WO2022211018A1 - 眼鏡レンズ - Google Patents

眼鏡レンズ Download PDF

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Publication number
WO2022211018A1
WO2022211018A1 PCT/JP2022/016492 JP2022016492W WO2022211018A1 WO 2022211018 A1 WO2022211018 A1 WO 2022211018A1 JP 2022016492 W JP2022016492 W JP 2022016492W WO 2022211018 A1 WO2022211018 A1 WO 2022211018A1
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WO
WIPO (PCT)
Prior art keywords
water
meth
layer
mass
spectacle lens
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.)
Ceased
Application number
PCT/JP2022/016492
Other languages
English (en)
French (fr)
Japanese (ja)
Inventor
雄治 星
健治 小島
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
Priority to JP2023511700A priority Critical patent/JP7499404B2/ja
Priority to EP22781228.6A priority patent/EP4318092A4/en
Priority to US18/284,115 priority patent/US20240174872A1/en
Priority to KR1020237033021A priority patent/KR102912156B1/ko
Priority to CN202280025135.6A priority patent/CN117083560B/zh
Publication of WO2022211018A1 publication Critical patent/WO2022211018A1/ja
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • GPHYSICS
    • G02OPTICS
    • G02CSPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
    • G02C7/00Optical parts
    • G02C7/02Lenses; Lens systems ; Methods of designing lenses
    • G02C7/022Ophthalmic lenses having special refractive features achieved by special materials or material structures
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40Additives
    • C09D7/60Additives non-macromolecular
    • C09D7/63Additives non-macromolecular organic
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10Esters
    • C08F220/20Esters of polyhydric alcohols or phenols, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10Esters
    • C08F220/26Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/28Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
    • C08F220/283Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing one or more carboxylic moiety in the chain, e.g. acetoacetoxyethyl(meth)acrylate
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/52Amides or imides
    • C08F220/54Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
    • C08F220/56Acrylamide; Methacrylamide
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F222/00Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/10Esters
    • C08F222/1006Esters of polyhydric alcohols or polyhydric phenols
    • C08F222/106Esters of polycondensation macromers
    • C08F222/1061Esters of polycondensation macromers of alcohol terminated polyesters or polycarbonates, e.g. polyester (meth)acrylates
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F230/00Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
    • C08F230/04Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
    • C08F230/08Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon
    • C08F230/085Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon the monomer being a polymerisable silane, e.g. (meth)acryloyloxy trialkoxy silanes or vinyl trialkoxysilanes
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40High-molecular-weight compounds
    • C08G18/4009Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
    • C08G18/4063Mixtures of compounds of group C08G18/62 with other macromolecular compounds
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40High-molecular-weight compounds
    • C08G18/42Polycondensates having carboxylic or carbonic ester groups in the main chain
    • C08G18/4266Polycondensates having carboxylic or carbonic ester groups in the main chain prepared from hydroxycarboxylic acids and/or lactones
    • C08G18/4269Lactones
    • C08G18/4277Caprolactone and/or substituted caprolactone
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40High-molecular-weight compounds
    • C08G18/62Polymers of compounds having carbon-to-carbon double bonds
    • C08G18/6216Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
    • C08G18/622Polymers of esters of alpha-beta ethylenically unsaturated carboxylic acids
    • C08G18/6225Polymers of esters of acrylic or methacrylic acid
    • C08G18/6229Polymers of hydroxy groups containing esters of acrylic or methacrylic acid with aliphatic polyalcohols
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72Polyisocyanates or polyisothiocyanates
    • C08G18/73Polyisocyanates or polyisothiocyanates acyclic
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72Polyisocyanates or polyisothiocyanates
    • C08G18/77Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
    • C08G18/78Nitrogen
    • C08G18/7806Nitrogen containing -N-C=0 groups
    • C08G18/7818Nitrogen containing -N-C=0 groups containing ureum or ureum derivative groups
    • C08G18/7831Nitrogen containing -N-C=0 groups containing ureum or ureum derivative groups containing biuret groups
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00Use of organic ingredients
    • C08K5/04Oxygen-containing compounds
    • C08K5/07Aldehydes; Ketones
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00Use of organic ingredients
    • C08K5/16Nitrogen-containing compounds
    • C08K5/34Heterocyclic compounds having nitrogen in the ring
    • C08K5/3467Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
    • C08K5/3472Five-membered rings
    • C08K5/3475Five-membered rings condensed with carbocyclic rings
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D175/00Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04Polyurethanes
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D175/00Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04Polyurethanes
    • C09D175/06Polyurethanes from polyesters
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D5/00Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D5/00Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/32Radiation-absorbing paints
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40Additives
    • C09D7/48Stabilisers against degradation by oxygen, light or heat
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40Additives
    • C09D7/60Additives non-macromolecular
    • C09D7/61Additives non-macromolecular inorganic
    • GPHYSICS
    • G02OPTICS
    • G02BOPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/10Optical coatings produced by application to, or surface treatment of, optical elements
    • G02B1/18Coatings for keeping optical surfaces clean, e.g. hydrophobic or photo-catalytic films
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    • G02OPTICS
    • G02CSPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
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    • G02C7/108Colouring materials
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    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
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Definitions

  • the present disclosure relates to spectacle lenses.
  • Patent Literature 1 describes providing an anti-fogging layer made of a water-absorbing layer on a spectacle lens.
  • the anti-fogging layer will have both water absorption and water repellency by blending a water absorbing component and a slipping component, thereby imparting scratch resistance and low friction resistance.
  • Patent Document 1 describes that it is preferable to incorporate an ultraviolet absorber into the water-absorbing layer when deterioration of the base material is a concern.
  • an object of the present disclosure is to provide a spectacle lens that has antifogging properties, excellent light resistance, and little color change.
  • the present disclosure provides the following [1] to [7].
  • [1] having a base material and a water-absorbing anti-fogging layer provided as the outermost layer on the base material,
  • the water-absorbing anti-fogging layer contains an ultraviolet absorber
  • the spectacle lens wherein the water-absorbing anti-fogging layer has spectral characteristics such that the light transmittance is less than 5% at least at 350 to 370 nm, and the wavelength at which the light transmittance is 5% or more is 370 nm or more.
  • a spectacle lens that has anti-fog properties, excellent light resistance, and little color change.
  • FIG. 1 is a schematic cross-sectional view and a partially enlarged view of a spectacle lens 10.
  • alkyl group includes an alkyl group having no substituent (unsubstituted alkyl group) and an alkyl group having a substituent (substituted alkyl group).
  • (meth)acryl used herein represents a concept that includes both acryl and methacryl. The same applies to similar notations such as "(meth)acrylate”.
