymerizable monomer moderately erodes the primer layer, so a laminate with high adhesion maintained and cloudiness suppressed can be achieved.

[0049] Hereinafter, each component will be described in detail.

[0050] <(A) Radically polymerizable monomer>

[0051] The radically polymerizable monomer (A) contains a first radically polymerizable monomer represented by the following formula (1) (A-1). Hereinafter, the first radically polymerizable monomer represented by the formula (1) will also be referred to as the component (A-1). The radically polymerizable monomer (A) will also be referred to as the component (A). The radically polymerizable monomer (A) may contain other radically polymerizable monomers according to the characteristics required for the cured product. As long as it is a polymerizable monomer capable of polymerizing with the component (A-1), there is no particular limitation, and known polymerizable monomers can be used. Radically polymerizable monomers having a (meth)acrylate group are preferred, and a radically polymerizable monomer (A-2) having three or more (meth)acryloyl groups in one molecule and a radically polymerizable monomer (A-3) having a (meth)acryloyl group are preferably used.

[0052] <(A-1) Component: Radically polymerizable monomer represented by the following formula (1)>

[0053]

[0054] In the formula, R 1 and R 7Each is independently a hydrogen atom or a methyl group. That is, the component (A-1) can be a diacrylate, dimethacrylate, or methacrylate acrylate represented by the above formula (1). When using the component (A-1) as a diacrylate, there is a tendency to obtain a cured product with a high fading rate of the photochromic pigment. If the component (A-1) is used as a dimethacrylate, there is a tendency to obtain a cured product with a high color development concentration of the photochromic pigment. R 1 and R 7 is preferably a methyl group.

[0055] R 4 is a linear or branched alkylene group having 1 to 7 carbon atoms which may optionally have a substituent. c is 2 to 20. c is a number greater than a, a number greater than b, a number greater than d, and a number greater than e.

[0056] That is, the repeating unit -(OCH2CH2R 4 )- with a subscript c is a first alkyleneoxy unit having 3 or more and 9 or less carbon atoms. The polymer part composed of this repeating unit can form a soft segment of the cured product. R 4 is preferably a linear alkylene group. The number of carbon atoms of the alkylene group is preferably 1 or more and 4 or less, more preferably 2 or more and 4 or less. When the number of carbon atoms of the alkylene group is large, the functionality of the cured product is further improved. On the other hand, when the number of carbon atoms of the alkylene group is too large, the amount of the soft segment per unit mass decreases, and thus the functionality of the cured product may decrease.

[0057] From the viewpoints of balancing functionality and hardness and adhesion, c is preferably 2 to 19, more preferably 2 to 18, further preferably 3 to 17, and particularly preferably 5 to 16. c can be 6 to 18 or can be 9 to 15.

[0058] R 2 、R 3 、R 5 、and R 6 are each independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. R 2 、R 3 、R 5 and R 6 are each independently preferably a hydrogen atom or a methyl group. R 2 and R 3 are different groups. R 5 and R 6 are different groups. R 2 and R 6 can be the same group. R 3 and R 5 can be the same group.

[0059] a and e are from 0 to 10. From the viewpoints of considering functionality and hardness, a and e are preferably from 0 to 5, more preferably from 0 to 2, further preferably 0 or 1, and most preferably 0.

[0060] b and d are from 0 to 20. From the viewpoints of considering functionality and hardness, preferably 0 to 15, more preferably 0 to 10, further preferably 0 to 5, and particularly preferably 0.

[0061] In other words, the component (A-1) can be a monomer further having at least one of a repeating unit to which b and d are added, i.e., a second alkyleneoxy unit, and a repeating unit to which a and e are added, i.e., a third alkyleneoxy unit.

[0062] For the component (A-1), it is preferred that a, b, d, and e are 0, that is, it is preferred to contain only the first alkyleneoxy unit. When using such a component (A-1), there is a tendency for the hardness of the cured product to increase. c can be 4 or more and 20 or less, and can also be 6 or more and 15 or less. c can be 5 or more and 10 or less, and can also be 9 or more and 14 or less.

[0063] The biomass degree of the component (A-1) is preferably 60% by mass or more, more preferably 70% by mass or more, and further preferably 90% by mass or more. The upper limit value of the biomass degree is, for example, 100% by mass or less, or 98% by mass or less.

[0064] The component (A-1) is represented, for example, by the following formula (3).

[0065]

[0066] In the above formula (3), R 1 , R 7 , and c have the same meanings as in formula (1).

[0067] R 11 is a linear alkylene having 1 to 7 carbon atoms. R 11 is preferably a linear alkylene having 1 to 5 carbon atoms, more preferably a linear alkylene having 1 to 3 carbon atoms, and most preferably a linear alkylene having 2 carbon atoms.

[0068] If specific examples of the compound represented by the above formula (3) are given, polytrimethylene glycol di(meth)acrylate, polytetramethylene glycol di(meth)acrylate, polypentamethylene glycol di(meth)acrylate, polyhexamethylene glycol di(meth)acrylate, etc. can be cited.

[0069] From the viewpoints of achieving both photochromism and hardness, and further considering the viscosity of the resulting curable composition, etc., the number-average molecular weight of the component (A-1) represented by the formula (3) is preferably 200 or more and 2000 or less. The number-average molecular weight of the component (A-1) may be 400 or more and 1500 or less, or may be 600 or more and 1000 or less. The number-average molecular weight of the component (A-1) represented by the formula (3) may be 400 or more and 1800 or less, may be 550 or more and 1700 or less, may be 650 or more and 1600 or less, may be 600 or more and 2000 or less. The number-average molecular weight may be 200 or more and 9000 or less, may be 200 or more and 7000 or less, may be 200 or more and 6000 or less, may be 250 or more and 5000 or less. The number-average molecular weight can be measured, for example, by gel permeation chromatography (GPC).

[0070] When using a component (A-1) in which a and e are 0 and b and d are 1 or more, that is, a component (A-1) further containing a second alkyleneoxy unit, there is a tendency to obtain a cured product having a high functionality of the functional pigment. b and d may be 2 or more and 15 or less, or may be 4 or more and 10 or less.

[0071] Specific examples of such a component (A-1) are as follows.

[0072]

[0073] In addition, the component (A-1) may be a monomer in which a, b, d, and e are 1 or more, that is, a monomer further having both a second alkyleneoxy unit and a third alkyleneoxy unit. In this case, the second alkyleneoxy unit and the third alkyleneoxy unit have different structures from each other.

[0074] Specific examples of such a component (A-1) are as follows.

[0075]

[0076] The component (A-1) can be produced, for example, by the following method.

[0077] The component (A-1) having an acryloyl group can be synthesized by esterification of a polyol compound represented by the following formula with acrylic acid. R of the following polyol compound 2 、R 3 、R 4 、R 5 、R 6 、a, b, c, d, and e have the same meanings as in the formula (1). The polyol compound may be derived from plants or may be derived from petroleum.

[0078]

[0079] Specifically, in the presence of inorganic acids such as sulfuric acid and hydrochloric acid, organic acids such as aromatic sulfonic acids, or Lewis acids such as boron fluoride ether, the above polyol compound dissolved in a solvent such as toluene and acrylic acid can be stirred while heating as needed, and the reaction can be carried out by azeotropically removing the generated water. It should be noted that in the esterification reaction, as a method for removing water, methods such as removing water using a desiccant such as anhydrous magnesium sulfate or molecular sieve, or removing water in the presence of a dehydrating agent represented by dicyclohexylcarbodiimide can be cited.

[0080] In addition, it can also be synthesized by carrying out an esterification reaction using acryloyl halide. Specifically, a method such as stirring the above polyol compound and acrylic acid dissolved in an ether solvent such as tetrahydrofuran while heating as needed in the presence of a base such as pyridine or dimethylaniline to remove the generated hydrogen halide can be adopted.

[0081] Furthermore, it can also be synthesized by carrying out a transesterification reaction with an ester compound such as acrylic anhydride or methyl acrylate. Specifically, a method such as stirring the above polyol compound and acrylic acid dissolved in a solvent such as toluene while heating as needed in the presence of an acidic catalyst such as aromatic sulfonic acid or a basic catalyst such as sodium acetate or pyridine can be adopted.

[0082] The component (A-1) having a methacryloyl group can be synthesized in the same manner as above by using methacrylic acid instead of acrylic acid.

[0083] Among the above polyol compounds, a polyol compound in which a and e are 0 and b and d are 1 or more, that is, a polyol having a second alkyleneoxy unit can be synthesized, for example, by the following method.

[0084] By reacting H-(OCH2CH2R 4 )c-OH with a cyclic ether compound such as ethylene oxide or propylene oxide, a polyol having a second alkyleneoxy unit can be synthesized. A polyol compound having a second alkyleneoxy unit can be synthesized, for example, by carrying out the reaction in a nitrogen-purged autoclave in the presence of a catalyst such as an alkali metal hydroxide such as potassium hydroxide under high temperature and high pressure.

[0085] Among the above polyol compounds, a polyol compound in which a, b, d, and e are 1 or more, that is, the component (A-1) further containing a second and a third alkyleneoxy unit can be synthesized, for example, by the following method.

[0086] A polyol compound having a second alkyleneoxy unit is reacted with a cyclic ether compound to synthesize a polyol compound having a third alkyleneoxy unit. The obtained polyol compound further having a third alkyleneoxy unit is reacted with acrylic acid or methacrylic acid by the same method as the method described above, whereby the component (A-1) further containing the second and third alkyleneoxy units can be synthesized.

[0087] <The second radically polymerizable monomer having three or more (meth)acryloyl groups in one molecule>

[0088] The curable composition of the embodiment may further contain a second radically polymerizable monomer having three or more (meth)acryloyl groups in one molecule. Hereinafter, the second radically polymerizable monomer having three or more (meth)acryloyl groups in one molecule is also referred to as the component (A-2). When a polyfunctional (meth)acrylate is contained, there is a tendency for the hardness of the cured product to increase.

[0089] Examples of the component (A-2) include polyfunctional (meth)acrylates represented by the following formula (I), polyfunctional (meth)acrylates having a urethane bond, and polyfunctional (meth)acrylates not belonging to the foregoing. Particularly preferred is the polyfunctional (meth)acrylate represented by the following formula (I).

[0090] <The polyfunctional (meth)acrylate represented by the following formula (I)>

[0091]

[0092] In formula (I), Q 10 is a methylene group. a1 is an integer of 0 or 1.

[0093] Q 11 is a linear or branched alkylene group having 1 or more and 3 or less carbon atoms. Q 11 is preferably a linear alkylene group. Q 11 is preferably an alkylene group having 2 or 3 carbon atoms. Q 11 More preferably, it is an ethylene group, a n-propylene group or a n-butylene group.

[0094] a2 is 0, 1, 2 or 3. a2 is preferably 1, 2 or 3.

[0095] Q 12 is a hydrogen atom or a methyl group. Q 12 is preferably a methyl group.

