Patent GB-611682-A (GB)
Title: New quaternary ammonium compounds and the treatment of textile materials therewith
IPC: A63H17/00
Filed: 1946-05-06
Abstract: Quaternary ammonium compounds are obtained by addition of aliphatic or heterocyclic tertiary amines to the reaction products of an aliphatic nitrile of more than seven carbon atoms, formaldehyde, and a dibasic organic acid chloride.  Suitable tertiary amines are triethylamine, triethanolamine, pyridine and picolines.  Suitable nitriles are those of caprylic, lauric, stearic and oleic acids and the mixed acids obtainable from fats and oils such as coconut and palm-kernel oil.  Suitable acid chlorides are those of oxalic, malonic, succinic, glutaric, adipic, sebacic and phthalic acids.  The nitrile, formaldehyde and the acid chloride may be reacted at 75-90 DEG  C., preferably in the presence of a catalyst such as zinc chloride, or the acid chloride may be treated with formaldehyde and the nitrile then added; the formaldehyde may be used as such or as a polymer.  Examples are given in which pyridine is added to reaction products obtained from (1) stearonitrile, succinyl chloride and paraformaldehyde, (2) stearonitrile, adipyl chloride and para - formaldehyde, (3) caprylonitrile, succinyl chloride and paraformaldehyde, and (4) stearonitrile, glutaryl chloride and paraformaldehyde, zinc chloride being present in each case.  The products are useful in the textile industry, e.g. in wetting, softening, water-proofing and crease-resisting processes.  They may be used in association with assistants such as alkaline substances such as sodium acetate, polyvalent metal salts such as aluminium acetate, waxes such as paraffin wax, montan wax, carnauba wax and beeswax, nitrogenous water-repellent agents such as methylolstearamide, methylene distearamide, methyloloctadecyl carbamate and methylene distearate and condensation products of formaldehyde with phenols or with urea or urea derivatives.ALSO:Quaternary ammonium compounds useful for treating textiles are obtained by addition of aliphatic or heterocyclic tertiary amines to the reaction products of an aliphatic nitrile of more than seven carbon atoms, formaldehyde, and a dibasic organic acid chloride.  Suitable tertiary amines are triethylamine, triethanolamine, pyridine and picolines.  Suitable nitriles are those of caprylic, lauric, stearic and oleic acids and the mixed acids obtainable from fats and oils such as coconut and palm-kernel oil. Suitable acid chlorides are those of oxalic, malonic, succinic, glutaric, adipic, sebacic and phthalic acids. Textile materials may be given a soft finish by treatment with aqueous solutions or suspensions of the compounds, and if the treated materials are heated, e.g. to about 150 DEG  C., a water-repellent finish is produced.  For these purposes the compounds may be used in association with other textile-finishing agents, e.g. alkaline substances such as sodium acetate, polyvalent metal salts such as aluminium acetate, waxes such as paraffin wax, montan wax, carnauba wax and beeswax, and other nitrogenous water-repellent agents such as methylolstearamide, methylene distearamide, methyloloctadecyl carbamate and methylene distearate.  The compounds may also be used in association with products which render textiles crease-resistant, e.g. condensation products of formaldehyde with phenols or with urea or urea derivatives, the two treatments being applied simultaneously or separately.  The compounds are also useful as wetting agents. Examples are given in which pyridine is added to reaction products obtained from (1) stearonitrile, succinyl chloride and paraformaldehyde, (2) stearonitrile, adipyl chloride and paraformaldehyde, (3) caprylonitrile, succinyl chloride and paraformaldehyde, and (4) stearonitrile, glutaryl chloride and para formaldehyde, zinc chloride being present in each case. Examples are given also in which (5) cotton gaberdine is padded with an aqueous alcoholic suspension containing the product of example (1) and sodium acetate, and then heated to 150 DEG  C.; (6) viscose staple fibre and cotton cambric are padded with an aqueous alcoholic suspension of the product of example (1) and then dried.