阅读说明：本技术 眼镜片、组合物 (Ophthalmic lens and composition ) 是由 伊神优香 于 2020-04-30 设计创作，主要内容包括：本发明提供表面电阻率低的眼镜片。本公开的眼镜片包含眼镜片基材和硬涂层,在眼镜片基材与硬涂层之间包含底涂层的情况下,底涂层和硬涂层中的至少一者包含选自由离子液体包覆纳米线和离子液体包覆纳米粒子组成的组中的至少一种导电性填料,所述离子液体包覆纳米线包含金属纳米线和包覆金属纳米线的离子液体,所述离子液体包覆纳米粒子包含金属纳米粒子和包覆金属纳米粒子的离子液体,在眼镜片基材与硬涂层之间不含底涂层的情况下,硬涂层包含选自由离子液体包覆纳米线和离子液体包覆纳米粒子组成的组中的至少一种导电性填料。(The invention provides ophthalmic lenses having low surface resistivity. The ophthalmic lenses of the present disclosure comprise an ophthalmic lens substrate and a hard coat layer, at least one of the primer layer and the hard coat layer comprising at least one conductive filler selected from the group consisting of ionic liquid coated nanowires comprising metal nanowires and ionic liquids coating the metal nanowires comprising ionic liquids of the metal nanowires and coated metal nanowires comprising metal nanoparticles and ionic liquids of the coated metal nanoparticles, with the primer layer being included between the ophthalmic lens substrate and the hard coat layer, the hard coat layer comprising at least one conductive filler selected from the group consisting of ionic liquid coated nanowires and ionic liquid coated nanoparticles, with the primer layer being absent between the ophthalmic lens substrate and the hard coat layer.)

1. An eyeglass lens comprises an eyeglass lens base material and a hard coating layer,

in the case of including an undercoat layer between the ophthalmic lens substrate and the hard coat layer, at least one of the undercoat layer and the hard coat layer includes at least one conductive filler selected from the group consisting of ionic liquid-coated nanowires including a metal nanowire and an ionic liquid coating the metal nanowire, and ionic liquid-coated nanoparticles including a metal nanoparticle and an ionic liquid coating the metal nanoparticle,

in the absence of a primer layer between the ophthalmic lens substrate and the hard coat layer, the hard coat layer comprises at least one electrically conductive filler selected from the group consisting of the ionic liquid-coated nanowires and the ionic liquid-coated nanoparticles.

2. An ophthalmic lens as defined by claim 1, wherein the ionic liquid comprises a compound selected from the group consisting of ammonium salts, imidazoles, and mixtures thereofSalt, pyridineSalt, pyrrolidineSalt,At least one of the group consisting of onium salts and sulfonium salts.

3. The eyeglass lens as set forth in claim 1 or 2, wherein the metal contained in the metal nano-particle and the metal nano-wire comprises at least one selected from the group consisting of silver, gold, copper, nickel, and platinum.

4. An ophthalmic lens as defined in any one of claims 1 to 3, wherein the hard coating layer comprises the electrically conductive filler,

the hard coat layer is formed using a hard coat layer-forming composition containing a polymerizable monomer and the conductive filler.

5. The eyeglass of claim 4, wherein the polymerizable monomer comprises a (meth) acrylate having at least one group selected from the group consisting of a phosphoric acid group and a sulfonic acid group.

6. The ophthalmic lens of claim 4 or 5, wherein the polymerizable monomer comprises a silsesquioxane having a radical polymerizable group.

7. An eyeglass lens as set forth in any one of claims 1 to 6, comprising an antireflection film disposed on the hard coat layer.

8. A composition comprising at least one conductive filler selected from the group consisting of ionic liquid coated nanoparticles comprising a metal nanoparticle and an ionic liquid coating the metal nanoparticle, and ionic liquid coated nanowires comprising a metal nanowire and an ionic liquid coating the metal nanowire.

9. The composition of claim 8, further comprising a polymerizable monomer.

10. The composition according to claim 9, wherein the polymerizable monomer comprises a (meth) acrylate having at least one group selected from the group consisting of a phosphoric acid group and a sulfonic acid group.

11. The composition of claim 9 or 10, wherein the polymerizable monomer comprises a silsesquioxane having a radical polymerizable group.

Technical Field

The present disclosure relates to ophthalmic lenses and compositions.

Background

A curable resin composition containing a silsesquioxane compound having a radical polymerizable group is useful as a hard coating agent (for example, patent document 1).

Documents of the prior art

Patent document

Patent document 1 Japanese laid-open patent publication No. 2015-224294

Disclosure of Invention

The present disclosure relates to an ophthalmic lens comprising an ophthalmic lens substrate and a hard coat layer, wherein, in the case of comprising a primer layer between the ophthalmic lens substrate and the hard coat layer, at least one of the primer layer and the hard coat layer comprises at least one conductive filler selected from the group consisting of ionic liquid coated nanowires comprising metal nanowires and ionic liquid coated metal nanowires comprising metal nanoparticles and ionic liquid coated metal nanoparticles, and in the case of not comprising a primer layer between the ophthalmic lens substrate and the hard coat layer, the hard coat layer comprises at least one conductive filler selected from the group consisting of ionic liquid coated nanowires and ionic liquid coated nanoparticles.

Drawings

FIG. 1 is a cross-sectional view of a first embodiment of an ophthalmic lens.

FIG. 2 is a cross-sectional view of a second embodiment of an ophthalmic lens.

Detailed Description

The spectacle lens of the present embodiment will be described in detail below.

As the spectacle lens, a spectacle lens having low surface resistivity is desired. The spectacle lens of the present embodiment can obtain the above characteristics. As described later, when the hard coat layer in the spectacle lens contains a conductive filler described later, the hard coat layer is excellent in abrasion resistance even when the antireflection film is disposed thereon. In addition, adjacent layers in the spectacle lens are excellent in adhesion to each other.

In the present specification, "to" is used to include values before and after the "to" as the lower limit value and the upper limit value.

< first embodiment >

FIG. 1 is a cross-sectional view of a first embodiment of an ophthalmic lens.

The spectacle lens 10A shown in fig. 1 includes a spectacle lens base material 12, and a hard coat layer 14A disposed on both sides of the spectacle lens base material 12.

In fig. 1, the hard coat layer 14A is disposed so as to be in direct contact with the spectacle lens base material 12, but is not limited to this embodiment, and another layer (for example, an undercoat layer) may be disposed between the spectacle lens base material 12 and the hard coat layer 14A as described later. That is, the hard coat layer 14A may be disposed directly on the spectacle lens base material 12 or may be disposed indirectly on the spectacle lens base material 12 via another layer.

In fig. 1, the hard coat layer 14A is disposed on both surfaces of the spectacle lens base material 12, but the hard coat layer 14A may be disposed on only one surface of the spectacle lens base material 12.

In the present embodiment, the hard coat layer 14A contains a predetermined conductive filler described later.

Each member included in the spectacle lens 10A will be described in detail below.

(spectacle lens base material)

The eyeglass piece base material is a member for supporting a hard coat layer described later.

The type of the spectacle lens base material is not particularly limited, and a general spectacle lens base material made of plastic, inorganic glass, or the like can be cited, and a plastic spectacle lens base material is preferable from the viewpoint of excellent handling property.

The type of the plastic eyeglass sheet base is not particularly limited, and examples thereof include: a finished lens in which both the convex surface and the concave surface are optically finished and molded according to a desired power, a semi-finished lens in which only the convex surface is finished as an optical surface (spherical surface, aspherical surface to be rotated, progressive surface, etc.), and a lens in which the concave surface of the semi-finished lens is finished and polished according to the prescription of the wearer.

The type of plastic (so-called resin) constituting the plastic spectacle lens base material is not particularly limited, and examples thereof include (meth) acrylic resins, thiourethane resins, allyl resins, episulfide resins, polycarbonate resins, polyurethane resins, polyester resins, polystyrene resins, polyether sulfone resins, poly-4-methylpentene-1 resins, and diethylene glycol bisallylcarbonate resins (CR-39).

The thickness of the plastic eyeglass sheet base is not particularly limited, and is usually about 1 to 30mm from the viewpoint of handling property.

The refractive index of the plastic eyeglass sheet base is not particularly limited.

