Method for producing polymerizable composition and method for producing photochromic article

Abstract

To provide means that enables improved solubility of an indeno-fused naphthopyran compound and improved liquid life of a polymerizable composition, the polymerizable composition containing the indeno-fused naphthopyran compound and a polymerizable compound.SOLUTION: Provided are indeno-fused naphthopyran compound particles having a crystallinity of 60.00% or more and a maximum melting rate of 25% or less at a temperature of 200°C or less in a melting curve.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to particles of indeno-fused naphthopyran compounds, a method for producing a polymerizable composition, and a method for producing a photochromic article. [Background technology]

[0002] Patent Document 1 discloses an indeno-fused naphthopyran compound. [Prior art documents] [Patent documents]

[0003] [Patent Document 1] U.S. Patent No. 5,645,767 Summary of the Invention [Problem to be solved by the invention]

[0004] Photochromic compounds are compounds that exhibit a color when irradiated with light in a photoresponsive wavelength range and exhibit a color fade when not irradiated (photochromic property) (see, for example, Patent Document 1). In recent years, the usefulness of indeno-fused naphthopyran compounds as photochromic compounds has been attracting attention.

[0005] Examples of articles (photochromic articles) to which photochromic properties have been imparted by a photochromic compound include optical articles such as eyeglass lenses. Methods for imparting photochromic properties to photochromic articles include a method of providing a photochromic layer on a substrate using a polymerizable composition containing a photochromic compound and a polymerizable compound, and a method of producing a substrate using a polymerizable composition containing a photochromic compound and a polymerizable compound.

[0006] The polymerizable composition containing a photochromic compound and a polymerizable compound includes: High solubility of the photochromic compound in the polymerizable composition; and The polymerizable composition has little deterioration in quality over time (in other words, a long liquid life). is desired. Regarding solubility, if the solubility of the photochromic compound can be increased, the dispersed particle size of the photochromic compound in the polymerizable composition can be reduced. Reducing the dispersed particle size of the photochromic compound can contribute to improving the optical homogeneity of the layer and / or substrate formed using the polymerizable composition, which is desirable from the viewpoint of improving the appearance quality of the photochromic article. Regarding the liquid life, if the polymerizable composition used to produce a photochromic article is one that undergoes little deterioration in quality over time, it is preferable from an industrial viewpoint to prepare a large amount of the polymerizable composition and use the required amount appropriately, since this makes it possible to mass-produce eyeglass lenses that exhibit good photochromic performance.

[0007] In view of the above, one aspect of the present invention aims to provide a means for improving the solubility of an indeno-fused naphthopyran compound and the liquid life of a polymerizable composition containing an indeno-fused naphthopyran compound and a polymerizable compound. [Means for solving the problem]

[0008] One aspect of the present invention is Particles of an indeno-fused naphthopyran compound having a crystallinity of 60.00% or more and a maximum melting rate of 25% or less at a temperature of 200°C or less on a melting curve (hereinafter also simply referred to as "particles"); Regarding. [Effects of the Invention]

[0009] According to one embodiment of the present invention, particles of an indeno-condensed naphthopyran compound can be provided, which is a polymerizable composition containing an indeno-condensed naphthopyran compound and a polymerizable compound, and which has high solubility of the indeno-condensed naphthopyran compound in the composition and a long liquid life. [Brief explanation of the drawings]

[0010] [Figure 1] 1 shows the melting curve obtained for the particles of Example 1. [Figure 2] 1 shows the melting curve obtained for the particles of Example 2. [Figure 3] 1 shows the melting curve obtained for the particles of Comparative Example 1. [Figure 4] 4 shows the melting curve obtained for the particles of Comparative Example 2. [Figure 5] 1 shows the melting curve obtained for the particles of Comparative Example 3. DETAILED DESCRIPTION OF THE INVENTION

[0011] [Indeno-fused naphthopyran compound particles] One aspect of the present invention relates to particles of an indeno-fused naphthopyran compound, the particles having a crystallinity of 60.00% or more and a maximum melting rate at a temperature of 200°C or less in a melting curve (hereinafter also referred to as "maximum melting rate at 200°C or less" or simply "maximum melting rate") of 25% or less.

[0012] The present inventors believe that particles of an indeno-fused naphthopyran compound having a crystallinity of 60.00% or more and a maximum melting rate of 25% or less are particles that exist in the form of aggregates of fine particles as highly stable crystals. The present inventors speculate that particles existing in such a state are easily dissociated by impact during the mixing process in preparing a polymerizable composition, and easily dispersed in the form of fine particles in the liquid, thereby exhibiting high solubility. The present inventors also believe that the fact that such particles are less likely to re-aggregate after dissociation contributes to improved liquid life. However, the present invention is not limited to the speculations described herein. In one embodiment, the particles can exhibit high solubility in the polymerizable compound. One method for increasing the solubility of the photochromic compound in a polymerizable composition containing the photochromic compound and the polymerizable compound is to use a solvent. In contrast, if the solubility of the photochromic compound in the polymerizable compound can be increased, the amount of solvent used to prepare the polymerizable composition can be reduced. Reducing the amount of solvent used is desirable for reasons such as, for example, being able to prevent the substrate from being altered by the solvent contained in the polymerizable composition when a photochromic layer is formed on a substrate using a polymerizable composition containing a photochromic compound and a polymerizable compound.

[0013] The particles will be described in more detail below.

[0014] The particles are particles of an indeno-fused naphthopyran compound. The indeno-fused naphthopyran compound refers to a compound containing an indeno-fused naphthopyran, which may have a substituent, in its structure. The indeno-fused naphthopyran has a structure in which an indeno group is condensed with naphthopyran. An example of the structure of the indeno-fused naphthopyran, which may have a substituent, is the structure of the following formula A. The particles may be so-called monomers containing only one indeno-fused naphthopyran, which may have a substituent, or may be so-called polymers containing two or more indeno-fused naphthopyrans, which may have a substituent. The multiple indeno-fused naphthopyrans contained in the polymer may each have the same or different substituents.

[0015] [ka] (In formula A, R 1 ~R 10 , A and A' each independently represent a hydrogen atom or a substituent.

[0016] For example, a photochromic compound undergoes structural transformation into a colored form upon irradiation with light such as sunlight, passing through an excited state. The structure after structural transformation via light irradiation can be called a "colored form." In contrast, the structure before light irradiation can be called a "colorless form." However, the term "colorless" in relation to a colorless form does not necessarily mean complete colorlessness, but also encompasses a form that is lighter in color than the colored form. An indeno-fused naphthopyran compound can exhibit the properties of a photochromic compound (photochromicity). The above description of the structure of an indeno-fused naphthopyran compound is a description of a colorless form. A photochromic compound can exhibit photochromic properties, for example, when exposed to ultraviolet light.

