Composition and eyeglass lens

Abstract

The present disclosure addresses the problem of providing a composition which is capable of forming a film that is excellent in terms of water repellency and wear resistance. A composition according to the present disclosure contains a silyl isocyanate compound, a polysiloxane that has a reactive functional group, and at least one compound that is selected from the group consisting of a silane coupling agent having an amino group, a hydrolysate thereof, and a hydrolysis condensate thereof.

Description

Composition, eyeglass lens

[0001] The present disclosure relates to compositions and eyeglass lenses.

[0002] Patent Document 1 discloses a primer layer containing a composite compound having a structure in which a titanium compound oligomer is reacted with a silicon compound having one or more alkoxy groups in the molecule or a mixture thereof, and a solvent, and a release agent layer using a silyl isocyanate compound as a curing agent.

[0003] JP 2009-126923 A

[0004] The present disclosure relates to a composition comprising a silyl isocyanate compound, a polysiloxane having a reactive functional group, and at least one compound selected from the group consisting of a silane coupling agent having an amino group, a hydrolyzate thereof, and a hydrolyzed condensate thereof.

[0005] The present disclosure will be described in detail below. The composition of the present disclosure can form a film having excellent water repellency and abrasion resistance. In the present disclosure, abrasion resistance refers to abrasion resistance of water repellency. The following description of the constituent elements may be based on a representative embodiment of the present disclosure, but the present disclosure is not limited to such an embodiment.

[0006] In this specification, a numerical range expressed using "to" means a range that includes the numerical values ​​written before and after "to" as the lower and upper limits. Furthermore, in this specification, when two or more types of a certain component are present, the "content" of that component means the total content of those two or more components. In this specification, in a numerical range described in stages, the upper or lower limit value described in a certain numerical range may be replaced with the upper or lower limit value of another numerical range described in stages. Furthermore, in a numerical range described in this specification, the upper or lower limit value described in a certain numerical range may be replaced with a value shown in the Examples. In this specification, a combination of two or more preferred embodiments is a more preferred embodiment.

[0007] In this specification, the "solid content" of a composition means components that form a layer (film) formed using the composition, and when the composition contains a solvent (e.g., an organic solvent, water, etc.), it means all components excluding the solvent. Furthermore, liquid components that form a layer (film) using the composition are also considered to be solid content.

[0008] The bonding direction of a divalent group represented in this specification is not limited unless otherwise specified. For example, when Y is -COO- in a compound represented by the formula "X-Y-Z", Y may be -CO-O- or -O-CO-. Furthermore, the compound may be "X-CO-O-Z" or "X-O-CO-Z". In this specification, unless otherwise specified, when there are multiple substituents and linking groups, etc. represented by specific symbols (hereinafter referred to as substituents, etc.), or when multiple substituents, etc. are specified simultaneously, this means that the respective substituents, etc. may be the same or different from each other. The same applies to the specification of the number of substituents, etc.

[0009] [Composition] The composition contains a silyl isocyanate compound, a polysiloxane having a reactive functional group (hereinafter also referred to as "specific polysiloxane"), and at least one compound selected from the group consisting of a silane coupling agent having an amino group, a hydrolyzate thereof, and a hydrolysis condensate thereof (hereinafter also referred to as "silane coupling agents having an amino group").

[0010] [Silyl isocyanate compound] The composition contains a silyl isocyanate compound. The silyl isocyanate compound is a compound having an isocyanate group directly bonded to a silicon atom. The number of isocyanate groups directly bonded to a 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.

[0011] The silyl isocyanate compound is preferably a compound represented by formula (A1). Ａ１４－ｎ１ -Si(NCO) ｎ１ Formula (A1) In formula (A1), R Ａ１ each independently represents a non-hydrolyzable group; n1 represents an integer of 1 to 4;

[0012] In formula (A1), R Ａ１ The non-hydrolyzable group represented by is not particularly limited as long as the bond to the silicon atom is not hydrolyzed, and examples thereof include hydrocarbon groups which may have a substituent. The hydrocarbon group is preferably an alkyl group or an aryl group, and more preferably an alkyl group. The alkyl group may be linear, branched, or cyclic, and is preferably linear or branched, and more preferably linear. The alkyl group preferably has 1 to 10 carbon atoms, more preferably 1 to 6, even more preferably 1 to 4, and particularly preferably 1 or 2. The aryl group may be monocyclic or polycyclic, and is preferably monocyclic. The aryl group preferably has 6 to 12 carbon atoms, and more preferably 6 to 10. Examples of substituents which the hydrocarbon group may have include an alkoxy group, an acyl group, and a halogen atom. R Ａ１ As the alkyl group, an alkyl group having 1 to 4 carbon atoms is preferable, and an alkyl group having 1 to 4 carbon atoms is more preferable.

