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WO2025205702A1 - Procédé de fabrication de verres de lunettes - Google Patents

Procédé de fabrication de verres de lunettes

Info

Publication number
WO2025205702A1
WO2025205702A1 PCT/JP2025/011612 JP2025011612W WO2025205702A1 WO 2025205702 A1 WO2025205702 A1 WO 2025205702A1 JP 2025011612 W JP2025011612 W JP 2025011612W WO 2025205702 A1 WO2025205702 A1 WO 2025205702A1
Authority
WO
WIPO (PCT)
Prior art keywords
coating
meth
lens substrate
layer
acrylate
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
PCT/JP2025/011612
Other languages
English (en)
Japanese (ja)
Inventor
拓哉 島田
巨樹 長嶋
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Hoya Lens Thailand Ltd
Original Assignee
Hoya Lens Thailand Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Hoya Lens Thailand Ltd filed Critical Hoya Lens Thailand Ltd
Publication of WO2025205702A1 publication Critical patent/WO2025205702A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D1/00—Processes for applying liquids or other fluent materials
    • B05D1/40—Distributing applied liquids or other fluent materials by members moving relatively to surface
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D7/00—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/10—Optical coatings produced by application to, or surface treatment of, optical elements
    • G02B1/14—Protective coatings, e.g. hard coatings
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/22—Absorbing filters
    • G02B5/23—Photochromic filters
    • G—PHYSICS
    • G02—OPTICS
    • G02C—SPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
    • G02C13/00—Assembling; Repairing; Cleaning
    • G—PHYSICS
    • G02—OPTICS
    • G02C—SPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
    • G02C7/00—Optical parts
    • G—PHYSICS
    • G02—OPTICS
    • G02C—SPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
    • G02C7/00—Optical parts
    • G02C7/10—Filters, e.g. for facilitating adaptation of the eyes to the dark; Sunglasses

Definitions

  • Spin coating is a known application method in which the central portion of the other surface of the lens substrate is fixed to a spin coating mechanism (a mechanism having the function of rotating the lens substrate), a curable composition is supplied to one surface of the lens substrate (the surface not fixed to the spin coating mechanism), and the spin coating mechanism is then rotated to spread the curable composition over the entire surface of the one surface of the lens substrate.
  • a spin coating mechanism a mechanism having the function of rotating the lens substrate
  • a curable composition is supplied to one surface of the lens substrate (the surface not fixed to the spin coating mechanism)
  • the spin coating mechanism is then rotated to spread the curable composition over the entire surface of the one surface of the lens substrate.
  • Patent Document 1 requires that the tip of the spatula be positioned so as to come into contact with the entire surface of the side surface (edge surface) of the lens substrate, and excessive contact between the tip of the spatula and the side surface (edge surface) of the lens substrate is thought to hinder the rotation of the spin coating mechanism.Furthermore, the method disclosed in Patent Document 1 is thought to be unable to prevent the photocurable composition (a curable composition that is cured by light) from spreading over to the other surface side of the lens substrate, and therefore the method of Patent Document 1 cannot be said to be necessarily simple and convenient. Furthermore, Patent Document 1 does not particularly consider reducing the thickness of the cured coating layer, and therefore it cannot necessarily be said to be an excellent method for reducing the thickness of the cured coating layer.
  • One aspect of the present disclosure aims to provide a simple method for manufacturing eyeglass lenses that reduces the thickness of the cured coating layer formed on one surface of the lens substrate and provides excellent antifouling properties on the other surface of the lens substrate.
  • Embodiments of the present disclosure relate to the following [1] to [7].
  • a method for manufacturing a spectacle lens having a cured coating layer on one surface of a lens substrate comprising: a coating step of coating at least a portion of the other surface of the lens substrate with a coating having one or more through holes; a decompression step of reducing the pressure between the other surface of the lens substrate and a spin-coating mechanism that rotates the lens substrate through the through-holes of the coating material, thereby fixing the other surface of the lens substrate to the spin-coating mechanism; a spin-coating step of spin-coating one surface of the lens substrate with a curable composition.
  • the inventors discovered that the above problems could be solved by covering at least a portion of the other surface of the lens substrate, on which the curable composition is not applied, with a coating having one or more through-holes, reducing the pressure between the other surface of the lens substrate and a spin-coating mechanism through the through-holes in the coating, fixing the other surface of the lens substrate to the spin-coating mechanism, and then spin-coating, thereby completing the present invention.
  • on the surface of X is a concept that includes not only “on the surface of X (contact state)” but also “above the surface of X (non-contact state).”
  • (meth)acrylate encompasses acrylate and methacrylate.
  • An “acrylate” is a compound having one or more acryloyl groups in one molecule.
  • a “methacrylate” is a compound having one or more methacryloyl groups in one molecule.
  • the functionality of a (meth)acrylate is the number of groups selected from the group consisting of acryloyl groups and methacryloyl groups contained in one molecule.
  • (meth)acryloyl group is used to mean an acryloyl group and a methacryloyl group
  • (meth)acryloyloxy group is used to mean an acryloyloxy group and a methacryloyloxy group.
  • the groups described may have a substituent or may be unsubstituted.
  • examples of the substituent include an alkyl group (e.g., a linear alkyl group having 1 to 6 carbon atoms or a branched alkyl group having 1 to 6 carbon atoms), a hydroxyl group, an alkoxy group (e.g., an alkoxy group having 1 to 6 carbon atoms), a halogen atom (e.g., a fluorine atom, a chlorine atom, a bromine atom), a cyano group, an amino group, a nitro group, an acyl group, a carboxy group, an aryl group, a polyether group, etc.
  • an alkyl group e.g., a linear alkyl group having 1 to 6 carbon atoms or a branched alkyl group having 1 to 6 carbon atoms
  • a hydroxyl group e.g., an alkoxy group having 1 to 6 carbon atoms
  • a halogen atom e.g., a fluorine
  • the "number of carbon atoms” refers to the number of carbon atoms in the portion excluding the substituent.
  • the term "straight-chain alkyl group or branched alkyl group” does not include a cycloalkyl group.
  • the straight-chain alkyl group or branched alkyl group may be unsubstituted or may have a substituent. It is acceptable for the straight-chain alkyl group or branched alkyl group to have a cycloalkyl group (e.g., a cyclohexyl group) as a substituent.
  • peripheral portion of the lens substrate refers to a portion of the lens substrate having a radius of 15 mm or more from the center thereof.
  • mid-peripheral portion of the lens substrate refers to a portion of the lens substrate that is more than 5 mm and less than 15 mm in radius from the center of the lens substrate.
  • central portion of the coating refers to the portion of the lens substrate that is no more than a radius of 5 mm from the center of the lens substrate.
  • peripheral portion of the coating refers to the portion 5 mm or less from the outer periphery of the coating.
  • the peripheral portion of the coating may be included in the central portion of the coating, but the portion 5 mm or less from the outer periphery of the coating is referred to as the "peripheral portion of the coating.” Furthermore, when the radius of the coating is less than 5 mm, the peripheral portion of the coating and the central portion of the coating refer to the same portion. In this disclosure and specification, the term “intermediate portion of the coating” refers to a portion that does not belong to the central portion of the coating or the peripheral portion of the coating. Note that when the radius of the coating is 10 mm or less, the "intermediate portion of the coating" does not exist.
  • a method for manufacturing a spectacle lens according to one aspect of the present disclosure is a method for manufacturing a spectacle lens having a cured coating layer on one surface of a lens substrate, and is not particularly limited as long as it includes: a coating step of coating at least a portion of the other surface of the lens substrate with a coating having one or more through holes; a depressurizing step of reducing the pressure between the other surface of the lens substrate and a spin coating mechanism that rotates the lens substrate via the through holes in the coating, thereby fixing the other surface of the lens substrate to the spin coating mechanism; and a spin coating step of spin-coating one surface of the lens substrate with a curable composition, and may further include other steps as necessary.
  • a spectacle lens that can be manufactured by the spectacle lens manufacturing method of the present disclosure has a lens substrate and a cured coating layer on one surface of the lens substrate, and is endowed with special properties (e.g., photochromic properties) based on the cured coating layer, making it suitable for use in eyeglasses.
