Patent GB-787735-A (GB)
Title: Manufacture and use of new condensation products containing nitrogen
IPC: D06M15/595
Filed: 1953-12-10
Abstract: The invention comprises condensation products containing 2 nitrogen atoms obtainable by condensing an aliphatic or cycloaliphatic carboxylic acid containing at least 8 carbon atoms or a functional derivative thereof with an alkylene diamine containing at least one hydrogen atom bound to nitrogen and comprising an aliphatic hydrocarbon radical containing 16 to 18 carbon atoms directly bound to nitrogen; it also comprises the compounds obtained from these condensation products by further condensation with formaldehyde or by hydroxyethylation and the water-soluble or dispersible salts and quaternary ammonium compounds of the resulting products and of the condensation products.  Suitable starting materials include caprylic, lauric, palmitic, stearic, oleic, linoleic, abietic and naphthenic acids or the acid chlorides or esters thereof and ethylene and trimethylene diamines N-substituted by the cetyl, octadecyl or octadecenyl radicals or mixtures thereof.  The condensation is effected at elevated temperature, e.g. 90-180 DEG  C., and, if desired, under reduced pressure or under an inert gas; a solvent may be present.  The reaction may be conducted to yield an open chain N-acylation product or by splitting-out 2 mols. of water a heterocyclic compound may be obtained.  The condensates or the products obtained therefrom by hydroxy ethylation or condensation with formaldehyde may be converted into salts with, for example, hydrochloric acid, sulphuric acid, and C1-4 aliphatic carboxylic acids such as formic, acetic or lactic acids; they may also be quaternated by reaction with alkylating or aralkylating agents, e.g. dimethyl sulphate, ethyl bromide, p-chlorbenzyl chloride or benzyl chloride or by reaction, in the form of their salts, with an alkylene oxide.  The salts and quaternary compounds may be used as textile assistants, especially for softening textile fibres (see Group IV (c)).  In examples: (1) N-octadecyl trimethylene diamine is condensed with stearic acid by heating at 155-170 DEG  C. in a current of nitrogen yielding apparently an amido-amine which is converted into its acetate salt with glacial acetic acid; (2) octadecyl-trimethylene diamine, stearic acid, and some boric acid are refluxed in toluene until no more water is evolved yielding a tetrahydropyrimidine which may be converted into its acetate salt or quaternated with epichlorhydrin or benzyl chloride; (3) the amido-amine prepared in (1) is treated with sodium and then hydroxyethylated with ethylene oxide and the product, which is soluble in warm glacial acetic acid, is quaternated with epichlorhydrin; (4) stearic acid is condensed as in (1) with a mixture of N-alkyl trimethylene diamines in which the alkyl radicals correspond to those of soya bean oil acids, the amido amide is condensed with paraformaldehyde with elimination of water and the product is converted into its acetate salt. Specifications 437,104, 533,155, 578,694 and 578,695 also are referred to.ALSO:As textile assistants, e.g. as wetting, foaming, levelling, dispersing, or particularly, softening agents in the treatment of textiles including wool, viscose rayon, cellulose acetate and polyacrylonitrile fibres, use is made of water-soluble or dispersible salts or quaternary ammonium compounds either of nitrogenous condensation products obtainable by condensing an aliphatic or cycloaliphatic carboxylic acid having at least 8 carbon atoms, or a functional derivative thereof, with an alkylene diamine having at least one amino-hydrogen atom and a C16-18 aliphatic hydrocarbon radical directly bound to nitrogen, or of compounds obtained from these condensation products by hydroxyethylation or further condensation with formaldehyde, (see Group IV (b)).  The condensation products may be open-chain or heterocyclic compounds.  In examples: (1) wool and artificial silk yarns are given a soft slippery feel by treatment in an aqueous bath containing the acetate salt of the amido-amine obtained by condensing stearic acid with N-octadecyl trimethylene diamine; (2) regenerated cellulose staple fibres dyed with the blue-dyeing copper compound of the azo dyestuff from tetrazotized dianisidine and 2-oxynaphthalene-3 : 6-disulphonic acid is foularded in an aqueous bath comprising the salt mentioned in (1), dimethylol urea, ammonium chloride and ammonia and is then dried, heated at 130-140 DEG  C. and washed, whereby it is given a soft feel and rendered crease-resistant.  Other softening agents are obtained (a) by condensing stearic acid with a mixture of N-alkyl trimethylene diamines, the alkyl radicals of which correspond to those of soya bean oil acids, further condensing the resulting product with paraformaldehyde and treating with acetic acid to form an acetate of the condensate; (b) condensing octadecyl-trimethylene diamine with stearic acid to give a tetrahydropyrimidine, which is then converted into its acetate or is quaternated with benzyl chloride or epichlorhydrin; (c) condensing octadecyl trimethylene diamine with stearic acid, hydroxyethylating the resulting amidoamine and then quaternating with epichlorhydrin.  In addition to the acetate salts, reference is made to the salts formed from hydrochloric sulphuric, formic and lactic acids.  Specifications 437,104, 533,155, 578,694, and 578,695 also are referred to.