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Polythiourea compound ands preparation method and application thereof

A compound and a technology for polythiourea, applied in the field of polythiourea compounds and their preparation, can solve the problems of limited types of isothiocyanates, expensive imidazole monomers, generation of by-products, etc. The effect of adaptability and high polymerization efficiency

Active Publication Date: 2021-08-24
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Methods A-D can only synthesize symmetrical polythioureas, and the resulting product structure is limited, and A requires microwave conditions and acid catalysts, the thiophosgene used in B is a highly toxic substance, the imidazole monomer used in C is expensive and has by-products, and D In the process, highly toxic gas hydrogen sulfide is produced; E and F two methods can synthesize symmetric and asymmetric polythiourea, but the type of isothiocyanate used in E is extremely limited and the synthesis is relatively difficult, and the isocyanide used in F Compounds also need to be finely synthesized, which greatly increases the cost

Method used

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  • Polythiourea compound ands preparation method and application thereof
  • Polythiourea compound ands preparation method and application thereof
  • Polythiourea compound ands preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] A symmetrical polythiourea compound whose structural formula is shown in P1; a thioformamide compound whose structural formula is shown in M1:

[0053]

[0054] The polythiourea compound and thioformamide compound are prepared by direct one-pot reaction of isonitrile, amine and carbon disulfide, and the reaction equation is as formula (2):

[0055]

[0056] Wherein, the monomers used can be purchased from the market. 1a is 1,4-xylylenediamine, purchased from Anaiji Chemical in this example. 2 is p-toluenesulfonylmethyl isonitrile, purchased from Biide Pharmaceutical Technology Co., Ltd. in this example. In this example, carbon disulfide was also purchased from Anaiji Chemical.

[0057] The preparation steps of described polythiourea compound and thioformamide compound are as follows:

[0058] Add monomers 1a (136mg, 1mmol) and 2 (195mg, 1mmol) sequentially into a 10ml polymerization tube, then add 2mL dimethyl sulfoxide, stir at room temperature, after the mono...

Embodiment 2

[0061] A symmetrical polythiourea compound whose structural formula is shown in P2, a thioformamide compound whose structural formula is shown in M1:

[0062]

[0063] The polythiourea compound and the thioformamide compound are prepared by direct one-pot reaction of isonitrile, amine and carbon disulfide, and the reaction equation is as formula (3):

[0064]

[0065] Wherein, the monomers used can be purchased from the market, and the monomer 1b is 1,2-bis(2-aminoethoxy)ethane, purchased from TCI Company in this example. 2 is p-toluenesulfonylmethyl isonitrile, purchased from Biide Pharmaceutical Technology Co., Ltd. in this example. In this example, carbon disulfide was purchased from Anaiji Chemical.

[0066] The preparation steps of described polythiourea compound and thioformamide compound are as follows:

[0067] Add monomers 1b (148mg, 1mmol) and 2 (195mg, 1mmol) sequentially into a 10ml polymerization tube, then add 2mL dimethyl sulfoxide, stir at room temperat...

Embodiment 3

[0070] A sequence-controllable asymmetric polythiourea compound whose structural formula is shown in P3, and a thioformamide compound whose structural formula is shown in M1:

[0071]

[0072] The polythiourea compound and thioformamide compound are prepared by a one-pot reaction of isonitrile, amine and carbon disulfide, and the reaction equation is as formula (4):

[0073]

[0074] Wherein, the monomers used can be purchased from the market. Monomer 1a is 1,4-xylylenediamine, purchased from Anaiji Chemicals in this example. Monomer 1c is 4,4'-diaminodiphenyl ether, purchased from TCI in this example. 2 is p-toluenesulfonylmethyl isonitrile, purchased from Biide Pharmaceutical Technology Co., Ltd. in this example. In this example, carbon disulfide was purchased from Anaiji Chemical.

[0075] The preparation steps of described polythiourea compound and thioformamide compound are as follows:

[0076] Add monomers 1a (136mg, 1mmol) and 2 (390mg, 2mmol) sequentially int...

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Abstract

The invention discloses a polythiourea compound and a preparation method and application thereof. The method comprises the following steps: reacting an amine compound monomer, an isonitrile compound monomer and carbon disulfide in an organic solvent, and carrying out post-treatment to obtain the polythiourea. The monomers used in the invention are all industrial raw materials, the cost is low, and large-scale gram-level production can be carried out; the utilization rate of reaction atoms is 100%, and no toxic or harmful by-product is generated; the reaction can be carried out under the conditions of room temperature and air, the operation is simple, and the polymerization reaction yield is high; the product is easy to separate, and a polythiourea product and another thioformamide product can be obtained in one pot; symmetrical polythiourea, asymmetrical polythiourea with a controllable sequence and polythiourea with a disordered structure can be prepared by adjusting the feeding type, mode and proportion; the obtained series of polythiourea also has excellent self-repairing performance and luminescence performance, can be applied to the field of self-repairing and the field of photoelectric devices, and promotes further development of polythiourea compounds.

Description

technical field [0001] The invention belongs to the fields of organic chemistry, macromolecular chemistry and material science, and specifically relates to a polythiourea compound and its preparation method and application. Background technique [0002] Polythiourea has attracted much attention due to its excellent properties, such as high refractive index, strong metal coordination ability, strong self-healing performance, excellent electrochemical and dielectric properties, etc.; thioformamide as an efficient Synthons are widely used in organic chemistry. However, the research on polythiourea is still quite limited and faces many challenges, especially in terms of the synthesis method of polythiourea, there are some defects in the existing methods, which seriously limit the development and further application of this type of polymer. . The synthesis method of polythiourea is shown in formula (1) (ACS Macro Lett.2017,6,500.; J.Hazard.Mater.2010,175,1113.; Science 2018,359...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G73/00
CPCC08G73/00
Inventor 唐本忠胡蓉蓉张杰秦安军赵祖金王志明
Owner SOUTH CHINA UNIV OF TECH
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