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Novel thiol compound and polymerizable composition containing same

A technology of polymeric composition and thiol compound, which is applied in thiol preparation, organic chemistry, instruments, etc., can solve the problems of high production cost, reduced reactivity, and increase in production cost of optical materials, and achieve the effect of saving production cost

Inactive Publication Date: 2017-02-22
KOC SOLUTION
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, compared with other plastic optical materials, urethane-based optical materials are mainly used as expensive high-refractive lenses due to their high production costs.
[0004] In particular, 2,3-bis(2-mercaptoethylthio)-3-propane-1-thiol (GST), 2-(2-mercaptoethylthio ) Propane-1,3-dithiol (GMT), pentaerythritol tetrakis (3-mercaptopropionate) (PETMP) and other thiol compounds are expensive, which is a factor that increases the production cost of optical materials
In addition, as the thiol compound, 3,8-bis(isocyanatomethyl)tricyclo[5,2,1,02,6]decane, 3,9-bis (isocyanatomethyl)tricyclo[5,2,1,02,6]decane, 4,8-bis(isocyanatomethyl)tricyclo[5,2,1,02,6] Decane, 4,9-bis(isocyanatomethyl)tricyclo[5,2,1,02,6]decane, 2,5-bis(isocyanatomethyl)bicyclo[2,2 ,1]heptane, 2,6-bis(isocyanatomethyl)bicyclo[2,2,1]heptane, etc., can obtain high quality Optical materials, but when using isophorone diisocyanate, dicyclohexylmethane-4,4-diisocyanate (H 12 Inexpensive general-purpose isocyanate compounds such as MDI) and 1,6-hexamethylene diisocyanate have lower reactivity, and quality deterioration such as streaks, whitening, and microfoam often occurs during polymerization.

Method used

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  • Novel thiol compound and polymerizable composition containing same
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  • Novel thiol compound and polymerizable composition containing same

Examples

Experimental program
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Effect test

Synthetic example 1

[0051] BMHS1 (bis(2-mercaptoethyl)-2-hydroxysuccinate (bis(2-mercaptoethyl)-2- hydroxysuccinate))

[0052] Install a Dean-Stark (Dean-stark) device in a 1L reactor with adjustable temperature, and add malic acid (134.09g, 1.00 mole), 2-mercaptoethanol (156.26g, 2.00 mole), 130g Toluene and p-toluenesulfonic acid (11.41 g, 0.06 mol) were stirred and reacted for 7 hours while maintaining a reduced pressure of 100 Torr and an internal temperature of 50°C. The reaction was performed while removing water generated during the reaction using a Dean-Stark apparatus. The reaction was terminated when the amount of theoretically produced water was 36 g and 2-mercaptoethanol as a starting material by high performance liquid chromatography (HPLC) disappeared. If the reaction ends, then reduce the temperature of the reactor, when reaching room temperature, in order to remove residual p-toluenesulfonic acid, utilize 200g of NaHCO of 5 weight percent (wt%) 3 (aq) Slowly carry out neutra...

Synthetic example 2

[0054] BMHS2 (bis(2-mercaptoethyl)-2-hydroxysuccinate (bis(2-mercaptoethyl)-2- hydroxysuccinate))

[0055] Install the Dean-Stark device in a 1L reactor with adjustable temperature, and add malic acid (134.09g, 1.00 mole), 2-mercaptoethanol (160.20g, 2.05 mole), 200g of toluene, p- Toluenesulfonic acid (11.41 g, 0.06 mol) was stirred and reacted for 7 hours while maintaining a reduced pressure state of 100 torr and an internal temperature of 50°C. The reaction was carried out while removing water generated during the reaction from the reactants using a Dean-Stark apparatus. The reaction was terminated when the theoretical amount of water and 2-mercaptoethanol as a starting material obtained by high performance liquid chromatography disappeared. If the reaction ends, then reduce the temperature of the reactor, when reaching room temperature, in order to remove residual p-toluenesulfonic acid, utilize 200g of NaHCO of 5 weight percent 3 (aq) Slowly carry out neutralization...

Embodiment 1

[0059] The compound (BMHS1) prepared in the above Synthesis Example 1, 53.37g of 2,5(6)-bis(isocyanatomethyl)bicyclo[2.2.1]heptane (NBDI), as a release agent 0.12 g of Zelec UN, 1.50 g of 2-(2'-hydroxy-5-methylphenyl)-2H-benzotriazole as UV absorber, 0.05 dibutyl dichloride as polymerization initiator Tin, 20ppm of 1-hydroxyl-4-p-toluidine) anthraquinone (Blue), 10ppm of perionone dyes as organic dyes are put into the matching barrel with agitator installed, and nitrogen is used to replace air, thereby removing Match the air in the barrel. The mixed solution was defoamed for 1 hour under the condition of 1 torr. Thereafter, it was filtered through a filter made of 1 μm polytetrafluoroethylene (PTFE, Polytetrafluoroethylene), and poured into a glass mold fixed with adhesive tape. This mold was put into a polymerization oven, and the temperature was gradually raised to 25° C. to 130° C. over 21 hours to perform polymerization. After the polymerization was complete, the mold w...

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Abstract

The invention discloses a novel thiol compound and a polymerizable composition containing the same. The present invention provides a thiol compound and a polymerizable composition containing the same. The thiol compound and the polymerizable composition containing the same, of the present invention, are suitable for the production of urethane-based plastic materials satisfying both product quality and economic feasibility, and are suitable for the production of, especially, urethane-based plastic materials required to have colorless transparency and high or middle refractive property.

Description

technical field [0001] The present invention relates to novel thiol compounds and polymerizable compositions comprising them. Background technique [0002] Compared with optical materials made of inorganic materials, plastic optical materials are light and less fragile, and can be dyed. Recently, plastic materials of various resins are used in optical materials, and their required physical properties are also becoming higher. [0003] Urethanes are obtained by thermally curing polyisocyanate compounds and polythiol compounds in Korean Granted Patents 10-0136698, 10-0051275, 10-0051939, 10-0056025, 10-0040546, 10-0113627, etc. optical lens. Compared with other optical materials, urethane-based optical materials have excellent optical properties such as moldability, transparency, Abbe number, heat resistance, light resistance, weather resistance, transmittance, and tensile strength, and are suitable for coating and processing. Sex is also excellent. However, urethane-based...

Claims

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Application Information

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IPC IPC(8): C07C321/04C07C319/08C08G18/38G02B1/04
CPCC07C319/08C07C321/04C08G18/38G02B1/04
Inventor 张东奎卢守均
Owner KOC SOLUTION
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