Patent GB-584914-A (GB)
Title: Process for the manufacture of new sulphamic acid derivatives
Filed: 1943-03-09
Abstract: New acylaminomethyl sulphamic acids or salts thereof are prepared by reacting with one another, in the presence of an acid condensing agent, formaldehyde, an amide of an aliphatic carboxylic acid having at least 12 carbon atoms and containing at least one <FORM:0584914/IV/1> group, and sulphamic acid or a salt thereof, advantageously, by heating in the presence of a solvent, such as methanol, acetone or glacial acetic acid.  In modifications, the amide or the sulphamic acid or salt thereof is reacted with formaldehyde to form the methylene or methylol compound which is then reacted with the other component; thus, the amide may be reacted with formaldehyde in a solvent, such as water, alcohol, acetone, glacial acetic acid, benzene, pyridine or mixtures thereof, at moderately elevated temperatures and, preferably, in the presence of an acid or alkaline condensing agent such as potassium carbonate, trimethylamine or hydrogen chloride.  Specified amides are those of lauric acid, coconut fatty acid, palmitic acid, stearic acid, olive acid, linoleic acid and hardened train oil fatty acid; the corresponding N- substituted products still containing amido-hydrogen, for example, N-methyl-, N-ethyl, N-hydroxyethyl-, or N-dihydroxypropyl-lauric acid amide, N-phenyl-stearic acid amide; diacylated methylene diamines, such as N : N1- distearylmethylene diamine.  Alkali salts of the sulphamic acid are preferred, whilst the formaldehyde may be used in aqueous solution or in polymeric form, such as paraformaldehyde.  The products are stated to be novel and may be used as textile assistants, for example, as wetting, dispersing, washing, softening, levelling, or foaming agents alone or in conjunction with other textile assistants.  In examples: (1) sodium sulphamate is reacted with an aqueous solution of formaldehyde in the presence of sodium carbonate and the resulting solution added to a solution of coconut fatty acid amide in glacial acetic acid followed by neutralising with sodium carbonate; the product is isolated by precipitating with ether or by distilling off the glacial acetic acid, neutralising and evaporating down; (2)-(4) similar products are obtained in like manner using stearic acid amide and oleic acid amide; (5) stearic acid amide is reacted with formaldehyde and the resulting methylolamide reacted with sodium sulphamate in glacial acetic acid; (6) stearic acid amide, sodium sulphamate and paraformaldehyde in water-methanol solution are reacted in the presence of hydrochloric acid; (7) a bath containing 0.3 gms. per litre of the product derived from oleic acid amide is employed for washing wool yarn.  The Specification as open to inspection under Sect. 91 relates to the above process wherein any amide containing at least one -CO.NH- group and any sulphamic acid of which the amido nitrogen carries at least one hydrogen atom are reacted with formaldehyde. Additional starting materials specified are aliphatic, aromatic, aliphatic-aromatic and heterocyclic amides, including amides of acetic acid, propionic acid, acrylic acid, butyric acid, caprylic acid, benzoic acid, naphthoic acid, para-stearylamino-benzoic acid, hexahydrobenzoic acid, and tetrahydronaphthylacetic acid, amides of resin or naphthenic acids, and amides of chloracetic acid, chlormethyl-benzoic acid, glycollic acid and the corresponding N- substituted products and phthalimide and diketopiperazine; ureas such as ethyl-, phenyl-, dodecyl, or octadecyl-urea or N : N1- di-dodecyl urea, and urethanes and diurethanes.  This subject-matter does not appear in the Specification as accepted.