Curable composition, cured article, laminate, optical article, lens, and spectacles

Abstract

The present disclosure provides a curable composition with which it is possible to provide a cured article having excellent functional dye performance and appearance, and also provides a cured article, a laminate, an optical article, a lens, and spectacles. One embodiment of the present invention provides a curable composition. The curable composition contains a first radically polymerizable monomer represented by formula (1) and a functional dye. In formula (1), R1 is a trivalent or more organic residue that contains at least one heteroatom selected from the group consisting of an oxygen atom and a nitrogen atom and that has 1-50 inclusive carbon atoms. R2 is a linear or branched alkylene group having 1-10 inclusive carbon atoms. a2 is 0-15 inclusive. b2 is 3 or more. Y is a monovalent group represented by formula (2) or a (meth)acryloyl group, provided that at least one of a plurality of Y groups is a monovalent group represented by formula (2), and a plurality of Y groups may be the same or different.

Description

Curable composition, cured product, laminate, optical article, lens, and eyeglasses

[0001] The present invention relates to a curable composition, a cured product, a laminate, an optical article, a lens, and eyeglasses.

[0002] Photochromic compounds, such as naphthopyran compounds, fulgide compounds, and spirooxazine compounds, are compounds that can reversibly convert into two isomers with different absorption spectra when irradiated with ultraviolet light, such as sunlight or light from a mercury lamp. Generally, when a colorless, bleached compound is irradiated with ultraviolet light, it quickly changes color and isomerizes (coloring reaction) to a colored state, and when the light irradiation is stopped and the compound is placed in a dark place, it returns to its original color (hereinafter also referred to as photochromic property). Taking advantage of this property, photochromic compounds are used in a variety of applications, particularly as optical materials.

[0003] For example, photochromic eyeglass lenses, which are given photochromic properties by using a photochromic compound, quickly become colored and function as sunglasses when exposed outdoors to light containing ultraviolet rays, such as sunlight, and fade and function as clear, ordinary eyeglasses indoors when not exposed to such light, and demand for such lenses has been increasing in recent years.

[0004] A known specific method for imparting photochromic properties to an optical material is a coating method in which a photochromic curable composition is applied to a plastic lens by spin coating or the like and then photocured to form a photochromic coating layer. The photochromic curable composition contains, for example, multiple types of (meth)acrylates and urethane oligomers.

[0005] International Publication No. WO 98 / 37115, U.S. Pat. No. 5,914,174, International Publication No. WO 01 / 02449, International Publication No. WO 03 / 11967, International Publication No. WO 2015 / 054036, International Publication No. WO 2009 / 075388, International Publication No. WO 2016 / 159263

[0006] An object of the present invention is to provide a curable composition capable of realizing a cured product having excellent performance and appearance of a functional dye, and a cured product, a laminate, a lens, and a pair of eyeglasses.

[0007] According to the present disclosure, there is provided a curable composition, the curable composition including a first radical polymerizable monomer represented by the following formula (1) and a functional dye:

[0008]

[0009] In formula (1), R １ R is a trivalent or higher organic residue having 1 to 50 carbon atoms and containing at least one heteroatom selected from the group consisting of oxygen atoms and nitrogen atoms. ２ is a linear or branched alkylene group having 1 to 10 carbon atoms. a2 is 0 to 15. b2 is 3 or greater. Y is a monovalent group represented by the following formula (2) or a (meth)acryloyl group, with the proviso that at least one of the multiple Ys is a monovalent group represented by the following formula (2), and the multiple Ys may be the same or different.

[0010]

[0011] In formula (2), the dashed line represents a bond to the oxygen atom in formula (1). ３ R is a linear or branched alkylene group having 1 to 6 carbon atoms. ４ is a hydrogen atom or a methyl group. c2 is 1 or more and 5 or less.

[0012] According to the present disclosure, a cured product is provided. The cured product is obtained by curing the curable composition according to an embodiment.

[0013] According to the present disclosure, there is provided a laminate, which includes an optical substrate and a cured body according to an embodiment, which is positioned on a surface of the optical substrate.

[0014] According to the present disclosure, an optical article is provided. The optical article includes a cured body according to an embodiment.

[0015] According to the present disclosure, a lens is provided, the lens including a cured body according to an embodiment.

[0016] According to the present disclosure, eyeglasses are provided, the eyeglasses including lenses according to an embodiment.

[0017] According to the present invention, there are provided a curable composition capable of realizing a cured product having excellent functional dye performance and appearance, as well as a cured product, a laminate, an optical article, a lens, and a pair of eyeglasses.

[0018] FIG. 1 is a cross-sectional view schematically illustrating an example of a laminate according to an embodiment.

[0019] The curable composition according to the embodiment includes a first radical polymerizable monomer and a functional dye. The first radical polymerizable monomer is a tri- or higher functional polyfunctional (meth)acrylate having a urethane bond. Use of such a curable composition makes it possible to realize a cured product having excellent performance and appearance of the functional dye. The reason for this has not been clearly elucidated, but the present inventors believe it to be as follows.

[0020] First, functional dyes such as photochromic compounds include compounds that undergo structural changes in response to energy such as light, resulting in color development, fading, or discoloration. For such functional dyes to easily undergo structural changes in a polymer solid matrix, it is important that the functional dye be located within the soft segments in the polymer solid matrix. Increasing the proportion of di(meth)acrylate in the curable composition is useful to increase the proportion of soft segments in the cured product. In particular, using a di(meth)acrylate with a high (meth)acrylic equivalent tends to increase the distance between crosslinking points, thereby further improving the performance of the functional dye. However, an excessively high proportion of di(meth)acrylate can reduce the number of crosslinking points, thereby reducing the curability of the polymer solid matrix. Reduced curability can also lead to poor appearance of the cured product obtained by curing the curable composition. Specifically, when a curable composition is applied to a substrate by spin coating or the like, thick puddles of the coating film may form around the periphery of the substrate. When a substrate having a relatively thin central coating film and a peripheral portion around the central portion where a liquid puddle forms is cured, the coating film may not cure sufficiently at the peripheral portion where the liquid puddle forms, resulting in wrinkled, poor appearance of the cured product. In particular, when a functional dye is contained, curing may be even more insufficient, resulting in significant poor appearance. The curable composition according to the embodiment is characterized in that the first radical polymerizable monomer has a urethane bond, and the urethane bond is located near a (meth)acryloyl group. The presence of the urethane bond enhances the cohesive force between molecules, reducing the intermolecular distance. Because the urethane bond in the first radical polymerizable monomer is located near the (meth)acryloyl group, the intermolecular (meth)acryloyl group distance is reduced. Furthermore, the first radical polymerizable monomer contains multiple (meth)acryloyl groups, which is believed to more efficiently improve curability. Furthermore, the cohesive force of the urethane bond contributes to the cured product, resulting in improved hardness. This makes it possible to increase the proportion of soft segments in the cured product.Therefore, in the cured product obtained by curing this curable composition, the performance of the functional dye can be fully exhibited and appearance defects can be reduced.

[0021] Each component will be described in detail below.

[0022] <(A) Radically Polymerizable Monomer> The radically polymerizable monomer (A) includes (A-1), i.e., a first radically polymerizable monomer represented by formula (1). Hereinafter, the first radically polymerizable monomer represented by formula (1) will also be referred to as component (A-1). The radically polymerizable monomer (A) will also be referred to as component (A). The radically polymerizable monomer (A) may include other radically polymerizable monomers depending on the desired properties of the cured product.

[0023] The other radical polymerizable monomer is not particularly limited as long as it is a polymerizable monomer that can be polymerized with the (A-1) component, and known monomers can be used, but a radical polymerizable monomer having a (meth)acryloyl group is preferred. As the radical polymerizable monomer having a (meth)acryloyl group, the following component (A-2), i.e., a second radical polymerizable monomer having two (meth)acryloyl groups in one molecule, component (A-3), i.e., a third radical polymerizable monomer other than the (A-1) component having three or more (meth)acryloyl groups in one molecule, and component (A-4), i.e., another third radical polymerizable monomer having a (meth)acryloyl group, are preferably used.

[0024] <Component (A-1): First Radically Polymerizable Monomer> The first radically polymerizable monomer is a (meth)acrylate compound represented by the following formula (1).

[0025]

[0026] R in formula (1) １is a trivalent or higher organic residue having 1 to 50 carbon atoms and containing at least one heteroatom selected from the group consisting of oxygen atoms and nitrogen atoms. The valence of the organic residue may be tetravalent or higher, pentavalent or higher, or hexavalent or higher, or may be 20 or lower, decavalent or lower, or octavalent or lower. The valence of the organic residue is preferably trivalent or higher and hexavalent or lower, and more preferably trivalent or higher and tetravalent or lower.

[0027] The organic residue typically consists only of the heteroatoms, carbon atoms, and hydrogen atoms. The organic residue preferably has oxygen atoms as bonds, and preferably consists only of O bonds. The number of heteroatoms in the organic residue is, for example, 1 or more, 2 or more, or 3 or more. This number may be 20 or less, 10 or less, or 5 or less. The heteroatom is preferably an oxygen atom. From the viewpoint of the appearance and hardness of the obtained cured body, the number of carbon atoms in the organic residue is preferably 1 or more and 40 or less, more preferably 2 or more and 30 or less, and even more preferably 3 or more and 10 or less. It is particularly preferable that the organic residue has any of the structures represented by the following formulas (1-A) to (1-I).

[0028]

[0029]

[0030]

[0031]

[0032]

[0033]

[0034]

[0035]

[0036]

[0037] In formulas (1-A) to (1-I), * represents -(R ２ -O) ａ２ -Y bond, i.e., R ２ or represents a bond to Y.

[0038] In formula (1-H), d2 is 4 or more and 10 or less. From the viewpoints of availability and easy-to-handle viscosity of the resulting curable composition, d2 is preferably 4 or more and 8 or less, more preferably 4 or more and 6 or less, more preferably 4 or more and 5 or less, and particularly preferably 4.

[0039] In formula (1), R ２ R is a linear or branched alkylene group having 1 to 10 carbon atoms. ２ is preferably a linear alkylene group having 1 to 10 carbon atoms, more preferably a linear alkylene group having 2 to 6 carbon atoms, and particularly preferably a linear alkylene group having 2 to 4 carbon atoms.

[0040] a2 is 0, 1, or 2 or more and 15 or less. When it is desired to further increase the hardness of the obtained cured body, a2 is preferably a number of 0 or more and 6 or less, more preferably a number of 0 or more and 4 or less, even more preferably a number of 0 or more and 2 or less, and particularly preferably 0. When it is desired to improve the performance of the functional dye in the obtained cured body, a2 is preferably a number of 5 or more and 15 or less, more preferably a number of 5 or more and 13 or less, even more preferably a number of 6 or more and 12 or less, and particularly preferably a number of 6 or more and 11 or less.

[0041] b2 represents the valence of R1 and is 3 or more. b2 may be 4 or more, 5 or more, or 6 or more, or may be 20 or less, 10 or less, or 8 or less. b2 is preferably 3 or more and 6 or less, and more preferably 3 or more and 4 or less.

[0042] Y is a monovalent group represented by the following formula (2) or a (meth)acryloyl group. However, at least one of the multiple Ys is a monovalent group represented by the following formula (2). The multiple Ys may be the same or different. In the first radical polymerizable monomer, the number of monovalent groups represented by the following formula (2) may be, for example, 2 or more, 3 or more, 4 or more, or 5 or less.

[0043] The plurality of Y's may be monovalent groups represented by the following formula (2) alone, or may contain (meth)acryloyl groups. The proportion of monovalent groups represented by the following formula (2) to the total of monovalent groups represented by the following formula (2) and (meth)acryloyl groups is preferably 10% or more, more preferably 15% or more, and particularly preferably 20% or more. The upper limit of the proportion of monovalent groups represented by the following formula (2) is 100%.

[0044]

[0045] In formula (2), the dashed line represents the oxygen atom or R １ Represents a bond with.

[0046] R ３ R is a linear or branched alkylene group having 1 to 6 carbon atoms. ３ is preferably a linear alkylene group having 1 to 6 carbon atoms, more preferably a linear alkylene group having 1 to 4 carbon atoms, and particularly preferably a linear alkylene group having 2 to 4 carbon atoms.

