Eyeglass lens, antifouling agent composition, and method for manufacturing eyeglass lens

Abstract

An embodiment of the present disclosure pertains to an eyeglass lens comprising an antifouling layer which is a condensate of an antifouling agent composition containing (A) a compound having a silyl group and a fluorinated alkyl group, (B) a compound having a silyl group at one end and a reactive group at the other end, and (C) a chain-like fluorine compound having no reactive group.

Description

[Technical Field]

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

[0002] When eyeglass lenses are used, stains caused by the adhesion of hand marks, fingerprints, sweat, cosmetics, etc. become easily noticeable. Therefore, an antifouling layer is provided on the surface to make the lenses less susceptible to staining or to make it easier to wipe off stains. For example, Patent Document 1 describes an eyeglass lens having a fluorine-containing antifouling film on its surface, in which the surface free energy is 10.0 mJ / m 2 The basic component of the surface free energy is 0.95 mJ / m 2 The following describes an eyeglass lens. [Prior art documents] [Patent documents]

[0003] [Patent Document 1] Japanese Patent Application Publication No. 2018-004921 Summary of the Invention [Problem to be solved by the invention]

[0004] The spectacle lenses with the antifouling layer disclosed in Patent Document 1 are easy to wipe clean of fingerprints and other surface deposits. However, they have the problem that the surface becomes slippery and axis misalignment is likely to occur during the edging process, in which the spectacle lenses are cut to fit the shape of the frame.

[0005] One embodiment of the present disclosure relates to a spectacle lens that has excellent wiping properties and suppresses the occurrence of axis misalignment during edging, an antifouling agent composition, and a method for manufacturing a spectacle lens. [Means for solving the problem]

[0006] The present inventors have discovered that by using an antifouling agent composition containing a compound (A) having a silyl group and a fluorinated alkyl group, a compound (B) having a silyl group at one end and a reactive group at the other end, and a chain fluorine compound (C) having no reactive group, it is possible to obtain eyeglass lenses that are excellent in wiping properties and that suppress the occurrence of axis misalignment during edging.

[0007] One embodiment of the present disclosure comprises: a compound (A) having a silyl group and a fluorinated alkyl group; A compound (B) having a silyl group at one end and a reactive group at the other end; The present invention relates to a spectacle lens having an antifouling layer which is a condensate of an antifouling agent composition containing a chain fluorine compound (C) having no reactive group.

[0008] One embodiment of the present disclosure comprises: a compound (A) having a silyl group and a fluorinated alkyl group; A compound (B) having a silyl group at one end and a reactive group at the other end; a chain fluorine compound (C) having no reactive group; The present invention relates to an antifouling composition comprising:

[0009] One embodiment of the present disclosure comprises: a compound (A) having a silyl group and a fluorinated alkyl group; A compound (B) having a silyl group at one end and a reactive group at the other end; The present invention relates to a method for producing an eyeglass lens, comprising a step of forming an antifouling layer on the eyeglass lens using an antifouling agent composition containing a chain fluorine compound (C) that does not have a reactive group. [Effects of the Invention]

[0010] According to one embodiment of the present disclosure, it is possible to provide an eyeglass lens, an antifouling agent composition, and a method for manufacturing an eyeglass lens that have excellent wiping properties and that suppress the occurrence of axial misalignment during edging. [Brief explanation of the drawings]

[0011] [Figure 1] FIG. 1 is a schematic cross-sectional view of a spectacle lens 1 of the present embodiment. [Figure 2] FIG. 2 is a diagram showing an outline of the axis misalignment test. DETAILED DESCRIPTION OF THE INVENTION

[0012] Hereinafter, embodiments of the present disclosure will be described in detail, but the present disclosure is not limited thereto and various modifications are possible without departing from the spirit of the present disclosure. In this specification, numerical ranges indicated using "to" include the numerical values ​​before and after "to" as the minimum and maximum values, respectively. When a component having a silyl group is contained in the antifouling composition, the content of each component is a value calculated based on the assumption that the silyl group is a trimethoxysilyl group.

[0013] [Eyeglass lenses] The eyeglass lens of this embodiment is a compound (A) having a silyl group and a fluorinated alkyl group; A compound (B) having a silyl group at one end and a reactive group at the other end; and a chain fluorine compound (C) having no reactive group, and an antifouling layer which is a vapor deposition of an antifouling composition containing the compound. The spectacle lens of this embodiment exhibits excellent wiping properties and suppresses the occurrence of axis misalignment. The reason for this effect is not clear, but the antifouling composition contains compound (A) that forms an antifouling layer with excellent wiping properties, compound (B) that forms an antifouling layer that can suppress axis misalignment, and a chain fluorine compound (C) that does not have a reactive group. The silyl groups of compound (A) and compound (B) condense during vapor deposition of the antifouling composition, forming an antifouling layer. On the other hand, it is thought that the inclusion of chain fluorine compound (C) that does not have a reactive group allows the fluorine compound to seep onto the surface of the antifouling layer, forming an antifouling layer that is particularly excellent in wiping properties.

[0014] 1 is a schematic cross-sectional view of a spectacle lens 1 of this embodiment. The spectacle lens 1 of this embodiment includes a lens substrate 11, a hard coat layer 21f provided on the object-side surface 11a of this lens substrate 11, a functional layer 31f provided on the object-side surface 21fa of this hard coat layer 21f, and an antifouling layer 41f provided on the object-side surface 31fa of this functional layer 31f.

[0015] When the lens substrate 11 is a finished lens, the eyeglass lens 1 of this embodiment further comprises a hard coat layer 21b provided on the eyeball-side surface 11b of the lens substrate 11, a functional layer 31b provided on the eyeball-side surface 21bb of this hard coat layer 21b, and an antifouling layer 41b provided on the eyeball-side surface 31bb of this functional layer 31b.

[0016] Although not shown, an underlayer may be provided between the lens substrate 11 and the hard coat layer 21f, or between the lens substrate 11 and the hard coat layer 21b. Each layer in the eyeglass lens of this embodiment will be described below.

[0017] <Anti-fouling layer> The antifouling layer is a condensate of an antifouling composition. The condensate is formed by condensing at least a portion of the antifouling composition. The antifouling layer may be formed on a hard coat layer or a functional layer, but is preferably formed on an antireflection layer. The antifouling layer is preferably located on the outermost surface.

