Polymerizable composition for optical material, optical material and use thereof

Abstract

The polymerizable composition for an optical material of the present disclosure includes (A) an isocyanate compound, (B) at least one active hydrogen compound selected from the group consisting of a polythiol compound having two or more mercapto groups, a hydroxythiol compound having one or more mercapto groups and one or more hydroxyl groups, a polyol compound having two or more hydroxyl groups, and an amine compound, and (C) an ultraviolet absorber represented by the following general formula (1):

Description

[Technical field]

[0001] The present disclosure relates to a polymerizable composition for an optical material, an optical material, and uses thereof. [Background technology]

[0002] The adverse effects of exposure of eyes to ultraviolet light have been a concern for some time. In recent years, the effects of blue light, which is contained in natural light, liquid crystal displays of office equipment, and displays of mobile devices such as smartphones and mobile phones, on the eyes, such as eye fatigue and eye pain, have become a problem, and it has been desired to reduce the amount of exposure of the eyes to blue light with a relatively short wavelength of about 420 nm from ultraviolet light.

[0003] The effects of short-wavelength blue light of about 420 nm on the eyes are described in Non-Patent Document 1. This document examines damage to retinal nerve cells (cultured rat retinal nerve R28 cells) caused by irradiation with blue LED light with different peak wavelengths of 411 nm and 470 nm. As a result, irradiation with blue light with a peak wavelength of 411 nm (4.5 W / m 2 ) causes cell death in retinal nerve cells within 24 hours, whereas blue light with a peak wavelength of 470 nm causes no changes in cells even with the same amount of exposure, indicating that limiting exposure to light with wavelengths of 400 to 420 nm is important for preventing eye damage.

[0004] In addition, there are concerns that prolonged exposure to blue light can cause eye fatigue and stress, and is thought to be a factor in causing age-related macular degeneration. Techniques aimed at suppressing the transmission of blue light include the following.

[0005] Patent Document 1 discloses a plastic lens containing an ultraviolet absorbing agent, which has an average light transmittance of 0.5% or less in the wavelength range of 300 nm or more and 400 nm or less. Patent Document 2 discloses a plastic lens obtained from a composition for plastic lenses that contains a resin material including a urethane resin material and at least two kinds of ultraviolet absorbents having different maximum absorption wavelengths.

[0006] Patent Document 3 discloses a plastic lens obtained from a composition for plastic lenses that contains a resin material including a urethane resin material and an ultraviolet absorber having a maximum absorption wavelength of 345 nm or more in a chloroform solution. The document describes that the plastic lens does not yellow the lens or change the refractive index due to the influence of the ultraviolet absorber, and further does not reduce the mechanical strength of the lens.

[0007] Patent Document 4 discloses a plastic eyeglass lens using a specific benzotriazole compound. The document describes that the plastic eyeglass lens has light transmittance within a predetermined range at wavelengths of 395 nm, 400 nm, and 405 nm. Patent Documents 5 and 6 disclose polymerizable compositions for optical materials that contain an isocyanate compound, an active hydrogen compound, and a specific ultraviolet absorber.

[0008] In addition, Patent Document 7 discloses a polymerizable composition for optical materials, which contains a compound containing an episulfide group or a compound containing a thietanyl group, and a specific benzotriazole-based compound as an ultraviolet absorbent, and a plastic lens obtained from the composition. This document discloses that the plastic lens has an excellent blocking effect of blue light of about 420 nm. However, this document does not disclose a benzotriazole-based compound having a group containing an ester bond. [Prior art documents] [Patent documents]

[0009] [Patent Document 1] Japanese Patent Application Publication No. 10-186291 [Patent Document 2] Japanese Patent Application Publication No. 11-218602 [Patent Document 3] Japanese Patent Application Publication No. 11-295502 [Patent Document 4] JP 2005-292240 A [Patent Document 5] Japanese Patent Application Publication No. 4-219703 [Patent Document 6] International Publication No. 2016 / 125736 [Patent Document 7] International Publication No. 2015 / 088011 [Non-patent literature]

[0010] [Non-Patent Document 1] The European journal of neuroscience, vol.34, Iss.4, 548-58, (2011) Summary of the Invention [Problem to be solved by the invention]

[0011] In order to increase the amount of ultraviolet light absorbed (also called the cut rate), it is necessary to increase the amount of ultraviolet light absorber added to the optical material. However, when the amount of ultraviolet light absorber added is increased, the optical material tends to become cloudy and lose transparency, or the color tends to become worse due to coloring. Thus, there is a trade-off between the blocking effect of ultraviolet light and blue light of about 420 nm and the design of the optical material (transparency, suppression of coloring, etc.). The present disclosure provides a polymerizable composition for optical materials, an optical material, and applications using the same, which improve the above-mentioned trade-off relationship and can achieve both a high cut rate and designability. [Means for solving the problem]

[0012] The present disclosure can be seen as follows: [1] (A) an isocyanate compound, (B) at least one active hydrogen compound selected from the group consisting of a polythiol compound having two or more mercapto groups, a hydroxythiol compound having one or more mercapto groups and one or more hydroxyl groups, a polyol compound having two or more hydroxyl groups, and an amine compound; (C) the following general formula (1) [ka] (In the above general formula (1), R1 and R2 represent alkyl groups having 1 to 8 carbon atoms and may be the same or different. A plurality of R1s or a plurality of R2s may be the same or different. m represents an integer of 0 to 3, n represents an integer of 0 to 3, and R3 represents a functional group having 4 to 10 carbon atoms including an ester bond.) and an ultraviolet absorber represented by the formula: A polymerizable composition for an optical material comprising the above compound. [2] (D) a compound having a cyclic structure containing a sulfur atom; (C) the following general formula (1) [ka] (In the above general formula (1), R1 and R2 represent alkyl groups having 1 to 8 carbon atoms and may be the same or different. A plurality of R1s or a plurality of R2s may be the same or different. m represents an integer of 0 to 3, n represents an integer of 0 to 3, and R3 represents a functional group having 4 to 10 carbon atoms including an ester bond.) and an ultraviolet absorber represented by the formula: A polymerizable composition for an optical material comprising the above compound. [3] The ultraviolet absorber (C) is represented by the following general formula (2): [ka] (In the above general formula (2), R1, R2, m, and n are the same as those in the above general formula (1), R4 represents a hydrocarbon group having 1 to 3 carbon atoms, and R5 represents a hydrocarbon group having 1 to 7 carbon atoms.) The polymerizable composition for an optical material according to [1] or [2], wherein the ultraviolet absorber is represented by the formula: [4] The ultraviolet absorber (C) is represented by the following general formula (3): [ka] (In the above general formula (3), R2, R4, and R5 are defined as in the above general formula (1) or (2).) The polymerizable composition for optical materials according to [2], wherein the ultraviolet absorber is represented by the formula: [5] The polymerizable composition for optical materials according to any one of [1] to [3], wherein the ultraviolet absorber (C) has a maximum absorption peak in the range of 340 nm or more and 370 nm or less. [6] The polymerizable composition for an optical material according to [1], wherein the isocyanate compound (A) includes at least one selected from an aromatic isocyanate compound and an araliphatic isocyanate compound. [7] The polymerizable composition for an optical material according to [6], wherein the isocyanate compound (A) is at least one selected from the group consisting of xylylene diisocyanate, phenylene diisocyanate, tolylene diisocyanate, and diphenylmethane diisocyanate. [8] The polymerizable composition for optical materials according to [2], wherein the compound (D) has two or more 3- to 5-membered cyclic structures containing S in one molecule and has a weight average molecular weight of 100 or more and 1,000 or less. [9] The compound (D) is represented by the following general formula (5): [ka] (wherein n is 0 or 1).

[10] The polythiol compound (B) is 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, pentaerythritol tetrakis(2-mercaptoacetate), pentaerythritol tetrakis(3-mercaptopropionate), 2,5-bis(mercaptomethyl)-1,4-dithiane, bithiaundecane, bis(mercaptomethyl)-1,4-dithiane ... the polymerizable composition for an optical material according to [1], which is at least one selected from the group consisting of bis(mercaptoethyl)sulfide, 1,1,3,3-tetrakis(mercaptomethylthio)propane, 4,6-bis(mercaptomethylthio)-1,3-dithiane, 2-(2,2-bis(mercaptomethylthio)ethyl)-1,3-dithietane, 1,1,2,2-tetrakis(mercaptomethylthio)ethane, 3-mercaptomethyl-1,5-dimercapto-2,4-dithiapentane, tris(mercaptomethylthio)methane, and ethylene glycol bis(3-mercaptopropionate).

[11] The polymerizable composition for an optical material according to [1], wherein the ultraviolet absorber (C) is contained in an amount of 0.1 to 10.0 parts by mass per 100 parts by mass of the polymerizable composition for an optical material.

[12] The polymerizable composition for an optical material according to

[11] , wherein the ultraviolet absorber (C) is contained in an amount of 0.1 to 2.0 parts by mass per 100 parts by mass of the polymerizable composition for an optical material.

[13] The polymerizable composition for an optical material according to [2], wherein the ultraviolet absorber (C) is contained in an amount of 0.1 to 3.0% by weight based on 100% by weight of the total weight of the compound (D) having a cyclic structure containing a sulfur atom and the polythiol (B) which is included as necessary.

