Naphthyl-bis (thioethyl acrylate) compound as well as preparation method and application thereof

Abstract

The invention discloses naphthyl-bis (thioethyl acrylate) as shown in a formula I and a preparation method and application thereof. A two-step synthesis process of oxygen-sulfur exchange and nucleophilic substitution is adopted, and the method comprises the following steps: step I, oxygen-sulfur exchange reaction: 1, 5-naphthalene diphenol and CS2 are subjected to nucleophilic addition under an alkaline condition, hydroxyl oxygen atoms attack carbon atoms of CS2, and a sodium xanthate intermediate is formed; after acidification, the sulfur anions convert phenolic hydroxyl groups into thiol groups through intramolecular nucleophilic attack. In the step II, two sulfydryl groups in 1, 5-naphthalene dithiol serve as nucleophilic groups, sulfur anions are formed under the alkaline condition, alpha-carbon of chloroethyl acrylate is attacked, nucleophilic substitution is carried out, and HCl is released. The generated naphthyl-bis (thioethyl acrylate) has the characteristics of high purity, high light transmittance and large refractive index, and can be used for preparing a modified acrylic optical material with relatively high refractive index and high light transmittance.

Description

Technical Field

[0001] This invention belongs to the field of organic polymer optical materials technology, specifically relating to a naphthyl-bis(thioethyl acrylate) compound, its preparation method, and its application. Background Technology

[0002] Acrylic monomers are polymerized to produce optical materials, which have advantages such as high light transmittance, low density and easy processing, and are widely used in lenses, screens and other fields.

[0003] However, existing materials have three major drawbacks: ① low refractive index, usually between 1.45 and 1.59; ② difficulty in dispersive control and unsatisfactory Abbe number; ③ poor weather resistance and prone to yellowing after long-term use.

[0004] In addition, high-end applications require extremely high purity (>99%), while traditional processes struggle to meet all performance indicators.

[0005] Due to their large usage and wide range of applications, medium- and high-refractive-index modified acrylates have become a major research direction for the future. By introducing heterocyclic, benzene ring, sulfur and other structures to optimize material properties, high optical and mechanical properties can be achieved while maintaining low dispersion. They are compatible with a variety of efficient curing processes and have important application value in optical systems, medium- and high-refractive-index optical lenses and electronic display devices. They are one of the key materials for achieving high transparency, lightweight and precision in high-performance optical components.

[0006] There is an urgent need to develop medium- and high-refractive-index modified acrylate optical materials, as well as efficient, environmentally friendly, and economical preparation technologies and processes, in order to meet the upgrading needs of the optical materials industry. Summary of the Invention

[0007] The present invention aims to provide a naphthyl-bis(thioethyl acrylate), its preparation method, and its applications. A two-step synthesis process of "oxygen-sulfur exchange and nucleophilic substitution" is employed to prepare a naphthyl-bis(thioethyl acrylate) compound composed of naphthyl, thioethyl, and acrylate groups, as shown in Formula A. This compound exhibits high purity, high light transmittance, and a high refractive index. This compound can be used as a monomer for preparing modified acrylic optical resins for the manufacture of high-precision acrylic optical components. Modified acrylic optical resin materials prepared using this compound as a raw material possess higher refractive index, better hydrostatic strength, and better aging resistance.

[0008] To achieve the above objectives, the present invention provides the following technical solution:

[0009] Naphthyl-bis(thioethyl acrylate) compound, the structural formula of which is shown in Formula A:

[0010]

[0011] On the other hand, the present invention provides a method for preparing the above-mentioned naphthyl-bis(thioethyl acrylate) compound.

