WO2022211044A1 - 眼鏡レンズ - Google Patents
眼鏡レンズ Download PDFInfo
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- WO2022211044A1 WO2022211044A1 PCT/JP2022/016607 JP2022016607W WO2022211044A1 WO 2022211044 A1 WO2022211044 A1 WO 2022211044A1 JP 2022016607 W JP2022016607 W JP 2022016607W WO 2022211044 A1 WO2022211044 A1 WO 2022211044A1
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- meth
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Classifications
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- G02—OPTICS
- G02C—SPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
- G02C7/00—Optical parts
- G02C7/02—Lenses; Lens systems ; Methods of designing lenses
- G02C7/022—Ophthalmic lenses having special refractive features achieved by special materials or material structures
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING 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
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/16—Antifouling paints; Underwater paints
- C09D5/1656—Antifouling paints; Underwater paints characterised by the film-forming substance
- C09D5/1662—Synthetic film-forming substance
- C09D5/1668—Vinyl-type polymers
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers 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
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
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- C08F220/20—Esters of polyhydric alcohols or phenols, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers 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
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
- C08F220/283—Esters 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
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers 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
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/52—Amides or imides
- C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F220/56—Acrylamide; Methacrylamide
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F230/00—Copolymers 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
- C08F230/04—Copolymers 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
- C08F230/08—Copolymers 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
- C08F230/085—Copolymers 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
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
- C08F290/061—Polyesters; Polycarbonates
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
- C08F290/068—Polysiloxanes
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
- C08G18/4063—Mixtures of compounds of group C08G18/62 with other macromolecular compounds
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4266—Polycondensates having carboxylic or carbonic ester groups in the main chain prepared from hydroxycarboxylic acids and/or lactones
- C08G18/4269—Lactones
- C08G18/4277—Caprolactone and/or substituted caprolactone
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
- C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
- C08G18/622—Polymers of esters of alpha-beta ethylenically unsaturated carboxylic acids
- C08G18/6225—Polymers of esters of acrylic or methacrylic acid
- C08G18/6229—Polymers of hydroxy groups containing esters of acrylic or methacrylic acid with aliphatic polyalcohols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/7806—Nitrogen containing -N-C=0 groups
- C08G18/7818—Nitrogen containing -N-C=0 groups containing ureum or ureum derivative groups
- C08G18/7831—Nitrogen containing -N-C=0 groups containing ureum or ureum derivative groups containing biuret groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING 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
- C09D143/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing boron, silicon, phosphorus, selenium, tellurium, or a metal; Coating compositions based on derivatives of such polymers
- C09D143/04—Homopolymers or copolymers of monomers containing silicon
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING 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
- C09D151/00—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
- C09D151/08—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers grafted on to macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING 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
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING 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
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
- C09D175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING 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
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/10—Block or graft copolymers containing polysiloxane sequences
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING 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
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/18—Materials not provided for elsewhere for application to surfaces to minimize adherence of ice, mist or water thereto; Thawing or antifreeze materials for application to surfaces
-
- 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
- G02B1/18—Coatings for keeping optical surfaces clean, e.g. hydrophobic or photo-catalytic films
-
- G—PHYSICS
- G02—OPTICS
- G02C—SPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
- G02C11/00—Non-optical adjuncts; Attachment thereof
- G02C11/08—Anti-misting means, e.g. ventilating, heating; Wipers
-
- 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
-
- G—PHYSICS
- G02—OPTICS
- G02C—SPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
- G02C7/00—Optical parts
- G02C7/02—Lenses; Lens systems ; Methods of designing lenses
Definitions
- the present disclosure relates to a spectacle lens having an antifogging layer.
- BACKGROUND ART Techniques for forming an antifogging layer on the surface of a lens substrate for preventing fogging (antifogging) of spectacle lenses are conventionally known. For example, a technique of coating the surface of a lens substrate with a surfactant is known. Also known is a technique for forming a water-absorbent resin layer and a water-repellent layer on the surface of the lens.
- Patent Document 1 a water absorbing layer mainly composed of urethane or acrylic resin having a specific polyoxyethylene chain is formed on the surface of a glass or plastic substrate, and amino-modified silicone or An antifogging optical article having a water-repellent layer containing at least one of mercapto-modified silicones as a main component is described.
- an anti-fogging layer made of a surfactant is formed on the surface of a lens substrate, the surfactant is easily peeled off from the lens surface when the surfactant is wiped with water. The durability was not sufficient, and the antifogging performance was not sufficient. Further, in the anti-fogging layer described in Patent Document 1, the water-absorbing layer is covered with the water-repellent layer constituting the outermost surface, so the water-absorbing performance of the water-absorbing layer is not sufficiently exhibited. In addition, the anti-fogging layer described in Patent Document 1 tends to wear the water-repellent layer during use, and the scratch resistance is not sufficient.
- An object of one embodiment of the present disclosure is to provide a spectacle lens that is excellent in anti-fogging properties and scratch resistance.
- Embodiments of the present disclosure relate to the following [1] to [7].
- a spectacle lens having a substrate and a water-absorbing anti-fogging layer, The water-absorbing anti-fog layer is the outermost layer of the spectacle lens, The spectacle lens, wherein the water-absorbing anti-fogging layer contains a resin having a siloxane bond unit.
- the water-absorbing anti-fogging layer contains a resin having a siloxane bond unit.
- the water-absorbing anti-fogging layer has a film thickness of 6 ⁇ m or more.
- the spectacle lens according to [1] or [2] above, wherein the water-absorbing anti-fogging layer is directly laminated on the base material.
- the coating composition has a solid content concentration of 10.0 to 40.0% by mass.
- the antifogging layer 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)
- Component (C) polyfunctional isocyanate compound (C) [In general formula (1), R 1 is a hydrogen atom or a methyl group, R 2 and R 3 are each independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and R 2 and R 3 may be the same or different.
- R 4 is a hydrogen atom or a methyl group, and n 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.
- 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)".
- solid content in the composition means the amount of ingredients other than the solvent.
- Solid content concentration or solid content ratio in a composition means the concentration or ratio of components other than the solvent in the composition.
- carbon number of a group having a substituent means the carbon number of the portion excluding the substituent.
- a spectacle lens according to an embodiment of the present disclosure is a spectacle lens having a base material and a water-absorbent anti-fog layer, wherein the water-absorbent anti-fog layer is the outermost layer of the spectacle lens, and the water-absorbent anti-fog layer is , containing resins having siloxane-bonded units.
- the water-absorbent anti-fog layer is the outermost layer of the spectacle lens, and the water-absorbent anti-fog layer is not covered with the water-repellent layer. It is sufficiently exhibited, and as a result, it is excellent in anti-fogging properties.
- the anti-fogging water-absorbing layer has improved slipperiness, resulting in excellent scratch resistance.
- "water-absorbing anti-fogging layer” means a layer containing a resin having siloxane bond units.
- the water-absorbing anti-fogging layer may be simply referred to as an anti-fogging layer.
- Resins made from various kinds of raw materials can be used as the base material.
- resins that form the substrate include polycarbonate resins, urethane urea resins, (thio)urethane resins, polysulfide resins, polyamide resins, polyester resins, acrylic allyl resins, and allyl carbonate resins.
- (Thio)urethane resin means at least one selected from thiourethane resins and urethane resins. Among these, (thio)urethane resins and polysulfide resins are preferred.
- the 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 substrate having a refractive index of 1.60 or more.
- plastic substrates include allyl carbonate plastic lens "HILUX 1.50” (manufactured by HOYA Corporation, refractive index 1.50), thiourethane plastic lens “MERIA” (manufactured by HOYA Corporation, refractive 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 plastic Lens “EYRY” (manufactured by HOYA Corporation, refractive index 1.70), polysulfide plastic lens "EYVIA” (manufactured by HOYA Corporation, refractive index 1.74), and the like.
