Benzothiazole heterocyclic azo type water-soluble dye and preparation method thereof

A technology for heterocyclic azo-type, water-soluble dyes, applied in the field of dyes, to achieve the effects of broad application prospects, high sensitivity, and excellent acid-base discoloration performance

Pending Publication Date: 2021-11-23
QINGDAO TECHNOLOGICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

2-Amino-6-nitrobenzothiazole is used in disperse dyes and In water-insoluble dyes such as direct dyes, it is often used as a diazo component for the synthesis of high-performance azo dyes, but it is rarely used in reactive and acid dyes with a wide range of uses

Method used

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  • Benzothiazole heterocyclic azo type water-soluble dye and preparation method thereof
  • Benzothiazole heterocyclic azo type water-soluble dye and preparation method thereof
  • Benzothiazole heterocyclic azo type water-soluble dye and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] A benzothiazole heterocyclic azo type water-soluble dye, the specific structure is as follows:

[0048]

[0049] A method for preparing the above-mentioned benzothiazole heterocyclic azo type water-soluble dye:

[0050] Diazotization reaction: After cooling 11.0g of concentrated sulfuric acid with a mass fraction of 98% in an ice bath at 0-5°C, gradually add 0.73g of solid sodium nitrite, stir, and heat until completely dissolved, and the solution becomes clear and transparent , stop heating and cooling, gradually add 1.99g of 2-amino-6-nitrobenzothiazole (0.01mol, 98%), stir, then continue the reaction at 0~5°C, and detect the end point of the reaction by thin layer chromatography (TLC). After the reaction is completed, add a small amount of sulfamic acid to remove excess nitrous acid;

[0051] Condensation reaction of cyanuric chloride: take 1.90g cyanuric chloride (0.0103mol) and 20g small ice cubes, mechanically stir until milky at 0-5°C, then add 4.0g (0.01mol, 8...

Embodiment 2

[0056] A benzothiazole heterocyclic azo type water-soluble dye, the specific structure is as follows:

[0057]

[0058] A method for preparing the above-mentioned benzothiazole heterocyclic azo type water-soluble dye:

[0059] Diazotization reaction: same as the preparation in Example 1;

[0060] Condensation reaction of cyanuric chloride: take 1.90g cyanuric chloride (0.0103mol) and 20g small ice cubes, mechanically stir until milky at 0-5°C, then add 4.0g (0.01mol, 85.6%) H acid mono The aqueous solution of sodium salt, the solution adjusts pH between 4~5, detects and determines reaction end point with Ehrlich reagent; After reaction finishes, add 2.81g between (beta-sulfate ethyl sulfone) aniline (0.01mol), will The temperature is raised to 20-30°C, and the pH value is controlled between 5-6 with 10% sodium carbonate solution. After 3-4 hours of reaction, TLC detects the reaction end point (developing agent is n-butanol: isopropanol: ethyl acetate ester:water=2:4:1:3, ...

Embodiment 3

[0063] A benzothiazole heterocyclic azo type water-soluble dye, the specific structure is as follows:

[0064]

[0065] A method for preparing the above-mentioned benzothiazole heterocyclic azo type water-soluble dye:

[0066] Diazotization reaction: same as the preparation in Example 1;

[0067] Condensation reaction of cyanuric chloride: take 1.90g cyanuric chloride (0.0103mol) and 20g small ice cubes, mechanically stir until milky at 0-5°C, then add 4.0g (0.01mol, 85.6%) H acid mono An aqueous solution of sodium salt, the pH of the solution is adjusted between 4 and 5, and the end point of the reaction is determined by Ehrlich reagent detection; after the reaction is finished, add 1.77g of anthranilic acid (0.01mol, 98%) to raise the temperature To 20~30℃, use 10% sodium carbonate solution to control the pH value between 5~6, after reacting for 3~4 hours, TLC detects the reaction end point (developing agent is n-butanol: isopropanol: ethyl acetate: water =2:4:1:3, v / v)...

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Abstract

The invention relates to the technical field of dyes, in particular to a benzothiazole heterocyclic azo type water-soluble dye and a preparation method thereof. Weakly alkaline arylamine containing a heterocyclic structure in a molecule is used as a diazo component to be introduced into a water-soluble acidic or reactive dye structure, so that the acid-base color-changing dye is formed. The preparation method comprises the following steps: carrying out condensation reaction on cyanuric chloride, cyanuric fluoride, acetic anhydride or benzoyl chloride and aminonaphthol sulfonic acid to obtain a condensation product; carrying out diazotization reaction on 2-amino-6-nitrobenzothiazole; and carrying out coupling reaction on the diazotization reaction product and the condensation product. The benzothiazole heterocyclic azo type water-soluble dye provided by the invention has excellent acid-base discoloration performance, is simple in synthesis process, does not need any optical device, can rapidly detect the pH value of a solution directly through naked eye observation, has the advantages of high sensitivity, high selectivity, rapidness, reversibility, macroscopic visibility and the like, and has a wide application prospect.

Description

technical field [0001] The invention relates to the technical field of dyes, in particular to a benzothiazole heterocyclic azo water-soluble dye and a preparation method thereof. Background technique [0002] Azo-type dyes are a very important class of dyes due to their readily available raw materials, simple synthesis methods, and high light absorption coefficients. Since the azo bond is prone to tautomerization of the azo-quinone hydrazone structure, many monoazo water-soluble dyes often show different color differences in different acid-base environments. Study the pH color-changing effect of azo structural dyes It has also become a research hotspot in the field of dyes. 2-Amino-6-nitrobenzothiazole is used in disperse dyes and In water-insoluble dyes such as direct dyes, it is often used as a diazo component in the synthesis of high-performance azo dyes, but it is rarely used in reactive and acid dyes that are widely used. Contents of the invention [0003] In view ...

Claims

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Application Information

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IPC IPC(8): C09B29/00C09B29/36C07D277/82
CPCC09B29/0011C09B29/3691C07D277/82
Inventor 单斌孟德泉马继平
Owner QINGDAO TECHNOLOGICAL UNIVERSITY
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