[14] A cured product of the polymerizable composition for optical materials described in [1].

[15] A cured product of the polymerizable composition for optical materials according to [2], which contains 0.1 to 3.0% by weight of an ultraviolet absorber (C).

[16] A plastic lens comprising the cured product according to

[14] or

[15] . Effect of the Invention

[0013] According to the polymerizable composition for optical materials of the present disclosure, by using a specific ultraviolet absorber, it is possible to provide an optical material that has an excellent blocking effect from ultraviolet light to blue light of about 420 nm and also has excellent design properties. [Brief description of the drawings]

[0014] The above objects, as well as other objects, features and advantages, will become more apparent from the following preferred embodiments and the accompanying drawings.

[0015] [Figure 1] 1 is a graph plotting YI / absorbance at a wavelength of 410 nm calculated in Examples a1 to a4 and Comparative Examples a1 and a2. [Diagram 2] 1 is a photograph showing the appearance of the lenses obtained in Example b1 and Comparative Example b1. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0016] Hereinafter, the embodiments of the present disclosure will be described in detail, but the present disclosure is not limited to these embodiments. In the present disclosure, a numerical range indicated using "~" indicates a range including the numerical values ​​before and after "~" as the minimum and maximum values, respectively.

[0017] The polymerizable composition for an optical material of the present disclosure contains a polymerization reactive compound and an ultraviolet absorber represented by the following general formula (1). As the polymerization reactive compound, any known compound can be used as long as the effects of the present invention can be obtained. Examples of the polymerizable reactive compound include isocyanate compounds, isothiocyanate compounds, active hydrogen compounds (polythiol compounds, hydroxythiol compounds, polyol compounds, amine compounds, etc.), epoxy compounds, compounds having a cyclic structure containing a sulfur atom, oxetanine compounds, (meth)acrylic compounds, and (meth)allyl compounds. One or more compounds selected from these can be used. Preferred examples of the polymerizable composition for an optical material and the cured product thereof according to the present disclosure will be described with reference to a first embodiment and a second embodiment.

[0018] First Embodiment The polymerizable composition for an optical material of the present disclosure includes (A) an isocyanate compound, (B) at least one active hydrogen compound selected from the group consisting of a polythiol compound having two or more mercapto groups, a hydroxythiol compound having one or more mercapto groups and one or more hydroxyl groups, a polyol compound having two or more hydroxyl groups, and an amine compound, and (C) an ultraviolet absorber represented by the following general formula (1).

[0019] [ka]

[0020] In the above general formula (1), R1 and R2 are alkyl groups having 1 to 8 carbon atoms and may be the same or different. A plurality of R1s or a plurality of R2s may be the same or different. m is an integer of 0 to 3, n is an integer of 0 to 3, and R3 is a functional group having 4 to 10 carbon atoms and including an ester bond. Each component will be described in detail below.

[0021] [(A) Isocyanate compound] In the present disclosure, the isocyanate compound (A) is not particularly limited and various isocyanate compounds can be used as long as they can exhibit the effects of the present disclosure. In the present disclosure, it is preferable to use an isocyanate compound having two or more isocyanato groups.

[0022] The isocyanate compound (A) may be an aliphatic isocyanate compound, an alicyclic isocyanate compound, an aromatic isocyanate compound, a heterocyclic isocyanate compound, an araliphatic isocyanate compound, etc., and may be used alone or in combination of two or more. These isocyanate compounds may include dimers, trimers, and prepolymers.

[0023] Examples of the aliphatic isocyanate compound include hexamethylene diisocyanate, 2,2,4-trimethylhexamethylene diisocyanate, 2,4,4-trimethylhexamethylene diisocyanate, pentamethylene diisocyanate, lysine diisocyanatomethyl ester, lysine triisocyanate, bis(isocyanatomethyl)sulfide, bis(isocyanatoethyl)sulfide, bis(isocyanatomethyl)disulfide, bis(isocyanatoethyl)disulfide, bis(isocyanatomethylthio)methane, bis(isocyanatoethylthio)methane, bis(isocyanatoethylthio)ethane, bis(isocyanatomethylthio)ethane, and the like, and at least one of them can be used.

[0024] Examples of the alicyclic isocyanate compound include isophorone diisocyanate, bis(isocyanatomethyl)cyclohexane, bis(isocyanatocyclohexyl)methane, cyclohexane diisocyanate, methylcyclohexane diisocyanate, dicyclohexyldimethylmethane isocyanate, 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, 3,8-bis(isocyanatomethyl)tricyclodecane, 3,9-bis(isocyanatomethyl)tricyclodecane, 4,8-bis(isocyanatomethyl)tricyclodecane, and 4,9-bis(isocyanatomethyl)tricyclodecane, and at least one of them can be used.

[0025] Examples of the aromatic isocyanate compound include tolylene diisocyanate, 4,4'-diphenylmethane diisocyanate, and phenylene diisocyanate, and the tolylene diisocyanate is one or more isocyanates selected from 2,4-tolylene diisocyanate and 2,6-tolylene diisocyanate. Examples of the tolylene diisocyanate include 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, and a mixture of 2,4-tolylene diisocyanate and 2,6-tolylene diisocyanate, and at least one of them can be used.

[0026] Examples of the heterocyclic isocyanate compound include 2,5-diisocyanatothiophene, 2,5-bis(isocyanatomethyl)thiophene, 2,5-diisocyanatotetrahydrothiophene, 2,5-bis(isocyanatomethyl)tetrahydrothiophene, 3,4-bis(isocyanatomethyl)tetrahydrothiophene, 2,5-diisocyanato-1,4-dithiane, 2,5-bis(isocyanatomethyl)-1,4-dithiane, 4,5-diisocyanato-1,3-dithiolane, and 4,5-bis(isocyanatomethyl)-1,3-dithiolane, and at least one of them can be used.

[0027] Examples of the aromatic aliphatic isocyanate compound include xylylene diisocyanate (1,3- or 1,4-xylylene diisocyanate or a mixture thereof) (XDI), tetramethyl xylylene diisocyanate (1,3- or 1,4-tetramethyl xylylene diisocyanate or a mixture thereof) (TMXDI), ω,ω'-diisocyanate-1,4-diethylbenzene, α,α,α',α'-tetramethyl xylylene diisocyanate, bis(isocyanatomethyl)naphthalene, mesitylene triisocyanate, and the like, and at least one of them can be used.

[0028] In the present disclosure, from the viewpoint of the effects of the present disclosure, the isocyanate compound (A) preferably contains at least one selected from an aliphatic isocyanate compound, an aromatic isocyanate compound, and an araliphatic isocyanate compound, more preferably contains at least one selected from an aromatic isocyanate compound and an araliphatic isocyanate compound, and further preferably contains at least one selected from xylylene diisocyanate, phenylene diisocyanate, tolylene diisocyanate, and diphenylmethane diisocyanate.

[0029] From the viewpoint of the effects of the present disclosure, the content of the isocyanate compound (A) in the polymerizable composition for an optical material is preferably 30 parts by mass or more, more preferably 40 parts by mass or more, and is preferably 70 parts by mass or less, more preferably 60 parts by mass or less, in 100 parts by mass of the polymerizable composition for an optical material.

[0030] [(B) Active hydrogen compounds] In the present disclosure, the active hydrogen compound (B) can be at least one selected from a polythiol compound having two or more mercapto groups, a hydroxythiol compound having one or more mercapto groups and one or more hydroxyl groups, a polyol compound having two or more hydroxyl groups, and an amine compound. From the viewpoint of the effects of the present disclosure, it is preferably at least one selected from a polythiol compound having two or more mercapto groups and a hydroxythiol compound having one or more mercapto groups and one or more hydroxyl groups, and more preferably at least one selected from a polythiol compound having two or more mercapto groups.

[0031] The polythiol compound can be selected from conventionally known compounds as long as it can obtain the effects of the present invention. For example, the compounds disclosed in WO2008 / 105138 can be used.

[0032] As the polythiol compound, preferably, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, pentaerythritol tetrakis(2-mercaptoacetate), pentaerythritol tetrakis(3-mercaptopropionate), 2,5-bis(mercaptomethyl)- At least one selected from 1,4-dithiane, bis(mercaptoethyl)sulfide, 1,1,3,3-tetrakis(mercaptomethylthio)propane, 4,6-bis(mercaptomethylthio)-1,3-dithiane, 2-(2,2-bis(mercaptomethylthio)ethyl)-1,3-dithietane, 1,1,2,2-tetrakis(mercaptomethylthio)ethane, 3-mercaptomethyl-1,5-dimercapto-2,4-dithiapentane, tris(mercaptomethylthio)methane, and ethylene glycol bis(3-mercaptopropionate) can be used. More preferably, at least one selected from 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, and pentaerythritol tetrakis(3-mercaptopropionate) can be used.