- the thickness and outer diameter of the substrate are not particularly limited, but the thickness is usually about 0.5 to 30 mm, for example 1 to 30 mm, and the outer diameter is usually about 50 to 100 mm.
- the substrate may be either a finished lens or a semi-finished lens.
- the surface shape of the substrate is not particularly limited, and may be flat, convex, concave, or the like.
- the spectacle lens of the present disclosure may be any of a monofocal lens, a multifocal lens, a progressive power lens, and the like.
- the progressive power lens the near portion region (near portion) and the progressive portion region (intermediate portion) are usually included in the aforementioned lower region, and the distance portion region (far portion) is included in the upper region.
- the antifogging layer is a layer having water absorption from the viewpoint of obtaining a spectacle lens having excellent antifogging properties.
- water absorption refers to the ability of a material to absorb moisture.
- Whether or not a spectacle lens having an anti-fog layer has water absorbency can also be judged by whether or not the time required from exposure to a moist atmosphere to the start of fogging is longer than that of a spectacle lens without an anti-fog layer. can.
- the antifogging layer is provided as the outermost layer of the spectacle lens from the viewpoint of sufficiently exhibiting antifogging properties.
- the antifogging layer may be provided only on one of the principal surfaces, or may be provided on both surfaces.
- the antifogging layer is preferably provided directly on the substrate from the viewpoint of antifogging durability. That is, the spectacle lens according to this embodiment preferably has an anti-fogging layer directly on the substrate.
- the thickness of the antifogging layer is preferably 1 to 100 ⁇ m, more preferably 3 to 60 ⁇ m, even more preferably 6 to 50 ⁇ m, even more preferably 8 to 40 ⁇ m, and even more preferably 8 to 40 ⁇ m, from the viewpoint of ease of production. , and more preferably 12 to 30 ⁇ m.
- the thickness of the 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 still more preferably 12 ⁇ m or more, from the viewpoint of improving anti-fogging properties. From the viewpoint of ease of production, 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 antifogging layer preferably has water repellency. Thereby, the anti-fogging performance is further improved.
- the antifogging 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 antifogging layer has a structural unit derived from a siloxane compound, the slipperiness of the antifogging layer is improved, and as a result, the scratch resistance of the antifogging layer is improved. In addition, since the antifogging layer has an amide group derived from acrylamide, the hydrophilicity of the antifogging layer increases, thereby improving the water absorption performance, and as a result, the antifogging property is improved.
- the solid content concentration of the coating composition is preferably 10.0 to 40.0% by mass. When it is 10.0% by mass or more, the film thickness of the antifogging layer can be increased. When it is 40.0% by mass or less, an antifogging layer having a uniform thickness can be obtained. From this point of view, the solid content concentration of the coating composition is more preferably 12.0 to 30.0% by mass, still more preferably 15.0 to 30.0% by mass, and even more preferably 16.5 to 24.5% by mass. % by mass.
- the antifogging 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)
- Component (C) polyfunctional isocyanate compound (C) [In general formula (1), R 1 is a hydrogen atom or a methyl group, and R 2 and R 3 are each independently a hydrogen atom or a linear or branched alkyl group having 1 to 3 carbon atoms.
- R 4 is a hydrogen atom or a methyl group, and n 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 component (A) (also referred to as (meth)acrylic resin) has an amide group, is highly hydrophilic, and easily holds moisture. For this reason, it is thought that the moisture adhering to the surface of the antifogging layer obtained by curing the coating composition is likely to be absorbed into the cured interior.
- the polyol compound (B) it is believed that by blending the polyol compound (B), it is possible to maintain the cross-linking density necessary for the antifogging layer and to create gaps through which water is sufficiently absorbed. For these reasons, it is believed that anti-fog properties are imparted.
- the structural unit (a-2) contained in component (A) is a structural unit having a polycaprolactone structure, and its flexible chemical skeleton contributes to improving the flexibility and elasticity of the antifogging layer.
- the inclusion of the structural unit (a-3) that is more rigid than the structural unit (a-2) ensures a balance between flexibility and elasticity.
- the polydimethylsiloxane chain possessed by the structural unit (a-4) contributes to improving the slipperiness of the antifogging layer.
- the anti-fogging layer when an external force is applied to the anti-fogging layer, the flexibility and elasticity of the anti-fogging layer absorb the external force, while the slipperiness allows the external force to escape to the outside of the anti-fogging layer. It is thought that the anti-fogging layer is less likely to be scratched as a result of synergistic expression.
- 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 of less than 1, and it is believed that the hardness of the antifogging layer can be increased to such an 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 cross-linking density of the anti-fogging layer is increased, and the solvent resistance of the anti-fogging layer is considered to be improved.
- 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.
- At least one type of the monomer (a-1) may be used, or two or more types may be used in combination.
- a (meth)acrylic resin may be obtained by performing a polymerization reaction using two or more of the monomers listed above.
- the monomer (a-1) particularly preferably contains N,N-dimethyl(meth)acrylamide and N,N-diethyl(meth)acrylamide.
- the structural units derived from the monomer (a-1) in the (meth)acrylic resin are preferably contained in an amount of 20 to 65% by mass based on the total structural units of the resin. More preferably 35 to 60% by mass, still more preferably 40 to 55% by mass.
- the structural unit derived from the monomer (a-1) is 20% by mass or more, it becomes easy to form an antifogging layer exhibiting antifogging performance suitable for practical use. A decrease in the ratio of structural units derived from other monomers is avoided, and the balance of the composition as a whole can be easily maintained.
- 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.
- the (meth)acrylic resin may contain a plurality of repeating units derived from the monomer (a-2).
- 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 like the monomer (a-2) and undergoes a cross-linking reaction with a polyfunctional isocyanate compound described later to form an antifogging layer.
- the monomer (a-2) alone is not used to cause a cross-linking reaction to form an anti-fogging layer. It can be an antifogging layer having the physical properties of
- the (meth)acrylic resin contains structural units derived from the monomer (a-2) and the monomer (a-3), so it has hydroxyl groups as a whole, that is, it has a hydroxyl value. Therefore, it can react with a polyfunctional isocyanate compound described later together with a polyol compound described later to form a crosslinked structure.
- 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 antifogging layer while maintaining the flexibility and elasticity of the antifogging layer. Therefore, it becomes easier to achieve a higher degree of compatibility between the scratch resistance of the antifogging layer, the reduction in frictional resistance, and the 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.
- the structural unit derived from the monomer (a-4) is 1% by mass or more, it becomes easier to obtain an antifogging layer that satisfies scratch resistance. If it is 10% by mass or less, it becomes easier to synthesize a homogeneous (meth)acrylic resin.
- any structural unit may or may not be included.
- Examples of 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
- a constitutional unit derived from a monomer that is an aryl group or an aralkyl group can be mentioned.
- this monomer examples include methyl (meth) acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, tert-butyl (meth) acrylate, 2-ethylhexyl (meth) Acrylate, isodecyl (meth)acrylate, n-lauryl (meth)acrylate, n-stearyl (meth)acrylate, phenyl (meth)acrylate, benzyl (meth)acrylate and the like.
- R' is an alkyl group having 1 to 8 carbon atoms are preferable, those in which R' is an alkyl group having 1 to 6 carbon atoms are more preferable, and those in which R' is an alkyl group having 1 to 4 carbon atoms are more preferable. More preferred.
- the (meth)acrylic resin may contain a plurality of repeating units corresponding to the structural unit (a-5).
- a (meth)acrylic resin may be obtained by performing a polymerization reaction using two or more of the monomers listed as specific examples above.
