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Acid anthraquinone dye and its prepn and application

An acid dye, anthraquinone type technology, applied in the field of dyes, can solve the problems of expensive dyes, limited application amount and high price, and achieve the effects of reducing dye costs, raw material costs, environmental protection and resource utilization.

Inactive Publication Date: 2007-12-19
SHENYANG RES INST OF CHEM IND +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the high price of the raw material aromatic amine, the price of this type of dye is expensive, and its application is limited to a certain extent.

Method used

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  • Acid anthraquinone dye and its prepn and application
  • Acid anthraquinone dye and its prepn and application
  • Acid anthraquinone dye and its prepn and application

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0029] Example 1: Separation and purification of 2-ethyl-6-sec-butylaniline

[0030] Rectification: Add 600g of industrial waste oil produced by DEA production into a 1000ml three-necked bottle, add zeolite, and pass nitrogen gas through the bottom tube. Distillation conditions: the diameter of the rectification tower is 30mm, the stainless steel triangular packing, the packing height is 1100mm, the vacuum degree is 10mmHg, and the reflux ratio is 5:1. When the liquid phase temperature reached 137°C, reflux occurred, and the fractions at 141-144°C were collected to obtain 300 g of the main fraction, which was 2-ethyl-6-sec-butylaniline with a content of 95%. The analysis data is as follows: 1 H NMR (DCCl 3 , 300MHz) δ 0.89-0.94 (m, 3H, CH 3 ), 1.22-1.29 (m, 6H, CH 3 ), 1.54-1.71 (m, 2H, CH 2 ), 2.49-2.57 (m, 2H, CH 2 ), 2.65-2.68(m, 1H, CH); 6.73-6.7(m, 1H, Ar), 6.94-7.01(m, 2H, Ar), 3.64(s, 2H, NH 2 ); m / z: 177.

example 2

[0031] Example 2: Separation and purification of 2-methyl-6-sec-butylaniline

[0032] Rectification: Add 600g of industrial waste oil produced in the production of MEA into a 1000ml three-necked bottle, add zeolite, and pass nitrogen gas through the bottom tube. Distillation conditions: the diameter of the rectification tower is 30mm, the stainless steel triangular packing, the packing height is 1100mm, the vacuum degree is 10mmHg, and the reflux ratio is 5:1. When the liquid phase temperature reached 127°C, reflux occurred, and the fraction at 130-133°C was collected to obtain 268g of the main fraction, which was 2-methyl-6-sec-butylaniline with a content of 93.5%. The analysis data is as follows: 1 H NMR (DCCl 3 , 300MHz) δ 0.88-0.92 (m, 3H, CH 3 ), 1.21-1.26 (m, 3H, CH 3 ), 1.54-1.71 (m, 2H, CH 2 ), 2.39-2.47 (m, 3H, CH 3 ), 2.65-2.68 (m, 1H, CH); 6.73-6.77 (m, 1H, Ar), 6.92-6.98 (m, 2H, Ar), 3.64 (s, 2H, NH 2 ); m / z: 163.

example 3

[0033] Example 3: Synthesis of dye a:

[0034] Add 8.7g (0.0362mol) 1,4-dihydroxyanthraquinone, 3.7g (0.0152mol) 1,4-dihydroxyanthraquinone leuco, 1.5g boric acid, 40g 2-ethyl - 6-sec-butylaniline, stir and raise the temperature to 150°C, while removing the water brought in by the raw materials and produced by the reaction. The reaction is controlled by thin-layer chromatography: when the yellow and orange raw material spots basically disappear, the reaction is considered to have reached the end, stop the reaction, lower the temperature to 90°C, add 6g of potassium hydroxide, and pass through air to oxidize, until the purple color disappears completely , which is the end point of oxidation, slowly analyze the reaction solution into 120ml hot ethanol, then cool down, filter and wash to obtain the blue intermediate dye 1,4-di(2-ethyl-6-sec-butylanilino)anthracene Quinone 20.0g. The analysis data is as follows: 1 H NMR (DCCl 3 , 300MHz) δ 0.77-0.83 (m, 3H, CH 3 ), 1.01-1.17 ...

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Abstract

The present invention belongs to the field of dye technology, and is especially one kind of acid anthraquinone dye and its preparation process and application. The acid anthraquinone dye in the structure as shown is prepared through extracting 2-ethyl-6-sec-butylamine or 2-methyl-6-sec-butylamine from waste industrial oil, condensation reaction with 1, 4-dihydroxy anthraquinone, and sulfonating in a solvent process. The acid anthraquinone dye is applied in dyeing wool and wool fabric to obtain glow blue or bright purple, and has fastness performance similar to available acid anthraquinone dye.

Description

technical field [0001] The invention belongs to the technical field of dyes, and in particular relates to a class of anthraquinone acid dyes and their preparation and application. Background technique [0002] Anthraquinone acid dyes are one of the main structural types of acid dyes, and are mainly used for dyeing and printing wool and wool fabrics. For example, anthraquinone-type acid dyes such as acid violet 43 and acid blue 80, which are mass-produced and applied in China, all use 1,4-dihydroxyanthraquinone as the starting material, and after single or double condensation reaction with aromatic amine, then Prepared by sulfonation reaction. Due to the high price of the raw material aromatic amine, the price of this kind of dye is expensive, and its application is limited to a certain extent. Taking acid blue 80 as an example, the consumption cost of the raw material mesitidine accounts for 40%-50% of the total raw material cost of the dye. Therefore, if a cheap aromatic...

Claims

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Application Information

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IPC IPC(8): C09B1/52D06P1/40D06P3/16
Inventor 黄海朱红卫温卫东
Owner SHENYANG RES INST OF CHEM IND
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