US2233805A - Triazoles - Google Patents

Description

Patented Mar. 4, 1941 UNITED STATES PATENT OFFICE in Anhalt, Germany, signments, to General assignors, by mesne as- Aniline & Film Corporation, New York, N. Y., a corporation of Delaware No Drawing. Application October 20, 1938, Serial No. 236,030. In Germany October 28, 1937 7 Claims.

The present invention relates to nitrogeneous condensation products, the manufacture thereof, and to a process of improving textiles. Specific details may be seen from the specification following hereafter.

It has been found that fatty acids containing more than 10 carbon atoms can in a simple manner be transformed into bases by melting them with amino-guanidine. For this purpose, the amino-guanidine may, for instance, be introduced into the molten fatty acid at a raised temperature (about 140 0.). Water vapor escapes, its amount being equivalent to 2 mols in case 1 mol of fatty acid has been caused to react with 1 mol of amino-guanidine.

In this condensation, there is probably formed with ring-closure a derivative of the aminotriazole, as is shown for stearic acid in the following formulae:

Instead of the free base there is preferably used one of its salts. The carbonate, for instance, is especially suitable in view of the high volatility of carbonic acid. If salts of less volatile acids, for instance, the chlorides, are used, it is preferable to bind the acid, after heating for a short time, by introduction of sodium carbonate or of other alkalies.

The temperature required for the condensation depends upon the nature of the components entering into reaction and upon the conditions of reaction. In general, it is necessary to apply temperatures above C. to about 200 0., a temperature of about C. is preferred. The water formed as a reaction product may also be removed by azeotropic distillation, for instance, by means of benzene.

The following examples illustrate the invention, the parts being by Weight:

Example 1.136 parts of amino-guanidine carbonate are slowly introduced, at 140 0., while stirring, into 284 parts of molten stearic acid.

The melt, which initially begins to foam, becomes gradually clear, carbon dioxide and water being split 01f. After 36 parts of water have been split off, the reaction is interrupted. The melt which solidifies to a wax-like body is soluble in dilute acids, such as hydrochloric acid.

The product may be purified by boiling it with a dilute sodium carbonate solution in order to eliminate small amounts of unaltered parent material, which may perhaps be present.

Instead of stearic acid, there may also be used with the same success coconut oil fatty acid, oleic acid, ricinoleic acid or also halogenated fatty acids and fatty acids having a branched chain.

The amines thus obtained are soluble in dilute acids and they remain stable even if their solution in such acids is heated for a prolonged period of time. They display valuable properties as textile adjuvants.

Example 2.A rayon skein having a weight of 100 grams is handled, for about 30 minutes, at 40 C. in 1000 cm. of a bath containing 0.1 gram of heptadecylaminotriazole hydrochloride. After thorough rinsing and drying, the silk is very soft to the touch.

The corresponding N-alkyl or N-hydroxyalkyl derivatives may be used with the same success.

The new softening agents bring about practically no change of shade on dyed skeins or fabrics. As some of them give rise to the formation of difiiculty soluble sulfates, it is preferable to avoid any separation in flakes-in the case of water containing sulfates-by operating in the presence of protective colloids. The above-described textile processing is suitable not only for pure rayon of. the most varied kinds, but also for mixed fabrics as well as for natural fibers of vegetable or animal origin, such as wool and linen.

The invention is not limited to the specific details described, for obvious modifications may occur to a person skilled in the art.

What we claim is:

1. Triazoles of the general formula R stands for alkyl with more than 9 carbon atoms, being soluble in dilute acids and being textile adjuvants.

2. The process of producing triazoles which comprises condensing dry amino-guanidine of the formula NH.NH:

HN=C

with an unsubstituted fatty acid containing more than 10 carbon atoms by heating to a temperature not exceeding substantially 200 C. until in one operation 2 mols of water are split ofi.

3. The process of producing triazoles which comprises condensing a dry salt of amino-guanidine with an unsubstituted fatty acid containing more than 10 carbon atoms by heating to a temuntil in one operation 2 mols of water are split off.

5. The process of producing triazoles which comprises condensing a. dry salt of amino-guanidine with stearic acid by heating to a temperature not exceeding substantially 200 C. until in one operation 2 mols of water are'split off.

6. The process of producing triazoles which comprises condensing a dry salt of amino-guanidine with oleic acid by heating to a temperature not exceeding substantially 200 C. until in one operation 2 mols of water are split oil.

7. The process of producing triazoles which comprises condensing a dry salt of amino-guanidine with coconut oil fatty acid by heating to a temperature not exceeding substantially 200 C. until in one operation 2 mols of water are split off.

KARL BRODERSEN.

MATHIAS QUAEDVLIEG.