Patent GB-442767-A (GB)
Title: Manufacture of quaternary ammonium salts
IPC: C07D213/20
Filed: 1935-04-23
Abstract: Quaternary ammonium salts are obtained by reacting a tertiary amine with (1) an acid of the formula XnRCOOH, where X is halogen, n is less than seven, and R is the residue of an aliphatic, cycloaliphatic, or aliphatic-cycloaliphatic hydrocarbon containing at least eight carbon atoms, or (2) an ester of such an acid with a mono- or poly-hydric alcohol containing less than six carbon atoms, or (3) an amide of such an acid, which may be substituted on the nitrogen atom by an alkyl, cycloalkyl or aryl group or groups. Specified acids are mono-, tetra- and hexa-chloropalmitic acids, a -bromolauric acid, a -bromomyristic acid, a -bromopalmitic acid, a -bromostearic acid, a -bromomontanic acid, 12-bromo-9-octadecene-1-carboxylic acid, a -iodostearic acid, and chlorinated or brominated naphthenic or resin acids; salts of these acids may also be used.  Specified esters are those of the acids mentioned with methyl, ethyl or amyl alcohol, glycol, or glycerol. Specified amides are a -bromolauric amide, a -bromolauric anilide, a -bromopalmitic hydroxyalkylamides, a -bromostearic amide, a -bromostearic anilide, a  - bromostearic - 2 : 5-dichloranilide, a -bromostearic - m-nitranilide, and a -bromostearic-o-anisidide.  The tertiary amines may contain alkyl, cycloalkyl or aryl groups or may be heterocyclic; specified amines are trimethylamine, triethylamine, triethanolamine, dimethylcyclohexylamine, dimethylaniline, and pyridine, quinoline and their homologues.  The amine must be so selected that it is capable of reacting only with the halogen atom in the acid, ester or amide; for example, a tertiary hydroxyamine is not used when a carboxylic acid is treated.  The reaction may be effected at atmospheric or raised temperature and pressure in the presence or absence of a solvent and a catalyst, e.g. subdivided copper, a copper compound, or sodium iodide.  The products have wetting, cleansing and emulsifying properties and may be used (a) as additions to acid dye baths, for instance in dyeing with chromium compounds, mordant dyes, or dyes used in an acetic acid bath, or (b) for softening textile fibres, or (c) for increasing the fastness of dyeings to water.  They may be used alone or with solvents, electrolytes, protective colloids, and soaps or saponaceous materials.  In the examples: (1) a -bromostearic ethyl ester is treated with pyridine; cotton dyed with Cotton yellow CH may be treated with a solution of the product, to increase the fastness of the dyeing to water; similar products are obtainable from pyridine and a -bromolauric ethyl ester or a -bromopalmitic acid; (2) a -bromostearic amide (from a -bromostearic acid bromide and ammonia) is treated with pyridine; the use of the product for softening viscose artificial silk is described; the product may also be added to a wool-dyeing bath containing Neolan bordeaux R and sulphuric acid; (3) a -bromostearic acid is treated with pyridine; (4) a -bromostearic anilide (from a -bromostearic acid bromide and aniline) is treated with pyridine; the use of the product for after-treating cotton dyed with Chlorantin light red 5BL is described; (5) a -bromolauric anilide (from a -bromolauric acid bromide and aniline) is treated with pyridine; (6) a -bromolauric anilide is treated with trimethylamine; the addition of the product to a wool-dyeing bath containing Neolan dark green B and sulphuric acid is described.ALSO:Quaternary ammonium salts having emulsifying and cleansing properties are obtained by reacting a tertiary amine with (1) an acid of the formula XnRCOOH, where X is halogen, n is less than seven and R is the residue of an aliphatic, cycloaliphatic, or aliphatic-cycloaliphatic hydrocarbon containing at least eight carbon atoms, or (2) an ester of such an acid with a mono- or poly-hydric alcohol containing less than six carbon atoms, or (3) an amide of such an acid, which may be substituted on the nitrogen p atom by an alkyl, cycloalkyl or aryl group or groups.  Specified acids are monotetra- and hexa-chloropalmitic acids, a -bromolauric acid, a -bromomyristic acid, a -bromopalmitic acid, a -bromostearic acid, a -bromomontanic acid, 12-bromo-9-octadecene-1-carboxylic acid, a -iodostearic acid, and chlorinated or brominated naphthenic or resin acids; salts of these acids may also be used.  Specified esters are those of the acids mentioned with methyl, ethyl or amyl alcohol, glycol, or glycerol.  Specified amides are a -bromolauric amide, a -bromolauric anilide, a -bromopalmitic hydroxyalkylamides, a -bromostearic amide, a -bromostearic anilide, a  - bromostearic - 2 : 5-dichloranilide, a  - bromostearic - m - nitranilide, and a -bromostearic-o-anisidide.  The tertiary amines may contain alkyl, cycloalkyl or aryl groups or may be heterocyclic; specified amines are trimethylamine, triethylamine, triethanolamine, dimethylcyclohexylamine, dimethylaniline, and pyridine, quinoline and their homologues.  The amine must be so selected that it is capable of reacting only with the halogen atom in the acid, ester or amide, for example, a tertiary hydroxyamine is not used when a carboxylic acid is treated.  The products may be used alone or with solvents, electrolytes, protective colloids, and soaps or saponaceous materials.  In the examples, a -bromostearic ethyl ester, a -bromolauric ethyl ester, a -bromopalmitic acid, a -bromostearic amide, a -bromostearic acid, a -bromostearic anilide and a -bromolauric anilide are treated with pyridine, and a -bromolauric anilide is treated with trimethylamine.