Episulfide compounds, resin compositions containing the same, and optical materials obtained by polymerizing and curing the resin composition.

Abstract

According to the present invention, an episulfide compound represented by the following formula (1) can be provided. [Formula 1] TIFF0007848949000027.tif50143(R1 and R2 each independently represent a group selected from the group consisting of hydrogen atoms, phenyl groups, naphthyl groups, alkyl groups, and halogen atoms. n and m each independently represent an integer from 0 to 5.) In particular, a configuration in which R1 and R2 represent groups selected from the group consisting of a hydrogen atom, a phenyl group, and a naphthyl group, and n and m represent 1, is preferred.

Description

Technical Field

[0001] The present invention relates to an episulfide compound, a resin composition containing the same, and an optical material obtained by polymerizing and curing the resin composition.

Background Art

[0002] Conventionally, curable compositions that can be cured into an arbitrary shape have been used in a wide range of industrial fields such as electric and electronic, OA equipment, heavy electrical machinery, precision machinery, and automotive fields. In particular, resin materials are lightweight, rich in toughness, and easy to process, and thus have been increasingly used in various optical members, especially lenses in recent years. Further, in recent years, optical devices such as cameras mounted on mobile products typified by mobile phones, smartphones, tablet terminals, mobile computers, etc. have made remarkable progress in miniaturization, weight reduction, and high performance. Along with this, there is an increasing demand for lenses used in these optical devices to be miniaturized, weight-reduced, and thinned.

[0003] When a cured product obtained by curing a curable composition is used as an optical member, various properties are required depending on its use. For example, when the cured product is used as an optical lens, in addition to having a desired refractive index and Abbe number, heat resistance, transparency, low water absorption, chemical resistance, low birefringence, moisture resistance, etc. may be required depending on the use of the optical lens. Further, it may also be required that the curable composition has a viscosity suitable for molding. Many studies have been made to develop curable compositions excellent in these properties. In recent years, due to the progress of technologies as described above, curable compositions capable of producing optical members having a high refractive index have been particularly demanded. For example, in the case of an optical lens, when the refractive index is high, a lens element having the same refractive index can be realized with a surface having a smaller curvature, and thus the amount of aberration generated on this surface can be reduced. As a result, it becomes possible to reduce the number of lenses, reduce the decentration sensitivity of the lenses, and reduce the lens thickness to reduce the weight. Further, in order to transfer the lens shape with high precision during lens molding, a resin composition having a low curing shrinkage rate may be required.

[0004] The epoxy resin described in Patent Document 1 is excellent in that it has a low curing shrinkage rate, but it has the problem that its refractive index is about 1.6 and the curable composition has high viscosity. On the other hand, the episulfide described in Patent Document 2 has a refractive index of 1.7 or higher and low viscosity, but it has the problem that it has a high curing shrinkage rate. [Prior art documents] [Patent Documents]

[0005] [Patent Document 1] Patent No. 6700369 [Patent Document 2] Patent No. 4639418 [Overview of the project] [Problems that the invention aims to solve]

[0006] The present invention aims to provide a resin composition with a low curing shrinkage rate, a high refractive index, and relatively low viscosity, as well as an optical material obtained by polymerizing and curing the same. [Means for solving the problem]

[0007] The inventors of the present invention have diligently studied and found that the above problems can be solved by the present invention described below. In other words, the present invention is as follows: <1> It is an episulfide compound represented by the following formula (1). [ka] (R1 and R2 each independently represent a group selected from the group consisting of hydrogen atoms, phenyl groups, naphthyl groups, alkyl groups, and halogen atoms. n and m each independently represent an integer from 0 to 5.) <2> The above equation (1) is the following equation (2), <1> It is an episulfide compound as described in [reference]. [ka] (R1, R2, n, and m are equivalent to those in equation (1).) <3> R1 and R2 represent groups selected from the group consisting of a hydrogen atom, a phenyl group, and a naphthyl group, and n and m represent 1, as described above. <1> or <2> It is an episulfide compound as described in [reference]. <4> the above <1> from <3> This is a resin composition containing an episulfide compound as described in any of the above. <5> the above <4> This optical material is obtained by polymerizing and curing the resin composition described above. <6> the above <5> This is an optical lens containing the optical materials described above. <7> It is an epoxy compound represented by the following formula (3). [ka] <8> the above <7> This is a resin composition containing the epoxy compound described above. <9> the above <8> This optical material is obtained by polymerizing and curing the resin composition described above. <10> the above <9> This is an optical lens containing the optical materials described above. [Effects of the Invention]

[0008] According to the present invention, it is possible to provide a resin composition with a low curing shrinkage rate, a high refractive index, and relatively low viscosity, as well as an optical material obtained by polymerizing and curing the same. [Brief explanation of the drawing]

[0009] [Figure 1] Figure 1 is a chart of the 1H-NMR spectra of the epoxy compound obtained in Example 1. [Figure 2] Figure 2 is a chart of the 1H-NMR spectra of the episulfide compounds obtained in Example 2. [Figure 3] Figure 3 is a chart of the 1H-NMR spectra of the episulfide compounds obtained in Example 3. [Figure 4] Figure 4 is a chart of the 1H-NMR spectra of the episulfide compounds obtained in Example 4. [Figure 5] Figure 5 is a chart of the 1H-NMR spectrum of the episulfide compound obtained in Example 5. [Figure 6] Figure 6 is a chart of the 1H-NMR spectrum of the episulfide compound obtained in Comparative Example 1.

Mode for Carrying Out the Invention

[0010] Hereinafter, embodiments of the present invention will be described in detail. The present inventors have found that a resin composition containing the episulfide compound represented by the above formula (1) and a cured product obtained by curing the same have physical properties particularly preferable for optical materials. According to the episulfide compound represented by the above formula (1), a resin composition and a cured product thereof having solubility, viscosity, refractive index, and curing shrinkage rate in a suitable range are obtained as compared with the conventionally used low molecular weight episulfide compound and the episulfide compound having a fluorene skeleton. Generally, when the refractive index of an optical material is high, a lens element having the same refractive index can be realized with a surface having a smaller curvature, so that the amount of aberration generated on this surface can be reduced. As a result, it becomes possible to reduce the number of lenses, reduce the decentration sensitivity of the lenses, and reduce the lens thickness to reduce the weight. In addition, since the resin composition has an appropriate viscosity and a small curing shrinkage rate, it has excellent moldability, so that it becomes possible to manufacture small and more complex-shaped members. In addition, although a compound having such properties generally has a large molecular weight and low solubility, the episulfide compound represented by the formula (1) has high solubility and does not cause problems such as precipitation and cloudiness of the resin composition. Thus, it can be said that the resin composition according to the embodiment of the present invention has preferable characteristics for an optical material in a well-balanced manner.