  • the structural unit derived from the monomer (a-1) is “structural unit (a-1)”
  • the structural unit derived from the monomer (a-2) is “structural unit (a-2)”
  • the monomer A structural unit derived from (a-3) may be referred to as “structural unit (a-3)”
  • a structural unit derived from monomer (a-4) may be referred to as “structural unit (a-4)".
  • a spectacle lens according to an embodiment of the present disclosure has a base material and a water-absorbing anti-fogging layer provided as an outermost layer on the base material, the water-absorbing anti-fog layer containing an ultraviolet absorber, and The water-absorbing anti-fogging layer has a spectral characteristic that the light transmittance at least at 350 to 370 nm is less than 5%, and the wavelength at which the light transmittance is 5% or more is 370 nm or more.
  • FIG. 1 is a schematic sectional view and a partially enlarged view of a spectacle lens 10, which is an example of the spectacle lens.
  • the structure of the spectacle lens 10 will be described with reference to FIG.
  • the spectacle lens 10 has a lens body.
  • the lens body is composed of a lens substrate 11, which will be described later.
  • the spectacle lens 10 has a spectacle lens substrate 11 (hereinafter also simply referred to as "lens substrate”) which is a substrate constituting a lens body.
  • the lens substrate 11 has a first principal surface 111 , a second principal surface 112 and an edge surface 113 .
  • a water-absorbing anti-fogging layer 20 is provided on the first main surface 111 of the lens substrate 11 .
  • a water-absorbing anti-fogging layer 21 is also provided on the second main surface 112 of the lens substrate 11 .
  • the water-absorbent anti-fog layers 20, 21 are the outermost layers of the spectacle lens 10, and the water-absorbent anti-fog layers 20, 21 are exposed to the external space.
  • the lens substrate 11 has a dyed layer 11a formed near the first main surface 111 and a dyed layer 11b formed near the second main surface 112. As shown in FIG.
  • the dyed layers 11a and 11b are layers dyed with a predetermined dye.
  • the spectacle lens can be colored in an arbitrary color (for example, gray).
  • the water-absorbent anti-fogging layer may be provided only on one of the main surfaces. For example, a mode in which only the water-absorbing anti-fogging layer 20 on the first main surface 111 in FIG. 1 is provided, or a mode in which only the water-absorbing anti-fogging layer 21 on the second main surface 112 in FIG. 1 is provided. It's okay.
  • the dye may be dispersed over the entire lens substrate by mixing a coloring agent into the raw material used to form the lens substrate.
  • the spectacle lens By providing the spectacle lens with an anti-fogging layer that has both water absorption and water repellency, such as the cured product of the coating composition described later, in addition to excellent anti-fog properties, scratch resistance and low friction resistance can be achieved. Granted.
  • the anti-fogging layer contains an ultraviolet absorber having specific physical properties, the anti-fogging layer has excellent light resistance, and has excellent light resistance, so that even if the spectacle lens is used for a long period of time, the color tone will be improved. change is small. Therefore, even if the lens substrate is dyed, and in particular is colored in an achromatic color such as gray, the tint is less likely to change.
  • the lens substrate is, for example, a spectacle lens substrate.
  • the lens substrate is preferably made of resin.
  • the lens substrate may be dyed with a coloring agent as described above, for example dyed gray.
  • resins forming the lens substrate include polycarbonate resins, urethane urea resins, acrylic allyl resins, (thio)urethane resins, polysulfide resins, polyamide resins, and polyester resins.
  • (Thio)urethane resin means at least one selected from thiourethane resins and urethane resins. Among these, (thio)urethane resins, polycarbonate resins and polysulfide resins are preferred.
  • the lens substrate used for the spectacle lens of the present embodiment preferably has a refractive index of 1.50 or more, and more preferably a plastic lens substrate having a refractive index of 1.60 or more.
  • Preferred commercially available plastic lens substrates include allyl polycarbonate plastic lens "HILUX 1.50" (manufactured by HOYA Corporation, refractive index 1.50), thiourethane plastic lens “MERIA” (manufactured by HOYA Corporation, refractive index index 1.60), thiourethane plastic lens "EYAS” (manufactured by HOYA Corporation, refractive index 1.60), thiourethane plastic lens "EYNOA” (manufactured by HOYA Corporation, refractive index 1.67), polysulfide system Plastic lens "EYRY” (manufactured by HOYA Corporation, refractive index 1.70), polysulfide-based plastic lens "EYVIA” (manufactured by HOYA Corporation, refractive
  • the coloring agent for dyeing the lens substrate is used by being added to the solution for dyeing the lens substrate.
  • Colorants for dyeing the substrate include dyes such as disperse dyes and oil-soluble dyes, and pigments. These dyes and pigments may be used singly or in combination of two or more.
  • the substrate is colored gray, the change in color due to yellowing is easily perceived by the human eye, and thus the effect of suppressing yellowing by providing the water-absorbing anti-fogging layer is remarkable.
  • Examples of dyes for coloring the base material gray include azo-based disperse dyes and anthraquinone-based disperse dyes.
  • the thickness and diameter of the substrate are not particularly limited, but the thickness is usually about 1 to 30 mm, and the diameter is usually about 50 to 100 mm.
  • the refractive index ne of the base material is preferably 1.50 or higher, more preferably 1.53 or higher, still more preferably 1.55 or higher, even more preferably 1.58 or higher, still more preferably 1.60 or higher, especially It is preferably 1.67 or more, preferably 1.80 or less, more preferably 1.70 or less.
  • the lens substrate may be either a finished lens or a semi-finished lens.
  • the surface shape of the lens substrate is not particularly limited, and may be flat, convex, concave, or the like.
  • the water-absorbing anti-fogging layer is located in the outermost layer of the spectacle lens, and has spectral characteristics such that the light transmittance at least at 350 to 370 nm is less than 5%, and the wavelength at which the light transmittance is 5% or more is 370 nm or more. have. Since the water-absorbing anti-fogging layer is positioned as the outermost layer of the spectacle lens, it prevents the spectacle lens from fogging due to moisture present in the external environment.
  • the water-absorbing anti-fogging layer has the above spectral characteristics, the ultraviolet rays contained in the light directed toward the spectacle lens from the outside are suppressed from entering the lens substrate, and the spectacle lens is exposed to ultraviolet rays for a long time. In this case, yellowing of the water-absorbing anti-fogging layer can be prevented, and fading of the dye when the lens substrate is dyed can be suppressed.
