Patent GB-467244-A (GB)
Title: Manufacture of quaternary nitrogen compounds
IPC: C07C237/00
Filed: 1935-12-18
Abstract: Quaternary ammonium compounds are obtained by reaction of an aliphatic halogencarboxylic acid, or a salt, ester or amide thereof, with an aliphatic aminocarboxylic-acid amide disubstituted at the amino nitrogen atom by substituted or unsubstituted hydrocarbon radicles.  Specified halogencarboxylic acids are chloracetic, b -chloropropionic, and a -bromostearic acids; the salts, esters and amides of these acids may also be used.  Suitable aminocarboxylic amides disubstituted at the amino nitrogen atom are obtainable by the action of secondary amines on aliphatic halogencarboxylic amides such as chloracetic acid butylamide, p-toluidide, stearylamide, and methylstearylamide, a -chloropropionic acid oleylamide and ethanolamide, b -chloropropionic acid diethanolamide, a -bromostearic acid amide, and the amide mixture from chloracetic acid and the primary amines obtainable from palmnut oil acids.  The quaternary compounds are useful (a) as wetting, emulsifying or washing agents in the textile and allied industries, e.g. in dyeing, and (b) as oiling, bucking or fulling agents; they may be used alone or with appropriate additions such as organic solvents, hydrocarbon oils, vegetable or animal oils, fats or waxes, soaps, soap-substitutes, other textile assistants, salts, or bleaching agents.  In the examples: (1) dimethylaminoacetostearylamide (from chloracetostearylamide and dimethylamine) is treated with methyl chloracetate; (2) dimethylaminoacetobutylamide (from chloracetobutylamide and dimethylamine) is treated with ethyl chloracetate; (3) dimethylaminoacetooleylamide (from chloracetooleylamide and dimethylamine) is treated with sodium chloracetate; (4) diethylaminoacetododecylamide (from diethylamine and chloracetododecylamide which is obtained from chloracetyl chloride and dodecylamine) is treated with methyl bromacetate; (5) dimethylaminoacetostearylamide is treated with chloracetododecylamide; (6) dimethylaminoacetomethylstearylamide (from dimethylamine and chloracetomethylstearylamide) is treated with methyl chloracetate; (7) dimethylaminoacetostearylamide is treated with dodecyl chloracetate; (8) b  - dimethylaminopropionystearylamide (from dimethylamine and b -chloropropionic acid stearylamide) is treated with methyl chloracetate; (9) methyl chloracetate is reacted with a tertiary polyamine, obtained by heating chloracetostearylamide with a polyethylenepolyamine consisting substantially of diethylenetriamine; (10) dimethylaminoacetododecylamide (from dimethylamine and chloracetododecylamide) is treated with sodium a -bromostearate; other specified amino-N-disubstituted aliphatic aminocarboxylic acid amides which may be treated are dimethylaminopropionyl diethanolamide (from dimethylamine and b -chloropropionic acid diethanolamide, which is obtainable from p  b -chloropropionyl chloride and diethanolamine), a -dimethylaminostearylamide (from dimethylamine and a -bromostearic acid amide), and b -diethylaminopropionyldodecylamide; reference is made also to the use of aliphatic aminocarboxylic acid amides disubstituted at the amino nitrogen atom by substituted or unsubstituted aryl or aralkylhydrocarbon radicles.  Samples have been furnished under Sect. 2 (5), of products prepared as follows: (1) di(hydroxylethyl)aminoacetostearylamide (from diethanolamine and chloracetostearylamide) is treated with methyl chloracetate; (2) methyl glucaminoacetobutylamide (from N - methylglucamine and chloracetobutylamide) is treated with ethyl chloracetate.ALSO:Quarternary ammonium compounds useful as emulsifying agents are obtained by reaction of an aliphatic halogencarboxylic acid, or a salt, ester or amide thereof, with an aliphatic aminocarboxylic acid amide disubstituted at the amino nitrogen atom by substituted or unsubstituted hydrocarbon radicles. Specified halogencarboxylic acids are chloracetic, b -chloropropionic, and a -bromostearic acids; the salts, esters and amides of these acids may also be used.  Suitable aminocarboxylic amides disubstituted at the amino nitrogen atoms are obtainable by the action of secondary amine on aliphatic halogencarboxylic amides such as chloracetic acid butylamide, p-toluidide, stearylamide, and methylstearylamide, a -chloropropionic acid oleylamide and ethanolamide, b -chloropropionic acid diethanolamide, a -bromostearic acid amide, and the amide mixture from chloracetic acid and the primary amines obtainable from palmnut oil acids. The quaternary compounds may be used alone or with appropriate additions such as organic solvents, hydrocarbon oils, vegetable or animal oil, fats or waxes, soaps, soap-substitutes, other textile assistants, salts or bleaching agents.  In the examples: (1) dimethylaminoacetostearylamide is treated with methyl chloracetate; (2) dimethylaminoacetobutylamide is treated with ethyl chloracetate; (3) dimethylaminoacetooleylamide is treated with sodium chloracetate; (4) diethylaminoacetododecylamide is treated with methyl bromacetate; (5) dimethylaminoacetostearylamide is treated with chloracetododecylamide; (6) dimethylaminoacetomethylstearylamide is treated with methyl chloracetate; (7) dimethylaminoacetostearylamide is treated with dodecyl chloracetate; (8) b -dimethylaminopropionylstearylamide is treated with methyl chloracetate; (9) methyl chloracetate is reacted with a tertiary polyamine, obtained by heating chloracetostearylamide with a polyethylenepolyamine consisting substantially of diethylenetriamine; (10) dimethylaminoacetodedecylamide is treated with sodium a -bromostearate; other specified amino-N-disubstituted aliphatic aminocarboxylic acid amides which may be treated are dimethylaminopropionyldiethanolamide, a -dimethylaminostearylamide, and b -diethylaminopropionyldodecylamide; reference is made also to the use of aliphatic aminocarboxylic acid amides disubstituted at the amino nitrogen atom by substituted or unsubstituted or aralkyl hydrocarbon radicles.  Samples have been furnished under Sect. 2 (5), of products prepared as follows: (1) di(hydroxyethyl)aminoacetostearylamide is treated with methyl chloracetate; (2) methylglucaminoacetobutylamide is treated with ethyl chloracetate.