Patent GB-870948-A (GB)
Title: New anthraquinone dyestuffs
Inventor: EATON DAVID CRAWFORD
IPC: C09B62/445
Filed: 1958-10-29
Abstract: The invention comprises water-insoluble dyestuffs of the formula:- <FORM:0870948/IV(c)/1> where A is a substituted or unsubstituted anthraquinone nucleus, B is hydrogen or hydroxy, X is a direct link or an alkylamino or arylamino residue connected to the anthraquinone nucleus through the nitrogen atom, Y is a bridging atom or group such as -SO2-, -SO2NH-, -SO2NR1-, -S-, -O-, -O Alkylene O-, -NH-, -NR1-, -NH Alkylene O-, -CONH-, -COO- or -COO Alkylene O-where R1 is a substituted or unsubstituted alkyl radical, R is an alkyl, phenyl, tolyl or chlorophenyl radical, m is 1 or 2, n is 0, 1 or 2 provided that n is not 0 when B is hydroxy and provided that A, X, Y and R are free from sulphonic acid and carboxylic acid groups. The dyestuffs are made by treating an anthraquinone of the general formula:- <FORM:0870948/IV(c)/2> with an acid halide of the formula R,SO2-halogen.  The dyestuffs dye and print polyamide and modified polyacrylonitrile fibres from aqueous dispersion.  The Provisional Specification also refers to dyestuffs of the above general formula where R is a substituted or unsubstituted hydrocarbon radical and where n may be any whole number.  Anthraquinone compounds of the general formula:-  <FORM:0870948/IV(c)/3> where A, X, Y, B, n and m are as above are made by the following methods:-(i) where X is alkylamino or arylamino by reacting A-(Br)m with <FORM:0870948/IV(c)/4> or by reacting A-(NH2)m with <FORM:0870948/IV(c)/5> where X1 is alkyl or aryl; (ii) where X is a direct link and Y is -SO2NH- or -SO2NR1- by reacting A-(SO2Cl)m with <FORM:0870948/IV(c)/6> or <FORM:0870948/IV(c)/7> where R1 is as above; (iii) where X is a direct link and Y is -O- or -O Alkylene-O- by reacting A(-OPh)m with <FORM:0870948/IV(c)/8> or <FORM:0870948/IV(c)/9> where pH is phenyl; (iv) where X is a direct link and Y is -COO- or -COO Alkylene-O- by reacting A-(CO Cl)m with <FORM:0870948/IV(c)/100> or <FORM:0870948/IV(c)/111> or by reacting A-(COOH)m with <FORM:0870948/IV(c)/122> or <FORM:0870948/IV(c)/133> (v) where x is a direct link and Y is -CONH-by reacting A-(CO Cl)m with <FORM:0870948/IV(c)/144> (vi) where X is a direct link and Y is -S- by reacting A-(SH)m with <FORM:0870948/IV(c)/155> (vii) where X is a direct link and Y is -SO2- by acetylating the corresponding compound where Y is -S-, treating with an oxidizing agent and hydrolysing off the acetyl group; and (viii) where X is a direct link and Y is a -NH- or -NH Alkylene -O- group by reacting A-(Br)m with <FORM:0870948/IV(c)/166> or <FORM:0870948/IV(c)/177> respectively. 1-Methylamino- 4-[21- b -hydroxyethylsulphamyl)-p-toluidino] anthraquinone and 1-amino- 2-[41-(sulphon-N-(b -hydroxyethyl) amido) phenoxy]- 4-[411-(sulphon-N-(b -hydroxyethyl) amido)-anilino anthroquinone are made by sulpho chlorinating 1-methylamino- 4-p-toluidino-anthraquinone and 1-amino- 2-phenoxy- 4-anilinoanthraquinone respectively and reacting the resulting sulphochlorides with ethanolamine.  1-Methylamino- 4-[b - (di-(b 1-hydroxyethyl) -amino)-ethyl]-amino-anthroquinone is made by reacting 1-methylamino- 4- b -chloroethylaminoanthraquinone with diethanolamine.  1 : 5- Di(g -hydroxypropylamino) anthraquinone is made by condensing g -hydroxypropylamine with 1 : 5-dichloroanthraquinone. Specifications 518,725, 639,266, 797,383 and 835,819 are referred to.