[0018] (Antifouling composition) The antifouling composition contains a compound (A) having a silyl group and a fluorinated alkyl group, a compound (B) having a silyl group at one end and a reactive group at the other end, and a chain fluorine compound (C) having no reactive group.

[0019] (Compound (A)) The antifouling agent composition contains a compound (A) having a silyl group and a fluorinated alkyl group (hereinafter also simply referred to as "compound (A)"), which can improve the wipeability of the formed antifouling layer from fingerprints, etc. Compound (A) is preferably linear.

[0020] The compound (A) contains a silyl group, which allows a condensation reaction to occur during vapor deposition to form an antifouling layer. Examples of the silyl group include trialkoxysilyl groups such as trimethoxysilyl, triethoxysilyl, tripropyloxysilyl, and trihexyloxysilyl. Compound (A) preferably contains a silyl group at the molecular terminal.

[0021] The compound (A) has a fluorinated alkyl group, which can improve the wipeability of fingerprints and the like from the antifouling layer. The fluorinated alkyl group is, for example, a perfluoroalkyl group. The number of carbon atoms in the fluorinated alkyl group is preferably 1 to 20, more preferably 1 to 10, and even more preferably 1 to 3. The compound (A) preferably has a fluorinated alkyl group at a molecular terminal.

[0022] From the viewpoint of improving the wipeability of fingerprints and the like from the stain-resistant layer, the compound (A) preferably has a fluorinated alkylene oxide chain. Examples of the fluorinated alkylene oxide chain include a polyperfluoromethylene oxide group, a polyperfluoroethylene oxide group, and a polyperfluoropropylene oxide group. The number of fluorinated alkylene oxide units in the fluorinated alkylene oxide chain is preferably 10 to 100, more preferably 30 to 100, and even more preferably 50 to 90.

[0023] More specifically, the compound (A) is represented by the formula (1): [ka] (In the formula, R 1 are each independently a monovalent hydrocarbon group having 1 to 6 carbon atoms, R2 are each independently a divalent hydrocarbon group having 1 to 6 carbon atoms, and n is 0 or 1; R 3 are each independently a divalent hydrocarbon group having 1 to 4 carbon atoms, and m is 0 to 10; Rf 4 are each independently a divalent fluorinated hydrocarbon group having 1 to 4 carbon atoms, and p is 10 to 100; Rf 5 is a fluorinated alkyl group having 1 to 20 carbon atoms. ) is preferred.

[0024] R 1 Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, and a hexyl group. Among these, a methyl group is preferred. R 2 Examples of the alkyl group include a methanediyl group, an ethanediyl group, a propanediyl group, and a hexanediyl group. R 3 Examples of m include a methanediyl group, an ethanediyl group, and a propanediyl group. m is preferably 1 to 5, more preferably 1 to 3, and even more preferably 1. Rf 4 Examples of the fluoroalkyl group include a difluoromethanediyl group, a tetrafluoroethanediyl group, and a hexafluoropropanediyl group. p is preferably 10-100, more preferably 30-100, and further preferably 50-90. Rf 5 Examples of the alkyl group include a perfluoromethyl group, a perfluoropropyl group, a perfluorohexyl group, and a perfluorododecyl group.

[0025] (ORf 4 ) p is preferably represented by formula (f4-1): [ka] (wherein a is 0 to 100, b is 0 to 100, c is 0 to 100, and a+b+c is 10 to 200). a is preferably 10-80, more preferably 20-70, and further preferably 30-50. a is preferably 10-80, more preferably 20-70, and further preferably 30-50. c is preferably 0 to 50, more preferably 0 to 30, and further preferably 0 to 10. a+b+c is preferably 30-180, more preferably 50-150, and even more preferably 60-120.

[0026] From the viewpoint of improving the wipeability of fingerprints and the like from the formed antifouling layer, the content of compound (A) is preferably 30% by mass to 89% by mass, more preferably 35% by mass to 80% by mass, and even more preferably 40% by mass to 70% by mass, relative to the solid content of the antifouling agent composition.

[0027] (Compound (B)) The antifouling agent composition contains a compound (B) (hereinafter simply referred to as "compound (B)") having a silyl group at one end and a reactive group at the other end, which can suppress axial misalignment during edging of the spectacle lens having an antifouling layer formed thereon. Compound (B) is preferably linear.

[0028] The compound (B) contains a silyl group, which allows a condensation reaction to proceed and form an antifouling layer. Examples of the silyl group include trialkoxysilyl groups such as trimethoxysilyl, triethoxysilyl, tripropyloxysilyl, and trihexyloxysilyl.

[0029] The compound (B) has a reactive group at the other end, which can appropriately suppress the slipperiness of the antifouling layer and can suppress axial deviation during edging. The reactive group is, for example, at least one selected from the group consisting of a hydroxy group, a vinyl group, a silyl group, an epoxy group, and an alkoxy group. Among these groups, a hydroxy group is preferred from the viewpoint of increasing the reactivity with the silyl groups of Compound (A) and Compound (B). The hydroxy group is preferably bonded to a carbon atom.

[0030] From the viewpoint of improving the wipeability of fingerprints and the like from the stain-resistant layer, the compound (B) preferably has a fluorinated alkylene oxide chain. Examples of the fluorinated alkylene oxide chain include a polyperfluoromethylene oxide group, a polyperfluoroethylene oxide group, and a polyperfluoropropylene oxide group. The number of fluorinated alkylene oxide units in the fluorinated alkylene oxide chain is preferably 10 to 100, more preferably 30 to 100, and even more preferably 50 to 90.

[0031] The compound (B) preferably has a siloxane chain structure. Examples of the siloxane chain include a polydimethylsiloxane group, a polydiethylsiloxane group, and a polydipropylsiloxane group. The number of siloxane units in the siloxane chain is preferably 1 to 100, more preferably 10 to 900, and even more preferably 20 to 80.

