Composition, eyeglass lenses

Abstract

To provide a composition that can form a film with excellent water-repellent and antistatic properties. [Solution] A composition comprising a silyl isocyanate compound, a polysiloxane having a reactive functional group such as a hydroxyl group, and an ionic liquid.

Description

[Technical Field]

[0001] This disclosure relates to compositions and eyeglass lenses. [Background technology]

[0002] Patent Document 1 discloses an eyeglass lens having a coating film on the surface of a lens substrate containing tungsten oxide particles, tin oxide particles, and silver particles. [Prior art documents] [Patent Documents]

[0003] [Patent Document 1] Japanese Patent Publication No. 2020-106751 [Overview of the project]

[0004] This disclosure relates to a composition comprising a silyl isocyanate compound, a polysiloxane having a reactive functional group, and an ionic liquid. [Modes for carrying out the invention]

[0005] The details of this disclosure are described below. The composition of this disclosure (hereinafter also simply referred to as "the composition") is capable of forming a film with excellent antistatic and water-repellent properties. The following descriptions of constituent elements may be based on representative embodiments of this disclosure, but this disclosure is not limited to such embodiments.

[0006] In this specification, a numerical range represented by "~" means a range that includes the numbers written before and after "~" as the lower and upper limits, respectively. Furthermore, in this specification, if there are two or more components, the "content" of those components means the total content of those two or more components. In this specification, in numerical ranges described in stages, the upper or lower limit stated in one numerical range may be replaced with the upper or lower limit of another numerical range described in stages. Furthermore, in numerical ranges described in this specification, the upper or lower limit stated in one numerical range may be replaced with the values ​​shown in the examples. In this specification, a combination of two or more preferred embodiments is a more preferred embodiment.

[0007] In this specification, "solids" of a composition means the components that form a film when the composition is used, and if the composition contains a solvent (e.g., an organic solvent and water), it means all components excluding the solvent. Furthermore, any liquid components that form a film when the composition is used are also considered to be solids. The bonding direction of divalent groups as expressed herein is not limited unless otherwise specified. For example, in a compound represented by the formula "XYZ", if Y is -COO-, Y may also be -CO-O- or -O-CO-. Furthermore, the above compound may also be "X-CO-OZ" or "XO-CO-Z". In this specification, unless otherwise specified, when there are multiple substituents and linking groups, etc. (hereinafter referred to as substituents, etc.) indicated by a specific symbol, or when multiple substituents, etc. are specified simultaneously, it means that each substituent, etc. may be identical or different from the others. The same applies to the specification of the number of substituents, etc.

[0008] [Composition] The composition comprises a silyl isocyanate compound, a polysiloxane having a reactive functional group (hereinafter also referred to as "specific polysiloxane"), and an ionic liquid.

[0009] [Silyl isocyanate compounds] The composition contains a silyl isocyanate compound. Silyl isocyanate compounds are compounds that have an isocyanate group directly bonded to a silicon atom. The number of isocyanate groups directly bonded to the silicon atom in the silyl isocyanate compound is 1 or more, preferably 1 to 4, more preferably 2 to 4, and even more preferably 3 or 4. The number of silicon atoms in the silyl isocyanate compound is preferably 1 to 4, more preferably 1 or 2, and even more preferably 1.

[0010] As the silyl isocyanate compound, a compound represented by the formula (A1) is preferable. R A1 4-n1 -Si(NCO) n1 Formula (A1) In formula (A1), R A1 represents a non-hydrolyzable group, and n1 represents an integer of 1 to 4.

[0011] In formula (A1), R A1 The non-hydrolyzable group represented by is not particularly limited as long as the bond with the silicon atom is not hydrolyzed, and examples thereof include a hydrocarbon group which may have a substituent. As the hydrocarbon group, an alkyl group or an aryl group is preferable, and an alkyl group is more preferable. The above alkyl group may be linear, branched or cyclic, preferably linear or branched, and more preferably linear. The carbon number of the above alkyl group is preferably 1 to 10, more preferably 1 to 6, even more preferably 1 to 4, and particularly preferably 1 or 2. The above aryl group may be monocyclic or polycyclic, and a monocyclic group is preferable. The carbon number of the above aryl group is preferably 6 to 12, and more preferably 6 to 10. Examples of the substituent that the above hydrocarbon group may have include an alkoxy group, an acyl group and a halogen atom. R A1 is preferably an alkyl group, and more preferably an alkyl group having 1 to 4 carbon atoms.

