Patent GB-923148-A (GB)
Title: New anthraquinone dyestuffs
Inventor: LODGE FRANK
IPC: C09B62/004
Filed: 1960-03-24
Abstract: The invention comprises dyes of the formula <FORM:0923148/IV(a)/1> where the ring A may contain a sulphonic acid group or up to two halogen atoms, the ring B may be substituted by halogen, alkoxy, alkyl, sulphonic acid or carboxylic acid, n and m are each 0 or 1, Y is -SO2-,-CO- or -NR2CO-where R2 is hydrogen or alkyl the carbonyl being attached to the alkylene radical, R and R1 are each hydrogen, alkyl, hydroxyalkyl, sulphatoalkyl, sulphoalkyl, cycloalkyl, aralkyl, sulphonated aralkyl, aryl or substituted aryl, X is a divalent aliphatic radical or for an aromatic radical if neither R nor R1 is aromatic, and Z is an aryl radical which contain a group capable of reaction with cellulose fibre to form a covalent bond. Specified acyl radicals are those of acrylic, a -chloracrylic, propiolic, maleic, mono- and dichloromaleic, chloroacetic, sulphochloroacetic, b -chloro- and b -bromopropionic and a :b -dichloropropionic acids and radicals derived by reaction of one of the halogen atoms of 2:4:6-tribromo- and trichloro-pyrimidine, 2:4:5:6-tetrachloropyrimidine 5-methyl-, 5-nitro- and 5-cyano-2:4:6-trichloropyrimidine, 5-carboxy-, 5-carboethoxy-, 5-nitro-6-methyl- and 5-nitro-2:4-dichloropyrimidine, cyanuric bromide, cyanuric chloride and primary condensation products of cyanuric chloride or bromide with ammonia, methanol, ethanol, isopropanol, phenol, o-, m- and p-chlorophenol, o-, m- and p-cresol, o-, m- and p-sulphophenol, thiophenol, thioglycollic acid, diethyldithiocarbamic acid, mercaptobenzthiazole, methyl-, dimethyl-, ethyl-, diethyl-, n-propyl-, isopropyl-, butyl-, hexyl- and cyclohexyl-amine, toluidine, piperidine, morpholine, methoxyethylamine, ethanolamine, aminoacetic acid, aniline-2:5-disulphonic acid, orthanilic, metanilic and sulphanilic acid, 2-, 3- and 4-aminobenzoic acid, 5-amino-2-hydroxybenzoic acid, 2-aminoethane-sulphonic acid, aminonaphthalene mono- and di-sulphonic acid and N-methylaminoethane sulphonic acid.  The dyes are made by acylating compounds of the above formula where Z is hydrogen and A, B, X, Y, R, R1, m and n are as above with an anhydride or acid halide of an acid containing a group capable of reacting with cellulose fibres.  The compounds where Z is hydrogen are made by reacting compounds of the formulae <FORM:0923148/IV(a)/2> or <FORM:0923148/IV(a)/3> where A, B, Y and n are as above, Q is halogen, an esterified hydroxyl group or -S-Z where Z is a heterocycle or a negatively substituted phenyl group and Q1 is an alkenyl group having the unsaturated link in a :b -position to Y, with a compound of the formula <FORM:0923148/IV(a)/4> and if desired sulphating or sulphonating the products, or by condensing a compound of the formula <FORM:0923148/IV(a)/5> where P is chlorine or bromine, with an amine of the formula <FORM:0923148/IV(a)/6> Examples are given.  The dyes dye and print cotton, viscose rayon, regenerated cellulose, wool, silk, cellulose acetate, polyamides, polyacrylonitrile and aromatic polyester fibres and dye and print cellulose fibres in conjunction with an acid-binding agent. Specifications 822,047, 848,742, 867,571, 885,059, 885,547, 885,814, 885,815, 887,723, 891,601 and 917,780 are referred to.