Compounds, methods of making the same, optical material compositions, cured compositions

Abstract

The present application relates to the technical field of optical material, and specifically provides a compound, a preparation method thereof, an optical material composition and a cured composition.The compound is shown as formula (1). Compared with the prior art, the compound has a dioxane polar structure, enhances the intermolecular force between the compound and a hardening liquid, makes the coating uniform, reduces the occurrence of hardening points, reduces the rework coating process, and improves the production efficiency.Meanwhile, the compound has the same double ring sulfur structure as the bis(beta-cyclopropyl sulfide) thioether compound, so that the compound has no negative effect on other performance indicators of the product.

Description

TECHNICAL FIELD

[0001] The present application relates to the technical field of optical materials, and more particularly to a compound and a preparation method thereof, an optical material composition, and a cured composition. BACKGROUND

[0002] In recent years, with the development of optical resin technology, it has become a goal to continuously improve the refractive index of optical resin lenses in the future. As raw materials for making super-high refractive index resin lenses, sulfur compounds, especially cyclic sulfur compounds and their formulation technology, have been developed. By utilizing the high reactivity of cyclic sulfur groups, various effective components can be added to the composition to improve the physical properties of optical materials.

[0003] In the manufacture of optical resin materials, in order to improve the wear resistance of resin lenses, surface hardening treatment, i.e., hardening, is performed on the substrate obtained after primary curing and secondary curing. A layer of hardening liquid of a certain thickness is coated on the substrate, and pre-curing is performed. After pre-curing, the lenses are inspected one by one, and it is found that the hardened lenses sometimes have abnormal hardening points. These lenses need to be reworked and coated with hardening liquid. SUMMARY

[0004] Therefore, the present application provides a compound and a preparation method thereof, an optical material composition, and a cured composition. The compound of the present application has a dioxane polar structure, which enhances the intermolecular force between the compound and the hardening liquid, makes the coating uniform, reduces the occurrence of hardening points, reduces the reworking and recoating process, and improves the production efficiency.

[0005] To achieve the above-mentioned purpose, the present application adopts the following technical solutions:

[0006] a compound as shown in formula (1),

[0007]

[0008] In formula (1), x = 1 or 2.

[0009] The present application also provides a preparation method of the above-mentioned compound, comprising:

[0010] reacting a compound as shown in formula (2) with a sulfurization reagent to obtain the compound;

[0011]

[0012] In formula (2), x = 1 or 2.

[0013] Preferably, the present application reacts the compound shown in formula (2) with a sulfuration reagent to perform sulfuration, the reaction is carried out under acidic conditions; the reaction temperature is preferably 60-70℃, the reaction time is 12-15h; the molar ratio of the compound shown in formula (2) to the sulfuration reagent is preferably 1:(1-3); the sulfuration reagent is preferably thiourea; the solvent used in the reaction is preferably methanol and / or toluene; after the reaction is completed, the organic layer is washed with water, the solvent is removed by distillation, and the crude product is separated and refined by a silica gel column.

[0014] The present application uses an epoxy compound as a raw material, and reacts with thiourea as a sulfuration reagent, and the reaction process includes the following stages: ring opening of an epoxy group, Walden inversion of a carbon atom ring, substitution of a sulfur atom for an oxygen atom, and finally ring closure of a sulfur ring to obtain a sulfur compound.

[0015] In the present application, the preparation method of the compound shown in formula (2) comprises:

[0016] The compound shown in formula (3) is subjected to a removal reaction under alkaline conditions; the temperature of the removal reaction is 30-40℃, and the reaction time is 4-6h; the alkaline condition is preferably provided by NaOH;

[0017]

[0018] In formula (3), x=1 or 2;

[0019] The preparation method of the compound shown in formula (3) comprises:

[0020]

[0021] The compound shown in formula (4) is reacted with epichlorohydrin to obtain The reaction temperature is preferably 60-70℃, and the reaction time is 2-5h; the molar ratio of the compound shown in formula (4) to epichlorohydrin is preferably 1:(1-2);

[0022] Alternatively, the compound shown in formula (4), an oxidizing agent and 1-chloro-3-mercapto-2-propanol are used to obtain The oxidizing agent is preferably elemental iodine; the molar ratio of the compound shown in formula (4), the oxidizing agent and 1-chloro-3-mercapto-2-propanol is preferably 1:(1-2):(1-2); the reaction temperature is preferably 40-50℃, and the reaction time is 6-8h;

