Method for producing a composition, method for producing an ophthalmic lens

Abstract

The present invention provides a composition production method whereby it becomes possible to produce a composition which shows a reduced change in viscosity over time and can be cured into a cured film having excellent hardness (particularly scratch hardness). The composition production method according to the present invention includes: a step 1 for heating a mixture comprising a silsesquioxane having a cation-polymerizable group and metal oxide particles to a temperature higher than 60°C; and a step 2 for mixing the mixture obtained in the step 1 with a cation polymerization initiator to produce a composition.

Description

[Technical Field]

[0001] The present disclosure relates to methods for making compositions and methods for making eyeglass lenses. [Background technology]

[0002] In order to impart scratch resistance to a plastic spectacle lens substrate, a hard coat layer is sometimes disposed on the plastic spectacle lens substrate (for example, Patent Document 1). [Prior art documents] [Patent documents]

[0003] [Patent Document 1] Special Publication No. 2010-515778 Summary of the Invention

[0004] The present disclosure relates to a method for producing a composition, comprising: step 1 of heating a mixture containing a silsesquioxane having a cationically polymerizable group and metal oxide particles at a temperature above 60°C; and step 2 of mixing the mixture obtained in step 1 with a cationic polymerization initiator to produce a composition. DETAILED DESCRIPTION OF THE INVENTION

[0005] The method for producing the composition of the present disclosure will be described in detail below. From the viewpoint of ease of handling, it is desirable for the composition to have little change in viscosity over time. Also, from the viewpoint of application to hard coating layers and the like, it is desirable for the cured film formed using the composition to have excellent hardness. The composition produced by the method for producing a composition of the present disclosure exhibits little change in viscosity over time, and the cured film obtained using this composition has excellent hardness (particularly scratch hardness). The method for producing the composition of this embodiment will be described in detail below. In this specification, the symbol "to" is used to mean that the numerical values before and after it are included as the lower limit and upper limit.

[0006] [Manufacturing Method of Composition] The manufacturing method of the composition of this embodiment is a manufacturing method having Step 1 and Step 2. The above Step 1 is a step of heat-treating a mixture containing a silsesquioxane having a cation-polymerizable group and metal oxide particles at a temperature exceeding 60°C. Further, the above Step 2 is a step of mixing the mixture obtained in the above Step 1 and a cation polymerization initiator to produce a composition. As will be described later, by performing the heat treatment of Step 1 prior to Step 2, the change in viscosity during storage of the composition is suppressed. In addition, the composition produced by the manufacturing method of the composition of the present disclosure contains a silsesquioxane having a cation-polymerizable group and metal oxide particles, and thus is also excellent in scratch hardness. Hereinafter, each step in the manufacturing method of the composition of this embodiment will be described in detail.

[0007] [Step 1] Step 1 is a step of heating a mixture containing a silsesquioxane having a cation-polymerizable group and metal oxide particles at a temperature exceeding 60°C. When this Step 1 is carried out, it is presumed that due to a trace amount of acid derived from the metal oxide particles, the polymerization of the cation-polymerizable group possessed by the silsesquioxane proceeds, and a part of the silsesquioxane is prepolymerized. Hereinafter, first, the materials used in Step 1 will be described in detail, and then the procedure of the step will be described in detail.

[0008] [Silsesquioxane Having a Cation-Polymerizable Group] In the above Step 1, a silsesquioxane having a cation-polymerizable group (hereinafter, also simply referred to as "specific silsesquioxane") is used. A silsesquioxane is generally a silane compound having a basic skeleton represented by formula (1), which is obtained by hydrolyzing a trifunctional silane compound such as an alkoxysilane, a chlorosilane, and a silanol. As the structure of the silsesquioxane, in addition to an irregular form called a random structure, a ladder structure, a cage type (fully condensed cage type) structure, and an incomplete cage type structure (a partially cleaved structure of the cage type structure, in which some of the silicon atoms are missing from the cage type structure or some of the silicon-oxygen bonds in the cage type structure are cleaved) are known. In the following formula (1), R 3 represents an organic group. Formula (1) R 3 -SiO 3 / 2 A specific silsesquioxane preferably has a basic skeleton in which R in formula (1) 3 is an organic group having a cationically polymerizable group.

