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Carbazyl dithio formate RAFT reagent and its preparation method and use

A technology of carbazole dithiocarboxylate and potassium carbazole dithiocarboxylate is applied in the field of living radical polymerization, carbazole dithiocarboxylate RAFT reagent and preparation, and can solve the problem of not being able to store and synthesize for a long time. Complex process, harsh reaction conditions and other problems, to achieve the effect of easy control, mild reaction conditions and good control ability

Inactive Publication Date: 2005-07-06
TIANJIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The reported dithioester RAFT agents are mainly based on benzene rings, pyrroles and alkanes [3，4] , dithioester RAFT reagents based on benzene rings and alkanes are mostly produced by the Grignard reaction of halogenated benzenes to disulfuric acid, and then added to olefins. The synthesis process is complex, the reaction conditions are harsh, and the yield is low.
The product is usually a viscous liquid, which is usually separated by column chromatography, and it is difficult to separate and purify
Poor stability, cannot be stored for a long time even at low temperature

Method used

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  • Carbazyl dithio formate RAFT reagent and its preparation method and use
  • Carbazyl dithio formate RAFT reagent and its preparation method and use
  • Carbazyl dithio formate RAFT reagent and its preparation method and use

Examples

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example 1

[0031] In a 100ml round bottom flask, add 3.34g (0.02mol) of carbazole and 40ml of tetrahydrofuran solvent, and then add 0.46g (0.02mol) of finely chopped metallic sodium. Under nitrogen protection, react in a water bath at 10° C. for 10 hours. The reaction was stopped and unreacted sodium was filtered off. Then add 1.52g (0.02mol) of carbon disulfide, and control the reaction temperature at 10°C for 4 hours. Sodium N-carbazole dithioformate is obtained.

example 2

[0033] In a 100ml round bottom flask, add 3.34g (0.02mol) carbazole and 40ml acetone solvent, then add 3.2g (0.08mol) sodium hydroxide. Under nitrogen protection, react in a water bath at 64° C. for 2 hours, stop the reaction, and filter out unreacted sodium hydroxide. Then add 6.08g (0.08mol) of carbon disulfide, and control the reaction temperature at 42°C for 1 hour. Sodium N-carbazole dithioformate is obtained.

example 3

[0035] In a 100ml round bottom flask, add 3.34g (0.02mol) carbazole and 40ml DMF solvent, then add 3.18g (0.03mol) sodium carbonate. Under nitrogen protection, react in a water bath at 55° C. for 5 hours, stop the reaction, and filter out unreacted sodium carbonate. Then add 3.04g (0.04mol) of carbon disulfide, and control the reaction temperature at 38°C for 2 hours. Sodium N-carbazole dithioformate is obtained.

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Abstract

The invention discloses a carbazyl dithio formate RAFT reagent and its preparation process and use, which belongs to active free radical polymerization technology. The preparation process of reagents with following constitutional general formula comprises solving the carbazole and alkali in solvent, after some time, adding carbon bisulfide to produce N-carbazyl dithio formate at some temperature; adding benzyl halide, alpha-methyl benzyl halide or alpha, alpha-dimethyl benzyl halide to produce said three reagents. The RAFT reagent has good control capability for free radical polymerization of conjugated monomer, for example styrene, methyl methacrylate, etc.

Description

technical field [0001] The invention relates to a carbazole dithioformate RAFT reagent, a preparation method and an application thereof, which belong to the living radical polymerization technology. Background technique [0002] Since the 1970s, polymer chemists have been working on the research of living radical polymerization. But the real breakthrough in the study of living radical polymerization was in 1982 when Takayuki Otsu proposed the concept of Iniferter and applied it to living polymerization. This method realizes the control of free radical activity and chain growth reaction from a chemical point of view, and makes the study of living free radical polymerization enter a new stage of development. In the 1990s, nitroxide free radicals (TEMPO) were successively realized [1] , atom transfer radical (ATRP) [2] And reversible addition-fragmentation chain transfer radicals (Reversibleaddition-fragmentation chain transfer, RAFT) [3] and ot...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/82C08F2/38C08F220/04C08F220/12C08F220/56
Inventor 郭睿威戚桂村金启明方道斌
Owner TIANJIN UNIV
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