[0012] In formula (A1), n1 represents an integer of 1 to 4, preferably an integer of 2 to 4, and more preferably 3 or 4.

[0013] Examples of the silyl isocyanate compound include methyltriisocyanate silane, tetraisocyanate silane, and dimethyldiisocyanate silane. Methyltriisocyanate silane or tetraisocyanate silane is preferable, and methyltriisocyanate silane is more preferable.

[0014] The silyl isocyanate compound may be used alone or in combination of two or more. The content of the silyl isocyanate compound is preferably 0.5 to 10% by mass, more preferably 1 to 5% by mass, and still more preferably 1 to 3.5% by mass based on the total mass of the composition.

[0015] 〔Specific polysiloxane〕 The composition contains a specific polysiloxane which is a polysiloxane having a reactive functional group. It is presumed that a film excellent in water repellency is formed by the reaction of the reactive functional group of the specific polysiloxane with the silyl isocyanate compound. The mode of the above reaction is not particularly limited. For example, the reactive functional group and the isocyanate group may react to form a bond (for example, a urethane bond), or the isocyanate group may be eliminated and the reactive functional group or a part thereof and the silicon atom of the silyl isocyanate compound may form a bond. As the reactive functional group, a functional group containing an active hydrogen atom is preferable. Specific examples of the reactive functional group include a hydroxyl group, an amino group, a carboxy group, a urethane group, and a urea group, etc. The hydroxyl group is preferable. The hydroxyl group may be a part of a silanol group (Si-OH). The reactive functional group may be an alkoxysilyl group. The number of reactive functional groups possessed by the specific polysiloxane is 1 or more, and may be 2 or more. Further, the reactive functional group may be present at the terminal of the specific polysiloxane or in the side chain.

[0016] The specific polysiloxane has a polysiloxane structure. As the polysiloxane structure, a dialkylpolysiloxane structure is preferred, and a dimethylpolysiloxane structure is preferred. The above polysiloxane structure may be any of linear, branched, and cyclic, and a linear structure is preferred.

[0017] The specific polysiloxane may be used alone or in combination of two or more. The total content of the silyl isocyanate compound and the specific polysiloxane is preferably 0.5 to 12% by mass, more preferably 1 to 5% by mass, based on the total mass of the composition.

[0018] [Ionic liquid] The composition contains an ionic liquid. The ionic liquid is composed of a cation and an anion, and means a substance having a melting temperature of less than 100 °C at 1 atm (1013 hPa). The above melting temperature is preferably less than 40 °C, more preferably less than 25 °C. In other words, the ionic liquid is preferably liquid under standard conditions (25 °C, 1 atm).

[0019] The ionic liquid may have a reactive group that reacts with at least one of the above-mentioned silyl isocyanate compound and specific polysiloxane. When the ionic liquid has the above reactive group, the ionic liquid reacts with the above components and is immobilized, improving the antistatic and abrasion resistance. Note that the ionic liquid does not necessarily have the above reactive group. When the ionic liquid does not have the above reactive group, the ionic liquid is more likely to be unevenly distributed on the surface of the film formed by the composition, further improving the antistatic property. Note that the ionic liquid having a reactive group means that at least one of the cation and anion in the ionic liquid has a reactive group, and it is preferable that the cation has a reactive group. As the above reactive group, a hydrolyzable silyl group is preferred. As the above hydrolyzable silyl group, for example, -Si(X) n2 (R B1 ) 3-n2 The group represented by is mentioned. Each X independently represents a hydrolyzable group or a hydroxyl group. Examples of hydrolyzable groups include alkoxy groups and halogen atoms, with alkoxy groups having 1 to 4 carbon atoms or chlorine atoms being preferred, and methoxy groups or ethoxy groups being more preferred. R B1 Each of these independently represents a non-hydrolyzable group. B1 As a non-hydrolyzable group represented by the above formula (A1), R A1 Examples of non-hydrolyzable groups represented by the above include the groups shown, and the preferred embodiments are the same. n2 represents an integer between 1 and 3, with 3 being preferred. The ionic liquid may have, as a reactive group, the groups exemplified as reactive functional groups possessed by the specific polysiloxane described above.

[0020] Furthermore, if the ionic liquid has hydrolyzable silyl groups, the composition may contain at least one selected from the group consisting of hydrolyzed products obtained by hydrolyzing at least a portion of the hydrolyzable silyl groups, and hydrolyzed condensates obtained by condensing the hydrolyzed hydrolyzable silyl groups.

