Novel episulfide compound and optical material composition thereof

Abstract

The present invention relates to a novel organic material field. The episulfide compound having a sulfoxide structure can effectively improve the alkali corrosion resistance of optical material substrates due to the presence of polar groups, thereby increasing the yield of substrates and reducing production costs.

Description

[Technical Field]

[0001] The present invention belongs to the field of novel organic materials and optical materials, and relates to optical materials suitable for use in plastic lenses, prisms, optical fibers, information storage substrates, filters, etc., and more specifically to novel episulfide compounds and optical material compositions thereof. [Background technology]

[0002] With the recent development of optical resin technology, the refractive index of optical resin lenses is expected to continue increasing. Sulfur-containing compounds, particularly polycyclic sulfur compounds, and their compounding techniques have been developed as raw materials for ultra-high refractive index resin lenses. In the optical resin lens manufacturing process, after the primary curing is completed, the mold is released and opened, and the resulting substrate undergoes edge processing and cleaning. The purpose of cleaning is to remove unreacted monomers and crushed solid powders. To ensure effective cleaning, a solution with a certain alkaline concentration must be used and the cleaning temperature must be controlled. During the cleaning process, the resin lens can corrode or burn due to the alkaline concentration and temperature, reducing substrate yield and increasing manufacturing costs. Conventional technology lacks a technical solution to address this issue.

[0003] Therefore, one of the most urgent issues in this field is to provide optical materials with better performance and resistance to alkaline corrosion. Summary of the Invention [Problem to be solved by the invention]

[0004] To fill the gaps in existing technology, the present invention provides a novel episulfide compound and an optical material composition using the same. The episulfide compound has a sulfoxide structure, and the presence of this polar group effectively improves the alkaline corrosion resistance of optical material substrates and reduces the substrate burning rate, thereby improving substrate yield and reducing manufacturing costs. The episulfide compound has the same bifunctional episulfide structure as bis(β-epithiopropyl) sulfide, and the sulfur content is not significantly different, so other performance indicators such as the refractive index of the product are not affected. [Means for solving the problem]

[0005] The specific technical solutions of the present application are as follows: The present inventor first provides an episulfide compound represented by formula (1).

[0006] [ka]

[0007] Methods for preparing the episulfide compound represented by the above formula (1) include, but are not limited to, the following methods: A method in which an epoxy compound represented by formula (3) is reacted with a sulfurizing reagent such as thiourea or thiocyanate under acidic conditions.

[0008] [ka]

[0009] Preferably, the sulfurizing reagent is selected from one or more of thiourea, potassium thiocyanate, ammonium thiocyanate, and sodium thiocyanate, with thiourea being preferred. The molar ratio of the amount of sulfurizing reagent to the epoxy functional group in formula (3) is 1.0 to 3.0, preferably 2.0 to 2.5. A molar ratio of less than 2.0 results in low raw material conversion, while a molar ratio of more than 2.5 results in low selectivity for the product represented by formula (1), both of which are undesirable.

