Patent GB-772223-A (GB)
Title: Improvements in imidazolinepropionates in the forms of metal salts, acid addition salts, and free acids, and preparation thereof
IPC: C07D233/18
Filed: 1955-10-18
Abstract: The invention comprises imidazolines of the formula <FORM:0772223/IV(b)/1> where R is a hydrocarbon radical, R1 is hydrogen or methyl and M is hydrogen or an equivalent of a metal, and their addition salts with strong inorganic acids.  These are made by reacting the corresponding 1-unsubstituted imidazolines with b -propiolactone, acrylonitrile or an alkyl acrylate, and in the latter cases hydrolysing the product to the free acid with aqueous alkali. Suitable temperatures are 75-150 DEG  C. in the case of the ester and 100-175 DEG  C. for the lactone.  The radical R is preferably an aliphatic group of 9-17 carbon atoms, and may be the residue of, e.g., tall oil acids which comprise a mixture of long-chain alkyl and rosin residues.  Examples show the reactions of (1) 2-heptadecyl-imidazoline and methyl acrylate, and product hydrolysed; (2) heptadecyl-4-methyl-imidazoline and methyl acrylate (hydrolysed); (3) 2-undecyl-imidazoline and methyl acrylate (hydrolysed), propiolactone, and acrylonitrile (hydrolysed); (4) 2-undecyl-4-methyl-imidazoline and methyl acrylate (hydrolysed); (5) 2-nonyl-imidazoline and methyl or ethyl acrylate (hydrolysed); (6) 2-heptadecenyl-imidazoline and methyl or butyl acrylate (hydrolysed); (7) 2-(tall oil residue)-imidazoline and methyl acrylate (hydrolysed).  The products may be obtained as sodium salts, free zwitter ions or hydrochlorides.  2-Substituted-imidazolines of the formula <FORM:0772223/IV(b)/2> are made by condensing 1 : 2-alkylene diamines with carboxylic acids or their salts or halides.  Examples are given of the preparation of 2-undecyl-imidazoline, 2-nonyl-imidazoline, 2-heptadecenyl-imidazoline, 2-(tall oil residue)-imidazoline and 2-undecyl-4-methyl-imidazoline.  The acid RCOOH may also be octyl-, nonyl- or dodecyl-benzoic acid.ALSO:Imidazolines of the formula <FORM:0772223/III/1> where R is a hydrocarbon radical, R1 is hydrogen or methyl and M is hydrogen or an equivalent of a metal, and their addition salts with strong inorganic acids, are surface-active cleansing agents effective in acid and alkaline solution.  They may be mixed with alkaline builders e.g. sodium carbonate or metasilicate, and/or with anion-active soaps and detergents.  The resulting compositions may be used in the form of bars powders, pastes or solutions.  Suitable imidazolines are mentioned.ALSO:Bactericidal compositions comprise quaternary ammonium salts and imidazolines of the formula <FORM:0772223/VI/1> where R is a hydrocarbon radical, R1 is hydrogen or methyl and M is hydrogen or an equivalent of a metal, or their addition salts with strong inorganic acids.  The ratio of quaternary salt to imidazoline may be 1:1 to 5:1 by weight.  A typical composition is octylphenoxyethoxyethyl - dimethyl-benzyl-ammonium chloride and the sodium salt of 2 - undecyl - 1 - (b  - carboxyethyl) - imidazoline. Other quaternary salts that may be used are dodecyl-trimethyl-ammonium chloride, dodecyl-dimethyl-benzyl-ammonium chloride, cetyl-pyridinium bromide and dodecylbenzyl-trimethyl-ammonium chloride.  Other suitable imidazolines are mentioned.