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Direct red/direct violet dye compound as well as preparation method and application thereof

A dye compound and direct technology, applied in the field of dyes, can solve the problems of destroying the structure of dye compounds, large investment in equipment, complicated methods, etc., and achieve the effect of good product quality, less investment in equipment, and simple processing

Pending Publication Date: 2022-05-27
INST OF ANALYSIS GUANGDONG ACAD OF SCI (CHINA NAT ANALYTICAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the transformation of direct dyes requires either complex methods and large investment in equipment, or when the dye is reduced, the azo bond will be destroyed and the structure of the dye compound will be destroyed.

Method used

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  • Direct red/direct violet dye compound as well as preparation method and application thereof
  • Direct red/direct violet dye compound as well as preparation method and application thereof
  • Direct red/direct violet dye compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046]

[0047] The preparation method of 8-amino-4-hydroxy-3-((4-aminophenyl)diazenyl)naphthalene-2-sodium sulfonate, comprising the steps:

[0048] (1) Preparation of intermediate 8-amino-4-hydroxy-3-((4-nitrophenyl)diazenyl)naphthalene-2-sulfonic acid sodium: weigh p-nitroaniline (2.76g, 20mmol) In a 250mL beaker, add 60mL of dilute hydrochloric acid with a concentration of 1M and 20g of crushed ice, stir evenly, and slowly add 22mL of sodium nitrite solution with a concentration of 1M dropwise into it. Aniline diazonium salt solution, set aside. Weigh sodium 8-amino-4-hydroxynaphthalene-2-sulfonate (5.22g, 20mmol) and sodium hydroxide (1.60g, 40mmol) into a 500mL beaker, add 100mL of 0.6M saturated sodium carbonate solution, and stir After homogeneous, the solution of p-nitroaniline diazonium salt was added dropwise thereto, and the dropwise addition was completed, and the reaction was continued for 120 minutes to obtain a reddish-brown suspension. Centrifuged and dri...

Embodiment 2

[0052]

[0053] The preparation method of 4-amino 5-hydroxyl-6-((4-aminophenyl)diazenyl)naphthalene-1-sulfonic acid, comprises the steps:

[0054] (1) Preparation of intermediate 4-amino-5-hydroxy-6-((4-nitrophenyl)diazenyl)naphthalene-1-sulfonic acid: p-nitroaniline (2.76 g, 20 mmol) was weighed to In a 250mL beaker, add 60mL of dilute hydrochloric acid with a concentration of 1M and 20g of crushed ice, stir evenly, and slowly add 22mL of sodium nitrite solution with a concentration of 1M dropwise into it. After the dropwise addition, continue stirring for 60 minutes to obtain p-nitroaniline diazonium salt solution, ready to use. Weigh 4-amino-5-hydroxynaphthalene-1-sulfonic acid (20 mmol) and sodium hydroxide (1.60 g, 40 mmol) into a 500 mL beaker, add 100 mL of saturated sodium carbonate solution with a concentration of 0.6 M, stir evenly, and add to it P-nitroaniline diazonium salt solution was added dropwise, the dropwise addition was completed, and the reaction was c...

Embodiment 3

[0058]

[0059] The preparation method of 7-amino-4-hydroxy-3-((4-aminophenyl)diazenyl)naphthalene-2-sodium sulfonate, comprises the steps:

[0060] (1) Preparation of intermediate 7-amino-4-hydroxy-3-((4-nitrophenyl)diazenyl)naphthalene-2-sulfonic acid sodium: weigh p-nitroaniline (2.76g, 20mmol) In a 250mL beaker, add 60mL of dilute hydrochloric acid with a concentration of 1M and 20g of crushed ice, stir evenly, and slowly add 22mL of sodium nitrite solution with a concentration of 1M dropwise into it. Aniline diazonium salt solution, set aside. Weigh sodium 7-amino-4-hydroxynaphthalene-2-sulfonate (5.22g, 20mmol) and sodium hydroxide (1.60g, 40mmol) into a 500mL beaker, add 100mL of 0.6M saturated sodium carbonate solution, stir After homogeneous, the solution of p-nitroaniline diazonium salt was added dropwise thereto, and the dropwise addition was completed, and the reaction was continued for 120 minutes to obtain a reddish-brown suspension. Centrifuged and dried to...

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Abstract

The invention discloses a direct red / direct purple dye compound as well as a preparation method and application thereof. The preparation method of the direct red / direct purple dye compound comprises the following steps: (1) carrying out diazotization reaction on paranitroaniline and polysubstituted naphthol to obtain an intermediate; and (2) dissolving the intermediate prepared in the step (1) in deionized water, reacting at 50-70 DEG C for 60-180 minutes by taking sodium sulfide as a reducing agent, and purifying the product to obtain the direct red / direct purple dye compound. The invention provides a reduction condition which is mild in condition, environment-friendly, simple in treatment and high in universality, the direct dye is modified, nitryl in the direct dye is selectively reduced, azo bonds of the nitryl are not damaged, and the purpose of prolonging the maximum absorption wavelength of the direct dye is achieved.

Description

technical field [0001] The invention relates to the technical field of dyes, in particular to a direct red / direct violet dye compound and a preparation method and application thereof. Background technique [0002] Reducing the nitro group in the dye to an amino group helps to improve the solubility of the dye in an acidic solution and the dyeing effect, and has an important improvement in the performance of the dye. At present, the transformation of direct dyes requires either complicated methods and large equipment investment, or when the dyes are reduced, the azo bonds in them will be destroyed, and the structure of the dye compounds will be destroyed. Especially for the polysubstituted polyazo direct dyes, the stability of the azo double bond is often the key to the reaction control during the modification of the nitro reduction structure, which has an important impact on the yield of the reaction and the purity of the product. . SUMMARY OF THE INVENTION [0003] The ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B29/30C09B29/01D06P1/02
CPCC09B29/30C09B29/0003D06P1/02
Inventor 朱国勋江集楷李正全宋化灿曾耀东
Owner INST OF ANALYSIS GUANGDONG ACAD OF SCI (CHINA NAT ANALYTICAL