Verfahren zur Herstellung von wasserloeslichen Azophthalocyaninfarbstoffen

摘要

The invention comprises compounds of the formula where Pc is a metal-free or metal-containing phthalocyanine nucleus which may contain further substituents, B is a direct link or a bivalent organic radical, R1 and R2 are H or an optionally substituted alkyl or aryl radical or form a ring with the N atom, R3 is H or an alkyl group which together with the N atom and the organic radical B may form a ring, a, b and c are 1-4 and the sum of a, b and c is at most 6 with the proviso that when c is 1 the molecule must contain groups imparting solubility in water, nucleus A may be substituted and X is the radical of a coupling component of the pyrazolone or b -ketocarboxylic acid arylamide which contains at least one group of the formula where R4 is H or an optionally substituted alkyl radical, m is 1 or 2 and Z is the radical of a monoor polybasic inorganic or organic acid or a derivative thereof capable of being split off as an anion or which contains at least one group of the formula The compounds are prepared by diazotizing a compound of the formula and coupling with a suitable coupling component which contains one of the above groups or a group of the formula to give a compound which may then be transformed to a dyestuff containing one of the other groups. Alternatively the compounds are prepared by condensing a phthalocyanine sulphonyl chloride with a compound of the formula where W is the radical of a coupling component of the pyrazolone or b -ketocarboxylic acid arylamide series which contains at least one of the above-mentioned groups, if desired in the presence of a compound of the formula R1-NH-R2, and, if desired, with simultaneous or subsequent saponification, and isolating the required dyestuff.ALSO:Cyanuric chloride is reacted with 1,3-diamino benzene-4-sulphonic acid, ethylene diamine and 1-amino benzene-3-sulphonic acid to yield a compound of the formula Cyanuric chloride is reacted with 1,3-diamino benzene-4-sulphonic acid and ethylene diamine to yield a compound of the formula The compound of the formula is prepared by treating N-acetyl-b -phenylethylamine with chlorosulphonic acid to give 1-(b -acetylaminoethyl) - benzene - 4 - sulphonic acid chloride which is then reacted with 1,4-diamino benzene-2-sulphonic acid and hydrolysed. N - (4 - Nitro - 2 - sulphophenyl)ethylene diamine is prepared by reacting 4-chloro-1-nitrobenzene-3-sulphonic acid with ethylene diamine.