[0012] Step one, the oxygen-sulfur exchange reaction: 1,5-naphthyldiphenol undergoes nucleophilic addition with CS2 under alkaline conditions. The hydroxyl oxygen atom attacks the carbon atom of CS2, forming a sodium xanthate intermediate. After acidification, the sulfide anion forms a six-membered ring transition state through intramolecular nucleophilic attack, resulting in a migration rearrangement. The CO bond breaks, the CS bond forms, and the phenolic hydroxyl group is converted into a thiol group. The entire rearrangement process does not require high-temperature activation. The specific reaction process is as follows:

[0013]

[0014] HO-C 10 H6-OH + 2CS2 + 2NaOH + 2HCl → HS-C 10 H6-SH + 2COS + 2NaCl + 2H2O

[0015] Step two, the nucleophilic substitution reaction, occurs under the basic action of pyridine. The thiol group of 1,5-naphthalenedithiol is deprotonated to form a thioanion, which acts as a nucleophile. This thioanion then attacks the α-carbon bonded to chlorine in ethyl chloroacrylate, undergoing an SN2 reaction. The chloride ion leaves as a leaving group, thus forming a thioether bond. The HCl generated in the reaction is rapidly captured by pyridine, forming a pyridine hydrochloride precipitate. After two substitutions, the naphthyl-bis(thioethyl acrylate) monomer is finally generated. The specific reaction process is as follows:

[0016]

[0017] HS-C 10 H6-SH+2ClCH2CH2OOCCH=CH2→

[0018] CH2=CHCOOCH2CH2S-C 10 H6-SCH2CH2OOCCH=CH2+2HCl

[0019] Specifically, the preparation reaction includes the following steps:

[0020] I. Oxygen-sulfur exchange reaction: 1,5-naphthol was added to a reaction vessel containing solvent with stirring, N2 was introduced, and the mixture was kept in an ice bath at 0-10°C. After complete dissolution, sodium hydroxide solution was added dropwise over 30-90 minutes, and the solution gradually turned dark red. Carbon disulfide was added dropwise over 30-70 minutes, and stirring was continued for 2-4 hours, during which the solution gradually turned orange-yellow. The mixture was then brought to room temperature, and N2 protection was continued. Hydrochloric acid was added dropwise until the pH reached 2-3, and stirring was continued at room temperature for 4-6.5 hours, during which a solid precipitated. The filtered solid product was dissolved in hot ethanol, and activated carbon was added for decolorization. The activated carbon was removed by hot filtration, and the mixture was cooled to 0-5°C to crystallize. The crystals were then filtered, washed, and dried under vacuum to obtain 1,5-naphthyl dithiol.

[0021] II. Nucleophilic substitution reaction: 1,5-naphthyl dithiol and pyridine catalyst were added to a reaction vessel containing solvent with stirring. N2 was introduced and the mixture was kept in an ice bath at 0-10°C. After dissolution, ethyl chloride acrylate was added dropwise over 30-60 minutes. The mixture was then brought to room temperature and stirred for 4-7 hours. The mixture was filtered to remove salts, washed, and the solvent was collected by distillation. The crude product was then eluted with a gradient of oil ether / ethyl acetate to obtain naphthyl-bis(thioethyl acrylate) compound (A).

[0022] In the preparation method described above, preferably, the solvent in step I is selected from at least one of diethyl ether, methanol, ethanol, acetone, isopropanol, and dichloromethane.

[0023] In the preparation method described above, preferably, the sodium hydroxide solution in step I has a percentage concentration of 20-35 wt%; and the hydrochloric acid has a percentage concentration of 30-36 wt%.

[0024] In the preparation method described above, preferably, the weight ratio of carbon disulfide, 1,5-naphthol, sodium hydroxide solution and solvent in step I is 1:(1-1.2):(1.5-3):(4-7).

[0025] In the preparation method described above, preferably, the solvent in step II is selected from at least one of acetonitrile, acetone, ethanol, xylene, isobutanol, tetrahydrofuran, and dichloromethane.

[0026] In the preparation method described above, preferably, the weight ratio of 1,5-naphthalenedithiol, pyridine, ethyl chloride acrylate and solvent in step II is 1:(1-1.5)(1.2-1.7):(3-7).

[0027] In another aspect, the present invention provides the application of naphthyl-bis(thioethyl acrylate) compounds in the preparation of modified acrylic optical resin materials.

