DE1060835B - Process for the production of water-insoluble azo dyes on the fiber - Google Patents

Description

GERMAN

F 21463 IVc / 8m

REGISTRATION DATE: OCTOBER 20, 1956

NOTICE THE REGISTRATION AND ISSUE OF THE EDITORIAL:

JULY 9, 1959

The subject of patent application F 19 481 IVc / 8m is a method for producing water-insoluble azo dyes on the fiber which consists in that one on the fibers the diazonium compounds from p-aminoazo compounds of the formula

-N = N

NH,

NO ₂ Cl

wherein the nitro group is in the m- or p-position to the azo group and R is hydrogen, a halogen atom, an alkyl or alkoxy group with arylamides of aromatic or heterocyclic o-oxycarboxylic acids or acyl acetic acids.

According to this process, in which solid diazonium compounds are advantageously obtained from p-aminoazo compounds with excellent durability, valuable azo dyes can be produced on the fiber, which are characterized by good fastness properties.

In pursuing this inventive concept it has now been found that dyes of similar good fastness properties obtained if one in the process of the main patent application Diazonium compounds from p-aminoazo compounds of the formula

/ -K_ _N _ _N

H ^

NO ₈

NH,

wherein the nitro group is in m- or p-S division to the azo group, R is hydrogen, a halogen atom, an alkyl or Alkoxy group and R 'denotes an alkyl or alkoxy group is used.

The procedure follows closely that of the main patent application.

The p-aminoazo compounds on which the present invention is based and not yet described in the literature can be produced by known processes. Appropriately one uses their solid, through very good durability excellent diazonium compounds, as they are according to German Auslegeschrift 1,047,787.

example 1

Cotton yarn is treated at a liquor ratio of 1:20 for 45 minutes at 35 ° C in the subsequent Grundierungsbad, centrifuged wet and fully colored in the developing bath at 20 ⁰ C. Then it is rinsed with 3 ecm hydrochloric acid of 20 ° bei liter water, first 15 minutes at 60 ° C, then 15 minutes at 95 ° C with 1 g of a one-process for the production

of water-insoluble azo dyes

on the fiber

Addition to patent application F 19481 IVc / 8m
(Interpretation document 1 056 582)

Applicant:

Farbwerke Hoechst Aktiengesellschaft

formerly Master Lucius & Brüning,

Frankfurt / M., Brüningstr. 45

Dr. Herbert Kracker, Offenbach / M.,

Dr. Ulrich Dreyer, Offenbach / M.-Bürgel,

and Dr. Walter Staab, Offenbach / M.,

have been named as inventors

Effective product of about 10 moles of ethylene oxide to 1 mole of isododecylphenol and 3 g of soda per liter of water soaped, rinsed and dried.

Primer bath

4.5 g of l- (2 ', 3'-oxynaphthoylamino) -2,4-dimethoxy-5-chlorobenzene are dissolved in 13.5 cm of denatured alcohol, 1.5 cm of sodium hydroxide solution at 38 ° Be, 1.5 cm of formaldehyde solution ( 33 ° / _o solution) and 4.5 cc of warm water and treated with water at 35 ° C, 3 g of a condensation product of higher molecular weight fatty acids and protein degradation products, and 10 cc of sodium hydroxide solution of 38 ° Be was adjusted to 11.

Developing bath

2.9 g of 4-amino-2-methyl-5-chloro-4'-nitrol-l, l'-azobenzene in the form of a diazonium compound prepared in the usual way are dissolved in 11% of water, which gives 1 g of an action product of about 20% Moles of ethylene oxide to 1 mole of octodecyl alcohol and 5 ecm of acetic acid (50 ° / ₀ ig) contains.

A dark garnet with a bluish cast and good fastness properties is obtained.

The dyeing process can also be carried out on other types of fiber, for example rayon or rayon

will. . .

Example 2

Cotton fabric is padded on the padder with the following solution and dried: 14 g of 2,3-oxynaphthoylaminobenzene are with 20 g of a wetting agent

909 560/379

of the type of Ölsulfonalc and 21 ecm sodium hydroxide solution of 38 ° Bc dissolved and adjusted to 1 l with boiling water.

The dried material is developed on the padder with a solution containing 14.5 g of 4-amino-2-methyl-5-chloro-4'-nitro-1, l'-azobenzene in one liter of water in the usual way diazonium compound prepared, 1 g of an action of the product of about 20 moles of ethylene oxide to 1 mole Octodccylalkohol and 10 cc acetic acid (50 ° / _o solution) contains.

After an air passage of 30 seconds, rinsed hot and cold, for 20 minutes at 95 ⁰ C and L g of a Einwirkungsproduktcs of about 10 moles of ethylene oxide to moles of t Isododccylphcnol and 3 g of soda per liter water, soaped, rinsed and dried.

You get a blue-tinged garnet of good realism tscigcnschaften.

