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Encyclopedia Britannica



PRIMULINE

This article appears in Volume V22, Page 342 of the Encyclopedia Britannica.

Encyclopedia Britannica - Main :: PRE-PYR
PRIMULINE , a dye-stuff containing the thiazole ring
system
  conjointly with a 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
sulphur
  for eighteen
hours
  at 18oxgo C. and then for a further six
hours
  at 2002200 C. (P. Jacobson, Ber., 1889, 22, p. 333; L. Gattermann, ibid. p. 1084). Dehydrothiotoluidine is not itself a dye-stuff, but if the
heating
  be carried out at a higher temperature in the presence of more
sulphur
 , then a base is formed, which gives primuline yellow on sulphonation (A. G. Green, Journ. 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 developed with other components, so yielding a
series
  of ingrain colours.
Thioflavine T is obtained by the methylation of dehydrothiotoluidine with methyl
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 bleaching powder or with lead peroxide, in alkaline solution yields chloramine yellow, which dyes
cotton
  a beautiful yellow.


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