[0010] Acids used in the reaction process include nitric acid, hydrochloric acid, sulfuric acid, boric acid, arsenic acid, arsenous acid, pyroarsenic acid, phosphoric acid, phosphorous acid, hypophosphorous acid, hydrocyanic acid, chromic acid, other inorganic acids, formic acid, acetic acid, peroxyacetic acid, thioacetic acid, oxalic acid, tartaric acid, propionic acid, butyric acid, succinic acid, valeric acid, hexanoic acid, octanoic acid, naphthenic acid, methylmercaptopropionic acid, malonic acid, glutaric acid, adipic acid, cyclohexanecarboxylic acid, thiodipropionic acid, dithiodipropionic acid, maleic acid, benzoic acid, phenylacetic acid, o-toluic acid, m- Organic carboxylic acids such as toluic acid, p-toluic acid, salicylic acid, 2-methoxybenzoic acid, 3-methoxybenzoic acid, benzoylbenzoic acid, phthalic acid, isophthalic acid, terephthalic acid, diphenylglycolic acid, naphthoic acid, acetic anhydride, propionic anhydride, butyric anhydride, succinic anhydride, maleic anhydride, benzoic anhydride, phthalic anhydride, pyromellitic anhydride, trimellitic anhydride, and trifluoroacetic anhydride; mono-, di-, and trimethyl phosphate; mono-, di-, and triethyl phosphate; mono-, di-, and triisobutyl phosphate; Organic phosphorus compounds such as mono-, di-, and trilauryl phosphate esters, phosphites consisting of phosphorous acid, and dialkyl dithiophosphates represented by dimethyl dithiophosphate, phenol, catechol, tert-butylcatechol, 2,6-di-tert-butyl-p-cresol, 2,6-di-tert-butylethylphenol, resorcinol, hydroquinone, phloroglucinol, pyrogallol, p-cresol, ethylphenol, butylphenol, nonylphenol, hydroxyphenylacetic acid, hydroxyphenylpropionic acid, hydroxyphenylacetamide, methyl hydroxyphenylacetate, ethyl hydroxyphenylacetate, p-hydroxyphenylethanol, p-hydroxyphenylethylamine, hydroxybenzaldehyde, phenylphenol, bisphenol A, 2,2'-methylene-bis(4-methyl-6-tert-butylphenol), bisphenol-F, bisphenol-S, α-naphthol, β-naphthol, aminophenol, chlorophenol, 2,4,Phenols such as 6-trichlorophenol, sulfonic acids such as methanesulfonic acid, ethanesulfonic acid, butanesulfonic acid, dodecanesulfonic acid, benzenesulfonic acid, o-toluenesulfonic acid, m-toluenesulfonic acid, p-toluenesulfonic acid, ethylbenzenesulfonic acid, butylbenzenesulfonic acid, dodecylbenzenesulfonic acid, p-phenolsulfonic acid, o-cresolsulfonic acid, aminobenzenesulfonic acid, p-aminobenzenesulfonic acid, 4B-acid, 2,2'-diaminestilbenesulfonic acid, biphenylsulfonic acid, α-naphthalenesulfonic acid, β-naphthalenesulfonic acid, peracid, Lorentz acid, and phenyl J acid. The acids may be used alone or in combination of two or more. Preferred organic carboxylic acids include formic acid, acetic acid, peroxyacetic acid, thioacetic acid, oxalic acid, tartaric acid, propionic acid, butyric acid, succinic acid, valeric acid, hexanoic acid, octanoic acid, naphthenic acid, methylmercaptopropionic acid, malonic acid, glutaric acid, adipic acid, cyclohexanecarboxylic acid, thiodipropionic acid, dithiodipropionic acid, maleic acid, benzoic acid, phenylacetic acid, o-toluic acid, m-toluic acid, p-toluic acid, salicylic acid, 2-methoxybenzoic acid, 3-methoxybenzoic acid, benzoylbenzoic acid, phthalic acid, isophthalic acid, terephthalic acid, diphenylglycolic acid, α-naphthoic acid, β-naphthoic acid, acetic anhydride, propionic anhydride, butyric anhydride, succinic anhydride, maleic anhydride, benzoic anhydride, phthalic anhydride, pyromellitic anhydride, trimellitic anhydride, and trifluoroacetic anhydride.

[0011] More preferred are formic acid, acetic acid, peracetic acid, oxalic acid, tartaric acid, propionic acid, butyric acid, succinic acid, valeric acid, acetic anhydride, propionic anhydride, butyric anhydride, succinic anhydride, maleic anhydride, benzoic anhydride, phthalic anhydride, pyromellitic anhydride, trimellitic anhydride, and trifluoroacetic acid. Acetic acid is most preferred.