[0032] More specifically, the compound (B) is represented by the formula (2): [ka] (In the formula, R a is a group containing a reactive group, R 10 are each independently a divalent hydrocarbon group having 1 to 4 carbon atoms, and a is 0 to 10; R 11 are each independently a monovalent hydrocarbon group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, b is an integer of 0 to 10, and c is an integer of 0 to 10; R 1 are each independently a monovalent hydrocarbon group having 1 to 6 carbon atoms, R 2 are each independently a divalent hydrocarbon group having 1 to 6 carbon atoms, and n is 0 or 1; R 3 are each independently a divalent hydrocarbon group having 1 to 4 carbon atoms, and m is 0 to 10; Rf 4 are each independently a divalent fluorinated hydrocarbon group having 1 to 4 carbon atoms, and p is 10 to 100. R 1 , R 2 , R 3 、 Rf 4 、 and p have the same meanings as in the above formula (1). 4 ) p is preferably a group represented by the above formula (f4-1). The definitions of the substituents in formula (f4-1) are the same as those described above. R 10 Examples of the alkyl group include a methanediyl group, an ethanediyl group, and a propanediyl group. R 11 Examples of the alkyl group include a methyl group, an ethyl group, a methoxy group, and an ethoxy group. Among these, a methyl group is preferred.

[0033] R a is preferably Formula (a1): [ka] or Formula (a2): [ka] (In the formula, R a1 , R a2 , R a3 , R a4 are each independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. R a1 , R a2 , R a3, R a4 is preferably a hydrogen atom. a is more preferably a group represented by formula (a1).

[0034] From the viewpoint of further suppressing axial misalignment during edging, the content of compound (B) is preferably 10% by mass to 70% by mass, more preferably 15% by mass to 60% by mass, and even more preferably 20% by mass to 50% by mass, relative to the solid content of the antifouling agent composition.

[0035] The ratio of the content of compound (A) to the content of compound (B) in the antifouling composition (compound (A) / compound (B)) is preferably 0.3 to 10, more preferably 0.5 to 8, and even more preferably 0.6 to 5.

[0036] (Compound (C)) The antifouling composition contains a chain-like fluorine compound (C) (hereinafter simply referred to as "compound (C)") that does not have a reactive group, thereby improving the wipeability of fingerprints and the like from the formed antifouling layer. Since the chain-like fluorine compound (C) does not have a reactive group, it does not form bonds with other components in the antifouling composition and exists in a free state in the antifouling layer. Therefore, a small amount of compound (C) seeps onto the surface of the antifouling layer during use, improving the wipeability of fingerprints and the like.

[0037] From the viewpoint of improving the wipeability of fingerprints and the like from the stain-resistant layer, the compound (C) preferably has a fluorinated alkylene oxide chain. Examples of the fluorinated alkylene oxide chain include a polyperfluoromethylene oxide group, a polyperfluoroethylene oxide group, and a polyperfluoropropylene oxide group. The number of fluorinated alkylene oxide units in the fluorinated alkylene oxide chain is preferably 10 to 100, more preferably 30 to 100, and even more preferably 50 to 90.

[0038] Compound (C) preferably has the formula (3): [ka] (In the formula, R 20 is a monovalent hydrocarbon group having 1 to 20 carbon atoms or a fluorinated alkyl group having 1 to 20 carbon atoms, R 2 are each independently a divalent hydrocarbon group having 1 to 6 carbon atoms, and n is 0 or 1; R 3 are each independently a divalent hydrocarbon group having 1 to 4 carbon atoms, and m is 0 to 10; Rf 4 are each independently a divalent fluorinated hydrocarbon group having 1 to 4 carbon atoms, and p is 10 to 100; Rf 5 is a fluorinated alkyl group having 1 to 20 carbon atoms.

[0039] R 2 , R 3 、 Rf 4 、 and p have the same meanings as in the above formula (1). 4 ) p is preferably a group represented by the above formula (f4-1). The definitions of the substituents in formula (f4-1) are the same as those described above.

[0040] R 20 Examples of the alkyl group include a methyl group, an ethyl group, a hexyl group, a dodecyl group, a hexadecyl group, a perfluoromethyl group, a perfluoroethyl group, a perfluorohexyl group, a perfluorododecyl group, and a perfluorohexadecyl group.

[0041] Rf 5 Examples of Rf include a perfluoromethyl group, a perfluoroethyl group, a perfluorohexyl group, a perfluorododecyl group, and a perfluorohexadecyl group. 5 Among these, a perfluoromethyl group is preferred.

[0042] The content of compound (C) is preferably 1 to 30% by mass, more preferably 5 to 25% by mass, and even more preferably 10 to 20% by mass, relative to the solid content of the antifouling composition, from the viewpoint of improving the wipeability of fingerprints and the like from the formed antifouling layer, and from the viewpoint of further suppressing axial misalignment during edging.

[0043] (Method of manufacturing eyeglass lenses: Formation of antifouling layer) The method for producing a spectacle lens according to this embodiment includes a step of forming an antifouling layer on a spectacle lens using an antifouling composition containing compound (A), compound (B), and chain fluorine compound (C). The antifouling layer can be obtained, for example, by vapor deposition or coating the antifouling composition, but is preferably obtained by vapor deposition.

[0044] The deposition is carried out by, for example, vacuum deposition. In the vacuum deposition, the heating temperature during deposition is preferably 400°C or higher, more preferably 550°C or higher, even more preferably 600°C or higher, and even more preferably 650°C or higher. The heating temperature for deposition refers to the temperature at which pellets or the like impregnated with the antifouling agent composition are heated during deposition. The heating temperature in vacuum deposition is preferably 400°C or higher, for example, in the range of 400°C to 1000°C. Note that vacuum deposition is carried out at a temperature of 3.0 x 10 -2 It is preferable to carry out the deposition in a deposition space controlled to a vacuum of 0.1 Pa or less.

[0045] Heating during vapor deposition can be performed using, for example, a halogen heater, resistance heating, or an electron gun, but among these, using an electron gun for heating and vapor deposition allows for the formation of a highly accurate thin film. The power of the electron gun varies depending on the material used, the vapor deposition device, the degree of vacuum, and the irradiation area, but the preferred conditions are an acceleration voltage of about 6 kV and an applied current of about 5 mA to 40 mA.

[0046] The deposition time is preferably, for example, 1000 seconds or less, more preferably 800 seconds or less, or even 600 seconds or less. By depositing within such a time, even if a water-repellent material containing multiple components with slightly different deposition start temperatures is used, the components can be deposited almost simultaneously, and a uniform film can be obtained.

