Alizarin red dye

Alizarin. There is only one significant plant anthraquinone dye, alizariu [72-48-0] (Cl Natural Red 6, 8, 9,10, 11, and 12 Cl 75330). In ancient times, alizaria was the preferred red dye. Cloth dyed with it has been found in Egyptian tombs dating 6000 years ago. The dye is found in the madder plant, a member of the Rubiaceae family. In 1944 about 35 species of this plant were known (1), but the use of more sophisticated analytical methods led to the detection of many more species by 1984 the number had increased to 50 (2). Of these, tinctorum and R peregrina yield the greatest amount of dye,... 

The use of the mordanting process with the natural red dye alizarin to form the metal complex dye Turkey Red (so-called because the color was like that found on a turkey s neck), was one of the first examples of the preparation and use of a metal complex colorant. 

The British are coming, the British are coming cried Paul Revere. Well, he could hardly have missed them, decked out in their bright red coats. The attire of the British soldier tended to undermine military strategy, but the color had nothing to do with battle tactics. It had to do with economics. The British uniforms were required, by royal decree, to be dyed red in order to support British agricultural interests, specifically the cultivation of the madder plant (Rubia tinctorum). It was from the roots of this plant that the brilliant red dye known as alizarin was extracted. Alizarin was not produced in the colonies, and... 

During the 1860s Perkin turned his attention to alizarin, wondering if this substance could also be produced synthetically. By 1869 he was making the red dye in his laboratory. The... 

Besides these, use is also made (especially for dyeing wool), under the name of alizarin red, of the sodium salts of the respective sulphonic derivatives, which form orange-yellow powders... 

Red-wood and other dye-woods generally behave like logwood. Add alizarin reds are also extracted. 

Ping et al. have fabricated an integrated microsensor array on a silicon wafer for pH imaging [89]. Six different pH-sensitive colorimetric dyes (methyl violet 6B, phenolic red, alizarin complexone, 5-carboxy-fluorescein, alizarin red and methylthymol blue) were used to cover the whole pH range. The dyes were adsorbed on microbeads and placed in etched microwells on the silicon wafer. The indicator array was also used as a cation sensor chip (see Sect. 2.4). 

Hydroxyanthraquinone derivatives, especially alizarine red S (fig. 67), also form 1 1 complexes with Ybm ions (Korovin et al., 1988). The observed lifetimes are very short, around 0.3 ps, but comparable to those listed in table 15 for the complexes with triphenylmethane dyes. The relative luminescence intensities of Ybm complexes with several different dyes are summarized in fig. 68. The intensities are given relative to the more luminescent complex, with phthalexon S. It is noteworthy that all these complexes have absorption maxima at wavelengths longer than 500 nm, between 505 nm for thorin I and 590 nm for methylthymol blue H475d, and can thus be excited by the 546 nm-emission line of a mercury lamp. 

Liu G, Wu T, Zhao J, Hidaka H, Serpone N. Photoassisted degradation of dye pollutants. 8. Irreversible degradation of alizarin red under visible light radiation in air-equilibrated aqueous Ti02 dispersions. Environ Sci Technol 1999 33 2081-7. 

Faouzi, A. M., Nasr, B. and Abdellatif, G. (2007), Electrochemical degradation of anthraquinone dye alizarin reds by anodic oxidation on boron-doped diamond. Dyes Pigments, 73(1) 86-89. 

The recently discovered methods of producing iron and steel, such as the processes of Bessemer, Siemens, Gilchrist-Thomas, etc., cut to a minimum at relatively small costs the formerly arduous processes. The making of alizarin, a red dye-stuff extracted from coal-tar, requires but a few weeks, and this by means of already existing coal-tar dye-producing installations, to yield the same results which formerly required years. It took a year for the madder to mature, and it was customary to let the roots grow a few years more before they were processed.8... 

Technical Observations Alizarin was the first naturally occurring coloring matter which was successfully prepared synthetically on a commercial scale. This synthesis was a triumph for the then young coal-tar dye industry, and for a long time alizarin was its most important product. The world production of alizarin (as 100 per cent material) was about 2,800,000 kilograms yearly, of which the Badische A.S.F. supplied 2,000,000 kilograms. In more recent times, the consumption of alizarin has been greatly reduced as a result of the competition of more easily applied red dyes of the azo series, especially some of the equally fast naphthol AS combinations. 

The blue dye indigo, derived from the plant Indigofera tinctoria, has been used in India for thousands of years. Traders introduced it to the Mediterranean area and then to Europe. Tyrian purple, a natural dark purple dye obtained from the mucous gland of a Mediterranean snail of the genus Murex, was a symbol of royalty before the collapse of the Roman empire. Alizarin, a bright red dye obtained from madder root Rubia tinctorum), a plant native to India and northeastern Asia, has been found in cloth entombed with Egyptian mummies. 

The type of complex can vary depending upon the dye, the metallic ion, and the reaction conditions. There are too many to be covered here, but commercial examples of the more familiar types might be considered. The first is the 1 1-chromium complex of acid alizarin red C, a zwitterion type 34) ... 

Nitro, amino and sulphonic acid derivatives of alizarin are also dyes of various colors and are known as alizarin orange, alizarin maroon, alizarin red, etc. Also there is present in the madder root another dye compound known as puipurin which is 1-2-4-tri-hydroxy anthraqui-none. Isomeric tri-hydroxy anthraquinones are dyes also but it is interesting that in all of these poly-hydroxy anthraquinones which are dyes two of the hydroxyls are always in the 1-2 positions. 

Thin sections were prepared /or 28 samples following impregnation with blue-dye epoxy resin, and stained for calcite and K-feldspar using alizarin red S and potassium ferrocyanide, respectively. The thin sections were systematically scanned by the senior author to determine rock composition, porosity and textural relationships. 

Four anthraquinonic dyes, Alizarin red S, Alizarin violet R, Acid green 25, and Acid blue 129 are presented. The simplest one, the Alizarin red S, is derived from alizarine by the introduction of a sulphonate group in the alizarine structure in position 3 (Fig. 7). 

Figure 9. Alizarin red S monohydrate dye UV-visible spectra (water, pathlength 2 mm).

Perkin left school after patenting his discovery, but promised himself that he would return to research one day. He and members of his family soon formed a company to mass-produce mauve from coal tar, and in 1859 the Perkin and Sons factory commenced production. Mauve mania, however, was short-lived, and within a few years the red dyes fuchsia (or magenta) and alizarin were the craze. Perkin was quick to capitalize on these manias, and made an immense fortune in the process. 

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