Abstract
Copper phthalocyanine is the dominant blue organic pigment by far, used extensively in printing ink, paint, plastics, and a range of other applications. A historical perspective of the development of phthalocyanine pigments, from their original serendipitous discovery, through the characterization of their molecular structures, to their development as pigments, is discussed in this chapter and in the separate chapter entitled Phthalocyanines: General Principles. Copper phthalocyanine exhibits polymorphism. The α- and β-forms are the most important crystal phases used as pigments, while the ε-form has only minor significance. Although structurally complex, the synthesis of copper phthalocyanine is relatively straightforward, involving readily available commodity starting materials to provide the products in high yield. After-treatments are required not only to convert the crude pigment into an appropriate pigmentary physical form, but also to provide stability towards crystal phase change and flocculation in application.
References
1. Moser FH, Thomas AL. The phthalocyanines vols I and II. Boca Raton, Florida: CRC Press Inc, 1983.Search in Google Scholar
2. Leznoff CC, Lever AB. Phthalocyanines: properties and applications. Weinheim: VCH, 1989.Search in Google Scholar
3. McKeown NB. Phthalocyanine materials: synthesis, structure and function. Cambridge: Cambridge University Press, 1998.Search in Google Scholar
4. Zollinger H. Color chemistry: syntheses, properties and applications of organic dyes and pigments, 3rd ed ch. 5. Weinheim: Wiley-VCH, 2003.Search in Google Scholar
5. Christie RM. Colour chemistry, 2nd ed, London: RSC, Ch 5: 2015.10.1039/9781782626510Search in Google Scholar
6. Hunger K, Schmidt MU. Industrial organic pigments, 4th ed, Weinheim: Wiley-VCH Verlag GmbH, Ch 3; 2019.Search in Google Scholar
7. de Diesbach H, Von Der Weid E. Quelques sels complexes des o-dinitriles avec le cuivre et la pyridine. Helv Chim Acta. 1927;10:886.10.1002/hlca.192701001110Search in Google Scholar
8. Fox M R. Dyemakers of Great Britain, 1856 – 1976. Manchester: Imperial Chemical Industries PLC; 1987.Search in Google Scholar
9. Eastaugh N, Walsh V, Chaplin T, Siddall R. Pigment compendium. Abingdon: Routledge 2008.10.4324/9780080943596Search in Google Scholar
10. Robertson JM. An X-ray study of the structure of the phthalocyanines. Part I. The metal-free; nickel, copper and platinum compounds. J Chem Soc. 1935;613.10.1039/jr9350000615Search in Google Scholar
11. Brown CJ. Crystal structure of β-copper phthalocyanine. J. Chem. Soc (A). 1968:2488.10.1039/J19680002488Search in Google Scholar
12. Honigman B, Lenne HU, Schrodel R. Beziehungen zwischen den Stukturen der Modifikation des Platin- und Kupferphthalocyanins und einiger Chlorderivate. Z Krystallog. 1965:122; 185–205.10.1524/zkri.1965.122.3-4.185Search in Google Scholar
13. Fryer JR, McKay RB, Mather RR, Sing KS. The technological importance of the crystallographic and surface properties of copper phthalocyanine pigments. J Chem Tech Biotechnol. 1981:31;371.10.1002/jctb.280310152Search in Google Scholar
14. Christie RM, Deans D. An investigation into the mechanism of the phthalonitrile route to copper phthalocyanines using differential scanning calorimetry. J Chem Soc Perkin. 1989:2; 193–8.10.1039/p29890000193Search in Google Scholar
15. Endriβ H. Brilliant solutions: Heliogen – the copper phthalocyanine pigments of BASF, 2nd ed. EFO 9906e, 2001.Search in Google Scholar
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