[0009] The structure of the specific silsesquioxane is not particularly limited, and it may be any of the above random structure, ladder structure, cage type structure, and incomplete cage type structure, or a mixture of plural types of structures.

[0010] The cationically polymerizable group equivalent in the specific silsesquioxane is not particularly limited, but is preferably 50 to 500 g / eq., more preferably 150 to 300 g / eq. in terms of the hardness of the cured film that can be formed using the composition being more excellent.

[0011] The cationically polymerizable group in the specific silsesquioxane is not particularly limited, and examples thereof include an oxetanyl group and an epoxy group.

[0012] The above oxetanyl group is a group represented by the following formula (2). R 2 represents a hydrogen atom or an alkyl group (for example, a methyl group, an ethyl group, and a propyl group, etc.). * represents the bonding position.

[0013]

Chemical formula

[0014] The above epoxy group is a group represented by the following formula (3). R 1 represents a hydrogen atom or an alkyl group (for example, a methyl group, an ethyl group, a propyl group, etc.). * represents the bonding position.

[0015] [Chemical formula]

[0016] The above specific silsesquioxane may be synthesized by a known method or a commercially available product may be used. Examples of commercially available products include those manufactured by Toagosei Co., Ltd.: OX-SQ TX-100, OX-SQ SI-20, OX-SQ HDX, and OX-SQ ME-20.

[0017] (Metal oxide particles) In the above step 1, metal oxide particles are used. The type of metal oxide particles is not particularly limited, and known metal oxide particles may be mentioned. Examples of metal oxide particles include particles of oxides of at least one metal selected from Si, Al, Sn, Sb, Ta, Ce, La, Fe, Zn, W, Zr, In, and Ti. Among them, from the viewpoint of handleability, the metal oxide particles are preferably particles of an oxide containing Si (silicon oxide particles), particles of an oxide containing Sn (tin oxide particles), particles of an oxide containing Zr (zirconium oxide particles), or particles of an oxide containing Ti (titanium oxide particles). That is, it is preferable that the metal oxide particles contain at least one atom selected from the group consisting of Si, Sn, Zr, and Ti. Note that the metal oxide particles may contain only one kind of metal (metal atom) exemplified above, or may contain two or more kinds of metals (metal atoms).

[0018] The average particle size of the metal oxide particles is not particularly limited. For example, 1 to 200 nm is preferable, and 5 to 30 nm is more preferable. If it is within the above range, the dispersion stability of the metal oxide particles in the composition is more excellent, and the whitening of the cured product can be more suppressed. In addition, the above average particle size is obtained by measuring the diameters of 100 or more metal oxide particles with a transmission microscope and calculating their arithmetic mean. When the metal oxide particles are not circular, the major axis is taken as the diameter.

[0019] The metal oxide particles may be used in a colloidal state dispersed in a solvent. For example, when the metal oxide particles contain Si as a metal, colloidal silica can be used.

[0020] When using colloidal silica as the metal oxide particles, examples of commercially available products include: “OSCAL” series manufactured by JGC Catalysts and Chemicals Ltd., “Snowtex” series manufactured by Nissan Chemical Industries, Ltd., and “QuattroN” series manufactured by Fuso Chemical Industry Co., Ltd.

[0021] In Step 1, other components other than the specific silsesquioxane and metal oxide particles described above may be used.

[0022] (Solvent) In the above Step 1, a solvent may be used. The solvent here may be a solvent added in Step 1, or when using commercially available metal oxide particles as a colloidal solution, it may be the dispersion medium thereof. The solvent is not particularly limited and may be water or an organic solvent. Examples of the organic solvent include alcohol solvents, ketone solvents, ether solvents, ester solvents, hydrocarbon solvents, halogenated hydrocarbon solvents, amide solvents, sulfone solvents, and sulfoxide solvents. As the alcohol-based solvent, an alcohol-based solvent having 10 or less carbon atoms is preferable, and an alcohol-based solvent having 5 or less carbon atoms (for example, isopropanol) is more preferable. Further, the alcohol-based solvent may be a polyhydric alcohol having two or more hydroxy groups in one molecule.

