Patent GB-950384-A (GB)
Title: Alkylbenzyldiethylenetriamine acetic acids
IPC: C23F11/14
Filed: 1962-04-19
Abstract: Compounds of formula (I), wherein R is C6-24 alkyl, M is H, alkali metal or ammonium (optionally alkyl- or hydroxyalkyl-substituted), m and q are each 1, 2, 3 or 4 and n is 0, 1, 2 or 3, such that (q + m + n) = 5 <FORM:0950384/C1/1> may be employed in the foam separation of e.g. radioactive strontium. The preferred compounds (I) are N-dodecylbenzyldiethylenetriamine mono-, di-, tri- and tetra-acetic acids; mention is made of the free acids, their hydrochlorides and the sodium, potassium, ammonium, triethanolamine, t - octylamine and dodecylamine salts, with particular reference to the di-acid.  In Example 4, details are given of the use of the disodium salt of dodecylbenzyldiethylenetriaminetriacetic acid in the foam separation of radio-active strontium in strontium chloride.ALSO:The invention comprises compounds of formula (I) wherein R is C6-24 alkyl; M is H, alkali metal or ammonium which may be alkyl-or hydroxyalkyl-substituted; m and q are each 1, 2, 3 or 4 and n is 0, 1, 2, or 3, such that (q+m+ n)=5. <FORM:0950384/C2/1> <FORM:0950384/C2/2> Such compounds are produced by reacting amines of formula (II), wherein n1 is 1, 2, 3 or 4 such that (q+n1)=5, with 1-4 moles of a compound introducing the -CH2CO2H group; where the latter is introduced in a modified form, the acid group is liberated and optionally reacted with alkali or ammonium ions.  The preferred compounds (I) are N-dodecylbenzyl-diethylenetriamine mono-, di-, tri- and tetraacetic acids; in examples, the parent triamine is reacted with sodium or potassium chloroacetate and the di-acid, in particular, may be isolated as the free acid, its hydrochloride, or the sodium, potassium, ammonium, triethanolamine, t-octylamine or dodecylamine salts. Reagents which may in general be used to introduce the acetic acid group are: monochloro- and monobromo-acetic acids, their salts, esters, amides and nitriles, formaldehyde cyanohydrin or mixtures of alkali a hydrogen cyanide with formaldehyde. U.S.A. Specification 2,952,635 is referred to.ALSO:Compounds of formula (I), wherein R is C6-2 4 alkyl, M is H, alkali metal or ammonium (optionally alkyl- or hydroxyalkyl-substituted), m and q are each 1, 2, 3 or 4 and n is 0, 1, 2 or 3, such that (q+m+n)=5, <FORM:0950384/C3/1> may be employed as additives to rubber and other plastic materials.  The preferred compounds (I) are N-dodecylbenzyldiethylenetriamine mono-, di-, tri- and tetra-acetic acids, mention is made of the free acids, their hydrochlorides and the sodium, potassium, ammonium, triethanolamine, t-octylamine and dodecylamine salts, with particular reference to the di-acid.ALSO:Compounds of formula (I), wherein R is C6-24 alkyl, M is H, alkali metal or ammonium (optionally alkyl- or hydroxyalkyl-substituted), m and q are each 1, 2, 3 or 4 and n is 0, 1, 2 or 3, such that (q+m+n) = 5, <FORM:0950384/C3/1> may be employed as wetting and foaming agents, as pigment dispersing agents, and for prevention of rancidity in soaps (solid or aqueous solutions).  The preferred compounds (I) are N - dodecylbenzyldiethylenetriamine mono-, di-, tri- and tetra-acetic acids, mention is made of the free acids, their hydrochlorides and the sodium, potassium, ammonium, triethanolamine, t-octylamine and dodecylamine salts, with particular reference to the di-acid.ALSO:Compounds of formula (I) wherein R is C6-24 alkyl, M is H, alkali metal or ammonium (optionally alkyl- or hydroxyalkyl-substituted), m and q are each 1, 2, 3 or 4 and n is 0, 1, 2 or 3, such that (q + m + n) = 5, <FORM:0950384/A5-A6/1> (I) may be employed as stabilizers/corrosion inhibitors in lubricating oils or in oleaginous-aqueous systems such as emulsions of dilute acetic acid and vegetable oils (e.g. olive and cottonseed oils), as detoxification agents for living organisms when contaminated (at least externally) with polyvalent radioactive metal ions and metals and other toxic metal ions and metals, as antienzyme agents for prevention of deterioration in living materials comprising calcium, e.g. for the prevention of dental caries in mammals and as stabilizers for aqueous oleaginous emulsions.  The preferred compounds (I) are N-dodecylbenzyldiethylenetriamine mono-, di-, tri- and tetra-acetic acids, mention is made of the free acids, their hydrochlorides and the sodium, potassium, ammonium, triethanolamine, t-octylamine and dodecylamine salts, with particular reference to the di-acid.ALSO:Compounds of formula (I), wherein R is C6-24 alkyl, M is H, alkali metal or ammonium (optionally alkyl- or hydroxyalkylsubstituted), m and q are each 1, 2, 3 or 4 and n is 0, 1, 2, or 3, such that (q + m + n) = 5, <FORM:0950384/D1-D2/1> may be employed as antistatic agents for the prevention of dust gathering on fabrics e.g. silk or nylon.  The preferred compounds (I) are N-dodecylbenzyldiethylenetriamine mono-, di-, tri- and tetra-acetic acids, mention is made of the free acids, their hydrochlorides and the sodium, potassium, ammonium, triethanolamine, t-octylamine and dodecylamine salts, with particular reference to the di-acid.ALSO:As stabilizers for oil-water emulsions, e.g. emulsions of olive oil and cottonseed oil in dilute acetic acid, are employed the surface active, chelating agents of formula: <FORM:0950384/A1-A3/1> wherein R is C6-24 alkyl, M is H, alkali metal or amonium (optionally alkyl- or hydroxyalkylsubstituted), m and q are each 1, 2, 3 or 4 and n is O, 1, 2 or 3, such that (q + m + n) = 5, may be employed.  The preferred compounds (1) are N-dodecyl-benzyldiethylenstriamine mono-, di, tri- and tetra-acetic acids, mention is made of the free acids, their hylrochlorides and the sodium, potassium, amonium, triethanolamine, t-octylamine and dodecylamine salts, with particular reference to the di-acid.