The plastic spectacle lens base material may be opaque as long as it has light transmittance, and may contain an ultraviolet absorber or a dye that absorbs a specific wavelength region from the ultraviolet region to the infrared region.

(hard coating)

The hard coat layer is a layer disposed on the spectacle lens base material and provides scratch resistance to the spectacle lens base material.

The hard coat layer is preferably a hard coat layer having a hardness of "H" or more in a pencil hardness meter according to a test method defined in JIS K5600.

The hard coat layer in the first embodiment contains at least one conductive filler (hereinafter also simply referred to as "specific filler") selected from the group consisting of an ionic-liquid-coated nanowire containing a metal nanowire and an ionic liquid coating the metal nanowire and an ionic-liquid-coated nanoparticle containing a metal nanoparticle and an ionic liquid coating the metal nanoparticle.

The type of the metal contained in the metal nanowire in the ionic liquid-coated nanowire is not particularly limited, and at least one selected from the group consisting of silver, gold, copper, nickel, and platinum is preferable from the viewpoint of further reducing the surface resistivity of the spectacle lens (hereinafter, also simply referred to as "the angle which provides a predetermined effect more excellent"), silver or gold is more preferable, and silver is further preferable.

The metal nanowires refer to: the material is metal, the shape is needle-like or linear, and the diameter is nanometer conductive substance. The metal nanowire may be linear or curved.

The diameter of the metal nanowire is not particularly limited, but is preferably 500nm or less, more preferably 200nm or less, further preferably 100nm or less, and particularly preferably 50nm or less, from the viewpoint of further improving the predetermined effect. The lower limit is usually 10nm or more.

The diameter of the metal nanowire is an average value, and is obtained by observing the cross section of the metal nanowire using a scanning electron microscope or a transmission electron microscope, measuring the diameter of the metal nanowire at 20 points, and arithmetically averaging the diameters. When the cross section is not a perfect circle, the major axis is defined as the diameter.

The length of the metal nanowire is not particularly limited, but is preferably 5 to 1000 μm, and more preferably 10 to 500 μm, from the viewpoint of further improving the predetermined effect.

The lengths of the metal nanowires are averaged, and the lengths of 20 metal nanowires are obtained by using a scanning electron microscope or a transmission electron microscope and arithmetically averaging the lengths.

The ratio of the diameter d to the length L (aspect ratio: L/d) of the metal nanowire is not particularly limited, but is preferably 10 to 100000, and more preferably 50 to 100000.

The diameter and length of the metal nanowires are determined as described above.

The type of the ionic liquid contained in the ionic liquid-coated nanowire is not particularly limited, and is preferably selected from the group consisting of ammonium salts and imidazoles in order to obtain a more excellent predetermined effectSalt, pyridineSalt, pyrrolidineSalt,At least one member selected from the group consisting of onium salts and sulfonium salts, more preferably ammonium salt and imidazoleAnd (3) salt.

The ionic liquid is a salt composed of a cation (e.g., an organic anion) and an anion (e.g., an organic anion or an inorganic anion) and having a melting point of 100 ℃ or lower. The ionic liquid is preferably a liquid that does not solidify at normal temperature (25 ℃) or normal pressure when used alone.

The cation contained in the ammonium salt (preferably quaternary ammonium salt) is an ammonium cation (quaternary ammonium cation).

ImidazoleThe cation contained in the salt is imidazoleA cation.

Pyridine compoundThe cation contained in the salt is pyridineA cation.

Pyrrolidine as a therapeutic agentThe cation contained in the salt is pyrrolidineA cation.

The cation contained in the salt isA cation.

The cation contained in the sulfonium salt is a sulfonium cation.

The anion contained in the ionic liquid is not particularly limited, and examples thereof include a halide ion, a cyanide ion, a dicyanamide anion, a trifluoromethanesulfonate ion, a nonafluorobutanesulfonate ion, a tetrafluoroethanesulfonate ion, a lactate anion, a salicylate ion, a thiosalicylate ion, a dibutylphosphate ion, an acetate ion, a hexafluoroantimonate ion, a hydrogen sulfate ion, a sulfate ion, an octylsulfonate ion, a tetrachloroaluminate ion, a thiocyanate ion, a tris (trifluoromethanesulfonyl) methide ion, an aminoacetate ion, an aminopropionate ion, a diethylphosphate ion, a dimethylphosphate ion, an ethylsulfate ion, a methylsulfate ion, a hydroxide ion, a bis (trimethylpentyl) phosphinate ion, a decanoate ion, a trifluoroacetate ion, a ferrite ion, a tetrafluoroborate ion, a decanoate ion, a trifluoroacetate ion, a ferrate ion, a tetrafluoroborate ion, a sulfate ion, a methyl sulfate ion, a hydroxide ion, a bis (trimethylpentyl) phosphinate ion, a decanoate ion, a trifluoroacetate, a ferrate ion, a tetrafluoroborate, and a tetrafluoroborate, Hexafluorophosphate ion, sulfonamide, butanesulfonate ion, methanesulfonate ion, ethanesulfonate ion, bis (trifluoromethanesulfonyl) imide anion, bis (trifluoroethylsulfonyl) imide anion, and bis (pentafluoroethanesulfonyl) imide anion.

The ionic liquid may have an intramolecular polar group (e.g., a hydroxyl group, a mercapto group, an amino group, a carboxyl group, a sulfoxy group, or the like). By providing the ionic liquid with a polar group, the ionic liquid becomes easily coordinated with the metal nanowire. Further, by providing the ionic liquid with a polar group (particularly, a hydroxyl group), the ionic liquid-coated nanowire has improved compatibility with other components (for example, polymerizable monomers) contained in the composition described later.

As the ionic liquid, a compound represented by the formula (1), a compound represented by the formula (2) and a compound represented by the formula (3) are preferable.

In the formula (1), R¹～R⁴Each independently represents an alkyl group which may have a substituent, or a diol group containing an alkyl group which may have a substituent. R¹～R⁴2 of which may be bonded to each other to form a ring. Examples of the ring to be formed include a piperidine ring and a pyrrolidine ring. Specific examples of the ring to be formed include pyrrolidinyl, 2-methylpyrrolidinyl, 3-methylpyrrolidinyl, 2-ethylpyrrolidinyl, 3-ethylpyrrolidinyl, 2-dimethylpyrrolidinyl, 2, 3-dimethylpyrrolidinyl, piperidinyl, 2-methylpiperidinyl, 3-methylpiperidinyl, 4-methylpiperidinyl, 2, 6-dimethylpiperidinyl and 2,2,6, 6-tetramethylpiperidinyl.

The number of carbon atoms of the alkyl group is not particularly limited, but is preferably 1 to 20, more preferably 1 to 6. The alkyl group may be linear, branched or cyclic. Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a neopentyl group, a hexyl group, an isohexyl group, a decyl group, a dodecyl group, an octadecyl group, a cyclopentyl group, and a cyclohexyl group.

Can be aligned with R¹～R⁴The kind of the substituent substituted with the alkyl group is not particularly limited, and examples thereof include an aryl group, a nitro group, a cyano group, an alkoxy group, and the above-mentioned polar group.

X in the formula (1)^–Represents an anion. Examples of the anion include the groups exemplified for the anions contained in the above-mentioned ionic liquids.

In the formula (2), R⁵～R⁶Each independently represents an alkyl group which may have a substituent.

As R⁵～R⁶Definitions and preferred modes of the alkyl radicals indicated, with R mentioned above¹～R⁴The alkyl groups shown are defined and preferred in the same manner.

As can be to R⁵～R⁶Examples of the substituent substituted with the alkyl group include R¹～R⁴Alkyl group shown is takenA substituent of a substituent group.

R⁷～R⁹Each independently represents a hydrogen atom or an alkyl group which may have a substituent.

As R⁷～R⁹Definitions and preferred modes of the alkyl radicals indicated, with R mentioned above¹～R⁴The alkyl groups shown are defined and preferred in the same manner.

As can be to R⁷～R⁹Examples of the substituent substituted with the alkyl group include R¹～R⁴Alkyl groups shown are substituted substituents.

X in the formula (2)^-The anion is exemplified by the groups exemplified for the anions contained in the above-mentioned ionic liquid.

In the formula (3), R¹⁰Represents an alkyl group which may have a substituent.