[0033] Examples of the hydroxythiol compound include 2-mercaptoethanol, 3-mercapto-1,2-propanediol, glycerin di(mercaptoacetate), 1-hydroxy-4-mercaptocyclohexane, 2,4-dimercaptophenol, 2-mercaptohydroquinone, 4-mercaptophenol, 3,4-dimercapto-2-propanol, 1,3-dimercapto-2-propanol, 2,3-dimercapto-1-propanol, 1,2-dimercapto-1,3-butanediol, pentaerythritol tris(3-mercaptopropionate), pentaerythritol mono(3-mercaptopropionate), pentaerythritol tetramercaptopropionate, ... Examples of the mercaptopropionate include pentaerythritol bis(3-mercaptopropionate), pentaerythritol tris(thioglycolate), pentaerythritol pentakis(3-mercaptopropionate), hydroxymethyl-tris(mercaptoethylthiomethyl)methane, 1-hydroxyethylthio-3-mercaptoethylthiobenzene, 4-hydroxy-4'-mercaptodiphenyl sulfone, 2-(2-mercaptoethylthio)ethanol, dihydroxyethyl sulfide mono(3-mercaptopropionate), dimercaptoethane mono(saltylate), and hydroxyethylthiomethyl-tris(mercaptoethylthio)methane.

[0034] The polyol compound is one or more aliphatic or alicyclic alcohol compounds. Specific examples of the polyol compound include linear or branched aliphatic alcohol compounds, alicyclic alcohol compounds, and alcohols obtained by adding these alcohols to ethylene oxide, propylene oxide, or ε-caprolactone. Examples of linear or branched aliphatic alcohol compounds include ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, tripropylene glycol, 1,3-propanediol, 2,2-dimethyl-1,3-propanediol, 2,2-diethyl-1,3-propanediol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, 3-methyl-1,3-butanediol, 1,2-pentanediol, 1,3-pentanediol, 1,5-pentanediol, 2,4-pentanediol, 2-methyl-2,4-pentanediol, 3-methyl-1,5-pentanediol, 1,6-hexanediol, 2,5-hexanediol, glycerol, diglycerol, polyglycerol, trimethylolpropane, pentaerythritol, and di(trimethylolpropane). Examples of alicyclic alcohol compounds include 1,2-cyclopentanediol, 1,3-cyclopentanediol, 3-methyl-1,2-cyclopentanediol, 1,2-cyclohexanediol, 1,3-cyclohexanediol, 1,4-cyclohexanediol, 4,4'-bicyclohexanol, and 1,4-cyclohexanedimethanol. Compounds obtained by adding these alcohols to ethylene oxide, propylene oxide, or ε-caprolactone may also be used, such as an ethylene oxide adduct of glycerol, an ethylene oxide adduct of trimethylolpropane, an ethylene oxide adduct of pentaerythritol, a propylene oxide adduct of glycerol, a propylene oxide adduct of trimethylolpropane, a propylene oxide adduct of pentaerythritol, caprolactone-modified glycerol, caprolactone-modified trimethylolpropane, and caprolactone-modified pentaerythritol.

[0035] The amine compound may have at least two primary and / or secondary amine groups (polyamines). Non-limiting examples of suitable polyamines include primary or secondary diamines or polyamines, where the groups attached to the nitrogen atom may be saturated or unsaturated, aliphatic, cycloaliphatic, aromatic, aromatic-substituted aliphatic, aliphatic-substituted aromatic, and heterocyclic. Non-limiting examples of suitable aliphatic and cycloaliphatic diamines include 1,2-ethylenediamine, 1,2-propylenediamine, 1,8-octanediamine, isophoronediamine, propane-2,2-cyclohexylamine, and the like. Non-limiting examples of suitable aromatic diamines include phenylenediamines and toluenediamines, such as o-phenylenediamine and p-tolylenediamine. Polynuclear aromatic diamines, such as 4,4'-biphenyldiamine, 4,4'-methylenedianiline, and monochloro and dichloro derivatives of 4,4'-methylenedianiline, are also suitable.

[0036] Polyamines suitable for use in the present disclosure can include, but are not limited to, materials having the following general formula (4):

[0037] [ka]

[0038] wherein R8 and R9 are each independently selected from the group consisting of methyl, ethyl, propyl, and isopropyl; R 10 can be selected from hydrogen and chlorine. Non-limiting examples of polyamines for use in the present disclosure include the following compounds manufactured by Lonza Ltd. (Basel, Switzerland): LONZACURE® M-DIPA: R8 = C3H7; R9 = C3H7; R 10 =H LONZACURE® MM-DMA: R8 = CH3; R9 = CH3; R 10 =H LONZACURE® MM-MEA: R8 = CH3; R9 = C2H5; R 10 =H LONZACURE® MM-DEA: R8 = C2H5; R9 = C2H5; R 10 =H LONZACURE® MM-MIPA: R8 = CH3; R9 = C3H7; R 10 =H LONZACURE® MM-CDEA: R8 = C2H5; R9 = C2H5; R 10 =Cl Among these, R8, R9 and R 10 corresponds to the above chemical formula.

[0039] Polyamines can include diamine reactive compounds such as 4,4'-methylenebis(3-chloro-2,6-diethylaniline), (Lonzacure® M-CDEA), 2,4-diamino-3,5-diethyl-toluene, 2,6-diamino-3,5-diethyl-toluene, and mixtures thereof available from Albemarle Corporation under the trade name Ethacure 100 (collectively "diethyltoluenediamine" or "DETDA"), dimethylthiotoluenediamine (DMTDA) available from Albemarle Corporation under the trade name Ethacure 300, and 4,4'-methylene-bis(2-chloroaniline) available from Kingyorker Chemicals as MOCA. DETDA has a viscosity of 156 cPs at 25°C and can be a liquid at room temperature. The DETDA may be isomeric, with the 2,4-isomer ranging from 75 to 81 percent, while the 2,6-isomer range may be from 18 to 24 percent. A color stabilized version of Ethacure 100 (i.e., a formulation containing an additive that reduces yellow color), commercially available under the trade name Ethacure 100S, may be used in the present disclosure.

[0040] Other examples of polyamines can include ethyleneamines. Suitable ethyleneamines can include, but are not limited to, ethylenediamine (EDA), diethylenetriamine (DETA), triethylenetetraamine (TETA), tetraethylenepentamine (TEPA), pentaethylenehexamine (PEHA), piperazine, morpholine, substituted morpholines, piperidine, substituted piperidine, diethylenediamine (DEDA), and 2-amino-1-ethylpiperazine. In certain embodiments, the polyamine can be selected from one or more isomers of dialkyl toluene diamines having 1 to 3 carbon atoms, such as, but not limited to, 3,5-dimethyl-2,4-toluene diamine, 3,5-dimethyl-2,6-toluene diamine, 3,5-diethyl-2,4-toluene diamine, 3,5-diethyl-2,6-toluene diamine, 3,5-diisopropyl-2,4-toluene diamine, 3,5-diisopropyl-2,6-toluene diamine, and mixtures thereof. Methylene dianiline and trimethylene glycol di(para-aminobenzoic acid) are also suitable.

[0041] Additional examples of suitable polyamines include methylene bisaniline, aniline sulfide, and bianiline, any of which may be hetero-substituted, provided that the substituents do not interfere with any reactions occurring between the reactants. Specific examples include 4,4'-methylene-bis(2,6-dimethylaniline), 4,4'-methylene-bis(2,6-diethylaniline), 4,4'-methylene-bis(2-ethyl-6-methylaniline), 4,4'-methylene-bis(2,6-diisopropylaniline), 4,4'-methylene-bis(2-isopropyl-6-methylaniline), and 4,4'-methylene-bis(2,6-diethyl-3-chloroaniline). Diaminotoluenes such as diethyltoluenediamine (DETDA) are also suitable.

[0042] From the viewpoint of the effects of the present disclosure, the content of the active hydrogen compound (B) in the polymerizable composition for an optical material is preferably 30 parts by mass or more, more preferably 40 parts by mass or more, and is preferably 70 parts by mass or less, more preferably 60 parts by mass or less, in 100 parts by mass of the polymerizable composition for an optical material.

[0043] [Ultraviolet absorber (C)] The ultraviolet absorbent (C) used in the present disclosure is represented by the following general formula (1): As the ultraviolet absorbent (C) in the present disclosure, one or more types selected from the ultraviolet absorbents represented by general formula (1) can be used.

[0044] [ka]

[0045] In the general formula (1), R1 and R2 are each an alkyl group having 1 to 8 carbon atoms, preferably an alkyl group having 2 to 6 carbon atoms, and may be the same or different. A plurality of R1s or a plurality of R2s may be the same or different. m represents an integer of 0 to 3, and is preferably 0 or 1. n represents an integer of 0 to 3, and is preferably 1 or 2. R3 represents a functional group having 4 to 10 carbon atoms containing an ester bond, and is preferably -R4-C(=O)OR5 or -R4-OC(=O)-R5, and more preferably -R4-C(=O)OR5. R4 represents a divalent hydrocarbon group having 1 to 3 carbon atoms, preferably a divalent hydrocarbon group having 1 to 2 carbon atoms, and more preferably an ethylene group. R5 represents a hydrocarbon group having 1 to 7 carbon atoms, preferably a hydrocarbon group having 1 to 5 carbon atoms, and more preferably an alkyl group having 1 to 3 carbon atoms. By using such an ultraviolet absorber (C), it is possible to provide an optical material which is highly effective in blocking harmful ultraviolet light and blue light of about 420 nm, and which also has excellent design properties.