[0047] Preferably, the deposition is carried out using a porous material that is impregnated with the antifouling composition. As the porous material, it is preferable to use a sintered filter made by sintering a fused silica porous body or a metal powder with high thermal conductivity such as copper or stainless steel. From the viewpoint of obtaining an appropriate deposition rate, the mesh size of the sintered filter is set to 40 μm to 200 μm, preferably 80 μm to 120 μm. Alternatively, a pellet in which steel wool is filled in a copper container can also be suitably used. The antifouling composition may be used as it is or in the form of a solution by impregnating the porous material.

[0048] To form an antifouling layer on a spectacle lens by coating, a method can be employed in which a fluorine-containing silane compound is dissolved in an organic solvent and then coated on the surface of the spectacle lens. Examples of the coating method include dipping, spin coating, spraying, flow coating, doctor blade coating, roll coating, gravure coating, and curtain flow coating.

[0049] After the formation of the antifouling layer, a heating step may be performed. In the heating step, the reaction between the antifouling agent composition and the spectacle lens surface is promoted. By carrying out this heat treatment, it is possible to suppress a decrease in water repellency due to physical and chemical stresses in daily use, such as wiping the spectacle lens surface or the adhesion of detergent, and thereby improve durability. The temperature for the heat treatment is preferably 40°C to 90°C, more preferably 50°C to 80°C, and even more preferably 55°C to 70°C. The time for the heat treatment is not particularly limited, but is, for example, 0.5 to 10 hours.

[0050] The thickness of the antifouling layer is preferably 1 nm to 5 μm, more preferably 1 nm to 100 nm, and even more preferably 2 nm to 10 nm.

[0051] (surface free energy) The total surface free energy of the antifouling layer is preferably 10.0 mJ / m 2 more preferably 10.1 mJ / m 2 The upper limit of the total surface free energy of the antifouling layer is not particularly limited, but it is, for example, 12.0 mJ / m 2 may be less than 11.5 mJ / m 2 may be less than 11.0 mJ / m 2 It may be the following:

[0052] The basic component of the surface free energy of the antifouling layer is preferably 0.95 mJ / m 2 more preferably 0.97 mJ / m 2 More preferably, it is 0.99 mJ / m or more. 2 The upper limit of the basic component of the surface free energy of the antifouling layer is not particularly limited, but is, for example, 3.0 mJ / m 2 may be less than 2.0 mJ / m 2 may be less than 11.5 mJ / m 2 It may be the following:

[0053] The surface free energy and the base component of the surface free energy in this disclosure are values ​​determined by acid-base theory. Water, diiodomethane, and ethylene glycol are used as the liquids for measuring contact angles, and 2 μL of each liquid is dropped onto the surface of the substrate, and the contact angle is measured using a DM700 made by Kyowa Interface Science Co., Ltd. From the measured contact angle, the surface free energy and the values ​​of each of its constituent components are calculated using the surface free energy calculation formula based on acid-base theory. The surface free energy and the basic component of the surface free energy can be set within the above ranges, for example, by adjusting the conditions for forming the antifouling agent composition and the antifouling layer.

[0054] Next, each configuration of the eyeglass lens of the embodiment will be described.

[0055] <Lens substrate> The lens substrate may be either a finished lens or a semi-finished lens. The surface shape of the lens substrate is not particularly limited, and may be flat, convex, concave, or the like. The lens substrate may be used for any of a single-vision lens, a multifocal lens, a progressive-power lens, etc. For example, in a progressive-power lens, the near-vision region (near vision region) and the progressive-power region (intermediate region) are usually included in the lower region, and the distance-vision region (distance vision region) is included in the upper region. As the lens substrate, a colorless one is usually used, but a colored one can also be used as long as the transparency is not impaired.

[0056] The lens substrate is preferably a meniscus type. By incorporating the above-mentioned compound 1 into a meniscus type lens substrate, astigmatism can be suppressed.

[0057] The optical center thickness of the lens substrate is not particularly limited, but is preferably 0.5 mm to 5.0 mm, more preferably 0.5 mm to 3.0 mm, and even more preferably 0.5 mm to 2.0 mm. The diameter of the lens substrate is not particularly limited, but is usually about 50 mm to 100 mm.

[0058] The refractive index ne of the lens substrate is preferably 1.53 or more, more preferably 1.55 or more, and even more preferably 1.60 or more. The upper limit of the refractive index ne of the lens substrate is not particularly limited, but may be, for example, 1.80 or less.

[0059] Examples of resins for the lens substrate include urethane resins, episulfide resins, polycarbonate resins, and acrylic resins. The resin is preferably at least one selected from the group consisting of polythiourethane resins, polysulfide resins, and polyurethane resins, and more preferably at least one selected from the group consisting of polythiourethane resins and polysulfide resins.

[0060] (Lens substrate manufacturing method) The lens substrate is not particularly limited, but may be, for example: curing the polymerizable composition; and A process to anneal the cured resin The composition can be obtained by a manufacturing method including the steps of:

[0061] The polymerization is preferably a cast polymerization method, and the lens substrate can be obtained, for example, by injecting a polymerizable composition into a mold formed by combining a glass or metal mold with a tape or a gasket, and then polymerizing the composition.

[0062] The polymerization conditions can be appropriately set depending on the polymerizable composition. The polymerization initiation temperature is preferably 0°C or higher, more preferably 10°C or higher, and preferably 50°C or lower, more preferably 40°C or lower. It is preferable to raise the temperature from the polymerization initiation temperature and then heat to harden and form the composition. For example, the maximum temperature is usually 110°C or higher and 130°C or lower.

[0063] After the polymerization is complete, the lens substrate may be released from the mold and then subjected to an annealing treatment, preferably at a temperature of 100 to 150°C.

[0064] <Hard coat layer> The hard coat layer is, for example, a cured film made of a curable composition containing an inorganic oxide and a silicon compound. The curable composition preferably further contains a polyfunctional epoxy compound.