  • special properties e.g., photochromic properties
  • eyeglass frames there are no particular restrictions on the eyeglass frames to which the above-mentioned eyeglass lenses can be applied, and publicly known technologies can be applied, and they may be full-rim frames that surround the entire eyeglass lens, half-rim frames (nylon frames) that surround only the upper half of the eyeglass lens, under-rim frames (reverse nylon frames) that surround only the lower half of the eyeglass lens, or rimless frames (rimless frames) that only have eyeglass lenses and no frame.
  • full-rim frames that surround the entire eyeglass lens
  • half-rim frames nylon frames
  • under-rim frames reverse nylon frames
  • rimless frames rimless frames
  • the coating step in the method for manufacturing a spectacle lens according to one embodiment of the present disclosure is a step of coating at least a portion of the other surface of the lens substrate with a coating having one or more through holes before the decompression step described below, and may or may not include other treatments.
  • the coverage ratio of the coating to the other surface of the lens substrate is not particularly limited, as long as it can cover at least a portion of the other surface of the lens substrate. From the viewpoint of preventing the curable composition from adhering to the other surface of the lens substrate, the coverage ratio is preferably 30% or more, more preferably 50% or more, even more preferably 70% or more, and particularly preferably 100% of the other surface of the lens substrate.
  • the coverage ratio of the coating material to the surface area of the other surface of the lens substrate is determined as follows. (surface area of the portion of the lens substrate where the coating is covering the other surface (including the surface area of the through-hole diameter)/surface area of the other surface of the lens substrate) ⁇ 100%
  • the lens substrate will be described in more detail below.
  • the material for the lens substrate is not particularly limited, and examples include (meth)acrylic resin; styrene resin; polycarbonate resin; allyl resin; allyl carbonate resin such as diethylene glycol bisallyl carbonate resin (CR-39); vinyl resin; polyester resin; polyether resin; urethane resin obtained by reacting an isocyanate compound with a hydroxy compound such as diethylene glycol; thiourethane resin obtained by reacting an isocyanate compound with a polythiol compound; a cured product (commonly referred to as a transparent resin) obtained by curing a curable composition containing a (thio)epoxy compound having one or more disulfide bonds in the molecule; and oxides such as boric oxide, aluminum oxide, and silicon oxide. These may be used alone or in combination of two or more.
  • the color of the lens substrate there are no particular restrictions on the color of the lens substrate, and it may be colorless (an undyed lens) or dyed.
  • the refractive index of the lens substrate there are no particular restrictions on the refractive index of the lens substrate, and examples include 1.50 to 1.75. Note that in this disclosure and specification, the refractive index refers to the refractive index for light with a wavelength of 546.07 nm, which is the mercury e-line.
  • focal point of the lens substrate there are no particular limitations on the focal point of the lens substrate, and examples include single-focus, multi-focus, and progressive-addition lenses.
  • the surface of the lens substrate is not particularly limited, and examples thereof include a convex surface, a concave surface, a flat surface, etc.
  • the object-side surface is a convex surface and the eyeball-side surface is a concave surface, but the present disclosure is not limited to this.
  • the one surface of the lens substrate and examples thereof include a convex surface, a concave surface, and a flat surface.
  • the other surface of the lens substrate is not particularly limited, and may be, for example, a convex, concave, or flat surface.
  • the thickness of the central portion of the lens substrate is preferably less than 9.1 mm, more preferably 0.8 to 2.4 mm, and particularly preferably 0.8 mm or more and less than 2.0 mm.
  • the thickness of the peripheral portion of the lens substrate is not particularly limited, but from the viewpoint of optical design, it is preferably thicker than the central portion, more preferably 0.8 to 16.5 mm, and particularly preferably 1.6 to 13.0 mm.
  • the peripheral portion does not have to have a uniform thickness, or it may have a uniform thickness.
  • the shape of the lens substrate is not particularly limited, and examples include a convex lens whose central portion is thicker than the peripheral portion, a concave lens whose peripheral portion is thicker than the central portion, and a flat lens whose central portion and peripheral portion are the same thickness. Furthermore, the shape of the lens substrate may or may not be a cylindrical lens whose peripheral portion does not have a uniform thickness.
  • the radius of the lens substrate is preferably 20 to 50 mm, more preferably 25 to 45 mm, and especially preferably 30 to less than 40 mm. If the radius is equal to or greater than the lower limit of the above range, it will be more suitable for use in a variety of eyeglass frames, while if it is equal to or less than the upper limit of the above range, the amount of polishing and grinding required on the outer periphery of the eyeglass lens will be reduced.
  • the material of the coating is not particularly limited and known materials can be used, such as acrylic resin, polyacetal resin, polycarbonate resin, ABS resin, PA resin, PLA resin, carbon, ultraviolet curable resin, silicone resin, acrylic resin, polyurethane resin, epoxy resin, polyamide resin, vinyl chloride resin, and phenolic resin. These may be used alone or in combination of two or more. Of these, polyacetal resin is preferred because it has high resistance to solvents used in cleaning and is easy to clean for recycling.
  • the coating material there are no particular restrictions on the coating material, as long as it can cover at least a portion of the other surface of the lens substrate, and the other surface of the lens substrate may be coated with one layer, or with two or more layers. Furthermore, when multiple coating materials are used, they may all be the same type of coating material, or two or more types may be used.
  • the form of the covering is not particularly limited, and examples include sheets and plates. These may be used alone or in combination of two or more types. Of these, plates are preferred from the standpoint of ease of attaching and removing the covering.
  • the thickness of the coating when it is in the plate state, but it is preferably 2.0 to 20.0 mm, more preferably 2.5 to 15.0 mm, and particularly preferably 3.0 to 10.0 mm. If it is at or above the lower limit of the above range, durability is more easily maintained, and if it is at or below the upper limit of the above range, high-speed rotation is more easily stabilized. Furthermore, the thickness of the coating may or may not be uniform, and the thickness may be varied to match the thickness of the peripheral portion of the lens substrate.
  • the thickness of the coating in the sheet state is preferably 0.1 to 2.0 mm, more preferably 0.3 to 1.8 mm, and especially preferably 0.5 to 1.5 mm. If the thickness is above the lower limit of the above range, durability is more easily maintained, and if it is below the upper limit of the above range, high-speed rotation is more easily stabilized.
  • a perfect circle there are no particular restrictions on the shape of the coating, but from the perspective of preventing decentering of the lens substrate and coating during rotation in spin coating, a perfect circle; or a point-symmetric polygon such as an equilateral triangle, square, rectangle, rhombus, parallelogram, regular hexagon, or regular octagon; and from the perspective of ease of availability and formation, a perfect circle is more preferred.
  • the dimensions of the coating are not particularly limited as long as they are large enough to cover at least a portion of the other surface of the lens substrate, but from the viewpoint of preventing the curable composition from adhering to the other surface of the lens substrate, the coating is preferably large enough to cover 30% or more of the surface area of the other surface of the lens substrate, more preferably 50% or more, even more preferably 70% or more, and particularly preferably 100%. Furthermore, the coating may be large enough to cover 100% or more of the other surface of the lens substrate, i.e., larger than the outer periphery of the lens substrate.
  • the coating can be the same size as the lens substrate (covering 100% of the other surface of the lens substrate). In another embodiment, if the lens substrate is a perfect circle with a radius of 35 mm, the coating can be a perfect circle with a radius of 30 mm, covering 73% of the other surface of the lens substrate.
  • the coverage ratio of the coating material to the surface area of the other surface of the lens substrate is determined as follows. (surface area of the portion of the lens substrate where the coating is covering the other surface (including the surface area of the through-hole diameter)/surface area of the other surface of the lens substrate) ⁇ 100%
  • the peripheral portion of the covering there are no particular restrictions on the peripheral portion of the covering, but it is preferable that it be provided with adhesive rubber (rubber 2 in Figures 1 and 3) in order to prevent the lens substrate and the covering from shifting before carrying out the decompression step described below.
  • the rubber material is not particularly limited as long as it has enough adhesiveness to prevent the lens substrate and the covering from slipping, and known materials can be used, such as urethane resin, silicone resin, Teflon, nitrile, neoprene, etc. These may be used alone or in combination of two or more. Among these, urethane resin is preferred.