[0017] <Crystallinity> The degree of crystallinity of particles in the present invention and this specification is a value determined from the following formula 1 by analyzing the results obtained by powder X-ray diffraction analysis using the Hermans method. Formula 1: Crystallinity Xc(%)=(Ic / (Ic+Ia))×100 In Equation 1, Ic is the crystalline scattering integrated intensity, and Ia is the amorphous scattering integrated intensity. The crystallinity can be calculated by a known method, such as a method using analysis software provided with an X-ray diffraction apparatus. The measurement conditions for the powder X-ray diffraction analysis are, for example, as follows. Target: Cu, X-ray tube current / voltage: 40mA / 45kV, scanning range: 2θ=4°~65°

[0018] The crystallinity of the particles is 60.00% or more, preferably 61.00% or more, more preferably 62.00% or more, and even more preferably 63.00% or more. The crystallinity of the particles can be, for example, 80.00% or less, 78.00% or less, 75.00% or less, 73.00% or less, 70.00% or less, 68.00% or less, or 66.00% or less, or can exceed the values exemplified herein.

[0019] <Maximum melting rate below 200°C> In the present invention and this specification, the maximum melting rate at 200°C or less is determined by the following method. The melting point of the particles to be measured is measured. The melting point measurement can be performed using a melting point measurement device with a known configuration that can measure the melting point of a solid sample. When the melting point measurement is performed, a melting curve is obtained. In the melting curve, the horizontal axis represents temperature, and a melting curve can be obtained in a temperature range of, for example, 0°C or higher. In the melting curve, the vertical axis represents the melting ratio. The maximum value of the melting ratio in the temperature range of 200°C or lower in the melting curve is defined as the maximum melting ratio (unit: %) at 200°C or lower.

[0020] The maximum melting rate of the particles at 200°C or less is 25% or less, preferably 24% or less, more preferably 23% or less, even more preferably 22% or less, even more preferably 21% or less, and even more preferably 20% or less. The maximum melting rate can be, for example, 5% or more, 7% or more, 10% or more, 12% or more, or 14% or more, or can be lower than the values exemplified herein.

[0021] The crystallinity and maximum melting rate of particles of an indeno-condensed naphthopyran compound can be controlled by increasing the purity of the indenonaphthopyran compound during synthesis, performing a solvent removal treatment during particle preparation, etc. For example, by increasing the purity and removing more solvent, the crystallinity can be increased and the maximum melting rate at 200°C or below can be reduced.

[0022] As described above, the particles can be aggregates of fine particles. The degree of association can be used as an indicator of the aggregation state of the aggregates. The degree of association is the ratio of the particle size in the aggregate state (i.e., secondary or higher-order particles) to the primary particle size (particle size in the aggregate state / primary particle size). Each particle size can be determined by observing the particles with a reflective optical microscope at a magnification of approximately 100x. The particle size is determined as the length of the longest line connecting two points on the particle's contour (i.e., the major axis). Five particles present in the aggregate state are randomly selected, and the arithmetic mean of the major axes determined for each of these particles is used as the particle size in the aggregate state. The primary particle size is the arithmetic mean of the major axes determined for each of the five randomly selected primary particles. The degree of association of the particles is preferably 50 or more, more preferably 55 or more. The degree of association of the particles can be, for example, 80 or less, 75 or less, or 70 or less. The degree of association can be controlled by known methods such as adjusting the heat treatment conditions during particle preparation or performing a pulverization treatment.

[0023] [Method of producing polymerizable composition] One aspect of the present invention relates to a method for producing a polymerizable composition, which comprises mixing the particles described above with one or more polymerizable compounds.

[0024] The particles can be dissolved in a polymerizable composition with high solubility. This allows the dispersed particle size of the indeno-fused naphthopyran compound in the polymerizable composition to be reduced. Furthermore, producing a polymerizable composition using the particles can contribute to providing a polymerizable composition with little deterioration in quality over time (i.e., long liquid life).

[0025] <particle> The particles of the indeno-fused naphthopyran compound used to prepare the polymerizable composition are as described above.

[0026] The indeno-fused naphthopyran compound can exhibit the properties of a photochromic compound (photochromicity). In one embodiment of the method for producing the polymerizable composition, only one or more of the above particles can be used as the photochromic compound. In another embodiment, one or more photochromic compounds can be used in combination with the above particles. Examples of photochromic compounds that can be used in combination include known compounds exhibiting photochromic properties. Specific examples of photochromic compounds include compounds having known skeletons that exhibit photochromic properties, such as fulgimide compounds, spirooxazine compounds, chromene compounds, and indeno-fused naphthopyran compounds. The content of the photochromic compound can be, for example, about 0.1 to 15.0% by mass relative to the total (100% by mass) of all components of the polymerizable composition, but is not limited to this range. Here, the total of all components refers to the total of all components excluding the solvent when a solvent is used to prepare the polymerizable composition. The content of the particles relative to the total amount (100% by mass) of the photochromic compound used to produce the polymerizable composition is preferably 50% by mass or more, more preferably 60% by mass or more, and even more preferably 70% by mass or more. The content of the particles relative to the total amount (100% by mass) of the photochromic compound used to produce the polymerizable composition can be, for example, 100% by mass, 100% by mass or less, 95% by mass or less, or 90% by mass or less.

[0027] In general, photochromic compounds tend to have low solubility in polymerizable compounds. To improve the solubility of photochromic compounds, a solvent is typically used, and the greater the amount of solvent used, the greater the solubility of the photochromic compound in a polymerizable composition containing the photochromic compound and the polymerizable composition. However, as described above, the solvent can cause deterioration of the substrate. Furthermore, when a solvent is used in the preparation of a polymerizable composition containing a photochromic compound and a polymerizable compound, a heat treatment is typically performed to volatilize the solvent component when the prepared polymerizable composition is polymerized and cured. However, depending on the solvent, high-temperature heat treatment is required to volatilize the solvent, and such high-temperature heat treatment can cause deterioration of the substrate. Furthermore, poor surface quality can also occur during solvent evaporation. Considering the above, it is desirable to reduce the amount of solvent used by improving the solubility of photochromic compounds in polymerizable compounds. In this regard, the indeno-fused naphthopyran compound, when in the form of the above particles, can exhibit high solubility in polymerizable compounds. Therefore, by using the above particles, the amount of solvent used in the preparation of the polymerizable composition can be reduced, and a solvent-free composition can also be achieved. Any solvent can be used as long as the polymerization reaction of the polymerizable compound can proceed in the presence of the solvent. The amount of solvent used in preparing the polymerizable composition can be, for example, 10.0 mass% or less, 5.0 mass% or less, 3.0 mass% or less, 1.0 mass% or less, or even 0 mass% based on the total (100 mass%) of all components (including the solvent, if used) used in preparing the composition.

