eyeglass lenses

Abstract

An embodiment pertaining to the present disclosure relates to a spectacle lens containing a compound represented by formula (1).

Description

[Technical Field]

[0001] The present disclosure relates to eyeglass lenses. [Background technology]

[0002] In eyeglass lenses, blocking light in the blue range (wavelengths between 380 and 500 nm) reduces glare and improves visibility and contrast. Furthermore, with regard to eye health, light in the blue range (380 to 500 nm) is said to be highly energetic and to cause damage to the retina and other organs. Damage caused by blue light is called "blue light hazard," with the lowest wavelengths, around 380 to 420 nm, being the most dangerous, and it is said that blocking light in this range is desirable.

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

[0004] [Patent Document 1] International Publication No. WO2014 / 133111 Summary of the Invention [Problem to be solved by the invention]

[0005] Conventional eyeglass lenses, such as those disclosed in Patent Document 1, can suppress the transmittance of light with a wavelength of 410 nm by incorporating a specific ultraviolet absorber. However, ultraviolet absorbers generally exhibit light absorption characteristics at a wavelength of 410 nm and also absorb light with wavelengths close to that wavelength. Therefore, suppressing the transmittance of light with a wavelength of 410 nm using an ultraviolet absorber also absorbs light in the visible light range, resulting in coloring issues such as a yellowish tint of the eyeglass lenses. Yellow-tinted eyeglass lenses tend to appear deteriorated, so colorants are often added to give them a gray or slightly bluish color, which increases costs and, in some cases, reduces transmittance. Therefore, we focused on suppressing the coloring of eyeglass lenses caused by ultraviolet absorbers by increasing the transmittance of light with a wavelength of 430 nm.

[0006] One embodiment of the present disclosure relates to a spectacle 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. [Means for solving the problem]

[0007] One embodiment of the present disclosure is a compound of formula (1): [ka] (In the formula, R 1 is an alkoxy group having 1 to 20 carbon atoms, R 2 is an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms, R 3 is an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms, n is an integer of 1 to 2, and m is an integer of 0 to 2. [Effects of the Invention]

[0008] According to one embodiment of the present disclosure, it is possible to provide a spectacle lens that suppresses the transmittance of light with a wavelength of 410 nm and has excellent transmittance at a wavelength of 430 nm. [Brief explanation of the drawings]

[0009] [Figure 1] FIG. 1 is a schematic cross-sectional view of a spectacle lens 1 of the present embodiment. DETAILED DESCRIPTION OF THE INVENTION

[0010] Hereinafter, embodiments of the present disclosure will be described in detail with reference to the drawings as necessary, but the present disclosure is not limited thereto and various modifications are possible without departing from the spirit thereof. In the drawings, the same elements are denoted by the same reference numerals, and redundant explanations will be omitted. Furthermore, positional relationships such as up, down, left, and right are based on the positional relationships shown in the drawings unless otherwise specified. Furthermore, the dimensional ratios of the drawings are not limited to those shown. In this specification, for example, when a numerical range is expressed as "1 to 100," it is intended to include both the lower limit value "1" and the upper limit value "100." The same applies to other numerical ranges. For example, "a cured product of an isocyanate component and an active hydrogen compound component" does not mean excluding other components, but means a cured product of a composition containing at least an isocyanate component and an active hydrogen compound component.

[0011] [Eyeglass lenses] The eyeglass lens according to this embodiment has a structure represented by the formula (1): [ka] (In the formula, R1 is an alkoxy group having 1 to 20 carbon atoms, R2 is an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms, R3 is an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms, and m is an integer of 0 to 2.) (hereinafter also referred to as "compound 1"). According to one embodiment of the present disclosure, it is possible to provide a spectacle lens that suppresses the transmittance of light with a wavelength of 410 nm and has excellent transmittance at a wavelength of 430 nm.

[0012] <Compound 1> The spectacle lens according to this embodiment contains compound 1 represented by formula (1), which suppresses the transmittance of light with a wavelength of 410 nm and has excellent transmittance at a wavelength of 430 nm. Light with a wavelength of 410 nm is in the visible light range, but has relatively high energy, and is therefore harmful to the eyes when viewed for a long period of time. Compound 1 contains -COR in the benzotriazole ring. 1 Because it has a - group, it can absorb light with a wavelength of 410 nm. Furthermore, since the inclusion of a compound that absorbs light in the visible light region makes it more likely to become discolored, it is desirable not to absorb light with wavelengths longer than 410 nm. However, when observing the absorption spectrum, the absorption peak of the compound also absorbs light at the peak wavelength and its surrounding wavelengths, resulting in a mountain-shaped spectrum. Therefore, if the absorption rate of light with a wavelength of 410 nm is increased, the surrounding light will also be absorbed, making it more likely to become discolored. This causes problems such as discoloration of eyeglass lenses, or the need to use a large amount of dye to make the hue neutral gray to make the discoloration less noticeable, which ultimately reduces the luminous transmittance. To address this issue, Compound 1 has a -COR group on the benzotriazole ring. 1 The presence of this group makes it possible to suppress absorption at a wavelength of 430 nm.

[0013] -COR 1 The substitution position of the group is preferably the 5-position of the benzotriazole ring from the viewpoint of suppressing the transmittance of light with a wavelength of 410 nm and suppressing the transmittance of light with a wavelength of 430 nm. In formula (1), R 1 is an alkoxy group having 1 to 20 carbon atoms. R 1The number of carbon atoms in the alkoxy group in R is preferably 2 to 20, more preferably 4 to 20, even more preferably 6 to 18, even more preferably 6 to 15, and even more preferably 6 to 12. As the number of carbon atoms in the alkoxy group increases, the solubility of Compound 1 in organic compounds such as isocyanate components and polythiol components increases. 1 The alkyl group in may be branched or linear, but is preferably branched. R 1 Examples of the alkoxy group in include a methoxy group, an ethoxy group, an n-propyloxy group, an isopropyloxy group, an n-butyloxy group, a sec-butyloxy group, a tert-butyloxy group, a pentyloxy group, a 1-methylpentyloxy group, a 2-methylpentyloxy group, a 3-methylpentyloxy group, a 1-ethylpentyloxy group, a 2-ethylpentyloxy group, a 3-ethylpentyloxy group, an n-hexyloxy group, a 1-methylhexyloxy group, a 2-methylhexyloxy group, a 3-methylhexyloxy group, a 1-ethylhexyloxy group, a 2-ethylhexyloxy group, a 3-ethylhexyloxy group, an n Examples of the alkyl group include tert-heptyloxy, 1-methylheptyloxy, 2-methylheptyloxy, 3-methylheptyloxy, 1-ethylheptyloxy, 2-ethylheptyloxy, 3-ethylheptyloxy, n-octyloxy, 1-methyloctyloxy, 2-methyloctyloxy, 3-methyloctyloxy, 1-ethyloctyloxy, 2-ethyloctyloxy, 3-ethyloctyloxy, n-decyloxy, n-dodecyloxy, n-dodecyloxy, n-tetradecyloxy, n-hexadecyloxy, n-octadecyloxy, and n-icosyloxy. Among these, tert-butyloxy, hexyloxy, n-octyloxy, and 2-ethylhexyloxy are more preferred, with 2-ethylhexyloxy being more preferred. That's all, R 1is preferably an alkoxy group having 4 to 20 carbon atoms, more preferably a branched alkoxy group having 4 to 20 carbon atoms, even more preferably a tert-butyloxy group, or a 2-ethylhexyloxy group, still more preferably a 2-ethylhexyloxy group. n is an integer of 1 to 2, and is preferably 1.

[0014] In formula (1), R 2 is an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms, and the number of carbon atoms in the alkyl group and the number of carbon atoms in the alkoxy group are each independently preferably 1 to 8, more preferably 2 to 8, and even more preferably 4 to 8. The alkyl group and the alkoxy group may be branched or linear. Of the alkyl group and the alkoxy group, an alkoxy group is preferred. Examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, an n-octyl group, a 1,1,3,3-tetramethylbutyl group, a nonyl group, a decyl group, an undecyl group, and a dodecyl group. Examples of alkoxy groups include methoxy, ethoxy, n-propyloxy, isopropyloxy, n-butyloxy, sec-butyloxy, tert-butyloxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, and dodecyloxy groups. Among these, methoxy and ethoxy groups are preferred.

[0015] In formula (1), R 3 is an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms. 3 Examples of alkyl and alkoxy groups in R 2 This is similar to the example in m is an integer of 0 to 2, and is preferably 0.

[0016] Specific examples of Compound 1 include, but are not limited to, 2-ethylhexyl 2-(2-hydroxy-4-methoxyphenyl)2H-benzotriazole-5-carboxylate (compound represented by the following formula (1-1)), [ka] 2-ethylhexyl 2-(2-hydroxy-4-ethoxyphenyl)2H-benzotriazole-5-carboxylate (compound represented by the following formula (1-2)), [ka] 2-ethylhexyl 2-(2-hydroxy-4-octyloxyphenyl)2H-benzotriazole-5-carboxylate, methyl 2-(2-hydroxy-4-methoxyphenyl)2H-benzotriazole-5-carboxylate, methyl 2-(2-hydroxy-4-ethoxyphenyl)2H-benzotriazole-5-carboxylate, methyl 2-(2-hydroxy-4-octyloxyphenyl)2H-benzotriazole-5-carboxylate, ethyl 2-(2-hydroxy-4-methoxyphenyl)2H-benzotriazole-5-carboxylate, ethyl 2-(2-hydroxy-4-ethoxyphenyl)2H-benzotriazole-5-carboxylate, ethyl 2-(2-hydroxy-4-octyloxyphenyl)2H-benzotriazole-5-carboxylate, n-octyl 2-(2-hydroxy-4-methoxyphenyl)2H-benzotriazole-5-carboxylate, n-Octyl 2-(2-hydroxy-4-ethoxyphenyl)2H-benzotriazole-5-carboxylate, and n-octyl 2-(2-hydroxy-4-octyloxyphenyl)2H-benzotriazole-5-carboxylate, Among these compounds 1, one kind may be used alone, or two or more kinds may be used in combination. Among these, 2-ethylhexyl 2-(2-hydroxy-4-methoxyphenyl)2H-benzotriazole-5-carboxylate and 2-ethylhexyl 2-(2-hydroxy-4-ethoxyphenyl)2H-benzotriazole-5-carboxylate are preferred.

