Patent GB-648768-A (GB)
Title: Process for the preparation of new capillary-active substances
IPC: C07C309/14
Filed: 1947-10-27
Abstract: New capillary active materials of the general formula <FORM:0648768/IV (b)/1> n which R denotes a straight or branched chain alkyl radical containing at least 10 carbon atoms, R1 denotes an alkylene or hydroxyalkylene radical with 2-6 carbon atoms, R2 denotes an alkyl radical with 1-6 carbon atoms or an hydroxyalkyl radical with 2-6 carbon atoms, R3 denotes an alkylene or hydroxyalkylene radical with 2-6 carbon atoms, the carbon atoms of which can be separated by an oxygen atom, and Y denotes a cation, are prepared by causing amides of the formula <FORM:0648768/IV (b)/2> to react with compounds of the formula XR3SO3Y, in which X denotes halogen, a sulphuric or sulphonic ester group or an epoxide oxygen atom.  Suitable amides are, for example, those obtained by the reaction between soap-forming fatty acids and monoethyl- or monohydroxy-ethylethylene-diamine, monoethyl- or monohydroxy-ethylaminopropylamine or a -b -dihydroxypropylaminoethylamine.  Compounds of the formula XR3SO3Y are, for example alkali salts of halogenethanesulphonic acids or ethionic acids, carbyl sulphate (ethionic anhydride), water-soluble salts of the chlorhydroxypropanesulphonic acids, the acid of formula <FORM:0648768/IV (b)/3> and chlorethoxyethanesulphonic acids.  The products can be used in the form of liquids or pastes or in powder form and can be used with salts of other capillary active materials. They are suitable for all purposes in which a foaming, cleaning, wetting, dissolving, penetrating, dispersing or emulsifying action is required and are suitable as softening agents.  In the examples: (1) the amide obtained from technical stearic acid and monohydroxyethylethylenediamine is reacted with g  - chlor - b  - hydroxypropanesulphonic acid in the presence of caustic soda to give <FORM:0648768/IV (b)/4> and the corresponding palmitic derivative.  A similar product is obtained if technical oleic acid is used instead of stearic acid; (2) the amide obtained from oleic acid and monohydroxyethylethylenediamine is reacted with sodium b -chlorethanesulphonate in the presence of caustic soda to give <FORM:0648768/IV (b)/5> A similar product is obtained if the sodium b -chlorethane sulphonate is replaced by sodium chlorethoxyethanesulphonate; (3) the glycerinecontaining amide obtained from coconut fat and monohydroxyethylethylene is reacted with sodium g -chlor-b -hydroxypropanesulphonate in the presence of caustic soda to give chiefly <FORM:0648768/IV (b)/6> in which R denotes the alkyl residue of the fatty acids present in coconut fat. This product may be used for the preparation of hair-washing lotions. Samples have been furnished under Sect. 2(5) of (A) the compound prepared from the amide obtained from technical stearic acid and monohydroxyethylethylene diamine by the action of b -chlorethanesulphonate and caustic soda; (B) the compound obtained by the action of g -chlor-b -hydroxypropanesulphonic acid and caustic soda on the amide obtained from coconut fatty acid and monohydroxyethylethylenediamine; (C) the compound obtained by the action of g -chlor-b -hydroxypropanesulphonic acid and caustic soda on the amide obtained from oleic acid and monohydroxyethylethylamine-diamine; (D) the compound obtained by the action of caustic soda and the sodium salt of g -chlor-b -hydroxypropane-sulphonic acid on the amide obtained from oleic acid and methylaminopropylamine, which is itself obtained by condensation of acrylonitrile and methylamine; (E) the compound obtained by the action of caustic soda and the sodium salt of g -chlor-b -hydroxypropane-sulphonic acid on the amide obtained from oleic acid and hydroxyethylaminopropylamine, which is itself prepared from 1,2-propylenediamine and ethylene oxide.ALSO:New capillary-active materials of the general formula <FORM:0648768/IV (c)/1> in which R is a straight or branched alkyl radical with at least 10 carbon atoms, R1 is an alkylene or hydroxyalkylene radical containing 2-6 carbon atoms, R2 is an alkylene radical with 1-6 carbon atoms or a hydroxyalkylene radical with 2-6 carbon atoms, R3 is an alkylene or hydroxyalkylene radical with 2-6 carbon atoms, the carbon chain of which may be interrupted by an oxygen atom and Y denotes a cation, are stated to be foaming, cleaning and wetting agents.  Compounds of the formul  <FORM:0648768/IV (c)/2> are stated to be particularly suitable for neutral or acid wool washing and the compound <FORM:0648768/IV (c)/3> in which R denotes the alkyl residue of the fatty acids present in coconut fat, can be used for the preparation of hair-washing lotions.  The method of preparation of these compounds is described (see Group IV (b)).ALSO:New capillary-active materials of the general formula <FORM:0648768/III/1> in which R is a straight or branched alkyl radical with at least 10 carbon atoms, R1 is an alkylene or hydroxyalkylene radical containing 2-6 carbon atoms, R2 is an alkylene radical with 1-6 carbon atoms or a hydroxyalkylene radical with 2-6 carbon atoms, R3 is an alkylene or hydroxyalkylene radical with 2-6 carbon atoms, the carbon chain of which may be interrupted by an oxygen atom and Y denotes a cation, are stated to be emulsifying agents.  The compounds of the formul <FORM:0648768/III/2> are stated to be emulsifying agents for calcium soaps.  The method of preparation of these compounds is described (see Group IV (b)).