Patent GB-567911-A (GB)
Title: Manufacture of sulphonated fatty amide products
Filed: 1943-03-12
Abstract: Sulphonated fatty amides are prepared by reacting sulphonated oils, fats, fatty acids or esters with amines, as hereinafter specified in the presence, as a catalyst, of a mineral acid salt of ammonia or an amine.  The amines specified as starting materials are monoethanolamine, di - ethanolamine, tri - ethanolamine, mono- and di-propanolamine, hydroxyethyl ethylene diamine, monoamylamine, octadecylamine, ethylene diamine, diethylene triamine, triethylene tetramine, tetraethylene pentamine, morpholine, diamino isopropanol, ethyl and butyl ethanolamine, and the hydroxy amines obtained by the reduction of aliphatic nitro-alcohols.  The catalyst may be any ammonium or amine salt of a mineral acid such as ammonium chloride; hydrochlorides of primary amines, such as methylamine, ethylamine, propylamine, ethanolamine and aniline; of secondary amines such as dimethylamine, diethylamine, di-isopropylamine methyl ethylamine and di-propylamine; of tertiary amines such as triethylamine and triethanolamine; or of tertiary organic nitrogen compounds such as pyridine.  Other mineral acid salts may be used, such as the sulphates, nitrates or phosphates.  In cases where the catalyst is a salt of the amine which is to enter into the reaction, the catalyst may be generated in situ by addition of a mineral acid and an excess quantity of the amine.  The reaction is carried out by heating the mixture for a period of 1/2 to 2 hours at temperatures between 100 DEG  and 250 DEG  C., or higher if secondary or tertiary amines are employed, but below the boiling points or decomposition temperatures of the reactants. Sulphonated fatty materials employed are high SO3 sulphonated fatty materials such as the sulphonated oils, fats, fatty acids and esters as produced from castor oil, corn oil, cottonseed oil, olive oil, palm oil, andiroba oil, peanut oil, sunflower oil, rice bran oil, rapeseed oil, mustard seed oil, teaseed oil, chaulmoagra oil, tomato seed oil, sesame oil, soyabean oil, cocoabutter, Chinese tallow; also from neat's-foot oil, beef tallow, bone fat, horse fat, wool fat, mutton tallow, cod-liver oil, cod oil, herring oil, menhaden oil, porpoise oil, seal oil, salmon oil, sardine oil, shark-liver oil, sperm oil, whale oil, tuna body oil; the sulphonated fatty acids and acid esters derived from these oils; the sulphonated mono- and di-glycerides of higher fatty acids and the sulphonated blown or hydroxylated derivatives of fats or fatty acids. The invention is particularly applicable to the treatment of sulphonated fatty materials containing less than about 3 per cent of water and 0.2 per cent inorganic salts and containing relatively high percentages of SO3 of the order of about 5 per cent to about 20 per cent combined SO3.  The sulphonated amide products are applicable in highly acid media, such as in viscose spinning baths, to prevent clogging of the spinnerettes or as penetrants in acid textile treating media such as wool-carbonising baths, and the like.  They are also textile softeners, wetting, dispersing and emulsifying agents, plasticizers, detergents, pour point depressors in fuels and lubricants, penetrants in leather and paper treatment, demulsifying agents for crude oil emulsions, blending and dewaxing agents in petroleum refining, for removing spray residues and as latex stabilizers; they may be incorporated in adhesive compositions, cosmetics, compositions for fat-liquoring and oiling leather, lubricants, cutting oils, wiredrawing compounds, and polishes.  In examples: (1) a sulphonated oleic acid containing 16 per cent SO3 and less than 3 per cent water and 0.2 per cent inorganic salts is condensed with mono-ethanolamine, using ammonium chloride as a catalyst, at 165 DEG  C.; (2) as in (1) above, but using ethanol ethylene diamine as the amine; (3) sulphonated oleic acid is condensed with tetraethylene pentamine using ammonium chloride as the catalyst and the product added to a viscose spinning bath in which it serves to prevent clogging of the viscose spinnerette; (4) a sulphonated red oil is condensed with tetraethylene pentamine using as a catalyst pyridine hydrochloride; in another example, trimethylamine hydrochloride replaces the pyridine salt as a catalyst.  The Specification as open to inspection under Sect. 91 refers to the use, as starting materials, of any amines or amides capable of reacting to form amides with the sulphonated fatty materials and includes aniline, acetamide and urea.  This subject-matter does not appear in the Specification as accepted.ALSO:Sulphonated fatty amides are prepared by reacting sulphonated oils, fats, fatty acids or esters with amines as hereinafter specified in the presence as a catalyst of a mineral acid salt of ammonia or an amine.  