[0028] In another aspect, the present invention provides a modified acrylic optical resin material, which is polymerized from naphthyl-bis(thioethyl acrylate) and acrylate monomers, wherein the weight ratio of naphthyl-bis(thioethyl acrylate) to methyl acrylate monomers is 1:(5-20).

[0029] The beneficial effects of this invention are:

[0030] (1) The naphthyl-bis(thioethyl acrylate) of the present invention has a thionaphthalene ring structure, which has high electron density and polarizability, effectively improving the refractive index and antioxidant properties of the material. At the same time, the rigid structure of the naphthalene ring copolymerizes with flexible monomers, which can further improve the mechanical properties of the material. The modified acrylic optical resin material prepared from it has a higher refractive index, ultraviolet absorption performance, better hydrostatic strength and aging resistance.

[0031] (2) The two-step reaction conditions for preparing naphthyl-bis(thioethyl acrylate) are relatively mild, do not require high temperature and high pressure equipment, are controllable stepwise, and have high yield.

[0032] (3) The raw materials used, such as 1,5-naphthol, CS2 and ethyl chloride acrylate, are readily available, have low cost, and are economically beneficial.

[0033] (4) Byproducts are easy to handle. COS can be absorbed and decomposed (alkaline treatment), which is environmentally friendly and in line with the principles of green chemistry. Attached Figure Description

[0034] Figure 1 The FT-IR infrared spectrum of the naphthyl-bis(thioethyl acrylate) compound prepared in Example 1 is shown.

[0035] Figure 2 The 1H NMR spectrum of the naphthyl-bis(thioethyl acrylate) compound prepared in Example 1. Detailed Implementation

[0036] The present invention will be further described below through specific embodiments, but this does not imply a limitation on the scope of protection of the present invention.

[0037] Example 1: Preparation of naphthyl-bis(thioethyl acrylate) compound.

[0038] 120g of 1,5-naphthyldithiol powder was added to a reaction vessel containing 600g of ethanol with stirring. N2 was introduced, and the mixture was kept in an ice bath at 5°C. After complete dissolution, 250g of 25wt% NaOH solution was added dropwise over 30 minutes, and the solution gradually turned dark red. 115g of carbon disulfide was added dropwise over 60 minutes, and stirring was continued for 3 hours, during which the solution gradually turned orange-yellow. The mixture was then brought to room temperature, kept under N2 protection, and hydrochloric acid was added dropwise until the pH reached 2.5. After stirring for 6 hours, a solid precipitated. The filtered solid product was dissolved in hot ethanol, decolorized with activated carbon, and hot-filtered to remove the activated carbon. The mixture was cooled to 5°C to crystallize, filtered, washed, and dried under vacuum to obtain 120.4g of 1,5-naphthyldithiol crystals.

[0039] 120 g of 1,5-naphthalenedithiol and 120 g of pyridine were added to a reaction vessel containing 300 g of acetonitrile and 180 g of acetone with stirring. N2 was introduced, and the mixture was kept in an ice bath at 5°C. After complete dissolution, 170 g of ethyl chloride acrylate was added dropwise over 45 minutes. The mixture was then brought to room temperature and stirred for 6 hours. The mixture was filtered to remove salts, washed, and the solvent was collected by distillation. The crude product was then eluted with a gradient of oil ether / ethyl acetate, finally yielding 208.2 g of naphthyl-bis(thioethyl acrylate) compound (A). Yield: 85.9%.