[0011] The episulfide compound of the present invention is represented by the following formula (1).

Chemical formula

[0012] A preferred embodiment of the present invention is an episulfide compound represented by the following formula (2). [ka] In equation (2) above, R1, R2, n, and m are equivalent to those in equation (1) above.

[0013] The episulfide compounds of the present invention are synthesized by reacting an aromatic diol compound with an epihalohydrin, such as epichlorohydrin, in the presence of an alkali to produce an epoxy compound represented by the following formula (4). [ka] (R1 and R2 each independently represent a group selected from the group consisting of hydrogen atoms, phenyl groups, naphthyl groups, alkyl groups, and halogen atoms. n and m each independently represent an integer from 0 to 5.) The epoxy compound can then be produced by reacting it with a thiatting agent such as a thiocyanate, thiourea, triphenylphosphine sulfide, or 3-methylbenzothiazole-2-thion, preferably with a thiocyanate or thiourea.

[0014] Among these, the epoxy compound represented by formula (3) below is one of the preferred embodiments. [ka]

[0015] In the method for producing the epoxy compound represented by formula (4) above, the preferred epihalohydrin compound is epichlorohydrin. Furthermore, while stoichiometrically, twice the molar amount of the aromatic diol compound is used for the epihalohydrin compound, less or more may be used if the purity of the product, reaction rate, and cost-effectiveness are important. Preferably, 2 to 20 times the molar amount is used for the reaction. The reaction can be carried out either without a solvent or in a solvent, but if a solvent is used, it is desirable to use one that is soluble in the aromatic diol compound. Specific examples include alcohols, ethyl compounds, aromatic hydrocarbons, and halogenated hydrocarbons. The reaction proceeds readily in the presence of more than stoichiometric amounts of base. That is, it can proceed in the presence of more than twice the molar amount of base relative to the aromatic diol compound.

[0016] Examples of bases include pyridine, triethylamine, tertiary amines such as diazabicycloundecene, and hydroxides of alkali or alkaline earth metals. Preferably, alkali or alkaline earth metal hydroxides are preferred, and more preferably, sodium hydroxide, potassium hydroxide, etc.

[0017] The reaction temperature is usually carried out at -10 to 100°C, but preferably at 20 to 70°C. The reaction time can be any time required for the reaction to be completed under the above conditions, but usually 10 hours or less is appropriate.

[0018] In a method for producing an episulfide compound represented by formula (1) from an epoxy compound represented by formula (4) above, when a thiocyanate is used as a thiatting agent, preferred thiocyanates are salts of amines, alkalis, or alkaline earth metals, and more preferably potassium thiocyanate and sodium thiocyanate. It is also preferable to use thiourea as a thiatting agent. Stoichiometrically, 2 times the molar amount of the epoxy compound represented by formula (4) above is used for thiourea or thiocyanate, but if the purity of the product, reaction rate, economy, etc. are important, less or more than this amount may be used. Preferably, 2 to 10 times the molar amount, more preferably 2 to 5 times the molar amount, is used for the reaction.

[0019] The reaction may be carried out either without a solvent or in a solvent, but if a solvent is used, it is preferable to use one that is soluble in thiocyanates, thioureas, or epoxy compounds represented by formula (4) above. Specific examples include water, methanol, ethanol, isopropanol, and other alcohols; ethers such as diethyl ether, tetrahydrofuran, and dioxane; hydroxyethers such as methyl cellsolve, ethyl cellsolve, and butyl cellsolve; aromatic hydrocarbons such as benzene, toluene, and xylene; and halogenated hydrocarbons such as dichloroethane, chloroform, and chlorobenzene. The combined use of these, for example, with ethers, hydroxyethers, halogenated hydrocarbons, or aromatic hydrocarbons and alcohols, is effective.

[0020] Furthermore, adding acids and acid anhydrides to the reaction solution as polymerization inhibitors is an effective way to improve reaction performance. Specific examples of acids and acid anhydrides include nitric acid, hydrochloric acid, sulfuric acid, fuming sulfuric acid, boric acid, arsenic acid, phosphoric acid, hydrocyanic acid, acetic acid, peracetic acid, thioacetic acid, oxalic acid, tartaric acid, propionic acid, butyric acid, succinic acid, maleic acid, benzoic acid, nitric anhydride, sulfuric acid anhydride, boron oxide, arsenic pentoxide, phosphorus pentoxide, chromic anhydride, acetic anhydride, propionic anhydride, butyric anhydride, succinic anhydride, maleic anhydride, benzoic anhydride, phthalic anhydride, silica gel, silica alumina, aluminum chloride, etc., and it is also possible to use some of these in combination. The amount added is usually 0.001 to 10% by mass relative to the total volume of the reaction solution.

[0021] The reaction temperature is usually 0 to 100°C, but preferably 20 to 70°C. The reaction time can be any time required for the reaction to be completed under the above conditions, but typically 1 to 50 hours is appropriate, and 5 to 30 hours is more preferable. The stability of the resulting compounds can be improved by washing the reaction products with an acidic aqueous solution. Specific examples of acids that can be used in the acidic aqueous solution include nitric acid, hydrochloric acid, sulfuric acid, boric acid, arsenic acid, phosphoric acid, hydrocyanic acid, acetic acid, peracetic acid, thioacetic acid, oxalic acid, tartaric acid, succinic acid, and maleic acid. These can be used individually or in mixtures of two or more. While aqueous solutions of these acids are usually effective at a pH of 6 or below, they are more effective at a pH of 3 or below.

