Patent GB-372389-A (GB)
Title: Improvements in the manufacture and production of wetting, cleansing and dispersing agents
IPC: D06M13/438
Filed: 1931-01-28
Abstract: Sulphamic acids, which are stated to be emulsifying and dispersing agents, are prepared by subjecting amines or carboxylic amides containing at least one aliphatic open chain or cycloaliphatic radicle having at least eight carbon atoms, to the customary methods for the production of sulphamic acids.  In a modification, similar products are obtained, by introducing aliphatic, cycloaliphatic or mixed aromatic aliphatic acyl radicles by the usual methods into amidosulphonic acid or aliphatic or cycloaliphatic sulphamic acids containing less than eight carbon atoms.  In examples: (1) palmitic acid amide is treated with chlorsulphonic acid in the presence of pyridine; (2) palmitic acid chloride is condensed with amidosulphonic acid in the presence of pyridine; in place of palmitic acid chloride lauric, oleic, naphthenic, or phenylstearic acid chlorides may be used; (3) naphthenic acid amide (obtained by amidation of a mixture of naphthenic acid boiling above 240 DEG  C.) is treated with chlorsulphonic acid in the presence of dimethylaniline; (4) sulphamic acids are similarly obtained from decylamine and monopalmitoylethylenediamine.  The sulphamic acids or their salts may be used in association with soaps, turkey red oils, salts of sulphonic acids, e.g. of alkylated naphthalene sulphonic acids and sulphonic acids from vegetable and animal fatty acids or mineral oils, higher alcohols such as cetyl or dodecyl alcohols or the alcohols obtained by reducing vegetable or animal fats or oils, sulphuric esters of these higher alcohols, amines, e.g. dodecyl or pentadecylamines, hydroxyalkylamines, e.g. N-dodecyl-N-ethanolamines, quaternary ammonium bases or their salts, e.g. trimethyldodecylammonium sulphate or N-dimethyl-N-ethanol-N-dodecylammonium sulphate, organic solvents, e.g. methylcyclohexanol, tetrahydronaphthalene, ethylglycolcresylether or trichlorethylene, protective colloids such as gelatine, starch, or vegetable mucilages.  The amides and acid amides are particularly suitable as starting materials which are derived from mixed aromatic aliphatic carboxylic acids, e.g. phenylstearic acid, carboxylic acids obtained by the oxidation of paraffin wax, and from resinic and naphthenic acids.  The amines produced from mineral acid esters of alcohols obtained by catalytic reduction of oils and fats and ammonia or primary amines according to the process of Specification 369,614, and the amines obtained from the fatty acids of fats and oils are also suitable.ALSO:Sulphamic acids, which are stated to be assistants in the textile and related industries as wetting, cleansing, softening and dispersing agents, are prepared by subjecting amines or carboxylic amides containing at least one aliphatic open chain or cycloaliphatic radicle having at least eight carbon atoms, to the customary methods for the production of sulphamic acids.  In a modification, similar products are obtained by introducing aliphatic, cycloaliphatic or mixed aromatic-aliphatic acyl radicles by the usual methods into amidosulphonic acid or aliphatic or cycloaliphatic sulphamic acids containing less than eight carbon atoms.  In examples: (1) palmitic acid amide is treated with chlorsulphonic acid in the presence of pyridine; the sodium salt may be precipitated by adding caustic soda or the free pyridine may be distilled off leaving the pyridine salt of the sulphamic acid, which is a strong foaming agent; (2) palmitic acid chloride is condensed with amidosulphonic acid in the presence of pyridine; in place of palmitic acid chloride, lauric, oleic, naphthenic or phenylstearic acid chlorides may be used; (3) naphthenic acid amide (obtained by amidation of a mixture of naphthenic acids boiling above 240 DEG  C.) is treated with chlorsulphonic acid in the presence of dimethylaniline; woollen piece goods may be washed with an aqueous solution of the sodium salt of the resulting sulphamic acid; (4) sulphamic acids are similarly obtained from decylamine and monopalmitoylethylenediamine (obtained from ethylenediamine and palmitic methyl ester); the latter yields a potassium salt which may be used for softening viscose silk.  A mercerizing lye may be prepared from the sulphamic acid of decylamine, caustic soda, and alcohol.  The sulphamic acids or their salts may be used in association with soaps, turkey red oils, salts of sulphonic acids, e.g. of alkylated naphthalene sulphonic acids and sulphonic acids from vegetable and animal fatty acids or mineral oils, higher alcohols such as cetyl or dodecyl alcohols or the alcohols obtained by reducing vegetable or animal fats or oils, sulphuric esters of these higher alcohols, amines, e.g. dodecyl of pentadecylamines, hydroxyalkylamines, e.g. N-dodecyl-N-ethanolamines (obtained from ethanolamine and dodecylsulphuric ester), quaternary ammonium bases or their salts, e.g. trimethyldodecylammoniumsulphate (obtained from dimethylsulphate and dodecylamine) or N-dimethyl-N-ethanol-N-dodecylammonium sulphate (obtained from dimethyl sulphate and N-dodecyl-N-ethanolamine), organic solvents, e.g. methylcyclohexanol, tetrahydronaphthalene, ethylglycolcresylether or trichlorethylene, protective colloids, salts, e.g. sodium carbonate or bicarbonate, waterglass, Glauber's salt or sodium chloride, bleaching agents, e.g. percarbonates, perborates, or p-toluenesulphochloramide sodium salt.  Oleum, sulphur trioxide, sulphuryl chloride, mixtures thereof with organic or inorganic anhydrides, e.g. phosphoric or acetic anhydride, and mixtures of sulphuric acid with said anhydrides are sulphonating agents which may also be used.  The sulphamic chlorides obtained when sulphurylchloride is used, are hydrolysed to produce the free sulphamic acids.  Ethylether and trichlorethylene are mentioned as diluents.  When double bonds or hydroxy groups are present and sulphonation is liable to take place on a carbon or oxygen atom, sufficient sulphonating agent must be used to effect sulphonation on the nitrogen atom.  The amines and acid amides are particularly suitable as starting materials which are derived from mixed aromatic aliphatic carboxylic acids, e.g. phenylstearic acid (obtained from oleic acid and benzene by means of aluminium chloride), carboxylic acids obtained by the oxidation of paraffin wax, and from resinic and naphthenic acids.  The amines are also suitable which are produced from mineral acid esters of alcohols, obtained by catalytic reduction of oils and fats, by treatment with ammonia or primary amines according to the process of Specification 369,614, and the amines obtained from the fatty acids of fats and oils by forming the urethane by treating the fatty acid chloramide, obtained from the corresponding fatty acid chloride, with sodium methylate and treating the urethane with mineral acids or calcium hydrate. Specification 319,805, [Class 2 (iii), Dyes &c.], is referred to.