Patent GB-808265-A (GB)
Title: Quaternary ammonium salts
Filed: 1957-08-23
Abstract: The invention comprises compounds of the formul  <FORM:0808265/IV (b)/1> <FORM:0808265/IV (b)/2> where R is hydrogen or a C12-18 aliphatic acyl radical, at least one R being said acyl radical, M is a C1-4 monovalent hydrocarbon group which may be saturated or ethylenically unsaturated, X is an anion and Z is the valence of X. The compounds are prepared by reacting a compound of the formula <FORM:0808265/IV (b)/3> with one or two equivalents of a quaternizing agent of the formula MzX.  The R's may be lauroyl, stearoyl, oleoyl, myristoyl, palmitoyl and/or ricinoleoyl.  X may be a chloride, bromide, iodide, sulphate, borate, phosphate, benzenesulphonate or toluenesulphonate ion.  M may be methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, allyl or crotyl.  The examples describe the preparation of the monoquaternary ammonium salts of N : N : N1 : N1 - tetrakis-(2-hydroxyethyl) - ethylenediamine monostearate and methyl chloride, methyl bromide, methyl iodide, ethyl bromide, n-propyl bromide, n-butyl bromide, isobutyl chloride, trimethyl phosphate, tributyl phosphate, trimethyl borate, dimethyl sulphate, diethyl sulphate, di-n-propyl sulphate, di-n-butyl sulphate, methyl benzenesulphonate and methyl para-toluenesulphonate respectively; the monoquaternary ammonium salts of N : N : N1 : N1 - tetrakis (2 - hydroxyethyl) - ethylenediamine distearate and methyl bromide, n-butyl bromide, allyl chloride, dimethyl sulphate and methyl para-toluenesulphonate respectively, the monoquaternary ammonium salts of N : N : N1 : N1-tetrakis - (2 - hydroxyethyl) - ethylenediamine dilaurate and dioleate and dimethyl sulphate, the diquaternary ammonium salts of N : N: N1 : N1 - tetrakis - (2 - hydroxyethyl - ethylenediamine mono- and di-stearates and dimethyl sulphate, and the mono- and diquaternary ammonium salts of N : N : N1 : N1-tetrakis - (2 - hydroxyethyl) - ethylenediamine tri- and tetra-stearates and dimethyl sulphate.  O-acylated N : N : N1 : N1-tetrakis-(2-hydroxyethyl)-ethylenediamine of the formula <FORM:0808265/IV (b)/4> where R is as above, are prepared by ester interchange between N : N : N1 : N1 - tetrakis - (2 - hydroxyethyl)-ethylenediamine and a C1-4 alkyl ester of a C12-18 fatty acid or fat acid.  Mixed esters may be prepared by using a mixture of ester reactants, e.g. butyl stearate and butyl laurate, in the ester interchange.  The interchange is catalysed by alkaline earth and alkali metal hydroxides and alkoxides, and also by aluminium isopropoxide.  Toluene and xylene may be used as solvents. Examples are given of the preparation of N : N : N1 : N1-tetrakis - (2 - hydroxyethyl) - ethylenediamine mono-, di-, tri- and tetra-stearates and corresponding dioleate and dilaurate compounds.ALSO:Quaternary O-acylated N : N : N1 : N1-tetrakis - (2 - hydroxyethyl) ethylenediamines of the formul  <FORM:0808265/IV (c)/1> and <FORM:0808265/IV (c)/2> where R is hydrogen or a C12-18 aliphatic acyl radical, at least one R being an acyl radical, M is a C1-4 monovalent hydrocarbon group which may be saturated or ethylenically unsaturated, X is an anion and Z is the valence of X, are applied as aqueous dispersions to textile fabrics prepared from cellulose acetate, nylon or vinyl chloride resins, to which they impart lubricity, softness of feel, anti-scorch properties and anti-static properties.  The compounds may be applied in aqueous urea- or melamine-formaldehyde resin baths.  In the above formul  the R's may be lauroyl, stearoyl, oleoyl, myristoyl, palmitoyl and/or ricinoleyl; M may be methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, allyl or crotyl; and X may be a chloride, bromide, iodide, sulphate, borate, phosphate, benzenesulphonate or toluenesulphonate ion.  In an example, an aqueous-dispersion of the monoquaternary ammonium salt prepared from N : N : N1 : N1-tetrakis-(2-hydroxyethyl) ethylenediamine distearate and dimethyl sulphate is padded on to nylon taffeta at 120 DEG  F. and the fabric dried at 225 DEG  F.