DE742940C - Process for the preparation of monoazo dyes - Google Patents

Description

Process for the preparation of monoazo dyes The subject of patent 727286 is a process for the preparation of monoazo dyes, which consists in that * diazo compounds from alkyl esters of carboxylic acids of the general formula H.INT-Aryl-S 02-alkyl-C OOH, in which the aryl radical - Belongs to the benzene series, with azo components of the general formula where R, hydrogen, alkyl or oxyalkyl and R 2 are alkyl or oxyalkyl and the benzene nucleus in the o- and m-positions to the amino group can contain further substituents with the exception of solubilizing groups, combined. The dyes thus obtained are particularly suitable for dyeing acetate rayon.

It has now been found that similar monoazo dyes are obtained if one uses dia.zo compounds from amides of carboxylic acids of the general formula H2 N-aryl-S 02-alkyl-CO OH, in which the aryl radical belongs to the benzene series and the hydrogen atoms to the carboxamide group may be completely or partially replaced by alkyl or oxyalkyl radicals with azo components of the general formula combined, in which R1 is a hydrogen atom, an allyl or oxalkyl radical, R "is an alkyl or oxalkyl radical and the denzene nucleus in the ortho- or in-position to the amino group can contain further substituents with the exception of solubilizing groups.

The dyes obtained in this way have the valuable property that Because of their good aim, they are made possible in very many cases without the addition of soap or soap-like agents for dyebathing on the acetat-artificial silk fibers.

The new dyes are also distinguished by the fact that they also dye tightly twisted fabrics or heavily twisted yarns well. In this important property, they are largely superior to the dyes known from French patent 80d.365 made from the same azo components and diazotized aminophenyloxalliyl sulfones. They are stronger in color than analogous dyes that are derived from the corresponding carboxylic acids. Example i 21.4 parts of 4 aminophyllsulfoyl acetic acid amide of the formula are diazotized in the usual way and combined with a solution of 20 parts of i-dioxäthylamino-3-methylbenzene. The dye formed after the addition of sodium acetate is filtered off with suction, washed and mixed with a dispersant. Acetate artificial silk turns a bath that contains only sodium sulfate, but no soap as an additive, into a strong and vivid orange. dyed, whereby tightly folded fabric is well dyed through. The dyeings are characterized by good fastness properties.

Similar dyes are obtained when using iN-oxethyl-N-methylamino-3-methylbenzene or i-dioxäthylamino-3-chlorobenzene as azo components. Example e The from 24.5 parts of 4,4minophenylsulfoylessigsäuredimethylamid.von the formula The prepared diazo solution is combined with a hydrochloric acid solution of -2o parts of r-Dioxätliylamino-3-methylbenzene. After addition of sodium acetate, the resulting dye is filtered off with suction and mixed with a dispersing agent. On acetate rayon, using the same dyeing method as given in Example i, vivid orange dyeings are obtained, with heavily twisted goods being dyed well through.

Dyes that have similar colorations with valuable fastness properties deliver, when using i-Dioxäthylamino-3-chlorobenzene, r-N-Oxäthyl-N-inetliylamino-3-methy benzene or -T-Oxäthy 1 - \ - inethylaminobenzol obtained as azole component. example 3 The diazo solution prepared from 24.5 parts of 4-aminoplienylsulfoylacetic acid dimethylamide When combined, it gives a finite hydrochloric acid solution of 15.5 parts of diethylaminobenzene after blunting the mineral acid with sodium acetate, an orange dye that is processed after suction and washing with a dispersing agent. At the Dyeing with the addition of soap gives an orange dye on acetate rayon with good fastness properties.

If the diazo component mentioned is replaced by 3-aminophenylsulfoylacetic acid dimethylamide off, then one obtains dyes that dye acetate silk in a reddish-tinged yellow. example .4 25.7 parts of 4-aminophenylsulfoylessigsäureoxäthylamid are in the usual way diazotized. The diazo solution obtained is with a hydrochloric acid solution of 15.5 Parts of Dietliylaminobenzene combined. After blunting the mineral acid with sodium acetate the resulting dye is separated off, washed and washed with a dispersing agent processed. When dyeing from a neutral 1 atrium sulfate bath, the prepared in this way delivers Dye on acetate rayon strong reddish orange colorations with good wet fastness properties own. Even heavily twisted goods are dyed well through.

A similar dye with also valuable: fastness properties is obtained if the diazo compound is used in place of the abovementioned diazo component from 3o parts of 4-aminophenylsulfoylessigsäuredioxäthylainid used. Example 5 The 2c9.2 parts of 3-chloro-4-aminophenylsulfoylessigsäureoxäthylainid as usual Diazo solution produced is treated with a hydrochloric acid solution of 16.5 parts of i - \ - Oxätliyl-N-methylainino-3-methylbenzene united. The resulting dye is deposited after the addition of sodium acetate. When mixed with a dispersing agent, it dyes acetate rayon the end neutral sodium sulphate bath, bright scarlet red. The dyeings have good wet fastness properties and good lightfastness.

Valuable dyes with similar hues are obtained when as azo component diethylaminobenzal or as diazo component the diazp compounds from 3-chloro-4-aminophenyls: ulfoylessigsäuredioxäthylamid or from 2-chloro-q.-aminophenylsulfoylessigsäureoxäthylatnid be used.

Claims (1)

PATENT CLAIM: Modification of the process for the production of monoazo dyes according to Patent 7: 27: 286, characterized in that diazo compounds from amides of carboxylic acids of the general formula H2 N-aryl-S 02-alkyl-C OOH, in which the aryl radical of the benzene series is used belongs and the hydrogen atoms of the carboxamide group can be wholly or partially replaced by alkyl or oxalkyl radicals, with azo components of .der general formula combined, where R1 is a hydrogen atom, an alkyl or oxalkyl radical, R2 is an alkyl or oxalkyl radical and the benzene nucleus in the o- or m-position to the amino group can contain further substituents with the exception of solubilizing groups. To distinguish the subject matter of the application from the state of the art, the following documents were taken into account in the grant procedure: French patents,. No. 804 365, 828 6x7.