[0023] The preparation method of the compound shown in formula (4) comprises:

[0024] The compound shown in formula (5) is reacted with a sulfuration reagent under acidic conditions to obtain an intermediate, and the intermediate is alkaline hydrolyzed to obtain the compound shown in formula (4); the molar ratio of the compound shown in formula (5) to the sulfuration reagent is preferably 1:(1-3); the sulfuration reagent is preferably thiourea; the reaction time is 12-15 h;

[0025]

[0026] The present application also provides an optical material composition, which comprises the compound shown in formula (1), the compound shown in formula (6) and an optical material base;

[0027]

[0028] In formula (1), x=1 or 2;

[0029]

[0030] In formula (6), m=1 or 2.

[0031] When m=1, the compound shown in formula (6) is bis(β-cyclopropylthio) sulfide; when m=2, the compound shown in formula (6) is bis(β-cyclopropylthio) disulfide.

[0032] The compound shown in formula (1) is added in the optical material, and the phenomenon of hardening point of the optical material can be improved.

[0033] The "hardening point" refers to the phenomenon that white points appear on the surface of the substrate in the process of hardening coating.

[0034] In the optical material composition of the present application, the optical material base further comprises a thiol compound and an isocyanate.

[0035] In the present application, the content of the compound shown in formula (1) in the optical material composition is 0.001-5.0 wt%, preferably 0.1-3 wt%; the content of the compound shown in formula (6) in the optical material composition is 50-99.999 wt%, preferably 70-99 wt%, more preferably 85-90 wt%.

[0036] In the present application, the optical material composition comprises, in parts by weight: 0.001-5 parts of the compound shown in formula (1); 50-99 parts of the compound shown in formula (6); 1-20 parts of a thiol compound; and 1-20 parts of an isocyanate; preferably, the optical material composition comprises: 0.1-3 parts of the compound shown in formula (1); 50-99 parts of the compound shown in formula (6); 1-20 parts of a thiol compound; and 1-20 parts of an isocyanate.

[0037] In the present application, the optical material composition consists of 0.1 to 5 parts of a compound represented by formula (1), 83 to 89 parts of a compound represented by formula (6), 5 to 6 parts of a thiol compound, and 5 to 6 parts of an isocyanate. The optical material composition preferably consists of 0.1 to 3 parts of a compound represented by formula (1), 83 to 89 parts of a compound represented by formula (6), 5 to 6 parts of a thiol compound, and 5 to 6 parts of an isocyanate.

[0038] The optical material composition described above is made into an optical material, and the thiol compound can improve the heat resistance of the optical material. Within the content range described above, the thiol compound can inhibit yellowing during molding of a lens and prevent a decrease in the heat resistance of the optical material.

[0039] In one embodiment of the present application, the optical material composition consists of 0.1 parts of a compound represented by formula (1) (x = 1), 88 parts of a compound represented by formula (6) (m = 1), 5 parts of a thiol compound, and 6 parts of an isocyanate.

[0040] In one embodiment of the present application, the optical material composition consists of 1 parts of a compound represented by formula (1) (x = 1), 88 parts of a compound represented by formula (6) (m = 1), 5 parts of a thiol compound, and 6 parts of an isocyanate.

[0041] In one embodiment of the present application, the optical material composition consists of 2 parts of a compound represented by formula (1) (x = 1), 87 parts of a compound represented by formula (6) (m = 1), 5 parts of a thiol compound, and 6 parts of an isocyanate.

[0042] In one embodiment of the present application, the optical material composition consists of 3 parts of a compound represented by formula (1) (x = 1), 86 parts of a compound represented by formula (6) (m = 1), 5 parts of a thiol compound, and 6 parts of an isocyanate.

[0043] In this invention, the thiol compound is selected from 2-mercaptoethanol, 3-mercaptopropanol, 2-hydroxypropylthiol, n-hexylthiol, n-octylthiol, 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, and 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithioundecane. One or more of 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithioundecane, 1,1,3,3-tetra(mercaptomethylthio)propane, pentaerythritol tetramercaptopropionate, pentaerythritol tetrathioethylene glycol ester, trimethylolpropane trithioethylene glycol ester, thiodiglycol, and trimethylolpropane trimercaptopropionate; preferably one or more of 2-mercaptoethanol, 3-mercaptopropanol, 2-hydroxypropylthiol, bis(2-mercaptoethyl) sulfide, thiodiglycol, and 4-mercaptomethyl-1,8-dimercapto-3,6-dithiooctane.

