WO2022211021A1 - 眼鏡レンズ防曇膜用組成物及び眼鏡レンズ - Google Patents
眼鏡レンズ防曇膜用組成物及び眼鏡レンズ Download PDFInfo
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- WO2022211021A1 WO2022211021A1 PCT/JP2022/016495 JP2022016495W WO2022211021A1 WO 2022211021 A1 WO2022211021 A1 WO 2022211021A1 JP 2022016495 W JP2022016495 W JP 2022016495W WO 2022211021 A1 WO2022211021 A1 WO 2022211021A1
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- 239000007800 oxidant agent Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
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- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000010421 standard material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- BWSZXUOMATYHHI-UHFFFAOYSA-N tert-butyl octaneperoxoate Chemical compound CCCCCCCC(=O)OOC(C)(C)C BWSZXUOMATYHHI-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
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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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- C08F220/00—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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- C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
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- 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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- 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
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/4269—Lactones
- C08G18/4277—Caprolactone and/or substituted caprolactone
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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
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- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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- 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
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- 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
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- C08G18/6229—Polymers of hydroxy groups containing esters of acrylic or methacrylic acid with aliphatic polyalcohols
- C08G18/6233—Polymers of hydroxy groups containing esters of acrylic or methacrylic acid with aliphatic polyalcohols the monomers or polymers being esterified with carboxylic acids or lactones
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- 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
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- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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- C08G18/40—High-molecular-weight compounds
- C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
- C08G18/6295—Polymers of silicium containing compounds having carbon-to-carbon double bonds
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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
- C08G18/70—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
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- 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
- C09D133/00—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 at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/24—Homopolymers or copolymers of amides or imides
- C09D133/26—Homopolymers or copolymers of acrylamide or methacrylamide
-
- 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
- C09D175/06—Polyurethanes from polyesters
-
- 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
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- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/10—Optical coatings produced by application to, or surface treatment of, optical elements
- G02B1/14—Protective coatings, e.g. hard coatings
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- 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
- G02C7/02—Lenses; Lens systems ; Methods of designing lenses
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- 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
- G02C7/022—Ophthalmic lenses having special refractive features achieved by special materials or material structures
-
- 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
- C08G2150/00—Compositions for coatings
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- 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
- C08G2290/00—Compositions for creating anti-fogging
Definitions
- the present disclosure relates to a spectacle lens antifogging film composition and a spectacle lens.
- the anti-fogging layer formed by coating the surface with a surfactant is insufficient in preventing "fogging" in a high-humidity environment, and there is room for improvement. Therefore, recently, instead of surfactants, a technique for preventing "fogging" by coating a water-absorbing substance on the article substrate to form an anti-fogging film with water-absorbing performance has been studied. ing.
- Patent Document 1 describes an anti-fogging optical article in which a water-absorbing film is formed on an optical article substrate, and the water-absorbing film has a multi-layer structure of two or more layers.
- a water-absorbing layer containing urethane or acrylic resin having a specific polyoxyethylene chain as a main component is formed on the surface of a glass or plastic substrate, and the surface of the water-absorbing layer is coated with amino-modified silicone or mercapto
- An antifogging optical article having a water-repellent layer containing at least one of modified silicones as a main component is described.
- the anti-fogging film having water absorption performance described in Patent Document 1 and Patent Document 2 is superior in anti-fogging properties and anti-fogging durability compared to conventional cases where a surfactant is applied to the surface to form an anti-fogging layer. It is.
- an anti-fogging film is usually formed by applying a liquid anti-fogging film-forming coating liquid to a substrate to form a film, the bubbles already contained in the coating liquid are removed. Also, bubbles caught during application may adhere to the substrate.
- one embodiment of the present disclosure provides a composition for spectacle lens anti-fog film that can produce a spectacle lens with excellent anti-fog properties and appearance, and a spectacle lens with excellent anti-fog properties and appearance. The task is to provide
- Embodiments of the present disclosure relate to the following [1] to [8].
