Bisacetoacetarylide pigments

The fact that only a few of these pigments enjoy commercial importance eliminates the need to treat each individual species separately. 

Bisacetoacetarylide pigments are considered disazo pigments that are obtained from bifunctional coupling components. The latter are obtained by bisacetoace-tylation of aromatic diamines, especially of 4,4 -diaminodiphenyl or 1,4-di-aminophenyl derivatives with 2 equivalents of diketene or acetoacetic ester  

Only common aromatic amines are used as diazonium components. Coupling reactions between aminobenzamides or aminobenzanilides and bisacetoacetylamino-phenylenes are described under disazo condensation pigments (see Sec. 2.9). Bisacetoacetarylide pigments thus have the general chemical structure  

Bisacetoacetarylide pigments are characterized by good solvent resistance and tinctorial strength although they are not quite as strong as diarylide yellow pigments. 

The large number of patents describing bisacetoacetarylide pigments based on the bifunctional coupling components 1,4-bisacetoacetylaminobenzene and its derivatives [9] is somewhat in contrast to the fact that the products have gained only limited commercial importance. 

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Bis(acetic acid)trifluoroborane, 4 144t Bisacetoacetarylide, pigment for plastics, 7 366t... 

Similarly, bisacetoacetarylide pigments obtained from 4,4 -bisacetoacetyl-aminodiphenyl derivatives as coupling components are of little commercial value. One exception is Pigment Yellow 16,20040 ... 

Commercially Available Bisacetoacetarylide Pigments and Their Properties... 

The pigment affords medium yellow shades. Regarding shades and performance it competes with some other pigments, such as the monoazo pigment P.Y.97 and the bisacetoacetarylide pigment P.Y.16. 

The yellow members of this pigment class are obtained by coupling a diazotized aminobenzoic acid with a bisacetoacetarylide, followed by conversion to a diacid chloride and reaction with a substituted aromatic amine. An example is Pigment Yellow 93 [5580-57-4] (Fig. 2b). 

Extension of bisacetoacetarylide disazo pigments by condensation of an anilide onto the diazobase unit carrying a carboxylic group to yield type I yellow pigments (1). 

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