Patent GB-703500-A (GB)
Title: Derivatives of dialkylene triamines and the process of preparing the same
IPC: D06P1/645
Filed: 1951-05-28
Abstract: The invention comprises N, N11-dibenzyl-N, N1, N11-trialkyl-dialkylene triamines of the formula <FORM:0703500/IV(b)/1> wherein Ar represents a phenyl or substituted phenyl radical, R represents alkyl of not more than six carbon atoms, and R1 represents alkylene, which are stated to be gas fading inhibitors for dyeings on cellulose derivatives.  They may be prepared by reacting an alkylamine with an alkylene dihalide at 70-90 DEG  C., cooling and distilling off unreacted amine, heating with caustic alkali at 70-90 DEG  C., distilling the remainder of the unreacted amine, cooling and adding benzene to form a slurry, filtering off the alkali salt, then either benzylating the crude reaction mixture or the amines separated therefrom by alternate addition of a benzyl halide and sodium hydroxide under controlled conditions, distilling off the benzene and treating the benzylated mixture with water to separate it into an oily layer and an aqueous layer, and fractionally distilling the oily layer, to recover the said N.  N11-dibenzyl triamines.  In examples, (1) methylamine and ethylene chloride are reacted as above, and the crude reaction product or the separated N. N1. N11-trimethyl diethylene triamine is benzylated with benzyl chloride; (2) methylamine and 1.2-dichloropropane or ethylamine and trimethylene chloride are similarly reacted with separation of the reaction product before benzylation; (3) ethylamine and ethylene dichloride are reacted, with benzylation of the total reaction product; (4) N. N1. N11-tripropyl diethylene triamine (prepared according to U.S.A.  Specification 2,279,294 from N.N1-di (n-propyl) ethylene diamine, isopropylamine, and ethylene dibromide) is benzylated as above.  In further examples, cellulose acetate fabric is dyed in a bath containing (5) 1-methylamino - 4 - ethylamino - anthraquinone, N.N11 - dibenzyl - N. N1. N11 - trimethyl - diethylene triamine, and the condensation product of ethylene oxide and diisobutyl phenol; (6) 1 - hydroxyethylamino - 4 - ethylamino - anthraquinone, the condensation product of (5), and N. N11 - dibenzyl - N. N1. N11 - trimethyl-dipropylene triamine.  Also, cellulose acetate fabric previously dyed with p  1.4-dimonomethylamino-anthraquinone is treated with a bath containing the condensation product of (5) and that from oleic acid chloride and N-methyltaurine, together with the benzylated crude reaction product of (1) above, or N. N11 - dibenzyl - N. N1. N11 - trimethyl - di (trimethylene) triamine, or N. N11-dibenzyl-N. N1. N11 - trimethyl - dipropylene triamine.  Other cellulose derivatives specified are the formate, propionate, butyrate, acetate-propionate, acetate-butyrate, or the methyl, ethyl, or benzyl ethers.  The substituents which may be present in radical Ar may be alkyl, halogen, chloro, bromo, dichloro, dibromo, alkoxy, carbalkoxy, aryloxy, cyano.  The products may also be used as fungicides, bactericides, anti-oxidants, or for the preparation of spirit-soluble azo dyestuffs.ALSO:The invention comprises N, N"-dibenzyl-N, N\sv, N"-trialkyl-dialkylene triamines of the formula: <FORM:0703500/IV(c)/1> wherein Ar represents a phenyl or substituted phenyl radical, R represents alkyl of not more than six carbon atoms, and R1 represents alkylene, (see Group IV(b)), which are stated to be gas fading inhibitors for dyeings on cellulose derivatives.  In examples, cellulose acetate fabric is dyed in a bath containing (5) 1-methylamino-4-ethylaminoanthraquinone, N, N"-dibenzyl-N, N\sv, N"-trimethyl-diethylene triamine, and the condensation product of ethylene oxide and diisobutyl phenol; (6) 1-hydroxyethylamino-4-ethylamino-anthraquinone, the condensation product of (5), and N, N"-dibenzyl-N, N\sv, N"-trimethyl-dipropylene triamine.  Also, cellulose acetate fabric previously dyed with 1.4-di-monomethylamino-anthraquinone is treated with a bath containing the condensation product of (5) and that from oleic acid chloride and N-methyltaurine, together with the benzylated crude reaction product of methylamine and ethylene chloride, or N, N"-dibenzyl-N, N\sv N"-trimethyl-di (trimethylene) triamine, or N, N"-dibenzyl-N, N\sv, N"-trimethyldipropylene triamine.  Other cellulose derivatives specified are the formate, propionate, butyrate, acetatepropionate, acetate-butyrate, or the methyl, ethyl, or benzyl ethers.  The substituents which may be present in radical Ar may be alkyl, halogen (chloro, bromo, dichloro, dibromo), alkoxy, carbalkoxy, aryloxy, cyano.