[0023] As other components, in addition to the above solvents, for example, ultraviolet absorbers, surfactants, polymerization inhibitors, anti-aging agents, coating film regulators, light stabilizers, antioxidants, anti-coloring agents, dyes, fillers, and internal release agents can be mentioned.

[0024] (Procedure of Step 1) In the above Step 1, a mixture containing a specific silsesquioxane and metal oxide particles is heated above 60°C. The method for obtaining a mixture containing a specific silsesquioxane and metal oxide particles is not particularly limited, and each component may be mixed all at once, or may be added and mixed separately. When obtaining the above mixture, a stirring treatment may be carried out as necessary.

[0025] The mixing ratio of the specific silsesquioxane and metal oxide particles in the mixture is not particularly limited, and the mass ratio of the content of the metal oxide particles to the content of the specific silsesquioxane in the mixture is preferably 0.2 to 10.0, and more preferably 0.5 to 2.0. The total content of the specific silsesquioxane and metal oxide particles in the mixture is not particularly limited, but the total content of the specific silsesquioxane and metal oxide particles is preferably 80 to 100% by mass, and more preferably 90 to 100% by mass, based on the total solid content in the mixture. Note that the solid content in the mixture means the components excluding the solvent in the mixture. Even if the component is liquid, it is calculated as the solid content.

[0026] As described above, the mixture may contain other components other than the specific silsesquioxane and metal oxide particles. Examples of other components include the above-mentioned solvents. The content of the solvent in the mixture is not particularly limited, but is preferably 30 to 60% by mass, more preferably 40 to 60% by mass, based on the total mass of the mixture.

[0027] The heating method of the mixture in Step 1 is not particularly limited, and examples include known methods and methods using known heating devices. Examples of the heating device include electric heaters such as hot plates and mantle heaters, infrared heaters, oil bath devices such as oil baths, and water bath devices such as water baths. Also, the above heating may be performed in an open system or a closed system. However, since the temperature of the mixture can be raised to a temperature higher than the boiling point of the solvent in the mixture, and even if there are volatile components contained in the mixture, it can be heated at a high temperature, it is preferably performed in a closed system. Also, during heating, a stirring treatment may be performed as necessary.

[0028] The heating temperature of the mixture is above 60°C, preferably 80°C or higher, more preferably 100°C or higher, even more preferably 120°C or higher, and particularly preferably 140°C or higher. Also, the upper limit of the heating temperature is not particularly limited, and is preferably 200°C or lower. Note that the above heating temperature refers to the set temperature in the heating device (such as a hot plate) used when heating the above mixture.

[0029] The heating time of the mixture is not particularly limited as long as it is appropriately selected according to the above heating temperature. For example, it is preferably 1 hour or longer, more preferably 3 hours or longer, even more preferably 4 hours or longer, and particularly preferably more than 4 hours. Also, as the upper limit of the heating time, for example, it is preferably 12 hours or shorter, more preferably 10 hours or shorter, even more preferably 8 hours or shorter, particularly preferably less than 8 hours, and most preferably 7 hours or shorter.

[0030] <Step 2> Step 2 is a step of producing a composition by mixing the mixture obtained in Step 1 and a cationic polymerization initiator. First, the materials used in Step 2 will be described in detail, and then the procedure of the step will be described in detail.

[0031] (Cationic polymerization initiator) In the above Step 2, a cationic polymerization initiator is used. The cationic polymerization initiator is not particularly limited, and examples thereof include a thermal cationic polymerization initiator and a photo cationic polymerization initiator.

[0032] The type of the thermal cationic polymerization initiator is not particularly limited, and known thermal cationic polymerization initiators can be mentioned. Examples of the thermal cationic polymerization initiator include onium salts such as sulfonium salts, anilinium salts, pyridinium salts, toluidinium salts, phosphonium salts, and iodonium salts. Note that these onium salts contain anions such as hexafluorophosphate anion (PF6 - ), tetrafluoroborate anion (BF4 - ), hexafluoroantimonate anion (SbF6 - ), and hexafluoroarsenate anion (AsF6 - ). In addition, the sulfonium cation can be a triaryl sulfonium cation. Examples of the triaryl sulfonium cation include a triphenyl sulfonium cation in which the aryl group has a substituted phenyl group having an alkyl group, a thioether group, an alkoxy group, etc. as a substituent. Specific examples of the triaryl sulfonium cation include diphenyl[4-(phenylthio)phenyl]sulfonium cation, triphenyl sulfonium cation, and alkyltriphenyl sulfonium cation. Commercially available products of the above thermal cationic polymerization initiator include, for example, Adeka Optron CP-66 manufactured by ADEKA Corporation, and Sun-Aid SI-150L manufactured by Sanshin Chemical Industry Co., Ltd.