Example 3

Cotton fabric is padded on the padder with the following solution and dried: 14g l- (2 ', 3'-Oxynaphthoylamino) -2-methylbenzene are added with 20 g

a wetting agent of the oil sulfonate type and 21 ecm sodium hydroxide solution of 38 ⁰ Be made into a paste and adjusted to 11 with boiling water. The dried fabric is printed with a printing paste, which is dissolved in 1 kg of 14.5 g of 4-amino-2-methyl-5-chloro-3'-nitro-l, l'-azobenzene in the form of a diazonium compound prepared in the usual way, 1 g of an action of the product of about 20 moles of ethylene oxide to 1 mole Octodecylalkohol and 6.5 cc of acetic acid (50 ° / ₀ solution) as a thickening agent and locust bean gum

ίο contains.

Then it is dried, washed with hot dilute soda solution, rinsed, 10 minutes at 95 ° C with 1 g of an action product of about 10 moles of ethylene oxide to 1 mole of isododecylphenol and 3 g of soda per liter Soaped in water, rinsed and dried.

A garnet-colored print with a bluish tinge is obtained.

The following table contains a number of

further components which can be used in accordance with the invention and the color shades of those obtainable therefrom on the fiber Azo dyes, which also have good fastness properties.

Diazo component Azo component hue 4-Amino-2-methyl-5-chloro-3'-nitro-l, l'-azo-
benzene 1- (2 ', 3'-oxynaphthoylamino) naphthalene bluish garnet 4-Amino-2-methyl-S-chloro-4'-nitro-1,1'-azo
bcnzol l- (2 ', 3'-oxynaphthoylamino) -4-methoxy-
bcnzol bluish garnet 4-amino-2-methyl-5-chloro-2'-methoxy-
4'-nitro-1,1'-azobenzene l- (2 ', 3'-oxynaphthoylarnino) -2-methoxy-
4-chloro-5-methylbenzene deep garnet the same l- (2 ', 3'-oxynaphthoylamino) -2-methyl-
4-methoxybenzene Corinth 4-amino-2-methyl-5-c] ilor-2'-methyl-
4'-nitro-1,1'-azobenzene l- (2 ', 3'-oxynaphthoylamino) -2-ethoxy-
benzene garnet the same l- (2 ', 3'-oxynaphthoylamino) -4-ethoxy-
benzene full garnet 4-amino-2-chloro-5-methoxy-4'-nitro-
1, l'-azobcnzol 2- (2 ', 3'-oxynaphthoylamino) -3-meth.oxy-
diphenylene oxide Corinth the same 1- (2 ', 3'-oxynaphthoylamino) -3-nitrobenzene Corinth the same l- (5 "-oxy-l ', 2', l", 2 "-benzocarbazole-
4 "-carboylamino) -4-methoxybenzene black 4-amino-2-chloro-5-methoxy-3'-nitro-
1, l'-azobcnzol 2- (2 ', 3'-oxynaphthoylamino) naphthalene bluish dark garnet the same l- (2 ', 3'-oxynaphthoylamino) -2,5-dimeth-
oxy-4-chlorobenzene bluish dark garnet the same 1- (2 ', 3'-oxynaphthoylamino) -2-methylbenzene Corinth the same l- (3'-Oxydiphenylenoxyd-2'-carboylamino) -
naphthalene reddish
Dark gray brown 4-amino-2,4'-dichloro-5-melhoxy-3'-nitro-
I, l'-azobcnzol i- (2 ', 3'-oxynaphthoylamino) -2-methyl-
4-chlorobenzene muted, dark
violet 4-amino-2,4-dichloro-5-methoxy-3'-nitro-
1, l'-azobcnzol 1 - (2 ', 3'-oxynaphthoylamino) -2,5-dimeth-
oxy-4-chlorobenzene muted, dark
violet the same Terephthaloyl-bis- (l-acetylamino-2-meth-
oxy-4-chloro-5-methylbenzene) orange 4-amino-2,2'-dichloro-5-methoxy-4'-nitro-
i, l'-azobcnzol 2- (2 ', 3'-oxynaphthoylamino) naphthalene Navy blue the same l- (2 ', 3'-oxynaphthoylamino) -2-methyl-
4-methoxybenzene Corinth the same 1- (2 ', 3'-oxynaphthoylamino) -2,5-dimeth-
oxybcnzol Corinth the same l- (6'-bromo-2 ', 3'-oxynaphthoylamino) -
2-ynethoxybenzene muted purple

Claims (1)

Claim: Further embodiment of the process for the production of water-insoluble azo dyes ^ on the Fiber according to patent application F 19 481 IVc / 8m, characterized in that diazonium compounds from p-aminoazo compounds of the formula NO ₂ wherein the nitro group is in the m- or p-position to the azo group, R is hydrogen, a halogen atom, an alkyl or alkoxy group and R 'an alkyl or alkoxy group with arylamides of aromatic or heterocyclic o-oxycarboxylic acids or acyl acetic acids. © 909 560/379 6.