SU424364A3 - METHOD OF OBTAINING WATER-SOLUBLE NITROGEN - Google Patents

Description

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This invention relates to the preparation of a water-insoluble azo dye containing a pyridone residue that can be used to dye synthetic materials.

A known method for producing a water-insoluble azo dye containing a pyridone residue of general formula I

R-dg and

where R is an aromatic or heterocyclic residue, free from water-soluble groups;

X is hydrogen, branched and / or substituted alkyl group, substituted or unsubstituted cycloalkyl, aralkyl, aryl or heterocyclic groups;

Y is hydrogen, branched and / or substituted by alkyl or alkenyl groups, substituted or unsubstituted cycloalkyl, aralkyl, aryl or heterocyclic groups, or a residue of the formula

.

or - aJ-No. R,

in which RI and Rs are hydrogen, substituted or unsubstituted cycloalkyl. aralkyl or aryl groups, wherein Ri and R2 can be directly linked via a hetero atom; alk means an alkylene residue.

The method of obtaining the above dye (I) consists in the fact that the prediazated amine, free from water-soluble groups, is combined with a suitably substituted 6-hydroxy-2-primer, followed by isolation of the desired product by a known technique. The dyes obtained in a known manner, although dyed synthetic materials with good color characteristics, however, the target product has, for example, low quality and low percentage of dye, which makes the process economically inexpedient. In addition, dye baths for dyeing materials obtained on the basis of the above dye (I) are unstable at elevated temperatures.

A new method for producing a dye of formula (I) is proposed. The method consists in the fact that the compound of General formula II

ABOUT

II

R-№N-CH-C-CZ

which may be in tautomeric form, where R, X have the above meaning; Z is alkyl condensed with a compound of general formula III

ABOUT

HYN-C-CH2-CN

where X has the above meaning,

in an organic solvent medium, for example ethanol, in the presence of an alkaline condensing agent, for example sodium or potassium ethylate, sodium or potassium carbonate, at-25 ° C, especially at-5 ° C, followed by isolation of the target product by a known technique.

Example. A mixture of 500 wt. including ethyl alcohol, 16.2 wt. including methyl ester 4benzoylbenzene- (1 -azo-a) -acetoacetic acid of the structural formula

n

-. CO f Cv- N - N SI

X -:. :: -: -.... / |

C 00 O K,

Ooh

IIil.

N N-CR-C-OZ + AND YI r-C-CH, -CN - R-yr l rY - N + ZOH 0 G-X

D

6.0 weight. including cyanacetate and 21.0 rses. h. anhydrous potash until stirred under external cooling with ice at a temperature of from 0 to + 5 ° C, while the sample of the reaction mixture will show in the thin-layer chromatogram not a single amount of the starting material. Then, by slowly adding 34.5 wt. including crude hydrochloric acid, the pH is set to 2 and, after stirring for 2 hours, the resulting dye of the structural formula is sucked off

SI,

S O - t N -rrV CN

BUT N O I CHZ

Then thoroughly washed with water and dried.

In the IR spectrum in a thin-layer chromatogram, by the color of the solution in sulfuric acid and the melting point, it is identical to the dye (see German patent P 1 813 385.2, at approx. 1, Table 1, No. 14) obtained by diazotizing p-aminobenzophenone and combinations with 1,4-dimethyl-3-cyano-6-hydroxypyriDone- (2).

The table shows other obtained by the proposed method, dyes.

X

J i

Y

Table

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