[0096] Q 13 is a trivalent to hexavalent organic group having 1 to 10 carbon atoms. As Q 13Examples of the organic group shown include a group derived from a polyhydric alcohol, a C3-6 valent hydrocarbon group, and a C3-6 valent organic group containing a urethane bond. Q 13 Preferably, it is a tetravalent hydrocarbon group or a hexavalent hydrocarbon group. Q 13 It may be a group derived from trimethylolpropane, a group derived from glycerol, a group derived from pentaerythritol, a group derived from ditrimethylolpropane, or a group derived from dipentaerythritol.

[0097] a3 is 3, 4, 5, or 6. a3 is preferably 3 or 4.

[0098] The polyfunctional (meth)acrylate represented by formula (I) more preferably contains a 3-4 functional (meth)acrylate represented by the following formula (II).

[0099]

[0100] In formula (II), Q 20 , Q 21 , Q 22 and Q 23 are each independently a methylene group. a4, a5, a6, and a7 are each independently an integer of 0 or 1.

[0101] Q 24 , Q 25 and Q 26 are each independently a monovalent group represented by the following formula (III). Q 24 , Q 25 and Q 26 may have different structures from each other or may have the same structure. Q 24 , Q 25 and Q 26 preferably have the same structure.

[0102] Q 27 is a hydrogen atom, a linear or branched alkyl group having 1 or more and 5 or less carbon atoms, a linear or branched alkoxy group having 1 or more and 5 or less carbon atoms, or a monovalent group represented by the following formula (III). Q 27 Preferably, it is a hydrogen atom, a linear alkyl group having 1 or more and 3 or less carbon atoms, or a monovalent group represented by the following formula (III).

[0103]

[0104] In formula (III), Q 11 , Q 12 , a2 have the same meanings as in formula (I).

[0105] Specific examples of the polyfunctional (meth)acrylate represented by the above formula (I) include trimethylolpropane trimethacrylate, trimethylolpropane triacrylate, pentaerythritol trimethacrylate, pentaerythritol triacrylate, pentaerythritol tetramethacrylate, pentaerythritol tetraacrylate, trimethylolpropane triethylene glycol trimethacrylate, trimethylolpropane triethylene glycol triacrylate, ditrimethylolpropane tetramethacrylate, ditrimethylolpropane tetraacrylate, dipentaerythritol hexaacrylate, dipentaerythritol pentaacrylate, dipentaerythritol hexamethacrylate, dipentaerythritol pentamethacrylate, glycerol trimethacrylate, glycerol triacrylate, ethoxylated trimethylolpropane trimethacrylate, propoxylated trimethylolpropane trimethacrylate, butoxylated trimethylolpropane trimethacrylate, ethoxylated trimethylolpropane triacrylate, propoxylated trimethylolpropane triacrylate, butoxylated trimethylolpropane triacrylate, ethoxylated glycerol trimethacrylate, propoxylated glycerol trimethacrylate, butoxylated glycerol trimethacrylate, ethoxylated glycerol triacrylate, propoxylated glycerol triacrylate, butoxylated glycerol triacrylate, ethoxylated pentaerythritol tetramethacrylate, propoxylated pentaerythritol tetramethacrylate, butoxylated pentaerythritol tetramethacrylate, ethoxylated pentaerythritol tetraacrylate, propoxylated pentaerythritol tetraacrylate, and butoxylated pentaerythritol tetraacrylate, etc.

[0106] <Polyfunctional (meth)acrylate having a urethane bond>

[0107] The polyfunctional (meth)acrylate having a urethane bond is obtained by reacting a polyisocyanate compound having three or more isocyanate groups in the molecule, a polyol compound having two or more hydroxyl groups in the molecule, and a hydroxyl group-containing (meth)acrylate. The polyfunctional (meth)acrylate having a urethane bond is preferably a polyfunctional (meth)acrylate having a urethane bond and having four or more (meth)acryloyl groups in the molecule. As commercially available products, U-4HA (molecular weight 596, functionality 4), U-6HA (molecular weight 1,019, functionality 6), U-6LPA (molecular weight 818, functionality 6), and U-15HA (molecular weight 2,300, functionality 15) manufactured by Shin-Nakamura Chemical Co., Ltd. can be cited.

[0108] <Polyfunctional (meth)acrylate not belonging to the above>

[0109] As polyfunctional (meth)acrylates other than the polyfunctional (meth)acrylates shown in the division formula (I) and the polyfunctional (meth)acrylates having urethane bonds, compounds obtained by modifying the terminals of polyester compounds with (meth)acryloyl groups can be cited. As such polyester (meth)acrylate compounds, various polyester (meth)acrylate compounds having different molecular weights of the polyester compounds as raw materials and different modification amounts of (meth)acryloyl groups are commercially available, and they can be used. Specifically, 4-functional polyester oligomers (molecular weight 2,500 to 3,500, Daicel-UCB, EB80, etc.), 6-functional polyester oligomers (molecular weight 6,000 to 8,000, Daicel-UCB, EB450, etc.), 6-functional polyester oligomers (molecular weight 45,000 to 55,000, Daicel-UCB, EB1830, etc.), 4-functional polyester oligomers (especially the first industrial pharmaceutical company with a molecular weight of 10,000, GX8488B, etc.) can be cited.

[0110] <(A-3) Other radically polymerizable monomers having a (meth)acryloyl group>

[0111] As other radically polymerizable monomers having a (meth)acryloyl group, radically polymerizable monomers having a (meth)acryloyl group in the molecular structure and not belonging to (A-1) and (A-2) can be cited. Such radically polymerizable monomers are not particularly limited, and known substances can be used, and they can also include bifunctional (meth)acrylates having two (meth)acryloyl groups in the molecule and monofunctional (meth)acrylates having only one (meth)acryloyl group.

[0112] <Bifunctional (meth)acrylates having two (meth)acryloyl groups in the molecule>

[0113] The curable composition of the embodiment can contain the following bifunctional (meth)acrylates. If a di(meth)acrylate other than the first radically polymerizable compound is contained, the functionality of the functional pigment can be improved. Specifically, bifunctional (meth)acrylates represented by the following formula (4), the following formula (5) or the following formula (6), bifunctional (meth)acrylates having a urethane bond, and bifunctional (meth)acrylates not belonging to the aforementioned ones can be cited.

[0114] <Bifunctional (meth)acrylate compound represented by the following formula (4)>

[0115]

[0116] R 12 and R 13Each is a hydrogen atom or a methyl group. j and k are each independently an integer of 0 or more, and j + k is an integer of 2 or more. In addition, the bifunctional (meth)acrylate compound represented by the formula (4) is mostly obtained in the form of a mixture in production. Therefore, j + k is 2 or more on average, and preferably an integer of 2 or more and 50 or less on average.

[0117] Specific examples of the compound represented by the above formula (4) are as follows.

[0118] Diethylene glycol dimethacrylate, triethylene glycol dimethacrylate, tetraethylene glycol dimethacrylate, pentaethylene glycol dimethacrylate, pentapropylene glycol dimethacrylate, diethylene glycol diacrylate, triethylene glycol diacrylate, tetraethylene glycol diacrylate, pentaethylene glycol diacrylate, tripropylene glycol diacrylate, tetrapropylene glycol diacrylate, pentapropylene glycol diacrylate, dimethacrylate formed from a mixture of polypropylene glycol and polyethylene glycol (polyethylene glycol dimethacrylate, tripropylene glycol dimethacrylate, tetrapropylene glycol dimethacrylate, polypropylene glycol dimethacrylate, polyethylene glycol diacrylate, polyethylene glycol diacrylate, polyethylene glycol methacrylate acrylate.

[0119] <Bifunctional (meth)acrylate represented by the following formula (5)>

[0120]

[0121] R 14 and R 15 Each is a hydrogen atom or a methyl group. R 16 and R 17 Each is a hydrogen atom or a methyl group.

[0122] A is a divalent organic group. A is a linear or branched alkylene group having 1 to 20 carbon atoms, a phenylene group optionally having a halogen or an alkyl group having 1 to 5 carbon atoms as a substituent, a cycloalkylene group, a bicycloalkylene group, a tricycloalkylene group, or a group represented by any of the following formulas.

[0123]

[0124] In the above formulas, R 18A , R 18B are a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a halogen atom. xx and xy are integers of 0 to 4 or 0 to 10. Ring X is a benzene ring or a cyclohexane ring. YY is -O-, -S-, -(SO2)-, -CO-, -CH2-, -CH=CH-, -C(CH3)2-, -C(CH3)(C6H5)-, or any of the groups represented by the following formulas.

[0125]

[0126] In the above formula (5), l and m are each an integer of 1 or more, and l + m is 2 or more and 30 or less on average.

[0127] As specific examples of the bifunctional (meth)acrylate represented by the above formula (5), for example, the following bisphenol A di(meth)acrylates can be cited.

[0128] 2,2-bis[4-(methacryloyloxyethoxy)phenyl]propane, 2,2-bis[3,5-dibromo-4-(methacryloyloxyethoxy)phenyl]propane, 2,2-bis(4-(methacryloyldipropoxy)phenyl)propane, 2,2-bis[4-(acryloyldiethoxy)phenyl]propane, 2,2-bis[4-(acryloyloxypolyethoxy)phenyl]propane, 2,2-bis[4-(methacryloyloxypolyethoxy)phenyl]propane, 1,3-adamantanediol dimethacrylate, di(trishydroxymethyl)cyclodecane diacrylate.

[0129] <The bifunctional (meth)acrylate represented by the following formula (6)>

[0130]

[0131] R 19 and R 20 are each a hydrogen atom or a methyl group.

[0132] n is a number of 1 to 20 on average.

[0133] B and B' are each independently a linear or branched alkylene group having 2 to 15 carbon atoms. B and B' may be the same or different from each other. In the case where there are a plurality of Bs, the plurality of Bs may be the same group or different groups.

[0134] The bifunctional (meth)acrylate represented by the above formula (6) can be produced by reacting a polycarbonate diol with (meth)acrylic acid.

[0135] Here, as the polycarbonate diol used, the following polycarbonate diols can be exemplified. Specifically, polycarbonate diols obtained by phosgenation of trimethylene glycol (average molecular weight 500 to 2000), polycarbonate diols obtained by phosgenation of tetramethylene glycol (average molecular weight 500 to 2000), polycarbonate diols obtained by phosgenation of pentamethylene glycol (average molecular weight 500 to 2000), polycarbonate diols obtained by phosgenation of hexamethylene glycol (average molecular weight 500 to 2000), polycarbonate diols obtained by phosgenation of octamethylene glycol (average molecular weight 500 to 2000), polycarbonate diols obtained by phosgenation with nonamethylene glycol (average molecular weight 500 to 2000), polycarbonate diols obtained by phosgenation of triethylene glycol and tetramethylene glycol (average molecular weight 500 to 2000), polycarbonate diols obtained by phosgenation of tetramethylene glycol and hexamethylene diglycol (average molecular weight 500 to 2000), polycarbonate diols obtained by phosgenation of pentamethylene glycol and hexamethylene glycol (average molecular weight 500 to 2000), polycarbonate diols obtained by phosgenation of tetramethylene glycol and octamethylene glycol (average molecular weight 500 to 2000), polycarbonate diols obtained by phosgenation of hexamethylene glycol and octamethylene glycol (average molecular weight 500 to 2000), and polycarbonate diols obtained by phosgenation with 1-methyltrimethylene glycol (average molecular weight 500 to 2000).

