CN1005264B

CN1005264B - Azoic diphenylamine yellow dispering dye

Info

Publication number: CN1005264B
Application number: CN87100778.9A
Authority: CN
Inventors: 王喆; 何连芳
Original assignee: DALIAN DYE FACTORY
Current assignee: DALIAN DYE FACTORY
Priority date: 1987-02-19
Filing date: 1987-02-19
Publication date: 1989-09-27
Also published as: CN87100778A

Abstract

The present invention relates to medium temperature type azoic diphenylamine yellow dispersion dye for dyeing and mixing colors for polyester fiber and dacron/cotton mixed fabric. A synthetic dyeing structure is 4-(2, 4-dinitro) benzoimine-4'-hydroxyazo-benzene, namely the dye has various kinds of excellent fastness and dyeing performance and has the advantages of brilliant color light, very high lifting capacity, simple production process and low price. A coloring rate is as high as 96%, and a hot melting color fixing rate can achieve more than 92%. Compared with dispersion yellow RGFL, the dispersion dye has high use value.

Description

A kind of azoic diphenylamine yellow dispering dye

The invention belongs to a kind of preparation method of Yellow disperse dye, particularly have the Yellow disperse dye of azoic diphenylamine structure, be applicable to the printing and dyeing and the colorant match of trevira and polyester/cotton blended fabric.

Yellow is a mass-tone in the dyestuff chromatogram.The structure type of Yellow disperse dye is a lot, and is wherein a lot of with domestic and international manufacturer, large usage quantity, and cheap Disperse Yellow RGFL kind has very big competitive power.It is a disazo dyes, but this kind is low temperature modification dispersed dye, and fastness to sublimation is low, is unsuitable for pad-dry-cure dyeing, handles undesirable to the heat setting type of DYED FABRICS simultaneously.Though the dispersed dye C.I.Disperse Yellow42 of pentanoic structure has better fastness, shortcoming is that tinting power is very low, and dyeing behavior is not good.

The objective of the invention is to make a kind of have excellent every fastness and dyeing behavior, the tinting power height, coloured light is bright-coloured, cheap Yellow disperse dye, temperature dyeing in being particularly useful for to cut down the consumption of energy, improves printing quality.

If on a disperse dyes structure, the constitutional features of existing azoic dyestuff has the constitutional features of pentanoic dyestuff again, and this has just constituted a kind of dispersed dye of composite structure.The dispersed dye of this azoic diphenylamine have two class dyestuffs more comprehensive advantage on fastness and dyeing behavior concurrently.

Azoic diphenylamine yellow dispering dye-4-(2, the 4-dinitrobenzene) benzene imines-4 '-synthesis route of hydroxyazobenzene, can pass through p-Nitraniline or right-amino acetanilide, through diazotization, with the phenol coupling, the former again through the reduction, the latter is hydrolyzed, all can obtain 4-amino-4 '-hydroxyazobenzene, then, with 2, the condensation of 4-dinitrochlorobenzene just can make dispersed dye.Also can be earlier with right-amino acetanilide and 2, the 4-dinitrochlorobenzene is carried out condensation, then, and with the condenses hydrolysis, diazotization again, last and phenol coupling makes azoic diphenylamine yellow dispering dye.

The 4-(2 that the present invention makes, the 4-dinitrobenzene) benzene imines-4 '-the hydroxyazobenzene Yellow disperse dye, 6 grades of light fastnesss (carbon arc), and have all other excellent fastness:

Warm molten in being suitable for, degree of fixation reaches more than 92% between 190～210 ℃, and the degree of fixation curve is smooth, and dye uptake is up to 96%, and this dye shade is bright-coloured, and good level-dyeing property also has very high load-carrying capacity.

4-(2,4-dinitrobenzene) benzene imines-4 '-structure of hydroxyazobenzene Yellow disperse dye is:

Its synthesis route is divided into condensation, hydrolysis, diazotization, coupling and makes.