[0017] The spectacle lens according to this embodiment includes, for example, a lens substrate. The spectacle lens according to this embodiment may include at least one layer selected from the group consisting of a hard coat layer, an undercoat layer, and an anti-reflection layer.

[0018] 1 is a schematic cross-sectional view of a spectacle lens 1 of this embodiment. The spectacle lens 1 of this embodiment includes a lens substrate 11, a hard coat layer 21f provided on the object-side surface 11a of this lens substrate 11, a functional layer 31f provided on the object-side surface 21fa of this hard coat layer 21f, and a water-repellent layer 41f provided on the object-side surface 31fa of this functional layer 31f.

[0019] Furthermore, when the lens substrate 11 is a finished lens, the eyeglass lens 1 of this embodiment further comprises a hard coat layer 21b provided on the eyeball-side surface 11b of the lens substrate 11, a functional layer 31b provided on the eyeball-side surface 21bb of this hard coat layer 21b, and a water-repellent layer 41b provided on the eyeball-side surface 31bb of this functional layer 31b.

[0020] Although not shown, an underlayer may be provided between the lens substrate 11 and the hard coat layer 21f, or between the lens substrate 11 and the hard coat layer 21b.

[0021] <Lens substrate> The lens substrate may contain Compound 1 and a resin. The spectacle lens preferably contains, relative to 100 parts by mass of the resin of the lens substrate, 0.05 parts by mass or more and 2.00 parts by mass or less 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 is preferably 0.10 parts by mass or more and 2.00 parts by mass or less, more preferably 0.15 parts by mass or more and 1.50 parts by mass or less, and even more preferably 0.20 parts by mass or more and 1.00 parts by mass or less, relative to 100 parts by mass of the resin of the lens substrate.

[0022] From the viewpoints 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 a decrease in the Abbe number, the content of Compound 1 is preferably from 0.05 to 0.60 parts by mass, more preferably from 0.10 to 0.55 parts by mass, and even more preferably from 0.20 to 0.50 parts by mass, relative to 100 parts by mass of the resin of the lens substrate.

[0023] 〔resin〕 Examples of resins for the lens substrate include urethane resins, episulfide resins, polycarbonate resins, and acrylic resins. The resin is preferably at least one selected from the group consisting of polythiourethane resins, polysulfide resins, and polyurethane resins, and more preferably at least one selected from the group consisting of polythiourethane resins and polysulfide resins.

[0024] (urethane resin) The urethane resin is a cured product of a polymerizable composition containing an isocyanate component and an active hydrogen compound component. Examples of the urethane resin include a thiourethane resin containing a polymerization site between an isocyanate component and a polythiol component; a urethane resin containing a polymerization site between an isocyanate component and a polyol component; and a urethane urea resin having a polythiourethane site, which is a polymerization site between an isocyanate component and a polythiol component or a polyol component, and a polyurea site, which is a polymer of an isocyanate component and a polyamine component.

[0025] (Isocyanate component) Examples of the isocyanate component include polyisocyanate compounds having an aromatic ring, polyisocyanate compounds having an aliphatic ring, and linear or branched aliphatic polyisocyanate compounds.

[0026] Examples of polyisocyanate compounds having an aromatic ring include diisocyanatobenzene, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, ethyl phenylene diisocyanate, isopropyl phenylene diisocyanate, dimethyl phenylene diisocyanate, diethyl phenylene diisocyanate, diisopropyl phenylene diisocyanate, trimethylbenzene triisocyanate, benzene triisocyanate, biphenyl diisocyanate, 4,4'-diphenylmethane diisocyanate, 4,4'-methylenebis(2-methylphenyl isocyanate), bibenzyl-4,4'-diisocyanate, bis(isocyanatophenyl)ethylene, 1,3-bis(isocyanatomethyl)benzene, 1,4-bis(isocyanatomethyl)benzene, 1,3-bis(isocyanatoethyl)benzene, bis(isocyanatopropyl)benzene, bis(isocyanatobutyl)benzene, α,α,α',α'-tetramethylxylylene diisocyanate, bis(isocyanatobutyl)benzene, bis(isocyanatomethyl)naphthalene, bis(isocyanatomethylphenyl)ether, 2-isocyanatophenyl-4-isocyanatophenyl sulfide, bis(4-isocyanatophenyl) sulfide, bis(4-isocyanatomethylphenyl) sulfide, bis(4-isocyanatophenyl) disulfide, bis(2-methyl-5-isocyanatophenyl) disulfide, bis(3-methyl-5-isocyanatophenyl) disulfide, bis(3-methyl-6-isocyanatophenyl) disulfide, bis(4-methyl-5-isocyanatophenyl) disulfide, bis(3-methyloxy-4-isocyanatophenyl) disulfide, bis(4-methyloxy-3-isocyanatophenyl) disulfide.

[0027] Examples of polyisocyanate compounds having an aliphatic ring include 1,3-diisocyanatocyclohexane, 1,4-diisocyanatocyclohexane, isophorone diisocyanate, 1,3-bis(isocyanatomethyl)cyclohexane, 1,4-bis(isocyanatomethyl)cyclohexane, dicyclohexylmethane-4,4'-diisocyanate, dicyclohexylmethane-2,4'-diisocyanate, and 2,5-bis(isocyanatomethyl)cyclohexane. Examples of such bis(isocyanatomethyl)-bicyclo[2.2.1]heptane include 2,6-bis(isocyanatomethyl)-bicyclo[2.2.1]heptane, 2,5-diisocyanato-1,4-dithiane, 2,5-bis(isocyanatomethyl)-1,4-dithiane, 4,5-diisocyanato-1,3-dithiolane, 4,5-bis(isocyanatomethyl)-1,3-dithiolane, and 4,5-bis(isocyanatomethyl)-2-methyl-1,3-dithiolane.

[0028] 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. Methylene triisocyanate, 1,8-diisocyanato-4-isocyanatomethyloctane, bis(isocyanatoethyl)carbonate, bis(isocyanatoethyl)ether, lysine diisocyanatomethyl ester, lysine triisocyanate, bis(isocyanatomethyl)sulfide, bis(isocyanatoethyl)sulfide, bis(isocyanatopropyl)sulfide, bis(isocyanatohexyl)sulfide, bis(isocyanatomethyl) methyl) sulfone, bis(isocyanatomethyl) disulfide, bis(isocyanatoethyl) disulfide, bis(isocyanatopropyl) disulfide, bis(isocyanatomethylthio)methane, bis(isocyanatoethylthio)methane, bis(isocyanatomethylthio)ethane, bis(isocyanatoethylthio)ethane, 1,5-diisocyanato-2-isocyanatomethyl-3-pentane, 1,2,3-tris(isocyanatomethylthio)propyl Examples of suitable isocyanatoisocyanates include pan, 1,2,3-tris(isocyanatoethylthio)propane, 3,5-dithia-1,2,6,7-heptanetetraisocyanate, 2,6-diisocyanatomethyl-3,5-dithia-1,7-heptanediisocyanate, 2,5-diisocyanatomethylthiophene, 4-isocyanatoethylthio-2,6-dithia-1,8-octanediisocyanate, 1,2-diisothiocyanatoethane, and 1,6-diisothiocyanatohexane. These may be used alone or in combination of two or more.

[0029] The isocyanate component preferably contains at least one selected from the group consisting of bis(isocyanatomethyl)bicyclo[2.2.1]heptane, bis(isocyanatomethyl)cyclohexane, bis(isocyanatomethyl)benzene, tolylene diisocyanate, diphenylmethane diisocyanate, dicyclohexylmethane diisocyanate, hexamethylene diisocyanate, and pentamethylene diisocyanate (hereinafter also referred to as a "suitable isocyanate compound"). Examples of bis(isocyanatomethyl)bicyclo[2.2.1]heptane include one or more selected from the group consisting of 2,5-bis(isocyanatomethyl)bicyclo[2.2.1]heptane and 2,6-bis(isocyanatomethyl)bicyclo[2.2.1]heptane, and preferably a mixture of 2,5-bis(isocyanatomethyl)bicyclo[2.2.1]heptane and 2,6-bis(isocyanatomethyl)bicyclo[2.2.1]heptane. Examples of bis(isocyanatomethyl)cyclohexane include 1,3-bis(isocyanatomethyl)cyclohexane and 1,4-bis(isocyanatomethyl)cyclohexane. Among these, 1,3-bis(isocyanatomethyl)cyclohexane is preferred. Examples of bis(isocyanatomethyl)benzene include 1,3-bis(isocyanatomethyl)benzene and 1,4-bis(isocyanatomethyl)benzene. Among these, 1,3-bis(isocyanatomethyl)benzene is preferred. Examples of tolylene diisocyanate include 2,4-tolylene diisocyanate and 2,6-tolylene diisocyanate. Among these, 2,4-tolylene diisocyanate is preferred. Examples of diphenylmethane diisocyanates include 4,4'-diphenylmethane diisocyanate and 2,4'-diphenylmethane diisocyanate. Dicyclohexylmethane diisocyanate includes, for example, dicyclohexylmethane-4,4'-diisocyanate.

