Patent GB-983517-A (GB)
Title: Anthraquinone dyestuffs
Inventor: BUDZIAREK RICHARD
IPC: C09B62/024
Filed: 1962-05-15
Abstract: The invention comprises dyes which, in the form of their free acids, have the general formula <FORM:0983517/C4-C5/1> where A is a divalent aromatic bridging group containing one or two benzene rings and which is optionally substituted by one or more sulphonic acid groups, R is hydrogen or an alkyl radical of 1 to 4 carbon atoms, n is 1 or 2, R1 and R2 are each methyl and R3 and R4 are each hydrogen or methyl, or when R3 and R4 are each hydrogen R1 and R2 are joined to form a tetramethylene or pentamethylene radical, or R1 and R3 and R2 and R4 are joined together to form in each case a trimethylene radical, and X is a divalent monochloro-, dichloro- or 5-cyano-monochloropyrimidyl radical or a divalent 1 : 3 : 5-triazinyl radical substituted in 6-position by hydrogen, alkyl or alkoxy of 1 to 4 carbon atoms, phenyl, phenoxy, sulphophenoxy, amino or a substituted amino group. Divalent aromatic bridging groups specified for A are phenylene, sulpho-phenylene and divalent stilbene and azobenzene groups substituted by sulpho groups.  The dyes are made by reacting a compound of the formula <FORM:0983517/C4-C5/2> where A, X, R and n are as above, with a hydrazine of the formula <FORM:0983517/C4-C5/3> where R1, R2, R3 and R4 are as above.  The dyes dye and print textile materials of cotton, viscose rayon, regenerated cellulose, wool, cellulose acetate, polyamides, polyacrylonitrile, modified polyacrylonitrile and aromatic polyesters in blue and green shades. The Provisional Specification also relates to dyes of the above general formula wherein the 1-amino group may be substituted by a substituted or unsubstituted alkyl, cycloalkyl or aryl radical, the 2-sulpho group may be replaced by hydrogen, chlorine, bromine, methoxy, phenoxy or sulphophenoxy and the other sulpho group shown may be replaced by chlorine or bromine, radical A may be any substituted or unsubstituted divalent aromatic radical, the grouping -N(R)- may be repleaced by -0-, -S- or a sulphonamido group, the triazine or pyrimidine ring may be substituted by hydrogen, chlorine, bromine, alkyl, aryl or a substituted or unsubstituted amino, hydroxy or mercapto group and the hydrazinium grouping shown is replaced by a group of the formula <FORM:0983517/C4-C5/4> wherein X is a direct link or a <FORM:0983517/C4-C5/5> or <FORM:0983517/C4-C5/6> group where Y is O, S or NR7, and W is a divalent bridging group such as a substituted or unsubstituted alkylene or arylene group, a diacyl group or an alkylenecarbonyl or arylenecarbonyl group, R1 and R2 are each substituted or unsubstituted hydrocarbon radicals, R3 and R4 are each hydrogen substituted, or unsubstituted hydrocarbon radicals or acyl, sulphonic acid or dithiocarboxylic acid groups, or R3 and R4 together form a substituted or unsubstituted alkylidene or arylidene group, or at least two of R1, R2, R3 and R4 together form one or more 5- or 6-membered heterocyclic rings, and R5, R6 and R7 are each hydrogen or substituted or unsubstituted hydrocarbon radicals. Lists of suitable starting materials are given.  Specifications 772,030, 781,930, 803,473, 822,047, 832,400, 838,335, and 874,508 are referred to.