Method for manufacturing eyeglass lens

Abstract

This method for manufacturing an eyeglass lens, which includes a lens substrate and a water-repellent layer formed on the lens substrate, comprises a water-repellent layer formation step for vapor-depositing a water-repellent layer composition containing a first compound and a second compound to form the water-repellent layer on the lens substrate, wherein: the vapor deposition start temperature of the first compound is at least 20ºC higher than the vapor deposition start temperature of the second compound; the water contact angle of the first compound is at least 4º smaller than the water contact angle of the second compound; and the artificial sebum liquid contact angle of the first compound is at least 5º smaller than the artificial sebum liquid contact angle of the second compound.

Description

Method of manufacturing eyeglass lenses

[0001] This disclosure relates to a method for manufacturing eyeglass lenses, and more particularly to a method for manufacturing eyeglass lenses that can be processed by clamping and that have excellent water-repellent and oil-repellent properties.

[0002] Eyeglass lenses are prone to noticeable dirt from fingerprints, sweat, and cosmetics during use. Therefore, a water-repellent layer (sometimes called an "anti-fouling film") is provided on the surface to make them less susceptible to dirt or easier to wipe off. For example, Patent Document 1 describes an eyeglass lens having a fluorine-containing anti-fouling film on its surface, with a surface free energy of 10.0 mJ / m². 2 The following is true, and the basic component of the surface free energy is 0.95 mJ / m 2 The following describes eyeglass lenses. The eyeglass lenses having an anti-fouling coating as shown in Patent Document 1 have high water and oil repellency and are easy to wipe off surface deposits such as fingerprints.

[0003] Japanese Patent Publication No. 2018-004921

[0004] However, the spectacle lenses having an anti-fouling coating as shown in Patent Document 1 have the problem that their water-repellent and oil-repellent properties decrease when subjected to repeated friction, such as wiping off dirt from the surface. Furthermore, they also have the problem that they are difficult to process by clamping them due to their high initial water-repellent and oil-repellent properties before the aforementioned repeated friction is applied.

[0005] Under these circumstances, one aspect of the present disclosure aims to provide a method for manufacturing spectacle lenses that can be processed by clamping and that have excellent water-repellent and oil-repellent properties.

[0006] The inventors have found that the above problem can be solved by depositing a water-repellent layer composition containing a first compound and a second compound having a deposition start temperature 20°C or more lower than the deposition start temperature of the first compound, a water contact angle 4° or more greater than the water contact angle of the first compound, and an artificial sebum liquid contact angle 5° or more greater than the artificial sebum liquid contact angle of the first compound onto a lens substrate to form a water-repellent layer on the lens substrate.

[0007] This disclosure relates to the following [1] to [9]. [1] A method for manufacturing an eyeglass lens comprising a lens substrate and a water-repellent layer formed on the lens substrate, comprising a water-repellent layer forming step of depositing a water-repellent layer composition containing a first compound and a second compound onto the lens substrate to form the water-repellent layer on the lens substrate, wherein the deposition start temperature of the first compound is 20°C or higher than the deposition start temperature of the second compound, the water contact angle of the first compound is 4° or lower than the water contact angle of the second compound, and the artificial sebum liquid contact angle of the first compound is 5° or lower than the artificial sebum liquid contact angle of the second compound. [2] The method for manufacturing an eyeglass lens according to [1], wherein the deposition start temperature of the first compound is 140 to 180°C, and the deposition start temperature of the second compound is 100 to 140°C. [3] The method for manufacturing eyeglass lenses according to [1] or [2] above, wherein the first compound has a water contact angle of 105 to 116° and an artificial sebum contact angle of 45 to 55°, and the second compound has a water contact angle of 112 to 125° and an artificial sebum contact angle of 55 to 70°. [4] The method for manufacturing eyeglass lenses according to any one of [1] to [3] above, wherein when the vertical axis is the mass retention rate (%) and the horizontal axis is the heating temperature (°C), the slope S (mass% / °C) of the deposition curve in the region of mass retention rate from 70 mass% to 60 mass%, the absolute value of the difference (S1-S2) between the slope S1 of the first compound and the slope S2 of the second compound is 0.00 to 1.00 (mass% / °C). [5] The method for manufacturing eyeglass lenses according to [4], wherein the slope S1 of the first compound is -2.00 to -0.10 (mass% / °C) and the slope S2 of the second compound is -2.00 to -0.10 (mass% / °C). [6] The method for manufacturing eyeglass lenses according to any one of [1] to [5], wherein the difference between the molecular weight distribution (Mw / Mn) of the first compound and the molecular weight distribution (Mw / Mn) of the second compound is 0.80 or less. [7] The method for manufacturing eyeglass lenses according to [6], wherein the molecular weight distribution (Mw / Mn) of the first compound is 1.00 to 1.20 and the molecular weight distribution (Mw / Mn) of the second compound is 1.00 to 1.80.[8] A method for manufacturing eyeglass lenses according to any one of [1] to [7] above, further comprising the step of depositing metal particles containing at least one metal onto the lens substrate to arrange the metal particles between the lens substrate and the water-repellent layer. [9] A method for manufacturing eyeglass lenses according to [8] above, wherein the metal particles include at least one selected from the group consisting of silver, platinum, gold, palladium, mercury, cadmium, cobalt, nickel, copper, zinc, titanium, molybdenum, and tungsten.

[0008] According to this disclosure, it is possible to provide a method for manufacturing spectacle lenses that can be processed by clamping and that have excellent water-repellent and oil-repellent properties.

[0009] Figure 1 is a schematic cross-sectional view of the eyeglass lens of this embodiment.

[0010] The following description is based on an example of an embodiment of this disclosure. However, the embodiments shown below are illustrative examples for embodying the technical concept of this disclosure, and this disclosure is not limited to the following description. Embodiments in which any selection or combination of the descriptions in this specification is also included in this disclosure. In this specification, preferred provisions can be selected at will, and combinations of preferred provisions can be said to be more preferred. In this specification, the description "XX to YY" means "XX or more and YY or less". In this specification, the lower limit and upper limit values ​​described in steps for a preferred numerical range (e.g., range of content, etc.) can be combined independently. For example, from the description "preferably 10 to 90, more preferably 30 to 60", the "preferred lower limit (10)" and the "more preferred upper limit (60)" can be combined to get "10 to 60". In this specification, the amount of each component contained in a composition means the total amount of multiple substances present in the composition if there are multiple substances corresponding to each component in the composition, unless otherwise specified. In this specification, "room temperature" refers to the ambient temperature without temperature control such as heating or cooling, and is generally around 20°C, but is not limited to the above temperature as it can vary depending on the weather and season. In this specification, "solid content" refers to the non-volatile content excluding volatile substances such as solvents, and indicates the components that remain without volatilization when the composition is dried, and includes liquid, syrup-like, and wax-like substances at room temperature. In this specification, the term "process" is included not only in the sense of an independent process, but also in the sense of achieving the intended purpose of the process even if it cannot be clearly distinguished from other processes. In this specification, the content of each component in the water-repellent layer composition is the value converted to the case where the silyl group is a trimethoxysilyl group when a component having a silyl group is included. In this specification, "deposition start temperature" refers to the deposition start temperature measured by the method described in the examples of this application. In this specification, "water contact angle" refers to the water contact angle measured by the method described in the examples of this application. In this specification, "artificial sebum solution contact angle" refers to the contact angle of the artificial sebum solution measured by the method described in the embodiment of this application.