  • the number of through holes in the coating is not particularly limited as long as it is one or more, and may be one, two or more, ten or more, or twenty or more. Furthermore, when one through-hole is provided, it is preferable that the center of the through-hole is positioned at the center of the covering, in order to prevent decentering of the lens and covering during rotation. Furthermore, when two or more through holes are provided, it is preferable that the through holes are provided so as to be point symmetrical in order to avoid decentering of the lens and coating during rotation.
  • the size of the through-holes in the coating is not particularly limited as long as they can be contained within the coating, and any diameter of through-holes can be used. Furthermore, when two or more through holes are provided, the diameters of the through holes may all be the same size or may be different, but it is preferable to design them so that the lens and coating do not become decentered during rotation.
  • the position of the through-hole in the coating is not particularly limited, as long as it is a position where the pressure between the lens substrate and the spin coating can be reduced via the through-hole in the decompression step described below, i.e., the through-hole is located within the area where the lens substrate and coating are in contact, and the outer periphery of the area does not come into contact with the outer periphery of the through-hole.
  • the through-hole may be located in the center of the coating, in the peripheral area of the coating, or in the middle area of the coating.
  • the method for manufacturing the above-mentioned coated object may be a manufacturing method in which a coating of the desired shape is cut from a plate or sheet made of the above-mentioned material that is larger than the desired coated object, through holes are drilled, and the coated object is obtained; or it may be a manufacturing method in which a composition that hardens with light, heat, drying, etc. to form a plate or sheet of the above-mentioned material is poured into a mold for the coating of the desired shape, forming a coated object of the desired shape, through holes are drilled, and the coated object is obtained.
  • the coating step may or may not include other treatments as necessary in addition to coating at least a portion of the other surface of the lens substrate with a coating having one or more through holes.
  • the other treatment in the coating step is not particularly limited, and examples thereof include pretreatment of the lens substrate carried out prior to coating the other surface of the lens substrate with a coating material. Pretreatment is preferably carried out from the viewpoint of improving adhesion between the cured coating layer of the curable composition and the lens substrate.
  • pretreatment there are no particular limitations on the type of pretreatment that can be used, and examples include chemical treatment using a basic or acidic aqueous solution, polishing treatment using an abrasive, plasma treatment using atmospheric pressure plasma or low pressure plasma, corona discharge treatment, and UV ozone treatment. These may be used alone or in combination of two or more.
  • the coating step in the method for manufacturing an eyeglass lens according to one aspect of the present disclosure is a step of reducing the pressure between the other surface of the lens substrate and a spin-coating mechanism that rotates the lens substrate through a through-hole in the coating material, prior to the spin-coating step described below, to fix the other surface of the lens substrate to the spin-coating mechanism, and may or may not include other processes.
  • spin-coating mechanism can be one that includes a V-ring (V-ring 41 in FIG. 1) and a fixing table (fixing table 42 in FIG. 1) for fixing a sample (object to be rotated), which is provided in a spin-coating apparatus of the known art (spin-coating mechanism 40 in FIG. 1). Because the spin-coating mechanism includes the V-ring between the object to be coated and the fixing table, it is possible to efficiently reduce the pressure between the other surface of the lens substrate and the spin-coating mechanism.
  • V-ring there are no particular limitations on the V-ring, and any known V-ring can be used. There are no particular restrictions on the diameter of the aperture of the V-ring, but from the viewpoint of vacuum efficiency and maintaining vacuum, it is preferable that the diameter be large enough to cover all of the through-holes provided within the area where the lens substrate and the coating are in contact. There are no particular limitations on commercially available V-rings, and examples thereof include silicone resin, Teflon, nitrile, neoprene, etc. These may be used alone or in combination of two or more.
  • the spin-coating step in the method for manufacturing a spectacle lens according to one embodiment of the present disclosure is a step of spin-coating a curable composition onto one surface of the lens substrate after the aforementioned decompression step, and may or may not include other treatments.
  • the spin coating is a known coating method, and one embodiment of the present disclosure can be a coating method in which a curable composition is supplied to one surface of a lens substrate, and then a spin coating mechanism is rotated to spread the curable composition over the entire surface of the one surface of the lens substrate.
  • the conditions for carrying out the spin coating are not particularly limited, and known conditions can be employed.
  • One example of conditions for carrying out the spin coating is an environment of a temperature of 25° C. and a relative humidity of 50%.
  • curable composition The curable composition will be described in more detail below.
  • a curable composition refers to, for example, a curable composition that has the property of curing when irradiated with light, a curable composition that has the property of curing when heat is applied, or a curable composition that has the property of curing when moisture is absorbed, and is a composition that exhibits one or more properties after curing, such as adhesion, photochromic properties, anti-reflection properties, anti-fouling properties, and scratch resistance.
  • the eyeglass lens By forming one or more cured coating layers, which are the cured products of the above-mentioned curable compositions, on the surface of a lens substrate, the eyeglass lens can acquire properties such as adhesion, photochromic properties, anti-reflection properties, anti-fouling properties, and scratch resistance.
  • primer layer composition ((Curable composition for forming primer layer))
  • a primer layer composition containing a polyisocyanate, a hydroxy group-containing polymerizable compound, and at least one polymerizable compound selected from the group consisting of (meth)acrylates and vinyl ethers, the polymerizable compound having a viscosity of 100 cP or less.
  • the components contained in the primer layer composition are not particularly limited, but it is preferable that the primer layer composition contain the above three components from the viewpoint of suppressing attenuation of photochromic properties caused by the primer layer, which is the cured product of the primer layer composition, and from the viewpoint of improving adhesion.
  • the various components contained in the primer layer composition will be described in more detail below.
  • the polyisocyanate is a compound having two or more isocyanate groups in one molecule.
  • the number of isocyanate groups contained in one molecule of the polyisocyanate is not particularly limited, but is preferably 2 to 6, more preferably 3 to 5, and particularly preferably 3 to 4. When the number is at least the lower limit of the above range, the water resistance of the primer layer is likely to be improved, and when the number is at most the upper limit of the above range, adhesion to the lens substrate is likely to be improved.
  • the molecular weight of the polyisocyanate is preferably 200 to 800, more preferably 300 to 700, and especially preferably 400 to 600. If it is above the lower limit of the above range, it will be easier to adhere to the lens substrate, and if it is below the upper limit of the above range, the water resistance of the primer layer will be improved.
  • polyisocyanate examples include, for example, aromatic diisocyanates such as xylylene diisocyanate, phenylene diisocyanate, tolylene diisocyanate, diphenylmethane diisocyanate, and naphthalene diisocyanate; aliphatic or alicyclic diisocyanates such as hexamethylene diisocyanate, lysine diisocyanate, cyclohexane diisocyanate, isophorone diisocyanate, 4,4'-dicyclohexylmethane diisocyanate, 1,3-bisisocyanatomethylcyclohexane, and tetramethylxylylene diisocyanate; etc.
  • aromatic diisocyanates such as xylylene diisocyanate, phenylene diisocyanate, tolylene diisocyanate, diphenylmethane diisocyanate, and naphthalene diisocyan
  • polyisocyanates exemplified above may be allophanate, adduct, biuret, or isocyanurate, and may be used alone or in combination of two or more.
  • commercially available polyisocyanates are not particularly limited, and examples thereof include those manufactured by Tosoh Corporation such as Coronate HX, Coronate HXR, Coronate HXLV, Coronate HK, Coronate 2715, Coronate HL, Coronate L, Coronate 2037, HDI, TDI, and MDI; and those manufactured by Mitsui Chemicals, Inc.
  • the number of hydroxy groups contained in one molecule of the hydroxy group-containing polymerizable compound is not particularly limited, but is preferably 1 to 6, more preferably 1 to 5, and particularly preferably 2 to 4.
  • the reaction efficiency with polyisocyanate tends to be good
  • the number is equal to or less than the upper limit of the above range
  • adhesion to the photochromic layer tends to be good.
  • the present inventors speculate that the urethane bond formed by reacting the isocyanate group of the polyisocyanate with the hydroxy group of the hydroxy group-containing polymerizable compound contributes to improving the adhesion of the primer layer.
