Patent GB-460858-A (GB)
Title: Manufacture of sulphuric acid derivatives of imidazolines
IPC: C07D233/10
Filed: 1935-08-09
Abstract: Imidazolines containing sulpho groups and at least ten carbon atoms which are stated to have wetting, washing, foaming, dispersing and levelling properties, are prepared by (a) sulphonation of the parent imidazolines; (b) exchanging a halogen present in the parent imidazolines for the sulphonic group by means of a sulphite; or (c) combining at the nitrogen alkyl or aralkyl groups containing sulpho groups, e.g. by means of bromethanesulphonic acid or benzylchloride-p-sulphonic acid. Alternatively, the products may be prepared from components, i.e. aliphatic diamines and fatty acids, containing sulpho groups.  In examples: (1) undecylimidazoline, obtained from lauric acid and ethylenediamine is condensed with sodium bromethane sulphonate; (2) aminoethyltaurine sodium salt obtained from ethylenediamine and sodium chlorethanesulphonate is condensed with stearic acid. For the preparation of the parent imidazolines, propylenediamine, diethylenetriamine and naphthenic acids are mentioned as components.  The imido group may be converted into the pentavalent form by alkylation.  The Specification as open to inspection under Sect. 91 comprises also the introduction of sulpho groups by any known method into imidazoles of high molecular weight or derivatives thereof other than a benzimidazole and includes the introduction of a sulpho group at any stage in the manufacture of imidazolines from amidines and a -halogenated aliphatic or aliphatic-aromatic carbonyl compounds.  When the halogenated carbonyl compound is of low molecular weight, e.g. chloracetone or bromlaevulinic acid, it is condensed with an amidine of an acid of high molecular weight, e.g. oleic acid amidine or ricinoleic acid amidinemethylether.  If the halogenated carbonyl compound is of high molecular weight, e.g. chlorstearone, an amidine such as acetamidine, guanidine or dicyandiamidine may be used.  An imidazoline obtained from components of low molecular weight, e.g. from chloracetosulphonic acid and acetamidine may be alkylated with dodecyl or octadecylbromide.  The condensation of a -bromstearicbromide with guanidine followed by sulphonation, and the condensation of chloracetonesulphonic acid with oleic acid amidine is referred to.  This subject-matter does not appear in the Specification as accepted.ALSO:Imidazolines containing sulpho groups and at least ten carbon atoms which are stated to have dispersing properties are prepared by (a) sulphonation of the parent imidazolines: (b) exchanging a halogen present in the parent imidazolines for the sulphonic group by means of a sulphite or (c) combining at the nitrogen alkyl or aralkyl groups containing sulpho groups, e.g. by means of bromethanesulphonic acid or benzylchloride p-sulphonic acid. Alternatively, the products may be prepared from components, i.e. aliphatic 1 : 2-diamines and fatty acids, containing sulpho groups.  In examples (1) undecylimidazoline, obtained from lauric acid and ethylenediamine is condensed with sodium bromethane sulphonate: (2) amino-ethyltaurine sodium salt obtained from ethylenediamine and sodium chlorethane-sulphonate is condensed with stearic acid.  For the preparation of the parent imidazolines, propylenediamine, diethylenetriamine and naphthenic acids are mentioned as components.  The imido group may be converted into the pentavalent form by alkylation.  The Specification as open to inspection under Sect. 91 comprises also the preparation of dispersing agents by the introduction of sulpho groups by any known method into imidazoles of high molecular weight or derivatives thereof other than a benzimidazole, and includes the introduction of a sulpho group at any stage in the manufacture of imidazolines from amidines and a -halogenated aliphatic or aliphatic-aromatic carbonyl compounds. When the halogenated carbonyl compound is of low molecular weight, e.g. chloracetone or bromlaevulinic acid, it is condensed with an amidine of an acid of high molecular weight, e.g. oleic acid amidine or ricinoleic acid amidinemethylether.  If the halogenated carbonyl compound is of high molecular weight, e.g. chlorstearone, an amidine such as acetamidine, guanidine or dicyandiamidine may be used.  An imidazoline obtained from components of low molecular weight, e.g. from chloracetosulphonic acid and acetamidine may be alkylated with dodecyl or octadecylbromide.  The condensation of a -brom stearic bromide with guanidine followed by sulphonation, and the condensation of chloracetonestulphonic acid with oleic acid amidine is referred to.  This subject-matter does not appear in the Specification as accepted.