Eyeglass lens

Abstract

One embodiment of the present application relates to an ophthalmic lens comprising a compound represented by formula (1).

Description

Technical Field

[0001] This invention relates to spectacle lenses. Background Technology

[0002] In eyeglass lenses, glare is reduced and visual clarity and contrast are improved by blocking light in the blue region (wavelength range of 380–500 nm). Furthermore, the high energy of light in the blue region (380–500 nm) is considered a cause of retinal damage and is believed to be a cause of eye health issues. Damage caused by blue light is termed "blue light hazard," and the 380–420 nm range, considered particularly dangerous, is considered to be the area around the lower wavelengths, with the aim of blocking light in this region.

[0003] Patent document 1 describes an optical material containing one or more ultraviolet absorbers (a) with a maximum absorption peak in the range of 350 nm or more and 370 nm or less, and the light transmittance measured at a thickness of 2 mm satisfies the following characteristics (1) to (3): (1) the light transmittance at a wavelength of 410 nm is less than 10%, (2) the light transmittance at a wavelength of 420 nm is less than 70%, and (3) the light transmittance at a wavelength of 440 nm is more than 80%.

[0004] Existing technical documents

[0005] Patent documents

[0006] Patent Document 1: International Publication No. WO2014 / 133111 Summary of the Invention

[0007] The problem the invention aims to solve

[0008] According to existing eyeglass lenses as shown in Patent Document 1, by containing a specific ultraviolet (UV) absorber, the transmittance of light with a wavelength of 410 nm can be suppressed. However, generally speaking, if a UV absorber exhibits light absorption characteristics at a wavelength of 410 nm, it also absorbs light of nearby wavelengths. Therefore, since suppressing the transmittance of light with a wavelength of 410 nm using a UV absorber also absorbs light in the visible light region, a problem arises where the eyeglass lens develops a yellowish tint. Since yellow-tinted eyeglass lenses give a degraded appearance, they are sometimes made gray or slightly bluish by adding coloring agents, which increases costs and sometimes reduces transmittance. Therefore, the aim is to suppress the tinting of eyeglass lenses caused by UV absorbers by increasing the transmittance of light with a wavelength of 430 nm.

[0009] One embodiment of the present invention relates to an eyeglass lens that suppresses the transmittance of light with a wavelength of 410 nm and has excellent transmittance of light with a wavelength of 430 nm.

[0010] Problem Solving Methods

[0011] One embodiment of the present invention relates to an eyeglass lens containing a compound represented by formula (1).

[0012] [Chemical Formula 1]

[0013]

[0014] In the formula,

[0015] R 1 It is an alkoxy group with 1 to 20 carbon atoms.

[0016] R 2 It is an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms.

[0017] R 3 It is an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms.

[0018] n is an integer from 1 to 2.

[0019] m is an integer from 0 to 2.

[0020] The effects of the invention

[0021] According to one embodiment of the present invention, an eyeglass lens is provided that has excellent transmittance for light with a wavelength of 410 nm and excellent transmittance for light with a wavelength of 430 nm. Attached Figure Description

[0022] Figure 1 This is a cross-sectional schematic diagram of the spectacle lens 1 in this embodiment. Detailed Implementation

[0023] Hereinafter, embodiments of the present invention will be described in detail with reference to the accompanying drawings, as needed. However, the present invention is not limited thereto, and various modifications can be made without departing from its spirit. It should be noted that in the drawings, the same elements are labeled with the same symbols, and repeated descriptions are omitted. Furthermore, unless otherwise specified, positional relationships such as up, down, left, and right are based on the positional relationships shown in the drawings. In addition, the scale of the drawings is not limited to the scale shown.

[0024] It should be noted that, in this specification, the description of a numerical range, such as "1 to 100", includes both its lower limit "1" and its upper limit "100". The same applies to the description of other numerical ranges.

[0025] For example, "a cured product of isocyanate and active hydrogen compound components" does not mean excluding other components, but refers to a cured product formed by curing a composition that contains at least isocyanate and active hydrogen compound components.

[0026] [Eyeglass lenses]

[0027] The spectacle lens of this embodiment contains the compound represented by formula (1) (hereinafter also referred to as "compound 1").

[0028] [Chemical Formula 2]

[0029]

[0030] In the formula,

[0031] R1 is an alkoxy group with 1 to 20 carbon atoms.

[0032] R2 is an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms.

[0033] R3 is an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms.

[0034] m is an integer from 0 to 2.

[0035] According to one embodiment of the present invention, an eyeglass lens is provided that has excellent transmittance for light with a wavelength of 410 nm and excellent transmittance for light with a wavelength of 430 nm.

[0036] <Compound 1>

[0037] The spectacle lens of this embodiment, by containing compound 1 represented by formula (1), can suppress the transmittance of light with a wavelength of 410 nm and has excellent transmittance of light with a wavelength of 430 nm. Although light with a wavelength of 410 nm is in the visible light region, it has relatively high energy, and therefore, prolonged viewing is harmful to the eyes. Compound 1 has a -COR on the benzotriazole ring. 1 Therefore, it can absorb light with a wavelength of 410 nm. Furthermore, if a compound contains light that absorbs light in the visible light region, it is prone to coloring; therefore, it is desirable not to absorb light closer to longer wavelengths than 410 nm. However, if the absorption spectrum is observed, the compound's absorption peak also absorbs light at its peak wavelength and surrounding wavelengths, resulting in a mountain-shaped spectrum. Therefore, if the absorption rate for light at a wavelength of 410 nm is increased, it also absorbs surrounding light, thus becoming prone to coloring. Therefore, to solve the problem of coloring spectacle lenses, or to make the coloring less noticeable, large amounts of dye must be used to make the hue a neutral gray, resulting in problems such as reduced light reflectance. In contrast, because compound 1 has a -COR group on the benzotriazole ring... 1 The base can therefore suppress the absorption of light with a wavelength of 430nm.

[0038] From the perspective of suppressing transmittance at wavelengths of 410 nm and 430 nm, -COR 1 The substitution position of the group is preferably at the 5th position of the benzotriazole ring.

[0039] In equation (1), R 1 It is an alkoxy group with 1 to 20 carbon atoms.

[0040] R 1 The alkoxy group in the compound preferably has 2 to 20 carbon atoms, more preferably 4 to 20, further preferably 6 to 18, even more preferably 6 to 15, and still more preferably 6 to 12. By increasing the number of carbon atoms in the alkoxy group, the solubility of compound 1 in organic compounds such as isocyanates and polythiols is improved. 1 The alkyl group can be branched or linear, but is preferably branched.

[0041] As R 1 Examples of alkoxy groups include: methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, tert-butoxy, pentoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 1-ethylpentoxy, 2-ethylpentoxy, 3-ethylpentoxy, n-hexoxy, 1-methylhexoxy, 2-methylhexoxy, 3-methylhexoxy, 1-ethylhexoxy, 2-ethylhexoxy, 3-ethylhexoxy, n-heptoxy, 1-methylheptoxy, 2-methylheptoxy, 3-methylheptoxy, 1-ethylheptoxy, 2-ethylheptoxy, 3-ethylheptoxy, n-octoxy, 1-methyloctoxy, 2-methyloctoxy, 3-methyloctoxy, 1-ethyloctoxy, 2-ethyloctoxy, 3-ethyloctoxy, n-decoxy, n-dodecyloxy, n-tetrazoloxy, n-tetradecyloxy, n-hexadecyloxy, n-octadecyloxy, n-eicosyloxy. Among these, tert-butoxy, hexoxy, n-octoxy, and 2-ethylhexoxy are more preferred, and 2-ethylhexoxy is even more preferred.

[0042] Above, R 1 Preferably, it is an alkoxy group with 4 to 20 carbon atoms, more preferably a branched alkoxy group with 4 to 20 carbon atoms, even more preferably a tert-butoxy group, even more preferably a 2-ethylhexyloxy group, and even more preferably a 2-ethylhexyloxy group.

[0043] n is an integer from 1 to 2, preferably 1.

[0044] In equation (1), R 2The alkyl group or alkoxy group having 1 to 12 carbon atoms is preferred, more preferably 2 to 8, and even more preferably 4 to 8. The alkyl group and alkoxy group can be branched or straight-chain. Alkoxy groups are preferred among the alkyl and alkoxy groups.

[0045] Examples of alkyl groups include: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, n-octyl, 1,1,3,3-tetramethylbutyl, nonyl, decyl, undecyl, and dodecyl.

[0046] Examples of alkoxy groups include: methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, tert-butoxy, pentoxy, hexoxy, heptoxy, octoxy, nonoxy, decoxy, undecyloxy, and dodecyloxy. Among these, methoxy or ethoxy is preferred.

[0047] In equation (1), R 3 It is an alkyl group or an alkoxy group having 1 to 12 carbon atoms. R 3 Examples of alkyl and alkoxy groups in R 2 The same applies to the examples in [the text].

[0048] m is an integer from 0 to 2, preferably 0.

[0049] As a specific example of compound 1, there is no particular limitation; for example, the following can be cited:

[0050] 2-(2-hydroxy-4-methoxyphenyl)2H-benzotriazole-5-carboxylic acid 2-ethylhexyl ester (the compound represented by formula (1-1) below),

[0051] [Chemical Formula 3]

[0052]

[0053] 2-(2-hydroxy-4-ethoxyphenyl)2H-benzotriazole-5-carboxylic acid 2-ethylhexyl ester (the compounds represented by formulas (1-2) below),

[0054] [Chemical Formula 4]

[0055]

[0056] 2-(2-hydroxy-4-octyloxyphenyl)2H-benzotriazole-5-carboxylic acid 2-ethylhexyl ester

[0057] 2-(2-hydroxy-4-methoxyphenyl)2H-benzotriazole-5-carboxylic acid methyl ester

[0058] 2-(2-hydroxy-4-ethoxyphenyl)2H-benzotriazole-5-carboxylic acid methyl ester

[0059] 2-(2-hydroxy-4-octyloxyphenyl)2H-benzotriazole-5-carboxylic acid methyl ester

[0060] 2-(2-hydroxy-4-methoxyphenyl)2H-benzotriazole-5-carboxylic acid ethyl ester

[0061] 2-(2-hydroxy-4-ethoxyphenyl)2H-benzotriazole-5-carboxylic acid ethyl ester

[0062] 2-(2-hydroxy-4-octyloxyphenyl)2H-benzotriazole-5-carboxylic acid ethyl ester

[0063] 2-(2-hydroxy-4-methoxyphenyl)2H-benzotriazole-5-carboxylic acid n-octyl ester,

[0064] 2-(2-hydroxy-4-ethoxyphenyl)2H-benzotriazole-5-carboxylic acid n-octyl ester, and

[0065] 2-(2-hydroxy-4-octyloxyphenyl)2H-benzotriazole-5-carboxylic acid n-octyl ester.

[0066] One of these compounds can be used alone, or two or more can be used.

[0067] Among these, 2-(2-hydroxy-4-methoxyphenyl)2H-benzotriazole-5-carboxylic acid 2-ethylhexyl ester and 2-(2-hydroxy-4-ethoxyphenyl)2H-benzotriazole-5-carboxylic acid 2-ethylhexyl ester are preferred.

