Patent GB-836647-A (GB)
Title: New phthalocyanine compounds
Inventor: CLARK PETER FREDERICK
IPC: C09B62/04
Filed: 1957-08-07
Abstract: Dichloro-thio-s-triazines are made by condensing cyanuric chloride with an equimolecular proportion of a mercaptan such as ethyl mercaptan, beta-hydroxy-ethyl mercaptan, thiophenol, thio-p-cresol, thiophenol-m-sulphonic acid, 2-thionaphthol-6-sulphonic acid, p-nitrothiophenol and p-chlorothiophenol.  Specifications 529,847, 569,200, 589,118, 717,137 and 724,212 also are referred to.ALSO:The invention comprises dyestuffs of the formula <FORM:0836647/IV(c)/1> where (Pc) is a metal-free phthalocyanine radical or a stable metal phthalocyanine radical, Y is a direct link or a divalent bridging radical and the system (Pc)-Y- contains at least one solubilizing group, R is hydrogen, alkyl, aralkyl or cycloalkyl, X is halogen, A is hydrogen or a hydrocarbon or substituted hydrocarbon radical attached directly or through a sulphur atom to the triazine nucleus and n is a whole number.  A large number of divalent bridging radicals is specified.  The dyestuffs are made (i) by interacting a compound of the formula (Pc)-(YNHR)n with a triazine of the formula <FORM:0836647/IV(c)/2> (ii) when Y is -SO2-or-CO-, by interacting a phthalocyanine sulphonic or carboxylic acid chloride of the formula (Pc)1-(Y11Cl)n, where (Pc)1 is a metal-free phthalocyanine radical or a stable metal phthalocyanine radical which contains a solubilizing group and Y11 is SO2 or CO, with a triazine of the formula <FORM:0836647/IV(c)/3> or (iii) where A is a radical attached through a sulphur atom, by condensing a compound of the formula <FORM:0836647/IV(c)/4> with one molecular proportion of a mercaptan. Examples are given. The dyestuffs dye wool, silk, superpolyamide or superpolymethane fibres, cotton, linen and viscose rayon blue to green shades, the colouring of cellulosic textile materials being conducted in conjunction with a treatment with an alkaline agent in aqueous medium.  The amino phthalocyanines mentioned above may be made by sulphonating the amines described in Specifications 529,847, 569,200, 589,118, 717,137 and 724,212, or by heating under conditions used for the manufacture of phthalocyanines appropriate derivatives of sulphonated phthalic acids and the substituted phthalic acids of Specifications 569,200 and 589,118 or mixtures of carboxy- or sulphophthalic acid derivatives with 3- or 4-nitrophthalic acid or an acylamino phthalic acid and reducing or hydrolysing the nitro- or acylaminophthalocyanine obtained.  Other amino phthalocyanines may be made by reacting nitroaniline or a monoacetyl alkylene diamine with a chlormethyl phthalocyanine sulphonic or carboxylic acid followed by reduction or hydrolysis; by reacting a chloromethyl phthalocyanine with a diaminobenzene sulphonic or carboxylic acid; by reacting a phthalocyanine containing sulphonyl chloride groups with a monoacetyl alkylene diamine or an amino-N-benzylacetamide followed by hydrolysis of the acetylamino groups; and by reacting a phthalocyanine containing carboxylic acid chloride groups with a diamino benzene sulphonic or carboxylic acid or with an aminobenzene sulphonic or carboxylic acid which also contains a nitro group followed by reduction or with an N-(aminobenzyl) acetamide followed by hydrolysis.  Specification 515,637 also is referred to.