- [1] A composition for an antifogging film for eyeglass lenses, having a viscosity at 15°C of 20 mPa ⁇ s or more and 80 mPa ⁇ s or less and a solid content of 10% by mass or more and 25% by mass or less.
- [2] The composition for spectacle lens antifogging film according to the above [1], wherein the viscosity is 24 mPa ⁇ s or more.
- composition for spectacle lens anti-fogging film comprising 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.
- a spectacle lens having an antifogging film obtained by curing the spectacle lens antifogging film composition according to any one of [1] to [4] above.
- R 6 is a divalent organic group, and n is an integer of 0 or 1 or more.
- [5] A spectacle lens having an antifogging film obtained by curing the spectacle lens antifogging film composition according to any one of [1] to [4] above.
- [6] The spectacle lens according to [5] above, wherein the anti-fogging film is the outermost layer.
- a spectacle lens anti-fog film composition that can produce a spectacle lens with excellent anti-fog properties and appearance, and a spectacle lens with excellent anti-fog properties and appearance.
- 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)".
- the "viscosity" of the composition for an antifogging film for spectacle lenses is based on JIS Z 8803:2011-11 (viscosity measurement method using a vibration viscometer). and measured at a temperature of 15°C.
- the vibration viscometer include a vibration viscometer "VM-10A” (manufactured by Sekonic Co., Ltd.).
- the “solid content” in the antifogging film composition means the amount of components other than the solvent.
- the “carbon number” of a group having a substituent means the carbon number of the portion excluding the substituent.
- composition for spectacle lens anti-fogging film has a viscosity at 15° C. of 20 mPa ⁇ s or more and 80 mPa ⁇ s or less, and a solid content of 10% by mass or more and 25% by mass or less.
- the composition for anti-fogging film has the above viscosity and the above solid content, it is possible to secure a film thickness capable of forming an antifogging film having excellent antifogging properties.
- the viscosity of the antifogging film composition at 15° C. is preferably 22 mPa ⁇ s or more, more preferably 23 mPa ⁇ s or more, and still more preferably 24 mPa ⁇ s or more, from the viewpoint of obtaining spectacle lenses with more excellent antifogging properties. From the viewpoint of obtaining spectacle lenses with excellent appearance, it is preferably 65 mPa ⁇ s or less, more preferably 50 mPa ⁇ s or less, and even more preferably 45 mPa ⁇ s or less.
- the solid content of the composition for an antifogging film is preferably 13% by mass or more, more preferably 15% by mass or more, still more preferably 16% by mass or more, and even more preferably, from the viewpoint of obtaining a spectacle lens with more excellent antifogging properties. is 17% by mass or more, and preferably 24.8% by mass or less from the viewpoint of obtaining spectacle lenses with excellent appearance.
- the antifogging film composition preferably contains the following components (A) to (C).
- 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 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 considered that the water adhering to the surface of the antifogging film obtained by curing the antifogging film composition is easily absorbed into the cured interior.
- the polyol compound (B) it is possible to maintain the cross-linking density necessary for an anti-fogging film while creating 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 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 antifogging film.
- 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 lubricity of the antifogging film.
- the anti-fogging film when an external force is applied to the anti-fogging film, the flexibility and elasticity of the anti-fogging film absorb the external force, while the slipperiness allows the external force to escape to the outside of the anti-fogging film. It is thought that the anti-fogging film is less likely to be scratched as a result of synergistic expression.
- the composition for an antifogging film contains 20% by mass or more and 65% by mass or less of the structural units derived from the monomer (a-1) with respect to 100% by mass of all the structural units constituting the component (A), and the monomer (a -2) is 10% by mass or more and 40% by mass or less, and the ratio of the structural units derived from the monomer (a-4) is 1% by mass or more and 10% by mass or less, and the component (C) Ratio of the total amount (OH) obtained by adding the number of isocyanate groups contained in (NCO) and the number of hydroxyl groups contained in component (A) and the number of hydroxyl groups contained in component (B) (NCO) / (OH ) is preferably 0.15 or more and 0.55 or less.