[0068] The spectacle lens of this embodiment includes, for example, a lens substrate. The spectacle lens of this embodiment may include at least one layer selected from a hard coating layer, a base layer, and an anti-reflective layer.

[0069] Figure 1 This is a cross-sectional schematic diagram of the spectacle lens 1 according to this embodiment. The spectacle lens 1 according to this embodiment includes: a lens substrate 11, a hard coating 21f disposed on the object-side surface 11a of the lens substrate 11, a functional layer 31f disposed on the object-side surface 21fa of the hard coating 21f, and a water-repellent layer 41f disposed on the object-side surface 31fa of the functional layer 31f.

[0070] In addition, when the lens substrate 11 is a precision-machined lens, the spectacle lens 1 of this embodiment further includes: a hard coating 21b disposed on the eyeball-side surface 11b side of the lens substrate 11, a functional layer 31b disposed on the eyeball-side surface 21bb side of the hard coating 21b, and a water-repellent layer 41b disposed on the eyeball-side surface 31bb side of the functional layer 31b.

[0071] It should be noted that, although not shown in the figure, a base layer may be provided between the lens substrate 11 and the hard coating 21f, or between the lens substrate 11 and the hard coating 21b.

[0072] <Lens Substrate>

[0073] The lens substrate may contain compound 1 and resin.

[0074] Relative to 100 parts by weight of the resin in the lens substrate, the spectacle lens preferably contains 0.05 parts by weight or more and 2.00 parts by weight of compound 1. From the viewpoint of further suppressing the transmittance of light with a wavelength of 410 nm and further improving the transmittance of light with a wavelength of 430 nm, the content of compound 1 relative to 100 parts by weight of the resin in the lens substrate is preferably 0.10 parts by weight or more and 2.00 parts by weight or less, more preferably 0.15 parts by weight or more and 1.50 parts by weight or less, and even more preferably 0.20 parts by weight or more and 1.00 parts by weight or less.

[0075] From the viewpoint of further suppressing the transmittance of light with a wavelength of 410 nm, further improving the transmittance of light with a wavelength of 430 nm, and suppressing the decrease of Abbe number, the content of compound 1 relative to 100 parts by mass of resin in the lens substrate is preferably 0.05 parts by mass or more and 0.60 parts by mass or less, more preferably 0.10 parts by mass or more and 0.55 parts by mass or less, and even more preferably 0.20 parts by mass or more and 0.50 parts by mass or less.

[0076] [Resin]

[0077] Examples of resins used as lens substrates include: urethane resins, cyclic sulfide resins, polycarbonate resins, and acrylic resins.

[0078] The resin is preferably selected from at least one of polysulfide urethane resin, polysulfide resin and polyurethane resin, and more preferably selected from at least one of polysulfide urethane resin and polysulfide resin.

[0079] (Carbamate resins)

[0080] Carbamate resins are cured products of polymerizable compositions comprising isocyanate and active hydrogen compounds. Examples of carbamate resins include thiocarbamate resins comprising polymerization sites of isocyanate and polythiol components; carbamate resins comprising polymerization sites of isocyanate and polyol components; and carbamate urea resins having polythiocarbamate and polyurea sites, wherein the polythiocarbamate sites are polymerization sites of isocyanate and polythiol or polyol components, and the polyurea sites are polymers of isocyanate and polyamine components.

[0081] (Isocyanate component)

[0082] Examples of isocyanate components include: polyisocyanate compounds having aromatic rings, polyisocyanate compounds having aliphatic rings, and aliphatic polyisocyanate compounds with straight or branched chains.

[0083] Examples of polyisocyanate compounds with aromatic rings include: phenyl diisocyanate, 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, ethyl phenyl diisocyanate, isopropyl phenyl diisocyanate, dimethyl phenyl diisocyanate, diethyl phenyl diisocyanate, diisopropyl phenyl diisocyanate, trimethyl phenyl triisocyanate, phenyl triisocyanate, biphenyl diisocyanate, 4,4'-diphenylmethane diisocyanate, 4,4'-methylene bis(2-methylphenyl isocyanate), bibenzyl-4,4'-diisocyanate, bis(isocyanate phenyl)ethylene, 1,3-bis(isocyanate methyl)benzene, 1,4-bis(isocyanate methyl)benzene, 1,3-bis(isocyanate ethyl)benzene, bis(isocyanate propyl)benzene, α, α,α',α'-Tetramethylphenyl dimethyl diisocyanate, bis(isocyanate butyl)benzene, bis(isocyanate methyl)naphthalene, bis(isocyanate methylphenyl) ether, 2-isocyanate phenyl-4-isocyanate phenyl sulfide, bis(4-isocyanate phenyl) sulfide, bis(4-isocyanate methylphenyl) sulfide, bis(4-isocyanate phenyl) disulfide, bis(2-methyl-5-isocyanate phenyl) disulfide, bis(3-methyl-5-isocyanate phenyl) disulfide, bis(3-methyl-6-isocyanate phenyl) disulfide, bis(4-methyl-5-isocyanate phenyl) disulfide, bis(3-methoxy-4-isocyanate phenyl) disulfide, bis(4-methoxy-3-isocyanate phenyl) disulfide.

[0084] Examples of polyisocyanate compounds with aliphatic rings include: 1,3-cyclohexane diisocyanate, 1,4-cyclohexane diisocyanate, isophorone diisocyanate, 1,3-bis(isocyanate methyl)cyclohexane, 1,4-bis(isocyanate methyl)cyclohexane, dicyclohexylmethane-4,4'-diisocyanate, dicyclohexylmethane-2,4'-diisocyanate, and 2,5-bis(isocyanate methyl)bicyclo[ [2.2.1] Heptane, 2,6-bis(isocyanate methyl)bicyclo[2.2.1] heptane, 2,5-diisocyanate-1,4-dithiane, 2,5-bis(isocyanate methyl)-1,4-dithiane, 4,5-diisocyanate-1,3-dithiopentane, 4,5-bis(isocyanate methyl)-1,3-dithiopentane, 4,5-bis(isocyanate methyl)-2-methyl-1,3-dithiopentane.

[0085] Examples of linear or branched aliphatic polyisocyanate compounds include: pentamethylene diisocyanate, hexamethylene diisocyanate, 2,2-dimethylpentane diisocyanate, 2,2,4-trimethylhexane diisocyanate, butene diisocyanate, 1,3-butadiene-1,4-diisocyanate, 2,4,4-trimethylhexamethylene diisocyanate, 1,6,11-undecane triisocyanate, and 1,3,6-hexamethylene diisocyanate. Methyl triisocyanate, 4-methyl octane-1,8-diisocyanate, bis(ethyl isocyanate) carbonate, bis(ethyl isocyanate) ether, lysine diisocyanate methyl ester, lysine triisocyanate, bis(methyl isocyanate) sulfide, bis(ethyl isocyanate) sulfide, bis(propyl isocyanate) sulfide, bis(hexyl isocyanate) sulfide, bis(methyl isocyanate) sulfone, bis(isocyanate) Di(isocyanate methyl) disulfide, bis(isocyanate ethyl) disulfide, bis(isocyanate propyl) disulfide, bis(isocyanate methylthio)methane, bis(isocyanate ethylthio)methane, bis(isocyanate methylthio)ethane, 2-isocyanate methyl-3-pentane-1,5-diisocyanate, 1,2,3-tris(isocyanate methylthio)propane, 1,2, 3-Tris(isocyanate ethylthio)propane, 3,5-dithio-1,2,6,7-heptane tetraisocyanate, 2,6-diisocyanate methyl-3,5-dithio-1,7-heptane diisocyanate, 2,5-diisocyanate methylthiophene, 4-isocyanate ethylthio-2,6-dithio-1,8-octane diisocyanate, 1,2-diisothiocyanate ethane, 1,6-diisothiocyanate hexane.

[0086] These can be used in one or more ways.

[0087] The isocyanate component preferably includes at least one selected from bis(isocyanatomethyl)bicyclo[2.2.1]heptane, bis(isocyanate methyl)cyclohexane, bis(isocyanate methyl)benzene, toluene diisocyanate, diphenylmethane diisocyanate, dicyclohexylmethane diisocyanate, hexamethylene diisocyanate, and pentamethylene diisocyanate (hereinafter also referred to as "preferred isocyanate compounds").

[0088] Examples of bis(isocyanate methyl)bicyclo[2.2.1]heptane include, for example, one or more selected from 2,5-bis(isocyanate methyl)bicyclo[2.2.1]heptane and 2,6-bis(isocyanate methyl)bicyclo[2.2.1]heptane, preferably a mixture of 2,5-bis(isocyanate methyl)bicyclo[2.2.1]heptane and 2,6-bis(isocyanate methyl)bicyclo[2.2.1]heptane.

[0089] Examples of bis(isocyanate methyl)cyclohexane include 1,3-bis(isocyanate methyl)cyclohexane and 1,4-bis(isocyanate methyl)cyclohexane. Among these, 1,3-bis(isocyanate methyl)cyclohexane is preferred.

[0090] Examples of bis(isocyanate methyl)benzene include 1,3-bis(isocyanate methyl)benzene and 1,4-bis(isocyanate methyl)benzene. Among these, 1,3-bis(isocyanate methyl)benzene is preferred.

[0091] Examples of toluene diisocyanates include 2,4-toluene diisocyanate and 2,6-toluene diisocyanate. Among these, 2,4-toluene diisocyanate is preferred.

[0092] Examples of diphenylmethane diisocyanates include 4,4'-diphenylmethane diisocyanate and 2,4'-diphenylmethane diisocyanate.

[0093] Examples of dicyclohexylmethane diisocyanates include, for instance, dicyclohexylmethane-4,4'-diisocyanate.

[0094] The content of the aforementioned "preferred isocyanate compound" in the isocyanate component is preferably 80% by mass or more, more preferably 90% by mass or more, and even more preferably 95% by mass or more and 100% by mass or less.

[0095] (Active hydrogen compound component)

[0096] Examples of active hydrogen compound components include polythiols, polyols, or polyamines.

[0097] (Polythiol component)

[0098] Examples of polythiols include: ester compounds formed from polyol compounds and thiol-containing carboxylic acid compounds; straight-chain or branched aliphatic polythiols; polythiols with aliphatic rings; and polythiols with aromatic rings.

[0099] Among ester compounds formed by polyol compounds and mercaptocarboxylic acid compounds, compounds having two or more hydroxyl groups within their molecules can be cited as examples of polyol compounds. Examples of polyol compounds include ethylene glycol, diethylene glycol, propylene glycol, glycerol, butanediol, trimethylolpropane, bis(2-hydroxyethyl) disulfide, pentaerythritol, and dipentaerythritol.

[0100] Examples of compounds containing thiol carboxylic acids include: mercaptoacetic acid, mercaptopropionic acid, thiolactic acid compounds, and thiosalicylic acid.