[0065] Examples of inorganic oxides include silicon oxide, aluminum oxide, titanium oxide, zirconium oxide, tungsten oxide, zinc oxide, tin oxide, beryllium oxide, and antimony oxide, as well as composite oxides of two or more of these inorganic oxides. These may be used alone or in combination of two or more. Among these inorganic oxides, silicon oxide is preferred. Colloidal silica may also be used as the inorganic oxide.

[0066] The content of the inorganic oxide is preferably 20% by mass or more and 80% by mass or less, more preferably 25% by mass or more and 70% by mass or less, and even more preferably 25% by mass or more and 50% by mass or less, based on the solid content of the curable composition.

[0067] The silicon compound is, for example, a silicon compound having a hydrolyzable group such as an alkoxy group.The silicon compound is preferably a silane coupling agent having an organic group bonded to a silicon atom and a hydrolyzable group.The organic group bonded to a silicon atom is preferably an organic group having a functional group such as an epoxy group such as a glycidoxy group, a vinyl group, a methacryloxy group, an acryloxy group, a mercapto group, an amino group, or a phenyl group, and more preferably an organic group having an epoxy group.In addition, the silicon compound may have an alkyl group bonded to silicon.

[0068] Commercially available products of the above-mentioned silane coupling agents include, for example, those manufactured by Shin-Etsu Chemical Co., Ltd. under the trade names KBM-303, KBM-402, KBM-403, KBE-402, KBE-403, KBM-1403, KBM-502, KBM-503, KBE-502, KBE-503, KBM-5103, KBM-602, KBM-603, KBM-903, KBE-903, KBE-9103, KBM-573, KBM-575, KBM-9659, KBE-585, KBM-802, KBM-803, KBE-846, and KBE-9007.

[0069] The content of the silicon compound is preferably 20% by mass to 90% by mass, more preferably 30% by mass to 75% by mass, and even more preferably 50% by mass to 75% by mass, based on the solid content of the curable composition.

[0070] The polyfunctional epoxy compound is a polyfunctional epoxy compound containing two or more epoxy groups in one molecule, more preferably a polyfunctional epoxy compound containing two or three epoxy groups in one molecule. Commercially available polyfunctional epoxy compounds include EX-201, EX-211, EX-212, EX-252, EX-313, EX-314, EX-321, EX-411, EX-421, EX-512, EX-521, EX-611, EX-612, EX-614, and EX-614B in the "Denacol" series manufactured by Nagase ChemteX Corporation.

[0071] The content of the polyfunctional epoxy compound is preferably 0 to 50% by mass, more preferably 10 to 40% by mass, and even more preferably 15 to 30% by mass, based on the solid content of the curable composition.

[0072] The above-mentioned curable composition can be prepared by mixing optional components such as an organic solvent, a leveling agent, a curing catalyst, etc., in addition to the components described above, as needed. The hard coat layer can be formed by applying a curable composition to a substrate and then subjecting it to a curing treatment (thermal curing, photocuring, etc.). Commonly used methods such as dipping, spin coating, and spraying can be used to apply the curable composition. For curable compositions containing polyfunctional epoxy compounds, the curing treatment is usually performed by heating. The heat curing treatment can be performed, for example, by placing the lens coated with the curable composition in an environment with an ambient temperature of 50°C to 150°C for about 30 minutes to 3 hours.

[0073] <Underlayer> The underlayer can be formed from, for example, an aqueous resin composition containing at least one type of resin particles selected from the group consisting of polyurethane resin, acrylic resin, and epoxy resin.

[0074] As the aqueous resin composition, commercially available aqueous polyurethanes can be used as they are, or diluted with an aqueous solvent as necessary. Examples of commercially available aqueous polyurethanes include the "Evaphanol" series manufactured by Nicca Chemical Co., Ltd., the "Superflex" series manufactured by Daiichi Kogyo Seiyaku Co., Ltd., the "Adeka Bontiter" series manufactured by ADEKA Corporation, the "Olestar" series manufactured by Mitsui Chemicals, Inc., the "Bondic" series and the "Hydran" series manufactured by Dainippon Ink and Chemicals, Inc., the "Impranil" series manufactured by Bayer, the "Sofranate" series manufactured by Nippon Soflan Co., Ltd., the "Poise" series manufactured by Kao Corporation, the "Sunprene" series manufactured by Sanyo Chemical Industries, Ltd., the "Eizelax" series manufactured by Hodogaya Chemical Co., Ltd., and the "Neolet's" series manufactured by Zeneca Corporation.

[0075] The underlayer can be formed, for example, by applying the above-mentioned aqueous resin composition to the surface of the substrate and drying it.

[0076] <Functional layer> Examples of the functional layer include an antireflection layer, an ultraviolet absorbing layer, an infrared absorbing layer, a photochromic layer, an antistatic layer, and an antifogging layer. These functional layers may be used alone or in combination of two or more. Publicly known techniques related to spectacle lenses can be applied to these functional layers. Among these, it is preferable to have an antireflection layer.

[0077] (Anti-reflection layer) The antireflection layer has, for example, low refractive index layers and high refractive index layers arranged alternately. The number of layers in the antireflection layer is preferably 4 to 11, and more preferably 5 to 8.

[0078] The refractive index of the low refractive index layer is preferably 1.35 to 1.80, more preferably 1.45 to 1.50 at a wavelength of 500 nm to 550 nm. The low refractive index layer is made of an inorganic oxide, preferably silicon oxide.

[0079] The refractive index of the high refractive index layer is preferably 1.90 to 2.60, more preferably 2.00 to 2.40, at a wavelength of 500 nm to 550 nm. The high refractive index layer is made of, for example, an inorganic oxide. The inorganic oxide used in the high refractive index layer is preferably at least one selected from the group consisting of zirconium oxide, tantalum oxide, yttrium oxide, titanium oxide, niobium oxide, and aluminum oxide, more preferably at least one selected from the group consisting of zirconium oxide and tantalum oxide.

[0080] The antireflection layer can be formed by alternately laminating low refractive index layers and high refractive index layers by vacuum deposition.

[0081] As described above, the present disclosure provides a spectacle lens, an antifouling agent composition, and a method for manufacturing a spectacle lens that have excellent wiping properties and suppress the occurrence of axis misalignment.