[0011] In this specification, "number-average molecular weight," "weight-average molecular weight," and "z-average molecular weight" refer to values ​​based on the molecular weight in terms of polymethyl methacrylate, measured by gel permeation chromatography, and measured under the following sample preparation and measurement conditions. Note that the molecular weight in terms of polymethyl methacrylate, measured by gel permeation chromatography, does not necessarily have to match the molecular weight obtained by other calculation methods. Other calculation methods are not particularly limited and include, for example, methods using matrix-assisted laser desorption / ionization mass spectrometry (MALDI-MS) and nuclear magnetic resonance spectrometry (NMR). <Sample Preparation Conditions> Add 5 mL of the measurement solvent described below (4 mL for the second compound) to 3 mg (4 mg for the second compound) of the residue sample dehydrated under a nitrogen stream, and gently stir at room temperature. After visually confirming that the sample has dissolved, prepare the sample by filtration using a 0.45 μm filter. The measurement sample is subjected to gel permeation chromatography under the following conditions. <Measurement Conditions> Apparatus: Gel permeation chromatograph GPC Detector: Differential refractive index detector RI (RI-504, sensitivity 32, manufactured by Showa Denko K.K. (now Resona Co., Ltd.)) Column: Shodex HFIP-G x 1 (6.0 mm x 5 cm, manufactured by Showa Denko K.K. (now Resona Co., Ltd.)), Shodex HFIP-606M x 2 (6.0 mm x 15 cm, manufactured by Showa Denko K.K. (now Resona Co., Ltd.)) Solvent: Hexafluoroisopropanol with 5 mM sodium trifluoroacetate Flow rate: 0.2 mL / min Column temperature: 40°C Injection volume: 0.020 mL Standard sample: Monodisperse polymethyl methacrylate (PMMA), manufactured by Showa Denko K.K. (now Resona Co., Ltd.) "z-average molecular weight" refers to the average molecular weight defined by the following formula (X). z-average molecular weight = ΣniMi ３ / ΣniMi ２ ... (X) [In formula (X), Mi is the molecular weight of component i in the compound, and ni is the mole fraction of component i.]

[0012] In this specification, "slope S" refers to the slope (mass% / °C) of the deposition curve in the region from a mass retention rate of 70 mass% to 60 mass%, where the vertical axis is the mass retention rate (%) and the horizontal axis is the heating temperature (°C).

[0013] [Method for Manufacturing Eyeglass Lenses] The method for manufacturing eyeglass lenses according to this embodiment is a method for manufacturing eyeglass lenses comprising a lens substrate and a water-repellent layer formed on the lens substrate, and includes a water-repellent layer formation step in which a water-repellent layer composition containing a first compound having a high deposition start temperature and a small contact angle and a second compound having a low deposition start temperature and a large contact angle is deposited on the lens substrate to form a water-repellent layer on the lens substrate.

[0014] In the method for manufacturing eyeglass lenses of this embodiment, a first compound with a small contact angle is formed as the main component on the side opposite to the lens substrate, and a second compound with a large contact angle is formed on the lens substrate, increasing toward the lens substrate. As a result, eyeglass lenses can be processed by clamping them, and the eyeglass lenses have excellent water-repellent and oil-repellent durability.

[0015] The method for manufacturing eyeglass lenses according to this embodiment includes a water-repellent layer formation step, and further includes, if necessary, a metal particle arrangement step and other steps.

[0016] <Water-repellent layer formation process> The water-repellent layer formation process is a process of depositing a water-repellent layer composition onto a lens substrate to form a water-repellent layer on the lens substrate.

[0017] <<Water-repellent layer composition>> The water-repellent layer composition contains the first compound and the second compound, and may contain other components as needed.

[0018] (First compound) The first compound (hereinafter also simply referred to as "the first compound") may or may not have a structure represented by -C(=O)NH-, and may or may not have a silyl group at at least one end (preferably both ends) of the molecular chain.

[0019] The first compound has a silyl group at at least one end (preferably both ends) of its molecular chain, which allows the condensation reaction to proceed and form a water-repellent layer. Examples of silyl groups include trialkoxysilyl groups such as trimethoxysilyl, triethoxysilyl, tripropyloxysilyl, and trihexyloxysilyl. These may be used individually or in combination of two or more.

[0020] The first compound preferably further has a siloxane chain structure. There are no particular restrictions on the siloxane chain, and examples include polydimethylsiloxane groups, polydiethylsiloxane groups, and polydipropylsiloxane groups. These may be used individually or in combination of two or more. Having a siloxane chain structure in the first compound tends to improve adhesion to the functional layer described later.

[0021] The deposition start temperature of the first compound is not particularly limited as long as it is at least 20°C higher than the deposition start temperature of the second compound, but is preferably 140 to 180°C, more preferably 145 to 175°C, and particularly preferably 150 to 170°C. If the deposition start temperature of the first compound is above the lower limit, the difference between the deposition start temperature of the first compound and the deposition start temperature of the second compound is increased, and the "first compound-containing layer, mainly composed of the first compound," can be reliably formed on the surface layer opposite to the substrate of the water-repellent layer. If it is below the upper limit, it is possible to prevent functional failure due to structural decomposition of the first compound due to overheating. The deposition start temperature of the first compound is measured by the method described in the Examples section below.

[0022] The water contact angle of the first compound is not particularly limited as long as it is at least 4° smaller than the water contact angle of the second compound, but is preferably 105 to 116°, more preferably 107 to 110°, and particularly preferably 107 to 109°. If the water contact angle of the first compound is above the lower limit, the water repellency of the "mixed layer of the first compound and the second compound (intermediate layer)" formed on the substrate side of the first compound-containing layer can be improved, and if it is below the upper limit, the clamping processability can be improved. The water contact angle of the first compound is measured by the method described in the Examples section below.

[0023] The contact angle of the first compound with artificial sebum solution is not particularly limited as long as it is 5° or more smaller than the contact angle of the second compound with artificial sebum solution, but is preferably 45 to 55°, more preferably 47 to 53°, and particularly preferably 49 to 51°. If the contact angle of the first compound with artificial sebum solution is above the lower limit, the oil repellency of the "mixed layer (intermediate layer) of the first compound and the second compound" can be improved, and if it is below the upper limit, the clamping processability can be improved. The contact angle of the first compound with artificial sebum solution is measured by the method described in the Examples section below.

[0024] The slope S1 of the first compound is not particularly limited, but is preferably -2.00 to -0.10 (mass% / °C), more preferably -1.80 to -0.80 (mass% / °C), and particularly preferably -1.50 to -1.20 (mass% / °C). The slope S1 of the first compound is measured by the method described in the Examples section below.

[0025] The molecular weight distribution (Mw / Mn) of the first compound is not particularly limited, but is preferably 1.00 to 1.50, more preferably 1.00 to 1.35, and most preferably 1.00 to 1.20. If the molecular weight distribution (Mw / Mn) of the first compound is below the upper limit, the deposition of the first compound can be stabilized. The molecular weight distribution (Mw / Mn) of the first compound is measured by the method described in the Examples section below.

[0026] There are no particular restrictions on the number-average molecular weight (Mn) of the first compound, but from the viewpoint of further improving the water-repellent durability of the water-repellent layer, it is preferably 100 to 10000, more preferably 400 to 2000, even more preferably 600 to 1500, and particularly preferably 800 to 1200.

[0027] Furthermore, there are no particular restrictions on the ratio (Mz / Mw) of the z-average molecular weight (Mz) to the weight-average molecular weight (Mw) of the first compound, but from the viewpoint of further improving the water-repellent durability of the water-repellent layer, it is preferably 1.00 to 1.50, more preferably 1.00 to 1.30, and particularly preferably 1.00 to 1.10.

[0028] The first compound may be either linear or branched. From the viewpoint of further improving the water repellency durability of the water-repellent layer, the first compound is preferably linear. However, the terminal silyl group is not considered in determining whether the compound is linear or branched. In addition, the first compound preferably has a fluorinated alkylene skeleton, and more preferably has a group represented by formula (1a). —(CF ２ O) ａ (C ２ F ４ O) ｂ (C ３ F ６ O) ｃ (C ４ F ８ O) ｄ —...(1a) (In formula (1a), a is 0 to 100, b is 0 to 100, c is 0 to 100, d is 0 to 30, and a+b+c+d is 10 to 200.) The physical properties of the first compound (e.g., deposition initiation temperature, water contact angle, artificial sebum contact angle, slope S1, molecular weight distribution (Mw / Mn), number average molecular weight (Mn), ratio of z-average molecular weight (Mz) to weight average molecular weight (Mw) (Mz / Mw)) can be adjusted by appropriately varying the values of a, b, c, and d.

