Spectacle lens and composition
A hydrolysis condensate coating on eyeglass lenses addresses the issue of high friction when wet by using a silane coupling agent and tetraalkoxysilane, enabling effective dirt removal.
Patent Information
- Authority / Receiving Office
- WO · WO
- Patent Type
- Applications
- Current Assignee / Owner
- NIKON ESSILOR
- Filing Date
- 2025-12-03
- Publication Date
- 2026-06-18
AI Technical Summary
Existing eyeglass lenses have high coefficients of dynamic friction when wet, making it difficult to remove dirt effectively from their surfaces.
A coating comprising a hydrolysis condensate of a silane coupling agent derived from a nonionic surfactant, tetraalkoxysilane, and a silane coupling agent with an amino group is applied to eyeglass lenses to reduce the coefficient of dynamic friction when wet, enhancing dirt removal.
The coating significantly reduces the friction coefficient of eyeglass lenses when wet, facilitating easy removal of dirt and improving surface cleanliness.
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Figure JPOXMLDOC01-APPB-C000003
Abstract
Description
Eyeglass lenses, compositions 【0001】 This disclosure relates to eyeglass lenses and compositions. 【0002】 Patent Document 1 discloses a hydrophilizing agent composition comprising only at least one selected from the group consisting of hydrolysates and hydrolysates of a surfactant silane coupling agent having a predetermined structure, and at least one selected from the group consisting of hydrolysates and hydrolysates of a trialkoxysilane compound or dialkoxysilane compound having a predetermined structure. 【0003】 Japanese Patent Publication No. 2021-098834 【0004】 This disclosure relates to an eyeglass lens comprising an eyeglass lens substrate and a coating, wherein the coating comprises a hydrolysis condensate of a silane coupling agent having a structure derived from a nonionic surfactant, a tetraalkoxysilane, and a silane coupling agent having an amino group. This disclosure also relates to a composition that satisfies at least one of requirements 1 and 2 described later. 【0005】 The present disclosure is described in detail below. The spectacle lenses of this disclosure have a low coefficient of dynamic friction when water is applied. From the viewpoint of making it easy to remove dirt adhering to the surface, it is desirable for spectacle lenses to have a low coefficient of dynamic friction when water is applied, and the spectacle lenses of this disclosure satisfy the above requirement. The following descriptions of constituent elements may be based on typical embodiments of this disclosure, but this disclosure is not limited to such embodiments. 【0006】In this specification, a numerical range expressed using "~" means a range that includes the numbers written before and after "~" as the lower and upper limits. Also in this specification, if there are two or more types of a component, the "content" of that component means the total content of those two or more types of components. In this specification, in numerical ranges described in steps, 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 steps. Also, in numerical ranges described in this specification, the upper or lower limit stated in one numerical range may be replaced with the value shown in the example. 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. 【0008】In this specification, a hydrolyzed silane compound having a hydrolyzable silyl group (e.g., a silane coupling agent) means a compound obtained by hydrolysis of the hydrolyzable groups of the hydrolyzable silane compound. The hydrolyzed silane compound may be a complete hydrolyzate obtained by hydrolysis of all hydrolyzable groups in the hydrolyzable silane compound, or a partial hydrolyzate obtained by hydrolysis of some of the hydrolyzable groups. In other words, the hydrolyzate may be a complete hydrolyzate, a partial hydrolyzate, or a mixture thereof. In this specification, a hydrolyzed condensate of a hydrolyzable silane compound means a compound obtained by condensation of hydrolyzed silane compounds. The hydrolyzed condensate of a hydrolyzable silane compound may be a complete hydrolyzed condensate obtained by hydrolysis of all hydrolyzable groups and condensation of all hydrolyzed silane compounds, or a partial hydrolyzed condensate obtained by hydrolysis of all hydrolyzable groups and condensation of some hydrolyzed silane compounds, or a partial hydrolyzed condensate obtained by hydrolysis of some hydrolyzable groups and condensation of some or all hydrolyzed silane compounds. In other words, the hydrolysis condensate may be a fully hydrolyzed condensate, a partially hydrolyzed condensate, or a mixture thereof. Furthermore, a hydrolysis condensate of two or more hydrolyzable silane compounds means a compound formed by the condensation of at least a portion of the hydrolysates of two or more hydrolyzable silane compounds, and may be a fully hydrolyzed condensate, a partially hydrolyzed condensate, or a mixture thereof. In this specification, a hydrolyzable silyl group represents a silicon atom to which a hydrolyzable group is attached. 【0009】 [Eyeglass Lens] The eyeglass lens of this disclosure includes an eyeglass lens substrate and a coating. 【0010】 [Coating] The coating included in the eyeglass lenses of this disclosure includes a hydrolysis condensate (hereinafter also referred to as "specific hydrolysis condensate") of a silane coupling agent having a structure derived from a nonionic surfactant (hereinafter also referred to as "silane coupling agent X"), a tetraalkoxysilane, and a silane coupling agent having an amino group (hereinafter also referred to as "silane coupling agent Z"). The meaning of hydrolysis condensate is as described above. 