[0013] In formula (A1), n1 represents an integer of 1 to 4, preferably an integer of 2 to 4, and more preferably 3 or 4.

[0014] Examples of the silyl isocyanate compound include methyl triisocyanate silane, tetraisocyanate silane, and dimethyl diisocyanate silane, with methyl triisocyanate silane or tetraisocyanate silane being preferred, and methyl triisocyanate silane being more preferred.

[0015] 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 mass %, more preferably 1 to 2.5 mass %, and even more preferably 1 to 2 mass %, based on the total mass of the composition.

[0016] [Specific Polysiloxane] The composition contains a specific polysiloxane, which is a polysiloxane having a reactive functional group. It is presumed that the reactive functional group of the specific polysiloxane reacts with a silyl isocyanate compound to form a film with excellent water repellency and abrasion resistance. The mode of the reaction is not particularly limited. For example, the reactive functional group may react with an isocyanate group to form a bond (e.g., a urethane bond), or the isocyanate group may be eliminated to form a bond between the reactive functional group or a portion thereof and a silicon atom of the silyl isocyanate compound. The reactive functional group is preferably a functional group containing an active hydrogen atom. Specific examples of the reactive functional group include a hydroxyl group, an amino group, a carboxyl group, a urethane group, and a urea group, with a hydroxyl group being preferred. The number of reactive functional groups contained in the specific polysiloxane is one or more, and may be two or more. The reactive functional group may be present at the terminal of the specific polysiloxane or in a side chain.

[0017] The specific polysiloxane has a polysiloxane structure. The polysiloxane structure is preferably a dialkylpolysiloxane structure, more preferably a dimethylpolysiloxane structure. The polysiloxane structure may be linear, branched, or cyclic, and is preferably linear.

[0018] 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, and more preferably 1 to 5% by mass, based on the total mass of the composition.

[0019] [Silane Coupling Agents Having an Amino Group] The composition contains at least one compound selected from the group consisting of silane coupling agents having an amino group, their hydrolysates, and their hydrolyzed condensates. The hydrolyzate of the silane coupling agent refers to a compound obtained by hydrolyzing the hydrolyzable groups of the silane coupling agent. The hydrolyzate of the silane coupling agent may be a complete hydrolyzate in which all of the hydrolyzable groups in the silane coupling agent are hydrolyzed, or a partial hydrolyzate in which only a portion of the hydrolyzable groups are hydrolyzed. In other words, the hydrolyzate may be a complete hydrolyzate, a partial hydrolyzate, or a mixture thereof. The hydrolyzed condensate of the silane coupling agent refers to a compound obtained by condensation of the hydrolyzed silane coupling agent. The hydrolyzed condensate of the silane coupling agent may be a complete hydrolyzed condensate in which all of the hydrolyzable groups are hydrolyzed and the entire hydrolyzate is condensed, or a partial hydrolyzed condensate in which only a portion of the hydrolyzable groups are hydrolyzed and some or all of the hydrolyzate is condensed. That is, the hydrolysis condensate may be a complete hydrolysis condensate, a partial hydrolysis condensate, or a mixture thereof. Note that the silane coupling agent having an amino group is a component different from the above-mentioned components (the silyl isocyanate compound and the specific polysiloxane).

[0020] In a silane coupling agent having an amino group, it is preferable that the amino group is not directly bonded to a silicon atom. That is, it is preferable that the silane coupling agent having an amino group has a hydrolyzable group or a hydroxyl group directly bonded to a silicon atom and an amino group not directly bonded to a silicon atom. The number of silicon atoms in the silane coupling agent having an amino group is 1 or more, preferably 1 to 5, more preferably 1 to 3, and even more preferably 1 or 2. Examples of the hydrolyzable group include an alkoxy group, a halogen atom, a cyano group, and an acetoxy group, with an alkoxy group or a halogen atom being preferred, and an alkoxy group being more preferred.

