Azo disperse dye compound, synthesis method thereof and application of compound

A technology of disperse dyes and compounds, applied in the direction of azo dyes, monoazo dyes, chemical instruments and methods, etc., can solve the problems of poor washing fastness and poor application performance, so as to improve affinity, dyeing performance and color Fastness, enhance the effect of van der Waals force

Active Publication Date: 2019-01-04
SHAOXING UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Disperse dyes are easy to enter and exit on the fiber, resulting in poor washing fastness and poor application performance

Method used

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  • Azo disperse dye compound, synthesis method thereof and application of compound
  • Azo disperse dye compound, synthesis method thereof and application of compound
  • Azo disperse dye compound, synthesis method thereof and application of compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Example 1: Dye 1a

Embodiment 1-1

[0049] Embodiment 1-1: Preparation of Dye 1a

[0050] (1) Ugi four-component reaction:

[0051] In a 250mL round bottom flask, add anhydrous methanol (150mL), aniline (4.39mL, 48.16mmol, 1.05eq), p-tolualdehyde (4.9mL, 48.16mmol, 1.05eq), formic acid (2.07mL, 55.04mmol , 1.2eq), and cyclohexylacetonitrile (5.69mL, 45.87mmol, 1.0eq). The reaction mixture was heated and stirred in an oil bath at 80° C. for 48 h, and analyzed by TLC, the reaction was complete. After the reaction solution was cooled to room temperature, it was cooled in the lower layer of the refrigerator overnight to produce a white solid. Suction filtration (washing with EA:PE=1:5 solution during suction filtration) obtained 7.0925 g of solid, the filtrate was spin-dried and weighed to obtain 4.6563 g. That is, the obtained Ugi products totaled 11.7488 g, and the total yield was 73%. The reaction equation is as follows:

[0052]

[0053] Product Confirmation:

[0054] IR (film) 3273, 3085, 2926, 1668, 1...

Embodiment 1-2

[0074] Spectral absorption performance: Weigh 0.05g of dye 1a, dissolve it in 50mL N,N-dimethylformamide, dilute it by a certain multiple to make the concentration 0.006g / L, and use a UV-2450 ultraviolet-visible spectrophotometer (Japan Shimadzu Corporation) measure the absorption spectrum curve, and compare with the same concentration 0.006g / L Disperse Orange 3 solution absorption spectrum curve, see image 3 .

[0075] From the absorption spectrum curve in the figure, it can be found that compared with Disperse Orange 3, the maximum absorption wavelength of the dye 1a shifted 3nm to the short wavelength direction, from the original 467nm to 464nm. After measurement, the specific performance indicators are shown in the following table 1-1:

[0076] Table 1-1. Performance parameters of dye absorption spectrum

[0077] dye name

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Abstract

The invention provides an azo disperse dye compound, a synthesis method thereof and an application of the compound. The synthesis method particularly includes the steps: (1) Ugi reaction: performing Ugi four-component reaction on aldehyde, aniline, methanoic acid and cyclohexyl isocyanides in organic solvents, filtering reaction liquid and washing the reaction liquid with the organic solvents to obtain Ugi products; (2) hydrolysis reaction: adding the Ugi products and acid into alcohols solvents to perform selective hydrolysis, and performing neutralization, organic solvent extraction, vacuumconcentration and drying on the reaction liquid to obtain hydrolysis products, namely, synthesizing coupling components of azo disperse dyes; (3) coupling reaction: coupling the obtained coupling components with 4-nitrophenyl diazonium salt in mixed solvents of alcohols and water, adjusting the pH (potential of hydrogen) value of the reaction liquid and filtering, washing and drying solids to obtain the azo disperse dye compound. The molecular weight and the molecular volume of the dyes can be effectively regulated, amide genes are led in, and dyeing properties for polyester fibers and polyamide fibers can be greatly improved.

Description

Technical field: [0001] The invention relates to an azo disperse dye compound and its synthesis method and application. Background technique: [0002] Disperse dyes were first used in the dyeing of acetate fibers, and then developed rapidly with the development of synthetic fibers, especially polyester fibers (polyester). Disperse dyes have various varieties, complete chromatograms and wide applications, and have become the most important branch of the dye industry. my country is the largest producer of disperse dyes in the world and has strong market competitiveness in the international market. Disperse dyes have a simple structure, low molecular weight, and no water-soluble groups. Although the molecules contain polar groups (such as hydroxyl, amino, hydroxyalkylamino, cyanoalkylamino, etc.), they are still non-ionic dyes. It is also the current hydrophobic dye. It is the most important type of dye for dyeing sexual fibers (such as polyester, polyamide, etc.). There are...

Claims

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Application Information

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IPC IPC(8): C09B29/08D06P1/18D06P3/56D06P3/28
CPCC09B29/0838D06P1/18D06P3/28D06P3/56
Inventor 冯高峰钱红飞李欢欢
Owner SHAOXING UNIVERSITY
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