[0044] In this invention, the isocyanate is a diisocyanate; the diisocyanate contains at least two isocyanate groups, and the isocyanate is preferably diethylidene diisocyanate, tetramethylene diisocyanate, hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, cyclohexane diisocyanate, 1,3-bis(isocyanate methyl)cyclohexane, 1,4-bis(isocyanate methyl)cyclohexane, isophorone diisocyanate, 2,6-bis(isocyanate methyl)decahydronaphthalene, toluene diisocyanate, o-toluidine diisocyanate, diphenylmethane diisocyanate, diphenyl ether diisocyanate, 2,2'-bis(4-isocyanate phenyl)propane, triphenylmethane triisocyanate, or bis(diisocyanate toluene)phenylmethane. One or more of the following: 1,3-phenylene diisocyanate, 1,4-phenylene diisocyanate, 4,4'-diisocyanate-biphenyl, dicyclohexylmethane-4,4'-diisocyanate, 1,1'-methylenebis(4-isocyanate-benzene), m-xylyl diisocyanate, p-xylyl diisocyanate, m-tetramethylxylyl diisocyanate, p-tetramethylxylyl diisocyanate, bis(isocyanate-methyl)norbornene, bis(isocyanate-methyl)adamantane, thiodiethyl diisocyanate, thiodipropyl diisocyanate, and thiodihexyl diisocyanate; more preferably, one or more of the following: isophorone diisocyanate, m-xylyl diisocyanate, and 1,3-bis(isocyanate-methyl)cyclohexane.

[0045] The thiol compounds and isocyanates in the optical material composition of the present invention do not affect the alkali corrosion resistance of the final material.

[0046] In the manufacture of the corresponding optical material, the optical material composition is added with an auxiliary agent, which can further improve the practicability of the obtained optical material.

[0047] In the present application, the optical material composition further comprises an auxiliary agent; the auxiliary agent comprises one or more of ultraviolet absorbers, release agents, blue agents and red agents.

[0048] In the present application, the ultraviolet absorber is selected from benzotriazole compounds, preferably 2-(2-hydroxy-tert-octylphenyl)-2H-benzotriazole, 2-(2-hydroxy-5-tert-octylphenyl)-2H-benzotriazole, and the addition amount is 0.001wt%-1wt% of the total weight of the optical material composition, further preferably 0.01wt%-0.5wt%; the blue agent and the red agent are added according to the actual needs of the optical material, and there is no specific requirement for the addition amount; the release agent is selected from one or more of di-n-butyl phosphate, El310, nonylphenol polyoxyethylene ether phosphate, Zelec UNTM, and is more preferably di-n-butyl phosphate; the addition amount is 0.001wt%-1wt% of the total weight of the optical material composition, further preferably 0.01wt%-0.5wt%.

[0049] The present application also provides a cured composition comprising the above-mentioned optical material composition and a catalyst.

[0050] The optical material can be prepared using the cured composition; the present application does not have special requirements for the preparation method of the optical material, and it can be prepared by using the conventional method of those skilled in the art; preferably, it is prepared by curing the optical material composition comprising the above-mentioned optical material composition and a catalyst; more preferably, it comprises the following steps: a) mixing the compound represented by formula (1), the compound represented by formula (6), a thiol compound, a catalyst and isocyanate to obtain a mixed reaction; b) injecting the reaction mixture obtained in step a) through a filter membrane into a mold to perform the first curing, and after demolding, continuing to perform edge grinding and multi-slot ultrasonic cleaning; after cleaning, performing the second curing to obtain a substrate; c) hardening and plating the substrate obtained in step b).

[0051] Preferably, in step b), the temperature rising procedure of the first curing is: the initial temperature is 15℃-25℃, the temperature is kept for 2.0h-3.5h, then it is sequentially raised to 45℃-60℃ for 10h-15h, raised to 75℃-90℃ for 2.0h-4.0h, and finally lowered to 60℃-75℃ for 1.5h-2.5h; the temperature of the second curing is 80℃-110℃, and the time is 2h-4h.