  • the water-absorbing anti-fogging layer has a light transmittance of less than 5% at least at 350 to 370 nm, and the wavelength at which the light transmittance is 5% or more is preferably 375 nm or more, more preferably 380 nm or more, and still more preferably 382 nm or more. and preferably has a spectral transmittance of 420 nm or less, more preferably 400 nm or less.
  • the light transmittance of the water-absorbing anti-fogging layer at wavelengths less than 350 nm is preferably 1% or less.
  • the water-absorbing anti-fogging layer is a layer with water absorption.
  • water absorbability means that the material exhibits a property of absorbing moisture.
  • the thickness of the water-absorbing anti-fogging layer is preferably 1 to 100 ⁇ m, more preferably 3 to 60 ⁇ m, still more preferably 6 to 50 ⁇ m, even more preferably 8 to 40 ⁇ m, still more preferably 8, from the viewpoint of ease of production. ⁇ 40 ⁇ m, more preferably 12-30 ⁇ m.
  • the thickness of the water-absorbing anti-fogging layer is preferably 1 ⁇ m or more, more preferably 3 ⁇ m or more, still more preferably 6 ⁇ m or more, still more preferably 8 ⁇ m or more, and even more preferably 12 ⁇ m or more, from the viewpoint of improving anti-fogging properties.
  • the thickness is preferably 100 ⁇ m or less, more preferably 60 ⁇ m or less, even more preferably 50 ⁇ m or less, even more preferably 40 ⁇ m or less, and even more preferably 30 ⁇ m or less.
  • the water-absorbing anti-fogging layer is preferably a cured film of a coating composition containing structural units derived from a siloxane compound and structural units derived from acrylamide. Since the water-absorbing anti-fogging layer has structural units derived from a siloxane compound, the slipping property of the water-absorbing anti-fogging layer is improved, and as a result, the scratch resistance of the water-absorbing anti-fogging layer is improved.
  • the water-absorbing anti-fogging layer has an amide group derived from acrylamide, the hydrophilicity of the water-absorbing anti-fogging layer increases, thereby improving the water absorption performance and, as a result, improving the anti-fogging property.
  • the water-absorbing anti-fogging layer preferably comprises a cured film of a coating composition containing the following components (A) to (C).
  • Component (A) structural units derived from the monomer (a-1) represented by the following general formula (1), structural units derived from the monomer (a-2) represented by the following general formula (2), hydroxy A (meth)acrylic resin component (B ): Polyol compound (B)
  • R 4 is a hydrogen atom or a methyl group, and m is an integer of 1 to 5.
  • R 5 is a hydrogen atom or a methyl group
  • R 6 is a divalent organic group
  • n is an integer of 0 or 1 or more.
  • the structural unit (a-1) contained in the resin (A) also called (meth)acrylic resin
  • the structural unit (a-1) contained in the resin (A) has an amide group, is highly hydrophilic, and easily retains moisture. For this reason, it is thought that the water adhering to the surface of the water-absorbing anti-fogging layer obtained by curing the coating composition is easily absorbed into the cured interior.
  • the polyol compound (B) it is possible to maintain the crosslink density necessary for the water-absorbing anti-fogging layer and to create gaps through which water is sufficiently absorbed. For these reasons, it is believed that antifogging properties are imparted to the cured film of the coating composition.
  • the structural unit (a-2) contained in the resin (A) is a structural unit having a polycaprolactone structure, and its flexible chemical skeleton contributes to improving the flexibility and elasticity of the water-absorbing anti-fogging layer.
  • the structural unit (a-3) which is more rigid than the structural unit (a-2) a balance between flexibility and elasticity is ensured.
  • the polydimethylsiloxane chain possessed by the structural unit (a-4) contributes to improving the slipperiness of the water-absorbing anti-fogging layer.
  • the ratio of structural units derived from the monomer (a-1) is 20% by mass or more and 65% by mass or less with respect to 100% by mass of all the structural units constituting the component (A), and the monomer (a-2)
  • the ratio of structural units derived from is 10% by mass or more and 40% by mass or less, and the ratio of structural units derived from monomer (a-4) is 1% by mass or more and 10% by mass or less, and is included in component (C)
  • the ratio of the number of isocyanate groups (NCO) to the total amount (OH) obtained by adding the number of hydroxyl groups contained in component (A) and the number of hydroxyl groups contained in component (B) (NCO)/(OH) is It is preferably 0.15 or more and 0.55 or less.
  • the equivalent ratio (NCO /OH) is set to a specific range smaller than 1, and it is thought that the hardness of the water-absorbing anti-fogging layer can be increased to the extent that the frictional resistance is improved.
  • a specific equivalent ratio (NCO/OH) of less than 1 while maintaining the structural balance of the structural unit (a-2) and the structural unit (a-3) having a hydroxyl group in the component (A) is set in the range of , the crosslinking density of the water-absorbing anti-fogging layer increases, and the solvent resistance of the water-absorbing anti-fogging layer improves.
  • the coating composition of the present embodiment comprises a (meth)acrylic resin as component (A), that is, structural units derived from the monomer (a-1) represented by the following general formula (1), the following general formula ( 2) a structural unit derived from the monomer (a-2) represented by, a structural unit derived from the hydroxyalkyl (meth)acrylate (a-3), and a monomer (a) represented by the following general formula (3) -4) preferably contains a (meth)acrylic resin having a structural unit derived from.
  • component (A) that is, structural units derived from the monomer (a-1) represented by the following general formula (1), the following general formula ( 2) a structural unit derived from the monomer (a-2) represented by, a structural unit derived from the hydroxyalkyl (meth)acrylate (a-3), and a monomer (a) represented by the following general formula (3) -4) preferably contains a (meth)acrylic resin having a structural unit derived from.
  • a (meth)acrylic resin can typically be obtained by polymerizing a monomer (a-1), a monomer (a-2), a monomer (a-3) and a monomer (a-4). Details of the polymerization method will be described later.
  • 100% of the structural units constituting the (meth)acrylic resin may not be structural units derived from (meth)acrylic monomers. That is, the (meth)acrylic resin may partially (but not entirely) contain structural units derived from non-(meth)acrylic monomers.
  • 50% by mass or more of the total structural units of the (meth)acrylic resin are structural units derived from (meth)acrylic monomers. is preferably More preferably, 80% by mass or more of the total structural units of the (meth)acrylic resin are structural units derived from (meth)acrylic monomers. More preferably, all (100%) structural units of the (meth)acrylic resin are structural units derived from (meth)acrylic monomers.