- the (meth)acrylic resin contains the structural unit (a-5)
- its content is preferably 1 to 40% by mass, more preferably 3 to 40% by mass, based on the total structural units of the (meth)acrylic resin. 30% by mass, more preferably 5 to 20% by mass.
- 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 obtained, and if it is 100,000 or less, there is a tendency for excellent coating suitability when coating 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 is not particularly limited, it is preferably 20 to 120°C, more preferably 30 to 110°C, and still more preferably 35 to 100°C.
- 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 antifogging layer) is the glass transition temperature obtained based on the above formula. means 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.
- Peroxide-based initiators such as barate, decanoyl peroxide, t-butylperoxy-2-ethylhexanoate, and t-butylperoxybenzoate, hydrogen peroxide and iron (II) salts, persulfates and Examples include redox initiators such as sodium hydrogen sulfite, which are a combination of an oxidizing
- 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 an 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 cured film can be further enhanced.
- Polycaprolactone polyol can be used without any particular restrictions as long as it is a compound that has 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 group of the polyol compound (B) and the polyfunctional isocyanate compound undergo a cross-linking reaction to form an anti-fogging layer having 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 within the cured film 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. When the equivalent ratio (NCO)/(OH) is within this range, the crosslink density is sufficiently high, and as a result, functions such as anti-fogging properties and solvent resistance as a cured film are sufficient. From this point of view, 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, and still more preferably 35 to 80% by mass, from the viewpoint of controlling the thickness of the antifogging layer. .
- 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 may optionally contain additives such as curing catalysts, ultraviolet absorbers, light stabilizers, surfactants, leveling agents, antifoaming agents and the like.
- additives such as curing catalysts, ultraviolet absorbers, 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, still more preferably 0.1 to 3% by mass, relative to the total mass of the coating composition. is.
- the coating composition can be prepared by dissolving or dispersing each of the above-described components used as necessary in a solvent. 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 spectacle lens may be provided with a functional layer other than the 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.
- the antifogging layer may be provided on the functional layer after providing the functional layer on the lens substrate, or the functional layer may be provided after providing the antifogging layer on the lens substrate. .
- the method for manufacturing a spectacle lens includes Step 1 of forming an anti-fogging layer.
- the antifogging layer coating composition is first prepared by dissolving or dispersing each of the above-described components that are used as necessary in a solvent. Subsequently, the obtained coating composition 1 is used to form an antifogging layer (step 1).
- the coating composition is applied onto a substrate or another layer formed on the substrate, followed by preferably 70 to 120°C, more preferably 75 to 110°C, and even more preferably 80 to 120°C. Precuring is preferably carried out at 100° C. for preferably 10 to 60 minutes, more preferably 15 to 50 minutes, still more preferably 20 to 40 minutes.
- the said process 1 may be performed once and may be performed twice or more. It becomes easy to thicken the thickness of an antifogging layer by carrying out twice or more.
- the method of coating the antifogging layer 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. From the viewpoint of productivity, the dipping method is preferred.
- a dipping method is used as the coating method, the film thickness of the part that is first pulled up from the dipping tank (coating composition tank) is usually thinner, and the film thickness of the part that is pulled up from the dipping tank the latest is thicker. . Therefore, when applying the coating composition 2, it is preferable to rotate the base material vertically by 180° C. and then dip it. By doing so, it becomes easier to obtain a spectacle lens in which the film thickness of the anti-fogging layer is uniform.
- the antifogging layer After forming the antifogging layer, it is preferably dried and cured at 20 to 160° C. for 10 to 140 minutes, preferably 60 to 130° C. for 20 to 150 minutes. 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. Further, if necessary, after providing the above functional layers (hard coat layer, primer layer, antireflection layer, etc.) on the lens substrate, an antifogging layer may be provided on the functional layer. After providing the antifogging layer on the material, the functional layer may be provided on the antifogging layer.
- the film thickness of the antifogging layer of the obtained spectacle lens was measured using a non-contact film thickness measurement system FF8 manufactured by System Road Co., Ltd.
- AFA-2 Anti-fogging property evaluation
- Kyowa Interface Science Co., Ltd. was used as an antifogging evaluation device.
- the spectacle lens thus obtained was placed in the sample chamber with the surface on which the antifogging layer was formed facing up, and the atmosphere in the sample chamber was changed to 10°C in the initial state (temperature 24°C, humidity 20%). held for a minute.
- the setting conditions of the atmosphere were switched so that the atmosphere was in the measurement state (temperature of 5° C., humidity of 70%), and the anti-fogging layer was photographed every 30 seconds from the start of switching to obtain the compression anti-fogging index. .
- the time required from the start of switching to the start of reduction in the compression antifogging index was defined as the fogging start time.
- Sctch resistance evaluation A wear test was performed under the following conditions, and the state after the wear test was visually evaluated.
- ⁇ Support eraser semi-sand (manufactured by Lion Business Machine Co., Ltd.), cut cross section 12 x 5 mm ⁇ Movement distance (one way): 30mm ⁇ Moving speed: 1,600 mm/min ⁇ Load: 2 kg/cm 2 ⁇ Number of times: 1,000 reciprocations (measurement of contact angle)
- the contact angle with water was measured under the following conditions before and after the scratch resistance evaluation.
- 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 A (solid content ratio: 40% by mass).
- the obtained (meth)acrylic resin A 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 A calculated from the compounding ratio of the monomers used was 32.8° C. based on the aforementioned Fox formula.
- coating composition 1 As a solvent, a mixture of 38% by mass of t-butanol, 24% by mass of diacetone alcohol, 18% by mass of methyl ethyl ketone, 10% by mass of ethyl acetate, and 10% by mass of propylene glycol monomethyl ether acetate was prepared. 100 parts by mass of the (meth)acrylic resin A obtained above, polycaprolactone diol (manufactured by Daicel Corporation, Praxel 205U, molecular weight 530, hydroxyl value 207 to 217 mgKOH / g) 30 parts by mass, and a polyfunctional isocyanate compound (Asahi Kasei Co., Ltd.
- Coating compositions 2 to 4 having solid concentrations of 18.5% by mass, 20.5% by mass, and 24.5% by mass were prepared in the same manner as coating composition 1 except that the amount of solvent was changed. .
- coating composition 5 As a solvent, a mixture of 38% by mass of t-butanol, 24% by mass of diacetone alcohol, 18% by mass of methyl ethyl ketone, 10% by mass of ethyl acetate, and 10% by mass of propylene glycol monomethyl ether acetate was prepared. 100 parts by mass of the (meth)acrylic resin B obtained above, polycaprolactone diol (manufactured by Daicel Corporation, Praxel 205U, molecular weight 530, hydroxyl value 207 to 217 mgKOH / g) 30 parts by mass, and a polyfunctional isocyanate compound (Asahi Kasei Co., Ltd.
- Example 1 A thiourethane-based 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 substrate, and the obtained coating composition 1 was applied to this. It was applied onto the base material using a dipping method (withdrawing speed: 5 mm/sec), heated at a temperature of 100° C. for 20 minutes, and then allowed to cool. After that, it was heated at 120° C. for 120 minutes to manufacture a spectacle lens having an antifogging layer on the base material. Table 1 shows the evaluation results of the obtained spectacle lenses.
- Examples 2 to 4 A spectacle lens was produced in the same manner as in Example 1, except that the coating composition shown in Table 1 was used. Tables 1 and 2 show the evaluation results of the obtained spectacle lenses.
- Example 5 A thiourethane-based 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 the obtained coating composition 4 was applied to this. After coating the base material using a dipping method (withdrawing speed: 5 mm/sec), the composition was heated at a temperature of 100° C. for 20 minutes and then allowed to cool (coating step). The coating process was performed twice. After that, it was heated at 120° C. for 120 minutes to manufacture a spectacle lens having an antifogging layer on the base material. Table 1 shows the evaluation results of the obtained spectacle lenses.