The amines specified as starting materials are mono-ethanolamine, di-ethanolamine, tri-ethanolamine, mono- and di-propanolamine, hydroxyethyl ethylene diamine, monoamylamine, acetadecyl amine, ethyline diamine, diethylene, triamine, triethylene tetramine, tetra-ethylene, pentamine, morpholine, diamino isopropanol, ethyl- and butyl-ethanolamine, and the hydroxy amines obtained by the reduction of aliphatic nitro-alcohols.  The catalyst may be any ammonium or amine salt of a mineral acid such as ammonium chloride; hydrochlorides of primary amines such as methylamine, ethylamine, propylamine, ethanolamine and aniline; of secondary amines such as dimethylamine, diethylamine; di-isopropylamine methyl ethylamine and di-propylamine, of tertiary amines such as triethylamine and triethanolamine; or of tertiary organic nitrogen compounds such as pyridine.  Other mineral acid salts may be used such as the sulphates, nitrates or phosphates.  In cases where the catalyst is a salt of the amine which is to enter into the reaction, the catalyst may be generated in situ by addition of a mineral acid and an excess quantity of the amine.  The reaction is carried out by heating the mixture for a period of 1/2 to 2 hours at temperatures between 100 DEG  and 250 DEG  C. or higher if secondary or tertiary amines are employed, but below the boiling points or decomposition temperatures of the reactants.  Sulphonated fatty materials employed are high SO3 sulphonated fatty materials such as the sulphonated oils, fats, fatty acids and esters as produced from castor oil, corn oil, cottonseed oil, olive oil, palm oil, andiroba oil, peanut oil sunflower oil, rice bean oil, rapeseed oil, mustard seed oil, teaseed oil, chaulmagra oil, tomato seed oil, sesame oil, soyabean oil, cocoabutter, chinese tallow; also from neatsfoot oil, beef tallow, bone fat, horse fat, wool fat, mutton tallow, cod liver oil, cod oil, herring oil, menhaden oil, porpoise oil, seal oil, salmon oil, sardine oil, shark liver oil, sperm oil, whale oil, tuna body oil; the sulhonated fatty acids and acid esters derived from these oils; the sulphonated mono- and diglycerides of higher fatty acids and the sulphonated blown or hydroxylated derivatives of fats or fatty acids.  The invention is particularly applicable to the treatment of sulphonated fatty materials containing less than about 3 per cent of water and 0.2 per cent inorganic salts and containing relatively high percentages of SO3 the order of about 5 per cent to about 20 per cent combined SO3.  They are latex stabilisers, and may be incorporated in adhesive compositions.  In examples: (1) a sulphonated oleic acid containing 16 per cent SO3 and less than 3 per cent water and 0.2% in organic salts, is condensed with monoethanolamine using ammonium chloride as a catalyst, at 165 DEG  C.; (2) as in (1) above but using ethanol ethylene diamine as the amine; (3) sulphonated oleic acid is condensed with tetraethylene pentamine using ammonium chloride as the catalyst; (4) a sulphonated red oil is condensed with tetraethylene pentamine using as a catalyst pyridine hydrochloride; in another example trimethylamine hydrochloride replaces the pyridine salt as a catalyst.  The Specification as open to inspection under Sect. 91 refers to the use, as starting materials, of any amines or amides capable of reacting to form amides with the sulphonated fatty materials and includes aniline acetamide and urea.  This subject-matter does not appear in the Specification as accepted.ALSO:Sulphonated fatty amides are prepared by reacting sulphonated oils, fats, fatty acids or esters with amines, as hereinafter specified in the presence, as a catalyst, of a mineral acid salt of ammonia or an amine.  The amines specified as starting materials are monoethanolamine, di - ethanolamine, tri - ethanolamine, mono- and di-propanolamine, hydroxyethyl ethylene diamine, monoamylamine, octadecylamine, ethylene diamine, diethylene triamine, triethylene tetramine, tetraethylene pentamine, morpholine, diamino isopropanol, ethyl and butyl ethanolamine, and the hydroxy amines obtained by the reduction of aliphatic nitro-alcohols.  The catalyst may be any ammonium or amine salt of a mineral acid such as ammonium chloride; hydrochlorides of primary amines, such as methylamine, ethylamine, propylamine, ethanolamine and aniline; of secondary amines such as dimethylamine, diethylamine, di-isopropylamine methyl ethylamine and di-propylamine; of tertiary amines such as triethylamine and triethanolamine; or of tertiary organic nitrogen compounds such as pyridine.  Other mineral acid salts may be used, such as the sulphates, nitrates or phosphates.  In cases where the catalyst is a salt of the amine which is to enter into the reaction, the catalyst may be generated in situ by addition of a mineral acid and an excess quantity of the amine.  The reaction is carried out by heating the mixture for a period of 1/2 to 2 hours at temperatures between 100 DEG  and 250 DEG  C., or higher if secondary or tertiary amines are employed, but below the boiling points or decomposition temperatures of the reactants. Sulphonated fatty materials e