[0021] The amino group may be a primary amino group (-NH２ Examples of the amino group include a primary amino group (-NH-), a secondary amino group (-NH-), and a tertiary amino group (>N-), and a primary amino group or a secondary amino group is preferred because it has excellent reactivity with a silyl isocyanate compound, improves adhesion between an adherend and a film formed from the composition, and provides more excellent abrasion resistance. The number of amino groups contained in the silane coupling agent is 1 or more, preferably 1 to 5, more preferably 1 to 3, and even more preferably 1 or 2.

[0022] The silane coupling agent having an amino group is preferably a compound represented by formula (X1) or a compound represented by formula (Y1).

[0023]

[0024] In formula (X1), R ｎ１ represents an alkyl group having an amino group. ｘ１ represents a hydroxyl group or a hydrolyzable group. ｘ２ represents a hydrocarbon group. mx represents an integer of 1 to 3. R ｘ１ If there are multiple ｘ１ R may be the same or different. ｘ２ If there are multiple ｘ２ They may be the same or different.

[0025] In formula (X1), R ｎ１ represents an alkyl group having an amino group. The alkyl group may be linear, branched, or cyclic, with linear being preferred. The alkyl group preferably has 1 to 20 carbon atoms, more preferably 2 to 12, and even more preferably 3 to 10. The alkyl group preferably has 1 to 5 amino groups, more preferably 1 to 3. The amino group in the alkyl group is preferably a primary amino group or a secondary amino group. When the alkyl group has two or more amino groups, the series numbers of the amino groups may be different from each other, and for example, the alkyl group may have a primary amino group and a secondary amino group.

[0026] In formula (X1), R ｘ１represents a hydroxyl group or a hydrolyzable group. Examples of the hydrolyzable group include an alkoxy group, a halogen atom, a cyano group, and an acetoxy group, with an alkoxy group or a halogen atom being preferred, and an alkoxy group being more preferred. The alkoxy group is preferably an alkoxy group having 1 to 4 carbon atoms, with a methoxy group or an ethoxy group being more preferred. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, with a chlorine atom being preferred.

[0027] In formula (X1), R ｘ２ 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. The hydrocarbon group is preferably an alkyl group. R ｘ２ Among these, alkyl groups having 1 to 5 carbon atoms are preferred.

[0028] In formula (X1), mx represents an integer of 1 to 3. mx is preferably 2 or 3, and more preferably 3.

[0029] The compound represented by formula (X1) is preferably a compound represented by formula (X2).

[0030]

[0031] In formula (X2), L ｘ１ and L ｘ３ each independently represents an alkylene group having 1 to 10 carbon atoms. ｘ２ represents a single bond or —NH— (secondary amino group). ｘ３ represents a hydroxyl group or a hydrolyzable group. ｘ４ represents a hydrocarbon group. nx represents an integer of 1 to 3. R ｘ３ If there are multiple ｘ３ R may be the same or different. ｘ４ If there are multiple ｘ４ They may be the same or different.

[0032] R in formula (X2) ｘ３ , R ｘ４ and nx are R in formula (X1),ｘ１ , R ｘ２ and mx, and the preferred embodiments are also the same.

[0033] In formula (X2), L ｘ１ and L ｘ３ each independently represents an alkylene group having 1 to 10 carbon atoms. The alkylene group may be linear, branched, or cyclic, and is preferably linear. The alkylene group has 1 to 10 carbon atoms, preferably 1 to 8 carbon atoms, and more preferably 1 to 5 carbon atoms. Furthermore, L ｘ１ and L ｘ２ The total number of carbon atoms is preferably 2 to 15, and more preferably 3 to 10.

[0034] Examples of the compound represented by formula (X1) include N-2-(aminoethyl)-3-aminopropyltrimethoxysilane, 3-aminopropyltrimethoxysilane, N-2-(aminoethyl)-8-aminooctyltrimethoxysilane, and N-2-(aminoethyl)-aminomethyltrimethoxysilane.

