Patent GB-448251-A (GB)
Title: Improvements in the manufacture and production of quaternary ammonium compounds
IPC: C08G59/50
Filed: 1934-12-10
Abstract: Quaternary ammonium compounds are obtained by treating tertiary amines containing one or more hydroxyalkyl groups with alkylene oxides under such conditions that the alkalinity of the mixture is reduced nearly to the neutral point, at least at the beginning of the reaction, by means of an acidic substance other than carbonic acid. Preferably, the pH value of the reaction mixture is less than 9, advantageously less than 8,5, at the beginning of the reaction, and is kept between 8 and 9,6 throughout the reaction.  The desired degree of alkalinity may be obtained by completely or partly neutralizing the amine with a weak organic acid, e.g. formic, acetic, butyric, stearic or lactic acid, or by partial neutralization with a strong acid, e.g. hydrochloric, sulphuric or phosphoric acid; acid salts of polybasic acids may also be used.  The acidic substance may be added partly before and partly during the reaction.  Methods are indicated whereby the products may be separated from the hydroxyalkyl ethers of the tertiary amines, which may be formed in subordinate amounts as by-products.  The products are useful (a) as assistants in the textile and related industries, e.g. as additions in cloth-printing and in making dyestuff pastes and powders; (b) as softening agents for artificial threads; (c) as additions to the spinning baths from which artificial threads are made, whereby threads of increased affinity for dyestuffs are obtained; and (d) for after-treating coloured threads, to improve their fastness to water and washing.  In the examples: (1) a soap prepared from triethanolamine and stearic acid is treated in water with ethylene oxide; the product is useful as a foaming agent, and may be converted into tetraethanolammonium hydroxide by treatment with caustic soda solution; the free base may be identified by conversion into its tetrabenzoyl compound; (2) triethanolamine and disodium phosphate are treated in water with ethylene oxide to yield tetraethanolammonium disodium phosphate, from which the free base may be recovered as in example 1; monosodium phosphate may also be used; (3) a solution of triethanolamine in aqueous hydrochloric acid is treated with ethylene oxide to yield tetraethanolammonium chloride and (as a by-product) the hydrochloride of the monohydroxyethyl ether of triethanolamine; the hydrochlorides may be separated by fractional solution in ethyl alcohol; (4) a solution of triethanolamine in aqueous sulphuric acid is treated in stages with ethylene oxide, with addition of sulphuric acid between the stages; the product is treated with barium hydroxide to recover tetraethanolammonium hydroxide; (5) a solution of triethanolamine in aqueous acetic acid is treated with ethylene oxide; (6) a solution of butyldiethanolamine in aqueous sulphuric acid is treated with ethylene oxide in stages, as described in example 4, and the product is worked up as in that example; butyltriethanolammonium hydroxide is obtained; (7) a solution of diethylethanolamine in aqueous sulphuric acid is treated with ethylene oxide, and the product is worked up as in example 4; diethyldiethanolammonium hydroxide is obtained.  Reference is made also to the use of propylene oxide and the treatment of tertiary hydroxyalkyl amines containing chains of more than six carbon atoms.