【0011】A coating containing a specific hydrolysis condensate can be formed, for example, by curing a coating of a coating composition. The coating composition is not particularly limited as long as it is a composition that can form the above-described coating, but it is preferable that it is a composition that satisfies the following requirement 1 (hereinafter also referred to as "composition 1") or a composition that satisfies the following requirement 2 (hereinafter also referred to as "composition 2"). In other words, it is preferable that the coating is a cured film of composition 1 or composition 2. Requirement 1: It comprises at least one compound X selected from the group consisting of silane coupling agent X, its hydrolysate, and its hydrolysis condensate, at least one compound Y selected from the group consisting of tetraalkoxysilane, its hydrolysate, and its hydrolysis condensate, and at least one compound Z selected from the group consisting of silane coupling agent Z, its hydrolysate, and its hydrolysis condensate. Requirement 2: It comprises hydrolysis condensates of silane coupling agent X, tetraalkoxysilane, and silane coupling agent Z. 【0012】 The following will provide a detailed description of the film-forming composition, followed by a detailed description of the film itself. 【0013】 <Composition 1> Composition 1 comprises at least one compound X selected from the group consisting of silane coupling agent X, its hydrolysate, and its hydrolyzed condensate; at least one compound Y selected from the group consisting of tetraalkoxysilane, its hydrolysate, and its hydrolyzed condensate; and at least one compound Z selected from the group consisting of silane coupling agent Z, its hydrolysate, and its hydrolyzed condensate. The definitions of hydrolysate and hydrolyzed condensate are as described above, and when composition 1 contains hydrolyzed condensates of each component, it is preferable that it also contains partial hydrolyzed condensates. 【0014】(Silane Coupling Agent X and Compound X) Silane coupling agent X is a silane coupling agent having a structure derived from a nonionic surfactant. It is presumed that because silane coupling agent X has a structure derived from a nonionic surfactant, the film can properly retain water when water is applied, and the effects of this disclosure are excellent. Silane coupling agent X usually has a hydrolyzable silyl group. Examples of hydrolyzable groups in the hydrolyzable silyl group include alkoxy groups, halogen atoms, cyano groups, and acetoxy groups, with alkoxy groups or halogen atoms being preferred, and alkoxy groups being more preferred. The number of hydrolyzable silyl groups in silane coupling agent X is one or more, preferably 1 to 5, more preferably 1 to 3, and even more preferably 1 or 2. 【0015】 The silane coupling agent X has a structure derived from a nonionic surfactant. The silane coupling agent X often includes a hydrophilic portion and a hydrophobic portion as the structure derived from the nonionic surfactant. The hydrophilic portion preferably includes a polyalkylene oxy structure. That is, the silane coupling agent X preferably has a polyalkylene oxy structure. The number of carbon atoms in the alkylene group in the polyalkylene oxy structure is preferably 1 to 6, more preferably 2 to 4, even more preferably 2 or 3, and particularly preferably 2. The polyalkylene oxy structure is preferably a polyethylene oxy structure, a polypropylene oxy structure, or a structure obtained by combining these, with the polyethylene oxy structure being more preferred. The hydrophobic portion may be, for example, a hydrocarbon group. The hydrocarbon group may be either an aliphatic hydrocarbon group or an aromatic hydrocarbon group. The hydrocarbon group may also contain an unsaturated bond. The number of carbon atoms in the hydrocarbon group is preferably 4 or more, more preferably 6 or more, even more preferably 8 or more, and particularly preferably 12 or more. There is no particular upper limit, but from the viewpoint of film formation, 30 or less is preferred, 24 or less is more preferred, and 20 or less is even more preferred. 【0016】The silane coupling agent X is preferably a reaction product of a nonionic surfactant having active hydrogen (hereinafter also referred to as "nonionic surfactant xa") and a silane coupling agent having a reactive group that can react with the nonionic surfactant xa (hereinafter also referred to as "silane coupling agent xa"). 【0017】 Examples of active hydrogen in a nonionic surfactant xa include active hydrogen in a hydroxyl group. In other words, it is preferable that the nonionic surfactant xa has a hydroxyl group as a functional group containing active hydrogen. The number of active hydrogens in the nonionic surfactant xa is 1 or more, preferably 2 or more, and more preferably 2 to 6. The nonionic surfactant xa often has a hydrophilic part and a hydrophobic part. Preferred configurations of the hydrophilic and hydrophobic parts in the nonionic surfactant xa are as described above for the hydrophobic and hydrophilic parts of the silane coupling agent X. In particular, it is preferable that the nonionic surfactant xa has a polyalkylene oxy structure. As the nonionic surfactant xa, known nonionic surfactants having active hydrogen can be used, and ether-type nonionic surfactants, ester-type nonionic surfactants, or ether-ester-type nonionic surfactants are preferred, and polyoxyalkylene sorbitan esters, polyoxyalkylene monoalkyl ethers, or polyoxyalkylene monoalkyl esters are more preferred. Examples of polyoxyalkylene sorbitan esters include Tween 20, Tween 40, Tween 60, Tween 65, and Tween 80. 【0018】The silane coupling agent xa has a reactive group that can react with the nonionic surfactant xa. Specifically, it is preferable that it has a reactive group that can react with the active hydrogen or a functional group containing the active hydrogen to form a bond. Examples of the reactive group include isocyanate groups, epoxy groups, acid anhydride groups, thiol groups, and amino groups, and isocyanate groups are preferred because they allow for easy reaction control. Examples of silane coupling agents X include 3-isocyanatetopropyltriethoxysilane, 3-isocyanatetopropyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-trimethoxysilylpropylsuccinic anhydride, 3-aminopropyltrimethoxysilane, 3-aminopropylmethyldimethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-mercaptopropylmethyldimethylsilane, N-2-(aminoethyl)-3-aminopropylmethyldimethoxysilane, N-2-(aminoethyl)-3-aminopropyltrimethoxysilane, and 3-mercaptopropylmethyldimethoxysilane. 