[0101] Examples of ester compounds formed from polyol compounds and mercaptocarboxylic acid compounds include: ethylene glycol bis(2-mercaptoacetate), ethylene glycol bis(3-mercaptopropionate), diethylene glycol bis(2-mercaptoacetate), diethylene glycol bis(3-mercaptopropionate), 1,4-butanediol bis(2-mercaptoacetate), 1,4-butanediol bis(3-mercaptopropionate), trimethylolpropane tri(2-mercaptoacetate), trimethylolpropane tri(3-mercaptopropionate), pentaerythritol tetra(2-mercaptoacetate), pentaerythritol tetra(3-mercaptopropionate), dipentaerythritol hexa(2-mercaptoacetate), and dipentaerythritol hexa(3-mercaptopropionate).

[0102] Examples of linear or branched aliphatic polythiols include: 1,2-ethanedithiol, 1,1-propanedithiol, 1,2-propanedithiol, 1,3-propanedithiol, 2,2-propanedithiol, 1,6-hexanedithiol, 1,2,3-propanetrithiol, 2,2-dimethylpropane-1,3-dithiol, 3,4-dimethoxybutane-1,2-dithiol, and 2,3-dimercapto-1- Propanol, 1,2-dimercaptopropylmethyl ether, 2,3-dimercaptopropylmethyl ether, dimercaptoethyl ether, 2-(2-mercaptoethylthio)propane-1,3-dithiol, 2,2-bis(mercaptomethyl)-1,3-propanedithiol, bis(mercaptomethylthio)methane, tri(mercaptomethylthio)methane, bis(2-mercaptoethylthio)methane, 1,2-bis(mercaptomethylthio)ethane, 1,2-bis(2-mercaptoethylthio)ethane 1,3-Di(2-mercaptoethylthio)ethane, 1,3-bis(mercaptomethylthio)propane, 1,1,2,2-tetra(mercaptoethylthio)ethane, 1,1,3,3-tetra(mercaptoethylthio)propane, 3-mercaptomethyl-1,5-dimercapto-2,4-dithiapentane, tetra(mercaptoethylthio)propane, bis(2-mercaptoethyl) ether, bis(2-mercaptoethyl) sulfide, Bis(2-mercaptoethyl) disulfide, 1,2-bis(2-mercaptoethylthio)-3-mercaptopropane, 4,7-bis(mercaptomethyl)-3,6,9-trithia-1,11-undecanedithiol, 4,8-bis(mercaptomethyl)-3,6,9-trithia-1,11-undecanedithiol, 5,7-bis(mercaptomethyl)-3,6,9-trithia-1,11-undecanedithiol.

[0103] Examples of polythiols with aliphatic rings include: 1,1-cyclohexanedithiol, 1,2-cyclohexanedithiol, methylcyclohexanedithiol, bis(mercaptomethyl)cyclohexane, 2-(2,2-bis(mercaptomethylthio)ethyl)-1,3-dithionecyclobutane, 2,5-bis(mercaptomethyl)-1,4-dithiane, and 4,8-bis(mercaptomethyl)-1,3-dithiane.

[0104] Examples of polythiols with aromatic rings include: 1,3-dimercaptobenzene, 1,4-dimercaptobenzene, 1,3-bis(mercaptomethyl)benzene, 1,4-bis(mercaptomethyl)benzene, 1,3-bis(mercaptoethyl)benzene, 1,4-bis(mercaptoethyl)benzene, 1,3,5-trimercaptobenzene, 1,3,5-tri(mercaptomethyl)benzene, 1,3,5-tri(mercaptoethyl)benzene, 4,4'-dimercaptobiphenyl, and 4,4'-dimercaptobibenzyl. 2,5-Toluenedithiol, 1,5-Naphthalenedithiol, 2,6-Naphthalenedithiol, 2,7-Naphthalenedithiol, 2,4-Dimethylbenzene-1,3-dithiol, 4,5-Dimethylbenzene-1,3-dithiol, 9,10-Anthracenedimethylthiol, 1,3-Di(p-methoxyphenyl)propane-2,2-dithiol, 1,3-Diphenylpropane-2,2-dithiol, phenylmethane-1,1-dithiol, 2,4-Di(p-mercaptophenyl)pentane.

[0105] These can be used in one or more ways.

[0106] (Polyol components)

[0107] Examples of polyol components include: ethylene glycol, diethylene glycol, propylene glycol, glycerol, butanediol, trimethylolpropane, bis(2-hydroxyethyl) disulfide, pentaerythritol, and dipentaerythritol.

[0108] (Polyamine components)

[0109] Examples of polyamine components include: polymethylene diamine, polyether diamine, diethylenetriamine, iminodipropylamine, bis(hexamethylenetriamine), diethylenetriamine, tetraethylenepentamine, pentaethylenehexamine, pentaethylenehexamine, dimethylaminopropylamine, aminoethylethanolamine, and methyliminodipropylamine. Alkyldiamine, N-aminomethylpiperazine, 1,3-diaminocyclohexane, isophorone diamine, m-phenylenediamine, tetrachloro-p-phenylenediamine, m-phenylenediamine, 4,4'-methylenediphenylamine, diaminodiphenyl sulfone, benzidine, diaminodiphenyl ether, 4,4'-thiodiphenylamine, 4,4'-bis(o-toluidine)dianisidine, o-phenylenediamine, 2,4-toluenediamine, 2,5-toluenediamine, methylenebis-o-chloroaniline, diaminodiphenyl sulfone, bis(3,4-diaminophenyl)sulfone, 2,6-diaminopyridine, 4-chloro-o-phenylenediamine Amines, 4-methoxy-6-methyl-m-phenylenediamine, m-aminobenzylamine, N,N,N',N'-tetramethyl-1,3-butanediamine, N,N,N',N'-tetramethyl-p-phenylenediamine, tetramethylguanidine, 2-dimethylamino-2-hydroxypropane, pyrazine, 2,4,6-tris(dimethylaminohydroxymethyl)phenol, N-methylpiperazine, N-β-(aminoethyl)-γ-aminopropyltrimethoxysilane, N-β-(aminoethyl)-γ-aminopropylmethyldimethoxysilane, γ-aminopropylmethyldimethoxysilane.

[0110] The active hydrogen compound preferably includes at least one selected from toluene diamine, pentaerythritol tetramercaptoacetate, pentaerythritol tetramercaptopropionate, trimethylolpropane trimercaptoacetate, trimethylolpropane trimercaptopropionate, bis(mercaptoethylthio)mercaptopropane, bis(mercaptomethyl)-3,6,9-trithiadecanedithiol, dimercaptoethyl sulfide, bis(mercaptomethyl)dithiane, dimercaptoethyl ether, and diethylene glycol.

[0111] Examples of toluene diamines include 2,4-toluene diamine and 2,5-toluene diamine.

[0112] Examples of pentaerythritol tetramercaptoacetate include, for instance, pentaerythritol tetra(2-mercaptoacetate).

[0113] Examples of pentaerythritol tetramercaptopropionate include pentaerythritol tetra(3-mercaptopropionate).

[0114] Examples of trimethylolpropane trimercaptoacetic acid esters include, for example, trimethylolpropane tri(2-mercaptoacetic acid ester).

[0115] Examples of trimethylolpropane trimercaptopropionate include, for example, trimethylolpropane tri(3-mercaptopropionate).

[0116] Examples of bis(mercaptoethio)mercaptopropane include 1,2-bis(2-mercaptoethio)-3-mercaptopropane.

[0117] Examples of bis(mercaptomethyl)-3,6,9-trithiaundecanedithiol include: 4,7-bis(mercaptomethyl)-3,6,9-trithia-1,11-undecanedithiol, 4,8-bis(mercaptomethyl)-3,6,9-trithia-1,11-undecanedithiol, and 5,7-bis(mercaptomethyl)-3,6,9-trithia-1,11-undecanedithiol. A mixture of 4,7-bis(mercaptomethyl)-3,6,9-trithia-1,11-undecanedithiol, 4,8-bis(mercaptomethyl)-3,6,9-trithia-1,11-undecanedithiol, and 5,7-bis(mercaptomethyl)-3,6,9-trithia-1,11-undecanedithiol is preferred.

[0118] The active hydrogen compound component is preferably a polythiol component.

[0119] The preferred polythiol component includes 2,5-bis(mercaptomethyl)-1,4-dithiane, pentaerythritol tetra(2-mercaptoacetate), pentaerythritol tetra(3-mercaptopropionate), 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 4,7-bis(mercaptomethyl)-3,6,9-trithia-1,11-undecanedithiol, 4,8-bis(mercaptomethyl)-3,6,9-trithia-1,4-dithiaoctane, At least one of 11-undecanedithiol, 5,7-bis(mercaptomethyl)-3,6,9-trithia-1,11-undecanedithiol, trimethylolpropane tris(2-mercaptoacetate), trimethylolpropane tris(3-mercaptopropionate), butanediol bis(2-mercaptoacetate), butanediol bis(3-mercaptopropionate), pentaerythritol hexa(2-mercaptoacetate), and pentaerythritol hexa(3-mercaptopropionate),

[0120] More preferably, it comprises at least one selected from 4,7-bis(mercaptomethyl)-3,6,9-trithia-1,11-undecanedithiol, 4,8-bis(mercaptomethyl)-3,6,9-trithia-1,11-undecanedithiol, 5,7-bis(mercaptomethyl)-3,6,9-trithia-1,11-undecanedithiol, 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, pentaerythritol tetra(3-mercaptopropionate), 2,5-bis(mercaptomethyl)-1,4-dithiane, and pentaerythritol tetra(2-mercaptoacetate).

[0121] Further preferably, it comprises at least one selected from 4,7-bis(mercaptomethyl)-3,6,9-trithia-1,11-undecanedithiol, 4,8-bis(mercaptomethyl)-3,6,9-trithia-1,11-undecanedithiol, and 5,7-bis(mercaptomethyl)-3,6,9-trithia-1,11-undecanedithiol.

[0122] A mixture comprising 4,7-bis(mercaptomethyl)-3,6,9-trithia-1,11-undecanedithiol, 4,8-bis(mercaptomethyl)-3,6,9-trithia-1,11-undecanedithiol and 5,7-bis(mercaptomethyl)-3,6,9-trithia-1,11-undecanedithiol is further preferred.

[0123] The amount of the preferred polythiol component is preferably 50% by mass or more, more preferably 70% by mass or more, further preferably 90% by mass or more, even more preferably 95% by mass or more, and less than 100% by mass.

[0124] The equivalence ratio (thiol group / isocyanate group) of the polythiol component to the isocyanate group of the polyisocyanate component is preferably 40 / 60 or more, more preferably 43 / 57 or more, and even more preferably 45 / 55 or more. In addition, it is preferably 60 / 40 or less, more preferably 55 / 45 or less, and even more preferably 53 / 47 or less.

[0125] The total content of the polythiol component and the polyisocyanate component in the polymerizable composition is preferably 80% by mass or more, more preferably 90% by mass or more, even more preferably 95% by mass or more, and is less than 100% by mass.

[0126] (Cyclosulfide resin)

[0127] Cyclosulfide resins are cured products of polymeric compositions containing cyclosulfide compounds. Here, the polymeric composition may contain other monomers.

