DE165139C - - Google Patents

Description

IMPERIAL

- PATENT OFFICE.

If one leaves the nitro derivatives obtainable by the process of patent 156759 If alkylated amidoanthraquinones act as primary aromatic amines, an exchange takes place the nitro group by the relevant alphylamine residue. Are several If nitro groups are present, they can be successively replaced (see also Patent 126542), whereby various amines can be used.

This leads to compounds which, depending on the relative position of the alphylamine group to the alkylamine group are colored red, blue to green (see patent 127458).

These compounds are identical to those obtained by condensation the halogen derivatives of the alkylamidoanthraquinones containing the substituents in the same position (See patents 139581 and 159129). Also is through that Patent 139581 the condensation of aromatic Amines with certain nitroalkylamidoanthraquinones, which at that time were already made by a method other than that of patent 156759 were already protected.

The following will accordingly focus on the description of embodiments of the method of patent 139581, which is based on the application of the not previously used, now available by the method of patent specification 156759 Nitroalkylamidoanthraquinones based.

Example 1.

10 kg of I · 4-nitromethylamidoanthraquinone are mixed with 100 kg of p-toluidine. Heated to the boil until the melt, which has gradually turned green-blue, does not change its color with further heating. The mixture is allowed to cool to about 70 ^0, mixed with an equal volume of methyl alcohol and allowed to stand for about 24 hours, wherein the dye formed precipitates crystallized. It is identical to the products obtainable according to example 1 of patent 159129 and described there (1 · 4-p-toluidomonomethylamidoanthraquinone).

Example 2.

10 kg of the p-dinitro derivative of the symmetrical one 1 · 5-dimethylamidoanthraquinones (Example 2 of patent 156759) heated to boiling with 100 kg of p-toluidine until the melt has turned green Color does not change with further heating. The reaction product is worked up as indicated in Example 1. The dye thus obtained is identical to the product obtainable according to Example 3 of patent 159129.

The formation of the dye takes place in two phases, by first forming one only one nitro group is substituted for the blue dye. Such a partial sub-

stitution of nitro groups, we explain in ^one the following examples:

Example 3.

10 kg of 4x5-dinitro-1-methylamidoanthraquinone

NHCH

NO.,

NO ₁ ,

(by nitrating 5 · I-nitromethylamidoanthraquinone available, see Example 4 of patent 156759) with 100 kg of p-toluidine only heated to 160 ° until the melt has turned a violet color Has. The method described several times by mixing the melt with methyl or Ethyl alcohol isolated, fairly sparingly soluble dye can crystallize through can be obtained completely pure in the form of dark purple crystals from hot 'pyridine. He was created by replacing just one nitro group and is very likely to have the following Constitution:

NHCH *

CO '

NHC ₇ N ₇ NO ₂ .

It is sparingly soluble in methyl and ethyl alcohol, slightly soluble in chloroform and pyridine of purple-red color, insoluble in hydrochloric acid. The solution in concentrated Sulfuric acid is yellow and turns gray-blue when heated.

The nitro group still obtained in the compound can be replaced by the amido group ... are replaced (by reduction) by alkylamine and arylamine residues, whereby a large number of new, blue to green-blue dyes can be obtained (see also following example).

Example 4.

In Example 2, the temperature is increased to the boiling point of p-toluidine and heated until the color of the melt has turned green-blue and changes with further Heating no longer changes, or one subjects the same treatment to the example 3 obtained red-violet dye is obtained by replacing both nitro groups the i-methylamido-4 through the p-toluidine residue 5 - di - ρ - toluidoanthraquinone

NHCH

NHC ₁ H ₁ NHC ₇ H ₇ .

The dye, isolated in the usual way, crystallizes from pyridine - | - methyl alcohol in dark blue crystals with a metallic sheen, which are in chloroform and pyridine with green-blue, dissolve in concentrated sulfuric acid with a brownish color. The latter solution turns purple-red when heated, adding a Sulphonic acid arises, which is pickled or unheated Dyes wool in green-blue shades.

If the dinitro derivative used in Examples 3 and 4 is replaced by the isomers, by nitrating i »8-nitromethylamidoanthraquinone (See Example 4 of patent 156759) available compound

NO,

NHCH

in this way one obtains quite similar dyes, namely a red-violet monoarylido derivative

NHC ₇ H ₇

NHCH

NO ₂

and a green-blue diarylido derivative NHC ₇ H _{7 NHCH 3}

NHC ₇ H ₇ .

The formation of the green-blue diarylido derivative is easier and faster than with the isomeric case of Example 4.

Example 5.

10 kg of that according to Example 7 of the patent 156759 by heavy nitriding of α-mono-

methylamidoanthraquinone available dinitro derivatives are heated with 100 kg of p-toluidine, until the melt has turned a pure green color. By adding alcohol the dye formed by replacing the nitro group in the p-position separates in long, dark green needles, which in organic solvents with pure green, in concentrated sulfuric acid ίο are soluble with yellow color. \

Claims (1)

Patent claim:
Further development of the process for the preparation of arylido derivatives of alkylamidoanthraquinones, which is protected by patent 139581, consists in condensing the nitro derivatives of alkylamidoanthraquinones and their derivatives with primary aromatic amines, which can be obtained by the process of patent 156759.