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Is there such a thing as a dye that can stain both oil and water? In other words, does anyone know of an amphiphilic dye? Maybe a surfactant that is also a pretty shade of blue? Or maybe turn one color in oil, but another in water, but stain both well?
Thanks

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  • $\begingroup$ Perhaps not a direct answer to your question, but I would imagine that anionic, water-soluble dyes could be transferred into organic solvents by use of a phase-transfer catalyst. $\endgroup$ – Greg E. Dec 20 '13 at 5:26
  • $\begingroup$ A napthalimide made with a PEO oligomer amine might split the difference in Day-Glo, doi:10.1016/j.jphotochem.2010.09.002 $\endgroup$ – Uncle Al Mar 13 '14 at 0:52
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The diazo dye (1), known as Solvent Yellow 124 or Somalia Yellow is soluble in aliphatic hydrocarbons. In the European Community, it is used to mark low-taxed diesel fuel (for heating purposes). In order to prevent its use in cars, samples are acidified. This results in acetal cleavage and protonation of the diazo-fragment, yielding the red, water-soluble iminoquinone species (2)

solvent-yellow-124 hydrolysis and protonation

Since this is probably not exactly what you wanted, what about dyes that exist in a neutral and a zwitterionic form, depending on the polarity of the solvent?

brooker' merocyanine: neutral and zwitterionic form

Brooker's merocyanine is one of the most prominent examples and show strong solvatochromism, i.e. the colour changes with the polarity of the solvent

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