[0030] In the isocyanate component, the content of the above-mentioned "suitable isocyanate compound" 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.

[0031] (active hydrogen compound component) Examples of the active hydrogen compound component include a polythiol component, a polyol component, and a polyamine component.

[0032] (Polythiol component) Examples of the polythiol component include an ester compound of a polyol compound and a mercapto group-containing carboxylic acid compound, a linear or branched aliphatic polythiol compound, a polythiol compound having an aliphatic ring, and a polythiol compound having an aromatic ring.

[0033] In the ester compound of a polyol compound and a mercapto group-containing carboxylic acid compound, the polyol compound may be a compound having two or more hydroxyl groups in the molecule, such as ethylene glycol, diethylene glycol, propanediol, propanetriol, butanediol, trimethylolpropane, bis(2-hydroxyethyl)disulfide, pentaerythritol, or dipentaerythritol. Examples of the mercapto group-containing carboxylic acid compound include thioglycolic acid, mercaptopropionic acid, thiolactic acid compounds, and thiosalicylic acid. Examples of the ester compound of a polyol compound and a mercapto group-containing carboxylic acid compound 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), pentaerythritol tetrakis(2-mercaptoacetate), pentaerythritol tetrakis(3-mercaptopropionate), dipentaerythritol hexakis(2-mercaptoacetate), dipentaerythritol hexakis(3-mercaptopropionate).

[0034] Examples of linear or branched aliphatic polythiol compounds 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-dimethyloxybutane-1,2-dithiol, 2,3-dimercapto-1-propanol, 1,2-dimethyl-2,3-dimethylpropane-1,3-dithiol, 3,4-dimethyloxybutane-1,2-dithiol, 2,3-dimercapto-1-propanol, 1,2-dimethyl-2,3-dimethylpropane-1,3-dithiol, 2,3 ... mercaptopropyl methyl ether, 2,3-dimercaptopropyl methyl ether, dimercaptoethyl ether, 2-(2-mercaptoethylthio)propane-1,3-dithiol, 2,2-bis(mercaptomethyl)-1,3-propanedithiol, bis(mercaptomethylthio)methane, tris(mercaptomethylthio)methane, bis(2-mercaptoethylthio)methane, 1,2-bis(mercaptomethylthio)ethane, 1,2-bis(2-mercaptomethylthio)ethane, 1,3-bis(mercaptomethylthio)propane, 1,3-bis(2-mercaptoethylthio)propane, 1,1,2,2-tetrakis(mercaptoethylthio)ethane, 1,1,3,3-tetrakis(mercaptoethylthio)propane, 3-mercaptomethyl-1,5-dimercapto-2,4-dithiapentane, tetrakis(mercaptoethylthio)propane, bis(2-mercaptoethyl)ether, bis(2-mercaptoethyl)ether bis(mercaptoethyl) sulfide, bis(2-mercaptoethyl) disulfide, 1,2-bis(2-mercaptoethylthio)-3-mercaptopropane, 4,7-bis(mercaptomethyl)-3,6,9-trithiaundecane-1,11-dithiol, 4,8-bis(mercaptomethyl)-3,6,9-trithiaundecane-1,11-dithiol, and 5,7-bis(mercaptomethyl)-3,6,9-trithiaundecane-1,11-dithiol.

[0035] Examples of polythiol compounds having an aliphatic ring include 1,1-cyclohexanedithiol, 1,2-cyclohexanedithiol, methylcyclohexanedithiol, bis(mercaptomethyl)cyclohexane, 2-(2,2-bis(mercaptomethylthio)ethyl)-1,3-dithietane, 2,5-bis(mercaptomethyl)-1,4-dithiane, and 4,8-bis(mercaptomethyl)-1,3-dithiane.

[0036] Examples of the polythiol compound having an aromatic ring 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-tris(mercaptomethyl)benzene, 1,3,5-tris(mercaptoethyl)benzene, 4,4'-dimercaptobiphenyl, 4,4'-dimercaptobiphenyl, Examples of such thiol include benzil, 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-anthracenedimethanethiol, 1,3-di(p-methyloxyphenyl)propane-2,2-dithiol, 1,3-diphenylpropane-2,2-dithiol, phenylmethane-1,1-dithiol, and 2,4-di(p-mercaptophenyl)pentane. These may be used alone or in combination of two or more.

[0037] (Polyol component) Examples of the polyol component include ethylene glycol, diethylene glycol, propanediol, propanetriol, butanediol, trimethylolpropane, bis(2-hydroxyethyl) disulfide, pentaerythritol, and dipentaerythritol.

[0038] (Polyamine component) Examples of the polyamine component include polymethylenediamine, polyetherdiamine, diethylenetriamine, iminobispropylamine, bishexamethylenetriamine, diethylenetriamine, tetraethylenepentamine, pentaethylenehexamine, pentaethylenehexamine, dimethylaminopropylamine, aminoethylethanolamine, methyliminobispropylamine, menthanediamine, N-aminomethylpiperazine, 1,3-diaminocyclohexane, isophoronediamine, metaxylenediamine, tetrachloroparaxylenediamine, metaphenylenediamine, 4,4'-methylenedianiline, diaminodiphenylsulfone, benzidine, diaminodiphenyl ether, 4,4'-thiodianiline, 4,4'-bis(o-toluidine)dianisidine, o-phenylenediamine, 2,4-toluidine ... Examples of suitable amines include enediamine, 2,5-toluenediamine, methylenebis(o-chloroaniline), diaminiditolylsulfone, bis(3,4-diaminophenyl)sulfone, 2,6-diaminopyridine, 4-chloro-o-phenylenediamine, 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(dimethylaminomethylol)phenol, N-methylpiperazine, N-β(aminoethyl)γ-aminopropyltrimethoxysilane, N-β(aminoethyl)γ-aminopropylmethyldimethoxysilane, and γ-aminopropylmethyldimethoxysilane.

[0039] The active hydrogen compound component preferably contains at least one selected from the group consisting of toluenediamine, pentaerythritol tetrakismercaptoacetate, pentaerythritol tetrakismercaptopropionate, trimethylolpropane trismercaptoacetate, trimethylolpropane trismercaptopropionate, bis(mercaptoethylthio)mercaptopropane, bis(mercaptomethyl)-3,6,9-trithiaundecanedithiol, dimercaptoethyl sulfide, bis(mercaptomethyl)dithiane, dimercaptoethyl ether, and diethylene glycol. Examples of toluenediamines include 2,4-toluenediamine and 2,5-toluenediamine. An example of pentaerythritol tetrakis mercaptoacetate is pentaerythritol tetrakis(2-mercaptoacetate). An example of pentaerythritol tetrakis mercaptopropionate is pentaerythritol tetrakis(3-mercaptopropionate). An example of trimethylolpropane tris-mercaptoacetate is trimethylolpropane tris(2-mercaptoacetate). An example of trimethylolpropane tris-mercaptopropionate is trimethylolpropane tris(3-mercaptopropionate). An example of the bis(mercaptoethylthio)mercaptopropane is 1,2-bis(2-mercaptoethylthio)-3-mercaptopropane. Examples of bis(mercaptomethyl)-3,6,9-trithiaundecane dithiol include 4,7-bis(mercaptomethyl)-3,6,9-trithiaundecane-1,11-dithiol, 4,8-bis(mercaptomethyl)-3,6,9-trithiaundecane-1,11-dithiol, and 5,7-bis(mercaptomethyl)-3,6,9-trithiaundecane-1,11-dithiol. The bis(mercaptomethyl)-3,6,9-trithiaundecanedithiol is preferably a mixture of 4,7-bis(mercaptomethyl)-3,6,9-trithiaundecane-1,11-dithiol, 4,8-bis(mercaptomethyl)-3,6,9-trithiaundecane-1,11-dithiol, and 5,7-bis(mercaptomethyl)-3,6,9-trithiaundecane-1,11-dithiol.

[0040] The active hydrogen compound component is preferably a polythiol component. The polythiol component is Preferably, 2,5-bis(mercaptomethyl)-1,4-dithiane, pentaerythritol tetrakis(2-mercaptoacetate), pentaerythritol tetrakis(3-mercaptopropionate), 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 4,7-bis(mercaptomethyl)-3,6,9-trithiaundecane-1,11-dithiol, 4,8-bis(mercaptomethyl)-3,6,9-trithiaundecane-1,11-dithiol, 5,7-bis(mercaptomethyl)- at least one selected from the group consisting of (methyl)-3,6,9-trithiaundecane-1,11-dithiol, trimethylolpropane tris(2-mercaptoacetate), trimethylolpropane tris(3-mercaptopropionate), butanediol bis(2-mercaptoacetate), butanediol bis(3-mercaptopropionate), dipentaerythritol hexakis(2-mercaptoacetate), and dipentaerythritol hexakis(3-mercaptopropionate); More preferably, the mercaptomethyl-1,8-dimercapto-3,6-dithiaundecane-1,11-dithiol is at least one selected from the group consisting of 4,7-bis(mercaptomethyl)-3,6,9-trithiaundecane-1,11-dithiol, 4,8-bis(mercaptomethyl)-3,6,9-trithiaundecane-1,11-dithiol, 5,7-bis(mercaptomethyl)-3,6,9-trithiaundecane-1,11-dithiol, 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, pentaerythritol tetrakis(3-mercaptopropionate), 2,5-bis(mercaptomethyl)-1,4-dithiane, and pentaerythritol tetrakis(2-mercaptoacetate), More preferably, the thiol-based copolymer contains at least one selected from the group consisting of 4,7-bis(mercaptomethyl)-3,6,9-trithiaundecane-1,11-dithiol, 4,8-bis(mercaptomethyl)-3,6,9-trithiaundecane-1,11-dithiol, and 5,7-bis(mercaptomethyl)-3,6,9-trithiaundecane-1,11-dithiol, More preferably, it contains a mixture of 4,7-bis(mercaptomethyl)-3,6,9-trithiaundecane-1,11-dithiol, 4,8-bis(mercaptomethyl)-3,6,9-trithiaundecane-1,11-dithiol, and 5,7-bis(mercaptomethyl)-3,6,9-trithiaundecane-1,11-dithiol.