  • the hydroxy group-containing polymerizable compound is a (meth)acrylate.
  • the number of functional groups of the (meth)acrylate is not particularly limited, but from the viewpoint of adhesion, it is preferably 1 (monofunctional) to 3, more preferably 2 to 3.
  • the (meth)acryloyl group, which is the functional group may contain only acryloyl groups, may contain only methacryloyl groups, or may contain acryloyl groups and methacryloyl groups. In one embodiment, from the viewpoint of adhesion, it is preferable that the hydroxy group-containing polymerizable compound contains only acryloyl groups as the (meth)acryloyl groups.
  • the molecular weight of the hydroxyl group-containing polymerizable compound is not particularly limited, but is preferably 100 to 600, more preferably 200 to 500, and particularly preferably 300 to 400. If the molecular weight is above the lower limit of the above range, the reaction efficiency with the polyisocyanate tends to be good, and if the molecular weight is below the upper limit of the above range, adhesion to the photochromic layer tends to be good.
  • the (meth)acrylate are not particularly limited and include, for example, 2-hydroxyethyl (meth)acrylate, hydroxypropyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, 1,4-cyclohexanedimethanol monoacrylate, 2-hydroxy-1-acryloxy-3-methadryloxypropane, 2-hydroxy-1-3-dimethacryloxypropane, pentaerythritol tetraacrylate, 2-hydroxy-3-phenoxypropyl acrylate, monoacryloxyethyl hexahydrophthalate, 2-acryloyloxyethyl phthalate, 2-(acryloxyoxy)ethyl 2-hydroxyethyl phthalate, and compounds represented by the following formula (1): These may be used alone or in combination of two or more.
  • hydroxy group-containing polymerizable compound is a hydroxy group-containing polymerizable compound having an amide group.
  • the hydroxy group-containing polymerizable compound having an amide group is not particularly limited, and examples thereof include N-(2-hydroxyethyl)acrylamide.
  • hydroxy group-containing polymerizable compounds having an epoxy ester structure are not particularly limited, and examples thereof include Epoxy Ester 40EM (manufactured by Kyoeisha Chemical Co., Ltd.), Epoxy Ester 70PA (manufactured by Kyoeisha Chemical Co., Ltd.), Epoxy Ester 80MFA (manufactured by Kyoeisha Chemical Co., Ltd.), Epoxy Ester 200PA (manufactured by Kyoeisha Chemical Co., Ltd.), Epoxy Ester 3002M(N) (manufactured by Kyoeisha Chemical Co., Ltd.), Epoxy Ester 3002A(N) (manufactured by Kyoeisha Chemical Co., Ltd.), Epoxy Ester 3000MK (manufactured by Kyoeisha Chemical Co., Ltd.), Epoxy Ester 3000A (manufactured by Kyoeisha Chemical Co., Ltd.), etc. These may be used alone or in combination of two or more.
  • the viscosity of the low-viscosity polymerizable compound there are no particular restrictions on the viscosity of the low-viscosity polymerizable compound, as long as it is 100 cP or less. However, from the viewpoints of ease of handling and preventing the occurrence of optical defects, it is preferably 5 to 70 cP, and more preferably 10 to 50 cP.
  • the number of functional groups of the (meth)acrylate, which is one form of the low-viscosity polymerizable compound, is not particularly limited, but from the viewpoint of adhesion, it is preferably 1 (monofunctional) to 3, more preferably 1 (monofunctional) to 2.
  • the (meth)acrylate, which is one form of the low-viscosity polymerizable compound can contain an aryl group (e.g., a phenyl group), an amide group, etc.
  • a "vinyl ether” refers to a compound having one or more vinyl groups and one or more ether bonds in one molecule, preferably having two or more vinyl groups in one molecule, and more preferably having two to four vinyl groups in one molecule.
  • the number of ether bonds contained in the vinyl ether is preferably two to four in one molecule.
  • the content of the polyisocyanate is not particularly limited, but is preferably 10.0 to 70.0 mass%, more preferably 20.0 to 60.0 mass%, and particularly preferably 30.0 to 50.0 mass%, relative to 100 mass% of the total of the low-viscosity polymerizable compound, the polyisocyanate, and the hydroxy group-containing polymerizable compound.
  • the thickness is equal to or greater than the lower limit of the above range, the water resistance of the primer layer is likely to be improved, and when the thickness is equal to or less than the upper limit of the above range, adhesion to the lens substrate is likely to be improved.
  • the polymerization initiator is not particularly limited, and known polymerization initiators can be used.
  • the known polymerization initiator is not particularly limited, and examples thereof include a photoradical polymerization initiator and a thermal polymerization initiator. These may be used alone or in combination of two or more. Among these, a photoradical polymerization initiator is preferred from the viewpoint of progressing the polymerization reaction in a short time.
  • the photoradical polymerization initiator reference can be made to the polymerization initiators that can be contained in the curable composition for forming a photochromic layer, which will be described later.
  • Component B-- Component B is a monofunctional (meth)acrylate represented by the following formula (4).
  • R 10 represents a hydrogen atom or a methyl group.
  • the monofunctional (meth)acrylate represented by formula (4) may be an acrylate or a methacrylate.
  • the content is equal to or greater than the lower limit of the above range, the color density of the photochromic layer tends to be high, whereas if the content is equal to or less than the upper limit of the above range, the photochromic compound tends to dissolve in the composition for the photochromic layer.
  • the polyfunctional (meth)acrylate other than Component A that may be contained in the two or more (meth)acrylates is not particularly limited, but from the viewpoint of increasing the (meth)acryloyl group content in the composition for photochromic layer and forming a rigid polymer network between molecules, a (meth)acrylate having a high proportion of (meth)acryloyl groups in the molecule is preferred. From this viewpoint, a polyfunctional (meth)acrylate having a smaller molecular weight than Component A is preferred.
  • the molecular weight of the polyfunctional (meth)acrylate other than Component A is not particularly limited, but from the above viewpoint, it is preferably 100 or more and less than 500, more preferably 100 to 400, and particularly preferably 100 to 350.
  • the number of functional groups of the polyfunctional (meth)acrylate other than Component A is preferred.
  • the number of functional groups of the polyfunctional (meth)acrylate can be, for example, 10 to 15.
  • polyfunctional (meth)acrylates having 10 to 15 functional groups include poly[(3-methacryloyloxypropyl)silsesquioxane] derivatives. These may be used alone or in combination of two or more.
  • the polyfunctional (meth)acrylate is not particularly limited, and examples thereof include a polyfunctional (meth)acrylate having neither a cyclic structure nor a branched structure (component C), a bifunctional (meth)acrylate having at least one structure selected from the group consisting of a cyclic structure and a branched structure (component D), etc. These may be used alone or in combination of two or more. Components C and D will be described in more detail below.
  • Component C-- Component C is a polyfunctional (meth)acrylate having neither a cyclic structure nor a branched structure, represented by the following formula (5).
  • R3 and R4 each independently represent a hydrogen atom or a methyl group.
  • m represents an integer of 1 or more, and may be 10 or less, 9 or less, 8 or less, 7 or less, or 6 or less.
  • component C there are no particular restrictions on the molecular weight of component C, but it is preferably 100 to 400, more preferably 140 to 350, and especially preferably 160 to 300. If it is above the lower limit of the above range, the fading rate tends to be improved, while if it is below the upper limit of the above range, the color density of the photochromic layer tends to be increased.
  • the component C may contain only acryloyl groups, only methacryloyl groups, or both acryloyl groups and methacryloyl groups as (meth)acryloyl groups.
  • Specific examples of the component C are not particularly limited and include, for example, 1,9-nonanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,10-decanediol di(meth)acrylate, etc. These may be used alone or in combination of two or more.
  • Component D-- Component D is a bifunctional (meth)acrylate containing at least one structure selected from the group consisting of a cyclic structure and a branched structure. It is presumed that the inclusion of the component D in the composition for photochromic layer contributes to improving the color density of the photochromic layer formed from the composition for photochromic layer.
