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A kind of polyimidazoline compound and preparation method thereof

A polyimidazoline compound technology, applied in the field of polyimidazoline compounds and their preparation, can solve the problems of blank polymer synthesis methods, etc., and achieve the effects of high polymerization efficiency, high thermal stability, and good functional group tolerance

Active Publication Date: 2020-11-24
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 heterocyclic compounds, imidazoline has been widely used in biomedicine and other fields, and its small molecule synthesis methods have been reported a lot. However, the polymer synthesis method of introducing imidazoline ring into the polymer backbone is still blank.

Method used

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  • A kind of polyimidazoline compound and preparation method thereof
  • A kind of polyimidazoline compound and preparation method thereof
  • A kind of polyimidazoline compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] (1) The synthetic method of the first monomer binary isocyano compound 1a is as follows,

[0057]

[0058] (2) The synthetic method of the second monomer disulfonimide compound 2a is as follows,

[0059]

[0060] (3) Polymerization of isocyano-sulfonimide to prepare polyimidazoline compounds P1a2a

[0061]

[0062] Add 50.5 mg (0.20 mmol) of the first monomer, 126.6 mg (0.20 mmol) of the second monomer, 2.0 mg (0.02 mmol) of cuprous chloride and 10.5 mg (0.04 mmol) of triphenylphosphine into a 10 mL polymerization tube, The nitrogen gas was replaced three times, 2 mL of dichloromethane was added, and after the monomer was completely dissolved, the temperature was raised to 40°C. React for 8 hours. After the reaction solution was diluted with 2 mL of dichloromethane, it was added dropwise into 150 mL of rapidly stirring n-hexane through a cotton filter to obtain a white flocculent precipitate. Stand overnight, filter and dry to obtain the target polymer.

[...

Embodiment 2～3

[0070] Examples 2-3 investigated the influence of triphenylphosphine in the catalyst 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) are shown in Table 1.

[0071] Table 1 Effect of triphenylphosphine on polymerization of monomers 1a and 2a a

[0072]

[0073] a Reaction in dichloromethane under nitrogen for 4h; T=40°C; [M] 0 = 100 mM.

[0074] b Determined by GPC, using linear polymethyl methacrylate as a calibration substance and DMF as a mobile phase.

[0075] By comparison, we found that the addition of triphenylphosphine greatly promoted the occurrence of the polymerization reaction. Under the same conditions, the polymerization reaction with addition of triphenylphosphine resulted in higher yield and higher molecular weight.

Embodiment 4～7

[0077] Examples 4-7 investigated the influence of different solvents on the reaction conditions. The preparation of the polymerized monomers is the same as in Example 1. The reaction conditions and results of step (3) are shown in Table 2.

[0078] Table 2 The influence of solvent on the polymerization of monomer 1a and 2a a

[0079]

[0080] a Reaction in different solvents under nitrogen for 4h; T=40°C; [M] 0 = 100 mM.

[0081] b Determined by GPC, using linear polymethyl methacrylate as a calibration substance and DMF as a mobile phase.

[0082] As can be seen in Table 2, DMF is not conducive to the occurrence of the polymerization reaction, and other solvents such as DCM, THF, chloroform, etc. can well occur the polymerization reaction. Considering productive rate, weight average molecular weight (M w ), the polydispersity coefficient We choose dichloromethane as the optimal conditions for the polymerization reaction.

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Abstract

The invention discloses a method for preparing a polyimidazoline compound. The method comprises the following step: carrying out a polymerization reaction on a binary isonitrile group compound, a binary sulfimide compound and a catalyst in an organic solvent, thereby obtaining the polyimidazoline compound, wherein the polymerization catalyst comprises cuprous chloride and triphenylphosphine. The method is simple to operate, efficient in reaction, free of heating and energy-saving and environmental-friendly, and can be carried out at the room temperature. The invention further discloses the polyimidazoline compound prepared by using the method. The polyimidazoline compound has good workability and high thermal stability.

Description

technical field [0001] The invention relates to high molecular polymers, in particular to a polyimidazoline compound and a preparation method thereof. Background technique [0002] As a class of nitrogen-containing heterocyclic compounds, imidazoline has been widely used in biomedicine and other fields, and its small molecule synthesis methods have been reported a lot. However, the polymer synthesis method of introducing imidazoline ring into the polymer backbone is still blank. Contents of the invention [0003] In order to overcome the above-mentioned shortcomings and deficiencies of the prior art, the object of the present invention is to provide a preparation method of polyimidazoline compounds, which is simple in operation, highly efficient in reaction, can be carried out at room temperature, does not need heating, and is energy-saving and environment-friendly. [0004] Another object of the present invention is to provide the polyimidazoline compound prepared by the ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G73/06
CPCC08G73/0616
Inventor 唐本忠程天宇秦安军赵祖金胡蓉蓉王志明
Owner SOUTH CHINA UNIV OF TECH
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