- 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 crosslink density of the antifogging film is increased, and the solvent resistance of the antifogging film is considered to be improved.
- composition for an antifogging film of the present embodiment has a (meth)acrylic resin as the component (A), that is, a structural unit derived from the monomer (a-1) represented by the general formula (1), the general formula Structural units derived from the monomer (a-2) represented by (2), structural units derived from the hydroxyalkyl (meth)acrylate (a-3), and the monomer (a) represented by the 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) is N,N-dimethyl(meth)acrylamide, N,N-diethyl, from the viewpoint of improving the breath antifogging performance of the antifogging film and suppressing the occurrence of fogging in the steam test. It is particularly preferred to contain (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 film 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 forms an antifogging film by undergoing a cross-linking reaction with a polyfunctional isocyanate compound described later.
- the monomer (a-2) alone is not used to cause a cross-linking reaction to form an anti-fogging film. It is possible to obtain an anti-fogging film 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 film while maintaining the flexibility and elasticity of the antifogging film. Therefore, it becomes easier to achieve a higher degree of compatibility between the scratch resistance of the antifogging film, 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 film 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 is the glass transition temperature determined 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.
- 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.
- composition for an antifogging film of the present embodiment preferably contains a polyol compound.
- a polyol compound By containing a polyol compound, it becomes possible to form an antifogging film having more excellent antifogging 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.
- composition for an antifogging film of the present embodiment preferably contains a polyfunctional isocyanate compound as component (C).
- a polyfunctional isocyanate compound in the composition for an antifogging film, the hydroxyl group of the structural unit (a-2) and the structural unit (a-3) contained in the (meth)acrylic resin that is the component (A) , and the hydroxyl group of the polyol compound as the component (B) and the polyfunctional isocyanate compound undergo a cross-linking reaction, resulting in an anti-fogging film 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 preferable.
- 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 anti-fogging film 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 anti-fogging film composition of the present embodiment may be of a two-liquid type. By adopting a two-liquid type, the storage stability of the composition for an antifogging film can be enhanced.
- the composition for an antifogging film of the present embodiment comprises (1) a liquid A containing a (meth)acrylic resin and/or a polyol compound and not containing a polyfunctional isocyanate compound, and (2) a polyfunctional isocyanate compound.
- a and B liquids are stored in separate containers, and the A and B liquids are mixed immediately before use (coating).
- 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 antifogging film composition may be a two-pack type. preferable.
- the antifogging film composition of the present embodiment may contain a solvent.
- a solvent By using a solvent, it becomes easy to adjust the viscosity and solid content of the composition for an antifogging film.
- 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 antifogging film 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 antifogging film thickness. %.
- 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 antifogging film composition may contain additives such as a curing catalyst, an ultraviolet absorber, a light stabilizer, a surfactant, a leveling agent, and an antifoaming agent, if necessary.
- the content of the additive is 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. .
- composition for an antifogging film can be prepared by dissolving or dispersing each of the above-mentioned components, which are 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.
- a spectacle lens according to an embodiment of the present disclosure has a substrate and an anti-fogging film provided on the substrate.
- the lens substrate is, for example, a spectacle lens substrate.
- 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 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 carbonate plastic lens "HILUX 1.50" (manufactured by HOYA Corporation, refractive index 1.50), thiourethane plastic lens "EYAS” (manufactured by HOYA Corporation, refractive index index 1.60), thiourethane plastic lens “MERIA” (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 index
- 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 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 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.
- an antifogging film suitable for a spectacle lens By curing the antifogging film composition of the present embodiment, an antifogging film suitable for a spectacle lens can be formed. By using the anti-fogging film composition of the present embodiment, inclusion of bubbles in the anti-fogging film is suppressed, and a spectacle lens with excellent anti-fogging properties and appearance can be produced.
- the anti-fogging film is preferably provided as the outermost layer of the spectacle lens from the viewpoint of sufficiently exhibiting anti-fogging properties.
- the anti-fogging film may be provided only on one of the principal surfaces, or may be provided on both surfaces.