  • the component D contains one or more cyclic structures and no branched structures in one molecule, in another embodiment, one or more branched structures and no cyclic structures in one molecule, and in still another embodiment, one or more cyclic structures and one or more branched structures in one molecule.
  • the number of at least one structure selected from the group consisting of cyclic structures and branched structures contained in the above component D is not particularly limited, but is preferably 1 to 3, more preferably 1 to 2, and particularly preferably 1.
  • the component D has a methacryloyl group
  • the branched structure contained in the methacryloyl group is not taken into consideration.
  • component D containing one or more cyclic structures is an alicyclic bifunctional (meth)acrylate.
  • the alicyclic bifunctional (meth)acrylate is not particularly limited, and examples thereof include compounds having a structure represented by R 111 -(L 11 ) n11 -Q-(L 22 ) n22 -R 222 .
  • Q represents a divalent alicyclic group
  • R 111 and R 222 each independently represent a (meth)acryloyl group or a (meth)acryloyloxy group
  • L 11 and L 22 each independently represent a linking group
  • n11 and n22 each independently represent 0 or 1.
  • Component D containing one or more branched structures is, for example, a bifunctional (meth)acrylate containing a branched alkylene group.
  • the number of carbon atoms in the branched alkylene group is not particularly limited, but is preferably 1 to 10, more preferably 2 to 9, even more preferably 3 to 8, and particularly preferably 4 to 7.
  • One embodiment of the branched alkylene group may contain a quaternary carbon (i.e., a carbon bonded to four carbons).
  • Component D may contain only acryloyl groups, only methacryloyl groups, or both acryloyl groups and methacryloyl groups as (meth)acryloyl groups.
  • the content of Component A is not particularly limited, but is preferably 50 to 95% by mass, more preferably 55 to 92% by mass, and particularly preferably 60 to 90% by mass, based on 100% by mass of all polymerizable compounds contained in the composition for photochromic layer.
  • the content is equal to or greater than the lower limit of the above range, the fading rate is likely to be improved, and when the content is equal to or less than the upper limit of the above range, weather resistance is likely to be improved.
  • a component that corresponds to both Component A and Component C, or Component A and Component D, is considered to be Component A.
  • Component A can be the component that accounts for the largest proportion of multiple polymerizable compounds contained in the composition.
  • the content of Component C is not particularly limited, but is preferably 1 to 30% by mass, and more preferably 3 to 27% by mass, relative to 100% by mass of all polymerizable compounds contained in the composition for photochromic layer. If the content is equal to or greater than the lower limit of the above range, the color density tends to increase, whereas if the content is equal to or less than the upper limit of the above range, the fading rate tends to increase.
  • the composition for photochromic layer may contain only one type of component C, and in another embodiment, it may contain two or more types of component C. When two or more types of component C are contained, the content of component C is the total content of the two or more types.
  • composition for the photochromic layer may contain a photochromic compound together with the polymerizable compound.
  • the photochromic compound is not particularly limited, and for example, any known compound that exhibits photochromic properties when exposed to ultraviolet light can be used.
  • the photochromic compound are not particularly limited and include compounds having a known skeleton that exhibits photochromic properties, such as azobenzenes, spiropyrans, spirooxazines, naphthopyrans, indenonaphthopyrans, phenanthropyrans, hexaallylbismidazoles, donor-acceptor Stenhouse adducts (DASA), salicylideneanilines, dihydropyrenes, anthracene dimers, fulgides, diarylethenes, phenoxynaphthacenequinones, and stilbenes; fulgimide compounds; spirooxazine compounds; chromene compounds; indeno-fused naphthopyran compounds; and at least one compound selected from the group consisting of photochromic compounds represented by general formula A, photochromic compounds represented by general formula B, and photochromic compounds represented by general formula C, as described in WO 2022/138966.
  • DASA
  • the composition for photochromic layer may contain, in addition to two or more types of (meth)acrylate and a photochromic compound, one or more of various additives that may be typically contained in a curable composition, in any amount, as needed.
  • the additives that may be contained in the composition for photochromic layer are not particularly limited, and examples thereof include a polymerization initiator for promoting a polymerization reaction.
  • the polymerization initiator is not particularly limited, and examples include photoradical polymerization initiators and thermal polymerization initiators. These may be used alone or in combination of two or more. Among these, photoradical polymerization initiators are preferred from the viewpoint of progressing the polymerization reaction in a short time.
  • the photoradical polymerization initiator is not particularly limited, and examples thereof include benzoin ketals such as 2,2-dimethoxy-1,2-diphenylethan-1-one; ⁇ -hydroxyketones such as 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, and 1-[4-(2-hydroxyethoxy)phenyl]-2-hydroxy-2-methyl-1-propan-1-one; ⁇ -aminoketones such as 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one and 1,2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one; oxime esters such as bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, bis(2,6-dimethoxybenzoyl)-2,4,4-trimethylpentylphosphine oxide, and 2,4,6-trimethylbenzo
  • 2,4,5-triarylimidazole dimers such as 2-(p-methoxyphenyl)-4,5-diphenylimidazole dimer and 2-(p-methoxyphenyl)-4,5-diphenylimidazole dimer; benzophenone compounds such as benzophenone, N,N'-tetramethyl-4,4'-diaminobenzophenone, N,N'-tetraethyl-4,4'-diaminobenzophenone, and 4-methoxy-4'-dimethylaminobenzophenone; 2-ethylanthraquinone, phenanthrenequinone, 2-tert-butylanthraquinone, octamethylanthraquinone, 1,2-benzanthraquinone, 2,3-benzanthraquinone, 2-phenylanthraquinone, 2, Examples of suitable compounds include quinone compounds such as 3-diphenylanthraquinone, 1-
  • These compounds may be used alone or in combination of two or more.
  • ⁇ -hydroxyketones and phosphine oxides are preferred from the viewpoints of curability, transparency, and heat resistance.
  • the substituents on the aryl groups of the two triarylimidazole moieties may be the same, making the compound symmetrical, or different, making the compound asymmetrical.
  • a thioxanthone compound may be combined with a tertiary amine, such as the combination of diethylthioxanthone and dimethylaminobenzoic acid.
  • the content of the polymerization initiator is not particularly limited, but is preferably about 0.1 to 5.0% by mass relative to 100% by mass of the composition for the photochromic layer.
  • the photochromic layer composition may further contain any amount of commonly used known additives, such as surfactants, antioxidants, radical scavengers, light stabilizers, UV absorbers, color inhibitors, antistatic agents, fluorescent dyes, dyes, pigments, fragrances, plasticizers, and silane coupling agents. These may be used alone or in combination of two or more.
  • additives such as surfactants, antioxidants, radical scavengers, light stabilizers, UV absorbers, color inhibitors, antistatic agents, fluorescent dyes, dyes, pigments, fragrances, plasticizers, and silane coupling agents.
  • the photochromic layer composition can be prepared by mixing the various components described above simultaneously or sequentially in any order.
  • an annealing treatment (heat treatment) can be carried out as necessary.
  • the conditions for the annealing treatment are not particularly limited, but it is preferable to carry out the annealing treatment in a heat treatment furnace with an atmospheric temperature of about 90 to 130°C.
  • the thickness of the photochromic layer is preferably 5 to 40 ⁇ m, more preferably 10 to 35 ⁇ m, and especially preferably 15 to 30 ⁇ m. If the thickness is above the lower limit of the above range, the color density tends to become stronger, while if the thickness is below the upper limit of the above range, it becomes easier to maintain transparency.
  • curable composition for forming a protective layer ((Curable composition for forming a protective layer))
  • One embodiment of the above-mentioned curable composition for forming a protective layer (hereinafter sometimes simply referred to as "protective layer composition") is a curable composition containing one or more types of (meth)acrylate and containing 70.0 mass% or more of an alicyclic bifunctional (meth)acrylate relative to 100 mass% of all (meth)acrylates.
  • the components contained in the protective layer composition are not particularly limited, but from the viewpoint of hardness and solvent resistance of the protective layer, it is preferable that the composition contains an alicyclic bifunctional (meth)acrylate.
  • the alicyclic bifunctional (meth)acrylate contained in the composition for forming the protective layer reference can be made to the alicyclic bifunctional (meth)acrylate as an example of the curable composition for forming the photochromic layer described above.
