Patent GB-498287-A (GB)
Title: Nitrogenous organic compounds and their application
Filed: 1937-06-30
Abstract: Products believed to be quaternary ammonium salts are obtained by reacting together (1) a carbamate of the formula ROCONH2, where R is the radicle (saturated or unsaturated) of an alcohol obtainable by reducing the carboxylic group of an acid obtainable from oils and fats by saponification, (2) formaldehyde or a reagent which yields it, and (3) a salt of a tertiary amine and (or) an addition product of a tertiary amine and an inorganic acid anhydride.  Specified reagents of type (3) are pyridine hydrochloride, m-nitrobenzenesulphonate, and nitrate, trimethylamine hydrobromide, quinoline hydrochloride, the reaction product of pyridine and sodium pyrosulphate, the addition compounds of pyridine with sulphur dioxide and sulphur trioxide, and the mixture of pyridine salt and pyridine addition product produced by the action of chlorsulphonic acid on pyridine.  The reagents may be brought to reaction simultaneously, or a methylol compound obtained from reagents (1) and (2) may be treated with reagent (3); as a further alternative, reagents (1) and (2), or the methylol compound obtained therefrom, may be dissolved in pyridine and the solution treated with sulphur dioxide.  The products yield foaming aqueous solutions which decompose when heated and then cease to foam.  They may be used as softening and (or) water-proofing agents for fabrics, threads and other fibrous materials of animal or vegetable origin, and for this purpose the fibrous material is impregnated with a solution of the quaternary compound in water or an organic solvent, and then heated to decompose the quaternary compound.  Preferably, the impregnated material is first dried at a temperature not above 80 DEG  C., preferably at 30-50 DEG  C., and then heated to 90-200 DEG  C. to decompose the quaternary compound. When cellulosic material is treated with a quaternary salt of a strong acid, an alkaline or buffering substance is preferably added to the impregnating solution or applied to the material before or after it is impregnated; suitable alkaline or buffering substances are pyridine, hexamethylenetetramine, and ammonium, alkali or alkaline-earth salts of weak acids, e.g. ammonium or sodium acetate or borax.  When an aqueous impregnating solution is used, its penetration into the material may be assisted by adding a small proportion of a water-soluble organic liquid, e.g. methyl or ethyl alcohol or acetone.  The quaternary compounds may be applied in conjunction with known textile-finishing agents, mention being made in this connection of aluminium salts such as aluminium formate or acetate, cellulose derivatives such as methyl, ethyl or glycol cellulose, resins or resin intermediates, gums or glues such as carrageen moss or gum tragacanth, and waxes or fatty substances such as paraffin wax, japan wax, montan wax, carnauba wax, aluminium stearate, or esters or amides of higher fatty acids.  The quaternary compounds may also be applied in conjunction with crease-proofing substances, such as condensation products of formaldehyde with phenols or with urea or its derivatives; these substances may be applied simultaneously with or separately from the quaternary compounds.  The latter may also be used in the resist printing of textiles by incorporating the compounds in resist printing pastes and printing and steaming the textiles; the pastes may include also ice-colour preparations which can be developed by treatment with an acid, and in this case the vapour of an acid, e.g. formic or acetic acid, may be added during steaming, whereby coloured resists are obtained; for producing the ground shade use may be made of vat dyes (applied as such from an alkaline reduction medium or in the form of leuco esters), azo dyes, which may be applied in the form of stabilized preparations containing a diazoamino compound and a coupling component, or mordant dyes.  Examples are given of the preparation of products from (1) pyridine hydrochloride, paraformaldehyde, and octadecyl carbamate, (2) paraformaldehyde, octadecyl carbamate, and the reaction product of pyridine with sodium pyrosulphate, (3) pyridine, paraformaldehyde, octadecyl carbamate and sulphur dioxide, (4) pyridine hydrochloride, paraformaldehyde, and dodecyl carbamate (obtainable from dodecyl alcohol and urea), (5) pyridine hydrochloride and the methylol compound obtained by condensing octadecyl carbamate with paraformaldehyde, (6) pyridine nitrate and methylol octadecyl carbamate, (7) pyridine hydrochloride and the methylol compound obtained by condensing dodecyl carbamate with paraformaldehyde, (8) quinoline hydrochloride and methylol octadecyl carbamate. Examples are given also in which (9) viscose artificial silk is impregnated with an aqueous solution of the product of example 1, dried at 40 DEG  C., and then heated to 120 DEG C., (10) wool gaberdine is impregnated with an aqueous solution of the product of example 6, dried at 50 DEG  C., heated to 150 DEG  C., and washed in a dilute ammoniacal soap solution, (11) a printed viscose fabric is impregnated in turn with an aqueous solution of sodium acetate and a benzene-alcohol solution of the product of example 3; it is then dried at 40 DEG  C., heated to 160 DEG  C., and washed in dilute ammoniacal soap solution.