(1), with 2, the 4-dinitrochlorobenzene is a raw material, carries out condensation with para aminoacet anilide, that is:

(2), condenses is hydrolyzed in acidic aqueous media, that is:

(3), hydrolysate carries out diazotization reaction, that is:

(4), diazonium salt and phenol carries out coupling, obtains Yellow disperse dye:

Most preferred embodiment is described below:

In 250 milliliters there-necked flask, add 20.25 grams 2,4-dinitrochlorobenzene, the 15.3 right-amino acetanilides of gram and 5.4 gram yellow soda ash, in 80～110 ℃ of water mediums, react, after reaction finishes, cold filtration, be washed to neutrality, dry that product 31.0～31.5 restrains fusing point: 235.8～240 ℃, yield 98.69%.

In 500 milliliters there-necked flask, add hydrochloric acid, water and 31.6 gram condensess, be warmed up to 95～110 ℃ under stirring, complete until hydrolysis reaction.Reduce to room temperature, cooling slowly with the sodium hydroxide neutrality that neutralizes, is filtered down, with 500 ml water filter washes also, after the drying product 27.4～28.4 restrains, dry product contains amine value 80.98～87.04%, average yield is 86.42%.

In 250 milliliters there-necked flask, add 15.8 milliliters of hydrochloric acid and 150 ml waters, stir the 16.4 gram hydrolyzates of adding down.Making beating is cooled to 0～5 ℃, drips sodium nitrite solution, is no more than 15 ℃, reacts 3 hours, keeps Starch iodide paper to be blue look.Reaction is poured material in the water into after finishing, and filters insolubles, washing filter residue, decoupling in the lump.

Take by weighing 4.3 gram phenol and 5 milliliters of liquid caustic sodas, add 100 ml waters, after the stirring and dissolving, add 6.5 gram yellow soda ash again.This coupling component is added in 2000 milliliters the there-necked flask, cools to below 15 ℃.Add the above-mentioned diazonium liquid for preparing, PH=8～8.5, reaction is to terminal.Filter, wash neutrality.Dry back product 17.5～18.4 grams, average yield 92.87%.

The 4-(2 that makes, the 4-dinitrobenzene) benzene imines-4 '-the hydroxyazobenzene dispersed dye are the yellowish brown powder.Water insoluble, be dissolved in dimethyl formamide or the acetone.Be dissolved in the vitriol oil; Be insoluble to diluted acid, diluted alkaline is slightly soluble in other organic solvent.

Claims

1, the preparation method of warm type Yellow disperse dye is characterized in that 2-(2, the 4-dinitrobenzene in a kind of) benzene imines-4 '-synthesis technique of hydroxyazobenzene dispersed dye makes through condensation, hydrolysis, diazotization, coupling.The raw material of condensation is with 2, and 4-dinitrochlorobenzene and right-amino acetanilide react:

With 20.25 grams 2,4-dinitrochlorobenzene and 15.3 gram para aminoacet anilides, in water medium, in the presence of 5.4 gram yellow soda ash, 80～110 ℃ are reacted and obtain 31.0～31.5 and restrain condensess.

Hydrolysis reaction is to carry out in acidic medium:

31.6 gram condensess are added in the entry, add hydrochloric acid again, till 95～110 ℃ of hydrolysis reaction are when complete.With sodium hydroxide neutralization, filtration, washing, drying, obtain 27.4～28.4 gram hydrolyzates, containing the amine value is 80.98～87.04%.

Carry out diazotization reaction with hydrochloric acid:

Earlier 15.8 milliliters of hydrochloric acid and 150 ml waters are added in the reactor, under agitation add 16.4 gram hydrolyzates then, be cooled to 0～5 ℃ after, drip sodium nitrite solution, be no more than 15 ℃, react end after 3 hours.Pour in the water, filter insolubles, washing filter residue, decoupling in the lump.

The coupling component is a phenol:

With 4.3 gram phenol and 5 milliliters of liquid caustic sodas, add 100 ml waters, after the stirring and dissolving, add 6.5 gram yellow soda ash again, cool to below 15 ℃, add the above-mentioned diazonium liquid for preparing, PH is 8～8.5, reaction to terminal, filter washing, drying, obtain Yellow disperse dye 4-(2, the 4-dinitrobenzene) benzene imines-4 '-hydroxyazobenzene 17.5～18.4 grams.