US2251892A - Capillary active compounds and process of preparing them - Google Patents

Description

Patented Aug. 5, 1941 CAPILLARY ACTIVE COMPOUNDS AND PROCESS OF PREPARING THEM Ludwig Orthner, Carl Platz, and HansKeller, Frankfort-on-the-Main, and Heinz Siinke, Bad

Soden in Taunus, Germany,

assignors to I. G.

Farbenindustrie Aktlengeselischaft, Frankforton-the-Main, Germany No Drawing.-

. No. 250,923. In Germany January 17,

8 Claims.

The present invention relates to capillary active compounds and to a process of preparing them.

' Application January 14, 1939, Serial We have found that agents of high capillary action are obtainable by introducing hydrophiiic groups, directly or indirectly, into an amine of the following general formula Such amines are, for instance, di-(n-hexyD- amine, diisohexylamine, di-alpha-ethylhexylamine, di-octylamine. butyldodecylamine, didodecylamine, di-octodecylamine, methyl-dihexylamine, diisoheptyl-hydroxyethyl-amine, diheptyl-benzylamine. Suchsecondary amines may be I obtained by known methods from carboxylic acids or mixtures of carboxylic acids, for instance, by transforming these acids into the nitriles and carbon to react with potassium cyanide and saponiiying the product obtained.

The amines may also be obtained by other known methods, for instance, by causing suitable halogenated hydrocarbons to react with ammonia or amines. v

- The method of rendering the products watersoluble consists in transforming the amines, by means of phosgene, into carbamic acid chlorides and then condensing these products with aminoacids, such as sarcosine, methyl-taurine, with albumin' decomposition products or with aminopoly-hydroxy-compounds such as methylgluca-' mine or hydroxy-sul'fonic acids, such as hydroxyethane-sulfonic acid.

The products obtained by the process of the invention have capillary active properties and may be used for treating materials of various kind, such as textiles, leather, paper and the like. They display a high wetting and emulsifying action; they may also be used with advantage as levelling and penetrative dyeing agents. Some hydrogenating the nitriles thus obtained. Primary amines which are simultaneously formed are separated by distillation. Suitable carboxylic acids are, for instance, caproic acid, caprylic acid, capric acid, lauric acid, palmitic acid, stearic acid, oleic acid, ricinolic acid, alpha-ethylhexylic acid. Theamlnes may be used as such or in admixture with one another. The parent materials may also be prepared from commercial mixtures of carboxylic acids. It is, for instance, possible to transform into amines, by way of nitriles, the carboxylic acid mixtures formed in the oxidation of paraflin or of mineral oils. There are further suitable the mixtures of carboxylic acids which are obtained by treating with alkali the alcohols 01 high molecular weight formed in the catalytic hydrogenation of carbon oxides.

Parent materials suitable for the preparation of amines are also carboxylic acids or mixtures of carboxylic acids which are obtained by treating carbon monoxide or carbon dioxide, in the presence of an oleflne and perhaps of hydrogen, with steam or by causing a halogenated hydroof the products have a washing power or may be used as softening agents. The wetting effect, even in mercerizlng liquors, is especially high with compounds inwhich the radicals R and R1 contain branched chains. The products may be used as such, in admixture with one another or with other capillary active substances, such as soap and other textile adjuvants, with colloidal substances such as mucilage, glue, water-soluble cellulose derivatives, starch, bentonite, saponine or the like or with organic solvents, such as butanol, xylenyl-glycol; but also with inorganic salts, such as Glaubers salt, sodium carbonate, sodium pyrophosphate, trisodium phosphate, sodium metaphosphate or with agents yielding oxygen such as sodium perborate or sodium hypochlorite.

The following examples serve to illustrate the invention, but they are not intended to limit it thereto; the parts are by weight:

(1) 213 parts of diisoheptylamine are dissolved in 450 parts of chlorobenzene and dry hydrochloric acid gas is then introduced, while cooling, until saturation. The temperature is then raised to C. to C. and phosgene is introduced,

'hvdrochloric acid gas being developed. When the developement of hydrochloric acid gas has ceased. phosgene and hydrochloric acid gas still present are removed by the introduction of dry air and the solvent is then distilled under reduced ressure. 240 parts of diisoheptyl'carbamic acid chloride boiling under a pressure of 2 mm. at 140 C. to 142 C. are obtained.

