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Antibiotic azo dye comprising quaternary ammonium salt group and its preparation and uses

A technology of quaternary ammonium salt groups and azo dyes, applied in the direction of azo dyes, monoazo dyes, organic dyes, etc., can solve the problems of large energy consumption, waste water environmental pollution, etc., achieve slow dyeing speed, and simple synthesis method The effect of easy, broad-spectrum antibacterial properties

Inactive Publication Date: 2009-05-27
DALIAN UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At this time, a large amount of energy will be consumed, and the waste water produced will pollute the environment.

Method used

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  • Antibiotic azo dye comprising quaternary ammonium salt group and its preparation and uses
  • Antibiotic azo dye comprising quaternary ammonium salt group and its preparation and uses
  • Antibiotic azo dye comprising quaternary ammonium salt group and its preparation and uses

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] preparation.

[0039] Synthetic route (1):

[0040]

[0041] Synthesis of Intermediate 1: Add 10g of 4-nitrophenol, 6g of sodium hydroxide, and 150ml of water into a four-neck flask, heat to dissolve, add 60g of dibromoethane, 0.25g of tetrabutylammonium bromide, and react at 90°C 12 hours. Remove water and dibromoethane under reduced pressure, dissolve the residue with hot ethanol, remove insoluble salt, cool, and the product is precipitated from ethanol to obtain 15 g of product; yield: 79%. The melting point of the product is 64°C, which is the target product;

[0042] Synthesis of Intermediate 2: Add 20 g of NN-dimethyldodecylamine to 8 g of Intermediate 1, and react at 60° C. for 7 hours; wash the crude product with cyclohexane to obtain 14.25 g of the product, yield: 95%;

[0043] Synthesis of Intermediate 3: 7g of Intermediate 2 was dissolved in 50ml of ethanol, and a mixture of 14g of tin protochloride and 19g of concentrated hydrochloric acid with a wei...

Embodiment 2

[0050]

[0051] As shown in the synthetic route (1), the synthesis of intermediates 1, 2 and 3 is shown in Example 1;

[0052] Synthesis of Dye 5: 0.8g of Intermediate 3, 1.6ml of concentrated hydrochloric acid was added, an aqueous solution containing 0.131g of sodium nitrite was added dropwise in an ice bath (0-2°C), and the reaction was stirred for 2 hours to obtain a diazonium solution. 0.35 g of 1-phenyl-3-methyl-5-pyrazolone was dissolved in 20 ml of sodium carbonate aqueous solution to obtain a coupling solution. Add the coupling solution to the diazo solution at one time, control the pH value of the system from slightly acidic to neutral, and react at 5-15°C for 5 hours. Salt out with sodium chloride, filter out the precipitate, dry, dissolve the precipitate with absolute ethanol, filter off the insoluble salt, and remove the ethanol under reduced pressure to obtain 0.977g of dye; yield: 85%.

[0053] The total yield of dye 5 is 47.8%;

[0054] IR (KBr, cm -1 ): ...

Embodiment 3

[0058] the preparation of

[0059] The synthetic route of the dye is as follows:

[0060]

[0061] Synthesis of Intermediate 6: Add 5 g of p-nitrobenzyl bromide, add 15 g of N,N-dimethyldodecylamine, and react at 60°C for 5 hours; wash the crude product with cyclohexane to obtain 9 g of the product, yield: 92.1%;

[0062] Synthesis of Intermediate 7: Dissolve 4g of Intermediate 6 in 30ml of ethanol, add dropwise 8g of stannous chloride and 10g of a mixture of concentrated hydrochloric acid with a weight concentration of 36% under stirring, and react at 50°C for 8 hours. After the reaction, cool down to room temperature, add concentrated alkali, adjust the pH value to be alkaline, filter, and decompress the filtrate to obtain the crude product, add absolute ethanol to dissolve, filter out the insoluble salt, and remove the ethanol under reduced pressure to obtain 2.98g of product , Yield: 80%;

[0063] Synthesis of dye 8: 1 g of intermediate 7 was added to 2.1 ml of conc...

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Abstract

This invention relates to a quaternary antibacterial azo dye, characterizing: structural formula is indicated as formula(1), wherein: A is a quaternary group, B is a coupling group comprising aromatic ammonia group, pyridinone or pyrazolone. This invented dye can dye acrylic fibre according to the conventional cation staining, with the color fastness meeting the using requirement. The dye water solution and dyed acrylic fibre can kill or suppress Gram-positive bacteria and Gram-negative bacteria like Staphylococcus aureus and Escherichia coli.

Description

technical field [0001] The invention relates to an azo dye, in particular to an antibacterial cationic azo dye containing a quaternary ammonium salt group and its preparation and application. Background technique [0002] There are many pores distributed on the surface of textiles, and the surface area is very large, so a large number of bacteria should grow under suitable temperature and humidity conditions. The presence of various harmful bacteria leads to the spread of diseases and adversely affects human health. Antibacterial finishing is an important step in textile finishing, especially for textiles that come into contact with children, medical staff, soldiers, etc. When the dyeing process is the same as the antibacterial finishing process, the two can be treated in the same bath; but when the two processes are different, antibacterial finishing can only be performed in another bath after dyeing. At this time, a large amount of energy will be consumed, and the waste ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09B29/36D06P1/02D06P3/70
Inventor 马疆刘深赵德丰
Owner DALIAN UNIV OF TECH
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