DE169579C - - Google Patents

Description

IMPERIAL

PATENT OFFICE.

The present invention relates to a method for the preparation of new azo dyes. It has been found that certain dyes of the composition RN = NR ¹ , where R denotes the remainder of a benzene derivative and R ¹ denotes m-amidophenol, have remarkable properties, both with regard to the vividness and intensity as well as the gloss that can be achieved with them

ίο colorations.

For example, the coupling of the diazo compounds of m- and p-sulfanilic acid * products formed with m-amidophenol are dyes of a darker shade and of greater coloring power than those, which by the method described in the patent 71229 thereby obtained that the same diazo compounds with m-amidophenolsulfonic acid be coupled.

Certain of these azo bodies, especially those made from diazotized amidoos - Oxycarboxylic acids or o-amidophenols are capable of pickling metals to draw and to dye the fiber with the formation of chrome lacquers.

The coupling can take place in acidic, neutral or alkaline solution. Depending on Type of coupling differ in individual cases, the products in certain Properties from each other, especially what the coloring in concentrated sulfuric acid concerns, as can be seen in the table below.

Example I. 18kg Parasulfanilic Acid converted into a diazo compound by adding 25 kg of hydrochloric acid and 7 kg of sodium nitrite and this to a solution of 11 kg Metaamidophenol in - 500 l of water added.

The reaction can be promoted by adding 50 kg of sodium acetate to the reaction liquid. The acetic acid soda can also be mixed with 20 kg carbonate soda or 20 kg caustic soda of 40 ⁰ Be. substitute.

The dye is isolated by salting out.

In acidic solution, a dye which is soluble in water with a yellow-brown color is obtained, which dyes wool yellow in an acid bath and soaks in concentrated sulfuric acid dissolves with brownish orange color; in alkaline solution one obtains one with more lively Brownish-yellow color soluble in water, which is almost the same on wool Gives a nuance, but is soluble in sulfuric acid with a vivid yellow-brown color.

In this example, the p-sulfanilic acid can be substituted for the m-sulfanilic acid; the aniline disulphonic acid 1: 2: 4 ^ur > d 1: 3: 5, the m-nitroaniline sulphonic acid (Nietzki), the ρ-amidop-nitro-o-sulphodiphenylamine, the metaamidobenzoic acid, the p-amidophenol-o-sulphonic acid.

Example IL. 27 kg of o-amido-o-nitrophenol-p-sulfonic acid (Potash salt) according to the patent specification 93443 are at normal temperature with the help of 35 kg of hydrochloric acid and 6 kg of sodium nitrite diazotized in a total amount of about 1000 1 of water. The received Diazo derivative is added to a solution of 1 kg of m-amidophenol in 500 l of water.

Diazo compounds
obtained from acting on m-amidophenol Art
of the reactant Shade on wool Solution in concentrated
sulfuric acid p-sulfanilic acid mineral or acetic acid Acid bath - yellow brownish orange m - sulfanilic acid mineral or acetic acid Acid bath - yellow greenish orange Aniline disulfonic acid 1: 2: 4 mineral acidic or alkaline Acid bath - yellow yellow-brown Aniline disulfonic acid 1: 3: 5 mineral acidic or alkaline Acid bath - yellow yellow-brown m-nitroaniline sulfonic acid (Nietzki) mineral or acetic acid Acid soon - greenish yellow orange brown ρ - amido - ρ ^l - nitro - ο ¹ - sulf 0-
diphenylamine acetic acid Acid bath - reddish chestnuts
Brown Brown black Metaamidobenzoic acid acetic acid Acid bath - yellow brownish yellow ρ-amidophenol - 0 - sulfonic acid acetic acid turmeric yellow red-brown 0 -amido - 0 - nitrophenol - ρ - sulfonic acid
OH: NH ₂ : SO ₃ H: NO ₂ =
1: 2: 4: 6 acetic acid
alkaline Acid bath - brown,
on chrome - bluish brown,
on clay - carob red,
on iron - brown
on chrome - purple brown > brown
brownish red 0-amidophenol - ρ - sulfonic acid
OH: NH ₂ : SO ₃ H = 1: 2: 4 acetic or alkaline on chrome - brown red-brown Picric acid acetic acid on chrome - violet brown,
on iron - reddish brown brownish red ρ - amidosalicylic acid acetic acid Acid bath - ■ yellow-brown,
on chrome - red-brown,
on iron - ■ gold beetle
chestnut colored > red-brown 0 - amido - ρ - cresol - 0 - carboxylic acid acetic acid Acid bath - brownish yellow
on chrome - brownish red red-brown.

f \

The combination of the components is made easier by adding 50 kg of acetic acid Soda and stir until completely dissolved. The dye is made by table salt dejected. It dyes wool reddish brown in an acid bath and produces metallic colors Mordants on wool different shades:

Bluish-brown-red on chrome; Carob red on clay, maroon brown on iron.

The coupling can take place in either mineral acid or acetic acid-containing solutions as well as in neutral or alkaline solution.

The dyes obtained in these different ways are, however, not identical; for example, the product obtained in acetic acid solution dissolves in sulfuric acid with yellow-brown color, while that obtained in alkaline solution dissolves with red-brown color.

In this example one can use the o-amidoo-nitrophenol-p-sulf acid

OH: NH ₂ : NO ₂ : SO ₃ H = 1: 2: 6: 4
by the o-amido-p-phenolsulfonic acid
OH: NH ₂ : SO ₃ H = 1: 2: 4,

picric acid, p-amidosalicylic acid and the ο-amido-ρ-cresol-ο-carboxylic acid substitute.

The nuances and the colorations of the dyes obtained by the present process are compiled in the table above. ,

Claims (1)

Patent claim: Process for the preparation of monoazo dyes which produce yellow to dark brown shades on wool in a neutral or acid bath with or without the use of metallic mordants, consisting in combining metaamidophenol in acidic, neutral or alkaline solution with the diazo compounds of the following substances: p-sulfanilic acid and m-sulfanilic acid, aniline disulfonic acid 1: 2: 4 ^{un (} 3 1: 3: 5, m-nitroaniline sulfonic acid (Nietzki), ρ -amido - ρ - nitro - ο - sulfodiphenylamine, metaamidobenzoic acid,
ρ - amidophenol - ο - sulfonic acid, ο - amido - ο - nitrophenol - ρ - sulfonic acid (OH: NH ₂ : NO ₂ : SO ₃ H 1: 2: 6: 4 ;, ο-amidophenol - ρ-sulfonic acid (OH: NH ₂ : SO ₃ H
Picric acid,
ρ - amidosalicylic acid,
ο -amido - ρ - cresol - ο - carboxylic acid. 1: 2: 4),