GB549328A - - Google Patents

Abstract

549,328. Imidazdlines ; textiles, treating. RICHARDS CHEMICAL WORKS. March 1, 1940, No. 3923. Convention date, March 11, 1939. Samples furnished. [Classes 2 (iii) and 15 (ii)] Salts of Á-alkyl-N-acylamidoalkyl-imidazolines are prepared by acylating and neutralizing imidazolines of the formula wherein X', X<SP>2</SP>, X<SP>3</SP> and X<SP>4</SP> are hydrogen atoms or alkyl groups and R represents a hydrogen atom or a (C 2 X<SP>1</SP>X<SP>2</SP>X<SP>3</SP>X<SP>4</SP>NH) n H group, n being a whole number. The acylating agent used may be one which simultaneously effects salt formation, e.g. acid anhydrides and halides ; moreover, the acylation and neutralization may be effected simultaneously. The products are useful as textile treating and finishing agents, as softening and plasticizing agents for cellulosic materials, as detergents and wetting agents, and for improving the dyeing qualities of cellulosic fabrics. The starting materials are prepared by condensing polyalkylene-polyamines with fatty acids or their esters, e.g. according to Specification 337,368, [Class 2 (iii)]. According to the examples, (1) acetic anhydride is gently heated with the mixed imidazolines resulting from the interaction of diethylenetriamine with the commercial mixture of stearic and palmitic acids ; the product comprises a mixture of Á-heptadecyl- and Á- pentadecyl - N - acetamidoethyl - imidazoline acetates ; by using benzoyl chloride in place of acetic anhydride a mixture of Á-heptadecyl- and Á-pentadecyl-N-benzamidoethyl-imidazoline hydrochlorides is obtained ; (2) diethylenetriamine is condensed with oleic acid and the product heated with acetic anhydride to give a mixture consisting mainly of Á-heptadecenyl- N-acetamidoethyl-imidazoline acetate ; (3) diethylenetriamine is condensed with stearic acid, the product heated with 2-ethylbutyric acid and neutralized with acetic acid to give Á- heptadecyl-N-(2-ethylbutyramidoethyl) - imidazoline acetate. The samples furnished under Sect. 2 (5) are prepared by treating the condensation product of diethylenetriamine and 2-ethylbutyric acid with (1) acetic anhydride, (2) stearic acid and (3) first with sebacic acid and then with formic acid ; (4) condensing dipropylenetriamine with stearic acid and treating with acetic anhydride ; condensing tetraethylenepentamine with stearic acid and treating with (5) acetic anhydride, (6) first with 2-ethylbutyric acid and then with formic acid, and (7) first with coconut fatty acids then with hydrochloric acid. The Specification as open to inspection under Sect. 91 also describes the formation of quaternary compounds in lieu of neutralization, e.g. by treatment with diethyl sulphate or benzyl chloride. This subject-matter does not appear in the Specification as accepted.