[0021] Organic cations are preferred as cations in ionic liquids, and examples include ammonium cations (preferably quaternary ammonium cations), pyridinium cations, pyrodinium cations, imidazolium cations, and phosphonium cations. In particular, the ionic liquid preferably contains at least one cation selected from the group consisting of quaternary ammonium cations and phosphonium cations, due to its excellent hydrophobicity and superior water repellency of the resulting film. The above cation may have functional groups other than the cation atom, for example, it may have the reactive group described above.

[0022] Among the above cations, the cation represented by formula (B1) or the cation represented by formula (B2) is preferred. R B2 3-N + -L B1 -Y formula (B1) R B3 3-P + -L B2 -Y formula (B2)

[0023] In equations (B1) and (B2), R B2 and R B3 Each of these independently represents a hydrocarbon group which may have substituents. The hydrocarbon group is preferably an alkyl group or an aryl group, with alkyl groups being more preferred. The alkyl group described above may be linear, branched, or cyclic, with linear or branched being preferred. The number of carbon atoms in the alkyl group is preferably 1 to 10, more preferably 1 to 6, and even more preferably 1 to 4. The number of carbon atoms in the above aryl group is preferably 6 to 12, more preferably 6 to 10, and even more preferably 6. Examples of substituents that the hydrocarbon group may have include alkoxy groups, acyl groups, and halogen atoms.

[0024] In formulas (B1) and (B2), L B1 and L B2 Each of these independently represents a divalent linking group. The above divalent linking groups include alkylene groups, -O-, -CO-, and -NR. N - and groups formed by combining two or more of these are examples. The number of carbon atoms in the above-mentioned divalent linking group is preferably 1 or more, more preferably 2 or more, and even more preferably 2 to 12. The alkylene group may be linear, branched, or cyclic, with linear being preferred. The number of carbon atoms in the alkylene group is preferably 1 to 12, more preferably 2 to 10, and even more preferably 2 to 6.

[0025] In formulas (B1) and (B2), Y represents a hydrogen atom or a reactive group. Examples of reactive groups are as described above, with hydrolyzable silyl groups being preferred. Details of hydrolyzable silyl groups are as described above.

[0026] From the viewpoint of water repellency, the number of carbon atoms in the above cation is preferably 6 or more, more preferably 10 or more, and even more preferably 14 or more. There is no particular upper limit, but it is often 30 or less.

[0027] Anions in ionic liquids are not particularly limited and include, for example, halide ions; cyanide ions; dicyanoamine anions; sulfonate ions such as butanesulfonate ions, methylsulfonate ions, ethylsulfonate ions, octylsulfonate ions, trifluoromethanesulfonate ions, tetrafluoroethanesulfonate ions, and nonafluorobutanesulfonate ions; carboxylate ions such as lactate ions, salicylate ions, thiosalicylate ions, dibutylphosphate ions, acetate ions, decanoate ions, and trifluoroacetate ions; hexafluoroantimonate ions; bisulfate ions; sulfate ions; tetrachloroaluminate ions; thiocyanate ions; tris( Examples include trifluoromethylsulfonyl(TRI)methide ions; aminocarboxylic acid ions such as aminoacetate and aminopropionate ions; phosphate ions such as diethyl phosphate, dimethyl phosphate, and hexafluorophosphate; alkyl sulfate ions such as ethyl sulfate and methyl sulfate; hydroxide ions; bis(trimethylpentyl)phosphinate ions; iron ions; tetrafluoroborate ions; sulfonylamide anions; and sulfonylimide anions such as bis(trifluoromethanesulfonyl)imide anions (TFSA), bis(trifluoroethanesulfonyl)imide anions, and bis(pentafluoroethanesulfonyl)imide anions. Among the anions, sulfonilimide anions are preferred, and TFSA is more preferred.

[0028] Ionic liquids may be used individually or in combination of two or more types. The ionic liquid content is preferably 0.01 to 5% by mass, more preferably 0.05 to 1.5% by mass, and even more preferably 0.5 to 1% by mass, based on the total mass of the composition. The content of the ionic liquid relative to the silyl isocyanate compound is preferably 0.5 to 44% by mass, more preferably 1.8 to 27% by mass, even more preferably 2 to 15% by mass, and particularly preferably 3 to 10% by mass.

