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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AI-Extracted Technical Summary

Problems solved by technology

It has not been reported that the benzenesulfonamide group is introduced into reactive dyes as a blocki...
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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.

Application Domain

Technology Topic

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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(27)
  • Effect test(1)

Example Embodiment

[0084] Example 1
[0085] Cyanur chloride condensation reaction: Weigh 3.14g of benzenesulfonamide, add 40mL of water and 0.8g of sodium hydroxide, heat to 20℃ and stir to dissolve to obtain a mixed solution; add dropwise to the mixed solution at 0~5℃ 1.84 g of cyanuric chloride dissolved in 20 mL of acetone was added dropwise within 40 minutes. The reaction was carried out at 0-5°C to the end of the condensation reaction. After the completion of the condensation, 10% hydrochloric acid was added to adjust the pH of the reaction solution to <3 to precipitate unreacted benzenesulfonamide, and a clear filtrate was obtained by filtration. During the second condensation, 4.0 g of H acid was added to the above-mentioned reaction filtrate, the reaction temperature was controlled at 25° C., pH 6-7, and thin-layer chromatography detected and controlled the reaction to the end point to obtain a condensation product.
[0086] Diazotization reaction: Weigh 0.01 mol of the para-ester solid, adjust the pH 5 to 6 and dissolve in 20 mL of water. Add 0.73g of sodium nitrite to dissolve it. The mixed solution was added to an acidic aqueous solution containing 2.5 mL of concentrated hydrochloric acid with a mass fraction of 37% and cooled to 0-5°C, and the Congo red test paper and starch-KI test paper were used to check whether the hydrochloric acid and sodium nitrite were sufficient. After 30 minutes, the end point of the reaction was detected with Elixi reagent. At the end of the diazotization, add sulfamic acid to the system to destroy the excess sodium nitrite to obtain the diazonium liquid
[0087] Coupling reaction: The above diazonium liquid is gradually added dropwise to the condensation product cyanuric chloride-benzenesulfonamide di-condensed H acid product solution, and the coupling pH is adjusted to 7-8 with a mass fraction of 10% sodium carbonate solution to obtain a coupling reaction System solution,
[0088] The coupling temperature is controlled at 0~5℃, and the reaction conditions of the diazonium component and the coupling component are detected by the percolation method at intervals of 10 minutes. The diazonium component is the above-mentioned diazonium liquid, and the coupling component is the solution of the combined reaction system. Combine TLC to detect the progress of the reaction. After the coupling reaction is over, 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 in batches of about 5% of the mass of the coupling reaction system to solid salting out of potassium acetate until a water circle appears in the percolation method. Continue to stir the system for 10 minutes, let the system stand for 20 minutes, and then filter with suction, and wash the filter cake with 50 mL of ethanol and dry to obtain the dye.

Example

[0089] Examples 2~3
[0090] Using p-carboxybenzenesulfonamide and p-toluenesulfonamide to replace benzenesulfonamide in Example 1, respectively, the structural dyes shown in Examples 2 and 3 can be prepared by the same synthesis method.

Example Embodiment

[0091] Example 4
[0092] The cyanuric chloride condensation reaction is the same as the reaction step in Example 1. In the second condensation step, 2.15 g of J acid is used instead of 4.0 g of H acid in Example 1.
[0093] Diazotization reaction: the same preparation method as in Example 1.
[0094] Coupling reaction: gradually add the above diazonium liquid to the above dicondensed product solution, adjust the coupling pH to 7-8 with a mass fraction of 10% sodium carbonate solution, control the coupling temperature from 0 to 5℃, and check with the percolation method at 10 min intervals The reaction conditions of the diazonium component and the coupling component are combined with TLC to detect the progress of the reaction. After the coupling reaction is over, 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 mass of the reaction system to the solid potassium acetate salting out in batches until a water circle appears in the percolation circle. Continue to stir the system for 10 minutes, let the system stand for 20 minutes, and then filter with suction, and wash the filter cake with 50 mL of ethanol and dry to obtain the dye.
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