[0035]

[0036] In formula (Y1), R ｙ１ and R ｙ３ R each independently represents a hydroxyl group or a hydrolyzable group. ｙ２ and R ｙ４ each independently represents a hydrocarbon group; ny1 and ny2 each independently represents an integer of 1 to 3; L ｙ１ represents a divalent linking group having at least —NH— (secondary amino group), and the divalent linking group further comprises —NR Ｌ１ -, -C(R Ｌ２ ) (R Ｌ３ )- and -Si(R Ｌ４ ) (R Ｌ５ )-. Ｌ１ represents a hydrogen atom or an alkyl group. Ｌ２ ~R Ｌ５ R in formula (Y1) each independently represents a hydrogen atom, a fluorine atom, or an alkyl group which may have a fluorine atom. ｙ１ and R ｙ３ is R in formula (X1).ｘ１ The meaning and preferred embodiments are also the same as those of the formula (Y1). ｙ２ and R ｙ４ is R in formula (X1). ｘ２ The definitions and preferred embodiments of ny1 and ny2 in formula (Y1) are the same as those of mx in formula (X1), and the preferred embodiments are also the same. ｙ１ If there are multiple ｙ１ R may be the same or different. ｙ２ If there are multiple ｙ２ R may be the same or different. ｙ３ If there are multiple ｙ３ R may be the same or different. ｙ４ If there are multiple ｙ４ R may be the same or different. Ｌ１ If there are multiple Ｌ１ R may be the same or different. Ｌ２ If there are multiple Ｌ２ R may be the same or different. Ｌ３ If there are multiple Ｌ３ R may be the same or different. Ｌ４ If there are multiple Ｌ４ R may be the same or different. Ｌ５ If there are multiple Ｌ５ They may be the same or different.

[0037] In formula (Y1), L ｙ１ represents a divalent linking group having at least —NH—, and the divalent linking group further comprises —NR Ｌ１ -, -C(R Ｌ２ ) (R Ｌ３ )- and -Si(R Ｌ４ ) (R Ｌ５ )-. ｙ１ As the alkyl group, -NH- and -C(R Ｌ２ ) (R Ｌ３ A divalent linking group consisting of at least two (preferably 2 to 3) —NH— and at least three (preferably 3 to 9) —C(R Ｌ２ ) (RＬ３ A divalent linking group consisting of R Ｌ１ represents a hydrogen atom or an alkyl group, and preferably a hydrogen atom. Ｌ１ When is a hydrogen atom, -NR Ｌ１ - represents a secondary amino group, R Ｌ１ is an alkyl group, Ｌ１ - represents a tertiary amino group. Ｌ１ The alkyl group represented by R may be linear, branched, or cyclic, and is preferably linear. The number of carbon atoms in the alkyl group is preferably 1 to 5, and more preferably 1 to 3. Ｌ２ ~R Ｌ５ each independently represents a hydrogen atom, a fluorine atom, or an alkyl group which may have a fluorine atom, with a hydrogen atom being preferred. The alkyl group which may have a fluorine atom may be linear, branched, or cyclic, with a linear group being preferred. The alkyl group preferably has 1 to 30 carbon atoms, more preferably 1 to 10. When the alkyl group has a fluorine atom, the alkyl group preferably has 1 to 10 fluorine atoms, more preferably 1 to 5 fluorine atoms.

[0038] The compound represented by formula (Y1) is preferably a compound represented by formula (Y2).

[0039]

[0040] In formula (Y2), R ｙ５ and R ｙ７ R each independently represents a hydroxyl group or a hydrolyzable group. ｙ６ and R ｙ８ each independently represents a hydrocarbon group; ny3 and ny4 each independently represents an integer of 1 to 3; L ｙ２ ~L ｙ４ R in formula (Y2) each independently represents an alkylene group which may have a fluorine atom. ｙ５ and R ｙ７ is R in formula (X1). ｘ１ The meaning and preferred embodiments are also the same as those of the formula (Y2). ｙ６ and R ｙ８ is R in formula (X1). ｘ２The definitions and preferred embodiments of ny3 and ny4 in formula (Y2) are the same as those of mx in formula (X1), and the preferred embodiments are also the same. ｙ５ If there are multiple ｙ５ R may be the same or different. ｙ６ If there are multiple ｙ６ R may be the same or different. ｙ７ If there are multiple ｙ７ R may be the same or different. ｙ８ If there are multiple ｙ８ They may be the same or different.

[0041] In formula (Y2), L ｙ２ ~L ｙ４ The alkylene group represented by the formula (I) may have a fluorine atom and may be linear, branched, or cyclic, with linear being preferred. The alkylene group preferably has 1 to 30 carbon atoms, more preferably 1 to 10, and even more preferably 1 to 5. ｙ２ ~L ｙ４ The total number of carbon atoms in the alkylene group is preferably 3 to 30, more preferably 3 to 15, and even more preferably 5 to 10. When the alkylene group has a fluorine atom, the number of fluorine atoms in the alkylene group is preferably 1 to 10, and more preferably 1 to 5. ｙ２ ~L ｙ４ Among these, alkylene groups are preferred, and alkylene groups having 1 to 10 carbon atoms are more preferred.