  • the monomer (a-1) is not particularly limited as long as it has the structure of general formula (1) above. Specifically, (meth)acrylamide, N-methylacrylamide, N,N-dimethyl(meth)acrylamide, N-ethyl(meth)acrylamide, N,N-diethyl(meth)acrylamide, Nn-propyl (meth) ) acrylamide, N-isopropyl(meth)acrylamide and the like.
  • the monomer (a-1) particularly preferably contains N,N-dimethyl(meth)acrylamide and N,N-diethyl(meth)acrylamide.
  • the monomer (a-2) is not particularly limited as long as it has the structure of general formula (2) above.
  • the (meth)acrylic resin preferably contains 10 to 40% by mass, more preferably 20 to 38% by mass of structural units derived from the monomer (a-2), based on the total structural units of the resin. % by mass, more preferably 25 to 35% by mass.
  • Monomer (a-3) is a hydroxyalkyl (meth)acrylate. Specific examples thereof include hydroxyethyl (meth)acrylate, hydroxypropyl (meth)acrylate, hydroxybutyl (meth)acrylate and the like. Among these, hydroxyethyl (meth)acrylate is preferred in the present embodiment.
  • the structural unit derived from the monomer (a-3) in the (meth)acrylic resin is preferably 1 to 30% by mass, more preferably 1 to 30% by mass, based on the total structural units of the (meth)acrylic resin. is contained in an amount of 2 to 20% by mass, more preferably 3 to 15% by mass.
  • the monomer (a-3) has a hydroxyl group similarly to the monomer (a-2), and undergoes a cross-linking reaction with a polyfunctional isocyanate compound to be described later to form a water-absorbing anti-fogging layer.
  • the monomer (a-2) alone does not cause a cross-linking reaction to form a water-absorbing anti-fogging layer, but the monomer (a-3) and the polyfunctional isocyanate compound cause a cross-linking reaction. It is possible to form a water-absorbing anti-fogging layer having various physical properties.
  • the (meth)acrylic resin preferably has a hydroxyl value of 40 to 150 mgKOH/g, more preferably 70 to 140 mgKOH/g, even more preferably 90 to 130 mgKOH/g.
  • a polyfunctional isocyanate compound (described later) together with a polyol compound (described later)
  • the crosslinked structure is easily controlled appropriately. Therefore, it is possible to harden the water-absorbing anti-fogging layer while maintaining the flexibility and elasticity of the water-absorbing anti-fogging layer. Therefore, it becomes easier to achieve a higher level of compatibility between the water-absorbing anti-fog layer's scratch resistance, reduction in frictional resistance, and solvent resistance.
  • the hydroxyl value means mg of potassium hydroxide required to neutralize acetic acid bound to hydroxyl groups when 1 g of sample is acetylated.
  • the monomer (a-4) is not particularly limited as long as it has the structure of general formula (3) above.
  • the (meth)acrylic resin may contain a plurality of repeating units derived from the monomer (a-4).
  • a (meth)acrylic resin may be obtained by performing a polymerization reaction using two or more of the monomers listed above.
  • the structural unit derived from the monomer (a-4) in the (meth)acrylic resin is preferably 1 to 10% by mass, more preferably 2 to 8, based on the total structural units of the resin. % by mass, more preferably 3 to 7% by mass.
  • any structural unit may or may not be included.
  • the structural unit (a-5) include structural units derived from the monomers shown below.
  • R is a hydrogen atom or a methyl group
  • R' is an alkyl group, a monocyclic or polycyclic cycloalkyl group, or an aryl or a structural unit derived from a monomer that is an aralkyl group.
  • the mass average molecular weight (Mw) of the (meth)acrylic resin is not particularly limited, but is preferably from 10,000 to 100,000, more preferably from 20,000 to 70,000. 000 to 60,000 is more preferred. If the weight average molecular weight is 10,000 or more, the desired anti-fogging performance tends to be easily obtained, and if it is 100,000 or less, there is a tendency for excellent coating suitability when applied to an object to be coated such as a spectacle lens.
  • the mass average molecular weight can be determined by gel permeation chromatography (GPC) using polystyrene as a standard substance.
  • the glass transition temperature of the (meth)acrylic resin (the glass transition temperature of the (meth)acrylic resin alone, not the glass transition temperature of the water-absorbing anti-fogging layer) was obtained based on the above formula. means glass transition temperature.
  • the glass transition temperatures are determined using only monomers with known glass transition temperatures.
  • (Meth)acrylic resins can typically be obtained through a polymerization reaction.
  • various methods such as radical polymerization, cationic polymerization, and anionic polymerization may be used, and among these, radical polymerization is preferred.
  • the polymerization may be any of solution polymerization, suspension polymerization, emulsion polymerization, and the like. Of these, solution polymerization is preferred from the viewpoint of precise control of polymerization.
  • a known polymerization initiator can be used as the polymerization initiator for radical polymerization.
  • azobisisobutyronitrile, 2,2-azobis(2-methylbutyronitrile), 2,2-azobis(2-methylpropionitrile), and 2,2-azobis(2,4-dimethylvalero nitrile) benzoyl peroxide, t-butyl peroxyoctanoate, diisobutyl peroxide, di(2-ethylhexyl) peroxypivalate, decanoyl peroxide, t-butylperoxy-2- Redox combining oxidizing agents and reducing agents, such as peroxide-based initiators such as ethylhexanoate and t-butyl peroxybenzoate, hydrogen peroxide and iron(II) salts, persulfates and sodium hydrogen sulfite system initiators and the like.
  • the amount of the polymerization initiator to be blended is not particularly limited, but is preferably 0.001 to 10 parts by mass when the entire mixture of monomers to be polymerized is 100 parts by mass.
  • the polymerization reaction may be carried out in one step or in two or more steps.
  • the temperature of the polymerization reaction is not particularly limited, it is typically in the range of 50°C to 200°C, preferably 80°C to 150°C.
  • the coating composition of the present embodiment preferably contains a polyol compound.
  • a polyol compound By containing a polyol compound, it becomes possible to form a water-absorbing anti-fogging layer having more excellent anti-fogging durability by reacting with a polyfunctional isocyanate compound described below together with the (meth)acrylic resin.
  • the number of hydroxyl groups in one molecule of the polyol compound is 2 or more, preferably 2-6, more preferably 2-4.
  • the polyol compound preferably contains at least one or more polyol compounds selected from the group consisting of polycaprolactone polyols, polycarbonate polyols, and polyether polyols. These chemical structures are moderately flexible and elastic. Therefore, the flexibility and elasticity of the water-absorbing anti-fogging layer can be further enhanced.