[0029] [Organic solvents] The composition may contain an organic solvent. Note that the organic solvent is a component different from the components described above (silyl isocyanate compounds, specific polysiloxanes, and ionic liquids). Examples of organic solvents include alcohol-based solvents, ketone-based solvents, ether-based solvents, ester-based solvents, hydrocarbon-based solvents, halogenated hydrocarbon-based solvents, amide-based solvents, sulfone-based solvents, and sulfoxide-based solvents. Examples of alcohol-based solvents include methanol, ethanol, isopropanol, n-butanol, t-butanol, isobutyl alcohol, pentanol, hexanol, propylene glycol, ethylene glycol, diethylene glycol, 2-methyl-1,3-propanediol, 1,3-propanediol, 2,2-dimethyl-1,3-propanediol, and 1,4-butanediol, with isopropanol being preferred. Examples of ester solvents include acetate ester solvents such as ethyl acetate and butyl acetate, and alkylene glycol ester solvents such as ethylene glycol monomethyl ether acetate, diethylene glycol monomethyl ether acetate, and propylene glycol monomethyl ether acetate, with acetate ester solvents being preferred. For superior storage stability, the organic solvent preferably contains at least one selected from the group consisting of alcohol-based solvents and ester-based solvents, and more preferably contains both alcohol-based and ester-based solvents. Organic solvents may be used individually or in combination of two or more types. The alcohol-based solvent content is preferably 1 to 100% by mass, more preferably 5 to 30% by mass, and even more preferably 5 to 15% by mass, relative to the total mass of the organic solvent. The content of the organic solvent is preferably 50 to 90% by mass, more preferably 60 to 90% by mass, and even more preferably 75 to 90% by mass, based on the total mass of the composition.

[0030] The composition may contain other components besides those described above. Other components include, for example, silane coupling agents without ionic groups, silanol condensation catalysts, antioxidants, rust inhibitors, ultraviolet absorbers, light stabilizers, fungicides, antibacterial agents, antifungal agents, deodorants, pigments, and flame retardants.

[0031] [Method for manufacturing the composition] The method for producing the composition is not particularly limited and can be produced by known methods. Specifically, one example is a method of mixing the above-mentioned components. More specifically, a method for mixing the above components is to add each component sequentially and then stir to mix them. When adding each component, it may be added all at once or in multiple steps.

[0032] 〔film〕 The composition disclosed herein can form a film with excellent water-repellent and antistatic properties. The above film preferably contains cured products of various components contained in the composition. That is, the film preferably contains cured products of a silyl isocyanate compound and a specific polysiloxane. In addition, at least a portion of the ionic liquid may react with a portion of the silyl isocyanate compound and the specific polysiloxane to form a portion of the cured product.

[0033] One method for manufacturing the above-mentioned film is to cure a coating film of the composition. More specifically, a method for curing a coating film of a composition includes applying the composition to a desired component to form a coating film, and then applying a curing treatment to the coating film as needed to form a film. From the viewpoint of uniformity of the formed film, it is preferable to form a coating film of a composition containing a solvent and then perform a drying treatment to remove the solvent. Methods for applying the composition include, for example, dipping coating, spin coating, spray coating, inkjet coating, and flow coating. Methods for the above-mentioned hardening treatment include drying and heating. The temperature for the curing treatment described above is preferably 40 to 120°C, and more preferably 60 to 80°C. The curing time described above is preferably 30 seconds to 60 minutes, and more preferably 5 to 30 minutes.

[0034] [Eyeglass lenses] The eyeglass lens of this disclosure comprises an eyeglass lens substrate and a layer formed by the composition of this disclosure (hereinafter also referred to as the "composition layer"). In addition to the above, eyeglass lenses preferably have an anti-reflective layer, and more preferably have the eyeglass lens substrate, anti-reflective layer, and composition layer in this order. The spectacle lens may have an anti-reflective layer and a composition layer on one surface of the spectacle lens substrate, or it may have an anti-reflective layer and a composition layer on both surfaces of the substrate. The anti-reflective layer is preferably arranged adjacent to the composition layer. In other words, the spectacle lens preferably has a spectacle lens substrate, an anti-reflective layer, and a composition layer arranged adjacent to the anti-reflective layer in this order.

