Anthraquinonoid pigments
-
Robert Christie
and
Adrian Abel
Abstract
Colorants based on the anthraquinone structure are categorized as a subclass of carbonyl colorants. Anthraquinone textile dyes rank second in importance to azo dyes, especially within the vat dye application class. Vat dyes became of interest to the pigment industry because of their insolubility. This insolubility and generally excellent fastness properties inspired investigations into the selection of suitable established anthraquinonoid vat dyes for use as pigments after conversion to a physical form that is appropriate for their applications. Originally this proved difficult, but was eventually achieved following the development of appropriate conditioning after treatment processes. The structural chemistry of the various types of anthraquinonoid pigments in relation to their technical and coloristic performance is discussed. The chapter concludes with an illustrated description of the main synthetic routes and finally with a description of the principal applications of the individual commercial products. Anthraquinonoid pigments are generally regarded as high-performance products, suitable for highly demanding applications, although they tend to be expensive.
References
1. Hunger K, Schmidt MU. Industrial organic pigments, 4th ed, Weinheim: Wiley-VCH Verlag GmbH, Ch 3 2019.Search in Google Scholar
2. Zollinger H. Color chemistry. Weinheim: Wiley VCH, Ch 8 2003.Search in Google Scholar
3. Christie RM. Colour chemistry, 2nd ed, London: RSC, Ch 4 2015.10.1039/9781782626510Search in Google Scholar
4. Bhardwaj H, Kamal K. Indian dyes and dyeing industry during the eighteenth-nineteenth century. Indian J Hist Sci. 1982;17:70–81.Search in Google Scholar
5. Graebe C, Liebermann C. Ueber Alizarin und Anthracen. Berichte der Deutschen Chemischen Gesellschaft. 1868;1:41–56.10.1002/cber.18680010120Search in Google Scholar
6. Ogawa K, Scheel HJ, Laves F. Kristallstrukturen organischer Pigmentfarbstoffe. II. 4,4′-Diamino-1,1′-dianthrachinonyl C28H16N2O4. Naturwissenschaften. 1966;53:700–1.10.1007/BF00602721Search in Google Scholar
7. Thetford D, Cherryman J, Chorlton AP, Docherty R. Intermolecular interactions of flavanthrone and indanthrone pigments. Dyes Pigm. 2005;67:139–44.10.1016/j.dyepig.2004.11.002Search in Google Scholar
8. Hallas G. In colorants and auxiliaries. In: Shore J, editor. Bradford: society of dyers and colourists. Ch 6 1990.Search in Google Scholar
9. Gordon PF, Gregory P. Organic chemistry in colour. Berlin: Springer-Verlag, Ch 2 1983.10.1515/9783112541746Search in Google Scholar
10. Gaertner H. Modern chemistry of organic pigments. J Oil Colour Chem Assoc. 1963;46:23–5.Search in Google Scholar
11. Bradley W, Leete E. Chemistry of indanthrone. Part 1. The mode of formation of indanthrone from 2-aminoanthraquinone and potassium hydroxide. J Chem Soc. 1951:2129.10.1039/jr9510002129Search in Google Scholar
© 2020 Walter de Gruyter GmbH, Berlin/Boston
