Perylene and perinone pigments
-
Robert Christie
and
Adrian Abel
Abstract
Perylenes and perinones are separate groups of pigments categorized within the carbonyl chemical class. The two pigment groups show similarities, for example, in their chemical structural features and, to an extent, in their technical and application properties as high-performance organic pigments. Perylenes constitute a series of firmly established high-performance pigments, offering red and violet colors, and also extending to black. Synthetically, they are derived from perylene-1,4,5,8-tetracarboxylic acid. The perylenes tend to be quite expensive pigments, but their high levels of fastness properties mean that they are suitable for highly demanding applications. In particular, they offer very high heat stability. Two perinone pigments are used commercially. In their synthesis from naphthalene-1,4,5,8-tetracarboxylic acid, they are formed as mixtures of the two isomers, which can be separated. The trans isomer, CI Pigment Orange 43, is a highly important commercial pigment, especially for plastics, while the cis isomer, CI Pigment Red 194, is bordeaux in color and is of much lesser importance. The perinone, CI Pigment Orange 43, provides a brilliant orange color and has very good fastness properties. Its commercial manufacture involves a challenging multistage procedure and consequently it is one of the most expensive organic pigments on the market.
References
1. Hunger K, Schmidt MU. Industrial organic pigments, 4th ed, Weinheim: Wiley-VCH Verlag GmbH, Ch 3 2019.Search in Google Scholar
2. Thompson B. Perylene pigments. In: Faulkner EB, Schwartz RJ, editors. High performance pigments, 2nd ed. Weinheim: Wiley-VCH Verlag GmbH, 2009 Ch 16.Search in Google Scholar
3. Christie RM. Colour chemistry, 2nd ed, London: RSC, Ch 9 2015.10.1039/9781782626510Search in Google Scholar
4. Lewis P. Colored organic pigments. Appl Polym Sci Twenty-first Century. 2000;493–526. .10.1016/B978-008043417-9/50029-5Search in Google Scholar
5. Nagao Y. Synthesis and properties of perylene pigments. Prog Org Coat. 1997;31:43–9.10.1016/S0300-9440(97)00017-9Search in Google Scholar
6. Klebe G, Graser F, Hadicke E, Berndt J. Crystallochromy as a solid-state effect; correlation of molecular conformation, crystal packing and color in perylene-3,4:9,10-bis(dicarboximide) pigments. Acta Crystallogr. 1989;B45:69–77.10.1107/S0108768188010407Search in Google Scholar
7. Mizuguchi J. Electronic structure of perylene pigments as viewed from the crystal structure and excitonic interactions. J Phys Chem. 2002;106:767–72.10.1021/jp012909pSearch in Google Scholar
8. Christie RM. Fluorescent dyes. Rev Prog Color. 1993;23:1–18.10.1533/9780857093974.2.562Search in Google Scholar
9. Christie RM. Fluorescent dyes. In: Clark M, editor. Handbook of textile and industrial dyeing: principles, processes and types of dyes. vol. 1, Cambridge: Woodhead Publishing, 2011 ch.17.10.1533/9780857093974.2.562Search in Google Scholar
10. Mizuguchi J. Crystal structure and electronic characterization of trans-and cis-perinone pigments. J Phys Chem B. 2004;108:8926–30.10.1021/jp031351dSearch in Google Scholar
11. Merkle K, Schäfer H. In: Patton TC, editor. In pigment handbook, vol. 3, New York: John Wiley and Sons, 1973:157–67.Search in Google Scholar
12. Tapmeyer L, Bolte M, Chierotti MR, Schmidt MU. Structure of the intermediates in the industrial separation of perinone isomers. Dyes Pigm. 2020;181:108442.10.1016/j.dyepig.2020.108442Search in Google Scholar
13. https://echa.europa.eu/documents/10162/c607549c-1c07-c5d6-d6e2-8d18bff91f3a. Accessed: 6 Apr 2021.Search in Google Scholar
14. https://www.clariant.com/en/Solutions/Products/2014/03/18/17/10/Hostaperm-Orange-GR-for-Paints-and-Coatings. Accessed: 6 Mar 2021.Search in Google Scholar
15. https://www.clariant.com/en/Solutions/Products/2014/03/18/17/14/PV-Fast-Orange-GRL. Accessed: 6 Mar 2021.Search in Google Scholar
16. https://www.clariant.com/en/Solutions/Products/2014/10/14/15/12/Hostaperm-Orange-GR-for-Printing. Accessed: 6 Mar 2021.Search in Google Scholar
© 2020 Walter de Gruyter GmbH, Berlin/Boston
