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Reactive dye substituted by benzene-containing sulfonamide and derivative of benzene-containing sulfonamide, and preparation method of reactive dye

A technology of reactive dyes and benzenesulfonamide, applied in the direction of reactive dyes, azo dyes, organic dyes, etc., to achieve the effect of broad application prospects and high light fastness

Active Publication Date: 2019-04-12
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It has not been reported that the benzenesulfonamide group is introduced into reactive dyes as a blocking group of the triazine ring, and it is prepared as a class of reactive dyes with higher light fastness

Method used

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  • Reactive dye substituted by benzene-containing sulfonamide and derivative of benzene-containing sulfonamide, and preparation method of reactive dye
  • Reactive dye substituted by benzene-containing sulfonamide and derivative of benzene-containing sulfonamide, and preparation method of reactive dye
  • Reactive dye substituted by benzene-containing sulfonamide and derivative of benzene-containing sulfonamide, and preparation method of reactive dye

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0085] Cyanuric chloride condensation reaction: Weigh 3.14g of benzenesulfonamide, add 40mL of water and 0.8g of sodium hydroxide, heat up to 20°C and stir until dissolved to obtain a mixed solution; add dropwise to the mixed solution at 0-5°C 1.84g of cyanuric chloride dissolved in 20mL of acetone was added dropwise within 40min. React at 0-5°C until the shrinkage reaction is completed. After the shrinkage is completed, add 10% hydrochloric acid to adjust the pH of the reaction solution to <3 to precipitate unreacted benzenesulfonamide, and filter to obtain a clear filtrate. Add 4.0 g of H acid to the above reaction filtrate during the second shrinkage, control the reaction temperature at 25° C., pH 6-7, and control the reaction to the end point by thin-layer chromatography to obtain the condensation product.

[0086] Diazotization reaction: weigh 0.01 mol of p-ester solid, adjust pH 5-6 and dissolve in 20 mL of water. 0.73 g of sodium nitrite was added to dissolve it. Add ...

Embodiment 2～3

[0090] Substitute p-carboxybenzenesulfonamide and p-toluenesulfonamide for benzenesulfonamide in Example 1 respectively, and use the same synthesis method to obtain the structural dyes shown in Examples 2 and 3.

Embodiment 4

[0092] The cyanuric chloride condensation reaction is identical with embodiment 1 reaction steps, replaces 4.0g H acid among the embodiment 1 with 2.15g J acid during two shrink steps.

[0093] Diazotization reaction: same as the preparation method of Example 1.

[0094] Coupling reaction: gradually add the above-mentioned diazo solution to the above-mentioned dicondensation product solution dropwise, adjust the coupling pH to 7-8 with a 10% mass fraction of sodium carbonate solution, control the coupling temperature at 0-5°C, and detect it by the percolation ring method at intervals of 10 minutes The reactions of the diazo component and the coupling component were combined with TLC to detect the progress of the reaction. After the coupling reaction is finished, adjust the reaction pH to about 7, and add buffer salt (Na 2 HPO 3 -NaH 2 PO 3 , 1%, w / v), and then slowly add about 5% of the reaction system quality potassium acetate solid salting out in batches until a water ri...

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Abstract

The invention relates to the field of reactive dye, and particularly relates to a reactive dye substituted by benzene-containing sulfonamide and a derivative of the benzene-containing sulfonamide, anda preparation method of the reactive dye. The reactive dye substituted by the benzene sulfonamide and the derivative of the benzene sulfonamide has a structure represented by a general formula I. Inmolecules of the reactive dye, benzene sulfonamide and substituted benzene sulfonamide groups are directly connected with halogenated s-triazine molecules, and the electron-cloud density of carbon atoms on a triazine ring is reduced through an electron-absorbing effect, so that a nucleophilic substitution reaction occurs easily, therefore, reaction activity of the triazine structure is equivalentto reaction activity of aniline ethyl sulfonyl sulfate, the reaction rate of the dye at 60 DEG C is equivalent to the reaction rate at 90 DEG C, and energy-saving dyeing under mild conditions can be realized. In addition, the dye has high light fastness and has a wide application prospect.

Description

technical field [0001] The invention relates to the field of reactive dyes, in particular to a reactive dye substituted with benzenesulfonamide and its derivatives and a preparation method thereof. Background technique [0002] Reactive dyes can be covalently bonded to fibers and have high wet fastness. Now they have become the main category of dyes for cellulose fiber printing and dyeing. Due to the advantages of cheap and easy-to-obtain raw materials, simple synthesis, bright shade, and complete chromatogram, about 80% of dyes use azo-based chromophores, but because azo bonds are easily affected by ultraviolet light, Oxygen, etc., are prone to redox reactions, resulting in lower light fastness (Dyes and Pigments, 1988, 9(3): 233-241; Surface and Coatings Technology, 2014, 253: 185-193; Dyes and Pigments, 2003, 59(3):269-275). There are two main ways to improve the light stability of dyes: one is to use chromophores with higher light fastness, such as: anthraquinone, phth...

Claims

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Application Information

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IPC IPC(8): C09B62/51C09B62/513C09B62/53C09B62/085
CPCC09B62/085C09B62/51C09B62/513C09B62/53
Inventor 张淑芬熊伟唐炳涛
Owner DALIAN UNIV OF TECH
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