[0046] From the viewpoint of the effects of the present disclosure, it is preferable to use, as the ultraviolet absorbent (C), one or more ultraviolet absorbents selected from compounds represented by the following general formula (2).

[0047] [ka]

[0048] In general formula (2), R1, R2, m, and n are defined the same as in general formula (1). R4 represents a divalent hydrocarbon group having 1 to 3 carbon atoms, preferably a divalent hydrocarbon group having 1 to 2 carbon atoms, and more preferably an ethylene group. R5 represents a hydrocarbon group having 1 to 7 carbon atoms, preferably a hydrocarbon group having 1 to 5 carbon atoms, and more preferably an alkyl group having 1 to 3 carbon atoms.

[0049] From the viewpoint of the effects of the present disclosure, it is more preferable to use, as the ultraviolet absorber (C), one or more ultraviolet absorbers selected from the compounds represented by the following general formula (3).

[0050] [ka]

[0051] In formula (3), R2, R4, and R5 have the same meanings as in formula (1) or (2).

[0052] From the viewpoint of the effect of blocking harmful ultraviolet rays and blue light of about 420 nm, the ultraviolet absorber (C) in the present disclosure preferably has a maximum absorption peak in the range of 340 nm or more and 370 nm or less when dissolved in a chloroform solution. As the ultraviolet absorbent (C), a compound represented by the following chemical formula can be particularly preferably used.

[0053] [ka]

[0054] As the ultraviolet absorber (C), methyl 3-[3-tert-butyl-5-(5-chloro-2H-benzotriazol-2-yl)-4-hydroxyphenyl]propionate represented by the above chemical formula can be used, such as EVERSORB88 (manufactured by EVER LIGHT).

[0055] From the viewpoint of the effects of the present disclosure, the composition of the present disclosure may contain the ultraviolet absorber (C) in an amount of 0.1 part by mass or more, preferably 0.5 part by mass or more, and more preferably 1.0 part by mass or more, and 10.0 parts by mass or less, preferably 5.0 parts by mass or less, and more preferably 2.0 parts by mass or less, per 100 parts by mass of the polymerizable composition for an optical material. The ultraviolet absorber (C) has excellent solubility and dispersibility in the isocyanate compound (A) and the active hydrogen compound (B), and can be easily added by mixing and stirring with these.

[0056] Since the ultraviolet absorber (C) has excellent solubility and dispersibility in the isocyanate compound (A) and the active hydrogen compound (B), a uniform polymerizable composition can be obtained in a short period of time, resulting in excellent productivity. Furthermore, since it has excellent solubility and dispersibility, a large amount of the ultraviolet absorbent (C) can be added, and even if a large amount is added, the ultraviolet absorbent (C) is unlikely to bleed out from the optical material, so that cloudiness is unlikely to occur. Therefore, by using the ultraviolet absorbent (C), it is possible to easily control the wavelength cut by the amount added, and it is possible to provide an optical material that has a high effect of blocking blue light of about 420 nm from harmful ultraviolet rays.

[0057] In the present disclosure, from the viewpoint of the effects of the present disclosure, specific examples of combinations of the isocyanate compound (A), the active hydrogen compound (B), and the ultraviolet absorber (C) include the following: The isocyanate compound (A) preferably contains at least one selected from an aliphatic isocyanate compound, an alicyclic isocyanate compound, an aromatic isocyanate compound, and an araliphatic isocyanate compound, more preferably contains at least one selected from an aromatic isocyanate compound and an araliphatic isocyanate compound, and further preferably contains at least one selected from xylylene diisocyanate, phenylene diisocyanate, tolylene diisocyanate, and diphenylmethane diisocyanate; The active hydrogen compound (B) is preferably at least one selected from the group consisting of a polythiol compound having two or more mercapto groups and a hydroxyl thiol compound having one or more mercapto groups and one or more hydroxyl groups, more preferably at least one selected from polythiol compounds having two or more mercapto groups, and even more preferably 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, pentaerythritol tetrakis(2-mercaptomethyl-1,8-di ... at least one selected from the group consisting of at least one selected from the group consisting of 1,1,3,3-tetrakis(mercaptomethylthio)propane, 4,6-bis(mercaptomethylthio)-1,3-dithiane, 2-(2,2-bis(mercaptomethylthio)ethyl)-1,3-dithietane, 1,1,2,2-tetrakis(mercaptomethylthio)ethane, 3-mercaptomethyl-1,5-dimercapto-2,4-dithiapentane, tris(mercaptomethylthio)methane, and ethylene glycol bis(3-mercaptopropionate); The ultraviolet absorber (C) is preferably at least one selected from the compounds represented by the above-mentioned general formula (2), more preferably at least one selected from the compounds represented by the above-mentioned general formula (3), and even more preferably methyl 3-[3-tert-butyl-5-(5-chloro-2H-benzotriazol-2-yl)-4-hydroxyphenyl]propionate; and combinations thereof.

[0058] In the present disclosure, other ultraviolet absorbents may be contained in addition to the ultraviolet absorbent (C), such as benzophenone compounds, triazine compounds, and benzotriazole compounds. Examples of the benzophenone compounds include 2,2'-dihydroxy-4,4'-dimethoxybenzophenone and 2,2'-4,4'-tetrahydroxybenzophenone. Examples of the triazine compound include Adeka STAB LA-F70 manufactured by ADEKA Corporation and TINUVIN 400 manufactured by BASF. The other ultraviolet absorbent preferably has a structure other than that of general formula (1) and has a maximum absorption peak in the range of 340 nm or more and 370 nm or less.

[0059] In the present disclosure, the molar ratio of active hydrogen groups in the active hydrogen compound (B) to the isocyanato groups in the isocyanate compound (A) is within a range of 0.8 to 1.2, preferably within a range of 0.85 to 1.15, and more preferably within a range of 0.9 to 1.1. Within the above range, a resin suitable for use as an optical material, particularly as a plastic lens material for spectacles, can be obtained.

[0060] (Other ingredients) The polymerizable composition for an optical material of the present disclosure may further contain, as other components, a polymerization catalyst, an internal mold releasing agent, a resin modifier, a light stabilizer, a bluing agent, and the like.

[0061] (catalyst) Examples of the catalyst include Lewis acids, amines, organic acids, and amine-organic acid salts. Lewis acids, amines, and amine-organic acid salts are preferred, and dimethyltin chloride, dibutyltin chloride, and dibutyltin laurate are more preferred.

[0062] (Internal release agent) As the internal mold release agent, an acidic phosphoric acid ester can be used. Examples of the acidic phosphoric acid ester include a phosphoric acid monoester and a phosphoric acid diester, and each of them can be used alone or in combination of two or more kinds. For example, ZelecUN manufactured by STEPAN, internal release agents for MR manufactured by Mitsui Chemicals, JP series manufactured by Johoku Chemical Industry Co., Ltd., Phosphanol series manufactured by Toho Chemical Industry Co., Ltd., AP and DP series manufactured by Daihachi Chemical Industry Co., Ltd., etc. can be used.

[0063] (Resin modifier) To the polymerizable composition for an optical material of the present disclosure, a resin modifier can be added for the purpose of adjusting various physical properties of the resulting resin, such as optical properties, impact resistance, and specific gravity, and adjusting the handleability of the polymerizable composition, within a range that does not impair the effects of the present disclosure.

[0064] Examples of the resin modifier include episulfide compounds, alcohol compounds, amine compounds, epoxy compounds, organic acids and their anhydrides, olefin compounds including (meth)acrylate compounds, and the like.

[0065] (Light stabilizer) As the light stabilizer, a hindered amine compound can be used. Examples of commercially available hindered amine compounds include Lowilite 76 and Lowilite 92 manufactured by Chemtura, Tinuvin 144, Tinuvin 292, and Tinuvin 765 manufactured by BASF, Adeka STAB LA-52 and LA-72 manufactured by ADEKA, and JF-95 manufactured by Johoku Chemical Industry Co., Ltd.

[0066] (Bluing agent) Examples of bluing agents include those that have an absorption band in the orange to yellow wavelength region of the visible light range and have the function of adjusting the hue of the optical material made of resin. More specifically, the bluing agent includes a substance that exhibits a blue to purple color.

[0067] The polymerizable composition for an optical material of the present disclosure can be obtained by mixing the isocyanate compound (A), the active hydrogen compound (B), the ultraviolet absorber (C), and, as necessary, other thiol compounds, catalysts, internal mold release agents, and other additives in a predetermined manner. The temperature during mixing is usually 25°C or lower. From the viewpoint of the pot life of the polymerizable composition for optical materials, it may be preferable to use an even lower temperature. However, if the solubility of the catalyst, internal mold release agent, or additive in the isocyanate compound (A) or active hydrogen compound (B) is not good, it is possible to heat the mixture in advance to dissolve it. The mixing order and method of each component in the composition are not particularly limited as long as each component can be mixed uniformly, and can be performed by a known method, such as a method of preparing a master batch containing a predetermined amount of additives and dispersing or dissolving this master batch in a solvent.