【0019】 The reaction product of a nonionic surfactant xa and a silane coupling agent xa can be produced, for example, by mixing the nonionic surfactant xa and the silane coupling agent xa and reacting the active hydrogen of the nonionic surfactant xa or a functional group containing the active hydrogen with the reactive group of the silane coupling agent xa. If the nonionic surfactant xa contains two or more active hydrogens, some of the active hydrogen of the nonionic surfactant xa may remain in the reaction product. The reaction between the active hydrogen and the reactive group can be carried out under known conditions, and a reaction catalyst may be used as necessary. 【0020】In composition 1, compound X may be used alone or in combination of two or more types. In composition 1, the content of compound X relative to the total content of compound X, compound Y, and compound Z is preferably 50 mol% or less, more preferably 40 mol% or less, and even more preferably 30 mol% or less. The lower limit is preferably 10 mol% or more, more preferably 15 mol% or more, and even more preferably 20 mol% or more. 【0021】 (Tetraalkoxysilane and compound Y) As for tetraalkoxysilane, Si-(OR) 4 Compounds represented by are examples. Each R independently represents an alkyl group, preferably an alkyl group having 1 to 8 carbon atoms, more preferably an alkyl group having 1 to 4 carbon atoms, and even more preferably an ethyl group. It is presumed that the tetraalkoxysilane functions as a crosslinking agent, allowing for the proper formation of a hydrolysis condensate film, and thus the effects of this disclosure are excellent. Examples of tetraalkoxysilanes include tetraethoxysilane, tetramethoxysilane, tetraisopropoxysilane, tetrabutoxysilane, tetra-n-propoxysilane, and tetrakis(2-ethylhexyloxy)silane, with tetraethoxysilane being preferred in terms of reactivity. 【0022】 In composition 1, compound Y may be used alone or in combination of two or more types. In composition 1, the content of compound Y relative to the total content of compound X, compound Y, and compound Z is preferably 70 mol% or less. The lower limit is preferably 10 mol% or more, more preferably 20 mol% or more, even more preferably 30 mol% or more, particularly preferably 40 mol% or more, and most preferably 55 mol% or more. 【0023】(Silane Coupling Agent Z and Compound Z) Silane coupling agent Z is a silane coupling agent having an amino group. Since silane coupling agent Z has an amino group, the condensation reaction of the above-described silane coupling agent X and tetraalkoxysilane is promoted to form a film, and it is presumed that the effect of the present disclosure is excellent. It is preferable that the amino group is not directly bonded to the silicon atom. That is, silane coupling agent Z preferably has a hydrolyzable silyl group and an amino group not directly bonded to the silicon atom. Examples of the hydrolyzable group are as described above, and an alkoxy group is preferable. The number of hydrolyzable silyl groups possessed by silane coupling agent Z is 1 or more, preferably 1 to 5, more preferably 1 to 3, and still more preferably 1 or 2. 【0024】 The amino group is preferably a primary amino group (-NH 2 ), a secondary amino group (-NH-), or a tertiary amino group (>N-), but a primary amino group or a secondary amino group is preferable. The number of amino groups possessed by the silane coupling agent is 1 or more, preferably 1 to 5, more preferably 1 to 3, and still more preferably 1 or 2. 【0025】 As silane coupling agent Z, a compound represented by formula (X1) or a compound represented by formula (Y1) is preferable. 【0026】 【0027】 In formula (X1), R n1 represents an alkyl group having an amino group. R x1 represents a hydroxyl group or a hydrolyzable group. R x2 represents a hydrocarbon group. mx represents an integer of 1 to 3. When there are a plurality of R x1 , R x1 may be the same or different from each other. When there are a plurality of R x2 , R x2 may be the same or different from each other. 【0028】 In formula (X1), R n1represents an alkyl group having an amino group. The alkyl group may be linear, branched, or cyclic, with linear being preferred. The number of carbon atoms in the alkyl group is preferably 1 to 20, more preferably 2 to 12, and even more preferably 3 to 10. The number of amino groups in the alkyl group is preferably 1 to 5, more preferably 1 to 3. The amino groups in the alkyl group are preferably primary or secondary amino groups. If the alkyl group has two or more amino groups, the amino groups may be of different classes; for example, it may have a primary amino group and a secondary amino group. 【0029】 In formula (X1), R x1 The symbol represents a hydroxyl group or a hydrolyzable group. Examples of hydrolyzable groups are as described above, with alkoxy groups or halogen atoms being preferred, and alkoxy groups being more preferred. As for the alkoxy group, alkoxy groups having 1 to 4 carbon atoms are preferred, and methoxy groups or ethoxy groups are more preferred. Examples of the halogen atom include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms, with chlorine atoms being preferred. 【0030】 In formula (X1), R x2 R represents a hydrocarbon group. The hydrocarbon group may be linear, branched, or cyclic. The number of carbon atoms in the hydrocarbon group is preferably 1 to 20, more preferably 1 to 10, and even more preferably 1 to 5. Alkyl alkyl groups are preferred as the hydrocarbon group. x2 Among these, alkyl groups having 1 to 5 carbon atoms are preferred. 【0031】 In formula (X1), mx represents an integer from 1 to 3. mx is preferably 2 or 3, and more preferably 3. 【0032】 The compound represented by formula (X1) is preferably the compound represented by formula (X2). 【0033】 【0034】 In formula (X2), L x1 and L x3 Each of these independently represents an alkylene group having 1 to 10 carbon atoms.x2 R represents a single bond or -NH-. x3 R represents a hydroxyl group or a hydrolyzable group. x4 represents a hydrocarbon group. nx represents an integer from 1 to 3. R x3 If multiple instances exist, R x3 They may be the same or different. x4 If multiple instances exist, R x4 They may be the same or different. 【0035】 R in equation (X2) x3 , R x4 and nx are R in equation (X1), respectively. x1 , R x2 , and are synonymous with mx, and the preferred embodiment is the same. L x1 and L x3 Each of these independently represents an alkylene group having 1 to 10 carbon atoms. The alkylene group may be linear, branched, or cyclic, with linear being preferred. The number of carbon atoms in the alkylene group is 1 to 10, preferably 1 to 8, and more preferably 1 to 5. Also, L x1 and L x3 The total number of carbon atoms is preferably 2 to 15, and more preferably 3 to 10. 