- solution is distinctly alkaline towards 55 parts of diisohcptylcarbamic acid chloride of the formula C1111: and caustic soda solution are added in the course of about hours at 75 C. to 80 C., while stirring, to 330 parts of a methyl taurine solution of 10 per cent strength so that the reaction of the phenolphthalein. The reaction product dissolves in wataurine.

2) Di- (alpha-ethylhexyl) -amine trans- I formed by means of phosgene into the carbamic acid chloride having the formula CaHn ' NC0.Cl

CaHn and 30 parts thereof are added, drop by drop, at 75 C. to 85 0. into an aqueous solution-containing 23 parts of sodium n-butyltaurine in the course of 10 to hours, the reaction being always alkaline towards phenolphthaiein. The solution is then rendered feebly alkaline to litmus paper. The reaction product has thefollowing constitution:

CZHB Gzlis CI13.(CHQMLYLCHLN-CflgnH.(CH2)3('"3 ,='-O CAHLILY-CHLCHZSOJNR Instead. of n-butyltaurine there may also be used another taurine; for instance, isobutyltaurine, alpha-ethylhexyltaurine or another aminosulionic acid, for instance, sulfanilie acid or metanilic acid or ethanol amine sulfuric acid ester.

(3) 33 parts of n -butyl-tetradecyl-carbamic acid chloride having the formula Cilia uHzo prepared from n-butyl-tetradecylamine and phosgene are run into a solution of 13 parts ofsodium sarcosine in parts, of water at 70 C. to 80 C., while well stirring, the reaction being always alkaline towards phenolphthalein and the whole is stirred until a test portion dissolves in dilute caustic soda solution to a clear solution. The reaction product has the following constitution:

cimmciimi i=0 cmr'tomcoomand may be used as washing agent.

(4) A mixture of carboxylic acids obtained by I the oxidation of paraflin and containing carboxylic acids with 7 to 9 carbon atoms, is trans performed after the following scheme:

O-som R being aliphatic radicals having from 7 to 9 carbon atoms.

We claim:

1. The process of preparing capillary active compounds which comprises causing compounds of the general formula wherein R and R1 stand for aliphatic hydrocarbonradicals containing at least 3 carbon atoms and R and R1 together containing at least 11 carbon atoms, to react with phosgene and subsequently causing the condensation products to react with a member of the group consisting of aliphatic and aromatic amino compounds substituted by a radical of the group consisting of SOaH, 03031! and COOH.

formed b, way of the nitriles and hydrogenation of these nitriles into a mixture of secondary amines, and then transformed into a mixture of carbamic acid chlorides by treatment with phosgene as described in Example 1. i 30 parts of this 2. The process of -preparing capillary active compounds which comprises causing compounds of the general formula wherein R and R1 stand for aliphatic hydrocarbon radicals containing at least 3 carbon atoms and R and R1 together containing at least 11 carbon atoms, to react with phosgene and subsequently causing the condensation products to re act with an aliphatic amino sulionic acid.

3. The process of preparing capillary active' compounds which comprises of the general formula R-III- R: H

causing compounds compounds which comprises causing compounds of the general formula R-N-Rl wherein R and R1 stand for aliphatic hydrocarbon radicals containing,at least 3 carbon atoms and R and R1 together containing at least 11 carbon atoms, to react with phosgene and subsequently causing the condensation product to react with an aliphatic amino carboxylic acid.

5. As new compounds having capillary active properties the products of the general formula:

wherein R and R1 stand for aliphatic hydrocarbon radicals containing at least 3 carbon atoms and R and R1 together containing at least 11 carbon atoms, R: stands for a member of the 10 group consisting of aliphatic and aromatic hydrocarbon radicals, R3 means a member of the group consisting of hydrogen and aliphatic hydrocarbon radicals and Y stands for a member of the group consisting .of scan, OSOsI-I and 15 COOH. 6. Compounds as defined in claim 5, wherein Y stands for COOH.

'7. As a new capillary active compound C1His-NC7H 5 00 I cH,-1 I-omom-so3rr 8. As a new capillary active compound om, c1115 omxomncnommomcuromnom =0 cmqi rcmcmsoai LUDWIG ORTHNER.

HEINZ StiNKE.