Patent GB-497856-A (GB)
Title: New nitrogeneous organic compounds and their application
IPC: D06M13/467
Filed: 1937-06-30
Abstract: Products believed to be quaternary ammonium salts are obtained by reacting (1) a urea derivative of the formula RCONHCONH2 or RR1NCONH2, or an allophanate of the formula ROCONHCONH2, where RCO in the first formula is the radicle (saturated or unsaturated) of an acid obtainable from oils or fats by saponification, R in the other formul  is a corresponding alkyl radicle, and R1 is hydrogen or an alkyl group, with (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 and m-nitrobenzene-sulphonate, trimethylamine hydrobromide, quinoline hydrochloride, 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 waterproofing 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 alkalineearth 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 acetate or formate, 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, and 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 stearylurea, (2) pyridine hydrochloride, paraformaldehyde and laurylurea (made from lauryl chloride and urea), (3) pyridine hydrochloride, paraformaldehyde, and heptadecylurea, (4) pyridine hydrochloride, paraformaldehyde, and N-cetyl-N-methylurea (made from nitrourea and cetylmethylamine), (5) pyridine hydrochloride and the methylol compound from heptadecylurea and paraformaldehyde, (6) pyridine hydrochloride, paraformaldehyde, and octadecyl allophanate (made from urea and octadecyl chloroformate).  Examples are given also in which (7) cotton sheeting is soaked with an aqueous solution of the product of example 1 and then dried at 40 DEG  C. and heated to 120 DEG  C.; (8) a silk fabric is impregnated with an aqueous solution of the product of example 1 and then dried at 40 DEG  C. and heated to 110 DEG  C.; (9) cotton sheeting is padded with an aqueous solution containing the product of example 1, ammonium dihydrogen phosphate, and a product obtained by boiling a urea solution for a short time with ammoniacal formaldehyde solution; the sheeting is dried at 40-50 DEG  C., heated to 150 DEG  C., and washed in a dilute solution of soap and soda; (10) cotton sheeting is padded with an aqueous solution of the product of example 6, dried at 50-60 DEG  C., heated to 150 DEG  C., and washed in a dilute solution of soap and soda.