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d Schorlemmer, and the Fischers--which led up to the discovery of the constitution of the colouring-matters of the rosaniline group, and, through this, to the far-reaching industrial developments of the discovery as traced in the last chapter. It is evident, from what has been said, that rosolic acid and its related colouring-matters are members of the triphenylmethane group. They are in fact the hydroxylic or acid analogues of the amido-containing or basic dyes of the rosaniline series. In the fragrant blossom of the meadowsweet (_Spiraea ulmaria_) there is contained an acid which is found also as an ether in the oil of wintergreen (_Gautheria procumbens_). This is salicylic acid, a white crystalline compound which has been known to chemists since 1839. In 1860 Kolbe prepared the sodium salt of this acid by passing carbon dioxide gas into phenol in which metallic sodium had been dissolved. It was found subsequently that the same transformation was brought about by heating the dry sodium salt of carbolic acid in an atmosphere of carbon dioxide. This process of Kolbe's is now worked on a manufacturing scale for the preparation of artificial salicylic acid. The acid and its salts and ethers find numerous applications as antiseptics, for the preservation of food, and in pharmacy. Salicylic acid is employed also for the manufacture of certain azo-dyes in a way that it will be very instructive to consider, because the process used may be taken as typical of the general method of preparing such compounds. Solutions of diazo-salts act not only upon amido- and diamido-compounds, as we have seen in the case of aniline yellow and chrysoidine, but also upon phenols, forming acid azo-colours. This important fact was made known in 1870 by the German chemists Kekule and Hidegh, but more than six years elapsed before this discovery was taken advantage of by the technologist. Large numbers of these acid azo-dyes are now made from various diazotised amido-compounds combined with different phenols and phenolic acids. The mode of procedure is to diazotise the amido-compound by sodium nitrite and hydrochloric acid in the manner already described, and then add the diazo-salt solution to the phenolic compound dissolved in alkali. The colouring-matter is at once formed. Salicylic acid possesses the characters both of an acid and a phenol. It combines readily with diazo-salts under the circumstances described, and gives rise to azo-dyes, so
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