Patent GB-979133-A (GB)
Title: Alkylated and peralkylated derivatives of acylated polyalkylene polyamines, a processfor their manufacture and their use
IPC: D06M13/405
Filed: 1961-02-13
Abstract: Alkylated or peralkylated derivatives of acylated polyalkylene polyamines are prepared by condensing 1 mol. of a polyalkylene polyamine of the formula H2N-(CnH2n-NH)m-CnH2n-NH2 in which m represents an integer of from 1 to 4 and n represents an integer which is at least 2, with 2 mols of at least one aliphatic carboxylic acid containing 9 to 31 carbon atoms, and alkylating or peralkylating the resulting diacylated compound of the formula R1-CONH-(CnH2n-NH)m-CnH2n-NH-COR2 in which R1 and R2 represent the same or different residues of the above defined acid or acids and m and n have the meanings given above, by treating it at a temperature of 30 to 70 DEG C. with an amount, as hereinafter defined, of an alkylating agent in an aqueous medium containing at least 1 mol. of an alkaline agent per -NH- group (to the nitrogen atom of which no acyl radicals are bound). In a modification of the above process, a diacylated polyalkylene polyamine having the formula given above and prepared according to the acylation procedure defined above is mixed with another such diacylated polyalkylene polyamine and the resulting mixture is then alkylated or peralkylated according to the procedure defined above.  If the diacylated polyalkylene polyamine contains only 1 or 2 -NH- groups (to the nitrogen atoms of which no acyl radicals are bound), then the compound is treated, in the alkylation stage, with at least 1 and up to about 2 mols of the alkylating agent per said -NH- group. If the diacylated polyalkylene polyamine contains more than 2 such -NH- groups, then it is treated with at least a quantity of alkylating agent sufficient to alkylate a major portion of the -NH- groups (to the nitrogen atoms of which no acyl radicals are bound) and with up to about 2 mols of the alkylating agent per said -NH- group.  The condensation of the polyalkylene polyamines with the carboxylic acids is carried out at elevated temperatures, preferably at 130 to 180 DEG C., and advantageously in the presence of nitrogen.  Polyalkylene polyamines specified are triethylene tetramine, tetraethylene pentamine, dipropylene triamine, tripropylene tetramine and the corresponding butylene amines. Carboxylic acids specified are lauric acid, myristic acid, palmitic acid, stearic acid, coconut fatty acid, linoleic acid, oleic acid, tallow oil fatty acid, sperm oil fatty acid, behenic acid and arachic acid.  The alkylating agents are preferably alkyl esters of strong inorganic acids, e.g. dimethyl sulphate, methyl iodide and ethyl iodide.  The alkaline agent used for the alkylating step is preferably an alkali metal hydroxide, e.g. sodium hydroxide. Examples illustrate the alkylation of various diacylated polyalkylene polyamines with dimethyl sulphate. The alkylated products are used for treating textiles (see Division D1).ALSO:Alkylated and peralkylated derivatives of acylated polyalkylene polyamines of the formula R1-CONH-(CnH2n - NH)m - CnH2n -NH-COR2 in which R1 and R2 contain 8 to 30 carbon atoms and are the same or different residues of aliphatic carboxylic acids containing 9 to 31 carbon atoms, m is an integer of from 1 to 4, and n is an integer which is at least 2, are used as softening agents for textiles, e.g. cellulosic textiles ("Alkylated" is used to indicate that the -NH- groups in the compounds of the above formula, to which no acyl groups are bound, are converted to tertiary amino groups and "peralkylated" is used to indicate that the said -NH- groups are converted to quaternary ammonium groups.)  The alkylated products also have good anti-electrostatic activity.  The acylated polyalkylene polyamines, from which the alkylated derivatives are prepared, are the condensation products of polyalkylene polyamines and carboxylic acids.  Polyalkylene polyamine components specified are triethylene tetramine, tetraethylene pentamine, dipropylene triamine, tripropylene tetramine and the corresponding butylene amines. Carboxylic acid components specified are lauric acid, myristic acid, palmitic acid, stearic acid, coconut fatty acid, linoleic acid, oleic acid, tallow oil fatty acid, sperm oil fatty acid, behenic acid and arachic acid.  Mixtures of the alkylated derivatives may also be used for softening textiles.  All the softening agents exemplified are methylated derivatives.  (For the preparation of the alkylated derivatives see Division C2).