[0035] [Eyeglass lens base material] Materials that make up the base material for eyeglass lenses include organic materials and inorganic materials, with organic materials being preferred. Examples of organic materials include acrylic acid ester resins, methacrylic acid ester resins, thiourethane resins, allyl resins, episulfide resins, polycarbonates, urethane resins, polyesters, polystyrene, polyethersulfone, poly-4-methylpentene-1, and diethylene glycol bisallyl carbonate resin (CR-39), with thiourethane resins, episulfide resins, or diethylene glycol bisallyl carbonate resins being preferred.

[0036] Thiourethane resin is a resin obtained by polymerizing a polyisocyanate compound and a polythiol compound. Preferred polyisocyanate compounds include m-xylylene diisocyanate, a mixture of 2,5-bis(isocyanatomethyl)-bicyclo[2,2,1]heptane and 2,6-bis(isocyanatomethyl)-bicyclo[2,2,1]-heptane, isophorone diisocyanate, hexamethylene diisocyanate, or tolylene diisocyanate. Preferred polythiol compounds include pentaerythritol tetrakis(3-mercaptopropionate), 1,2-bis[(2-mercaptoethyl)thio]-3-mercaptopropane, or a mixture of 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, and 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane. Episulfide resins are resins obtained by ring-opening polymerization of monomers having an episulfide group (epithio group), or mixed monomers containing such monomers. Preferred monomers having an episulfide group are bis(2,3-epithiopropyl)sulfide or bis(2,3-epithiopropyl)disulfide.

[0037] Examples of spectacle lens substrates include finished lenses in which the convex and concave surfaces are optically finished and molded to the desired prescription, semi-finished lenses in which only the convex surface is finished as an optical surface (e.g., spherical, rotationally symmetric aspherical, and progressive surfaces), and semi-finished lenses in which the concave surface is processed and polished according to the wearer's prescription.

[0038] The thickness of the spectacle lens base material is preferably 0.8 to 30.0 mm, and more preferably 1.0 to 10.0 mm, in terms of handling. The refractive index of the spectacle lens substrate is preferably 1.50 or higher, more preferably 1.60 to 1.80, and even more preferably 1.60 to 1.74.

[0039] [Anti-reflection layer] Eyeglass lenses preferably have an anti-reflective coating. The anti-reflective layer may be a single-layer or multi-layer structure. An inorganic anti-reflective layer is preferred as the anti-reflective layer. An inorganic anti-reflective layer refers to an anti-reflective layer composed of an inorganic compound. The multilayer anti-reflective layer may have a structure in which low refractive index layers and high refractive index layers are alternately stacked. Examples of materials that constitute the high refractive index layer include metal oxides selected from titanium, zirconium, aluminum, niobium, tantalum, and lanthanum. Examples of materials that constitute the low refractive index layer include silicon oxide.

[0040] Methods for forming an anti-reflective layer include, for example, dry methods such as vacuum deposition, sputtering, ion plating, ion beam-assisted deposition, and CVD.

[0041] The thickness of the anti-reflective layer is preferably 100 to 10,000 nm, and more preferably 300 to 700 nm.

[0042] [Composition layer] The eyeglass lens has a composition layer. The composition layer is a layer formed using the composition of the present disclosure described above. The composition layer preferably contains cured products of the various components contained in the composition. As a method for forming the composition layer, the film formation method described above can be used, and a method of curing the coating film of the composition is preferred. The method for forming the coating film of the composition is as described above.

[0043] It is also preferable to apply a surface treatment to the surface of the layer forming the coating film of the composition layer (preferably the surface of the anti-reflective layer) in order to ensure that the composition layer adheres more firmly to the adherend and has superior abrasion resistance. Examples of surface treatments include surface activation treatment and cleaning treatment. Examples of surface treatments include plasma treatment, corona treatment, ozone treatment, and UV treatment, with plasma treatment being preferred.

[0044] The thickness of the composition layer is preferably 2 to 50 nm, and more preferably 5 to 30 nm.

[0045] [Primer layer] Eyeglass lenses may have a primer layer. It is preferable to place the primer layer between the spectacle lens substrate and the hard coat layer described later. In this case, the adhesion between the spectacle lens substrate and the hard coat layer is easily improved, and the impact resistance of the laminate may be improved.

[0046] The primer layer preferably contains a resin. The resin may be in particulate form. Examples of resins include urethane resins, epoxy resins, phenolic resins, polyimides, polyesters, bismaleimide resins, and polyolefins, with urethane resins being preferred. The primer layer may contain additives such as surfactants.

