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1,3,5-tris(4-aminophenylmercapto)benzene as well as preparation method and application thereof

A kind of aminophenylthio group, aminothiophenol technology, applied in the field of 1,3,5-triphenyl and its preparation, can solve the problems of the improvement of refractive index, few reports and the like

Inactive Publication Date: 2015-05-06
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the introduction of sulfur and the improvement of the refractive index by halogen-modified end groups in hyperbranched systems have rarely been reported.

Method used

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  • 1,3,5-tris(4-aminophenylmercapto)benzene as well as preparation method and application thereof
  • 1,3,5-tris(4-aminophenylmercapto)benzene as well as preparation method and application thereof
  • 1,3,5-tris(4-aminophenylmercapto)benzene as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] 0.036mol (6.534g) 1,3,5-trichlorobenzene, 0.108mol (13.5g) 4-aminothiophenol, 0.9mol (87mL) N-methylpyrrolidone 1, 0.072mol (9.936g) anhydrous Potassium carbonate and 0.288mol (30mL) toluene were added to the reactor equipped with a water tank and a reflux condenser. Under mechanical stirring and nitrogen protection, the toluene was evaporated after heating to reflux with water for 4 hours, and the temperature was raised to 160°C to continue the reaction. After 12 hours, after cooling down to room temperature, discharge the material in deionized water, and wash 3 times with deionized water until the filtrate is colorless, then wash 2 times with ethanol, and dry in vacuum at 80°C for 4 to 8 hours to obtain 1,3,5 - Tris(4-aminophenylthio)benzene.

[0053] figure 1 The 300MHz test hydrogen spectrum of the monomer is given, and the chemical shifts of 1, 2, 3, and 4 marked in the figure correspond to the hydrogen on the benzene ring and the amine group respectively, and the...

Embodiment 2

[0057] Change the amount of 4-aminothiophenol to 0.1134mol (14.175g), the amount of N-methylpyrrolidone 1 to 1.08mol (104mL), the amount of potassium carbonate to 0.108mol (14.904g), and the amount of toluene Change it to 0.36mol (38mL), change the time of heating and refluxing with water to 6 hours, change the reaction temperature to 170°C, change the reaction time to 16 hours, change the number of deionized water washings to 4 times, and the number of ethanol washings to 3 times, Example 1 was repeated.

[0058] The characterization results are similar to Example 1.

Embodiment 3

[0060] Dissolve 2mmol (0.888g) of hexafluorodianhydride monomer in 0.08mol (7.73mL) of N-methylpyrrolidone 2 to obtain reaction solution 1; base) benzene was dissolved in 0.08mol (7.73mL) N-methylpyrrolidone 3 to obtain a reaction solution 2; at room temperature, the reaction solution 2 was added dropwise to the reaction solution 1 within 2 hours; during the polymerization process The viscosity of the medium solution gradually increased, and 0.2mol (19.32mL) of N-methylpyrrolidone 4 was added. After 8 hours of reaction, a polyamic acid solution was obtained, and the polyamic acid solution was cast onto a glass plate, and the temperature was raised as follows Steps for imidization: 60°C for 2 hours, 80°C for 2 hours, 100°C for 1 hour, 150°C for 1 hour, 200°C for 1 hour, and 250°C for 1 hour. After cooling down to room temperature naturally, take out the glass plate and place it in deionized water , A2+B3 type hyperbranched polyimide terminated by acid anhydride was obtained aft...

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Abstract

The invention belongs to the field of polymer materials and technical synthesis thereof, and particularly relates to 1,3,5-tris(4-aminophenylmercapto)benzene as well as a preparation method and application thereof. Thioether bonds are introduced into a triamine monomer to obtain 1,3,5-tris(4-aminophenylmercapto)benzene; and 1,3,5-tris(4-aminophenylmercapto)benzene and dianhydride, dianhydride and tetrachlorophthalic anhydride, or dianhydride and 3,5-dichloroaniline are taken as raw materials to prepare an anhydride-terminated, tetrachlorophthalic anhydride-terminated or 3,5-dichloroaniline-terminated A2+B3 type hyperbranched polyimide. According to the invention, the 1,3,5-tris(4-aminophenylmercapto)benzene monomer contains thioether bonds, so that the sulfur content of the hyperbranched polyimide is increased, and the thermal stability, solvent resistance, high refractive index and the like of the polymer are improved. Meanwhile, the branched structure and the end groups of the hyperbranched polyimide can be subjected to termination modification, so that the hyperbranched polyimide has a wide application prospect in many fields.

Description

technical field [0001] The invention relates to the field of polymer materials, in particular to 1,3,5-tris(4-aminophenylthio)benzene and its preparation method and application. Background technique [0002] Polyimide is an organic polymer material with excellent comprehensive properties, which is widely used in high-tech fields such as microelectronics, optoelectronics and aerospace. The imide ring structure in the polyimide molecular structure not only endows it with excellent heat resistance stability, mechanical properties, chemical stability, radiation resistance and dielectric properties, but also endows it with a high refractive index. Because of its anisotropy, linear polyimide has a high birefringence value, which limits its application in the optoelectronic field. [0003] The highly branched molecular structure of hyperbranched polyimide endows it with unique physical and chemical properties, such as three-dimensional spherical molecular shape, amorphous, low cha...

Claims

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Application Information

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IPC IPC(8): C07C319/14C07C323/37C08G73/10
Inventor 关绍巍宋颖刘善友姚洪岩檀海维由凯元
Owner JILIN UNIV
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