【0036】 Examples of compounds represented by formula (X1) include N-2-(aminoethyl)-3-aminopropyltrimethoxysilane, 3-aminopropyltrimethoxysilane, N-2-(aminoethyl)-8-aminooctyltrimethoxysilane, and N-2-(aminoethyl)-aminomethyltrimethoxysilane. 【0037】 【0038】 In formula (Y1), R y1 and R y3 Each of these independently represents either a hydroxyl group or a hydrolyzable group. y2 and R y4 Each of these independently represents a hydrocarbon group. ny1 and ny2 each independently represent an integer from 1 to 3. y1 is at least -N(R L1) represents a divalent linking group having -, and the above divalent linking group is further -N(R L1 )-,-C(R L2 ) (Caution L3 )-, and -Si(R L4 ) (Caution L5 ) - may have a group selected from the group consisting of . L1 R represents a hydrogen atom or an alkyl group. L2 ~R L5 Each of these independently represents a hydrogen atom, a fluorine atom, or an alkyl group which may have a fluorine atom. y1 and R y3 R in equation (X1) x1 This is synonymous with the same as the preferred embodiment. R in formula (Y1) y2 and R y4 R in equation (X1) x2 This is synonymous, and the preferred embodiment is the same. In formula (Y1), ny1 and ny2 are synonymous with mx in formula (X1), and the preferred embodiment is the same. R y1 If multiple instances exist, R y1 They may be the same or different. y2 If multiple instances exist, R y2 They may be the same or different. y3 If multiple instances exist, R y3 They may be the same or different. y4 If multiple instances exist, R y4 They may be the same or different. L1 If multiple instances exist, R L1 They may be the same or different. L2 If multiple instances exist, R L2 They may be the same or different. L3 If multiple instances exist, R L3 They may be the same or different. L4 If multiple instances exist, R L4 They may be the same or different. L5 If multiple instances exist, R L5 They may be the same or different. 【0039】 In formula (Y1), L y1represents a divalent linking group having at least -N(R L1 ), and the divalent linking group may further have a group selected from the group consisting of -N(R L1 ), -C(R L2 )(R L3 ), and -Si(R L4 )(R L5 ). As L y1 , a divalent linking group consisting of -N(R L1 ) and -C(R L2 )(R L3 ) is preferable, and a divalent linking group consisting of at least two (preferably 2 to 3) -N(R L1 ) and at least three (preferably 3 to 9) -C(R L2 )(R L3 ) is more preferable. R L1 represents a hydrogen atom or an alkyl group, and a hydrogen atom is preferable. The alkyl group represented by R L1 may be linear, branched, or cyclic, and linear is preferable. The number of carbon atoms of the alkyl group is preferably 1 to 5, and more preferably 1 to 3. R L2 to R L5 each independently represent a hydrogen atom, a fluorine atom, or an alkyl group which may have a fluorine atom, and a hydrogen atom is preferable. The alkyl group which may have a fluorine atom may be linear, branched, or cyclic, and linear is preferable. The number of carbon atoms of the alkyl group is preferably 1 to 30, and more preferably 1 to 10. When the alkyl group has a fluorine atom, the number of fluorine atoms of the alkyl group is preferably 1 to 10, and more preferably 1 to 5. 【0040】 As the compound represented by the formula (Y1), a compound represented by the formula (Y2) is preferable. 【0041】 【0042】 In the formula (Y2), R y5 and R y7 each independently represent a hydroxyl group or a hydrolyzable group. R y6 and R y8Each independently represents a hydrocarbon group. ny3 and ny4 each independently represent an integer of 1 to 3. R L6 and R L7 each independently represent a hydrogen atom or an alkyl group. L y2 to L y4 each independently represent an alkylene group which may have a fluorine atom. R in formula (Y2) y5 and R y7 are synonymous with R in formula (X1) x1 and have the same preferred embodiments. R in formula (Y2) y6 and R y8 are synonymous with R in formula (X1) x2 and have the same preferred embodiments. ny3 and ny4 in formula (Y2) are synonymous with mx in formula (X1) and have the same preferred embodiments. R in formula (Y2) L6 and R L7 are synonymous with R in formula (Y1) L1 and have the same preferred embodiments. When there are a plurality of R y5 , R y5 may be the same or different from each other. When there are a plurality of R y6 , R y6 may be the same or different from each other. When there are a plurality of R y7 , R y7 may be the same or different from each other. When there are a plurality of R y8 , R y8 may be the same or different from each other. 【0043】 L y2 to L y4 The alkylene group which may have a fluorine atom represented by may be linear, branched, or cyclic, and a linear form is preferred. The number of carbon atoms of the above alkylene group is preferably 1 to 30, more preferably 1 to 10, and still more preferably 1 to 5. Also, the total number of carbon atoms of L y2 to L y4 is preferably 3 to 30, more preferably 3 to 15, and still more preferably 5 to 10. When the above alkylene group has a fluorine atom, the number of fluorine atoms of the above alkylene group is preferably 1 to 10, and more preferably 1 to 5. L y2 to Ly4 Among these, alkylene groups are preferred, and alkylene groups having 1 to 10 carbon atoms are more preferred. 【0044】 Examples of compounds represented by formula (Y1) include N,N'-bis[3-(trimethoxysilyl)propyl]-1,2-ethanediamine (X12-5263HP, manufactured by Shin-Etsu Chemical Co., Ltd.). 【0045】 In composition 1, compound Z may be used alone or in combination of two or more types. In composition 1, the content of compound Z relative to the total content of compound X, compound Y, and compound Z is preferably 65 mol% or less, more preferably 45 mol% or less, even more preferably 30 mol% or less, and particularly preferably 20 mol% or less. The lower limit is preferably 5 mol% or more, and more preferably 10 mol% or more. 