[0068] <Cured product> The polymerizable composition for optical materials of the present disclosure can be polymerized to obtain a cured product, and the cured product can have various shapes depending on the shape of the mold. The polymerization method can be a conventionally known method, and the conditions are not particularly limited. In the present disclosure, the method for producing the cured product is not particularly limited, but a preferred method is cast polymerization. First, the polymerizable composition for optical materials is poured between a mold held by a gasket or tape. At this time, depending on the physical properties required for the obtained cured product, it is often preferable to perform a degassing treatment under reduced pressure, a filtration treatment under pressure or reduced pressure, etc., as necessary.

[0069] The polymerization conditions are not limited because they vary depending on the types and amounts of components (A) to (C), the type and amount of catalyst, the shape of the mold, etc., but are generally carried out at a temperature of -50 to 150°C for 1 to 50 hours. In some cases, it is preferable to maintain or gradually increase the temperature within a range of 10 to 150°C and cure for 1 to 25 hours.

[0070] The cured product of the present disclosure may be subjected to a treatment such as annealing, if necessary. The treatment is usually performed at a temperature between 50 and 150°C, preferably between 90 and 140°C, and more preferably between 100 and 130°C.

[0071] In addition, in the present disclosure, the cured product obtained by heat-curing the polymerizable composition for optical materials can be used as an optical material, and can constitute a part of the optical material. The cured product of the present disclosure is colorless and transparent, has excellent appearance, has excellent blocking effect from ultraviolet light to blue light of about 420 nm, and is excellent in design, and has excellent optical properties such as high refractive index and high Abbe number, and excellent physical properties such as heat resistance. By forming the cured product into a desired shape and providing it with a coating layer or other members formed as necessary, it can be used as various optical materials.

[0072] From the viewpoint of the effects of the present disclosure, the ultraviolet absorber (C) contained in the cured product of the present disclosure can be contained in an amount of 0.1 part by mass or more, preferably 0.5 part by mass or more, and more preferably 1.0 part by mass or more, and can be contained in an amount of 10.0 parts by mass or less, preferably 5.0 parts by mass or less, and more preferably 2.0 parts by mass or less, per 100 parts by mass of the polymerizable composition for optical materials. <Second embodiment> The polymerizable composition for an optical material of the present disclosure contains (D) a compound having a cyclic structure containing a sulfur atom, and (C) an ultraviolet absorber represented by general formula (1). Each component will be described in detail below.

[0073] [(D) Compounds having a cyclic structure containing a sulfur atom] In the present disclosure, the compound (D) having a cyclic structure containing a sulfur atom is not particularly limited, and various compounds can be used as long as they have the structure and can exert the effects of the present disclosure. An example of the compound (D) is a compound having two or more 3- to 5-membered ring structures containing S in one molecule. Examples of the 3- to 5-membered ring containing S include an episulfide group, a thietanyl group, a thiolanyl group, and a thienyl group. The weight average molecular weight of the compound (D) can be, for example, 100 or more and 1,000 or less, and preferably 150 or more and 500 or less.

[0074] Compound (D) is preferably a compound having two or more episulfide groups or thietanyl groups. Specific examples of the compound having two or more episulfide groups (hereinafter, episulfide compound (D1)) and the compound having two or more thietanyl groups (hereinafter, thietanyl compound (D2)) include the following compounds.

[0075] As the episulfide compound (D1), a compound having two or more episulfide groups in the molecule as disclosed in WO2009 / 104385 can be used. Specifically, the episulfide compound (D1) is a compound represented by the general formula (5): Examples of the bis(1,2-epithioethyl)sulfide include bis(1,2-epithioethyl)disulfide, 1,3-bis(2,3-epithiopropylthio)cyclohexane, 1,4-bis(2,3-epithiopropylthio)cyclohexane, 1,2-bis(2,3-epithiopropylthio)benzene, 1,3-bis(2,3-epithiopropylthio)benzene, bis(2,3-epithiopropyl)ether, bis(2,3-epithiopropyloxy)methane, 1,3-bis(2,3-epithiopropyloxy)cyclohexane, and 1,2-bis(2,3-epithiopropyloxy)benzene. At least one selected from these can be used.

[0076] [ka]

[0077] In formula (5), n represents 0 or 1.

[0078] From the viewpoint of the effects of the present invention, the episulfide compound (D1) is preferably bis(1,2-epithioethyl)sulfide, bis(1,2-epithioethyl)disulfide, or a compound represented by the above general formula (5), and more preferably a compound represented by the above general formula (5). The compound represented by the general formula (5) is bis(2,3-epithiopropyl)sulfide or bis(2,3-epithiopropyl)disulfide.

[0079] The thietanyl compound (D2) is a compound containing a total of two or more thietanyl groups in the molecule, as disclosed in WO2005-95490 and JP2003-327583A. Specific examples of the thietanyl compound (D2) include compounds represented by general formula (6), polysulfide-based thietane compounds such as bis(3-thietanylthio) disulfide, bis(3-thietanylthio) methane, 3-(((3'-thietanylthio) methylthio) methylthio) thietane, bis(3-thietanyl) trisulfide, bis(3-thietanyl) tetrasulfide, and bis(3-thietanyl) pentasulfide. At least one selected from these can be used.

[0080] [ka]

[0081] In formula (6), n represents 0 or 1.

[0082] From the viewpoint of the effects of the present invention, the thietanyl compound (D2) is preferably a compound represented by the above general formula (6), bisthietanyl trisulfide, bisthietanyl tetrasulfide, or bisthietanyl pentasulfide, and more preferably a compound represented by the above general formula (6), specifically, bisthietanyl sulfide or bisthietanyl disulfide. These episulfide compounds (D1) and thietanyl compounds (D2) can be used alone or in combination of two or more. In the present disclosure, it is particularly preferable to use bis(2,3-epithiopropyl)sulfide and bis(2,3-epithiopropyl)disulfide, which are compounds represented by general formula (5), as the compound (D).

[0083] [Ultraviolet absorber (C)] The ultraviolet absorbent (C) used in the present disclosure may be the same as that in the first embodiment.

[0084] Since the ultraviolet absorber (C) has excellent solubility and dispersibility in the compound (D) having a cyclic structure containing a sulfur atom and the polythiol compound described later, a uniform polymerizable composition can be obtained in a short period of time, resulting in excellent productivity. Furthermore, since it has excellent solubility and dispersibility, a large amount of the ultraviolet absorbent (C) can be added, and even if a large amount is added, the ultraviolet absorbent (C) does not bleed out from the optical material, so that cloudiness is unlikely to occur. Therefore, by using the ultraviolet absorbent (C), it is possible to easily control the wavelength cut by the amount added, and it is possible to provide an optical material that has a high effect of blocking blue light of about 420 nm from harmful ultraviolet rays.

[0085] [Polythiol compounds] The compositions of the present disclosure can further include a polythiol compound having two or more mercapto groups.

[0086] As the polythiol compound, the same compounds as those in the first embodiment can be used.

[0087] Specific examples of the polythiol compound include pentaerythritol tetrakis(2-mercaptoacetate), pentaerythritol tetrakis(3-mercaptopropionate), bis(mercaptoethyl)sulfide, 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6, 9-trithiaundecane, 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 2,5-dimercaptomethyl-1,4-dithiane, 1,1,3,3-tetrakis(mercaptomethylthio)propane, 4,6-bis(mercaptomethylthio)-1,3-dithiane, 2-(2,2-bis(mercaptomethylthio)ethyl)-1,3-dithietane, ethylene glycol bis(3-mercaptopropionate), etc. At least one selected from these can be used.

[0088] In the composition of the present disclosure, the ultraviolet absorber (C) is contained in an amount of 0.1 to 3.0% by weight, and preferably 0.5 to 2.0% by weight, relative to 100% by weight of the compound (D), from the viewpoint of the effects of the present disclosure. When the polythiol is further contained, the ultraviolet absorber (C) is contained in an amount of 0.1 to 3.0% by weight, preferably 0.5 to 2.0% by weight, relative to the total weight of the compound (D) and the polythiol compound being 100% by weight, from the viewpoint of the effects of the present disclosure.

[0089] In the present disclosure, from the viewpoint of the effects of the present disclosure, specific examples of the combination of the compound (D) having a cyclic structure containing a sulfur atom and the ultraviolet absorber (C) include: The compound (D) preferably includes at least one selected from the episulfide compound (D1) of the general formula (5) and the thietanyl compound (D2) of the general formula (6), more preferably includes at least one selected from the episulfide compound (D1) of the general formula (5), and further preferably includes bis(2,3-epithiopropyl)sulfide and / or bis(2,3-epithiopropyl)disulfide; The ultraviolet absorber (C) preferably contains at least one compound selected from the compounds represented by the general formula (2) described above, more preferably contains at least one compound selected from the compounds represented by the general formula (3) described above, and even more preferably is methyl 3-[3-tert-butyl-5-(5-chloro-2H-benzotriazol-2-yl)-4-hydroxyphenyl]propionate; and combinations thereof are also included. When the composition of the present disclosure further comprises a polythiol compound, The polythiol compound preferably includes at least one selected from an aliphatic polythiol compound, an aromatic polythiol compound, and a heterocyclic polythiol compound, and more preferably includes at least one selected from pentaerythritol tetrakis(2-mercaptoacetate), pentaerythritol tetrakis(3-mercaptopropionate), bis(mercaptoethyl)sulfide, 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercapto It may contain at least one selected from the group consisting of methyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 2,5-dimercaptomethyl-1,4-dithiane, 1,1,3,3-tetrakis(mercaptomethylthio)propane, 4,6-bis(mercaptomethylthio)-1,3-dithiane, 2-(2,2-bis(mercaptomethylthio)ethyl)-1,3-dithietane, and ethylene glycol bis(3-mercaptopropionate).