[0040] Fourier transform infrared (FT-IR) spectroscopy was performed on the product prepared in Example 1. Figure 1 As shown in the figure, the curve analysis shows that the range is 3080–3010 cm. -1 The absorption peak at 3002–2853 cm⁻¹ corresponds to the aromatic CH stretching vibration (naphthalene ring). -1 The absorption peak at 2985–2964 cm⁻¹ is due to the stretching vibration of aliphatic CH (-CH₂-). -1 The absorption peak at this point is due to the asymmetric stretching of =CH2, 2920–2852 cm⁻¹. -1 The absorption peak at 1724–1735 cm⁻¹ is due to the -CH₂- symmetric and asymmetric stretching vibrations. -1 The absorption peak at 1635–1620 cm⁻¹ is a characteristic peak of the C=O stretching vibration. -1 The absorption peak at 1610–1583 cm⁻¹ corresponds to the C=C stretching vibration in acrylates. -1 The absorption peak at 1511–1447 cm⁻¹ corresponds to the naphthalene ring skeletal vibration. -1 The absorption peak at 1318–1147 cm⁻¹ is due to C=C stretching of the naphthalene ring. -1 The absorption peak at 985–810 cm⁻¹ corresponds to the asymmetric and symmetric stretching vibrations of the ester group COC. -1 The absorption peak at this point is due to the out-of-plane bending vibration of =CH, 758–696 cm⁻¹. -1 The absorption peak at 709-622 cm⁻¹ is a characteristic absorption of naphthalene ring substitution. -1The absorption peak at that point is due to the CS stretching vibration.

[0041] 1H NMR spectroscopy analysis: δ = 7.90–7.32 ppm (m, 6H, C) 10 H6), 6.35–6.44 ppm (dd, 2H, 2×-CH=CH2 in -CH=CH2), 6.12–6.19 ppm (dd, 2H, -CH=CH2 in trans=CH2), 5.82–5.90 ppm (dd, 2H, -CH=CH2 in cis=CH2), 4.22–4.35 ppm (t, 4H, -OCO-CH j -CH2-), 2.96~3.10ppm(t,4H,-CH2-CH2-S-).

[0042] High-performance liquid chromatography (HPLC) quantitative detection and analysis: The content of the product prepared in Example 1 was determined and analyzed. The external standard method was used, and the specific steps were as follows: Preparation of mixed standards: Accurately weigh the pure product and prepare a series of standard solutions with at least five concentration gradients (e.g., 10%, 5%, 3%, 1%, 0.5%). Inject the mixed standard solutions sequentially from high to low concentration, record the chromatograms, and read the peak areas of two isomers. Plot a standard curve using the least squares method with the standard concentration (x) as the abscissa and the corresponding peak area (y) as the ordinate, and obtain the regression equation (e.g., y = ax + b) to establish a linear relationship. Then, compare the peak area measured in the sample of Example 1 with the standard peak area to calculate the content range of each isomer. The detection results showed that the naphthyl-bis(thioethyl acrylate) content in the sample of Example 1 was 98.1%.

[0043] Example 2 Preparation of naphthyl-bis(thioethyl acrylate).

[0044] 90g of 1,5-naphthyldithiol powder was added to a reaction vessel containing 450g of acetone with stirring. N2 was introduced, and the mixture was kept in an ice bath at 5°C. After complete dissolution, 185g of 25wt% NaOH solution was added dropwise over 30 minutes, and the solution gradually turned dark red. 86g of carbon disulfide was added dropwise over 60 minutes, and stirring was continued for 3 hours, during which the solution gradually turned orange-yellow. The mixture was then brought to room temperature, kept under N2 protection, and hydrochloric acid was added dropwise until the pH reached 2.4. After stirring for 6 hours, a solid precipitated. The filtered solid product was dissolved in hot ethanol, decolorized with activated carbon, and removed by hot filtration. The product was cooled to 3°C to crystallize, filtered, washed, and dried under vacuum to obtain 90.1g of 1,5-naphthyldithiol crystals.

[0045] 90 g of 1,5-naphthyl dithiol and 110 g of pyridine were added to a reaction vessel containing 270 g of acetonitrile and 100 g of acetone with stirring. N2 was introduced, and the mixture was kept in an ice bath at 5 °C. After complete dissolution, 130 g of ethyl chloride acrylate was added dropwise over 40 minutes. The mixture was then brought to room temperature and stirred for 5.5 hours. The mixture was filtered to remove salts, washed, and the solvent was collected by distillation. The crude product was then eluted with a gradient of oil ether / ethyl acetate to give 155.7 g of naphthyl-bis(thioethyl acrylate) compound (A), with a yield of 85.6%.

