Perinone dyes

Dyes. l-Phenalone-6,7-dicarboxylic acid refluxed 3 hrs. with 1,8-diaminonaph-thalene in glacial acetic acid perinone dye. Y 90-95%. F. e. s. J. Arient, J. Dvorak, and V. Stepanek, Coll. 26, 1542 (1961). 

Keywords anthraquinone dyes, azine dyes, azo dyes, benzodifuranone dyes, color index, methine dyes, quinopthalone dyes, perinone dyes, photochromic dyes, sulfur dyes, vat dyes. 

The chemical classes of vat colours from which suitable pigments have been developed are anthraquinones, perinones, perylenes and thioindigos. Many vat dyes have been tested, but only about a dozen have met the stringent fastness standards demanded. Seven of those found suitable in all respects are shown in Table 2.1 and their chemical structures are given as 2.4 to 2.10. 

In this section a number of polycyclic pigments are discussed which have been used for a long time as vat dyes for textile fibers. Heading the list are perylene, perinone, and thioindigo pigments, as well as pigments derived from anthraquinone. 

Members of both groups are manufactured by essentially the same route. Starting from the anhydrides of 67 and 68, formation of bisimido or, respectively, bisim-idazole compounds is accomplished with amines or diamines. The compounds have been known as vat dyes since 1913 (perylenes) and 1924 (perinones). 

Of particular interest, especially in the production of greenish-yellow dyes, are the naphthoylbenzimidazoles (44). Depending upon the nature of the substitution of the molecule the whole spectrum of colours from yellow to blue is obtainable (66FRP1440053, 71GEP2036136). The structurally somewhat similar pendant quaternary perinones (45) have also proved to be of interest (67FRP1489639). 

The two major classes of dyes used in melt coloring polymeric materials are the anthraquinones and the perinones. Between the two they offer the colorist a complete range of colors from yellow to violet - and many are suitable for use in polyamide blends and alloys. 

Newly developed perinones are being offered for mass coloration of nylon. As these dyes are non-reactive to the polyamide carrier, they give good performance in these resin systems. Structures have not been disclosed. Perinones show excellent light and heat stability in most resins. 

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