[0012] The molar ratio of the amount of acid to the epoxy functional group in formula (3) is 0.001 to 1.0, and more preferably 0.01 to 0.5. If the molar ratio is less than 0.01, the raw material conversion rate is low, and if the molar ratio exceeds 0.5, the selectivity to the episulfide compound represented by formula (1) is low, so either is not preferred.

[0013] The above-mentioned production method preferably uses a solvent. Examples of the reaction solvent include alcohols such as methanol and ethanol, diethyl ether, tetrahydrofuran, dioxane, and other ethers, hydroxyethers such as methyl cellosolve, ethyl cellosolve, and butyl cellosolve, aromatic hydrocarbons such as benzene and toluene, dichloromethane, chloroform, chlorobenzene, and other halogenated hydrocarbons, and water. Preferably, a mixed solvent of one or two solvents selected from the group consisting of methanol, isopropyl alcohol, toluene, and methylene chloride is used. There are no special requirements for the volume of the solvent, as long as it can completely dissolve the sulfurizing reagent.

[0014] The reaction temperature is usually 10 to 60° C., preferably 25 to 40° C. The sulfurizing reagent has poor solubility at temperatures below 10° C., and above 60° C. polymers are produced and side reactions increase.

[0015] After obtaining the episulfide compound, the present invention further provides a composition for optical materials containing a polymer compound mainly composed of a compound represented by formula (1) and a compound represented by formula (2). The compound represented by formula (1) accounts for 0.001 to 6.0% of the total weight of the optical material composition, and more preferably the compound represented by formula (2) accounts for 0.1 to 3%.

[0016] [ka]

[0017] If the content of the compound of formula (1) is less than 0.001%, the alkali resistance is poor, and if it exceeds 6.0%, the impact resistance of the optical material is affected, making subsequent processing and use disadvantageous. Furthermore, when the compound represented by formula (2) is used as the polymerizable compound, the proportion of the compound represented by formula (2) in the optical material composition of the present invention to the total weight of the optical material composition is 50 to 99.999%, more preferably 70 to 99%.

[0018] The polymerizable compound described herein may be present together with a thiol compound and an isocyanate compound in addition to the compound represented by formula (2).

[0019] When the total weight of the composition for optical materials is taken as 100%, the content of the thiol compound is usually 1 to 20%, preferably 3 to 15%, which can improve the heat resistance of the optical material. If the content of the thiol compound is 1% or more, yellowing during lens molding can be suppressed, and if it is 20% or less, a decrease in heat resistance can be prevented. The thiol compounds used in the present invention may be used alone or in combination of two or more.

[0020] Specific candidates for thiol compounds include 2-mercaptoethanol, 3-mercaptopropanol, 2-hydroxypropyl mercaptan, n-hexyl mercaptan, n-octyl mercaptan, bis(2-mercaptoethyl) sulfide, 2,5-dimercaptomethyl-1,4-dithiane, 1,3-bis(mercaptomethyl)benzene, 1,4-bis(mercaptomethyl)benzene, 4-mercaptomethyl-1,8-dimercapto-3,6-dithiooctane, 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithioundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithioundecane, and 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithioundecane. The mercaptomethyl-1,11-dimercapto-3,6,9-trithioundecane is one or more of dimercaptomethyl-1,11-dimercapto-3,6,9-trithioundecane, 1,1,3,3-tetrakis(mercaptomethylthio)propane, pentaerythritol tetramercaptopropionate, pentaerythritol tetrakis(mercaptoacetate), trimethylolpropane tris(thioglycolate), trimethylolpropane trimercaptopropionate, preferably 2-mercaptoethanol, 3-mercaptopropanol, 2-hydroxypropyl mercaptan, bis(2-mercaptoethyl)sulfide, and 4-mercaptomethyl-1,8-dimercapto-3,6-dithiooctane.