[0022] The episulfide compound of the present invention or a resin composition containing the episulfide compound can be subjected to thermal polymerization in or out of the presence of a curing catalyst to produce cured products such as optical materials. A preferred method is one using a curing catalyst, and suitable curing catalysts include amines, phosphines, mineral acids, Lewis acids, organic acids, silicic acids, tetrafluoroboric acid, and the like. Specific examples include: (1) Ethylamine, n-propylamine, sec-propylamine, n-butylamine, sec-butylamine, i-butylamine, t-butylamine, pentylamine, hexylamine, heptylamine, octylamine, decylamine, laurylamine, mystyrylamine, 1,2-dimethylhexylamine, 3-pentylamine, 2-ethylhexylamine, allylamine, aminoethanol, 1-aminopropanol, 2-aminopropanol, aminobutanol, aminopentanol, aminohexanol, 3-ethoxypropylamine, 3 Primary amines such as -propoxypropylamine, 3-isopropoxypropylamine, 3-butoxypropylamine, 3-isobutoxypropylamine, 3-(2-ethylhexyloxy)propylamine, aminocyclopentane, aminocyclohexane, aminonorbornene, aminomethylcyclohexane, aminobenzene, benzylamine, phenethylamine, α-phenylethylamine, naphthylamine, furfurylamine, etc.; ethylenediamine, 1,2-diaminopropane, 1,3-diaminopropane, 1,2-diaminobutane, 1,3-diaminobutane 1,4-diaminobutane, 1,5-diaminopentane, 1,6-diaminohexane, 1,7-diaminoheptane, 1,8-diaminooctane, dimethylaminopropylamine, diethylaminopropylamine, bis-(3-aminopropyl) ether, 1,2-bis-(3-aminopropoxy)ethane, 1,3-bis-(3-aminopropoxy)-2,2'-dimethylpropane, aminoethylethanolamine, 1,2-, 1,3- or 1,4-bisaminocyclohexane, 1,3- or 1,4-bisaminomethylcyclohexane, 1,3- Or 1,4-bisaminoethylcyclohexane, 1,3- or 1,4-bisaminopropylcyclohexane, hydrogenated 4,4'-diaminodiphenylmethane, 2- or 4-aminopiperidine, 2- or 4-aminomethylpiperidine, 2- or 4-aminoethylpiperidine, N-aminoethylpiperidine, N-aminopropylpiperidine, N-aminoethylmorpholine, N-aminopropylmorpholine, isophoronediamine, menthanediamine, 1,4-bisaminopropylpiperazine, o-, m-, or p-phenylenediamine, 2,4- or 2,6-tolylenediamine, 2,4-toluenediamine, m-aminobenzylamine, 4-chloro-o-phenylenediamine, tetrachloro-p-xylylenediamine, 4-methoxy-6-methyl-m-phenylenediamine, m- or p-xylylenediamine, 1,5- or 2,6-naphthalenediamine, benzidine, 4,4'-bis(o-toluidine), dianisidine, 4,4'-diaminodiphenylmethane, 2,2-(4,4'-diaminodiphenyl)propane, 4,4'-diaminodiphenyl ether, 4,4'-thiodia Dilin, 4,4'-diaminodiphenylsulfone, 4,4'-diaminoditolylsulfone, methylenebis(o-chloroaniline), 3,9-bis(3-aminopropyl)2,4,8,10-tetraoxaspiro[5,5]undecane, diethylenetriamine, iminobispropylamine, methyliminobispropylamine, bis(hexamethylene)triamine, triethylenetetramine, tetraethylenepentamine, pentaethylenehexamine, N-aminoethylpiperazine, N-aminopropylpiperazine, 1,4-bis(aminoethylpiperazine), 1 Primary polyamines such as 4-bis(aminopropylpiperazine), 2,6-diaminopyridine, and bis(3,4-diaminophenyl)sulfone; diethylamine, dipropylamine, di-n-butylamine, di-sec-butylamine, diisobutylamine, di-n-pentylamine, di-3-pentylamine, dihexylamine, octylamine, di(2-ethylhexyl)amine, methylhexylamine, diallylamine, pyrrolidine, piperidine, 2-, 3-, 4-picoline, 2,4-, 2,6-, 3,5-lupetidine, diphenylamine, N-methyl Secondary amines such as dilin, N-ethylaniline, dibenzylamine, methylbenzylamine, dinaphthylamine, pyrrole, indoline, indole, morpholine, etc.; N,N'-dimethylethylenediamine, N,N'-dimethyl-1,2-diaminopropane, N,N'-dimethyl-1,3-diaminopropane, N,N'-dimethyl-1,2-diaminobutane, N,N'-dimethyl-1,3-diaminobutane, N,N'-dimethyl-1,4-diaminobutane, N,N'-dimethyl-1,5-diaminopentane, N,N'-dimethyl-1,6-diaminohexane, N,N'-dimethyl-1,7-diaminoheptane, N,N'-diethylethylenediamine, N,N'-diethyl-1,2-diaminopropane, N,N'-diethyl-1,3-diaminopropane, N,N'-diethyl-1,2-diaminobutane, N,N'-diethyl-1,3-diaminobutane, N,N'-diethyl-1,4-diaminobutane, N,N'-diethyl-1,6-diaminohexane, piperazine, 2-methylpiperazine, 2,5-or 2,6-dimethylpiperazine, homopiperazine, 1,1-di-(4-piperidyl)methane, 1,2- Secondary polyamines such as di-(4-piperidyl)ethane, 1,3-di-(4-piperidyl)propane, 1,4-di-(4-piperidyl)butane, tetramethylguanidine; trimethylamine, triethylamine, tri-n-propylamine, tri-iso-propylamine, tri-1,2-dimethylpropylamine, tri-3-methoxypropylamine, tri-n-butylamine, tri-iso-butylamine, tri-sec-butylamine, tri-pentylamine, tri-3-pentylamine, tri-n-hexylamine, tri-n-octylamine N, tri-2-ethylhexylamine, tri-dodecylamine, tri-laurylamine, tricyclohexylamine, N,N-dimethylhexylamine, N-methyldihexylamine, N,N-dimethylcyclohexylamine, N-methyldicyclohexylamine, triethanolamine, tribenzylamine, N,N-dimethylbenzylamine, diethylbenzylamine, triphenylamine, N,N-dimethylamino-p-cresol, N,N-dimethylaminomethylphenol, 2-(N,N-dimethylaminomethyl)phenol, N, Tertiary amines such as N-dimethylaniline, N,N-diethylaniline, pyridine, quinoline, N-methylmorpholine, N-methylpiperidine, 2-(2-dimethylaminoethoxy)-4-methyl-1,3,2-dioxabornane; tetramethylethylenediamine, pyrazine, N,N'-dimethylpiperazine, N,N'-bis((2-hydroxy)propyl)piperazine, hexamethylenetetramine, N,N,N',N'-tetramethyl-1,3-butanamine, 2-dimethylamino-2-hydroxypropane, diethylaminoethanol, N,N,Tertiary polyamines such as N-tris(3-dimethylaminopropyl)amine, 2,4,6-tris(N,N-dimethylaminomethyl)phenol, and heptamethylisobiguanide; imidazole, N-methylimidazole, 2-methylimidazole, 4-methylimidazole, N-ethylimidazole, 2-ethylimidazole, 4-ethylimidazole, N-butylimidazole, 2-butylimidazole, N-undecylimidazole, 2-undecylimidazole, N-phenylimidazole, 2-phenylimidazole, N-benzylimidazole, 2-benzylimidazole, and 1-benzyl-2-methylimidazole Various imidazoles such as N-(2'-cyanoethyl)-2-methylimidazole, N-(2'-cyanoethyl)-2-undecylimidazole, N-(2'-cyanoethyl)-2-phenylimidazole, 3,3-bis-(2-ethyl-4-methylimidazolyl)methane, adducts of alkylimidazole and isocyanuric acid, and condensates of alkylimidazole and formaldehyde; amidines such as 1,8-diazabicyclo(5,4,0)undecene-7, 1,5-diazabicyclo(4,3,0)nonene-5, and 6-dibutylamino-1,8-diazabicyclo(5,4,0)undecene-7; and amine compounds represented above.