[0047] R ４ is a hydrogen atom or a methyl group. That is, the component (A-1) may be a compound having only urethane-bonded acryloyl groups, as represented by the above formula (2), a compound having only urethane-bonded methacryloyl groups, or a compound having functional groups of both urethane-bonded acryloyl groups and methacryloyl groups. When a component (A-1) having a high proportion of methacryloyl groups is used, the color density of the photochromic dye tends to be high and a cured product having excellent durability against repeated use tends to be obtained. When a component (A-1) having a high proportion of acryloyl groups is used, a cured product having excellent appearance tends to be obtained. R ４ is preferably a methyl group.

[0048] c2 is 1 or more and 5 or less.

[0049] From the viewpoints of achieving both functionality and hardness, appearance, and easy-to-handle viscosity, the number average molecular weight of the first radical polymerizable monomer is preferably less than 3,000, more preferably 2,500 or less, even more preferably 2,000 or less, particularly preferably 1,700 or less, and most preferably 1,500 or less. The lower limit of the number average molecular weight of the first radical polymerizable monomer is, for example, 370 or more, and in another example, 410 or more. The number average molecular weight can be measured, for example, by gel permeation chromatography (GPC) or a mass spectrometer.

[0050] Specific examples of the first radical polymerizable monomer represented by the above formula (1) include the following.

[0051]

[0052]

[0053]

[0054] <Component (A-2): Second Radically Polymerizable Monomer Having Two (Meth)acryloyl Groups in One Molecule> The curable composition according to the embodiment preferably further contains component (A-2): a second radically polymerizable monomer having two (meth)acryloyl groups in one molecule. When component (A-2) is contained, a cured product having high performance of the functional dye tends to be obtained.

[0055] Component (A-2) preferably has one or more methacryloyl groups, and more preferably has two methacryloyl groups. The presence of methacryloyl groups tends to suppress deterioration of the functional dye and improve the appearance of the cured product.

[0056] The component (A-2) preferably contains an alkylene oxide chain. Use of such a component (A-2) tends to enhance the functionality of the cured body. In particular, it is preferable to use a second radically polymerizable monomer having at least one polyalkylene glycol chain structure with a number-average molecular weight of 250 or more. The number of carbon atoms in the alkylene oxide chain is preferably 1 to 10, and more preferably 2 to 5. The proportion N2 / N1 of the number-average molecular weight N1 of the component (A-2) accounted for by the number-average molecular weight N2 of the alkylene oxide chain is preferably 50% or more, more preferably 60% or more, and even more preferably 80% or more. This proportion may be 95% or less, or may be 90% or less.

[0057] From the viewpoint of achieving both the performance of the functional dye and hardness, and also taking into consideration the viscosity of the resulting curable composition, the number average molecular weight of the component (A-2) is preferably from 350 to 9,000, more preferably from 400 to 7,000, even more preferably from 500 to 6,000, and most preferably from 600 to 3,500. The number average molecular weight of the component (A-2) may be from 400 to 3,500, or may be from 600 to 2,500. The number average molecular weight can be measured, for example, by gel permeation chromatography (GPC).

[0058] The second radical polymerizable monomer may contain at least one structure selected from the group consisting of an ester bond, a urethane bond, a urea bond, a carbonate bond, and a carbonyl group. Preferably, the second radical polymerizable monomer does not contain at least one structure selected from the group consisting of an ester bond, a urethane bond, a urea bond, a carbonate bond, and a carbonyl group.

[0059] The second radically polymerizable monomer preferably contains a di(meth)acrylate represented by the following formula (3).

[0060]

[0061] In formula (3), Q ３ and Q ６are each independently a hydrogen atom or a methyl group. That is, the compound represented by formula (3) may be a diacrylate, a dimethacrylate, or a methacrylate acrylate. ３ and Q ６ is preferably a methyl group.

[0062] Q ４ and Q ５ are each independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. ４ and Q ５ are each independently preferably a hydrogen atom or a methyl group, and particularly preferably a hydrogen atom.

[0063] a and b each independently represent 0 or more and 10 or less, preferably 0 or more and 5 or less, more preferably 0 or more and 3 or less, and particularly preferably 0 or more and 2 or less.

[0064] Z 1 and Z ２ are each independently 0 or 1, and Z 1 and Z ２ is preferably 0.

[0065] Q ７ is a divalent group having a number average molecular weight of 250 or more and represented by the following formula (3a):

[0066]

[0067] Q in formula (3a) ７ａ , Q ７ｂ , Q ７ｄ , and Q ７ｅ are each independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. ７ａ , Q ７ｂ , Q ７ｄ , and Q ７ｅ are each independently preferably a hydrogen atom or a methyl group. ７ａ and Q ７ｂ are different groups. ７ｄ and Q ７ｅ are different groups. ７ａ and Q ７ｅ may be the same group. ７ｂand Q ７ｄ may be the same group.

[0068] Q ７ｃ represents a linear or branched alkylene group having 2 to 20 carbon atoms which may have a substituent, and f is 3 or more and 100 or less.

[0069] Repeating unit with subscript f - (OQ ７ｃ )- is a first alkylene oxide unit. The polymer portion formed by this repeating unit can form the soft segment of the cured product. ７ｃ is preferably a linear alkylene group. The number of carbon atoms in the alkylene group is preferably 3 to 10, more preferably 3 to 6, and particularly preferably 3 to 4. The greater the number of carbon atoms in the alkylene group, the higher the functionality of the cured body. On the other hand, if the number of carbon atoms in the alkylene group is too large, the amount of soft segments per unit mass decreases, which may reduce the functionality of the cured body.

[0070] From the viewpoint of achieving both functionality and hardness, f is preferably 6 or more and 85 or less, more preferably 7 or more and 60 or less, even more preferably 8 or more and 45 or less, and particularly preferably 9 or more and 30 or less.

[0071] d and h are 0 or more and 10 or less. From the viewpoint of achieving both functionality and hardness, d and h are preferably 0 or more and 5 or less, more preferably 0 or more and 2 or less, even more preferably 0 or 1, and most preferably 0.

[0072] e and g are 0 or more and 20 or less. From the viewpoint of achieving both functionality and hardness, e and g are preferably 0 or more and 15 or less, more preferably 0 or more and 10 or less, even more preferably 0 or more and 5 or less, and particularly preferably 0.

[0073] In other words, the di(meth)acrylate represented by formula (3) may be a monomer further comprising at least one of a second alkylene oxide unit which is a repeating unit having e and g attached thereto, and a third alkylene oxide unit which is a repeating unit having d and h attached thereto.

[0074] The di(meth)acrylate represented by formula (3) is Z1 and Z ２ is preferably 0. Such a compound is represented by the following formula (3b).

[0075]

[0076] In the above formula (3b), Q ３ , and Q ６ is a hydrogen atom or a methyl group. ７ａ , Q ７ｂ , Q ７ｃ , Q ７ｄ , Q ７ｅ , d, e, f, g, and h have the same meanings as in formula (3a).

[0077] The di(meth)acrylate represented by formula (3b) preferably has d, e, g, and h all equal to 0, i.e., contains only a first alkylene oxide unit. The use of such a di(meth)acrylate represented by formula (3b) tends to increase the hardness of the cured product. f may be 6 or more and 85 or less, or 9 or more and 30 or less. Such a compound is, for example, represented by formula (3c) below.

[0078]

[0079] In the above formula (3c), Q ３ , Q ６ , Q ７ｃ and f are defined as in formula (3b). Specific examples of the compound represented by formula (3c) include polyethylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, polytrimethylene glycol di(meth)acrylate, polytetramethylene glycol di(meth)acrylate, polypentamethylene glycol di(meth)acrylate, and polyhexamethylene glycol di(meth)acrylate.

[0080] When a di(meth)acrylate represented by formula (3b) in which d and h are 0 and e and g are 1 or greater is used, i.e., a di(meth)acrylate represented by formula (3b) further containing a second alkylene oxide unit, a cured product with high functionality of the functional dye tends to be obtained. In such a di(meth)acrylate represented by formula (3b), b and d may be 2 or greater and 15 or less, or 4 or greater and 10 or less.

[0081] Specific examples of such di(meth)acrylates represented by formula (3b) are as follows:

[0082]

[0083]

[0084]

[0085] The di(meth)acrylate represented by formula (3b) may be a monomer in which d, e, g, and h are each 1 or more, i.e., further comprising both a second alkylene oxide unit and a third alkylene oxide unit, wherein the second alkylene oxide unit and the third alkylene oxide unit have different structures.

[0086] Specific examples of such di(meth)acrylates represented by formula (3b) are as follows:

[0087]

[0088]

[0089] The di(meth)acrylate represented by formula (3) can be produced, for example, by the following method: First, an isocyanate compound represented by the following formula (4) is prepared. This compound contains one isocyanate group and one (meth)acryloyl group.

[0090]

[0091] In formula (4), Q ５ , Q ６, and b have the same meanings as in formula (3). The di(meth)acrylate represented by formula (3) is obtained by reacting the isocyanate compound represented by formula (4) with the polyol compound represented by the following formula (3d). The di(meth)acrylate represented by formula (3) obtained by the above method has Q ４ and Q ５ and a and b are the same. This reaction may be carried out in the presence of a solvent. Examples of the solvent that can be used include acetone, methyl ethyl ketone, methyl isobutyl ketone, diethyl ketone, cyclohexanone, dioxane, toluene, hexane, heptane, ethyl acetate, butyl acetate, dimethylformamide, and tetrahydrofuran.

[0092]

[0093] Q of the polyol compound of formula (3d) ７ａ , Q ７ｂ , Q ７ｃ , Q ７ｄ , Q ７ｅ , d, e, f, g, and h have the same meanings as in formula (3b). The polyol compound of formula (3d) may be derived from plants or petroleum.

[0094] In the formula (3), when Z1 and Z2 are 0, that is, the di(meth)acrylate represented by the formula (3b) can be produced, for example, by the following method.

[0095] The diacrylate represented by formula (3b) having an acryloyl group can be synthesized by esterification of a polyol compound represented by formula (3d) with acrylic acid.

[0096] Specifically, the polyol compound and acrylic acid dissolved in a solvent such as toluene are stirred in the presence of a mineral acid such as sulfuric acid or hydrochloric acid, an organic acid such as an aromatic sulfonic acid, or a Lewis acid such as boron fluoride ether, while heating as necessary, and the resulting water is removed by azeotropy to cause the reaction. Examples of methods for removing water in the esterification reaction include a method using a drying agent such as anhydrous magnesium sulfate or molecular sieves, and a method in which water is removed in the presence of a dehydrating agent typified by dicyclohexylcarbodiimide.

[0097] Alternatively, the compound can be synthesized by esterification using an acrylic acid halide. Specifically, the polyol compound and acrylic acid dissolved in an ether solvent such as tetrahydrofuran are stirred in the presence of a base such as pyridine or dimethylaniline, with heating as necessary, and the resulting hydrogen halide is removed.

[0098] Furthermore, it can also be synthesized by a transesterification reaction with an ester compound such as acrylic anhydride or methyl acrylate. Specifically, a method can be employed in which the polyol compound and acrylic acid are dissolved in a solvent such as toluene in the presence of an acidic catalyst such as an aromatic sulfonic acid or a basic catalyst such as sodium acetate or pyridine, and then stirred while heating as necessary.

[0099] The compound represented by formula (3b) having a methacryloyl group can be synthesized in the same manner as above, for example, by using methacrylic acid instead of acrylic acid.

[0100] Among the above polyol compounds, a polyol compound in which d and h are 0 and e and g are 1 or more, that is, a polyol having a second alkylene oxide unit, can be synthesized, for example, by the following method.

[0101] H-(OQ ７ｃ ) ｆA polyol having a second alkylene oxide unit can be synthesized by reacting —OH with a cyclic ether compound such as ethylene oxide or propylene oxide. The polyol compound having a second alkylene oxide unit can be synthesized, for example, by carrying out the reaction in a nitrogen-substituted autoclave at high temperature and pressure in the presence of a catalyst such as an alkali metal hydroxide, e.g., potassium hydroxide.

