Carbonyl dyes

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Carbonyl dyes are dyes which comprise at least two conjugated carbonyl groups. Both anthraquinone dyes and indigo dyes belong to the group of carbonyl dyes. The most important natural dyes - indigo, Tyrian purple, alizarin and carmine - have this partial structure. The most important synthetic carbonyl dyes are based on anthraquinone.

The main advantages of carbonyl dyes are the possibility of reducing the carbonyl groups to water-soluble dienols (→Vat dyes), which is advantageous in industrial applications. On the other hand, by introducing suitable electron donating groups, the absorption maximum of the resulting dyes can be shifted to almost any region of the VIS spectrum. [1]

Carbonyl-Farbstoffe.svg
Reduction/Oxidation of carbonyl dyestuffs / examples: anthraquinone and indigo

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<span class="mw-page-title-main">Indigo</span> Shade of blue

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<span class="mw-page-title-main">Indigo dye</span> Chemical compound, food additive and dye

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<span class="mw-page-title-main">Anthraquinone</span> Chemical compound

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14
H
8
O
2
. Isomers include various quinone derivatives. The term anthraquinone however refers to the isomer, 9,10-anthraquinone wherein the keto groups are located on the central ring. It is a building block of many dyes and is used in bleaching pulp for papermaking. It is a yellow, highly crystalline solid, poorly soluble in water but soluble in hot organic solvents. It is almost completely insoluble in ethanol near room temperature but 2.25 g will dissolve in 100 g of boiling ethanol. It is found in nature as the rare mineral hoelite.

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<span class="mw-page-title-main">Anthraquinones</span>

For the parent molecule 9,10-anthraquinone, see anthraquinone

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A dihydroxyanthraquinone is any of several isomeric organic compounds with formula C
14
H
8
O
4
, formally derived from 9,10-anthraquinone by replacing two hydrogen atoms by hydroxyl groups. Dihyroxyantraquinones have been studied since the early 1900s, and include some compounds of historical and current importance. The isomers differ in the position of the hydroxyl groups, and of the carbonyl oxygens (=O) of the underlying anthraquinone.

<span class="mw-page-title-main">Anthraquinone dyes</span>

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Disperse dye is a category of synthetic dye intended for polyester and related hydrophobic fibers. Disperse dyes are polar molecules containing anthraquinone or azo groups. It is estimated that 85% of disperse dyes are azos or anthraquinone dyes.

The Bohn–Schmidt reaction, a named reaction in chemistry, introduces a hydroxy group at an anthraquinone system. The anthraquinone must already have at least one hydroxy group. The reaction was first described in 1889 by René Bohn (1862–1922) and in 1891 by Robert Emanuel Schmidt (1864–1938), two German industrial chemists.

References

  1. Heinrich Zollinger (2003), Color Chemistry: Syntheses, Properties, and Applications of Organic Dyes and Pigments (3. ed.), Weinheim: WILEY-VCH Verlag, pp. 255 ff., ISBN   3-906390-23-3