[0052] In the present application, the catalyst is an imidazole catalyst and / or a phosphine catalyst; the phosphine catalyst is preferably tetrabutylphosphonium bromide; and the mass ratio of the catalyst to the optical material composition is (0.01-1):100. The amount of the catalyst to be added varies depending on the components of the optical material composition, the mixing ratio, and the polymerization and curing method, and cannot be generalized, and is preferably 0.03-0.5 wt% with respect to the total weight of the optical material composition, and when the amount of the catalyst to be added is more than 1 wt%, there is a case of rapid polymerization, and when the amount of the polymerization catalyst to be added is less than 0.01 wt%, there is a case of insufficient curing of the optical material composition and poor heat resistance.

[0053] The compound of formula 1 provided by the present application has a dioxane polar structure, enhances the intermolecular force between the compound and the hardening liquid, makes the plating film uniform, reduces the occurrence of hardening points, reduces the rework plating film process, and improves production efficiency. At the same time, the structure of the compound of the present application has the same double-ring sulfur structure as the bis(β-cyclotropyl) sulfide compound, so it has no negative impact on other performance indicators of the product. BRIEF DESCRIPTION OF DRAWINGS

[0054] Figure 1 The mass spectrum of the cyclotrop compound of Example 1 of the present application;

[0055] Figure 2 The mass spectrum of the cyclotrop compound of Example 1 of the present application; 13 The C NMR spectrum;

[0056] Figure 3 The mass spectrum of the cyclotrop compound of Example 1 of the present application; 1 The H NMR spectrum. DETAILED DESCRIPTION

[0057] The technical solutions of the present application will be described in detail below with reference to the embodiments of the present application. Obviously, the described embodiments are only a part of the embodiments of the present application, not all. Based on the embodiments in the present application, all other embodiments obtained by those skilled in the art without creative labor are within the scope of protection of the present application.

[0058] In order to further illustrate the present application, the following examples are used to illustrate the present application in detail. The raw materials used in the following examples of the present application are all commercially available.

[0059] Example 1

[0060] The preparation method of the cyclotrop compound represented by formula (1) (x = 1) is as follows:

[0061]

[0062] Specifically includes the following steps:

[0063] 1) 74 g (0.5 mol) of compound A, 98.8 g (1.3 mol) of thiourea, and 101 g (36%) of hydrochloric acid were added and refluxed for 12 hours. Then sodium hydroxide was added for alkaline hydrolysis to prepare 87.5 g (0.486 mol) of compound B.

[0064] 2) Add 87.5g (0.486mol) of compound B, 437.5g of methanol, and 94.5g (1.02mol) of epichlorohydrin to the reaction flask, and react at 60℃ for 5h. After the reaction is completed, add 30% NaOH to the reaction flask and react at 30℃ for 4h. Perform solvent removal treatment on the reaction solution. After solvent removal, 163.8g (0.45mol) of product compound D is obtained.

[0065] 3) Compound D 131.4 g (0.45 mol), methanol 788.4 g, toluene 394.2 g, thiourea 76 g (1 mol), and acetic anhydride 1.638 g were added to the reaction flask. The reaction was carried out at 60 °C for 12 h. After the reaction, the resulting organic layer was washed with 3% NaCl aqueous solution, and the solvent was removed by distillation. The crude product was purified by conventional separation using silica gel column chromatography to obtain 116.64 g (0.36 mol) of cyclic sulfur compound (x = 1). Mass spectrometry analysis of the cyclic sulfur compound was performed, and the mass spectrum is shown below. Figure 1 As shown, NMR analysis was performed on the cyclic sulfur compound to obtain... 13 The C NMR spectrum is as follows Figure 2 As shown, 1 H NMR spectrum as shown Figure 3 As shown.

[0066] Example 2

[0067] The preparation process of the cyclic sulfur compound (x=2) represented by formula (1) is as follows:

[0068]

[0069] Specifically, the following steps are included:

[0070] 1) 74g (0.5mol) of compound A, 98.8g (1.3mol) of thiourea and 101g (36%) of hydrochloric acid were added and refluxed for 12 hours. Then sodium hydroxide was added for alkaline hydrolysis to prepare 87.5g (0.486mol) of compound B.

[0071] 2) To the reaction bottle, compound B 87.5 g (0.486 mol), methanol 437.5 g, 1-chloro-3-mercapto-2-propanol 129.1 g (1.02 mol), I2 117 g (0.5 mol) were added, and reacted at 40 °C for 6 h. After the reaction was completed, 30% NaOH was continuously added to the reaction bottle, and reacted at 30 °C for 4 h. The reaction solution was subjected to desolventization treatment. After the desolventization was completed, product compound F 106.8 g (0.30 mol) was obtained.