[0136] <Bifunctional (meth)acrylate having a urethane bond>

[0137] As the bifunctional (meth)acrylate having a urethane bond, a substance obtained by reacting a polyisocyanate compound having two or more isocyanate groups in the molecule, a polyol compound having two or more hydroxyl groups in the molecule, and a hydroxyl group-containing (meth)acrylate can be cited.

[0138] As the polyisocyanate, for example, hexamethylene diisocyanate, isophorone diisocyanate, lysine isocyanate, 2,2,4-hexamethylene diisocyanate, dimer acid diisocyanate, isopropylidene bis-4-cyclohexyl isocyanate, dicyclohexylmethane diisocyanate, norbornene diisocyanate, or methylcyclohexane diisocyanate can be cited as suitable substances.

[0139] Examples of the polyol include polyalkylene glycols having repeating units of ethylene oxide, propylene oxide, or hexylene oxide with 2 to 4 carbon atoms, or polyester diols such as polycaprolactone diol. In addition, polycarbonate diol, polybutadiene diol, or pentaerythritol, ethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, 1,9-nonanediol, 1,8-nonanediol, neopentyl glycol, diethylene glycol, dipropylene glycol, 1,4-cyclohexanediol, 1,4-cyclohexanedimethanol, glycerin, trimethylolpropane, etc. can also be exemplified.

[0140] In addition, a reaction mixture obtained by further reacting a urethane prepolymer prepared by the reaction of these polyisocyanates and polyols with 2-hydroxy(meth)acrylate, or a urethane(meth)acrylate monomer as a reaction mixture obtained by directly reacting the aforementioned diisocyanate with 2-hydroxy(meth)acrylate can also be used.

[0141] Examples of the hydroxy-containing (meth)acrylate include 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 3-hydroxybutyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, etc.

[0142] Commercially available products of the bifunctional (meth)acrylate having a urethane bond can be used without any limitation. For example, as commercially available products, U-2PPA (molecular weight 482), UA-122P (molecular weight 1,100), U-122P (molecular weight 1,100) manufactured by Shin-Nakamura Chemical Co., Ltd., and EB4858 (molecular weight 454) manufactured by Daicel-UCB Co., Ltd. can be cited.

[0143] <Not belonging to the aforementioned bifunctional (meth)acrylate>

[0144] As the "2-functional (meth)acrylate that does not belong to the aforementioned ones" other than the 2-functional (meth)acrylate shown in the above formula (4), the above formula (5), or the above formula (6) and the 2-functional (meth)acrylate having a urethane bond, a 2-functional (meth)acrylate containing a sulfur atom can also be cited. The sulfur atom preferably forms a part of the molecular chain in the form of a thioether group. Specifically, bis(2-methacryloyloxyethyl thioethyl) sulfide, bis(methacryloyloxyethyl) sulfide, bis(acryloyloxyethyl) sulfide, 1,2-bis(methacryloyloxyethyl thio)ethane, 1,2-bis(acryloyloxyethyl)ethane, bis(2-methacryloyloxyethyl thioethyl) sulfide, bis(2-acryloyloxyethyl thioethyl) sulfide, 1,2-bis(methacryloyloxyethyl thioethyl thio)ethane, 1,2-bis(acryloyloxyethyl thioethyl thio)ethane, 1,2-bis(methacryloyloxyisopropyl thioisopropyl) sulfide, 1,2-bis(acryloyloxyisopropyl thioisopropyl) sulfide can be cited.

[0145] The above 2-functional (meth)acrylate compounds can use a single component among the components described separately, or can use multiple components. In addition, multiple components described separately can also be used in combination. In the case of using multiple components or multiple combinations, the mass as a reference is the total measurement of the multiple components.

[0146] <The third radically polymerizable monomer having one (meth)acryloyl group in one molecule>

[0147] The curable composition of the embodiment can further contain a third radically polymerizable monomer having one (meth)acryloyl group in one molecule. The third radically polymerizable monomer can be a monofunctional (meth)acrylate.

[0148] As the monofunctional (meth)acrylate, the monofunctional (meth)acrylate shown in the following formula (7) can be cited.

[0149]

[0150] R 21 is a hydrogen atom, methyldimethoxysilyl, trimethoxysilyl, glycidyl, pentamethylpiperidyl, 2,2,6,6-tetramethylpiperidyl, or piperidyl. R 22 is a hydrogen atom or a methyl group. o is an integer from 0 to 10. p is an integer from 0 to 20.

[0151] R 21 is preferably methyldimethoxysilyl, trimethoxysilyl, or glycidyl. When a monofunctional acrylate having such a functional group is included, there is a tendency for the adhesion between the cured product and the substrate to be improved.

[0152] When specifically showing the monofunctional (meth)acrylate shown in the above formula (7), examples thereof include methoxypolyethylene glycol methacrylate, methoxypolyethylene glycol acrylate, stearyl methacrylate, lauryl methacrylate, methyl acrylate, ethyl acrylate, butyl acrylate, octyl acrylate, lauryl acrylate, γ-methacryloyloxypropyltrimethoxysilane, γ-methacryloyloxypropylmethyldimethoxysilane, glycidyl methacrylate, 1,2,2,6,6-pentamethyl-4-piperidyl methacrylate, 2,2,6,6-tetramethyl-4-piperidyl methacrylate, etc.

[0153] <Other radically polymerizable monomers>

[0154] The curable composition of the embodiment may further contain other radically polymerizable monomers. As the other radically polymerizable monomers, as long as they are radically polymerizable monomers capable of polymerizing with the component (A-1), there is no particular limitation, and known radically polymerizable monomers can be used. For example, radically polymerizable polyrotaxanes, radically polymerizable silsesquioxane compounds, allyl-based compounds, and vinyl-based compounds are preferably used.

[0155] <Radically polymerizable polyrotaxane>

[0156] The polyrotaxane has a composite molecular structure composed of an axle molecule and a plurality of cyclic molecules that encapsulate the axle molecule. Bulky end groups are formed at both ends of the axle molecule to prevent the cyclic molecules from falling off the axle molecule. The radically polymerizable polyrotaxane is a polyrotaxane in which a radically polymerizable group is introduced into the side chain of the cyclic molecule. The radically polymerizable group is introduced, for example, by modifying 1 mol% or more and less than 100 mol% of the hydroxyl groups of the cyclic molecule into radically polymerizable groups. The modification ratio can be calculated by (the number of moles of the introduced polymerizable group) / (the total number of OH groups in the side chain) × 100. It should be noted that from the viewpoints of adhesion, the mechanical strength of the obtained cured product, and functionality, the modification ratio is preferably 10 mol% or more and 95 mol% or less.

[0157] When the weight average molecular weight of the axle molecule is too large, there is a tendency for the compatibility with other polymerizable monomers, etc. to decrease, and when it is too small, there is a tendency for the mobility of the cyclic molecules to decrease. The weight average molecular weight of the axle molecule is preferably in the range of 1,000 to 100,000, more preferably in the range of 5,000 to 80,000, and most preferably in the range of 8,000 to 50,000.

[0158] The cyclic molecule is preferably a cyclodextrin ring, a crown ether ring, a benzo crown ring, a dibenzo crown ring, or a dicyclohexano crown ring, particularly preferably a cyclodextrin ring or a crown ether ring, and most preferably a cyclodextrin ring. In addition, in the cyclodextrin ring, there are α-form (inner ring diameter 0.45 - 0.6 nm), β-form (inner ring diameter 0.6 - 0.8 nm), and γ-form (inner ring diameter 0.8 - 0.95 nm), with α-cyclodextrin ring and β-cyclodextrin ring being preferred, and α-cyclodextrin ring being most preferred. When the inclusion number when all cyclic molecules are introduced into the axle molecule is set to 1, the inclusion number of the cyclic molecule is preferably in the range of 0.001 - 0.6, more preferably in the range of 0.002 - 0.5, and most preferably in the range of 0.003 - 0.4.

[0159] As the radically polymerizable group, considering the reactivity with other polymerizable monomers, etc., (meth)acryloyl is preferred. The number of radically polymerizable groups is not particularly limited, and is preferably 0 - 5000 in one molecule.

[0160] The above-mentioned polyrotaxane having a (meth)acryloyl group is described in International Publication No. 2018 / 030257.

[0161] <Sesquisiloxane radically polymerizable compound>

[0162] The sesquisiloxane radically polymerizable compound adopts various molecular structures such as cage-like, ladder-like, and random, and has a radically polymerizable group such as (meth)acryloyl.

[0163] As an example of such a sesquisiloxane polymerizable compound, the compound represented by the following formula (8) can be cited.

[0164]

[0165] In formula (8), q is the degree of polymerization and is an integer of 3 - 100.

[0166] Multiple Rs 23 may be the same or different from each other and are a radically polymerizable group, an organic group containing a radically polymerizable group, a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, or a phenyl group. At least one of the multiple Rs 23 is a radically polymerizable group or an organic group containing a radically polymerizable group. 23 Here, as R

[0167] 23 ​Examples of the free-radical polymerizable group or the organic group containing a free-radical polymerizable group include (meth)acryloyl group; organic groups having a (meth)acryloyl group such as (meth)acryloyloxypropyl group and (3-(meth)acryloyloxypropyl)dimethylsiloxy group; allyl group; organic groups having an allyl group such as allylpropyl group and allylpropyldimethylsiloxy group; vinyl group; organic groups having a vinyl group such as vinylpropyl group and vinyldimethylsiloxy group, etc.

[0168] <Allyl-based polymerizable compound>

[0169] Examples of the allyl-based polymerizable compound having an allyl group include the following compounds. Diethylene glycol diallyl carbonate, methoxypolyethylene glycol allyl ether, methoxypolyethylene glycol-polypropylene glycol allyl ether, butoxypolyethylene glycol-polypropylene glycol allyl ether, phenoxypolyethylene glycol allyl ether, ethenoxypolyethylene glycol allyl ether, styrenoxypolyethylene glycol allyl ether, methoxypolyethylene dithiol allyl sulfide.

[0170] <Vinyl-based polymerizable compound>

[0171] Examples of the vinyl-based polymerizable compound having a vinyl group include methyl vinyl ketone, ethyl vinyl ketone, ethyl vinyl ether, styrene, vinylcyclohexane, butadiene, 1,4-pentadiene, divinyl sulfide, divinyl sulfone, 1,2-divinylbenzene, 1,3-divinyl-1,1,3,3-tetramethylpropanedisiloxane, diethylene glycol divinyl ether, divinyl adipate, divinyl sebacate, ethylene glycol divinyl ether, divinyl sulfoxide, divinyl sulfide, dimethyldivinylsilane, 1,2,4-trivinylcyclohexane, methyltrivinylsilane, α-methylstyrene and α-methylstyrene dimer, etc.