- Example 6 A spectacle lens was manufactured in the same manner as in Example 5, except that the coating step was performed three times. Table 1 shows the evaluation results of the obtained spectacle lenses.
- a spectacle lens of Comparative Example 1 is made of only a base material of a thiourethane-based plastic lens MERIA (manufactured by HOYA Corporation, refractive index 1.60, degree S-4.00D, thickness 1.0 mm, outer diameter 75 mm). used as Table 1 shows the evaluation results of the spectacle lens.
- a thiourethane-based plastic lens MERIA manufactured by HOYA Corporation, refractive index 1.60, degree S-4.00D, thickness 1.0 mm, outer diameter 75 mm
- MERIA manufactured by HOYA Corporation, refractive index 1.60, degree S-4.00D, thickness 1.0 mm, outer diameter 75 mm
- the base material on which the antifogging layer was formed was immersed in pure water and washed for 30 minutes under conditions of 200 W and 35 kHz using an ultrasonic cleaner.
- the substrate taken out after washing was dried by heating at a temperature of 80° C. for 10 minutes.
- processing was performed at an oxygen gas flow rate of 50 ml/min and 250 W for 40 seconds.
- the substrate having the antifogging layer formed thereon was immersed in a solution of amino-modified silicone processed material (HF-869 manufactured by Shin-Etsu Chemical Co., Ltd.) diluted to 0.3% by mass with n-hexane, and taken out. C. for 15 minutes to cure. After curing, excess deposits were wiped off with acetone.
- amino-modified silicone processed material HF-869 manufactured by Shin-Etsu Chemical Co., Ltd.
- a spectacle lens that is an embodiment of the present disclosure is a spectacle lens that has a base material and a water-absorbing anti-fogging layer,
- the water-absorbing anti-fog layer is the outermost layer of the spectacle lens
- the water-absorbing anti-fogging layer is a spectacle lens containing a resin having a siloxane bond unit. According to the embodiment described above, it is possible to provide a spectacle lens with excellent anti-fogging properties.
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Abstract
Description
例えば、レンズ基材の表面に、界面活性剤を被覆する技術が知られている。
また、レンズ記載の表面に吸水性樹脂層及び撥水層を形成する技術も知られている。例えば、特許文献1には、ガラス又はプラスチック基材の表面に、特定のポリオキシエチレン鎖を有するウレタン又はアクリル樹脂を主成分とする吸水層を形成し、同吸水層の表面にアミノ変性シリコーン又はメルカプト変性シリコーンの少なくとも一方を主成分とする撥水層を形成する防曇性光学物品が記載されている。
また、特許文献1に記載の防曇層は、最表面を構成する撥水層によって吸水層が覆われてしまっているため、吸水層の吸水性能が十分に発揮されなかった。また、特許文献1に記載の防曇層は、使用により撥水層が摩耗し易く、耐擦傷性が十分ではなかった。
本開示の一実施形態は、防曇性及び耐擦傷性に優れる眼鏡レンズを提供することを課題とする。
[1]基材及び吸水性防曇層を有する眼鏡レンズであって、
前記吸水性防曇層は前記眼鏡レンズの最外層であり、
前記吸水性防曇層は、シロキサン結合単位を有する樹脂を含む、眼鏡レンズ。
[2]前記吸水性防曇層の膜厚が6μm以上である、上記[1]に記載の眼鏡レンズ。
[3]前記吸水性防曇層が前記基材に直接に積層されている、上記[1]又は[2]に記載の眼鏡レンズ。
[4]前記吸水性防曇層は撥水性能を有する、上記[1]~[3]のいずれかに記載の眼鏡レンズ。
[5]前記吸水性防曇層は、シロキサン化合物に由来する構成単位及びアクリルアミドに由来する構成単位を含む塗布組成物の硬化膜である、上記[1]~[4]のいずれかに記載の眼鏡レンズ。
[6]前記塗布組成物の固形分濃度が10.0~40.0質量%である、上記[5]に記載の眼鏡レンズ。
[7]前記防曇層が、下記の成分(A)~(C)を含む塗布組成物の硬化膜からなる、上記[1]~[6]のいずれかに記載の眼鏡レンズ。
成分(A):下記一般式(1)で表されるモノマー(a-1)に由来する構成単位、下記一般式(2)で表されるモノマー(a-2)に由来する構成単位、ヒドロキシアルキル(メタ)アクリレート(a-3)に由来する構成単位、及び、下記一般式(3)で表されるモノマー(a-4)に由来する構成単位を有する(メタ)アクリル系樹脂
成分(B):ポリオール化合物(B)
成分(C):多官能イソシアネート化合物(C)
[一般式(1)中、R1は、水素原子又はメチル基であり、R2及びR3は、それぞれ独立して、水素原子又は炭素数1~3のアルキル基であり、R2及びR3は同一でも、異なっていてもよい。]
[一般式(2)中、R4は水素原子又はメチル基であり、nは1~5の整数である。]
[一般式(3)中、R5は水素原子又はメチル基であり、R6は2価の有機基であり、nは0又は1以上の整数である。]
本明細書における「(メタ)アクリル」との表記は、アクリルとメタアクリルの両方を包含する概念を表す。「(メタ)アクリレート」等の類似の表記についても同様である。