【0046】 In composition 1, the molar equivalence ratio of tetraalkoxysilane to the number of hydrolyzable silyl groups in the silane coupling agent X (= tetraalkoxysilane content (mol%) / (silane coupling agent X content (mol%) × number of hydrolyzable silyl groups in silane coupling agent X)) is preferably 1 to 10, more preferably 2 to 7, and even more preferably 3 to 5. When it is above the lower limit, it is preferable in that it provides better adhesion to the lower layer of the coating. Also, when it is below the upper limit, it is preferable in that it can suppress gelation and the generation of fine particles. In composition 1, the molar equivalence ratio of the silane coupling agent Z content to the number of hydrolyzable silyl groups in the silane coupling agent X (= silane coupling agent Z content (mol%) / (silane coupling agent X content (mol%) × number of hydrolyzable silyl groups in silane coupling agent X)) is preferably 0.01 to 2.5, more preferably 0.1 to 2, and even more preferably 0.5 to 1 in that it provides better effects of the present disclosure. 【0047】 In composition 1, the total content of compound X, compound Y, and compound Z is preferably 80% by mass, more preferably 90% by mass or more, and even more preferably 95% by mass or more, based on the total solid content of the composition. The upper limit is 100% by mass. 【0048】Composition 1 may also preferably contain a solvent. Examples of solvents include water and organic solvents. 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, with alcohol-based solvents being preferred. 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 ethanol or isopropanol being preferred. 【0049】 The solvent may be a single solvent used alone, or a mixed solvent combining two or more solvents. The solvent content is preferably 80 to 99.9% by mass, and more preferably 95 to 99.9% by mass, based on the total mass of composition 1. 【0050】 Composition 1 may contain other components besides those mentioned above. Examples of other components besides those mentioned above include silane coupling agents, antioxidants, rust inhibitors, ultraviolet absorbers, light stabilizers, fungicides, antibacterial agents, biofouling inhibitors, deodorants, pigments, flame retardants, and antistatic agents, which are different from compounds X, Y, and Z. 【0051】 The method for producing composition 1 is not particularly limited and can be produced by known methods. Specifically, for example, one method involves mixing compound X, compound Y, and compound Z with an optional component such as a solvent as needed. When adding each component, they may be added all at once or in multiple steps. 【0052】<Composition 2> Composition 2 contains hydrolysis condensates of silane coupling agent X, tetraalkoxysilane, and silane coupling agent Z. The definitions and preferred embodiments of silane coupling agent X, tetraalkoxysilane, and silane coupling agent Z in Composition 2 are the same as those of silane coupling agent X, tetraalkoxysilane, and silane coupling agent Z in Composition 1 described above. The definition of hydrolysis condensates is as described above, and it is preferable that Composition 2 contains partially hydrolysis condensates. Note that the hydrolysis condensates in Composition 2 may be specific hydrolysis condensates. 【0053】 Composition 2 may also preferably contain a solvent. Examples of solvents include those that may be contained in Composition 1. The solvent may be a single solvent used alone, or a mixed solvent consisting of two or more solvents. The solvent content is preferably 80 to 99.9% by mass, and more preferably 95 to 99.9% by mass, based on the total mass of Composition 2. 【0054】 Composition 2 may contain other components besides the hydrolysis condensate described above. Examples of other components include the components exemplified above as other components that may be contained in Composition 1, compound X, compound Y, and compound Z. In Composition 2, the total content of the hydrolysis condensate, compound X, compound Y, and compound Z described above is preferably 80% by mass, more preferably 90% by mass or more, and even more preferably 95% by mass or more, based on the total solid content of the composition. The upper limit is 100% by mass. 【0055】 The method for producing composition 2 is not particularly limited, but the method of heating composition 1 as described above is preferred. By heating composition 1, hydrolysis and condensation reactions of compound X, compound Y, and compound Z proceed, and composition 2 is obtained. The heating temperature is preferably 30 to 80°C, and more preferably 40 to 80°C. The heating time is preferably 0.2 to 36 hours, and more preferably 6 to 24 hours. 【0056】<Specific Hydrolyzed Condensate> As described above, the coating contains a specific hydrolyzed condensate, which is a hydrolyzed condensate of silane coupling agent X, tetraalkoxysilane, and silane coupling agent Z. The specific hydrolyzed condensate contains units based on silane coupling agent X, units based on tetraalkoxysilane, and units based on silane coupling agent Z. The molar ratio of each unit in the specific hydrolyzed condensate is usually approximately the same as the molar ratio of the compounds that give each unit in the coating-forming composition described above. 【0057】 The specified hydrolysis condensate may contain one unit based on silane coupling agent X, one unit based on tetraalkoxysilane, and one unit based on silane coupling agent Z, or two or more units. In the specified hydrolysis condensate, the content of units based on silane coupling agent X relative to the total content of units based on silane coupling agent X, units based on tetraalkoxysilane, and units based on silane coupling agent Z is preferably 50 mol% or less, more preferably 40 mol% or less, and even more preferably 30 mol% or less. The lower limit is preferably 10 mol% or more, more preferably 15 mol% or more, and even more preferably 20 mol% or more. In the specified hydrolysis condensate, the content of units based on tetraalkoxysilane relative to the total content of units based on silane coupling agent X, units based on tetraalkoxysilane, and units based on silane coupling agent Z is preferably 70 mol% or less. The lower limit is preferably 10 mol% or more, more preferably 20 mol% or more, even more preferably 30 mol% or more, particularly preferably 40 mol% or more, and most preferably 55 mol% or more. In the specific hydrolysis condensate, the content of units based on silane coupling agent Z relative to the total content of units based on silane coupling agent X, units based on tetraalkoxysilane, and units based on silane coupling agent Z is preferably 65 mol% or less, more preferably 45 mol% or less, even more preferably 30 mol% or less, and particularly preferably 20 mol% or less. The lower limit is preferably 5 mol% or more, and more preferably 10 mol% or more. 