A kind of azo dye compound containing methanesulfonamide group and its preparation method and application

Abstract

The invention relates to an azo dyestuff compound containing methanesulfonamide group as well as a preparation method and application thereof. A structural formula of the compound is as follows: a formula is shown in the description. The azo dyestuff compound is applied to dyeing or printing of a hydrophobic material or a blending material containing the hydrophobic material. The compound providedby the invention has excellent perspiration resistance, color fastness to rubbing, water resistance, sublimation resistance and color fastness to bleaching. Even if the dyeing concentration is improved, the color fastness of obtained textiles is very excellent. The dyestuff provided by the invention has good comprehensive performance.

Description

technical field

[0001] The invention belongs to the field of azo dyes, in particular to an azo dye compound containing a methanesulfonamide group and a preparation method and application thereof. Background technique

[0002] Azo dyes based on aminophthalimides as diazotization components have been widely used. However, it has been found that dyeings or prints obtained using currently known dyes do not meet today's needs in all cases. There is still a need for a dye with excellent comprehensive properties of sublimation resistance and perspiration resistance. Contents of the invention

[0003] The technical problem to be solved by the present invention is to provide an azo dye compound containing a methanesulfonamide group and its preparation method and application. The compound overcomes the problems of insufficient dye sublimation resistance and perspiration resistance in the prior art.

[0004] The invention provides an azo dye compound containing a methanesulfonamide...

Examples

Embodiment 1

[0037]

[0038] step 1

[0039]

[0040] Add 112g of sulfuric acid into a 150ml three-necked flask, stir, slowly add 27g of the compound of formula II-1 below 60°C, stir until clarified, then cool down to 5-10°C and slowly add 31.5g of nitrosyl sulfuric acid (40%), add Incubate the diazo at 5-10°C for 3 hours and wait for coupling.

[0041] step 2

[0042]

[0043] Add 500g of ice-water mixture into a 1000ml beaker, stir, add 2.5g of sulfamic acid, slowly add 33g of the compound of formula (III-1) at 5°C, and then slowly add the coupling components of the above step 1, and finish adding in 10 The temperature was kept at about ℃ for 5-6 hours, and the temperature was directly raised to 65°C, stirred, kept for 1 hour, filtered, washed with water until neutral, separated by column chromatography to obtain 50 g of the compound of formula (I-1), and the HPLC purity was >90%. 1H-NMR (DMSO, 300MHz): 1.15 (9H, m), 3.22 (3H, s), 3.40 (2H, m), 3.46 (2H, m), 3.52 (4H, m), 3.63...

Embodiment 2

[0045] According to the method of Example 1, the following compounds were synthesized

[0046] Table 1

[0047]

Embodiment 3

[0049] The compound of above-mentioned embodiment I-1~I-9 is mixed with MF, dry, and the disperse dye composition that makes is mixed with water respectively and is the disperse dye suspension that mass percent concentration is 1% and 3%, imbibes 20ml disperse dye Mix the suspension with 80m of water, adjust the pH of the dyeing bath to 5 with acetic acid, and then raise the temperature to 60°C. At the same time, put 2g of polyester fiber into it for high-temperature and high-pressure dyeing, heat up to 130°C within 35 minutes, keep it warm for 30 minutes, and cool to Sampling at 80°C.

technical field

[0001] The invention belongs to the field of azo dyes, in particular to an azo dye compound containing a methanesulfonamide group and a preparation method and application thereof. Background technique

[0002] Azo dyes based on aminophthalimides as diazotization components have been widely used. However, it has been found that dyeings or prints obtained using currently known dyes do not meet today's needs in all cases. There is still a need for a dye with excellent comprehensive properties of sublimation resistance and perspiration resistance. Contents of the invention

[0003] The technical problem to be solved by the present invention is to provide an azo dye compound containing a methanesulfonamide group and its preparation method and application. The compound overcomes the problems of insufficient dye sublimation resistance and perspiration resistance in the prior art.

[0004] The invention provides an azo dye compound containing a methanesulfonamide...

Examples

Embodiment 1

[0037]

[0038] step 1

[0039]

[0040] Add 112g of sulfuric acid into a 150ml three-necked flask, stir, slowly add 27g of the compound of formula II-1 below 60°C, stir until clarified, then cool down to 5-10°C and slowly add 31.5g of nitrosyl sulfuric acid (40%), add Incubate the diazo at 5-10°C for 3 hours and wait for coupling.

[0041] step 2

[0042]

[0043] Add 500g of ice-water mixture into a 1000ml beaker, stir, add 2.5g of sulfamic acid, slowly add 33g of the compound of formula (III-1) at 5°C, and then slowly add the coupling components of the above step 1, and finish adding in 10 The temperature was kept at about ℃ for 5-6 hours, and the temperature was directly raised to 65°C, stirred, kept for 1 hour, filtered, washed with water until neutral, separated by column chromatography to obtain 50 g of the compound of formula (I-1), and the HPLC purity was >90%. 1H-NMR (DMSO, 300MHz): 1.15 (9H, m), 3.22 (3H, s), 3.40 (2H, m), 3.46 (2H, m), 3.52 (4H, m), 3.63...

Embodiment 2

[0045] According to the method of Example 1, the following compounds were synthesized

[0046] Table 1

[0047]

Embodiment 3

[0049] The compound of above-mentioned embodiment I-1~I-9 is mixed with MF, dry, and the disperse dye composition that makes is mixed with water respectively and is the disperse dye suspension that mass percent concentration is 1% and 3%, imbibes 20ml disperse dye Mix the suspension with 80m of water, adjust the pH of the dyeing bath to 5 with acetic acid, and then raise the temperature to 60°C. At the same time, put 2g of polyester fiber into it for high-temperature and high-pressure dyeing, heat up to 130°C within 35 minutes, keep it warm for 30 minutes, and cool to Sampling at 80°C.

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