[0102] Among the above polyol compounds, a polyol compound in which d, e, g, and h are 1 or more, i.e., a di(meth)acrylate represented by formula (3b) further containing second and third alkylene oxide units, can be synthesized, for example, by the following method.

[0103] A polyol compound having a second alkylene oxide unit is reacted with a cyclic ether compound to synthesize a polyol compound having a third alkylene oxide unit, and the resulting polyol compound further having a third alkylene oxide unit is reacted with acrylic acid or methacrylic acid in the same manner as described above to synthesize a di(meth)acrylate represented by formula (3b) further containing second and third alkylene oxide units.

[0104] The component (A-2) may contain a di(meth)acrylate represented by the following formula (5):

[0105]

[0106] R in formula (5) １４ and R １５ are each a hydrogen atom or a methyl group. １６ and R １７ are each a hydrogen atom or a methyl group.

[0107] A is a divalent organic group, and is a linear or branched alkylene group having from 1 to 20 carbon atoms, a phenylene group which may have a halogen or an alkyl group having from 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:

[0108]

[0109]

[0110]

[0111]

[0112]

[0113] In the above formula, R １８Ａ , R １８Ｂ represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a halogen atom. xx and xy each represent an integer of 0 to 4 or an integer of 0 to 10. Ring X represents a benzene ring or a cyclohexane ring. YY represents an integer of -O-, -S-, -(SO ２ )-,-CO-,-CH ２ -, -CH=CH-, -C(CH ３ ) ２ -, -C(CH ３ ) (C ６ H ５ )—, or a group represented by any of the following formulae:

[0114]

[0115]

[0116] In formula (5), l and m are each an integer of 0 or 1 or more, and l+m is an average value of 2 or more and 30 or less.

[0117] Specific examples of the bifunctional (meth)acrylate represented by the above formula (5) include alkoxylated bisphenol A diacrylate and alkoxylated bisphenol A dimethacrylate.

[0118] The component (A-2) may contain a di(meth)acrylate represented by the following formula (6):

[0119]

[0120] R in formula (6) １９ and R ２０ are each a hydrogen atom or a methyl group.

[0121] n is a number between 1 and 20 on average.

[0122] B and B' are each independently a linear or branched alkylene group having from 2 to 15 carbon atoms. B and B' may be the same or different. When there are multiple Bs, the multiple Bs may be the same or different groups.

[0123] The bifunctional (meth)acrylate represented by the above formula (6) can be produced by reacting a polycarbonate diol with (meth)acrylic acid.

[0124] Examples of the polycarbonate diol to be used here include the following: Specifically, polycarbonate diol (average molecular weight 800 to 2000) obtained by phosgenation of trimethylene glycol, polycarbonate diol (average molecular weight 800 to 2000) obtained by phosgenation of tetramethylene glycol, polycarbonate diol (average molecular weight 800 to 2000) obtained by phosgenation of pentamethylene glycol, polycarbonate diol (average molecular weight 800 to 2000) obtained by phosgenation of hexamethylene glycol, polycarbonate diol (average molecular weight 800 to 2000) obtained by phosgenation of octamethylene glycol, polycarbonate diol (average molecular weight 800 to 2000) obtained by phosgenation with nonamethylene glycol, polycarbonate diol (average molecular weight 800 to 2000) obtained by phosgenation of triethylene glycol and tetramethylene glycol, Examples thereof include recarbonate diol (average molecular weight 800 to 2000), polycarbonate diol (average molecular weight 800 to 2000) obtained by phosgenation of tetramethylene glycol and hexamethylene diglycol, polycarbonate diol (average molecular weight 800 to 2000) obtained by phosgenation of pentamethylene glycol and hexamethylene glycol, polycarbonate diol (average molecular weight 800 to 2000) obtained by phosgenation of tetramethylene glycol and octamethylene glycol, polycarbonate diol (average molecular weight 800 to 2000) obtained by phosgenation of hexamethylene glycol and octamethylene glycol, and polycarbonate diol (average molecular weight 800 to 2000) obtained by phosgenation of 1-methyltrimethylene glycol.

[0125] The component (A-2) may contain a di(meth)acrylate having a urethane bond. The urethane di(meth)acrylate can be obtained, for example, by reacting a polyisocyanate compound having two isocyanate groups in the molecule, a polyol compound having two hydroxyl groups in the molecule, and a hydroxyl group-containing (meth)acrylate.

[0126] Suitable examples of the polyisocyanate include hexamethylene diisocyanate, isophorone diisocyanate, lysine isocyanate, 2,2,4-hexamethylene diisocyanate, dimer acid diisocyanate, isopropylidenebis-4-cyclohexyl isocyanate, dicyclohexylmethane diisocyanate, norbornene diisocyanate, and methylcyclohexane diisocyanate.

[0127] Examples of polyols include polyalkylene glycols having 2 to 4 carbon atoms and having repeating units of ethylene oxide, propylene oxide, or hexamethylene oxide, and polyester diols such as polycaprolactone diol. Other examples include polycarbonate diol, polybutadiene diol, pentaerythritol, ethylene glycol, propylene glycol, 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, and trimethylolpropane.

[0128] In addition, a reaction mixture obtained by further reacting a urethane prepolymer having an isocyanate group at its terminal by the reaction of such a polyisocyanate and a polyol with 2-hydroxy(meth)acrylate, or a reaction mixture obtained by directly reacting the diisocyanate with 2-hydroxy(meth)acrylate, such as a urethane(meth)acrylate monomer, can also be used.

[0129] As the di(meth)acrylate having a urethane bond, a compound represented by the above formula (1), in which the organic residue is divalent and b2 is 2, may be used.

[0130] Examples of hydroxyl group-containing (meth)acrylates include 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 3-hydroxybutyl (meth)acrylate, and 4-hydroxybutyl (meth)acrylate.

[0131] As the bifunctional (meth)acrylate having a urethane bond, commercially available products can be used without any restrictions, and examples thereof include UA-122P (molecular weight 1,100) and U-122P (molecular weight 1,100).

[0132] The component (A-2) may contain a bifunctional (meth)acrylate other than those mentioned above. Examples of the bifunctional (meth)acrylate other than those mentioned above include a bifunctional (meth)acrylate containing a sulfur atom and a di(meth)acrylate of an alkylene diol. Preferably, the sulfur atom of the bifunctional (meth)acrylate containing a sulfur atom forms part of the molecular chain as a sulfide group. Specific examples include bis(2-methacryloyloxyethylthioethyl)sulfide, bis(methacryloyloxyethyl)sulfide, bis(acryloyloxyethyl)sulfide, 1,2-bis(methacryloyloxyethylthio)ethane, 1,2-bis(acryloyloxyethyl)ethane, bis(2-methacryloyloxyethylthioethyl)sulfide, bis(2-acryloyloxyethylthioethyl)sulfide, 1,2-bis(methacryloyloxyethylthioethylthio)ethane, 1,2-bis(acryloyloxyethylthioethylthio)ethane, 1,2-bis(methacryloyloxyisopropylthioisopropyl)sulfide, and 1,2-bis(acryloyloxyisopropylthioisopropyl)sulfide.

[0133] The di(meth)acrylate of an alkyldiol is preferably an alkylene diol having a linear or branched alkylene group having from 2 to 30 carbon atoms. Specific examples include ethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, 1,3-propanediol di(meth)acrylate, neopentyl glycol di(meth)acrylate, 1,4-butanediol di(meth)acrylate, 1,5-pentanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,9-nonanediol di(meth)acrylate, and 1,10-decanediol di(meth)acrylate.

[0134] <(A-3): A third radically polymerizable monomer having a structure different from that of the component (A-1) and having three or more (meth)acryloyl groups in one molecule> The curable composition according to the embodiment may further include, as the component (A-3), a third radically polymerizable monomer having a structure different from that of the component (A-1) and having three or more (meth)acryloyl groups in one molecule. Hereinafter, the third radically polymerizable monomer having a structure different from that of the component (A-1) and having three or more (meth)acryloyl groups in one molecule will also be referred to as the component (A-3). The inclusion of the third radically polymerizable monomer tends to increase the hardness of the cured body.

[0135] Examples of the component (A-3) include polyfunctional (meth)acrylates represented by the following formula (I), polyfunctional (meth)acrylates having a urethane bond, and polyfunctional (meth)acrylates other than those described above. The component (A-3) is particularly preferably a polyfunctional (meth)acrylate represented by the following formula (I):

[0136] <Polyfunctional (meth)acrylate represented by the following formula (I)>

[0137]

[0138] In formula (I), Q １０ is a linear or branched alkylene group having 1 to 3 carbon atoms. １０ is preferably a linear alkylene group having 1 to 3 carbon atoms, and particularly preferably a methylene group.

[0139] Q １１ is a linear or branched alkylene group having 1 to 10 carbon atoms. １１ is preferably a linear alkylene group having 1 to 10 carbon atoms, more preferably a linear alkylene group having 2 to 6 carbon atoms, and particularly preferably a linear alkylene group having 2 to 4 carbon atoms.

[0140] Q １２ is a hydrogen atom or a methyl group. １２ is preferably a methyl group.

[0141] Q １３ is a trivalent to hexavalent organic group having 1 to 10 carbon atoms. １３ Examples of the organic group represented by the formula Q include a group derived from a polyol, a trivalent to hexavalent hydrocarbon group, and an organic group containing a trivalent to hexavalent urethane bond. １３ is preferably a group derived from a polyol or a trivalent to hexavalent hydrocarbon group, and is preferably a group derived from glycerin, a group derived from trimethylolpropane, a group derived from pentaerythritol, a group derived from ditrimethylolpropane, or a group derived from dipentaerythritol.

[0142] a1 is 0 or 1.

[0143] b1 is a number of 0 or more and 15 or less. If it is desired to further increase the hardness of the resulting cured body, b1 is preferably a number of 0 or more and 6 or less, more preferably a number of 0 or more and 4 or less, even more preferably a number of 0 or more and 2 or less, and particularly preferably 0.

[0144] Furthermore, when it is desired to improve the performance of the functional dye in the resulting cured body, b1 is preferably a number of 5 or more and 15 or less, more preferably a number of 5 or more and 13 or less, even more preferably a number of 6 or more and 12 or less, and particularly preferably a number of 6 or more and 11 or less.

[0145] c1 is 3 or more and 6 or less.

[0146] The polyfunctional (meth)acrylate represented by the following formula (I) more preferably contains a tri- or tetrafunctional (meth)acrylate represented by the following formula (II).

[0147]

[0148] In formula (II), Q ２０ , Q ２１ , Q ２２ , and Q ２３ are each independently an alkylene group having 1 to 3 carbon atoms. ２０ , Q ２１ , Q ２２ , and Q ２３ is preferably a methylene group. a4, a5, a6, and a7 each independently represent an integer of 0 or 1.

[0149] Q ２４ , Q ２５ , and Q ２６ are each independently a monovalent group represented by the following formula (III):

[0150]

[0151] In formula (III), Q １１ , Q １２ , b1 have the same meanings as in formula (I).

[0152] Q ２４ , Q ２５ , and Q ２６ may have different structures from each other or may have the same structure. ２４ , Q ２５ , and Q ２６ Preferably, the structures of the two compounds are the same.

[0153] Q ２７ Q is a hydrogen atom, a linear or branched alkyl group having from 1 to 5 carbon atoms, a linear or branched alkoxy group having from 1 to 5 carbon atoms, or a monovalent group represented by formula (III). ２７ is preferably a hydrogen atom, a linear alkyl group having 1 to 3 carbon atoms, or a monovalent group represented by formula (III).