[0029] In the above formula (1a), the arrangement of the repeating units whose number of units is represented by a, b, c, and d is random or block. a is not particularly limited as long as it is 0 to 100, but is preferably 1 to 80, more preferably 3 to 70, and particularly preferably 5 to 50. b is not particularly limited as long as it is 0 to 100, but is preferably 1 to 80, more preferably 3 to 70, and particularly preferably 5 to 50. c is not particularly limited as long as it is 0 to 100, but is preferably 0 to 50, more preferably 0 to 30, and particularly preferably 0 to 20. d is not particularly limited as long as it is 0 to 30, but is preferably 0 to 25, more preferably 0 to 20, and particularly preferably 0 to 10. a+b+c+d is not particularly limited as long as it is 10 to 200, but is preferably 20 to 200, more preferably 30 to 150, and particularly preferably 40 to 100.

[0030] One method for introducing the group represented by formula (1a) into the water-repellent layer is to form the water-repellent layer with a water-repellent layer composition containing the first compound.

[0031] There are no particular restrictions on the content of the first compound, but from the viewpoint of further improving the load-bearing capacity and water-repellent durability of the water-repellent layer, it is preferably 20 to 99% by mass, more preferably 35 to 96% by mass, even more preferably 50 to 93% by mass, and particularly preferably 60 to 90% by mass, relative to the solid content of the water-repellent layer composition. If the content of the first compound is above the lower limit, the clamping processability can be improved, and if it is below the upper limit, the water-repellent and oil-repellent properties of the "mixed layer of the first compound and the second compound (intermediate layer)" can be maintained at a high level.

[0032] (Second Compound) The second compound (hereinafter also simply referred to as "the second compound") may or may not have a structure represented by -C(=O)NH-, and may or may not have a silyl group at at least one end (preferably both ends) of the molecular chain.

[0033] The deposition start temperature of the second compound is not particularly limited as long as it is at least 20°C lower than the deposition start temperature of the first compound, but is preferably 100 to 140°C, more preferably 105 to 135°C, and particularly preferably 110 to 130°C. If the deposition start temperature of the second compound is above the lower limit, the water-repellent and oil-repellent properties of the "mixed layer (intermediate layer) of the first and second compounds" can be improved, and if it is below the upper limit, the difference between the deposition start temperature of the first compound and the deposition start temperature of the second compound can be increased, and the "first compound-containing layer, mainly composed of the first compound" can be reliably formed on the surface layer opposite to the substrate of the water-repellent layer. The deposition start temperature of the second compound is measured by the method described in the Examples section below.

[0034] The water contact angle of the second compound is not particularly limited as long as it is 4° or more greater than the water contact angle of the first compound, but is preferably 112 to 125°, more preferably 113 to 122°, and particularly preferably 114 to 118°. If the water contact angle of the second compound is above the lower limit, the difference between the water contact angles of the first compound and the second compound can be increased, improving the water repellency of the "mixed layer (intermediate layer) of the first and second compounds". The water contact angle of the second compound is measured by the method described in the Examples section below.

[0035] The contact angle of the second compound with artificial sebum solution is not particularly limited as long as it is 5° or more greater than the contact angle of the first compound with artificial sebum solution, but is preferably 55 to 70°, more preferably 58 to 67°, and particularly preferably 61 to 65°. If the contact angle of the second compound with artificial sebum solution is above the lower limit, the difference between the contact angle of the first compound with artificial sebum solution and the contact angle of the second compound with artificial sebum solution can be increased, thereby improving the oil repellency of the "mixed layer (intermediate layer) of the first and second compounds." The contact angle of the second compound with artificial sebum solution is measured by the method described in the Examples section below.

[0036] The slope S2 of the second compound is not particularly limited, but is preferably -2.00 to -0.10 (mass% / °C), more preferably -1.60 to -0.30 (mass% / °C), and particularly preferably -1.20 to -0.60 (mass% / °C). The slope S2 of the second compound is measured by the method described in the Examples section below.

[0037] The molecular weight distribution (Mw / Mn) of the second compound is not particularly limited, but is preferably 1.00 to 1.80, more preferably 1.05 to 1.55, and most preferably 1.10 to 1.30. If the molecular weight distribution (Mw / Mn) of the second compound is below the upper limit, the deposition of the second compound can be stabilized. The molecular weight distribution (Mw / Mn) of the second compound is measured by the method described in the Examples section below.

[0038] There are no particular restrictions on the number-average molecular weight (Mn) of the second compound, but from the viewpoint of further improving the water-repellent durability of the water-repellent layer, it is preferably 100 to 10000, more preferably 400 to 2000, even more preferably 600 to 1500, and particularly preferably 800 to 1200.

[0039] Furthermore, there are no particular restrictions on the ratio of the z-average molecular weight (Mz) to the weight-average molecular weight (Mw) of the second compound (Mz / Mw), but from the viewpoint of further improving the water-repellent durability of the water-repellent layer, it is preferably 1.00 to 1.50, more preferably 1.00 to 1.30, and particularly preferably 1.00 to 1.10.

[0040] The second compound preferably has a poly(fluorinated alkylene oxy)fluorinated alkyl ether group, and more preferably has a group represented by the following formula (2a), from the viewpoint of improving the load-bearing capacity of the water-repellent layer. The poly(fluorinated alkylene oxy)fluorinated alkyl ether group may be linear or branched. However, terminal silyl groups are not considered when determining whether it is linear or branched. Furthermore, the second compound preferably has a fluorinated alkylene skeleton, and more preferably has a group represented by the formula (2a). - (CF ２ O) ｅ (C ２ F ４ O) ｆ (C ３ F ６ O) ｇ (C ４ F ８ O) ｈ - ... (2a) (In formula (2a), e is between 0 and 100, f is between 0 and 100, g is between 0 and 100, h is between 0 and 30, and e + f + g + h is between 10 and 200.) The physical properties of the second compound (e.g., deposition start temperature, water contact angle, artificial sebum contact angle, slope S2, molecular weight distribution (Mw / Mn), number average molecular weight (Mn), ratio of z-average molecular weight (Mz) to weight average molecular weight (Mw) (Mz / Mw)) can be adjusted by appropriately varying the values ​​of e, f, g, and h.

[0041] In the above formula (2a), the sequence of repeating units, where the number of units is represented by e, f, g, and h, is random or blocky. There are no particular restrictions on e as long as it is between 0 and 100, but it is preferably between 1 and 80, more preferably between 3 and 70, and especially preferably between 5 and 50. There are no particular restrictions on f as long as it is between 0 and 100, but it is preferably between 1 and 80, more preferably between 3 and 70, and especially preferably between 5 and 50. There are no particular restrictions on g as long as it is between 0 and 100, but it is preferably between 0 and 50, more preferably between 0 and 30, and especially preferably between 0 and 20. There are no particular restrictions on h as long as it is between 0 and 30, but it is preferably between 0 and 25, more preferably between 0 and 20, and especially preferably between 0 and 10. There are no particular restrictions on e + f + g + h as long as it is between 10 and 200, but it is preferably between 20 and 200, more preferably between 30 and 150, and especially preferably between 40 and 100.

[0042] One method for introducing the group represented by formula (2a) into the water-repellent layer is to form the water-repellent layer with a water-repellent layer composition containing the second compound.

[0043] There are no particular restrictions on the content of the second compound, but from the viewpoint of further improving the load-bearing capacity and water-repellent durability of the water-repellent layer, it is preferably 1 to 80% by mass, more preferably 4 to 65% by mass, even more preferably 7 to 50% by mass, and particularly preferably 10 to 40% by mass, relative to the solid content of the water-repellent layer composition. If the content of the second compound is above the lower limit, the water-repellent and oil-repellent properties of the "mixed layer of the first compound and the second compound (intermediate layer)" can be maintained at a high level, and if it is below the upper limit, the clamping processability can be improved.

[0044] The difference between the deposition start temperature of the first compound and the deposition start temperature of the second compound (deposition start temperature of the first compound - deposition start temperature of the second compound) is not particularly limited as long as it is 20°C or higher, but is preferably 25 to 80°C, more preferably 30 to 65°C, and particularly preferably 35 to 50°C. If the difference between the deposition start temperature of the first compound and the deposition start temperature of the second compound is above the lower limit, the "first compound-containing layer mainly composed of the first compound" can be reliably formed on the surface layer opposite to the substrate of the water-repellent layer.

