Patent GB-382718-A (GB)
Title: Improvements in the manufacture and production of wetting, cleansing, dispersing andlike agents
IPC: D06M13/402
Filed: 1931-09-28
Abstract: Products having wetting, cleansing, and dispersing properties are prepared by the reaction of neutral sulphites with carboxylic amides or N-substituted amides containing a mineral acid ester residue and an aliphatic or cycloaliphatic chain of more than five carbon atoms. The said chain may form part of the carboxylic acid residue of the amide or may be linked to the nitrogen atom, and the mineral acid residue may be present in either component of the amide.  Such amides may be prepared by esterifying a hydroxycarboxylic amide with a mineral acid, e.g. sulphuric or phosphoric acid or a hydrogen halide, or by treating a hydroxycarboxylic amide with chlorsulphonic acid, or by adding halogen or hydrogen halide or sulphuric acid to an unsaturated carboxylic acid or its amide, or by halogenating a saturated carboxylic acid or its amide, the acid being subsequently converted into the amide if necessary.  Suitable amides may thus be derived on the one hand from halogenated carboxylic acids such as chlor- or brom-acetic acid, a -chloro-propionic or -butyric acid, or a -bromo-caproic, -lauric, -myristic, -palmitic, or -stearic acid, or from unsaturated acids such as crotonic, maleic, fumaric, or undecenic acid, or from halogenated cycloaliphatic acids such as chloronaphthenic acids or from hydroxycarboxylic acids such as lactic or salicylic acid, and on the other hand from ammonia or any primary or secondary aliphatic, cycloaliphatic, aliphatic-aromatic or aromatic amine such as methylamine, mono- or di-alkylol amines such as ethanol- or propanol-amines, n-butylamines, dodecyl-, tetradecyl-, oleyl-, or octadecyl-amine, cyclohexylamine, benzylamine, aniline, or ethyl-or methyl-aniline. The reaction of the amides with the sulphites is generally effected at 80-250 DEG  C., if desired under pressure and preferably in an aqueous medium which may contain a solvent, e.g. methyl or ethyl alcohol, acetone, ordioxane, and an emulsifying agent, e.g. soap, turkey-red oil, or a sulphonate, particularly a sulphonate obtainable in the process.  The products may be applied, as such or as alkali salts, in the textile, leather, and paper industries, and may be used alone or associated with salts, acids, alkalies, glue, mineral, animal or vegetable oils, and solvents such as trichlorethylene, carbon tetrachloride, cyclohexanol, or ethyl alcohol.  The products may be converted into their salts with other metals such as calcium, strontium, barium, magnesium, or aluminium, such salts being useful as emulsifying agents.  In the examples, (1) chloracetic acid octadecylamide is heated with sodium sulphite in aqueous ethyl alcohol; (2) a mixture of dodecylamine and tetradecylamine is treated with chloracetyl chloride in dimethylaniline, and the amide mixture so obtained is heated with sodium sulphite in aqueous ethyl alcohol; (3) a -bromolauric acid ethylanilide is heated with sodium sulphite in aqueous ethyl alcohol; (4) a -bromopalmitic acid amide is treated as in examples 1 and 3; (5) a -bromopalmitic acid ethylanilide is treated as in examples 1 and 3.  Specification 360,539 is referred to.  Chloracetic acid octadecylamide is prepared by treating octadecylamine with chloracetyl chloride in dimethylaniline. Ethylanilides of a -bromo-lauric and -palmitic acids are prepared by treating the corresponding acid chlorides with ethylaniline.ALSO:Products having cleansing and dispersing properties are prepared by the reaction of neutral sulphites with carboxylic amides or N-substituted amides containing a mineral acid ester residue and an aliphatic or cycloaliphatic chain of more than five carbon atoms.  The said chain may form part of the carboxylic acid residue of the amide or may be linked to the nitrogen atom, and the mineral acid residue may be present in either component of the amide. Suitable amides may be derived on the one hand from halogenated carboxylic acids such as chlor- or brom-acetic acid, a -chloropropionic or -butyric acid, or a -bromo-caproic, -lauric, -myristic, -palmitic, or -stearic acid, or from addition products of unsaturated acids such as crotonic, maleic, fumaric, or undecenic acid, and halogen, hydrogen halide or sulphuric acid, or from halogenated cycloaliphatic acids such as chloronaphthenic acids or from hydroxycarboxylic acids such as lactic or Salicylic acid esterified with a mineral acid, and on the other hand from ammonia or any primary or secondary aliphatic, cycloaliphatic, aliphatic-aromatic or aromatic amine such as methylamine, mono- or di-alkylol amines such as ethanol- or propanolamines, n-butylamines, dodecyl-, tetradecyl-, oleyl- or octadecyl-amine, cyclohexylamine, benzylamine, aniline, or ethyl- or methylaniline.  The products may be applied, as such or as alkali salts, in the textile, leather, and paper industries, and may be used alone or associated with salts, acids, alkalies, glue, mineral, animal or vegetable oils, and solvents such as trichlorethylene, carbon tetrachloride, cyclohexanol or ethyl alcohol.  The products may be converted into their salts with other metals such as calcium, strontium, barium, magnesium or aluminium, such salts being useful as emulsifying agents.  In the examples, (1) chloracetic acid octadecylamide is heated with sodium sulphite in aqueous ethyl alcohol; (2) a mixture of dodecylamine and tetradecylamine is treated with chloracetyl chloride in dimethylaniline, and the amide mixture so obtained is heated with sodium sulphite in aqueous ethyl alcohol; (3) a -bromolauric acid ethylanilide is heated with sodium sulphite in aqueous ethyl alcohol; (4) a -bromopalmitic acid amide is treated as in examples (1) and (3); (5) a -bromopalmitic acid ethylanilide is treated as in examples (1) and (3).  Specification 360,539 is referred to.