[0021] The content of the isocyanate compound is usually 1 to 20%, preferably 3 to 15%, when the total weight of the composition for optical materials is taken as 100%. When the content of the isocyanate compound is 1% or more, the strength of the optical material can be improved, and when it is 20% or less, deterioration in color tone can be suppressed. The isocyanate compound used in the present invention may be used alone or in a mixture of two or more types.

[0022] Preferably, the isocyanate compound contains at least two isocyanate groups, and the isocyanate compound is selected from the group consisting of diethylene diisocyanate, tetramethylene diisocyanate, hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, cyclohexane diisocyanate, 1,3-bis(isocyanatemethyl)cyclohexane, 1,4-bis(isocyanatemethyl)cyclohexane, isophorone diisocyanate, 2,6-bis(isocyanatemethyl)decalin, tolyl diisocyanate, o-toluidine diisocyanate, diphenylmethane diisocyanate, and diphenyl The diisocyanate may be selected from ether diisocyanate, 2,2'-bis(4-isocyanatophenyl)propane, triphenylmethane triisocyanate, bis(diisocyanatotolyl)phenylmethane, 1,3-phenylene diisocyanate, 1,4-phenylene diisocyanate, 4,4'-diisocyanatobiphenyl, dicyclohexylmethane-4,4'-diisocyanate, 1,1'-methylenebis(4-isocyanatobenzene), m-xylyl diisocyanate, p-xylyl diisocyanate, m-tetramethylxylyl diisocyanate, p-tetramethylxylyl diisocyanate, bis(isocyanatomethyl)norbornene, bis(isocyanatomethyl)adamantane, thiodiethyl diisocyanate, thiodipropyl diisocyanate, and thiodihexyl diisocyanate. Preferably, it is selected from isophorone diisocyanate, m-xylyl diisocyanate, and 1,3-bis(isocyanatomethyl)cyclohexane.

[0023] Even if the above-mentioned thiol compound and isocyanate compound are added to the polymer compound mainly composed of the compounds represented by general formula (1) and general formula (2), the alkali corrosion resistance of the final material is not affected.

[0024] Based on the above-mentioned composition for optical materials, the present inventors provide a polymerizable and curable composition containing any one of the above-mentioned combinations of compositions for optical materials and 0.01% to 1% of a polymerization catalyst based on the total weight of the composition for optical materials. As the polymerization catalyst, imidazoles and phosphines can be used, and tetrabutylphosphonium bromide can be used as a more preferred polymerization catalyst.

[0025] The amount of polymerization catalyst added varies depending on the components of the composition, the mixing ratio, and the polymerization and curing method, and cannot be generalized, but is preferably 0.03% to 0.5% based on the total weight of the composition for optical materials. If the amount of polymerization catalyst added exceeds 1%, rapid polymerization may occur, and if the amount of polymerization catalyst added is less than 0.01%, the composition for optical materials may not be cured sufficiently, resulting in a decrease in heat resistance.

[0026] Furthermore, when producing a corresponding optical material, adding additives to the polymerizable and curable composition can further improve the practicality of the resulting optical material. Specifically, the polymerizable and curable composition of the present invention may contain additives such as an ultraviolet absorber, a release agent, a blue agent, and a red agent. The ultraviolet absorber is a benzotriazole compound, particularly preferably 2-(2-hydroxy-tert-octylphenyl)-2H-benzotriazole (UV-329), added in an amount of 0.001% to 1%, more preferably 0.01% to 0.5%, of the total weight of the polymerizable and curable composition. The blue agent and red agent are added depending on the actual needs of the optical material, and there are no particular restrictions on their amounts. The release agent is one or more selected from di-n-butyl phosphate, El310, nonylphenol polyoxyethylene ether phosphate, and Zelec® UN, added in an amount of 0.001% to 1%, more preferably 0.01% to 0.5%, of the total weight of the polymerizable and curable composition.