[0033] The type of the photo cationic polymerization initiator is not particularly limited, and known photo cationic polymerization initiators can be mentioned. Examples of the photo cationic polymerization initiator include onium salts such as iodonium salts (for example, aromatic iodonium salts) and sulfonium salts (for example, aromatic sulfonium salts), halogen-containing compounds such as s-triazine derivatives, sulfone compounds, sulfonic acid compounds, sulfonimide compounds, and diazomethane compounds. Among them, from the viewpoint of curability, an aromatic sulfonium salt is preferably used as the photo cationic polymerization initiator.

[0034] (Other components) In Step 2, other components other than the cationic polymerization initiator may be used. Examples of the other components include solvents, ultraviolet absorbers, surfactants, polymerization inhibitors, anti-aging agents, coating film regulators, light stabilizers, antioxidants, anti-coloring agents, dyes, fillers, and internal mold release agents. Examples of the solvent include the solvents described in Step 1 above.

[0035] Examples of the above ultraviolet absorber include hydroxy phenyl triazine-based ultraviolet absorbers having a structure in which three hydrogen atoms on the triazine ring are substituted with phenyl groups, and benzotriazole-based ultraviolet absorbers having a benzotriazole structure. Examples of the surfactant include polyether-modified silicone-based surfactants having a polyether structure.

[0036] (Procedure of Step 2) In the above Step 2, the mixture obtained in the above Step 1 and the cationic polymerization initiator are mixed to produce a composition. The method of mixing the mixture and the cationic polymerization initiator is not particularly limited, and the cationic polymerization initiator may be added to the mixture in portions or added all at once. During mixing, a stirring treatment may be carried out as necessary.

[0037] The amount of the cationic polymerization initiator used is not particularly limited, but as described below, 0.1 to 2.0% by mass is preferable, and 0.5 to 1.0% by mass is more preferable, based on the total amount of the specific silsesquioxane used in Step 1 and the amount of the metal oxide particles used in Step 1.

[0038] In the method for producing the composition of the present embodiment, the amount of the metal oxide particles used in Step 1 is not particularly limited with respect to the total amount of the specific silsesquioxane used in Step 1, the amount of the metal oxide particles used in Step 1, and the amount of the cationic polymerization initiator used in Step 2, but 40 to 60% by mass is preferable, and more preferably more than 40% by mass and less than 60% by mass.

[0039] <Other steps> The method for producing the composition of the present embodiment may have other steps in addition to Step 1 and Step 2. As the other step, when the mixture obtained in Step 1 contains a solvent, Step 3 of replacing the solvent in the mixture with another solvent may be carried out between Step 1 and Step 2. The procedure of Step 3 is not particularly limited. For example, a method of volatilizing and removing the first solvent contained in the mixture obtained in Step 1 and adding a second solvent of a different type from the first solvent that has been volatilized to the obtained mixture can be mentioned. Also, a method of adding a second solvent of a different type from the first solvent contained in the mixture obtained in Step 1 to the mixture and then volatilizing and removing the first solvent from the obtained mixture may also be used. The method of volatilizing the solvent is not particularly limited. For example, a method of volatilizing the solvent by setting reduced pressure conditions can be mentioned.

[0040] The solvent (the above-mentioned other solvent) used in Step 3 is not particularly limited, and examples include the solvents described in Step 1 above. Among them, methanol, butyl cellosolve, or methyl ethyl ketone is preferable.

[0041] 〔Composition〕 The composition produced by the manufacturing method of the composition of the present embodiment contains a cationic polymerization initiator, and thus can be used as a curable composition. The composition contains the specific silsesquioxane and metal oxide particles described above. Also, as described above, it is presumed that the composition contains a prepolymerized specific silsesquioxane.