  • the content of the alicyclic bifunctional (meth)acrylate is not particularly limited, but from the viewpoint of obtaining higher hardness and better solvent resistance of the protective layer, it is preferably 70.0 mass% or more, more preferably 75.0 mass% or more, even more preferably 85.0 mass% or more, and particularly preferably 95.0 mass% or more, based on 100 mass% of all (meth)acrylates.
  • the total amount of (meth)acrylate may be the alicyclic bifunctional (meth)acrylate.
  • the protective layer composition may contain one or more other (meth)acrylates in addition to an alicyclic bifunctional (meth)acrylate as the (meth)acrylate.
  • the (meth)acrylate may contain only an alicyclic bifunctional (meth)acrylate.
  • the other (meth)acrylate contained together with the alicyclic bifunctional (meth)acrylate is not particularly limited, and one or more of various (meth)acrylates can be used.
  • Specific examples of the other (meth)acrylate are not particularly limited, and include, for example, monofunctional, bifunctional, trifunctional, tetrafunctional, and pentafunctional (meth)acrylates, which may be acyclic or cyclic.
  • the (meth)acrylate containing a cyclic structure may have an alicyclic structure as the cyclic structure, or may have another cyclic structure.
  • the content of the other (meth)acrylates is not particularly limited, but from the viewpoint of obtaining high hardness and excellent solvent resistance in the protective layer of the present disclosure, the content is preferably 0 to 30.0 mass%, more preferably 1.0 to 25.0 mass%, and particularly preferably 5.0 to 20.0 mass%, relative to 100 mass% of all (meth)acrylates.
  • the composition for a protective layer contains at least one (meth)acrylate as a polymerizable compound, and in one embodiment, may contain one or more polymerizable compounds other than (meth)acrylate, or in another embodiment, may contain only (meth)acrylate as a polymerizable compound.
  • the other polymerizable compound is not particularly limited, and one or more known polymerizable compounds may be used.
  • the content of the (meth)acrylate is not particularly limited, but from the viewpoint of durability, it is preferably 80.0% by mass or more, more preferably 90.0% by mass or more, and particularly preferably 100% by mass, of all polymerizable compounds in the composition for the protective layer (100% by mass).
  • the content of the (meth)acrylate (the total amount when two or more (meth)acrylates are contained) is preferably 80.0% by mass or more, more preferably 90.0% by mass or more, and particularly preferably 95.0% by mass or more, based on 100% by mass of the protective layer composition.
  • the protective layer composition may or may not contain a solvent. If a solvent is contained, there are no particular restrictions on the solvent that can be used, and any solvent can be used in any amount as long as it does not inhibit the polymerization reaction of the curable composition.
  • the composition for a protective layer may further contain one or more additives in any content, as required.
  • the additives are not particularly limited, and examples thereof include various known additives such as a polymerization initiator for promoting a polymerization reaction, a leveling agent for improving the coating suitability of the composition, etc. These may be used alone or in combination of two or more.
  • the polymerization initiator is not particularly limited, and examples thereof include a photoradical polymerization initiator and a thermal polymerization initiator. These may be used alone or in combination of two or more. Among these, a photoradical polymerization initiator is preferred from the viewpoint of progressing the polymerization reaction in a short time. Specific examples of the photoradical polymerization initiator can be found in the polymerization initiators that can be contained in the photochromic layer-forming curable composition described above.
  • the content of the polymerization initiator is not particularly limited, but from the viewpoint of the efficiency of forming the protective layer, it is preferably 0.1 to 5.0% by mass in 100% by mass of the composition for protective layer.
  • the composition for the protective layer may further contain an ultraviolet absorber, if necessary.
  • the ultraviolet absorber is not particularly limited, and examples thereof include hydroxyphenyl triazine compounds such as 2,4-bis(2,4-dimethylphenyl)-6-(2-hydroxy-4-n-octyloxyphenyl)-s-triazine, 2,4,6-tris(2-hydroxy-4-hexyloxy-3-methylphenyl)-s-triazine, 2-[2-hydroxy-4-(2-ethylhexyloxy)phenyl]-4,6-diviphenyl-s-triazine, and 2-[[2-hydroxy-4-[1-(2-ethylhexyloxycarbonyl)ethyloxy]phenyl]]-4,6-diphenyl-s-triazine; and benzotriazole compounds such as 2-(5-chloro-2H-benzotriazol-2-yl)-6-tert-butyl-4-methylphenol and 2-(
  • the ultraviolet absorber contained in the composition for a protective layer can contribute to improving the weather resistance of the protective layer.
  • the content of the ultraviolet absorber is not particularly limited, but is preferably 0.1 to 1.0% by mass in 100% by mass of the composition for protective layer from the viewpoint of optical properties such as transparency.
  • the protective layer composition can be prepared by mixing the various components described above simultaneously or sequentially in any order.
  • the protective layer can be formed on one surface of the lens substrate by spin-coating the above-mentioned protective layer composition onto one surface of the lens substrate and then curing the spin-coated protective layer composition.
  • the protective layer has scratch resistance.
  • the position of the protective layer is not particularly limited, but is preferably on the cured coating layer (e.g., photochromic layer) from the viewpoint of protecting the cured coating layer (e.g., photochromic layer). From this viewpoint, the protective layer preferably has high hardness.
  • the protective layer is not particularly limited, but preferably has excellent solvent resistance.
  • a wiping treatment with a solvent is usually performed to clean the surface of the formed layer, but if the protective layer is damaged in this wiping treatment, it may cause fogging or optical defects in the eyeglass lens.
  • the curing treatment is not particularly limited, and examples thereof include light irradiation, heat treatment, etc. These may be used alone or in combination of two or more. Among these, light irradiation is preferred from the viewpoint of progressing the curing reaction in a short time.
  • the curing treatment conditions can be determined depending on the types of various components contained in the composition for protective layer and the composition of the composition for protective layer. After the hardening treatment, an annealing treatment (heat treatment) can be carried out as necessary.
  • the conditions for the annealing treatment are not particularly limited, but it is preferable to carry out the annealing treatment in a heat treatment furnace with an atmospheric temperature of about 90 to 130°C.
  • the thickness of the protective layer is preferably 5 to 40 ⁇ m, more preferably 10 to 35 ⁇ m, and especially preferably 15 to 30 ⁇ m. If it is at or above the lower limit of the above range, the durability of the eyeglass lens will be good, and if it is at or below the upper limit of the above range, it will be easier to maintain the transmittance (transparency) of the cured coating layer.
  • an eyeglass lens manufactured by a spectacle lens manufacturing method can have a layer structure of "photochromic layer/protective layer.”
  • the layer structure “/" is used to encompass both a structure in which the two layers are in direct contact without any other layer in between, and a structure in which one or more other layers are provided between them.
  • the optical article can have a layer structure of "photochromic layer/protective layer/other cured coating layer.”
  • the other cured coating layer is not particularly limited, but examples include a cured coating layer generally referred to as a hard coat layer. These may be used alone, or two or more types may be used.
  • Providing a hard coat layer in addition to the protective layer can further enhance the durability of the optical article.
  • providing a hard coat layer can also enhance the impact resistance of the optical article.
  • the other cured coating layer can be in direct contact with the protective layer without any other layer in between.
  • the thickness of the other cured coating layer is preferably 1 to 10 ⁇ m, more preferably 1 to 8 ⁇ m, and particularly preferably 1 to 5 ⁇ m.
  • the other cured coating layer can be thinner than the protective layer.
  • the hard coat layer can be formed by irradiating and/or heating a curable composition for forming a hard coat layer (hereinafter, sometimes simply referred to as a "hard coat layer composition").
  • the hard coat layer is not particularly limited, and examples thereof include an organosilicon-based cured coating layer.
  • An organosilicon-based cured coating layer is generally preferred because it has excellent impact resistance.
  • an antireflection layer is further provided as one embodiment, an organosilicon-based cured coating layer is generally preferred because it has excellent adhesion to the antireflection layer.
  • the organosilicon-based cured coating layer is a cured coating layer obtained by curing a composition for hard coat layer containing an organosilicon compound.