[0028] <Polymerizable compound> In the method for producing a polymerizable composition, the polymerizable compound mixed with the particles is at least one type, and may be two or more, or three or more types, and may be, for example, five or less, or four or less types. In the present invention and this specification, a "polymerizable compound" refers to a compound having a polymerizable group, and a "polymerizable composition" refers to a composition containing one or more polymerizable compounds. Specific examples of polymerizable groups include acryloyl groups, methacryloyl groups, acryloyloxy groups, and methacryloyloxy groups, and specific examples of polymerizable compounds include (meth)acrylates. In the present invention and this specification, the term "(meth)acrylate" encompasses acrylates and methacrylates. An "acrylate" refers to a compound having one or more acryloyl groups in one molecule. A "methacrylate" refers to a compound having one or more methacryloyl groups in one molecule. The functionality of a (meth)acrylate refers to the number of groups selected from the group consisting of acryloyl groups and methacryloyl groups contained in one molecule. In the present invention and this specification, "methacrylate" refers to a group containing only methacryloyl groups as (meth)acryloyl groups, and a group containing both acryloyl and methacryloyl groups as (meth)acryloyl groups is called an acrylate. The acryloyl group may be contained in the form of an acryloyloxy group, and the methacryloyl group may be contained in the form of a methacryloyloxy group. The "(meth)acryloyl group" described below is used to encompass both acryloyl and methacryloyl groups, and the "(meth)acryloyloxy group" is used to encompass both acryloyloxy and methacryloyloxy groups. Furthermore, unless otherwise specified, the groups described may be substituted or unsubstituted. When a certain group has a substituent, examples of the substituent include an alkyl group (e.g., an alkyl group having 1 to 6 carbon atoms), a hydroxyl group, an alkoxy group (e.g., an alkoxy group having 1 to 6 carbon atoms), a halogen atom (e.g., a fluorine atom, a chlorine atom, a bromine atom), a cyano group, an amino group, a nitro group, an acyl group, a carboxy group, etc. Furthermore, the "number of carbon atoms" of a substituted group means the number of carbon atoms in the portion excluding the substituent.

[0029] (Component A) In one embodiment, the polymerizable compound mixed with the particles in the method for producing a polymerizable composition can contain one or more (meth)acrylates. Among (meth)acrylates, acyclic methacrylates with a molecular weight of 500 or more tend to have low solubility in photochromic compounds. "Acyclic methacrylates with a molecular weight of 500 or more" are also referred to as "component A." In the method for producing a polymerizable composition, even when the polymerizable compound mixed with the photochromic compound contains component A, mixing the component A in the form of particles can increase the solubility of the indeno-fused naphthopyran compound in component A.

[0030] In the present invention and this specification, the term "non-cyclic" means that it does not contain a cyclic structure. An non-cyclic methacrylate refers to a monofunctional or higher functional methacrylate that does not contain a cyclic structure.

[0031] Component A can be a monofunctional or di- or higher functional methacrylate, preferably a di- or tri-functional methacrylate, and more preferably a di-functional methacrylate. Component A can be exemplified by polyalkylene glycol dimethacrylate. Polyalkylene glycol dimethacrylate is represented by the following formula 1: [ka] where R represents an alkylene group, and n represents the number of repeating alkoxy groups represented by RO and is 2 or more. Examples of the alkylene group represented by R include an ethylene group, a propylene group, and a tetramethylene group. n is 2 or more and can be, for example, 30 or less, 25 or less, or 20 or less. Specific examples of polyalkylene glycol dimethacrylate include polyethylene glycol dimethacrylate, polypropylene glycol dimethacrylate, and polytetramethylene glycol dimethacrylate.

[0032] The molecular weight of component A is 500 or more. It is believed that the inclusion of an acyclic bifunctional methacrylate (component A) having a molecular weight of 500 or more together with component B (described later) can contribute to the high color development of the photochromic compound upon exposure to light in a photochromic layer formed from a polymerizable composition containing these components and a photochromic compound. In the present invention and this specification, the molecular weight of the polymer refers to the structural formula determined by structural analysis of the compound or the theoretical molecular weight calculated from the raw material charge ratio during production. The molecular weight of component A is 500 or more, preferably 510 or more, more preferably 520 or more, more preferably 550 or more, more preferably 570 or more, even more preferably 600 or more, even more preferably 630 or more, and even more preferably 650 or more. From the viewpoint of increasing the hardness of the photochromic layer, the molecular weight of component A is preferably, for example, 2000 or less, 1500 or less, 1200 or less, 1000 or less, or 800 or less.

[0033] Component A may be the component that is contained in the largest amount among the (meth)acrylates used to produce the polymerizable composition, or may be the component that is contained in the largest amount among the polymerizable compounds used to produce the polymerizable composition.

[0034] (Component B) The polymerizable compound to be mixed with the particles in the method for producing the polymerizable composition may be a bifunctional (meth)acrylate having a structure selected from the group consisting of a cyclic structure and a branched structure. The "bifunctional (meth)acrylate having a structure selected from the group consisting of a cyclic structure and a branched structure" is also referred to as "Component B."

[0035] Component B is a bifunctional (meth)acrylate containing a structure selected from the group consisting of a cyclic structure and a branched structure. It is believed that the inclusion of component A together with component B contributes to the ability of the photochromic compound irradiated with light to develop color at a high concentration in a photochromic layer formed from a polymerizable composition containing these components and a photochromic compound. In one embodiment, component B contains one or more cyclic structures but no branched structures per molecule; in another embodiment, it contains one or more branched structures but no cyclic structures per molecule; and in another embodiment, it contains one or more cyclic structures and one or more branched structures per molecule. The number of structures selected from the group consisting of cyclic structures and branched structures per molecule is one or more, and can be, for example, one, two, or three, preferably one or two, and more preferably one. Regarding the branched structure, when component B contains a methacryloyl group, the branched structure contained in the methacryloyl group is not considered.

[0036] In one embodiment, component B containing one or more cyclic structures can be an alicyclic difunctional (meth)acrylate. The alicyclic difunctional (meth)acrylate can be, for example, R 1 -(L 1 )n1-Q-(L 2 )n2-R 2 where Q represents a divalent alicyclic group, and R 1 and R 2 each independently represents a (meth)acryloyl group or a (meth)acryloyloxy group, L 1 and L 2 each independently represents a linking group, and n1 and n2 each independently represent 0 or 1. The divalent alicyclic group represented by Q is preferably an alicyclic hydrocarbon group having 3 to 20 carbon atoms, and examples thereof include a cyclopentylene group, a cyclohexylene group, a cycloheptylene group, a cyclooctylene group, a tricyclodecanylene group, and an adamantylene group. 1 and L 2 An example of the linking group represented by the formula: can be an alkylene group. The alkylene group can be, for example, an alkylene group having 1 to 6 carbon atoms.