  • Any polycaprolactone polyol can be used without any particular limitation as long as it is a compound having an open ring structure of caprolactone and two or more hydroxyl groups in one molecule.
  • Polycarbonate polyols can be used without particular limitation as long as they are compounds having a carbonate group represented by —O—(C ⁇ O)—O— and two or more hydroxyl groups in one molecule.
  • Polycarbonate polyol can be obtained by reacting one or more polyol raw materials (polyhydric alcohol) with carbonic acid ester or phosgene.
  • Polyol raw materials are not particularly limited, and examples thereof include aliphatic polyols, polyols having an alicyclic structure, and aromatic polyols. In the present embodiment, an aliphatic polyol having no alicyclic structure is preferred from the viewpoint of the flexibility of the cured film.
  • Carbonic acid esters include, for example, aliphatic carbonic acid esters such as dimethyl carbonate and diethyl carbonate, aromatic carbonic acid esters such as diphenyl carbonate, and cyclic carbonic acid esters such as ethylene carbonate. Of these, aliphatic carbonates are preferred, and dimethyl carbonate is particularly preferred, because of their availability and ease of production.
  • any compound having an ether bond (--O--) and two or more hydroxyl groups in one molecule can be used as the polyether polyol without any particular limitation.
  • Specific compounds include, for example, ethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, 1,5 - pentanediol, 1,6-hexanediol, 1,8-octanediol, 1,9-nonanediol, 3-methyl-1,5-pentanediol, 3,3-dimethylolheptane, diethylene glycol, dipropylene glycol, Neopentyl glycol, cyclohexane-1,4-diol, cyclohexane-1,4-dimethanol, dimer acid diol, bisphenol A, bis( ⁇ -hydroxyeth
  • polyether polyols obtained by addition polymerization of alkylene oxides such as ethylene oxide, propylene oxide and butylene oxide using compounds as initiators, alkyl glycidyl ethers such as methyl glycidyl ether, and aryls such as phenyl glycidyl ether Examples include polyether polyols obtained by ring-opening polymerization of cyclic ether monomers such as glycidyl ethers and tetrahydrofuran.
  • the polyol compound may be a compound corresponding to a plurality of polycaprolactone polyols, polycarbonate polyols, and polyether polyols.
  • the polyol compound may be a polyether polyester polyol or the like having an ether bond and an ester bond.
  • the polyol compound may contain more than one of polycaprolactone polyol, polycarbonate polyol, and polyether polyol.
  • the hydroxyl value of the polyol compound is preferably 50-500 mgKOH/g, more preferably 100-350 mgKOH/g, still more preferably 150-250 mgKOH/g.
  • the mass average molecular weight (Mw) of the polyol compound is preferably 450-2,500, more preferably 500-1,500, still more preferably 500-700.
  • the content of the polyol compound in the coating composition is preferably 5 to 200 parts by mass, more preferably 15 to 180 parts by mass, and still more preferably 20 to 150 parts by mass with respect to 100 parts by mass of the (meth)acrylic resin. , Still more preferably 20 to 100 parts by mass, still more preferably 20 to 50 parts by mass, still more preferably 20 to 40 parts by mass. By setting it as this numerical range, it becomes easy to obtain the performance derived from a polyol compound, and it becomes easy to balance with other components.
  • the polyol compound preferably contains polycaprolactone polyol among the above-described polycaprolactone polyol, polycarbonate polyol, and polyether polyol.
  • polycaprolactone polyols polycaprolactone diol (having a caprolactone structure and , a compound having two hydroxyl groups).
  • the (meth)acrylic resin, which is the component (A) has the structure of the general formula (2) described above, that is, the caprolactone structure, so that the polyol compound tends to have good compatibility with the resin.
  • the antifogging performance tends to be improved without excessively increasing the crosslink density.
  • Component (C) polyfunctional isocyanate compound
  • the coating composition of the present embodiment preferably contains a polyfunctional isocyanate compound as component (C).
  • a polyfunctional isocyanate compound By including a polyfunctional isocyanate compound in the coating composition, the hydroxyl groups of the structural units (a-2) and structural units (a-3) contained in the (meth)acrylic resin that is component (A), and the component
  • the hydroxyl groups of the polyol compound (B) and the polyfunctional isocyanate compound undergo a cross-linking reaction to form a water-absorbing anti-fogging layer with excellent anti-fogging durability.
  • a polyfunctional isocyanate compound is a compound having two or more isocyanate groups (including an isocyanate group protected by a leaving group) in one molecule.
  • the polyfunctional isocyanate compound has 2 to 6 functional groups per molecule, and still more preferably 2 to 4 functional groups per molecule.
  • Polyfunctional isocyanate compounds include aliphatic diisocyanates such as lysine isocyanate, hexamethylene diisocyanate and trimethylhexane diisocyanate, hydrogenated xylylene diisocyanate, isophorone diisocyanate, methylcyclohexane-2,4-(or 2,6)-diisocyanate, 4, Cycloaliphatic diisocyanates such as 4′-methylenebis(cyclohexyl isocyanate) and 1,3-(isocyanatomethyl)cyclohexane, and tri- or higher functional isocyanates such as lysine triisocyanate.
  • aliphatic diisocyanates such as lysine isocyanate, hexamethylene diisocyanate and trimethylhexane diisocyanate
  • hydrogenated xylylene diisocyanate isophorone diisocyanate
  • polyfunctional isocyanate compound as component (C) in addition to the above compounds, polymers thereof such as biuret type, isocyanurate type, and adduct type may be used. Among them, a biuret-type polyfunctional isocyanate compound having appropriate rigidity is preferred.
  • the content of the polyfunctional isocyanate compound in the coating composition is not particularly limited as long as it is blended according to the equivalent ratio (NCO) / (OH) described later, but usually (meth)acrylic resin 100 5 to 100 parts by mass, preferably 7 to 75 parts by mass, more preferably 10 to 60 parts by mass, still more preferably 10 to 50 parts by mass, even more preferably 15 to 40 parts by mass, still more preferably is 20 to 30 parts by mass. It is considered that the necessary and sufficient cross-linking is achieved in the water-absorbing anti-fogging layer by setting the value within this numerical range.
  • the molar amount of the isocyanate groups (including blocked isocyanate groups) contained in the polyfunctional isocyanate compound relative to the hydroxyl groups possessed by the (meth)acrylic resin and the polyol compound is preferably It ranges from 0.15 to 0.55.
  • the equivalent ratio (NCO)/(OH) is within this range, the crosslink density is sufficiently high, and as a result, functions such as antifogging properties and solvent resistance as a water-absorbing antifogging layer are sufficient.