[0041] The amount of the above-mentioned preferred polythiol component in the polythiol component is preferably 50% by mass or more, more preferably 70% by mass or more, even more preferably 90% by mass or more, and even more preferably 95% by mass or more, and is 100% by mass or less.

[0042] The equivalent ratio of mercapto groups in the polythiol component to isocyanato groups in the polyisocyanate component (mercapto groups / isocyanato groups) is preferably 40 / 60 or more, more preferably 43 / 57 or more, even more preferably 45 / 55 or more, and is preferably 60 / 40 or less, more preferably 55 / 45 or less, even more preferably 53 / 47 or less.

[0043] 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, and even more preferably 95% by mass or more, and 100% by mass or less.

[0044] (episulfide resin) The episulfide resin is a cured product of a polymerizable composition containing an epithio compound. The polymerizable composition may contain other monomers.

[0045] (epithio compounds) An epithio compound is a compound having an episulfide group (epithio group). Examples of the epithio compound include episulfide compounds having a linear or branched aliphatic skeleton, episulfide compounds having an alicyclic skeleton, episulfide compounds having an aromatic skeleton, and episulfide compounds having a dithiane ring skeleton.

[0046] Examples of episulfide compounds having a linear or branched aliphatic skeleton include bis-(β-epithiopropyl)sulfide, bis-(β-epithiopropyl)disulfide, 2-(2-β-epithiopropylthioethylthio)-1,3-bis(β-epithiopropylthio)propane, 1,2-bis[(2-β-epithiopropylthioethyl)thio]-3-(β-epithiopropylthio)propane, tetrakis(β-epithiopropylthiomethyl)methane, and 1,1,1-tris(β-epithiopropylthiomethyl)propane.

[0047] Examples of the episulfide compound having an alicyclic skeleton include 1,3-bis(β-epithiopropylthio)cyclohexane, 1,4-bis(β-epithiopropylthio)cyclohexane, 1,3-bis(β-epithiopropylthiomethyl)cyclohexane, 1,4-bis(β-epithiopropylthiomethyl)cyclohexane, bis[4-(β-epithiopropylthio)cyclohexyl]methane, 2,2-bis[4-(β-epithiopropylthio)cyclohexyl]propane, and bis[4-(β-epithiopropylthio)cyclohexyl]sulfide.

[0048] Examples of episulfide compounds having an aromatic skeleton include 1,3-bis(β-epithiopropylthio)benzene, 1,4-bis(β-epithiopropylthio)benzene, 1,3-bis(β-epithiopropylthiomethyl)benzene, 1,4-bis(β-epithiopropylthiomethyl)benzene, bis[4-(β-epithiopropylthio)phenyl]methane, 2,2-bis[4-(β-epithiopropylthio)phenyl]propane, bis[4-(β-epithiopropylthio)phenyl]sulfide, bis[4-(β-epithiopropylthio)phenyl]sulfine, and 4,4-bis(β-epithiopropylthio)biphenyl.

[0049] Examples of episulfide compounds having a dithiane ring skeleton include 2,5-bis(β-epithiopropylthiomethyl)-1,4-dithiane, 2,5-bis(β-epithiopropylthioethylthiomethyl)-1,4-dithiane, 2,5-bis(β-epithiopropylthioethyl)-1,4-dithiane, and 2,3,5-tri(β-epithiopropylthioethyl)-1,4-dithiane. In addition to the epithio compound, other polymerizable components such as the polyisocyanate component and polythiol component described above may be added. Among these, episulfide compounds having a linear or branched aliphatic skeleton are preferred, and bis-(β-epithiopropyl) sulfide or bis-(β-epithiopropyl) disulfide is more preferred. The content of the epithio compound in the polymerizable composition is preferably 50% by mass or more, more preferably 60% by mass or more, even more preferably 70% by mass or more, even more preferably 80% by mass or more, even more preferably 90% by mass or more, and preferably 98% by mass or less, more preferably 96% by mass or less.

[0050] Preferably, the polymerizable composition further contains sulfur or a polythiol compound in combination with the epithio compound. 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. Examples of the polythiol compound include the compounds exemplified above. When used in combination with an epithio compound, the content of the polythiol compound 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, even more preferably 30% by mass or less, even more preferably 20% by mass or less, and even more preferably 10% by mass or less.

[0051] When the polymerizable composition includes a polyisocyanate component and a polythiol component, or an epithio compound, it preferably includes a polymerization catalyst. Examples of the polymerization catalyst include tin compounds and nitrogen-containing compounds. Examples of the tin compound include alkyltin compounds and alkyltin halide compounds. Examples of alkyltin compounds include dibutyltin diacetate and dibutyltin dilaurate. Examples of alkyltin halide compounds include dibutyltin dichloride, dimethyltin dichloride, monomethyltin trichloride, trimethyltin chloride, tributyltin chloride, tributyltin fluoride, and dimethyltin dibromide. Among these, dibutyltin diacetate, dibutyltin dilaurate, dibutyltin dichloride, and dimethyltin dichloride are preferred, with dimethyltin dichloride being more preferred.

[0052] Examples of the nitrogen-containing compound include tertiary amines, quaternary ammonium salts, imidazole compounds, and pyrazole compounds. The tertiary amine is preferably a hindered amine.

[0053] 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).

[0054] Examples of the hindered amine 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-piperidyl sebacate, a mixture of methyl-1,2,2,6,6-pentamethyl-4-piperidyl sebacate and bis(1,2,2,6,6-pentamethyl-4-piperidyl) sebacate, and bis(1,2,2,6,6 -pentamethyl-4-piperidyl)sebacate, bis(2,2,6,6-tetramethyl-1-(octyloxy)-4-piperidyl)sebacate, bis(1,2,2,6,6-pentamethyl-4-piperidyl)[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methyl]butylmalonate, and tetrakis(1,2,2,6,6-pentamethyl-4-piperidyl)butane-1,2,3,4-tetracarboxylate.

[0055] An example of the quaternary ammonium salt is tetraethylammonium hydroxide. Examples of imidazole compounds include imidazole, 1-methyl-2-mercapto-1H-imidazole, 1,2-dimethylimidazole, benzylmethylimidazole, and 2-ethyl-4-imidazole. Examples of pyrazole compounds include pyrazole and 3,5-dimethylpyrazole. Among these, tertiary amines such as hindered amines, imidazole compounds, and pyrazole compounds are preferred, imidazole compounds are more preferred, and 1-methyl-2-mercapto-1H-imidazole is even more preferred.

[0056] When the polymerizable composition contains an isocyanate component and an active hydrogen compound component, the amount of the polymerization catalyst added in the polymerizable composition is preferably 0.001 part by mass or more, more preferably 0.005 part by mass or more, even more preferably 0.007 part by mass or more, and is preferably 2 parts by mass or less, more preferably 1 part by mass or less, even more preferably 0.5 parts by mass or less, relative to 100 parts by mass of the total amount of the isocyanate component and the active hydrogen compound component.

[0057] When an epithio compound is contained, the amount of the polymerization catalyst added in the polymerizable composition is preferably 0.001 part by mass or more, more preferably 0.005 part by mass or more, even more preferably 0.007 part by mass or more, and preferably 2 parts by mass or less, more preferably 1 part by mass or less, even more preferably 0.5 parts by mass or less, relative to 100 parts by mass of the total amount of the polymerizable components.

[0058] (Polycarbonate resin) The polycarbonate resin is preferably a cured product of a polymerizable composition containing diethylene glycol bisallyl carbonate.

[0059] The monomer preferably contains a monomer having two or more polymerizable unsaturated bonds in the molecule in order to obtain a three-dimensionally crosslinked optical resin. Examples of the polymerizable unsaturated bond include a (meth)acrylate group, an allyl group, a vinyl group, etc. The (meth)acrylate group is at least one selected from the group consisting of a methacrylate group and an acrylate group. Among these, at least one selected from the group consisting of a methacrylate group and an allyl group is preferred.

[0060] The monomer having two or more polymerizable unsaturated bonds in the molecule preferably includes diethylene glycol bisallyl carbonate, and more preferably includes diethylene glycol bisallyl carbonate, benzyl methacrylate, diallyl phthalate, and alkyl methacrylate in which the alkyl group has 1 to 4 carbon atoms.

[0061] The amount of diethylene glycol bisallyl carbonate blended is preferably 5% by mass or more, more preferably 10% by mass or more, even more preferably 20% by mass or more, and is preferably 100% by mass or less, more preferably 80% by mass or less, even more preferably 50% by mass or less, even more preferably 40% by mass or less, based on the total amount of monomers.

[0062] When used in combination with benzyl methacrylate, diallyl phthalate, and an alkyl methacrylate having an alkyl group with 1 to 4 carbon atoms, the amount of diethylene glycol bisallyl carbonate blended is more preferably 5% by mass or more, more preferably 10% by mass or more, even more preferably 20% by mass or more, and more preferably 40% by mass or less, more preferably 35% by mass or less, based on the total amount of monomers.

[0063] The amount of benzyl methacrylate to be blended 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, based on the total amount of monomers.

[0064] The diallyl phthalate may be one or two selected from the group consisting of diallyl isophthalate and diallyl terephthalate.

[0065] The amount of diallyl phthalate blended is preferably 14% by mass or more, more preferably 20% by mass or more, even more preferably 30% by mass or more, based on the total amount of monomers, and is preferably 88% by mass or less, more preferably 70% by mass or less, even more preferably 60% by mass or less.

