Phthalocyanine pigments: general principles
-
Robert Christie
und
Adrian Abel
Abstract
This chapter describes some of the fundamental chemical and structural principles underlying the phthalocyanine system. Historically, phthalocyanines had been isolated as insoluble blue products in the early twentieth century, although the structures were not established at the time. After the serendipitous re-discovery of metal complex phthalocyanines by industry, and the elucidation of their structures, copper phthalocyanine (CuPc) pigments were introduced industrially in the 1930s to become, and remain, by far the most important blue and green organic pigments, finding almost universal use as colorants for paints, printing inks, plastics, and a wide range of other applications. The phthalocyanines have become one of the most extensively studied classes of organic compounds, because of their unique molecular structures, light absorption properties that produce strong, bright colors, and their exceptionally high stability. While their dominant use is as colorants, they are also of interest for a range of other applications, for example in electronic devices, biological applications, and as catalysts.
References
1. Moser FH, Thomas AL. The phthalocyanines vols I and II. Boca Raton, Florida: CRC Press Inc; 1983.Suche in Google Scholar
2. Leznoff CC, Lever AB. Phthalocyanines: properties and applications. Weinheim: VCH; 1989.Suche in Google Scholar
3. McKeown NB. Phthalocyanine materials: synthesis, structure and function. Cambridge: Cambridge University Press; 1998.Suche in Google Scholar
4. H. Zollinger, Color Chemistry: Syntheses, Properties and Applications of Organic Dyes and Pigments, 3rd ed., ch. 5, Wiley-VCH, Weinheim, 2003.Suche in Google Scholar
5. Christie RM. Colour chemistry, 2nd ed. London: RSC, Ch 5: 2015.10.1039/9781782626510Suche in Google Scholar
6. Hunger K, Schmidt MU. Industrial organic pigments, 4th ed. Weinheim: Wiley-VCH Verlag GmbH, Ch 3; 2019.Suche in Google Scholar
7. De La Torre G, Bottari G, Hahn U, Torres T. Functional Phthalocyanines. Berlin: Springer-Verlag; 2010.Suche in Google Scholar
8. Tanaka M. Phthalocyanines – high performance pigments with new applications. In: Smith H, editor. High performance pigments. Wiley VCH, 2002; Ch. 17.10.1002/3527600493.ch17Suche in Google Scholar
9. Wainwright M. Photodynamic therapy - from dyestuffs to high-tech clinical practice. Rev Prog Color. 2004:34;95–109.10.1111/j.1478-4408.2004.tb00155.xSuche in Google Scholar
10. Wainwright M. Therapeutic applications of near-infrared dyes. Color Technol. 2010;26:115–26.10.1111/j.1478-4408.2010.00244.xSuche in Google Scholar
11. Nyokonga T, Gledhill I. The use of phthalocyanines in cancer therapy. Proc AIP Conf. 2013:49;1517.10.1063/1.4794220Suche in Google Scholar
12. Braun A, Tcherniak J. Über die Produkte der Einwirkung von Acetanhydrid auf Phthalamid. Ber Dtsch Chem Ges. 1907:40;2709.10.1002/cber.190704002202Suche in Google Scholar
13. 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.192701001110Suche in Google Scholar
14. Dandridge AG, Drescher HA, Thomas J. GB 322,169. 16 May 1928.Suche in Google Scholar
15. Bourne GT, Linstead RP, Lowe AR. Phthalocyanines. Part II. The preparation of phthalocyanine and some metallic derivatives from o-cyanobenzamide and phthalimide. J. Chem. Soc. 1934:1017.10.1039/jr9340001017Suche in Google Scholar
16. 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/jr9350000615Suche in Google Scholar
17. The discovery of a new pigment – the story of monastral blue by imperial chemical industries. http://www.colorantshistory.org/PhthaloDiscovery.html. Accessed: 14 Feb 2021.Suche in Google Scholar
18. Christie RM. Colour & constitution relationships in organic pigments, part 5, the influence of solvents, the central metal atom and substituents on the electronic spectra of phthalocyanines. Dyes Pigm. 1995:27;35–43.10.1016/0143-7208(94)00047-6Suche in Google Scholar
© 2020 Walter de Gruyter GmbH, Berlin/Boston