As R¹⁰Definitions and preferred modes of the alkyl radicals indicated, with R mentioned above¹～R⁴The alkyl groups shown are defined and preferred in the same manner.

As can be to R¹⁰Examples of the substituent substituted with the alkyl group include R¹～R⁴Alkyl groups shown are substituted substituents.

R¹¹～R¹⁵Each independently represents a hydrogen atom or an alkyl group which may have a substituent.

As R¹¹～R¹⁵Definitions and preferred modes of the alkyl radicals indicated, with R mentioned above¹～R⁴The alkyl groups shown are defined and preferred in the same manner.

As can be to R¹¹～R¹⁵Examples of the substituent substituted with the alkyl group include R¹～R⁴Alkyl groups shown are substituted substituents.

X in the formula (3)^-The anion is exemplified by the groups exemplified for the anions contained in the above-mentioned ionic liquid.

The ionic liquid coats the metal nanowire. That is, the ionic liquid is disposed on the metal nanowire so as to coat the metal nanowire. The ionic liquid is likely to interact with (e.g., coordinate bond) the metal nanowire, and as described later, the ionic liquid-coated nanowire can be obtained by mixing the two under prescribed conditions.

As a method for confirming the presence of the ionic liquid-coated nanowire, for example, a method for confirming the absorption characteristics from the ionic liquid-coated nanowire by measuring an absorption spectrum of a solution containing the ionic liquid-coated nanowire can be cited. Further, there is a method of detecting an element derived from the ionic liquid around the metal nanowire by performing energy dispersive X-ray analysis (EDX) on the ionic liquid-coated nanowire to confirm the presence of the ionic liquid-coated nanowire.

The kind of the metal contained in the metal nanoparticles in the ionic liquid-coated nanoparticles is not particularly limited, and at least one selected from the group consisting of silver, gold, copper, nickel, and platinum is preferable, and silver or gold is more preferable, from the viewpoint of further improving the predetermined effect.

The metal nanoparticles mean: the material is metal and is a granular conductive substance.

The average particle diameter of the metal nanoparticles is not particularly limited, but is preferably 1 to 500nm, more preferably 5 to 100nm, from the viewpoint of further improving the predetermined effect.

The average particle diameter is determined by measuring the diameters of 20 or more metal particles with a transmission electron microscope and arithmetically averaging the measured diameters. When the metal nanoparticles are not in a perfect circle shape, the major axis is defined as the diameter.

Examples of the ionic liquid contained in the ionic liquid-coated nanoparticle include the compounds exemplified in the ionic liquid contained in the ionic liquid-coated nanowire described above.

As described above, the ionic liquid may have an intramolecular polar group (e.g., a hydroxyl group, a mercapto group, an amino group, a carboxyl group, a sulfoxy group, or the like). By providing the ionic liquid with a polar group, the ionic liquid becomes easily coordinated to the metal nanoparticles. Further, by providing the ionic liquid with a polar group (particularly, a hydroxyl group), the ionic liquid-coated nanoparticles have improved compatibility with other components (for example, polymerizable monomers) contained in the composition described later.

The ionic liquid is coated on the metal nanoparticles. That is, the ionic liquid is disposed on the metal nanoparticle as in the case of coating the metal nanowire. The ionic liquid is likely to interact with (for example, coordinate-bond) the metal nanoparticles, and the ionic liquid-coated nanoparticles can be obtained by mixing the ionic liquid and the metal nanoparticles under predetermined conditions, as described later.

As a method for confirming the presence of the ionic liquid-coated nanoparticles, for example, a method for confirming the absorption characteristics from the ionic liquid-coated nanoparticles by measuring an absorption spectrum of a solution containing the ionic liquid-coated nanoparticles can be cited. Further, there is a method of detecting an element derived from the ionic liquid around the metal nanoparticles by performing energy dispersive X-ray analysis (EDX) on the ionic liquid-coated nanoparticles to confirm the presence of the ionic liquid-coated nanoparticles.

The method for producing the specific filler (ionic liquid-coated nanowire and ionic liquid-coated nanoparticle) is not particularly limited, and a method in which a metal nanowire or metal nanoparticle is mixed with an ionic liquid and heated may be mentioned.

The heating conditions may be selected as appropriate depending on the type of ionic liquid to be used, and the specific filler can be uniformly dispersed in various solvents including alcohols by heating at a temperature of 70 ℃ or higher (preferably 1 hour or more).

When the above method is carried out, it may be carried out in the presence of a solvent, if necessary. Examples thereof include: mixing the metal nano wire or the metal nano particle with the ionic liquid and the solvent, and heating.

The mixing mass ratio of the metal nanowire or metal nanoparticle to the ionic liquid (mass of metal nanowire or metal nanoparticle/mass of ionic liquid) is not particularly limited, but is preferably 0.5 to 5, and more preferably 1.0 to 2.5.

Examples of the solvent include water and an organic solvent. The type of the organic solvent is not particularly limited, and examples thereof include alcohol solvents (e.g., ethanol), ketone solvents, ether solvents, ester solvents, hydrocarbon solvents, halogenated hydrocarbon solvents, amide solvents, sulfone solvents, and sulfoxide solvents.

In addition, when the above method is carried out, it may be carried out in the presence of an acid, if necessary.

As the acid used, nitric acid, hydrochloric acid and sulfuric acid are cited.

In forming the hard coat layer containing the specific filler, a residue (a solid containing the specific filler, or a mixed solution of the specific filler and the ionic liquid) obtained by removing a solvent by heat treatment of a mixture (which may contain an acid if necessary) containing the metal nanowire or the metal nanoparticle and the ionic liquid and the solvent may be used. That is, the hard coat layer may contain the above-described residue.

The hard coating may also contain an ionic liquid that is not coated with metal nanowires or metal nanoparticles.

In addition, the hard coat layer may contain metal nanowires or metal nanoparticles that are not coated with an ionic liquid.

The total content of the metal nanowires and the metal nanoparticles in the hard coat layer is not particularly limited, but is preferably 1.0 to 50 mass%, more preferably 2.0 to 30 mass%, and further preferably 3.0 to 10 mass% with respect to the total mass of the hard coat layer, from the viewpoint of further improving the predetermined effect.

The "total content of the metal nanowires and the metal nanoparticles in the hard coat layer" means: the sum of the combined content of metal nanowires and metal nanoparticles from the specific filler and the combined content of metal nanowires and metal nanoparticles that are not coated with the ionic liquid.

The content of the ionic liquid in the hard coat layer is not particularly limited, and is preferably 0.5 to 20% by mass, more preferably 1.0 to 10% by mass, based on the total mass of the hard coat layer, from the viewpoint of further improving the predetermined effect.

The "content of the ionic liquid in the hard coat layer" means: the sum of the amount of ionic liquid from a particular filler and the amount of ionic liquid not contained in a particular filler.

The hard coat layer in the first embodiment may contain other components than the specific filler described above.

Examples of the other component include a polymer of a polymerizable monomer (a polymer obtained by polymerizing a polymerizable monomer) such as a hard coat layer.

The polymerizable monomer is not particularly limited, and examples thereof include specific (meth) acrylates, silsesquioxanes having a radical polymerizable group, and multifunctional acrylates, which will be described later. Among them, the hard coat layer particularly preferably contains a polymer obtained by polymerizing polymerizable monomers containing 3 kinds of substances, namely, a specific (meth) acrylate, a silsesquioxane having a radical polymerizable group, and a multifunctional acrylate.

The hard coat layer may contain metal oxide particles described later.

The method for forming the hard coat layer is not particularly limited, and a method of forming the hard coat layer using a composition for forming a hard coat layer containing a specific filler is exemplified. Among these, a method using a composition for forming a hard coat layer containing a polymerizable monomer and a specific filler is preferable.

The form of the composition for forming a hard coat layer will be described in detail later.

As a method for forming the hard coat layer, there is a method in which a composition for forming a hard coat layer is applied to a base material for an eyeglass lens to form a coating film, and the coating film is subjected to a curing treatment such as a light irradiation treatment.

After the coating film is formed, a drying treatment such as a heating treatment may be performed as necessary to remove the solvent from the coating film.

When the undercoat layer is disposed on the eyeglass lens base material, a method of forming the hard coat layer includes a method of forming a coating film by applying a composition for forming a hard coat layer on the undercoat layer and subjecting the coating film to a curing treatment such as a light irradiation treatment.