[0128] (cyclic sulfur compounds)

[0129] Cyclic sulfur compounds are compounds that contain cyclic sulfide groups (cyclic sulfur groups).

[0130] Examples of cyclic sulfide compounds include: cyclic sulfide compounds having a straight or branched aliphatic skeleton, cyclic sulfide compounds having an alicyclic skeleton, cyclic sulfide compounds having an aromatic skeleton, and cyclic sulfide compounds having a dithiane ring skeleton.

[0131] Examples of cyclic sulfide compounds having a straight-chain or branched aliphatic skeleton include: bis-(β-cyclothiopropyl) sulfide, bis-(β-cyclothiopropyl) disulfide, 2-(2-β-cyclothiopropylthioethylthio)-1,3-bis(β-cyclothiopropylthio)propane, 1,2-bis[(2-β-cyclothiopropylthioethyl)thio]-3-(β-cyclothiopropylthio)propane, tetra(β-cyclothiopropylthiomethyl)methane, and 1,1,1-tris(β-cyclothiopropylthiomethyl)propane.

[0132] Examples of cyclothioether compounds with an alicyclic skeleton include: 1,3-bis(β-cyclothiopropylthio)cyclohexane, 1,4-bis(β-cyclothiopropylthio)cyclohexane, 1,3-bis(β-cyclothiopropylthiomethyl)cyclohexane, 1,4-bis(β-cyclothiopropylthiomethyl)cyclohexane, bis[4-(β-cyclothiopropylthio)cyclohexyl]methane, 2,2-bis[4-(β-cyclothiopropylthio)cyclohexyl]propane, and bis[4-(β-cyclothiopropylthio)cyclohexyl]sulfide.

[0133] Examples of cyclic sulfide compounds with an aromatic skeleton include: 1,3-bis(β-cyclothiopropylthio)benzene, 1,4-bis(β-cyclothiopropylthio)benzene, 1,3-bis(β-cyclothiopropylthiomethyl)benzene, 1,4-bis(β-cyclothiopropylthiomethyl)benzene, bis[4-(β-cyclothiopropylthio)phenyl]methane, 2,2-bis[4-(β-cyclothiopropylthio)phenyl]propane, bis[4-(β-cyclothiopropylthio)phenyl]sulfide, bis[4-(β-cyclothiopropylthio)phenyl]sulfone, and 4,4-bis(β-cyclothiopropylthio)biphenyl.

[0134] Examples of cyclic sulfide compounds having a dithiane ring skeleton include 2,5-bis(β-cyclothiopropylthiomethyl)-1,4-dithiane, 2,5-bis(β-cyclothiopropylthioethylthiomethyl)-1,4-dithiane, 2,5-bis(β-cyclothiopropylthioethyl)-1,4-dithiane, and 2,3,5-tris(β-cyclothiopropylthioethyl)-1,4-dithiane.

[0135] In addition to cyclic sulfur compounds, other polymeric components such as the aforementioned polyisocyanates and polythiols can also be added.

[0136] Among these, cyclic sulfide compounds having a straight-chain or branched aliphatic skeleton are preferred, and more preferably bis(β-cyclothiopropyl) sulfides or bis(β-cyclothiopropyl) disulfides are preferred.

[0137] The content of the cyclic sulfur compound in the polymerizable composition is preferably 50% by mass or more, more preferably 60% by mass or more, further preferably 70% by mass or more, even more preferably 80% by mass or more, and even more preferably 90% by mass or more, and preferably 98% by mass or less, more preferably 96% by mass or less.

[0138] The polymerizable composition preferably contains sulfur or polythiol compounds by combining it with cyclic sulfur compounds.

[0139] The sulfur content in the polymerizable composition is preferably 1% by mass or more, more preferably 5% by mass or more, even more preferably 10% by mass or more, and preferably 30% by mass or less, more preferably 20% by mass or less.

[0140] Examples of polythiol compounds can be cited above.

[0141] When used in combination with cyclic sulfur compounds, the content of polythiol compounds in the polymerizable component is preferably 2% by mass or more, more preferably 4% by mass or more, and preferably 50% by mass or less, more preferably 40% by mass or less, further preferably 30% by mass or less, even more preferably 20% by mass or less, and even more preferably 10% by mass or less.

[0142] When the polymerizable composition contains polyisocyanate and polythiol components, or cyclic sulfur compounds, it preferably contains a polymerization catalyst.

[0143] Examples of polymerization catalysts include tin compounds and nitrogen-containing compounds.

[0144] Examples of tin compounds include alkyltin compounds and alkyltin halides.

[0145] Examples of alkyltin compounds include dibutyltin diacetate and dibutyltin dilaurate.

[0146] Examples of alkyl tin halide compounds include: dibutyltin dichloride, dimethyltin dichloride, monomethyltin trichloride, trimethyltin chloride, tributyltin chloride, tributyltin fluoride, dimethyltin dibromide, etc.

[0147] Among these, dibutyltin diacetate, dibutyltin dilaurate, dibutyltin dichloride, and dimethyltin dichloride are preferred, with dimethyltin dichloride being more preferred.

[0148] Examples of nitrogen-containing compounds include tertiary amines, quaternary ammonium salts, imidazole compounds, and pyrazole compounds. Tertiary amines are preferably hindered amines.

[0149] Examples of tertiary amines include: triethylamine, tri-n-propylamine, triisopropylamine, tri-n-butylamine, triisobutylamine, N,N-dimethylbenzylamine, N-methylmorpholine, N,N-dimethylcyclohexylamine, pentamethyldiethylenetriamine, bis(2-dimethylaminoethyl) ether, N-methylmorpholine, N,N'-dimethylpiperazine, N,N,N',N'-tetramethylethylenediamine, and 1,4-diazabicyclo[2.2.2]octane (DABCO).

[0150] Examples of hindered amines include: 1,2,2,6,6-pentamethyl-4-piperidinol, 1,2,2,6,6-pentamethyl-4-hydroxyethyl-4-piperidinol, methyl-1,2,2,6,6-pentamethyl-4-piperidinyl sebacate, mixtures of methyl-1,2,2,6,6-pentamethyl-4-piperidinyl sebacate and bis(1,2,2,6,6-pentamethyl-4-piperidinyl) sebacate, and bis(1,2, 2,6,6-pentamethyl-4-piperidinyl) sebacate, bis(2,2,6,6-tetramethyl-1-(octoxy)-4-piperidinyl) sebacate, bis(1,2,2,6,6-pentamethyl-4-piperidinyl)[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methyl] butylmalonate, tetra(1,2,2,6,6-pentamethyl-4-piperidinyl)butane-1,2,3,4-tetracarboxylate.

[0151] Examples of quaternary ammonium salts include tetraethylammonium hydroxide.

[0152] Examples of imidazole compounds include: imidazole, 1-methyl-2-mercapto-1H-imidazol, 1,2-dimethylimidazol, benzylmethylimidazol, and 2-ethyl-4-imidazol.

[0153] Examples of pyrazole compounds include pyrazole and 3,5-dimethylpyrazole.

[0154] Among these, hindered tertiary amines, imidazole compounds, and pyrazole compounds are preferred, imidazole compounds are more preferred, and 1-methyl-2-mercapto-1H-imidazolium is even more preferred.

[0155] When isocyanate and active hydrogen compound components are included, the amount of polymerization catalyst added in the polymerizable composition is preferably 0.001 parts by mass or more, more preferably 0.005 parts by mass or more, and even more preferably 0.007 parts by mass or more, and preferably 2 parts by mass or less, more preferably 1 part by mass or less, and even more preferably 0.5 parts by mass or less, relative to the total amount of isocyanate and active hydrogen compound components of 100 parts by mass.

[0156] In the case of containing cyclic sulfur compounds, the amount of polymerization catalyst added in the polymerizable composition is preferably 0.001 parts by mass or more, more preferably 0.005 parts by mass or more, and even more preferably 0.007 parts by mass or more, and preferably 2 parts by mass or less, more preferably 1 part by mass or less, and even more preferably 0.5 parts by mass or less, relative to the total amount of polymerizable components (100 parts by mass).

[0157] (Polycarbonate resin)

[0158] The polycarbonate resin is preferably a cured product of a polymeric composition comprising diethylene glycol dielyl carbonate.

[0159] To obtain a three-dimensionally cross-linked optical resin, the monomer preferably contains monomers having two or more polymerizable unsaturated bonds within the molecule.

[0160] Examples of polymerizable unsaturated bonds include (meth)acrylate, allyl, and vinyl groups. It should be noted that the (meth)acrylate group refers to at least one selected from methacrylate and acrylic groups.

[0161] Among these, at least one is selected from methacrylate and allyl groups.

[0162] As a monomer having two or more polymerizable unsaturated bonds in the molecule, it preferably includes diethylene glycol diallyl carbonate, and more preferably includes diethylene glycol diallyl carbonate, benzyl methacrylate, diallyl phthalate, and alkyl methacrylate having 1 to 4 carbon atoms in the alkyl group.

[0163] The amount of diethylene glycol dielyl carbonate in combination relative to the total amount of monomers is preferably 5% by mass or more, more preferably 10% by mass or more, even more preferably 20% by mass or more, and preferably 100% by mass or less, more preferably 80% by mass or less, even more preferably 50% by mass or less, and even more preferably 40% by mass or less.

[0164] When used in combination with benzyl methacrylate, diallyl phthalate, and alkyl methacrylates having 1 to 4 carbon atoms in the alkyl group, the amount of diethylene glycol diallyl carbonate is more preferably 5% by mass or more, further preferably 10% by mass or more, even more preferably 20% by mass or more, and more preferably 40% by mass or less, and even more preferably 35% by mass or less, relative to the total amount of monomers.

[0165] The amount of benzyl methacrylate incorporated relative to the total amount of monomers is preferably 5% by mass or more, more preferably 10% by mass or more, even more preferably 15% by mass or more, and preferably 40% by mass or less, more preferably 30% by mass or less, even more preferably 25% by mass or less.

[0166] As diallyl phthalate, examples include one or both selected from diallyl isophthalate and allyl terephthalate.

[0167] The amount of diallyl phthalate incorporated relative to the total amount of monomers is preferably 14% by mass or more, more preferably 20% by mass or more, even more preferably 30% by mass or more, and preferably 88% by mass or less, more preferably 70% by mass or less, even more preferably 60% by mass or less.

[0168] Alkyl methacrylates having 1 to 4 carbon atoms as alkyl groups include at least one selected from methyl methacrylate, ethyl methacrylate, n-propyl methacrylate, isopropyl methacrylate, n-butyl methacrylate, sec-butyl methacrylate, isobutyl methacrylate, and tert-butyl methacrylate.

[0169] The amount of alkyl methacrylate incorporated relative to the total amount of monomers is preferably 1% by mass or more, more preferably 2% by mass or more, even more preferably 3% by mass or more, and preferably 6% by mass or less, more preferably 5% by mass or less.

[0170] Examples of free radical initiators used for polymerization include 1,1-azobiscyclohexane carbonate, diisopropyl peroxide carbonate, 1,1'-azobiscyclohexane nitrate, and di-tert-butyl peroxide.