[0172] <Blending ratio in the curable composition>

[0173] In the curable composition of the embodiment, the proportion of the first free-radical polymerizable monomer is 15% by mass or more and 34% by mass or less. When this proportion is high, the performance of the functional pigment in the cured product tends to improve. This proportion can be 16% by mass or more, preferably 17% by mass or more, more preferably 19% by mass or more, further preferably 20% by mass or more, and particularly preferably 21% by mass or more. On the other hand, if this proportion is too high, the adhesion tends to decrease. This proportion is preferably 33% by mass or less, more preferably 32% by mass or less.

[0174] From the aspect of improving the hardness of the cured product, the curable composition of the embodiment preferably contains a second radically polymerizable monomer. The proportion of the second radically polymerizable monomer is preferably 1% by mass or more, more preferably 10% by mass or more, still more preferably 20% by mass or more, and particularly preferably 25% by mass or more. On the other hand, when this proportion is too high, there is a tendency for the performance of the functional pigment in the cured product and the appearance to deteriorate. This proportion is preferably 85% by mass or less, more preferably 50% by mass or less, and still more preferably 35% by mass or less.

[0175] From the aspect of improving the adhesion of the cured product, the curable composition of the embodiment preferably contains a third radically polymerizable monomer. The proportion of the third radically polymerizable monomer is preferably 0.1% by mass or more, more preferably 1% by mass or more, and still more preferably 3% by mass or more. On the other hand, when this proportion is too high, there is a tendency for the performance of the functional pigment in the cured product to deteriorate. This proportion is preferably 20% by mass or less, more preferably 10% by mass or less, and still more preferably 7% by mass or less.

[0176] From the aspect of improving the adhesion of the cured product, the curable composition of the embodiment preferably contains a third radically polymerizable monomer. The proportion of the third radically polymerizable monomer is preferably 0.1% by mass or more, more preferably 1% by mass or more, and still more preferably 3% by mass or more. On the other hand, when this proportion is too high, there is a tendency for the performance of the functional pigment in the cured product to deteriorate. This proportion is preferably 20% by mass or less, more preferably 10% by mass or less, and still more preferably 7% by mass or less.

[0177] In the curable composition of the embodiment, the content of di(meth)acrylate other than the first radically polymerizable monomer is preferably 70% by mass or less. That is, when the content of di(meth)acrylate such as (meth)acrylate having an alkyleneoxy chain with 2 or less carbon atoms, polyalkylene carbonate polyol di(meth)acrylate, etc. is large, the performance of the functional pigment in the cured product may be reduced. The content of di(meth)acrylate other than the first radically polymerizable monomer may be 60% by mass or less, may be 55% by mass or less, may be 30% by mass or less, may be 20% by mass or less. The lower limit of this content is 0% by mass according to one example, and 5% by mass or more according to another example. In particular, among the di(meth)acrylates other than the first radically polymerizable monomer, from the viewpoints of improving the compatibility between the first radically polymerizable monomer and the primer layer and being able to further improve the appearance and adhesion of the laminate, (poly)ethylene glycol di(meth)acrylate is preferably used in combination with the first radically polymerizable monomer. If considering both the hardness of the cured product and the performance of the functional pigment, its content is preferably 60% by mass or less. The content of (poly)ethylene glycol di(meth)acrylate may be 30% by mass or less, may be 20% by mass or less, and may also be 10% by mass or less. The content of (poly)ethylene glycol di(meth)acrylate may be 55% by mass or less, and may also be 50% by mass or less. The lower limit of this content is 0% by mass according to one example, and 5% by mass or more according to another example.

[0178] In the curable composition containing the first to third radically polymerizable monomers, the content of the first radically polymerizable monomer is 15% by mass or more and 34% by mass or less, the content of the second radically polymerizable monomer is 10% by mass or more and 85% by mass or less, the content of the third radically polymerizable monomer is 1% by mass or more and 10% by mass or less, and the balance may be the ratio of the functional pigment and the additive.

[0179] In the curable composition of the embodiment, the proportion of methacrylate is preferably 50% by mass or more. When this proportion is high, there is a tendency to obtain a cured product with high function of the functional pigment. This proportion is preferably 60% by mass or more, more preferably 70% by mass or more, and further preferably 90% by mass or more. The upper limit of this proportion is 99% by mass or less according to one example, and 95% by mass or less according to another example.

[0180] In the curable composition of the embodiment, the ratio M10 / M11 of the mass M10 of methacrylate to the mass M11 of acrylate may be 0.1 or more and 10 or less, may be 0.5 or more and 5 or less, and may be 1.2 or more and 6 or less.

[0181] The ratio M1 / M3 of the mass M1 of the first radically polymerizable monomer to the mass M3 of the second radically polymerizable monomer is preferably 0.1 or more and 20 or less. When using a curable composition with M1 / M3 within this range, there is a tendency for the properties and hardness of the functional pigment in the cured product to be further improved. The ratio M1 / M3 is more preferably 0.5 or more and 10 or less, and even more preferably 1 or more and 5 or less.

[0182] The ratio M1 / M4 of the mass M1 of the first radically polymerizable monomer to the mass M4 of the third radically polymerizable monomer is preferably 0.1 or more and 50 or less. When using a curable composition with M1 / M3 within this range, there is a tendency for the properties and hardness of the functional pigment in the cured product to be further improved. The ratio M1 / M3 is more preferably 1 or more and 30 or less, and even more preferably 5 or more and 15 or less.

[0183] When the component (A) is 100 parts by mass, the component (A-1) can be 15 to 34 parts by mass, can be 16 to 33 parts by mass, can be 17 to 34 parts by mass, can be 17 to 33 parts by mass.

[0184] When compounding the component (A-2), when the component (A-1) is 100 parts by mass, the component (A-2) can be 1 to 570 parts by mass, can be 1 to 300 parts by mass, can be 3 to 300 parts by mass, can be 5 to 250 parts by mass.

[0185] When further containing the component (A-3), when the component (A) is 100 parts by mass, the component (A-3) can be 0.01 to 500 parts by mass, can be 0.1 to 450 parts by mass, can also be 0.5 to 430 parts by mass.

[0186] <(B) Functional pigment>

[0187] The functional pigment includes a compound having a selective absorption ability for visible light, and a compound that develops color, fades, or changes color by energy such as light, heat, an electric field, or pressure. Such a functional pigment can exhibit a specific function by undergoing a structural change under specific conditions. The functional pigment includes, for example, at least one selected from the group consisting of photochromic compounds, ultraviolet absorbers, blue light absorbers, infrared absorbers, and electrochromic compounds.

[0188] The ratio M1 / M2 of the mass M1 of the first radically polymerizable monomer to the mass M2 of the functional pigment is, for example, 10 or more and 10000 or less. The ratio M1 / M2 is preferably 15 or more and 1000 or less, and more preferably 20 or more and 100 or less.

[0189] The content of the functional pigment in the curable composition is, for example, 0.01% by mass or more and 10% by mass or less. The content of the functional pigment is preferably 0.1% by mass or more and 8% by mass or less, more preferably 1% by mass or more and 5% by mass or less.

[0190] <Photochromic compound>

[0191] The photochromic compound is used in a compounding amount capable of obtaining desired photochromic properties. Preferably, it is used in an amount of 0.01 to 10 parts by mass relative to 100 parts by mass of the component (A).

[0192] This compounding amount is preferably adjusted to an optimal compounding amount according to the intended use.

[0193] Specifically, in the case of forming a thin film such as a coating film from the curable composition containing the photochromic compound, for example, a thin film of about 100 μm (a polymer film formed by polymerizing the photochromic curable composition), the hue can be adjusted by compounding 0.1 to 10 parts by mass of the photochromic compound relative to 100 parts by mass of the polymerizable compound.

[0194] In addition, in the case of forming a thick cured product (a polymer molded body formed by polymerizing the photochromic curable composition), for example, in the case of a cured product having a thickness of 1 mm or more, the hue can be adjusted by compounding 0.01 to 1 part by mass of the photochromic compound relative to 100 parts by mass of the thick cured product or 100 parts by mass of the polymerizable compound imparted to the thick cured product.

[0195] There are no particular limitations on the photochromic compound, and known compounds can be used. They can be used alone or in combination of two or more. Representative compounds of such photochromic compounds are chromene compounds, fulgide compounds, fulgimide compounds, and spirooxazine compounds, which are disclosed, for example, in many documents such as Japanese Patent Laid-Open No. 2-28154, Japanese Patent Laid-Open No. 62-288830, International Publication No. 94 / 22850, International Publication No. 96 / 14596, International Publication No. 2022 / 075330, and International Publication No. 2022 / 168989.

[0196] Among these photochromic compounds, chromene compounds and spirooxazine compounds are preferably used. Chromene compounds are particularly preferred. Chromene compounds include compounds having a 1-benzopyran skeleton, spiro pyran compounds having a spiro pyran skeleton, and naphtho pyran compounds having a naphtho pyran skeleton.

[0197] The naphtho pyran compound preferably includes compounds represented by the following formula (9), the following formula (10), the following formula (11), the following formula (12), the following formula (13), and the following formula (14).

[0198]

[0199] In formula (9), ring AA is a substituted or unsubstituted aromatic hydrocarbon ring, a substituted or unsubstituted aromatic heterocyclic ring, or a substituted or unsubstituted fused polycyclic ring in which an aromatic ring or an aromatic heterocyclic ring is fused to these rings. Ring AA may also be absent.

[0200] Ring AB is a substituted or unsubstituted aromatic hydrocarbon ring, a substituted or unsubstituted aromatic heterocyclic ring, or a substituted or unsubstituted fused polycyclic ring in which an aromatic ring or an aromatic heterocyclic ring is fused to these rings.

[0201] R 24 and R 25 are each independently a hydrogen atom or a substituent, and two or more substituents may be bonded to form a ring structure.

[0202] As the substituent, it is a hydroxyl group, an alkyl group, a haloalkyl group, a cycloalkyl group, an alkoxy group, an alkoxyalkyl group, a formyl group, a hydroxycarbonyl group, an alkylcarbonyl group, an alkoxycarbonyl group, a halogen atom, an aralkyl group optionally having a substituent, an aralkyloxy group optionally having a substituent, an aryloxy group optionally having a substituent, an alkylthio group, an arylthio group optionally having a substituent, an aryl group optionally having a substituent, an amino group, a substituted amino group, a heterocyclic group optionally having a substituent, and is preferably at least one selected from the group consisting of a haloalkylthio group, a cycloalkylthio group optionally having a substituent, an oligomer group, and the group represented by the following formula (15).

[0203] -Q 1 -(P 1 Q 2 ) aa -P 2 Q 3 (15)

[0204] Q 1 is an alkylene group optionally containing a halogen atom in the substituent. Q 2 is an alkylene group optionally containing a halogen atom in the substituent. Q 3 is an alkyl group optionally containing a halogen atom in the substituent. P 1 and P 2 are each independently O, S, NR 700 , PR 701 or P(=O). R 700 is a hydrogen atom, an alkyl group optionally having a substituent, a cycloalkyl group optionally having a substituent, an aryl group optionally having a substituent, or a heteroaryl group optionally having a substituent. R 701 is a hydrogen atom, an alkyl group optionally having a substituent, a cycloalkyl group optionally having a substituent, an aryl group optionally having a substituent, or a heteroaryl group optionally having a substituent. aa is 0 or 1 or more and 10 or less.

