Sun-proof emerald pyridinone reactive dye compound as well as preparation method and application thereof

Abstract

The invention discloses a sun-proof emerald pyridinone reactive dye compound as well as a preparation method and an application thereof. The dye compound has the following structural general formula (I): a+b+c=3.5, wherein CuPc, M, n, X, R1, R2, R3 and R4 are defined in the description. The invention further provides the preparation method of the reactive dye compound. The sun-proof emerald pyridinone reactive dye compound prepared with the method contains yellow and blue double chromogens in the molecule, intramolecular color matching can be realized directly, and a series of problems duringdye compounding are thoroughly solved; the reactive dye compound has excellent light fastness, good application effect and better development prospect.

Description

technical field

[0001] The invention belongs to the technical field of dyes and their preparation, and in particular relates to an intramolecular color-matched dichroic light-fast emerald green pyridone reactive dye compound containing yellow and blue, and a preparation method and application thereof. Background technique

[0002] Reactive dyes have the characteristics of bright color, complete chromatogram, and excellent wet fastness, and are widely used in the dyeing and printing of cellulose fibers and protein fibers. With the improvement of people's living standards, the requirements for the styles and colors of textiles are getting higher and higher. At present, green dyes are mostly prepared by compounding two or three kinds of dyes, but due to the differences in the solubility of compound dyes, directness to fibers during dyeing, reactivity to alkali fixation and other performance differences, resulting in poor dyeing stability, Easy to dye flowers, large difference ...

Examples

Embodiment 1

[0044] This embodiment discloses a sunfast emerald green pyridone reactive dye compound and a preparation method thereof, the specific steps are as follows:

[0045] (a) Chlorosulfonation reaction: at 40°C, slowly (within half an hour) add 0.100mol of copper phthalocyanine powder to 220mL of chlorosulfonic acid, stir for 30min, then raise the temperature to 135-140°C, maintain the reaction for 3h; cool down to 80°C, and dropwise added 0.504mol thionyl chloride within 2h, then raised the temperature to 90°C, and kept the temperature for 2h; after the reaction was completed, it was lowered to room temperature, poured into ice water while stirring, and precipitated; stood still, filtered, The filter cake was washed with ice water until neutral to obtain the copper phthalocyaninesulfonyl chloride filter cake, which was set aside;

[0046] (b) Primary condensation reaction: 0.101mol cyanuric chloride and 60g crushed ice were beaten for 30 minutes at 0°C; 0.100mol 2,4-diaminobenzene...

Embodiment 2～9

[0052] The examples respectively disclose a sunfast emerald green pyridone reactive dye compound and a preparation method thereof, and the specific steps are similar to Example 1. The difference is: the 4-(β-sulfate group ethyl sulfone group) aniline in step (f) is changed into 4-(β-sulfate group ethyl sulfone group) aniline-2-sulfonic acid, 2-methoxy Base-4-(β-sulfate ethylsulfone)aniline, 2,5-dimethoxy-4-(β-sulfate ethylsulfone)aniline, 2-amino-5-(β- Sulfateethylsulfone)benzoic acid, 3-(β-sulfateethylsulfone)aniline, 3-(β-sulfateethylsulfone)aniline-6-sulfonic acid, 2-methoxy Base-5-(β-sulfate group ethyl sulfone group) aniline and 2-hydroxyl-5-(β-sulfate group ethyl sulfone group) aniline, consumption is 0.100mol; Through step (f), finally obtain The emerald green pyridone reactive dye compound containing copper phthalocyanine and pyridone dichromate has the structures shown in formula (I-2A) to formula (I-9A) in Table 1.

Embodiment 10～18

[0054] The examples respectively disclose a light-fast emerald green pyridone reactive dye compound and a preparation method thereof, and the specific steps are similar to those in Examples 1 to 9. The difference is: the 2,4-diaminobenzenesulfonic acid in the step (b) is changed to m-phenylenediamine-4,6-bissulfonic acid, and the dosage is 0.100mol; after the step (f), the copper-containing phthalein The emerald green pyridone reactive dye compound of cyanine and pyridone dichromophore has the structure shown in the formula (I-10A) ~ formula (I-18A) in Table 1.

technical field

[0001] The invention belongs to the technical field of dyes and their preparation, and in particular relates to an intramolecular color-matched dichroic light-fast emerald green pyridone reactive dye compound containing yellow and blue, and a preparation method and application thereof. Background technique

[0002] Reactive dyes have the characteristics of bright color, complete chromatogram, and excellent wet fastness, and are widely used in the dyeing and printing of cellulose fibers and protein fibers. With the improvement of people's living standards, the requirements for the styles and colors of textiles are getting higher and higher. At present, green dyes are mostly prepared by compounding two or three kinds of dyes, but due to the differences in the solubility of compound dyes, directness to fibers during dyeing, reactivity to alkali fixation and other performance differences, resulting in poor dyeing stability, Easy to dye flowers, large difference ...

Examples

Embodiment 1

[0044] This embodiment discloses a sunfast emerald green pyridone reactive dye compound and a preparation method thereof, the specific steps are as follows:

[0045] (a) Chlorosulfonation reaction: at 40°C, slowly (within half an hour) add 0.100mol of copper phthalocyanine powder to 220mL of chlorosulfonic acid, stir for 30min, then raise the temperature to 135-140°C, maintain the reaction for 3h; cool down to 80°C, and dropwise added 0.504mol thionyl chloride within 2h, then raised the temperature to 90°C, and kept the temperature for 2h; after the reaction was completed, it was lowered to room temperature, poured into ice water while stirring, and precipitated; stood still, filtered, The filter cake was washed with ice water until neutral to obtain the copper phthalocyaninesulfonyl chloride filter cake, which was set aside;

[0046] (b) Primary condensation reaction: 0.101mol cyanuric chloride and 60g crushed ice were beaten for 30 minutes at 0°C; 0.100mol 2,4-diaminobenzene...

Embodiment 2～9

[0052] The examples respectively disclose a sunfast emerald green pyridone reactive dye compound and a preparation method thereof, and the specific steps are similar to Example 1. The difference is: the 4-(β-sulfate group ethyl sulfone group) aniline in step (f) is changed into 4-(β-sulfate group ethyl sulfone group) aniline-2-sulfonic acid, 2-methoxy Base-4-(β-sulfate ethylsulfone)aniline, 2,5-dimethoxy-4-(β-sulfate ethylsulfone)aniline, 2-amino-5-(β- Sulfateethylsulfone)benzoic acid, 3-(β-sulfateethylsulfone)aniline, 3-(β-sulfateethylsulfone)aniline-6-sulfonic acid, 2-methoxy Base-5-(β-sulfate group ethyl sulfone group) aniline and 2-hydroxyl-5-(β-sulfate group ethyl sulfone group) aniline, consumption is 0.100mol; Through step (f), finally obtain The emerald green pyridone reactive dye compound containing copper phthalocyanine and pyridone dichromate has the structures shown in formula (I-2A) to formula (I-9A) in Table 1.

Embodiment 10～18

[0054] The examples respectively disclose a light-fast emerald green pyridone reactive dye compound and a preparation method thereof, and the specific steps are similar to those in Examples 1 to 9. The difference is: the 2,4-diaminobenzenesulfonic acid in the step (b) is changed to m-phenylenediamine-4,6-bissulfonic acid, and the dosage is 0.100mol; after the step (f), the copper-containing phthalein The emerald green pyridone reactive dye compound of cyanine and pyridone dichromophore has the structure shown in the formula (I-10A) ~ formula (I-18A) in Table 1.

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