[0171] The amount of free radical initiator relative to 100 parts by mass of monomer is preferably 0.1 parts by mass or more, more preferably 0.5 parts by mass or more, even more preferably 1.0 parts by mass or more, and preferably 10 parts by mass or less, more preferably 8 parts by mass or less, even more preferably 5 parts by mass or less.

[0172] (Acrylic resin)

[0173] Acrylic resin is a cured product of a polymeric composition containing acrylic compounds. The polymeric composition may also contain other monomers.

[0174] Examples of acrylic compounds include polyfunctional (meth)acrylates with aromatic rings, polyalkylene glycol di(meth)acrylates, and monofunctional acrylates.

[0175] Among these, polyfunctional (meth)acrylate compounds with aromatic rings and polyalkylene glycol di(meth)acrylates are preferred.

[0176] Examples of polyfunctional (meth)acrylate compounds with aromatic rings include oxoolefin-modified bisphenol A with (meth)acryloyl groups at both ends, oxoolefin-modified bisphenol A with (meth)acryloyl groups at both ends, and carbamate-modified bisphenol A.

[0177] Among these, oxyolefin-modified bisphenol A with (meth)acryloyl groups at both ends is preferred.

[0178] As an oxidized olefin modified bisphenol A having (meth)acryloyl groups at both ends, the compound represented by formula (2) is preferred.

[0179] [Chemical Formula 5]

[0180]

[0181] [In the formula, R] 51 It is ethylene or propylene, R 52 X is hydrogen or methyl, X is an oxygen atom or a sulfur atom, preferably an oxygen atom, m and n are the average molar number of additions, and m+n is 1.5 to 6, preferably 2 to 4.

[0182] Examples of bisphenol A modified with oxidized olefins having (meth)acryloyl groups at both ends include 2,2-bis[4-[2-((meth)acryloyloxy)ethoxy]phenyl]propane and 2,2-bis[4-[2-((meth)acryloyloxy)ethoxy]-3,5-dibromophenyl]propane.

[0183] The content of the polyfunctional (meth)acrylate compound having an aromatic ring in the polymerizable composition is preferably 40% by mass or more, more preferably 50% by mass or more, even more preferably 55% by mass or more, and preferably 90% by mass or less, more preferably 80% by mass or less, even more preferably 70% by mass or less.

[0184] Examples of polyalkylene glycol di(meth)acrylates include: diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, dipropylene glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, tetrapropylene glycol di(meth)acrylate, dibutylene glycol di(meth)acrylate, tributylene glycol di(meth)acrylate, and tetrabutylene glycol di(meth)acrylate.

[0185] The content of polyalkylene glycol di(meth)acrylate in the polymerizable composition is preferably 10% by mass or more, more preferably 20% by mass or more, further preferably 30% by mass or more, and preferably 60% by mass or less, more preferably 50% by mass or less, and further preferably 45% by mass or less.

[0186] Examples of monofunctional (meth)acrylates include: phenyl (meth)acrylate, benzyl (meth)acrylate, phenoxyethyl (meth)acrylate, 3-phenoxy-2-hydroxypropyl (meth)acrylate, 2-phenylphenyl (meth)acrylate, 4-phenylphenyl (meth)acrylate, 3-(2-phenylphenyl)-2-hydroxypropyl (meth)acrylate, 3-(4-phenylphenyl)-2-hydroxypropyl (meth)acrylate, 1-naphthoxyethyl (meth)acrylate, 2-naphthoxyethyl (meth)acrylate, 2,4,6-tribromophenyl (meth)acrylate, 2,4,6-tribromophenoxyethyl (meth)acrylate, 2,4,6-tribromophenyl di(oxyethyl) ester, and 2,4,6-tribromobenzyl (meth)acrylate.

[0187] The total content of the polymerizable component in the polymerizable composition is preferably 80% by mass or more, more preferably 85% by mass or more, even more preferably 90% by mass or more, and preferably 99% by mass or less, more preferably 95% by mass or less.

[0188] When the polymerizable composition contains acrylic compounds, it is preferable to contain a free radical polymerization initiator.

[0189] Examples of free radical polymerization initiators include energy-ray-sensitive polymerization initiators and heat-sensitive polymerization initiators.

[0190] Examples of energy-ray-induced polymerization initiators include: 2-hydroxy-2-methyl-1-phenylpropane-1-one, hydroxycyclohexylphenyl ketone, methyl phenyl glyoxylate, and 2,4,6-trimethylbenzoyl diphenylphosphine oxide.

[0191] Examples of thermosensitive polymerization initiators include organic peroxides and azo compounds.

[0192] Examples of organic peroxides include: tert-butyl peroxyneodecanoate, tert-butyl perpentanoate, tert-butyl perisobutyrate, tert-butyl peracetic acid, cumyl peroxyneodecanoate, tert-butyl peroctanoate, tert-butyl perisopropyl carbonate, cumyl peroctanoate, tert-hexyl peroxyneodecanoate, tert-hexyl perpentanoate, and tert-butyl peroxohexanoate; 1,1-bis(tert-butylperoxy)- Peroxide ketals such as 3,3,5-trimethylcyclohexane, 1,1-bis(tert-butylperoxy)cyclohexane, 2,2-bis(tert-butylperoxy)octane, and 2,2-bis(tert-butylperoxy)butane; peroxide diacyls such as acetyl peroxide, isobutyryl peroxide, octyl peroxide, lauroyl peroxide, benzoyl peroxide, and o-benzoyl peroxide; and peroxide dicarbonates such as diisopropyl peroxide and di-n-propyl peroxide.

[0193] Examples of azo compounds include: 2,2'-azobisisobutyronitrile, 1,1'-azobis(cyclohexane-1-carboxylonitrile), 2,2'-azobis(2-methylbutyronitrile), 2,2'-azobis(2,4-dimethylpentanitrile), dimethyl 2,2'-azobisisobutyrate, and 2,2'-azobis(2,4,4-trimethylpentane).

[0194] The amount of free radical polymerization initiator added relative to the total amount of acrylic compounds (100 parts by mass) is preferably 0.01 parts by mass or more, more preferably 0.1 parts by mass or more, even more preferably 0.5 parts by mass or more, and preferably 10 parts by mass or less, more preferably 5 parts by mass or less, even more preferably 3 parts by mass or less.

[0195] The lens substrate may contain mold release agents, colorants, antioxidants, anti-coloring agents, fluorescent whitening agents, and other additives, and one or more of these may be used.

[0196] [Mold Release Agent]

[0197] Examples of release agents include isopropyl phosphate, butyl phosphate, octyl phosphate, nonyl phosphate, decyl phosphate, isodecanyl phosphate, isodecanyl phosphate, tridecyl phosphate, stearyl phosphate, propylphenyl phosphate, butylphenyl phosphate, and butoxyethyl phosphate. The phosphate ester compound can be either a monophosphate compound or a diester compound, but a mixture of monophosphate and diester compounds is preferred.

[0198] The amount of release agent added relative to 100 parts by weight of the total amount of resin is preferably 0.01 parts by weight or more, more preferably 0.05 parts by weight or more, and preferably 1.00 parts by weight or less, more preferably 0.50 parts by weight or less.

[0199] [Coloring agent]

[0200] The lens substrate may contain colorants within a range that does not impair the light reflectivity described later.

[0201] From the viewpoint of making the coloring associated with the addition of compound 1 less noticeable, the lens substrate may contain a colorant L (hereinafter also referred to as "colorant L") having a maximum absorption wavelength of 550 nm or higher and 600 nm or lower in a toluene solution of 20 ppm by mass. From the viewpoint of making the coloring associated with the addition of compound 1 less noticeable, the lens substrate may contain a colorant S (hereinafter also referred to as "colorant S") having a maximum absorption wavelength of 500 nm or higher and less than 550 nm in a toluene solution of 20 ppm by mass.

[0202] (Coloring agent L)

[0203] From the perspective of obtaining a lens substrate with a slightly bluish tint, colorant L exhibits a maximum absorption wavelength above 550 nm and below 600 nm in a 20 ppm toluene solution. It should be noted that 20 ppm toluene solution refers to the proportion of the solute relative to the total toluene solution.

[0204] Furthermore, from the viewpoint of obtaining a lens substrate with a slightly bluish hue, the maximum absorption wavelength of the colorant L is preferably 550 nm or more, more preferably 560 nm or more, and even more preferably 580 nm or more. Moreover, from the viewpoint of obtaining a resin composition with a slightly bluish hue, the maximum absorption wavelength of the colorant L is preferably 600 nm or less, more preferably 590 nm or less.

[0205] Examples of colorants L include: CI Solvent Violet 11, 13, 14, 26, 31, 33, 36, 37, 38, 45, 47, 48, 51, 59, 60; and CI Disperse Violet 26, 27, 28. Among these, CI Disperse Violet 27, CI Solvent Violet 13, and 31 are preferred. From the viewpoint that they have high polymerization stability even in polymerizable compositions and minimal hue variation, CI Disperse Violet 27 and CI Solvent Violet 13 are more preferred, and CI Disperse Violet 27 is even more preferred.

[0206] From the viewpoint of obtaining a lens substrate with a slightly bluish tint, the amount of colorant L added relative to the resin is preferably 10,000 ppb by mass or less, more preferably 3,000 ppb by mass or less, and even more preferably 1,500 ppb by mass or less. From the viewpoint of obtaining a lens substrate with a slightly bluish tint, the amount of colorant L added is preferably 200 ppb by mass or more, more preferably 300 ppb by mass or more, and even more preferably 400 ppb by mass or more.

[0207] (Colorant S)

[0208] From the viewpoint of obtaining a lens substrate with a slightly bluish tint, colorant S has a maximum absorption wavelength above 500 nm and below 550 nm in a toluene solution of 20 ppm by mass.

[0209] Furthermore, from the viewpoint of obtaining a lens substrate with a slightly bluish tint, the maximum absorption wavelength of the colorant S is preferably 500 nm or more, more preferably 510 nm or more, and even more preferably 530 nm or more. Moreover, from the viewpoint of obtaining a lens substrate with a slightly bluish tint, the maximum absorption wavelength of the colorant L is preferably 545 nm or less.

[0210] From the viewpoint of obtaining a lens substrate with a slightly bluish hue, examples of colorant S include: CI Solvent Red 24, 49, 52, 90, 91, 111, 118, 119, 122, 124, 125, 127, 130, 132, 143, 145, 146, 150, 151, 155, 160, 168, 169, 172, 175, 181, 207, 218, 222, 227, 230, 245, 247; and CI Acid Red 73, 80, 91, 92, 97, 138, 151, 211, 274, 289. Among these, CI Solvent Red 52 and 146 are preferred, and CI Solvent Red 52 is more preferred from the viewpoint that it has high polymerization stability even in polymerizable compositions and minimal hue variation.