[0205] M is CR 26 R 27 、SiR 26 R 27 、GeR 26 R 27 or NR 26 。R 26 and R 27 are each independently a hydrogen atom or a substituent, and two or more substituents may be bonded to form a ring structure.

[0206] As the substituent, it is preferably at least one selected from the group consisting of a hydroxyl group, an alkyl group, a haloalkyl group, a cycloalkyl group, an alkoxy group, an alkoxyalkyl group, a formyl group, a hydroxycarbonyl group, an alkylcarbonyl group, an alkoxycarbonyl group, a halogen atom, an aralkyl group optionally having a substituent, an aralkyloxy group optionally having a substituent, an aryloxy group optionally having a substituent, an alkylthio group, an arylthio group optionally having a substituent, an aryl group optionally having a substituent, an amino group, a substituted amino group, a heterocyclic group optionally having a substituent, and the group represented by the above formula (15).

[0207] In addition, when R 26 and R 27 form a ring structure together, it is preferably an aliphatic ring having 3 to 20 ring carbon atoms, a fused polycyclic ring in which an aromatic ring or an aromatic heterocyclic ring is fused to the aliphatic ring, a heterocyclic ring having 3 to 20 ring atoms, or a fused polycyclic ring in which an aromatic ring or an aromatic heterocyclic ring is fused to the heterocyclic ring.

[0208]

[0209] In formula (10), R 1000 、R 1001 and R 1002 are each independently a hydrogen atom or a substituent, and two or more substituents may be bonded to form a ring structure. The substituent may be the same as the group described in formula (9). mm is an integer from 1 to 10.

[0210]

[0211] In formula (11), R 1003 、R 1004 and R 1005 are each independently a hydrogen atom or a substituent, and two or more substituents may be bonded to form a ring structure. The substituent may be the same as the group described in formula (9). nn is an integer from 1 to 10.

[0212]

[0213] In formula (12), R 1006 、R1007 and R 1008 Each independently represents a hydrogen atom or a substituent, and two or more substituents may bond to form a ring structure. The substituent may be the same type of group as the group described in formula (9). oo is an integer of 1 to 12.

[0214]

[0215] In formula (13), R 1009 , R 1010 and R 1011 Each independently represents a hydrogen atom or a substituent, and two or more substituents may bond to form a ring structure. The substituent may be the same type of group as the group described in formula (9). pp is an integer of 1 to 12.

[0216]

[0217] In formula (14), R 1012 , R 1013 and R 1014 Each independently represents a hydrogen atom or a substituent, and two or more substituents may bond to form a ring structure. The substituent may be the same type of group as the group described in formula (9). qq is an integer of 1 to 12.

[0218] The naphthopyran compound includes an indeno[2,1-f]naphtho[1,2-b]pyran compound having an indeno[2,1-f]naphtho[1,2-b]pyran skeleton. The indeno[2,1-f]naphtho[1,2-b]pyran compound preferably has an indeno[2,1-f]naphtho[1,2-b]pyran skeleton.

[0219] As indeno[2,1-f]naphtho[1,2-b]pyran, for example, compounds described in International Publication No. WO1996 / 014596, International Publication No. WO2001 / 019813, International Publication No. WO2001 / 060811, International Publication No. WO2005 / 028465, International Publication No. WO2006 / 110221, International Publication No. WO2007 / 073462, International Publication No. WO2007 / 140071, International Publication No. WO2008 / 054942, International Publication No. WO2010 / 065393, International Publication No. WO2011 / 10744, International Publication No. WO2011 / 016582, International Publication No. WO2011 / 025056, International Publication No. WO2011 / 034202, International Publication No. WO2011 / 078030, International Publication No. WO2012 / 102409, International Publication No. WO2012 / 102410, International Publication No. WO2012 / 121414, etc. can be used without limitation.

[0220] In addition to the above, a photochromic compound having an oligomer chain group in the molecule may also be preferably used. As such a photochromic compound having an oligomer chain group, it is disclosed in many documents such as International Publication No. 2000 / 015630, International Publication No. 2004 / 041961, International Publication No. 2009 / 146509, International Publication No. 2012 / 149599, International Publication No. 2012 / 162725, International Publication No. 2013 / 078086, International Publication No. 2019 / 013249, International Publication No. 2019 / 203205, etc. Among these photochromic compounds having an oligomer chain group in the molecule, in order to exhibit more excellent photochromism and durability, the photochromic compounds having an oligomer chain group described in International Publication No. 2019 / 013249 and International Publication No. 2019 / 203205 are preferably used.

[0221] The indeno[1,2 - b]naphtho[2,3 - d]pyran compound preferably contains a compound represented by the following formula (16).

[0222]

[0223] In the formula, R 24 、R 25 、R 26 and R 27 are the same as those above.

[0224] r is an integer from 0 to 4. s is an integer from 0 to 4. When r is 2 - 4, the plurality of R 28 may be the same or different from each other. When s is 2 - 4, the plurality of R 29 may be the same or different from each other. In addition, when r is 2 - 4 and there are adjacent R 28 , the two adjacent R 28 can together with the carbon atom bonded to these R 28 form a ring optionally containing at least 1 heteroatom selected from oxygen atom, carbon atom, sulfur atom and nitrogen atom, and further the ring may have a substituent. In addition, when s is 2 - 4 and there are adjacent R 29 , the two adjacent R 29 can together with the carbon atom bonded to these R 29 form a ring optionally containing at least 1 heteroatom selected from oxygen atom, carbon atom, sulfur atom, or nitrogen atom, and further the ring may have a substituent.

[0225] R 28 and R 29Each independently represents a group represented by formula (15), a hydroxyl group, an alkyl group, a haloalkyl group, an optionally substituted cycloalkyl group, an alkoxy group, an amino group, a substituted amino group, an optionally substituted heterocyclic group, a cyano group, a halogen atom, an alkylthio group, an optionally substituted arylthio group, a nitro group, a formyl group, a hydroxycarbonyl group, an alkylcarbonyl group, an alkoxycarbonyl group, an optionally substituted aralkyl group, an optionally substituted aralkoxy group, an optionally substituted aryloxy group, an optionally substituted aryl group, an optionally substituted heteroaryl group, a mercapto group, an alkoxyalkylthio group, a haloalkylthio group, or an optionally substituted cycloalkylthio group, an optionally substituted silyl group, an optionally substituted oxysilyl group, a group represented by the following formula (17), or L-R 400 The group represented.

[0226]

[0227] E is an oxygen atom or NR 101 , R 101 is a hydrogen atom or an alkyl group. F is an oxygen atom or a sulfur atom. G is an oxygen atom, a sulfur atom or NR 202 . R 202 is a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a heteroaryl group. gg is an integer of 0 or 1. R 201 is a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a heteroaryl group. When G is an oxygen atom or a sulfur atom, R 201 is a group other than a hydrogen atom.

[0228] R 400 is a hydrogen atom, an alkyl group, an aryl group, a substituted silyl group, a polymer group or a photochromic group. The substituent of the silyl group is an alkyl group, an alkoxy group or an aryl group. L is a group represented by the following formula (18).

[0229]

[0230] J is a divalent group, each independently a direct bond, a substituted methylene group, an oxygen atom, a sulfur atom or NR 301 . R 301 is a hydrogen atom or an alkyl group. L in formula (18) is an oxygen atom or a sulfur atom. R 300 is an alkylene group, or a silylene group having an alkyl group or an aryl group as a substituent. R 302 , R 303 and R 304 are alkylene groups. hh, jj, kk and ll are 0 or 1. ii is an integer from 1 to 200. The units of multiple ii's can be the same or different. The dashed line represents the bond to R 400 .

[0231] <Other additives>

[0232] The curable composition contains the above component (A) and component (B) as essential components. In the curable composition, various known compounding agents can be compounded within the range that does not impair the effects. The compounding agents include, for example, various stabilizers such as mold release agents, ultraviolet absorbers, infrared absorbers, ultraviolet stabilizers, antioxidants, anti-coloring agents, antistatic agents, fluorescent dyes, dyes, pigments, and fragrances. In addition, a solvent and a leveling agent can also be compounded. Mercaptans such as tert-dodecyl mercaptan can be compounded as a polymerization regulator.

[0233] <Ultraviolet stabilizer>

[0234] If an ultraviolet stabilizer is used in combination, the durability of the photochromic compound can be further improved, so it is preferably compounded. As the ultraviolet stabilizer, a hindered amine light stabilizer, a hindered phenol antioxidant, and a sulfur-based antioxidant can be preferably used. There is no particular limitation on the hindered amine light stabilizer. In particular, from the aspect of preventing the deterioration of the photochromic compound, bis(1,2,2,6,6-pentamethyl-4-piperidyl) sebacate is preferred. In addition, hindered amine-based light stabilizers commercially available under the trade names Adekastab LA-52, LA-57, LA-62, LA-63, LA-67, LA-77, LA-87, etc. by ADEKA Corporation can also be preferably used.

[0235] As the hindered phenol antioxidant, it is preferred in terms of preventing the deterioration of the photochromic compound. For example, 2,6-di-tert-butyl-4-methylphenol, IRGANOX245 manufactured by BASF Japan Ltd.: ethylenebis(oxyethylene)bis[3,5-di-tert-butyl-4-hydroxy-m-tolyl] propionate, IRGANOX1076 manufactured by BASF Japan Ltd.: octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl) propionate, IRGANOX1010 manufactured by BASF Japan Ltd.: pentaerythritol tetra[3-(3,5-di-tert-butyl-4-hydroxyphenyl) propionate], and IRGANOX1035, 1075, 1098, 1135, 1141, 1222, 1330, 1425, 1520, 259, 3114, 3790, 5057, 565, etc. manufactured by BASF Japan Ltd. can also be cited. The amount of such an ultraviolet stabilizer used is not particularly limited as long as the effects are not impaired, and it is usually in the range of 0.001 to 10 parts by mass, particularly 0.01 to 1 part by mass, relative to 100 parts by mass of the curable composition.

[0236] <Polymerization initiator>

[0237] The polymerization initiator includes a thermal polymerization initiator and a photopolymerization initiator, and specific examples thereof are as described below.

[0238] As thermal polymerization initiators, examples include: Diacyl peroxides: Benzoyl peroxide, p-Chlorobenzoyl peroxide, Decanoyl peroxide, Lauroyl peroxide, Acetyl peroxide,

[0239] Peroxyesters: tert-Butyl 2-ethylhexyl peroxide, tert-Butyl neodecanoate, Cumyl tert-butyl peroxyneodecanoate, tert-Butyl benzoate,

[0240] Peroxycarbonates: Diisopropyl peroxydicarbonate, Di-sec-butyl peroxydicarbonate,

[0241] Azocompounds: Azobisisobutyronitrile;

[0242] etc.