The method for applying the composition for forming a hard coat layer on the base material for an ophthalmic lens is not particularly limited, and known methods (for example, dip coating, spin coating, spray coating, inkjet coating, and flow coating) can be mentioned. For example, in the case of using the dip coating method, a coating film having a predetermined thickness can be formed on a plastic eyeglass lens base material by dipping the eyeglass lens base material in the hard coat layer-forming composition, and then lifting and drying the eyeglass lens base material.

The film thickness of the coating film formed on the spectacle lens base material is not particularly limited, and the film thickness is appropriately selected so as to achieve a predetermined film thickness of the hard coat layer.

The conditions for the light irradiation treatment are not particularly limited, and suitable conditions are selected depending on the kind of the polymerization initiator used.

The type of light to be irradiated with light is not particularly limited, and examples thereof include ultraviolet rays and visible light. The light source may be, for example, a high-pressure mercury lamp.

The cumulative light amount upon irradiation with light is not particularly limited, but is preferably 100 to 5000mJ/cm from the viewpoint of productivity and curability of the coating film²More preferably 100 to 2000mJ/cm²。

The film thickness of the hard coat layer is not particularly limited, but is preferably 1 μm or more, more preferably 5 μm or more, and still more preferably 10 μm or more. The upper limit of the film thickness may be set to 30 μm or less, for example.

The film thickness is an average film thickness, and the film thickness at any 5 points of the hard coat layer is measured and the film thickness is obtained by arithmetic averaging the film thicknesses.

(other Components)

The first embodiment of the spectacle lens may contain other members than the above-described spectacle lens base material and hard coat layer.

Examples of the other members include an undercoat layer and an antireflection film.

The primer layer is a layer disposed between the eyeglass lens base material and the hard coat layer, and is a layer for improving the adhesion of the hard coat layer to the eyeglass lens base material and imparting impact resistance to the eyeglass lens base material.

The material constituting the undercoat layer is not particularly limited, and a known material, for example, a resin, can be used. The kind of the resin to be used is not particularly limited, and examples thereof include polyurethane resin, epoxy resin, phenol resin, polyimide resin, polyester resin, bismaleimide resin, and polyolefin resin, and polyurethane resin is preferable.

The undercoat layer may contain other components than the above-described resin.

Examples of the other component include fine oxide particles of at least one metal selected from the group consisting of Si, Al, Sn, Sb, Ta, Ce, La, Fe, Zn, W, Zr, In and Ti, or composite oxide particles thereof, a hydrolyzable silicon compound and/or a hydrolysis condensate thereof, the above-mentioned specific filler, and a surfactant.

In addition, the base coat may contain a specific filler. That is, both the primer layer and the hard coat layer may contain a specific filler.

The preferable ranges of the total content of the metal nanowires and the metal nanoparticles in the undercoat layer and the content of the ionic liquid in the undercoat layer include the ranges described in the second embodiment described later.

The method of forming the primer layer is not particularly limited, and a known method can be used, and examples thereof include a method of forming a primer layer by applying a primer layer forming composition containing a predetermined resin to an ophthalmic lens substrate and, if necessary, performing a curing treatment.

The method for applying the composition for forming a primer layer is not particularly limited, and examples thereof include the methods exemplified in the method for applying the composition for forming a hard coat layer on an ophthalmic lens substrate.

The thickness of the primer layer is not particularly limited, but is preferably 0.3 to 2 μm.

The ophthalmic lens may further comprise an anti-reflective film disposed on the hard coat layer.

The antireflection film is a layer having a function of preventing reflection of incident light. Specifically, the low-reflection coating composition can have a low-reflection characteristic (broadband low-reflection characteristic) over the entire visible light region of 400 to 780 nm.

The structure of the antireflection film is not particularly limited, and may be a single-layer structure or a multilayer structure.

As the antireflection film, an inorganic antireflection film is preferable. The inorganic anti-reflective coating is an anti-reflective coating made of an inorganic compound.

In the case of a multilayer structure, a structure in which low refractive index layers and high refractive index layers are alternately laminated is preferable. Examples of the material constituting the high refractive index layer include oxides of titanium, zirconium, aluminum, niobium, tantalum, or lanthanum. Examples of the material constituting the low refractive index layer include an oxide of silicon dioxide.

The method for producing the antireflection film is not particularly limited, and examples thereof include dry methods such as a vacuum deposition method, a sputtering method, an ion plating method, an ion beam assist method, and a CVD method.

< second embodiment >

FIG. 2 is a cross-sectional view of a second embodiment of an ophthalmic lens.

The spectacle lens 10B shown in fig. 2 includes a spectacle lens substrate 12, a primer layer 16 disposed on both sides of the spectacle lens substrate 12, and a hard coat layer 14B disposed on the primer layer 16.

In fig. 2, the primer layer 16 and the hard coat layer 14B are disposed on both surfaces of the spectacle lens base material 12, but the primer layer 16 and the hard coat layer 14B may be disposed on only one surface of the spectacle lens base material 12.

In the present embodiment, the primer layer 16 contains the above-described specific filler. The hard coat layer 14B does not contain a specific filler.

Each member included in the spectacle lens 10B will be described in detail below.

The spectacle lens base material included in the second embodiment of the spectacle lens is the same as that included in the above-described first embodiment of the spectacle lens, and therefore, the description thereof is omitted.

The hard coat layer included in the second embodiment of the spectacle lens is the same as the hard coat layer included in the first embodiment of the spectacle lens described above, except that the hard coat layer included in the second embodiment of the spectacle lens does not contain a specific filler, and therefore, the description thereof is omitted.

The primer layer included in the second embodiment of the spectacle lens is the same as the primer layer included in the second embodiment of the spectacle lens described above, except that the primer layer included in the second embodiment of the spectacle lens includes a specific filler, and therefore only the difference between the two is described in detail below.

The primer layer of the second embodiment of the ophthalmic lens contains the above-mentioned specific filler (ionic liquid-coated nanowire, ionic liquid-coated nanoparticle). The description of the specific filler is as described above.

The base coat may contain other ingredients in addition to the specific filler. As the other component, for example, the resin described in the first embodiment of the spectacle lens can be cited.

The undercoating layer may comprise an ionic liquid that is not coated with metal nanowires or metal nanoparticles.

In addition, the undercoat layer may contain metal nanowires or metal nanoparticles that are not coated with an ionic liquid.

The total content of the metal nanowires and the metal nanoparticles in the undercoat layer is not particularly limited, but is preferably 1.0 to 50 mass%, more preferably 2.0 to 30 mass%, and still more preferably 3.0 to 10 mass% with respect to the total mass of the undercoat layer, from the viewpoint of further improving the predetermined effect.

The "total content of the metal nanowires and the metal nanoparticles in the undercoat layer" means: the sum of the combined content of metal nanowires and metal nanoparticles from the specific filler and the combined content of metal nanowires and metal nanoparticles that are not coated with the ionic liquid.

The content of the ionic liquid in the undercoat layer is not particularly limited, but is preferably 0.5 to 20% by mass, more preferably 1.0 to 10% by mass, based on the total mass of the undercoat layer, from the viewpoint of further improving the predetermined effect.

The "content of the ionic liquid in the undercoat layer" means: the sum of the amount of ionic liquid from a particular filler and the amount of ionic liquid not contained in a particular filler.

The method for forming the undercoat layer is not particularly limited, and a method using a composition for forming an undercoat layer containing a specific filler and the above-mentioned resin is exemplified.

The first embodiment includes the following 3 modes.

Mode 1A: ophthalmic lens comprising a lens substrate and a hard coat layer disposed on the lens substrate, the hard coat layer comprising a specific filler

Mode 1B: spectacle lens comprising spectacle lens base material, primer layer disposed on spectacle lens base material, and hard coat layer disposed on primer layer, wherein hard coat layer contains specific filler

Mode 1C: ophthalmic lens comprising an ophthalmic lens substrate, a primer layer disposed on the ophthalmic lens substrate, and a hard coat layer disposed on the primer layer, both the primer layer and the hard coat layer comprising a specific filler

The second embodiment corresponds to an eyeglass lens comprising an eyeglass lens base, a primer layer disposed on the eyeglass lens base, and a hard coat layer disposed on the primer layer, wherein the primer layer comprises a specific filler.

