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Cyanide-containing orange-yellow azo dye

A technology of orange-yellow azo dyes, applied in azo dyes, organic dyes, reactive dyes, etc.

Active Publication Date: 2017-06-27
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

N-cyanoethylaniline derivatives containing cyano groups are currently mainly used as synthetic disperse dyes. Among reactive dyes, yellow dyes are mainly pyrazolone, pyridone, 2,4-diaminobenzenesulfonic acid and their Derivatives are monoazo dyes as coupling components, but there is no research report on the synthesis of azo-type reactive dyes using N-cyanoethylaniline derivatives in dye molecules as coupling components

Method used

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  • Cyanide-containing orange-yellow azo dye
  • Cyanide-containing orange-yellow azo dye
  • Cyanide-containing orange-yellow azo dye

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] The specific structure of Embodiment 1 is as follows:

[0035]

[0036] Condensation reaction of cyanuric chloride: Add 1.90g cyanuric chloride (0.0103mol) and 20g small ice cubes in a 250mL beaker, and beat for 30min to milky. The aqueous solution (0.01mol, 98%) containing 3.11g m-phenylenediamine-4,6-bissulfonic acid was slowly added dropwise to the above-mentioned beating solution, and reacted at 0~5℃, using 10% Na 2 CO 3 The pH value of the solution is adjusted to be 4~5, and the end point of the reaction is detected by TLC (the developing solvent is isobutanol: n-propanol: ethyl acetate: water = 2:4:1:3, v / v, the R of the product f Value is 0.74), after the reaction is completed, add 0.75g glycine (0.01mol), raise the temperature to 20~30℃, use 10% Na 2 CO 3 The pH value of the solution is controlled between 6 and 7, after 3 to 4 hours of reaction, TLC detects the end of the reaction (developing solvent is n-butanol: isopropanol: ethyl acetate: water = 2:4:1:3, v / v , R...

Embodiment 2

[0040] The specific structure of Embodiment 2 is as follows:

[0041]

[0042] Condensation reaction of cyanuric chloride: Add 1.90g cyanuric chloride (0.0103mol) and 20g small ice cubes in a 250mL beaker, and beat for 30min to milky. The aqueous solution (0.01mol, 98%) containing 3.11g m-phenylenediamine-4,6-bissulfonic acid was slowly added dropwise to the above-mentioned beating solution, and reacted at 0~5℃, using 10% Na 2 CO 3 The pH value of the solution is adjusted to 4~5, and the end point of the reaction is detected by TLC (the developing solvent is isobutanol: n-propanol: ethyl acetate: water = 2:4:1:3, v / v, the R of the product f Value is 0.74), after the reaction is completed, add 0.89g alanine (0.01mol), raise the temperature to 20~30℃, use 10% Na 2 CO 3 The pH value of the solution is controlled between 6 and 7, after 3 to 4 hours of reaction, the end of the reaction is detected by TLC (developing solvent is n-butanol: isopropanol: ethyl acetate: water = 2:4:1:3, v / v ...

Embodiment 3

[0046] The specific structure of Embodiment 3 is as follows:

[0047]

[0048] Condensation reaction of cyanuric chloride: Add 1.90g cyanuric chloride (0.0103mol) and 20g small ice cubes in a 250mL beaker, and beat for 30min to milky. The aqueous solution (0.01mol, 98%) containing 3.11g m-phenylenediamine-4,6-bissulfonic acid was slowly added dropwise to the above-mentioned beating solution, and reacted at 0~5℃, using 10% Na 2 CO 3 The pH value of the solution is adjusted to 4~5, and the end point of the reaction is detected by TLC (the developing solvent is isobutanol: n-propanol: ethyl acetate: water = 2:4:1:3, v / v, the R of the product f Value is 0.74), after the reaction is completed, add 1.17g valine (0.01mol), raise the temperature to 20~30℃, use 10% Na 2 CO 3 The pH value of the solution is controlled between 6 and 7, after 3 to 4 hours of reaction, TLC detects the end of the reaction (developing solvent is n-butanol: isopropanol: ethyl acetate: water = 2:4:1:3, v / v );

[00...

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Abstract

The invention discloses a cyano-containing orange-yellow azo type dye which has a structure of formula I as shown in the specification. The cyano-containing orange-yellow azo type dye is high in light fastness, and relatively high in color fixation rate and dyeing rate in the dyeing process and can be used for dyeing cellulosic fiber and leather, problems of a conventional azo type active dye are well solved, the environment pollution is greatly reduced, and novel ways are provided for application of the azo type active dye.

Description

Technical field [0001] The invention relates to a cyano group-containing orange-yellow azo dye and a preparation method thereof. This type of dye has the characteristics of excellent light fastness, high fixation rate and dye uptake, and can be well applied to the dyeing of cellulose fibers and leather, and has broad application prospects. Background technique [0002] Among the reactive dyes, azo reactive dyes are a very important category of reactive dyes. Azo reactive dyes are the most produced and used in the world due to the easy availability of raw materials, simple synthesis method and high molar absorption coefficient. Dyestuffs, but the azo bond is prone to oxidation-reduction reaction in the corresponding environment, so its light resistance stability is low. Studies have shown that when there is an electron withdrawing group at the ortho position of the azo bond in the molecular structure of the dye, the electron cloud density on the azo bond can be reduced, and the l...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D251/26C07D251/00C09B62/665
CPCC09B62/665
Inventor 张淑芬单斌唐炳涛
Owner DALIAN UNIV OF TECH
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