[0066] Examples of alkyl methacrylates having an alkyl group with 1 to 4 carbon atoms include at least one selected from the group consisting of methyl methacrylate, ethyl methacrylate, n-propyl methacrylate, iso-propyl methacrylate, n-butyl methacrylate, sec-butyl methacrylate, iso-butyl methacrylate, and tert-butyl methacrylate.

[0067] The amount of alkyl methacrylate to be blended is preferably 1% by mass or more, more preferably 2% by mass or more, and even more preferably 3% by mass or more, and is preferably 6% by mass or less, and more preferably 5% by mass or less, based on the total amount of monomers.

[0068] Examples of the radical initiator used in the polymerization include 1,1-azobiscyclohexane carbonate, diisopropyl peroxycarbonate, 1,1'-azobiscyclohexane nitrate, and di-tert-butyl peroxide. The amount of the radical initiator to be added is preferably 0.1 part by mass or more, more preferably 0.5 part by mass or more, even more preferably 1.0 part 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, relative to 100 parts by mass of the monomer.

[0069] (acrylic resin) The acrylic resin is a cured product of a polymerizable composition containing an acrylic compound, which may also contain other monomers.

[0070] Examples of the acrylic compound include polyfunctional (meth)acrylate compounds having an aromatic ring, polyalkylene glycol di(meth)acrylates, and monofunctional acrylates. Among these, it is preferable to include a polyfunctional (meth)acrylate compound having an aromatic ring and a polyalkylene glycol di(meth)acrylate.

[0071] Examples of polyfunctional (meth)acrylate compounds having an aromatic ring include alkylene oxide-modified bisphenol A having (meth)acryloyl groups at both ends, and alkylene oxide-modified and urethane-modified bisphenol A having (meth)acryloyl groups at both ends. Among these, alkylene oxide-modified bisphenol A having (meth)acryloyl groups at both ends is preferred. The alkylene oxide-modified bisphenol A having (meth)acryloyl groups at both ends is preferably a bisphenol A represented by the formula (2): [ka] [In the formula, R 51 is an ethylene group or a propylene group, and R 52 is hydrogen or a methyl group, X is an oxygen atom or a sulfur atom, preferably an oxygen atom, m and n are each the average number of moles added, and m+n is 1.5 to 6, preferably 2 to 4. Examples of alkylene oxide-modified bisphenol A 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.

[0072] 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.

[0073] 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.

[0074] The content of the polyalkylene glycol di(meth)acrylate in the polymerizable composition is preferably 10% by mass or more, more preferably 20% by mass or more, even more preferably 30% by mass or more, and preferably 60% by mass or less, more preferably 50% by mass or less, even more preferably 45% by mass or less.

[0075] 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-naphthyloxyethyl (meth)acrylate, 2-naphthyloxyethyl (meth)acrylate, 2,4,6-tribromophenyl (meth)acrylate, 2,4,6-tribromophenoxyethyl (meth)acrylate, 2,4,6-tribromophenyl-di(oxyethyl)-(meth)acrylate, and 2,4,6-tribromobenzyl (meth)acrylate.

[0076] The total content of the polymerizable components 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 is preferably 99% by mass or less, more preferably 95% by mass or less.

[0077] When the polymerizable composition contains an acrylic compound, it preferably contains a radical polymerization initiator. Examples of the radical polymerization initiator include an energy ray-sensitive polymerization initiator and a heat-sensitive polymerization initiator. Examples of the energy ray-sensitive polymerization initiator include 2-hydroxy-2-methyl-1-phenylpropan-1-one, hydroxycyclohexyl phenyl ketone, methylphenyl glyoxylate, and 2,4,6-trimethylbenzoyldiphenylphosphine oxide.

[0078] Examples of the heat-sensitive polymerization initiator include organic peroxides and azo compounds. Examples of organic peroxides include peroxyesters such as tert-butyl peroxyneodecanoate, tert-butyl peroxypivalate, tert-butyl peroxyisobutyrate, tert-butyl peroxyacetate, cumyl peroxyneodecanoate, tert-butyl peroxyoctoate, tert-butyl peroxyisopropyl carbonate, cumyl peroxyoctoate, tert-hexyl peroxyneodecanoate, tert-hexyl peroxypivalate, and tert-butyl peroxyneohexanoate; peroxyketals such as 2,2-bis(tert-butylperoxy)-3,3,5-trimethylcyclohexane, 1,1-bis(tert-butylperoxy)cyclohexane, 2,2-bis(tert-butylperoxy)octane, and 2,2-bis(tert-butylperoxy)butane; diacyl peroxides such as acetyl peroxide, isobutyryl peroxide, octanoyl peroxide, lauroyl peroxide, benzoyl peroxide, and m-toluoyl peroxide; and peroxydicarbonates such as diisopropyl peroxydicarbonate and di-n-propyl peroxydicarbonate.

[0079] Examples of azo compounds include 2,2'-azobisisobutyronitrile, 1,1'-azobis(cyclohexane-1-carbonitrile), 2,2'-azobis(2-methylbutyronitrile), 2,2'-azobis(2,4-dimethylvaleronitrile), dimethyl-2,2'-azobisisobutyrate, and 2,2'-azobis(2,4,4-trimethylpentane).

[0080] The amount of the radical polymerization initiator added 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 is preferably 10 parts by mass or less, more preferably 5 parts by mass or less, even more preferably 3 parts by mass or less, relative to 100 parts by mass of the total amount of the acrylic compounds.

[0081] The lens substrate may contain other additives such as a release agent, a colorant, an antioxidant, a color prevention agent, a fluorescent brightener, etc. These may be used alone or in combination of two or more kinds.

[0082] [Release agent] Examples of the release agent include phosphoric acid ester compounds such as isopropyl acid phosphate, butyl acid phosphate, octyl acid phosphate, nonyl acid phosphate, decyl acid phosphate, isodecyl acid phosphate, isodecyl acid phosphate, tridecyl acid phosphate, stearyl acid phosphate, propylphenyl acid phosphate, butylphenyl acid phosphate, and butoxyethyl acid phosphate. The phosphoric acid ester compound may be either a phosphoric acid monoester compound or a phosphoric acid diester compound, but a mixture of a phosphoric acid monoester compound and a phosphoric acid diester compound is preferred.

[0083] The amount of release agent added is preferably 0.01 part by mass or more, preferably 0.05 part by mass or more, and preferably 1.00 part by mass or less, preferably 0.50 part by mass or less, per 100 parts by mass of the total amount of resin.

[0084] [Coloring Agent] The lens substrate may contain a colorant to the extent that the luminous transmittance, which will be described later, is not impaired. In order to make the coloring caused by the addition of the above-mentioned compound 1 less noticeable, the lens substrate may contain colorant L (hereinafter simply referred to as "colorant L") that has a maximum absorption wavelength of 550 nm or more and 600 nm or less in a 20 ppm by mass toluene solution. In order to make the coloring caused by the addition of the above-mentioned compound 1 less noticeable, the lens substrate may contain colorant S (hereinafter simply referred to as "colorant S") that has a maximum absorption wavelength of 500 nm or more and less than 550 nm in a 20 ppm by mass toluene solution.

[0085] (Colorant L) In order to obtain a lens substrate with a good, slightly bluish color tone, colorant L has a maximum absorption wavelength of 550 nm or more and 600 nm or less in a 20 ppm by mass toluene solution. Note that the 20 ppm by mass toluene solution refers to the ratio of the solute to the entire toluene solution. The maximum absorption wavelength of colorant L is preferably 550 nm or longer, more preferably 560 nm or longer, and even more preferably 580 nm or longer, from the viewpoint of obtaining a lens substrate with a slightly bluish, favorable color tone. The maximum absorption wavelength of colorant L is preferably 600 nm or shorter, and even more preferably 590 nm or shorter, from the viewpoint of obtaining a resin composition with a slightly bluish, favorable color tone.

[0086] Examples of colorant L include CI Solvent Violet 11, 13, 14, 26, 31, 33, 36, 37, 38, 45, 47, 48, 51, 59, and 60; and CI Disperse Violet 26, 27, and 28. Among these, CI Disperse Violet 27, CI Solvent Violet 13, and 31 are preferred, and CI Disperse Violet 27 and CI Solvent Violet 13 are more preferred, with CI Disperse Violet 27 being even more preferred, from the viewpoint of high stability and little change in color tone even when the polymerizable composition is polymerized.

[0087] The amount of colorant L added is preferably 10,000 mass ppb or less, more preferably 3,000 mass ppb or less, and even more preferably 1,500 mass ppb or less, relative to the resin, from the viewpoint of obtaining a lens substrate with a slightly bluish, favorable color tone. The amount of colorant L added is preferably 200 mass ppb or more, more preferably 300 mass ppb or more, and even more preferably 400 mass ppb or more, from the viewpoint of obtaining a lens substrate with a slightly bluish, favorable color tone.

[0088] (Colorant S) From the viewpoint of obtaining a lens substrate with a good slightly bluish color tone, colorant S has a maximum absorption wavelength of 500 nm or more and less than 550 nm in a 20 ppm by mass toluene solution. The maximum absorption wavelength of colorant S is preferably 500 nm or longer, more preferably 510 nm or longer, and even more preferably 530 nm or longer, from the viewpoint of obtaining a lens substrate with a slightly bluish, favorable color tone. The maximum absorption wavelength of colorant L is preferably 545 nm or shorter, from the viewpoint of obtaining a lens substrate with a slightly bluish, favorable color tone.

[0089] 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, and 247; and CI Acid Red 73, 80, 91, 92, 97, 138, 151, 211, 274, and 289, from the viewpoint of obtaining a lens substrate with a slightly bluish and favorable color tone. Among these, CI Solvent Red 52 and 146 are preferred, with CI Solvent Red 52 being more preferred from the viewpoint of high stability and little change in color tone due to polymerization of the polymerizable composition.

