Patent GB-532439-A (GB)
Title: Manufacture of acylated ammonium-diarylmethane compounds
IPC: F16F1/12
Filed: 1939-08-31
Abstract: 532,439. Textile assistants. GEIGY AKT.- GES., J. R. Aug. 31, 1939, No. 24990. Convention date, Sept. 1, 1938. Samples furnished. [Classes 2 (iii) and 15 (ii)] Acylated aminoniumdiarylmetbanes are prepared by re-acting a diarylmethane containing at least one primary, secondary or tertiary amino group and at least one other amino nitrogen or oxygen atom having reactive hydrogen united thereto with a higher aliphatic, cycloaliphatic or hydroaromatic carboxylic acid in such quantity that at least one amino group remains unacylated, and converting at least one amino group of the product into a quaternary ammonium group by treating with an alkylating or aralkylating agent. The higher carboxylic acids should contain at least 12 carbon atoms and may be replaced by derivatives thereof capable of acylation. The products are capillary active and are auxilary agents for the textile industry. In examples (1) 4-amino-41-dimethylaminodiphenylmethane is acylated with stearic acid chloride and then treated with dimethylsulphate : (2) 2:4-diamino-3<SP>1</SP>-methyl-4<SP>1</SP>-dimethylamino-diphenylmethane is acylated with the chlorides of coconut fatty acids and treated with diethylsulphate: (3) 4-dimethylamino-4<SP>1</SP>-(N- methyl - N - hydroxyethyl) - aminodiphenylmethane is acylated with oleic acid chloride and the resulting ester treated with dimethylsulphate ; a bis quaternary salt may be obtained by using increased quantity of alkylating agent: (4) 3 - chlor - 4 - dimethylamino-3<SP>1</SP>-(1V- methyl - N - hydroxyethyl) - amino - 4<SP>1</SP> - amino - diphenylmethane is acylated with lauric acid chloride and treated with diethylsulphate. Products containing one or more ammonium and/or acyl groups are specified derived from the following amino diarylmethanes : N- methyl-N-hydroxyethylaminodiphenylmethane, 4 - (N - methyl - N -hydroxy - ethyl) dimethylamino hydroxydiphenylmethane, aminodiphenylmethane, 4 - (N - aminoethyl) amino- 41 - dimethylaminodiphenylmethane, 4 - hydroxy - 4<SP>1</SP> - dimethylaminodiphenylmethane, 2:4 - dimethylamino - 4<SP>1</SP> - dimethylaminodiphenylmethane, 4:4<SP>1</SP> - diaminoditolylmethane, 4 - dimethylamino - 3<SP>1</SP> - ethyl - 2<SP>1</SP> - aminodiphenylmethane, 4 - dimethylamino - 3<SP>1</SP>- methoxy (or ethoxy) - 4<SP>1</SP> - aminodiphenylmethane, 4 - ethylbenzylamino - 4<SP>1</SP> - aminodiphenylmethane, 4 - diethylamino - 4<SP>1</SP> - aminodiphenylmethane, 4<SP>1</SP> - diethylamino - 2<SP>1</SP> - (or 3<SP>1</SP>-) carboxy - 4<SP>1</SP> - aminodiphenylmethane, 4 - dimethylamino - 3<SP>1</SP> - methyl - 1<SP>1</SP> - ethylaminodiphenylmethane, 4 - diethylamino - 4<SP>1</SP>- (N - methyl - N - dihydroxypropyl) - aminodiphenylmethane, 4 - dimethylamino - 4<SP>1</SP> - N- methyl - N - hydroxylethylaminodiphenylmethane and 4<SP>1</SP> - diethylamino - 2 - (N - methyl- N - hydroxyethyl) amino - 4 - aminodiphenylmethane. The use of diarylmethanes containing a tertiary nitrogen atom which belongs to a heterocyclic nucleus, e.g. a morpholine, piperazine or imidazol ring, and of resin, abietic and naphthenic acids for the acylation is mentioned. Starting materials containing alkylradicles having up to 18 carbon atoms attached to a tertiary nitrogen atom may also be used. Samples have been furnished under Sect. 2 (5) of products prepared by treating first withstearic acid chloride and then with dimethylsulphate (1) 2-hydroxy-5-amyl-4-dimethylaminodiphenylmethane, (2) 3-methyl-4-amino- 4<SP>1</SP> - morpholinyldiphenylmethane and (3) 3- amino - 4:4<SP>1</SP> - bis - dimethylaminodiphenyl methane (prepared from the corresponding nitro or nitroso compound by reduction).