[0027] The present invention also provides an optical material obtained by curing the above-mentioned polymerizable and curable composition. The specific steps are as follows: a) uniformly mixing the optical material composition to obtain a mixed reaction product; b) injecting the reaction mixture obtained in step a) into a mold through a filter membrane to perform a primary curing. After demolding, edge grinding and multi-tank ultrasonic cleaning are performed. After cleaning is complete, a secondary curing is performed to obtain an optical resin material.

[0028] The temperature program for the first curing described in step b) is to maintain the temperature at an initial temperature of 15-25°C for 2.0-3.5 hours, then heat for 10-15 hours, raise the temperature to 45-60°C, continue heating for 2.0-4.0 hours, raise the temperature to 75-90°C, and finally cool down to 60-75°C over 1.5-2.5 hours. The temperature for the second curing in step b) is 80-110°C, and the time is 2-4 hours.

[0029] The process parameters for the multi-tank ultrasonic cleaning are as follows:

[0030] [Table 1]

[0031] The specific cleaning process and reagents used can refer to the methods and reagents recorded in the existing patent CN104802430B. The optical material obtained above can be used to make optical lenses.

[0032] In summary, compared with the prior art, the episulfide compound obtained in the present application introduces a sulfoxide structure, and the presence of this polar group can effectively improve the alkali corrosion resistance of optical material substrates and reduce substrate burns caused by impurity spots caused by corrosion, thereby improving substrate yield and reducing production costs. [Brief explanation of the drawings]

[0033] [Figure 1] 1 shows a mass spectrum of the novel episulfide compound in Example 1. [Figure 2] 1 is a H NMR spectrum of the novel episulfide compound of Example 1. [Figure 3] 13C NMR spectra of the novel episulfide compound of Example 1. In Figures 2 and 3, H NMR (CDCl) δ = 2.21 ppm (1H), δ = 2.32 ppm (2H), δ = 3.02 ppm (2H); C NMR (CDCl) δ = 24.8 ppm, 28.6 ppm, 63.7 ppm. DETAILED DESCRIPTION OF THE INVENTION

[0034] The above content of the present invention will be specifically explained in the form of examples below, but this does not mean that the scope of the above subject matter of the present invention is limited to the following examples. All techniques implemented based on the above content of the present invention belong to the scope of the present invention, and unless otherwise specified, all raw materials used in the following examples are commercially available products.

[0035] To further explain the present invention, the following examples are described in detail. 1) Scaling rate: Scaling refers to the phenomenon in which impurity spots appear near the center of a substrate during the substrate cleaning process due to the influence of alkali concentration and temperature. In the examples of the present invention, 100 substrates that had been ultrasonically cleaned were visually observed to identify substrates with scaling, and the scalding rate was calculated.

[0036] 2) Yield: Product A has no impurity spots within a 3 cm radius of the center. Product B has no impurity spots within a 1.5 cm radius of the center, but has impurity spots between 1.5 and 3 cm. Product C contains leaf-like impurities within a 1.5 cm radius of the center. Of these, products A and B are acceptable products, while product C is unacceptable. In the examples of the present invention, 100 ultrasonically cleaned substrates were visually observed to determine whether there were impurity spots within different radiuses, and the yield was calculated.

[0037] (Example 1) Method for producing an episulfide compound represented by formula (1):

[0038] [ka]

[0039] 81 g (0.5 mol) of the compound represented by the above formula (3), 500 mL of methanol, 500 mL of toluene, 87.4 g (1.15 mol) of thiourea, and 6 g (0.1 mol) of acetic acid were added and reacted for 12 hours at 30° C. This crude product was separated and purified using a silica gel column in a conventional manner to obtain 48.5 g (0.25 mol) of the episulfide compound represented by the above formula (1).

[0040] [ka]

[0041] The episulfide compound represented by formula (1) was characterized by mass spectrometry and nuclear magnetic resonance spectrometry. The results are shown in Figures 1-3. Mass spectrum (ESI): [M+H] + =194.9972.