【0058】The specified hydrolysis condensate may contain units other than those based on the silane coupling agent X, tetraalkoxysilane, and silane coupling agent Z described above. Examples of other units include units based on silane coupling agents other than silane coupling agent X and silane coupling agent Z. The total content of units based on silane coupling agent X, tetraalkoxysilane, and silane coupling agent Z is preferably 80 mol% or more, more preferably 90 mol% or more, and even more preferably 95 mol% or more, relative to the total units of the specified hydrolysis condensate. The upper limit is 100 mol%. 【0059】 The coating may contain components other than the specified hydrolysis condensate. Examples of components other than the specified hydrolysis condensate include antioxidants, rust inhibitors, ultraviolet absorbers, light stabilizers, antifungal agents, antibacterial agents, anti-fouling agents, deodorants, pigments, flame retardants, and antistatic agents. From the viewpoint of the curability of the coating, the content of the specified hydrolysis condensate in the coating is preferably 80% by mass, more preferably 90% by mass or more, and even more preferably 95% by mass or more, based on the total mass of the coating. The upper limit is 100% by mass. 【0060】 The thickness of the coating is preferably 1 to 1000 nm, as this provides superior effects compared to the present disclosure. 【0061】 The spectacle lens of this disclosure preferably has a coating on its outermost surface. The spectacle lens of this disclosure may have a coating on only one side of the spectacle lens substrate, or it may have a coating on both sides. 【0062】<Method for Manufacturing a Coating> The preferred method for manufacturing a coating is to apply a coating-forming composition onto a desired member to form a coating film, and then cure the coating film. More preferably, the method for manufacturing a coating includes a step of forming a coating film of a coating-forming composition containing a solvent, and a step of removing the solvent to cure the coating film, from the viewpoint of uniformity of the formed film. Examples of methods for applying the coating-forming composition include dipping coating, spin coating, spray coating, inkjet coating, and flow coating. Examples of curing treatment methods include drying and heat treatment. The temperature for the curing treatment is preferably 25 to 90°C, and more preferably 40 to 80°C. The curing treatment time is preferably 0.2 to 2 hours, and more preferably 0.5 to 1 hour. 【0063】 It is preferable to apply a surface treatment to the surface of the layer forming the coating of the coating composition (preferably the surface of the anti-reflective layer described later) in order to ensure that the coating adheres more firmly to the adherend and has superior abrasion resistance. Examples of surface treatments include surface activation treatment and cleaning treatment. Specifically, examples of surface treatments include plasma treatment, corona treatment, ozone treatment, and UV treatment, with plasma treatment being preferred. 【0064】 In particular, the coating is preferably a film obtained by curing a coating film of the composition obtained by heat-treating composition 1. The heat treatment causes at least a portion of the hydrolysis and condensation of compound X, compound Y, and compound Z to proceed, leading to prepolymerization and facilitating the formation of a coating. The composition obtained by heat-treating composition 1 may be the composition 2 described above. In particular, the method for producing the coating preferably includes the steps of: heat-treating composition 1 to obtain composition 2; forming a coating film of composition 2; and curing the coating film to obtain a coating. The conditions for the heat treatment can be appropriately adjusted depending on the composition of the coating and the coating-forming composition. The heating temperature is preferably 30 to 80°C, and more preferably 40 to 80°C. The heating time is preferably 0.2 to 36 hours, and more preferably 6 to 24 hours. 【0065】[Eyeglass Lens Substrate] Materials constituting the eyeglass lens substrate included in the eyeglass lenses of this disclosure include organic materials and inorganic materials, with organic materials being preferred. Examples of organic materials include acrylic acid ester resin, methacrylic acid ester resin, thiourethane resin, allyl resin, episulfide resin, polycarbonate, urethane resin, polyester, polystyrene, polyethersulfone, poly-methylpentene-1, and diethylene glycol bisallyl carbonate resin (CR-39), with thiourethane resin, episulfide resin, or diethylene glycol bisallyl carbonate resin being preferred. 【0066】 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. The episulfide resin is a resin obtained by ring-opening polymerization of a monomer having an episulfide group (epithio group), or a mixed monomer containing such monomer. Preferred monomers having an episulfide group are bis(2,3-epithiopropyl)sulfide or bis(2,3-epithiopropyl)disulfide. 【0067】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. 【0068】 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, from the standpoint of ease of handling. The refractive index of the spectacle lens base material is preferably 1.50 or higher, more preferably 1.60 to 1.80, and even more preferably 1.60 to 1.74. 【0069】 The spectacle lenses of this disclosure may include layers other than the spectacle lens substrate and coating. The spectacle lens preferably has an anti-reflective layer, and more preferably has the spectacle lens substrate, anti-reflective layer, and coating in this order. The spectacle lens may have the anti-reflective layer and coating on one surface of the spectacle lens substrate, or it may have the anti-reflective layer and coating on both sides of the substrate. The anti-reflective layer is preferably arranged adjacent to the coating. In other words, the spectacle lens preferably has the spectacle lens substrate, anti-reflective layer, and coating arranged adjacent to the anti-reflective layer in this order. 