[0045] The difference between the water contact angle of the first compound and the water contact angle of the second compound (water contact angle of the second compound - water contact angle of the first compound) is not particularly limited as long as it is 4° or more, but is preferably 5 to 30°, more preferably 6 to 20°, and especially preferably 7 to 10°. If the difference between the water contact angle of the first compound and the water contact angle of the second compound is above the lower limit, both clamping processability and water-repellent durability can be achieved at a high level.

[0046] The difference between the contact angle of the artificial sebum solution of the first compound and the contact angle of the artificial sebum solution of the second compound (artificial sebum solution contact angle of the second compound - artificial sebum solution contact angle of the first compound) is not particularly limited as long as it is 5° or more, but is preferably 10 to 40°, more preferably 11 to 30°, and particularly preferably 12 to 20°. If the difference between the contact angle of the artificial sebum solution of the first compound and the contact angle of the artificial sebum solution of the second compound is above the lower limit, both clamping processability and oil-repellent durability can be achieved at a high level.

[0047] There are no particular restrictions on the absolute value of the difference (S1-S2) between the slope S1 of the first compound and the slope S2 of the second compound, but it is preferably 0.00 to 1.00 (mass% / °C), more preferably 0.00 to 0.80 (mass% / °C), and particularly preferably 0.00 to 0.60 (mass% / °C). When the absolute value of the difference (S1-S2) between the slope S1 of the first compound and the slope S2 of the second compound is less than or equal to the upper limit, the "mixed layer (intermediate layer) of the first compound and the second compound" can be efficiently and uniformly formed.

[0048] There are no particular restrictions on the difference between the molecular weight distribution (Mw / Mn) of the first compound and the molecular weight distribution (Mw / Mn) of the second compound, but it is preferably 0.80 or less, more preferably 0.01 to 0.60, and particularly preferably 0.01 to 0.40.

[0049] Furthermore, there are no particular restrictions on the ratio of the number average molecular weight (Mn) of the second compound to the number average molecular weight (Mn) of the first compound (number average molecular weight (Mn) of the second compound / number average molecular weight (Mn) of the first compound. However, from the viewpoint of further improving the water-repellent durability of the water-repellent layer, it is preferably 0.1 to 5.0, more preferably 0.1 to 3.0, and particularly preferably 0.1 to 1.0.

[0050] There are no particular restrictions on the total content of the first compound and the second compound in the water-repellent layer composition, but from the viewpoint of not impairing the effects of this disclosure, it is preferably 80 to 100% by mass, more preferably 90 to 100% by mass, and particularly preferably 95 to 100% by mass.

[0051] There are no particular restrictions on the mass ratio (second compound / first compound) of the content of the second compound to the content of the first compound in the water-repellent layer composition. However, from the viewpoint of further improving the load-bearing capacity and water-repellent durability of the water-repellent layer, it is preferably 0.01 to 1.00, more preferably 0.05 to 0.85, and particularly preferably 0.10 to 0.70.

[0052] There are no particular restrictions on the total content of other components in the water-repellent layer composition, but from the viewpoint of not impairing the effects of this disclosure, it is preferably 0 to 20% by mass, more preferably 0 to 10% by mass, and particularly preferably 0 to 5% by mass.

[0053] <<Vapor Deposition>> Vapor deposition may be carried out by, for example, vacuum deposition, or it may not be carried out by vacuum deposition. In vacuum deposition, there are no particular restrictions on the heating temperature during deposition, but it is preferably 400 to 1000°C, more preferably 550 to 1000°C, even more preferably 600 to 1000°C, and particularly preferably 650 to 1000°C. The heating temperature for deposition refers to the temperature at which pellets impregnated with the water-repellent layer composition are heated during deposition. Vacuum deposition is 3.0 × 10 －２ It is preferable to carry out the process in a deposition space controlled to a vacuum level of Pa or less.

[0054] Heating during vapor deposition can be achieved using, for example, halogen heaters, resistance heating, or electron guns. Among these methods, using an electron gun allows for the formation of high-precision thin films. The power of the electron gun varies depending on the material used, the deposition apparatus, the vacuum level, and the irradiation area, but preferred conditions are an acceleration voltage of around 6 kV and an applied current of approximately 5 to 40 mA.

[0055] There are no particular restrictions on the deposition time, but it is preferably within 1000 seconds, more preferably within 800 seconds, and most preferably within 600 seconds. By performing deposition within this time, even if multiple water-repellent materials with slightly different deposition start temperatures are used, deposition can be performed almost simultaneously, and a uniform film can be obtained.

[0056] Vapor deposition is preferably carried out using a porous material impregnated with a water-repellent layer composition. As the porous material, fused silica porous bodies and sintered filters made by sintering highly thermally conductive metal powders such as copper or stainless steel are preferred. From the viewpoint of obtaining an appropriate deposition rate, the mesh size of the sintered filter should be 40 to 200 μm, preferably 80 to 120 μm. In addition, pellets made by filling a copper container with steel wool are also suitably used. The water-repellent layer composition may be used as is or as a solution, impregnating the porous material with it.

[0057] <<Lens Substrate>> The lens substrate may be either a finished lens or a semi-finished lens. There are no particular restrictions on the surface shape of the lens substrate; it may be flat, convex, concave, etc. The lens substrate may be used for any application, such as for single-focus lenses, multifocal lenses, or progressive lenses. For example, in the case of a progressive lens, the near-vision region (near-vision) and the progressive region (intermediate-vision) are usually included in the aforementioned lower region, and the far-vision region (far-vision) is included in the upper region. Colorless materials are usually used as lens substrates, but colored materials can also be used as long as transparency is not impaired.

[0058] The lens substrate is preferably of the meniscus type. By incorporating a predetermined compound into the meniscus-type lens substrate, astigmatism can be suppressed.

[0059] There are no particular restrictions on the optical center thickness of the lens substrate, but it is preferably 0.5 to 5.0 mm, more preferably 0.5 to 3.0 mm, and most preferably 0.5 to 2.0 mm. There are no particular restrictions on the diameter of the lens substrate, but it is usually about 50 mm to 100 mm.

[0060] There are no particular restrictions on the refractive index ne of the lens substrate, but it is preferably 1.49 or higher. There are no particular upper limits on the refractive index ne of the lens substrate, and it may be, for example, 1.80 or lower.

[0061] There are no particular restrictions on the resin used for the lens substrate. Examples include urethane resins (e.g., polythiourethane resin, polyurethane resin), polysulfide resin, episulfide resin, polycarbonate resin, acrylic resin, etc. These may be used individually or in combination of two or more. Among these, polythiourethane resin, polysulfide resin, and polyurethane resin are preferred, with polythiourethane resin and polysulfide resin being more preferred.

[0062] (Method for manufacturing lens substrate) The lens substrate is not particularly limited, but can be obtained by a manufacturing method that includes the steps of polymerizing and curing a polymerizable composition capable of preparing the above-mentioned resin, and annealing the cured resin.

[0063] Polymerization is preferably carried out by casting polymerization. The lens substrate can be obtained, for example, by injecting a polymerizable composition into a mold that combines a glass or metal mold with a tape or gasket and then carrying out polymerization.

[0064] Polymerization conditions can be appropriately set depending on the polymerizable composition. There are no particular restrictions on the polymerization start temperature, but it is preferably 0 to 50°C, more preferably 10 to 40°C. It is preferable to raise the temperature from the polymerization start temperature and then heat to cure and form the polymer. The maximum temperature to which the mixture is raised is usually, for example, 110°C to 130°C.

[0065] After polymerization is complete, the lens substrate may be released from the mold and annealed. There are no particular restrictions on the temperature of the annealing treatment, but it is preferably 100 to 150°C.

[0066] <<Water-repellent layer>> The water-repellent layer is preferably a condensate of the water-repellent layer composition. A condensate is a product in which at least a portion of the water-repellent layer composition has condensed. The water-repellent layer may be formed on the hard coat layer or on the functional layer, but it is preferably formed on the anti-reflective layer. Furthermore, it is preferable that the water-repellent layer be located on the outermost surface.

[0067] There are no particular restrictions on the thickness t of the water-repellent layer, but it is preferably 0.1 to 100 nm, more preferably 0.1 to 50 nm, and most preferably 0.1 to 20 nm.