< composition >

A layer containing a specific filler (e.g., a hard coat layer containing a specific filler, a base coat layer containing a specific filler) can be formed using a composition containing a specific filler.

For example, a hard coat layer containing a specific filler can be formed using a composition (hard coat layer-forming composition) containing a polymerizable monomer and a specific filler. Further, the undercoat layer containing a specific filler can be formed using a composition (undercoat layer-forming composition) containing a resin and a specific filler.

The composition for forming a hard coat layer will be described in more detail below.

(meth) acrylate having at least one group selected from the group consisting of phosphoric acid group and sulfonic acid group)

As the polymerizable monomer that can be contained in the composition for forming a hard coat layer, there can be mentioned (meth) acrylate having at least one group (hereinafter also simply referred to as "specific group") selected from the group consisting of a phosphoric acid group and a sulfonic acid group (hereinafter also simply referred to as "specific (meth) acrylate").

The term (meth) acrylate refers to acrylate or methacrylate.

As the specific group, a phosphate group is preferable.

The number of the specific groups in the specific (meth) acrylate may be 1 or more, or may be 2 or more. The upper limit may be set to, for example, 5 or less.

The specific (meth) acrylate may be monofunctional or polyfunctional. The term "polyfunctional" means that a specific (meth) acrylate has 2 or more specific groups.

The phosphate group is a group represented by the following formula. Denotes the bonding site.

The sulfonic acid group is a group represented by the following formula.

As the specific (meth) acrylate, a compound represented by the formula (A) is preferable.

Formula (A) CH₂＝CR^a-COO-L^a-X

R^aRepresents a hydrogen atom or a methyl group.

L^aRepresents a 2-valent hydrocarbon group that may contain a hetero atom (e.g., oxygen atom, nitrogen atom, sulfur atom). The number of carbon atoms of the 2-valent hydrocarbon group is not particularly limited, but is preferably 1 to 10 (preferably 1 to 5, more preferably 1 to 3). Examples of the 2-valent hydrocarbon group include an alkylene group, an alkenylene group, an alkynylene group, an arylene group, and a combination of these groups, and an alkylene group which may contain a hetero atom (e.g., -O-alkylene-, alkylene) is preferable.

X represents a group selected from the group consisting of a phosphoric acid group and a sulfonic acid group.

(silsesquioxane having radical polymerizable group)

Examples of the polymerizable monomer that can be contained in the composition for forming a hard coat layer include silsesquioxane having a radical polymerizable group.

The radical polymerizable group is preferably a group having an ethylenically unsaturated bond. Examples of the group having an ethylenically unsaturated bond include a (meth) acryloyl group, a styryl group, and a vinyl group.

The term (meth) acryloyl means acryloyl or methacryloyl.

In general, the silsesquioxane compound means: a silane compound having a basic skeleton represented by the formula (B) which is obtained by hydrolyzing a trifunctional silane compound such as alkoxysilane, chlorosilane, silanol or the like. As the structure of the silsesquioxane compound, in addition to an irregular form called a random structure, a ladder structure, a cage (fully condensed cage) structure, and an incomplete cage structure (a structure in which a part of silicon atoms is absent in the cage structure or a structure in which a part of silicon-oxygen bonds in the cage structure are broken) are known.

In the following formula (B), R^bRepresents an organic group.

Formula (B) R^b-SiO_3/2

The structure of the silsesquioxane compound having a radical polymerizable group is not particularly limited, and may be any of the random structure, the ladder structure, the cage structure, and the incomplete cage structure, or may be a mixture of a plurality of structures.

The equivalent weight of the radical polymerizable group contained in the silsesquioxane compound is not particularly limited, but is preferably 30 to 500g/eq, and more preferably 30 to 150g/eq, from the viewpoint of further improving the hardness of the hard coat layer.

The silsesquioxane compound having a radical polymerizable group can be synthesized by a known method, and a commercially available product can be used.

(polyfunctional acrylate)

Examples of the polymerizable monomer that can be contained in the composition for forming a hard coat layer include polyfunctional (meth) acrylates different from both the specific (meth) acrylates and the silsesquioxane having a radical polymerizable group.

The polyfunctional (meth) acrylate refers to a compound having two or more (meth) acryloyl groups. The number of (meth) acryloyl groups is not particularly limited, but is preferably 2 to 6, and more preferably 2 to 3.

As the polyfunctional (meth) acrylate, a compound represented by the formula (C) is preferable.

Formula (C) CH₂＝CR^c1-CO-L^c1-CO-CR^c2＝CH₂

R^c1And R^c2Each independently represents a hydrogen atom or a methyl group.

L^c1Represents a 2-valent hydrocarbon group that may contain a hetero atom (e.g., oxygen atom, nitrogen atom, sulfur atom). The number of carbon atoms of the 2-valent hydrocarbon group is not particularly limited, but is preferably 1 to 10. Examples of the 2-valent hydrocarbon group include an alkylene group, an alkenylene group, an alkynylene group, an arylene group, and a combination of these groups, and an alkylene group which may contain a hetero atom is preferable.

Among them, alkylene groups containing an oxygen atom are preferred, and-O- (L) is preferred^c2-O)_m-a group represented. In addition, L is^c2Represents an alkylene group (preferably having 1 to 3 carbon atoms). m represents an integer of 1 or more, preferably an integer of 1 to 10, more preferably an integer of 2 to 5.

(Metal oxide particles)

The composition for forming a hard coat layer may contain metal oxide particles.

The type of the metal oxide particles is not particularly limited, and known metal oxide particles can be used. Examples of the metal oxide particles include particles of an oxide of at least one metal selected from Si, Al, Sn, Sb, Ta, Ce, La, Fe, Zn, W, Zr, In, and Ti. Among them, from the viewpoint of handling properties, the metal oxide particles are preferably particles containing an oxide of Si (silicon oxide particles), particles containing an oxide of Sn (tin oxide particles), particles containing an oxide of Zr (zirconium oxide particles), or particles containing an oxide of Ti (titanium oxide particles).

The metal oxide particles may contain only one metal (metal atom) as exemplified above, or may contain two or more metals (metal atoms).

In addition, Si (silicon) is sometimes classified as a semimetal, but Si belongs to a metal in this specification.

The average particle diameter of the metal oxide particles is not particularly limited, and is, for example, preferably 1nm to 200nm, more preferably 5nm to 30 nm. When the amount is within the above range, the dispersion stability of the metal oxide particles in the composition for forming a hard coat layer is more excellent, and whitening of the cured product can be further suppressed.

The average particle diameter is determined by measuring the diameters of 20 or more metal oxide particles by a transmission electron microscope and arithmetically averaging the measured diameters. When the metal oxide particles are not perfectly circular, the major axis is defined as the diameter.

Various functional groups can be introduced to the surface of the metal oxide particle as necessary.

(other Components)

The composition for forming a hard coat layer may contain components other than the above components (the specific (meth) acrylate, the silsesquioxane compound having a radical polymerizable group, and the metal oxide particles).

The composition for forming a hard coat layer may contain a radical polymerization initiator. Examples of the radical polymerization initiator include a photo radical polymerization initiator and a thermal radical polymerization initiator.

Examples of the radical polymerization initiator include IRGACURE127, 184, 07, 651, 1700, 1800, 819, 369, 261, TPO, DAROCUR1173 manufactured by BASF, エザキュアー KIP150 and TZT manufactured by シイベルヘグナー, KAYACURE BMS manufactured by japan chemical corporation, and KAYACURE DMBI.

The hard coat layer-forming composition may contain a solvent.

The solvent may be water or an organic solvent.

The type of the organic solvent is not particularly limited, and examples thereof include alcohol solvents, ketone solvents, ether solvents, ester solvents, hydrocarbon solvents, halogenated hydrocarbon solvents, amide solvents, sulfone solvents, and sulfoxide solvents.

The composition for forming a hard coat layer may contain various additives such as an ultraviolet absorber, an anti-aging agent, a coating film regulator, a light stabilizer, an antioxidant, an anti-coloring agent, a dye, a filler, and an internal mold release agent, as required.

The method for producing the composition for forming a hard coat layer is not particularly limited, and for example, the above components may be mixed at once, or the components may be mixed in stages in batches.