  • the organosilicon compound is not particularly limited and examples thereof include organosilicon compounds that can generate silanol groups by polymerization treatment, such as ⁇ -glycidoxypropyltrimethoxysilane; organopolysiloxanes such as water-dispersed colloidal silica having reactive groups such as halogen atoms or amino groups that undergo condensation reaction with silanol groups; silane coupling agents having a polymerizable group such as a vinyl group, allyl group, (meth)acryloyl group, or (meth)acryloyloxy group, and a hydrolyzable group such as an alkoxy group; etc.
  • the hard coat layer composition containing an organosilicon compound may further contain silicon oxide; particles of an inorganic substance such as titanium oxide; etc., as necessary, for adjusting the refractive index, etc.
  • the hard coat layer composition containing an organosilicon compound may further contain, as necessary, a curing agent such as aluminum acetylacetonate to improve the hardness of the hard coat layer; a surfactant such as a silicone surfactant to control liquid dispersibility and interfacial tension; etc.
  • a curing agent such as aluminum acetylacetonate to improve the hardness of the hard coat layer
  • a surfactant such as a silicone surfactant to control liquid dispersibility and interfacial tension
  • known techniques related to organosilicon-based cured coating layers that can function as hard coat layers can be applied.
  • the curable composition containing an organosilicon compound can be cured by proceeding with a polymerization reaction through light irradiation and/or heat treatment, depending on the types of components contained
  • the hard coat layer composition may or may not contain a solvent. If a solvent is contained, there are no particular restrictions on the solvent that can be used, and any solvent can be used in any amount as long as it does not inhibit the polymerization reaction of the curable composition.
  • the other cured coating layer on the protective layer there are no particular restrictions, but it is preferable to wipe the surface of the protective layer with a solvent to prevent foreign matter from becoming interposed between the protective layer and the other cured coating layer.
  • the solvent wiping process can damage the protective layer (e.g., cause surface roughness), which can cause clouding or optical defects in eyeglass lenses that include the protective layer.
  • a protective layer formed from the protective layer composition described above exhibits excellent solvent resistance, and is therefore suitable for providing the other cured coating layer on the protective layer.
  • the wiping treatment with a solvent is not particularly limited and can be carried out by known methods, such as wiping the surface of the protective layer with a cloth soaked in the solvent.
  • the solvent is not particularly limited and examples include ketone solvents such as acetone; alcohol solvents such as ethanol and isopropyl alcohol; and the like. These may be used alone or in combination of two or more.
  • the protective layer preferably has high resistance to ketone solvents, which are commonly used as wiping solvents during the production of optical articles.
  • the curable composition may or may not further contain other curable compositions as necessary in addition to the above-mentioned primer layer composition, photochromic layer composition, and protective layer composition.
  • the other curable compositions are not particularly limited and include, for example, compositions that exhibit antireflection properties after curing, compositions that exhibit antifouling properties, curable compositions that exhibit antifogging properties, etc. These may be used alone or in combination of two or more.
  • the cured coating layer which is the cured product of the curable composition, is not particularly limited, and examples include the above-mentioned primer layer, photochromic layer, protective layer, hard coat layer, and other cured coating layers formed by curing a curable composition. These may be used alone or in combination of two or more.
  • One form of the cured coating layer may have a primer layer, a photochromic layer, and a protective layer.
  • the thickness of the cured coating layer is preferably 5 to 100 ⁇ m, more preferably 5 to 70 ⁇ m, and especially preferably 5 to 50 ⁇ m. If the thickness is equal to or greater than the lower limit of the above range, adhesion is more easily maintained. If the thickness is equal to or less than the upper limit of the above range, the transmittance (transparency) of the cured coating layer is more easily maintained and the effect of the present disclosure (reduced thickness of the cured coating layer) is more easily achieved. Note that if the cured coating layer has multiple layers, the thickness of the cured coating layer is the total thickness of the primer layer, photochromic layer, and protective layer.
  • Photochromic Layer Composition 1 In a plastic container, 65 parts by mass of trimethylolpropane polyoxyethylene ether trimethacrylate (molecular weight 1264), 5 parts by mass of n-lauryl methacrylate (molecular weight 254), 5 parts by mass of 1,9-nonanediol dimethacrylate (molecular weight 296), 20 parts by mass of n-butyl methacrylate (molecular weight 142), and 5 parts by mass of a poly[(3-methacryloyloxypropyl)silsesquioxane] derivative (a compound represented by the structural formula (7) below) were mixed to obtain a mixture of polymerizable compounds.
  • a poly[(3-methacryloyloxypropyl)silsesquioxane] derivative a compound represented by the structural formula (7) below
  • the thus-obtained mixture of polymerizable compounds was mixed with a photochromic compound (an indeno-fused naphthopyran compound represented by the following structural formula (6) described in U.S. Pat. No. 5,645,767), a photoradical polymerization initiator (bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, manufactured by IGM Resin B.V., Omnirad 819), an antioxidant (ethylene bis(oxyethylene)bis-(3-(5-tert-butyl-4-hydroxy-m-tolyl)propionate)), and a light stabilizer (a mixture of bis(1,2,2,6,6-pentamethyl-4-piperidinyl)sebacate and methyl(1,2,2,6,6-pentamethyl-4-piperidinyl)sebacate) and thoroughly stirred.
  • a photochromic compound an indeno-fused naphthopyran compound represented by the following structural formula (6) described in U.S. Pat. No.
  • primer layer composition 1 In a plastic container, 10 parts by mass of a hydroxyl group-containing bifunctional acrylate having a compound represented by the following structural formula (1), 40 parts by mass of a polyisocyanate (Coronate 2715, manufactured by Tosoh Corporation), and 50 parts by mass of 2-phenoxyethyl acrylate (viscosity: 13 cP) were mixed. To the mixture thus obtained, 0.02 parts by mass of a photoradical polymerization initiator (bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, Omnirad 819, manufactured by IGM Resin B.V.) was added relative to the total amount of 100 parts by mass of the mixture, and the mixture was thoroughly stirred. The mixture was then degassed using a rotation-revolution type stirring/degassing apparatus. Thus, primer layer composition 1 was obtained.
  • a photoradical polymerization initiator bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, Omnirad 819, manufactured
  • protective layer composition 1 In a plastic container, 99.0 parts by mass of tricyclodecane dimethanol diacrylate (alicyclic bifunctional (meth)acrylate) and 1.0 part by mass of a photoradical polymerization initiator (bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, Omnirad 819, manufactured by IGM Resin B.V.) were mixed and thoroughly stirred, and then degassed using a rotation-revolution type stirring and degassing apparatus. In this way, protective layer composition 1 was obtained.
  • a photoradical polymerization initiator bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, Omnirad 819, manufactured by IGM Resin B.V.
  • the (meth)acrylate is only an alicyclic bifunctional (meth)acrylate, and therefore the content of the alicyclic bifunctional (meth)acrylate is 100% by mass out of 100% by mass of all (meth)acrylates.
  • a coated material 3 (state: sheet, material: silicone resin, thickness: 1.0 mm, shape: perfect circle, radius: 35.0 mm, number of through-holes: 1 (located at the center of coated material 3 in FIG. 3 ), through-hole diameter: 3.0 mm, no rubber on the periphery) was obtained from PT-CUS (manufactured by Sekisui Chemical Co., Ltd.).
  • Coating 7 (state: plate, material: polyacetal resin, thickness: 5.0 mm, shape: perfect circle, radius: 35.0 mm, number of through-holes: 0, rubber (urethane resin) present on the periphery (see rubber 2 on the periphery in Figure 3 )) was obtained in the same manner as the coating 1, except that no through-holes were provided.
  • primer layer composition 1 coated on lens substrate 1 was irradiated with light (light wavelength: 405 nm, light irradiation intensity: 250 mW/cm 2 , light irradiation time: 5 seconds, light irradiation exposure amount: 1.25 J/cm 2 ) in a nitrogen atmosphere (oxygen concentration: 500 volume ppm or less) at room temperature to cure the composition and form a primer layer.
  • the formed primer layer had a thickness of 10 ⁇ m.
  • the other surface (concave surface) of lens substrate 1 Fig.