[0243] As photopolymerization initiators, examples include Acetophenone-based compounds: 1-Phenyl-2-hydroxy-2-methylpropan-1-one, 1-Hydroxycyclohexyl phenyl ketone, 1-(4-Isopropylphenyl)-2-hydroxy-2-methylpropan-1-one,

[0244] α-Dicarbonyl-based compounds: 1,2-Diphenylethane-1,2-dione, Methyl phenylglyoxylate,

[0245] Acylphosphine oxide-based compounds: 2,6-Dimethylbenzoyl diphenylphosphine oxide, 2,4,6-Trimethylbenzoyl diphenylphosphine oxide, Methyl 2,4,6-trimethylbenzoyldiphenylphosphinate, 2,6-Dichlorobenzoyl diphenylphosphine oxide, 2,6-Dimethoxybenzoyl diphenylphosphine oxide.

[0246] It should be noted that when using a photopolymerization initiator, known polymerization and curing accelerator aids such as tertiary amines can also be used in combination.

[0247] <Surfactant>

[0248] When a surfactant is added, the wettability to the optical substrate and the primer layer can be improved, and the occurrence of appearance defects can be prevented. As surfactants, known surfactants such as silicone surfactants having a silicone chain (polyalkylsiloxane unit) as a hydrophobic group and fluorosurfactants having a fluorocarbon chain can be cited. When using a surfactant, two or more kinds can be used in combination. Furthermore, it can be a surfactant capable of polymerizing with the component (A) or a non-polymerizable surfactant.

[0249] Examples of silicone surfactants and fluorosurfactants that can be preferably used in specific examples include L-7001, L-7002, L-7604, FZ-2123, FZ-2110 manufactured by Dow Toray Co., Ltd., MEGAFAC F-470, MEGAFAC F-1405, MEGAFAC F-479 manufactured by DIC Corporation, Fluorad FC-430 manufactured by 3M Japan Ltd., TEGORAD2100, TEGORAD2300 manufactured by Evonik Japan Co., Ltd., BYK-UV3505, BYK-UV3505, BYK-UV3510, BYK-UV3530, BYK-3550, BYK-3560, BYK-UV3565, BYK-3566, BYK-UV3500, BYK-UV3535, BYK-UV3570, BYK-UV3575, BYK-UV3576 manufactured by BYK-Chemie Japan, KR-513, X-22-2445, X-40-9296, X-22-164, X-22-164A, X-22-164B, X-22-164C, X-22-164E, etc. manufactured by Shin-Etsu Chemical Co., Ltd.

[0250] <Ultraviolet absorber>

[0251] As the ultraviolet absorber, known ultraviolet absorbers such as benzophenone compounds, benzotriazole compounds, cyanoacrylate compounds, triazine compounds, benzoate compounds, cinnamate compounds, and oxanilide compounds can be used, and cyanoacrylate compounds, benzophenone compounds, benzotriazole compounds, and cinnamate compounds are particularly preferred. With respect to 100 parts by mass of the curable composition containing the photochromic compound and the polymerizable compound, the above ultraviolet stabilizer is preferably used in the range of 0.001 to 5 parts by mass.

[0252] <Cured product>

[0253] The cured product is obtained by curing the curable composition. The curing of the curable composition is carried out by causing a radical polymerization reaction by irradiation with active energy rays such as ultraviolet rays, α-rays, β-rays, γ-rays, LEDs, heat, or a combination of both. That is, depending on the types of the polymerizable monomer and the polymerization curing accelerator used and the form of the cured product formed, an appropriate curing means can be adopted. In the case of forming a laminate by the coating method described later, photopolymerization is preferably adopted for the reason of obtaining a uniform film thickness.

[0254] When thermally polymerizing a curable composition compounded with a polymerizable compound, the thermal polymerization temperature affects the properties of the resulting cured product. This temperature condition is affected by the type and amount of the thermal polymerization initiator and the type of the polymerizable compound, and thus cannot be generally defined. However, a method of initiating polymerization at a relatively low temperature and gradually increasing the temperature is usually preferred. The polymerization time also varies depending on various factors as with the temperature. Therefore, it is preferred to pre-determine the optimal time corresponding to these conditions, but generally, the conditions are preferably selected such that the polymerization is completed within 2 to 48 hours. When obtaining a photochromic laminate, it is preferred to perform polymerization at a temperature at which the reaction between the polymerizable functional groups proceeds. At this time, the optimal temperature and time are determined so as to achieve the target molecular weight.

[0255] In addition, when photopolymerizing the curable composition, among the polymerization conditions, in particular, the UV intensity affects the properties of the resulting photochromic cured product. This illuminance condition is affected by the type and amount of the photopolymerization initiator and the type of the polymerizable monomer, and thus cannot be generally defined. However, the conditions are usually preferably selected such that UV light with a wavelength of 365 nm is irradiated for 0.5 to 5 minutes at 50 to 500 mW / cm 2 ².

[0256] The bioplastic degree of the cured product is preferably 10% by mass or more. The bioplastic degree can be calculated by the method according to ISO standard 16620-3. The bioplastic degree of the cured product is preferably 25% by mass or more, more preferably 30% by mass or more, and further preferably 40% by mass or more. There is no particular upper limit value for this bioplastic degree. According to one example, it is 100% by mass or less, and according to another example, it is 80% by mass or less.

[0257] <Laminate>

[0258] According to another embodiment, a laminate is provided. The laminate includes an optical substrate and the cured product of the embodiment located on the surface of the optical substrate. The optical substrate includes, for example, resins such as diallyl carbonate resin, urethane resin, and thiourethane resin. The optical substrate can be a lens substrate. A primer layer can be provided between the laminate and the cured product. The primer layer includes urethane resin. The laminate of the embodiment preferably includes an optical substrate containing an allyl-based resin.

[0259] The bioplastic degree of the optical substrate is preferably 25% by mass or more. The bioplastic degree can be calculated by the method according to ISO standard 16620-3. The bioplastic degree of the optical substrate is preferably 30% by mass or more, more preferably 40% by mass or more. There is no particular upper limit value for this bioplastic degree. According to one example, it is 100% by mass or less, and according to another example, it is 80% by mass or less.

[0260] Figure 1 It is a cross-sectional view schematically showing an example of the laminate of the embodiment. Figure 1 The laminate 10 shown includes an optical substrate 11, a primer layer 1 provided on one main surface of the optical substrate 11, and a functional resin layer 12 provided on the main surface of the primer layer 1. The functional resin layer 12 contains the cured product of the embodiment. The optical substrate 11 is a convex meniscus lens having an uneven shape.

[0261] <Optical article>

[0262] The cured product of the embodiment can be widely used as an optical article. For example, it can be used as various storage materials, copying materials, photosensitive members for printing, storage materials for cathode ray tubes, photosensitive materials for lasers, photosensitive materials for holography, etc. instead of silver salt photosensitive materials, as well as lenses. The lens is suitable for glasses. A photochromic cured product containing a photochromic compound can also be used as a photochromic lens material, an optical filter material, a display material, a light meter, a decorative material, etc.

[0263] The cured product of the embodiment is particularly suitable for photochromic lens applications. Photochromic lenses are suitable as spectacle lenses such as sunglasses. As long as the method for manufacturing the photochromic lens can obtain uniform light control performance, a known method can be adopted.

[0264] In the case where photochromism is exhibited by the kneading method, the above-mentioned curable composition is injected between glass molds held by an elastomeric gasket or spacer, and casting polymerization is carried out by heating in an air furnace, irradiation with active energy rays such as ultraviolet rays, etc., according to the types of the polymerizable compound and the polymerization curing accelerator, whereby a photochromic cured product formed in the form of an optical material such as a lens can be obtained.

[0265] In the case where photochromism is exhibited by the lamination method, a coating solution is prepared by appropriately dissolving the curable composition in an organic solvent, the coating solution is applied to the surface of an optical substrate such as a lens substrate by spin coating, dipping, etc., and the organic solvent is removed by drying. Then, polymerization curing is carried out by UV irradiation, heating, etc. in an inert gas such as nitrogen, whereby a photochromic layer formed of a photochromic cured product is formed on the surface of the optical substrate (coating method).

[0266] In addition, an optical substrate such as a lens substrate is disposed opposite to a glass mold so as to form a predetermined gap, the curable composition is injected into the gap, and in this state, a photochromic layer composed of a photochromic cured product can also be formed on the surface of the optical substrate by casting polymerization using an internal mold by UV irradiation, heating, etc. (casting polymerization method).

[0267] When a photochromic layer is formed on the surface of an optical substrate by the lamination method (coating method and casting polymerization method) as described above, the adhesion between the photochromic layer and the optical substrate can also be improved by previously subjecting the surface of the optical substrate to chemical treatment using an alkali solution, an acid solution, etc., or physical treatment using corona discharge, plasma discharge, polishing, etc. Of course, a transparent adhesive resin layer may also be provided on the surface of the optical substrate.

[0268] In addition, the cured product formed from the curable composition can be post-processed according to its use. Examples of the post-processing include dyeing using a dye such as a disperse dye, lamination of a protective layer containing a urethane resin, an epoxy resin, etc., formation of a hard coating film of a hard coat agent mainly composed of a sol of a silane coupling agent, silicon, zirconium, antimony, aluminum, tin, tungsten, etc., formation of a thin film by vapor deposition of a metal oxide such as SiO2, TiO2, ZrO2, antireflection treatment of a thin film formed by coating an organic polymer, antistatic treatment, etc.

[0269] Examples

[0270] Next, the present invention will be described in detail using examples and comparative examples, but the present invention is not limited to these examples. The description of each component and the evaluation method, etc. are as follows.