[0211] From the viewpoint of obtaining a lens substrate with a slightly bluish tint, the amount of colorant S added relative to the resin is preferably 500 ppb or less by mass, more preferably 100 ppb or less by mass, and even more preferably 50 ppb or less by mass. From the viewpoint of obtaining a lens substrate with a slightly bluish tint, the amount of colorant S added is preferably 1 ppb or more by mass, more preferably 3 ppb or more by mass, and even more preferably 5 ppb or more by mass.

[0212] From the viewpoint of obtaining a lens substrate with a slightly bluish tint, the mass ratio of colorant L to colorant S [mass of colorant L / mass of colorant S] is preferably 5 or more and 500 or less.

[0213] The mass ratio of colorant L to colorant S is preferably 5 or more, more preferably 10 or more, further preferably 15 or more, and even more preferably 20 or more. Furthermore, the mass ratio of colorant L to colorant S is preferably 500 or less, more preferably 200 or less, further preferably 100 or less, and even more preferably 80 or less.

[0214] [Structure of lens substrate, etc.]

[0215] As a lens substrate, it can be any lens among finished lenses and semi-finished lenses.

[0216] There are no special limitations on the surface shape of the substrate for eyeglass lenses; it can be any shape, such as flat, convex, or concave.

[0217] The lens substrate can be used for any purpose, such as for monofocal lenses, multifocal lenses, or progressive lenses. For example, for progressive lenses, the near vision region (near region) and the progressive region (intermediate region) are typically included in the lower region mentioned above, while the distance vision region (distance region) is included in the upper region.

[0218] As a lens substrate, colorless lens substrates are usually used, but colored lens substrates can also be used within the limits of not compromising transparency.

[0219] The preferred lens substrate is meniscus-shaped. A "meniscus-shaped" lens substrate refers to a lens substrate with curved surfaces formed on both sides. By containing the aforementioned compound 1 in the meniscus-shaped lens substrate, astigmatism can be suppressed.

[0220] The optical center thickness of the lens substrate is not particularly limited, but is preferably 0.5 mm or more and 10.0 mm or less, more preferably 0.5 mm or more and 5.0 mm or less, further preferably 0.5 mm or more and 3.0 mm or less, and even more preferably 0.5 mm or more and 2.0 mm or less.

[0221] There is no particular limitation on the diameter of the lens substrate, which is usually around 50 to 100 mm.

[0222] The refractive index ne of the lens substrate is preferably 1.52 or higher, more preferably 1.53 or higher, even more preferably 1.55 or higher, even more preferably 1.58 or higher, and still even more preferably 1.60 or higher.

[0223] From the viewpoint of improving the Abbe number increase effect brought about by the presence of compound 1, the refractive index ne of the lens substrate is preferably 1.70 or more, and more preferably 1.74 or more.

[0224] It should be noted that there is no specific upper limit to the refractive index ne of the lens substrate; for example, it can be below 1.80.

[0225] From the viewpoint of reducing blue light hazards, the transmittance of the lens substrate to light with a wavelength of 410 nm is preferably 5% or less, more preferably 3% or less, and even more preferably 1.0% or less. There is no particular limitation on the lower limit of the transmittance to light with a wavelength of 410 nm; for example, it may be 0.0% or more.

[0226] The transmittance of the lens substrate to light with a wavelength of 430 nm is preferably 70% or more, more preferably 72% or more, and even more preferably 75% or more. By having the above-mentioned transmittance to light with a wavelength of 410 nm and achieving the same transmittance to light with a wavelength of 430 nm, it is possible to reduce blue light hazards while suppressing coloring or reducing the amount of the aforementioned dyeing agent. There is no particular upper limit to the transmittance to light with a wavelength of 430 nm, for example, it is 90% or less.

[0227] From the viewpoint of reducing the transmission of harmful ultraviolet rays, the transmittance of the lens substrate to light with a wavelength of 400 nm is preferably 3% or less, more preferably 1% or less, and even more preferably 0.0% or less.

[0228] The transmittance of the lens substrate to light with a wavelength of 420 nm is preferably 50% or less, more preferably 30% or less, and even more preferably 20% or less. By having the above-mentioned transmittance to light with a wavelength of 410 nm and achieving the same transmittance to light with a wavelength of 420 nm, blue light hazard can be reduced. There is no particular limitation on the lower limit of the transmittance to light with a wavelength of 420 nm, for example, it is 0% or more.

[0229] The transmittance of the lens substrate to light with a wavelength of 440 nm is preferably 70% or more, more preferably 72% or more, and even more preferably 75% or more. By achieving this transmittance to light with a wavelength of 440 nm, coloring can be suppressed or the amount of the aforementioned dye can be reduced. There is no particular upper limit to the transmittance to light with a wavelength of 440 nm, for example, it is 95% or less.

[0230] The transmittance of the lens substrate to light with a wavelength of 450 nm is preferably 70% or more, more preferably 72% or more, and even more preferably 75% or more. By achieving this transmittance to light with a wavelength of 450 nm, coloring can be suppressed or the amount of the aforementioned dye can be reduced. There is no particular upper limit to the transmittance to light with a wavelength of 450 nm, for example, it is 95% or less.

[0231] The transmittance of the lens substrate to light with a wavelength of 550 nm is preferably 70% or more, more preferably 80% or more, and even more preferably 85% or more. There is no particular limitation on the upper limit of this transmittance to light with a wavelength of 550 nm; for example, it may be 95% or less.

[0232] The light reflectance of the lens substrate is preferably 70% or more, more preferably 80% or more, further preferably 85% or more, and even more preferably 90% or more. There is no particular limitation on the upper limit of the light reflectance; for example, it can be 100% or less, or 95% or less.

[0233] The aforementioned transmittance refers to the transmittance at the optical center of the lens substrate, which can be measured using a spectrophotometer. For example, a spectrophotometer such as the "U-4100" (trade name, manufactured by Hitachi, Ltd.) can be used. The aforementioned transmittance can be achieved by adjusting the content of compound 1 accordingly to the thickness of the lens substrate.

[0234] [Manufacturing method of lens substrate]

[0235] The lens substrate is not particularly limited, and can be obtained, for example, through a manufacturing method that includes the following steps:

[0236] The process of curing the above-mentioned polymeric composition; and

[0237] The process of annealing the cured resin.

[0238] Polymerization is preferably carried out by casting polymerization. The lens substrate can be obtained, for example, by injecting a polymerizable composition into a molding die made of glass or metal and a combination of tape or gaskets, and then polymerizing it.

[0239] The polymerization conditions can be appropriately set according to the polymerizable composition. The polymerization initiation temperature is preferably 0°C or higher, more preferably 10°C or higher, and preferably 50°C or lower, more preferably 40°C or lower. It is preferable to start heating from the polymerization initiation temperature and then heat to solidify the product. For example, the maximum heating temperature is typically 110°C or higher and 130°C or lower.

[0240] After polymerization, the lens substrate can be demolded and annealed. The preferred annealing temperature is 100–150°C.

[0241] <Hard coating>

[0242] The hard coating is, for example, a cured film formed from a curable composition comprising inorganic oxides and silicon compounds. The curable composition preferably further comprises a multifunctional epoxy compound.

[0243] Examples of inorganic oxides include: silicon oxide, aluminum oxide, titanium oxide, zirconium oxide, tungsten oxide, zinc oxide, tin oxide, beryllium oxide, antimony oxide, and composite oxides formed from two or more of these inorganic oxides. These can be used individually or in combination. Silicon oxide is preferred among these inorganic oxides. It should be noted that colloidal silicon dioxide can also be used as an inorganic oxide.

[0244] The content of inorganic oxides in the solid component of the curable composition is preferably 20% by mass or more and 80% by mass or less, more preferably 25% by mass or more and 70% by mass or less, and even more preferably 25% by mass or more and 50% by mass or less.

[0245] Silicon compounds, for example, are silicon compounds having hydrolyzable groups such as alkoxy groups. Silicon compounds are preferably silane coupling agents having organic groups bonded to silicon atoms and hydrolyzable groups. The organic groups bonded to silicon atoms are preferably organic groups having functional groups such as epoxy, vinyl, methacryloxy, acryloyloxy, mercapto, amino, and phenyl groups, and more preferably organic groups having epoxy groups. It should be noted that silicon compounds may have alkyl groups bonded to silicon.

[0246] Commercially available examples of the aforementioned silane coupling agents include: those manufactured by Shin-Etsu Chemical Industry Co., Ltd., with trade names such as KBM-303, KBM-402, KBM-403, KBE-402, KBE-403, KBM-1403, KBM-502, KBM-503, KBE-502, KBE-503, KBM-5103, KBM-602, KBM-603, KBM-903, KBE-903, KBE-9103, KBM-573, KBM-575, KBM-9659, KBE-585, KBM-802, KBM-803, KBE-846, and KBE-9007.

[0247] The content of silicon compound in the solid component of the curable composition is preferably 20% by mass or more and 90% by mass or less, more preferably 30% by mass or more and 75% by mass or less, and even more preferably 50% by mass or more and 75% by mass or less.

[0248] The polyfunctional epoxy compound is preferably a polyfunctional epoxy compound having two or more epoxy groups in one molecule, and more preferably a polyfunctional epoxy compound having two or three epoxy groups in one molecule. Commercially available polyfunctional epoxy compounds include those manufactured by Nagase ChemteX Co., Ltd. under the trade name "DENACOL", such as EX-201, EX-211, EX-212, EX-252, EX-313, EX-314, EX-321, EX-411, EX-421, EX-512, EX-521, EX-611, EX-612, EX-614, and EX-614B.

[0249] The content of the multifunctional epoxy compound in the solid component of the curable composition is preferably 0% or more and 50% or less by mass, more preferably 10% or more and 40% or less by mass, and even more preferably 15% or more and 30% or less by mass.

[0250] In addition to the components described above, the curable composition can also be prepared by mixing any components such as organic solvents, leveling agents, and curing catalysts as needed.

[0251] The aforementioned hard coating can be formed by applying a curable composition to a substrate and then performing a curing process (thermal curing, photocuring, etc.). Common methods for applying the curable composition include dip coating, spin coating, and spray coating. The curing process is typically performed by heating the curable composition containing a polyfunctional epoxy compound. For example, heat curing can be performed by placing a lens coated with the aforementioned curable composition in an atmosphere with a temperature of 50–150°C for 30 minutes to 3 hours.

[0252] <Basal layer>

[0253] The aforementioned base layer may be formed, for example, from an aqueous resin composition comprising at least one resin particle selected from polyurethane resin, acrylic resin, and epoxy resin.

[0254] As the above-mentioned waterborne resin composition, commercially available waterborne polyurethane can be used directly, or it can be used after being diluted with a waterborne solvent as needed. Commercially available waterborne polyurethanes include, for example: the "EVAFANOL" series manufactured by Nichika Chemical Co., Ltd.; the "SUPERFLEX" series manufactured by Daiichi Kogyo Pharmaceutical Co., Ltd.; the "ADEKA BONTIGHTER" series manufactured by ADEKA Co., Ltd.; the "OLESTER" series manufactured by Mitsui Chemicals Co., Ltd.; the "Vondic" series and the "Hydran" series manufactured by Dai Nippon Ink & Chemical Co., Ltd.; the "Impranil" series manufactured by Bayer Co., Ltd.; the "SOFLANATE" series manufactured by SOFLAN Co., Ltd.; the "Poise" series manufactured by Kao Corporation; the "Sanprene" series manufactured by Sanyo Chemical Co., Ltd.; the "Izelax" series manufactured by Hodogaya Chemical Co., Ltd.; and the "Noerez" series manufactured by Zeneca Co., Ltd.

