Patent GB-541071-A (GB)
Title: Manufacture and application of new condensation products
IPC: D06M13/322
Filed: 1940-03-14
Abstract: 541,071. Carboxylic acid amide derivatives; waterproofing fabrics ; wetting &c. agents. SOC. OF CHEMICAL INDUSTRY IN BASLE. March 14, 1940, Nos. 4799 and 4800. Convention dates, March 15, 1939 and Feb. 9, 1940. Addition to 537,221. Sample furnished. [Classes 2 (iii) and 15 (ii)] [Also in Group VIII] Carboxylic acid amides and urethanes which may be substituted once at the nitrogen atom are condensed with halogenmethyl ethers of unsubstituted alcohols containing at the most 5 carbon atoms. The products, which contain halogen may be converted into quaternary ammonium compounds to render them soluble by treatment with tertiary amines such as trimethylamine, triethylamine, triethanolamine, pyridine or N-methylpyridine. They may also be treated with thiourea or its derivatives which re-act in the iso form. When the products contain a radicle having at least 12 carbon atoms, they are wetting, foaming and softening agents. They are also disinfectants and preservatives. By de-composing the products, by heating or saponifying, while on a base such as a textile material, the latter is rendered water-repellent. Salts, such as sodium or ammonium acetate and aluminium formate, solvents, ureas, thioureas, ammonium sulphocyanide, soaps, protective colloids, methylolureas and weighting, softening and matting agents may be used in conjunction with the products. Their use in the leather and paper industries is mentioned. The amides used as starting material may be derived from mono or polybasic carboxylic acids of the aliphatic, aromatic or aliphatic-aromatic series, e.g. formic, propionic, valeric, capric, lauric, behenic, undecylenic, linoleic, chloracetic, bromacetic, α-bromlauric, succinic, adipic, maleic, benzoic, salicylic, oxynaphthoic, phenylacetic, phthalic, hexahydrobenzoic, naphthenic and resin acids and aliphatic, cycloaliphatic, aromatic or aliphatic-aromatic amines, e.g. methyl, amyl, dodecyl, diethylaminoethylamine, ethanolamine, triethylenetetramine, methylcyclohexylamine, #-naphthylamine and benzylamine, chloraniline, dimethylaminoaniline and toluidine. Chlor- and brommethylethers of methyl, propyl, butyl and amyl alcohols are mentioned. In examples the amide of hardened train oil acid and also stearic acid anilide are condensed with chlormethyl ethylether, and the products, dissolved in acetone, reacted with thiourea. Dyed cotton poplin is rendered soft and waterrepellent by immersing in a bath containing alcohol, sodium acetate and the product obtained from stearic acid anilide, pressing and heating. A sample has been furnished under Sect. 2 (5) of the Acts of a product obtained by reacting pyridine with the condensation products of octadecylurethane and chlormethylethylether. The Specification, as open to inspection under Sect. 91 comprises also the condensation of any compound containing an amide group, e.g. urea, with α-halogen methyl ethers of alcohols containing no reactive substituents, and the halogen present in the products may be converted into any group which produces or enhances water solubility, e.g. sulphonic, thiosulphuric, phosphonium, sulphonium and polyether groups. Instead of treating with thiourea, amino, cyanamide, dicyandiamide, or dicyandiamidine groups may be introduced and the products converted into salts. This subject-matter does not appear in the Specification as accepted.