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Compound containing pentazole ring bisazo structure, as well as preparation method and application thereof

A technology of azole ring bisazo and azole ring azo is applied in the field of compounds containing five-membered azole bicyclic azo structures, and can solve the problem that the coverage of chromophore bopp is not wide enough, the monomer conversion rate is not high enough, and the polymerization rate is not enough. It is not fast enough to achieve the effects of increasing solubility and catalytic performance, broadening the range of chromophores, and narrowing the molecular weight distribution.

Inactive Publication Date: 2013-09-04
YANCHENG INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The purpose of the present invention is to provide a compound containing five-membered azole ring disazo structure and its preparation method, and the application of this type of compound in ATRP polymerization, so as to solve the problem that the polymerization rate of monoazo structure is not fast enough at room temperature. The reaction time monomer conversion rate is not high enough, the conjugation is not high enough, and the coverage of chromophore pop is not wide enough

Method used

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  • Compound containing pentazole ring bisazo structure, as well as preparation method and application thereof
  • Compound containing pentazole ring bisazo structure, as well as preparation method and application thereof
  • Compound containing pentazole ring bisazo structure, as well as preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0030] Take 0.5-3g of 2-aminoimidazole to make a sulfate solution, and cool it in an ice bath. Take 0.5-2g of aniline and 0.5-2g of sodium nitrite, add hydrochloric acid aqueous solution to form a solution, and cool it to below 2°C with an ice bath. The aniline solution was slowly added dropwise to the sulfate solution with stirring while keeping the temperature below 2 °C. After the dropwise addition, continue to stir at below 5°C for 5 hours, adjust to neutrality with ammonia water, filter the reaction solution with suction and wash with a large amount of deionized water to obtain an intermediate containing an azo structure of an imidazole ring.

[0031] Take 0.5-3g of the intermediate containing the imidazole ring azo structure to make a sulfate solution, and cool it in an ice bath. Take 0.5-2g of phenol and 0.5-2g of sodium nitrite, add sodium hydroxide aqueous solution to form a solution, and cool it to below 2°C with an ice bath. The phenol solution was slowly added dr...

Embodiment 2

[0035] Take 0.5-3g of 2-amino-5-nitro-imidazole to make a sulfate solution, and cool it in an ice bath. Take 0.5-2g of aniline and 0.5-2g of sodium nitrite, add hydrochloric acid aqueous solution to form a solution, and cool it to below 2°C with an ice bath. The aniline solution was slowly added dropwise to the sulfate solution with stirring while keeping the temperature below 2 °C. After the dropwise addition, continue to stir at below 5°C for 5 hours, adjust to neutrality with ammonia water, filter the reaction solution with suction and wash with a large amount of deionized water to obtain an intermediate containing 5-nitroimidazole ring azo structure.

[0036] Take 0.5-3g of the intermediate containing 5-nitroimidazole ring azo structure to prepare a sulfate solution, and cool it in an ice bath. Take 0.5-2g of phenol and 0.5-2g of sodium nitrite, add sodium hydroxide aqueous solution to form a solution, and cool it to below 2°C with an ice bath. The phenol solution was sl...

Embodiment 3

[0040] Take 0.5-3g of 2-amino-5-methoxy-imidazole to make a sulfate solution, and cool it in an ice bath. Take 0.5-2g of aniline and 0.5-2g of sodium nitrite, add hydrochloric acid aqueous solution to form a solution, and cool it to below 2°C with an ice bath. The aniline solution was slowly added dropwise to the sulfate solution with stirring while keeping the temperature below 2 °C. After the dropwise addition, continue to stir at below 5°C for 5 hours, adjust to neutrality with ammonia water, filter the reaction solution with suction and wash with a large amount of deionized water to obtain an intermediate containing 5-methoxyimidazole ring azo structure.

[0041] Take 0.5-3g of the intermediate containing 5-methoxyimidazole ring azo structure to make a sulfate solution, and cool it in an ice bath. Take 0.5-2g of phenol and 0.5-2g of sodium nitrite, add sodium hydroxide aqueous solution to form a solution, and cool it to below 2°C with an ice bath. The phenol solution was...

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Abstract

The invention discloses an initiator containing a pentazole ring bisazo structure, which has an ATRP (atom transfer radical polymerization) performance at the room temperature of 30 DEG C on a (methyl) acrylic monomer. The preparation of the initiator comprises the steps that 5-substituted aminoimidazole, aniline and phenol have diazonium-coupling reaction twice, an intermediate containing the pentazole ring bisazo structure is obtained, and the intermediate reacts with bromo-isobutyryl bromide, so that the initiator containing the pentazole ring bisazo structure is obtained. The initiator is used for initiating the (methyl) acrylic monomer to perform ATRP at the room temperature of 30 DEG C, so that obtained polymers are controllable in molecular weight and narrow in molecular weight distribution, and further, polymers with different molecular weight have different colors according to different R groups.

Description

technical field [0001] The invention relates to a compound containing a five-membered azole bicyclic azo structure, in particular to a compound containing a five-membered azole ring bicyclic azo structure which has the characteristics of initiating ATRP polymerization of (meth)acrylate monomers at room temperature (30°C) compound. Background technique [0002] In 1995, Matyjaszewski's research group and Sawamoto and their colleagues independently discovered a "living" free radical polymerization method - atom transfer radical polymerization (ATRP). [0003] At present, the effective initiators of ATRP are mostly α-halogenated phenyl compounds, α-halogenated carbonyl compounds and α-halogenated nitrile compounds. Such as α-chlorophenylethane, α-butyl bromopropionate, α-chloroacetonitrile, etc. Functionalized ATRP initiators include α-halogenated esters and benzyl halides containing hydroxyl, amine, ester, epoxy, vinyl, and alkyl groups. [0004] As a polymerization method,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/88C07D233/92C08F120/14C08F4/04
Inventor 张良
Owner YANCHENG INST OF TECH
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