[0271] <Each component>

[0272] (A) component

[0273] (A-1) component

[0274] M-PPG: Dimethacrylate of the following formula

[0275]

[0276] M-PTMG65: Polytetramethylene glycol dimethacrylate (average molecular weight 786, c = 9)

[0277] M-PTMG65Bio: Polytetramethylene glycol dimethacrylate using polytetramethylene glycol with a biomass content of 95% by mass (average molecular weight 803, c = 9, biomass content 76.8% by mass)

[0278] M-PTMG85: Polytetramethylene glycol dimethacrylate (average molecular weight 986, c = 11.8)

[0279] M-PTMG100: Polytetramethylene glycol dimethacrylate (average molecular weight 1136, c = 13.9)

[0280] M-PTMG130: Polytetramethylene glycol dimethacrylate (average molecular weight 1456, c = 17.8)

[0281] M-PTMG100Bio: Poly(tetramethylene glycol) dimethacrylate using poly(tetramethylene glycol) with a biomass content of 95 mass% (average molecular weight 1171, c = 14.1, biomass content 82.5 mass%)

[0282] M-EGTMG160: Dimethacrylate of the following formula

[0283]

[0284] M-EGTMG130: Dimethacrylate of the following formula

[0285]

[0286] M-EGTMG110: Dimethacrylate of the following formula

[0287]

[0288] (A-2)

[0289] TMPT: Trimethylolpropane trimethacrylate

[0290] D-TMP: Bis(trimethylolpropane) tetramethacrylate

[0291] A-TMMT: Pentaerythritol tetraacrylate

[0292] M-TMMT: Pentaerythritol tetramethacrylate

[0293] A-TMMT-43: Mixture of pentaerythritol triacrylate:pentaerythritol tetraacrylate = 57:43 (weight ratio)

[0294] M-TMMT-80: Mixture of pentaerythritol trimethacrylate:pentaerythritol tetramethacrylate = 18:82 (weight ratio)

[0295] A-DPEHA: Dipentaerythritol hexaacrylate

[0296] (A-3)

[0297] 9G: Poly(ethylene glycol) dimethacrylate (average molecular weight 550)

[0298] 14G: Poly(ethylene glycol) dimethacrylate (average molecular weight 770)

[0299] APC56: Dimethacrylate of polycarbonate diol obtained by phosgenation of pentamethylene glycol and hexamethylene glycol (average molecular weight 606)

[0300] MPCD56: Dimethacrylate of polycarbonate diol obtained by phosgenation of pentamethylene glycol and hexamethylene glycol (average molecular weight 634)

[0301] M-GDM: Glycerol dimethacrylate

[0302] M-NEO: Neopentyl glycol dimethacrylate

[0303] LA82: 1,2,2,6,6-Pentamethyl-4-piperidyl methacrylate

[0304] TSL: γ-Methacryloxypropyltrimethoxysilane

[0305] M-PTMG200: Poly(tetramethylene glycol) dimethacrylate (average molecular weight 2209, c = 28.5)

[0306] (Other radically polymerizable monomers)

[0307] RX-1: Polyrotaxane having an acryloyl group

[0308] A polyrotaxane having an acryloyl group satisfying the following characteristics was synthesized according to the method described in International Publication No. 2018 / 030257.

[0309] Weight-average molecular weight Mw (GPC) of polyrotaxane (RX-1) having an acryloyl group: 180,000.

[0310] Modification ratio of acryloyl group in the side chain: 80 mol%.

[0311] Ratio of OH groups remaining in the side chain: 20 mol%.

[0312] Axle molecule: Linear polyethylene glycol (PEG) with a molecular weight of 11,000.

[0313] Inclusion ring: α-Cyclodextrin (α-CD) introduction ratio 0.25.

[0314] Ends of the axle molecule: Blocked with adamantane.

[0315] Side chain introduced into the inclusion ring; (Average) molecular weight of the side chain is about 500.

[0316] Number of acryloyl groups per molecule: About 90.

[0317] The weight-average molecular weight Mw of polyrotaxane (RX-1) was measured by gel permeation chromatography (GPC method). As the apparatus, a liquid chromatography apparatus (manufactured by Waters Corporation, Japan) was used. As the columns, 2 TSKgel SuperHM-M (exclusion limit molecular weight: 4,000,000, manufactured by Tosoh Corporation) were used in series.

[0318] In addition, tetrahydrofuran was used as the developing solution, and the measurement was carried out under the conditions of a flow rate of 0.6 ml / min and a temperature of 40°C. Polystyrene was used as the standard sample, and the weight-average molecular weight was obtained by comparative conversion. As a result, the weight-average molecular weight of RX-1 was 180,000.

[0319] SO-1: A silsesquioxane having a methacryloyl group and having the following characteristics.

[0320] The number of methacrylate groups per 1 molecule: 20.

[0321] Weight-average molecular weight: 4,800.

[0322] In addition, SO-1 was synthesized by the following method. First, 248 g (1.0 mol) of 3-trimethoxysilylpropyl methacrylate was added with 248 ml of ethanol and 54 g (3.0 mol) of water, and 0.20 g (0.005 mol) of sodium hydroxide as a catalyst was added, and the reaction was carried out at 30°C for 3 hours. After 1 confirming the disappearance of the raw materials by 1H-NMR, it was neutralized with dilute hydrochloric acid, 174 ml of toluene, 174 ml of heptane and 174 g of water were added, and the aqueous layer was removed. Then, the organic layer was washed with water until the aqueous layer became neutral, and the solvent was concentrated to obtain SO-1. It should be noted that by 29 Si-NMR, it was confirmed that SO-1 was a mixture of cage structure, ladder structure and random structure.

[0323] The weight-average molecular weight Mw of SO-1 was measured by gel permeation chromatography (GPC method). As the device, a liquid chromatography device (manufactured by Waters Corporation, Japan) was used. As the columns, three columns of Shodex GPC KF-802 (exclusion limit molecular weight: 5000, manufactured by Showa Denko KK), Shodex GPC KF802.5 (exclusion limit molecular weight: 20000, manufactured by Showa Denko KK) and Shodex GPC KF-803 (exclusion limit molecular weight: 70000, manufactured by Showa Denko KK) were used in series.

[0324] In addition, tetrahydrofuran was used as the developing solution, and the measurement was carried out under the conditions of a flow rate of 1 ml / min and a temperature of 40°C. Polystyrene was used as the standard sample, and the weight-average molecular weight was obtained by comparative conversion.

[0325] (Component (B))

[0326] PC1: A compound represented by the following formula.

[0327]

[0328] PC2: A compound represented by the following formula.

[0329]

[0330] PC3: A compound represented by the following formula.

[0331]

[0332] PC4: A compound represented by the following formula.

[0333]

[0334] PC5: A compound represented by the following formula.

[0335]

[0336] PC6: A compound represented by the following formula.

[0337]

[0338] PC7: A compound represented by the following formula.

[0339]

[0340] (Other compounding agents)

[0341] (Stabilizer)

[0342] HALS: Bis(1,2,2,6,6-pentamethyl-4-piperidyl) sebacate

[0343] HP: Ethylene bis(oxyethylene) bis[3-(5-tert-butyl-4-hydroxy-m-tolyl) propionate] (manufactured by BASF Japan Ltd., Irganox 245).

[0344] (Photoinitiator)

[0345] PI: Phenylbis(2,4,6-trimethylbenzoyl)-phosphine oxide (manufactured by IGM, Omnirad 819)

[0346] Example 1

[0347] (Manufacture of photochromic curable composition)

[0348] First, prepare each component according to the following formulation.

[0349] (Component (A))

[0350] (Component (A-1)): 31.5 parts by mass of M-PTMG65.

[0351] Component (A-2): 62.9 parts by mass of TMPT.

[0352] Component (A-3): 5.6 parts by mass of TSL.

[0353] Component (B): 1.6 parts by mass of PC1.

[0354] (Other compounding agents)

[0355] (Polymerization initiator): 0.3 parts by mass of PI.

[0356] (Stabilizer): 1 part by mass of HP.

[0357] 31 parts by mass of HALS.

[0358] Next, after mixing all the compounds equivalent to component (A), component (B) and other additives are mixed therein to obtain a mixture. 1000 ppm of a leveling agent L7001 manufactured by Dow Toray Co., Ltd. is added to the obtained mixture and mixed, whereby a photochromic curable composition is obtained.

[0359] (Manufacture of optical article)

[0360] Using this photochromic curable composition, a photochromic laminate is obtained by a lamination method of polymerization as follows.

[0361] First, as an optical substrate, a thiocarbamate-based plastic lens having a center thickness of 2 mm and a refractive index of 1.60 is prepared. It should be noted that this thiocarbamate-based plastic lens is previously subjected to alkali etching with a 5% aqueous sodium hydroxide solution at 50 °C for 5 minutes, and then thoroughly washed with distilled water.

[0362] Using a spin coater (1H-DX2, manufactured by MIKASA), a moisture-curing primer (product name: TR-SC-P, manufactured by Tokuyama Corporation) is coated on the surface of the above plastic lens at a rotation speed of 70 rpm for 15 seconds, and then coated at 700 rpm for 10 seconds. Then, about 1 g of the above-obtained photochromic curable composition is spin-coated so that the film thickness of the photochromic coating is 40 μm.

[0363] In a nitrogen atmosphere, using a metal halide lamp with an output power of 200 mW / cm 2 The lens having the photochromic curable composition (photochromic coating) coated on its surface is irradiated with light for 90 seconds to cure the coating film. Then, it is further heated at 90 °C for 1 hour to produce a photochromic laminate having a photochromic layer.

[0364] Evaluation is carried out according to the following evaluation method, and the results are shown in Table 5.

[0365] <Evaluation method>

[0366] The obtained photochromic laminate is evaluated by the method shown below.

[0367] (1) Photochromic properties

[0368] [1] Maximum absorption wavelength (λmax):

[0369] The maximum absorption wavelength after color development obtained by a spectrophotometer (instantaneous multi-channel photodetector MCPD3000) manufactured by Otsuka Electronics Co., Ltd. is used as an index of the hue at the time of color development.

[0370] [2] Color development concentration at 23°C (A 23 ):

[0371] It is the difference between the absorbance {ε(240)} after 240 seconds of light irradiation at 23°C and the absorbance ε(0) without light irradiation at the above maximum absorption wavelength, and is used as an index of the color development concentration. The higher this value, the more excellent the photochromic property can be said to be.

[0372] [3] Half-life of fading at 23°C [τ1 / 2 (sec.)]:

[0373] At 23°C, after 300 seconds of light irradiation, when the light irradiation is stopped, the time required for the absorbance of the sample at the above maximum absorption wavelength to decrease to 1 / 2 of {ε(300) - ε(0)} is used as an index of the fading speed. The shorter this time, the faster the fading speed.

[0374] (2) Vickers hardness

[0375] The Vickers hardness is measured using a micro-Vickers hardness tester PMT-X7A (manufactured by Matsuzawa Co., Ltd.). A square pyramid-shaped diamond indenter is used, and the measurement is carried out under the conditions of a load of 10 gf and a holding time of the indenter of 30 seconds. The measurement results are measured a total of 4 times, and are expressed as the average value of a total of 3 times after removing the first value with a large measurement error.

[0376] (3) Crack evaluation

[0377] Twenty photochromic laminates are produced, and the presence or absence of cracks is visually confirmed, and the cracks are evaluated according to the following criteria.

[0378] A: No cracks are observed in all 20 photochromic laminates.

[0379] B: One photochromic laminate with cracks is observed among the 20 photochromic laminates.

[0380] C: Among 20 photochromic laminates, there are 1 to 3 or more photochromic laminates in which cracks are observed.

[0381] D: Among 20 photochromic laminates, there are 5 or more photochromic laminates in which cracks are observed in a part of the surface.

[0382] (4) Appearance evaluation

[0383] Using an allyl plastic lens with a center thickness of 2 mm and a refractive index of 1.50 as the optical substrate, an optical article with a photochromic laminate laminated on the optical substrate was prepared by the same method as above. For the obtained photochromic laminate, light was transmitted through a fluorescent lamp in a black box, and the appearance was evaluated according to the following criteria.

[0384] A: No cloudiness was observed.

[0385] B: Very little cloudiness was observed.

[0386] C: A small amount of cloudiness.

[0387] D: Cloudiness.

[0388] (5) Adhesion evaluation

[0389] The optical article obtained in the (4) appearance evaluation was immersed in boiling distilled water and boiled for 5 hours. The adhesion was evaluated 3 hours and 5 hours after boiling, respectively.