[0042] The content of the specific silsesquioxane in the composition of the present embodiment is not particularly limited, but in terms of the scratch hardness of the cured film formed using the composition being more excellent and the change in viscosity of the composition over time being smaller, 35 to 70% by mass is preferable, and 35 to 60% by mass is more preferable, based on the total solid content in the composition of the present embodiment. The solid content in the composition refers to the components constituting the cured film formed using the above composition, and the specific silsesquioxane, metal oxide particles, and thermal cationic polymerization initiator described above are applicable, and the solvent is not included in the solid content. Also, even if the component is liquid, if it is a component constituting the cured film, it is calculated as the solid content.

[0043] The content of the metal oxide particles in the composition of the present embodiment is not particularly limited, but in terms of the scratch hardness of the cured film formed using the composition being more excellent and the change in viscosity of the composition over time being smaller, 35 to 70% by mass is preferable, and 35 to 60% by mass is more preferable, based on the total solid content in the composition of the present embodiment.

[0044] The content of the cationic polymerization initiator in the composition of the present embodiment is not particularly limited, but in terms of the scratch hardness of the cured film formed using the composition being more excellent and the change in viscosity of the composition over time being smaller, 0.1 to 3.0% by mass is preferable, and 0.2 to 1.5% by mass is more preferable, based on the total solid content in the composition of the present embodiment.

[0045] When the composition of the present embodiment contains an ultraviolet absorber, the content of the ultraviolet absorber is not particularly limited, but 0.1 to 10% by mass is preferable, and 0.5 to 2.0% by mass is more preferable, based on the total solid content in the composition of the present embodiment. When the composition of the present embodiment contains a surfactant, the content of the surfactant is not particularly limited. However, with respect to the total solid content in the composition of the present embodiment, 0.1 to 10% by mass is preferable, and 0.5 to 2.0% by mass is more preferable.

[0046] The viscosity (20 °C) of the above composition is not particularly limited. However, from the viewpoint of more excellent scratch hardness of the cured film formed using the composition or excellent workability when forming the hard coat layer, 60.0 cP or less is preferable, 30.0 cP or less is more preferable, and 20.0 cP or less is even more preferable. The lower limit is not particularly limited, but it is often 5.0 cP or more, and more often 10.0 cP or more. The above viscosity can be measured using a known measuring device (for example, a cone plate type viscometer, etc.).

[0047] The solid content concentration of the above composition is not particularly limited. However, with respect to the total mass of the composition, 40 to 70% by mass is preferable, and 50 to 60% by mass is more preferable.

[0048] The above composition can be used, for example, as a composition for forming a cured film on a spectacle lens substrate.

[0049] 〔Method for manufacturing spectacle lenses〕 The present disclosure also includes a method for manufacturing a spectacle lens, which includes a step of forming a cured film on a spectacle lens substrate using the composition manufactured by the method for manufacturing the composition of the present embodiment. Hereinafter, first, the materials and members used in this step will be described in detail, and then the procedure of the step will be described in detail.

[0050] The composition used in this step is as described above. Examples of the type of the spectacle lens substrate used in this step include a spectacle lens substrate composed of an organic material or an inorganic material. Examples of the spectacle lens substrate include a finish lens that is optically finished on both the convex and concave surfaces and molded to the desired diopter, a semi-finish lens in which only the convex surface is finished as an optical surface (e.g., a spherical surface, a rotationally symmetric aspherical surface, a progressive surface, etc.), and a lens in which the concave surface of the semi-finish lens is machined and polished according to the prescription of the wearer. Examples of the organic material (so-called resin) include (meth)acrylic resins, thiourethane resins, allyl resins, episulfide resins, polycarbonate resins, polyurethane resins, polyester resins, polystyrene resins, polyethersulfone resins, poly-4-methylpentene-1 resins, and diethylene glycol bisallyl carbonate resins (CR-39). Examples of the inorganic material include glass.

[0051] A primer layer may be disposed on the spectacle lens substrate.