  • the equivalent ratio (NCO)/(OH) is preferably 0.25 to 0.50, more preferably 0.35 to 0.45.
  • the coating composition of the present embodiment may be of a one-liquid type, that is, in a state in which all components other than the solvent are substantially uniformly mixed (dissolved or dispersed) in the solvent.
  • a one-liquid type is preferred.
  • the coating composition of the present embodiment may be of a two-liquid type. By adopting a two-liquid type, the storage stability of the coating composition can be enhanced.
  • the coating composition of the present embodiment includes (1) liquid A containing a (meth)acrylic resin and/or polyol compound and not containing a polyfunctional isocyanate compound, and (2) a polyfunctional isocyanate compound, ( It consists of a meth)acrylic resin and a liquid B that does not contain a polyol compound, the liquids A and B are stored in separate containers, and the liquids A and B are mixed immediately before use (coating). good too.
  • components (additives, etc.) other than (meth)acrylic resins, polyol compounds, and polyfunctional isocyanate compounds may be contained in liquid A, liquid B, or other containers may be prepared with
  • the polyfunctional isocyanate compound is not a blocked isocyanate (that is, when the isocyanate group exists in the form of —NCO in the system)
  • the coating composition is preferably a two-component type.
  • the coating composition of this embodiment may contain a solvent.
  • a solvent facilitates adjustment of the viscosity and solid content of the coating composition.
  • solvents include aromatic hydrocarbon solvents such as toluene and xylene, alcohol solvents such as methanol, ethanol, isopropyl alcohol, n-butanol, t-butanol, isobutanol, and diacetone alcohol, acetone, methyl ethyl ketone, and methyl isobutyl.
  • ketone-based solvents such as ketones and cyclohexanone
  • ester-based solvents such as ethyl acetate, propyl acetate, butyl acetate, and isobutyl acetate
  • glycol ether-based solvents such as propylene glycol monomethyl acetate, propylene glycol monomethyl ether, and propylene glycol monomethyl ether acetate
  • t-butanol, diacetone alcohol, methyl ethyl ketone, ethyl acetate, and propylene glycol monomethyl ether acetate are preferred from the viewpoints of low reactivity with isocyanate, solubility and drying properties.
  • the content of the solvent in the coating composition is preferably 20 to 90% by mass, more preferably 30 to 85% by mass, still more preferably 35 to 80% by mass, from the viewpoint of controlling the film thickness of the water-absorbing antifogging layer. % by mass.
  • the solid content of the coating composition is preferably 5% by mass or more, more preferably 10% by mass or more, and still more preferably 15% by mass or more, from the viewpoint of obtaining spectacle lenses with more excellent anti-fogging properties, and spectacles with excellent appearance. From the viewpoint of obtaining a lens, the content is preferably 50% by mass or less, more preferably 40% by mass or less, and even more preferably 30% by mass or less.
  • the total content of components (A), (B) and (C) in the solid content of the coating composition is preferably 60% by mass or more, more preferably It is 80% by mass or more, more preferably 90% by mass or more, still more preferably 95% by mass or more, and preferably 100% by mass or less, for example 100% by mass.
  • the coating composition can be prepared by dissolving or dispersing each of the above components, an ultraviolet absorber, and optionally other additives in a solvent.
  • additives include curing catalysts, light stabilizers, surfactants, leveling agents, antifoaming agents and the like.
  • the content of the additive is, for example, preferably 0.001 to 5% by mass, more preferably 0.01 to 4% by mass, and still more preferably 0.1 to 3% by mass, relative to the total mass of the coating composition. %.
  • Each component can be dissolved or dispersed in the solvent simultaneously or sequentially in any order. There are no particular restrictions on the specific dissolving or dispersing method, and known methods can be employed without any restrictions.
  • the ultraviolet absorber contained in the water-absorbing anti-fogging layer has a light transmittance of less than 5% at least at 350 to 370 nm, and a light transmittance of 5% or more. It is an ultraviolet absorber that imparts a spectral transmittance with a wavelength of 370 nm or more to the water-absorbing anti-fogging layer.
  • the water-absorbing anti-fogging layer contains the ultraviolet absorber, so that yellowing of the anti-fogging layer is prevented when the spectacle lens is exposed to ultraviolet rays for a long time, and the lens substrate is dyed. It is possible to suppress the fading of the dye when it is used.
  • Examples of the ultraviolet absorber include compounds represented by the following formula (4) and compounds represented by the following formula (5).
  • a plurality of hydroxy groups bonded to the benzene ring are in a meta-position or para-position relationship with each other, and at least one hydroxy group is attached to the carbon to which the benzotriazole skeleton is bonded. It is preferable that the hydroxy group is bonded to the carbon at the ortho position with respect to the carbon to which the benzotriazole skeleton is bonded. More preferably, a hydroxy group is bonded to the carbon ortho to the carbon to which the triazole skeleton is bonded, and n1 is 2.
  • a specific example of the compound represented by formula (4) is 2-(2,4-dihydroxyphenyl)-2H-benzotriazole (CAS number: 22607-31-4).
  • a plurality of hydroxy groups bonded to the benzene rings are preferably in a meta-position or para-position relationship, and at least one hydroxy group is It is preferable that the hydroxy group is bonded to the carbon at the ortho-position to the carbon to which the carbonyl group is bonded, and the hydroxy group is more preferably bonded to the carbon at the ortho- and para-positions to the carbon to which the carbonyl group is bonded. More preferably, the hydroxy group is bonded to the carbon ortho to the carbon to which the carbonyl group is bonded, and n2 and n3 are both 2.
  • a specific example of the compound represented by formula (5) is 2,2',4,4'-tetrahydroxybenzophenone (CAS number: 131-55-5).
  • the above ultraviolet absorber has high absorption performance on the long wavelength side, and when used in the water-absorbing anti-fogging layer constructed using the above-described specific coating composition, exhibits high light resistance and absorbs water. It is possible to suppress the color change of the spectacle lens having the antifogging layer, and in particular, suppress the yellowing of the spectacle lens colored gray.
  • 2-(2,4-dihydroxyphenyl)-2H-benzotriazole does not excessively increase reactivity regardless of the type of monomer such as isocyanate, does not easily lower the UV absorption effect, and has a short pot life. There is an advantage that it is difficult to One type of ultraviolet absorber may be used alone, or two or more types may be used in combination.
  • the content of the UV absorber in the coating composition is preferably 0.01 to 5 with respect to the total mass of the coating composition, from the viewpoint of at least one of the protection of the lens substrate and the solubility of the UV absorber. % by mass, more preferably 0.1 to 4.5% by mass, still more preferably 0.5 to 3% by mass.
