Perinone pigments

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. 

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. 

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 ... 

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. 

Commercially Available Perinone Pigments and Their Application... 

Perinones. The most important pigment in this family is the orange perinone, Pigment Orange 43 [4424-06-0] which is obtained by reaction of naphthalene-1,4,5,8-tetracarboxylic dianhydride with tf-phenylenediamine. The result is a mixture of the cis- and trans-isomers. The commercial product is the orange trans-compound which must be separated from the dull, bluish red cis-isomer, and then conditioned for pigment use. The pigment is fairly weatherfast and heat stable, and is used primarily in plastics and fiber applications. 

Perinones. The most important pigment in this family is the orange perinone. Pigment Orange 43 is fairly weatherfast and heat stable, and is used primarily in plastics and fiber applications. 

Loutfy et al. (1991) described the use of various vapor-deposited bisaiylimidazole perinone pigments as generation layers. These showed high sensitivity and excellent cycling stability. These materials usually show sensitivity to approximately 600 nm. With the bis(2,3-naphthimidazole) perinones, however, the sensitivity was extended to beyond 700 nm. 

Pyrene is mainly used in the production of 1,4,5,8-naphthalenetetracarboxylic acid, a starting material for perinone pigments, which are characterized e.g. by their good heat stability. 

Perylene and perinone pigments are closely related chemically and are manufaemred by essentially the same route. Perylenes are diimide derivatives of perylene-3,4,9,10-tetracarboxylic acid, while perinones are derivatives of naphthalene-1,4,5,8-tetracarboxylic acid (Herbst and Hunger, 1997). 

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