Red azo reactive dye containing sulfanilamide structure

Abstract

The invention provides a red azo reactive dye containing a sulfanilamide structure, which is of a structure shown in a general formula I. The dye is prepared by taking a H acid as a parent, taking chlorine or fluorine substituted s-triazine, ethyl sulfone sulphate as active groups, taking sulfanilamide and derivatives thereof or (beta-sulphate ethyl sulfone) aniline as diazo components, and taking sulfanilamide and derivatives thereof, (beta-sulphate ethyl sulfone) aniline, aminobenzophenone or long carbon chain fatty amine as condensation components. The introduction of a sulfanilamide-like structure increases the structure size of the dye; because the introduction of the sulfanilamide structure reduces the solubility of the reactive dye to a certain extent, the adsorption of the dye on fibers is promoted, so that the dye has a better fixation rate.

Description

technical field

[0001] The invention relates to a reactive dye, in particular to a red azo reactive dye containing a sulfonamide structure. Background technique

[0002] Reactive dyes are a class of textile dyes with excellent performance, mainly used for dyeing and printing of cellulose fibers, such as cotton, linen and their blended fibers. Reactive dyes have complete chromatograms and bright colors. The reactive groups in the structure react with the hydroxyl groups on the cellulose fibers to form covalent bonds to achieve the fixation of dyes on the fibers. It is precisely because of the formation of strong covalent bonds that reactive dyes have higher color fastness than other applied dyes, especially wet treatment fastness, so reactive dyes are unique among dyes for cellulose fibers and are widely used . Although there are many advantages, reactive dyes also have the problem of low dye utilization rate, and the fixation rate is mostly 50-70%, resulting in a lot of dy...

Examples

Embodiment 1

[0071] 9.7g of cyanuric chloride was beaten for about 30 minutes under ice bath conditions, and 16.6g of H acid was dissolved and added dropwise to cyanuric chloride, reacted in ice bath for about 1 hour, and the pH was controlled to 3-5, and the reaction was completed (Ehrlich reagent Discoloration after detection), suction filtration, take the filtrate, weigh 8.6g sulfonamide and dissolve it in 100ml0.15mol / L hydrochloric acid solution, weigh 3.7g sodium nitrite and dissolve it in 50ml water, drop the sodium nitrite solution into the acid solution of sulfonamide , carry out diazotization reaction, add the diazonium salt obtained above to the solution obtained by H acid condensation, react in ice bath for 1 h, pH7-9, salt out after the reaction is completed, filter out the red dye, and dry it in vacuum. Yield 95%.

Embodiment 2-4

[0073] The method is the same as in Example 1, but sulfapyridine, sulfathiazole, and sulfaguanidine are used instead of sulfaguanidine to synthesize the corresponding diazonium salts, and then the corresponding red reactive dyes are obtained through the coupling reaction. Other conditions are consistent with Example 1.

[0074] Among them, the dye synthesized with sulfathiazole instead of sulfonamide (dye 1, i.e. Example 3) has the following structure:

[0075]

Embodiment 5

[0077] Weigh 9.7g of cyanuric chloride and beat for about 30 minutes under ice bath conditions; dissolve 16.6g of H acid and add it dropwise to cyanuric chloride, react in ice bath for about 1 hour, control pH3-5, pump out after the reaction is completed Filtrate and take the filtrate; dissolve 8.6g of sulfonamide under acidic conditions, slowly add the above-mentioned condensed product to the sulfonamide solution, control the pH to 6-7, react at 35°C for 4 hours, and then cool in an ice bath to obtain the condensed solution; weigh 8.6g of sulfonamide Dissolve in 100ml of 0.15mol / L hydrochloric acid solution, weigh 3.7g of sodium nitrite and dissolve in 50ml of water, drop the sodium nitrite solution into the acid solution of sulfonamide for diazotization reaction; The solution was reacted in an ice bath for 1 h, and the pH was controlled to be 7-9. After the reaction was completed, the salt was precipitated, and the red dye was obtained by suction filtration, and dried in vacu...

technical field

[0001] The invention relates to a reactive dye, in particular to a red azo reactive dye containing a sulfonamide structure. Background technique

[0002] Reactive dyes are a class of textile dyes with excellent performance, mainly used for dyeing and printing of cellulose fibers, such as cotton, linen and their blended fibers. Reactive dyes have complete chromatograms and bright colors. The reactive groups in the structure react with the hydroxyl groups on the cellulose fibers to form covalent bonds to achieve the fixation of dyes on the fibers. It is precisely because of the formation of strong covalent bonds that reactive dyes have higher color fastness than other applied dyes, especially wet treatment fastness, so reactive dyes are unique among dyes for cellulose fibers and are widely used . Although there are many advantages, reactive dyes also have the problem of low dye utilization rate, and the fixation rate is mostly 50-70%, resulting in a lot of dy...

Examples

Embodiment 1

[0071] 9.7g of cyanuric chloride was beaten for about 30 minutes under ice bath conditions, and 16.6g of H acid was dissolved and added dropwise to cyanuric chloride, reacted in ice bath for about 1 hour, and the pH was controlled to 3-5, and the reaction was completed (Ehrlich reagent Discoloration after detection), suction filtration, take the filtrate, weigh 8.6g sulfonamide and dissolve it in 100ml0.15mol / L hydrochloric acid solution, weigh 3.7g sodium nitrite and dissolve it in 50ml water, drop the sodium nitrite solution into the acid solution of sulfonamide , carry out diazotization reaction, add the diazonium salt obtained above to the solution obtained by H acid condensation, react in ice bath for 1 h, pH7-9, salt out after the reaction is completed, filter out the red dye, and dry it in vacuum. Yield 95%.

Embodiment 2-4

[0073] The method is the same as in Example 1, but sulfapyridine, sulfathiazole, and sulfaguanidine are used instead of sulfaguanidine to synthesize the corresponding diazonium salts, and then the corresponding red reactive dyes are obtained through the coupling reaction. Other conditions are consistent with Example 1.

[0074] Among them, the dye synthesized with sulfathiazole instead of sulfonamide (dye 1, i.e. Example 3) has the following structure:

[0075]

Embodiment 5

[0077] Weigh 9.7g of cyanuric chloride and beat for about 30 minutes under ice bath conditions; dissolve 16.6g of H acid and add it dropwise to cyanuric chloride, react in ice bath for about 1 hour, control pH3-5, pump out after the reaction is completed Filtrate and take the filtrate; dissolve 8.6g of sulfonamide under acidic conditions, slowly add the above-mentioned condensed product to the sulfonamide solution, control the pH to 6-7, react at 35°C for 4 hours, and then cool in an ice bath to obtain the condensed solution; weigh 8.6g of sulfonamide Dissolve in 100ml of 0.15mol / L hydrochloric acid solution, weigh 3.7g of sodium nitrite and dissolve in 50ml of water, drop the sodium nitrite solution into the acid solution of sulfonamide for diazotization reaction; The solution was reacted in an ice bath for 1 h, and the pH was controlled to be 7-9. After the reaction was completed, the salt was precipitated, and the red dye was obtained by suction filtration, and dried in vacu...

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