Monoazo compounds, preparation method and uses thereof

A monoazo, compound technology, applied in the field of monoazo compounds, can solve the problems of poor washing fastness, poor washing fastness, difficult to dye deep, etc., and achieves good moisture resistance, good sublimation fastness, and good temperature dependence. Effect

Active Publication Date: 2008-10-22
阮伟刚
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Washing fastness becomes poor due to fine fibers and use of a large amount of disperse dyes
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Method used

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  • Monoazo compounds, preparation method and uses thereof
  • Monoazo compounds, preparation method and uses thereof
  • Monoazo compounds, preparation method and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] 2,4-dinitro-6-bromoaniline shown in formula (2)

[0038]

[0039] Carry out diazotization with nitrosyl sulfuric acid in sulfuric acid medium, the diazonium salt that obtains is coupled with the compound shown in formula (3) in acidic medium,

[0040]

[0041] where R 1 , R 2 , R 3 , R 4 and R 5 With the definition of the above-mentioned formula (1), then the obtained coupled compound is reacted with CuCN or NaCN+CuCN in an organic solvent to replace the bromine substituent, and the monoazo compound of the present invention shown in the formula (1) is obtained. compound.

[0042]

[0043] The diazo component (2) is known and readily available commercially, and the coupling component (3) can be prepared by well-known methods.

[0044] The present invention also relates to a mixture containing at least two azo compounds of different structures of the formula (1), which has better application properties. The mixture of the present invention can be prepared ...

Embodiment 2

[0047] Put 66.0ml of sulfuric acid into the flask, add 52.4g of 2,4-dinitro-6-bromoaniline at controlled room temperature, continue to stir for 30 minutes, cool with ice bath to reach 20-30°C, at this temperature 68.0g 42% nitrosyl sulfuric acid was added dropwise to the reaction mixture, and stirring was continued at this temperature for 4 hours. After completing the reaction, the mixture was dropped into a mixture of 30.0ml sulfuric acid, 900.0g ice water and 56.0g of the compound of the following formula within 30 minutes at 0-5°C,

[0048]

[0049] Stirring was continued for 2 hrs, then 1000 ml of water was added, and the temperature was slowly raised to 60° C. over 1 hour and kept for 1 hr. The resulting suspension was suction filtered, washed with water and dried.

[0050] A dye of the formula is obtained,

[0051]

[0052] Stir and mix 55.0g dry product of the above formula (4), 9.8g cuprous cyanide and 300g DMF, slowly raise the temperature to 60°C in 1 hour an...

Embodiment 3

[0058]Put 66.0ml of sulfuric acid into the flask, add 52.4g of 2,4-dinitro-6-bromoaniline at controlled room temperature, continue to stir for 30 minutes, cool with ice bath to reach 20-30°C, at this temperature 68.0g 42% nitrosyl sulfuric acid was added dropwise to the reaction mixture, and stirring was continued at this temperature for 4 hours. After completing the reaction, the mixture was dropped into a mixture of 30.0ml sulfuric acid, 900.0g ice water and 50.5g of the compound of the following formula within 30 minutes at 0-5°C,

[0059]

[0060] Stirring was continued for 2 hrs, then 1000 ml of water was added, and the temperature was slowly raised to 60° C. over 1 hour and kept for 1 hr. The resulting suspension was suction filtered, washed with water and dried.

[0061] A dye of the formula is obtained,

[0062]

[0063] Stir and mix 52.6g of the dry product of the above formula (4b), 9.8g of cuprous cyanide and 300g of DMF, slowly heat up to 60°C in 1 hour and...

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PUM

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Abstract

The invention relates to a monoazo compound, a preparation method and an application thereof. The azo compound is shown in the formula (1), wherein, R1 is hydrogen, methyl, ethyl, allyl, butyl, methoxy carbonyl ethyl and an ethoxy carbonyl ethyl; R2 is the hydrogen, the methyl and the ethyl; R3 is C1-6 alkyl, wherein, atoms can be included or not included for the alkyl chain; R4 is the hydrogen, the methyl, the ethyl, -NHCO-C1-4 alkyl and halogen, and the C1-4 alkyl in the -NHCO-C1-4 alkyl is the methyl, the ethyl, 2-methicillin ethyl and chloroethane; R5 is the hydrogen, the methoxy, the ethoxy, the 2-methicillin ethyl and the halogen. The preparation method comprises: the monoazo dye which contains the halogen is first prepared; and then cyan is used for replacing the halogen substituent. The monoazo compound of the invention which can be applied in polyester dyeing has the advantage of excellent application fastness.

Description

technical field [0001] The invention relates to a monoazo compound, a preparation method and its use. Background technique [0002] Disperse azo dyes having a 2,4-dinitro-6-cyanoaniline diazo component and an aniline coupling component have been known for a long time and have been used to dye hydrophobic fiber materials such as C.I. Disperse Blue 165:1. However, the known structural dyes and conventional disperse dyes dye polyester, especially superfine fibers, which are difficult to obtain dark colors. When dyeing dark blue, navy blue and black, the amount of dye must be greatly increased. Due to the fine fibers and the use of a large amount of disperse dyes, the washing fastness becomes very poor. Blended fabrics of polyester and spandex are more difficult to dye deep and have poorer wash fastness. Therefore, there is a need for an economical new dye with good depth and high wash fastness. Contents of the invention [0003] The object of the present invention is to ...

Claims

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Application Information

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IPC IPC(8): C07C245/08C09B62/008
Inventor 阮伟刚
Owner 阮伟刚
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