[0046] The naphthyl-bis(thioethyl acrylate) compound prepared in Example 2 was subjected to FT-IR and 1H NMR nuclear magnetic resonance spectroscopy. The test results were basically the same as those in Example 1.

[0047] Example 3 Preparation of naphthyl-bis(thioethyl acrylate).

[0048] 102g of 1,5-naphthyldithiol powder was added to a reaction vessel containing 500g of ethanol with stirring. N2 was introduced, and the mixture was kept in an ice bath at 5°C. After complete dissolution, 210g of 25wt% NaOH solution was added dropwise over 30 minutes, and the solution gradually turned dark red. 97g of carbon disulfide was added dropwise over 60 minutes, and stirring was continued for 3 hours, during which the solution gradually turned orange-yellow. The mixture was then brought to room temperature, kept under N2 protection, and hydrochloric acid was added dropwise until the pH reached 2.3. After stirring for 6 hours, a solid precipitated. The filtered solid product was dissolved in hot ethanol, decolorized with activated carbon, and removed by hot filtration. The product was cooled to 5°C to crystallize, filtered, washed, and dried under vacuum to obtain 97.5g of 1,5-naphthyldithiol crystals.

[0049] 65 g of 1,5-naphthyl dithiol and 75 g of pyridine were added to a reaction vessel containing 160 g of acetonitrile and 80 g of acetone with stirring. N2 was introduced, and the mixture was kept in an ice bath at 5 °C. After complete dissolution, 95 g of ethyl chloride acrylate was added dropwise over 40 minutes. The mixture was then brought to room temperature and stirred for 5 hours. The mixture was filtered to remove salts, washed, and the solvent was collected by distillation. The crude product was then eluted with a gradient of oil ether / ethyl acetate to obtain 113.9 g of naphthyl-bis(thioethyl acrylate) compound (A), with a yield of 86.7%.

[0050] Example 4: Preparation of naphthyl-bis(thioethyl acrylate).

[0051] 60g of 1,5-naphthyldithiol powder was added to a reaction vessel containing 300g of ethanol with stirring. N2 was introduced, and the mixture was kept in an ice bath at 5°C. After complete dissolution, 160g of 20wt% NaOH solution was added dropwise over 30 minutes, and the solution gradually turned dark red. 57g of carbon disulfide was added dropwise over 60 minutes, and stirring was continued for 3 hours, during which the solution gradually turned orange-yellow. The mixture was then brought to room temperature, kept under N2 protection, and hydrochloric acid was added dropwise until the pH reached 2.5. After stirring for 5.5 hours, a solid precipitated. The filtered solid product was dissolved in hot ethanol, decolorized with activated carbon, and removed by hot filtration. The product was cooled to 5°C to crystallize, filtered, washed, and dried under vacuum to obtain 60.1g of 1,5-naphthyldithiol crystals.

[0052] 155g of 1,5-naphthalenedithiol and 170g of pyridine were added to a reaction vessel containing 450g of acetonitrile and 200g of acetone with stirring. N2 was introduced, and the mixture was kept in an ice bath at 5°C. After complete dissolution, 225g of ethyl chloride acrylate was added dropwise over 45 minutes. The mixture was then brought to room temperature and stirred for 6 hours. The mixture was filtered to remove salts, washed, and the solvent was collected by distillation. The crude product was then eluted with a gradient of oil ether / ethyl acetate to obtain 267.5g of naphthyl-bis(thioethyl acrylate) compound (A), with a yield of 85.4%.

[0053] Example 5: Preparation of naphthyl-bis(thioethyl acrylate).

[0054] 66g of 1,5-naphthyldithiol powder was added to a reaction vessel containing 330g of ethanol with stirring. N2 was introduced, and the mixture was kept in an ice bath at 5°C. After complete dissolution, 135g of 25wt% NaOH solution was added dropwise over 30 minutes, and the solution gradually turned dark red. 63g of carbon disulfide was added dropwise over 60 minutes, and stirring was continued for 3 hours, during which the solution gradually turned orange-yellow. The mixture was then brought to room temperature, kept under N2 protection, and hydrochloric acid was added dropwise until the pH reached 2.3. After stirring for 6 hours, a solid precipitated. The filtered solid product was dissolved in hot ethanol, decolorized with activated carbon, and removed by hot filtration. The product was cooled to 5°C to crystallize, filtered, washed, and dried under vacuum to obtain 65.3g of 1,5-naphthyldithiol crystals.