[0037] Specific examples of the alicyclic bifunctional (meth)acrylate include cyclohexanedimethanol di(meth)acrylate, ethoxylated cyclohexanedimethanol di(meth)acrylate, propoxylated cyclohexanedimethanol di(meth)acrylate, ethoxylated propoxylated cyclohexanedimethanol di(meth)acrylate, tricyclodecane dimethanol di(meth)acrylate, ethoxylated tricyclodecane dimethanol di(meth)acrylate, propoxylated tricyclodecane dimethanol di(meth)acrylate, and ethoxylated propoxylated tricyclodecane dimethanol di(meth)acrylate.

[0038] In one embodiment, Component B containing one or more branched structures can be a bifunctional (meth)acrylate containing a branched alkylene group. The branched alkylene group can have 1 or more, 2 or more, 3 or more, or 4 or more carbon atoms. The branched alkylene group can have 10 or less, 9 or less, 8 or less, 7 or less, 6 or less, or 5 or less carbon atoms. In one embodiment, the branched alkylene group can contain a quaternary carbon (i.e., a carbon bonded to four carbons). Specific examples of Component B containing one or more branched structures include neopentyl glycol di(meth)acrylate, ethoxylated neopentyl glycol di(meth)acrylate, and propoxylated neopentyl glycol di(meth)acrylate.

[0039] The molecular weight of Component B is not particularly limited, but in one embodiment, it can be, for example, in the range of 200 to 400. Component B may contain only acryloyl groups, only methacryloyl groups, or both acryloyl groups and methacryloyl groups as (meth)acryloyl groups.

[0040] In the method for producing a polymerizable composition, when component A and component B are used as polymerizable compounds, the content of component A is preferably 50.0% by mass or more, more preferably 60.0% by mass or more, and even more preferably 70.0% by mass or more, relative to the total amount (100% by mass) of (meth)acrylates used in producing the polymerizable composition. The content of component A can be, for example, 95.0% by mass or less, or 90.0% by mass or less. Only one type of component A may be used, or two or more types of component A may be used. When two or more types of component A are used, the content is the total content of the two or more types of component A. This also applies to the content of other components such as component B. In the present invention and this specification, a component that corresponds to both component A and component B is considered to be component A. On the other hand, the content of component B can be 1.0% by mass or more, preferably 5.0% by mass or more, and more preferably 10.0% by mass or more, based on the total amount (100% by mass) of (meth)acrylates used in the preparation of the polymerizable composition. The content of component B can be, for example, 30.0% by mass or less, 25.0% by mass or less, or 20.0% by mass or less. As the polymerizable compound used in the preparation of the polymerizable composition, a (meth)acrylate other than components A and B may or may not be used. When a (meth)acrylate other than components A and B is used, the content thereof is preferably 10.0% by mass or less, more preferably 5.0% by mass or less, based on the total amount (100% by mass) of (meth)acrylates used in the preparation of the polymerizable composition. As the polymerizable compound used in the preparation of the polymerizable composition, a polymerizable compound other than a (meth)acrylate may or may not be used. The (meth)acrylate can be used in a proportion of, for example, 80.0 to 99.9 mass % relative to the total (100 mass %) of all components used in producing the polymerizable composition. Here, the total of all components refers to the total of all components excluding the solvent when a solvent is used.

[0041] (Component C) In the method for producing a polymerizable composition, the polymerizable compound to be mixed with the particles has a molecular weight of 400 or less and is represented by the following formula 2: [ka] Examples of such (meth)acrylates include (meth)acrylates represented by the following formula: These (meth)acrylates are also referred to as "component C."

[0042] In formula 2, R 1 and R 2 each independently represents a hydrogen atom or a methyl group, and m represents an integer of 1 or greater. m is 1 or greater and can be, for example, 10 or less, 9 or less, 8 or less, 7 or less, or 6 or less.

[0043] The molecular weight of component C is 400 or less, and from the viewpoint of further increasing the color density of the photochromic layer formed from the polymerizable composition containing component C and a photochromic compound, it is preferably 350 or less, more preferably 300 or less, and even more preferably 250 or less. The molecular weight of component C can be, for example, 100 or more, 150 or more, or 200 or more.

[0044] Component C may contain only acryloyl groups, only methacryloyl groups, or both acryloyl and methacryloyl groups as (meth)acryloyl groups. In one embodiment, component C preferably contains only acryloyl groups as (meth)acryloyl groups. Specific examples of component C include 1,9-nonanediol diacrylate, 1,6-hexanediol diacrylate, and 1,10-decanediol diacrylate. According to the inventors' studies, in a photochromic layer formed from a polymerizable composition containing component A and component C as polymerizable compounds together with a photochromic compound, the photochromic compound can develop a high color concentration upon exposure to light, and the photochromic layer can exhibit excellent visible light transmittance in the absence of irradiation.

[0045] (Component D) In the method for producing the polymerizable composition, the polymerizable compound to be mixed with the particles can be an acyclic tri- or higher functional (meth)acrylate. Component D can contribute to improving performance such as the coatability of the polymerizable composition and the adhesion between a photochromic layer formed from the polymerizable composition and an adjacent layer. Component D is preferably a tri- to pentafunctional (meth)acrylate, more preferably a tri- or tetrafunctional (meth)acrylate, and even more preferably a trifunctional (meth)acrylate. Specific examples of component D include pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol tetra(meth)acrylate, trimethylolethane tri(meth)acrylate, trimethylolpropane tri(meth)acrylate, ditrimethylolpropane tetra(meth)acrylate, tetramethylolmethane tetra(meth)acrylate, and tetramethylolmethane tri(meth)acrylate. The molecular weight of Component D can be, for example, in the range of 200 to 400, but is not limited to this range. Component D may contain only acryloyl groups, only methacryloyl groups, or acryloyl groups and methacryloyl groups as (meth)acryloyl groups. In one embodiment, the acyclic tri- or higher functional (meth)acrylate preferably contains only methacryloyl groups as (meth)acryloyl groups, i.e., is a methacrylate.

