Disazo (Bishydrazone) pigments based on acetoacetanilides

Abstract

Disazoacetoacetanilide pigments, more commonly known as diarylide yellows, are the most important group of yellow classical organic pigments. They were commercialized in the early 20th century many years after the introduction of the structurally related monazoacetoacetanilides (Hansa yellows). The molecules adopt the bis-ketohydrazone tautomeric form. X-ray single crystal structure investigations have provided an insight into the influence of the molecular geometry and crystal packing arrangements in the solid state on the properties of the pigments in application. The synthesis of diarylide pigments is relatively straightforward, the conditions essentially following those used for the corresponding monoazo pigments, so that the products are economically priced. In the case of these disazo pigments, suitable aromatic amines (1 mol) are bis-diazotized and the resulting bis-diazonium salts reacted with acetoacetanilide coupling components (2 mol), the two azo coupling reactions occurring at the same time. They are by far the dominant group of yellow pigments used in printing inks, well-suited for most standard process yellow inks. They were formerly important in the coloration of plastics but are no longer recommended for polymers processed above 200 °C, under which conditions toxic decomposition products are formed. Diarylide yellow pigments are characterized by high color strength, good to excellent solvent fastness, and good chemical stability, although they generally show inferior lightfastness.