[0023] (2) Quaternary ammonium salts of the amines in (1) with halogens, mineral acids, Lewis acids, organic acids, silicic acid, tetrafluoroboric acid, etc. (3) A complex of the amines of (1) with borane and boron trifluoride. (4) Phosphines such as trimethylphosphine, triethylphosphine, tri-iso-propylphosphine, tri-n-butylphosphine, tri-n-cyclohexylphosphine, tri-n-octylphosphine, tricyclohexylphosphine, triphenylphosphine, trybenzylphosphine, tris(2-methylphenyl)phosphine, tris(3-methylphenyl)phosphine, tris(4-methylphenyl)phosphine, tris(diethylamino)phosphine, dimethylphenylphosphine, diethylphenylphosphine, dicyclohexylphenylphosphine, diethylphenylphosphine, dicyclohexylphenylphosphine, ethyldiphenylphosphine, diphenylcyclohexylphosphine, chlorodiphenylphosphine, and other phosphines. (5) Mineral acids such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, and carbonic acid, and their semi-esters. (6) Lewis acids, such as boron trifluoride and boron trifluoride etherate. (7) Organic acids, such as carboxylic acids, and their semi-esters. (8) Silicic acid, tetrafluoroboric acid And so on.

[0024] Among these, those preferred for their low discoloration of the cured product are primary monoamines, secondary monoamines, tertiary monoamines, tertiary polyamines, imidazoles, amidines, quaternary ammonium salts, and phosphines. More preferred are secondary monoamines, tertiary monoamines, tertiary polyamines, imidazoles, amidines, quaternary ammonium salts, and phosphines having one or less groups that can react with an episulfide group. These may be used individually or in combination of two or more types.

[0025] The curing catalyst described above is typically used in amounts of 0.0001 to 1.0 mole per mole of episulfide compound, preferably 0.0001 to 0.5 moles, more preferably 0.0001 to less than 0.1 moles, and most preferably 0.0001 to 0.05 moles. If the amount of curing catalyst is greater than this, the refractive index and heat resistance of the cured product will decrease, and discoloration may occur. If the amount is less than this, the curing may not be sufficient, resulting in insufficient heat resistance.

[0026] Furthermore, the episulfide compounds of the present invention can be cured and polymerized with compounds having two or more functional groups that can react with an episulfide group, compounds having one or more of these functional groups and one or more other homopolymerizable functional groups, and compounds having one functional group that can react with an episulfide group and is also homopolymerizable, in order to produce optical materials. Examples of compounds having two or more functional groups that can react with an episulfide group include epoxy compounds, known episulfide compounds, polycarboxylic acids, polycarboxylic acid anhydrides, mercaptocarboxylic acids, polymercaptans, mercapto alcohols, mercaptophenols, polyphenols, amines, amides, and the like. On the other hand, examples of compounds having one or more functional groups that can react with an episulfide group and one or more other homopolymerizable functional groups include epoxy compounds having unsaturated groups such as vinyl, aromatic vinyl, methacrylic, acrylic, and allyl, episulfide compounds, carboxylic acids, carboxylic acid anhydrides, mercaptocarboxylic acids, mercaptans, phenols, amines, and amides. Specific examples of compounds having two or more functional groups that can react with an episulfide group are shown below.

[0027] Specific examples of epoxy compounds include phenolic epoxy compounds produced by the condensation of polyhydric phenolic compounds such as hydroquinone, catechol, resorcinol, bisphenol A, bisphenol F, bisphenol sulfone, bisphenol ether, bisphenol sulfide, halogenated bisphenol A, and novolac resins with epihalohydrins; ethylene glycol, diethylene glycol, triethylene glycol, polyethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, 1,3-propane Alcohol-based epoxy compounds produced by the condensation of polyhydric alcohol compounds such as benzoyl diol, 1,4-butanediol, 1,6-hexanediol, neopentyl glycol, glycerin, trimethylolpropane trimethacrylate, pentaerythritol, 1,3- and 1,4-cyclohexanediol, 1,3- and 1,4-cyclohexanedimethanol, hydrogenated bisphenol A, bisphenol A ethylene oxide adduct, and bisphenol A propylene oxide adduct with epihalohydrins; adipic acid, sebatic acid, dodecandyl Glycidyl ester epoxy compounds produced by the condensation of polycarboxylic acid compounds such as carboxylic acids, dimer acids, phthalic acids, iso, terephthalic acid, tetrahydrophthalic acid, methyltetrahydrophthalic acid, hexahydrophthalic acid, hetic acid, nadic acid, maleic acid, succinic acid, fumaric acid, trimellitic acid, benzenetetracarboxylic acid, benzophenonetetracarboxylic acid, naphthalenedicarboxylic acid, and diphenyldicarboxylic acid with epihalohydrins; ethylenediamine, 1,2-diaminopropane, 1,3-diaminopropane, 1,2-diaminobutane, 1,3-diaminobutane, 1,4-diaminobutane, 1,5-diaminopentane, 1,6-diaminohexane, 1,7-diaminoheptane, 1,8-diaminooctane, bis-(3-aminopropyl)ether, 1,2-bis-(3-aminopropoxy)ethane, 1,3-bis-(3-aminopropoxy)-2,2'-dimethylpropane, 1,2-, 1,3- or 1,4-bisaminocyclohexane, 1,3- or 1,4-bisaminomethylcyclohexane, 1,3- or 1,4-bisaminoethylcyclohexane, 1,3- or 1,4-Bisaminopropylcyclohexane, hydrogenated 4,4'-diaminodiphenylmethane, isophoronediamine, 1,4-bisaminopropylpiperazine, m- or p-phenylenediamine, 2,4- or 2,6-tolylenediamine, m- or p-xylylenediamine, 1,5- or 2,6-naphthalenediamine, 4,4'-diaminodiphenylmethane, 4,4'-diaminodiphenyl ether, primary diamines such as 2,2-(4,4'-diaminodiphenyl)propane, N,N'-dimethylethylenediamine, N,N'-dimethyl-1,2-diaminopropane, N,N'-dimethyl-1,3-diaminopropane, N,N'-dimethyl-1,2-diaminobutane, N,N'-dimethyl-1,4 -Diaminobutane, N,N'-dimethyl-1,5-diaminopentane, N,N'-dimethyl-1,6-diaminohexane, N,N'-dimethyl-1,7-diaminoheptane, N,N'-diethylethylenediamine, N,N'-diethyl-1,2-diaminopropane, N,N'-diethyl-1,3-diaminopropane, N,N'-diethyl-1,2-diaminobutane, N,N'-di Ethyl-1,3-diaminobutane, N,N'-diethyl-1,4-diaminobutane, N,N'-diethyl-1,6-diaminohexane, piperazine, 2-methylpiperazine, 2,5-or 2,6-dimethylpiperazine, homopiperazine, 1,1-di-(4-piperidyl)-methane, 1,2-di-(4-piperidyl)-ethane, 1,3-di-(4-piperidyl)-propane, 1,Examples include amine-based epoxy compounds produced by the condensation of secondary diamines such as 4-di-(4-piperidyl)-butane with epihalohydrins; alicyclic epoxy compounds such as 3,4-epoxycyclohexyl-3,4-epoxycyclohexanecarboxylate, vinylcyclihexane dioxide, 2-(3,4-epoxycyclohexyl)-5,5-spiro-3,4-epoxycyclohexane-meth-dioxane, and bis(3,4-epoxycyclohexyl) adipate; epoxy compounds produced by the epoxidation of unsaturated compounds such as cyclopentadiene epoxide, epoxidized soybean oil, epoxidized polybutadiene, and vinylcyclohexene epoxide; and urethane-based epoxy compounds produced from the aforementioned polyhydric alcohols, phenolic compounds, diisocyanates, and glycidol.