[0046] (Component E) The polymerizable compound to be mixed with the particles in the method for producing the polymerizable composition may also include a polymerizable compound having a viscosity of 100 cP (centipoise) or less and selected from the group consisting of (meth)acrylates and vinyl ethers. Such a polymerizable compound is also referred to as "Component E." Component D can contribute to improving performance, such as the coatability of the polymerizable composition and the adhesion between a photochromic layer formed from the polymerizable composition and an adjacent layer. The "viscosity" in the present invention and this specification is a value measured using a vibration viscometer in an atmospheric atmosphere at a temperature of 25°C. The viscosity of Component E is 100 cP or less, preferably 70 cP or less, and more preferably 50 cP or less. The viscosity of Component E may be, for example, 5 cP or more or 10 cP or more. The (meth)acrylate, which is one form of Component E, may be monofunctional to trifunctional, and preferably monofunctional to difunctional. The (meth)acrylate, which is one form of Component E, may contain an aryl group (e.g., a phenyl group), an amide group, or the like. In the present invention and this specification, a "vinyl ether" refers to a compound having one or more vinyl groups and one or more ether bonds in one molecule, preferably two or more vinyl groups, and more preferably two to four vinyl groups in one molecule. The number of ether bonds contained in the vinyl ether is preferably two to four in one molecule. The molecular weight of component E can be, for example, in the range of 150 to 250, but is not limited to this range.Specific examples of component E include 2-phenoxyethyl (meth)acrylate, acrylamide, methoxypolyethylene glycol (meth)acrylate, phenoxypolyethylene glycol (meth)acrylate, stearyl (meth)acrylate, 1,10-decanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,9-nonanediol di(meth)acrylate, dipropylene glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, Propylene glycol di(meth)acrylate, ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, tricyclodecane dimethanol di(meth)acrylate, ethoxylated propylene glycol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, ethyl (meth)acrylate, butyl (meth)acrylate, isobutyl (meth)acrylate, tert-butyl Cetyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, isodecyl (meth)acrylate, dodecyl (meth)acrylate, tridecyl (meth)acrylate, diethylene glycol butyl ether (meth)acrylate, cyclohexyl (meth)acrylate, tetrahydrofurfuryl (meth)acrylate, benzyl (meth)acrylate, isobornyl (meth)acrylate, 2-(dimethylamino)ethyl (meth)acrylate, 2-(diethylamino)ethyl (meth)acrylate Examples of the vinyl acrylate include glycidyl (meth)acrylate, polyethylene glycol di(meth)acrylate, tetramethylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, nonamethylene glycol di(meth)acrylate, isoamyl (meth)acrylate, ethylene glycol monovinyl ether, tetramethylene glycol monovinyl ether, diethylene glycol monovinyl ether, 2-ethylhexyl vinyl ether, 2-propenoic acid, 2-[2-(ethenyloxy)ethoxy]ethyl ester, and 2-(2-ethenoxyethoxy)ethyl 2-methylprop-2-enoate.

[0047] In the method for producing a polymerizable composition, when Components A and C are used as the polymerizable compounds, the content of Component A is preferably 50.0% by mass or more, more preferably 55.0% by mass or more, and even more preferably 60.0% by mass or more, relative to the total amount of polymerizable compounds used in producing the polymerizable composition (100% by mass). The content of Component A may be 90.0% by mass or less, 85.0% by mass or less, 80.0% by mass or less, or 75.0% by mass or less.

[0048] Regarding component C, the inventors' investigations have shown that the higher the content of component C, the higher the color density of the photochromic compound when colored upon light irradiation in a photochromic layer formed from a polymerizable composition containing this component. On the other hand, the inventors' investigations have also shown that the higher the content of component C, the slower the fading rate of the photochromic compound after light irradiation. From the viewpoint of color density, the content of component C is preferably 5.0% by mass or more, more preferably 10.0% by mass or more, and even more preferably 15.0% by mass or more, based on 100% by mass of the total amount of polymerizable compounds used in producing the polymerizable composition. Furthermore, from the viewpoint of preventing a slowdown in the fading rate, the content of component C is preferably 30.0% by mass or less, and more preferably 25.0% by mass or less.

[0049] With respect to Component D, the content of Component D may be 0% by mass, or may be 0% by mass or more, greater than 0% by mass, 1.0% by mass or more, 3.0% by mass or more, 5% by mass or more, or 7% by mass or more, where the total amount of polymerizable compounds used in producing the polymerizable composition is 100% by mass. The content of Component D may be, for example, 20.0% by mass or less or 15.0% by mass or less. In one embodiment, Component D may be mixed with the particles together with Component A and Component B.

[0050] With respect to component E, the content of component E may be 0% by mass, or may be 0% by mass or more, greater than 0% by mass, 1.0% by mass or more, 3.0% by mass or more, 5.0% by mass or more, or 7.0% by mass or more, where the total amount of polymerizable compounds used in the production of the polymerizable composition is 100% by mass. The content of component E may be, for example, 20.0% by mass or less or 15.0% by mass or less. In one embodiment, component E may be used together with component A and component B, or further together with component D, to produce the polymerizable composition.

[0051] In the method for producing the polymerizable composition, the content of the polymerizable compound relative to the total (100% by mass) of all components of the polymerizable composition can be, for example, 80.0% by mass or more, 85.0% by mass or more, or 90.0% by mass or more. Here, the total of all components refers to the total of all components excluding the solvent when a solvent is used. Furthermore, the content of the polymerizable compound can be, for example, 99.0% by mass or less, 95.0% by mass or less, 90.0% by mass or less, or 85.0% by mass or less.

[0052] <Other ingredients> In addition to the particles and polymerizable compound, the components of the polymerizable composition may include one or more of various additives that are typically contained in polymerizable compositions. One or more of these components may be used in any ratio. One example of such an additive is a polymerization initiator for promoting the polymerization reaction.

[0053] For example, the polymerization initiator may be a known polymerization initiator, preferably a radical polymerization initiator, and more preferably a polymerization initiator containing only a radical polymerization initiator. Further, the polymerization initiator may be a photopolymerization initiator or a thermal polymerization initiator, and a photopolymerization initiator is preferred from the viewpoint of progressing the polymerization reaction in a short time. Examples of the photoradical polymerization initiator include benzoin ketals such as 2,2-dimethoxy-1,2-diphenylethan-1-one; α-hydroxyketones such as 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, and 1-[4-(2-hydroxyethoxy)phenyl]-2-hydroxy-2-methyl-1-propan-1-one; α-aminoketones such as 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one and 1,2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one; oxime esters such as 1-[(4-phenylthio)phenyl]-1,2-octadione-2-(benzoyl)oxime; bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, bis(2,6-dimethoxybenzoyl)phenylphosphine oxide, and the like. phosphine oxides such as 2-(o-chlorophenyl)-4,5-diphenylimidazole dimer, 2-(o-chlorophenyl)-4,5-di(methoxyphenyl)imidazole dimer, 2-(o-fluorophenyl)-4,5-diphenylimidazole dimer, 2-(o-methoxyphenyl)-4,5-diphenylimidazole dimer, and 2-(p-methoxyphenyl)-4,5-diphenylimidazole dimer; benzophenone compounds such as benzophenone, N,N'-tetramethyl-4,4'-diaminobenzophenone, N,N'-tetraethyl-4,4'-diaminobenzophenone, and 4-methoxy-4'-dimethylaminobenzophenone;quinone compounds such as 2-ethylanthraquinone, phenanthrenequinone, 2-tert-butylanthraquinone, octamethylanthraquinone, 1,2-benzanthraquinone, 2,3-benzanthraquinone, 2-phenylanthraquinone, 2,3-diphenylanthraquinone, 1-chloroanthraquinone, 2-methylanthraquinone, 1,4-naphthoquinone, 9,10-phenanthraquinone, 2-methyl-1,4-naphthoquinone, and 2,3-dimethylanthraquinone; benzoin ethers such as benzoin methyl ether, benzoin ethyl ether, and benzoin phenyl ether; benzoin compounds such as benzoin, methylbenzoin, and ethylbenzoin; benzyl compounds such as benzil dimethyl ketal; acridine compounds such as 9-phenylacridine and 1,7-bis(9,9'-acridinylheptane); N-phenylglycine, coumarin, and the like. In addition, in the 2,4,5-triarylimidazole dimer, the substituents on the aryl groups of the two triarylimidazole moieties may be the same to give a symmetrical compound, or may be different to give an asymmetrical compound. Furthermore, a thioxanthone compound may be combined with a tertiary amine, such as the combination of diethylthioxanthone and dimethylaminobenzoic acid. Among these, α-hydroxyketone and phosphine oxide are preferred from the viewpoints of curability, transparency, and heat resistance. The content of the polymerization initiator may be, for example, in the range of 0.1 to 5.0% by mass relative to the total (100% by mass) of all components of the polymerizable composition. The "total of all components" refers to the total of all components excluding the solvent when a solvent is used.

