Monoazo lake pigment and preparation method thereof

Abstract

The invention discloses a monoazo lake pigment. The structural general formula of the monoazo lake pigment is one of the structures described in the description: M is one of Ca, Ba and Sr; R is H, OH,NO2, Cl, Br or C1 to C4 alkyl, and n is a positive integer from 1 to 3; and Ar is described in the description. According to the preparation method of the monoazo lake pigment, sodium chloride or sodium hydrogen sulfate / sodium sulfate can be prevented from being generated in the process of preparing the aromatic primary amine diazonium salt. Meanwhile, in the coupling reaction process, alkali containing a sodium element is not adopted, generation of inorganic sodium salt can be avoided in the manufacturing process of the monoazo lake pigment, and conditions are provided for clean treatment and comprehensive utilization of coupling reaction liquid.

Description

technical field

[0001] The invention belongs to the technical field of fine chemicals, and in particular relates to a structure of a monoazo lake pigment and a preparation method thereof. Background technique

[0002] The precursor of monoazo lake pigment is monoazo acid dye, which contains at least one sulfonic acid or sodium sulfonate group in its molecule, so it is water-soluble. The monoazo lake pigment is insoluble in water because it converts the sulfonic acid or sodium sulfonate group in the monoazo acid dye into a group such as calcium sulfonate or barium sulfonate.

[0003] The coupling components used in existing monoazoic acid dyes are mainly aromatic amines, phenols, pyrazolones or pyridones. They are coupled with the diazonium salts of various aromatic primary amines, and the obtained reaction products are water-soluble. In order to obtain solid state dyes, the method of salting out is often used. Restricted by solubility, some dyes must not be precipitated fr...

Examples

Embodiment 1

[0045] The first step, diazotization reaction of aromatic primary amine sulfonic acid

[0046] Mix p-aminobenzenesulfonic acid (industrial product, Hebei Jianxin Chemical Co., Ltd., 17.4g, 0.1mol) with water (800ml), stir until the solids are completely dissolved, and obtain an aqueous solution of p-aminobenzenesulfonic acid (pH=1-2 ), cooled with an ice / water bath to reduce the solution temperature to <10°C. Under stirring, slowly add 40% nitrosylsulfuric acid (industrial product, 40% sulfuric acid solution, Zhejiang Sanmen Jieshi Chemical Co., Ltd., 33g, 0.105mol) into the above solution for about 30 minutes, during which the temperature is controlled <10°C. After the addition, continue to stir for 20 minutes to obtain a cloudy water solution of diazonium p-aminobenzenesulfonic acid, pH = 1, and the starch-potassium iodide test paper detects that there is a slight excess of nitrous acid.

[0047] The second step, the preparation of barbituric acid coupling solution

[0048...

Embodiment 2

[0056] The first step to the third step are the same as in Example 1.

[0057] The fourth step, the laking reaction

[0058] After the third step of the reaction, directly heat the reactant to 60°C and keep it warm for 1 hour to obtain a transparent and clear solution, adjust the pH to 5-6 with 10% KOH, and add CaCl dropwise 2 (Industrial product, 11.3g, 0.1mol) aqueous solution, after the dropwise addition, stop heating, cool naturally, and let stand overnight. The precipitated filter cake was filtered, washed with water until neutral, and dried at 120°C to obtain 33.2 g of a brilliant bright yellow solid, which was monoazo lake pigment I-1-1.

Embodiment 3

[0060] The first step, diazotization reaction of aromatic primary amine sulfonic acid

[0061] Mix Turmeric's Acid (industrial product, Inner Mongolia Xinya Chemical Co., Ltd., 22.7g, 0.1mol) and water (600ml), heat to 50°C under stirring, add 10% KOH solution dropwise until the solids are completely dissolved, and get Turmeric's Acid The aqueous solution of potassium salt is naturally cooled to room temperature, and the pH is adjusted to 1-2 with sulfuric acid. Turmeric acid is precipitated from the water to form a turbid solution. Use an ice / water bath to reduce the temperature of the turbid solution to <10°C. Under stirring, slowly add 40% nitrosylsulfuric acid (industrial product, 40% sulfuric acid solution, 33g, 0.105mol) into the above solution dropwise for about 30 minutes, during which the temperature is controlled to <10°C. After the addition, continue stirring for 20 minutes to obtain The diazonium salt of the acid (cloudy liquid, light yellow), pH = 1, starch-potass...

