Patent GB-418247-A (GB)
Title: Improvement in emulsifying detergent and wetting agents
IPC: D06M15/423
Filed: 1933-07-11
Abstract: Products useful as cleansing and emulsifying agents are prepared by condensing a primary amide of a mono- or di-carboxylic acid of the aliphatic, hydroaromatic or naphthenic series, containing more than eight carbon atoms, with formaldehyde (or paraformaldehyde) and a secondary amine of the formula RNHR<1>, where R and R<1> are alkyl or alkylene groups containing together less than seven carbon atoms; the acyl radicle of the amide may contain substituents, such as aryl, hydroxy, alkoxy, ketonic, amino or sulphonic groups or chlorine. Specified amides are those of pelargonic, lauric, myristic, melissic, sebacic, palmitic, arachidic, oleic, sulphooleic, ricinoleic, sulphoricinoleic, stearic, 10-aminostearic, 10-chlorostearic, 10-hydroxystearic, 10-phenylstearic, 9 : 10-dehydroxystearic, linoleic, eleaostearic, carnaubic, cerotic, abietic, montanic, erucic, undecylenic, w-benzoyl pelargonic, campholic, fencholic, naphthenic, cetyloxybutyric, cetyloxyacetic, and capryloxyacetic acids, and the mixed acids of cocoanut oil, castor oil, linseed oil, olive oil, tallow, and rapeseed oil.  Specified secondary amines are dimethylamine, diethylamine, dipropylamines, methylethylamine, diethanolamine, and piperidine; salts of the amines may also be used. The products emulsify water in hydrocarbon oils, or fatty oils and hydrocarbons in aqueous media acidified, e.g. by acetic, lactic, sulphuric, hydrochloric acids; they may also be used as cleansing and levelling agents in the treatment of rayon and other textiles, or they may be mixed with sulphonated oils and sulphonated alcohols to form.  Examples are given describing the manufacture of products from (1) stearamide, formaldehyde, and dimethylamine; (2) stearamide, paraformaldehyde, and diethylamine; (3) capryloxyacetamide, formaldehyde, and diethylamine; (4) oleic amide, formaldehyde, and dimethylamine; (5) sebacic diamide, formaldehyde, and diethylamine; (6) stearamide, formaldehyde, and piperidine; (7) oleic amide, formaldehyde, and di-n-propylamine or diisopropylamine or piperidine; (8) amides of cocoanut oil acids, formaldehyde and diethylamine, this products may be combined with oleic or other fatty acid to form soaps which are soluble in hydrocarbons; (9) naphthenic amide, formaldehyde, and diethylamine; (10) amides of cocoanut oil acids, formaldehyde, and dimethylamine; (11) amides of cocoanut oil acids and formaldehyde followed by condensation with dimethylamine.ALSO:Products useful as wetting, cleansing and emulsifying agents are prepared by condensing a primary amide of a mono- or di-carboxylic acid of the aliphatic, hydroaromatic or naphthenic series, containing more than eight carbon atoms, with formaldehyde (or paraformaldehyde) and a secondary amine of the formula RNHR<1>, where R and R<1> are alkyl or alkylene groups containing together less than seven carbon atoms; the acyl radicle of the amide may contain substituents, such as aryl, hydroxy, alkoxy, ketonic, amino or sulphonic groups or chlorine.  Specified amides are those of pelargonic, lauric, myristic, melissic, sebacic, palmitic, arachidic, oleic, sulphooleic, ricinoleic, sulphoricinoleic, stearic, 10 - aminostearic, 10-chlorostearic, 10 - hydroxystearic, 10 - phenylstearic, 9 : 10-dihydroxystearic, linoleic, eleaostearic, carnaubic, cerotic, abietic, montanic, erucic, undecylenic, o -benzoylpelargonic, campholic, fencholic, naphthenic, cetyloxybutyric, cetyloxyacetic, and capryloxyacetic acids, and the mixed acids of coco-nut oil, castor oil, linseed oil, olive oil, tallow, and rapeseed oil; a method of preparing such amides consists in heating the corresponding acids or their esters with an excess of urea to 180--220 DEG  C. at atmospheric pressure.  Specified secondary amines are dimethylamine, diethylamine, dipropylamines, methylethylamine, diethanolamine, and piperidine; salts of the amines may also be used.  The reaction may be effected by heating the three components together to 50--150 DEG  C., or the condensation product of the amide and formaldehyde may be heated with the amine, in either event in the presence or absence of water or an inert organic solvent such as a volatile hydrocarbon or ether.  The reaction may be accelerated by addition of a small proportion of a trialkylamine or an oxide, hydroxide or carbonate of an alkali or alkaline earth metal.  The products emulsify water in hydrocarbon oils, or fatty oils and hydrocarbons in acidic aqueous media; they may also be used as cleansing, wetting and levelling agents in the treatment of rayon and other textiles, or they may be mixed with sulphonated oils and sulphonated alcohols to form cleansing compositions.  Examples are given describing the manufacture of products from (1) stearamide, formaldehyde, and dimethylamine; (2) stearamide, paraformaldehyde, and diethylamine; (3) capryloxyacetamide, formaldehyde, and diethylamine; (4) oleic amide, formaldehyde, and dimethylamine; (5) sebacic diamide, formaldehyde, and diethylamine; (6) stearamide, formaldehyde, and piperidine; (7) oleic amide, formaldehyde, and di-n-propylamine or diisopropylamine or piperidine; (8) amides of coco-nut oil acids, formaldehyde, and diethylamine; (9) naphthenic amide, formaldehyde, and diethylamine; (10) amides of coco-nut oil acids, formaldehyde, and dimethylamine; (11) amides of coco-nut oil acids and formaldehyde, followed by condensation with dimethylamine. Examples 7 and 8 describe also the preparation of the amides by heating the corresponding acids with urea.  o -Benzoylpelargonamide is obtainable by condensing sebacic anhydride with benzene and aluminium chloride, and converting the acid obtained into its amide. Capryloxyacetamide is obtainable from ammonia and the chloride of capryloxyacetic acid, which is obtained by condensing chloracetic acid with the sodium compound of capryl alcohol.