Online Encyclopedia

PRIMULINE

Online Encyclopedia
Originally appearing in Volume V22, Page 342 of the 1911 Encyclopedia Britannica.
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PRIMULINE  , a dye-stuff containing the thiazole

ring
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system conjointly with a
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benzene ring . The primulines are to be considered as derivatives of dehydrothiotoluidine (aminobenzenyltoluylmercaptan), which is obtained when para-tolui- S\ CH „/\/ •CBH4.NH,(p) \/\N/ Primuline . dine is heated with
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sulphur for eighteen hours at 18o–xgo C. and then for a further six hours at 200–2200 C . (P . Jacobson, Ber., 1889, 22, p . 333; L . Gattermann, ibid. p . 1084) . Dehydrothiotoluidine is not itself a dye-stuff, but if the
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heating be carried out at a higher temperature in the presence of more sulphur, then a
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base is formed, which gives primuline yellow on sulphonation (A . G . Green, Journ .
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Soc .

Chem . Ind., 1888, r, p . 194) . Primuline-yellow is a mixture of

sodium salts and probably contains in the molecule at least three thiazole rings in combination . It is a substantive cotton dye of rather fugitive shade, but can be diazotized on the fibre and then
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developed with other components, so yielding a series of ingrain colours . Thioflavine T is obtained by the methylation of dehydrothiotoluidine with methyl
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alcohol in the presence of hydrochloric acid [German Patent 51738 (1888)] . Thioflavine S results from the methylation of dehydrothiotoluidine sulphonic acid . This sulphonic acid on oxidation with
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bleaching powder or with lead peroxide, in alkaline solution yields chloramine yellow, which dyes cotton a beautiful yellow .

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