[0154] Specific examples of the polyfunctional (meth)acrylate represented by the above formula (I) include glycerin trimethacrylate, glycerin triacrylate, glycerin dimethacrylate acrylate, trimethylolpropane trimethacrylate, trimethylolpropane triacrylate, tetramethylolmethane trimethacrylate, tetramethylolmethane triacrylate, tetramethylolmethane tetramethacrylate, tetramethylolmethane tetraacrylate, trimethylolpropane triethylene glycol trimethacrylate, trimethylolpropane triethylene glycol triacrylate, ditrimethylolpropane tetramethacrylate, ditrimethylolpropane tetraacrylate, dipentaerythritol hexaacrylate, dipentaerythritol pentaacrylate, dipentaerythritol hexamethacrylate, dipentaerythritol pentamethacrylate, ethoxylated glycerin trimethacrylate, Examples of the acrylate include propoxylated glycerin trimethacrylate, butoxylated glycerin trimethacrylate, ethoxylated glycerin triacrylate, propoxylated glycerin triacrylate, butoxylated glycerin triacrylate, ethoxylated trimethylolpropane trimethacrylate, propoxylated trimethylolpropane trimethacrylate, butoxylated trimethylolpropane trimethacrylate, ethoxylated trimethylolpropane triacrylate, propoxylated trimethylolpropane triacrylate, butoxylated trimethylolpropane triacrylate, ethoxylated pentaerythritol tetramethacrylate, propoxylated pentaerythritol tetramethacrylate, butoxylated pentaerythritol tetramethacrylate, ethoxylated pentaerythritol tetraacrylate, propoxylated pentaerythritol tetraacrylate, and butoxylated pentaerythritol tetraacrylate.

[0155] <Polyfunctional (meth)acrylate having a urethane bond> The polyfunctional (meth)acrylate having a urethane bond is obtained by reacting a polyisocyanate compound having three or more isocyanate groups in the molecule with a polyol compound having two or more hydroxyl groups in the molecule and a hydroxyl group-containing (meth)acrylate, and is a polyfunctional (meth)acrylate with a structure different from that of the first radically polymerizable monomer of the present invention. The polyfunctional (meth)acrylate having a urethane bond is preferably a polyfunctional (meth)acrylate having a urethane bond with four or more (meth)acryloyl groups in the molecule. Commercially available products include U-4HA (molecular weight 596, number of functional groups 4), U-6HA (molecular weight 1,019, number of functional groups 6), U-6LPA (molecular weight 818, number of functional groups 6), and U-15HA (molecular weight 2,300, number of functional groups 15), all manufactured by Shin-Nakamura Chemical Co., Ltd.

[0156] <Polyfunctional (meth)acrylates other than those described above> Examples of polyfunctional (meth)acrylates other than the polyfunctional (meth)acrylates represented by formula (I) and the polyfunctional (meth)acrylates having a urethane bond include compounds in which the terminals of polyester compounds are modified with (meth)acryloyl groups. As such polyester (meth)acrylate compounds, various polyester (meth)acrylate compounds having different molecular weights of raw polyester compounds and different amounts of modification with (meth)acryloyl groups are commercially available, and these can be used. Specific examples include tetrafunctional polyester oligomers (molecular weight 2,500 to 3,500, Daicel-UCB, EB80, etc.), hexafunctional polyester oligomers (molecular weight 6,000 to 8,000, Daicel-UCB, EB450, etc.), hexafunctional polyester oligomers (molecular weight 45,000 to 55,000, Daicel-UCB, EB1830, etc.), and tetrafunctional polyester oligomers (particularly GX8488B, molecular weight 10,000, Dai-ichi Kogyo Seiyaku Co., Ltd., etc.).

[0157] In the curable composition according to the embodiment, a high proportion of the third radically polymerizable monomer tends to increase the hardness of the cured product. This proportion may be 5% by mass or more, preferably 10% by mass or more, more preferably 15% by mass or more, even more preferably 20% by mass or more, and particularly preferably 25% by mass or more. On the other hand, if this proportion is excessively high, the performance of the functional dye tends to decrease. This proportion may be 95% by mass or less, preferably 80% by mass or less, more preferably 70% by mass or less, and even more preferably 60% by mass or less.

[0158] <Component (A-4): Other radically polymerizable monomers having a (meth)acryloyl group> Examples of other radically polymerizable monomers having a (meth)acryloyl group include radically polymerizable monomers that have a (meth)acryloyl group in their molecular structure and do not fall under (A-1), (A-2), or (A-3). Such radically polymerizable monomers are not particularly limited, and known monomers can be used, and may also include monofunctional (meth)acrylates having only one (meth)acryloyl group.

[0159] The monofunctional (meth)acrylate may be a monofunctional (meth)acrylate represented by the following formula (7).

[0160]

[0161] R in formula (7) ２１ is a hydrogen atom, a methyldimethoxysilyl group, a trimethoxysilyl group, a glycidyl group, a pentamethylpiperidino group, or a 2,2,6,6-tetramethylpiperidino group. ２２ is a hydrogen atom or a methyl group. o is an integer of 0 to 10. p is an integer of 0 to 20.

[0162] R ２１ is preferably a methyldimethoxysilyl group, a trimethoxysilyl group, or a glycidyl group. When a monofunctional acrylate having such a functional group is contained, the adhesion between the cured product and the substrate tends to be improved.

[0163] Specific examples of the monofunctional (meth)acrylate represented by the above formula (7) 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, and 2,2,6,6-tetramethyl-4-piperidyl methacrylate.

[0164] <Other radical polymerizable monomers> The curable composition according to the embodiment may further contain other radical polymerizable monomers. There are no particular limitations on the radical polymerizable monomers, and any known monomers can be used as long as they are polymerizable with the first radical polymerizable monomer. For example, radical polymerizable polyrotaxanes, radical polymerizable silsesquioxane compounds, allyl compounds, and vinyl compounds are preferably used.

[0165] <Radically Polymerizable Polyrotaxane> Polyrotaxane has a composite molecular structure consisting of an axis molecule and multiple cyclic molecules that encapsulate the axis molecule. Bulky terminal groups are formed at both ends of the axis molecule, preventing the cyclic molecules from detaching from the axis molecule. Radical-polymerizable polyrotaxane is a polyrotaxane in which radically polymerizable groups are introduced into the side chains of the cyclic molecules. The radically polymerizable groups are introduced, for example, by modifying 1 mol % or more but less than 100 mol % of the hydroxyl groups of the cyclic molecules with radically polymerizable groups. The modification ratio can be calculated by (number of moles of polymerizable groups introduced) / (number of moles of total OH groups in the side chains) × 100. From the viewpoints of adhesion and the mechanical strength and functionality of the resulting cured product, the modification ratio is preferably 10 mol % or more but less than 95 mol %.

[0166] If the weight-average molecular weight of the axial molecule is too large, the compatibility with other polymerizable monomers, etc. tends to decrease, while if it is too small, the mobility of the cyclic molecule tends to decrease. The weight-average molecular weight of the axial molecule is preferably in the range of 1,000 to 10,0000, more preferably in the range of 5,000 to 80,000, and most preferably in the range of 8,000 to 50,000.

[0167] The cyclic molecule is preferably a cyclodextrin ring, a crown ether ring, a benzocrown ring, a dibenzocrown ring, or a dicyclohexanocrown ring, with a cyclodextrin ring and a crown ether ring being particularly preferred, and a cyclodextrin ring being most preferred. Furthermore, among cyclodextrin rings, there are α-cyclodextrin rings (inner ring diameter 0.45 to 0.6 nm), β-cyclodextrin rings (inner ring diameter 0.6 to 0.8 nm), and γ-cyclodextrin rings (inner ring diameter 0.8 to 0.95 nm), with α-cyclodextrin rings and β-cyclodextrin rings being preferred, and an α-cyclodextrin ring being most preferred. When the inclusion number when all cyclic molecules are introduced into the axial molecule is taken as 1, the inclusion number of the cyclic molecules is preferably in the range of 0.001 to 0.6, more preferably in the range of 0.002 to 0.5, and most preferably in the range of 0.003 to 0.4.

[0168] As the radical polymerizable group, a (meth)acryloyl group is preferred in consideration of reactivity with other polymerizable monomers, etc. The number of radical polymerizable groups is not particularly limited, and is preferably 0 to 5,000 per molecule.

[0169] The above-described polyrotaxane having a (meth)acryloyl group is described, for example, in WO 2018 / 030257.

[0170] <Silsesquioxane Radically Polymerizable Compound> Silsesquioxane radically polymerizable compounds have various molecular structures such as cage-like, ladder-like, and random structures, and have a radically polymerizable group such as a (meth)acrylic group.

[0171] An example of such a silsesquioxane polymerizable compound is one represented by the following formula (8).

[0172]

[0173] In formula (8), q is the degree of polymerization and is an integer of 3 to 100.

[0174] Multiple R ２３ may be the same or different and are a radical polymerizable group, an organic group containing a radical polymerizable group, a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, or a phenyl group, and at least one R ２３ is a radically polymerizable group or an organic group containing a radically polymerizable group.

[0175] Here, R ２３ Examples of the radically polymerizable group represented by the formula (I) or an organic group containing a radically polymerizable group include a (meth)acrylic group; an organic group having a (meth)acrylic group such as a (meth)acryloyloxypropyl group or a (3-(meth)acryloyloxypropyl)dimethylsiloxy group; an allyl group; an organic group having an allyl group such as an allylpropyl group or an allylpropyldimethylsiloxy group; a vinyl group; and an organic group having a vinyl group such as a vinylpropyl group or a vinyldimethylsiloxy group.

[0176] <Allyl-Based Polymerizable Compound> Examples of allyl-based polymerizable compounds having an allyl group include the following: diethylene glycol bisallyl carbonate, methoxypolyethylene glycol allyl ether, methoxypolyethylene glycol-polypropylene glycol allyl ether, butoxypolyethylene glycol-polypropylene glycol allyl ether, phenoxypolyethylene glycol allyl ether, vinyloxypolyethylene glycol allyl ether, styryloxypolyethylene glycol allyl ether, and methoxypolyethylene thioglycol allyl thioether.

[0177] <Vinyl-Based Polymerizable Compounds> Examples of vinyl-based polymerizable compounds 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 persulfide, dimethyldivinylsilane, 1,2,4-trivinylcyclohexane, methyltrivinylsilane, α-methylstyrene, and α-methylstyrene dimer.

[0178] <Bundling ratio in the curable composition> In the curable composition according to the embodiment, when the ratio of the first radical polymerizable monomer is high, the appearance and hardness of the cured product tend to be improved. This ratio may be 5% by mass or more, preferably 10% by mass or more, more preferably 15% by mass or more, even more preferably 20% by mass or more, and particularly preferably 25% by mass or more. On the other hand, if this ratio is excessively high, the performance of the functional dye tends to be reduced. This ratio may be 95% by mass or less, preferably 80% by mass or less, and more preferably 60% by mass or less.

[0179] In the curable composition according to the embodiment, the proportion of the second radically polymerizable monomer is, for example, 10% by mass or more and 90% by mass or less. When this proportion is high, the performance of the functional dye in the cured product tends to be enhanced. This proportion may be 35% by mass or more, preferably 40% by mass or more, more preferably 45% by mass or more, even more preferably 50% by mass or more, and particularly preferably 60% by mass or more. On the other hand, when this proportion is excessively high, the hardness of the cured product tends to decrease. This proportion is preferably 85% by mass or less, more preferably 80% by mass or less.

[0180] In the curable composition according to the embodiment, the content of di(meth)acrylates other than the second radical polymerizable monomer is preferably 50% by mass or less. That is, if the content of di(meth)acrylates such as polyalkylene carbonate polyol di(meth)acrylates is high, the performance of the functional dye in the cured product may be reduced. The content of di(meth)acrylates other than the second radical polymerizable monomer is more preferably 30% by mass or less, and even more preferably 20% by mass or less. The lower limit of this content is, for example, 0% by mass, and, in another example, 5% by mass or more.

[0181] In the curable composition according to the embodiment, it is preferable to further contain a third radical polymerizable monomer in order to enhance the curability and hardness of the cured body. The proportion of the third radical polymerizable monomer in the curable composition according to the embodiment is preferably 5% by mass or more, more preferably 7% by mass or more, even more preferably 10% by mass or more, and particularly preferably 15% by mass or more. On the other hand, if this proportion is excessively high, the performance of the functional dye in the cured body tends to decrease. This proportion is preferably 95% by mass or less, more preferably 85% by mass or less, and even more preferably 75% by mass or less.

