DE60494C - Process for the preparation of real azo dyes for dyeing and printing from amidocarboxylic acids - Google Patents

Description

^IMPERIAL

PATENT OFFICE.

PATENT LETTERING

CLASS 22: dyes, varnishes, lacquers.

Patented in the German Empire on November 30, 1890. Longest duration: November 9, 1904.

In patent specification no. 58271 are simple * Described azo dyes which are derived from the diazo compounds of the amidocarboxylic acids.

The components listed there can be replaced with the following with great advantage :

i. Dioxynaphthalene monosulfonic acid S (from 'a-naphthalene disulfonic acid of Patent No. 40571 or their sulton obtained by fusing with alkalis);

2. Dioxynaphthalene disulfonic acid S, which when the a-naphtholtrisulfonic acid S arises;

3. Dioxynaphthalene disulfonic acid obtained from the Naphthalene trisulfonic acid of Patent No. 38281 by nitriding, reducing, converting the α-naphthylamine trisulfonic acid thus obtained into the corresponding naphtholtrisulfonic acid and by finally fusing the latter with , Alkalis is obtained;

4. Amidonaphthol disulfonic acid, which is derived from the α-naphthylamine trisulfonic acid mentioned in 3. can be obtained by fusing with alkalis.

In this way, dyes are obtained which are identical to those of the main patent are suitable for dyeing and printing purposes. The new dyes are capable of the colorations obtained with them form a part of the gaps still present in this area to fill in the printing inks.

The process for their preparation is that of the main patent and from the following Example can be seen:

Dye made from o-amidosalicylic acid and dioxynaphthalene monosulfonic acid. S.

15.3 kg of o-amidosalicylic acid are used in more common Way diazotized with 7 kg of sodium nitrite in hydrochloric acid solution. The obtained diazo compound is added with stirring to an ice-cold solution of sodium acetate 28 kg of sodium dioxynaphthalene monosulfonate and let the whole stand for 24 hours. Part of the dye is precipitated, the rest is precipitated by the addition of table salt, filtered and dried.

It dyes unheated wool violet in an acid bath, chrome-stained wool with a beautiful bluish tinge gray on. It produces blue-gray tones when printing with chromium salts.

In an analogous manner, the corresponding dyes are the (18) -Dioxynaphthalene-α-monosulfosäiire S, the (1 x 8) -dioxynaphthalene-α-disulfonic acid S, the (1 x 8) -dioxynaphthalene-β-disulfonic acid and the (1 ■ 8) -Amidonaphtoldisulfo-

acid with the diazo compounds of the following amido acids:

o-, m- and ρ-amidobenzoic acid, o- and p-amidosalicylic acid, amido-p-oxybenzoic acid, o-amido-m-cresolcarboxylic acid, amidoanisic acid, amidosulfobenzoic acid, amidosulfosalicylic acid, amidosulfocresolcarboxylic acid, amidophthalic acid. ¹ The nuances that are achieved using these new dyes can be seen in the following tables:

I. Dye from (i · 8) -dioxynaphthalene-ct-mono-sulfonic acid and

on ordinary wool

on chrome-stained wool

m-amidobenzoic acid

o-amidosalicylic acid

ο - amido - m - cresol carboxylic acid.

Amidoanisic acid

Amidosulfobenzoic acid

Amidosulfosalicylic acid

Amidophthalic acid

bluish red purple black violet blue-gray violet . blue gray * bluish red dark purple bluish red purple black red-violet blue-violet bluish red dark purple

II. Dye from (i · 8) -dioxynaphthalene-a-disulfoic acid and

on ordinary on chrome-stained Wool Wool dull bluish red purple black bluish red dark purple bluish red blue blue-violet blue violet green Blue violet green Blue blue-violet greenish black bluish red blue black red black purple purple. blue violet greenish black bluish red blue-violet

ο-amidobenzoic acid

m-amidobenzoic acid

ρ-amidobenzoic acid.

