Excerpt from The Influence of Sulphur on the Color of Azo Dyes: Dissertation Submitted to the Board of University Studies of the Johns Hopkins University in Conformity With the Requirements for the Degree of Doctor of Philosophy

The dyes from thio-aniline, thio-aniline sulfone and the diamine from mustard gas when c6upled with various intermediates are contrasted with those from benzidine. The color? Are given in Table XIV. This series of colors indicates that where the diphenyl rings are separated by sulfur, sulfone and other groups, they no longer possess the properties of benzidine, which gives colors varying from deep reds to blues and violets. The thio-aniline and its sulfone give much lighter colors, differing Slightly but practically in the same range of the spectrum as those obtained from the mono-amines coupled with the same acids, though the molecular weight is greater than that of the benzidine dyes and approximately double that of the mono-amine series. The dyes containing three sulfur atoms, with the mustard gas residue between, are also slightly lighter than those from thio-aniline.

In this series the sulfur divides the molecules, so that the colors obtained appear as if each half were acting as a unit, while with benzidine the effect of each group is felt in the opposite ring.

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