Patent GB-912127-A (GB)
Title: Azo phthalocyanine dyestuffs
IPC: C09B62/443
Filed: 1960-03-21
Abstract: The invention comprises dyes of the formula:-<FORM:0912127/IV (b)/1> where Pc is a phthalocyanine radical, R6 and R16 are -SO2- and/or -CO- groups, R7 is an amino group-containing radical of a coupling component of the benzen, naphthalene, pyrazolone or acylacetic acid amide series having the azo linkage attached in a coupling position and which is linked to R6 via the amino group, R8 is the residue of a diazo compound, R is a group -CH2-CH2OSO3H, -CH2-CH2OSO3X, -NH-R1-OSO3H, -NH-R1-OSO3X, -NH-R2-halogen or - <FORM:0912127/IV (b)/2> -R3-R4-R5-W, X being an alkali metal cation, R1 and R2 are straight or branched chain bridge members of 2 to 3 carbon atoms between -N-and -O- or halogen and may be acyl groups such as acetyl or propionyl groups, halogen is chlorine or bromine, R3 is alkylene or cycloalkylene, R5 is alkylene of 2 to 3 carbon atoms between R4 and W, R4 is -O-, -S- or <FORM:0912127/IV (b)/3> , Y and Z are hydrogen atoms or araliphatic, cycloaliphatic or aliphatic substituents which may be joined to form with the nitrogen atoms a heterocyclic ring, W is a substituent capable of being split off as a negative ion in the presence of an acid-binding agent, such as sulphate or phosphate acid ester groups, sulphonyloxy groups and chlorine and bromine atoms, g is 0 or 1, n is a number from 1 to 8, and m is a whole number, and wherein the grouping (R16-R) may also be a chloropyrimidyl radical linked by an oxygen atom or by an amino or amido group.  The dyes may be made by coupling an amide of the formula Pc-(R6-R7) with a diazo component containing at least one (R16-R) group with a diazo component having sulphonic or carboxylic acid groups, converting to the acid halide and condensing with an alkanolamine sulphuric acid ester or with an alkanolamine followed by esterification, or with a diazo component not containing sulphonic acid groups followed by sulphonation and conversion to acid halide or by chlorosulphonation and condensation with an alkanolamine sulphuric acid ester or with an alkanolamine followed esterification, or with a diazo component containing a sulphonyl- or carbonyl-alkanolamide group followed by esterification.  The dyes are also made by condensing a phthalocyanine sulphochloride with an amino-azo dye containing a sulphon-alkanolamide sulphuric acid ester group.  When the group (R16-R) is a pyrimidyl radical, a diazo compound containing amino or amido groups may be condensed with a di- or tri-halopyrimidine and coupled with the phthalocyanine amide or the coupling may be effected before the condensation.  Alternatively a phthalocyanine acid chloride may be condensed with an amino-azo-compound and when the latter contains no pyrimidyl group, one is introduced.  Examples are given.  The dyes dye and print fibrous materials containing amide groups such as wool, silk and synthetic polyamides and polyurethanes and, in conjunction with an alkali and heat treatment, fibrous materials containing hydroxyl groups such as cellulose.  Specification 830,920 is referred to. Reference has been directed by the Comptroller to Specifications 822,047, 830,920, 837,750 and 852,960.