Patent GB-386966-A (GB)
Title: Improvements in the manufacture and production of agents suitable for use as assistants in the textile and allied industries
Filed: 1931-06-25
Abstract: Products stated to be useful, for example, as wetting, washing, dispersing, and softening agents in the textile and allied industries are prepared by condensing sulphuric esters of hydroxyalkylamines, which contain at least one hydrogen atom attached to a nitrogen atom, with compounds having the formula RCO-Halogen, in which R is a hydrocarbon radicle which may be substituted by hydroxy groups and which is connected to the carbon atom either directly or by means of an oxygen atom, in the presence of metal compounds having an alkaline reaction.  In examples: (1) ethanolaminesulphuric ester is condensed by means of caustic soda with stearic chloride and b -naphthoic chloride: (2) N-n-butyl-N-ethanolaminesulphuric ester (obtained by sulphonating the product prepared from ethyleneoxide and n-butylamine) is condensed with octodecylchlorcarbonicester and with coco nut fatty acid chlorides: (3) secondary aminobutanolsulphuricester is condensed with chloroformic-n-butylester and with phenolchlorcarbonicester: (4) ethanolaminesulphuricester and iso-propylaminesulphuricester are condensed with oleic acid chloride: (5) isobutanolaminesulphuricester is condensed with the chlorcarbonicesters of the alcohols obtained by the catalytic reduction of coco nut oil.  The products may advantageously be used with other assistants, e.g. for washing purposes they may be used with organic solvents such as carbontetrachloride, benzylalcohol, cyclohexanol, cyclohexanone, ethylene or propylene glycols or ethyleneglycolethers, and for the preparation of emulsions, glue and gum-like substances may be added. Soaps, Turkey red oils, true sulphonic acids, condensation products of acid chlorides with hydroxyalkyl sulphonic acids, and salts, e.g. sodium sulphate, sodium bicarbonate and perborates may also be present.  The following starting components are specified in addition to those used in the examples: mono- and di-N-a -hydroxybutylamine (obtained by treating acetaldol with hydrogen in the presence of ammonia and a nickel hydrogenation catalyst), N-ethylmonopropylamine, N-laurylmonoethanolamine (obtained by heating laurylamine with ethyleneoxide), di-isopropanolamine, b -ethylhexylbutanolamine (obtained from b -ethylhexylamine and a -butyleneoxide), N-phenyl or cyclohexyl-N-ethanolamine, N-octyl-N-ethanolamine, mono- and di-ethanolethylenediamine, acetylchloride, propionylchloride, palmitylchloride, phthalicacidchloride, acetylbromide, stearylbromide, lauryl and amylchlorcarbonic esters.  The metal compounds having an alkaline reaction comprise alkali and alkaline-earth oxides, hydroxides, carbonates and acetates, aluminium hydroxide or acetate and sodium silicate may also be used.  Soluble solvents such as ethyl alcohol, glycerol and dioxane may be present during the reaction.  According to the Provisional Specification, the sulphuric esters of hydroxyalkylamines may be reacted with any organic halogen compound, dyestuffs having exchangeable halogen atoms, chloracetic esters and chlorpropionic esters being specified. Chlorcarbonic esters used in the examples are prepared by treating the appropriate alcohol with phosgene.ALSO:Products stated to be useful, for example, as dispersing agents in the textile and allied industries are prepared by condensing sulphuric esters of hydroxyalkylamines, which contain at least one hydrogen atom attached to a nitrogen atom, with compounds having the formula RCO-Halogen, in which R is a hydrocarbon radicle which may be substituted by hydroxy groups and which is connected to the carbon atom either directly or by means of an oxygen atom, in the presence of metal compounds, having an alkaline reaction. In examples: (1) ethanolaminesulphuric ester is condensed by means of caustic soda with stearic chloride and naphthoic chloride, (2) N - n - butyl - N - ethanolaminesulphuricester (obtained by sulphonating the product prepared from ethyleneoxide and n-butylamine) is condensed with octodecylchlorcarbonicester and with coco nut fatty acid chlorides: (3) secondary aminobutanol sulphuricester is condensed with chloroformic-n-butylester and with phenolchlorcarbonicester: (4) ethanolaminesulphuricester and iso-propylaminesulphuricester are condensed with oleic acid chloride: (5) iso-butanolaminesulphuricester is condensed with the chlorcarbonicesters of the alcohols obtained by the catalytic reduction of coco nut oil: The products may advantageously be used with other assistants, e.g., for the preparation of emulsions, glue and gum-like substances, soaps, Turkey red oils, true sulphonic acids, condensation products of acid chlorides with hydroxyalkyl sulphonic acids, and salts, e.g. sodium sulphate, sodium bicarbonate and perborates may also be added.  The following starting components are specified in addition to those used in the examples: mono and di--N-g -hydroxybutylamine (obtained by treating acetaldol with hydrogen in the presence of ammonia and a nickel hydrogenation catalyst), N-ethyl monopropylamine, N-lauryl mono-ethanolamine (obtained by heating lauryl amine with ethyleneoxide), di-iso-propanolamine, b -ethylhexylbutanolamine (obtained from b -ethylhexylamine and a -butyleneoxide), N - phenyl or cyclohexyl - N-ethanolamine, N - octyl - N - ethanolamine, mono - and di - ethanolethylenediamine, acetylchloride, propionylchloride, palmitylchloride, phthalic-acidchloride, acetylbromide, stearylbromide, lauryl and amyl-chlorcarbonic esters.