[0182] In the curable composition according to the embodiment, it is preferable to contain a monofunctional (meth)acrylate in order to reduce the viscosity of the curable composition and improve adhesion. The proportion of the monofunctional (meth)acrylate in the curable composition according to the embodiment is preferably 1% by mass or more, more preferably 3% by mass or more, and even more preferably 5% by mass or more. On the other hand, if this proportion is excessively high, the performance of the functional dye in the cured product tends to decrease. This proportion is preferably 20% by mass or less, more preferably 10% by mass or less, and even more preferably 8% by mass or less.

[0183] In the curable composition containing the first to third radical polymerizable monomers, the content of the first radical polymerizable monomer may be 5% by mass or more and 80% by mass or less, the content of the second radical polymerizable monomer may be 10% by mass or more and 80% by mass or less, the content of the third radical polymerizable monomer may be 5% by mass or more and 75% by mass or less, and the remainder may be the proportion of functional dyes and additives.

[0184] In the curable composition according to the embodiment, the proportion of methacrylate is preferably 30% by mass or more. A higher proportion tends to result in a cured product with high functionality of the functional dye. This proportion is preferably 60% by mass or more. The upper limit of this proportion is, for example, 100% by mass, and, for another example, 90% by mass or less.

[0185] The ratio M2 / M1 of the mass M1 of the first radical polymerizable monomer to the mass M2 of the second radical polymerizable monomer is preferably 0.1 or more and 20 or less. When a curable composition having a ratio M2 / M1 within this range is used, the performance and hardness of the functional dye in the cured product tend to be further improved. The ratio M2 / M1 is more preferably 0.5 or more and 10 or less, and even more preferably 1 or more and 5 or less.

[0186] The ratio M1 / M3 of the mass M1 of the first radical polymerizable monomer to the mass M3 of the third radical polymerizable monomer is preferably 0.1 or more and 20 or less. When a curable composition having a ratio M1 / M3 within this range is used, the performance and hardness of the functional dye in the cured product tend 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.

[0187] The ratio M2 / M3 of the mass M2 of the second radical polymerizable monomer to the mass M3 of the third radical polymerizable monomer is preferably 0.1 or more and 20 or less. When a curable composition having a ratio M2 / M3 within this range is used, the performance and hardness of the functional dye in the cured product tend to be further improved. The ratio M2 / M3 is more preferably 0.5 or more and 10 or less, and even more preferably 1 or more and 5 or less.

[0188] <(B) Functional Dye> Functional dyes include compounds capable of selectively absorbing visible light, as well as compounds that develop, lose, or change color in response to energy such as light, heat, an electric field, or pressure. Such functional dyes can exhibit specific functions by undergoing a structural change under specific conditions. The functional dye includes, for example, at least one selected from the group consisting of a photochromic compound, an ultraviolet absorber, a blue light absorber, an infrared absorber, and an electrochromic compound. The content of the functional dye in the curable composition is, for example, 0.01% by mass or more and 10% by mass or less. The content of the functional dye is preferably 0.1% by mass or more and 8% by mass or less, and more preferably 1% by mass or more and 5% by mass or less.

[0189] <Photochromic Compound> The photochromic compound is used in an amount that will provide the desired photochromic properties. The photochromic compound is preferably used in an amount of 0.01 to 10 parts by mass per 100 parts by mass of component (A).

[0190] It is preferable to adjust the blending amount optimally depending on the intended use. Specifically, when the curable composition containing a photochromic compound is formed into a thin film such as a coating, for example, a thin film of about 100 μm (a polymer film formed by polymerizing the curable composition containing a photochromic compound), it is preferable to blend 0.1 to 10 parts by mass of the photochromic compound with 100 parts by mass of the polymerizable compound to adjust the color tone.

[0191] Furthermore, when a thick cured product (a polymer molded product obtained by polymerizing a curable composition containing a photochromic compound) is to be produced, for example, in the case of a cured product having a thickness of 1 mm or more, it is preferable to adjust the color tone by blending 0.01 to 1 part by mass of a photochromic compound with 100 parts by mass of the thick cured product or with 100 parts by mass of the polymerizable compound of component (A) that will give the thick cured product.

[0192] The photochromic compound is not particularly limited and any known compound can be used. These compounds can be used alone or in combination of two or more. While both inorganic photochromic compounds such as metal oxides and organic photochromic compounds based on organic molecules can be used as such photochromic compounds, organic photochromic compounds are preferred, and T-type organic photochromic compounds are particularly preferred. Representative examples include chromene compounds, fulgide compounds, fulgimide compounds, and spirooxazine compounds. Among these photochromic compounds, chromene compounds and spirooxazine compounds are preferred. Chromene compounds are particularly preferred. Examples of chromene compounds include compounds having a 1-benzopyran skeleton, spiropyran compounds containing a spiropyran skeleton, and naphthopyran compounds having a naphthopyran skeleton.

[0193] The naphthopyran compound preferably contains at least one of the compounds represented by the following formula (9), (10), (11), (12), (13), and (14):

[0194]

[0195] In formula (9), ring AA is a substituted or unsubstituted aromatic hydrocarbon ring, a substituted or unsubstituted aromatic heterocycle, or a substituted or unsubstituted fused polycycle in which an aromatic ring or an aromatic heterocycle is fused to the ring. Ring AA may not be present. Ring AB is a substituted or unsubstituted aromatic hydrocarbon ring, a substituted or unsubstituted aromatic heterocycle, or a substituted or unsubstituted fused polycycle in which an aromatic ring or an aromatic heterocycle is fused to the ring.

[0196] 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.

[0197] The substituent 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 which may have a substituent, an aralkoxy group which may have a substituent, an aryloxy group which may have a substituent, an alkylthio group, an arylthio group which may have a substituent, an aryl group which may have a substituent, an amino group, a substituted amino group, or a heterocyclic group which may have a substituent, and is preferably at least one selected from the group consisting of a haloalkylthio group, a cycloalkylthio group which may have a substituent, an oligomer group, and a group represented by the following formula (15):

[0198] -Q １ - (P １ Q ２ ) ａａ -P ２ Q ３ (15) In equation (15), Q １ is an alkylene group which may contain a halogen atom as a substituent. ２ is an alkylene group which may contain a halogen atom as a substituent. ３ is an alkyl group which may contain a halogen atom as a substituent. １ , and P ２ are each independently O, S, or NR ７００ , P.R. ７０１ , or P(=O). ７００ R is a hydrogen atom, an alkyl group which may have a substituent, a cycloalkyl group which may have a substituent, an aryl group which may have a substituent, or a heteroaryl group which may have a substituent. ７０１ represents a hydrogen atom, an alkyl group which may have a substituent, a cycloalkyl group which may have a substituent, an aryl group which may have a substituent, or a heteroaryl group which may have a substituent. aa is 0 or 1 to 10.

[0199] In equation (9), M is CR ２６ R ２７ , SiR ２６ R ２７ , GeR ２６ R２７ , or NR ２６ It is. 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.

[0200] The substituent 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 which may have a substituent, an aralkoxy group which may have a substituent, an aryloxy group which may have a substituent, an alkylthio group, an arylthio group which may have a substituent, an aryl group which may have a substituent, an amino group, a substituted amino group, a heterocyclic group which may have a substituent, and a group represented by the above formula (15). ２６ and R ２７ When two of these are taken together to form a ring structure, it is preferable that they form an aliphatic ring having 3 to 20 ring carbon atoms, a condensed polycycle in which an aromatic ring or an aromatic heterocycle is condensed to an aliphatic ring, a heterocycle having 3 to 20 ring atoms, or a condensed polycycle in which an aromatic ring or an aromatic heterocycle is condensed to a heterocycle.

[0201]

[0202] 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 substituents may be the same as those described in formula (9). mm is 1 to 10.

[0203]

[0204] In formula (11), R １００３ , R １００４ and R １００５are each independently a hydrogen atom or a substituent, and two or more substituents may be bonded to form a ring structure. The substituents may be the same as those described in formula (9). nn is 1 to 10.

[0205]

[0206] In formula (12), R １００６ , R １００７ and R １００８ are each independently a hydrogen atom or a substituent, and two or more substituents may be bonded to form a ring structure. The substituents may be the same as those described in formula (9). oo is 1 to 12.

[0207]

[0208] In formula (13), R １００９ , R １０１０ and R １０１１ are each independently a hydrogen atom or a substituent, and two or more substituents may be bonded to form a ring structure. The substituents may be the same as those described in formula (9). pp is 1 to 12.

[0209]

[0210] In formula (14), R １０１２ , R １０１３ and R １０１４ are each independently a hydrogen atom or a substituent, and two or more substituents may be bonded to form a ring structure. The substituents may be the same as those described in formula (9). qq is 1 to 12.

[0211] The naphthopyran compound includes an indenonaphthopyran compound having an indenonaphthopyran skeleton, and the indenonaphthopyran compound preferably has an indeno[2,1-f]naphtho[1,2-b]pyran skeleton.

[0212] The indenonaphthopyran compound preferably includes a compound represented by the following formula (16).

[0213]

[0214] In formula (16), R ２４ , R ２５ , R ２６ and R ２７ is the same as above.

[0215] r is an integer of 0 to 4. s is an integer of 0 to 4. When r is 2 to 4, multiple R ２８ may be the same or different. When s is 2 to 4, multiple R ２９ may be the same or different. ２８ If there is a ２８ Together they ２８ and the carbon atom bonded to the adjacent R may form a ring which may contain at least one heteroatom selected from the group consisting of an oxygen atom, a carbon atom, a sulfur atom, and a nitrogen atom, and the ring may further have a substituent. ２９ If there is a ２９ Together they ２９ and the carbon atom bonded to the aryl group may form a ring which may contain at least one heteroatom selected from the group consisting of an oxygen atom, a carbon atom, a sulfur atom, or a nitrogen atom, and the ring may further have a substituent.

[0216] R ２８ , and R ２９are each independently a group represented by formula (15), a hydroxyl group, an alkyl group, a haloalkyl group, a cycloalkyl group which may have a substituent, an alkoxy group, an amino group, a substituted amino group, a heterocyclic group which may have a substituent, a cyano group, a halogen atom, an alkylthio group, an arylthio group which may have a substituent, a nitro group, a formyl group, a hydroxycarbonyl group, an alkylcarbonyl group, an alkoxycarbonyl group, an aralkyl group which may have a substituent, an aralkoxy group which may have a substituent, an aryloxy group which may have a substituent, an aryl group which may have a substituent, a heteroaryl group which may have a substituent, a thiol group, an alkoxyalkylthio group, a haloalkylthio group, or a cycloalkylthio group which may have a substituent, a silyl group which may have a substituent, an oxysilyl group which may have a substituent, a group represented by formula (17) below, or L-R ４００ It is a group represented by:

[0217]

[0218] In formula (17), E is an oxygen atom or NR １０１ and 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 It is. 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.

[0219] L-R ４００ In the group represented by ４００ is a hydrogen atom, an alkyl group, an aryl group, a silyl group having a substituent, a polymerizable group, or a photochromic group. The substituent of the silyl group is an alkyl group, an alkoxyl group, or an aryl group. L is a group represented by the following formula (18):

[0220]

[0221] In formula (18), J is a divalent group, and each J is independently a direct bond, a substituted methylene group, an oxygen atom, a sulfur atom, or NR ３０１ And. 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. ３０２ , R ３０３ and R ３０４ is an alkylene group. hh, jj, kk, and 11 are integers of 0 or 1. ii is an integer from 1 to 200. When ii is 2 or more, the multiple ii units may be the same or different. The dashed line represents R ４００ Represents a bond with.

[0222] <Other Additives> Various known additives can be added to the curable composition as long as the effects are not impaired. Examples of additives include various stabilizers such as release agents, ultraviolet absorbers, infrared absorbers, ultraviolet stabilizers, antioxidants, coloring inhibitors, antistatic agents, fluorescent dyes, dyes, pigments, and fragrances. Solvents and leveling agents can also be added. Thiols such as t-dodecyl mercaptan can be added as polymerization regulators.