[0054] Usable additives include known additives that are usually added to compositions containing photochromic compounds, such as surfactants, antioxidants, radical scavengers, light stabilizers, ultraviolet absorbers, color inhibitors, antistatic agents, fluorescent dyes, dyes, pigments, fragrances, plasticizers, silane coupling agents, etc. Known compounds can be used as these additives.

[0055] When producing the polymerizable composition, the various components described above can be added and mixed simultaneously or sequentially in any order.

[0056] The particles and polymerizable compound can be mixed alone or in combination with one or more other components. Examples of the mixing method include various mixing methods that can mix multiple components.

[0057] From the viewpoint of further improving the solubility of the photochromic compound, a preferred mixing method is mixing using an ultrasonic homogenizer. An ultrasonic homogenizer is a device that can generate bubbles in a liquid due to a pressure difference called cavitation by ultrasonic vibration. When the generated bubbles disappear, shock waves are generated, which break down and micronize the particles of the photochromic compound mixed with the polymerizable compound. Furthermore, it is presumed that the polymerizable compound is heated by the energy of the ultrasonic waves, which promotes molecular motion, making the micronized particles of the photochromic compound more easily dispersible in the polymerizable compound. The inventors presume that these factors contribute to further improving the solubility of the photochromic compound in the polymerizable compound (specifically, further reducing the dispersed particle size in the composition). However, the presumptions described herein do not limit the present invention.

[0058] Commercially available ultrasonic homogenizers can be used. Examples of commercially available products include the THU-80 manufactured by ASONE and the SR-500HD-T ultrasonic reaction device manufactured by Shinka Sangyo Co., Ltd., but are not limited to these. The mixing conditions for the ultrasonic homogenizer can be determined based on the types of photochromic compounds and polymerizable compositions to be mixed, the concentrations of each component in the composition, and other factors. For example, the ultrasonic homogenizer can have an output power of 80 to 500 W, a frequency of 20 to 80 kHz (preferably 30 to 80 kHz), and an ultrasonic application time (hereinafter also referred to as "treatment time") of 5 to 240 minutes. However, the mixing conditions for the ultrasonic homogenizer in the method for producing the polymerizable composition are not limited to the above ranges.

[0059] During mixing using an ultrasonic homogenizer, in one embodiment, the temperature of the polymerizable composition can be controlled using a temperature control device. In another embodiment, mixing using an ultrasonic homogenizer can be performed without temperature control using a temperature control device. As described above, when mixing using an ultrasonic homogenizer, the polymerizable composition is heated by ultrasonic energy. Therefore, even without temperature control using a temperature control device, the temperature of the polymerizable composition during mixing may be higher than before mixing. From the viewpoint of further increasing the solubility of the photochromic compound in the polymerizable compound, temperature control using a temperature control device is preferred. Specifically, it is preferred to heat the polymerizable composition being mixed using an ultrasonic homogenizer using a heating device. Known heating devices such as an oil bath, a water bath, and a heater can be used as the heating device. Mixing using an ultrasonic homogenizer can be performed at a temperature of, for example, 80°C or higher, preferably 90°C or higher, and more preferably 100°C or higher. The temperature can be, for example, 150°C or lower, 140°C or lower, 130°C or lower, or 120°C or lower. The temperatures described in this invention and this specification regarding mixing are the maximum temperature that the polymerizable composition reaches during mixing. In one embodiment, mixing using an ultrasonic homogenizer is preferably performed using an oil bath at a temperature of 100°C or higher. Furthermore, mixing using an ultrasonic homogenizer can also be performed in combination with a stirring means such as a magnetic stirrer. The use of such a stirring means can induce liquid convection in the polymerizable composition. This is preferable from the viewpoint of homogenizing the liquid temperature and the treatment using the ultrasonic homogenizer.

[0060] [Method of manufacturing photochromic articles] One aspect of the present invention is Producing a polymerizable composition by the above production method; and curing the produced polymerizable composition to form a cured product containing a photochromic compound; a method for producing a photochromic article, comprising: Regarding.

[0061] In the present invention and this specification, the term "photochromic article" refers to an article containing a photochromic compound. The photochromic article produced by the above-mentioned production method can be a photochromic article to which photochromic properties are imparted by the indeno-condensed naphthopyran compound contained in the cured product of the polymerizable composition produced by the above-mentioned method for producing a polymerizable composition.

[0062] In one embodiment, the cured product can be a substrate containing a photochromic compound, and in another embodiment, it can be a photochromic layer provided directly or indirectly on a substrate.

[0063] The substrate containing the photochromic compound can be obtained by polymerizing and curing the polymerizable composition produced by the above-described method for producing a polymerizable composition by a known method such as cast polymerization, and molding it into the shape of the substrate.