[0255] The base layer can be formed, for example, by applying the above-described aqueous resin composition to the surface of the substrate and allowing it to dry.

[0256] <Functional Layer>

[0257] Examples of the aforementioned functional layers include: anti-reflective layers, ultraviolet absorption layers, infrared absorption layers, photochromic layers, antistatic layers, and anti-fog layers. These functional layers can be used individually or in combination of two or more. Known technologies related to eyeglass lenses can be applied to these functional layers. Among these, an anti-reflective layer is preferred.

[0258] (Anti-reflective layer)

[0259] The anti-reflective layer may have, for example, alternating low-refractive-index layers and high-refractive-index layers. The anti-reflective layer preferably has 4 to 11 layers, more preferably 5 to 8 layers.

[0260] The refractive index of the low-refractive-index layer is preferably 1.35 to 1.80, more preferably 1.45 to 1.50, at a wavelength of 500 to 550 nm. The low-refractive-index layer comprises an inorganic oxide, preferably silicon oxide.

[0261] The refractive index of the high refractive index layer is preferably 1.90 to 2.60, more preferably 2.00 to 2.40, at a wavelength of 500 to 550 nm. The high refractive index layer may contain, for example, an inorganic oxide. The inorganic oxide used in the high refractive index layer is preferably at least one selected from zirconium oxide, tantalum oxide, yttrium oxide, titanium oxide, niobium oxide, and aluminum oxide, more preferably at least one selected from zirconium oxide and tantalum oxide.

[0262] For anti-reflective layers, low-refractive-index and high-refractive-index layers can be alternately stacked using vacuum evaporation to form the anti-reflective layer.

[0263] <Water-repellent layer>

[0264] The water-repellent layer is formed using the water-repellent material composition described later. The water-repellent layer can be formed on a hard coating layer or a functional layer, but is preferably formed on an anti-reflective layer. Furthermore, the water-repellent layer is preferably located on the outermost surface.

[0265] <Properties of Spectacle Lenses>

[0266] From the perspective of reducing the harm of blue light, the overall transmittance of eyeglass lenses to light with a wavelength of 410 nm is preferably 5% or less, more preferably 3% or less, and even more preferably 1.0% or less. There is no particular limitation on the lower limit of the transmittance to light with a wavelength of 410 nm, for example, it is 0.0% or more.

[0267] The overall transmittance of the eyeglass lens to light with a wavelength of 430 nm is preferably 70% or more, more preferably 72% or more, and even more preferably 75% or more. By having the above-mentioned transmittance to light with a wavelength of 410 nm and achieving the same transmittance to light with a wavelength of 430 nm, it is possible to reduce blue light hazards while suppressing coloring or reducing the amount of the aforementioned dyes used. There is no particular upper limit to the transmittance to light with a wavelength of 430 nm, for example, it is 90% or less.

[0268] From the viewpoint of reducing the transmission of harmful ultraviolet rays, the overall transmittance of the eyeglass lens to light with a wavelength of 400 nm is preferably 3% or less, more preferably 1% or less, and even more preferably 0.0% or less.

[0269] The overall transmittance of the eyeglass lens to light with a wavelength of 420 nm is preferably 50% or less, more preferably 30% or less, and even more preferably 20% or less. By having the above-mentioned transmittance to light with a wavelength of 410 nm, and achieving the same transmittance to light with a wavelength of 420 nm, blue light hazard can be reduced. There is no particular limitation on the lower limit of the transmittance to light with a wavelength of 420 nm; for example, it can be 0% or more.

[0270] The overall transmittance of the spectacle lens to light with a wavelength of 440 nm is preferably 70% or more, more preferably 72% or more, and even more preferably 75% or more. By achieving this transmittance to light with a wavelength of 440 nm, it is possible to suppress coloring or reduce the amount of the aforementioned dyeing agent used. There is no particular upper limit to the transmittance to light with a wavelength of 440 nm, for example, it is 95% or less.

[0271] The overall transmittance of the eyeglass lens to light with a wavelength of 450 nm is preferably 70% or more, more preferably 72% or more, and even more preferably 75% or more. By achieving this transmittance to light with a wavelength of 450 nm, it is possible to suppress coloring or reduce the amount of the aforementioned dyeing agent. There is no particular upper limit to the transmittance to light with a wavelength of 450 nm, for example, it is 95% or less.

[0272] The overall transmittance of the eyeglass lens to light with a wavelength of 550 nm is preferably 70% or more, more preferably 80% or more, and even more preferably 85% or more. There is no particular limitation on the upper limit of this transmittance to light with a wavelength of 550 nm; for example, it may be 95% or less.

[0273] The light reflectance of the spectacle lens is preferably 70% or more, more preferably 80% or more, further preferably 85% or more, and even more preferably 90% or more. There is no particular upper limit to the light reflectance; for example, it can be 100% or less, or 95% or less.

[0274] The aforementioned transmittance refers to the transmittance at the optical center of the spectacle lens, which can be measured using a spectrophotometer. For example, a spectrophotometer such as the "U-4100" (trade name, manufactured by Hitachi, Ltd.) can be used. The aforementioned transmittance can be achieved by adjusting the content of compound 1 according to the thickness of the spectacle lens.

[0275] Example

[0276] The present invention will now be described in more detail using examples and comparative examples. It should be noted that the present invention is not limited to the following examples.

[0277] [Determination Method]

[0278] <Transmittance>

[0279] The transmittance at various wavelengths of light was measured using a spectrophotometer "U-4100" (trade name, manufactured by Hitachi, Ltd.). It should be noted that the transmittance measurement point was set at the optical center of the spectacle lens and the lens substrate.

[0280] <Maximum absorption wavelength (λmax)>

[0281] The maximum absorption wavelength (λmax) of the colorant was measured using a spectrophotometer “U-4100” (trade name, manufactured by Hitachi, Ltd.) under the following conditions.

[0282] Sample: Toluene solution (colorant content: 20 ppm by mass)

[0283] Measurement mode: transmittance

[0284] Optical path length: 10mm

[0285] <Light reflectivity>

[0286] The light reflectance was measured according to JIS T7333:2005. It should be noted that the measurement point for transmittance was set at the optical center of the spectacle lens and the lens substrate.

[0287] <Refractive index and Abbe number of the lens>

[0288] The refractive index of the spectacle lens was measured at 25°C using a precision refractometer, model "KPR-2000" (manufactured by Kalnew Optical Industries, Ltd.), via F' rays (488.0 nm), C' rays (643.9 nm), and e- rays (546.1 nm). The Abbe number was then calculated using the following formula.

[0289] Abbe number νe=(ne-1) / (nF'-nC')

[0290] ne is the refractive index measured by e-rays, nF' is the refractive index measured by F'-rays, and nC' is the refractive index measured by C'-rays.

[0291] <Blue LP Test>

[0292] A laser pointer (LP) with an emission wavelength of 405±10nm (output <1mW) was used to illuminate the optical center of the eyeglass lens, and it was confirmed whether the laser passed through.

[0293] (Evaluation Criteria)

[0294] ○: Lasers are significantly reduced

[0295] △: Laser intensity slightly reduced

[0296] ×: Laser transmission

[0297] <Example 1>

[0298] A mixture of 50.28 parts by mass of 2,5-bis(isocyanate-methyl)bicyclo[2.2.1]heptane and 2,6-bis(isocyanate-methyl)bicyclo[2.2.1]heptane was mixed with 0.06 parts by mass of dimethyltin chloride as a catalyst, 0.15 parts by mass of acidic phosphate ester "JP-506H" (trade name, manufactured by Jōhoku Chemical Industry Co., Ltd.) as a release agent, 0.55 parts by mass of 2-(2-hydroxy-4-ethoxyphenyl)2H-benzotriazole-5-carboxylic acid 2-ethylhexyl ester, 0.1037 parts by mass of Disperse Violet 27 (with a maximum absorption wavelength of 586 nm in a 20 ppm toluene solution), and 0.0013 parts by mass of Solvent Red 52 (with a maximum absorption wavelength of 543 nm in a 20 ppm toluene solution), and stirred. Then, 25.50 parts by weight of pentaerythritol tetra(3-mercaptopropionate) and 24.22 parts by weight of 1,2-bis(2-mercaptoethylthio)-3-mercaptopropane were added, and the mixture was stirred and mixed under reduced pressure of 10 mmHg for 30 minutes to prepare a curable composition. Next, this curable composition was injected into a pre-prepared lens molding mold (set to 0.00D, wall thickness 1.6 mm) consisting of a glass mold and a resin gasket, and polymerized in an electric furnace at 20°C–120°C for 24 hours. After polymerization, the gasket and mold were removed, and the mixture was heat-treated at 120°C for 2 hours to obtain the lens substrate. The optical properties and spectral transmittance of the obtained lens substrate are shown in Table 2. It should be noted that the light reflectance is 88.6%.

[0299] <Examples 2-4, Comparative Examples 1-8>

[0300] The composition of the raw materials was set as shown in Table 1. Otherwise, the lens substrate was obtained using the same method as in Example 1. The optical properties and spectral transmittance of the obtained lens substrate were measured, and the results are shown in Table 2. It should be noted that the light reflectance of the lens substrate in Example 3 was 88.0%.

[0301] <Example 5>

[0302] In a 300 mL flask, 79.92 parts by weight of bis-(β-cyclothiopropyl) sulfide, 14.00 parts by weight of sulfur, and 0.25 parts by weight of compound 1-1 were added. The mixture was heated to 60 °C and degassed for 60 minutes. Then, 0.467 parts by weight of 1-methyl-2-mercapto-1H-imidazole were added, and a pre-reaction was carried out at 60 °C for 60 minutes with stirring under a closed system at atmospheric pressure. The mixture was then cooled to 20 °C, and 0.13 parts by weight of dibutyltin chloride were added to stop the pre-reaction.

[0303] In another container, 1050 ppb of Disperse Violet 27 (with a maximum absorption wavelength of 586 nm in a 20 ppm toluene solution) and 450 ppb of Solvent Red 52 (with a maximum absorption wavelength of 543 nm in a 20 ppm toluene solution) were added as blueing agents and mixed and dissolved to carry out a pre-reaction. 6.08 parts by weight of bis-(2-mercaptoethyl) sulfide, 0.001 parts by weight of acid phosphate ester "JP506H" (trade name, manufactured by Jōhoku Chemical Industry Co., Ltd.), and 0.020 parts by weight of tetrabutylphosphine bromide were added to the product obtained from the pre-reaction. The mixture was stirred at 20°C while being degassed to prepare a homogeneous liquid.

