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5-chloronitroaniline-containing azoic disperse dyes and preparation method and application thereof

A chloronitroaniline, disperse dye technology, applied in azo dyes, monoazo dyes, dyeing methods and other directions, can solve problems such as harm to health, unstable dye crystal form, environmental pollution, etc., to achieve environmental friendly, wet Excellent handling fastness and sublimation fastness, the effect of stable dye crystal form

Inactive Publication Date: 2010-06-16
烟台澳土复合材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The use of highly toxic cyanide in the preparation process not only endangers people's health but also pollutes the environment, and the crystal form of some dyes is unstable

Method used

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  • 5-chloronitroaniline-containing azoic disperse dyes and preparation method and application thereof
  • 5-chloronitroaniline-containing azoic disperse dyes and preparation method and application thereof
  • 5-chloronitroaniline-containing azoic disperse dyes and preparation method and application thereof

Examples

Experimental program
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Effect test

preparation example Construction

[0034] Preparation of diazo compounds:

[0035] (1) Add 250ml of concentrated sulfuric acid to a 1000ml flask, add 65ml of fuming nitric acid at room temperature, exotherm, the temperature rises to 40°C, add 70ml of m-dichlorobenzene dropwise, control the feeding speed and cool down with a water bath, so that the feeding temperature is controlled at 60- 75°C, 1-1.5 hours to complete the addition. Raise the temperature to 80-85°C, and keep it warm for 3 hours. Then add 125ml of 50% fuming sulfuric acid dropwise at a temperature of 80-85°C and finish adding in 1.5 hours. After maintaining the reaction at this temperature for 3 hours, the temperature was then raised to 100-110° C., and the reaction was continued for 3 hours. When the mononitride content is lower than 1.0%, the reaction is terminated, and the temperature is cooled to room temperature. Add water and a large amount of ice to a 2000ml beaker, control the temperature below 10°C, slowly add the above reaction soluti...

Embodiment 1

[0040] Add 30ml of concentrated sulfuric acid and 34g of 40% nitrosylsulfuric acid into a 250ml flask, stir, cool down to 10-15°C in an ice-water bath, slowly add 21.8g of 2,4-dinitro-5-chloroaniline, and control the temperature for 10 -15°C, 20-30min to complete the addition. And keep it warm at this temperature for 3 hours and set it aside. Add 200ml of water, 9ml of concentrated sulfuric acid, and 1g of sulfamic acid into a 2000ml beaker, stir evenly, add 0.102mol of dark blue esterification solution and crushed ice, add the above diazo solution dropwise in the range of 0-5°C, and add sodium acetate to adjust pH=2.0-2.5, stirred for 1 hour, the diazo component disappeared, raised the temperature to 35-40°C, kept it warm for 1 hour, filtered and washed with water until neutral. The blue dye compound represented by formula (I-1) was obtained.

[0041]

[0042] (I-1)

Embodiment 2

[0044] At room temperature, put 90ml of water, 36g of 4-methoxy-3-aminoacetanilide, 122g of β-methoxyethyl p-toluenesulfonate, and 12g of magnesium oxide into a 250ml flask in sequence, start stirring, and slowly Raise the temperature to 80-85°C, react for 6 hours, then raise the temperature to 92-95°C and keep the reaction for 12 hours. When the content of the main product is ≥ 96% as detected by HPLC, cool down to 30°C, filter, and wash with water to obtain 4-methoxy-3 -N,N-bis(β-methoxyethyl)aminoacetanilide.

[0045]According to the preparation method described in Example 1, 0.1mol of 2,4-dinitro-5-chloroaniline and 4-methoxy-3-N, N-di(β-methoxyethyl)aminoacetanilide 0.102mol reaction can prepare the dye compound shown in formula (I-2).

[0046]

[0047] (I-2)

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Abstract

The invention provides 5-chloronitroaniline-containing azoic disperse dyes and a preparation method thereof. The structural general formula of the disperse dyes is shown in a formula (I), wherein X is hydrogen or bromine; R is hydrogen, methyl or -NHCO-C1-C4 alkyl; R1 is ethyl, cyanoethyl, phenmethyl, allyl or -CH2CH2OR4, wherein R4 is methyl, ethyl or carbonyl; R2 is independent of R1 but has the definition of the R1; and R3 is hydrogen, methoxyl or ethyoxyl. The 5-chloronitroaniline-containing azoic disperse dyes are characterized in that: a diazonium component contains 2,4-binitro-5-chloroaniline or bromide thereof. The dyes have the advantages of excellent wet fastness and sublimation fastness, are suitable for dyeing terylene and blend fabrics thereof, and have low cost and wide application prospect.

Description

Technical field: [0001] The invention relates to azo disperse dyes containing 5-chloronitroaniline, and relates to the preparation method and application of these dyes. Background technique: [0002] At present, the disperse dyes with 2,4-dinitro-6-bromo(chloro)aniline as the diazo component are mostly used as dark varieties, and are widely used in polyester printing and dyeing, such as C.I. Disperse Blue 79:1, C.I. Disperse blue 291 and C.I. disperse violet 93, etc., but the wet fastness of these dyes is poor. After the polyester fabric is heat-set at high temperature, part of the dye will re-migrate to the surface of the fiber and contaminate the adjacent fabric. For this reason, disperse dyes of some new structures have appeared to solve the above problems. The diazo components of these new structure disperse dyes may be phthalimide bromides or single cyanide and double cyanide substitutions of bromides. Objects, or single cyanide, dicyanide structure of aniline. The co...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B67/40C09B67/38C09B29/085D06P3/86D06P1/18
Inventor 鲍明松高景庆
Owner 烟台澳土复合材料有限公司
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