Patent GB-615838-A (GB)
Title: Manufacture and application of new textile treatment agents
IPC: D06M13/322
Filed: 1946-08-14
Abstract: Quaternary carbamic compounds are made by reacting an aliphatic or heterocyclic tertiary amine or thiourea or a derivative thereof with one or more halogemethyl compounds, of the formula R(O.CO.NR1-CH2-X)n where R stands for an aliphatic radical, substituted or not, R1 stands for hydrogen or an organic residue, X stands for a halogen, and n stands for a whole number greater than one.  The reactants may be mixed alone or in a solvent or diluent.  Textile materials of animal or vegetable origin, or made of regenerated cellulose esters or ethers, may be impregnated with a solution or suspension of the products, followed by drying and heating, to improve shrink-resistance, water-repellence, and softness.  An alkaline substance or acid-binding agent, e.g. sodium acetate may be added to the impregnating fluid, together with polyvalent metal salts, e.g. aluminium acetate or stearate, or water-repellent waxes, e.g. paraffin wax, montan wax, carnauba wax, and beeswax, or other water-repellent agents such as methylolstearamide, methylenedistearamide, methyloloctadecylcarbamate, methylenedistearate and methylol and alkoxymethyl derivatives of polycarbamates.  Phenol-formaldehyde or ureaformaldehyde condensation products may be applied simultaneously.  Tertiary amines specified are trimethylamine, triethylamine, p  N.N1-tetramethylethylene diamine, dimethyl-cyclohexylamine, diethylcyclohexylamine, N-methyl-piperidine, pyridine, a -picoline, hexamethylene tetramine, thiourea tetramethylthiourea In examples, the chlomethyl bodies derived from the following polycarbamates are reacted with pyridine: (1) octodecane-1.12-diol bis-carbamate; (2) tristearin-11.111.1111-triol tris-carbamate (obtained from hydrogenated castor oil-see below); (3) triolein-11.111.1111-triol triscarbamate (obtained from castor oil); (4) triolein - 11.111.1111 - triol - tris - N - methylcarbamate; (5) tristearin-11.111.1111-triol tris-N-phenyl-carbamate; (6) the polycarbamates obtained by treating 11-hydroxystearic-N : N-dihydroxytehylamide with phosgene first and then ammonia; (7) ethylene-1.2-bis-carbamate; (8) trimethylene-1.3-bis-carbamate; (9) tetramethylene-1.4-bis-carbamate; (10) decamethylene-1.10-bis-carbamate; (11) hexamethylene-1.6-bis carbamate; (12) the polycarbamates obtained from castor oil, phosgene, and monoethanolamine.  Also in examples (13) trimethylamine is reacted with tristearin- or triolein-11.111.1111-triol-tris-carbamate; (14) tristearin-11.111.1111-triol-tris-carbamate is reacted with theiourea or tetramethylthiourea to give the isothiouronium compounds. Examples also describe the impregnation of flannel with the products of (2) and (3) above.  The polycarbomates above referred to are obtained by treating the appropriate polyhydroxy body with phosgene to give the chloroformate and then with ammonia or a primary amine; glycerol and N.N1-ethylene-bis-ricinoleamide are referred to as starting materials for this preparation.  The N-halogenmethyl polycarbamates are obtained by (1) treating the polycarbamates with formaldehyde and either a hydrogen halide or other halogenating agent, e.g. phosgene, thionyl chloride, or phosphorous pentachloride; (2) treating the polycarbamates with a di-halogendimethyl ether; (3) reacting the polycarbamate with part or all the formaldehyde to give a methylol body, which is then reacted with the hydrogen halide or other halogenating agent or dihalogendimethyl ether; (4) reacting the polycarbamate hydrohalide with formaldehyde.  Alkoxymethyl bodies may replace the corresponding methylol derivatives.