[0090] In the present disclosure, other ultraviolet absorbents may be contained in addition to the ultraviolet absorbent (C), such as benzophenone compounds, triazine compounds, and benzotriazole compounds. Examples of the benzophenone compounds include 2,2'-dihydroxy-4,4'-dimethoxybenzophenone and 2,2'-4,4'-tetrahydroxybenzophenone. Examples of the triazine compound include Adeka STAB LA-F70 manufactured by ADEKA Corporation and TINUVIN 400 manufactured by BASF. The other ultraviolet absorbent preferably has a structure other than that of general formula (1) and has a maximum absorption peak in the range of 340 nm or more and 370 nm or less.

[0091] (Other ingredients) The polymerizable composition for an optical material of the present disclosure may further contain, as other components, the polymerization catalyst, internal mold release agent, resin modifier, light stabilizer, bluing agent, and the like described in the first embodiment.

[0092] The polymerizable composition for optical materials can be obtained by mixing the compound (D) having a cyclic structure containing a sulfur atom, the ultraviolet absorber (C), and, if necessary, a polythiol compound, and, if necessary, a catalyst, an internal mold release agent, and other additives, in a predetermined manner. The temperature during mixing is usually 25°C or lower. From the viewpoint of the pot life of the polymerizable composition for optical materials, it may be preferable to use an even lower temperature. However, if the solubility of the catalyst, internal mold release agent, or additive in the compound (D) is not good, it is also possible to heat the mixture in advance to dissolve it. The mixing order and method of each component in the composition are not particularly limited as long as each component can be mixed uniformly, and can be performed by a known method, such as a method of preparing a master batch containing a predetermined amount of additives and dispersing or dissolving this master batch in a solvent.

[0093] <Cured product> A cured product can be obtained from the polymerizable composition for an optical material of the present disclosure by the method described in the first embodiment, and molded articles of various shapes can be obtained depending on the shape of the mold.

[0094] The polymerization conditions are not limited because they vary depending on the components (D) and (C), the type and amount of polythiol compound added as needed, the type and amount of catalyst used, the shape of the mold, etc., but are generally carried out at a temperature of -50 to 150°C for 1 to 50 hours. In some cases, it is preferable to maintain or gradually increase the temperature within a range of 10 to 150°C and cure for 1 to 25 hours.

[0095] The cured product of the present disclosure may be subjected to treatment such as annealing as in the first embodiment, if necessary.

[0096] In addition, in the present disclosure, the cured product obtained by heat-curing the polymerizable composition for optical materials can be used as an optical material, and can constitute a part of the optical material. The cured product of the present disclosure is colorless and transparent, has excellent appearance, has excellent blocking effect from ultraviolet light to blue light of about 420 nm, and is excellent in design, and has excellent optical properties such as high refractive index and high Abbe number, and excellent physical properties such as heat resistance. By forming the cured product into a desired shape and providing it with a coating layer or other members formed as necessary, it can be used as various optical materials.

[0097] From the viewpoint of the effects of the present disclosure, the ultraviolet absorber (C) is contained in an amount of 0.1 to 3.0% by weight, and preferably 0.5 to 2.0% by weight, based on 100% by weight of the cured product.

[0098] <Optical materials> Examples of the optical material of the present disclosure include plastic lenses, camera lenses, light-emitting diodes (LEDs), prisms, optical fibers, information recording substrates, filters, light-emitting diodes, etc. In particular, the optical material is suitable for optical elements such as plastic lenses, camera lenses, and light-emitting diodes.

[0099] The plastic lens containing the cured product of the present disclosure may be used by applying a coating layer to one or both sides of the lens substrate made of the cured product, as necessary. Examples of the coating layer include a primer layer, a hard coat layer, an anti-reflection film layer, an anti-fogging coating film layer, an anti-staining layer, and a water-repellent layer. Each of these coating layers may be used alone or multiple coating layers may be used in a multi-layered configuration. When applying coating layers to both sides, the same coating layer may be applied to each side, or different coating layers may be applied to each side.

[0100] These coating layers may each contain an infrared absorbing agent for protecting the eyes from infrared rays, a light stabilizer or an antioxidant for improving the weather resistance of the lens, a dye or pigment for enhancing the fashionability of the lens, a photochromic dye or a photochromic pigment, an antistatic agent, or other known additives for improving the performance of the lens. A coating layer such as a hard coat or an antireflection coat, or a primer layer may also be provided.

[0101] A plastic lens containing the cured product of the present disclosure may be dyed using a dye according to the purpose for which it is intended, such as to impart fashionability or photochromic properties, etc. The lens can be dyed by a known dyeing method. Moreover, the method for producing an optical material according to the present disclosure includes, for example, a step of casting polymerizing the polymerizable composition for an optical material according to the present disclosure.

[0102] Although the present disclosure has been described above based on the present disclosure, various configurations can be adopted within a range that does not impair the effects of the present disclosure. EXAMPLES

[0103] The present disclosure will be described in more detail below with reference to examples, but the present disclosure is not limited thereto. The present disclosure will be described below with reference to examples a and b. <Example a> The evaluation methods in Example a are as follows.

[0104] <Evaluation method> Time until UV absorber dissolves In Example a, the time required for complete dissolution of the various additives containing the ultraviolet absorber after the isocyanate solution was added was visually confirmed. ·Light transmittance The measurement equipment used was a Shimadzu UV-1800 spectrophotometer manufactured by Shimadzu Corporation, and the ultraviolet-visible light spectrum was measured using a 2 mm thick plano lens to measure the transmittance at a specific wavelength (410 nm).

[0105] ·Absorbance In the above light transmittance measurement, the transmittance at 410 nm and 800 nm was calculated using the following formula, where T% [410 nm] and T% [800 nm] are the transmittances at 410 nm and 800 nm, respectively. Absorbance at 410 nm = - [log (T% [410 nm] / 100) - log (T% [800 nm] / 100)] In resins without anti-reflection properties, even at the non-absorbent wavelength of 800 nm, the transmittance drops by about 10% due to reflection, etc. In order to eliminate the effects of this reflection, etc., the absorbance was calculated by subtracting the absorbance at 800 nm from the absorbance calculated from the transmittance at a wavelength of 410 nm.

[0106] ·YI (Yellow Index) A circular flat plastic lens with a thickness of 9 mm and a diameter of 75 mm was prepared, and the chromaticity coordinates x and y were measured using a spectrophotometer CM-5 manufactured by MINOLTA Corp. Based on the measured values ​​of x and y, YI was calculated using the following formula (1). YI=(234*x+106*y+106) / y (1)

[0107] <Maximum absorption peak of UV absorber> The maximum absorption peak of the ultraviolet absorbent used in Example a was as follows: Measurement method: The measurement instrument used was a Shimadzu UV-1800 spectrophotometer manufactured by Shimadzu Corporation, and the ultraviolet-visible light spectrum was measured using a 2 mm thick plano lens. EVERSORB88: The maximum absorption peak was in the range of 340 nm to 370 nm. TINUVIN326: The maximum absorption peak was in the range of 340 nm to 370 nm.

[0108] [Example a1] 0.1 parts by weight of ZelecUN (STEPAN), 1.5 parts by weight of 3-[3-tert-butyl-5-(5-chloro-2H-benzotriazol-2-yl)-4-hydroxyphenyl]methyl propionate (EVERSORB88, EVER LIGHT), and 52.0 parts by weight of xylylene diisocyanate were mixed and stirred at 20°C to obtain a homogeneous solution. 48.0 parts by weight of 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane and 0.15 parts by weight of dibutyltin (II) dichloride were added to this homogeneous solution and mixed and stirred at 20°C to obtain a mixed solution. This mixed solution was degassed at 600 Pa for 1 hour, filtered with a 1 μm PTFE filter, and then poured into a mold consisting of a 2C (curve, the same applies below) planar glass mold with a center thickness of 2 mm and a diameter of 80 mm and a flat glass mold with a center thickness of 2 mm and a diameter of 78 mm. This mold was placed in a polymerization oven, and the temperature was gradually raised from 20°C to 130°C over 21 hours to polymerize. After polymerization was completed, the mold was removed from the oven. The resulting plano lens was further annealed at 130°C for 2 hours. The resulting 2mm-thick plano lens was transparent and suitable as a transparent resin for optical materials. The ultraviolet-visible spectrum of the resulting plano lens was measured using a spectrophotometer UV-1800 (manufactured by Shimadzu Corporation). The evaluation results are shown in Table 1.

[0109] [Example a2] A plano lens having a thickness of 2 mm was obtained in the same manner as in Example a1, except that 1.5 parts by weight of 3-[3-tert-butyl-5-(5-chloro-2H-benzotriazol-2-yl)-4-hydroxyphenyl]methyl propionate (EVERSORB88 manufactured by EVER LIGHT) was changed to 2.0 parts by weight. The plano lens obtained was transparent and suitable as a transparent resin for optical materials. The ultraviolet-visible spectrum of the plano lens obtained was measured using a spectrophotometer UV-1800 (manufactured by Shimadzu Corporation). The evaluation results are shown in Table 1.