  • the water-absorbing anti-fogging layer may contain additives other than the ultraviolet absorber.
  • additives include, for example, antistatic agents, antioxidants, and the like.
  • the content of other additives is, for example, preferably 0.001 to 5% by mass, more preferably 0.01 to 4% by mass, and still more preferably 0.1 to 3%, based on the total mass of the coating composition. % by mass.
  • the UV absorber and additives other than the UV absorber are added to the coating composition and dissolved or dispersed, and then the coating composition is coated on a substrate to form a water-absorbing anti-fogging film. By forming, it can be blended in the water-absorbing anti-fogging film.
  • the spectacle lens may be provided with a functional layer other than the water-absorbing anti-fogging layer.
  • the functional layer include a hard coat layer, an antireflection layer, a primer layer, and the like.
  • the functional layer may be provided on the first main surface of the lens substrate, may be provided on the second main surface of the lens substrate, or may be provided on the first main surface of the lens substrate and It may be provided on both of the second main surfaces.
  • One aspect of the method for manufacturing a plastic spectacle lens includes at least the following steps (1) to (3).
  • Step (1) A lens substrate made of a polymer of a polymerizable composition is prepared.
  • Step (2) A solution containing a coloring agent is applied to the surface of the lens substrate to dye the lens substrate.
  • Step (3) forming a water-absorbing anti-fog layer on at least one main surface of the dyed base material.
  • Step (1) Preparation of lens substrate
  • the polymerizable composition is polymerized to prepare a lens substrate composed of a polymer of the polymerizable composition.
  • the polymerization conditions for the polymerizable composition for optical members can be appropriately set according to the polymerizable composition.
  • the polymerization initiation temperature is preferably 0° C. or higher, more preferably 10° C. or higher, and preferably 50° C. or lower, more preferably 40° C. or lower. It is preferable to raise the temperature from the polymerization initiation temperature and then heat to cure.
  • the maximum heating temperature is usually 110° C. or higher and 130° C. or lower.
  • the spectacle lens may be released from the mold and subjected to annealing treatment.
  • the annealing temperature is preferably 100-150°C.
  • the polymerization method is not particularly limited, and various known polymerization methods can be employed, but cast polymerization is preferred.
  • a spectacle lens can be obtained, for example, by injecting a polymerizable composition into a mold formed by combining a glass or metal mold and a tape or gasket, followed by polymerization.
  • Step (2) dyeing treatment
  • a solution containing a coloring agent is applied to the surface of the lens substrate to dye the lens substrate.
  • the substrate is dyed by immersing it in a solution containing a coloring agent.
  • Dyeing can be accelerated by immersing in a solution containing a coloring agent and heating for a predetermined time.
  • Step (3) Formation of water-absorbing anti-fogging layer
  • a water-absorbing anti-fogging layer is formed on at least one of the first main surface and the second main surface of the lens substrate obtained by the dyeing treatment.
  • the water-absorbing anti-fogging layer is formed by coating a coating composition obtained by dissolving or dispersing each of the above components in a solvent (in the case of a two-liquid type, a mixture of two liquids) on a lens substrate, and forming a coating film. It is formed by drying and curing at a predetermined temperature.
  • the coating method is not particularly limited, and examples thereof include an air spray method, an airless spray method, an electrostatic coating method, a roll coater method, a flow coater method, a spin coat method, and a dipping method.
  • After coating it is dried and cured at 20 to 160°C for 10 to 120 minutes, preferably at 60 to 120°C for 20 to 90 minutes, and further allowed to cool at room temperature to obtain a cured film that will be a water-absorbing anti-fogging layer. be done.
  • the temperature and time for drying and curing may be appropriately adjusted in consideration of the type of solvent, the heat resistance of the lens substrate, and the like.
  • the present disclosure will be specifically described below with reference to examples.
  • the hydroxyl value, number average molecular weight (Mn), mass average molecular weight (Mw) and polydispersity (Mw/Mn) of the components obtained in the following examples were obtained by the following methods.
  • measurement of the thickness of the water-absorbing anti-fogging layer of the spectacle lenses obtained in the examples and the comparative examples and the light resistance test were carried out according to the following procedures.
  • the thickness of the water-absorbing anti-fogging layer was measured using a non-contact film thickness measurement system FF8 manufactured by System Road Co., Ltd.
  • a thiourethane-based plastic lens MERIA manufactured by HOYA Corporation, refractive index 1.60, power S-4 00D, thickness 1.0 mm, outer diameter 75 mm
  • a water-absorbing anti-fogging layer was formed on the substrate for measurement by the procedure shown in Examples or Comparative Examples described later.
  • DMAA dimethylacrylamide
  • PLAXEL FA2D polycaprolactone-modified hydroxyethyl acrylate
  • HEMA 2-hydroxyethyl methacrylate
  • one end methacrylate-modified poly Dimethylsiloxane manufactured by JNC Co., Ltd., Silaplane FM-0721, molecular weight 5000
  • methyl methacrylate 25 parts by mass and 1,1'-azobis (cyclohexane-1-carbonitrile) (Wako Pure Chemical Industries, Ltd.) 1 part by mass of V-40 (manufactured by the company) was mixed.
  • This mixed monomer was added dropwise to the 500 ml flask over 2 hours while stirring, and reacted for 5 hours. The heating was stopped and the mixture was cooled to room temperature to obtain a resin solution containing (meth)acrylic resin (solid content ratio: about 40% by mass).
  • the resulting (meth)acrylic resin had a hydroxyl value of 57 mgKOH/g, a number average molecular weight (Mn) of 12,000, a mass average molecular weight (Mw) of 44,000, and a polydispersity (Mw /Mn) was 3.67. Further, the glass transition temperature (Tg) of the (meth)acrylic resin calculated from the compounding ratio of the monomers used was 32.8° C. based on the aforementioned Fox formula.
  • the amount of (meth)acrylic resin is not the amount of the resin solution (solid content ratio: about 40% by mass), but the amount of the resin (solid content) contained in the resin solution.
  • the amount of also represents the amount as a solid content. Further, when the (meth)acrylic resin and the polyol compound were uniformly mixed in the above amounts, the hydroxyl value of the mixture was measured to be 93 mgKOH/g.
  • an ultraviolet absorber 2-(2,4-dihydroxyphenyl)-2H-benzotriazole (CAS number: 22607-31-4) is added to 2% by weight of the total weight of the coating composition.
