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Ethoxy (2) bisphenol S diacrylate and preparation method thereof

A technology of diacrylate and ethoxylation, which is applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc. It can solve the problems that small and medium-sized enterprises cannot afford, the catalyst regeneration process is complicated, and the catalytic efficiency is low, so as to achieve safety High, low cost, high catalytic efficiency

Active Publication Date: 2015-01-28
SHANGHAI WEIKAI CHEM +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Solid acids such as strongly acidic ion exchange resins are unaffordable for small and medium-sized enterprises due to their high cost, low catalytic efficiency, complex catalyst regeneration process, and complex equipment.

Method used

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  • Ethoxy (2) bisphenol S diacrylate and preparation method thereof
  • Ethoxy (2) bisphenol S diacrylate and preparation method thereof
  • Ethoxy (2) bisphenol S diacrylate and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041]Add 19.0 grams of dihydroxyethyl bisphenol S (0.056mol, 0.112mol-OH, 1eq, 2eq-OH) and 12.1 grams of acrylic acid ( 0.16mol, 3.0eq, 1.5eq-OH), 46 grams of toluene, 0.54 grams of methanesulfonic acid (0.0056mol, 10eq%), 0.16 grams of p-hydroxyanisole (0.5wt%), nitrogen protection has been passed during the reaction , after reflux reaction at 110-115°C for 6 hours, a brownish-red liquid was obtained, and about 2.0 ml of water was generated. TLC analysis (exhibiting liquid: volume of ethyl acetate / volume of cyclohexane=1 / 1) has not observed dihydroxy Ethyl bisphenol S(R f =0.07) points; and only the product ethoxylated (2) bisphenol S diacrylate (R f =0.86), the reaction was stopped.

[0042] After the reaction, the reaction mixture was washed twice with 5% aqueous sodium hydroxide solution, then washed three times with distilled water, and finally dried with anhydrous magnesium sulfate, and then 0.03 p-hydroxyanisole, a polymerization inhibitor, was added to the dried sol...

Embodiment 2

[0044] Add 19.0 grams of dihydroxyethyl bisphenol S (0.056mol, 0.112mol-OH, 1eq, 2eq-OH) and 12.1 grams of acrylic acid ( 0.16mol, 3.0eq, 1.5eq-OH), 46 grams of toluene, 0.96 grams of p-toluenesulfonic acid (0.0056mol, 10eq%), 0.16 grams of p-hydroxyanisole (0.5wt%), nitrogen protection has been passed during the reaction , after reflux reaction at 110-115°C for 6.5 hours, a brownish-red liquid was obtained, and about 2.0 ml of water was generated. TLC analysis (exhibited liquid: volume of ethyl acetate / volume of cyclohexane=1 / 1) has not observed dihydroxy Ethyl bisphenol S(R f =0.07) points; and only the product ethoxylated (2) bisphenol S diacrylate (R f =0.86), the reaction was stopped.

[0045] After the reaction, the reaction mixture was washed twice with 5% aqueous sodium hydroxide solution, then washed three times with distilled water, and finally dried with anhydrous magnesium sulfate, and then 0.03 p-hydroxyanisole, a polymerization inhibitor, was added to the dried...

Embodiment 3

[0047] The technical scheme of embodiment 3 is identical with embodiment 1, only difference is as follows:

[0048] (1) The mol ratio of dihydroxyethyl bisphenol S and acrylic acid is 1:2.2;

[0049] (2) The consumption of solvent toluene is 0.8 times of the weight sum of dihydroxyethyl bisphenol S and acrylic acid;

[0050] (3) The consumption of p-toluenesulfonic acid is 2% of the molar weight of dihydroxyethyl bisphenol S;

[0051] (4) polymerization inhibitor is p-hydroxyanisole, and its consumption is 0.1% of the gross weight of dihydroxyethyl bisphenol S and acrylic acid;

[0052] (5) The esterification reaction time is 8 hours.

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Abstract

The invention provides an ethoxy (2) bisphenol S diacrylate and a preparation method thereof. The method comprises the following steps: carrying out esterification reaction on dihydroxyethyl bisphenol S and acrylic acid in a nitrogen protective atmosphere by using toluene as a solvent, organic acid as a catalyst and p-hydroxyanisole as a polymerization inhibitor; and after the esterification reaction finishes, removing the toluene by alkali washing, water washing, drying and depressurizing, recrystallizing the product with ethanol to obtain the ethoxy (2) bisphenol S diacrylate. The method is simple in technique, and can be used for preparing the bifunctional high-refractivity monomer ethoxy (2) bisphenol S diacrylate which simultaneously contains sulfur and benzene ring.

Description

technical field [0001] The invention relates to an ethoxylated (2) bisphenol S diacrylate and a preparation method thereof. Background technique [0002] In recent years, due to the rapid development of the optical material industry such as optical fiber, plastic grating, optical film for TFT-LCD backlight module, optical coating, optical adhesive, optical lens and resin lens manufacturing, the demand for high refractive index polymer materials more and more urgent. Therefore, the development of raw materials for high refractive index polymer materials - high refractive index monomers and resins has become a top priority. [0003] The traditional method is to introduce aromatic compounds or fused ring compounds to increase the refractive index, but the dispersion of the resulting polymer is relatively large. At present, the method of introducing sulfur into the polymer to increase the refractive index has received widespread attention in the academic circles. It is conside...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C317/22C07C315/04
Inventor 虞明东王艳梅蒋天龙王晨
Owner SHANGHAI WEIKAI CHEM
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