Patent GB-533439-A (GB)
Title: Improvements in dyeing
IPC: C09B31/043
Filed: 1939-08-08
Abstract: 533,439. Dyeing textiles. OLPIN, H. C., and WRIGHT, J. Aug. 8, 1939, No. 22884. [Classes 2 (iii) and 15 (ii)] Azo dyes are formed on textile materials, especially such materials made of or containing a cellulose ester or ether, by coupling thereon a diazotized aminoazo compound with an N-substituted m-aminophenol ether in which the N-substituent, or each N-substituent if two are present, is a hydrocarbon radicle. The dyeings are readily dischargeable, e.g. with formaldehydesulphoxylates. Specified ether groups in the coupling component are methoxy, ethoxy, #-hydroxyethoxy, #-ethoxyethoxy, phenoxy and benzyloxy. The hydrocarbon radicle substituents may be alkyl, aryl, aralkyl or cycloalkyl groups or the radicle may form with the nitrogen atom a heterocyclic radicle, e.g. piperidyl. Specified coupling components are the N-dimethyl, N-diethyl-, N-cyclohexyl-, N-ethyl-N-cyclohexyl- and N- ethyl-N-benzyl-derivatives of m-anisidine and m-phenetidine and the N-diethyl-derivatives of 3 - amino - 1 - # - hydroxyethoxy benzene and 3 - amino - 1 - benzyloxy benzene. The aminoazo components may be azobenzenes, azo- α-naphthalenes or benzene - azo - a - naphthalenes, e.g. the components described in Specifications 506,740, 523,287 and 529,454. For cotton or regenerated cellulose materials, such components may be substantive aminoazo dyes. In examples, (1) a knitted cellulose acetate fabric is impregnated with an aqueous soapy dispersion of the aminoazo compound, 4 - nitroaniline # 2 : 5 - dimethoxyaniline, rinsed, treated for ¢-hour with a cold aqueous solution of sodium nitrite and hydrochloric acid, washed, entered into an aqueous turkey red oil dispersion at 30‹C. of N-diethyl-manisidine, N-diethyl-m-phenetidine or 3-diethylamino - 1 - # - hydroxyethoxybenzene, with raising of the temperature during ¢-hour to 60‹C. and so maintaining for a further ¢-hour, followed by soaping and drying to obtain a full reddish navy blue dyeing ; (2) a knitted mixed fabric of cellulose acetate and viscose artificial silks is dyed by treatment for 1 ¢ hours in an aqueous solution at 75-80‹C. containing aminoazobenzene and Chlorazol black BH with addition of Glauber salt to assist exhaustion of the direct cotton dye, rinsed, treated for ¢ hour with an aqueous solution at 10-20‹C. containing sodium nitrite and hydrochloric acid, rinsed, entered into an aqueous turkey red oil dispersion at 20‹C. of N-diethyl-manisidine, with raising of the temperature during “-hour to 60‹C. and so maintaining for ¥-hour, followed by washing and soaping to obtain a full bluish red on the cellulose acetate and a navy blue on the viscose. N-Diethyl-m-anisidine is obtained by the action of ethyl bromide on m-anisidine. N-Cyclohexyl derivatives of m-anisidine and m-phenetidine are obtained by the action of cyclohexyl chloride on m-anisidine and mphenetidine respectively. N - Ethyl- N -cyclohexyl derivatives of m-anisidine and m-phenetidine are obtained by ethylation of the N-cyclohexyl derivatives. N-ethyl- N-benzyl-m-anisidine is obtained by the action of methyl iodide on N-ethyl-N- benzyl-m-aminophenol. N-diethyl - 3 - amino - 1 - # - hydroxyethoxybenzene is obtained by the action of ethylenechlorhydrin on 3-diethylaminophenol in presence of caustic alkali. N - diethyl - 3 - amino - 1 - benzyloxybenzene is obtained by ethylation of 3-amino-1-benzyloxybenzene.