[0068] <Metal Particle Arrangement Process> The metal particle arrangement process involves depositing metal particles containing at least one type of metal onto a lens substrate to arrange the metal particles between the lens substrate and the water-repellent layer. Here, "arranging metal particles between the lens substrate and the water-repellent layer" means, for example, that the metal particles may be arranged inside the multilayer structure of the anti-reflective layer described later, or a metal-containing layer may be formed between the lens substrate and the water-repellent layer, but it is preferable to arrange the metal particles inside the outermost layer formed on the side opposite the lens substrate in the multilayer structure of the anti-reflective layer.

[0069] <<Metal Particles>> There are no particular restrictions on the metals to be contained in the metal particles. Examples include silver (Ag), platinum (Pt), gold (Au), palladium (Pd), mercury (Hg), cadmium (Cd), cobalt (Co), nickel (Ni), copper (Cu), zinc (Zn), titanium (Ti), molybdenum (Mo), tungsten (W), etc. These may be used individually or in combination of two or more. Among these, silver (Ag) and platinum (Pt) are preferred, with silver (Ag) being more preferred, from the viewpoint of their ability to suppress bacterial growth (i.e., antibacterial properties).

[0070] There are no particular restrictions on the form in which metal exists in metal particles. Examples include elemental metal, alloy, inorganic compounds such as metal oxides, organic compounds, and metal ions. In metal particles, for example, silver (Ag) can exist in multiple forms. This is also true for other metals. The inventors of this invention surmise that at least a portion of silver (Ag) can be ionized by oxidation to exhibit antibacterial properties, and that this contributes to the ability of metal particles containing silver (Ag) to function as antibacterial particles. Furthermore, in metal particles containing silver (Ag) as a first metal, along with one or more metals selected from the group consisting of platinum (Pt), gold (Au), palladium (Pd), mercury (Hg), cadmium (Cd), cobalt (Co), nickel (Ni), copper (Cu), zinc (Zn), titanium (Ti), molybdenum (Mo), and tungsten (W) as a second metal, it is presumed that selecting a second metal that has the effect of controlling the progression of silver oxidation contributes to enhancing the persistence of antibacterial properties. However, this disclosure is not limited to the presumptions described herein.

[0071] Metal particles may, in one form, be metal-containing inorganic particles. Metal-containing inorganic particles may contain metal in the form of an inorganic substance such as a pure metal, an alloy, or an inorganic compound. Inorganic substances are preferred as components for eyeglass lenses, which are often subjected to heating processes during the manufacturing process, because they have high thermal stability and tend not to decompose easily with heat.

[0072] There are no particular restrictions on the average particle size of the metal particles, but it is preferably 1 to 15 nm, more preferably 1 to 10 nm, and most preferably 2 to 5 nm. The average particle size of the metal particles can be measured using a laser diffraction scattering particle size analyzer (Nikkiso Co., Ltd., model name "Microtrac MT3300EXII").

[0073] There are no particular restrictions on the method for placing metal particles inside the outermost layer of the anti-reflective coating. Examples include thermal deposition, electron beam deposition, and ion-assisted deposition. These can be used individually or in combination of two or more. Thermal deposition is a method in which the deposition material is heated and vaporized by heating the internal atmosphere of the deposition apparatus using a heating means (such as a heater) placed inside the deposition apparatus. Electron beam deposition is a film formation method in which an electron beam is irradiated from an electron gun onto a deposition source in a vacuum, heating and vaporizing the deposition material contained in the deposition source, and depositing it onto the object to be deposited, thereby forming a deposited film. Ion-assisted deposition is a film formation method in which ionized gas particles from a device called an ion gun are irradiated onto the object to be deposited during deposition, thereby pressing the deposition material onto the object.

[0074] If the metal contained in the metal particles is a combination of a first metal (silver) and one or more second metals, the deposition source can be prepared, for example, by the following method: Prepare a liquid containing silver particles (silver particles), which are the first metal (hereinafter also referred to as the "first metal particle-containing liquid"). Such the first metal particle-containing liquid may be, for example, an aqueous dispersion of silver particles. The concentration (content) of silver particles in the first metal particle-containing liquid may be, for example, in the range of 1,000 to 10,000 ppm by mass. Separately from the first metal particle-containing liquid, prepare a liquid containing one or more second metal particles (hereinafter also referred to as the "second metal particle-containing liquid"). Such the second metal particle-containing liquid may be, for example, an aqueous dispersion of second metal particles. Furthermore, as the second metal particle-containing liquid, only one second metal particle-containing liquid containing one or more types of second metal particles may be used, or two or more second metal particle-containing liquids containing one or more types of second metal particles may be used. In either case, the concentration (content) of the second metal particles in the second metal particle-containing liquid may be, for example, in the range of 1,000 to 10,000 ppm by mass. Here, if the second metal particle-containing liquid contains two or more types of second metal particles, the concentration (content) refers to the total concentration (content) of those two or more types of metal particles. As each metal particle-containing liquid, for example, commercially available products sold as aqueous dispersions of metal particles may be used as is, or commercially available products may be diluted before use. After preparing the metal particle-containing liquids in this way, the metal particle-containing liquids are impregnated into the carrier. Multiple types of metal particle-containing liquids may be impregnated into the carrier separately, simultaneously, or a mixture of multiple types of metal particle-containing liquids may be impregnated into the carrier. The volume of the first metal particle-containing liquid impregnated into the carrier may be, for example, in the range of 0.1 to 5.0 mL. The volume of the second metal particle-containing liquid impregnated into the carrier may be, for example, in the range of 0.1 to 5.0 mL. Furthermore, the volume of the second metal particle-containing liquid may be in the range of 0.1 to 5 times the volume of the first metal particle-containing liquid.Here, when two or more second metal particle-containing liquids are used as the second metal particle-containing liquid, the liquid volume refers to the total liquid volume of those two or more second metal particle-containing liquids. Methods for impregnating the carrier with the metal particle-containing liquid include, for example, injecting or spraying the metal particle-containing liquid onto the carrier, or immersing the carrier in the metal particle-containing liquid.

[0075] After impregnating a carrier with a metal particle-containing liquid, a drying process is performed, causing the solvent component (water) in the metal particle-containing liquid to evaporate and the metal particles to be retained on the carrier.

[0076] The above explanation described the formation of metal particles containing two or more types of metals as an example, but metal particles may contain only one type of metal in one form. The above explanation can also be used to describe the formation of such metal particles.

[0077] <Eyeglass Lens> Figure 1 is a schematic cross-sectional view of the eyeglass lens 1 of this embodiment. The eyeglass lens 1 of this embodiment comprises a lens base material 11, a hard coat layer 21f provided on the surface 11a of the lens base material 11 opposite to the eyeball (hereinafter sometimes referred to as the "object side"), a functional layer 31f provided on the object side surface 21fa of the hard coat layer 21f, and a water-repellent layer 41f provided on the object side surface 31fa of the functional layer 31f.

[0078] 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-facing surface 11b of the lens substrate 11, a functional layer 31b provided on the eyeball-facing surface 21bb of the hard coat layer 21b, and a water-repellent layer 41b provided on the eyeball-facing surface 31bb of the functional layer 31b.

[0079] Although not shown in the figures, 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. The following describes each layer (other than the lens substrate and the water-repellent layer) in the eyeglass lens of this embodiment.

[0080] <<Hard Coat Layer>> The hard coat layer is a cured film made of a curable composition containing, for example, an inorganic oxide and a silicon compound. The curable composition preferably further contains a polyfunctional epoxy compound.

[0081] There are no particular restrictions on the inorganic oxide, and examples include silicon oxide, aluminum oxide, titanium oxide, zirconium oxide, tungsten oxide, zinc oxide, tin oxide, beryllium oxide, and antimony oxide. These may be used individually or in combination of two or more. Among these, silicon oxide is preferred. Colloidal silica may also be used as the inorganic oxide.

[0082] There are no particular restrictions on the inorganic oxide content, but it is preferably 20 to 80% by mass, more preferably 25 to 70% by mass, and most preferably 25 to 50% by mass, of the solid content of the curable composition.

