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JP-7856853-B2 - Novel episulfide compounds and their optical material compositions

JP7856853B2JP 7856853 B2JP7856853 B2JP 7856853B2JP-7856853-B2

Inventors

  • 丁 宗旺
  • 梁 万根
  • 崔 衛華
  • 張 建林
  • 易 先君
  • 高 艶麗
  • 張 金国

Assignees

  • 益豊新材料股▲ふん▼有限公司

Dates

Publication Date
20260511
Application Date
20240328
Priority Date
20230331

Claims (9)

  1. A novel episulfide compound characterized by being a compound represented by the chemical formula (1).
  2. A polymerizable compound mainly composed of the compound represented by formula (1) and the compound represented by formula (2) as described in claim 1, Herein, 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. Furthermore, it contains thiol compounds and isocyanate compounds, The optical material composition according to claim 2, characterized in that the compound represented by formula (1) accounts for 0.1 to 3.0% of the total weight of the composition.
  4. The optical material composition according to claim 2 or 3, characterized in that the compound represented by formula (2) accounts for 50.0 to 99.999% of the total weight of the composition.
  5. The optical material composition according to claim 4, characterized in that the compound represented by formula (2) accounts for 70.0 to 99.999% of the total weight of the optical material composition.
  6. A polymerization-curable composition characterized by containing the optical material composition described in claim 2 and a polymerization catalyst in an amount of 0.01 to 1% relative to the total weight of the optical material composition.
  7. The polymerization catalyst is imidazole or phosphine, and the amount added is 0.03% to 0.5% of the total weight of the optical material composition, characterized in that it is the polymerization catalyst according to claim 6.
  8. An optical material characterized by being obtained by curing the polymerization-curable composition described in claim 6 or 7.
  9. An optical lens characterized by being manufactured using the optical material described in claim 8.

Description

This invention belongs to the field of novel organic and optical materials, and relates to optical materials suitable for use in plastic lenses, prisms, optical fibers, information storage substrates, filters, and the like, more specifically, to novel episulfide compounds and their optical material compositions. In recent years, with the advancement of optical resin technology, continuously increasing the refractive index of optical resin lenses has become a goal for future lenses. Sulfur-containing compounds, particularly polycyclic sulfur compounds, and their compounding technologies have been developed as raw materials for ultra-high refractive index resin lenses. In the manufacturing process of optical resin lenses, after primary curing is complete, demolding and mold opening are performed, followed by edge processing and cleaning of the resulting substrate. The purpose of cleaning is to remove unreacted monomers and pulverized solid powder. To ensure effective cleaning, it is necessary to use a solution with a specific alkali concentration and control the cleaning temperature. During the cleaning process, the resin lens can corrode or burn due to the effects of alkali concentration and temperature, reducing substrate yield and increasing manufacturing costs. Conventional technology lacks a technical solution to this problem. Therefore, providing optical materials with superior performance and alkali corrosion resistance has become one of the most pressing challenges in this field. This is the mass spectrum of the novel episulfide compound in Example 1.This is the 1H NMR spectrum of the novel episulfide compound of Example 1.Figures 2 and 3 show the 13C NMR spectra of the novel episulfide compound of Example 1. 1H NMR ( CDCl3 ) δ = 2.21 ppm (1H), δ = 2.32 ppm (2H), δ = 3.02 ppm (2H); 13C NMR ( CDCl3 ) δ = 24.8 ppm, 28.6 ppm, 63.7 ppm. The above-mentioned content of the present invention will be specifically described below in the form of examples, but this does not mean that the scope of the subject matter of the present invention is limited to the following examples. All techniques implemented based on the above-mentioned content of the present invention fall within the scope of the present invention, and unless otherwise specified, all raw materials used in the following examples are commercially available products. To further illustrate the present invention, the following embodiments will be described in detail. 1) Burnt Shard Rate: Burnt shards refer to the phenomenon where impurity spots appear near the center of the substrate during the substrate cleaning process, due to the influence of alkali concentration and temperature. In the embodiments of the present invention, 100 ultrasonically cleaned substrates were visually inspected to identify those with burnt shards, and the burnt shard rate was calculated. 2) Yield: Product A has no impurity spots within a central radius of 3 cm. Product B has no impurity spots within a central radius of 1.5 cm, but has impurity spots between 1.5 and 3 cm. Product C contains leaf-like impurities within a central radius of 1.5 cm. Of these, Products A and B are acceptable, while Product C is unacceptable. In the examples of the present invention, 100 ultrasonically cleaned substrates were visually inspected to confirm whether impurity spots were present within different central radii, and the yield was calculated. (Example 1) Method for producing the episulfide compound represented by formula (1): 81 g (0.5 mol) of the compound represented by formula (3) above, 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 at 30°C for 12 hours. This crude product was separated and purified using a silica gel column by a conventional method to obtain 48.5 g (0.25 mol) of the episulfide compound represented by formula (1) above. The episulfide compound represented by equation (1) was characterized by mass spectrometry and nuclear magnetic resonance spectroscopy. The results are shown in Figure 1-3. Mass spectrum (ESI): [M + H] + = 194.9972. (Example 2) 88.4 g of bis(β-epithiopropyl) sulfide, 0.1 g of an 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 are mixed and stirred for 50 minutes to obtain a prepolymer solution. The density ρ before solidification is measured using a liquid densimeter. After vacuum degassing the prepolymer solution for 30 minutes, it is filtered through a polytetrafluoroethylene filter membrane with a pore size of 3 μm and poured into a glass mold. Next, this mold is placed in a programmed temperature curing oven for primary curing to obtain a primary cured resin lens. The heating program for primary curing is as follows: The initial temperature was 20°C, and after holding for 2 hour