[0223] <UV Stabilizer> The use of a mixed UV stabilizer can further improve the durability of the photochromic compound, and therefore is preferable. Examples of suitable UV stabilizers include hindered amine light stabilizers, hindered phenol antioxidants, and sulfur-based antioxidants. The hindered amine light stabilizer is not particularly limited, but bis(1,2,2,6,6-pentamethyl-4-piperidyl) sebacate is preferred, particularly in terms of preventing deterioration of the photochromic compound. Furthermore, hindered amine light stabilizers commercially available from ADEKA Corporation under the trade names Adekastab LA-52, LA-57, LA-62, LA-63, LA-67, LA-77, LA-87, and the like can also be used.

[0224] The hindered phenol antioxidant is preferable in terms of preventing deterioration of the photochromic compound. For example, 2,6-di-t-butyl-4-methyl-phenol, IRGANOX 245 (ethylene bis(oxyethylene)bis[3,5-tert-butyl-4-hydroxy-m-toluyl]propionate) manufactured by BASF Japan Ltd., IRGANOX 1076 (octadecyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate) manufactured by BASF Japan Ltd. IRGANOX 1010: pentaerythritol tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate] manufactured by BASF Japan Ltd., and other examples include IRGANOX 1035, 1075, 1098, 1135, 1141, 1222, 1330, 1425, 1520, 259, 3114, 3790, 5057, and 565 manufactured by BASF Japan Ltd.

[0225] The amount of such an ultraviolet stabilizer used is not particularly limited as long as the effect is not impaired, but is usually in the range of 0.001 to 10 parts by mass, particularly 0.01 to 1 part by mass, per 100 parts by mass of the curable composition.

[0226] <Polymerization Initiator> Polymerization initiators include thermal polymerization initiators and photopolymerization initiators, and specific examples thereof are as follows.

[0227] Examples of the thermal polymerization initiator include diacyl peroxides; benzoyl peroxide, p-chlorobenzoyl peroxide, decanoyl peroxide, lauroyl peroxide, acetyl peroxide; peroxy esters; t-butylperoxy-2-ethylhexanate, t-butylperoxyneodecanate, cumylperoxyneodecanate, t-butylperoxybenzoate; percarbonates; diisopropyl peroxydicarbonate, di-sec-butyl peroxydicarbonate; azo compounds; azobisisobutyronitrile; and the like.

[0228] Examples of the photopolymerization initiator include acetophenone compounds such as 1-phenyl-2-hydroxy-2-methylpropan-1-one, 1-hydroxycyclohexyl phenyl ketone, and 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropan-1-one; α-dicarbonyl compounds such as 1,2-diphenylethanedione and methylphenylglycoxylate; and acylphosphine oxide compounds such as 2,6-dimethylbenzoyldiphenylphosphine oxide, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, 2,4,6-trimethylbenzoyldiphenylphosphine acid methyl ester, 2,6-dichlorobenzoyldiphenylphosphine oxide and 2,6-dimethoxybenzoyldiphenylphosphine oxide.

[0229] When a photopolymerization initiator is used, a known polymerization curing accelerator such as a tertiary amine may be used in combination.

[0230] <Surfactant> Addition of a surfactant can improve the wettability of the optical substrate and the primer layer and prevent the occurrence of poor appearance. Examples of surfactants include known surfactants such as silicone surfactants having a silicone chain (polyalkylsiloxane unit) as the hydrophobic group and fluorine surfactants having a fluorocarbon chain. When using surfactants, two or more types may be mixed and used. Furthermore, the surfactant may be either polymerizable with component (A) or non-polymerizable.

[0231] Specific examples of silicone surfactants and fluorosurfactants that can be suitably used include L-7001, L-7002, L-7604, FZ-2123, and FZ-2110 manufactured by Dow Toray Co., Ltd.; Megafac F-470, Megafac F-1405, and Megafac F-479 manufactured by DIC Corporation; FLORAD FC-430 manufactured by Sumitomo 3M Limited; TEGORAD 2100 and TEGORAD 2300 manufactured by Evonik Japan Co., Ltd.; and BYK-UV3505 and BYK-UV4505 manufactured by BYK Japan Co., Ltd. Examples of such a resin include K-UV3505, BYK-UV3510, BYK-UV3530, BYK-3550, BYK-3560, BYK-UV3565, BYK-3566, BYK-UV3500, BYK-UV3535, BYK-UV3570, BYK-UV3575, BYK-UV3576, and KR-513, X-22-2445, X-40-9296, X-22-164, X-22-164A, X-22-164B, X-22-164C, and X-22-164E manufactured by Shin-Etsu Chemical Co., Ltd.

[0232] <Ultraviolet Absorber> As the ultraviolet absorber, known ultraviolet absorbers such as benzophenone-based compounds, benzotriazole-based compounds, cyanoacrylate-based compounds, triazine-based compounds, benzoate-based compounds, cinnamate ester-based compounds, and oxanilide-based compounds can be used, with cyanoacrylate-based compounds, benzophenone-based compounds, benzotriazole-based compounds, and cinnamate ester-based compounds being particularly preferred. The ultraviolet stabilizer is preferably used in an amount of 0.001 to 5 parts by mass relative to 100 parts by mass of the curable composition containing the photochromic compound and the polymerizable compound.

[0233] <Cured Product> A cured product is obtained by curing a curable composition. The curable composition is cured by inducing a radical polymerization reaction by irradiation with active energy rays such as ultraviolet rays, α-rays, β-rays, γ-rays, or LED, heat, or a combination of both. That is, an appropriate curing method may be adopted depending on the type of polymerizable monomer and polymerization curing accelerator used and the form of the cured product to be formed. When forming a laminate by the coating method described below, it is preferable to adopt photopolymerization because a uniform film thickness can be obtained.

[0234] When thermally polymerizing a curable composition containing a polymerizable compound, the thermal polymerization temperature affects the properties of the resulting cured product. While temperature conditions cannot be generally defined because they are influenced by the type and amount of thermal polymerization initiator and the type of polymerizable compound, a generally preferred method is to initiate polymerization at a relatively low temperature and slowly increase the temperature. Like temperature, polymerization time also varies depending on various factors, so it is best to determine the optimal time based on these conditions in advance. Generally, however, it is preferable to select conditions so that polymerization is complete within 2 to 48 hours. When obtaining a photochromic laminate sheet, polymerization is preferably carried out at a temperature at which the reaction between polymerizable functional groups proceeds, and the optimal temperature and time are determined to achieve the desired molecular weight.

[0235] Furthermore, when photopolymerizing a curable composition, among the polymerization conditions, UV intensity in particular affects the properties of the resulting photochromic cured product. The illuminance conditions cannot be generally limited because they are affected by the type and amount of the photopolymerization initiator and the type of polymerizable monomer, but generally range from 50 to 500 mW / cm at a wavelength of 365 nm. ２ It is preferable to select the conditions so that the UV light is irradiated for 0.5 to 5 minutes.

[0236] The biomass plastic degree of the cured body is, for example, 10% by mass or more. The biomass plastic degree can be calculated by a method in accordance with ISO standard 16620-3. The biomass plastic degree of the cured body is preferably 25% by mass or more, more preferably 30% by mass or more, and even more preferably 40% by mass or more. There is no particular upper limit to this biomass plastic degree, but in one example it is 100% by mass or less, and in another example it is 80% by mass or less.

[0237] <Laminate> According to another embodiment, a laminate is provided. The laminate includes an optical substrate and a cured product according to the embodiment located on the surface of the optical substrate. The optical substrate includes a resin such as a diallyl carbonate resin, a urethane resin, or a thiourethane resin. The optical substrate may be a lens substrate. A primer layer may be provided between the laminate and the cured product. The primer layer includes a urethane resin.

[0238] The biomass plastic content of the optical substrate is preferably 25% by mass or more. The biomass plastic content can be calculated by a method in accordance with ISO standard 16620-3. The biomass plastic content of the optical substrate is preferably 30% by mass or more, and more preferably 40% by mass or more. There is no particular upper limit to this biomass plastic content, but in one example it is 100% by mass or less, and in another example it is 80% by mass or less.

[0239] Fig. 1 is a cross-sectional view schematically illustrating an example of a laminate according to an embodiment. The laminate 10 shown in Fig. 1 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 includes a cured product according to an embodiment. The optical substrate 11 is a convex meniscus lens having an uneven shape.

[0240] <Optical Articles> The cured product according to the embodiment can be used in a wide range of applications as an optical article, including, for example, various memory materials such as various memory materials replacing silver halide photosensitive materials, copying materials, printing photosensitive materials, memory materials for cathode ray tubes, photosensitive materials for lasers, and photosensitive materials for holography, as well as lenses. Lenses are suitable for eyeglasses. Photochromic cured products containing a photochromic compound can also be used as photochromic lens materials, optical filter materials, display materials, actinometers, decorative materials, and the like.

[0241] The cured product according to the embodiment is particularly suitable for use in photochromic lenses. Photochromic lenses are suitable as lenses for spectacles such as sunglasses. Any known method can be used to manufacture photochromic lenses, as long as it can provide uniform photochromic performance.

[0242] When photochromic properties are expressed by the kneading method, the above-mentioned curable composition is injected between glass molds held by elastomer gaskets or spacers, and depending on the types of polymerizable compound and polymerization curing accelerator, a photochromic cured product molded into the shape of an optical material such as a lens can be obtained by casting polymerization using heating in an air oven or irradiation with active energy rays such as ultraviolet rays.

[0243] When photochromic properties are expressed by a lamination method, a coating liquid is prepared by dissolving a curable composition in an appropriate organic solvent, and the coating liquid is applied to the surface of an optical substrate such as a lens substrate by spin coating, dipping, or the like, and then dried to remove the organic solvent. Subsequently, polymerization and curing are carried out by UV irradiation or heating in an inert gas such as nitrogen, thereby forming a photochromic layer made of a photochromic cured product on the surface of the optical substrate (coating method).

[0244] Alternatively, a photochromic layer made of a photochromic cured product can be formed on the surface of an optical substrate by cast polymerization using an inner mold in which an optical substrate such as a lens substrate is placed facing a glass mold so that a predetermined gap is formed, a curable composition is injected into this gap, and polymerization and curing are carried out in this state by UV irradiation, heating, etc. (cast polymerization method).

[0245] When a photochromic layer is formed on the surface of an optical substrate by the above-mentioned lamination methods (coating method and cast polymerization method), the adhesion between the photochromic layer and the optical substrate can be improved by previously subjecting the surface of the optical substrate to a chemical treatment using an alkaline solution, an acid solution, etc., or a physical treatment using corona discharge, plasma discharge, polishing, etc. Of course, it is also possible to provide a transparent adhesive resin layer on the surface of the optical substrate.

[0246] The cured product formed from the curable composition may be subjected to post-processing depending on its intended use. Examples of post-processing include dyeing with a dye such as a disperse dye, laminating a protective layer containing a urethane resin or an epoxy resin, forming a hard coat film using a hard coat agent mainly composed of a silane coupling agent or a sol of silicon, zirconium, antimony, aluminum, tin, tungsten, or the like, and forming a SiO ２ , TiO ２ , ZrO ２ Examples of such methods include forming a thin film by vapor deposition of a metal oxide such as the above, anti-reflection treatment using a thin film by coating an organic polymer, and anti-static treatment.

[0247] EXAMPLES 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 notation of each component and the evaluation methods are as follows.

[0248] <Components> Component (A) Component (A-1) TMM57-UMA: a mixture of methacrylate of the following formula and pentaerythritol tetraacrylate (the mixing ratio of methacrylate of the following formula:pentaerythritol tetraacrylate was 57:43.)

[0249]

[0250] GDM-UMA: a mixture of isomers of methacrylates of the following formula:

[0251]

[0252] (Synthesis of GDM-UMA) 500 mL of toluene was added to 22.8 g (100.0 mmol) of glycerin dimethacrylate and 11.4 mg of 4-methoxyphenol, and 0.15 g of dibutyltin dilaurate was added and the mixture was heated to 60°C. 15.8 g (102.0 mmol) of 2-methacryloyloxyethyl isocyanate was slowly added dropwise thereto. After the dropwise addition, the mixture was heated to 80°C and continued to be heated until the raw materials were consumed. After the reaction was completed, the mixture was cooled to room temperature, and 500 mL of water was added and the mixture was separated. Celite was added to the obtained organic layer, and the mixture was stirred and then filtered. 39 g of Wakogel C300 was added to the obtained filtrate and the mixture was stirred for 30 minutes. After stirring for 30 minutes, the mixture was filtered, and the obtained organic layer was concentrated to obtain GDM-UMA. The proton nuclear magnetic resonance spectrum of the obtained concentrate was measured, and it showed a 9H peak due to a methyl group at around δ 1.0 to 2.0 ppm, a 9H peak due to a 1,2,3-trioxypropyl group and an ethyloxy group at around δ 3.0 to 4.5 ppm, and a 6H peak due to a methacryl group proton at around δ 5.5 to 6.5 ppm.

