Abstract
A series of synthetic organic pigments (SOP’s) with azo-containing linkages have been synthesized and characterized by Fourier transform infrared (FTIR) and Raman spectroscopies and laser desorption ionization mass spectrometry (LDI-MS). These pigments include representatives of the chemical classes arylide (Hansa) yellow, diarylide yellow and oranges, and Naphthol AS. Certain of these (PR7, PR10, PR11, PR18, PR19, PO14, PO15, PO16, PY49, PY98, PY106, PY113, PY124, PY203) are historical pigments, that is they were manufactured but subsequently were removed from production. Of these, some have been brought back into limited production. In addition to the above-mentioned pigments, 18 products of azo-linkage reactions formed between N,N′-bis(acetoacetyl)-o-toluidine and substituted anilines have been synthesized and characterized by the methods listed above as well as by visible reflectance spectroscopy. While not commercially available azo pigments, these colorants will serve as model systems to study substituent effects on pigment color.
Highlights
Materials or substances pre-exist every created object, whether cultural, as a work of art, or chemical, as in a pigment or dyestuff
We found for the compounds we synthesized, the amount of acetonitrile did not change the nature of the solution so much that the product dissolved, thereby maintaining one of the defining characteristics of a pigment: its insolubility
In preparation for investigation of substituent-effects on extended conjugated pigment systems in synthetic organic pigment (SOP)’s, we report on the synthesis a series of azo pigments based on
Summary
Materials or substances pre-exist every created object, whether cultural, as a work of art, or chemical, as in a pigment or dyestuff. LDI-MS, which can be performed in both positive and negative ion modes, provides pigment-specific information including the molecular weight and fragmentations [5, 6]. The pigments were synthesized by a classic diazotization reaction, reacting an in situ generated diazonium salt with an appropriately functionalized coupling component.
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