- the antifogging film is preferably a layer having water absorption properties.
- the antifogging film "has water absorption” means that the material constituting the antifogging film exhibits a characteristic of absorbing moisture, and the transparent substrate on which the antifogging film is formed is allowed to stand at room temperature. After storage at , the transparent substrate with the antifogging film was placed at a position 35 mm away from the surface of hot water at 40 ° C. and steam from the hot water was applied for 15 seconds. It means that there is no distortion due to dew condensation in the image seen through the transparent substrate with an antifogging film after contact with steam.
- the antifogging film is preferably obtained by curing a composition for an antifogging film containing the components (A) to (C). If it is obtained by curing the antifogging film composition containing the components (A) to (C), it exhibits high durability even if the antifogging film is located in the outermost layer of the spectacle lens. be able to.
- the anti-fogging film is directly provided on the substrate.
- the anti-fogging film may be a single layer or an anti-fogging film consisting of multiple layers. From the viewpoint of productivity, the anti-fogging film is preferably a single layer.
- the thickness of the antifogging film is preferably 1 to 50 ⁇ m, more preferably 3 to 40 ⁇ m, still more preferably 5 to 30 ⁇ m, and even more preferably 8 to 25 ⁇ m, from the viewpoint of improving antifogging properties.
- the spectacle lens may be provided with a functional layer other than the anti-fogging film.
- 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 film 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 film on the lens substrate. .
- a composition for an antifogging film (in the case of a two-liquid type, , a mixture of two liquids) is coated on the lens substrate, and the coating film is dried and cured at a predetermined temperature to form an anti-fogging film, thereby obtaining a spectacle lens.
- 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. From the viewpoint of productivity, the dipping method is preferred. After coating, it is dried and cured at 20 to 160° C.
- an antifogging film may be provided on the functional layer.
- the functional layer may be provided on the antifogging film.
- Viscosity measurement It was measured at a measurement temperature of 15° C. using a vibrating viscometer “VM-10A” (manufactured by Sekonic Co., Ltd.). The measurement method conformed to JIS Z 8803:2011-11 (viscosity measurement method using a vibration viscometer).
- the anti-fogging film thickness of the obtained spectacle lens was measured using a non-contact film thickness measurement system "FF8" (manufactured by System Road Co., Ltd.).
- Appearance evaluation Appearance evaluation of the obtained spectacle lens was performed according to the following evaluation criteria.
- 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.
- composition for antifogging film (Meth) acrylic resin obtained above, polycaprolactone diol (manufactured by Daicel Corporation, Praxel 205U, molecular weight 530, hydroxyl value 207 to 217 mgKOH / g), polyfunctional isocyanate compound (manufactured by Asahi Kasei Corporation, 24A-100, hexa Biuret type methylene diisocyanate, isocyanate group content 23.5% by mass, solid content 100% by mass), propylene glycol monomethyl ether acetate, diacetone alcohol, methyl ethyl ketone, t-butanol, and ethyl acetate were mixed to obtain a mixture.
- polycaprolactone diol manufactured by Daicel Corporation, Praxel 205U, molecular weight 530, hydroxyl value 207 to 217 mgKOH / g
- polyfunctional isocyanate compound manufactured by Asahi Kasei Corporation, 24A
- each content in the obtained mixture is as follows.
- Polyfunctional isocyanate compound 3.4% by mass
- ethyl acetate, methyl ethyl ketone, and diacetone alcohol are added to the mixture and mixed so that the viscosity is 47.1 mPa ⁇ s and the solid content is 22.5% by mass, thereby preparing an antifogging film composition.
- the amount of (meth)acrylic resin is not the amount of the resin solution (solid content: mass%), but the amount of resin (solid content) contained in the resin solution. It represents the amount as a solid content. Further, when 100 parts by mass of the (meth)acrylic resin and 30 parts by mass of the polyol compound (polycaprolactone diol) were uniformly mixed, the hydroxyl value of the mixture was measured to be 93 mgKOH/g.