[0028] Specific examples of known episulfide compounds include episulfide compounds obtained by episulfidizing some or all of the epoxy groups of the epoxy compounds mentioned above.

[0029] Specific examples of polycarboxylic acids, polycarboxylic acid anhydrides, polyphenols, and amines include those mentioned above as starting materials to react with epihalohydrins, as explained in the section on epoxy compounds.

[0030] Polymercaptans specifically include linear dimercaptan compounds such as 1,2-dimercaptoethane, 1,3-dimercaptopropane, 1,4-dimercaptobutane, 1,6-dimercaptohexane, di(2-mercaptoethyl) sulfide, and 1,2-[bis(2-mercaptoethylthio)]ethane; branched aliphatic polymercaptan compounds such as 2-mercaptomethyl-1,3-dimercaptopropane, 2-mercaptomethyl-1,4-dimercaptobutane, 2-(2-mercaptoethylthio)-1,3-dimercaptopropane, 1,2-bis[(2-mercaptoethylthio)]-3-mercaptopropane, 1,1,1-tris(mercaptomethyl)propane, and tetrakismercaptomethylmethane; ethylene glycol dithioglycolate, ethylene glycol dithiopropionate, and 1,4-butane Examples include ester-containing aliphatic polymer mercaptan compounds such as diol dithioglycolate, 1,4-butanediol dithiopropionate, trimethylolpropanetris (β-thioglycolate), trimethylolpropanetris (β-thiopropionate), pentaerythritol tetrakis (β-thioglycolate), and pentaerythritol tetrakis (β-thiopropionate); and aliphatic cyclic dimercaptan compounds such as 1,4-dimercaptocyclohexane, 1,3-dimercaptocyclohexane, 1,4-dimercaptomethylcyclohexane, 1,3-dimercaptomethylcyclohexane, 2,5-dimercaptomethyl-1,4-dithiane, 2,5-dimercaptoethyl-1,4-dithiane, 2,5-dimercaptomethyl-1-thiane, and 2,5-dimercaptoethyl-1-thiane.

[0031] Furthermore, representative specific examples of compounds having one or more functional groups that can react with an episulfide group and one or more other homopolymerizable functional groups are shown below. Examples of epoxy compounds having an unsaturated group include vinylphenyl glycidyl ether, vinyl benzyl glycidyl ether, glycidyl methacrylate, glycidyl acrylate, and allyl glycidyl ether. Examples of episulfide compounds having an unsaturated group include compounds in which the epoxy group of the above-mentioned epoxy compounds having an unsaturated group has been episulfidized, such as vinylphenyl thioglycidyl ether, vinyl benzyl thioglycidyl ether, thioglycidyl methacrylate, thioglycidyl acrylate, and allyl thioglycidyl ether.

[0032] Examples of carboxylic acid compounds containing unsaturated groups include α,β-unsaturated carboxylic acids such as acrylic acid, methacrylic acid, maleic acid, maleic anhydride, and fumaric acid. Examples of amides containing unsaturated groups include amides of the above-mentioned α,β-unsaturated carboxylic acids.

[0033] Furthermore, preferred specific examples of compounds having one functional group that can react with an episulfide group and can also be homopolymerized include compounds having one epoxy group or one episulfide group. More specifically, examples include monoepoxy compounds such as ethylene oxide and propylene oxide, glycidyl esters of monocarboxylic acids such as acetic acid, propionic acid, and benzoic acid, glycidyl ethers such as methyl glycidyl ether, ethyl glycidyl ether, propyl glycidyl ether, and butyl glycidyl ether, or monoepisulfide compounds such as ethylene sulfide and propylene sulfide, thioglycidyl esters having a structure derived from the above-mentioned monocarboxylic acids and thioglycidol (1,2-epithio-3-hydroxypropane), and thioglycidyl ethers such as methyl thioglycidyl ether (1,2-epithiopropyloxymethane), ethyl thioglycidyl ether, propyl thioglycidyl ether, and butyl thioglycidyl ether. Among these, compounds having one episulfide group are more preferred.

[0034] Compounds having two or more functional groups that can react with an episulfide group, compounds having one or more of these functional groups and one or more other homopolymerizable functional groups, and compounds having one functional group that can react with an episulfide group and is homopolymerizable can be produced by curative polymerization in the presence of a curative polymerization catalyst. Examples of curative catalysts include the aforementioned amines, phosphines, acids, etc. Specific examples of those used here are also mentioned above.