[0064] On the other hand, when a photochromic layer is provided directly or indirectly on a substrate, a substrate selected depending on the type of photochromic article can be used as the substrate. In one embodiment, the photochromic article can be an optical article. Optical articles include various articles such as eyeglass lenses, goggle lenses, sun visor visors, and helmet shields. As an example of the substrate, an eyeglass lens substrate can be a plastic lens substrate or a glass lens substrate. The glass lens substrate can be, for example, a lens substrate made of inorganic glass. As the lens substrate, a plastic lens substrate is preferred from the viewpoints of being lightweight, shatter-resistant, and easy to handle. Examples of plastic lens substrates include styrene resins such as (meth)acrylic resins, polycarbonate resins, allyl resins, allyl carbonate resins such as diethylene glycol bisallyl carbonate resin (CR-39), vinyl resins, polyester resins, polyether resins, urethane resins obtained by reacting an isocyanate compound with a hydroxy compound such as diethylene glycol, thiourethane resins obtained by reacting an isocyanate compound with a polythiol compound, and cured products (commonly referred to as transparent resins) obtained by curing a curable composition containing a (thio)epoxy compound having one or more disulfide bonds in the molecule. Lens substrates may be undyed (colorless lenses) or dyed (dyed lenses). The refractive index of the lens substrate may be, for example, approximately 1.60 to 1.75. However, the refractive index of the lens substrate is not limited to the above range and may be within the above range or may deviate above or below the range. In the present invention and this specification, the refractive index refers to the refractive index for light with a wavelength of 500 nm. The lens substrate may be a lens with refractive power (a so-called prescription lens) or a lens without refractive power (a so-called non-prescription lens). Before forming one or more layers thereon, the substrate surface may be optionally subjected to one or more known pretreatments, such as alkali treatment and UV ozone treatment, for cleaning the substrate surface.

[0065] The spectacle lens can be any of various lenses, such as a single-vision lens, a multifocal lens, or a progressive-power lens. The type of lens is determined by the surface shapes of both sides of the lens substrate. The surface of the lens substrate may be convex, concave, or flat. In typical lens substrates and spectacle lenses, the object-side surface is convex and the eyeball-side surface is concave. However, the present invention is not limited to this. The photochromic layer can usually be provided on the object-side surface of the lens substrate, but it may also be provided on the eyeball-side surface.

[0066] The polymerizable composition produced by the above-described method for producing a polymerizable composition is applied directly or indirectly via one or more other layers to the surface of a substrate, and the applied composition is then cured to form a photochromic layer as a cured layer formed by curing the composition. Examples of such other layers include a primer layer for improving adhesion between the photochromic layer and the substrate. Such primer layers are known. Known coating methods such as spin coating and dip coating can be used to apply the polymerizable composition, with spin coating being preferred from the viewpoint of uniformity of application. The curing treatment can be light irradiation and / or heat treatment, with light irradiation being preferred from the viewpoint of progressing the curing reaction in a short period of time. The curing treatment conditions can be determined depending on the types of various components (polymerizable compound, polymerization initiator, etc.) contained in the polymerizable composition and the composition of the polymerizable composition. The thickness of the photochromic layer thus formed is preferably in the range of 5 to 80 μm, and more preferably in the range of 20 to 60 μm.

[0067] The photochromic article having the photochromic layer may or may not have one or more functional layers in addition to the photochromic layer. Specific examples of the functional layer include layers known as functional layers for optical articles, such as a protective layer for improving durability, an anti-reflection layer, a water-repellent or hydrophilic anti-fouling layer, and an anti-fogging layer.

[0068] One example of a photochromic article is a spectacle lens. Other examples of photochromic articles include lenses for goggles, sun visors, and helmet shields. These articles can exhibit anti-glare properties by containing a photochromic compound.

[0069] Furthermore, because the spectacle lenses are photochromic articles, eyeglasses equipped with such spectacle lenses can exhibit anti-glare effects similar to sunglasses when outdoors, for example, as the photochromic compound contained in the spectacle lenses changes color when irradiated with sunlight, and when returning indoors, the photochromic compound fades, allowing the eyeglasses to regain their transparency. Known technologies can be applied to the construction of frames and other components of the eyeglasses. [Example]

[0070] The present invention will be further described below with reference to examples, but the present invention is not limited to the embodiments shown in the examples.

[0071] [Examples 1 and 2, Comparative Examples 1 to 3] For the indeno-fused naphthopyran compound having the same structure as that represented by the formula A described above, the purity adjustment method during synthesis and / or the treatment conditions for solvent removal during particle preparation were changed to obtain the particles of Examples 1 and 2 and Comparative Examples 1 to 3. For each particle, the crystallinity and the maximum melting rate at 200° C. or less in the melting curve were determined by the method described above. Specifically, for the crystallinity, approximately 10 mg of each particle sample was packed into a silicon non-reflective plate, and X-ray diffraction analysis was performed using an X'Pert PROMPD X-ray diffractometer manufactured by Spectris PANalytical Division, and the results were analyzed by the Hermans method using the analysis software provided with the above-mentioned instrument, and the crystallinity was calculated using the above-mentioned formula 1. The measurement conditions for the X-ray diffraction analysis were as follows: target: Cu, X-ray tube current / voltage: 40 mA / 45 kV, scan range: 2θ = 4° to 65°. The melting curves were obtained by measuring the melting point using an image analysis method using a BUCHI M-565 melting point analyzer. The melting point analyzer had three sample introduction tubes, and for measuring the melting point of each particle, particles were introduced into each of the three sample introduction tubes, and a melting curve was obtained for the particles in each sample introduction tube. The maximum value of the melting rate at 200°C or less in the three melting curves thus obtained was taken as the maximum melting rate at 200°C or less. The melting curves obtained for the particles of Examples 1 to 5 are shown in Figures 1 to 5. The degree of association was also measured by the method described above (magnification of a reflected light microscope: 100x) for each of the particles of Example 1, Example 2, and Comparative Examples 2 and 3. The degree of association was 58 for Example 1, 64 for Example 2, 9 for Comparative Example 2, and 24.3 for Comparative Example 3.

[0072] [Evaluation of solubility] The solubility of each of the particles of Examples 1 and 2 and Comparative Examples 1 to 3 was evaluated by the following method.

[0073] <Preparation of Polymerizable Composition> In a glass container, 85 parts by mass of polyethylene glycol dimethacrylate (in the above formula 1, n=14, R is an ethylene group, molecular weight 736) and 15 parts by mass of tricyclodecane dimethanol dimethacrylate (molecular weight 332) were mixed to obtain a mixture of polymerizable compounds. The particles and polymerization initiator from the Examples and Comparative Examples were added to the mixture of polymerizable compounds obtained above, and mixing was carried out using an ultrasonic homogenizer. A photoradical polymerization initiator (bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide (Omnirad 819, manufactured by IGM Resin BV)) was used as the polymerization initiator. 2.25 parts by mass of each of the particles and 0.8 parts by mass of the polymerization initiator were added per 100 parts by mass of the mixture of polymerizable compounds. Mixing using the ultrasonic homogenizer was carried out at a frequency of 20 kHz, an output of 80 W, and a processing time of 9 minutes. A magnetic stirrer was also used during mixing using the ultrasonic homogenizer. Specifically, a THU-80 manufactured by ASONE was used as the ultrasonic homogenizer. The THU-80 manufactured by ASONE is an ultrasonic homogenizer equipped with an ultrasonic oscillator and a vibrator. Mixing was performed by placing the container on a magnetic stirrer, inserting a vibrator into the mixture of photochromic compound, polymerizable compound, and polymerization initiator in the container, and generating ultrasonic waves from an ultrasonic oscillator to apply ultrasonic vibrations to the mixture in the container using the vibrator. At this time, the magnetic stirrer was also used to rotate a rotor in the mixture in the container using magnetic force, thereby stirring the mixture. During mixing, an oil bath was used as a heating means to heat the mixture in the container (maximum temperature reached: 118°C). In this way, a polymerizable composition was prepared.