[0072] 3) To the reaction bottle, compound F 106.8 g (0.30 mol), methanol 320 g, toluene 320 g, thiourea 76 g (1 mol), acetic anhydride 1.068 g were added, and reacted at 50 °C for 18 h. After the reaction was completed, the obtained organic layer was subjected to water washing using 3% NaCl aqueous solution. The solvent was distilled off. The crude product was subjected to a general separation and purification using a silica gel column, thereby obtaining the cyclic sulfur compound (x = 2) represented by the aforementioned formula (1) 81.48 g (0.21 mol).

[0073] Example 3

[0074] 1) Bis(β-cyclo-sulfur propyl) sulfide 88.4 g, the cyclic sulfur compound synthesized in Example 1 0.1 g, isophorone diisocyanate 5.1 g, thiodiglycol 6.3 g, tetrabutylphosphonium bromide 0.1 g, 2-(2-hydroxy-tert-octylphenyl)-2H-benzotriazole (UV-329) 0.3 g, di-n-butyl phosphate 0.2 g were mixed and stirred for 50 min, thereby obtaining a prepolymer solution.

[0075] 2) After the obtained prepolymer solution was vacuum degassed for 30 min, it was filtered through a polytetrafluoroethylene filter membrane with a pore size of 3 μm, and then injected into a glass mold. The mold was then placed in a programmed temperature curing oven for primary curing, thereby obtaining a resin lens after primary curing. The temperature program for primary curing was as follows: the initial temperature was 20 °C, and the temperature was maintained for 2 h. Then, the temperature was increased to 45 °C over 3.5 h, increased to 55 °C over 3 h, and increased to 100 °C over 6 h, and maintained at 100 °C for 4 h. Finally, the temperature was decreased to 70 °C over 2 h.

[0076] 3) The resin lens after primary curing was subjected to release demolding and multi-tank ultrasonic cleaning. After the cleaning was completed, the resin lens was continuously placed in a programmed temperature curing oven for secondary curing. After the secondary curing was completed, a substrate was obtained. The temperature program for secondary curing was as follows: 80 °C to 110 °C, and the time was 2 h to 4 h.

[0077] 4) The substrate was placed in a lens holder and immersed in H673 hardening solution. The lens holder was raised at a certain speed, so that the lens surface was coated with a uniform layer of hardening solution with a certain thickness. Then, the lens holder was placed in a pre-curing channel for pre-curing, and the resin lens was subjected to hardening treatment. The lenses after the hardening treatment were inspected one by one.

[0078] Example 4

[0079] The difference from Example 3 is that bis(β-epithiopropyl) sulfide 87.5 g, the episulfide compound synthesized in Example 1 1.0 g are added, and the other added amounts or processes are the same as in Example 3.

[0080] Example 5

[0081] The difference from Example 3 is that bis(β-epithiopropyl) sulfide 86.5 g, the episulfide compound synthesized in Example 1 2.0 g are added, and the other added amounts or processes are the same as in Example 3.

[0082] Example 6

[0083] The difference from Example 3 is that bis(β-epithiopropyl) sulfide 85.5 g, the episulfide compound synthesized in Example 1 3.0 g are added, and the other added amounts or processes are the same as in Example 3.

[0084] Example 7

[0085] The difference from Example 3 is that bis(β-epithiopropyl) sulfide 84.5 g, the episulfide compound synthesized in Example 1 4.0 g are added, and the other added amounts or processes are the same as in Example 3.

[0086] Example 8

[0087] The difference from Example 3 is that bis(β-epithiopropyl) sulfide 83.5 g, the episulfide compound synthesized in Example 1 5.0 g are added, and the other added amounts or processes are the same as in Example 3.

[0088] Example 9

[0089] The difference from Example 3 is that bis(β-epithiopropyl) disulfide 88.4 g, the episulfide compound synthesized in Example 2 0.1 g are added, and the other added amounts or processes are the same as in Example 3.

[0090] Example 10

[0091] The difference from Example 3 is that bis(β-epithiopropyl) disulfide 85.5 g, the episulfide compound synthesized in Example 2 (x = 2) 3 g are added, and the other added amounts or processes are the same as in Example 3.

[0092] Comparative Example 1

[0093] The difference from Example 3 is that bis(β-epithiopropyl) sulfide 88.5 g, the episulfide compound synthesized in Example 1 0 g are added, and the other added amounts or processes are the same as in Example 3.

