Patent GB-507628-A (GB)
Title: Process for rendering animal or vegetable fibrous materials water-repellent
IPC: D06M13/432
Filed: 1937-12-15
Abstract: 507,628. Treating textiles with liquids. GROVES, W. W. (I. G. Farbenindustrie Akt.- Ges.) Dec. 15, 1937, No. 34736. [Classes 2 (ii), 2 (iii), and 15 (ii)] [Also in Group VIII] Fibrous materials such as cotton, wool, silk, viscose or mixtures thereof are rendered water repellent by impregnation with an isothiourea salt containing the group wherein K stands for an aliphatic, aliphaticcycloaliphatic, or aliphatic-aromatic radical containing at least 11 carbon atoms, which may. contain substituents and/or may contain an oxygen, sulphur or nitrogen atom as a heteroatom in an aliphatic carbon chain or as a bridge directly linking an aliphatic portion of the radical to a cycloaliphatic or aromatic nucleus. R1 stands for an alkyl radical, X stands for oxygen, sulphur, or oxyphenyl or the group in which R2 stands for hydrogen or alkyl, and X1 stands for the group -CO.N#<R> or R -O.CO.N#<R> and subjecting the material to a heat treatment at a temperature from about 80 C. to about 150 C. Suitable compounds are the reaction products of thiourea or an alkyl-, aralkyl-, cycloalkyl- or aryl-compound thereof capable of reacting in the iso-form, such as ethyl-thiourea, triethyl-thiourea, benzyl thiourea, diphenylthiourea, cyclohexyl-dimethyl - thiourea, phenyl - ethyl - thiourea, ethylene-thiourea, with one of the following halogenmethyl compounds: halogenmethyl ethers of mono- or polyhydric alcohols (obtainable by the action of formaldehyde and hydrochloric acid on the alcohol) for example, dodecyl bromomethyl ether, octadecyl chloromethyl ether, the dichloromethyl ether of octadecanediol, the chloromethyl ether of octodecylglycol, the chloromethyl ether of isododecylphenylglycol and the chloromethyl ether of iso-octylphenyl-triglycol ; halogenmethyl thioethers, for example, octodecyl chloromethyl sulphide and dodecyl chloromethyl sulphides ; halogenmethyl compounds from carboxylic acid amides, ureas or carbamic acid esters (obtainable as described in Specification 507,207) such as N-dodecyl-acetochloromethyl amide, lauric acid methyl-chloromethyl amide, stearic acid chloromethyl amide, iso-octyl-phenoxy acetic acid chloromethylamide, the chloromethylamide of hydroxy-stearic acid from hardened castor oil, the chloromethyl compounds of 9 : 10-dichlorostearic acid amide, N-octadecyl-N-chloromethylcarbamic acid ethyl ester, N-methyl-N-chloromethyl-carbamic acid octadecyl ester, N-chloromethyl-carbamic acid 9 : 10-dichloro-octadecyl ester ; octadecyl-chloromethyl-urea; halogenmethyl compounds from aromatic hydroxyl compounds (obtainable as described in Specification 507,207) such as chloromethyl-isododecylphenol and halogen-methyl compounds of intermediate products obtained in the alkaline condensation of dodecylphenol with formaldehyde. Typical compounds are octadecyloxymethyl-isothiourea hydrochloride, stearylamidomethyl - isothiourea hydrochloride, the reaction product of para-n-dodecyl-ortho-chloromethylphenol and thiourea, S-stearyl-amidomethyl-N-dodecyloxymethyl-isothiourea hydrochloride (prepared from stearic acid chloromethyl amide and dodecyloxymethylthiourea, the latter being obtained from dodecyloxymethyl-isothiocyanate and ammonia (Am. Chem. Journ. 41, page 342), and the reaction product of thiourea or a compound thereof as above mentioned with a halogen-methyl compound prepared by the action of formaldehyde or a polymer thereof and a hydrohalic acid on stearic acid nitrile. The compounds may be used in the presence of buffering substances such as sodium acetate, lactate, tartrate or phosphate and may be applied in solution in an organic solvent or in aqueous solutions or dispersions at temperatures between 0 and 100 C. The impregnated material may be preliminarily dried at temperatures up to 80 C. before the heat treatment. The compounds may be applied in admixture with other water-proofing agents, e.g. paraffin, aluminium stearate, stearic acid anhydride and .the compounds described in Specifications 463,300 and 463,472 and in French Specification 819,945. The treatment may be. combined with softening, delustring, creaseproofing, filling and finishing processes, involving the use of, for example, stearic acid methylolamide (example 7) dimethylolurea (examples 10, 13 and 19), water-soluble formaldehyde - thiourea condensation products (example 12), and water-soluble condensation products from urea, formaldehyde and ammonium polysulphide (example 14). Other examples describe the use of (4) a compound made from N : N<11>-triethylthiourea and the chloromethyl compound of the amide from hardened fish oil fatty acid (iodine number 10-15) ; (6) a thiourea salt from octadecylchloromethyl ether and octadecyl-oxymethylpyridinium chloride ; (18) a compound made from thiourea and the chloromethyl compound of sym-adipic acid di-dodecylamide.