[0082] This specification discloses the following embodiments. <1> a compound (A) having a silyl group and a fluorinated alkyl group; A compound (B) having a silyl group at one end and a reactive group at the other end; A spectacle lens provided with an antifouling layer which is a condensate of an antifouling agent composition containing a chain fluorine compound (C) having no reactive group. <2> The antifouling composition contains 30% by mass to 89% by mass of compound (A). <1> The eyeglass lens according to claim 1. <3> The antifouling composition contains 10% by mass to 70% by mass of compound (B). <1> or <2> The eyeglass lens according to claim 1. <4> The antifouling composition contains 1% by mass to 30% by mass of compound (C). <1> ~ <3> The eyeglass lens according to any one of the preceding items. <5> the compound (A) has the silyl group at one end and the fluorinated alkyl group at the other end; <1> ~ <4> The eyeglass lens according to any one of the preceding items. <6> The compound (A) is linear. <1> ~ <5> The eyeglass lens according to any one of the preceding items. <7> The compound (A) is represented by the formula (1): [ka] (In the formula, R 1 are each independently a monovalent hydrocarbon group having 1 to 6 carbon atoms, R 2 are each independently a divalent hydrocarbon group having 1 to 6 carbon atoms, and n is 0 or 1; R 3 are each independently a divalent hydrocarbon group having 1 to 4 carbon atoms, and m is 0 to 10; Rf 4 are each independently a divalent fluorinated hydrocarbon group having 1 to 4 carbon atoms, and p is 10 to 100; Rf 5 is a fluorinated alkyl group having 1 to 20 carbon atoms. <1> ~ <6> The eyeglass lens according to any one of the preceding items. <8> (ORf 4 ) p But equation (f4-1): [ka] (wherein a is 0 to 100, b is 0 to 100, c is 0 to 100, and a+b+c is 10 to 200), <7> The eyeglass lens according to claim 1. <9> The compound (B) is linear. <1> ~ <8> The eyeglass lens according to any one of the preceding items. <10> The compound (B) is represented by the formula (2): [ka] (In the formula, R a is a group containing a reactive group, R 10 are each independently a divalent hydrocarbon group having 1 to 4 carbon atoms, and a is 0 to 10; R 11 are each independently a monovalent hydrocarbon group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, b is an integer of 0 to 10, and c is an integer of 0 to 10; R 1 are each independently a monovalent hydrocarbon group having 1 to 6 carbon atoms, R 2 are each independently a divalent hydrocarbon group having 1 to 6 carbon atoms, and n is 0 or 1; R 3 are each independently a divalent hydrocarbon group having 1 to 4 carbon atoms, and m is 0 to 10; Rf 4 are each independently a divalent fluorinated hydrocarbon group having 1 to 4 carbon atoms, and p is 10 to 100. <1> ~ <9> The eyeglass lens according to any one of the preceding items. <11> The reactive group is at least one selected from the group consisting of a hydroxy group, a vinyl group, a silyl group, an epoxy group, and an alkoxy group. <1> ~ <10> The eyeglass lens according to any one of the preceding items. <12> R a is expressed as equation (a1): [ka] Or, Formula (a2): [ka] (In the formula, R a1 , R a2 , R a3 , R a4 are each independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. <10> The eyeglass lens according to claim 1. <13> (ORf 4 ) p But equation (f4-1): [ka] (wherein a is 0 to 100, b is 0 to 100, c is 0 to 100, and a+b+c is 10 to 200), <10> ~ <12> The eyeglass lens according to any one of the preceding items. <14> The compound (C) is represented by the formula (3): [ka] (In the formula, R 20 is a monovalent hydrocarbon group having 1 to 20 carbon atoms or a fluorinated alkyl group having 1 to 20 carbon atoms, R 2 are each independently a divalent hydrocarbon group having 1 to 6 carbon atoms, and n is 0 or 1; R 3 are each independently a divalent hydrocarbon group having 1 to 4 carbon atoms, and m is 0 to 10; Rf 4 are each independently a divalent fluorinated hydrocarbon group having 1 to 4 carbon atoms, and p is 10 to 100; Rf 5 is a fluorinated alkyl group having 1 to 20 carbon atoms. <1> ~ <13> The eyeglass lens according to any one of the preceding items. <15> (ORf 4 ) p But equation (f4-1): [ka] (wherein a is 0 to 100, b is 0 to 100, c is 0 to 100, and a+b+c is 10 to 100), <14> The eyeglass lens according to claim 1. <16> The total surface free energy of the antifouling layer is 10.0 mJ / m 2 It is super, <1> ~ <15> The eyeglass lens according to any one of the preceding items. <17> The basic component of the surface free energy of the antifouling layer is 0.95 mJ / m 2 It is super, <1> ~ <16> The eyeglass lens according to any one of the preceding items. <18> a compound (A) having a silyl group and a fluorinated alkyl group; A compound (B) having a silyl group at one end and a reactive group at the other end; a chain fluorine compound (C) having no reactive group; A stain-proofing composition comprising: <19> a compound (A) having a silyl group and a fluorinated alkyl group; A compound (B) having a silyl group at one end and a reactive group at the other end; A method for producing a spectacle lens, comprising the step of forming an antifouling layer on the spectacle lens using an antifouling agent composition containing a chain fluorine compound (C) having no reactive group. [Example]

[0083] The present embodiment will be described in more detail below using examples and comparative examples, but the present invention is not limited to the following examples.

[0084] [Preparation of antifouling agent composition and preparation of antifouling agent pellets] [Production Examples 1 to 4, Comparative Production Examples 1 and 2] A 20% by mass solution was prepared by mixing the compounds shown in Table 1, and this solution was impregnated into a metal pellet in a copper container filled with steel wool so that the solid content after solvent evaporation would be 15 mg. After impregnation with the 20% by mass solution, the pellet was heated in an oven set to 80°C for 20 minutes to evaporate the solvent and leave a solid content of 15 mg.