[0052] From the viewpoint of handleability, the thickness of the spectacle lens substrate may be 1 to 30 mm. The above thickness (average thickness) is obtained, for example, by measuring the thicknesses at any five points and calculating their arithmetic mean. The spectacle lens substrate preferably has translucency and may be either transparent or opaque. It may also be colored.

[0053] (Procedure of the process) The method for forming a cured film on the spectacle lens substrate using the composition is not particularly limited, and examples include a method in which the spectacle lens substrate and the composition are brought into contact to form a coating film on the spectacle lens substrate, and then the coating film is subjected to a curing treatment to form a cured film. Hereinafter, the procedure of the above method will be described in detail.

[0054] The method for bringing the spectacle lens substrate and the composition into contact is not particularly limited, and the composition may be applied onto the spectacle lens substrate, or the spectacle lens substrate may be immersed in the composition. The procedure for the curing treatment is not particularly limited, and heat treatment is preferred. The conditions for the heat treatment are not particularly limited, and the optimal conditions are selected according to the type of the thermal cationic polymerization initiator used. Among them, the heating temperature is preferably 30 to 120 °C, more preferably 50 to 100 °C, the heating time is preferably 5 to 360 minutes, and more preferably 10 to 60 minutes.

[0055] The film thickness of the cured film is not particularly limited. For example, it can be 1.0 μm or more, and preferably 5.0 μm or more. The upper limit of the film thickness can be, for example, 30.0 μm or less, and preferably 20.0 μm or less. The above film thickness is the average film thickness. As the measurement method, the film thicknesses of any five points of the cured film are measured and their arithmetic mean is obtained. An optical film thickness meter can also be used.

Examples

[0056] Hereinafter, the compositions of the present disclosure will be described in more detail with reference to Examples and Comparative Examples, but they are not limited by these Examples.

[0057] <Example 1> (Preparation of Composition (Step 1)) The composition of Example 1 was prepared according to the following procedure. Into a glass container equipped with a stir bar, (A) a cationic curable silsesquioxane (manufactured by Toagosei Co., Ltd.: OX-SQ TX-100) (27.13 g) as a silsesquioxane, and (B) colloidal silica (manufactured by JGC Catalysts and Chemicals Ltd.: OSCAL-1432E, isopropanol dispersion, solid content 30% by mass) (90.45 g) as metal oxide particles were added to form a mixture. The obtained mixture was stirred for 6 hours while heating on a hot plate set at 160 °C. At this time, the glass container was in a sealed state with a lid, and the solvent in the mixture was in a reflux state.

[0058] (Preparation of Composition (Step 3)) After the completion of heating, the obtained reaction solution was cooled to room temperature over night, and then butyl cellosolve (10.85 g) was added to the cooled reaction solution as a solvent for film formation. Next, isopropanol was distilled off from the reaction solution over 2 hours under reduced pressure at 40 °C. Methanol (33.40 g) was added to the obtained crude product to obtain a liquid composition X1.

[0059] (Preparation of Composition (Step 2)) To a glass container equipped with a stir bar, the liquid composition X1 (98.52 g) obtained in Step 1 above, as a (D) cationic polymerization initiator, SbF6 - system sulfonium salt (manufactured by Sanshin Chemical Industry Co., Ltd.: Sun-Aid SI-150L) (0.52 g), as an (F) ultraviolet absorber, hydroxyphenyltriazine-based ultraviolet absorber (manufactured by BASF Japan Ltd.: Tinuvin 477) (0.62 g), and as a (G) surfactant, polyether-modified silicone (manufactured by Toray Dow Corning Co., Ltd.: DOWSIL L-7001) (0.33 g) were added and mixed to obtain Composition 1.

[0060] <Examples 2, 5 to 9, Comparative Examples 2 to 3> When heating the mixture, Compositions 2, 5 to 9, and Compositions C2 to C3 were obtained according to the same procedure as in Example 1, except that the set temperature of the hot plate and the heating time were changed to the values described in Table 1. Note that Comparative Example 2 corresponds to an example in which the heat treatment in Step 1 was not performed.