本明細書中、モノマー(a-1)に由来する構成単位を「構成単位(a-1)」、モノマー(a-2)に由来する構成単位を「構成単位(a-2)」、モノマー(a-3)に由来する構成単位を「構成単位(a-3)」、モノマー(a-4)に由来する構成単位を「構成単位(a-4)」と称することがある。
組成物における「固形分濃度」又は「固形分比率」とは、組成物における溶媒以外の成分の濃度又は比率を意味する。
置換基を有する基についての「炭素数」とは、該置換基を除く部分の炭素数をいうものとする。
本開示の実施形態に係る眼鏡レンズは、基材及び吸水性防曇層を有する眼鏡レンズであって、前記吸水性防曇層は前記眼鏡レンズの最外層であり、前記吸水性防曇層は、シロキサン結合単位を有する樹脂を含むものである。
本開示の実施形態に係る眼鏡レンズは、吸水性防曇層が眼鏡レンズの最外層であり、吸水性防曇層が撥水層によって覆われていないため、吸水性防曇層の吸水性能が十分に発揮され、その結果防曇性に優れている。また、本開示の実施形態に係る眼鏡レンズは、シロキサン結合単位を有する樹脂を含むため、防曇性吸水層の滑り性が向上し、その結果、耐擦傷性に優れている。
本開示において、「吸水性防曇層」とは、シロキサン結合単位を有する樹脂を含む層を意味する。
なお、本開示において、吸水性防曇層を単に防曇層と称することが有る。
基材としては、様々な種類の原料からなる樹脂を用いることができる。
基材を形成する樹脂としては、例えば、ポリカーボネート樹脂、ウレタンウレア樹脂、(チオ)ウレタン樹脂、ポリスルフィド樹脂、ポリアミド樹脂、ポリエステル樹脂、アクリルアリル樹脂、アリルカーボネート樹脂等が挙げられる。(チオ)ウレタン樹脂とは、チオウレタン樹脂、及びウレタン樹脂から選ばれる少なくとも1種を意味する。これらの中でも(チオ)ウレタン樹脂、ポリスルフィド樹脂が好ましい。
好ましいプラスチック製基材の市販品としては、アリルカーボネート系プラスチックレンズ「HILUX1.50」(HOYA株式会社製、屈折率1.50)、チオウレタン系プラスチックレンズ「MERIA」(HOYA株式会社製、屈折率1.60)、チオウレタン系プラスチックレンズ「EYAS」(HOYA株式会社製、屈折率1.60)、チオウレタン系プラスチックレンズ「EYNOA」(HOYA株式会社製、屈折率1.67)、ポリスルフィド系プラスチックレンズ「EYRY」(HOYA株式会社製、屈折率1.70)、ポリスルフィド系プラスチックレンズ「EYVIA」(HOYA株式会社製、屈折率1.74)等が挙げられる。
基材としては、フィニッシュレンズ、セミフィニッシュレンズのいずれであってもよい。
基材の表面形状は特に限定されず、平面、凸面、凹面等のいずれであってもよい。
本開示の眼鏡レンズは、単焦点レンズ、多焦点レンズ、累進屈折力レンズ等のいずれであってもよい。累進屈折力レンズについては、通常、近用部領域(近用部)及び累進部領域(中間領域)が、前述の下方領域に含まれ、遠用部領域(遠用部)が上方領域に含まれる。
防曇層は、防曇性に優れる眼鏡レンズを得る観点から、吸水性を有する層である。ここで吸水性とは、材料が水分を取り込む特性を示す。防曇層を有する眼鏡レンズの吸水性の有無は、湿潤雰囲気に晒されてから曇り始めるまでの所要時間が、防曇層を有しない眼鏡レンズと比べて長いか否かによっても判断することができる。
防曇層は、防曇性を十分に発揮する観点から、眼鏡レンズの最外層として設けられる。
防曇層はいずれか一方の主面のみに設けられていてもよく、両面に設けられていてもよい。
本実施形態に係る一態様として、防曇耐久性の観点から、防曇層は、基材上に直接設けられることが好ましい。すなわち、本実施形態に係る眼鏡レンズは、基材上に直接防曇層を有することが好ましい。
防曇層は、シロキサン化合物に由来する構成単位及びアクリルアミドに由来する構成単位を含む塗布組成物の硬化膜であることが好ましい。
防曇層がシロキサン化合物に由来する構成単位を有することにより、防曇層の滑り性が向上し、その結果、防曇層の耐擦傷性が向上する。また、防曇層がアクリルアミドに由来するアミド基を有することにより、防曇層の親水性が大きくなり、これにより吸水性能が向上し、その結果、防曇性が向上する。
成分(A):下記一般式(1)で表されるモノマー(a-1)に由来する構成単位、下記一般式(2)で表されるモノマー(a-2)に由来する構成単位、ヒドロキシアルキル(メタ)アクリレート(a-3)に由来する構成単位、及び、下記一般式(3)で表されるモノマー(a-4)に由来する構成単位を有する(メタ)アクリル系樹脂
成分(B):ポリオール化合物(B)
成分(C):多官能イソシアネート化合物(C)
[一般式(1)中、R1は水素原子又はメチル基であり、R2及びR3はそれぞれ独立に水素原子又は炭素数1~3の直鎖もしくは分岐のアルキル基である。]
[一般式(2)中、R4は水素原子又はメチル基であり、nは1~5の整数である。]
[一般式(3)中、R5は水素原子又はメチル基であり、R6は2価の有機基であり、nは0又は1以上の整数である。]
塗布組成物の組成をこのようにすると、成分(A)中の、水酸基を有する構成単位(a-2)及び構成単位(a-3)のバランス(量比)を取りつつ、当量比(NCO/OH)が1よりも小さい特定の範囲に設定され、摩擦抵抗が向上する程度にまで防曇層の硬さを高めることができると考えられる。加えて、成分(A)中の、水酸基を有する構成単位(a-2)及び構成単位(a-3)の構成バランスを取りつつ、かつ、当量比(NCO/OH)が1よりも小さい特定の範囲に設定され、防曇層の架橋密度が高くなり、防曇層の耐溶剤性が向上すると考えられる。
(成分(A):(メタ)アクリル系樹脂)
本実施形態の塗布組成物は、成分(A)である(メタ)アクリル系樹脂、すなわち、下記一般式(1)で表されるモノマー(a-1)に由来する構成単位、下記一般式(2)で表されるモノマー(a-2)に由来する構成単位、ヒドロキシアルキル(メタ)アクリレート(a-3)に由来する構成単位、及び、下記一般式(3)で表されるモノマー(a-4)に由来する構成単位を有する(メタ)アクリル樹脂を含むことが好ましい。
(メタ)アクリル系樹脂は、典型的には、モノマー(a-1)、モノマー(a-2)、モノマー(a-3)及びモノマー(a-4)を重合させることで得ることができる。重合方法の詳細については後に述べる。
(メタ)アクリル構造に由来する効果を十二分に得るためには、(メタ)アクリル系樹脂は、全構成単位中の50質量%以上が、(メタ)アクリル系のモノマーに由来する構成単位であることが好ましい。より好ましくは、(メタ)アクリル系樹脂の全構成単位中の80質量%以上が、(メタ)アクリル系のモノマーに由来する構成単位である。更に好ましくは、(メタ)アクリル系樹脂の全て(100%)の構成単位が、(メタ)アクリル系のモノマーに由来する構成単位である。
本実施形態において、(メタ)アクリル系樹脂は、モノマー(a-2)に由来する構成単位を、当該樹脂の全構成単位に対して、好ましくは10~40質量%、より好ましくは20~38質量%、更に好ましくは25~35質量%含む。
(メタ)アクリル系樹脂は、モノマー(a-2)に由来する繰り返し単位を複数種含んでいてもよい。
本実施形態において、(メタ)アクリル系樹脂中のモノマー(a-3)に由来する構成単位は、(メタ)アクリル系樹脂の全構成単位に対して、好ましくは1~30質量%、より好ましくは2~20質量%、更に好ましくは3~15質量%含まれる。
本実施形態においては、モノマー(a-2)だけで架橋反応を生じさせ、防曇層を形成するのではなく、モノマー(a-3)とともに多官能イソシアネート化合物と架橋反応を生じさせることで種々の物性を兼ね備えた防曇層とすることができる。
