Perinones

Pigment Orange 43 [4424-06-0] 71105 Perinone condensation of naphthalene-1,4,5,8-tetracarboxyhc acid dianhydride with o-phenylenediamine, and separation of trans isomer... 

Perilla ketone — see Ketone, 3-furyl isopentyl Perillene synthesis, 4, 668 Perinones, 1, 327, 337 Periodinane, bromo-synthesis, 1, 571 Periodinane, difluoro-reactions, 1, 571 Periodinanes cyclic... 

Perylenes (70) are diimides of perylene-3,4,9,10-tetracarboxylic acid, and may be prepared by reaction of the bis-anhydride of this acid, 89 (1 mol) with the appropriate amine (2 mol) in a high-boiling solvent as illustrated in Scheme 4.11. The synthesis of perinones 71 and 72 involves condensation of naphthalene-1,4,5,8-tetracarboxylic acid with benzene-1,2-diamine in refluxing acetic acid. This affords a mixture of the two isomers, which may be separated by a variety of methods, generally involving their differential solubility in acids and alkalis. 

Carbonyl pigments of a variety of types may also be classed as high-performance products. These include some anthraquinones, quinac-ridones, perylenes, perinones, isoindolines and diketopyrrolopyrroles. The chemistry of these groups of colorant is discussed in Chapter 4. Some representative examples of chemical structures of important high-performance carbonyl pigments are illustrated in Figure 9.4. 

Perikinetic flocculation, 22 55 Perindopril, molecular formula and structure, 5 15 It Perinone Orange... 

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. 

Perylene pigments include the dianhydride and diimide of perylene tetracarboxylic acid along with derivatives of the diimide while perinone pigments are derived from naphthalene tetracarboxylic acid. 

To obtain the necessary fastness properties, high-quality pigments are generally used for security printing. The range of suitable products covers disazo, disazo condensation, benzimidazolone, naphthol AS, isoindolin, perinone, anthanthrone, dioxazine and quinacridone pigments. 

P.O.5 is in high demand in the field of the textile printing. As far as most of the relevant fastness properties are concerned, P.O.5 performs less well than the somewhat yellower and much more expensive perinone pigment P.O.43. Compared to the somewhat yellower P.O.34, however, its fastness to light is superior. 1/3 SD P.O.5 samples equal step 7 on the Blue Scale, as opposed to step 5-6 reached by P.O.34. In other respects, such as fastness to dry-cleaning with perchloroethylene or petrolether, to laundering with peroxide bleach or alkali, P.O.5 performs less well than P.O.34. 

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. 

Perylene and perinone pigments are chemically related. The group of perylene pigments is derived from perylene-3,4,9,10-tetracarboxylic acid 67, while perinone pigments are derivatives of napthalene-l,4,5,8-tetracarboxylic acid 68 ... 

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). 

Perinone pigments are obtained from naphthalene-1,4,5,8-tetracarboxylic acid or its monoanhydride. 

The synthetic route to perinone pigments, as to perylene pigments, starts from an anhydride, in this case from the monoanhydride of naphthalene tetracarboxylic acid. 

The perinone ring system is thus formed by condensation with aromatic o-di-amines. Reaction of o-phenylenediamine with the monoanhydride is typically achieved in glacial acetic acid at 120°C. A mixture of the cis and trans isomers evolves, which appear as mixed crystals ... 

Commercially Available Perinone Pigments and Their Application... 

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