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Benzothiazole azo compound, synthesizing method and usage thereof

A benzothiazole azo compound technology, applied in the field of benzothiazole azo compounds, can solve the problem of high temperature of ATRP polymerization, and achieve the effects of narrow molecular weight distribution, reduced energy consumption, and controllable molecular weight

Inactive Publication Date: 2007-09-26
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The object of the present invention is to provide a kind of benzothiazole azo compound and its preparation method, and the application of this kind of compound in ATRP polymerization reaction, to solve the problem of high temperature of ATRP polymerization

Method used

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  • Benzothiazole azo compound, synthesizing method and usage thereof
  • Benzothiazole azo compound, synthesizing method and usage thereof
  • Benzothiazole azo compound, synthesizing method and usage thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0026] Take 1-3g of 2-aminobenzothiazole to make a sulfate solution, cool it in an ice bath, add 5-6g of 15-20% sodium nitrite aqueous solution dropwise, and react in an ice bath for 1 hour to obtain benzothiazole diazonium salt solution. Take 1 g of phenol, add 10 g of absolute ethanol and stir to dissolve, cool the ethanol solution of phenol to below 15°C, add the above diazonium salt solution dropwise, and react under ice bath for 24 hours. Filtration and washing with plenty of water yielded the benzothiazole azo intermediate.

[0027] Take 2-3g of benzothiazole azo intermediate, dissolve it in 40ml of tetrahydrofuran, add 1-3ml of triethylamine, and stir evenly under ice bath. Take 3-5g of bromoisobutyryl bromide and slowly add it dropwise to the above solution, react under ice bath for 1-3 hours, and then react at room temperature for 4-6 hours. The reaction solution was poured into water to precipitate and recrystallized to obtain the benzothiazole azo initiator.

[0...

Embodiment 2

[0030] Take 1-3g of 2-amino-6-nitrobenzothiazole to make a sulfate solution, cool it in an ice bath, add 5-6g of 15-20% sodium nitrite aqueous solution dropwise, and react in an ice bath for 1 hour to obtain 6- Nitrobenzothiazole diazonium salt solution. Take 1 g of phenol, add 10 g of absolute ethanol and stir to dissolve, cool the ethanol solution of phenol to below 15°C, add the above diazonium salt solution dropwise, and react under ice bath for 24 hours. Filtration and washing with plenty of water gave 6-nitrobenzothiazolyl azo intermediate.

[0031] Take 2-3g of 6-nitrobenzothiazole azo intermediate, dissolve it in 40ml of tetrahydrofuran, add 1-3ml of triethylamine, and stir evenly under ice bath. Take 3-5g of bromoisobutyryl bromide and slowly add it dropwise to the above solution, react under ice bath for 1-3 hours, and then react at room temperature for 4-6 hours. The reaction solution was poured into water to precipitate and recrystallized to obtain 6-nitrobenzoth...

Embodiment 3

[0034] Take 1-3g of 2-amino-6-methoxybenzothiazole to make a sulfate solution, cool it in an ice bath, add 5-6g of 15-20% sodium nitrite aqueous solution dropwise, and react in an ice bath for 1 hour to obtain 6 -Methoxybenzothiazole diazonium salt solution. Take 1 g of phenol, add 10 g of absolute ethanol and stir to dissolve, cool the ethanol solution of phenol to below 15°C, add the above diazonium salt solution dropwise, and react under ice bath for 24 hours. Filtration and washing with plenty of water gave 6-methoxybenzothiazolyl azo intermediate.

[0035] Take 2-3g of 6-methoxybenzothiazole azo intermediate, dissolve it in 40ml of tetrahydrofuran, add 1-3ml of triethylamine, and stir evenly under ice bath. Take 3-5g of bromoisobutyryl bromide and slowly add it dropwise to the above solution, react under ice bath for 1-3 hours, and then react at room temperature for 4-6 hours. The reaction solution was poured into water to precipitate and recrystallized to obtain 6-meth...

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Abstract

The invention discloses an o-(methyl)-acrylic ester monomer, which is characterized by the following: adopting polymeric benzopyrene azo under 30 deg.c; coupling 6-subsituted amino acid benzopyrene and phenol to obtain the intermediate of benzopyrene azo; reacting with bromo-isobutyryl to obtain the product with different colors.

Description

technical field [0001] The invention relates to a benzothiazole azo compound, in particular to a benzothiazole azo compound with the property of initiating ATRP polymerization of (meth)acrylate monomers at room temperature (30° C.). 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, ATRP has the following advantages: activity / controllability, molecular wei...

Claims

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Application Information

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IPC IPC(8): C07D277/82C08F4/04C08F20/10
Inventor 路建美张良徐庆锋夏雪伟王丽华
Owner SUZHOU UNIV
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