[0094] Comparative Example 2

[0095] Different from Example 3 is that: adding bis(β-epithiopropyl) sulfide 82.5 g, the synthesized epithiocompound 6 g in Example 1, and other additive amounts or processes are the same as those in Example 3.

[0096] Comparative Example 3

[0097] Different from Example 3 is that: adding bis(β-epithiopropyl) sulfide 80.5 g, the synthesized epithiocompound 8 g in Example 1, and other additive amounts or processes are the same as those in Example 3.

[0098] Comparative Example 4

[0099] Different from Example 3 is that: adding bis(β-epithiopropyl) disulfide 88.5 g, the synthesized epithiocompound 0 g in Example 2, and other additive amounts or processes are the same as those in Example 3.

[0100] Comparative Example 5

[0101] Different from Example 3 is that: adding bis(β-epithiopropyl) disulfide 82.5 g, the synthesized epithiocompound 6 g in Example 2, and other additive amounts or processes are the same as those in Example 3.

[0102] In this example, 1000 pieces of the substrate after hardening coating are observed to determine the substrate with hardening points. More than 20 pieces are recorded as poor, 5-20 pieces are recorded as good, and 0-5 pieces are recorded as excellent.

[0103] The optical materials obtained from the examples and comparative examples are tested for hardening points and refractive index. The specific results are shown in Table 1 below.

[0104] Table 1

[0105]

[0106] As can be seen from the results in Table 1, the addition of the compound of formula (1) has little effect on the refractive index of the optical material. When the addition amount of the epithiocompound represented by formula (1) is 0.1%-3.0wt%, the number of pieces with hardening points during the hardening of the substrate of the optical resin material lens is <0.5%, the rework rate is the lowest, and the production efficiency is the highest; when the addition amount of the epithiocompound represented by formula (1) is >4wt%, the number of pieces with hardening points during the hardening of the substrate is low, but the refractive index of the lens also decreases, which does not meet the use requirements.

[0107] The foregoing description of the disclosed embodiments enables one of ordinary skill in the art to make or use the application. Various modifications to these embodiments will be readily apparent to those skilled in the art, and the generic principles defined herein can be applied to other embodiments without departing from the spirit or scope of the application. Thus, the present application 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. The compound as shown in formula (1), （1）； In equation (1), x = 1 or 2.

2. The method for preparing the compound according to claim 1, characterized in that, include: The compound shown in formula (2) was reacted with thiourea to undergo sulfur hybridization, yielding the compound; （2）； In equation (2), x = 1 or 2; The molar ratio of the compound shown in formula (2) to the sulfiding reagent is 1:(1~3).

3. The method for preparing the compound according to claim 2, characterized in that, The preparation method of the compound represented by formula (2) includes: The compound shown in formula (3) is subjected to a removal reaction under alkaline conditions; （3）； In equation (3), x = 1 or 2.

4. The method for preparing the compound according to claim 3, characterized in that, The preparation method of the compound represented by formula (3) includes: （4）； The compound shown in formula (4) is reacted with epichlorohydrin, or the compound shown in formula (4), an oxidant, and 1-chloro-3-mercapto-2-propanol are reacted; The preparation method of the compound represented by formula (4) includes: The compound shown in formula (5) was reacted with thiourea under acidic conditions to obtain an intermediate. The intermediate was then hydrolyzed with an alkaline solution to obtain the compound shown in formula (4). （5）。 5. An optical material composition, characterized in that, Includes the compound shown in formula (1), the compound shown in formula (6), and the optical material matrix; （1）， In equation (1), x = 1 or 2; （6）； In equation (6), m = 1 or 2.

6. The optical material composition according to claim 5, characterized in that, The optical material matrix also includes thiols and isocyanates.

7. The optical material composition according to claim 6, characterized in that, The compound comprises, by weight: 0.001 to 5 parts of the compound shown in formula (1); 50 to 99 parts of the compound shown in formula (6); 1 to 20 parts of the thiol compound; and 1 to 20 parts of the isocyanate.

8. The optical material composition according to claim 5, characterized in that, It also includes additives; the additives are selected from one or more of ultraviolet absorbers, release agents, blue agents and red agents.

9. A cured composition, characterized in that, Includes the optical material composition and catalyst as described in any one of claims 5-8.

10. The curing composition according to claim 9, characterized in that, The catalyst is an imidazole catalyst and / or a phosphine catalyst.

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