  • a coating composition containing an ultraviolet absorber was prepared by adding and mixing as follows.
  • a thiourethane plastic lens MERIA manufactured by HOYA Corporation, refractive index 1.60, degree S-4.00D, thickness 1.0 mm, outer diameter 75 mm was used as a base material and colored by the following procedure.
  • the plastic lens was immersed in the dyeing immersion solution, dyed at 92° C. for 60 minutes, and then annealed at 115° C. for 30 minutes to color the plastic lens gray.
  • the coating composition is applied onto the substrate by a dip-pulling method and heated at 120° C. for 2 hours to cure the coating film.
  • a single-layer water-absorbing anti-fogging layer was formed on the The thickness of the water-absorbing anti-fogging layer was 11.3 ⁇ m.
  • the substrate on which the water-absorbing antifogging layer was formed had a light transmittance of less than 5% at 350 to 370 nm, and the wavelength at which the light transmittance reached 5% was 373.7 nm.
  • Example 2 2,2′,4,4′-Tetrahydroxybenzophenone (CAS number: 131-55-5) was used as an ultraviolet absorber, and its blending amount was 3% by mass with respect to the total mass of the coating composition.
  • a single-layer water-absorbing anti-fogging layer was formed in the same procedure as in Example 1, except for the above, to prepare a spectacle lens.
  • the thickness of the water-absorbing anti-fogging layer was 12.6 ⁇ m.
  • the water-absorbing anti-fogging layer had a light transmittance of less than 5% at 350-370 nm, and the wavelength at which the light transmittance reached 5% was 382.1 nm.
  • Example 2 A spectacle lens was produced in the same procedure as in Example 1, except that the above composition before the addition of the ultraviolet absorber was used as the coating composition.
  • the thickness of the water-absorbent anti-fogging layer was 12.4 ⁇ m.
  • the light transmittance of the water-absorbing anti-fogging layer at 350-420 nm was greater than 80%.
  • Table 1 shows the results of the light resistance test of Examples 1 and 2 and Comparative Examples 1 and 2.
  • Table 2 shows the results of measuring the lightness and chromaticity of Example 1 and Comparative Example 2 before and after the lightfastness test.
  • the light transmittance of the water-absorbing anti-fogging layer always exceeds 5% at least at 350 to 420 nm.
  • "-" is entered in the "Attained Wavelength” column.
  • the lens of Example 1 does not show a large change in chromaticity (values of a * and b * ) even after irradiation with light, and it can be seen that there is no large change in tint.
  • the lens of Comparative Example 2 does not contain an ultraviolet absorber, the b * value after light irradiation is greatly increased, indicating that the lens becomes yellowish due to light irradiation. I understand.
  • a spectacle lens that is an embodiment of the present disclosure includes a base material having first and second main surfaces, and a water-absorbing anti-fogging lens made of a single layer formed on the second main surface side of the base material. a layer, a light-transmitting hard layer formed on the first main surface of the substrate, and a hydrophilic anti-fogging layer formed on the light-transmitting hard layer. According to the embodiment described above, it is possible to provide a spectacle lens with excellent anti-fogging properties and scratch resistance.
  • Spectacle lens 11 Substrates 11a, 11b: Dyed regions 20, 21: Water-absorbing anti-fog layer

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  • Medicinal Chemistry (AREA)
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  • Paints Or Removers (AREA)
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PCT/JP2022/016492 2021-03-31 2022-03-31 眼鏡レンズ Ceased WO2022211018A1 (ja)

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EP22781228.6A EP4318092A4 (en) 2021-03-31 2022-03-31 LENSES
US18/284,115 US20240174872A1 (en) 2021-03-31 2022-03-31 Spectacle lens
KR1020237033021A KR102912156B1 (ko) 2021-03-31 2022-03-31 안경 렌즈
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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS50137557A (https=) * 1974-04-18 1975-10-31
WO2013005710A1 (ja) 2011-07-06 2013-01-10 東海光学株式会社 防曇性光学物品及びその製造方法
WO2018143329A1 (ja) * 2017-02-03 2018-08-09 株式会社ニコン・エシロール 眼鏡レンズ、及び眼鏡レンズの製造方法
JP2019094468A (ja) * 2017-11-28 2019-06-20 ナトコ株式会社 塗料組成物、硬化膜、硬化膜を備えた物品
WO2020262658A1 (ja) * 2019-06-28 2020-12-30 ホヤ レンズ タイランド リミテッド 硬化性組成物およびその製造方法、眼鏡レンズ、眼鏡ならびに眼鏡レンズの製造方法

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5434707A (en) * 1993-09-14 1995-07-18 Polaroid Corporation Shaped plastic light-polarizing lens and method of making same
JP4097768B2 (ja) * 1998-04-06 2008-06-11 日油株式会社 共重合体、メガネレンズ用処理剤及び処理レンズ
JP3547662B2 (ja) * 1999-09-20 2004-07-28 Hoya株式会社 紫外線吸収性に優れたプラスチック眼鏡レンズ及びその製造方法
CN103554890A (zh) * 2013-11-08 2014-02-05 苏州市双赢包装材料有限公司 一种聚碳酸酯塑料片
EP3312662B1 (de) * 2016-10-21 2019-07-17 Carl Zeiss Vision International GmbH Brillenglas und verfahren zu dessen herstellung
JP6568294B2 (ja) * 2018-02-21 2019-08-28 デクセリアルズ株式会社 活性エネルギー線硬化性樹脂組成物、防曇防汚積層体、及びその製造方法、物品、並びに防曇方法

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS50137557A (https=) * 1974-04-18 1975-10-31
WO2013005710A1 (ja) 2011-07-06 2013-01-10 東海光学株式会社 防曇性光学物品及びその製造方法
WO2018143329A1 (ja) * 2017-02-03 2018-08-09 株式会社ニコン・エシロール 眼鏡レンズ、及び眼鏡レンズの製造方法
JP2019094468A (ja) * 2017-11-28 2019-06-20 ナトコ株式会社 塗料組成物、硬化膜、硬化膜を備えた物品
WO2020262658A1 (ja) * 2019-06-28 2020-12-30 ホヤ レンズ タイランド リミテッド 硬化性組成物およびその製造方法、眼鏡レンズ、眼鏡ならびに眼鏡レンズの製造方法

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of EP4318092A4

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EP4318092A4 (en) 2025-03-26
CN117083560A (zh) 2023-11-17
KR102912156B1 (ko) 2026-01-14
JPWO2022211018A1 (https=) 2022-10-06
US20240174872A1 (en) 2024-05-30

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