[0074] <Measurement of dispersed particle size> Two hours after the completion of the mixing, when the liquid temperature had dropped, a sample liquid for particle size distribution measurement was collected from the polymerizable composition, and the particle size distribution of the particles in the collected sample liquid was measured using a Zeta Potential / Particle Size Measurement System ELSZ-2 manufactured by Otsuka Electronics Co., Ltd. It can be evaluated that the smaller the dispersed particle size (average particle size) in the sample liquid measured by the particle size distribution meter, the higher the solubility of the indeno-fused naphthopyran compound in the polymerizable compound in the prepared polymerizable composition. The dispersibility was evaluated according to the following evaluation criteria. A: Dispersed particle size is 100 nm or less B: Dispersed particle size is over 100 nm

[0075] [Evaluation of liquid life] For each of the particles of Examples 1 and 2 and Comparative Examples 2 and 3, the liquid life of the polymerizable composition prepared using each particle was evaluated by the following method.

[0076] <Production of eyeglass lenses> A portion was taken out of the polymer composition prepared above on the day of preparation and N days after preparation, and eyeglass lenses having a photochromic layer were fabricated by the following method. A plastic lens substrate (manufactured by HOYA Corporation under the trade name EYAS; center thickness 2.5 mm, radius 75 mm, S-4.00) was immersed in a 10% by mass aqueous solution of sodium hydroxide (liquid temperature 60°C) for 5 minutes, then washed with pure water and dried. The polymeric composition was then applied by spin coating. Spin coating was performed using the method described in JP 2005-218994 A. The composition applied to the plastic lens substrate was then irradiated with ultraviolet light (wavelength 405 nm) in a nitrogen atmosphere (oxygen concentration 500 ppm or less) to cure the composition and form a photochromic layer. The photochromic layer thus formed was 40 μm thick. In this way, a spectacle lens having a photochromic layer was produced.

[0077] <Performance evaluation of photochromic layer> The surface of the photochromic layer of each eyeglass lens was irradiated with light from a xenon lamp through an aeromass filter for 15 minutes (900 seconds) to cause the photochromic compound in the photochromic layer to develop color. The transmittance (measurement wavelength: 550 nm) during this color development was measured using a spectrophotometer manufactured by Otsuka Electronics Co., Ltd. The light irradiation was carried out so that the irradiance and irradiance tolerance, as specified in JIS T7333:2005, were as shown in Table 1 below.

[0078] [Table 1]

[0079] The above transmittance (hereinafter referred to as "transmittance when colored") was compared between an eyeglass lens in which a photochromic layer was formed using a polymerizable composition on the day the polymerizable composition was prepared (initial sample) and an eyeglass lens in which a photochromic layer was formed using a polymerizable composition N days after preparation (aged sample). The longest number of days N during which the value obtained by subtracting the transmittance when colored of the initial sample from the transmittance when colored of the aged sample was within 1% is shown in Table 2 as the liquid life. It can be said that the longer the number of days N, the less the quality deterioration of the polymerizable composition over time.

[0080] The results are shown in Table 1.

[0081] [Table 2]

[0082] The results shown in Table 2 confirm that the particles of Examples 1 and 2 have excellent solubility in polymerizable compounds and that the polymerizable compositions prepared using the particles of Examples 1 and 2 have long liquid life.

[0083] For example, the polymerizable composition prepared in the above examples can be applied to a substrate and cured by irradiation with light to form a photochromic layer on the substrate.

[0084] Finally, the above-mentioned aspects will be summarized.

[0085] According to one embodiment, there is provided particles of an indeno-fused naphthopyran compound having a crystallinity of 60.00% or more and a maximum melting rate of 25% or less at a temperature of 200° C. or less on the melting curve.

[0086] The particles make it possible to produce a polymerizable composition in which the indeno-fused naphthopyran compound is dissolved in the polymerizable compound with high solubility and which has a long liquid life.

[0087] In one embodiment, the degree of association of the particles can be 50 or greater.

[0088] According to one aspect, there is provided a method for producing a photochromic article, the method comprising producing a polymerizable composition by the above-described production method, and curing the produced polymerizable composition to form a cured product containing a photochromic compound.

[0089] In one embodiment, the cured product can be a photochromic layer, and the method for producing the photochromic article can include forming the photochromic layer directly or indirectly on a substrate.

[0090] In one form, the photochromic article can be an eyeglass lens.

[0091] In one form, the photochromic article can be a lens for goggles.

[0092] In one form, the photochromic article can be the visor portion of a sun visor.

[0093] In one form, the photochromic article can be a shield member of a helmet.

[0094] The various aspects and configurations described herein may be combined in any combination of two or more.

[0095] The embodiments disclosed herein should be considered to be illustrative in all respects and not restrictive. The scope of the present invention is defined by the claims, not by the above description, and is intended to include all modifications within the meaning and scope of the claims. [Industrial Applicability]

[0096] The present invention is useful in the technical fields of eyeglasses, goggles, sun visors, helmets, etc.

Claims

1. A method for producing a polymerizable composition, comprising mixing particles of an indeno-fused naphthopyran compound with one or more polymerizable compounds, the indeno-fused naphthopyran compound has a crystallinity of 60.00% or more and a maximum melting rate of 25% or less at a temperature of 200°C or less on its melting curve; The method for producing a polymerizable composition, wherein the polymerizable compound contains an acyclic methacrylate having a molecular weight of 650 or more.

2. A method for producing a polymerizable composition as described in claim 1, wherein the degree of association of the indeno-condensed naphthopyran compound is 50 or more.

3. A method for producing a polymerizable composition described in claim 1 or 2, wherein the acyclic methacrylate having a molecular weight of 650 or more is polyalkylene glycol dimethacrylate.

4. Producing a polymerizable composition by the production method according to any one of claims 1 to 3; and curing the produced polymerizable composition to form a cured product containing a photochromic compound; A method for producing a photochromic article, comprising:

5. the cured product is a photochromic layer, 5. The method of making a photochromic article according to claim 4, comprising forming the photochromic layer directly or indirectly on a substrate.

6. The method for producing a photochromic article according to claim 4 or 5, wherein the photochromic article is a spectacle lens.

7. The method for producing a photochromic article according to claim 4 or 5, wherein the photochromic article is a lens for goggles.

8. The method for producing a photochromic article according to claim 4 or 5, wherein the photochromic article is a visor portion of a sun visor.

9. The method for producing a photochromic article according to claim 4 or 5, wherein the photochromic article is a shield member of a helmet.

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