Patent GB-1072713-A (GB)
Title: Water-insoluble anthraquinone dyestuffs containing a reactive group
Inventor: BLACKHALL JOHN ANDERSON
IPC: C09B62/80
Filed: 1965-01-26
Abstract: The invention comprises water-insoluble anthraquinone dyestuffs and mixtures thereof of the formula <FORM:1072713/C4-C5/1> wherein one of R1 and R2 represents a g -chloro-b -hydroxypropyl, a g -bromo-b -hydroxypropyl or a b :g -epoxypropyl radical and the other of R1 and R2 represents a H, g -chloro-b -hydroxypropyl, a g -bromo-b -hydroxypropyl or a b :g -epoxypropyl radical or C1-C5 alkyl, a hydroxy-(C1-C5 alkyl or a hydroxy(C1-C5)alkoxy-(C1-C5)alkyl radical; and the anthraquinone nucleus and the benzene ring may be further substituted by Cl, Br or C1-C5 alkyl radicals. Compounds wherein R1 represents a g -chloro-b -hydroxypropyl or g -bromo-b -hydroxypropyl radical may be prepared by treating with epichlorohydrin or with epibromohydrin in a non-basic organic solvent an anthraquinone compound or the formula <FORM:1072713/C4-C5/2> wherein R1 represents a hydrogen atom or a g -chloro-b -hydroxypropyl, g -bromo-b -hydroxypropyl, b :g -epoxypropyl, C1-C5 alkyl, hydroxy(C1-C5)alkyl or a hydroxy(C1-C5)alkoxy-(C1-C5)alkyl radical, and the anthraquinone nucleus and the benzene ring may be further substituted as above. Compounds wherein R2 represents a g  - chloro - b  - hydroxypropyl g - bromo - b  - hydroxypropyl or b :g  - epoxypropyl radical may be obtained by treating with epichlorohydrin or epibromohydrin in alkaline medium an anthraquinone compound of the formula <FORM:1072713/C4-C5/3> whereby a dye in which R2 represents a b :g -epoxypropyl radical is obtained which may be converted into a dye in which R2 represents g -chloro- or -bromo-b -hydroxypropyl radical by treatment with HCl or HBr.  Also, compounds in which R1 represents hydrogen and R2 represents a g -chloro- or -bromo-b -hydroxypropyl or b :g -epoxypropyl radical may be obtained by desulphonating an anthraquinone sulphonic acid of the formula <FORM:1072713/C4-C5/4> wherein R5 represents a g -chloro- or bromo-b -hydroxypropyl or b :g -epoxypropyl radical, and the anthraquinone nucleus and benzene radical may be substituted as above.  Examples are given for the preparation of the dyes.  They may be used for colouring wool and synthetic fibres.  Anthraquinone sulphonic acids of Formula III may be obtained by reacting 1-amino-4-bromoanthraquinone-2-sulphonic acid with an amine of the formula <FORM:1072713/C4-C5/5>ALSO:Textile materials are coloured with water insoluble anthraquinone dyes of the formula:  <FORM:1072713/D1-D2/1> wherein one of R1 and R2 represents a g -chloro -or-bromo-b -hydroxypropyl or a b :g - epoxy-propyl radical, and the other represents hydrogen, g -chloro-or-bromo-b -hydroxypropyl, b : g -epoxypropyl, C1-C5 alkyl, hydroxy C1-C5 alkyl or hydroxy (C1-C5) alkoxy (C1-C5) alkyl radical, and the anthraquinone nucleus and the benzene ring may be further substituted by Cl or Br atoms or C1-C5 alkyl. Specified fibres are wool, polyesters, cellulose esters, polymers and copolymers of acrylonitrile, polyolefins and polyamides.  An example is given where a woven synthetic polyamide textile is dyed in the presence of an aqueous solution of NaHCO3 and a condensate of ethylene oxide and cetyl alcohol.