[0035] Furthermore, when using compounds containing unsaturated groups, it is preferable to use radical polymerization initiators as polymerization accelerators. Radical polymerization initiators can be any agents that generate radicals by heating or by ultraviolet light or electron beams, such as cumyl peroxyneodecanoate, diisopropyl peroxydicarbonate, diallyl peroxydicarbonate, di-n-propyl peroxydicarbonate, dimyristil peroxydicarbonate, cumyl peroxyneohexanoate, ter-hexyl peroxyneodecanoate, ter-butyl peroxyneodecanoate, ter-hexyl peroxyneohexanoate, ter-butyl peroxyneohexanoate, 2,4-dichlorobenzoyl peroxide, benzoyl peroxide, dicumyl peroxide, di-ter-butyl peroxide, and other peroxides; cumene hydroperoxide, ter-butyl hydroperoxide Examples of known thermal polymerization catalysts include hydroperoxides such as phosphates; azo compounds such as 2,2'-azobis(4-methoxy-2,4-dimethylvaleronitrile), 2,2'-azobis(2-cyclopropylpropionitrile), 2,2'-azobis(2,4-dimethylvaleronitrile), 2,2'-azobisisobutyronitrile, 2,2'-azobis(2-methylbutyronitrile), 1,1'-azobis(cyclohexane-1-carbonnitrile), 1-[(1-cyano-1-methylethyl)azo]formamide, 2-phenylazo-4-methoxy-2,4-dimethylvaleronitrile, 2,2'-azobis(2-methylpropane), and 2,2'-azobis(2,4,4-trimethylpentane); and known photopolymerization catalysts such as benzophenone, benzoin, and benzoin methyl ether.

[0036] Among these, preferred are peroxides, hydroperoxides, and azo compounds; more preferred are peroxides and azo compounds; and most preferred are azo compounds such as 2,2'-azobis(4-methoxy-2,4-dimethylvaleronitrile), 2,2'-azobis(2-cyclopropylpropionitrile), 2,2'-azobis(2,4-dimethylvaleronitrile), 2,2'-azobisisobutyronitrile, 2,2'-azobis(2-methylbutyronitrile), 1,1'-azobis(cyclohexane-1-carbonitride), 1-[(1-cyano-1-methylethyl)azo]formamide, 2-phenylazo-4-methoxy-2,4-dimethylvaleronitrile, 2,2'-azobis(2-methylpropane), and 2,2'-azobis(2,4,4-trimethylpentane). Furthermore, all of these can be used in combination. The amount of radical polymerization initiator to be added varies depending on the components of the composition and the curing method, so it cannot be determined in general terms, but it is usually in the range of 0.01% to 5.0% by mass, preferably 0.1% to 2.0% by mass, relative to the total amount of the composition.

[0037] Furthermore, when polymerizing and curing the episulfide compound of the present invention or a resin composition containing the episulfide compound to obtain an optical material, it is certainly possible to further improve the practicality of the obtained optical material by adding known additives such as antioxidants and ultraviolet absorbers. It is also possible to improve the release properties of the obtained optical material from the mold by using or adding known external and / or internal release agents. Examples of internal release agents include fluorine-based nonionic surfactants, silicone-based nonionic surfactants, alkyl quaternary ammonium salts, phosphate esters, acidic phosphate esters, alkali metal salts of acidic phosphate esters, metal salts of higher fatty acids, higher fatty acid esters, paraffin, wax, higher aliphatic amides, higher aliphatic alcohols, polysiloxanes, aliphatic amine ethylene oxide adducts, and the like.

[0038] When polymerizing and curing the episulfide compound of the present invention or a resin composition containing the episulfide compound to obtain an optical material, if the raw material is an episulfide compound, and optionally the aforementioned curing catalyst, and reactable with an episulfide group having an unsaturated group, such as glycidyl methacrylate or thioglycidyl methacrylate (glycidyl methacrylate with the epoxy group episulfide modified), then after mixing in additives such as a radical polymerization initiator, a radically polymerizable monomer, and a mold release agent, antioxidant, and ultraviolet absorber, the optical material such as a lens can be manufactured by polymerizing and curing as follows. That is, the mixed raw materials are poured into a glass or metal mold, the polymerization and curing reaction is advanced by heating, and then the material is removed from the mold to manufacture the product.

[0039] The curing time is 0.1 to 100 hours, typically 1 to 48 hours, and the curing temperature is -10 to 160°C, typically -10 to 140°C. Furthermore, after curing, annealing the material at a temperature of 50 to 150°C for 10 minutes to 5 hours is a preferred treatment to remove distortion from the optical material of the present invention. Surface treatments such as hard coating, anti-reflective coating, and anti-fogging treatment can be performed as needed. The method for manufacturing the optical material of the present invention is described in more detail below. As described above, the main raw material and auxiliary raw materials can be mixed and then injected into a mold to cure. The main raw material is an episulfide compound, and optionally a compound having two or more functional groups that can react with an episulfide group, or a compound having one or more of these functional groups and one or more other homopolymerizable functional groups, and a compound having one functional group that can react with an episulfide group and is homopolymerizable. Furthermore, optional curing catalysts, radical polymerization initiators, release agents, stabilizers, etc., can all be mixed simultaneously under stirring in the same container, or each raw material can be added and mixed in stages, or several components can be mixed separately and then remixed in the same container.

[0040] When mixing, the set temperature and the time required should basically be such that each component is thoroughly mixed. However, excessive temperature and time are unsuitable as they can cause undesirable reactions between the raw materials and additives, increase viscosity, and make casting difficult. The mixing temperature should be in the range of -10°C to 100°C, with a preferred temperature range of -10°C to 50°C, and a more preferred range of -5°C to 30°C. The mixing time should be from 1 minute to 5 hours, preferably from 5 minutes to 2 hours, more preferably from 5 minutes to 30 minutes, and most preferably from 5 minutes to 15 minutes. Performing a degassing operation under reduced pressure before, during, or after mixing each raw material and additive is a preferred method in that it prevents the generation of bubbles during subsequent casting polymerization curing. The degree of reduced pressure at this time should be from 0.1 mmHg to 700 mmHg, but a preferred range is from 10 mmHg to 300 mmHg. Furthermore, filtering and removing impurities using a microfilter or the like during injection into the mold is preferable in order to further improve the quality of the optical material of the present invention. [Examples]

[0041] The present invention will be described below with reference to examples, but the present invention is not limited in any way to the following examples.