[0042] Example 2: 88.4 g of bis(β-epithiopropyl) sulfide, 0.1 g of the episulfide compound represented by formula (1), 5.1 g of isophorone diisocyanate, 6.3 g of mercaptoethanol, 0.1 g of tetrabutylphosphonium bromide, 0.3 g of 2-(2-hydroxy-tert-octylphenyl)-2H-benzotriazole (UV-329), and 0.2 g of di-n-butyl phosphate were mixed and stirred for 50 minutes to obtain a prepolymer liquid. The density ρ before solidification was measured using a liquid densitometer. The prepolymer liquid was vacuum degassed for 30 minutes, filtered through a polytetrafluoroethylene filter membrane with a pore size of 3 μm, and poured into a glass mold. The mold was then placed in a programmable temperature curing oven for primary curing, yielding a primary-cured resin lens. The heating program for primary curing was as follows: After maintaining the initial temperature at 20°C for 2 hours, the temperature was raised to 45°C after 3.5 hours of heating, then raised to 55°C after 3 hours of heating, then raised to 100°C after 6 hours of heating, and held there for 4 hours. The temperature was then lowered over 2 hours to 70°C. The resulting primarily cured resin lens substrate was demolded and subjected to multi-tank ultrasonic cleaning. After visual inspection, the sintering rate and yield were calculated. The process parameters for multi-tank ultrasonic cleaning were as follows:

[0043] [Table 2]

[0044] The specific cleaning process and reagents used can refer to the methods and reagents recorded in the existing patent CN104802430B, in which the alkali concentration is 3% or 6%.

[0045] Example 3 The difference from Example 2 is that 87.5 g of bis(β-epithiopropyl) sulfide and 1.0 g of the episulfide compound represented by formula (1) were added, but the other amounts added and steps were the same as in Example 2.

[0046] Example 4 The difference from Example 2 is that 86.5 g of bis(β-epithiopropyl) sulfide and 2.0 g of the episulfide compound represented by formula (1) were added, but the other amounts added and steps were the same as in Example 2.

[0047] Example 5 The difference from Example 2 is that 85.5 g of bis(β-epithiopropyl) sulfide and 3.0 g of the episulfide compound represented by formula (1) were added, but the other amounts added and steps were the same as in Example 2.

[0048] Example 6 differs from Example 2 in that 88.4 g of bis(β-epithiopropyl) sulfide and 0.1 g of the episulfide compound represented by formula (1) were added, and after primary curing and demolding, the alkali concentration in the multi-tank ultrasonic cleaning was set to 6%. Other additive amounts and processes were the same as in Example 2.

[0049] Example 7 differs from Example 2 in that 87.5 g of bis(β-epithiopropyl) sulfide and 1.0 g of the episulfide compound represented by formula (1) were added, and after primary curing and demolding, the alkali concentration in the multi-tank ultrasonic cleaning was set to 6%. Other additive amounts and processes were the same as in Example 2.

[0050] Example 8 differs from Example 2 in that 86.5 g of bis(β-epithiopropyl) sulfide and 2.0 g of the episulfide compound represented by formula (1) were added, and after primary curing and demolding, the alkali concentration in the multi-tank ultrasonic cleaning was set to 6%. Other additive amounts and processes were the same as in Example 2.

[0051] Example 9 differs from Example 2 in that 85.5 g of bis(β-epithiopropyl) sulfide and 3.0 g of the episulfide compound represented by formula (1) were added, and after primary curing and demolding, the alkali concentration in the multi-tank ultrasonic cleaning was set to 6%. Other additive amounts and processes were the same as in Example 2.

[0052] Comparative Example 1 The difference from Example 2 is that 88.5 g of bis(β-epithiopropyl) sulfide and 0 g of the episulfide compound represented by formula (1) were added, but the other amounts added and steps were the same as in Example 2.

