Patent GB-341053-A (GB)
Title: Improved process for the production of wetting, cleansing and dispersing agents
IPC: D06M13/402
Filed: 1929-08-07
Abstract: Sulphonated amides of aliphatic or cycloaliphatic carboxylic acids, prepared by treating the latter with secondary amines, in the absence of metal halides, and sulphonating the resulting amides if they do not already contain a sufficient number of sulphonic or sulphuric ester-groups are used for dispersing unsoluble substances, such as alkaline-earth metal soaps, and colouring materials, and also as cleansing agents.  The secondary amines may belong to the aliphatic, heterocylic, aliphatic-aromatic or aromatic series, but must be free from hydroxy groups and aryl and aralkyl groups containing any substituent other than sulphonic groups.  The products may be used associated with soaps, turkey red oils, aromatic sulphonic acids, hydroxyalkylamines, quarternary ammonium bases and their salts, protective colloids, e.g. glue, gelatine, or vegetable mucilages or gums, organic solvents, e.g. monocresylethyleneglycolether, trichlorethylene, salts e.g. sodium chloride, carbonate or bicarbonate, waterglass, or normal or acid sodium sulphate and bleaching agents, e.g. perborates, percarbonates, sodium paratoluenesulphonicchloramide.  According to examples: (1) oleic diethylamide (obtained by boiling an alcoholic solution of oleic methyl ester and diethylamine) is sulphonated with sulphuric acid in the presence of trichclorethylene: (2) oleicethylanilide (obtained by heating oleic acid with ethylaniline) is similarly sulphonated.  (3) oleic diphenylamide (obtained from oleic acid chloride and diphenylamine) is sulphonated.  An emulsion formed with the product and oleic acid is used for oiling wool: (4) ethylaniline-m-sulphonic acid is condensed with oleic chloride: (5) stearic acid is condensed with ethylnaphthylamine and sulphonated by means of oleum.  Lactic acid, propionic acid, resinic acids, naphthenic acids, fatty acids obtained by oxidation of paraffin wax, oleic sulphonic acid, oleic sulphonic methyl ester, oleic methyl ester sulphuric ester, ricinoleic sulphuric ester, castor, and other vegetable and animal oils or their free acids, caproic acid, sulphoacetic acid, and sodium palmitic sulphonate are mentioned as suitable aliphatic carboxylic acids and derivatives, and further secondary amines which are specified are piperidine, morpholine, benzylnaphthylamine, alkylnaphthylamines, diphenylamine, methylbenzylamine, diethylamine and secondary amines containing, cyclohexyl, butyl, hexyl or cetyl groups.ALSO:Sulphonated amides of aliphatic and cyclo aliphatic carboxylic acids are prepared by treating the latter with secondary amines of the aliphatic, cycloaliphatic, heterocyclic, aromatic-aliphatic or aromatic series, in the absence of metal halides having a condensing action, and sulphonating the resulting amides, if they do not already contain a sufficient number of sulphuric ester or sulphonic groups.  Instead of the carboxylic acids, their derivatives may be used, e.g. their esters, halides or anhydrides. The secondary amines must be free from hydroxy groups and any aryl or aralkyl radicle attached to the nitrogen must not contain any substituent other than sulphonic groups.  The products are wetting, dispersing, washing, scouring and emulsifying agents and may be used in the textile, leather and allied industries, in acid, neutral or alkaline baths.  They may be used associated with soaps, turkey red oils, aromatic sulphonic acids, hydroxyalkylamines, quarternary ammonium bases and their salts, protective colloids, e.g. glue, gelatine or vegetable mucilages or gums, organic solvents, e.g. monocresylethyleneglycolether, trichlorethylene, salts e.g. sodium chloride, carbonate or bicarbonate, waterglass, or normal or acid sodium sulphate and bleaching agents, e.g. perborates, percarbonates, sodium paratoluenesulphonicchlor amide.  The products emulsify or disperse water insoluble substances, such as alkaline-earth soaps, dyestuffs or other colouring materials, fats or waxes.  According to examples: (1) oleic diethylamide (obtained by boiling an alcoholic solution of oleic methyl ester and diethylamine) is sulphonated with sulphuric acid in the presence of trichlorethylene: (2) oleicethylanilide (obtained by heating oleic acid with ethylaniline) is similarly sulphonated.  The product enables level dyeings on cotton to be obtained using poor vat dyes: (3) oleic diphenylamide (obtained from oleic acid chloride and diphenylamine) is similarly sulphonated.  An emulsion formed with the product and oleic acid is used for oiling wool: (4) ethylaniline-m-sulphonic acid is condensed with oleic chloride: (5) stearic acid is condensed with ethyl-a-naphthylamine and sulphonated by means of oleum.  Carbon tetrachloride, nitrobenzene, and acetic acid are mentioned as diluents, lactic acid, propionic acid, resinic acids, naphthenic acids, fatty acids obtained by oxidation of paraffin wax, oleic sulphonic acid, oleic sulphonic methyl ester (obtained by sulphonating oleic methyl ester with chlorsulphonic acid in the presence of ether), oleic methyl ester sulphuric ester (obtained by acting with dimethyl sulphate on the sodium salt of oleic sulphuric ester), ricinoleic sulphuric ester, castor and other vegetable and animal oils, their free acids, caproic acid, sulphoacetic acid, and sodium palmitic sulphonate are mentioned as suitable aliphatic carboxylic acids and derivatives, and further secondary amines which are specified are piperidine, morpholine, benzylnaphthylamine, alkylnaphthylamines, diphenylamine, methylbenzylamine, diethylamine and secondary amines containing, cyclohexyl, butyl, hexyl or cetyl groups.