[0090] From the viewpoint of obtaining a lens substrate with a good, slightly bluish color tone, the amount of colorant S added is preferably 500 ppb by mass or less, more preferably 100 ppb by mass or less, and even more preferably 50 ppb by mass or less, relative to the resin. From the viewpoint of obtaining a lens substrate with a good, slightly bluish color tone, the amount of colorant S added is preferably 1 ppb by mass or more, more preferably 3 ppb by mass or more, and even more preferably 5 ppb by mass or more.

[0091] 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, from the viewpoint of obtaining a lens substrate with a good slightly bluish color tone. The mass ratio of colorant L to colorant S is preferably 5 or more, more preferably 10 or more, more preferably 15 or more, and more preferably 20 or more. In addition, the mass ratio of colorant L to colorant S is preferably 500 or less, more preferably 200 or less, even more preferably 100 or less, and even more preferably 80 or less.

[0092] [Lens substrate structure, etc.] The lens substrate may be either a finished lens or a semi-finished lens. The surface shape of the lens substrate is not particularly limited, and may be flat, convex, concave, or the like. The lens substrate may be used for any of a single-vision lens, a multifocal lens, a progressive-power lens, etc. For example, in a progressive-power lens, the near-vision region (near vision region) and the progressive-power region (intermediate region) are usually included in the lower region, and the distance-vision region (distance vision region) is included in the upper region. As the lens substrate, a colorless one is usually used, but a colored one can also be used as long as the transparency is not impaired.

[0093] The lens substrate is preferably a meniscus type. A "meniscus type" lens substrate refers to a lens substrate having curved surfaces on both sides. By incorporating the above-mentioned Compound 1 into a meniscus type lens substrate, astigmatism can be suppressed.

[0094] 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, even more 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. The diameter of the lens substrate is not particularly limited, but is usually about 50 to 100 mm.

[0095] The refractive index ne of the lens substrate is preferably 1.52 or more, more preferably 1.53 or more, even more preferably 1.55 or more, even more preferably 1.58 or more, and even more preferably 1.60 or more. From the viewpoint of enhancing the effect of improving the Abbe number by including Compound 1, the refractive index ne of the lens substrate is preferably 1.70 or more, and more preferably 1.74 or more. The upper limit of the refractive index ne of the lens substrate is not particularly limited, but may be, for example, 1.80 or less.

[0096] From the viewpoint of reducing blue light hazard, the transmittance of the lens substrate for 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. The lower limit of the transmittance for light with a wavelength of 410 nm is not particularly limited, but is, for example, 0.0% or more.

[0097] The transmittance of the lens substrate at 430 nm wavelength is preferably 70% or more, more preferably 72% or more, and even more preferably 75% or more. By achieving the transmittance at 430 nm wavelength while maintaining the transmittance at 410 nm wavelength, it is possible to suppress coloring or reduce the amount of dye used while reducing blue light hazard. The upper limit of the transmittance at 430 nm wavelength is not particularly limited, but is, for example, 90% or less.

[0098] The transmittance of light with a wavelength of 400 nm through the lens substrate is preferably 3% or less, more preferably 1% or less, and even more preferably 0.0% or less, from the viewpoint of reducing the transmission of ultraviolet rays that are harmful to the eyes.

[0099] The transmittance of the lens substrate for 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 maintaining the transmittance for light with a wavelength of 410 nm while also achieving the transmittance for light with a wavelength of 420 nm, blue light hazard can be reduced. The lower limit of the transmittance for light with a wavelength of 420 nm is not particularly limited, but is, for example, 0% or more.

[0100] The transmittance of the lens substrate for 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 for light with a wavelength of 440 nm, it is possible to suppress coloring or reduce the amount of the dye used. The upper limit of the transmittance for light with a wavelength of 440 nm is not particularly limited, but it is, for example, 95% or less.

[0101] The transmittance of the lens substrate for 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 for light with a wavelength of 450 nm, it is possible to suppress coloring or reduce the amount of the dye used. The upper limit of the transmittance for light with a wavelength of 450 nm is not particularly limited, but it is, for example, 95% or less.

[0102] The transmittance of the lens substrate for 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 upper limit to the transmittance for light with a wavelength of 550 nm, but it is, for example, 95% or less.

[0103] The luminous transmittance of the lens substrate is preferably 70% or more, more preferably 80% or more, even more preferably 85% or more, and even more preferably 90% or more. The upper limit of the luminous transmittance is not particularly limited, but may be, for example, 100% or less, or 95% or less.

[0104] The above-mentioned transmittance is the transmittance at the optical center of the lens substrate, and can be measured using a spectrophotometer. For example, a "U-4100" (trade name, manufactured by Hitachi, Ltd.) can be used as the spectrophotometer. The above-mentioned transmittance can be achieved by adjusting the content of Compound 1 according to the thickness of the lens substrate.

[0105] [Method for manufacturing lens substrate] The lens substrate is not particularly limited, but may be, for example: curing the polymerizable composition; and A process to anneal the cured resin The composition can be obtained by a manufacturing method including the steps of:

[0106] The polymerization is preferably a cast polymerization method, and the lens substrate can be obtained, for example, by injecting a polymerizable composition into a mold formed by combining a glass or metal mold with a tape or a gasket, and then polymerizing the composition.

[0107] The polymerization conditions can be appropriately set depending on 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 raise the temperature from the polymerization initiation temperature and then heat to harden and form the composition. For example, the maximum temperature is usually 110°C or higher and 130°C or lower.

[0108] After the polymerization is complete, the lens substrate may be released from the mold and then subjected to an annealing treatment, preferably at a temperature of 100 to 150°C.

[0109] <Hard coat layer> The hard coat layer is, for example, a cured film made of a curable composition containing an inorganic oxide and a silicon compound. The curable composition preferably further contains a polyfunctional epoxy compound.

[0110] Examples of inorganic oxides include silicon oxide, aluminum oxide, titanium oxide, zirconium oxide, tungsten oxide, zinc oxide, tin oxide, beryllium oxide, and antimony oxide, as well as composite oxides of two or more of these inorganic oxides. These may be used alone or in combination of two or more. Among these inorganic oxides, silicon oxide is preferred. Colloidal silica may also be used as the inorganic oxide.

[0111] The content of the inorganic oxide 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, based on the solid content of the curable composition.

[0112] The silicon compound is, for example, a silicon compound having a hydrolyzable group such as an alkoxy group.The silicon compound is preferably a silane coupling agent having an organic group bonded to a silicon atom and a hydrolyzable group.The organic group bonded to a silicon atom is preferably an organic group having a functional group such as an epoxy group such as a glycidoxy group, a vinyl group, a methacryloxy group, an acryloxy group, a mercapto group, an amino group, or a phenyl group, and more preferably an organic group having an epoxy group.In addition, the silicon compound may have an alkyl group bonded to silicon.

[0113] Commercially available products of the above-mentioned silane coupling agents include, for example, those manufactured by Shin-Etsu Chemical Co., Ltd. under the trade names 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.

[0114] The content of the silicon compound 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, of the solid content of the curable composition.

[0115] The polyfunctional epoxy compound is a polyfunctional epoxy compound containing two or more epoxy groups in one molecule, more preferably a polyfunctional epoxy compound containing two or three epoxy groups in one molecule. Commercially available polyfunctional epoxy compounds include 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 in the "Denacol" series manufactured by Nagase ChemteX Corporation.

[0116] The content of the polyfunctional epoxy compound is preferably 0% by mass or more and 50% by mass or less, more preferably 10% by mass or more and 40% by mass or less, and even more preferably 15% by mass or more and 30% by mass or less, of the solid content of the curable composition.

[0117] The above-mentioned curable composition can be prepared by mixing optional components such as an organic solvent, a leveling agent, a curing catalyst, etc., in addition to the components described above, as needed. The hard coat layer can be formed by applying a curable composition to a substrate and then subjecting it to a curing treatment (thermal curing, photocuring, etc.). Commonly used methods such as dipping, spin coating, and spraying can be used to apply the curable composition. For curable compositions containing polyfunctional epoxy compounds, the curing treatment is usually carried out by heating. The heat curing treatment can be carried out, for example, by placing the lens coated with the curable composition in an environment with an ambient temperature of 50 to 150°C for about 30 minutes to 3 hours.

[0118] <Underlayer> The underlayer can be formed from, for example, an aqueous resin composition containing at least one type of resin particles selected from the group consisting of polyurethane resin, acrylic resin, and epoxy resin.

[0119] As the aqueous resin composition, commercially available aqueous polyurethanes can be used as they are, or diluted with an aqueous solvent as necessary. Examples of commercially available aqueous polyurethanes include the "Evaphanol" series manufactured by Nicca Chemical Co., Ltd., the "Superflex" series manufactured by Daiichi Kogyo Seiyaku Co., Ltd., the "Adeka Bontiter" series manufactured by ADEKA Corporation, the "Olestar" series manufactured by Mitsui Chemicals, Inc., the "Bondic" series and the "Hydran" series manufactured by Dainippon Ink and Chemicals, Inc., the "Impranil" series manufactured by Bayer, the "Sofranate" series manufactured by Nippon Soflan Co., Ltd., the "Poise" series manufactured by Kao Corporation, the "Sunprene" series manufactured by Sanyo Chemical Industries, Ltd., the "Eizelax" series manufactured by Hodogaya Chemical Co., Ltd., and the "Neolet's" series manufactured by Zeneca Corporation.

[0120] The underlayer can be formed, for example, by applying the above-mentioned aqueous resin composition to the surface of the substrate and drying it.

