Patent GB-523287-A (GB)
Title: New dyes and textile and other materials coloured therewith
IPC: C09B31/043
Filed: 1938-12-31
Abstract: 523,287. Dyes ; dyeing cellulose derivatives. ELLIS, G. H., OLPIN, H. C., and WRIGHT, J. Dec. 31, 1938. Nos. 37980/38 and 31559/39, (both divided out of 529,454). [Classes 2 (ii), 2 (iii) and 15 (ii)] Azo dyes, suitable for the colouration of materials made of or containing cellulose esters or ethers, are obtained by coupling a diazotized aminoazo compound, including a tetrazotized diaminoazo compound, with a monoacidyl-mphenylenediamine capable of coupling in pposition to the non-acidylated amino group, and of which the non-acidylated amino group carries at least one substituent. Two such substituents may together form with the N atom a piperidyl or like heterocyclic ring. Specified aminoazo and diaminoazo compounds are those obtainable by coupling diazotized aniline, toluidines, anisidines, phenetidines, 1-naphthylamine and their halogen and/or nitro derivatives with mtoluidine, cresidine, p-xylidine, 2:5-dimethoxy- or diethoxy-aniline, 3-acetylaminoaniline, 4- acetylamino-2-aminotoluene, 4-acetylamino-2- aminoanisole, 2-amino-4-acetylamino-1-#-hydroxyethoxybenzene, 3-benzoylamino aniline or 3-acetylmethylamino-aniline, e.g. 4-nitro- 41-amino-21:51-dimethoxy (or diethoxy)-azobenzene, 4-nitrobenzene-azo-α-naphthylamine and its 2-chloro derivative, 4-nitro-2-chloro-41- amino - 2<SP>1</SP> - methyl - 5<SP>1</SP> - methoxy-azo - benzene, 4 - nitro - 4<SP>1</SP> - amino - 2<SP>1</SP> - acetylamino - 51 - methoxy-azo-benzene, 4-nitro-2-chloro-4<SP>1</SP>-amino - 2<SP>1</SP>:5<SP>1</SP> - dimethoxyazobenzene 4 - nitro - 4<SP>1</SP> - amino-azo-benzene and its 21-methyl derivative, 4 - chloro - 4<SP>1</SP> - amino - 2<SP>1</SP> - acetylamino - 51 - methoxy-azo-benzene, and its 3-nitro derivative, 4:41 - diamino - 2<SP>1</SP> - acetylamino - 5 - methoxy - azo - benzene and 4 - amino - 2 - acetylamino - 5 - methoxy - 1:1<SP>1</SP> - benzene - azo - α - naphthalene. Specified coupling components are the 3 - acetylamino - and 3 - benzoylamino - derivatives of N-dimethyl-, N-diethyl-, N-di- (#-hydroxyethyl)- and N-ethyl-N-#-hydroxyethyl-anilines and the 6-methyl- and 6-methoxy derivatives of 3-acetylamino-N-diethyl-aniline (obtained by ethylating 2-amino-4-acetylaminotoluene and 2-amino-4-acetylaminoanisole respectively). The dyes may be produced on textile materials, straws, foils or the like made of or containing a cellulose ester or ether by incorporating the aminoazo component in the material, (e.g., according to the first Provisional Specification, from solution in an organic solvent as described in Specification 479,490) diazotizing and coupling. Alternatively, filaments, straws, films and the like may be formed from solutions of the cellulose esters or ethers in which the dyes are incorporated. Examples relate to the production of the dyestuff, 4-nitro-4<SP>1</SP>-amino-2<SP>1</SP>:5<SP>1</SP>-dimethoxy-azo-benzene # 3 - acetylamino - N - diethyl - aniline (1) on a cellulose acetate fabric by impregnating with an aqueous soap and turkey red oil dispersion of the aminoazo component, diazotizing on the material and developing with an aqueous turkey red oil dispersion of the coupling component; the dyeing is readily dischargeable with zinc formaldehydesulphoxylate; (2) on a mixed cellulose acetate-viscose fabric, with simultaneous dyeing of the viscose fibres, by impregnating with an aqueous soap and turkey red oil dispersion of the aminoazo component containing Diazo indigo blue BR, Oxydiaminogen OT, Diazo brilliant orange 5G, Diazo fast red 7BL, Diazo brilliant blue BBLA, Diazo fast green GL or GFL or Chlorazol black BH, diazotizing on the material and developing with an aqueous turkey red oil dispersion of the coupling component ; (3) similarly on the cellulose acetate fibres of a similar mixed fabric, leaving the viscose fibres uncoloured ; (4) in substance by diazotizing the aminoazo component with ' nitrosylsulphuric acid, adding sulphamic acid and coupling in sodium acetate solution ; the product may be incorporated in a solution of cellulose acetate in acetone and the solution dry-spun. A table is also given showing the shades obtainable on cellulose acetate materials by diazotizing thereon various aminoazo compounds and coupling with 3-acetylamino- N-diethylaniline. 2 - Amino - 4 - acetylamino - 1 - # - hydroxyethoxybenzene is obtained by reducing the nitro group in the reaction product from 2-nitro-4- acetylaminophenol and glycol chlorhydrin. 3- Acetylmethylaminoaniline is obtained by reducing the nitro group of 3-acetyl-methylamino- 1-nitrobenzene.