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Poly(enamine nitrile) compound and preparation method thereof

A technology of polyenaminonitrile and compound, which is applied in the field of polyenaminonitrile compounds and their preparation, can solve the problems of blank polymers and their synthesis methods, and achieve high polymerization efficiency, easy availability of reaction raw materials, and high thermal stability Effect

Active Publication Date: 2021-12-07
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] As a class of nitrogen-containing compounds, enaminonitrile has been widely used in organic synthesis, biosensing and other fields, and its small molecule synthesis methods have been reported in large numbers. but still blank

Method used

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  • Poly(enamine nitrile) compound and preparation method thereof
  • Poly(enamine nitrile) compound and preparation method thereof
  • Poly(enamine nitrile) compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] (1) The synthetic method of the first monomer binary isocyanide compound 1a is as follows,

[0060]

[0061] (2) The synthetic method of the second monomer binary nitrile compound 2a is as follows,

[0062]

[0063] (3) Preparation of polyenylamine nitrile compounds P1a2a by nitrile-isonitrile polymerization

[0064]

[0065] Add 69.5mg (0.20mmol) of the first monomer 1a, 60.5mg (0.20mmol) of the second monomer 2a, 3.8mg (0.02mmol) of cuprous iodide and 53.9mg (0.48mmol) of potassium tert-butoxide into a 10mL polymerization tube ), replace nitrogen three times, add 2mL of N,N-dimethylformamide, after the monomer is completely dissolved, raise the temperature to 40°C. React for 4 hours. The reaction solution was diluted with 2 mL of N,N-dimethylformamide, and added dropwise into 150 mL of rapidly stirring methanol through a cotton filter to obtain a white flocculent precipitate. Stand overnight, filter and dry to obtain the target polymer.

[0066] The polym...

Embodiment 2～3

[0073] Examples 2-7 investigated the influence of the reaction solvent on this polymerization reaction. The preparation of the polymer monomer was the same as in Example 1. The reaction conditions and results of step (3) were shown in Table 1.

[0074] The effect of table 1 reaction solvent on monomer 1a and 2a polymerization a

[0075]

[0076] a Reaction in different solvents under nitrogen for 4h; T=40°C; [M] 0 = 100 mM.

[0077] b Determined by GPC, using linear polymethyl methacrylate as a calibration substance and DMF as a mobile phase.

[0078] By comparing the data in Table 1, we found that the polymerization reaction can only occur in polar solvents N,N-dimethylformamide and dimethyl sulfoxide, because the prepared polyenamide can only be dissolved in polar solvents , poor solubility in solvents such as tetrahydrofuran, which limits the chain growth of the polymer. Compared with the polymerization results of N,N-dimethylformamide and dimethyl sulfoxide as poly...

Embodiment 8～14

[0080] Examples 8-14 investigated the influence of different temperatures on the reaction conditions. The preparation of polymerized monomers is the same as in Example 1. The reaction conditions and results of step (3) are shown in Table 2.

[0081] Table 2 Effect of Temperature on the Polymerization of Monomers 1a and 2a a

[0082]

[0083] a Reaction in N,N-dimethylformamide for 4h in nitrogen; [M] 0 = 100 mM.

[0084] b Determined by GPC, using linear polymethyl methacrylate as a calibration substance and DMF as a mobile phase.

[0085] As can be seen from Table 2, at room temperature (25 ° C), the polymerization reaction can also occur, and the yield is higher (70%), and the molecular weight is larger (M w =11200), which shows that the polymerization reaction can be economical, energy-saving and environmentally friendly at room temperature. When the reaction temperature is below 40°C, the higher the temperature, the higher the polymerization yield and the larger t...

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Abstract

The invention discloses a preparation method of a poly(enamine nitrile) compound, wherein the preparation method comprises the following steps: carrying out polymerization reaction on a binary nitrile compound, a binary isonitrile compound and a polymerization catalyst in an organic solvent to obtain the poly(enamine nitrile) compound, wherein the polymerization catalyst comprises cuprous iodide and potassium tert-butoxide. A polymerization reaction implementation process is simple in process, and reaction raw materials are easy to obtain and can be directly purchased or prepared through a simple reaction; polymerization reaction conditions are mild, polymerization can be carried out at room temperature, and energy is saved; the polymerization efficiency is high, and a polymer with relatively high molecular weight can be obtained after 4 hours of reaction; and no by-product is generated in the polymerization process, and the atom economy is met. The invention also discloses the poly(enamine nitrile) compound which has good processability and high thermal stability.

Description

technical field [0001] The invention relates to high molecular polymers, in particular to a polyenylaminonitrile compound and a preparation method thereof. Background technique [0002] As a class of nitrogen-containing compounds, enaminonitrile has been widely used in the fields of organic synthesis and biosensing, and its small molecule synthesis methods have been widely reported. But still blank. Contents of the invention [0003] In order to overcome the above-mentioned shortcomings and deficiencies of the prior art, the purpose of the present invention is to provide a polyenaminonitrile compound, which has good processability and high thermal stability by introducing enaminonitrile into the polymer main chain. [0004] Another object of the present invention is to provide a method for preparing polyenaminonitrile compounds, which is simple in operation and highly efficient in reaction. [0005] The object of the present invention is achieved through the following te...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G73/02
CPCC08G73/024
Inventor 唐本忠秦安军程天宇
Owner SOUTH CHINA UNIV OF TECH
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