  • lens substrate 1 FIG. 1
  • spin-coating mechanism 40 FIG. 1
  • Protective layer composition 1 was then supplied onto the photochromic layer, and spin-coated by rotating spin-coating mechanism 40 ( FIG. 1 ) at a rotation speed of 1,600 rpm for 15 seconds in an environment of 25° C. and 50% relative humidity.
  • the protective layer composition 1 coated on the photochromic layer was irradiated with light (light wavelength: 405 nm, light irradiation intensity: 250 mW/cm 2 , light irradiation time: 15 seconds, light exposure dose: 3.75 J/cm 2 ) in a nitrogen atmosphere (oxygen concentration: 500 volume ppm or less) at room temperature to cure the coating layer and form a protective layer.
  • the thickness of the protective layer formed was 15 ⁇ m.
  • the thickness of the cured coating layer was calculated by measuring the reflectance (interference waveform) of the sample using a non-contact film thickness measurement system (FF8, manufactured by System Road Co., Ltd.) and analyzing the film thickness value using FFT (fast Fourier transform).
  • the "intensity of light irradiation” is a value measured using an actinometer (UIT-250, manufactured by USHIO Corporation) by lighting a lens base 300 mm away from the center of the light source to the light receiving unit (center wavelength 365 mm).
  • the above-mentioned "exposure amount of light irradiation” is the integrated value of irradiation time (light irradiation intensity (mW/cm 2 ) ⁇ irradiation time (seconds)) measured by using a light meter (UIT-250, manufactured by USHIO Corporation) to illuminate a lens base 300 mm away from the center of the light source to the light receiving unit (center wavelength 365 mm). In this way, the eyeglass lens of Example 1 was obtained.
  • Examples 2 to 6 The spectacle lenses of Examples 2 to 6 were obtained in the same manner as in Example 1, except that the coatings shown in Table 1 were used.
  • Comparative Example 1 An eyeglass lens of Comparative Example 1 was obtained in the same manner as in Example 1, except that Coating 1 in Example 1 was not used.
  • Comparative Example 2 Comparative Example 2 was carried out in the same manner as Example 1, except that coating 7 was used and the edge surface of coating 7 and the edge surface of the lens substrate were fixed with adhesive tape (Scotch 600, manufactured by 3M) in Example 1. However, the lens substrate came off coating 7 during rotation during spin coating of the primer layer, and the eyeglass lens of Comparative Example 2 could not be obtained.
  • Comparative Example 3 Comparative Example 3 was carried out in the same manner as Example 1, except that coating 8 was used, 5% by mass of agar was filled between the other surface of the lens substrate and coating 8, and the edge surface of coating 8 and the edge surface of the lens substrate were fixed with adhesive tape (Scotch 600, manufactured by 3M). However, the lens substrate came off coating 8 during rotation during spin coating of the primer layer, and the eyeglass lens of Comparative Example 3 could not be obtained.
  • ⁇ High-speed rotation durability evaluation> The other surface (concave surface) of a lens substrate (manufactured by HOYA Corporation, HILUX 1.67, central thickness 1.0 mm, peripheral thickness 9.1 mm, radius 35.0 mm) was coated with the produced coating, and the lens substrate was placed in a spin coating mechanism. The other surface of the lens substrate and the spin coating mechanism were then fixed under reduced pressure via the through-holes in the coating 1. Thereafter, the spin coating mechanism was rotated, and the practicable rotation speed (rpm) was measured and evaluated according to the following evaluation criteria.
  • the thickness of the cured coating layer is a value calculated from the analysis of the film thickness value by FFT (fast Fourier transform) after measuring the reflectance (interference waveform) of the sample using a non-contact film thickness measurement system (FF8, manufactured by System Road Co., Ltd.).
  • FFT fast Fourier transform
  • FF8 non-contact film thickness measurement system
  • the spectacle lens manufacturing methods of Examples 1 to 7 are capable of carrying out the spin coating step under conditions similar to those of the spectacle lens manufacturing method of Comparative Example 1, and are capable of carrying out the spin coating step at rotational speeds that cannot be carried out in the spectacle lens manufacturing methods of Comparative Examples 2 and 3. Because the spectacle lens manufacturing method of the present disclosure is capable of carrying out the spin coating step at rotational speeds, it can be said to be a spectacle lens manufacturing method that excels in reducing the thickness of the cured coating layer.
  • the method for manufacturing a spectacle lens according to the present disclosure is a simple manufacturing method that reduces the thickness of the cured coating layer formed on one surface of the lens substrate and provides excellent antifouling properties to the other surface of the lens substrate.
  • This disclosure is useful in the field of eyewear.

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  • Physics & Mathematics (AREA)
  • Health & Medical Sciences (AREA)
  • General Physics & Mathematics (AREA)
  • Ophthalmology & Optometry (AREA)
  • Optics & Photonics (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Eyeglasses (AREA)

Abstract

L'invention concerne un procédé de fabrication de verres de lunettes ayant une couche de revêtement durcie sur une surface d'un matériau de base de verre comprenant : une étape de recouvrement pour recouvrir au moins une partie de l'autre surface du matériau de base de verre avec un matériau de recouvrement ayant un ou plusieurs trous traversants ; une étape de réduction de pression pour réduire la pression entre l'autre surface du matériau de base de verre et un mécanisme de revêtement par centrifugation qui fait tourner le matériau de base de verre, à travers les trous traversants dans le matériau de revêtement, pour fixer l'autre surface du matériau de base de verre au mécanisme de revêtement par centrifugation ; et une étape de revêtement par centrifugation pour revêtir par centrifugation la surface du matériau de base de verre avec une composition durcissable.
PCT/JP2025/011612 2024-03-28 2025-03-25 Procédé de fabrication de verres de lunettes Pending WO2025205702A1 (fr)

Applications Claiming Priority (2)

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JP2024054924 2024-03-28
JP2024-054924 2024-03-28

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WO2025205702A1 true WO2025205702A1 (fr) 2025-10-02

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Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH02126964A (ja) * 1988-11-07 1990-05-15 Sony Corp 吸着装置
JPH1120037A (ja) * 1997-07-07 1999-01-26 Asahi Optical Co Ltd 薄膜形成装置、薄膜形成方法及びそれを用いる複合レンズの製造方法
JP2007021355A (ja) * 2005-07-15 2007-02-01 Seiko Epson Corp スピンコート用保持具、および、スピンコート装置
JP2007136344A (ja) * 2005-11-18 2007-06-07 Pioneer Electronic Corp スピンコート方法及び装置
JP2007157309A (ja) * 2005-12-09 2007-06-21 Ricoh Co Ltd 光ディスク製造方法、スピンコート装置及び光ディスク製造装置
JP2010219190A (ja) * 2009-03-16 2010-09-30 Dainippon Printing Co Ltd 薄膜形成装置及び薄膜形成方法
JP2013215643A (ja) * 2012-04-05 2013-10-24 Olympus Corp スピンコート方法およびスピンコート装置
JP2016093874A (ja) * 2014-11-17 2016-05-26 株式会社ディスコ パッケージ基板の加工方法

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH02126964A (ja) * 1988-11-07 1990-05-15 Sony Corp 吸着装置
JPH1120037A (ja) * 1997-07-07 1999-01-26 Asahi Optical Co Ltd 薄膜形成装置、薄膜形成方法及びそれを用いる複合レンズの製造方法
JP2007021355A (ja) * 2005-07-15 2007-02-01 Seiko Epson Corp スピンコート用保持具、および、スピンコート装置
JP2007136344A (ja) * 2005-11-18 2007-06-07 Pioneer Electronic Corp スピンコート方法及び装置
JP2007157309A (ja) * 2005-12-09 2007-06-21 Ricoh Co Ltd 光ディスク製造方法、スピンコート装置及び光ディスク製造装置
JP2010219190A (ja) * 2009-03-16 2010-09-30 Dainippon Printing Co Ltd 薄膜形成装置及び薄膜形成方法
JP2013215643A (ja) * 2012-04-05 2013-10-24 Olympus Corp スピンコート方法およびスピンコート装置
JP2016093874A (ja) * 2014-11-17 2016-05-26 株式会社ディスコ パッケージ基板の加工方法

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