[0121] <Functional layer> Examples of the functional layer include an antireflection layer, an ultraviolet absorbing layer, an infrared absorbing layer, a photochromic layer, an antistatic layer, and an antifogging layer. These functional layers may be used alone or in combination of two or more. Publicly known techniques related to spectacle lenses can be applied to these functional layers. Among these, it is preferable to have an antireflection layer.

[0122] (Anti-reflection layer) The antireflection layer has, for example, low refractive index layers and high refractive index layers arranged alternately. The number of layers in the antireflection layer is preferably 4 to 11, and more preferably 5 to 8.

[0123] 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 is made of an inorganic oxide, preferably silicon oxide.

[0124] 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 is made of, for example, an inorganic oxide. The inorganic oxide used in the high refractive index layer is preferably at least one selected from the group consisting of zirconium oxide, tantalum oxide, yttrium oxide, titanium oxide, niobium oxide, and aluminum oxide, more preferably at least one selected from the group consisting of zirconium oxide and tantalum oxide.

[0125] The antireflection layer can be formed by alternately laminating low refractive index layers and high refractive index layers by vacuum deposition.

[0126] <Water-repellent layer> The water-repellent layer is formed using a water-repellent material composition described below. The water-repellent layer may be formed on a hard coat layer or a functional layer, but is preferably formed on an antireflection layer. The water-repellent layer is preferably located on the outermost surface.

[0127] <Physical properties of eyeglass lenses> From the viewpoint of reducing blue light hazard, the transmittance of light with a wavelength of 410 nm throughout the entire spectacle lens is preferably 5% or less, more preferably 3% or less, and even more preferably 1.0% or less. The lower limit of the transmittance of light with a wavelength of 410 nm is not particularly limited, but is, for example, 0.0% or more.

[0128] The transmittance of light with a wavelength of 430 nm throughout the entire spectacle lens is preferably 70% or more, more preferably 72% or more, and even more preferably 75% or more. By achieving the transmittance of light with a wavelength of 430 nm while maintaining the transmittance of light with the wavelength of 410 nm, it is possible to suppress coloring or reduce the amount of the dye used while reducing blue light hazard. The upper limit of the transmittance of light with a wavelength of 430 nm is not particularly limited, but is, for example, 90% or less.

[0129] The transmittance of light with a wavelength of 400 nm throughout the entire spectacle lens is preferably 3% or less, more preferably 1% or less, and even more preferably 0.0% or less, from the viewpoint of reducing the transmission of ultraviolet rays that are harmful to the eyes.

[0130] The transmittance of light with a wavelength of 420 nm throughout the entire spectacle lens is preferably 50% or less, more preferably 30% or less, and even more preferably 20% or less. By maintaining the transmittance of light with a wavelength of 410 nm while also achieving the transmittance of light with a wavelength of 420 nm, blue light hazard can be reduced. The lower limit of the transmittance of light with a wavelength of 420 nm is not particularly limited, but is, for example, 0% or more.

[0131] The transmittance of light with a wavelength of 440 nm throughout the entire spectacle lens is preferably 70% or more, more preferably 72% or more, and even more preferably 75% or more. By achieving this transmittance of light with a wavelength of 440 nm, it is possible to suppress coloring or reduce the amount of the dye used. The upper limit of the transmittance of light with a wavelength of 440 nm is not particularly limited, but it is, for example, 95% or less.

[0132] The transmittance of light with a wavelength of 450 nm throughout the entire spectacle lens is preferably 70% or more, more preferably 72% or more, and even more preferably 75% or more. By achieving this transmittance of light with a wavelength of 450 nm, it is possible to suppress coloring or reduce the amount of the dye used. The upper limit of the transmittance of light with a wavelength of 450 nm is not particularly limited, but it is, for example, 95% or less.

[0133] The transmittance of light with a wavelength of 550 nm throughout the entire spectacle lens is preferably 70% or more, more preferably 80% or more, and even more preferably 85% or more. There is no particular upper limit to the transmittance of light with a wavelength of 550 nm, but it is, for example, 95% or less.

[0134] The luminous transmittance of the spectacle lens is preferably 70% or more, more preferably 80% or more, even more preferably 85% or more, and even more preferably 90% or more. The upper limit of the luminous transmittance is not particularly limited, but may be, for example, 100% or less, or 95% or less.

[0135] The above-mentioned transmittance is the transmittance at the optical center of the eyeglass lens, and can be measured using a spectrophotometer. For example, a "U-4100" (trade name, manufactured by Hitachi, Ltd.) can be used as the spectrophotometer. The above-mentioned transmittance can be achieved by adjusting the content of Compound 1 according to the thickness of the eyeglass lens. [Example]

[0136] The present embodiment will be described in more detail below using examples and comparative examples, but the present invention is not limited to the following examples.

[0137] [Measurement method] <Transmittance> The transmittance for light of each wavelength was measured using a spectrophotometer "U-4100" (product name, manufactured by Hitachi, Ltd.) The transmittance was measured at the optical center of the eyeglass lens and the lens substrate.

[0138] <Maximum absorption wavelength (λmax)> 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. Sample: Toluene solution (colorant content: 20 ppm by mass) Measurement mode: Transmittance Optical path length: 10mm

[0139] <Luminous transmittance> The luminous transmittance was measured in accordance with JIS T7333: 2005. The transmittance was measured at the optical center of the spectacle lens and the lens substrate.

[0140] <Lens refractive index and Abbe number> Using a precision refractometer "KPR-2000" (manufactured by Kalnew Optical Co., Ltd.), the refractive index of the eyeglass lens was measured at 25°C using F' line (488.0 nm), C' line (643.9 nm), and e line (546.1 nm). The Abbe number was then calculated using the following formula. Abbe number νe=(ne-1) / (nF'-nC') ne is the refractive index measured at the e-line, nF' is the refractive index measured at the F' line, and nC' is the refractive index measured at the C' line.

[0141] <Blue LP test> Laser light was applied to the optical center of the eyeglass lens from a laser pointer (LP) (output <1 mW) with an emission wavelength of 405 ± 10 nm, and it was confirmed whether the laser light was transmitted. (Evaluation criteria) ○: Laser light has decreased significantly △: Laser light is slightly reduced ×: Laser light was transmitted

[0142] Example 1 To 50.28 parts by mass of a mixture of 2,5-bis(isocyanatomethyl)-bicyclo[2.2.1]heptane and 2,6-bis(isocyanatomethyl)-bicyclo[2.2.1]heptane, 0.06 parts by mass of dimethyltin dichloride as a catalyst, 0.15 parts by mass of acidic phosphate ester "JP-506H" (trade name, manufactured by Johoku Chemical Industry Co., Ltd.) as a release agent, 0.55 parts by mass of 2-ethylhexyl 2-(2-hydroxy-4-ethoxyphenyl)2H-benzotriazole-5-carboxylate, 0.1037 parts by mass of Disperse Violet 27 (maximum absorption wavelength in a 20 ppm by mass toluene solution: 586 nm), and 0.0013 parts by mass of Solvent Red 52 (maximum absorption wavelength in a 20 ppm by mass toluene solution: 543 nm) were added and mixed by stirring. Next, 25.50 parts by mass of pentaerythritol tetrakis(3-mercaptopropionate) and 24.22 parts by mass of 1,2-bis(2-mercaptoethylthio)-3-mercaptopropane were added, and the mixture was stirred and mixed under a reduced pressure of 10 mmHg for 30 minutes to prepare a curable composition. This curable composition was then poured into a lens-molding mold (set to 0.00D and 1.6 mm wall thickness) consisting of a glass mold and a resin gasket, and polymerization was carried out in an electric furnace at temperatures ranging from 20 to 120°C for 24 hours. After polymerization, the gasket and mold were removed, and the lens substrate was heat-treated at 120°C for 2 hours to obtain a lens substrate. The optical properties and spectral transmittance of the resulting lens substrate were measured, and the results are shown in Table 2. The luminous transmittance was 88.6%.

[0143] <Examples 2 to 4 and Comparative Examples 1 to 8> A lens substrate was obtained in the same manner as in Example 1, except that the composition of the raw materials was as shown in Table 1. The optical properties and spectral transmittance of the obtained lens substrate were measured, and the results are shown in Table 2. The luminous transmittance of the lens substrate of Example 3 was 88.0%.

[0144] <Example 5> 79.92 parts by mass of bis-(β-epithiopropyl) sulfide, 14.00 parts by mass of sulfur, and 0.25 parts by mass of compound 1-1 were added to a 300 mL recovery flask, and degassing was carried out for 60 minutes while heating to 60°C. Then, 0.467 parts by mass of 1-methyl-2-mercapto-1H-imidazole was added, and a preliminary reaction was carried out at 60°C for 60 minutes while stirring under normal pressure in a sealed state. After that, the mixture was cooled to 20°C, and 0.13 parts by mass of dibutyltin dichloride was added to terminate the preliminary reaction. In a separate container, 6.08 parts by mass of bis-(2-mercaptoethyl) sulfide, 0.001 part by mass of acidic phosphate ester "JP506H" (trade name, manufactured by Johoku Chemical Industry Co., Ltd.), 0.020 parts by mass of tetrabutylphosphonium bromide, and 1050 ppb by mass of Disperse Violet 27 (maximum absorption wavelength in a 20 ppm by mass toluene solution is 586 nm) and 450 ppb by mass of Solvent Red 52 (maximum absorption wavelength in a 20 ppm by mass toluene solution is 543 nm) as bluing agents were added, and this solution was mixed and dissolved. This solution was then added to the pre-reacted solution, and the mixture was degassed while stirring at 20°C to obtain a homogeneous solution. The mixture was then filtered through a 3 micron polyethylene terephthalate filter and poured into a lens casting mold (set to 0.00D, wall thickness 2.00 mm) consisting of a glass mold and a resin gasket, and the temperature was raised from 30°C to 100°C over 24 hours in an oven to polymerize and harden, after which the material was demolded to obtain a lens substrate. The optical properties and spectral transmittance of the obtained lens substrate were measured, and the results are shown in Table 4. The luminous transmittance was 84.2%.