[0061] <Example 3> The amount of cationically curable silsesquioxane (manufactured by Toagosei Co., Ltd.: OX-SQ TX-100) used was changed from 27.13 g to 32.56 g, and the amount of colloidal silica (manufactured by JGC Catalysts & Chemicals Ltd.: OSCAL-1432E, isopropanol dispersion, solid content 30 mass%) used was changed from 90.45 g to 72.36 g. According to the same procedure as in Example 1, Composition 3 was obtained.

[0062] <Example 4> The amount of the cation-curable silsesquioxane (manufactured by Toagosei Co., Ltd.: OX-SQ TX-100) was changed from 27.13 g to 21.71 g, and the amount of the colloidal silica (manufactured by JGC Catalysts & Chemicals Ltd.: OSCAL-1432E, isopropanol dispersion, solid content 30% by mass) was changed from 90.45 g to 108.7 g. Composition 4 was obtained according to the same procedure as in Example 1 except for the above changes.

[0063] <Comparative Example 1> Into a glass container equipped with a stir bar, 3-glycidoxypropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd.: KBM403) (19.70 g) was added as the (C) hydrolyzable silicon compound, and while stirring the mixture, 0.1 N hydrochloric acid (4.50 g) was gradually added dropwise. After the addition was completed, the mixture was stirred at room temperature for 24 hours. Subsequently, to the obtained mixture, as the (B) metal oxide particles, titanium oxide colloid (manufactured by JGC Catalysts & Chemicals Ltd.: NE58, solid content 30% by mass) (35.60 g), as the (E) catalyst, aluminum acetylacetonate (manufactured by Kishida Chemical Co., Ltd.) (1.60 g), methanol (38.50 g), and as the (G) surfactant, polyether-modified silicone (manufactured by Toray Dow Corning Co., Ltd.: DOWSIL L-7001) (0.10 g) were added and mixed to obtain Composition C1 of Comparative Example 1.

[0064] <Evaluation> Using the compositions obtained in the above Examples and Comparative Examples, the following evaluations were carried out. The results are summarized in Table 1 described later.

[0065] (Viscosity stability over time) For each composition of the Examples or Comparative Examples, the viscosity stability over time was measured by the following method. Before the standing treatment described later, the temperature of the composition was adjusted to 20 °C, and the initial viscosity of the composition was measured using a vibrating viscometer (manufactured by Yamakita Electric Co., Ltd.: VM-100). After the measurement of the above initial viscosity, the composition was allowed to stand for 24 hours under the conditions of 5 °C and in the dark, and then the viscosity of the composition after the standing treatment was measured as the viscosity over time in the same manner as the measurement of the above initial viscosity. From the values of the above initial viscosity and the viscosity over time, the rate of change of viscosity over time was determined as follows, and the viscosity stability over time was evaluated based on the following evaluation criteria.

[0066] Rate of change of viscosity over time (%) = 100 × (|(viscosity over time) - (initial viscosity)| / (initial viscosity)) (Evaluation criteria for viscosity stability over time) A: Rate of change of viscosity over time is 10% or less B: Rate of change of viscosity over time is more than 10% and 50% or less C: Rate of change of viscosity over time is more than 50% and 200% or less D: Rate of change of viscosity over time is more than 200%

[0067] (Evaluation of pencil hardness) Using the compositions of each example or comparative example, a plastic spectacle lens substrate with a cured film was produced by the following method. First, as the plastic spectacle lens substrate, a lens with a refractive index of 1.60 ((manufactured by Nikon Essilor Co., Ltd.): Nikon Lite AS fabric S - 3.00D) was used. By the spin - coating method, the composition of each example or comparative example was applied to one surface of this plastic spectacle lens substrate. Specifically, the plastic spectacle lens substrate was rotated at 300 rpm for 1 second, and while rotating, 4 ml of the above composition was dropped from the center part to the outer peripheral part of the plastic spectacle lens substrate. Then, the plastic spectacle lens substrate coated with the above composition was rotated at 300 rpm for 15 seconds, further, it was made to reach 400 rpm in 5 seconds and then rotated for 1 second, further, it was made to reach 700 rpm in 5 seconds and then rotated for 1 second, further, it was made to reach 2000 rpm in 9.9 seconds and then rotated for 1 second, and a plastic spectacle lens substrate with a coating film was obtained. Next, the obtained plastic spectacle lens substrate with a coating film was heated at 100 °C for 20 minutes, and then further heated at 100 °C for 1 hour to form a cured film, and a plastic spectacle lens substrate with a cured film was obtained. The film thickness of the obtained cured film was 15 μm.