この数値範囲とすることで、ポリオール化合物(後述)とともに、多官能イソシアネート化合物(後述)と反応し、架橋構造が適切に制御されやすくなる。そのため、防曇層の柔軟性・弾力性を維持しつつ、防曇層を硬くすることが可能となる。よって、防曇層の耐擦傷性、摩擦抵抗の低減、及び耐溶剤性とのより高度な両立を図りやすくなる。
なお、水酸基価とは、試料1gをアセチル化させたとき、水酸基と結合した酢酸を中和するのに必要とする水酸化カリウムのmg数を意味する。
本実施形態において、(メタ)アクリル系樹脂中のモノマー(a-4)に由来する構成単位は、当該樹脂の全構成単位に対して、好ましくは1~10質量%、より好ましくは2~8質量%、更に好ましくは3~7質量%含まれる。
このモノマーの具体例としては、例えば、メチル(メタ)アクリレート、エチル(メタ)アクリレート、n-ブチル(メタ)アクリレート、イソブチル(メタ)アクリレート、tert-ブチル(メタ)アクリレート、2-エチルヘキシル(メタ)アクリレート、イソデシル(メタ)アクリレート、n-ラウリル(メタ)アクリレート、n-ステアリル(メタ)アクリレート、フェニル(メタ)アクリレート、ベンジル(メタ)アクリレート等が挙げられる。
これらの中でも、R’が炭素数1~8のアルキル基であるものが好ましく、R’が1~6のアルキル基であるものがより好ましく、R’が1~4のアルキル基であるものが更に好ましい。
(メタ)アクリル系樹脂が構成単位(a-5)を含む場合、その含有量は、(メタ)アクリル系樹脂の全構成単位に対して、好ましくは1~40質量%、より好ましくは3~30質量%、更に好ましくは5~20質量%である。
なお、質量平均分子量は、ゲルパーミエーションクロマトグラフィー(GPC)により、標準物質としてポリスチレンを用いることで求めることができる。
なお、(メタ)アクリル系樹脂のガラス転移温度は、種々の方法で求めることが可能であるが、例えば以下のフォックス(Fox)の式に基づいて求めることができる。
1/Tg=(W1/Tg1)+(W2/Tg2)+(W3/Tg3)+・・・+(Wn/Tgn)
〔式中、Tgは、(メタ)アクリル系樹脂のガラス転移温度(K)、W1、W2、W3・・・Wnは、それぞれのモノマーの質量分率、Tg1、Tg2、Tg3・・・Tgnは、それぞれ各モノマーの質量分率に対応するモノマーからなる単独重合体のガラス転移温度(K)を示す。〕
重合開始剤の配合量は、特に限定されないが、重合するモノマーの混合液全体を100質量部とした場合に0.001~10質量部とすることが好ましい。
本実施形態の塗布組成物は、ポリオール化合物を含むことが好ましい。ポリオール化合物を含むことにより、(メタ)アクリル系樹脂とともに後述の多官能イソシアネート化合物と反応し、より防曇耐久性に優れた防曇層を形成することが可能となる。ポリオール化合物が1分子中に有する水酸基の個数は2以上で、好ましくは2~6、より好ましくは2~4である。
ポリオール原料としては、特に制限されないが、例えば、脂肪族ポリオール、脂環構造を有するポリオール、芳香族ポリオール等が挙げられる。本実施形態においては、硬化膜の柔軟性の観点から、脂環構脂を有しない脂肪族ポリオールが好ましい。
炭酸エステルとしては、例えば、ジメチルカーボネート、ジエチルカーボネート等の脂肪族炭酸エステル、ジフェニルカーボネート等の芳香族炭酸エステル、エチレンカーボネート等の環状炭酸エステルが挙げられる。中でも、入手や製造のしやすさから、脂肪族炭酸エステルが好ましく、ジメチルカーボネートが特に好ましい。
具体的な化合物としては、例えば、エチレングリコール、1,2-プロパンジオール、1,3-プロパンジオール、1,2-ブタンジオール、1,3-ブタンジオール、1,4-ブタンジオール、1,5-ペンタンジオール、1,6-ヘキサンジオール、1,8-オクタンジオール、1,9-ノナンジオール、3-メチル-1,5-ペンタンジオール、3,3-ジメチロールヘプタン、ジエチレングリコール、ジプロピレングリコール、ネオペンチルグリコール、シクロヘキサン-1,4-ジオール、シクロヘキサン-1,4-ジメタノール、ダイマー酸ジオール、ビスフェノールA、ビス(β-ヒドロキシエチル)ベンゼン、キシリレングリコール、グリセリン、トリメチロールプロパン、ペンタエリスリトール等の低分子ポリオール類、又はエチレンジアミン、プロピレンジアミン、トルエンジアミン、メタフェニレンジアミン、ジフェニルメタンジアミン、キシリレンジアミン等の低分子ポリアミン類等のような活性水素基を2個以上、好ましくは2~3個有する化合物を開始剤として、エチレンオキサイド、プロピレンオキサイド、ブチレンオキサイド等のようなアルキレンオキサイド類を付加重合させることによって得られるポリエーテルポリオール、或いはメチルグリシジルエーテル等のアルキルグリシジルエーテル類、フェニルグリシジルエーテル等のアリールグリシジルエーテル類、テトラヒドロフラン等の環状エーテルモノマーを開環重合することで得られるポリエーテルポリオールを挙げることができる。
また、ポリオール化合物は、ポリカプロラクトンポリオール、ポリカーボネートポリオール、及びポリエーテルポリオールのうち、複数種を含んでいてもよい。
これは、成分(A)である(メタ)アクリル系樹脂が前述の一般式(2)の構造、すなわちカプロラクトン構造を持つため、ポリオール化合物としては当該樹脂との相溶性が良好となりやすい傾向があるということと、架橋密度を上げ過ぎずに防曇性能を向上させやすい傾向があるためである。
本実施形態の塗布組成物は、成分(C)として、多官能イソシアネート化合物を含むことが好ましい。塗布組成物が、多官能イソシアネート化合物を含むことにより、成分(A)である(メタ)アクリル系樹脂に含まれる構成単位(a-2)及び構成単位(a-3)が有する水酸基、並びに成分(B)であるポリオール化合物の水酸基と多官能イソシアネート化合物が架橋反応を起こし、防曇耐久性に優れる防曇層となる。
多官能イソシアネート化合物は、1分子中に2個以上のイソシアネート基(脱離性基で保護されたイソシアネート基を含む)を有する化合物である。好ましくは、多官能イソシアネート化合物は、その官能基数は、より好ましくは1分子あたり2~6個、更に好ましくは1分子あたり2~4個である。
当該観点から、当該当量比(NCO)/(OH)は、好ましくは0.25~0.50、より好ましくは0.35~0.45である。
本実施形態の塗布組成物は、1液型、すなわち、溶剤以外の全成分が、溶剤に実質的に均一に混合(溶解又は分散)された状態であってよい。多官能イソシアネート化合物がブロックイソシアネートである場合には、1液型が好ましい。
また、別の態様として、本実施形態の塗布組成物は、2液型であってもよい。2液型にすることで、塗布組成物の保存性を高めることができる。
例えば、本実施形態の塗布組成物は、(1)(メタ)アクリル系樹脂及び/又はポリオール化合物を含み、多官能イソシアネート化合物を含まないA液と、(2)多官能イソシアネート化合物を含み、(メタ)アクリル系樹脂及びポリオール化合物を含まないB液とから構成され、A液とB液は別々の容器で保存され、使用(塗工)直前にA液とB液を混合する形態であってもよい。
この場合、(メタ)アクリル系樹脂、ポリオール化合物、及び多官能イソシアネート化合物以外の成分(添加剤等)は、A液に含まれていても、B液に含まれていても、あるいはその他の容器で準備されていてもよい。
特に、多官能イソシアネート化合物が、ブロックイソシアネートではない場合(すなわち、系中でイソシアネート基が-NCOの形で存在している場合)には、塗布組成物は2液型であることが好ましい。
本実施形態の塗布組成物は、溶剤を含んでもよい。溶剤を用いることにより、塗布組成物の粘度及び固形分量の調整が容易となる。