[0055] 80 g of 1,5-naphthyl dithiol and 92 g of pyridine were added to a reaction vessel containing 220 g of acetonitrile and 100 g of acetone with stirring. N2 was introduced, and the mixture was kept in an ice bath at 5 °C. After complete dissolution, 115 g of ethyl chloride acrylate was added dropwise over 40 minutes. The mixture was then brought to room temperature and stirred for 5 hours. The mixture was filtered to remove salts, washed, and the solvent was collected by distillation. The crude product was then eluted with a gradient of oil ether / ethyl acetate to obtain 139.7 g of naphthyl-bis(thioethyl acrylate) compound (A), with a yield of 86.4%.

[0056] Example 6: Preparation of modified acrylic optical materials.

[0057] Take 18g of naphthyl-bis(thioethyl acrylate) prepared in Example 1, stir and add it to a reaction vessel containing 12g of hydroxyethyl methacrylate and 95g of methyl methacrylate. Heat to 45°C and stir for 30 minutes. Then add 0.06g of azobisisoheptanenitrile and 0.03g of tert-butyl peroxide-2-ethylacetate and stir for 25 minutes to obtain a prepolymer. Degas under vacuum for 20 minutes, filter under pressure and cast. Place the cast mold in a curing oven, heat to 45°C and cure for 2.5 hours, heat to 50°C and cure for 3 hours, heat to 70°C and cure for 3 hours, heat to 85°C and cure for 2 hours, anneal at 70°C and hold for 1 hour, cool to room temperature, demold and take samples to obtain modified acrylic optical material.

[0058] Comparative Example 1: Preparation of acrylic optical materials.

[0059] 30g of hydroxyethyl methacrylate was added to a reaction vessel containing 95g of methyl methacrylate and heated to 45℃ and stirred for 30 minutes. Then, 0.06g of azobisisobutyronitrile and 0.03g of tert-butyl peroxide-2-ethylacetate were added and stirred for 25 minutes to obtain a prepolymer. The prepolymer was degassed under vacuum for 20 minutes, filtered under pressure, and poured. The mold after pouring was placed in a curing oven and cured at 45℃ for 2.5 hours, then at 50℃ for 3 hours, then at 70℃ for 3 hours, then at 85℃ for 2 hours. The prepolymer was then annealed at 70℃ for 1 hour, cooled to room temperature, demolded, and sampled to obtain acrylic optical material.

[0060] Example 7: Optical performance testing experiments were conducted on the product.

[0061] The optical properties of the products and optical materials prepared in Examples 1-6 and Comparative Example 1 were tested. Transmittance was measured using a Lambda 650S UV-Vis spectrophotometer (PerkinElmer Chemical Analysis Instruments, Inc.), and refractive index was measured using an Rx-7000 digital refractometer (Shanghai Optical Instrument Equipment Co., Ltd.). The testing method involved directly dissolving the prepared sample and coating or placing it onto the prism of the UV-Vis spectrophotometer or refractometer for measurement.

[0062] Table 1 Optical properties of the prepared samples

[0063]

[0064] The test results show that the naphthyl-bis(thioethylpropyl acrylate) created in this invention can copolymerize with other monomers and effectively improve the refractive index; the naphthalene ring-containing compounds and products have strong absorption in the ultraviolet region.

[0065] Example 8: Static compressive strength test experiment.