[0042] (Example 1) 3.00 g (0.006 mol) of 2,2'-[(6,6'-diphenyl[1,1'-binaphthalene]-2,2'-diyl)bis(oxy)]di(ethane-1-ol), represented by the following structural formula, was charged into a 100 mL glass reaction vessel equipped with a stirrer, condenser, and thermometer, and the reaction vessel was purged with nitrogen at room temperature. 5.27 g (0.057 mol) of epichlorohydrin and 0.06 g (0.001 mol) of tetramethylammonium chloride were then added. The temperature was then raised to 55°C, and 0.68 g (0.017 mol) of granular sodium hydroxide was added in installments over 15 minutes, and the mixture was stirred at the same temperature for 5 hours. 50 g of ethyl acetate and 50 g of water were added to the resulting reaction mixture, and the aqueous layer was separated and removed. Next, the organic layer was washed several times with water, and the resulting extract was concentrated under reduced pressure. The extract was then purified by silica gel column chromatography (elution solvent: ethyl acetate:n-hexane = 1:1) to obtain 3.10 g of a colorless, viscous liquid (apparent yield 85%). NMR measurement identified the obtained product as an epoxy compound represented by the following structural formula. The epoxy compound obtained in Example 1 1 The H-NMR spectrum chart is shown in Figure 1. [ka] 2,2'-[(6,6'-diphenyl[1,1'-binaphthalene]-2,2'-diyl)bis(oxy)]di(ethane-1-ol) [ka]

[0043] (Example 2) In a 500 mL glass reaction vessel equipped with a stirrer and thermometer, 12.89 g (0.020 mol) of the epoxy compound obtained in Example 1, 29 g of tetrahydrofuran, and 26 g of methanol were charged and stirred at 25°C until dissolved. Then, 6.14 g (0.081 mol) of thiourea and 0.25 g (0.003 mol) of acetic anhydride were added and the mixture was stirred at 25°C for 23 hours. 100 g of 0.5 mol / L sulfuric acid was added to the resulting reaction mixture and stirred. Then, 100 g of ethyl acetate was added and the aqueous layer was separated and removed. The organic layer was then washed several times with water, and the extract obtained by concentrated under reduced pressure was purified by silica gel column (elution solvent: ethyl acetate:n-hexane = 1:3) to obtain 8.17 g of a colorless viscous liquid (apparent yield 60%). By NMR measurement, the obtained product was identified as an episulfide compound represented by the following structural formula. The episulfide compound obtained in Example 2 1 The H-NMR spectrum chart is shown in Figure 2. [ka]

[0044] (Example 3) In a 500 mL glass reaction vessel equipped with a stirrer and thermometer, 20.00 g (0.041 mol) of the epoxy compound represented by the following structural formula, 59 g of tetrahydrofuran, and 53 g of methanol were charged and stirred at 25°C until dissolved. Then, 12.52 g (0.164 mol) of thiourea and 0.50 g (0.005 mol) of acetic anhydride were added and the mixture was stirred at 25°C for 23 hours. 100 g of 0.5 mol / L sulfuric acid was added to the resulting reaction mixture and stirred. Subsequently, 100 g of ethyl acetate was added and the aqueous layer was separated and removed. The organic layer was then washed several times with water, and the extract obtained by concentrated under reduced pressure was purified by silica gel column (elution solvent: ethyl acetate:n-hexane = 1:3) to obtain 15.80 g of a colorless viscous liquid (apparent yield 74%). NMR measurement identified the obtained product as an episulfide compound represented by the following structural formula. The episulfide compound obtained in Example 3 1The H-NMR spectrum chart is shown in Figure 3. [ka] [ka]

[0045] (Example 4) In a 500 mL glass reaction vessel equipped with a stirrer and thermometer, 10.00 g (0.014 mol) of the epoxy compound represented by the following structural formula, 190 g of tetrahydrofuran, and 112 g of methanol were charged and stirred at 25°C until dissolved. Then, 16.48 g (0.217 mol) of thiourea and 0.17 g (0.002 mol) of acetic anhydride were added and the mixture was stirred at 25°C for 48 hours. 200 g of 0.5 mol / L sulfuric acid was added to the resulting reaction mixture and stirred. Subsequently, 200 g of toluene was added and the aqueous layer was separated and removed. The organic layer was then washed several times with water, and the extract obtained by concentrated under reduced pressure was purified by silica gel column (elution solvent: ethyl acetate:n-hexane = 1:3) to obtain 5.22 g of a white solid (apparent yield 50%). NMR measurement identified the obtained product as an episulfide compound represented by the following structural formula. The episulfide compound obtained in Example 4 1 The H-NMR spectrum chart is shown in Figure 4. [ka] [ka]

[0046] (Example 5) In a 500 mL glass reaction vessel equipped with a stirrer and thermometer, 20.00 g (0.041 mol) of the epoxy compound represented by the following structural formula, 59 g of tetrahydrofuran, and 53 g of methanol were charged and stirred at 25°C until dissolved. Then, 12.52 g (0.164 mol) of thiourea and 0.50 g (0.005 mol) of acetic anhydride were added and the mixture was stirred at 25°C for 23 hours. 100 g of 0.5 mol / L sulfuric acid was added to the resulting reaction mixture and stirred. Subsequently, 200 g of toluene was added and the aqueous layer was separated and removed. The organic layer was then washed several times with water, and the extract obtained by concentrated under reduced pressure was purified by silica gel column (elution solvent: ethyl acetate:n-hexane = 1:20) to obtain 3.42 g of a colorless viscous liquid (apparent yield 26%). NMR measurement identified the obtained product as an episulfide compound represented by the following structural formula. The episulfide compound obtained in Example 5 1 The H-NMR spectrum chart is shown in Figure 5. [ka] [ka]

[0047] (Comparative Example 1) In a 500 mL glass reaction vessel equipped with a stirrer and thermometer, 10.00 g (0.022 mol) of the epoxy compound represented by the following structural formula, 143 g of tetrahydrofuran, and 143 g of methanol were charged and stirred at 25°C until dissolved. Then, 13.69 g (0.086 mol) of thiourea and 0.26 g (0.003 mol) of acetic anhydride were added and the mixture was stirred at 25°C for 23 hours. 100 g of 0.5 mol / L sulfuric acid was added to the resulting reaction mixture and stirred. Subsequently, 100 g of ethyl acetate was added and the aqueous layer was separated and removed. The organic layer was then washed several times with water, and the extract obtained by concentrated under reduced pressure was purified by silica gel column (elution solvent: ethyl acetate:n-hexane = 1:3) to obtain 7.61 g of a white solid (apparent yield 71%). NMR measurement identified the obtained product as an episulfide compound represented by the following structural formula. The episulfide compound obtained in Comparative Example 1 1 The H-NMR spectrum chart is shown in Figure 6. [ka] [ka]

[0048] (Examples 6-9, Comparative Examples 2-4) A curable resin composition was obtained by mixing and stirring the components shown in Table 1 in predetermined ratios until uniform, and then evaporating and distilling off the solvent. The units of the components in Table 1 are expressed in parts by mass. A curable resin composition was sandwiched between two opposing glass plates separated by a 0.25 mm thick spacer. The composition was heated and cured under the following conditions: the temperature was increased from 30°C to 100°C over 10 hours, then from 100°C to 150°C over 1 hour, held at 150°C for 1 hour, and finally cooled from 150°C to 30°C over 1 hour. The glass plates were then removed to obtain the cured resin product. The physical properties of the obtained cured resin product were evaluated.