ο - amidosalicylic acid

p-amidosalicylic acid

Amido-p-oxybenzoic acid ο - amido - m - cresolcarboxylic acid.

Amidoanisic acid

Amidosulfobenzoic acid

Amidosulfosalicylic acid

Amidosulfocresolcarboxylic acid. . . Amidophthalic acid,

III. Dye from (1 x 8) -dioxynaphthalene-ß-disulfonic acid and

on ordinary wool

on chrome-stained wool ■>

21. 22.
23
24.
25th
26th
27
28.
29
30th
31.

ο-amidobenzoic acid

m-amidobenzoic acid

ρ-amidobenzoic acid

ο -Amidosalicylic acid

ρ - amidosalicylic acid

Amido - ρ - oxybenzoic acid ...... ο -amido - m - cresol carboxylic acid.

Amidoanisic acid

Amidosulfobenzoic acid

Amidosulfosalicylic acid

Amidosulfocresolcarboxylic acid. . . Amidophthalic acid

red

red

red

blue-red blue-red blue-red blue-violet blue-red

red

blue-red blue-red

red

black-violet black-violet black-violet

blue

green-blue green-blue green-blue

blue

red violet

blue

blue

violet

IV. Dye from fi

donaphtoldisulfosäu re and on ordinary on chrome-stained Wool Wool red violet blue brownish red brownish red brownish red brownish red brownish red brownish red bluish red blue-violet bluish red blue red-violet blue brownish red brownish red red blue blue-violet blue purple blue-violet blue purple red blue

ο-amidobenzoic acid ......

m-amidobenzoic acid

ρ-amidobenzoic acid

o-amidosalicylic acid

p-amidosalicylic acid

Amido-p-oxybenzoic acid. . Amidocresol carboxylic acid ....

Amidoanisic acid

Amidosulfobenzoic acid ....

Amidosulfosalicylic acid

Amidosulfocresolcarbonsaure Amidophthalic acid

Similar tones are also obtained when using the above dyes for printing purposes obtain.

Claims (4)

Patent claim: innovation in the process of patent no. 58271 for the preparation of real azo dyes for dyeing and printing purposes, consisting in using the diazo compounds of o-, m- and p-amidobenzoic acid, ο -amidosalicylic acid (COOH: OH: N H2 = 1: 2: 6), p- Amidosalicylic acid (CO OH: OH: NH2 = 1: 2: 5), amido-p-oxybenzoic acid (from p-oxybenzoic acid by nitriding and reducing), o-amido-m-cresolcarboxylic acid (COOH: OH: C H3: NH2 = 1 : 2: 4: 5), amido anisic acid (from anisic acid by nitrifying and reducing), amidosulfobenzoic acid (from sulfated benzoic acid by nitrifying and reducing), amidosulfosalicylic acid (from sulfated salicylic acid by nitrifying and reducing), amidosulfo-cresol carboxylic acid (from cresol H3: OH: COOH = 1: 3: 4) by nitriding and reducing) and from amidophthalic acid (from phthalic acid by nitrifying and reducing), combined with one of the following oxynaphthalene sulfonic acids: 1. (1 · 8) -Dioxynaphthalene-α-monosulfonic acid (from a-Naphthol disulfonic acid desPalentes No. 40571 or its sultone by fusing with Alkalis obtained); 2. (1 ■ 8) -Dioxynaphthalene-a-disulfonic acid (which obtained by fusing with alkali from those α - naphthol nulfonic acid which is used in sulphizing the α-naphthol disulphonic acid of patent no. 40571 is created) ; 3. (1 × 8) -Dioxynaphthalene-ß-disulfonic acid, derived from the naphthalene trisulfonic acid of the patent No. 38281 by nitriding and reducing, conversion of the amidonaphthalene trisulfonic acid thus obtained into the corresponding naphthol sulfonic acid and by fusing the latter with alkalis; 4. (1 x 8) -Amidonaphtholdisulfonicäure, which from the in this claim under 3. mentioned Naphthylamine trisulfonic acid is formed when it is fused with alkalis.