[0042] An example of the compound represented by formula (Y1) is N,N'-bis[3-(trimethoxysilyl)propyl]-1,2-ethanediamine (X12-5263HP, manufactured by Shin-Etsu Chemical Co., Ltd.).

[0043] The silane coupling agents having an amino group may be used alone or in combination of two or more. The content of the silane coupling agents having an amino group relative to the content of the silyl isocyanate compound is preferably 0.5 to 44 mass%, more preferably 1.8 to 27 mass%, and even more preferably 2 to 15 mass%, in terms of better abrasion resistance. The content of the silane coupling agents having an amino group refers to the total content of the silane coupling agent having an amino group, its hydrolysate, and its hydrolyzed condensate.

[0044] [Organic Solvent] The composition may contain an organic solvent. 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-based solvents include acetate-based solvents such as ethyl acetate and butyl acetate, and alkylene glycol ester-based solvents such as ethylene glycol monomethyl ether acetate, diethylene glycol monomethyl ether acetate, and propylene glycol monomethyl ether acetate, with acetate-based solvents being preferred. In terms of achieving better storage stability, the solvent preferably includes at least one selected from the group consisting of alcohol-based solvents and ester-based solvents, and more preferably includes an alcohol-based solvent. One organic solvent may be used alone, or two or more organic solvents may be used in combination. The content of the alcohol-based solvent is preferably 1 to 100% by mass, more preferably 8 to 90% by mass, and even more preferably 40 to 85% by mass, relative to the total mass of the organic solvents. The content of the organic solvent is preferably 7 to 99 parts by mass, more preferably 9 to 60 parts by mass, relative to 1 part by mass of the total solids content of the composition.

[0045] The composition may contain other components in addition to the above-mentioned components, such as a silanol condensation catalyst, an antioxidant, a rust inhibitor, an ultraviolet absorber, a light stabilizer, an antifungal agent, an antibacterial agent, an anti-biofouling agent, a deodorizer, a pigment, a flame retardant, and an antistatic agent.

[0046] [Method for Producing the Composition] The method for producing the composition is not particularly limited and can be produced by a known method. Specific examples include a method of mixing the above-mentioned components. The order of mixing the above-mentioned components is not particularly limited, but since the silyl isocyanate compound and the aminosilane coupling agent react quickly, a method of mixing Solution 1 containing the silyl isocyanate compound and a solvent with Solution 2 containing the aminosilane coupling agent and a solvent is preferred in terms of the uniformity and abrasion resistance of the film formed. The specific polysiloxane may be mixed as Solution 3 containing the specific polysiloxane and a solvent, and at least one of Solution 1 and Solution 2 may contain the specific polysiloxane, with Solution 1 preferably containing the specific polysiloxane. Examples of solvents contained in each of the above solutions include organic solvents that may be contained in the above-mentioned composition. In terms of component solubility, the composition preferably contains at least one of an alcohol-based solvent and an ester-based solvent, and in terms of storage stability, it is more preferable to contain an alcohol-based solvent. More specifically, a method of mixing the above-mentioned components includes sequentially adding each component or each of the above-mentioned solutions and then stirring to mix. The components may be added all at once or in multiple batches. The mixing of the solutions is preferably carried out immediately before the formation of the film.

[0047] [Film] The composition of the present disclosure can form a film having excellent water repellency and abrasion resistance. The film preferably contains a cured product of various components other than the solvent contained in the composition. That is, the film preferably contains a cured product of a silyl isocyanate compound, a specific polysiloxane, and a silane coupling agent having an amino group.

[0048] Examples of methods for producing the film include a method of curing a coating film of the composition. More specifically, methods for curing a coating film of the composition include a method of applying the composition to a desired member to form a coating film, and then subjecting the coating film to a curing treatment as necessary to form a film. From the viewpoint of uniformity of the formed film, it is preferable to form a coating film of a solvent-containing composition and then subject the coating film to a drying treatment to remove the solvent. Examples of methods for applying the composition include dipping coating, spin coating, spray coating, inkjet coating, and flow coating. Examples of methods for the curing treatment include drying and heat treatment. The temperature for the curing treatment is preferably 40 to 120°C, more preferably 60 to 80°C. The time for the curing treatment is preferably 30 seconds to 60 minutes, more preferably 5 to 30 minutes.