溶剤としては、トルエン、及びキシレン等の芳香族炭化水素系溶剤、メタノール、エタノール、イソプロピルアルコール、n-ブタノール、t-ブタノール、イソブタノール、ジアセトンアルコール等のアルコール系溶剤、アセトン、メチルエチルケトン、メチルイソブチルケトン、及びシクロヘキサノン等のケトン系溶剤、酢酸エチル、酢酸プロピル、酢酸ブチル、及び酢酸イソブチル等のエステル系溶剤、プロピレングリコールモノメチルアセテート、プロピレングリコールモノメチルエーテル、プロピレングリコールモノメチルエーテルアセテート等のグリコールエーテル系溶剤等が挙げられる。
これらの中でも、イソシアネートとの反応性が低く、溶解性及び乾燥性等の観点から、t-ブタノール、ジアセトンアルコール、メチルエチルケトン、酢酸エチル、及びプロピレングリコールモノメチルエーテルアセテートが好ましい。
塗布組成物は、必要に応じて、硬化触媒、紫外線吸収剤、光安定剤、界面活性剤、レベリング剤、消泡剤等の添加剤を含んでもよい。
添加剤の含有量は、例えば、塗布組成物の全質量に対して、好ましくは0.001~5質量%、より好ましくは0.01~4質量%、更に好ましくは0.1~3質量%である。
各成分は、同時に、又は、任意の順序で順次、溶媒に溶解又は分散させることすることができる。具体的な溶解又は分散させる方法には、特に制限はなく、公知の方法を何ら制限なく採用することができる。
眼鏡レンズには、防曇層以外の機能層が設けられていてもよい。
上記機能層としては、ハードコート層、反射防止層、プライマー層等が挙げられる。
上記機能層は、レンズ基材の第1主面上に設けられていてもよいし、レンズ基材の第2主面上に設けられていてもよいし、レンズ基材の第1主面及び第2主面の両方の上に設けられていてもよい。また、レンズ基材上に上記機能層を設けた後、上記機能層上に防曇層を設けてもよく、レンズ基材上に防曇層を設けた後に、上記機能層を設けてもよい。
本実施形態に係る眼鏡レンズの製造方法は、防曇層を形成する工程1を含む。
一態様において、まず、必要に応じて用いられる上記各成分を、溶媒に溶解又は分散させることにより、防曇層用塗布組成物を調製する。
続いて、得られた塗布組成物1を用いて、防曇層を形成する(工程1)。工程1は、塗布組成物を基材もしくは基材上に形成された他の層上に塗工し、続いて、好ましくは70~120℃、より好ましくは75~110℃、さらに好ましくは80~100℃で、好ましくは10~60分、より好ましくは15~50分、さらに好ましくは20~40分、プレキュアを行うことが好ましい。
なお、当該工程1は、1回行っても良く、2回以上行っても良い。2回以上行うことにより、防曇層の厚さを厚くすることが容易となる。
塗工方法としてディッピング法を用いる場合、通常、ディッピング槽(塗布組成物槽)から、先に引き上げられた部分の膜厚は薄くなり、最も遅くディッピング槽から引き上げられた部分の膜厚は厚くなる。したがって、塗布組成物2を塗工する際には、塗布組成物1を塗工する際とは、基材の上下方向を180℃回転させてディッピングすることが好ましい。このようにすることで、防曇層の膜厚が均一な眼鏡レンズを得られ易くなる。
また、必要に応じて、上述した機能層(ハードコート層、プライマー層、反射防止層等)を、レンズ基材上に設けた後、機能層上に防曇層を設けてもよく、レンズ基材上に防曇層を設けた後、防曇層上に機能層を設けてもよい。
また、実施例に記載した組成に対し、発明の詳細な説明に記載した組成に調整を行えば、クレームした組成範囲全域にわたって実施例と同様に発明を実施することができる。
また、実施例に記載した組成に対し、発明の詳細な説明に記載した組成に調整を行えば、クレームした組成範囲全域にわたって実施例と同様に発明を実施することができる。
以下の実施例及び比較例で得られた塗布組成物と眼鏡レンズについて、以下の項目の測定評価を行った。これらの測定評価結果を表1に示す。
JIS K 0070:1992「化学製品の酸価,けん化価,エステル価,よう素価,水酸基価及び不けん化物の試験方法」の、「7.1 中和滴定法」に規定された方法に準じて測定及び算出した。
なお、水酸基価の算出に用いる酸価の値は、上記JIS規格の「3.1 中和滴定法」に規定された方法に準じて測定及び算出した。
ゲルパーミエーションクロマトグラフィー(GPC)により測定、算出した。用いた装置、条件等は以下の通りである。
・使用機器:HLC8220GPC(株式会社東ソー製)
使用カラム:TSKgel SuperHZM-M、TSKgel GMHXL-H、TSKgel G2500HXL、TSKgel G5000HXL(株式会社東ソー製)
・カラム温度:40℃
標準物質:TSKgel 標準ポリスチレンA1000、A2500、A5000、F1、F2、F4、F10(株式会社東ソー製)
・検出器:RI(示差屈折)検出器
・溶離液:テトラヒドロフラン
・流速:1ml/min
得られた眼鏡レンズの防曇層の膜厚は株式会社システムロード製 非接触膜厚測定システムFF8を用いて測定した。
防曇性評価装置として、協和界面科学株式会社製「AFA-2」を用いた。得られた眼鏡レンズを、その防曇層が形成された面が上になるようにして試料室内に載置し、試料室内の雰囲気を、初期状態(温度24℃、湿度20%)にて10分間保持した。次いで、雰囲気が測定状態(温度5℃、湿度70%)となるように雰囲気の設定条件の切替を行い、切替開始時から30秒毎に防曇層を撮影し、圧縮防曇指数を得た。当該切替開始時から当該圧縮防曇指数の低下が開始するまでの所要時間を、曇り開始時間とした。
(耐擦傷性評価)
下記条件で摩耗試験を行い、摩耗試験後の状態を目視にて評価した。
・装置名:往復摩耗試験機 TRIBOGEAR 30S(新東科学社製)
・摩耗材:レンズクリーニングペーパー ダスパーK3(小津産業社製)
・支持体:消ゴム 半砂(ライオン事務機社製)、カット断面12×5mm
・移動距離(片道):30mm
・移動速度:1,600mm/分
・荷重:2kg/cm2
・回数:1,000往復
(接触角の測定)
上記の耐擦傷性評価を行う前と行った後とにおいて、下記条件で、水に対する接触角を測定した。
・装置名 :全自動接触角計DM700(協和界面科学株式会社製)
・手法 :液滴法
・方法 :楕円フィッティング法
・水滴 :20μL
・測定時 :滴下後20秒後
・測定回数:3点測定の平均
撹拌器、温度計、コンデンサーおよび窒素ガス同入管を備えた500ml形のフラスコにプロピレングリコールモノメチルアセテート(PGMAC)150質量部を仕込み、110℃まで昇温した。
これとは別に、ジメチルアクリルアミド(DMAA)25質量部、ポリカプロラクトン変性ヒドロキシエチルアクリレート(株式会社ダイセル製、プラクセルFA2D)35質量部、2-ヒドロキシルエチルメタクリレート(HEMA)10質量部、片末端メタクリレート変性ポリジメチルシロキサン(JNC株式会社製、サイラプレーンFM-0721、分子量5000)5質量部、メタクリル酸メチル25質量部、及び、1,1’-アゾビス(シクロヘキサン-1-カルボニトリル)(和光純薬工業株式会社製、V-40)1質量部を混合した。この混合モノマーを撹拌しながら2時間かけて、上記の500ml形のフラスコに滴下し、5時間反応させた。
加熱を止めて室温まで冷却し、(メタ)アクリル系樹脂Aを含む樹脂溶液(固形分比率:40質量%)を得た。
得られた(メタ)アクリル系樹脂Aの水酸基価は57mgKOH/gであり、数平均分子量(Mn)は12,000であり、質量平均分子量(Mw)は44,000であり、多分散度(Mw/Mn)は3.67であった。また、前述のフォックス(Fox)の式に基づいて、使用したモノマーの配合比から計算した(メタ)アクリル系樹脂Aのガラス転移温度(Tg)は32.8℃であった。
溶剤として、t-ブタノール38質量%、ジアセトンアルコール24質量%、メチルエチルケトン18質量%、酢酸エチル10質量%、プロピレングリコールモノメチルエーテルアセテート10質量%を混合したものを調製した。