- Examples 2-3, Comparative Examples 1-4 A spectacle lens was produced in the same manner as in Example 1, except that ethyl acetate, methyl ethyl ketone, and diacetone alcohol were used to adjust the solid content and viscosity to the values shown in Table 1.
- the spectacle lens antifogging film composition according to the embodiment of the present disclosure has a viscosity of 20 mPa ⁇ s or more and 80 mPa ⁇ s or less at 15° C. and a solid content of 10% by mass or more and 25% by mass or less. According to the embodiment described above, it is possible to provide a composition for an anti-fogging film for a spectacle lens that can produce a spectacle lens with excellent anti-fogging properties and appearance, and a spectacle lens with excellent anti-fogging properties and appearance.
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Abstract
Description
しかしながら、このような防曇膜は、通常、液体状の防曇膜形成用塗布液を基材に塗布し、成膜することによって形成されるため、該塗布液中に既に含まれていた泡や、塗布時に巻き込まれた泡が基材上に付着する場合がある。このように、泡が基材上に付着した状態で防曇膜が乾燥及び硬化されると、泡の形状が残った状態で防曇膜が形成され、得られる物品の外観が損なわれるという問題があった。特に、眼鏡レンズにおいては、それぞれの人の眼に適した眼鏡レンズを製造する必要があり、形状も様々であり、形状によっては泡が多量に基材上に付着する場合があった。このような問題に対し、泡の発生が抑制された防曇液が求められていた。
上述のような問題に対して、本開示の一実施形態は、防曇性及び外観に優れる眼鏡レンズを製造し得る眼鏡レンズ防曇膜用組成物、並びに防曇性及び外観に優れる眼鏡レンズを提供することを課題とする。
[1]15℃における粘度が、20mPa・s以上80mPa・s以下であり、固形分量が10質量%以上25質量%以下である、眼鏡レンズ防曇膜用組成物。
[2]前記粘度が24mPa・s以上である、上記[1]に記載の眼鏡レンズ防曇膜用組成物。
[3]前記固形分量が、17質量%以上である、上記[1]又は[2]に記載の眼鏡レンズ防曇膜用組成物。
[4]成分(A)~(C)を含む、上記[1]~[3]のいずれかに記載の眼鏡レンズ防曇膜用組成物。
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、m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。]
[5]上記[1]~[4]のいずれかに記載の眼鏡レンズ防曇膜用組成物を硬化してなる防曇膜を有する、眼鏡レンズ。
[6]前記防曇膜が、最外層である、上記[5]に記載の眼鏡レンズ。
[7]前記眼鏡レンズが、基材を有し、前記基材上に直接防曇膜を有する、上記[5]又は[6]に記載の眼鏡レンズ。
[8]前記防曇膜が単層である、上記[5]~[7]のいずれかに記載の眼鏡レンズ。
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。
防曇膜用組成物における「固形分量」とは、溶媒以外の成分の量を意味する。
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防曇膜用組成物は、15℃における粘度が、20mPa・s以上80mPa・s以下であり、固形分量が10質量%以上25質量%以下である。
このように防曇膜用組成物の粘度と固形分量を上記範囲とすることにより、防曇膜用組成物に既に含まれていた泡や、塗布時に巻き込まれた泡はすぐに浮上することが可能となり、防曇膜用組成物が眼鏡レンズ用基材上に泡を含む状態で塗膜及び硬化されることが抑制されると考えられる。その結果、泡の形状が残った状態で防曇膜が形成されることを抑制できる。さらに、防曇膜用組成物の粘度と固形分量を上記範囲とすることにより、レンズ周辺部に防曇膜用組成物起因の液だまりが発生して、その部分の防曇膜の膜厚が厚くなり、外観不良となることを抑制できる。
また、防曇膜用組成物が、前記粘度と前記固形分量を有することで、優れた防曇性を有する防曇膜となり得る膜厚を確保することができる。
防曇膜用組成物の粘度は、15℃において、より防曇性に優れる眼鏡レンズを得る観点から、好ましくは22mPa・s以上、より好ましくは23mPa・s以上、更に好ましくは24mPa・s以上であり、外観に優れる眼鏡レンズを得る観点から、好ましくは65mPa・s以下、より好ましくは50mPa・s以下、更に好ましくは45mPa・s以下である。
防曇膜用組成物の固形分は、より防曇性に優れる眼鏡レンズを得る観点から、好ましくは13質量%以上、より好ましくは15質量%以上、更に好ましくは16質量%以上、より更に好ましくは17質量%以上であり、外観に優れる眼鏡レンズを得る観点から、好ましくは24.8質量%以下である。
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、m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。]