[0049] <Temporal stability of the liquid> The prepared curable resin compositions were stored at 25°C for one week, and their appearance was visually inspected for any changes such as crystal precipitation or solid sedimentation. The long-term stability of the liquid was then evaluated according to the following criteria. Criteria for evaluating the long-term stability of liquids ○: There was no change in appearance, and it remained transparent. ×: Crystal precipitation and solid sedimentation were observed.

[0050] <Viscosity (mPa s)> The viscosity was measured at 23°C using an EMS viscometer (product name "EMS-1000S," manufactured by Kyoto Electronics Manufacturing Co., Ltd.).

[0051] <Refractive index, Abbe number> The refractive index (nd) and Abbe number (νd) were measured using a refractometer (product name "KPR-3000", manufactured by Shimadzu Corporation). The measurement temperature was 25°C.

[0052] <Hardening shrinkage rate> The curing shrinkage rate was calculated using the following formula. Curing shrinkage rate (%) = (Specific gravity of cured product - Specific gravity of monomer) ÷ Specific gravity of cured product × 100 The specific gravity of the cured material was measured using an electronic hydrometer (product name "ELECTRONIC DENSIMETER ED-120T," manufactured by ALFA MiRAGE Co., Ltd.). The specific gravity of the monomer was measured using a density hydrometer (product name "DA-130N," manufactured by Kyoto Electronics Manufacturing Co., Ltd.). In both cases, the measurement temperature was 25°C.

[0053] [Table 1] A1: Bis(2,3-epithiopropyl) sulfide [ka] B1: Episulfide compound obtained in Example 2 B2: Episulfide compound obtained in Example 3 B3: Episulfide compound obtained in Comparative Example 1 C1: Tetra-n-butylphosphonium bromide [ka]

[0054] (Examples 10-14) When the physical properties of the epoxy compound (DPBN-EEP) obtained in Example 1 were investigated, it was found to be a liquid despite having a high refractive index of nd > 1.6. This is in comparison to the compounds (BN-EEP and DNBN-EEP) below, which are both solids, indicating that the novel epoxy compound obtained in Example 1 is extremely useful. [ka]

[0055] Table 2 shows the results of measuring the physical properties of the epoxy compound (DPBN-EEP) obtained in Example 1, which were then prepared as shown in Table 2. Specifically, the curable resin composition was obtained by mixing and stirring the components shown in Table 2 in a predetermined ratio until uniform, and then evaporating and distilling off the solvent. The units of the components in Table 2 are expressed in parts by mass. A curable resin composition is sandwiched between two opposing glass plates separated by a 0.25 mm thick spacer, and irradiated at 50 mW / cm² using a UV-LED light irradiation device 365 (manufactured by Foseon Technology Japan Co., Ltd., peak wavelength 365 nm). 2 The material was cured by repeating the light irradiation for 10 minutes twice. Next, the temperature was raised from 30°C to 140°C in 1 hour, held at 140°C for 4 hours, and then cooled from 140°C to 30°C in 1 hour for annealing. After that, the glass plate was removed to obtain a cured resin product. The physical properties of the obtained cured resin product were evaluated.

[0056] <Temporal stability of the liquid> The prepared curable resin compositions were stored at 25°C for one week, and their appearance was visually inspected for any changes such as crystal precipitation or solid sedimentation. The long-term stability of the liquid was then evaluated according to the following criteria. Criteria for evaluating the long-term stability of liquids ○: There was no change in appearance, and it remained transparent. ×: Crystal precipitation and solid sedimentation were observed.

[0057] <Viscosity (mPa s)> The measurement was taken at 40°C using an EMS viscometer (product name "EMS-1000S", manufactured by Kyoto Electronics Manufacturing Co., Ltd.).

[0058] <Refractive index> The refractive index (nd) was measured using a refractometer (product name "KPR-3000", manufactured by Shimadzu Corporation). The measurement temperature was 25°C. [Table 2] • jER1750: Product name "jER1750", a bisphenol F type epoxy resin manufactured by Mitsubishi Chemical Corporation. • KR-470: Product name "KR-470", a cyclic siloxane tetrafunctional oligomer containing alicyclic epoxy groups, manufactured by Shin-Etsu Chemical Co., Ltd. • X-40-2678: Product name "X-40-2678", a bifunctional oligomer containing alicyclic epoxy groups and containing cyclic siloxane, manufactured by Shin-Etsu Chemical Co., Ltd. • Celoxide 8010: Product name "Celoxide 8010", an alicyclic epoxy resin manufactured by Daicel Corporation. • CPI-210S: Product name "CPI-210S", photoacid generator manufactured by Sunapro Co., Ltd.

Claims

1. An episulfide compound represented by the following formula (1). 【Chemistry 1】 (R １ and R ２ Each of these independently represents a group selected from the group consisting of a hydrogen atom, a phenyl group, a naphthyl group, an alkyl group, and a halogen atom. n and m each independently represent an integer from 0 to 5.

2. The episulfide compound according to claim 1, wherein formula (1) is the following formula (2). 【Chemistry 2】 (R １ , R ２ n and m are equivalent to those in equation (1).

3. R １ and R ２ The episulfide compound according to claim 1, wherein n represents a group selected from the group consisting of a hydrogen atom, a phenyl group, and a naphthyl group, and n and m represent 1.

4. A resin composition containing the episulfide compound according to any one of claims 1 to 3.

5. An optical material obtained by polymerizing and curing the resin composition described in claim 4.

6. An optical lens comprising the optical material described in claim 5.

7. An epoxy compound represented by the following formula (3). 【Transformation 3】

8. A resin composition containing the epoxy compound described in claim 7.

9. An optical material obtained by polymerizing and curing the resin composition described in claim 8.

10. An optical lens comprising the optical material described in claim 9.

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