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Method for preparing polythiourea by means of polymerizing multiple components of isocyanide, sulfur and amine and application of polythiourea

A polythiourea, multi-component technology, used in the analysis of materials, material excitation analysis, material analysis by optical means, etc., to achieve high yield, high atom economy, and good film formation.

Active Publication Date: 2018-09-25
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] There are various reactions for the synthesis of sulfur-containing polymers, but there is no report on the synthesis of polythiourea directly using elemental sulfur as a reactant

Method used

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  • Method for preparing polythiourea by means of polymerizing multiple components of isocyanide, sulfur and amine and application of polythiourea
  • Method for preparing polythiourea by means of polymerizing multiple components of isocyanide, sulfur and amine and application of polythiourea
  • Method for preparing polythiourea by means of polymerizing multiple components of isocyanide, sulfur and amine and application of polythiourea

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] A method for preparing polythiourea by multicomponent polymerization of isonitrile, sulfur and amine, the steps are as follows:

[0048] (1) Under the protection of inert gas, 81.7 mg of p-xylylenediamine, 93.7 mg of p-xylylenediacetonitrile and 76.9 mg of sublimed sulfur were added to 0.4 mL of N,N-dimethylformamide and 0.2 mL of toluene and mixed Dissolve in the solvent, heat up to 100 °C, and stir for 1 h;

[0049] (2) Cool to room temperature after the reaction, dilute the reaction mother liquor with 5 mL of N,N-dimethylformamide solution, and add it dropwise (the rate of dropwise addition is 2 drops / sec) into 100 mL of methanol solution for precipitation , the precipitate was collected, dried (the drying temperature was 60° C.) to constant weight, and the polythiourea was obtained. The product yield of this example was 88%, the weight-average molecular weight was 30,000 g / mol, and the PDI was 1.42.

[0050] The terephthalic acid nitrile of this embodiment is disc...

Embodiment 2

[0063] A method for preparing polythiourea by multicomponent polymerization of isonitrile, sulfur and amine, the steps are as follows:

[0064] (1) Under the protection of inert gas or air, mix 72 μL of dimethylpropanediamine (0.6 mmol), 229.5 mg of 1,2-bis-p-isocyanophenyl-1,2-diphenylethylene and 76.9 mg of Sublimation sulfur was added to 0.4 mL of N,N-dimethylformamide and 0.2 mL of toluene mixed solvent to dissolve, heated to 100°C, and reacted under stirring for 1 h;

[0065] (2) Cool to room temperature after the reaction, dilute the reaction mother liquor with 5 mL of N,N-dimethylformamide solution, and then add it dropwise (the rate of dropwise addition is 2 drops / sec) into 100 mL of methanol solution for precipitation , collect the precipitate, and dry (the drying temperature is 60° C.) to constant weight to obtain polythiourea P2. The product yield of this example was 89%, the weight average molecular weight was 24300 g / mol, and the PDI was 1.39.

[0066] The p-xyl...

Embodiment 3

[0077] A method for preparing polythiourea by multicomponent polymerization of isonitrile, sulfur and amine, the steps are as follows:

[0078] (1) Under the protection of inert gas or air, add 72 μL of dimethylpropanediamine, 81.6 mg of 1,6-adiponitrile and 76.9 mg of sublimed sulfur to 0.4 mL of N,N-dimethylmethane The amide was dissolved in a mixed solvent of 0.2 mL of toluene, heated to 100 °C, and reacted under stirring for 1 h;

[0079] (2) Cool to room temperature after the reaction, dilute the reaction mother liquor with 5 mL of N,N-dimethylformamide solution, and then add it dropwise (the rate of dropwise addition is 2 drops / sec) into 100 mL of methanol solution for precipitation , the precipitate was collected, dried (the drying temperature was 60° C.) to constant weight, and the polythiourea P3 was obtained. The yield of the reaction was >99%, the weight average molecular weight was 122500 g / mol, and the PDI was 2.35.

[0080] The reaction equation involved in thi...

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Abstract

The invention belongs to the technical field of sulfur-containing organic polymer preparation, and discloses a method for preparing polythiourea by means of polymerizing multiple components of isocyanide, sulfur and amine and application of the polythiourea. The method includes carrying out reaction on amine monomers, isocyanide monomers and elemental sulfur in solvents; cooling, precipitating anddrying reaction products to obtain the polythiourea. The amine monomers are diamine compounds, and the isocyanide monomers are binary isocyanide compounds. The method and the application have the advantages that the method can be implemented under room-temperature and air conditions, is simple and is high in polymerization reaction yield and atom economy, and the polythiourea which is a product is easy to separate; the polythiourea prepared by the aid of the method contains abundant N and S heteroatoms, has special photoelectric properties and has a potential unique application value in the field of biological and chemical fluorescence detection, metallic mercury ion detection and mercury ion removal; the polythiourea is high in metallic mercury ion detection sensitivity, good mercury ionremoval effects can be realized by the polythiourea, and the removal efficiency of the polythiourea is higher than 99.99% and can reach drinking water standards.

Description

technical field [0001] The invention belongs to the technical field of preparation of sulfur-containing organic polymers, in particular to a method for preparing polythiourea by multi-component polymerization of isonitrile, sulfur and amine and the application of the polythiourea obtained by the method. Background technique [0002] The introduction of heteroatoms such as O, N, S, and P into the polymer molecular chain can make the polymer have some special properties. The introduction of sulfur atoms into the molecular chain can make the polymer have a higher refractive index on the one hand, and on the other hand, the formation of some sulfur-containing functional groups can promote the polymer to form a metal coordination polymer, so that the polymer can be detected and enriched in metal ions. It has potential unique application value in terms of collection. At present, sulfur elements in polymers are usually introduced in the form of thioester bonds, thioether bonds, su...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G75/00C08G73/00G01N21/64
CPCC08G73/00C08G75/00G01N21/643G01N2021/6432
Inventor 唐本忠田甜胡蓉蓉秦安军赵祖金
Owner SOUTH CHINA UNIV OF TECH
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