Patent GB-437566-A (GB)
Title: Manufacture of textile assistants
IPC: C07D295/03
Filed: 1935-02-15
Abstract: Tertiary amines containing an aliphatic or hydroaromatic radicle of at least six carbon atoms are treated with an oxidizing-agent capable of converting a tertiary amine into its oxide.  The amines treated may be of the type NRR<1>R<11>, where R is capryl, lauryl, stearyl, cetyl, octadecenyl or like radicle and R<1> and R<11> are the same or different lower alkyl groups such as methyl or ethyl; alternatively, R<1>, R<11> and the nitrogen atom may form a heterocyclic ring, such as a piperidine or pyrollidine ring.  The radicle R is not necessarily linked directly to the nitrogen atom, but may be linked through an aromatic nucleus or a group such as --OCH2CH2-- or --C(O)-NHCH2CH2--. Specified oxidizing agents are Caro's acid, hydrogen peroxide and ozone.  The reaction may be effected in the cold in water or an organic solvent such as acetone or chloroform. The products are useful as textile assistants, particularly as wetting, washing, levelling, emulsifying and softening agents, and agents for rendering direct dyeings fast to water.  Examples are given of the preparation of oxides from (1) 4-dimethylamino-1-laurophenone, prepared from dimethylaniline and lauric acid chloride in the presence of zinc chloride, (2) a ketone obtained from dimethylaniline and stearic acid chloride, (3) 1-dodecyl-4-dimethylaminobenzene, prepared by reducing the ketone used in example 1, (4) lauryldimethylamine, (5) cetyldimethylamine, (6) stearoyldiethylethylenediamine, (7) cetyldiethylamine, (8) lauryldiethylamine, (9) N-lauryl- or N-cetyl-piperidine and (10) the reaction product of chlorinated paraffin wax and dimethylamine.  In examples of the use of the products, (a) wool in the yolk is washed in a bath containing sodium carbonate and the product of example 1; (b) woollen rags soiled with mineral oil are washed in a bath containing the product of example 1; (c) cotton is dyed with Cibanone blue 3G in a bath containing sodium hydrosulphite, sodium hydroxide and the product of example 1; (d) wool is dyed with the chromium compound of the dye 5-nitro-2-aminophenol --> 2-aminonaphthalene-6-sulphonic acid in a bath containing sulphuric acid and the product of example 4; (e) wool yarn is wetted with an aqueous solution of the product of example 4.ALSO:As emulsifying agents in the textile industry, use is made of the oxides of tertiary amines containing an aliphatic or hydroaromatic radicle of at least six carbon atoms.  The amines from which the oxides are derived may be of the type NRR<1>R<11>, where R is capryl, lauryl, stearyl, cetyl, octadecenyl or like radicle and R<1> and R<11> are the same or different lower alkyl groups such as methyl or ethyl; alterantively, R<1>, R<11> and the nitrogen atom may form a heterocyclic ring, such as a piperidine or pyrollidine ring. The radicle R is not necessarily linked directly to the nitrogen atom, but may be linked through an aromatic nucleus or a group such as -OCH2CH2- or -C(O)NHCH2CH2-. Examples are given of the preparation of oxides from (1) 4-dimethylamino-1-laurophenone, (2) a ketone obtained from dimethylaniline and stearic acid chloride, (3) 1-dodecyl-4-dimethylaminobenzene, (4) lauryldimethylamine, (5) p cetyldimethylamine, (6) stearoyldiethylethylenediamine, (7) cetyldiethylamine, (8) lauryldiethylamine, (9) N-lauryl- or N-cetyl-piperidine and (10) the reaction product of chlorinated paraffin wax and dimethylamine.