The content of the specific filler in the composition for forming a hard coat layer is not particularly limited, but is preferably 1.0 to 30% by mass, more preferably 3.0 to 20% by mass, based on the total solid content (hard coat layer-constituting component) in the composition for forming a hard coat layer, from the viewpoint of further improving the predetermined effect.

The total solid content (hard coat layer-constituting component) is a component constituting the hard coat layer by curing treatment, and corresponds to the above-mentioned specific filler, specific (meth) acrylate, silsesquioxane compound having a radical polymerizable group, metal oxide particles, polyfunctional (meth) acrylate, radical polymerization initiator, and the like, and the solid content does not include a solvent. Even if the component is in a liquid state, the solid component is calculated as long as the component constitutes the hard coat layer.

When the specific (meth) acrylate is contained in the composition for forming a hard coat layer, the content of the specific (meth) acrylate in the composition for forming a hard coat layer is not particularly limited, but is preferably 1 to 30% by mass, more preferably 5 to 20% by mass, based on the total solid content (hard coat layer-constituting component) in the composition for forming a hard coat layer, from the viewpoint of further improving the predetermined effect.

When the silsesquioxane compound having a radical polymerizable group is contained in the composition for forming a hard coat layer, the content of the silsesquioxane compound having a radical polymerizable group in the composition for forming a hard coat layer is not particularly limited, but is preferably 5 to 85 mass%, and more preferably 10 to 50 mass%, based on the total solid content in the composition for forming a hard coat layer, from the viewpoint of further improving the predetermined effect.

The content of the metal oxide particles in the composition for forming a hard coat layer is not particularly limited, but is preferably 10 to 90% by mass, more preferably 25 to 80% by mass, based on the total solid content in the composition for forming a hard coat layer, from the viewpoint of further improving the predetermined effect.

When the composition for forming a hard coat layer contains the polyfunctional (meth) acrylate, the content of the polyfunctional (meth) acrylate is not particularly limited, but is preferably 1 to 20% by mass, more preferably 3 to 10% by mass, based on the total solid content in the composition for forming a hard coat layer, from the viewpoint of further improving the predetermined effect.

When the radical polymerization initiator is contained in the composition for forming a hard coat layer, the content of the radical polymerization initiator is not particularly limited, but is preferably 0.05 to 5% by mass, more preferably 0.1 to 3% by mass, based on the total solid content in the composition for forming a hard coat layer, from the viewpoint of further improving the predetermined effect.

Examples

The above-described embodiments are further illustrated in detail by examples and comparative examples, but are not limited to these examples.

< comparative example A1 >

(formation of undercoat layer)

Pure water (289 parts by mass), propylene glycol monomethyl ether (10.6 parts by mass), L77 (Momentive) (0.2 parts by mass) and L7604(Dow Chemical) (0.2 parts by mass) as surfactants were added to an aqueous urethane dispersion (エバファール HA170, manufactured by hitachi Chemical corporation, solid content concentration 37%) (200 parts by mass) and stirred to prepare a primer layer forming composition 1 having a solid content concentration of 14.8% by mass.

As the plastic spectacle lens base material, a lens (Nikon Lite 3AS blank S0.00D, Nikon Lite Co., Ltd.) having a refractive index of 1.60 was used.

The plastic eyeglass sheet base material was immersed at 90 mm/min in the composition 1 for forming an undercoat layer, and baked at 90 ℃ for 20 minutes, thereby forming an undercoat layer.

(hard coat layer formation)

Acid phosphoryloxyethyl methacrylate (manufactured by Phosmer M, ユニケミカル Co.) (6 parts by mass), methacrylic silsesquioxane (AC-SQTA-100, manufactured by Toyo Synthesis Co., Ltd.) (15 parts by mass) as silsesquioxane having a radical polymerizable group, and a zirconium dioxide dispersion (manufactured by Kanto electric chemical industries Co., Ltd.) (185 parts by mass) (40% by mass of zirconium dioxide nanoparticle/propylene glycol monomethyl ether dispersion, zirconium dioxide solid (74 parts by mass)), polyethylene glycol dimethacrylate (LIGHT ACRYLATE 4EG-A, product of Kyoeisha chemical Co.) (5 parts by mass), IRGACURE127 (photopolymerization initiator, product of BASF corporation) (3 parts by mass), and IL-OH2(1- (hydroxypropyl) pyridine), which is an ionic liquid containing an OH functional group.Bis (trifluoromethanesulfonyl) imide (2 parts by mass) was mixed together to obtain a composition C1 for forming a hard coat layer.

After dropping the hard coat layer-forming composition C1(1.5ml) onto the primer layer, the plastic spectacle lens substrate coated with the hard coat layer-forming composition C1 was rotated at 1000rpm for 10 seconds by a spin coater. Then, the obtained plastic spectacle lens base material was heated at 90 ℃ for 10 minutes and then, a high pressure mercury lamp (100 mW/cm) was used²) As a light source, UV irradiation (cumulative light amount: 1.6J/cm²) Thereby forming a hard coating layer.

The other surface of the plastic spectacle lens base material was also subjected to the same treatment as described above, thereby obtaining a spectacle lens having hard coat layers disposed on both surfaces of the plastic spectacle lens base material.

< comparative example A2 >

An ophthalmic lens was obtained in the same manner as in comparative example a1 except that silver nanowires (solvent-free) (ACS Materials, Agnw-L30) (5 parts by mass) of the silver nanowire solution were used instead of IL-OH2(2 parts by mass) which is an ionic liquid containing OH functional groups.

The above "silver nanowires (without solvent) using a silver nanowire solution" means: silver nanowires remaining after removing the entire solution from a commercially available silver nanowire solution were used.

The silver nanowires have a diameter of 30nm and a length of 100 to 200 μm.

< comparative example A3 >

An ophthalmic lens was obtained in the same manner as in comparative example a1 except that an ionic liquid containing an OH functional group, IL-OH2(2 parts by mass), and silver nanowires (solvent-free) (ACS Materials, Agnw-L30) (5 parts by mass) of a silver nanowire solution were used in place of the ionic liquid containing an OH functional group, IL-OH2(2 parts by mass).

In comparative example a3, the ionic liquid and the silver nanowires were used, but the silver nanowires were not coated with the ionic liquid.

< example A1 >

The undercoat layer was formed by the same procedure as in comparative example A1.

A silver nanowire isopropanol solution (concentration 20mg/ml, 10 parts by mass) (ACS Materials, Agnw-L30), a 1mol/L nitric acid aqueous solution (10 parts by mass), and an ionic liquid IL-OH2(0.08 part by mass) containing OH functional groups were mixed and stirred at 75 ℃ for 1 hour. Then, all of the isopropyl alcohol and water were evaporated from the obtained solution, and the ionic liquid-coated silver nanowire 1 was obtained as a residue.

Acid phosphoryloxyethyl methacrylate (manufactured by Phosmer M, ユニケミカル Co.) (6 parts by mass), methacrylic silsesquioxane (AC-SQTA-100, manufactured by Toyo Synthesis Co., Ltd.) (15 parts by mass), zirconium dioxide dispersion (manufactured by Kanto electric chemical industries Co., Ltd.) (185 parts by mass) (40% by mass zirconium dioxide nanoparticle/propylene glycol monomethyl ether dispersion, zirconium dioxide solid content (74 parts by mass)) as silsesquioxane having a radical polymerizable group were mixed, polyethylene glycol dimethacrylate (LIGHT ACRYLATE 4EG-A, manufactured by Kyoeisha chemical Co.) (5 parts by mass), IRGACURE127 (photopolymerization initiator, manufactured by BASF corporation) (3 parts by mass), and ionic liquid-coated silver nanowire 1(7 parts by mass) were mixed to obtain composition 1 for forming a hard coat layer.

After dropping the composition 1 for forming a hard coat layer (1.5ml) onto the primer layer, the plastic spectacle lens substrate coated with the composition 1 for forming a hard coat layer was rotated at 1000rpm for 10 seconds by a spin coater. Then, the obtained plastic spectacle lens base material was heated at 90 ℃ for 10 minutes and then, a high pressure mercury lamp (100 mW/cm) was used²) As a light source, UV irradiation (cumulative light amount: 1.6J/cm²) Thereby forming a hard coating layer.