上記で得た(メタ)アクリル系樹脂A100質量部、ポリカプロラクトンジオール(株式会社ダイセル製、プラクセル205U、分子量530、水酸基価207~217mgKOH/g)30質量部、及び、多官能イソシアネート化合物(旭化成株式会社製、24A-100、ヘキサメチレンジイソシアネートのビウレットタイプ、イソシアネート基含有率23.5質量%、固形分100質量%)23.5質量部を、上記溶剤に混合し、固形分濃度が16.5質量%の塗布組成物1を調製した。
なお、(メタ)アクリル系樹脂Aの量は、樹脂溶液(固形分量:質量%)としての量ではなく、樹脂溶液中に含まれる樹脂(固形分)の量を表し、多官能イソシアネート化合物の量も固形分としての量を表している。
また、上記(メタ)アクリル系樹脂Aとポリオール化合物とを、上記の量で均一に混合したときの混合物の水酸基価の測定値は93mgKOH/gであった。
溶剤の量を変更したこと以外は塗布組成物1と同様にして、固形分濃度が各々18.5質量%、20.5質量%、24.5質量%の塗布組成物2~4を調製した。
撹拌器、温度計、コンデンサーおよび窒素ガス同入管を備えた500ml形のフラスコにプロピレングリコールモノメチルアセテート(PGMAC)150質量部を仕込み、110℃まで昇温した。
これとは別に、ジメチルアクリルアミド(DMAA)25質量部、ポリカプロラクトン変性ヒドロキシエチルアクリレート(株式会社ダイセル製、プラクセルFA2D)35質量部、2-ヒドロキシルエチルメタクリレート(HEMA)10質量部、メタクリル酸メチル25質量部、及び、1,1’-アゾビス(シクロヘキサン-1-カルボニトリル)(和光純薬工業株式会社製、V-40)1質量部を混合した。この混合モノマーを撹拌しながら2時間かけて、上記の500ml形のフラスコに滴下し、5時間反応させた。
加熱を止めて室温まで冷却し、(メタ)アクリル系樹脂Bを含む樹脂溶液(固形分比率:40質量%)を得た。
溶剤として、t-ブタノール38質量%、ジアセトンアルコール24質量%、メチルエチルケトン18質量%、酢酸エチル10質量%、プロピレングリコールモノメチルエーテルアセテート10質量%を混合したものを調製した。
上記で得た(メタ)アクリル系樹脂B100質量部、ポリカプロラクトンジオール(株式会社ダイセル製、プラクセル205U、分子量530、水酸基価207~217mgKOH/g)30質量部、及び、多官能イソシアネート化合物(旭化成株式会社製、24A-100、ヘキサメチレンジイソシアネートのビウレットタイプ、イソシアネート基含有率23.5質量%、固形分100質量%)23.5質量部を、上記溶剤に混合し、固形分濃度が19.5質量%の塗布組成物5を調製した。
チオウレタン系プラスチックレンズMERIA(HOYA株式会社製、屈折率1.60、度数S-4.00D、厚さ1.0mm、外径75mm)を基材として用い、得られた塗布組成物1をこの基材上にディッピング法(引き上げ速度:5mm/秒)を用いて塗布した後、温度100℃で20分加熱し、その後に放冷した。
その後、120℃で120分加熱し、上記基材上に防曇層を有する眼鏡レンズを製造した。得られた眼鏡レンズの評価結果を表1に示す。
実施例1において、塗布組成物を表1に示すものとしたこと以外は同様の操作により、眼鏡レンズを製造した。得られた眼鏡レンズの評価結果を表1及び表2に示す。
チオウレタン系プラスチックレンズMERIA(HOYA株式会社製、屈折率1.60、度数S-4.00D、厚さ1.0mm、外径75mm)を基材として用い、得られた塗布組成物4をこの基材上にディッピング法(引き上げ速度:5mm/秒)を用いて塗布した後、温度100℃で20分加熱し、その後に放冷した(塗布工程)。当該塗布工程を2回行った。
その後、120℃で120分加熱し、上記基材上に防曇層を有する眼鏡レンズを製造した。得られた眼鏡レンズの評価結果を表1に示す。
実施例5において、塗布工程を3回行ったことと以外は同様の操作により、眼鏡レンズを製造した。得られた眼鏡レンズの評価結果を表1に示す。
チオウレタン系プラスチックレンズMERIA(HOYA株式会社製、屈折率1.60、度数S-4.00D、厚さ1.0mm、外径75mm)の基材のみからなる眼鏡レンズを比較例1の眼鏡レンズとして用いた。当該眼鏡レンズの評価結果を表1に示す。
チオウレタン系プラスチックレンズMERIA(HOYA株式会社製、屈折率1.60、度数S-4.00D、厚さ1.0mm、外径75mm)を基材として用い、得られた塗布組成物5をこの基材上にディッピング法(引き上げ速度:5mm/秒)を用いて塗布した後、温度100℃で20分加熱し、その後に放冷した。
その後、120℃で120分加熱し、上記基材上に防曇層形成した。
次に、この防曇層を形成した基材を純水中に浸漬し、超音波洗浄機を使い200W 35kHzの条件下で30分洗浄した。洗浄後取り出した基材を温度80℃で10分加熱し乾燥させた。
次にプラズマ処理装置で、酸素ガス流量50ml/分、250Wで40秒処理を行った。
次に、アミノ変性シリコーン加工物(信越化学工業製 HF-869)をn-ヘキサンで0.3質量%に希釈した溶液に、防曇層を形成した基材を浸漬し取り出した後、温度100℃で15分加熱し硬化させた。硬化後にアセトンで余剰付着分を拭き取った。
本開示の実施の形態である眼鏡レンズは、基材及び吸水性防曇層を有する眼鏡レンズであって、
前記吸水性防曇層は前記眼鏡レンズの最外層であり、
前記吸水性防曇層は、シロキサン結合単位を有する樹脂を含む、眼鏡レンズである。
上述した実施の態様によれば、防曇性に優れる眼鏡レンズを提供することができる。
本開示は、上記各成分の例、含有量、各種物性については、発明の詳細な説明に例示又は好ましい範囲として記載された事項を任意に組み合わせてもよい。
また、実施例に記載した組成に対し、発明の詳細な説明に記載した組成となるように調整を行えば、クレームした組成範囲全域にわたって実施例と同様に開示の実施の形態を実施することができる。
Claims (7)
- 基材及び吸水性防曇層を有する眼鏡レンズであって、
前記吸水性防曇層は前記眼鏡レンズの最外層であり、
前記吸水性防曇層は、シロキサン結合単位を有する樹脂を含む、眼鏡レンズ。 - 前記吸水性防曇層の膜厚が6μm以上である、請求項1に記載の眼鏡レンズ。
- 前記吸水性防曇層が前記基材に直接に積層されている、請求項1又は2に記載の眼鏡レンズ。
- 前記吸水性防曇層は撥水性能を有する、請求項1~3のいずれかに記載の眼鏡レンズ。
- 前記吸水性防曇層は、シロキサン化合物に由来する構成単位及びアクリルアミドに由来する構成単位を含む塗布組成物の硬化膜である、請求項1~4のいずれかに記載の眼鏡レンズ。
- 前記塗布組成物の固形分濃度が10.0~40.0質量%である、請求項5に記載の眼鏡レンズ。
- 前記防曇層が、下記の成分(A)~(C)を含む塗布組成物の硬化膜からなる、請求項1~6のいずれかに記載の眼鏡レンズ。
成分(A):下記一般式(1)で表されるモノマー(a-1)に由来する構成単位、下記一般式(2)で表されるモノマー(a-2)に由来する構成単位、ヒドロキシアルキル(メタ)アクリレート(a-3)に由来する構成単位、及び、下記一般式(3)で表されるモノマー(a-4)に由来する構成単位を有する(メタ)アクリル系樹脂(A)
成分(B):ポリオール化合物(B)
成分(C):多官能イソシアネート化合物(C)
[一般式(1)中、R1は、水素原子又はメチル基であり、R2及びR3は、それぞれ独立して、水素原子又は炭素数1~3のアルキル基であり、R2及びR3は同一でも、異なっていてもよい。]
[一般式(2)中、R4は水素原子又はメチル基であり、nは1~5の整数である。]
[一般式(3)中、R5は水素原子又はメチル基であり、R6は2価の有機基であり、nは0又は1以上の整数である。]
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