[0068] Using the plastic spectacle lens substrate with a cured film produced using the composition of each example or comparative example, the scratch hardness (pencil hardness) was evaluated according to the following procedure. Specifically, in accordance with the method specified in JIS K5600-5-4 (1999), the pencil hardness of the cured film was measured and evaluated based on the following evaluation criteria. A: Pencil hardness is 4H or higher B: Pencil hardness is higher than 3H and less than 4H C: Pencil hardness is higher than 2H and less than 3H

[0069] (Evaluation of scratch hardness) Using the method described in (Evaluation of pencil hardness), a plastic spectacle lens substrate with a cured film was produced using the composition of each example or comparative example. Using the obtained plastic spectacle lens substrate with a cured film, the scratch hardness was evaluated according to the following procedure. Using a friction and wear tester (manufactured by Shin-Tech Co., Ltd.: Tribogear TYPE40), a sapphire scratching needle (manufactured by Shin-Tech Co., Ltd.: BH0001-02) with a tip radius of 0.01 mm and a vertex angle of 60° was vertically contacted with the convex surface (the surface with the cured film) of the plastic spectacle lens substrate with a cured film produced by the above procedure. While applying a vertical load of 10 g to the scratching needle, it was moved once at a speed of 60 mm / min for a length of 10 mm. Using a scanning white light interference microscope (manufactured by Hitachi, Ltd.: VS1000), the depth of the scratch mark on the convex surface of the above plastic spectacle lens substrate with a cured film was measured, and the scratch hardness was evaluated based on the following evaluation criteria. A: The depth of the scratch mark is 50 nm or less B: The depth of the scratch mark is more than 50 nm and 80 nm or less C: The depth of the scratch mark is more than 80 nm

[0070] The above evaluation results are shown in Table 1. The description of each numerical value shown in the table indicates the usage amount (parts by mass) of each component in the composition. In the table, the column of "B / A + B + D (mass%)" indicates the amount of the (B) metal oxide particles used with respect to the total amount of the amounts of the (A) silsesquioxane, the (B) metal oxide particles, and the (D) cationic polymerization initiator used in the production method of the present disclosure (unit: mass%). In the table, the column of "heating temperature" indicates the set temperature of the hot plate when heating the mixture in the above step 1. In the table, the column of "heating time" indicates the heating time (stirring time) when heating the mixture in the above step 1. In the table, the column of "film thickness" indicates the film thickness of the cured film. The film thickness is a value measured by an optical film thickness meter. In the table, the column of "hardness - 1" indicates the result of the above (evaluation of pencil hardness), the column of "hardness - 2" indicates the result of the above (evaluation of scratch hardness), and the column of "viscosity" indicates the result of the above (viscosity stability over time).

[0071]

Table 1

[0072] As shown in Table 1, it was confirmed that the composition of the present disclosure exhibits the desired effects.

Claims

1. Step 1 of heating a mixture containing a silsesquioxane having a cation-polymerizable group and metal oxide particles at 80°C or higher; Step 2 of mixing the mixture obtained in Step 1 with a cationic polymerization initiator to produce a composition, A method for producing a composition, comprising: The method for producing a composition, wherein the metal oxide particles are selected from the group consisting of particles of an oxide containing Si and particles of an oxide containing Sn.

2. The method for producing a composition according to Claim 1, wherein the heating time is 1 hour or longer.

3. The method for producing a composition according to Claim 1, wherein the heating temperature is 100°C or higher.

4. The method for producing a composition according to Claim 1, wherein the amount of the metal oxide particles used is 40 to 60% by mass based on the total amount of the amount of the silsesquioxane having a cation-polymerizable group used, the amount of the metal oxide particles used, and the amount of the cationic polymerization initiator used.

5. The method for producing a composition according to Claim 1, wherein the cation-polymerizable group is an oxetanyl group.

6. A method for producing an eyeglass lens, comprising a step of forming a cured film on an eyeglass lens substrate using the composition produced by the production method according to any one of Claims 1 to 5.

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