DE1056582B - Process for the production of water-insoluble azo dyes on the fiber - Google Patents

Description

F19481IVc / 8m

REGISTRATION DATE: FEBRUARY 9, 1956

NOTICE THE REGISTRATION AND ISSUE OF THE EDITORIAL: MAY 6, 1959

For creating garnet tones on natural or regenerated cellulose fibers using the ice color method in dyeing technology, mainly p-aminoazo compounds of the 4-amino-3,2'-dimethyl-l, l'-azobenzene type are used or of 4-amino-2,3'-dimethyl-1,1'-azobenzenes, those in the form of their diazonium compounds on the fiber with aryl amides of 2,3-oxynaphtoic acid be united. In this way, dyeings with good fastness properties are obtained. A sensitive disadvantage in the production of these dyeings, however, is the inadequate durability of the Diazonium compounds of these p-aminoazo compounds in the dye baths and printing pastes, which are complete Utilization in the case of dyeing processes that are extended over time, for example when dyeing on the fly Bathing, impaired and precludes their use in the tropics.

It has now been found that one can obtain water-insoluble azo dyes of similar shades and the same good fastness properties on the fiber can be produced if one diazonium compounds from p-aminoazo compounds the formula

NO ₈

NH,

Cl

wherein the nitro group is in the m- or p-position to the azo group and R is hydrogen, 1 halogen atom, an alkyl or alkoxy group, with arylamides of aromatic or heterocyclic o-oxycarboxylic acids or acyl acetic acids.

The method according to the invention is distinguished from one another the known method in that here diazonium compounds of p-aminoazo compounds come to use, the durability previously used for the production of garnet tones Outperform p-diazoazo compounds. The preparations of the diazonium compounds in the form of their dye baths or printing pastes are stable for days even at temperatures of 30 to 35 ° C, so that when used in in practice there are no losses due to premature decomposition. In addition, you get when using of the new compounds stronger colorations than with the known p-aminoazo compounds, so that the Production of the new azo dyes is also more economical than the known azo dyes.

The generation of the new azo dyes on the fiber requires compared to the usual for this class of dyes Methods no new or additional operations or devices. Rather, the new dyes fit together Method of production

of water-insoluble azo dyes

on the fiber

Applicant:

Farbwerke Hoechst Aktiengesellschaft

formerly Master Lucius & Brüning,

Frankfurt / M., Brüningstr. 45

Dr. Herbert Kracker, Dr. Ulrich Dreyer

and Dr. Walter Staab, Offenbach / M.,

have been named as inventors

organically belong to the class of ice colors and represent an essential enrichment of this class of colorants.

The p-aminoazo compounds on which the present invention is based and not yet described in the literature can be obtained by known methods. Appropriately one uses their firm ones, through very good ones Durability of excellent diazonium compounds, as obtained according to patent 1008310.

example 1

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

2.1 g of l- (2 ', 3'-oxynaphthoylamino) -2,5-dimethoxy-4-chlorobenzene are dissolved in 2.1 ecm denatured alcohol, 0.85 ecm sodium hydroxide solution at 38 °, 3.1 ecm formaldehyde solution 33 % and 4.2 ecm warm water and adjusted with water at 35 ° C ₁ 3 g of a condensation product of higher molecular weight fatty acids and protein degradation products and 10 ecm sodium hydroxide solution from 38 ° Βέ to 11.

Developing bath

2.7 g of 4-amino-3-clilor-3'-nitro-l, l'-azobenzene become made into a paste with 4 ecm hydrochloric acid of 20 ° Be, with 1 g of an action product of about 20 mol of ethylene oxide

909 509/400

1 mole of octodccyl alcohol, dissolved in 10 ecm of water, and 0.8 g of sodium nitrite, dissolved in 4 ecm of water, added and stirred for 15 minutes. The solution thus obtained is poured into water, which S g sodium acetate, and 5 cc of acetic acid containing 50 ° _o ig / and adjusted to 11 with water.

A range of good authenticity properties is obtained.

Using that has been stored for 3 to 4 days at · 35 to 4O ⁰ C or 14 days at 2O ⁰ C as a coloration that in terms of tinting strength and color tone is obtained not from the above-obtained, a developing bath, protected from light, Color differs.

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

Example 2

Cotton fabric is made on the foulard using the following Solution padded and dried:

I4gl- (2 ', 3'-oxynaphthoylamino) -4-methoxybenzene dissolved with 20 g of a wetting agent of the oil sulfonate type and 35 ecm sodium hydroxide solution of 38 ° Bc and with boiling water set to 1 1.

The dried fabric is developed on the padder with the following solution:

13.8 g of 4-amino-3-chloro-4'-nitro-l, l'-azobenzene are made into a paste with 20 ecm hydrochloric acid of 20 "Bc, with 2 g of an action product of about 20 moles of ethylene oxide to 1 mole of octodccyl alcohol in 20 cc of water, and 5 g of sodium nitrite dissolved in 20 cc of water were added and J is stirred 5 minutes. the solution thus obtained is added in water, 50 containing 20 g of sodium acetate and 20 cc acetic ° / ₀ ig and provides with water to 1 1 a.