[0047] One method for forming a primer layer is to apply a primer layer-forming composition containing a resin onto a desired member to form a coating film, and then to perform a curing treatment (e.g., drying treatment) on the coating film as needed to form a primer layer. In other words, it is preferable that the primer layer is a layer obtained by applying a primer layer-forming composition onto a desired member to form a coating film, and then curing the coating film. One method for applying the primer layer-forming composition is, for example, the method of applying the composition described above.

[0048] The thickness of the primer layer is preferably 0.3 to 2.0 μm.

[0049] [Hard court layer] Eyeglass lenses may have a hard coat layer. The hard coat layer is preferably placed on the primer layer, and more preferably between the primer layer and the anti-reflective layer. When an eyeglass lens has a hard coat layer, the scratch resistance of the eyeglass lens can be improved. The hard coat layer preferably exhibits a hardness of H or higher on the pencil hardness scale, in accordance with JIS K5600. As the hard coat layer, known hard coat layers can be used, such as organic hard coat layers, inorganic hard coat layers, and organic-inorganic hybrid hard coat layers. For example, in the field of eyeglass lenses, organic-inorganic hybrid hard coat layers are commonly used.

[0050] One method for forming a hard coat layer is to apply a hard coat layer-forming composition onto a desired member to form a coating film, and then, if necessary, to perform a curing treatment (e.g., light irradiation and drying treatment) on the coating film to form a hard coat layer. In other words, it is preferable that the hard coat layer is a layer obtained by applying a hard coat layer-forming composition onto a desired member to form a coating film, and then curing the coating film. One method for applying the hard coat layer formation composition onto a substrate is, for example, the method of applying the composition described above.

[0051] The thickness of the hard coat layer is preferably 1 to 20 μm, and more preferably 2 to 18 μm.

[0052] [Method of manufacturing eyeglass lenses] Known manufacturing methods can be used for manufacturing eyeglass lenses. Specifically, one example is a method that includes the step of forming a composition layer on at least one side of an eyeglass lens substrate. In particular, the method for manufacturing eyeglass lenses preferably includes the steps of forming an anti-reflective layer on at least one surface of an eyeglass lens substrate and forming a composition layer on the anti-reflective layer. The method for forming each layer is as described above.

[0053] [Application] As described above, the compositions of this disclosure can be used in eyeglass lenses. The compositions of this disclosure can also be used to form laminates having a substrate other than eyeglass lenses and a composition layer formed by the compositions of this disclosure. One application of the above-mentioned laminate is as a front panel (window film) in flexible display devices. The flexible display device described above preferably consists of a laminate for flexible display devices and an organic electroluminescent display panel, wherein the laminate for flexible display devices is positioned on the viewing side relative to the organic electroluminescent display panel and is configured to be bendable. The laminate for the flexible display device may further include a polarizing plate (preferably a circular polarizing plate) and a touch sensor. In the laminate for the flexible display device, it is preferable that the laminate (window film), polarizing plate, and touch sensor are stacked in that order from the viewing side, or from the viewing side, in that order. It is preferable that the polarizing plate is located on the viewing side of the touch sensor, as this makes the pattern of the touch sensor harder to see and improves the visibility of the displayed image. Each component can be stacked using adhesives and other adhesives. [Examples]

[0054] The present disclosure will be described in more detail below with reference to examples, but the present disclosure is not limited in any way by these examples.

[0055] [Raw materials] The raw materials used in the preparation of the compositions of the examples and comparative examples are described below. • SIC-434: Manufactured by Matsumoto Fine Chemical Co., Ltd., it contains monomethyltriisocyanate silane (10% by mass), a polysiloxane having a reactive functional group, and ethyl acetate as a solvent. • Compound 1: An ionic liquid consisting of a cation and anion with the following structure.

[0056] [ka]

[0057] • Compound 2: An ionic liquid consisting of a cation and anion with the following structure.

[0058] [ka]

[0059] • Acetic acid solution: Manufactured by Kanto Chemical Co., Ltd., 1 mol / L acetic acid (1N)

[0060] [Preparation of the composition] <Composition 1> Composition 1 was obtained by mixing ethyl acetate (3.66 parts by mass) and compound 1 to a solution with the composition shown in Table 1, then mixing in SIC-434 (1.02 parts by mass), and finally mixing in isopropanol (0.41 parts by mass).