[0083] The silicon compound is, for example, a silicon compound having a hydrolyzable group such as an alkoxy group. Preferably, the silicon compound is a silane coupling agent having an organic group bonded to a silicon atom and a hydrolyzable group. The organic group bonded to the 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. The silicon compound may also have an alkyl group bonded to silicon.

[0084] There are no particular restrictions on the commercially available silane coupling agents mentioned above. Examples include those manufactured by Shin-Etsu Chemical Co., Ltd., with trade names such as KBM-303, KBM-402, KBM-403, KBE402, KBE403, 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. These may be used individually or in combination of two or more.

[0085] There are no particular restrictions on the silicon compound content, but it is preferably 20 to 90% by mass, more preferably 30 to 75% by mass, and most preferably 50 to 75% by mass, of the solid content of the curable composition.

[0086] A polyfunctional epoxy compound is a polyfunctional epoxy compound containing two or more epoxy groups in one molecule, preferably a polyfunctional epoxy compound containing two or three epoxy groups in one molecule. There are no particular restrictions on commercially available polyfunctional epoxy compounds, and examples 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, EX-614B, etc., manufactured by Nagase ChemteX Corporation under the trade name "Denacol". These may be used individually or in combination of two or more.

[0087] There are no particular restrictions on the content of the polyfunctional epoxy compound, but it is preferably 0 to 50% by mass, more preferably 10 to 40% by mass, and most preferably 15 to 30% by mass, of the solid content of the curable composition.

[0088] The curable composition described above can be prepared by mixing, as necessary, any components such as organic solvents, leveling agents, curing catalysts, surfactants, and ultraviolet absorbers, in addition to the components described above. The hard coat layer described above can be formed by applying the curable composition onto a substrate and performing a curing treatment (thermal curing, photocuring, etc.). There are no particular restrictions on the means of applying the curable composition, and commonly used methods such as dipping, spin coating, and spraying can be applied. For curable compositions containing polyfunctional epoxy compounds, the curing treatment is usually performed by heating. Heat curing treatment can be performed, for example, by placing a lens coated with the curable composition described above in an environment with an ambient temperature of 50 to 150°C for about 30 minutes to 3 hours.

[0089] <<Underlayment>> The above-mentioned underlayment can be formed from, for example, an aqueous resin composition containing at least one type of resin particle selected from the group consisting of polyurethane resin, acrylic resin, and epoxy resin.

[0090] As the above-mentioned aqueous resin composition, commercially available aqueous polyurethanes can be used as is, or diluted with an aqueous solvent as needed. There are no particular restrictions on commercially available aqueous polyurethanes, and examples include the "Evaphanol" series from Nikka Chemical Co., Ltd., the "Superflex" series from Daiichi Kogyo Seiyaku Co., Ltd., the "Adekabontiter" series from ADEKA Corporation, the "Orestar" series from Mitsui Chemicals, Inc., the "Bondic" series and "Hydran" series from Dainippon Ink and Chemicals, Inc., the "Impranil" series from Bayer AG, the "Sofranate" series from Nippon Sofran Co., Ltd., the "Poise" series from Kao Corporation, the "Samplen" series from Sanyo Chemical Industries, Ltd., the "Aizelax" series from Hodogaya Chemical Co., Ltd., and the "Neoretz" series from Zeneca Corporation. These may be used individually or in combination of two or more.

[0091] The base layer can be formed, for example, by coating the above-mentioned aqueous resin composition onto the surface of the substrate and drying it.

[0092] <<Functional Layers>> Examples of the functional layers mentioned above include anti-reflective layers, ultraviolet absorbing layers, infrared absorbing layers, photochromic layers, antistatic layers, and anti-fogging layers. These may be used individually or in combination of two or more types. Known technologies related to eyeglass lenses can be applied to these functional layers. Among these, it is preferable to have an anti-reflective layer.

[0093] (Anti-reflective layer) The anti-reflective layer has, for example, alternating low-refractive-index layers and high-refractive-index layers. There are no particular restrictions on the number of layers in the anti-reflective layer, but it is preferably 4 to 11 layers, more preferably 5 to 9 layers.

[0094] There are no particular restrictions on the refractive index of the low refractive index layer, but it is preferably 1.35 to 1.80, and more preferably 1.45 to 1.50, at a wavelength of 500 to 550 nm. The low refractive index layer is made of an inorganic oxide, preferably silicon oxide (also called silica).

[0095] There are no particular restrictions on the refractive index of the high refractive index layer, but it is preferably 1.90 to 2.60, and more preferably 2.00 to 2.40, at a wavelength of 500 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 (also called zirconia), tantalum oxide, yttrium oxide, titanium oxide, niobium oxide, and aluminum oxide, and more preferably at least one selected from the group consisting of zirconium oxide and tantalum oxide.

[0096] An anti-reflective layer can be formed by alternately stacking low-refractive-index layers and high-refractive-index layers using a vacuum deposition method.

[0097] In summary, this disclosure provides a method for manufacturing spectacle lenses that can be processed by clamping and that have excellent water-repellent and oil-repellent properties.

[0098] The present embodiment will be described in more detail below using examples and comparative examples. However, this disclosure is not limited in any way by the following examples.

[0099] [Gel Permeation Chromatography (Mn, Mw, Mz)] 3 mg (4 mg in the case of the second compound) of the residue sample dehydrated under a nitrogen stream was added to 5 mL (4 mL in the case of the second compound) of the measurement solvent described below. The mixture was gently stirred at room temperature, and it was visually confirmed that the sample had dissolved in the measurement solvent. Subsequently, the sample was filtered using a 0.45 μm filter to prepare the measurement sample. The measurement sample was subjected to gel permeation chromatography under the following conditions. <Conditions> Apparatus: Gel permeation chromatography (GPC) Detector: Differential refractive index detector RI (RI-504, sensitivity 32, manufactured by Showa Denko K.K. (now Resona Corporation)) Column: Shodex HFIP-G x 1 (6.0 mm x 5 cm, manufactured by Showa Denko K.K. (now Resona Corporation)) Shodex HFIP-606M x 2 (6.0 mm x 15 cm, manufactured by Showa Denko K.K. (now Resona Corporation)) Solvent: Hexafluoroisopropanol with 5 mM sodium trifluoroacetate Flow rate: 0.2 mL / min Column temperature: 40°C Injection volume: 0.020 mL Standard sample: Monodisperse polymethyl methacrylate (PMMA), manufactured by Showa Denko K.K. (now Resona Corporation)

[0100] [Number of repeating units of perfluoroalkylene oxy moieties] The number of repeating units of perfluoroalkylene oxy moieties in compounds 1 to 5 was determined from the mass / z measured by matrix-assisted laser desorption / ionization mass spectrometry (MALDI-MS). From the structures identified by NMR, the molecular weight of the parts other than the perfluoroalkylene oxy moieties was calculated, (CF ２ O), (CF ２ CF ２ O), (CF ２ CF ２ CF ２ O), and (CF ２ CF ２ CF ２ CF ２ The number of repeating units for O) was calculated.

[0101] [Evaporation Initiation Temperature] The evaporation initiation temperatures of compounds 1 to 5 were measured by thermogravimetric analysis using a thermogravimetric analyzer (product name: TGA / DSC1, manufactured by Mettler-Toledo) under reduced pressure (absolute pressure less than 0.2 Pa). The measurement results are shown in Table 1.

[0102] [Slope of Evaporation Curve] Evaporation curves for compounds 1 to 5 were obtained by performing thermogravimetric analysis using a thermogravimetric analyzer (product name: TGA / DSC1, manufactured by Mettler Toledo) under reduced pressure (absolute pressure less than 0.2 Pa). Based on the obtained evaporation curves, the slope S was calculated using the following formula. The calculation results are shown in Table 1. However, T70 represents the temperature at a mass retention rate of 70%, and T60 represents the temperature at a mass retention rate of 60%. S = (70 - 60) / (T70 - T60)

[0103] [Water Contact Angle] The water contact angle was measured using "DMo-702" manufactured by Kyowa Interface Science Co., Ltd. The water contact angles (0-time water contact angle) of the first and second compounds were measured. Water was used as the liquid for measuring the contact angle, and 2 μL of water was dropped onto the surface of the test sample to measure the water contact angle (0-time water contact angle). The measurement results are shown in Table 1. The test sample was prepared by depositing a single layer on a white glass plate using the first or second compound, and was a 10 nm thick water-repellent film consisting of the first or second compound. The same test sample was used for measuring the contact angle of the artificial sebum solution described later.