[0253] GDM-UA: a mixture of isomers of the following formula

[0254]

[0255] (Synthesis of GDM-UA) GDM-UA was synthesized in the same manner as in the synthesis of GDM-UMA, except that 2-acryloyloxyethyl isocyanate was used instead of 2-methacryloyloxyethyl isocyanate.

[0256] When the proton nuclear magnetic resonance spectrum was measured, it showed a 6H peak due to a methyl group at around δ 1.0 to 2.0 ppm, a 9H peak due to a 1,2,3-trioxypropyl group and an ethyloxy group at around δ 3.0 to 4.5 ppm, and a 7H peak due to a methacryl group proton at around δ 5.5 to 6.5 ppm.

[0257] GDM-UEOMA: a mixture of isomers of methacrylate of the following formula:

[0258]

[0259] (Synthesis of GDM-UEOMA) GDM-UEOMA was synthesized by the same reaction as for GDM-UMA, except that 2-(2-methacryloyloxyethyl)ethyl isocyanate was used instead of 2-methacryloyloxyethyl isocyanate. When the proton nuclear magnetic resonance spectrum was measured, it showed a 9H peak due to the methyl group at around δ 1.0 to 2.0 ppm, a 13H peak due to the 1,2,3-trioxypropyl group and ethyloxy group at around δ 3.0 to 4.5 ppm, and a 6H peak due to the proton of the methacryl group at around δ 5.5 to 6.5 ppm.

[0260] TMPTUMA: methacrylate of the following formula

[0261]

[0262] TMPTUMA of the above formula was synthesized according to the method described in WO 2022 / 209922.

[0263] GT-19EO-UMA: methacrylate of the following formula

[0264]

[0265] (Synthesis of GT-19EO-UMA) The reaction for synthesizing GT-19EO-UMA was carried out in the same manner as for GDM-UMA, except that ethoxylated glycerol was used instead of glycerin dimethacrylate. After the reaction, toluene was concentrated under reduced pressure, and 2000 mL of chloroform and 500 mL of water were added, followed by separation. Celite was added to the obtained organic layer, and the mixture was stirred and then filtered. GT-19EO-UMA was obtained by concentrating the obtained organic layer.

[0266] The proton nuclear magnetic resonance spectrum of the obtained concentrate was measured, and it showed a 9H peak due to a methyl group at around δ 1.0 to 2.0 ppm, a peak of about 91H due to a 1,2,3-trioxypropyl group and an ethyloxy group at around δ 3.0 to 4.5 ppm, and a 6H peak due to a methacryl group proton at around δ 5.5 to 6.5 ppm.

[0267] (A-2) component 14G: polyethylene glycol dimethacrylate (number average molecular weight 770) A-PTMG65: polytetramethylene glycol diacrylate (number average molecular weight 775) M-PTMG65: polytetramethylene glycol dimethacrylate (number average molecular weight 803) M-PTMG65Bio: polytetramethylene glycol dimethacrylate using polytetramethylene glycol with a biomass plastic content of 95% by mass (number average molecular weight 803, biomass plastic content 76.8% by mass) M-PTMG100: polytetramethylene glycol dimethacrylate (number average molecular weight 1156) M-PTMG100Bio: polytetramethylene glycol dimethacrylate using polytetramethylene glycol with a biomass plastic content of 95% by mass (number average molecular weight 1171, biomass plastic content 82.5% by mass) M-EGTMG130: dimethacrylate of the following formula

[0268]

[0269] PTG25CD100: Dimethacrylate of the following formula

[0270]

[0271] (Synthesis of PTG25CD100) 330 mL of dehydrated toluene, 1.0 mg of p-methoxyphenol, and 2.86 g of p-toluenesulfonic acid monohydrate were added to 100 g of NT1002 (manufactured by Mitsubishi Chemical Corporation) having a molecular weight of 1000 calculated from the hydroxyl value, and the mixture was stirred. 18.9 g of methacrylic acid was added thereto, and the mixture was reacted for 20 hours under azeotropic conditions. After the reaction was completed, 1000 mL of 5% aqueous sodium bicarbonate was added, and the mixture was separated. Celite was added to the obtained organic layer, and the mixture was stirred and then filtered. 20 g of Wakogel 60N was added to the obtained organic layer, and the mixture was stirred and then filtered. 1 mL of a 0.1 mg / mL p-methoxyphenol toluene solution was added to the obtained organic layer, and the mixture was concentrated to synthesize PTG25CD100.

[0272] Measurement of the proton nuclear magnetic resonance spectrum showed a peak of about 55H due to the tetramethyleneoxy group and methacryl group at around δ1.0 to 2.5 ppm, a peak of about 49H due to the tetramethyleneoxy group at around δ3.0 to 4.5 ppm, and a peak of 4H due to the protons of the acrylic group at around δ5.5 to 6.5 ppm.

[0273] PTG65CD200: Dimethacrylate of the following formula

[0274]

[0275] (Synthesis of PTG65CD200) PTG65CD200 was synthesized in the same manner as in the synthesis of PTG25CD100, except that NT2006 was used instead of NT1002.

[0276] Measurement of the proton nuclear magnetic resonance spectrum showed a peak of about 114H due to the tetramethyleneoxy group and methacryl group at around δ 1.0 to 2.5 ppm, a peak of about 108H due to the tetramethyleneoxy group at around δ 3.0 to 4.5 ppm, and a peak of 4H due to the protons of the acrylic group at around δ 5.5 to 6.5 ppm.

[0277] APC56: Diacrylate of polycarbonated diol obtained by phosgenation of pentamethylene glycol and hexamethylene glycol (number average molecular weight 606)

[0278] Component (A-3) A-TMMT: pentaerythritol tetraacrylate A-TMPT: trimethylolpropane triacrylate TMPT: trimethylolpropane trimethacrylate GT-19EO-MA: ethoxylated glycerin trimethacrylate (number average molecular weight 1110)

[0279] Component (A-4) LA82: 1,2,2,6,6-pentamethyl-4-piperidyl methacrylate TSL: γ-methacryloyloxypropyltrimethoxysilane

[0280] (Other radically polymerizable monomers) RX-1: Polyrotaxane having acryloyl groups According to the method described in WO 2018 / 030257, a polyrotaxane having acryloyl groups satisfying the following properties was synthesized. Weight average molecular weight Mw (GPC) of polyrotaxane having acryloyl groups (RX-1): 180,000. Proportion of acryloyl group modification in side chains: 80 mol%. Proportion of OH groups remaining in side chains: 20 mol%. Axial molecule: Linear polyethylene glycol (PEG) with a molecular weight of 11,000. Inclusion ring: α-cyclodextrin (α-CD) introduction ratio: 0.25. Axial molecule end: Capped with adamantane. Side chain introduced into inclusion ring: Side chain (average) molecular weight: approximately 500. Number of acryloyl groups per molecule: approximately 90.

[0281] The weight-average molecular weight Mw of polyrotaxane (RX-1) was measured by gel permeation chromatography (GPC). A liquid chromatograph (manufactured by Nihon Waters K.K.) was used. Two TSKgel Super HM-M columns (exclusion limit: 4,000,000, manufactured by Tosoh Corporation) were used in series.

[0282] Further, tetrahydrofuran was used as the developing liquid, and the measurement was carried out under conditions of a flow rate of 0.6 ml / min and a temperature of 40° C. When the weight average molecular weight was determined by comparative conversion using polystyrene as a standard sample, the weight average molecular weight of RX-1 was found to be 180,000.

[0283] SO-1: Silsesquioxane having a methacryloyl group and the following properties: Number of methacrylate groups per molecule: 20; Weight average molecular weight: 4,800. SO-1 was synthesized by the following method: First, 248 ml of ethanol and 54 g of water (3.0 mol) were added to 248 g (1.0 mol) of 3-trimethoxysilylpropyl methacrylate, and 0.20 g (0.005 mol) of sodium hydroxide was added as a catalyst, followed by a reaction at 30°C for 3 hours. １After confirmation by H-NMR, the mixture was neutralized with dilute hydrochloric acid, and 174 ml of toluene, 174 ml of heptane, and 174 g of water were added, and the aqueous layer was removed. Thereafter, the organic layer was washed with water until the aqueous layer became neutral, and the solvent was concentrated to obtain SO-1. ２９ Si-NMR confirmed that SO-1 was a mixture of cage-like, ladder-like and random structures.

[0284] The weight-average molecular weight Mw of SO-1 was measured by gel permeation chromatography (GPC). A liquid chromatograph (manufactured by Nihon Waters) was used as the apparatus. Three columns were used in series: Shodex GPC KF-802 (exclusion limit molecular weight: 5000, manufactured by Showa Denko K.K.), Shodex GPC GPC KF802.5 (exclusion limit molecular weight: 20000, manufactured by Showa Denko K.K.), and Shodex GPC KF-803 (exclusion limit molecular weight: 70000, manufactured by Showa Denko K.K.). Tetrahydrofuran was used as the developing solution, and measurements were performed at a flow rate of 1 ml / min and a temperature of 40°C. Polystyrene was used as a standard sample, and the weight-average molecular weight was determined by comparative conversion.

[0285] Component (B) PC1: A compound represented by the following formula: In the formula, "Me" represents a methyl group.

[0286]

[0287] PC2: A compound represented by the following formula: In the formula, "Me" represents a methyl group.

[0288]

[0289] (Other compounding ingredients) (Stabilizers) HALS: bis(1,2,2,6,6-pentamethyl-4-piperidyl) sebacate HP: ethylene bis(oxyethylene) bis[3-(5-tert-butyl-4-hydroxy-m-tolyl) propionate] (manufactured by BASF Japan Ltd., Irganox 245).

[0290] (Photopolymerization initiator) PI: phenylbis(2,4,6-trimethylbenzoyl)-phosphine oxide (manufactured by IGM, Omnirad 819)

[0291] Example 1 (Production of Photochromic Curable Composition) First, the components were prepared according to the following formulation.

[0292] (A) Component (A-1) Component: TMM57-UMA 28.3 parts by mass. (A-2) Component: 14G 66.1 parts by mass. (A-4) Component: TSL 5.6 parts by mass. LA82 2.0 parts by mass.

[0293] Component (B): 2.0 parts by mass of PC1. (Other compounding ingredients) (Polymerization initiator): 0.3 parts by mass of PI. (Stabilizer): 1.0 part by mass of HP.

[0294] Next, all of the compounds corresponding to component (A) were mixed together, and then component (B) and other additives were mixed therewith to obtain a mixture. 1000 ppm of leveling agent L-7001 manufactured by Dow Toray Industries, Inc. was added to the obtained mixture, and the mixture was mixed to obtain a photochromic curable composition.

[0295] (Production of Optical Article) Using this photochromic curable composition, a polymerization reaction was carried out as follows, and a photochromic laminate was obtained by a lamination method.

[0296] First, a thiourethane-based plastic lens with a center thickness of 2 mm and a refractive index of 1.60 was prepared as an optical substrate. This thiourethane-based plastic lens was previously subjected to alkaline etching using a 5% aqueous solution of sodium hydroxide at 50°C for 5 minutes, and then thoroughly washed with distilled water.

[0297] Using a spin coater (1H-DX2, manufactured by MIKASA), the surface of the plastic lens was coated with a moisture-curable primer (product name: TR-SC-P, manufactured by Tokuyama Corporation) at a rotation speed of 70 rpm for 15 seconds, followed by 10 seconds at 700 rpm. Approximately 1 g of the photochromic curable composition obtained above was then spin coated onto the surface so that the photochromic coating layer had a thickness of 40 μm.

