Patent GB-533219-A (GB)
Title: Manufacture of mercapto-acidamide condensation products
IPC: C07C233/00
Filed: 1939-08-02
Abstract: 533,219. Textile assistants; proofing textiles. SOC. OF CHEMICAL INDUSTRY IN BASLE. Aug. 2, 1939, Nos. 22395 and 22396. Convention dates, Aug. 11, 1938 and July 19, 1939. [Classes 2 (iii) and 15 (ii)] [Also in Groups III and VIII] An aliphatic mercaptan or salt thereof is condensed with a methylol compound of a carboxylic acid amide or the corresponding halogen methyl derivative thereof. The reaction components may contain groups which determine or enhance the water solubility of the products, namely sulphonic, thiosulphuric acid, sulphuric acid ester, carboxylic quaternary ammonium groups or glycerol, polyglycerol or polyglycol residues or an amino or imino group in salt form. Water solubilizing groups may also be formed by converting a product containing a hydroxy group into a sulphuric acid ester group or a halogen atom into a sulphonic or thiosulphuric acid ester group. The halogen may also be reacted with ammonia, an amine or an isothiourea. In examples : (1) stearic acid methylolamide is condensed with thioglycollic acid ; a mixture of the sodium salt of the product with the disodium salt of the mono carboxylic acid ester derived from 4- sulphophthalic acid and a mixture of hexa- and octa-decyl alcohols is used for softening viscose artificial silk ; (2) lauric acid methyl olamide is condensed with thioglycollic acid and with glycerinmercaptan; the product obtained with the latter is treated with sulphuric acid, neutralized and extracted with alcohol ; (3) the N-chlor methyl compound of N-methylstearic acid amide is condensed with thioglycollic acid ; (4) lauric acid-N-methylolamide is condensed with sodium #-mercaptoethanesulphonate. The products may be used in the textile, leather and paper industries. The insoluble products are suitable for use as waxes and when the products contain high aliphatic or cycloaliphatic residues and are soluble they are stated to be wetting, washing, emulsifying, foaming, softening and levelling agents. They may be used in association with soaps, solvents, colloids, dressing agents and salts such as sodium acetate. Methylol amides of acetic, propionic, acrylic, butyric, capric, undecylic, palmitic, myristic, oleic, chlorpropionic and chloracetic acids are mentioned as starting materials. Urea and urethane and substitution products thereof such as ethyl and octyl urethane may be used. The methylol compounds may be obtained by reacting the amide, in acetone, benzene, pyridine or other solvent with formaldehyde in the presence of trimethylamine, potassium carbonate, barium hydroxide, hydrogen chloride sulphuric acid or zinc chloride as catalyst. The Specification as open to inspection under Sect. 91 comprises also the condensation of any mercaptan with a methylolamide of any carboxylic acid or functional derivative thereof. The use of methylolamides of benzoic, naphthoic, hexahydrobenzoic, resinic, naphthenic chlormethylbenzoic and salicyclic acids is mentioned. Methylol derivatives of thiourea, melamine, palmitoylthiourea, benzylurethane, cyclohexyl urethane and sulphophthalimide may also be used as starting material. The products may be converted into, insoluble compounds by means of heat or saponifying agents. When this is effected in the presence of textiles, the properties of the latter are modified. Thus their resistance to creasing, their water repelling properties, their insulating properties to heat and electricity are increased. Diminution of lustre, displacement of fibres, prevention of felting and shrinking, and improvement in the fastness of dyeings may also be effected. By applying the agents locally, calendering, matt and damask effect may be produced. This subject-matter does not appear in the Specification as accepted.