[0049] [Eyeglass Lens] The eyeglass lens of the present disclosure includes an eyeglass lens substrate and a layer formed from the composition of the present disclosure (hereinafter also referred to as "composition layer"). In addition to the above, the eyeglass lens preferably has an antireflection layer, and more preferably has an eyeglass lens substrate, an antireflection layer, and a composition layer in this order. The eyeglass lens may have an antireflection layer and a composition layer on one surface of the eyeglass lens substrate, or may have an antireflection layer and a composition layer on both surfaces of the substrate. The antireflection layer is preferably disposed adjacent to the composition layer. In other words, the eyeglass lens preferably has an eyeglass lens substrate, an antireflection layer, and a composition layer disposed adjacent to the antireflection layer, in this order.

[0050] [Eyeglass Lens Substrate] Materials constituting the eyeglass lens substrate include organic and inorganic materials, with organic materials being preferred. Examples of organic materials include acrylate resins, methacrylate resins, thiourethane resins, allyl resins, episulfide resins, polycarbonates, urethane resins, polyesters, polystyrene, polyethersulfone, poly-4-methylpentene-1, and diethylene glycol bisallyl carbonate resins (CR-39), with thiourethane resins, episulfide resins, and diethylene glycol bisallyl carbonate resins being preferred.

[0051] The 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, and 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 a monomer. Preferred episulfide group-containing monomers are bis(2,3-epithiopropyl)sulfide or bis(2,3-epithiopropyl)disulfide.

[0052] Examples of spectacle lens substrates include finished lenses in which the convex and concave surfaces are optically finished and molded to match the desired diopter, semi-finished lenses in which only the convex surface is finished as an optical surface (for example, a spherical surface, a rotationally symmetric aspherical surface, and a progressive surface), and semi-finished lenses in which the concave surface is processed and polished to match the wearer's prescription.

[0053] From the viewpoint of ease of handling, the thickness of the spectacle lens substrate is preferably 0.8 to 30.0 mm, more preferably 1.0 to 10.0 mm. The refractive index of the spectacle lens substrate is preferably 1.50 or more, more preferably 1.60 to 1.80, and even more preferably 1.60 to 1.74.

[0054] [Anti-Reflection Layer] The spectacle lens preferably has an anti-reflection layer. The anti-reflection layer may have either a single-layer structure or a multi-layer structure. The anti-reflection layer is preferably an inorganic anti-reflection layer. The inorganic anti-reflection layer refers to an anti-reflection layer composed of an inorganic compound. The multi-layer anti-reflection layer may have a structure in which low-refractive-index layers and high-refractive-index layers are alternately laminated. 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.

[0055] Examples of methods for forming the antireflection layer include dry methods such as vacuum deposition, sputtering, ion plating, ion beam assisted deposition, and CVD.

[0056] The thickness of the antireflection layer is preferably from 100 to 10,000 nm, more preferably from 300 to 700 nm.

[0057] [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 a cured product of various components other than the solvent contained in the composition. The method for forming the composition layer can be the film formation method described above, and a method of curing a coating film of the composition is preferred.

[0058] In order to ensure that the composition layer adheres more firmly to the substrate and has better abrasion resistance, it is also preferable to subject the surface of the layer forming the coating film of the composition layer (preferably the surface of the antireflection layer) to a surface treatment. Examples of the surface treatment include surface activation treatment and cleaning treatment. Examples of the surface treatment include plasma treatment, corona treatment, ozone treatment, and UV treatment, with plasma treatment being preferred.

[0059] The thickness of the composition layer is preferably from 2 to 50 nm, more preferably from 5 to 30 nm.

[0060] [Primer layer] The eyeglass lens may have a primer layer. The primer layer is preferably disposed between the eyeglass lens substrate and the hard coat layer described below. In this case, adhesion between the eyeglass lens substrate and the hard coat layer is likely to be improved, and the impact resistance of the laminate can be improved.

[0061] The primer layer preferably contains a resin. The resin may be in particulate form. Examples of the resin include urethane resin, epoxy resin, phenol resin, polyimide, polyester, bismaleimide resin, and polyolefin, with urethane resin being preferred. The primer layer may contain an additive such as a surfactant.

