Patent GB-926975-A (GB)
Title: Process for dyeing and padding hydrophobic materials
IPC: D06P1/32
Filed: 1961-06-23
Abstract: Materials of aromatic polyesters, polyamides, polyurethanes, polyacrylonitrile and its copolymerisates, cellulose esters and polyolefins are dyed mainly dark shades, particularly black, by treating consecutively (in either sequence) with aromatic compounds containing primary and/or secondary amino groups or their salts and with (a) quinones or (b) N-haloquinone-imines or N,N1-dihaloquinone-diimines of optionally substituted quinones or (c) with compounds containing the grouping <FORM:0926975/IV(a)/1> in a non-aromatic carbocyclic ring, where X and Y denote carbon-carbon bonds or hydrogen or halogen atoms; alternatively with (d) compounds convertible into quinoid compounds by action of oxidizing agents and (e) organic or inorganic oxidizing agents, or mixtures of (a) and/or (b) and/or (c) and/or (d) and (e).  The amino group containing compounds specified are: 4-amino-diphenylamine, 4-amino-41-methoxy-diphenylamine, 1,8-diamino-naphthalene, benzidine, 4-amino-naphthalene-1,11-azo-41-aminobenzene, 3-methoxy-4-aminodiphenylamine, 4-amino-41-cyclohexyl-diphenylamine, 4-amino-41-methyl-diphenylamine, 4-amino-41-naphthyl-diphenylamine, 2,4-diamino-diphenylamine, diamisidine, m-phenylenediamine, 4-amino-2-chloro-41-(N-dihydroxyethyl)-amino-1,11 -azobenzene, 4-benzoylamido-2,5-dimethoxy-1-aminobenzene, N,N1-bis-(4-aminophenyl)-4,41-diaminodiphenylamine, N,N1-bis-(4-aminophenyl)-4,41-diaminodiphenylether, N,N1-bis-(4-aminophenyl)-4,41-diamino-diphenylmethane, 4,41-diaminostilbene, N,N1-bis-(4-aminophenyl)-4,41-diaminostilbene, N,N1-bis-(4-aminophenyl)-4,41-diamino-3, 31-dimethoxy-diphenyl, 1-phenylamino-4-amino-naphthalene, 4,41-diamino-azobenzene, 4-(41-amino-phenylamino)-benzophenone and 1-(41-amino-phenylamino)-2-methoxy benzene.  Specified (a) are: benzoquinone-(1,4), naphthoquinone-(1,4), 2,5-dichlorobenzoquinone-(1,4), 2,3,5,6-tetrachlorobenzoquinone-(1,4), 2,6-dichlorobenzoquinone-(1,4), 2,3,6-trichlorobenzoquinone-(1,4), the corresponding bromine derivatives, 1,2-benzo- or naphthoquinone or their derivatives, 2-phenyl-1,4- or 1,2-benzoquinone, diphenylquinone and their substitution products.  Specified (b) are: N,N1-dichloro-p-benzoquinone-imine, 2,6-dichloro-4-monochloriminobenzoquinone, 2,5- and 2,6-dichloro-N,N1-dichloro-p-benzoquinone-diimine, 2-chloro-N,N1-dichloro-p-benzoquinone-diimine, 2,5-dichloro-N-chloro-N1-acetyl-p-benzoquinone-diimine, N-chloro-N1-acetyl-p-benzoquinone-diimine, N-methyl-N1-chloro-p-benzoquinone-diimine, 2-methyl-4-monochlorimino-p-benzoquinone, N,N1-dichloro-diphenylquinone-diimine and naphthoquinone-1,4-dichloro-diimine.  Specified (c) are: cyclohexanone, cyclohexane-dienone, heptachlorocyclohexenone, pentachlorotetralone and hexachlorocyclohexadienone.  Specified (d) are: p-benzohydroquinone, p-phenylenediamine, 1,4-naphthylene-diamine, 1,4-dihydroxynaphthalene, monochlorohydroquinone, 2,6- and 2,5-dichloro-hydroquinone, p-aminophenyl, monochlorophenylene-1,4-diamine, 2- and 3-chloro-4-amino-phenol, 2,6-dichloro-4-aminophenol, 2,5-dichloro-p-phenylene-diamine, 2-nitro-4-aminophenol, 4-amino-phenol sulphate, o-phenylenediamine, phenylenediamine, o-amino-phenol, pyrocatechol and 1-amino-2-hydroxy-3-chlorobenzene and specified (e) are: benzoyl peroxide, acetyl peroxide, alkali metal bichromates, permanganates and persulphates and sodium chlorite with or without an acid or alkali.  The components may be applied as an aqueous solution or dispersion at temperatures of up to 140 DEG C. in the presence of normal carriers, emulsifying and dispersing agents.  The amino group containing compound may be stabilized with a reducing agent and if it is in the form of a salt, the free base is liberated by the addition of an alkali.  Between the two application stages described above may be interposed drying, thermofixing and soaping steps.  An after-treatment with alkaline reducing agents or acidic oxidizing agents may also be included. Many examples of dyeing are given.  Specifications 414,932, 645,594 and 870,045 are referred to.