The other surface of the plastic spectacle lens base material was also subjected to the same treatment as described above, thereby obtaining a spectacle lens having hard coat layers disposed on both surfaces of the plastic spectacle lens base material.

< example A2 >

A spectacle lens was obtained in the same manner as in example a1, except that the ionic liquid-coated nanowire 2 obtained by the method described later was used in place of the ionic liquid-coated silver nanowire 1, and the metal concentration and the ionic liquid concentration described in table 1 were adjusted so as to be achieved.

(production of Ionic liquid-coated silver nanowire 2)

A silver nanowire isopropanol solution (concentration 20mg/ml, 10 parts by mass) (ACS Materials, Agnw-L30), a 1mol/L nitric acid aqueous solution (10 parts by mass), and an ionic liquid IL-OH2(0.2 part by mass) containing OH functional groups were mixed and stirred at 75 ℃ for 1 hour. Then, all of the isopropyl alcohol and water were evaporated from the obtained solution, and the ionic liquid-coated silver nanowire 2 was obtained as a residue.

< example A3 >

A spectacle lens was obtained in the same manner as in example a1, except that the ionic liquid-coated silver nanowire 3 obtained by the method described later was used in place of the ionic liquid-coated silver nanowire 1, and the metal concentration and the ionic liquid concentration described in table 1 were adjusted so as to be achieved.

(production of Ionic liquid-coated silver nanowire 3)

A silver nanowire isopropanol solution (concentration 20mg/ml, 10 parts by mass) (ACS Materials, Agnw-L30), a 1mol/L nitric acid aqueous solution (10 parts by mass), and an ionic liquid IL-OH2(0.4 part by mass) containing OH functional groups were mixed and stirred at 75 ℃ for 1 hour. Then, all of the isopropyl alcohol and water were evaporated from the obtained solution, and the ionic liquid-coated silver nanowire 3 was obtained as a residue.

< example A4 >

An ophthalmic lens was obtained in the same manner as in example a1 except that an OH functional group-containing ionic liquid IL-OH8 (bis (ethylene glycol 1-oxyethyl) alkylmethylammonium ═ bis (trifluoromethanesulfonyl) imide (manufactured by gorgon chemical industries)) (0.08 parts by mass) was used in place of the OH functional group-containing ionic liquid IL-OH 2.

< example A5 >

An ophthalmic lens was obtained in the same manner as in example A2 except that an ionic liquid IL-OH8 containing OH functional groups was used in place of the ionic liquid IL-OH2 containing OH functional groups.

< example A6 >

An ophthalmic lens was obtained in the same manner as in example A3 except that an ionic liquid IL-OH8 containing OH functional groups was used in place of the ionic liquid IL-OH2 containing OH functional groups.

< evaluation >

The following evaluations were carried out using the spectacle lenses obtained in the above examples and comparative examples and a spectacle lens containing an antireflection film described later. The results are summarized in table 1 below.

(surface resistivity 1)

The surface resistivity of the ophthalmic lenses was measured using HIRESTA UP MCP-HT450(ミツビシケミカルアナリテック) as a surface resistivity meter. Specifically, the electrode was vertically brought into contact with the hard coat surface of the spectacle lens, and a voltage of 500V was applied. After 30 seconds of contact, the surface resistivity was determined as the value measured at the 30 th second.

(surface resistivity 2)

The surface resistivity of the spectacle lens containing the antireflection film was measured using HIRESTA UP MCP-HT450(ミツビシケミカルアナリテック) as a surface resistivity meter. Specifically, the electrode was brought into vertical contact with the surface of the antireflection film of the spectacle lens containing the antireflection film produced in the evaluation (adhesion) described later, and a voltage of 500V was applied. After 30 seconds of contact, the surface resistivity was determined as the value measured at the 30 th second.

(Adhesivity)

The adhesion was evaluated by a cross cut adhesive tape test in accordance with JIS-K5600.

Specifically, first, an antireflection film is formed on the hard coat layer in accordance with the procedure (formation of an antireflection film) described later, and a spectacle lens containing the antireflection film is obtained.

Then, cuts reaching as deep as the plastic spectacle lens base material were formed on the surface of the antireflection film of the spectacle lens containing the antireflection film at 1mm intervals by a knife, thereby forming 100 checkerboards. Then, SCOTCH TAPE (manufactured by 3M) was pressed strongly against the anti-reflection film having the cut. The SCOTCH TAPE was then rapidly pulled and peeled off from the surface of the antireflection film in a direction of 60 ° with a load of 4kg, and the number of checkerboards remaining on the plastic eyeglass lens base material was counted.

(formation of antireflection film)

Placing the obtained spectacle lens on a rotary drum arranged in a vacuum tank, heating the temperature in the vacuum tank to 70 deg.C, and exhausting until the pressure reaches 1.0 × 10^-3Pa is up to. Then, one hard coat layer was subjected to Ar ion beam cleaning for 60 seconds under conditions of an acceleration voltage of 500V and an acceleration current of 100mA, and then a first SiO layer was laminated in this order on the cleaned hard coat layer in an optical film thickness of 0.090 λ₂(refractive index: 1.47) and a second layer of ZrO was laminated at an optical film thickness of 0.038. lambda₂(refractive index 2.00) and an optical film thickness of 0.393 λ₂(refractive index: 1.47) and a fourth layer of ZrO laminated at an optical film thickness of 0.104. lambda.₂(refractive index 2.00) and an optical film thickness of 0.069 lambda₂(refractive index: 1.47) and a sixth layer of ZrO laminated at an optical film thickness of 0.289. lambda₂(refractive index 2.00) and a seventh SiO layer was laminated at an optical film thickness of 0.263. lambda.₂(refractive index 1.47), thereby forming an antireflection film. λ is a designed center wavelength and is set to 500 nm.

In addition, the other hard coat layer is also subjected to the same treatment as described above, whereby the antireflection film is formed on both surfaces of the spectacle lens, and the spectacle lens containing the antireflection film is obtained.

(scratch resistance)

The surface of the antireflection film in the spectacle lens containing the antireflection film produced in the above evaluation (adhesion) was subjected to reciprocal rubbing 50 times by applying a load of 2kg to Bonstar #0000 steel wool (manufactured by japan スチールウール corporation), and the degree of scratching on the hard coat surface (1cm × 3cm) was evaluated by visually classifying the degree into the following grades.

Good: excellent (no scratch observed)

Δ: good (shallow scratches of less than 30 were observed, but there was no problem in practical use)

X: bad (more than 30 scratches were observed, which was problematic in practical use)

(visual transmittance)

The visual transmittance of the spectacle lens with the antireflection film produced in the above evaluation (adhesion) was measured using an LED transmittance meter manufactured by fuji photo electric industries, ltd, LDM-200.

In table 1, "metal" indicates the metal nanowire or metal nanoparticle used, and AgNW indicates a silver nanowire.

In table 1, "ionic liquid" indicates the kind of ionic liquid used.

In table 1, "metal concentration (% by mass)" represents the content of the above-mentioned "metal" with respect to the total mass of the hard coating layer, and the content of the silver nanowires with respect to the total mass of the hard coating layer is shown in table 1.

In table 1, "ionic liquid concentration (% by mass)" represents the content of the above-mentioned "ionic liquid" with respect to the total mass of the hard coat layer.

In table 1, "presence or absence of coating" indicates whether or not the ionic liquid is coated on the metal nanowire or metal nanoparticle indicated by "metal". The term "present" means "present" in the case of coating, and "absent" means "not coated.

In table 1, "film thickness (μm)" represents the film thickness of the hard coat layer.

In Table 1, "1.0E 15 <" means more than 1.0E 15.

[ Table 1]

As shown in table 1, it was confirmed that the desired effect was obtained in the case of a predetermined spectacle lens.

< comparative example B1 >

An ophthalmic lens was obtained in the same manner as in comparative example A2 except that silver nanoparticles (. phi.2-3.5 μm, 327085, Sigma-Aldrich) (5 parts by mass) were used in place of the silver nanowires (solvent-free) (ACS Materials, Agnw-L30) (5 parts by mass) of the silver nanowire solution.