[0062] As a method for forming a primer layer, for example, a method can be mentioned in which a primer layer-forming composition containing a resin is applied to a desired member to form a coating film, and the coating film is subjected to a curing treatment (for example, drying treatment) as necessary to form a primer layer. In other words, the primer layer is preferably a layer obtained by applying a primer layer-forming composition to a desired member to form a coating film, and then curing the coating film. As a method for applying a primer layer-forming composition, for example, a method can be mentioned in which the above-mentioned composition is applied.

[0063] The thickness of the primer layer is preferably 0.3 to 2.0 μm.

[0064] [Hard Coat Layer] The eyeglass lens may have a hard coat layer. The hard coat layer is preferably disposed on the primer layer, and more preferably disposed between the primer layer and the antireflection layer. When the 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 in pencil hardness according to JIS K5600. As the hard coat layer, a known hard coat layer can be used, and examples thereof include an organic hard coat layer, an inorganic hard coat layer, and an organic-inorganic hybrid hard coat layer. For example, in the field of eyeglass lenses, an organic-inorganic hybrid hard coat layer is commonly used.

[0065] As a method for forming a hard coat layer, for example, a method can be mentioned in which a composition for forming a hard coat layer is applied to a desired member to form a coating film, and the coating film is subjected to a curing treatment (for example, a light irradiation treatment and a drying treatment) as necessary to form a hard coat layer.In other words, the hard coat layer is preferably a layer obtained by applying a composition for forming a hard coat layer to a desired member to form a coating film, and then curing the coating film.As a method for applying a composition for forming a hard coat layer to a substrate, for example, the method of applying the above-mentioned composition can be mentioned.

[0066] The thickness of the hard coat layer is preferably from 1 to 20 μm, more preferably from 2 to 18 μm.

[0067] [Method for manufacturing eyeglass lenses] Known manufacturing methods can be used to manufacture eyeglass lenses. Specific examples include methods that include a step of forming a composition layer on at least one side of an eyeglass lens substrate. Of these, the method for manufacturing eyeglass lenses preferably includes a step of forming an antireflection layer on at least one side of an eyeglass lens substrate, and a step of forming a composition layer on the antireflection layer. The methods for forming each layer are as described above.

[0068] [Uses] As described above, the composition of the present disclosure can be used for eyeglass lenses. The composition of the present disclosure can also be used to form a laminate having a substrate other than an eyeglass lens and a composition layer formed from the composition of the present disclosure. Examples of uses for the laminate include a front panel (window film) for a flexible display device. The flexible display device preferably comprises a laminate for a flexible display device and an organic electroluminescent display panel, and the laminate for a flexible display device is disposed on the viewing side of the organic electroluminescent display panel and configured to be foldable. The laminate for a flexible display device may further include a polarizing plate (preferably a circular polarizing plate) and a touch sensor. In the laminate for a flexible display device, the laminate (window film), polarizing plate, and touch sensor are preferably stacked in this order from the viewing side, and the laminate (window film), touch sensor, and polarizing plate are preferably stacked from the viewing side. The presence of a polarizing plate on the viewing side of the touch sensor is preferable in that the touch sensor pattern is less visible, improving the visibility of the displayed image. Each component can be laminated using an adhesive, pressure-sensitive adhesive, or the like.

[0069] The present disclosure will be explained in more detail below using examples, but the present disclosure is not limited to these examples in any way.

[0070] The raw materials used in preparing the compositions of the examples and comparative examples are described below. SIC-434: manufactured by Matsumoto Fine Chemical Co., Ltd., contains monomethyltriisocyanatesilane (10% by mass), polysiloxane having a reactive functional group, and ethyl acetate as a solvent. X12-5263HP: manufactured by Shin-Etsu Chemical Co., Ltd., a silane coupling agent having an amino group with the following structure.

[0071]

[0072] A0876: A silane coupling agent having an amino group of the following structure, manufactured by TCI.

[0073]

[0074] H0879: A silane coupling agent having the following structure, manufactured by TCI, which does not have an amino group.

[0075]

[0076] [Preparation of Compositions] <Composition 1> Composition 1 was obtained by mixing isopropanol (12.0 parts by mass) and a silane coupling agent, X12-5263HP, so as to obtain the composition shown in Table 1, and then mixing SIC-434 (3.0 parts by mass) into the resulting solution.

