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Heterocyclyl-azo-dialkyl aminophenol pigments and process for synthesizing the same

A technology of an alkylaminophenol and a synthesis method, applied in the directions of azo dyes, monoazo dyes, organic dyes, etc., can solve the problems of inconvenient laboratory operation, difficult to fully contact, increased product separation and purification, and easy to achieve reaction conditions. Control, excellent optical properties, simple instrument effect

Inactive Publication Date: 2004-12-29
HEILONGJIANG UNIV
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AI Technical Summary

Problems solved by technology

Heterocyclic azo dyes have good light and thermal stability, spectral properties and solubility properties, but it is difficult to achieve the desired effect by using some common azo synthesis methods. Therefore, seeking to have good photothermal stability, spectral properties and The efficient synthesis of new azo dyes with solubility properties has become an important problem to be solved urgently
In 2001, United States Patent 6214519B1 reported the synthesis of some heterocyclic azo dyes, but the yield was very low, only 26-42%
This method mainly has the following disadvantages: (1) the scope of application of this method is relatively narrow, and some new azo materials are difficult to synthesize by this method
If the novel azo dyes synthesized in this paper are carried out using phosphoric acid system, the reaction yield is very low (<30%), and it also increases difficulties for the separation and purification of the product
(2) Due to the poor solubility of general organic diazo components in phosphoric acid, the temperature of the reaction system should not be too high, which is not conducive to the smooth progress of the reaction
(3) Because sodium nitrite is a kind of easily hygroscopic deliquescence, the substance with bigger toxicity, its solid is directly added in the system slowly, on the one hand is not convenient for laboratory operation, easily loses, causes pollution; On the other hand, nitrous acid Sodium solid and viscous reaction liquid are not easy to fully contact, and it is not conducive to the smooth progress of the reaction

Method used

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  • Heterocyclyl-azo-dialkyl aminophenol pigments and process for synthesizing the same
  • Heterocyclyl-azo-dialkyl aminophenol pigments and process for synthesizing the same
  • Heterocyclyl-azo-dialkyl aminophenol pigments and process for synthesizing the same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] (1) Dissolve 0.4045 g (4.0 mmol) of the diazo component 2-amino-1,3,4-thiadiazole in 4 ml of acetic acid and 2 ml of propionic acid, then stir, at -10-5°C, Add 0.4 ml of sulfuric acid, slowly add 1.22 g (4.8 mmol) of 50% nitrosyl sulfuric acid, and carry out a diazotization reaction for 2 hours to prepare a diazonium salt solution.

[0017] (2) Dissolve 0.6035 g (4.4 mmol) of the coupling component N, N-dimethyl-3-aminophenol, 0.16 g of urea and 1.6 g of sodium acetate in 20 ml of methanol, cool to -10-5 ° C, and stir , slowly drop the above diazonium salt solution into the reaction system, continue to stir for 4 hours, let stand overnight, filter, wash with water, and dry to obtain the azo dye 2-[2-(1,3,4-thiadiazolyl) Azo]-5-(N,N-dimethylamino)phenol 0.788 grams.

[0018] Yield: 79%, melting point: 241-242°C.

[0019] The characteristic absorption peaks of infrared spectrum (FT-IR) are: 3075, 2955, 2928, 2872, 1637, 1534, 1471, 1318, 1289, 1195, 1143, 1072, 895, 808...

Embodiment 2

[0029] (1) Dissolve 0.4606 g (4.0 mmol) of the diazo component 2-amino-5-methyl-1,3,4-thiadiazole in 4 ml of acetic acid and 2 ml of propionic acid, then stir, at -10-5 Under the condition of ℃, add 0.4ml sulfuric acid, slowly add 1.22 grams (4.8mmol) of 50% nitrosyl sulfuric acid, carry out diazotization reaction for 2 hours, and prepare diazonium salt solution.

[0030] (2) Dissolve 0.6035 g (4.4 mmol) of the coupling component N, N-dimethyl-3-aminophenol, 0.16 g of urea and 1.6 g of sodium acetate in 20 ml of methanol, cool to -10-5 ° C, and stir , slowly drop the above diazonium salt solution into the reaction system, continue to stir for 4 hours, let stand overnight, filter, wash with water, and dry to obtain the azo dye 2-[2-(5-methyl-1,3,4- Thiadiazolyl)azo]-5-(N,N-dimethylamino)phenol 0.705 g.

[0031] Yield: 67%, melting point: 229-230°C.

[0032] The characteristic absorption peaks of infrared spectrum (FT-IR) are: 3127, 2960, 2925, 2872, 1644, 1535, 1440, 1384, 13...

Embodiment 3

[0042] (1) Dissolve 0.5167 g (4.0 mmol) of the diazo component 2-amino-5-ethyl-1,3,4-thiadiazole in 4 ml of acetic acid and 2 ml of propionic acid, then stir, at -10-5 Under the condition of ℃, add 0.4ml sulfuric acid, slowly add 1.22 grams (4.8mmol) of 50% nitrosyl sulfuric acid, carry out diazotization reaction for 2 hours, and prepare diazonium salt solution.

[0043] (2) Dissolve 0.6035 g (4.4 mmol) of the coupling component N, N-dimethyl-3-aminophenol, 0.16 g of urea and 1.6 g of sodium acetate in 20 ml of methanol, cool to -10-5 ° C, and stir , slowly drop the above diazonium salt solution into the reaction system, continue to stir for 4 hours, let it stand overnight, filter, wash with water, and dry to obtain the azo dye 2-[2-(5-ethyl-1,3,4- Thiadiazolyl)azo]-5-(N,N-dimethylamino)phenol 0.798g. Yield: 72%.

[0044]

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Abstract

The present invention is heterocyclic azo-dialkyl phenol dye and its synthesis, and relates to chemical product and its preparation technology. The synthesis process includes dissolving diazo component in organic solvent through stirring, adding concentrated inorganic acid at certain temperature, adding nitrosulfonic acid slowly to obtain diazo solution; and through dissolving the coupling component, urea and sodium acetate in organic solvent via stirring at certain temperature, dropping the diazo solution slowly into the reaction system through stirring, letting stand for a night, filtering, washing and drying, azo dye is prepared. The dye has high dissolvability, good optical property, high light and heat stability, and the process has high yield, simple reaction system and easily controlled reaction condition.

Description

technical field [0001] The invention relates to a heterocyclic monoazo dye, namely 2-[2-(5-alkyl-1,3,4-thiadiazolyl)azo]-5-(N,N-dialkyl Amino)phenol and 2-[2-(5-alkyl-3-isoxazolyl)azo-5-(N,N-dialkyl)phenol dyes and methods for their synthesis, especially with respect to amino-substituted A heterocyclic monoazo dye with nitrogen-containing aromatic heterocycles such as thiadiazole and isoxazole as diazo components and aromatic amine derivatives as coupling components and a synthesis method thereof. The method of the invention can be widely used in the synthesis of heterocyclic azo dyes. Background technique [0002] Azo compounds are widely used as dyes, organic synthesis intermediates, analytical reagents, oil-soluble dyes in modern color photography technology, etc. The structure of azo is modifiable, and there can be various substituents on both sides of the azo bond, such as aromatic derivatives and heterocyclic derivatives, etc., especially some azo dyes can form chela...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B29/36
Inventor 陈志敏吴谊群左霞
Owner HEILONGJIANG UNIV
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