Patent GB-458033-A (GB)
Title: Process for the manufacture of new quaternary ammonium compounds
IPC: A01N31/12
Filed: 1935-06-08
Abstract: Quaternary ammonium compounds containing attached to the nitrogen atom or atoms a nuclear-halogenated aralkyl radicle of the benzene series and a high-molecular aliphatic radicle of at least 8 carbon atoms, which may be interrupted by an oxygen, sulphur or nitrogen atom, are prepared by methods analogous to those of the parent Specification.  The products possess therapeutic properties and may be made up into antiseptic, disinfecting and preserving preparations with one another and with dispersing agents, or with diluents, e.g. water and alcohol, or carriers, e.g. talc, waxes, higher paraffins and water-soluble cellulose derivatives, if desired also with other known disinfecting or preserving media.  The products also have wetting properties.  Examples are given of the preparation of quaternary ammonium compounds from (1) N-dimethyl-o-chlorobenzylamine and n-octyl bromide; (2) N-dimethyl-p-iodobenzlamine and decyl bromide; also N - diethyl - p - bromobenzylamine and dodecyl bromide; (3) 3 : 4-dichlorobenzyl chloride and N - dimethyl - dodecylamine; (4) 2 : 4 : 5 - trichlorobenzyl chloride and N-dimethyl-dodecylamine; (5) N - dimethyl - 2 : 4 : 5 - trichlorobenzylamine and b  - hydroxy - g  - dodecyloxypropyl chloride; (6) N-methyl-N-(o-chlorobenzyl)-dodecylamine and dimethyl sulphate; (7) N-ethyl-o-chlorobenzyl-aminoethyl chloride and dodecyl mercaptan; (8) N-diethyl-N<1>-methyl-N<1> - (o - chlorobenzyl) - ethylene diamine and n - octyl bromide; (9) o - chlorobenzyl chloride and N : N<1>-dimethyl-N : N<1>-didodecylethylene diamine; (10) o-hydroxy-p-chlorobenzyldimethylamine and octodecyl bromide. Specification 441,473 is referred to.  Benzylamine derivatives.--N - Dimethyl - o - chlorobenzylamine is prepared by reacting o-chlorobenzyl chloride with dimethylamine, N-dimethyl-p-iodobenzylamine by reacting p-diazo - benzyldimethylamine with potassium iodide, N - dimethyl - 2 : 4 : 5 - trichlorobenzylamine by reacting the corresponding chloride with dimethylamine, N - methyl - N - (o - chlorobenzyl)-dodecylamine by treating o-chlorobenzyl chloride with methyl-dodecylamine, N-ethyl-o-chlorobenzyl-aminoethyl chloride by reacting o-chlorobenzyl chloride with ethylaminoethyl chloride, and o-hydroxy-p-chlorobenzyldimethylamine by treating p-chlorophenol with formaldehyde and dimethylamine.  N - Diethyl - N<1> - methyl - N<1> - (o - chlorobenzyl)-ethylene diamine is obtained by heating methyl-o-chlorobenzylamine with diethylaminoethyl chloride.ALSO:Quaternary ammonium compounds containing attached to the nitrogen atom or atoms a nuclear-halogenated aralkyl radicle of the benzene series and a high-molecular aliphatic radicle of at least 8 carbon atoms, which may be interrupted by an oxygen, sulphur or nitrogen atom, may be made up into antiseptic, disinfecting and preserving preparations with one another or with dispersing agents, or with diluents, e.g. water and alcohol, or carriers, e.g. talc, waxes, higher paraffins and water-soluble cellulose derivatives, if desired also with other known disinfecting or preserving media.