防曇膜用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膜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、防曇膜の架橋密度が高くなり、防曇膜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>
本実施形態の防曇膜用組成物は、成分(A)である(メタ)アクリル系樹脂、すなわち、一般式(1)で表されるモノマー(a-1)に由来する構成単位、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、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、防曇膜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膜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、防曇膜の柔軟性・弾力性を維持しつつ、防曇膜を硬くすることが可能となる。よって、防曇膜の耐擦傷性、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。
本実施形態の防曇膜用組成物は、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膜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。
本実施形態の防曇膜用組成物は、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。防曇膜用組成物が、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膜となる。
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。
本実施形態の防曇膜用組成物は、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、本実施形態の防曇膜用組成物は、2液型であってもよい。2液型にすることで、防曇膜用組成物の保存性を高めることができる。
例えば、本実施形態の防曇膜用組成物は、(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、防曇膜用組成物は2液型であることが好ましい。
本実施形態の防曇膜用組成物は、溶剤を含んでもよい。溶剤を用いることにより、防曇膜用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。
塗布組成物の固形分中における、成分(A)、(B)及び(C)の合計含有量は、防曇性及び耐擦傷性を向上させる観点から、好ましくは60質量%以上、より好ましくは80質量%以上、更に好ましくは90質量%以上、より更に好ましくは95質量%以上であり、好ましくは100質量%以下であり、例えば100質量%である。
防曇膜用組成物は、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、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。
本開示の実施形態に係る眼鏡レンズは、基材と、該基材上に設けられた防曇膜とを有する。
レンズ基材は、例えば、眼鏡レンズ基材である。
レンズ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、アクリルアリル樹脂、(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レンズ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「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「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「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。
レンズ基材としては、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。
レンズ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。
本実施形態の防曇膜用組成物を硬化することにより眼鏡レンズに適した防曇膜を形成することができる。本実施形態の防曇膜用組成物を用いると、防曇膜に泡が含有されることが抑制され、防曇性及び外観に優れる眼鏡レンズを製造することができる。
前記防曇膜は、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ことが好ましい。また、前記防曇膜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。
前記防曇膜は、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とが好ましい。
ここで、防曇膜が「吸水性を有する」とは、防曇膜を構成する材料が水分を取り込む特性を示すことを意味し、また、防曇膜が形成された透明基材を室温下で保管した後、当該防曇膜付き透明基材を40℃の温水の水面から35mm離れた位置に設置して温水からの蒸気を15秒間当てたときに、細かい水滴による防曇膜表面の乱反射が無く、かつ、蒸気を接触させた後の防曇膜付き透明基材を通して見た像に結露による歪みが無いことを意味する。
また、前記防曇膜は、前記成分(A)~(C)を含む防曇膜用組成物を硬化して得られるものであることが好ましい。前記成分(A)~(C)を含む防曇膜用組成物を硬化して得られるものであると、防曇膜が眼鏡レンズの最外層に位置していても、高い耐久性を発揮することができる。