[0061] <Composition 2~4> Compositions 2 to 4 were prepared in the same manner as Composition 1, except that the type of ionic liquid and the amounts of ionic liquid, SIC-434, and solvent used were changed as shown in Table 1. Composition 3 did not use an ionic liquid. Composition 4 was prepared without using SIC-434, by adding the aforementioned aqueous acetic acid solution as a hydrolysis catalyst for the alkoxysilyl groups contained in the ionic liquid and mixing for 15 minutes.

[0062] In Table 1, the amount of each component used is in parts by mass. In Table 1, the "Ionic Liquid / Silyl Isocyanate Compound (mass%)" column shows the content of the ionic liquid relative to the silyl isocyanate compound in the composition (unit: mass%).

[0063] [Table 1]

[0064] [Formation of eyeglass lenses] The composition layers of each example and comparative example were formed according to the following procedure, and eyeglass lenses were manufactured.

[0065] <Example 1> As a lens, an anti-reflective lens (a lens with a structure similar to the ECC (manufactured by Nikon-Essilor) but without the top coat layer, having a spectacle lens substrate, primer layer, hard coat layer, and anti-reflective layer in that order; the top coat layer is not formed from the beginning) was prepared, and the anti-reflective layer was cleaned with a plasma dry cleaner (Yamato Scientific PDC210, 400W, for a processing time of 30 seconds). The obtained composition 1 was then coated onto the cleaned anti-reflective layer by spin coating (500 rpm for 30 seconds, followed by 2000 rpm for 1 second). Next, the lens on which the coating film of composition 1 was formed was heated and cured in an 80°C constant temperature bath for 15 minutes to form a composition layer, thereby obtaining the spectacle lens of Example 1.

[0066] <Example 2, Comparative Example 1> Eyeglass lenses for Example 2 and Comparative Example 1 were prepared in the same manner as in Example 1, except that composition 1 was changed to one of the compositions listed in Table 2.

[0067] <Comparative Example 2> The anti-reflective layer, cleaned in the same manner as in Example 1, was immersed in composition 4 at room temperature (25°C) for 1 hour, after which the lens was removed from composition 2 and excess composition 4 was removed. Next, the lens on which the coating of composition 4 was formed was heated and cured in an 80°C constant temperature bath for 15 minutes to form a composition layer. Furthermore, the surface of the obtained composition layer was wiped with a Kimwipe soaked in acetone and then dried with an air gun to remove components that were not fixed to the anti-reflective layer, thereby obtaining the spectacle lens of Comparative Example 2.

[0068] [evaluation] The surface of the resulting spectacle lens composition layer was wiped with a Kimwipe soaked in acetone, then dried with an air gun, and the water contact angle of the central portion was measured using a contact angle meter (Kyowa Interface Science Co., Ltd., DM500). The measurement temperature for the water contact angle was 25°C. A larger water contact angle indicates superior water repellency.

[0069] [Antistatic properties] The surface of the resulting spectacle lens composition layer was wiped with a Kimwipe soaked in acetone, then dried with an air gun. The surface resistance of the central portion was measured using a resistivity meter (Mitsubishi Chemical Analytec, Highresta UP MCP-HT450). A lower surface resistance indicates superior antistatic properties.

[0070] [result] Table 2 shows the compositions used in each example and comparative example, as well as the evaluation results for water repellency and antistatic properties.

[0071] [Table 2]

[0072] The evaluation results confirmed that the composition of this disclosure can form a film that is excellent in water repellency and antistatic properties. Compared to the films formed by the compositions of this disclosure, the film formed by composition 3 of Comparative Example 1, which does not contain an ionic liquid, had inferior antistatic properties, and the film formed by composition 4 of Comparative Example 2, which does not contain a specific polysiloxane, had inferior water repellency.

Claims

1. Silyl isocyanate compounds and Polysiloxanes having reactive functional groups, A composition comprising an ionic liquid.

2. The composition according to claim 1, wherein the reactive functional group is a hydroxyl group.

3. The composition according to claim 1 or 2, wherein the ionic liquid comprises at least one cation selected from the group consisting of quaternary ammonium cations and phosphonium cations.

4. The composition according to any one of claims 1 to 3, wherein the content of the ionic liquid relative to the silyl isocyanate compound is 0.5 to 44% by mass.

5. Eyeglass lens base material, An eyeglass lens having a layer formed using the composition described in any one of claims 1 to 4.

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