[0104] [Contact Angle of Artificial Sebum Solution] For measuring the contact angle of the artificial sebum solution, "DMo-702" manufactured by Kyowa Interface Science Co., Ltd. was used. The contact angles of the artificial sebum solution of the first compound and the second compound were measured. The following artificial sebum solution was used as the liquid for measuring the contact angle, and 2 μL of the artificial sebum solution was dropped onto the surface of the test sample, and the artificial sebum solution contact angle (artificial sebum solution contact angle at 0 points) was measured. The measurement results are shown in Table 1. <Artificial Sebum Solution> A solution (concentration 20% by mass) prepared by diluting a mixture of 20% by mass squalene, 20% by mass cholesterol, 20% by mass palmitic acid, and 40% by mass triolein with isopropanol (IPA) was used as the "artificial sebum solution".

[0105] [Clamping Processability (Axis Misalignment Test)] Clamping processability tests (axis misalignment tests) were performed on each of the spectacle lenses in Examples 1 to 5 and Comparative Examples 1 to 5. Specifically, the axis misalignment state was determined by the angle of deviation from the reference line after processing an S-7.50 lens with a refractive index of 1.53 (manufactured by HOYA Corporation, product name Phoenix) into a predetermined shape, and evaluated according to the following evaluation criteria. The evaluation results are shown in Table 1. <Evaluation Criteria for Clamping Processability (Axis Misalignment Test)> A: No axis misalignment of 1 degree or more occurred in any of the three axis misalignment tests. B: An axis misalignment of 1 degree or more occurred once in the three axis misalignment tests. C: An axis misalignment of 1 degree or more occurred two or more times in the three axis misalignment tests. Note that A is good, and B or C is outside the acceptable range.

[0106] [Water-repellent durability (water contact angle after wiping with a 2 kg load)] Water-repellent durability tests were conducted on each of the spectacle lenses in Examples 1 to 5 and Comparative Examples 1 to 5. Specifically, the spectacle lenses were set in a friction and wear testing machine designed to perform sliding tests on the substrate under evaluation at a constant load, constant speed, and constant stroke. The media (sliding terminal) used for the test was an eraser wrapped in lens tissue paper. The media was attached to the friction and wear testing machine, pressed against the convex surface of the spectacle lens with a 2 kg load, the stroke was set to 30 mm, and the lens was wiped by sliding it back and forth 1000 times. The water contact angle was measured using the method described above and evaluated according to the evaluation criteria below. The evaluation results are shown in Table 1. <Evaluation Criteria for Water-Repellent Durability> A: Greater than or equal to the "initial (before 1000 reciprocating slides) water contact angle" B: Greater than or equal to "initial water contact angle -2°" and less than "initial water contact angle" C: Greater than or equal to "initial water contact angle -4°" and less than "initial water contact angle -2°" D: Greater than or equal to "initial water contact angle -6°" and less than "initial water contact angle -4°" E: Less than "initial water contact angle -6°" Note that A or B is good, and C, D, or E is outside the acceptable range.

[0107] [Oil-repellent durability (contact angle of artificial sebum solution after wiping with a 2 kg load)] Oil-repellent durability tests were conducted on each of the spectacle lenses in Examples 1 to 5 and Comparative Examples 1 to 5. Specifically, the spectacle lenses were set in a friction and wear testing machine designed to allow sliding tests of the substrate under evaluation at a constant load, constant speed, and constant stroke. The media (sliding terminal) used for the test was an eraser wrapped in lens tissue paper. The media was attached to the friction and wear testing machine, pressed against the convex surface of the spectacle lens with a 2 kg load, the stroke was set to 30 mm, and the lens was wiped by sliding it back and forth 1000 times. The contact angle of the artificial sebum solution was measured using the method described above and evaluated according to the evaluation criteria below. The evaluation results are shown in Table 1. <Evaluation Criteria for Oil-Repellent Durability> A: Greater than or equal to the "initial (before 1000 reciprocating sliding) contact angle of artificial sebum liquid" B: Greater than or equal to "initial artificial sebum liquid contact angle -2°" and less than "initial artificial sebum liquid contact angle" C: Greater than or equal to "initial artificial sebum liquid contact angle -4°" and less than "initial artificial sebum liquid contact angle -2°" D: Greater than or equal to "initial artificial sebum liquid contact angle -6°" and less than "initial artificial sebum liquid contact angle -4°" E: Less than "initial artificial sebum liquid contact angle -6°" Note that A or B is good, and C, D, or E is outside the acceptable range.

[0108] [Antibacterial Durability] Antibacterial durability tests were conducted on each of the spectacle lenses in Example 5 and Comparative Examples 3-5. Specifically, the samples after the water-repellent durability test were placed in a sterile petri dish with the layered surface facing upwards. Then, 1.0 × 10 ５ pieces ~ 4.0×10 ５ A 0.4 mL bacterial solution containing one test bacterium (E. coli) was dropped onto the center of the sample surface and covered with a polyethylene film cut to a size of 40 mm x 40 mm. This petri dish was left in an environment with a relative humidity of 90% or higher for 24 hours, and then the 1 cm sample was taken. ２ The number of viable bacteria per unit area was measured, and the following antibacterial activity value was calculated: Antibacterial activity value = Ut - At ≥ 2.0 Ut: 1 cm after 24 hours of incubation of an unprocessed test piece (reference sample) ２ Average value of the logarithmic number of viable bacteria per unit area At: 1 cm after 24 hours of incubation of the antimicrobial treated test piece (example or comparative example sample) ２The average of the logarithmic values ​​of the number of viable bacteria per unit area. The SIAA (Society of International Antimicrobial Agents for Products) stipulates that a product has an antimicrobial effect if its antimicrobial activity value is 2 or higher. Therefore, for each eyeglass lens in Example 5 and Comparative Examples 3 to 5, the antimicrobial properties were evaluated based on the antimicrobial activity values ​​obtained above, according to the following criteria. The evaluation results are shown in Table 1. <Criteria for evaluation of antimicrobial durability> A: Antimicrobial activity value of 2.0 or higher B: Antimicrobial activity value less than 2.0 Note that A is considered good.

[0109] [Preparation of water-repellent layer composition and water-repellent pellets] (Production Examples 1-5, Comparative Production Examples 1-5) A composition prepared by mixing the first compound and the second compound to the contents shown in Table 1 was made into a 20% by mass solution and impregnated into metal pellets filled with steel wool in a copper container so that the solid content after solvent evaporation was 15 mg. After impregnation with the 20% by mass solution, the solvent was evaporated by heating in an oven set to 80°C for 20 minutes to obtain a solid content of 15 mg. Furthermore, as a result of measuring the molecular weight using the method described above, the first compound had a number average molecular weight of Mn = 1080, a weight average molecular weight of Mw = 1190, a z average molecular weight of Mz = 1330, and a molecular weight distribution of Mw / Mn = 1.10 and Mz / Mw = 1.10. The second compound had a number average molecular weight of Mn = 700, a weight average molecular weight of Mw = 760, a z average molecular weight of Mz = 820, and a molecular weight distribution of Mw / Mn = 1.10 and Mz / Mw = 1.10. The third compound had a number average molecular weight of Mn = 770, a weight average molecular weight of Mw = 890, a z average molecular weight of Mz = 1060, and a molecular weight distribution of Mw / Mn = 1.20 and Mz / Mw = 1.20. The fourth compound has a number-average molecular weight of Mn = 7650, a weight-average molecular weight of Mw = 16900, a z-average molecular weight of Mz = 29300, and a molecular weight distribution of Mw / Mn = 2.21 and Mz / Mw = 1.73. The fifth compound has a number-average molecular weight of Mn = 1310, a weight-average molecular weight of Mw = 2050, a z-average molecular weight of Mz = 3410, and a molecular weight distribution of Mw / Mn = 1.56 and Mz / Mw = 1.66.