眼鏡レンズには、防曇膜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膜を設けてもよく、レンズ基材上に防曇膜を設けた後に、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の一態様においては、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調製した防曇膜用組成物(2液型の場合は、2液を混合したもの)をレンズ基材上に塗工し、塗布膜を所定温度で乾燥・硬化することによって防曇膜を形成し、眼鏡レンズを得る。
塗工方法は特に限定されず、例えばエアスプレー法、エアレススプレー法、静電塗装法、ロールコーター法、フローコーター法、スピンコート法、ディッピング法等が挙げられる。生産性の観点から、ディッピング法が好ましい。
塗工後、20~160℃で10~120分間、好ましくは60~120℃で20~90分間乾燥・硬化し、さらに常温で放冷することで、防曇膜が得られる。なお、乾燥・硬化の温度や時間は、溶剤の種類やレンズ基材の耐熱性等を考慮して適宜調整すればよい。
なお、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、機能層上に防曇膜を設けてもよく、レンズ基材上に防曇膜を設けた後、防曇膜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。
以下、本開示を実施例により具体的に説明する。
以下の実施例1及び2、並びに比較例1~3で得られた防曇膜用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「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
振動式粘度計「VM-10A」(株式会社セコニック製)を用い、測定温度15℃にて測定した。なお、測定方法は、JIS Z 8803:2011の11(振動粘度計による粘度測定方法)に準拠した。
得られた眼鏡レンズの防曇膜厚は、非接触膜厚測定システム「FF8」(株式会社システムロード製)を用いて測定した。
室温25℃、湿度40%の条件下で、得られた眼鏡レンズの防曇膜表面に、10秒間呼気を吹きかけた。呼気を吹きかけ始めから、吹きかけ終わるまでの防曇膜の状態について目視観察を行い、以下の評価基準に従って評価を行なった。
A:曇りが全く認められない(防曇性に優れる)
B:曇りが1秒以内で消える
C:曇りが認められ、曇りが解消されるのに10秒以上かかる(防曇性に劣る)
得られた眼鏡レンズの外観評価を、以下の評価基準に従って行った。
A:防曇膜に泡が含まれておらず、眼鏡レンズ周辺部に防曇膜用組成物起因の液だまりも確認できない
B:防曇膜に泡は含まれていないが、眼鏡レンズ周辺部に防曇膜用組成物起因の液だまりがわずかに確認できる
C:防曇膜に泡は含まれていないが、眼鏡レンズ周辺部に防曇膜用組成物起因の液だまりが確認できる
D:防曇膜に泡が含まれている
((メタ)アクリル系樹脂の合成)
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)アクリル系樹脂を含む樹脂溶液(固形分比率:約40質量%)を得た。
得られた(メタ)アクリル系樹脂の水酸基価は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)アクリル系樹脂のガラス転移温度(Tg)は32.8℃であった。
上記で得た(メタ)アクリル系樹脂、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)、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%)、プロピレングリコールモノメチルエーテルアセテート、ジアセトンアルコール、メチルエチルケトン、t-ブタノール、及び酢酸エチルを混合し、混合物を得た。なお、得られた混合物中のそれぞれの含有量は下記のとおりである。
(メタ)アクリル系樹脂:14.7質量%
ポリカプロラクトンジオール:4.4質量%
多官能イソシアネート化合物:3.4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:28.5質量%
ジアセトンアルコール:18.5質量%
メチルエチルケトン:13.5質量%
t-ブタノール:8.5質量%
酢酸エチル:8.5質量%
そして、粘度が47.1mPa・s、固形分が22.5質量%となるように、酢酸エチル、メチルエチルケトン、及びジアセトンアルコールを混合物に添加、混合して調整し、防曇膜用組成物を得た。
なお、(メタ)アクリル系樹脂の量は、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100質量部とポリオール化合物(ポリカプロラクトンジオール)30質量部とを、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。
チオウレタン系プラスチックレンズMERIA(度数S0.00)を基材として用い、得られた防曇膜用組成物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、塗膜を形成した後、温度120℃、120分にて加熱することにより、上記基材上に単層の防曇膜を有する眼鏡レンズを製造した。得られた眼鏡レンズの防曇膜厚、防曇性評価、及び外観評価の結果を表1に示す。
実施例1において、酢酸エチル、メチルエチルケトン、及びジアセトンアルコールを用いて固形分量及び粘度が表1に記載の値となるように調製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。
本開示の実施の形態である眼鏡レンズ防曇膜用組成物は、15℃における粘度が20mPa・s以上80mPa・s以下であり、固形分量が10質量%以上25質量%以下である。
上述した実施の態様によれば、防曇性及び外観に優れる眼鏡レンズを製造し得る眼鏡レンズ防曇膜用組成物、並びに防曇性及び外観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 (8)
