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Pyridone heterocyclic azo disperse dye and preparation method thereof
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一种杂环偶氮、吡啶酮基的技术，应用在杂环偶氮分散染料及其制备领域，能够解决难以获得染料等问题
Inactive Publication Date: 2017-02-15
DALIAN UNIV OF TECH
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However, heterocyclic active methylene compounds and heterocyclic phenolic compounds need to be coupled under alkaline conditions, and weakly basic aromatic amines are diazotized in concentrated sulfuric acid. When the system is adjusted to alkaline, a large amount of inorganic salts will be produced. It is difficult to obtain the corresponding dye
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[0137] On the other hand, the present invention also provides the preparation method of above-mentioned compound, and this preparation method is to carry out diazotization to diazonium component in organic solvent in the presence of concentrated sulfuric acid, precipitates stable diazonium salt solid, After the solid is obtained by filtration, the coupling reaction with the coupling component is carried out under alkaline conditions to obtain the target dye. Specifically include the following steps:
[0138] (1) Add the diazo component, concentrated sulfuric acid, organic solvent and stabilizer according to the present invention into the reaction vessel A, after cooling down to 0010°C, add the diazotization reagent in batches, react for 0.1010h, and filter to obtain diazo Component diazonium salt solid;
[0139] (2) Add the coupling component and water described in claim 1 in the reaction vessel B, adjust the pH value to 8012 with 10% sodiumhydroxide, dissolve the coupling c...
Embodiment 1
[0150] The preparation of embodiment 1 compound 1#
[0151] (1) Add 1.5g of 5-aminobenzimidazolone, 1g of concentrated sulfuric acid, 80ml of ethylene glycol diethyl ether, and 5g of 1,5-naphthalene disulfonic acid into a three-necked flask, cool down to 5°C in an ice-water bath, and drop 3g of tert-butyl nitrite, the time of dropping is 0.5h, and the reaction is 2 hours after the dropwise addition is completed; the diazonium salt solid is obtained after filtration; (2) 1.34g 3-methyl-1-phenyl-5 pyrazolone 100ml of water was added to the reactor, the pH value was adjusted to 10 with 10% sodiumhydroxide solution, cooled to 5°C, and the 5-aminobenzimidazolone diazonium salt obtained in step (1) was added under stirring, and mixed with 10% carbonic acid The pH value of the sodium solution was controlled at 9, and the addition was completed within half an hour, and reacted at 5°C for 2 hours; after the reaction was completed, filtered, washed with ice water until the filtrate was...
Embodiment 2
[0154] The preparation of embodiment 2 compound 2#
[0155] (1) Add 1.83g of 2,4-dinitroaniline, 2g of concentrated sulfuric acid, 40ml of ethylene glycol dimethyl ether, and 4g of 1,5-naphthalene disulfonic acid into a three-necked flask, cool to 3°C in an ice-water bath, drop Add 3g of nitrosyl sulfuric acid, dropwise time is 0.5h, and react for 2 hours after the dropwise addition is completed; after filtration, the diazonium salt solid is obtained; (2) Add 0.81g 3-methyl-5-pyrazolone and 80ml water In the reactor, use 10% sodium hydroxide solution to adjust the pH value to 11, cool to 4 ° C, add the 2,4-dinitroaniline diazonium salt obtained in step (1) under stirring, and use 10% sodium carbonate solution to control The pH value was 9, the addition was completed within half an hour, and the reaction was carried out at 5°C for 2 hours; the reaction was completed, filtered, washed with ice water until the filtrate was neutral, and dried to obtain a heterocyclic azo disperse ...
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Abstract
The present invention relates to a pyridone heterocyclic azo disperse dye and a preparation method thereof. The pyridone heterocyclic azo disperse dye is composed of two parts: namely a diazo component and a coupling component. The coupling component is composed of a heterocyclic active methylene compound or a heterocyclic phenolic compound that is coupled under the basic condition. The diazo component is composed of a weakly basic heterocyclic aromatic amine or a weakly basic aniline derivative. The preparation method comprises the steps of in the presence of a stabilizing agent, subjecting the weakly basic heterocyclic aromatic amine or the weakly basic aniline derivative to diazotization treatment in an organic solvent to precipitate a stable diazonium salt solid, filtering to obtain the solid, and applying the solid to alkaline coupling to obtain a target dye. The dye can be applied to the dyeing process of polyester fibers, polyamide fibers, polylactic acid fibers, polypropylene fibers and cellulose acetate fibers, and is excellent in dyeing brightness.
Description
technical field [0001] The invention relates to a heterocyclic azo disperse dye and a preparation method thereof. Background technique [0002] Synthetic fibers have a compact structure, high crystallinity, and are difficult to dye. Generally, disperse dyes are used for dyeing to improve the binding force between dyes and hydrophobic fibers. [0003] The structure of disperse dyes does not contain water-soluble groups such as sulfonic acid groups or carboxyl groups, and is difficult to dissolve in water. When it is commercialized, it needs to be ground together with a dispersant. When it is applied, it is dispersed in water with insoluble fine particles by means of a dispersant, and is used for high-temperature, high-pressure or high-temperature hot-melt dyeing of synthetic fibers. Disperse dyes for synthetic fibers mainly include azo, anthraquinone, nitrodiphenylamine and other types according to their structure, and azo-type disperse dyes are extremely important in disper...
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