[0085] [Table 1]

[0086] The various abbreviations in Table 1 are as follows: Compound A-1: ​​Compound (A) represented by formula (1) (R 1 =-CH3, R 2 =-C3H6-, n=1, R 3 =-C3H6-, Rf 4 =(OCF2) 38 (OCF2CF2) 40 (OCF2CF2CF2) 0.5 , Rf 5 =-CF3.) Compound B-1: Compound (B) represented by formula (2) (R a =-C2H4OH, R 10 =-C3H6-, a=1, R 11 =-CH3, b=1, c=20, R 1 =-CH3, R 2 =-C3H6-, n=1, R 3 =-C3H6-, Rf 4 =(OCF2) 38 (OCF2CF2) 40 (OCF2CF2CF2) 0.5 ) Compound B-2: Compound (B) represented by formula (2) (R a =-C2H4OH, a=0, b=0, c=0, R 1 =-CH3, R 2 =-C2H4-, n=1, R 3 =-C3H6-, Rf 4 =(OCF2)9(OCF2CF2)9.) Compound C-1: Compound (C) represented by formula (3) (R 20 =-CH3, R 2 =-C3H6-, n=1, R 3 =-C3H6-, Rf 4 =(OCF2) 38 (OCF2CF2) 40 (OCF2CF2CF2) 0.5 , Rf 5 =-CF3.)

[0087] [Examples 1 to 4, Comparative Examples 1 and 2] (Vapor deposition of antifouling composition on eyeglass lenses) A glass vessel was charged with 90 parts by weight of colloidal silica (Snowtex-40, Nissan Chemical Industries, Ltd.), 81.6 parts by weight of the organosilicon compound methyltrimethoxysilane, 176 parts by weight of γ-glycidoxypropyltrimethoxysilane, 2.0 parts by weight of 0.5N hydrochloric acid, 20 parts by weight of acetic acid, and 90 parts by weight of water. The resulting mixture was stirred at room temperature for 8 hours and then allowed to stand at room temperature for 16 hours to obtain a hydrolysis solution. To this solution, 120 parts by weight of isopropyl alcohol, 120 parts by weight of n-butyl alcohol, 16 parts by weight of aluminum acetylacetone, 0.2 parts by weight of a silicone surfactant, and 0.1 parts by weight of an ultraviolet absorber were added, stirred at room temperature for 8 hours, and then aged at room temperature for 24 hours to obtain a coating solution. A plastic lens substrate (manufactured by HOYA Corporation, product name EYAS, formulation S0.00, C0.00) pretreated with an alkaline aqueous solution was immersed in the above-mentioned coating solution, and after immersion, the lens substrate was pulled up at a speed of 20 cm / min and heated at 120°C for 2 hours to form a cured film and a hard coat layer (Layer A). Next, an antireflection layer consisting of alternating layers of silica and zirconia was formed on the hard coat layer by vacuum deposition. After the deposition of the anti-reflection layer, an ion gun treatment was carried out to activate the surface under the following conditions. Accelerating voltage: 500V Accelerating current: 230mA Inlet gas: oxygen (20sccm) Ion irradiation time: 30 seconds The dome with the substrate set thereon was then moved to a chamber for vapor deposition of the antifouling composition. In the chamber, pellets impregnated with the antifouling composition (see Table 2) prepared in the above-mentioned Production Example were set on a halogen heater heating table. The pellets were heated with the halogen heater, and the antifouling composition in the pellets was vapor-deposited. The temperature reached during heating was approximately 600°C. The eyeglass lens after the antifouling composition was vapor-deposited was taken out and placed in an oven set at 60° C., and annealed by holding it for 4 hours.

[0088] The resulting eyeglass lenses were evaluated by the following methods, and the results are shown in Tables 2 and 3.

[0089] [Wipeability test] An artificial sebum was prepared with the following composition: Cholesterol: 2% by mass Squalene: 2% by mass Palmitic acid: 2% by mass Triolein: 4% by mass Ethanol: 90% by mass This was applied to a glass substrate by spin coating, and a silicone stopper, which had been previously roughened by polishing with #240 abrasive paper, was pressed against the glass substrate with a 2 kg load, allowing the artificial sebum to adhere to the end of the silicone stopper. Next, the silicone plug was pressed against the spectacle lens to be evaluated with a load of 2 kg. Note that the spectacle lens obtained above was used as the evaluation spectacle lens. Next, the eyeglass lens was set in a friction and abrasion tester. This friction and abrasion tester was designed to perform a sliding test on the evaluation substrate at a constant load, constant speed, and constant stroke. The media (sliding terminal) used in the test was an eraser wrapped in Silbon paper. This was attached to a friction and wear tester, and a load of 500 g was pressed against the evaluation eyeglass lens, the stroke was set to 30 mm, and the wipe was performed by sliding back and forth 10 times. The state of wiping off of the artificial sebum was checked every 10 times. The wiping condition was evaluated by measuring the haze value and converting it into a numerical value. When the haze was 1 or less, fingerprints were barely noticeable.

[0090] [Axis misalignment test] As shown in Figure 2, two straight lines (line a and line b) were drawn on the resulting eyeglass lens in the horizontal (X-axis) and vertical (Y-axis) directions, perpendicular to each other and passing through the geometric center (GC). Point A was designated as point A on line a and 5 mm away from the geometric center (GC), and a straight line (line c) passing through point A and parallel to line b was drawn on the eyeglass lens. Point B was designated as point B on line a, 20 mm away from point A in the opposite direction from the geometric center (GC). Next, a eyeglass processing jig (blocker) was fixed to the convex side using eyeglass processing tape. The eyeglass processing tape used was "RD-6364" (manufactured by Big Technos Co., Ltd.). It was attached so that the center of the eyeglass processing tape was point A and the long axis of the tape was parallel to line a. Next, protective tape "AT-22LH" (manufactured by Big Technos Co., Ltd.) was used to attach the protective tape to the concave surface so that its center was at point A and its long axis was parallel to line a. The blocker with the eyeglass lens attached was then placed and fixed on the holder of an optical microscope, the holder of which was fixed on the stage. Next, assuming that the X coordinate of the geometric center (GC) was 0 and the Y coordinate was 0, the coordinates of points A and B were measured using the optical microscope, and defined as coordinates A and B. Next, the eyeglass lens with the blocker attached was fixed on a wet edging machine "ACCEL-EDGER" (manufactured by HOYA Corporation), and edged based on the frame data. Next, the edged eyeglass lens was fixed to the holder, and the coordinates of points A and B were measured using the optical microscope, and defined as coordinates A' and B'. The acute angle between the line passing through coordinates A and B and the line passing through coordinates A' and B' was defined as the axis deviation angle. Furthermore, if the axial deviation angle during edging is 0.5° or less, the lens can be used as an eyeglass lens without any problems.