After an air passage of 30 seconds, rinsed hot and cold, for 20 minutes at 95 ⁰ C with 1 g of the action product of about 10 moles of ethylene oxide to 1 mole Isododecylphsnol and 3 g of soda per liter water, soaped, rinsed and dried.

A garnet with good fastness properties is obtained.

Example 3

Cotton fabric is made on the foulard, using the following Solution padded and dried.

ίο 8 g of 2,3-oxynaphthoylaminobenzene with 15 g of a wetting agent of the oil sulfonate type and 12 ecm Sodium hydroxide solution at 38 ° Bc made into a paste and adjusted to 1 liter with boiling water. The dried fabric is with printed with the following printing paste:

9.5 g of 4-amino-3-chloro-3'-nitro-l, l'-azobenzene become with 13.7 ecm hydrochloric acid of 20 ° Bc and 2.8 g sodium nitrite with the addition of 2 g of an action product of about 20 moles of ethylene oxide to 1 mole of octodecyl alcohol diazotized and with water, 10 g sodium acetate and 15 ecm acetic acid 50% with the addition of locust bean gum adjusted to 1 kg as a thickener.

Then it is dried, washed with hot, dilute soda solution, rinsed, 10 minutes at 95 ⁰ C with

1 g of an action product of about 10 moles of ethylene oxide to 1 mole of isododccylphenol and 3 g of soda per liter Soaped in water, rinsed and dried.

A full, border-red print is obtained.

The following table also contains a number of further components which can be used according to the invention as well as the color shades of the azo dyes obtained therefrom on the fiber, which also have good fastness properties own.

Diazo component Azo component c hue 4-Amino-2-chloro-4'-nitro-l, l'-azobenzene 2,3-Ox3'naphthoylaminobenzene garnet the same 1- (2 ', 3'-oxynaphthoylamino) -2-methoxybenzene Bordo garnet the same l- (2 ', 3'-oxynaphthoylamino) -2-methoxy-5-chloro-
bcnzol garnet 4-Amino-3-chloro-4'-nitro-l, l'-azobenzene l- (2 ', 3'-oxynaphthoylamino) -2,4-dimethoxy-5-chloro-
benzene bluish tint
garnet the same ! - (S'-Oxydiphcnylenoxyd ^ '- carboylaminoJ ^^ - di-
methoxy benzene reddish
Brown the same l- (5 "-Oxy-l ', 2', l", 2 "-benzocarbazole-4" -carboyl-
amino) -2-methyl-4-methoxybenzene black 4-Amino-2-chloro-3'-nitro-1,1'-azobenzene 1- (2 ', 3'-oxynaphthoylamino) -2-ethoxybenzene Bordo garnet the same l- (2 ', 3'-oxynaphthoylamino) -2-methyl-4-methoxy-
benzene garnet the same l- (6'-bromo-2 ', 3'-oxynaphthoylamino) -2-methoxy-
bcnzol Bordo garnet the same Tcrepht ha loyl-bis- (1 -acetylami no-2-methoxy-4-chloro-
5-methylbenzene) brownish
yellow 4-Amino-3-clilor-3'-nitro-1,1'-azobenzene 1- (2 ', 3'-oxynaphthoylamino) -4-ethoxybenzene Bordo garnet 4-Amino-2,2'-dichloro-4'-nitro-1,1'-azobenzene 1- (2 ', 3'-oxynaphthoylamino) -2-methylbenzene Corinth the same 1- (2 ', 3'-oxynaphthoylamino) -2,5-dimethoxybenzene Garnet corinth the same 2- (2 ', 3'-oxynaphthoylamino) -3-methoxy-diphenylcn-
oxide Corinth 4-Amino-3,2'-dichloro-4'-nitro-1, r-azobenzene 2- (2 ', 3'-oxynaphthoylamino) naphthalene bluish tint
garnet the same ! - (S'-Oxydiphenylcnoxyd ^ '- carboylaminoJ-naph-
thalin reddish
Gray-brown

5 6th Azo component c hue Diazo component 1- (2 ', 3'-oxynaphthoylamino) naphthalene Corinth 4-amino-2-chloro-2'-methoxy-4'-nitro-
l, l'-azobenzene l- (2 ', 3'-oxynaphthoylamino) -2,4-dimethoxy-5-chloro-
benzene brownish
Corinth the same l- (2 ', 3'-oxynaphthoylamino) -2-methoxy-4-chloro-
5-methylbenzene garnet the same 1- (2 ', 3'-oxynaphthoylamino) -2-methyl-4-chlorobenzene garnet 4-amino-3-chloro-2'-methoxy-4'-nitro-
l, l'-azobenzene 4,4'-bis-acetoacetylamino-3,3'-dimethyldiphenyl brownish
orange the same

Claims (1)

PATENT CLAIM: Process for the production of water-insoluble azo dyes on the fiber, characterized in that that on these the diazonium compounds from p-aminoazo compounds of the formula NO ₂ NH, wherein the nitro group is in the m- or p-position to the azo group and R is hydrogen, 1 halogen atom, an alkyl or alkoxy group, with arylamides of aromatic or heterocyclic o-oxycarboxylic acids or acyl acetic acids, the use Diazonium compounds previously deposited in solid form together with arylamides of 2,3-oxynaphthoic acid is excluded. Cl Legacy Patents Considered:
German Patent No. 1 008 310. © 909 509/400 4.59