[0145] <Comparative Examples 9 to 10> A lens substrate was obtained in the same manner as in Example 9, except that the raw material composition was as shown in Table 3. The optical properties and spectral transmittance of the obtained lens substrate were measured, and the results are shown in Table 4.

[0146] Example 6 A 300 mL recovery flask was charged with 95.00 parts by mass of bis-(β-epithiopropyl) disulfide, 5.00 parts by mass of a mixture of 4,7-bis(mercaptomethyl)-3,6,9-trithiaundecane-1,11-dithiol, 4,8-bis(mercaptomethyl)-3,6,9-trithiaundecane-1,11-dithiol, and 5,7-bis(mercaptomethyl)-3,6,9-trithiaundecane-1,11-dithiol, 0.40 parts by mass of Compound 1-1, and acidic phosphorus 0.001 parts by mass of acid ester "JP506H" (trade name, manufactured by Johoku Chemical Industry Co., Ltd.), 1400 ppb by mass of Disperse Violet 27 (maximum absorption wavelength of 586 nm in a 20 ppm by mass toluene solution) and 600 ppb by mass of Solvent Red 52 (maximum absorption wavelength of 543 nm in a 20 ppm by mass toluene solution) as bluing agents, and 0.10 parts by mass of dicyclohexylmethylamine were added, and the mixture was degassed at 20°C for 60 minutes to obtain a homogeneous solution. The mixture was then filtered through a 3 micron polyethylene terephthalate filter and poured into a lens casting mold (set to 0.00D, wall thickness 2.00mm) consisting of a glass mold and a resin gasket, and the temperature was raised from 30°C to 100°C over 24 hours in an oven to polymerize and harden, after which the mold was demolded to obtain a lens substrate. The optical properties and spectral transmittance of the obtained lens substrate were measured, and the results are shown in Table 4.

[0147] <Comparative Example 11> A lens substrate was obtained in the same manner as in Example 6, except that the raw material composition was as shown in Table 3. The optical properties and spectral transmittance of the obtained lens substrate were measured, and the results are shown in Table 4.

[0148] [Table 1]

[0149] [Table 2]

[0150] [Table 3]

[0151] [Table 4]

[0152] The abbreviations in the table are as follows: Compound 1-1: 2-Ethylhexyl 2-(2-hydroxy-4-ethoxyphenyl) 2H-benzotriazole-5-carboxylate Compound 51: 2-(2-hydroxy-4-octyloxyphenyl) 2H-benzotriazole Compound 52: 2-(3-tert-butyl-2-hydroxy-5-methylphenyl)-5-chloro-2H-benzotriazole Compound 53: 2-(2-hydroxy-5-methylphenyl) 2H-benzotriazole Compound 54: 2-(2-hydroxy-4-ethoxyphenyl) 2H-benzotriazole NBDI: A mixture of 2,5-bis(isocyanatomethyl)-bicyclo[2.2.1]heptane and 2,6-bis(isocyanatomethyl)-bicyclo[2.2.1]heptane PETMP: Pentaerythritol tetrakis(3-mercaptopropionate) TFSH: 1,2-bis(2-mercaptoethylthio)-3-mercaptopropane HXDI: 1,3-bis(isocyanatomethyl)cyclohexane PETMA: Pentaerythritol tetrakis(2-mercaptoacetate) DMMD: 2,5-bis(mercaptomethyl)-1,4-dithiane XDI: 1,3-bis(isocyanatomethyl)benzene FFSH: a mixture of 4,7-bis(mercaptomethyl)-3,6,9-trithiaundecane-1,11-dithiol, 4,8-bis(mercaptomethyl)-3,6,9-trithiaundecane-1,11-dithiol, and 5,7-bis(mercaptomethyl)-3,6,9-trithiaundecane-1,11-dithiol ETPS: Bis-(β-epithiopropyl) sulfide MES: Bis-(2-mercaptoethyl) sulfide ETPDS: Bis-(β-epithiopropyl) disulfide

Claims

1. Formula (1): 【Chemical 1】 (In the formula, R 1 is an alkoxy group having 1 to 20 carbon atoms, R 2 is an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms, R 3 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, and m is an integer of 0 to 2.) and a lens substrate containing a resin, A spectacle lens, wherein the refractive index ne of the lens substrate is 1.52 or more and 1.80 or less.

2. The R 1 is an alkoxy group having 4 to 20 carbon atoms, The R 2 is an alkoxy group having 1 to 12 carbon atoms, wherein n is 1; The eyeglass lens according to claim 1 , wherein m is 0.

3. The R 1 The eyeglass lens according to claim 1 or 2, wherein is a branched alkoxy group having 4 to 20 carbon atoms.

4. The compound represented by formula (1) 2-ethylhexyl 2-(2-hydroxy-4-methoxyphenyl)2H-benzotriazole-5-carboxylate, 2-ethylhexyl 2-(2-hydroxy-4-ethoxyphenyl)2H-benzotriazole-5-carboxylate, 2-ethylhexyl 2-(2-hydroxy-4-octyloxyphenyl)2H-benzotriazole-5-carboxylate, methyl 2-(2-hydroxy-4-methoxyphenyl)2H-benzotriazole-5-carboxylate, methyl 2-(2-hydroxy-4-ethoxyphenyl)2H-benzotriazole-5-carboxylate, methyl 2-(2-hydroxy-4-octyloxyphenyl)2H-benzotriazole-5-carboxylate, ethyl 2-(2-hydroxy-4-methoxyphenyl)2H-benzotriazole-5-carboxylate, ethyl 2-(2-hydroxy-4-ethoxyphenyl)2H-benzotriazole-5-carboxylate, ethyl 2-(2-hydroxy-4-octyloxyphenyl)2H-benzotriazole-5-carboxylate, n-octyl 2-(2-hydroxy-4-methoxyphenyl)2H-benzotriazole-5-carboxylate, n-Octyl 2-(2-hydroxy-4-ethoxyphenyl)2H-benzotriazole-5-carboxylate, and n-Octyl 2-(2-hydroxy-4-octyloxyphenyl)2H-benzotriazole-5-carboxylate The spectacle lens according to any one of claims 1 to 3, which is at least one selected from the group consisting of:

5. The compound represented by formula (1) 2-ethylhexyl 2-(2-hydroxy-4-methoxyphenyl)2H-benzotriazole-5-carboxylate, or 2-Ethylhexyl 2-(2-hydroxy-4-ethoxyphenyl)2H-benzotriazole-5-carboxylate The eyeglass lens according to any one of claims 1 to 4, wherein

6. The transmittance of light having a wavelength of 410 nm in the entire eyeglass lens is 5% or less, The eyeglass lens according to any one of claims 1 to 5, wherein the transmittance of light with a wavelength of 430 nm throughout the entire eyeglass lens is 70% or more.

7. 7. The eyeglass lens according to claim 1, comprising a colorant L having a maximum absorption wavelength of 550 nm or more and 600 nm or less in a 20 ppm by mass toluene solution.

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

9. The spectacle lens according to any one of claims 1 to 8, wherein the resin is a cured product of an isocyanate component including at least one selected from the group consisting of bis(isocyanatomethyl)bicyclo[2.2.1]heptane, bis(isocyanatomethyl)cyclohexane, bis(isocyanatomethyl)benzene, tolylene diisocyanate, diphenylmethane diisocyanate, dicyclohexylmethane diisocyanate, hexamethylene diisocyanate, and pentamethylene diisocyanate, and an active hydrogen compound component.

10. 10. The spectacle lens according to claim 9, wherein the active hydrogen compound component comprises at least one selected from the group consisting of toluenediamine, pentaerythritol tetrakismercaptoacetate, pentaerythritol tetrakismercaptopropionate, trimethylolpropane trismercaptoacetate, trimethylolpropane trismercaptopropionate, bis(mercaptoethylthio)mercaptopropane, bis(mercaptomethyl)-3,6,9-trithiaundecanedithiol, dimercaptoethyl sulfide, bis(mercaptomethyl)dithiane, dimercaptoethyl ether, and diethylene glycol.

11. The eyeglass lens of claim 10, wherein the bis(mercaptomethyl)-3,6,9-trithiaundecanedithiol is a mixture of 4,7-bis(mercaptomethyl)-3,6,9-trithiaundecane-1,11-dithiol, 4,8-bis(mercaptomethyl)-3,6,9-trithiaundecane-1,11-dithiol, and 5,7-bis(mercaptomethyl)-3,6,9-trithiaundecane-1,11-dithiol.

12. The eyeglass lens according to any one of claims 1 to 8, wherein the resin is an episulfide resin.

13. 13. The eyeglass lens according to claim 1, comprising 0.05 parts by mass or more and 2.00 parts by mass or less of the compound represented by formula (1) relative to 100 parts by mass of the resin.

14. The eyeglass lens according to any one of claims 1 to 13, comprising 0.05 parts by mass or more and 0.60 parts by mass or less of the compound represented by formula (1) relative to 100 parts by mass of the resin.

15. The spectacle lens according to any one of claims 1 to 14, wherein the refractive index ne of the lens substrate is 1.70 or more and 1.80 or less.

16. The eyeglass lens according to any one of claims 1 to 15, comprising at least one layer selected from the group consisting of a hard coat layer, an undercoat layer, and an anti-reflection layer.

17. The spectacle lens according to any one of claims 1 to 16, wherein the lens substrate is of a meniscus type.

18. 18. The eyeglass lens according to claim 17, 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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