[0091] [Table 2]

[0092] [Table 3]

[0093] [Surface free energy measurement] The surface free energy characteristics were measured using the "DM700" manufactured by Kyowa Interface Science Co., Ltd. The contact angle of the antifouling layer surface formed on the eyeglass lens was measured. Water, diiodomethane, and ethylene glycol were used as the liquids for measuring the contact angle. 2 μL of each liquid was dropped onto the eyeglass lens surface, and the contact angle was measured. From the measured contact angle, the surface free energy and the values ​​of each component that makes it up were calculated using the surface free energy calculation formula based on acid-base theory. The results are shown in Table 4.

[0094] [Table 4]

[0095] From the results of the Examples and Comparative Examples described above, it can be seen that the present embodiment provides an eyeglass lens, an antifouling agent composition, and a method for manufacturing an eyeglass lens that have excellent wiping properties and that suppress the occurrence of axial misalignment during edging. [Explanation of symbols]

[0096] 1... eyeglass lens, 11... eyeglass lens substrate, 11a, 21fa, 31fa... object side surface, 11b, 21bb, 31bb... eyeball side surface, 21f, 21b... hard coat layer, 31f, 31b... functional layer, 41f, 41b... antifouling layer

Claims

1. a compound (A) having a silyl group and a fluorinated alkyl group; a compound (B) having a silyl group at one end and a reactive group at the other end; and a chain-like fluorine compound (C) having a fluorinated alkylene oxide chain and no reactive group.

2. 2. The spectacle lens according to claim 1, wherein the antifouling agent composition contains 30% by mass to 89% by mass of compound (A).

3. 2. The spectacle lens according to claim 1, wherein the antifouling agent composition contains 10% by mass to 70% by mass of the compound (B).

4. 2. The spectacle lens according to claim 1, wherein the antifouling agent composition contains 1% by mass to 30% by mass of the compound (C).

5. The eyeglass lens according to claim 1 , wherein the compound (A) has the silyl group at one end and the fluorinated alkyl group at the other end.

6. The compound (A) is represented by the formula (1): 【Chemical 1】 (In the formula, R １ are each independently a monovalent hydrocarbon group having 1 to 6 carbon atoms, R ２ are each independently a divalent hydrocarbon group having 1 to 6 carbon atoms, and n is 0 or 1; R ３ are each independently a divalent hydrocarbon group having 1 to 4 carbon atoms, and m is 0 to 10; Rf ４ are each independently a divalent fluorinated hydrocarbon group having 1 to 4 carbon atoms, and p is 10 to 100; Rf ５ The spectacle lens according to claim 1, wherein:

7. (ORf) in formula (1) ４ ) ｐ But, formula (f4-1): 【Chemistry 2】 (wherein a is 0 to 100, b is 0 to 100, c is 0 to 100, and a+b+c is 10 to 200).

8. The compound (B) is represented by the formula (2): 【Chemistry 3】 (In the formula, R ａ is a group containing a reactive group, R １０ are each independently a divalent hydrocarbon group having 1 to 4 carbon atoms, and a is 0 to 10; R １１ are each independently a monovalent hydrocarbon group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, b is 0 to 10, and c is 0 to 10; R １ are each independently a monovalent hydrocarbon group having 1 to 6 carbon atoms, R ２ are each independently a divalent hydrocarbon group having 1 to 6 carbon atoms, and n is 0 or 1; R ３ are each independently a divalent hydrocarbon group having 1 to 4 carbon atoms, and m is 0 to 10; Rf ４ are each independently a divalent fluorinated hydrocarbon group having 1 to 4 carbon atoms, and p is 10 to 100.

9. 2. The spectacle lens according to claim 1, wherein the reactive group is at least one selected from the group consisting of a hydroxy group, a vinyl group, a silyl group, an epoxy group, and an alkoxy group.

10. The R ａ is represented by formula (a1): 【Chemistry 4】 Or, Formula (a2): 【Chemistry 5】 (In the formula, R ａ１ , R ａ２ , R ａ３ , R ａ４ and each independently represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.

11. (ORf) in formula (2) ４ ) ｐ But, formula (f4-1): 【Chemistry 6】 (wherein a is 0 to 100, b is 0 to 100, c is 0 to 100, and a+b+c is 10 to 200).

12. The compound (C) is represented by the formula (3): 【Chemistry 7】 (In the formula, R ２０ is a monovalent hydrocarbon group having 1 to 20 carbon atoms or a fluorinated alkyl group having 1 to 20 carbon atoms, R ２ are each independently a divalent hydrocarbon group having 1 to 6 carbon atoms, and n is 0 or 1; R ３ are each independently a divalent hydrocarbon group having 1 to 4 carbon atoms, and m is 0 to 10; Rf ４ are each independently a divalent fluorinated hydrocarbon group having 1 to 4 carbon atoms, and p is 10 to 100; Rf ５ The spectacle lens according to claim 1, wherein:

13. (ORf) in formula (3) ４ ) ｐ But, formula (f4-1): 【Chemistry 8】 (wherein a is 0 to 100, b is 0 to 100, c is 0 to 100, and a+b+c is 10 to 100).

14. The total surface free energy of the antifouling layer is 10.0 mJ / m 2 The spectacle lens according to any one of claims 1 to 13, wherein the refractive index is greater than 1 / 2.

15. The surface free energy of the base component of the antifouling layer is 0.95 mJ / m 2 The spectacle lens according to any one of claims 1 to 13, wherein the refractive index is greater than 1 / 2.

16. a compound (A) having a silyl group and a fluorinated alkyl group; a compound (B) having a silyl group at one end and a reactive group at the other end; a chain fluorine compound (C) having a fluorinated alkylene oxide chain and no reactive group; A stain-proofing composition comprising:

17. a compound (A) having a silyl group and a fluorinated alkyl group; a compound (B) having a silyl group at one end and a reactive group at the other end; A method for manufacturing a spectacle lens, comprising a step of forming an antifouling layer on the spectacle lens using an antifouling agent composition containing: (C) a chain-like fluorine compound having a fluorinated alkylene oxide chain and no reactive group.

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