[0066] The optical materials prepared in Example 6 and Comparative Example 1 were subjected to hydrostatic pressure tests. The test method involved selecting a substrate with a certain curvature at its center thickness, fixing it convex-side up on a steel structure support. A cylindrical groove was located within the steel structure support. A sheet of white paper was placed at the bottom of the groove, and a sheet of carbon paper was placed on top of the white paper. A load of 105 N was applied to the sample at a speed of 350 mm / min, and the appearance of imprints on the white paper or cracks in the sample was observed. The hydrostatic pressure test results showed that the white paper under the Comparative Example 1 sample showed imprints, while the white paper under the Example 6 sample showed no imprints. The Example 6 sample cracked under a pressure of 109 N, indicating that the Example 6 sample had superior hydrostatic pressure resistance.

[0067] Example 9: An aging resistance test was conducted.

[0068] The optical materials prepared in Example 6 and Comparative Example 1 were subjected to aging resistance tests. They were irradiated at 40°C / UV for 48 hours in an aging resistance test chamber, with the irradiation intensity selected as the extreme irradiation condition. One set of unaged optical materials was reserved as a blank control group. The yellowing index and visible light spectrum of the samples were measured before and after irradiation. The change in visible light transmittance was T = T1 - T2, and the change in yellowing index was ΔY = ΔY2 - ΔY1. Data comparison showed that the change in the sample of Example 6 was significantly lower than that of the sample of Comparative Example 1 (see Table 2).

[0069] Table 2 Comparison of aging resistance of samples

[0070]

Claims

1. A naphthyl-bis(thioethyl acrylate) compound characterized in that, The structural formula of the compound is shown as formula A:

2. The method for preparing the naphthyl-bis(thioethyl acrylate) compound as described in claim 1, characterized in that, The method comprises the following steps: I. Oxygen-sulfur exchange reaction: stirring 1,5-naphthalenediol into a reaction container containing a solvent, N2inlet, ice bath to 0-10℃, complete dissolution, drop 60 hours sodium hydroxide solution, the solution gradually turns into deep red; drop carbon disulfide, continue stirring for 2-4 hours, the solution gradually turns into orange yellow; rise to room temperature, continue N2protection, drop hydrochloric acid to pH=2-3, continue stirring at room temperature for 4-6.5 hours, solid precipitates; the solid product collected by filtration is dissolved in hot ethanol, activated carbon is added for decolorization, activated carbon is removed by hot filtration, cooling to 0-5℃, crystallization, suction filtration, washing, vacuum drying, 1,5-naphthalene dithiol is obtained; II. Nucleophilic substitution reaction: stirring 1,5-naphthalene dithiol and pyridine catalyst into a reaction container containing a solvent, N2inlet, ice bath to 0-10℃, drop chloroethyl acrylate after dissolution, rise to room temperature and stir for 4-7 hours; filter out salt, wash, distill the solvent, then gradient elute the obtained crude product with petroleum ether / ethyl acetate, finally, naphthyl-bis(thioethyl acrylate) compound (A) is obtained.

3. The production method according to claim 2, wherein The solvent in step I is at least one selected from the group consisting of diethyl ether, methanol, ethanol, acetone, isopropanol, dichloromethane.

4. The production method according to claim 2, wherein The percentage concentration of sodium hydroxide solution in step I is 20-35wt%; the percentage concentration of hydrochloric acid is 30-36wt%.

5. The production method according to claim 2, wherein The weight ratio of carbon disulfide, 1,5-naphthalenediol, sodium hydroxide solution and solvent in step I is 1:(1-1.2):(1.5-3):(4-7).

6. The production method according to claim 2, wherein The solvent in step II is at least one selected from the group consisting of diethyl ether, acetone, ethanol, dimethylbenzene, isobutanol, tetrahydrofuran and dichloromethane.

7. The production method according to claim 2, wherein The weight ratio of 1,5-naphthalene dithiol, pyridine, chloroethyl acrylate and solvent in step II is 1:(1-1.5)(1.2-1.7):(3-7).

8. Use of naphthyl-bis(thioethyl acrylate) compound in preparing modified acrylic optical resin material.

9. A modified acrylic optical resin material, characterized by, It is polymerized from naphthyl-bis(thioethyl acrylate) and acrylic ester monomer, the weight ratio of naphthyl-bis(thioethyl acrylate) and methyl acrylate monomer is 1:(5-20).

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