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Poly(alpha-carbonyl diazo alkane) as well as preparation method and application thereof

A carbonyldiazoalkane, carbonyl technology, applied in the field of polymer synthesis, can solve the problems of inability to obtain polymers, limit the application of C1 polymer products, etc., and achieve the effect of strong fluorescence performance

Inactive Publication Date: 2015-01-07
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, diazo compounds react violently in the presence of metals to release nitrogen gas, which cannot obtain polymers with carbon-nitrogen bonds in the main chain, thus limiting the further application of C1 polymerization products.

Method used

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  • Poly(alpha-carbonyl diazo alkane) as well as preparation method and application thereof
  • Poly(alpha-carbonyl diazo alkane) as well as preparation method and application thereof
  • Poly(alpha-carbonyl diazo alkane) as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037]Under anhydrous and oxygen-free conditions, using chloroform as a solvent, add the catalyst poly(N-isopropylacrylamide-co-N-isopropenylimidazole) base-copper(Ⅱ) under the condition of constant stirring and feeding argon gas , adding ethyl diazoacetate dropwise at a mass ratio of catalyst to ethyl diazoacetate of 1:50, heating and reacting at 60°C for 24 hours, after the reaction, filter out the catalyst, and use diethyl ether as a precipitating agent to obtain A large amount of white flocculent precipitates were dried to obtain a poly(ethyl diazoacetate) polymer product, and the conversion rate of the polymer was calculated to be 95.40%.

Embodiment 2

[0039] Under anhydrous and oxygen-free conditions, using toluene as a solvent, adding poly(N-isopropylacrylamide-co-N-isopropenylimidazole)-copper(II) catalyst under the condition of constant stirring and feeding argon , add ethyl diazoacetate drop by drop according to the mass ratio of catalyst to ethyl diazoacetate at a ratio of 1:20, heat and react at 20°C for 16 hours, after the reaction is over, filter out the catalyst, and use n-hexane as a precipitant A white flocculent precipitate was obtained, and the polymer product was obtained after the precipitate was dried, and the conversion rate of the poly(ethyl diazoacetate) polymer was calculated to be 53.67%.

Embodiment 3

[0041] Under anhydrous and oxygen-free conditions, using tetrahydrofuran as a solvent, add poly(N-isopropylacrylamide-co-N-isopropenylimidazole)-copper(II) catalyst under the condition of constant stirring and flowing argon gas , add ethyl diazoacetate dropwise at a ratio of 1:70 by weight of the catalyst and ethyl diazoacetate, heat and react at 60°C for 18 hours, after the reaction, filter out the catalyst, and use petroleum ether as a precipitant A white flocculent precipitate was obtained, and the polymer product was obtained after the precipitate was dried, and the conversion rate of the poly(ethyl diazoacetate) polymer was calculated to be 71.74%.

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Abstract

The invention discloses a polymer, namely poly(alpha-carbonyl diazo alkane), of which a main chain contains diazo groups as well as a preparation method and an application thereof. The preparation method comprises the following steps: by adopting polyheterocyclic radical-copper (II) as a catalyst, catalyzing an alpha-carbonyl diazo compound, preparing highly-functionalized poly(alpha-carbonyl diazo alkane) by virtue of polymerization, and ensuring that nitrogen is not easy to release by virtue of stabilization effects of polyheterocyclic radicals on reactive intermediate diazo free radicals, so that poly(alpha-carbonyl diazo alkane) of which a main chain contains the diazo groups and a side chain contains carbonyl functional groups can be prepared by participating in polymerization reaction by virtue of gradual transfer and insert steps. The preparation method disclosed by the invention is of a novel method for preparing the polymer with optical performance and high functionalization, and can be applied to the fields of optics, dyes, oil paint, printing, blending materials and the like.

Description

technical field [0001] The invention belongs to the field of polymer synthesis, and in particular relates to a poly(alpha-carbodiazoalkane) polymer and its preparation method and application. Background technique [0002] Metal catalysts catalyze diazonium compounds to release nitrogen to form metal carbenes, which can be used as active intermediates to participate in various reactions such as carbon-hydrogen bond functionalization reactions, cyclopropanation reactions of olefins, and carbene polymerization reactions. The metal-catalyzed polymerization reaction based on α-carbonyl diazo compound (C1 polymerization reaction) can obtain a polymer with a polar group attached to each carbon atom in the carbon chain, breaking through the conventional olefins that are inactive for free radical polymerization and cannot be obtained The limitations of highly functionalized polymers have attracted extensive attention from scholars at home and abroad. The polymerization of diazocarbo...

Claims

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Application Information

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IPC IPC(8): C08G73/00
Inventor 刘立建李非非肖龙强
Owner WUHAN UNIV
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