[0110] [Example a3] 0.1 parts by weight of ZelecUN (STEPAN), 1.5 parts by weight of 3-[3-tert-butyl-5-(5-chloro-2H-benzotriazol-2-yl)-4-hydroxyphenyl]methyl propionate (EVERSORB88, EVER LIGHT), and 50.6 parts by weight of xylylene diisocyanate were mixed and stirred at 20° C. to obtain a homogeneous solution. 49.4 parts by weight of a mixture of 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, and 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, and 0.10 parts by weight of dibutyltin(II) dichloride were added to the homogeneous solution and mixed and stirred at 20° C. to obtain a mixed solution. The mixture was degassed at 600 Pa for 1 hour, filtered with a 1 μm PTFE filter, and then poured into a mold consisting of a 2C (curve, the same applies below) plano glass mold with a center thickness of 2 mm and a diameter of 80 mm and a flat glass mold with a center thickness of 2 mm and a diameter of 78 mm. The mold was placed in a polymerization oven and gradually heated from 20°C to 130°C over 21 hours to polymerize. After polymerization was completed, the mold was removed from the oven. The obtained plano lens was further annealed at 130°C for 2 hours. The obtained 2 mm thick plano lens was transparent and suitable as a transparent resin for optical materials. The ultraviolet-visible spectrum of the obtained plano lens was measured using a spectrophotometer UV-1800 (manufactured by Shimadzu Corporation). The evaluation results are shown in Table 1.

[0111] [Example a4] A plano lens having a thickness of 2 mm was obtained in the same manner as in Example a3, except that 1.5 parts by weight of 3-[3-tert-butyl-5-(5-chloro-2H-benzotriazol-2-yl)-4-hydroxyphenyl]methyl propionate (EVERSORB88 manufactured by EVER LIGHT) was changed to 2.0 parts by weight. The plano lens obtained was transparent and suitable as a transparent resin for optical materials. The ultraviolet-visible spectrum of the plano lens obtained was measured using a spectrophotometer UV-1800 (manufactured by Shimadzu Corporation). The evaluation results are shown in Table 1.

[0112] [Comparative Example a1] A plano lens having a thickness of 2 mm was obtained in the same manner as in Example a1, except that 1.5 parts by weight of 3-[3-tert-butyl-5-(5-chloro-2H-benzotriazol-2-yl)-4-hydroxyphenyl]methyl propionate (EVERSORB88 manufactured by EVER LIGHT) was replaced with 0.5 parts by weight of 2-(2-hydroxy-3-t-butyl-5-methylphenyl)-chlorobenzotriazole (TINUVIN326 manufactured by BASF). The plano lens obtained was transparent and suitable as a transparent resin for optical materials. The ultraviolet-visible spectrum of the plano lens obtained was measured using a spectrophotometer UV-1800 (manufactured by Shimadzu Corporation). The evaluation results are shown in Table 1.

[0113] [Comparative example a2] A plano lens having a thickness of 2 mm was obtained in the same manner as in Comparative Example a1, except that 0.5 parts by weight of 2-(2-hydroxy-3-t-butyl-5-methylphenyl)-chlorobenzotriazole (TINUVIN326 manufactured by BASF) was changed to 0.7 parts by weight. The plano lens obtained was transparent and suitable as a transparent resin for optical materials. The ultraviolet-visible spectrum of the plano lens obtained was measured using a spectrophotometer UV-1800 (manufactured by Shimadzu Corporation). The evaluation results are shown in Table 1.

[0114] [Table 1]

[0115] The isocyanate compounds, active hydrogen compounds, and UV absorbers listed in Table 1 are as follows: a-1: Xylylene diisocyanate b-1: 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane b-2: A mixture of 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, and 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane C-1: 3-[3-tert-butyl-5-(5-chloro-2H-benzotriazol-2-yl)-4-hydroxyphenyl]propionic acid methyl ester C-2: 2-(2-hydroxy-3-t-butyl-5-methylphenyl)-chlorobenzotriazole

[0116] From the results in Table 1, the lens of Example a had an excellent effect of blocking light ranging from ultraviolet rays to blue light of about 420 nm, and was transparent and had suppressed coloring, so that it also had excellent design properties. The effects of Example a can be compared with those of Comparative Example a as follows. The absorbance at a wavelength of 410 nm is an index of the effectiveness of the UV absorber, and the higher the value, the higher the blue light blocking effect, which is preferable. On the other hand, the coloration of the lens due to the addition of the UV absorber is indicated by YI, and the smaller the value, the less coloration of the lens, which is preferable. In this Example a, the balance between the color degree of the lens due to the addition of a specified ultraviolet absorbent and the blue light blocking effect is confirmed by calculating "YI / absorbance at a wavelength of 410 nm". A smaller value indicates a better balance. The results of "YI / absorbance at wavelength 410 nm" listed in Table 1 are shown in Figure 1. As shown in Figure 1, it was confirmed that the lens of Example a has a significantly better balance between coloring degree and blue light blocking effect than that of Comparative Example a.

[0117] <Example b> The evaluation methods in Example b are as follows. <Evaluation method> ·Light transmittance The measurement equipment used was a Shimadzu UV-1800 spectrophotometer manufactured by Shimadzu Corporation, and the ultraviolet-visible light spectrum was measured using a 2 mm thick plano lens to measure the transmittance at specific wavelengths (410 nm, 420 nm, 430 nm, 800 nm).

[0118] ·YI (Yellow Index) A circular flat plastic lens with a thickness of 9 mm and a diameter of 75 mm was prepared, and the chromaticity coordinates x and y were measured using a MINOLTA CM-5 spectrophotometer in accordance with ASTM E313-73. Based on the measured values ​​of x and y, YI was calculated using the following formula (1). YI=(234*x+106*y+106) / y (1)

[0119] ·Absorbance In the above light transmittance measurement, the transmittance at 420 nm, 410 nm, and 800 nm was calculated using the following formula, where T% [410 nm], T% [420 nm], and T% [800 nm]. Absorbance at 410 nm = - [log (T% [410 nm] / 100) - log (T% [800 nm] / 100)] Absorbance at 420 nm = - [log (T% [420 nm] / 100) - log (T% [800 nm] / 100)] In resins without anti-reflection properties, even at the non-absorbent wavelength of 800 nm, the transmittance drops by about 10% due to reflection, etc. In order to eliminate the effects of this reflection, etc., the absorbance at 800 nm was subtracted from the absorbance calculated from the transmittance at wavelengths of 410 nm or 420 nm to obtain the absorbance.

[0120] Maximum absorption peak of UV absorber The maximum absorption peak of the ultraviolet absorbent used in Example b was as follows: Measurement method: The measurement instrument used was a Shimadzu UV-1800 spectrophotometer manufactured by Shimadzu Corporation, and the ultraviolet-visible light spectrum was measured using a 2 mm thick plano lens. EVERSORB88: The maximum absorption peak was in the range of 340 nm to 370 nm. EVERSORB109: The maximum absorption peak was in the range of 340 nm to 370 nm.

[0121] [Example b1] 1.2 parts by weight of methyl 3-[3-tert-butyl-5-(5-chloro-2H-benzotriazol-2-yl)-4-hydroxyphenyl]propionate (EVERSORB88 manufactured by EVER LIGHT) and 90.9 parts by weight of bis(2,3-epithiopropyl)disulfide were mixed with stirring at 30° C. to obtain a homogeneous solution. To this homogeneous solution, 9.1 parts by weight of a mixture of 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, and 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 0.09 parts by weight of N,N-dicyclohexylmethylamine, and 0.02 parts by weight of N,N-dimethylcyclohexylamine were added and stirred and mixed at 20° C. to obtain a mixed solution. This mixed solution was degassed at 600 Pa for 1 hour, filtered with a 1 μm PTFE filter, and then poured into a mold consisting of a 2C (curve, the same applies below) planar glass mold with a center thickness of 2 mm and a diameter of 80 mm and a flat glass mold with a center thickness of 9 mm and a diameter of 78 mm. This mold was placed in a polymerization oven and the temperature was gradually raised from 30°C to 120°C over 21 hours to polymerize. After polymerization was completed, the mold was removed from the oven. The resulting plano lens was further annealed at 120°C for 1 hour. The resulting lens was transparent as shown in Figure 1, and was suitable as a transparent resin for optical materials. The ultraviolet-visible spectrum of the resulting plano lens was measured using a spectrophotometer UV-1800 (manufactured by Shimadzu Corporation). The evaluation results are shown in Table 2.

