Preparation method of blue dye based on pyridine/2-aminothiophene/barbituric acid ternary system

A technology of dimethyl barbituric acid and blue dyes, which is applied in the preparation of azo dyes, azo dyes, organic dyes, etc., can solve the problems of small quantity and types of disperse blue dyes, and achieve simple operation steps Effect

Inactive Publication Date: 2020-04-28
CHANGZHOU INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, among the existing commercial heterocyclic disperse dyes, there are a large number of disperse yellow, orange and red dyes, and the number and types of disperse blue dyes are relatively small, and most of the classic disperse blue dyes currently used were invented a hundred years ago of

Method used

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  • Preparation method of blue dye based on pyridine/2-aminothiophene/barbituric acid ternary system
  • Preparation method of blue dye based on pyridine/2-aminothiophene/barbituric acid ternary system
  • Preparation method of blue dye based on pyridine/2-aminothiophene/barbituric acid ternary system

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Experimental program
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Effect test

Embodiment 1

[0023] First follow [Zhao XL, Geng J, Huang W. pH-induced azo-keto and azo-enoltautomerism for 6-(3-methoxypropylamino)pyridin-2-one based thiophene azodyes. Dyes Pigm 2017; 147:318-26.] Compound 1 and Compound 2 were prepared by the above process, namely 7 and 13 in Scheme 1, respectively.

[0024] Preparation 1 of compound 3:

[0025] Weigh 2.59g (5mmol) of compound 1, 1.17g (7.5mmol) of 1,3-dimethylbarbituric acid in an eggplant-shaped bottle, add 5ml of anhydride to fully dissolve it, and reflux at 90°C for 3 hours; After the reaction was monitored by TLC, the heating was stopped, the reaction solution was returned to room temperature, and a solid was precipitated. Then filter under reduced pressure, and wash the filter residue with sufficient water and isopropanol. The crude product was recrystallized from methanol and dichloromethane to obtain compound 3 in 80% yield (2.62 g). 1 H NMR (400MHz, CDCl 3 , ppm): δ=13.14(s, 1H), 8.82(s, 1H), 4.41-4.32(m, 2H), 4.00(m, J=11...

Embodiment 2

[0032] The concentration is respectively configured as 3.0×10 -5 The dichloromethane solution of mol / L dyestuff 3-4, test its UV-Vis absorption spectrum asfigure 1 shown. The maximum absorption wavelength of the corresponding compound (λ max ), molar extinction coefficient (ε) and width at half maximum (FWHM) are shown in Table 1.

[0033] Table 1 Compounds 1-4 in CH 2 Cl 2 The wavelength of maximum absorption in the solvent (λ max ), molar extinction coefficient (ε) and width at half maximum (FWHM)

[0034]

[0035] It can be seen from the figure that the prepared dye 3 is different from our previously reported reaction precursor dye 1 (derived from [ZhaoXL, Geng J, Huang W. pH-induced azo-keto and azo-enol tautomerism for 6-(3- Compared with methoxypropylamino) pyridin-2-one based thiophene azo dyes. Dyes Pigm 2017; 147:318-26.]), its maximum absorption wavelength is red-shifted from the original 517nm to 582nm. This phenomenon can be interpreted as the introduction...

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Abstract

The invention discloses a preparation method of a blue dye based on a pyridine / 2-aminothiophene / barbituric acid ternary system, which comprises the following steps: controlling the molar ratio of compounds 1 or 2, 1, 3-dimethyl barbituric acid to acetic anhydride to be 1: (1-2): 0.5, dissolving the compounds 1 or 2 and 1, 3-dimethyl barbituric acid in acetic anhydride, heating, stirring and refluxing; recovering to room temperature after the reaction, and separating out solid; and carrying out reduced pressure suction filtration, washing filter residues with water and isopropanol, and recrystallizing the crude product with methanol and dichloromethane to obtain the dye. The invention further discloses a blue dye based on the pyridine / 2-aminothiophene / barbituric acid ternary system. The blue dye is synthesized for the first time, a UV-Vis absorption spectrum result shows that by expanding a Donor-pi-acceptor (D-pi-A) conjugated system of dye molecules, the maximum absorption wavelength(lambda max) of the Donor-pi-acceptor (D-pi-A) conjugated system has obvious red shift compared with a raw material, and finally the blue dye is obtained.

Description

technical field [0001] The invention relates to a preparation method of a blue dye based on a pyridine / 2-aminothiophene / barbituric acid ternary system, and belongs to the technical field of dye synthesis. Background technique [0002] Compared with aniline dyes, heterocyclic dyes not only have better dyeing ability and coloring ability, but also they have a wide range of applications in nonlinear optical materials, anticancer, antibacterial and antioxidant activities, optical sensing of metal ions, and electronics industry . However, among the existing commercial heterocyclic disperse dyes, there are a large number of disperse yellow, orange and red dyes, and the number and types of disperse blue dyes are relatively small, and most of the classic disperse blue dyes currently used were invented a hundred years ago of. Therefore, it is a very meaningful work to design and synthesize blue dyes and explore their potential applications. Contents of the invention [0003] In ...

Claims

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Application Information

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IPC IPC(8): C09B43/00
CPCC09B43/00
Inventor 赵晓蕾张金涛汪敏许鹏丁琳琳王昌英
Owner CHANGZHOU INST OF TECH
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