technical field

[0001] The invention belongs to the technical field of fine chemicals, and in particular relates to a structure of a monoazo lake pigment and a preparation method thereof. Background technique

[0002] The precursor of monoazo lake pigment is monoazo acid dye, which contains at least one sulfonic acid or sodium sulfonate group in its molecule, so it is water-soluble. The monoazo lake pigment is insoluble in water because it converts the sulfonic acid or sodium sulfonate group in the monoazo acid dye into a group such as calcium sulfonate or barium sulfonate.

[0003] The coupling components used in existing monoazoic acid dyes are mainly aromatic amines, phenols, pyrazolones or pyridones. They are coupled with the diazonium salts of various aromatic primary amines, and the obtained reaction products are water-soluble. In order to obtain solid state dyes, the method of salting out is often used. Restricted by solubility, some dyes must not be precipitated fr...

Examples

Embodiment 1

[0045] The first step, diazotization reaction of aromatic primary amine sulfonic acid

[0046] Mix p-aminobenzenesulfonic acid (industrial product, Hebei Jianxin Chemical Co., Ltd., 17.4g, 0.1mol) with water (800ml), stir until the solids are completely dissolved, and obtain an aqueous solution of p-aminobenzenesulfonic acid (pH=1-2 ), cooled with an ice / water bath to reduce the solution temperature to <10°C. Under stirring, slowly add 40% nitrosylsulfuric acid (industrial product, 40% sulfuric acid solution, Zhejiang Sanmen Jieshi Chemical Co., Ltd., 33g, 0.105mol) into the above solution for about 30 minutes, during which the temperature is controlled <10°C. After the addition, continue to stir for 20 minutes to obtain a cloudy water solution of diazonium p-aminobenzenesulfonic acid, pH = 1, and the starch-potassium iodide test paper detects that there is a slight excess of nitrous acid.

[0047] The second step, the preparation of barbituric acid coupling solution

[0048...

Embodiment 2

[0056] The first step to the third step are the same as in Example 1.

[0057] The fourth step, the laking reaction

[0058] After the third step of the reaction, directly heat the reactant to 60°C and keep it warm for 1 hour to obtain a transparent and clear solution, adjust the pH to 5-6 with 10% KOH, and add CaCl dropwise 2 (Industrial product, 11.3g, 0.1mol) aqueous solution, after the dropwise addition, stop heating, cool naturally, and let stand overnight. The precipitated filter cake was filtered, washed with water until neutral, and dried at 120°C to obtain 33.2 g of a brilliant bright yellow solid, which was monoazo lake pigment I-1-1.

Embodiment 3

[0060] The first step, diazotization reaction of aromatic primary amine sulfonic acid

[0061] Mix Turmeric's Acid (industrial product, Inner Mongolia Xinya Chemical Co., Ltd., 22.7g, 0.1mol) and water (600ml), heat to 50°C under stirring, add 10% KOH solution dropwise until the solids are completely dissolved, and get Turmeric's Acid The aqueous solution of potassium salt is naturally cooled to room temperature, and the pH is adjusted to 1-2 with sulfuric acid. Turmeric acid is precipitated from the water to form a turbid solution. Use an ice / water bath to reduce the temperature of the turbid solution to <10°C. Under stirring, slowly add 40% nitrosylsulfuric acid (industrial product, 40% sulfuric acid solution, 33g, 0.105mol) into the above solution dropwise for about 30 minutes, during which the temperature is controlled to <10°C. After the addition, continue stirring for 20 minutes to obtain The diazonium salt of the acid (cloudy liquid, light yellow), pH = 1, starch-potass...

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