[0122] [Example b2] 0.6 parts by weight of methyl 3-[3-tert-butyl-5-(5-chloro-2H-benzotriazol-2-yl)-4-hydroxyphenyl]propionate (EVERSORB88 manufactured by EVER LIGHT) and 90.9 parts by weight of bis(2,3-epithiopropyl)disulfide were mixed with stirring at 30° C. to obtain a homogeneous solution. To this homogeneous solution, 9.1 parts by weight of a mixture of 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, and 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 0.09 parts by weight of N,N-dicyclohexylmethylamine, and 0.02 parts by weight of N,N-dimethylcyclohexylamine were added and stirred and mixed at 20° C. to obtain a mixed solution. This mixed solution was degassed at 600 Pa for 1 hour, filtered with a 1 μm PTFE filter, and then poured into a mold consisting of a 2C (curve, the same applies below) planar glass mold with a center thickness of 2 mm and a diameter of 80 mm and a flat glass mold with a center thickness of 9 mm and a diameter of 78 mm. This mold was placed in a polymerization oven and the temperature was gradually raised from 30°C to 120°C over 21 hours to polymerize. After polymerization was completed, the mold was removed from the oven. The resulting plano lens was further annealed at 120°C for 1 hour. The resulting lens was transparent as shown in Figure 2, and was suitable as a transparent resin for optical materials. The ultraviolet-visible spectrum of the resulting plano lens was measured using a spectrophotometer UV-1800 (manufactured by Shimadzu Corporation). The evaluation results are shown in Table 2.

[0123] [Example b3] 0.9 parts by weight of methyl 3-[3-tert-butyl-5-(5-chloro-2H-benzotriazol-2-yl)-4-hydroxyphenyl]propionate (EVERSORB88 manufactured by EVER LIGHT) and 90.9 parts by weight of bis(2,3-epithiopropyl)disulfide were mixed with stirring at 30° C. to obtain a homogeneous solution. To this homogeneous solution, 9.1 parts by weight of a mixture of 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, and 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 0.09 parts by weight of N,N-dicyclohexylmethylamine, and 0.02 parts by weight of N,N-dimethylcyclohexylamine were added and stirred and mixed at 20° C. to obtain a mixed solution. This mixed solution was degassed at 600 Pa for 1 hour, filtered with a 1 μm PTFE filter, and then poured into a mold consisting of a 2C (curve, the same applies below) planar glass mold with a center thickness of 2 mm and a diameter of 80 mm and a flat glass mold with a center thickness of 9 mm and a diameter of 78 mm. This mold was placed in a polymerization oven and the temperature was gradually raised from 30°C to 120°C over 21 hours to polymerize. After polymerization was completed, the mold was removed from the oven. The resulting plano lens was further annealed at 120°C for 1 hour. The resulting lens was transparent as shown in Figure 1, and was suitable as a transparent resin for optical materials. The ultraviolet-visible spectrum of the resulting plano lens was measured using a spectrophotometer UV-1800 (manufactured by Shimadzu Corporation). The evaluation results are shown in Table 2.

[0124] [Comparative Example b1] A plano lens having a thickness of 2 mm and a flat plate having a thickness of 9 mm were obtained in the same manner as in Example b1, except that 3-[3-tert-butyl-5-(5-chloro-2H-benzotriazol-2-yl)-4-hydroxyphenyl]methyl propionate (EVERSORB88 manufactured by EVER LIGHT) was replaced with 3-[3-tert-butyl-5-(5-chloro-2H-benzotriazol-2-yl)-4-hydroxyphenyl]octyl propionate (EVERSORB109 manufactured by EVER LIGHT). The obtained lens was opaque as shown in FIG. 2, so the light transmittance, YI, and absorbance were not measured. The evaluation results are shown in Table 2.

[0125] [Table 2]

[0126] The compounds having a cyclic structure containing a sulfur atom, the polythiol compounds, and the UV absorbers listed in Table 2 are as follows: d-1: Bis(2,3-epithiopropyl) disulfide b-1: A mixture of 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, and 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane C-1: 3-[3-tert-butyl-5-(5-chloro-2H-benzotriazol-2-yl)-4-hydroxyphenyl]propionic acid methyl ester c-2: Octyl 3-[3-tert-butyl-5-(5-chloro-2H-benzotriazol-2-yl)-4-hydroxyphenyl]propionate

[0127] From the results in Table 2, the lens of Example b had an excellent effect of blocking blue light from ultraviolet rays to about 420 nm, and was transparent and had suppressed coloring, so that it also had excellent design properties.

[0128] This application claims priority based on Japanese Patent Application No. 2019-021646, filed February 8, 2019, and Japanese Patent Application No. 2019-052771, filed March 20, 2019, the disclosures of which are incorporated herein in their entirety.

Claims

1. (A) an isocyanate compound; (B) at least one active hydrogen compound selected from the group consisting of a polythiol compound having two or more mercapto groups, a hydroxythiol compound having one or more mercapto groups and one or more hydroxyl groups, a polyol compound having two or more hydroxyl groups, and an amine compound; (C) a compound represented by the following general formula (2): 【Chemistry 1】 (In the above general formula (2), R １ , R ２ R represents an alkyl group having 1 to 8 carbon atoms, and may be the same or different. １ R ２ may be the same or different. m is an integer of 0 to 3, n is an integer of 0 to 3, R 4 is a hydrocarbon group having 1 to 3 carbon atoms, and R 5 is a hydrocarbon group having 1 to 7 carbon atoms. and an ultraviolet absorber represented by the formula: and does not contain a polyhydric phenol compound.

2. (D) a compound having a cyclic structure containing a sulfur atom; (C) a compound represented by the following general formula (2): 【Chemistry 2】 (In the above general formula (2), R １ , R ２ R represents an alkyl group having 1 to 8 carbon atoms, and may be the same or different. １ R ２ may be the same or different. m is an integer of 0 to 3, n is an integer of 0 to 3, R 4 is a hydrocarbon group having 1 to 3 carbon atoms, and R 5 is a hydrocarbon group having 1 to 7 carbon atoms. and an ultraviolet absorber represented by the formula: A polymerizable composition for an optical material comprising the above compound.

3. The ultraviolet absorber (C) is represented by the following general formula (3): 【Chemistry 3】 (In the above general formula (3), R ２ , R ４ , R ５ has the same meaning as in general formula (2). The polymerizable composition for an optical material according to claim 2 , wherein the ultraviolet absorber is represented by the formula:

4. The polymerizable composition for an optical material according to claim 1 or 2, wherein the ultraviolet absorber (C) has a maximum absorption peak within a range of 340 nm or more and 370 nm or less.

5. The polymerizable composition for an optical material according to claim 1 , wherein the isocyanate compound (A) comprises at least one selected from an aromatic isocyanate compound and an araliphatic isocyanate compound.

6. 6. The polymerizable composition for an optical material according to claim 5, wherein the isocyanate compound (A) is at least one selected from the group consisting of xylylene diisocyanate, phenylene diisocyanate, tolylene diisocyanate, and diphenylmethane diisocyanate.

7. The polymerizable composition for an optical material according to claim 2, wherein the compound (D) has two or more 3- to 5-membered cyclic structures containing S in one molecule and has a weight average molecular weight of 100 or more and 1,000 or less.

8. The compound (D) is represented by the following general formula (5): 【Chemistry 5】 The polymerizable composition for an optical material according to claim 7, which is a compound containing an episulfide group represented by the formula: (wherein n is 0 or 1).

9. The polythiol compound (B) is, for example, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, pentaerythritol tetrakis(2-mercaptoacetate), pentaerythritol tetrakis(3-mercaptopropionate), 2,5-bis(mercaptomethyl)-1,4-dithiane, bimercaptomethyl-1,8-dimercaptomethyl-1,8-dimercaptomethyl-1,9-dithiaoctane, pentaerythritol tetrakis(2-mercaptoacetate), pentaerythritol tetrakis(3-mercaptopropionate), 2,5-bis(mercaptomethyl)-1,4-dithiane, bi ...8-dimercaptomethyl-1,9-dithiaoctane, pentaerythritol tetrakis(2-mercaptoacetate), pentaerythritol tetrakis(3-mercaptopropionate), 2. The polymerizable composition for optical materials according to claim 1, wherein the polymerizable compound is at least one selected from the group consisting of bis(mercaptoethyl)sulfide, 1,1,3,3-tetrakis(mercaptomethylthio)propane, 4,6-bis(mercaptomethylthio)-1,3-dithiane, 2-(2,2-bis(mercaptomethylthio)ethyl)-1,3-dithietane, 1,1,2,2-tetrakis(mercaptomethylthio)ethane, 3-mercaptomethyl-1,5-dimercapto-2,4-dithiapentane, tris(mercaptomethylthio)methane, and ethylene glycol bis(3-mercaptopropionate).

10. 2. The polymerizable composition for an optical material according to claim 1, wherein the ultraviolet absorber (C) is contained in an amount of 0.1 to 10.0 parts by mass per 100 parts by mass of the polymerizable composition for an optical material.

11. The polymerizable composition for an optical material according to claim 10, wherein the ultraviolet absorber (C) is contained in an amount of 0.1 to 2.0 parts by mass per 100 parts by mass of the polymerizable composition for an optical material.

12. 3. The polymerizable composition for an optical material according to claim 2, wherein the ultraviolet absorber (C) is contained in an amount of 0.1 to 3.0% by weight based on a total weight of 100% by weight of the compound (D) having a cyclic structure containing a sulfur atom and the polythiol (B) contained as necessary.

13. A cured product of the polymerizable composition for an optical material according to claim 1 .

14. 3. The cured product of the polymerizable composition for optical materials according to claim 2, which contains 0.1 to 3.0% by weight of an ultraviolet absorber (C).

15. A plastic lens comprising the cured product according to claim 13 or 14.

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