[0110]

[0111] The meanings of the various abbreviations in Table 1 are as follows: (1) First compound: Compound having the structure of formula (1) below: (CH３ O) ３ SiCH ２ CH ２ CH ２ Si(CH ３ ) ２ -O-Si(CH ３ ) ２ CH ２ CH ２ OCH ２ CF ２ -O-(CF ２ O) ａ -(CF ２ CF ２ O) ｂ -(CF ２ CF ２ CF ２ O) ｃ -CF ２ CH ２ OCH ２ CH ２ Si(CH ３ ) ２ -O-Si(CH ３ ) ２ -CH ２ CH ２ CH ２ Si(OCH ３ ) ３ ... Formula (1) [In Formula (1), a=24, b=26, c=1, and the arrangement of repeating units whose number of units is represented by a, b and c is random.] (2) Second compound: a compound having a structure of the following formula (2) Formula (2): (CH ３ O) ３ SiCH ２ -NHCO-(CF ２ O) ｍ -(CF ２ CH ２ O) ｎ -(CF ２ CH ２ CH ２ O) ｏ -(CF ２ CH ２ CH ２ CH ２ O) ｐ -CF ３...Equation (2) [In equation (2), m = 48, n = 50, o = 1, and p = 1, and the arrangement of repeating units where the number of units is represented by m, n, o, and p is random.]

[0112] [Deposition of water-repellent layer composition onto eyeglass lenses] (Examples 1-4, Comparative Examples 1-5) In a glass container, 90 parts by mass of colloidal silica (Snowtex-40, Nissan Chemical Industries, Ltd.), 81.6 parts by mass of the organosilicon compound methyltrimethoxysilane, 176 parts by mass of γ-glycidoxypropyltrimethoxysilane, 2.0 parts by mass of 0.5N hydrochloric acid, 20 parts by mass of acetic acid, and 90 parts by mass of water were added to the solution. The mixture was stirred at room temperature for 8 hours, and then left to stand at room temperature for 16 hours to obtain a hydrolysis solution. To this solution, 120 parts by mass of isopropyl alcohol, 120 parts by mass of n-butyl alcohol, 16 parts by mass of aluminum acetylacetone, 0.2 parts by mass of a silicone-based surfactant, and 0.1 parts by mass of an ultraviolet absorber were added. The mixture was 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. After immersion, the lens substrate was lifted at a rate of 20 cm / min and heated at 120°C for 2 hours to form a hard coat layer. Next, an anti-reflective layer was formed on the hard coat layer by vacuum deposition, consisting of nine alternating layers of silica and zirconia. After deposition of the anti-reflective layer, ion gun treatment was performed to activate the surface. The ion gun treatment was performed under the following conditions: Acceleration voltage: 500V, Acceleration current: 230mA, Introduced gas: Oxygen (20 sccm), Ion irradiation time: 30 seconds. Then, the dome on which the lens substrate was set was moved to a chamber for deposition of the water-repellent layer composition. In the chamber, pellets impregnated with the water-repellent layer composition prepared in the above-mentioned manufacturing example (see Table 1) were set on a halogen heater heating stand. The pellets were heated with a halogen heater to deposit the water-repellent layer composition. The temperature reached during heating was approximately 600°C.

[0113] (Example 5) In Example 2, after performing ion gun treatment to activate the surface after vapor deposition of the antireflection layer, and before moving the dome having the lens base material set therein to the water-repellent layer composition vapor deposition chamber, vapor deposition of a water-repellent layer composition on a spectacle lens was performed in the same manner as in Example 2, except that the following "formation of metal particles by a heating vapor deposition method" was performed. <Formation of Metal Particles by Heating Vapor Deposition Method> A spectacle lens having an antireflection layer formed thereon and a vapor deposition source were placed in a vacuum chamber of a vacuum vapor deposition apparatus. The internal atmosphere temperature in the vacuum chamber was controlled by two halogen heaters. Specifically, in the temperature profile of one heater, the temperature was raised to 600°C over 1 minute and 30 seconds, and then raised from 600°C to 650°C over 4 minutes and 30 seconds. In the temperature profile of the other heater, the heating start time was delayed by 1 minute and 30 seconds from the heating start time of one heater, the temperature was raised to 600°C over 2 minutes, and then raised from 600°C to 650°C over 4 minutes. In addition, the pressure in the vacuum chamber was 2×10 －２ Pa or less. In this way, silver particles and platinum particles were heated and vaporized, so that the SiO layer, which is the outermost layer formed on the side opposite to the lens base material in the multilayer structure of the antireflection layer ２ has metal particles present inside the layer.

[0114] Each of the above-described evaluations was performed on the spectacle lens obtained by the above method. The results are shown in Table 1.

[0115] As described above, from the results of Examples and Comparative Examples (Table 1), it can be understood that according to the present embodiment, there is provided a method for manufacturing a spectacle lens, the method being capable of manufacturing a spectacle lens that can be processed while being held, and is excellent in water repellency durability and oil repellency durability. It is presumed that, in the water-repellent layer, the first compound having a small contact angle is formed as a main component on the side opposite to the lens base material, and the second compound having a large contact angle increases toward the lens base material, whereby a spectacle lens that can be processed while being held and is excellent in water repellency durability and oil repellency durability can be obtained.

[0116] 1 Spectacle lens 11 Base material for spectacle lens 11a, 21fa, 31fa Object-side surface 11b, 21bb, 31bb Eyeball-side surface 21f, 21b Hard coat layer 31f, 31b Functional layer 41f, 41b Water-repellent layer

Claims

1. A method for manufacturing an eyeglass lens comprising a lens substrate and a water-repellent layer formed on the lens substrate, comprising a water-repellent layer formation step of depositing a water-repellent layer composition containing a first compound and a second compound onto the lens substrate to form the water-repellent layer on the lens substrate, wherein the deposition start temperature of the first compound is 20°C or higher than the deposition start temperature of the second compound, the water contact angle of the first compound is 4° or lower than the water contact angle of the second compound, and the artificial sebum liquid contact angle of the first compound is 5° or lower than the artificial sebum liquid contact angle of the second compound.

2. The method for manufacturing eyeglass lenses according to claim 1, wherein the first compound has a deposition start temperature of 140 to 180°C, and the second compound has a deposition start temperature of 100 to 140°C.

3. The method for manufacturing eyeglass lenses according to claim 1 or 2, wherein the first compound has a water contact angle of 105 to 116° and an artificial sebum contact angle of 45 to 55°, and the second compound has a water contact angle of 112 to 125° and an artificial sebum contact angle of 55 to 70°.

4. The method for manufacturing spectacle lenses according to claim 1 or 2, wherein, when the vertical axis is the mass retention rate (%) and the horizontal axis is the heating temperature (°C), the slope S (mass% / °C) of the deposition curve in the region from a mass retention rate of 70 mass% to 60 mass%, the absolute value of the difference (S1-S2) between the slope S1 of the first compound and the slope S2 of the second compound is 0.00 to 1.00 (mass% / °C).

5. The method for manufacturing spectacle lenses according to claim 4, wherein the slope S1 of the first compound is -2.00 to -0.10 (mass% / °C) and the slope S2 of the second compound is -2.00 to -0.10 (mass% / °C).

6. The method for manufacturing eyeglass lenses according to claim 1 or 2, wherein the difference between the molecular weight distribution (Mw / Mn) of the first compound and the molecular weight distribution (Mw / Mn) of the second compound is 0.80 or less.

7. The method for manufacturing eyeglass lenses according to claim 6, wherein the molecular weight distribution (Mw / Mn) of the first compound is 1.00 to 1.20, and the molecular weight distribution (Mw / Mn) of the second compound is 1.00 to 1.

80.

8. A method for manufacturing an eyeglass lens according to claim 1 or 2, further comprising the step of depositing metal particles containing at least one metal onto the lens substrate to arrange the metal particles between the lens substrate and the water-repellent layer.

9. The method for manufacturing eyeglass lenses according to claim 8, wherein the metal particles include at least one selected from the group consisting of silver, platinum, gold, palladium, mercury, cadmium, cobalt, nickel, copper, zinc, titanium, molybdenum, and tungsten.

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