- 15℃における粘度が、20mPa・s以上80mPa・s以下であり、固形分量が10質量%以上25質量%以下である、眼鏡レンズ防曇膜用組成物。
- 前記粘度が24mPa・s以上である、請求項1に記載の眼鏡レンズ防曇膜用組成物。
- 前記固形分量が、17質量%以上である、請求項1又は2に記載の眼鏡レンズ防曇膜用組成物。
- 成分(A)~(C)を含む、請求項1~3のいずれか1項に記載の眼鏡レンズ防曇膜用組成物。
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、m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。] - 請求項1~4のいずれか1項に記載の眼鏡レンズ防曇膜用組成物を硬化してなる防曇膜を有する、眼鏡レンズ。
- 前記防曇膜が、最外層である、請求項5に記載の眼鏡レンズ。
- 前記眼鏡レンズが、基材を有し、
前記基材上に直接防曇膜を有する、請求項5又は6に記載の眼鏡レンズ。 - 前記防曇膜が単層である、請求項5~7のいずれか1項に記載の眼鏡レンズ。
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EP22781231.0A EP4318095A1 (en) | 2021-03-31 | 2022-03-31 | Spectacle lens anti-fogging composition and spectacle lens |
CN202280024465.3A CN117120915A (zh) | 2021-03-31 | 2022-03-31 | 眼镜镜片防雾膜用组合物和眼镜镜片 |
JP2023511703A JPWO2022211021A1 (ja) | 2021-03-31 | 2022-03-31 | |
US18/284,137 US20240184019A1 (en) | 2021-03-31 | 2022-03-31 | Spectacle lens anti-fogging composition and spectacle lens |
KR1020237033024A KR20230152718A (ko) | 2021-03-31 | 2022-03-31 | 안경 렌즈 방담막용 조성물 및 안경 렌즈 |
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Citations (6)
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JP2000075104A (ja) | 1998-09-02 | 2000-03-14 | Canon Inc | 防曇光学物品およびその製造方法 |
JP2007083447A (ja) * | 2005-09-20 | 2007-04-05 | Fujifilm Corp | 凹凸状シートの製造方法及び装置 |
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 |
JP2015030803A (ja) * | 2013-08-02 | 2015-02-16 | セントラル硝子株式会社 | 防曇膜形成材料、防曇膜形成用塗布液、防曇性物品、及びそれらの製法 |
JP2016110033A (ja) * | 2014-12-10 | 2016-06-20 | 凸版印刷株式会社 | 光学フィルム |
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 |
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KR20130005710A (ko) | 2011-07-07 | 2013-01-16 | 김정탁 | 실리콘튜브용 노즐 |
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- 2022-03-31 CN CN202280024465.3A patent/CN117120915A/zh active Pending
- 2022-03-31 JP JP2023511703A patent/JPWO2022211021A1/ja active Pending
- 2022-03-31 KR KR1020237033024A patent/KR20230152718A/ko unknown
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
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JP2000075104A (ja) | 1998-09-02 | 2000-03-14 | Canon Inc | 防曇光学物品およびその製造方法 |
JP2007083447A (ja) * | 2005-09-20 | 2007-04-05 | Fujifilm Corp | 凹凸状シートの製造方法及び装置 |
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 |
JP2015030803A (ja) * | 2013-08-02 | 2015-02-16 | セントラル硝子株式会社 | 防曇膜形成材料、防曇膜形成用塗布液、防曇性物品、及びそれらの製法 |
JP2016110033A (ja) * | 2014-12-10 | 2016-06-20 | 凸版印刷株式会社 | 光学フィルム |
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 |
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KR20230152718A (ko) | 2023-11-03 |
EP4318095A1 (en) | 2024-02-07 |
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