DE24229C - Preparation of red dyes by the action of paradiamines on the amidated ethers of phenols - Google Patents

Description

IMPERIAL

PATENT OFFICE.

PATENT LETTERING

CLASS 22: dyes, varnishes, lacquers.

KALLE & CO. in BIEBRICH a. Rh.

of phenols.

Paternity in the German Empire from October 27, 1882.

In a manner analogous to that of safranine, through the oxidation of a mixture of paradiamines with primary monamines of the benzene series (aniline, toluidine etc.), the inventors provide dyes by combining the paradiamines with the amidated ethers of the phenols under the An oxidizing agent.

In this reaction 1 molecule of paradiamine acts on 2 molecules of amidophenol ether a.

When using paraphenylenediamine and anisidine, the process seems to be as follows Equation to run:

B, (NH,), + 2 (α Ή
= C ₁₈ H ₁₂ N _A (O CIf ₃ J ₂

SIf.

Instead of the paradiamines, their substitution products, e.g. B. Dimethylparaphenylenediamine, or also use those bodies which pass into paradiamines through reduction, e.g., nitrosodimethylaniline and dichloroquinonimide. When using the latter, the Oxidizing agents are unnecessary, since the above bodies themselves have an oxidizing effect. Of the amiders Phenolic ethers are mainly the orthobodies (orthoanisidine, orthoamidophenetol, orthoamidobutylphenol etc.) of importance; however, half of them can be replaced by the corresponding Parabodies are replaced. Half of the phenol ether also leaks through other monamines, e.g. B. replace with aniline, toluidine or dimethylaniline.

Such a body is created e.g. B. according to the scheme:

amin NH , what the latter

C ₆ H ₄ (NH ₂ J ₂ + C ₆ H, ⁰ ^ H * ₊ Q _Hs - C _1S H ₁₃ O CH, Ν ** + 8 H.

The inventors also produced dyes of this last-mentioned class by oxidation of one Mixture of 1 molecule of the amidated phenol ether with 1 molecule of paradiamidodiphenyl-

¹ ^ ₇ ¹ ^ l ^C J JV H ₂ C ₆

Body can to a certain extent be regarded as aniline-substituted paraphenylenediamine.

Example:

1. 18 kg of hydrochloric acid paraphenylenediamine (or the equivalent amount of toluenediamine), 32 kg of hydrochloric orthoanisidine are mixed with 500 1 of water heated to boiling and in this solution 20 kg of potassium dichromate in powder form or in the form entered the aqueous solution.

It is boiled for 2 to 3 hours, after cooling the dye is precipitated with table salt and cleaned him in a known manner by dissolving and salting out.

2. 18 kg of hydrochloric acid paraphenylenediamine, 16 kg. hydrochloric orthoanisidine, 13 kg. hydrochloric acid Aniline and 20 kg of potassium dichromate are treated as in Example 1.

3. 27 kg of hydrochloric acid para diamidodiphenylamine, 16 kg of hydrochloric acid orthoanisidine and 17 kg Potassium dichromate are treated as in Example 1.

4 · 24 kg of orthoanisidine are mixed with 500 1 Water is heated to the boil and in this solution

gradually 18 kg dichloroquinonimide C ₆ JT ₁ ^ "_. registered. The liquid remains boiling until a sample taken out shows the desired shade. The further processing takes place as in example 1.

5. 18 kg of nitrosodimethylaniline are added under the conditions given in Example 4 24 kg of orthoanisidine combined.

The potassium dichromate can be replaced by all similarly acting oxidizing agents (lead peroxide, Brownstone etc.) must be replaced. The resulting dyes are usually very beautiful red and have strong fluorescence. The shade of that obtained from the alcohol-substituted diamines Bodies are drawn a little more into the violet.

Claims (1)

Patent claim:
Representation of red dyes:
i. by the action of paraphenylenediamine or paratoluylenediamine on the methyl, ethyl isobutyl or amyl ethers of orthoamidophenol or the orthoamido meta-, para- or orthocresols alone or in the presence of the methyl, ethyl, isobutyl and amyl ethers of paraamidophenol, as well of paraamido, ortho- or metacresol, under the influence of oxidizing agents;
by the action of paraphenylenediamine or paratoluylenediamine on mixtures of aniline, toluidine or xylidine on the one hand with the methyl, ethyl, isobutyl or amyl ethers of ortho- or para-amidophenol, as well as the ortho- and para-amidocresol ethers mentioned under 1. under the influence of oxidizing agents; by oxidation of paradiamidodiphenylamine or paradiamidoditolylamine Presence of the methyl, ethyl, isobutyl or amyl ethers of ortho- or para-amidophenol or the amidocresols mentioned under 1.; by the action of nitrosodimethylaniline, nitrosodiethylaniline, nitrosodimethyl and äthylorthotoluidins, as well as dichloroquinonimides and dichlorotoluchinonimides the amidophenol ethers mentioned under 1., as well as mixtures of these with aniline, Toluidine or xylidine.