< comparative example B2 >

An ophthalmic lens was obtained in the same manner as in comparative example B1, except that ionic liquid IL-OH2(10 parts by mass) having OH functional groups and silver nanoparticles (. phi.2-3.5 μm, 327085, Sigma-Aldrich) (5 parts by mass) were used in place of the silver nanowires.

In comparative example B2, the ionic liquid and the silver nanoparticles were used, but the ionic liquid did not coat the silver nanoparticles.

< example B1 >

A spectacle lens was obtained in the same manner as in comparative example B1, except that the ionic liquid-coated silver nanoparticles (15 parts by mass) prepared by the steps described below were used instead of the silver nanowires.

(production of Ionic liquid-coated silver nanoparticle)

Silver nanoparticles (1.8 parts by mass) (2-3.5 μm, 327085, Sigma-Aldrich) and 1mol/l aqueous nitric acid (9 parts by mass) were mixed with IL-OH2(3.6 parts by mass) which is an ionic liquid containing OH functional groups, and stirred at 75 ℃ for 1 hour. Then, all the water was evaporated from the obtained solution, and ionic liquid-coated silver nanoparticles were obtained as a residue.

The above-mentioned < evaluation > was carried out using the obtained spectacle lens. The results are summarized in Table 2.

In table 2, "AgNP" represents silver nanoparticles.

[ Table 2]

As shown in table 2, it was confirmed that the desired effect was obtained in the case of a predetermined spectacle lens.

< comparative example C1 >

The undercoat layer was formed by the same procedure as in comparative example A1.

Methacrylic silsesquioxane (AC-SQ TA-100, manufactured by Toyo Synthesis Co., Ltd.) (50 parts by mass), 1-methoxy-2-propanol (50 parts by mass), IRGACURE127 (photopolymerization initiator, manufactured by BASF Co., Ltd.) (3 parts by mass), and 1-ethyl-3-methylimidazole were used as silsesquioxane having a radical polymerizable groupBis (trifluoromethanesulfonyl) imide (hereinafter also referred to as "Im-IL") (2 parts by mass) was mixed to obtain composition 2 for forming a hard coat layer.

After dropping the composition 2 for forming a hard coat layer (1.5ml) on the undercoat layer, the plastic spectacle lens substrate coated with the composition 2 for forming a hard coat layer was rotated at 1000rpm for 10 seconds by a spin coater. Then, the obtained plastic spectacle lens base material was heated at 90 ℃ for 10 minutes and then, a high pressure mercury lamp (100 mW/cm) was used²) The coating film was UV-irradiated as a light source (cumulative light amount: 1.6J/cm²) Thereby forming a hard coating layer.

The other surface of the plastic spectacle lens base material was also subjected to the same treatment as described above, thereby obtaining a spectacle lens having hard coat layers disposed on both surfaces of the plastic spectacle lens base material.

< comparative example C2 >

A spectacle lens was obtained in the same manner as in comparative example C1, except that Im-IL (2 parts by mass) and Au nanoparticles (Sigma-Aldrich, product No. 636347) (5 parts by mass) were used in place of Im-IL (2 parts by mass).

In comparative example C2, the ionic liquid and the gold nanoparticles were used, but the gold nanoparticles were not coated with the ionic liquid.

The average particle diameter of the Au nanoparticles was 100 nm.

< example C1 >

A spectacle lens was obtained in the same manner as in comparative example C1, except that Im-IL (2 parts by mass) was replaced with Au nanoparticle 1(7 parts by mass) coated with an ionic liquid prepared in the following procedure.

(preparation of Ionic liquid-coated Au nanoparticle 1)

Au nanoparticles (Sigma-Aldrich, product No. 636347) (5 parts by mass), Im-IL (2 parts by mass), and pure water (50 parts by mass) were mixed and stirred at 75 ℃ for 1 hour. The entire amount of water was evaporated from the obtained solution, and the ionic liquid-coated Au nanoparticles 1 were obtained as a residue.

The above-mentioned < evaluation > was carried out using the obtained spectacle lens. The results are summarized in Table 3.

In table 3, "AuNP" represents gold nanoparticles.

[ Table 3]

As shown in table 3, it was confirmed that the desired effect was obtained in the case of a predetermined spectacle lens.

< comparative example D1 >

(formation of undercoat layer)

To an aqueous urethane dispersion (エバファール HA170, manufactured by hitachi Chemical corporation, solid content concentration 37%) (200 parts by mass), pure water (289 parts by mass), propylene glycol monomethyl ether (10.6 parts by mass), L77 (manufactured by Momentive) (0.2 parts by mass) and L7604 (manufactured by Dow Chemical) (0.2 parts by mass), an ionic liquid IL-OH9 containing an OH functional group (bis (hydroxyethyl) oleylmethylammonium-bis (trifluoromethanesulfonyl) imide, manufactured by shangro Chemical industry)) (3 parts by mass) were added and stirred to prepare a primer layer forming composition 2 having a solid content concentration of 15% by mass.

As the plastic spectacle lens base material, a lens (Nikon Lite 3AS blank S0.00D, Nikon Lite Co., Ltd.) having a refractive index of 1.60 was used.

The plastic eyeglass lens base material was immersed at 90 mm/min in the composition 2 for forming an undercoat layer, and baked at 90 ℃ for 20 minutes, thereby forming an undercoat layer.

(hard coat layer formation)

Acid phosphoryloxyethyl methacrylate (Phosmer M, manufactured by ユニケミカル) (6 parts by mass), methacrylic silsesquioxane (AC-SQ TA-100, manufactured by east asian synthesis corporation) as silsesquioxane having a radical polymerizable group (15 parts by mass), a zirconium dioxide dispersion (manufactured by kanto electrical industries, inc.) (185 parts by mass) (40% by mass of zirconium dioxide nanoparticle/propylene glycol monomethyl ether dispersion, zirconium dioxide solid content (74 parts by mass)), a polyethylene glycol dimethacrylate (LIGHT ACRYLATE 4EG-a, manufactured by coohnko chemical corporation) (5 parts by mass), and IRGACURE127 (photopolymerization initiator, manufactured by BASF corporation) (3 parts by mass) were mixed to obtain a composition C2 for forming a hard coat layer.

After dropping the hard coat layer-forming composition C2(1.5ml) on the primer layer, the plastic spectacle lens substrate coated with the hard coat layer-forming composition C2 was rotated at 1000rpm for 10 seconds by a spin coater. Then, the obtained plastic spectacle lens base material was heated at 90 ℃ for 10 minutes and then, a high pressure mercury lamp (100 mW/cm) was used²) The coating film was UV-irradiated as a light source (cumulative light amount: 1.6J/cm²) Thereby forming a hard coating layer.

The other surface of the plastic spectacle lens base material was also subjected to the same treatment as described above, thereby obtaining a spectacle lens having hard coat layers disposed on both surfaces of the plastic spectacle lens base material.

< example D1 >

A spectacle lens was obtained in the same manner as in comparative example D1, except that the ionic liquid-coated Au nanoparticles 2 prepared by the procedure described later was used in place of the ionic liquid IL-OH9(3 parts by mass) having an OH functional group, and the metal concentration and the ionic liquid concentration described in table 4 were adjusted so as to be achieved.

(preparation of Ionic liquid-coated Au nanoparticle 2)

Au nanoparticles (Sigma-Aldrich, product No. 636347) (10 parts by mass), an ionic liquid containing OH functional groups IL-OH9(4 parts by mass), and pure water (50 parts by mass) were mixed and stirred at 75 ℃ for 1 hour. The entire amount of water was evaporated from the obtained solution, and the ionic liquid-coated Au nanoparticles 2 were obtained as a residue.

The above-mentioned < evaluation > was carried out using the obtained spectacle lens. The results are summarized in Table 4.

In table 4, "metal concentration (% by mass)" represents the content of the above-mentioned "metal" with respect to the total mass of the undercoat layer, and the content of the gold nanoparticles with respect to the total mass of the undercoat layer is shown in table 1.

In table 1, "ionic liquid concentration (% by mass)" represents the content of the above-mentioned "ionic liquid" with respect to the total mass of the undercoat layer.

[ Table 4]

As shown in table 4, it was confirmed that the desired effect can be obtained for a predetermined spectacle lens.

Description of the symbols

10A, 10B spectacle lens

12 spectacle lens base material

14A, 14B hard coat layer

16 base coat