[0304] Next, while filtering through a 3-micron polyethylene terephthalate filter, the sample was poured into a lens-forming mold (set to 0.00D, wall thickness 2.00mm) consisting of a glass mold and a resin gasket. The mold was then heated in an oven from 30°C to 100°C over 24 hours to polymerize and solidify. After demolding, the lens substrate was obtained. The optical properties and spectral transmittance of the obtained lens substrate were measured, and the results are shown in Table 4. It should be noted that the light reflectance was 84.2%.

[0305] <Comparative Examples 9-10>

[0306] The composition of the raw materials was set as shown in Table 3. Otherwise, the lens substrate was obtained by the same method as in Example 9. The optical properties and spectral transmittance of the obtained lens substrate were measured, and the results are shown in Table 4.

[0307] <Example 6>

[0308] Add 95.00 parts by weight of bis-(β-cyclothiopropyl) disulfide, 5.00 parts by weight of a mixture of 4,7-bis(mercaptomethyl)-3,6,9-trisulfide-1,11-undecanedithiol, 4,8-bis(mercaptomethyl)-3,6,9-trisulfide-1,11-undecanedithiol, and 5,7-bis(mercaptomethyl)-3,6,9-trisulfide-1,11-undecanedithiol, and compound 1-1 to a 300 mL flask. A homogeneous liquid was prepared by degassing 0.40 parts by weight of acid phosphate ester "JP506H" (trade name, manufactured by Jōhoku Chemical Industry Co., Ltd.), 1400 ppb by weight of dispersible violet 27 (maximum absorption wavelength of 586 nm in 20 ppm toluene solution) as a blueing agent, 600 ppb by weight of solvant red 52 (maximum absorption wavelength of 543 nm in 20 ppm toluene solution), and 0.10 parts by weight of dicyclohexylmethylamine at 20°C for 60 minutes.

[0309] Next, the sample was filtered through a 3-micron polyethylene terephthalate filter and poured into a lens-forming mold (set to 0.00D, wall thickness 2.00mm) consisting of a glass mold and a resin gasket. The mold was then heated in an oven from 30°C to 100°C over 24 hours to polymerize and solidify. After demolding, the lens substrate was obtained. The optical properties and spectral transmittance of the obtained lens substrate were measured, and the results are shown in Table 4.

[0310] <Comparative Example 11>

[0311] The composition of the raw materials was set as shown in Table 3. Otherwise, the lens substrate was obtained by the same method as in Example 6. The optical properties and spectral transmittance of the obtained lens substrate were measured, and the results are shown in Table 4.

[0312]

[0313] [Table 2]

[0314]

[0315]

[0316] [Table 4]

[0317]

[0318] The abbreviations in the table are as follows.

[0319] Compound 1-1: 2-(2-hydroxy-4-ethoxyphenyl)2H-benzotriazole-5-carboxylic acid 2-ethylhexyl ester

[0320] Compound 51: 2-(2-hydroxy-4-octyloxyphenyl)2H-benzotriazole

[0321] Compound 52: 2-(3-tert-butyl-2-hydroxy-5-methylphenyl)-5-chloro-2H-benzotriazole

[0322] Compound 53: 2-(2-hydroxy-5-methylphenyl)2H-benzotriazole

[0323] Compound 54: 2-(2-hydroxy-4-ethoxyphenyl)2H-benzotriazole

[0324] NBDI: A mixture of 2,5-bis(isocyanate-methyl)bicyclo[2.2.1]heptane and 2,6-bis(isocyanate-methyl)bicyclo[2.2.1]heptane.

[0325] PETMP: Pentaerythritol tetra(3-mercaptopropionate)

[0326] TFSH: 1,2-bis(2-mercaptoethio)-3-mercaptopropane

[0327] HXDI: 1,3-bis(isocyanate methyl)cyclohexane

[0328] PETMA: Pentaerythritol tetra(2-mercaptoacetate)

[0329] DMMD: 2,5-bis(mercaptomethyl)-1,4-dithiane

[0330] XDI: 1,3-bis(isocyanate methyl)benzene

[0331] FFSH: A mixture of 4,7-bis(mercaptomethyl)-3,6,9-trithia-1,11-undecanedithiol, 4,8-bis(mercaptomethyl)-3,6,9-trithia-1,11-undecanedithiol, and 5,7-bis(mercaptomethyl)-3,6,9-trithia-1,11-undecanedithiol.

[0332] ETPS: Bis(β-cyclothiopropyl) sulfides

[0333] MES: Bis(2-mercaptoethyl) sulfide

[0334] ETPDS: Bis(β-cyclothiopropyl)disulfide

Claims

1. A spectacle lens comprising a lens substrate containing a compound represented by formula (1) and a resin, wherein the refractive index ne of the lens substrate is 1.52 or higher and 1.80 or lower. The resin comprises at least one selected from urethane resins and cyclic sulfide resins. The compound represented by formula (1) comprises, relative to 100 parts by weight of the resin, 0.05 parts by weight and 0.60 parts by weight or less. In the formula, R 1 It consists of alkoxy groups with 1 to 20 carbon atoms. R 2 It is an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms. R 3 It is an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms. n is an integer from 1 to 2. m is an integer from 0 to 2.

2. The spectacle lens according to claim 1, wherein, The R 1 It consists of alkoxy groups with 4 to 20 carbon atoms. The R 2 It is an alkoxy group with 1 to 12 carbon atoms. n is 1, The value of m is 0.

3. The spectacle lens according to claim 1 or 2, wherein, The R 1 It consists of branched alkoxy groups with 4 to 20 carbon atoms.

4. The spectacle lens according to claim 1 or 2, wherein, The compound represented by formula (1) is selected from at least one of the following: 2-(2-hydroxy-4-methoxyphenyl)2H-benzotriazole-5-carboxylic acid 2-ethylhexyl ester 2-(2-hydroxy-4-ethoxyphenyl)2H-benzotriazole-5-carboxylic acid 2-ethylhexyl ester 2-(2-hydroxy-4-octyloxyphenyl)2H-benzotriazole-5-carboxylic acid 2-ethylhexyl ester 2-(2-hydroxy-4-methoxyphenyl)2H-benzotriazole-5-carboxylic acid methyl ester 2-(2-hydroxy-4-ethoxyphenyl)2H-benzotriazole-5-carboxylic acid methyl ester 2-(2-hydroxy-4-octyloxyphenyl)2H-benzotriazole-5-carboxylic acid methyl ester 2-(2-hydroxy-4-methoxyphenyl)2H-benzotriazole-5-carboxylic acid ethyl ester 2-(2-hydroxy-4-ethoxyphenyl)2H-benzotriazole-5-carboxylic acid ethyl ester 2-(2-hydroxy-4-octyloxyphenyl)2H-benzotriazole-5-carboxylic acid ethyl ester 2-(2-hydroxy-4-methoxyphenyl)2H-benzotriazole-5-carboxylic acid n-octyl ester, 2-(2-hydroxy-4-ethoxyphenyl)2H-benzotriazole-5-carboxylic acid n-octyl ester, and 2-(2-hydroxy-4-octyloxyphenyl)2H-benzotriazole-5-carboxylic acid n-octyl ester.

5. The spectacle lens according to claim 1 or 2, wherein, The compound represented by formula (1) is 2-(2-hydroxy-4-methoxyphenyl)2H-benzotriazole-5-carboxylic acid 2-ethylhexyl ester or 2-(2-hydroxy-4-ethoxyphenyl)2H-benzotriazole-5-carboxylic acid 2-ethylhexyl ester.

6. The spectacle lens according to claim 1 or 2, wherein, The overall transmittance of the eyeglass lenses to light with a wavelength of 410nm is less than 5%. The overall transmittance of the eyeglass lenses to light with a wavelength of 430nm is over 70%.

7. The spectacle lens according to claim 6, wherein, The overall transmittance of the eyeglass lenses to light with a wavelength of 410nm is less than 3%.

8. The spectacle lens according to claim 6, wherein, The overall transmittance of the eyeglass lenses to light with a wavelength of 410nm is less than 1.0%.

9. The spectacle lens according to claim 6, wherein, The overall transmittance of the eyeglass lenses to light with a wavelength of 430nm is less than 90%.

10. The spectacle lens according to claim 1 or 2, comprising a colorant (L) having a maximum absorption wavelength of 550 nm or higher and 600 nm or lower in a toluene solution of 20 ppm by mass.

11. The spectacle lens according to claim 1 or 2, comprising a colorant (S) having a maximum absorption wavelength of 500 nm or more and less than 550 nm in a toluene solution of 20 ppm by mass.

12. The spectacle lens according to claim 1 or 2, wherein, The resin is a cured product of isocyanate component and active hydrogen compound component, wherein the isocyanate component includes at least one selected from bis(isocyanate methyl)bicyclo[2.2.1]heptane, bis(isocyanate methyl)cyclohexane, bis(isocyanate methyl)benzene, toluene diisocyanate, diphenylmethane diisocyanate, dicyclohexylmethane diisocyanate, hexamethylene diisocyanate, and pentamethylene diisocyanate.

13. The spectacle lens according to claim 12, wherein, The active hydrogen compound component comprises at least one selected from toluene diamine, pentaerythritol tetramercaptoacetate, pentaerythritol tetramercaptopropionate, trimethylolpropane trimercaptoacetate, trimethylolpropane trimercaptopropionate, bis(mercaptoethylthio)mercaptopropane, bis(mercaptomethyl)-3,6,9-trithiadecanedithiol, dimercaptoethyl sulfide, bis(mercaptomethyl)dithiane, dimercaptoethyl ether, and diethylene glycol.

14. The spectacle lens according to claim 13, wherein, The bis(mercaptomethyl)-3,6,9-trithiaundecanedithiol is a mixture of 4,7-bis(mercaptomethyl)-3,6,9-trithia-1,11-undecanedithiol, 4,8-bis(mercaptomethyl)-3,6,9-trithia-1,11-undecanedithiol, and 5,7-bis(mercaptomethyl)-3,6,9-trithia-1,11-undecanedithiol.

15. The spectacle lens according to claim 1 or 2, wherein, The resin is a cyclic sulfide resin.

16. The spectacle lens according to claim 1 or 2, wherein, The compound represented by formula (1) comprises 0.10 to 0.55 parts by weight of the compound relative to 100 parts by weight of the resin.

17. The spectacle lens according to claim 1 or 2, wherein, The compound represented by formula (1) comprises 0.20 parts by mass and less than 0.55 parts by mass relative to 100 parts by mass of the resin.

18. The spectacle lens according to claim 1 or 2, wherein, The refractive index ne of the lens substrate is above 1.55 and below 1.

80.

19. The spectacle lens according to claim 1 or 2, wherein, The refractive index ne of the lens substrate is above 1.60 and below 1.

80.

20. The spectacle lens according to claim 1 or 2, wherein, The refractive index ne of the lens substrate is above 1.70 and below 1.

80.

21. The spectacle lens according to claim 1 or 2, comprising at least one layer selected from a hard coating layer, a base layer, and an anti-reflective layer.

22. The spectacle lens according to claim 1 or 2, wherein, The lens substrate is crescent-shaped.

23. The spectacle lens according to claim 22, wherein, The optical center thickness of the eyeglass lens is 0.5 mm or more and 10.0 mm or less.

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