[0053] Comparative Example 2 The difference from Example 2 is that 84.5 g of bis(β-epithiopropyl) sulfide and 4 g of the episulfide compound represented by formula (1) were added, but the other amounts added and steps were the same as in Example 2.

[0054] Comparative Example 3 The difference from Example 2 is that 82.5 g of bis(β-epithiopropyl) sulfide and 6 g of the episulfide compound represented by formula (1) were added, but the other amounts added and the process were the same as in Example 2.

[0055] (Comparative Example 4) The difference from Example 2 is that 88.5 g of bis(β-epithiopropyl) sulfide and 0 g of the episulfide compound represented by formula (1) were added, and after primary curing and demolding, the mixture was washed with alkali in a multi-tank ultrasonic cleaning bath. The other addition amounts and processes were the same as in Example 2.

[0056] Comparative Example 5 differs from Example 2 in that 84.5 g of bis(β-epithiopropyl) sulfide and 4 g of the episulfide compound represented by formula (1) were added, and after primary curing and demolding, the alkali concentration in the multi-tank ultrasonic cleaning was set to 6%. Other additive amounts and processes were the same as in Example 2.

[0057] Comparative Example 6 differs from Example 2 in that 82.5 g of bis(β-epithiopropyl) sulfide and 6 g of the episulfide compound represented by formula (1) were added, and after primary curing and demolding, the alkali concentration in the multi-tank ultrasonic cleaning was set to 6%. Other additive amounts and processes were the same as those in Example 2.

[0058] The sintering rate and yield of the substrate were calculated using the examples and comparative examples, and the specific results are shown in the table below.

[0059] [Table 3]

[0060] In the table, BEPSO is an episulfide compound represented by formula (1). From the results in the table above, when the amount of episulfide compound represented by formula (1) added is 0.1 to 3.0 mass%, the sintering rate of the optical resin material lens is approximately 10%, the substrate yield is >95%, and stability is at its highest. When the amount of episulfide compound represented by formula (1) added exceeds 3%, the sintering rate and yield do not change significantly. When the amount added is 0, the sintering rate exceeds 20%, the yield is less than 90%, and costs increase.

[0061] The above-described embodiments enable those skilled in the art to make or use the present invention. Various modifications to these embodiments will be apparent to those skilled in the art. The general principles defined herein may be implemented in other embodiments without departing from the spirit or scope of the present invention. Thus, the present invention is not intended to be limited to the embodiments shown herein but is to be accorded the widest scope consistent with the principles and novel features disclosed herein.

Claims

1. A novel episulfide compound characterized by being a compound represented by formula (1): 【Chemical 1】

2. A polymerizable compound containing the compound represented by formula (1) and the compound represented by formula (2) as main components, 【Chemistry 2】 The optical material composition is characterized in that the compound represented by formula (1) accounts for 0.001 to 6.0% of the total weight of the composition.

3. Further containing a thiol compound and an isocyanate compound, 3. The composition for optical materials according to claim 2, wherein the compound represented by formula (1) accounts for 0.1 to 3.0% of the total weight of the composition.

4. The composition for optical materials according to claim 2 or 3, wherein the compound represented by formula (2) accounts for 50.0 to 99.999% of the total weight of the composition for optical materials.

5. The composition for optical materials according to claim 4, wherein the compound represented by formula (2) accounts for 70.0 to 99.999% of the total weight of the composition for optical materials.

6. 3. A polymerizable and curable composition comprising the optical material composition according to claim 2 and a polymerization catalyst in an amount of 0.01 to 1% based on the total weight of the optical material composition.

7. 7. The polymerizable and curable composition according to claim 6, wherein the polymerization catalyst is imidazole or phosphine, and the amount of the polymerization catalyst added is 0.03% to 0.5% of the total weight of the composition for optical materials.

8. An optical material obtained by curing the polymerizable and curable composition according to claim 6 or 7.

9. An optical lens produced using the optical material according to claim 8.

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