[0077] <Compositions 2 to 10> Compositions 2 to 9 were obtained in the same manner as composition 1, except that the type and amount of silane coupling agent were changed as shown in Table 1. Note that no silane coupling agent was added to composition 8.

[0078] In Table 1, the amount of silane coupling agent added is the amount (mass %) relative to the silyl isocyanate compound contained in SIC-434.

[0079]

[0080] [Formation of Spectacle Lenses] A composition layer of each of the Examples and Comparative Examples was formed according to the following procedure to prepare a spectacle lens.

[0081] Example 1 A lens with an antireflection layer (a lens having a configuration obtained by removing the top coat layer from the product name ECC (manufactured by Nikon-Essilor Co., Ltd.), and having a spectacle lens substrate, primer layer, hard coat layer, and antireflection layer, in that order; the top coat layer was not formed initially) was prepared, and the antireflection layer was cleaned using a plasma dry cleaner (PDC210, manufactured by Yamato Scientific Co., Ltd., 400 W, treatment time: 30 seconds). The obtained composition 1 was coated onto the cleaned antireflection layer by spin coating (500 rpm for 30 seconds, followed by 2000 rpm for 1 second). Subsequently, the lens on which a coating of composition 1 had been formed was heat-cured in an 80°C constant temperature bath for 15 minutes to form a composition layer, and the spectacle lens of Example 1 was obtained.

[0082] Examples 2 to 7, Comparative Examples 1 and 2 Spectacle lenses of Examples 2 to 7 and Comparative Examples 1 and 2 were produced in the same manner as in Example 1, except that composition 1 was replaced with the composition shown in Table 2.

[0083] [Evaluation] [Water contact angle] The surface of the composition layer of the obtained eyeglass lens was wiped with a Kimwipe soaked in ethanol, then dried with an air gun, and the water contact angle of the central part was measured using a contact angle meter (DM500, manufactured by Kyowa Interface Science Co., Ltd.). The temperature for measuring the water contact angle was 25°C. Before the abrasion resistance test described later, the water contact angle was 100° or more in all cases, indicating good water repellency.

[0084] [Abrasion Resistance] A paper cloth (Kimwipe, manufactured by Nippon Paper Crecia Co., Ltd.) was wrapped six times around the tip of a 1.5 cm cube-shaped silicone rubber terminal attached to a rubbing tester (Taihei Rika Kogyo Co., Ltd., rubbing tester). The silicone rubber terminal was then pressed against the surface of the composition layer of a spectacle lens fixed to the rubbing tester with a load of 200 g, and the lens surface was rubbed at a speed of 90 reciprocating strokes per minute over a distance of 5 cm. After every 1000 rubs, the rubbing tester was stopped, and the rubbed surface was wiped with a Kimwipe soaked in ethanol and then dried with an air gun. The water contact angle of the rubbed surface was measured. When the contact angle fell below 100°, the coating was deemed to have fallen off, and the measurement was discontinued. The number of rubs immediately before (i.e., the maximum number of rubs at which a contact angle of 100° or more was maintained) was recorded as the abrasion resistance. The water contact angle was measured at 25°C. In practice, the abrasion resistance (the number of times of friction during which water repellency is maintained) is preferably 3,000 or more times.

[0085] [Results] Table 2 shows the compositions used in each of the examples and comparative examples and the evaluation results of the abrasion resistance.

[0086]

[0087] The evaluation results shown in Table 2 confirm that the composition of the present disclosure can form a film that is excellent in water repellency and abrasion resistance. A comparison of Examples 1 to 6 confirms that the abrasion resistance is superior when the content of silane coupling agents relative to the content of silyl isocyanate compound is 1.8 to 27 mass%, and that the abrasion resistance is even superior when the content is 2 to 15 mass%.

Claims

1. A composition comprising a silyl isocyanate compound, a polysiloxane having a reactive functional group, and at least one compound selected from the group consisting of a silane coupling agent having an amino group, a hydrolyzate thereof, and a hydrolyzed condensate thereof.

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

3. The composition according to claim 1 or 2, wherein the amino group is a primary amino group or a secondary amino group.

4. The composition according to any one of claims 1 to 3, wherein the total content of the silane coupling agent, its hydrolysate, and its hydrolysis condensate relative to the content of the silyl isocyanate compound is 0.5 to 44 mass%.

5. A spectacle lens comprising: a spectacle lens substrate; and a layer formed using the composition according to any one of claims 1 to 4.

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