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Pyridone-type azo disperse dyes containing sulfonate groups and synthesis method thereof

A pyridone-based azo and disperse dye technology, applied in azo dyes, monoazo dyes, organic dyes, etc., can solve the problems of high price of m-aminophenol, many reaction steps, three waste pollution, etc., and achieve high production value , The effect of simple synthesis and excellent comprehensive performance

Active Publication Date: 2021-11-16
JIANGSU D I A N CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, the diazo component of Disperse Yellow 114, 3-benzenesulfonyloxyaniline, uses m-aminophenol as a raw material at home and abroad, and undergoes a three-step reaction of acetylation protection of the amino group, benzenesulfonate esterification of the hydroxyl group, and deacetylation. Synthesis, there are many reaction steps, serious pollution of three wastes, and high price of m-aminophenol, which restrict the use of this dye variety, so it is of great significance to find alternative varieties with similar or better performance

Method used

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  • Pyridone-type azo disperse dyes containing sulfonate groups and synthesis method thereof
  • Pyridone-type azo disperse dyes containing sulfonate groups and synthesis method thereof
  • Pyridone-type azo disperse dyes containing sulfonate groups and synthesis method thereof

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Experimental program
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Effect test

Embodiment 1

[0041] The synthesis of embodiment 1 compound 3

[0042] Coupling of 3-Benzenesulfonyloxyaniline with 3-cyano-4-methyl-6-hydroxy-1-(2-propoxyethyl)-2-pyridone

[0043] Add 180mL hydrochloric acid and 99.6g (0.4mol) 3-benzenesulfonyloxyaniline into a 1000mL four-necked bottle, stir for 30min, cool to below 8°C, keep adding sodium nitrite solution dropwise at this temperature, and keep warm for 3h , detect the end point, filter, and reserve. Another 96.8g (0.41mol) of 3-cyano-4-methyl-6-hydroxy-1-(2-propoxyethyl)-2-pyridone was added to water, and liquid caustic soda was added and stirred to completely dissolve, 10 Below ℃, add diazo solution dropwise to control pH around 5. Incubate at 5°C for 1 hour, at 10°C for 1 hour, then at 60°C for 2 hours, filter, wash with hot water, and drain to obtain compound 3 as a dye filter cake. The analytical results of the refined product obtained by recrystallization are as follows: MS (m / z): 497 [M+H] + , elemental analysis C 24 h 24 N ...

Embodiment 2

[0044] The synthesis of embodiment 2 compound 8

[0045] Coupling of 3-benzenesulfonyloxyaniline with 3-cyano-4-methyl-6-hydroxy-1-[2-(2-ethoxyethoxy)ethyl]-2-pyridone

[0046] Add 160mL of hydrochloric acid and 99.6g (0.4mol) of 3-benzenesulfonyloxyaniline into a 1000mL four-necked bottle, stir for 30min, cool to below 6°C, keep adding sodium nitrite solution dropwise at this temperature, and keep warm for 4h after dropping , detect the end point, filter, and reserve. Another 109.1g (0.41mol) of 3-cyano-4-methyl-6-hydroxy-1-[2-(2-ethoxyethoxy)ethyl]-2-pyridone was added to water, and liquid caustic soda was added Stir to dissolve completely, add diazo solution dropwise below 10°C, and control the pH to about 5. Incubate at 6°C for 2h, then at 80°C for 1h, filter, wash with hot water, and drain to obtain compound 8 as a dye filter cake. The analytical results of the refined product obtained by recrystallization are as follows: MS (m / z): 527 [M+H] + , elemental analysis C ...

Embodiment 3

[0047] The synthesis of embodiment 3 compound 12

[0048]Coupling of 3-benzenesulfonyloxyaniline with 3-cyano-4-methyl-6-hydroxy-1-[2-(3-propoxypropoxy)ethyl]-2-pyridone

[0049] Add 60mL of sulfuric acid, 140mL of water, and 99.6g (0.4mol) of 3-benzenesulfonyloxyaniline into a 1000mL four-necked bottle, stir for 30min, cool to below 5°C, and add sodium nitrite solution dropwise at this temperature until the end of the dropwise Incubate and react for 2 hours, detect the end point, filter, and set aside. Another 120.5g (0.41mol) 3-cyano-4-methyl-6-hydroxy-1-[2-(3-propoxypropoxy)ethyl]-2-pyridone was added to water, and liquid caustic soda was added Stir to dissolve completely, add diazo solution dropwise below 12°C, and control the pH to about 5. Incubate at 5°C for 1h, at 10°C for 1h, then at 80°C for 1h, filter, wash with hot water, and drain to obtain dye cake compound 12. The analytical results of the refined product obtained by recrystallization are as follows: MS (m / z)...

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Abstract

The invention discloses a sulfonate group-containing pyridone-type azo disperse dye and a synthesis method thereof. The general chemical structure formula is as follows:. The method uses 3-benzenesulfonyloxyaniline as a raw material, and obtains a product through diazotization and coupling reaction. The product of the invention has novel structure, simple synthesis and excellent performance, and is suitable for industrial production.

Description

technical field [0001] The invention relates to a sulfonate group-containing pyridone-type azo disperse dye and a synthesis method thereof, belonging to the field of dye chemical industry. Background technique [0002] Disperse dyes are a kind of water-insoluble dyes mainly used for dyeing and printing of polyester and its blended fabrics, which need to be processed commercially with the help of various auxiliaries. The structures of disperse dyes mainly include azo type, anthraquinone type, quinophthalone type, styrene type, etc. Among them, heterocyclic disperse dyes have high color development strength, bright color, good lifting power, high dyeing rate, and level dyeing. Excellent performance, excellent color fastness and other characteristics have become one of the fastest developing directions of disperse dyes in recent decades. Pyridone-type heterocyclic disperse dye Disperse Yellow 114 is a typical disperse dye with heterocyclic azo structure. Well, it can be used ...

Claims

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Application Information

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IPC IPC(8): C09B29/42
CPCC09B29/363
Inventor 王一键胡效奎过介生牟忠岳李见魏斌郑土才
Owner JIANGSU D I A N CHEM CO LTD
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