[0390] The adhesion was evaluated by the cross cut tape test in accordance with the method of JIS D-0202. That is, using a cutter, cut slits at 1 mm intervals on the surface of the obtained photochromic optical article to form 25 grids. A cellophane adhesive tape (Cellotape (registered trademark), manufactured by NICHIBAN Co., Ltd.) was firmly pasted thereon. Then, after stretching and peeling it off in one go from the surface in the 60° direction, the number and state of the grids where the photochromic laminate remained were visually confirmed, and the evaluation was carried out according to the following criteria.

[0391] A: No peeling at all

[0392] B: The peeling position is only at the intersection of the cuts, and the number of peeled grids is less than 5.

[0393] C: The peeling position is not only at the intersection of the cuts, but also partially or entirely along the cut edges, and the number of peeled grids is less than 5.

[0394] D: The peeling position is not only at the intersection of the cuts, but also partially or entirely along the cut edges, and the number of peeled grids is less than 10.

[0395] E: The peeling position is not only the intersecting part of the cutting but also significantly peeled partially or entirely along the edge of the cutting, and the number of peeled parts is more than 10 grids.

[0396] Examples 2 to 24 and Comparative Examples 1 to 8

[0397] Except for using the photochromic curable compositions described in Tables 1 to 5, photochromic cured products were produced in the same manner as in Example 1 and evaluated according to the same evaluation items. The results are shown in Tables 6 to 8.

[0398] [Table 1]

[0399]

[0400] [Table 2]

[0401]

[0402] [Table 3]

[0403]

[0404] [Table 4]

[0405]

[0406] [Table 5]

[0407]

[0408] [Table 6]

[0409]

[0410] [Table 7]

[0411]

[0412] [Table 8]

[0413]

[0414] It is clearly understood from Tables 6 and 7 that, in the comparison between the examples and the comparative examples using the same photochromic compound, the curable composition using the first radically polymerizable monomer represented by the formula (1) of the present invention has excellent photochromism, particularly excellent fading rate. In addition, it is understood that the appearance and adhesion are also excellent by making the content of the first radically polymerizable monomer arbitrary.

[0415] The preferred embodiments of the present invention are noted below. [1]

[0417] A curable composition comprising a first radically polymerizable monomer represented by the following formula (1) and a functional pigment, wherein the content of the first radically polymerizable monomer is 15% by mass or more and 34% by mass or less,

[0418]

[0419] In formula (1), R 1 is a hydrogen atom or a methyl group,

[0420] R 2 is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms,

[0421] R 3 is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms,

[0422] R 4 is a linear or branched alkylene group having 1 to 7 carbon atoms which may optionally have a substituent,

[0423] R 5 is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms,

[0424] R 6 is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms,

[0425] R 7 is a hydrogen atom or a methyl group,

[0426] a is 0 to 10,

[0427] b is 0 to 20,

[0428] c is 2 to 20 and is a number larger than each of a, b, d, and e,

[0429] d is 0 to 20,

[0430] e is 0 to 10. [2]

[0432] The curable composition according to [1], wherein the ratio M1 / M2 of the mass M1 of the first radically polymerizable monomer to the mass M2 of the functional pigment is 10 or more and 10,000 or less. [3]

[0434] The curable composition according to [1] or [2], wherein the content of the first radically polymerizable monomer is 17% by mass or more and 32% by mass or less. [4]

[0436] The curable composition according to any one of [1] to [3], wherein the content of the functional pigment is 0.01% by mass or more and 10% by mass or less. [5]

[0438] The curable composition according to any one of [1] to [4] further comprises a second radically polymerizable monomer having three or more (meth)acryloyl groups in one molecule. [6]

[0440] In the curable composition according to [5], the second radically polymerizable monomer comprises a polyfunctional (meth)acrylate represented by the following formula (I).

[0441]

[0442] In the formula (I),

[0443] Q 10 is methylene.

[0444] Q 11 is a linear or branched alkylene group having 1 to 3 carbon atoms.

[0445] Q 12 is a hydrogen atom or a methyl group.

[0446] Q 13 is a 3- to 6-valent organic group having 1 to 10 carbon atoms.

[0447] a1 is 0 or 1.

[0448] a2 is 0, 1, 2, or 3.

[0449] a3 is 3, 4, 5, or 6. [7]

[0451] In the curable composition according to [5] or [6], the content of the second radically polymerizable monomer is 1% by mass or more and 85% by mass or less. [8]

[0453] In the curable composition according to any one of [5] to [7], the ratio M1 / M3 of the mass M1 of the first radically polymerizable monomer to the mass M3 of the second radically polymerizable monomer is 0.1 or more and 20 or less. [9]

[0455] In the curable composition according to any one of [1] to [8], the first radically polymerizable monomer comprises a bifunctional (meth)acrylate represented by the following formula (3).

[0456]

[0457] In the formula (3),

[0458] R1 , R 7 and c have the same meanings as in the above formula (1),

[0459] R 11 is a linear alkylene group having 1 to 7 carbon atoms.

[10]

[0461] The curable composition according to any one of [1] to [9], wherein the number average molecular weight of the aforementioned first radically polymerizable monomer is 200 or more and 2000 or less.

[11]

[0463] The curable composition according to any one of [1] to

[10] , wherein the aforementioned functional pigment contains at least one compound selected from the group consisting of chromene compounds and spiropyran compounds.

[12]

[0465] The curable composition according to any one of [1] to

[11] , which further contains a third radically polymerizable monomer having one (meth)acryloyl group in one molecule.

[13]

[0467] The curable composition according to

[12] , wherein the content of the aforementioned third radically polymerizable monomer is 0.1% by mass or more and 20% by mass or less.

[14]

[0469] The curable composition according to

[12] or

[13] , wherein the ratio M1 / M4 of the mass M1 of the aforementioned first radically polymerizable monomer to the mass M4 of the aforementioned third radically polymerizable monomer is 0.1 or more and 50 or less.

[15]

[0471] The curable composition according to any one of [1] to

[14] , wherein the content of (poly)ethylene glycol di(meth)acrylate is 60% by mass or less.

[16]

[0473] A cured product obtained by curing the curable composition according to any one of [1] to

[15] .

[17]

[0475] A laminate comprising an optical substrate and the cured product according to

[16] provided on the surface of the aforementioned optical substrate.

[18]

[0477] A laminate comprising:

[0478] an optical substrate,

[0479] A primer layer that covers at least a part of the surface of the aforementioned optical substrate and contains a urethane resin, and

[0480] The cured product described in

[16] that covers at least a part of the aforementioned primer layer.

[19]

[0482] A lens that includes a lens substrate and the cured product described in

[16] located on the surface of the aforementioned lens substrate.

[20]

[0484] A pair of glasses that includes the lens described in

[19] .

[21]

[0486] The cured product described in

[16] , the bioplastic degree of which obtained by the method according to ISO standard 16620-3 is 10% by mass or more.

[22]

[0488] The laminate described in

[17] or

[18] , the bioplastic degree of the aforementioned optical substrate of which obtained by the method according to ISO standard 16620-3 is 25% by mass or more.

Claims

1. A curable composition comprising a first radically polymerizable monomer represented by the following formula (1) and a functional pigment, wherein the content of the first radically polymerizable monomer is 15% by mass or more and 34% by mass or less, In formula (1), R 1 is a hydrogen atom or a methyl group, R 2 is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, R 3 is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, R 4 is an optionally substituted linear or branched alkylene group having 1 to 7 carbon atoms, R 5 is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, R 6 is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, R 7 is a hydrogen atom or a methyl group, a is from 0 to 10, b is from 0 to 20, c is from 2 to 20 and is a number larger than each of a, b, d, and e, d is from 0 to 20, e is from 0 to 10.

2. The curable composition according to claim 1, wherein, The ratio M1 / M2 of the mass M1 of the first radically polymerizable monomer to the mass M2 of the functional pigment is 10 or more and 10000 or less.

3. The curable composition according to claim 1, wherein, The content of the first radically polymerizable monomer is 17% by mass or more and 32% by mass or less.

4. The curable composition according to claim 1, wherein, The content of the functional pigment is 0.01% by mass or more and 10% by mass or less.

5. The curable composition according to claim 1, further comprising a second radically polymerizable monomer having three or more (meth)acryloyl groups in one molecule.

6. The curable composition according to claim 5, wherein, The second radically polymerizable monomer comprises a polyfunctional (meth)acrylate represented by the following formula (I), In the formula (I), Q 10 is methylene, Q 11 is a linear or branched alkylene group having 1 to 3 carbon atoms, Q 12 is a hydrogen atom or a methyl group, Q 13 is an organic group having a valence of 3 to 6 and 1 to 10 carbon atoms, a1 is 0 or 1, a2 is 0, 1, 2, or 3, a3 is 3, 4, 5, or 6.

7. The curable composition according to claim 5, wherein, The content of the second radically polymerizable monomer is 1% by mass or more and 85% by mass or less.

8. The curable composition according to claim 5, wherein, The ratio M1 / M3 of the mass M1 of the first radically polymerizable monomer to the mass M3 of the second radically polymerizable monomer is 0.1 or more and 20 or less.

9. The curable composition according to claim 1, wherein, The first radically polymerizable monomer comprises a bifunctional (meth)acrylate represented by the following formula (3), In the formula (3), R 1 、R 7 and c have the same meanings as in the formula (1), R 11 is a linear alkylene group having 1 to 7 carbon atoms.

10. The curable composition according to claim 1, wherein, The number-average molecular weight of the first radically polymerizable monomer is 200 or more and 2000 or less.

11. The curable composition according to claim 1, wherein, The functional pigment comprises at least one compound selected from the group consisting of chromene compounds and spirooxazine compounds.

12. The curable composition according to claim 1, further comprising a third radically polymerizable monomer having one (meth)acryloyl group in one molecule.

13. The curable composition according to claim 12, wherein, The content of the third radically polymerizable monomer is 0.1% by mass or more and 20% by mass or less.

14. The curable composition according to claim 12, wherein, The ratio M1 / M4 of the mass M1 of the first radically polymerizable monomer to the mass M4 of the third radically polymerizable monomer is 0.1 or more and 50 or less.

15. The curable composition according to claim 1, wherein, The content of (poly)ethylene glycol di(meth)acrylate is 60% by mass or less.

16. A cured product obtained by curing the curable composition according to claim 1.

17. A laminate comprising an optical substrate and the cured product according to claim 16 on the surface of the optical substrate.

18. A laminate comprising: an optical substrate, a primer layer covering at least a part of the surface of the optical substrate and containing a urethane resin, and the cured product according to claim 16 covering at least a part of the primer layer.

19. A lens comprising a lens substrate and the cured product according to claim 16 on the surface of the lens substrate.

20. A pair of glasses comprising the lens according to claim 19.

21. The cured product according to claim 16, having a bioplasticity degree of 10% by mass or more obtained by the method according to ISO standard 16620-3.

22. The laminate according to claim 17 or 18, wherein the biomass plastic content of the optical substrate obtained by the method according to ISO standard 16620-3 is 25% by mass or more.

Images