【0070】 [Anti-reflective layer] Eyeglass lenses preferably have an anti-reflective layer. 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 means an anti-reflective layer composed of an inorganic compound. A multi-layer anti-reflective layer may have a structure in which low refractive index layers and high refractive index layers are alternately stacked. Examples of materials constituting the high refractive index layer include oxides of metals selected from titanium, zirconium, aluminum, niobium, tantalum, and lanthanum. Examples of materials constituting the low refractive index layer include silicon oxide. 【0071】Methods for forming an anti-reflective layer include, for example, vacuum deposition, sputtering, ion plating, ion beam-assisted deposition, and dry methods such as CVD. 【0072】 The thickness of the anti-reflective layer is preferably 100 to 10,000 nm, and more preferably 300 to 700 nm. 【0073】 [Primer layer] The spectacle lens may have a primer layer. It is preferable that the primer layer be placed 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. 【0074】 The primer layer preferably contains a resin. The resin may be in particulate form. Examples of resins include urethane resin, epoxy resin, phenolic resin, polyimide, polyester, bismaleimide resin, and polyolefin, with urethane resin being preferred. The primer layer may also contain additives such as surfactants. 【0075】 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 to apply the coating film-forming composition described above. 【0076】 The thickness of the primer layer is preferably 0.3 to 2.0 μm. 【0077】[Hard Coat 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 eyeglass lenses have a hard coat layer, the scratch resistance of the eyeglass lenses can be improved. The hard coat layer preferably exhibits a hardness of H or higher on the pencil hardness scale according to JIS K5600. 【0078】 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. 【0079】 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 forming composition onto a substrate is to apply the coating composition described above. 【0080】 The thickness of the hard coat layer is preferably 1 to 20 μm, and more preferably 2 to 18 μm. 【0081】 [Method for Manufacturing Eyeglass Lenses] Known manufacturing methods can be used for manufacturing eyeglass lenses. Specifically, for example, a method that includes the step of forming a coating on at least one surface of an eyeglass lens substrate can be used. In particular, a method for manufacturing eyeglass lenses is preferably one that includes the step of forming an anti-reflective layer on at least one surface of an eyeglass lens substrate and the step of forming a coating on the anti-reflective layer. The method for forming each layer is as described above. 【0082】[Composition] The composition of the present disclosure is a composition that satisfies at least one of the following requirements 1 and 2. The composition of the present disclosure is a composition that can form the above-described coating of the present disclosure. Requirement 1: comprises at least one compound X selected from the group consisting of silane coupling agent X, its hydrolysates, and hydrolyzed condensates; at least one compound Y selected from the group consisting of tetraalkoxysilane, its hydrolysates, and hydrolyzed condensates; and at least one compound Z selected from the group consisting of silane coupling agent Z, its hydrolysates, and hydrolyzed condensates. Requirement 2: comprises hydrolyzed condensates of silane coupling agent X, tetraalkoxysilane, and silane coupling agent Z. 【0083】 Requirements 1 and 2 in the compositions of this disclosure are the same as requirements 1 and 2 in the above-described coating compositions, the definition and preferred embodiment of a composition that satisfies requirement 1 is the same as composition 1 above-described as a coating composition, and the definition and preferred embodiment of a composition that satisfies requirement 2 is the same as composition 2 above-described as a coating composition. 【0084】As described above, the compositions of this disclosure can be used in the manufacture of eyeglass lenses. The compositions of this disclosure can also be used to form laminates having a substrate other than an eyeglass lens substrate and a coating formed by the compositions of this disclosure. An example of the application of the above laminate is as a front panel (window film) in a flexible display device. The above flexible display device 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 of the organic electroluminescent display panel and is configured to be bendable. The laminate for flexible display devices may further have a polarizing plate (preferably a circular polarizing plate) and a touch sensor. In the laminate for flexible display devices, it is preferable that the laminate (window film), polarizing plate, and touch sensor are laminated in that order from the viewing side, and also preferable that the laminate (window film), touch sensor, and polarizing plate are laminated in that order from the viewing side. 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 laminated using adhesives and other adhesives. 【0085】 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. 【0086】 The raw materials used in the preparation of the compositions of the examples and comparative examples are described below. • Tween 20: Polyoxyethylene sorbitan monolaurate, manufactured by TCI, a nonionic surfactant having three hydroxyl groups in its molecule. • Isocyanate silane: 3-(triethoxysilyl)propyl isocyanate, manufactured by TCI. • DBTDL: Dibutyltin dilaurate, manufactured by Merck. • TEOS: Tetraethoxysilane, manufactured by TCI. • Silane coupling agent Z: N-2-(aminoethyl)-8-aminooctyltrimethoxysilane, manufactured by Shin-Etsu Chemical Co., Ltd., trade name KBM-6803. 【0087】 [Manufacturing of eyeglass lenses] [Preparation of composition] A coating composition was prepared according to the following procedure. 