Patent GB-593567-A (GB)
Title: Azo dyes
IPC: C09B29/08
Filed: 1941-05-12
Abstract: Azo dyes are obtained by coupling a diazotized arylamine with an amine of the general formula <FORM:0593567/IV/1> wherein B represents an aryl radicle, R represents an unsubstituted alkyl radicle, R1 represents a polyalkylene glycol radicle of the general formula -(CH2)x-(O-CH2-CH2)y-, wherein x and y each represent 1, 2, 3 or 4, and X represents H, alkyl, aralkyl, hydroxyalkyl, alkoxyalkyl or polyalkoxyalkyl, i.e. a group of the general formula -(CH2)x-(O-CH2-CH2)y-OR. Specified diazo components are aniline, 2 : 5-dichloroaniline, 3- or 4-nitroaniline, 2-chloro-4-nitroaniline, 4- or 5-nitro-2-aminotoluene, 5-nitro-2-anisidine, 4-aminoacetanilide, 6 - chloro- or bromo - 2 : 4 - dinitroaniline, 2 : 6 - dichloro - 4 - nitroaniline, 2 - naphthylamine, sul - phanilic acid anthranilic acid, and 1 : 4-diamino-benzene --> the anilide of 2 : 3-hydroxynaphthoic acid (in substance or on the fibre). Specified coupling components are N-b -methoxyethoxyethyl-aniline and its N-methyl, N-ethyl, N-benzyl, N-b -hydroxyethyl, and N-b -methoxyethyl derivatives, N - b  - ethoxyethoxyethyl - aniline and its N-methyl and N-ethyl p  derivatives, N : N-di-(b -methoxyethoxyethyl)-aniline, N - b  - methoxyethoxyethoxyethyl - N - ethyl - aniline, N-b -methoxyethoxyethoxyethoxyethyl-N-ethyl aniline, 3-chloro- or 3-methyl-N-b -methoxyethoxyethyl - aniline, N - b  - methoxy - ethoxyethyl - cresidine, N - b  - n - butoxyethoxy - ethyl-aniline and its N-methyl derivative, 3 - methyl - N - b  - ethoxyethoxyethyl - N - ethyl - aniline and N - b  - methoxyethoxyethyl - N - ethyl - 1-naphthylamine.  The products free from water-solubilizing groups are applicable for colouring fibres of cellulose esters or of vinyl halide-vinyl acetate copolymers.  The water-soluble products are suitable for dyeing animal fibres, e.g. wool or silk.  Examples relate to the production of the dyestuffs: (1), (2) and (3), 4 - nitroaniline --> (1) N - b  - methoxyethoxy - ethyl - N - ethyl - aniline, (2) N - b  - ethoxyethoxy - ethyl - N - methyl - aniline, (3) N : N - di - (b  - methoxyethoxyethyl)-aniline; (4) 2 - chloro - 4 - nitroaniline --> N - b  - ethoxyethoxyethyl - N - ethyl - aniline; (5) 6 - bromo - 2 : 4 - dinitroaniline --> N - b  - methoxyethoxyethyl - N - ethyl - 1 - naphthylamine; (6) 4 - aminoacetanilide --> N - methoxyethoxyethyl - N - ethyl - aniline; (7) the anilide of 2 : 3-hydroxynaphthoic acid (on cotton fibre) \sM 1 : 4-diaminobenzene --> N - b  - methoxyethoxyethyl - N - ethyl - aniline; (8) sulphanilic acid --> N - b  - methoxyethoxyethyl - N - ethyl - aniline; (9) 2 : 6 - dichloro - 4- nitro - aniline --> b  - methoxyethoxyethyl - N - ethyl - aniline; (10), (11) and (12) 4-nitroaniline --> (10) N - b  - methoxyethoxyethyl - N - b  - methoxy - ethyl-aniline; (11) N - b  - methoxyethoxyethoxy - ethyl - N - ethyl - aniline; (12) N - b  - methoxy - ethoxyethoxyethoxyethyl - N -ethyl - aniline.  A table is also given showing the shades obtainable with various combinations of diazo and coupling components.  Amines of the above general formula are obtainable by (A) condensation of a compound of the general formula Aryl-SO2-O-(CH2)x-(O-CH2-CH2) yOR with a primary amine of the benzene or naphthalene series in presence of an agent binding acid and, if necessary, introducing the desired group X, e.g. by treatment with dimethyl sulphate, benzyl chloride or ethylene chlorohydrin; (B) condensation of an arylsulphonic acid ester as in (A) with a secondary amine of the general formula Ar-NHX of the benzene or anphthalene series; (C) condensation of a compound Hal-(CH2)x-(O-CH2-CH2)y-OR, wherein Hal represents Cl or Br, with an appropriate primary or secondary amine of the benzene or naphthalene series.  The Specification as open to inspection under Sect. 91 comprises also the use as coupling components of N-b -ethoxyethoxypropylaniline, N-b  - ethoxyethoxybutylaniline, N - b  - methoxy - ethoxyethyl - N - b  - butoxyethoxyethyl - aniline, N - b - ethoxyethoxyethyl - N - b  - methoxyethylaniline, N - b  - methoxyethoxyethoxyethyl - N - ethyl - aniline and N - b  - ethoxyethoxyethoxyethoxyethyl - N - ethyl - aniline.  This subject-matter does not appear in the Specification as accepted.