[0298] The lens having the photochromic curable composition (photochromic coating layer) applied to its surface was heated in a nitrogen gas atmosphere at an output of 200 mW / cm２ The coating was cured by irradiating the coating with light for 90 seconds using a metal halide lamp, and then heated at 90°C for 1 hour to prepare a photochromic laminate having a photochromic layer.

[0299] <Examples 2 to 3 and Comparative Example 1> As shown in Table 1, curable compositions were prepared in the same manner as in Example 1, except that the types and amounts of each radically polymerizable monomer were changed, and photochromic laminates were obtained.

[0300] Examples 4 to 24 and Comparative Examples 2 to 6 Curable compositions were prepared and photochromic laminates were obtained in the same manner as in Example 1, except that the types and amounts of each radically polymerizable monomer and the types and amounts of the photochromic compound and additives were changed as shown in Tables 2 to 4. Note that 1.6 parts by mass of PC2 was used as the photochromic compound. 3 parts by mass of HALS, 1 part by mass of HP, and 0.3 parts by mass of PI were used as the additives.

[0301] <Evaluation Method> The photochromic laminates obtained in the Examples and Comparative Examples were evaluated by the following methods: (1) Photochromic Properties [1] Maximum absorption wavelength (λmax (nm)): This is the maximum absorption wavelength after color development determined using a spectrophotometer (instant multichannel photodetector MCPD3000) manufactured by Otsuka Electronics Co., Ltd., and was used as an index of the color tone during color development.

[0302] [2] 23 ° C color density (A ２３ ε(240) is the difference between the absorbance {ε(240)} after 240 seconds of light irradiation at 23°C and the absorbance ε(0) before light irradiation at the maximum absorption wavelength. This is used as an index of color density. The higher this value, the better the photochromic properties.

[0303] [3] 23°C fading half-life [τ1 / 2 (sec.)]: This is the time required for the absorbance of the sample at the maximum absorption wavelength to decrease to 1 / 2 of {ε(300) - ε(0)} when the light irradiation is stopped after 300 seconds of light irradiation at 23°C, and is used as an index of the fading rate. The shorter this time, the faster the fading rate.

[0304] (2) Vickers hardness Vickers hardness was measured using a micro Vickers hardness tester PMT-X7A (manufactured by Matsuzawa Co., Ltd.). A square pyramidal diamond indenter was used as the indenter, and the measurement was performed under the conditions of a load of 10 gf and a holding time of the indenter of 30 seconds. A total of four measurements were performed, and the measurement results were shown as the average value of three measurements, excluding the value of the first measurement, which had a large measurement error.

[0305] (3) Appearance Evaluation The photochromic laminate was exposed to fluorescent light in a black box, and the appearance was evaluated according to the following criteria. A: No defects in appearance were observed. B: Wrinkles due to uneven shrinkage occurred in one to two lenses out of ten. C: Wrinkles due to uneven shrinkage occurred in one to five lenses out of ten. D: Wrinkles due to uneven shrinkage occurred in one to five lenses out of ten. E: Wrinkles due to uneven shrinkage occurred around the entire periphery of the lens. F: Wrinkles due to uneven shrinkage occurred in the periphery of the lens, and partial peeling of the photochromic layer occurred.

[0306]

[0307]

[0308]

[0309]

[0310]

[0023] Preferred embodiments of the present disclosure are described below. [1] A curable composition comprising a first radical polymerizable monomer represented by the following formula (1) and a functional dye:

[0311]

[0312] In formula (1), R １ is a trivalent or higher organic residue having 1 to 50 carbon atoms and containing at least one heteroatom selected from the group consisting of oxygen atoms and nitrogen atoms; R ２is a linear or branched alkylene group having from 1 to 10 carbon atoms, a2 is from 0 to 15, b2 is 3 or more, Y is a monovalent group represented by the following formula (2) or a (meth)acryloyl group, provided that at least one of the multiple Ys is a monovalent group represented by the following formula (2), and the multiple Ys may be the same or different,

[0313]

[0314] In formula (2), the dashed line represents the oxygen atom or R １ represents a bond with ３ is a linear or branched alkylene group having 1 to 6 carbon atoms, ４ is a hydrogen atom or a methyl group, and c2 is 1 or more and 5 or less. [2] The curable composition according to [1], wherein a proportion of the first radical polymerizable monomer in the curable composition is 5% by mass or more and 95% by mass or less. [3] The curable composition according to [1] or [2], wherein a proportion of the functional dye in the curable composition is 0.001% by mass or more and 10% by mass or less. [4] R in formula (1) １ The curable composition according to any one of [1] to [3], wherein R represents any one of the following formulas (1-A) to (1-I):

[0315]

[0316]

[0317]

[0318]

[0319]

[0320]

[0321]

[0322]

[0323]

[0324] In formula (1-A) to formula (1-I), * represents -(R ２ -O) ａ２ represents a bond to -Y, and in formula (1-H), d2 is 4 or more and 10 or less. [5] The curable composition according to any one of [1] to [4], further comprising a second radical polymerizable monomer having, in one molecule, at least one polyalkylene glycol chain structure having a number average molecular weight of 250 or more and two (meth)acryloyl groups. [6] The curable composition according to [5], wherein the second radical polymerizable monomer is a (meth)acrylate represented by the following formula (3):

[0325]

[0326] In the formula (3), Q ３ and Q ６ are each independently a hydrogen atom or a methyl group, and Q ４ and Q ５ are each independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and Q ７ is a divalent group represented by the following formula (3a) having a number average molecular weight of 250 or more, a and b each independently represent 0 or more and 10 or less, Z 1 and Z ２ are each independently 0 or 1,

[0327]

[0328] In the formula (3a), Q ７ａ and Q ７ｅ is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and Q ７ｂ and Q ７ｄ is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and Q ７ａ and Q ７ｂ are different groups, and Q ７ｄ and Q ７ｅ are different groups, and Q ７ｃis a linear or branched alkylene group having 2 to 20 carbon atoms which may have a substituent, d and h are 0 or more and 10 or less, e and g are 0 or more and 20 or less, and f is 3 or more and 100 or less. [7] The curable composition according to any one of [1] to [6], further comprising a third radically polymerizable monomer having three or more (meth)acryloyl groups in one molecule. [8] The curable composition according to [7], wherein the third radically polymerizable monomer comprises a polyfunctional (meth)acrylate represented by the following formula (I):

[0329]

[0330] In the formula (I), Q １０ is a linear or branched alkylene group having 1 to 3 carbon atoms, １１ is a linear or branched alkylene group having from 1 to 10 carbon atoms, １２ is a hydrogen atom or a methyl group, and Q １３represents a trivalent to hexavalent organic group having 1 to 10 carbon atoms, a1 is 0 or 1, b1 is 0 to 15, and c1 is 3 to 6. [9] The curable composition according to [5] or [6], wherein the second radical polymerizable monomer accounts for 10% by mass to 90% by mass in the curable composition.

[10] The curable composition according to [7] or [8], wherein the third radical polymerizable monomer accounts for 5% by mass to 95% by mass in the curable composition.

[11] The curable composition according to any of [1] to

[10] , wherein the functional dye includes a photochromic compound.

[12] The curable composition according to any of [1] to

[11] , further including a monofunctional (meth)acrylate.

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

[12] .

[14] A laminate comprising an optical substrate and a resin layer comprising the cured product according to

[13] .

[15] A laminate comprising an optical substrate, a primer layer comprising a urethane resin, and a resin layer comprising the cured product according to

[13] laminated on the primer layer.

[16] An optical article comprising the cured product according to

[13] .

[17] A lens comprising the cured product according to

[13] .

[18] Eyeglasses comprising the lens according to

[17] .

[19] The cured product according to

[13] , having a biomass plastic content of 10% by mass or more according to a method in accordance with ISO standard 16620-3.

[20] The laminate according to

[14] or

[15] , wherein the biomass plastic content of the optical substrate is 25% by mass or more according to a method in accordance with ISO standard 16620-3.

Claims

1. A curable composition comprising a first radical polymerizable monomer represented by the following formula (1) and a functional dye: In formula (1), R １ R is a trivalent or higher organic residue having 1 to 50 carbon atoms and containing at least one heteroatom selected from the group consisting of oxygen atoms and nitrogen atoms; ２ is a linear or branched alkylene group having 1 to 10 carbon atoms, a2 is 0 to 15, b2 is 3 or more, Y is a monovalent group represented by the following formula (2) or a (meth)acryloyl group, with the proviso that at least one of a plurality of Y's is a monovalent group represented by the following formula (2), and the plurality of Y's may be the same or different, In formula (2), the dashed line represents an oxygen atom or R １ represents a bond with ３ R is a linear or branched alkylene group having 1 to 6 carbon atoms; ４ represents a hydrogen atom or a methyl group; c2 represents an integer of 1 to 5.

2. The curable composition according to claim 1, wherein the proportion of the first radically polymerizable monomer in the curable composition is 5% by mass or more and 95% by mass or less.

3. The curable composition according to claim 1, wherein the proportion of the functional dye in the curable composition is 0.001% by mass or more and 10% by mass or less.

4. R in formula (1) １ The curable composition according to claim 1, wherein the compound represented by the formula (1-A) to the formula (1-I) is any one of the following formulas: In formula (1-A) to formula (1-I), * represents -(R ２ -O) ａ２ represents a bond to —Y, and in formula (1-H), d2 is 4 or more and 10 or less.

5. The curable composition according to claim 1, further comprising a second radically polymerizable monomer having, in one molecule, at least one polyalkylene glycol chain structure having a number average molecular weight of 250 or more and two (meth)acryloyl groups.

6. The curable composition according to claim 5, wherein the second radical polymerizable monomer is a (meth)acrylate represented by the following formula (3): In the formula (3), Q ３ and Q. ６ are each independently a hydrogen atom or a methyl group; ４ and Q. ５ each independently represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms; ７ is a divalent group having a number average molecular weight of 250 or more and represented by the following formula (3a), a and b each independently represent 0 or more and 10 or less, Z 1 and Z ２ are each independently 0 or 1, In the formula (3a), Q ７ａ and Q. ７ｅ is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms; ７ｂ and Q. ７ｄ is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms; ７ａ and Q ７ｂ are different groups, and Q ７ｄ and Q ７ｅ are different groups, ７ｃ represents a linear or branched alkylene group having 2 to 20 carbon atoms which may have a substituent; d and h are 0 or more and 10 or less; e and g are 0 or more and 20 or less; and f is 3 or more and 100 or less.

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

8. The curable composition according to claim 7, wherein the third radical polymerizable monomer comprises a polyfunctional (meth)acrylate represented by the following formula (I): In the formula (I), Q １０ is a linear or branched alkylene group having 1 to 3 carbon atoms; １１ is a linear or branched alkylene group having 1 to 10 carbon atoms; １２ is a hydrogen atom or a methyl group, Q １３ represents a trivalent to hexavalent organic group having 1 to 10 carbon atoms; a1 is 0 or 1; b1 is 0 or more and 15 or less; and c1 is 3 or more and 6 or less.

9. The curable composition according to claim 5, wherein the proportion of the second radically polymerizable monomer in the curable composition is 10% by mass or more and 90% by mass or less.

10. The curable composition described in claim 7, wherein the proportion of the third radically polymerizable monomer in the curable composition is 5 mass % or more and 95 mass % or less.

11. The curable composition of claim 1, wherein the functional dye comprises a photochromic compound.

12. The curable composition of claim 1, further comprising a monofunctional (meth)acrylate.

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

14. A laminate comprising an optical substrate and a resin layer containing the cured product according to claim 13.

15. A laminate comprising: an optical substrate; a primer layer containing a urethane resin; and a resin layer containing the cured product according to claim 13 laminated on the primer layer.

16. An optical article comprising the cured product according to claim 13.

17. A lens comprising the cured product according to claim 13.

18. Eyeglasses comprising the lens of claim 17.

19. The hardened body according to claim 13, having a biomass plastic content of 10% by mass or more as measured according to a method in accordance with ISO standard 16620-3.

20. The laminate according to claim 14, wherein the biomass plastic content of the optical substrate is 25% by mass or more, as determined by a method in accordance with ISO standard 16620-3.

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