Add time:09/07/2019         Source:sciencedirect.com

Leucoquinizarin reacted with butylamine to give 1-butylamino-4-hydroxyanthraquinone and 1,4-bis(butylamino)anthraquinone. Their structures were elucidated and the reaction mechanism was discussed from the kinetic studies. Quinizarin reacted with butylamine to give 2-butylaminoquinizarin selectively, even in the presence of sodium dithionite. Under a nitrogen atmosphere, quinizarin was butylaminated to give 1-butylamino-4-hydroxyanthraquinone and/or 1,4-bis(butylamino)anthraquinone, even in the absence of sodium dithionite. Effects of sodium dithionite, solvent, and reaction atmosphere were examined and the animation mechanism was also discussed. The structures of leuco compounds of naphthazarin, its butylamino derivatives were clarified and the amination mechanism was also discussed. Leuconaphthazarin dyed wool and human hair in water without any oxidants at 30 °C to give reddish purple and an addition of benzyl alcohol accelerated the dyeing, which did not remove at all, even in 25% pyridine solution under refluxing conditions. The chemical interaction between naphthazarin and keratin was proposed from Raman and microphotomeric spectra. Leuco-2-butylaminonaphthazarin dyed wool and human hair in the presence of ammonia. On the other hand, the dyeabilities of leuco compounds of quinizarin, 1-butylamino-4-hydroxyanthraquinone and 1,4-bis(butylamino)anthraquinone was quite low compared to naphthazarin derivatives. This method which utilize isolable leuco compounds is the first attempt for dyeing wool and human hair.

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