【0088】[Preparation of Silane Coupling Agent X] Tween 20 (4.79 parts by mass, 3.90 mmol), isocyanate silane (0.80 parts by mass, 3.23 mmol), and DBTDL (one drop) as a catalyst were mixed and stirred at 50°C for 7 hours in a nitrogen gas atmosphere to obtain silane coupling agent X, which is a reaction product of Tween 20:isocyanate silane in a 1:1 molar ratio. Further, deionized water (1.46 parts by mass) and ethanol (13.01 parts by mass) were added as solvents to obtain a solution of silane coupling agent X. 【0089】 <Preparation of Composition 1> To a silane coupling agent X solution (0.20 parts by mass), TEOS (0.017 parts by mass), silane coupling agent Z (0.005 parts by mass), and ethanol (3.20 parts by mass) were added and mixed, and the mixture was heated at 70°C for 19 hours to form a prepolymer. At this time, the molar ratio of silane coupling agent X, TEOS, and silane coupling agent Z in Composition 1 was 1:2.5:0.5. 【0090】 <Preparation of Compositions 2-7> Compositions 2-7 were prepared in the same procedure as for Composition 1, except that the amounts of TEOS and silane coupling agent Z used were adjusted so that the molar ratio of silane coupling agent X, TEOS, and silane coupling agent Z in the composition was as shown in Table 1. Compositions 5 and 7 did not use TEOS. 【0091】 【0092】[Manufacturing of Eyeglass Lens 1] An anti-reflective lens (a lens with the same structure as the product name ECC (manufactured by Nikon-Essilor) but without the top coat layer, having an eyeglass lens base, primer layer, hard coat layer, and anti-reflective layer in that order. The top coat layer is not formed from the beginning) was prepared as a base material, and the anti-reflective layer was cleaned with a plasma dry cleaner (Yamato Scientific Co., Ltd. PDC210, 400W, processing time 120 seconds). The obtained composition 1 was coated onto the cleaned anti-reflective layer by spin coating (500 rpm for 30 seconds, followed by 2000 rpm for 1 second). Subsequently, the lens on which the coating of composition 1 was formed was heated and cured in an 80°C constant temperature bath for 30 minutes to form a film. Furthermore, excess composition that was not adhering to the lens was removed by rubbing the surface with a finger while running tap water over it, and eyeglass lens 1 was obtained. 【0093】 [Manufacturing of eyeglass lenses 2-7] Eyeglass lenses 2-7 were manufactured in the same manner as eyeglass lens 1, except that compositions 2-7 were used instead of composition 1. 【0094】 [Evaluation] The coefficient of dynamic friction of the spectacle lenses of each example and comparative example when water was applied was evaluated according to the following procedure. Using a constant load measurement with a Tribogear (surface properties measuring instrument TYPE: 38) manufactured by Shinto Kagaku Co., Ltd., the coefficient of dynamic friction μk was measured when the convex surface on which the coating of the lens was formed while wet with tap water was wiped with a spectacle cloth (manufactured by Pearl Co., Ltd., product name "Dot Clean"). The measurement conditions were: load: 200 g, travel distance: 20 mm, travel speed: 400 mm / min, temperature: 25 °C. A coefficient of dynamic friction μk of 0.450 or less is preferable for practical purposes. 【0095】 [Results] Table 2 shows the type of spectacle lens, the type of composition used in the manufacture of the spectacle lens, and the coefficient of dynamic friction μk for each example and comparative example. 【0096】 【0097】The evaluation results confirmed that the spectacle lenses of this disclosure have a low coefficient of dynamic friction when water is applied. A comparison of Examples 1 to 4 confirmed that in composition 1, the coefficient of dynamic friction μk is smaller when the content of compound Z relative to the total content of compound X, compound Y, and compound Z is 45 mol% or less, even smaller when it is 30 mol% or less, and particularly small when it is 20 mol% or less.
Claims
1. An eyeglass lens comprising an eyeglass lens substrate and a coating, wherein the coating comprises a hydrolysis condensate of a silane coupling agent having a structure derived from a nonionic surfactant, a tetraalkoxysilane, and a silane coupling agent having an amino group.
2. The spectacle lens according to claim 1, wherein the silane coupling agent having a structure derived from the nonionic surfactant is a reaction product of a nonionic surfactant having active hydrogen and a silane coupling agent having a reactive group that can react with the nonionic surfactant having active hydrogen.
3. The spectacle lens according to claim 2, wherein the nonionic surfactant has two or more active hydrogens.
4. The spectacle lens according to any one of claims 1 to 3, wherein the silane coupling agent having a structure derived from the nonionic surfactant has a polyalkylene oxy structure.
5. A composition that satisfies at least one of requirement 1 and requirement 2. Requirement 1: A composition comprising at least one compound X selected from the group consisting of silane coupling agents having a structure derived from a nonionic surfactant, their hydrolysates, and their hydrolyzed condensates; at least one compound Y selected from the group consisting of tetraalkoxysilanes, their hydrolysates, and their hydrolyzed condensates; and at least one compound Z selected from the group consisting of silane coupling agents having an amino group, their hydrolysates, and their hydrolyzed condensates. Requirement 2: A composition comprising the silane coupling agent having a structure derived from a nonionic surfactant, the tetraalkoxysilane, and the hydrolyzed condensates of the silane coupling agent having an amino group.
6. The composition according to claim 5, wherein the silane coupling agent having a structure derived from the nonionic surfactant is a reaction product of a nonionic surfactant having active hydrogen and a silane coupling agent having a reactive group that can react with the nonionic surfactant having active hydrogen.
7. The composition according to claim 6, wherein the nonionic surfactant has two or more active hydrogens.
8. The composition according to any one of claims 5 to 7, which satisfies requirement 1, and wherein the content of compound Z relative to the total content of compound X, compound Y, and compound Z is 65 mol% or less.
9. The composition according to any one of claims 5 to 8, wherein the silane coupling agent having a structure derived from the nonionic surfactant has a polyalkylene oxy structure.